# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_1-DEF
_database_code_depnum_ccdc_archive 'CCDC 1504253'
_audit_update_record             
;
2016-09-15 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H32 Cl N5 O4 S'
_chemical_formula_moiety         'C25 H32 Cl N5 O4 S'
_chemical_formula_weight         534.07
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.26161(11)
_cell_length_b                   25.9240(5)
_cell_length_c                   8.62429(16)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.2264(7)
_cell_angle_gamma                90.0000
_cell_volume                     1368.19(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13125
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564.00
_exptl_absorpt_coefficient_mu    2.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.420
_exptl_absorpt_correction_T_max  0.634

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            14234
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_min         3.410
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4864
_reflns_number_gt                4055
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    0.938

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.2054
_refine_ls_wR_factor_gt          0.1847
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4864
_refine_ls_number_parameters     329
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1289P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.48
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.00(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.9288(7) 0.38357(10) 0.2103(5) 0.1318(14) Uani 1 1 d . . . . .
S1 S 0.3263(2) 0.59154(5) 0.63211(15) 0.0416(4) Uani 1 1 d . . . . .
O1 O 0.5566(7) 0.5924(2) 0.6247(5) 0.0539(10) Uani 1 1 d . . . . .
O2 O 0.1872(8) 0.59971(18) 0.4780(5) 0.0562(11) Uani 1 1 d . . . . .
O3 O 0.2789(9) 0.62566(18) 0.7525(6) 0.0608(13) Uani 1 1 d . . . . .
O4 O 0.5973(10) 0.7270(2) 0.3809(9) 0.0809(17) Uani 1 1 d . . . . .
N1 N 0.1218(10) 0.3805(2) 0.8396(8) 0.0590(14) Uani 1 1 d . . . . .
N2 N 0.2801(10) 0.3546(2) 0.9146(7) 0.0524(13) Uani 1 1 d . . . . .
N3 N 0.1264(10) 0.1571(2) 1.1269(7) 0.0532(13) Uani 1 1 d . . . . .
H3A H 0.2374 0.1381 1.1704 0.064 Uiso 1 1 calc R U . . .
H3B H -0.0059 0.1453 1.1169 0.064 Uiso 1 1 calc R U . . .
N4 N 0.7428(10) 0.6276(2) 0.3747(7) 0.0521(13) Uani 1 1 d . . . . .
H4A H 0.8879 0.6234 0.4082 0.063 Uiso 1 1 calc R U . . .
H4B H 0.6727 0.6104 0.4397 0.063 Uiso 1 1 calc R U . . .
H4C H 0.7096 0.6614 0.3755 0.063 Uiso 1 1 calc R U . . .
N5 N 0.3179(12) 0.7726(3) 0.4413(11) 0.079(2) Uani 1 1 d . . . . .
C1 C 0.2728(11) 0.5283(2) 0.6921(7) 0.0469(14) Uani 1 1 d . . . . .
C2 C 0.4360(12) 0.4990(3) 0.7820(9) 0.0592(17) Uani 1 1 d . . . . .
H2 H 0.5790 0.5122 0.8084 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3933(11) 0.4504(3) 0.8341(9) 0.0574(17) Uani 1 1 d . . . . .
H3 H 0.5062 0.4311 0.8975 0.069 Uiso 1 1 calc R U . . .
C4 C 0.1863(12) 0.4302(3) 0.7932(9) 0.0553(16) Uani 1 1 d . . . . .
C5 C 0.0217(15) 0.4595(4) 0.7043(14) 0.091(3) Uani 1 1 d . . . . .
H5 H -0.1213 0.4463 0.6776 0.110 Uiso 1 1 calc R U . . .
C6 C 0.0666(13) 0.5085(3) 0.6538(13) 0.086(3) Uani 1 1 d . . . . .
H6 H -0.0466 0.5282 0.5926 0.104 Uiso 1 1 calc R U . . .
C7 C 0.2225(11) 0.3055(2) 0.9642(7) 0.0460(14) Uani 1 1 d . . . . .
C8 C 0.3987(12) 0.2749(3) 1.0349(9) 0.0546(16) Uani 1 1 d . . . . .
H8 H 0.5411 0.2880 1.0464 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3700(11) 0.2258(3) 1.0885(8) 0.0503(14) Uani 1 1 d . . . . .
H9 H 0.4921 0.2058 1.1348 0.060 Uiso 1 1 calc R U . . .
C10 C 0.1599(10) 0.2058(2) 1.0741(7) 0.0422(13) Uani 1 1 d . . . . .
C11 C -0.0175(11) 0.2362(3) 1.0018(8) 0.0482(14) Uani 1 1 d . . . . .
H11 H -0.1600 0.2230 0.9891 0.058 Uiso 1 1 calc R U . . .
C12 C 0.0138(10) 0.2857(2) 0.9482(7) 0.0458(14) Uani 1 1 d . . . . .
H12 H -0.1076 0.3058 0.9009 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7345(12) 0.5506(3) 0.2094(8) 0.0546(16) Uani 1 1 d . . . . .
C14 C 0.9047(13) 0.5353(3) 0.1388(10) 0.0631(18) Uani 1 1 d . . . . .
H14 H 0.9782 0.5600 0.0896 0.076 Uiso 1 1 calc R U . . .
C15 C 0.9666(15) 0.4835(4) 0.1409(10) 0.075(2) Uani 1 1 d . . . . .
H15 H 1.0845 0.4731 0.0966 0.090 Uiso 1 1 calc R U . . .
C16 C 0.8513(19) 0.4480(3) 0.2091(11) 0.084(3) Uani 1 1 d . . . . .
C17 C 0.6833(19) 0.4628(4) 0.2778(12) 0.088(3) Uani 1 1 d . . . . .
H17 H 0.6077 0.4381 0.3251 0.105 Uiso 1 1 calc R U . . .
C18 C 0.6260(17) 0.5135(3) 0.2773(10) 0.073(2) Uani 1 1 d . . . . .
H18 H 0.5098 0.5234 0.3243 0.088 Uiso 1 1 calc R U . . .
C19 C 0.6736(12) 0.6071(3) 0.2108(8) 0.0525(16) Uani 1 1 d . . . . .
H19 H 0.7549 0.6260 0.1419 0.063 Uiso 1 1 calc R U . . .
C20 C 0.4311(14) 0.6172(4) 0.1501(9) 0.073(2) Uani 1 1 d . . . . .
H20A H 0.3829 0.6007 0.0478 0.087 Uiso 1 1 calc R U . . .
H20B H 0.4059 0.6541 0.1389 0.087 Uiso 1 1 calc R U . . .
H20C H 0.3499 0.6034 0.2247 0.087 Uiso 1 1 calc R U . . .
C21 C 0.488(3) 0.8248(10) 0.535(2) 0.212(15) Uani 1 1 d . . . . .
H21A H 0.4250 0.8450 0.6100 0.255 Uiso 1 1 calc R U . . .
H21B H 0.6396 0.8150 0.5796 0.255 Uiso 1 1 calc R U . . .
C22 C 0.460(3) 0.8424(11) 0.408(2) 0.192(12) Uani 1 1 d . . . . .
H22A H 0.3095 0.8536 0.3750 0.230 Uiso 1 1 calc R U . . .
H22B H 0.4909 0.8165 0.3341 0.230 Uiso 1 1 calc R U . . .
H22C H 0.5567 0.8717 0.4081 0.230 Uiso 1 1 calc R U . . .
C23 C 0.0917(13) 0.7733(4) 0.4603(10) 0.072(2) Uani 1 1 d . . . . .
H23A H 0.0029 0.7512 0.3793 0.086 Uiso 1 1 calc R U . . .
H23B H 0.0345 0.8085 0.4440 0.086 Uiso 1 1 calc R U . . .
C24 C 0.0719(17) 0.7549(4) 0.6218(11) 0.079(2) Uani 1 1 d . . . . .
H24A H -0.0800 0.7561 0.6302 0.095 Uiso 1 1 calc R U . . .
H24B H 0.1581 0.7770 0.7022 0.095 Uiso 1 1 calc R U . . .
H24C H 0.1251 0.7197 0.6374 0.095 Uiso 1 1 calc R U . . .
C25 C 0.4074(12) 0.7310(3) 0.3997(10) 0.0629(18) Uani 1 1 d . . . . .
H25 H 0.3199 0.7013 0.3822 0.075 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.739(10) . ?
S1 O3 1.442(5) . ?
S1 O2 1.442(5) . ?
S1 O1 1.458(4) . ?
S1 C1 1.772(6) . ?
O4 C25 1.238(9) . ?
N1 N2 1.256(8) . ?
N1 C4 1.434(9) . ?
N2 C7 1.415(8) . ?
N3 C10 1.373(8) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N4 C19 1.486(9) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N4 H4C 0.9000 . ?
N5 C25 1.299(11) . ?
N5 C23 1.460(10) . ?
N5 C21 1.80(3) . ?
C1 C6 1.364(10) . ?
C1 C2 1.374(9) . ?
C2 C3 1.383(10) . ?
C2 H2 0.9400 . ?
C3 C4 1.373(10) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(11) . ?
C5 C6 1.391(11) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.383(9) . ?
C7 C8 1.390(9) . ?
C8 C9 1.378(9) . ?
C8 H8 0.9400 . ?
C9 C10 1.395(9) . ?
C9 H9 0.9400 . ?
C10 C11 1.396(9) . ?
C11 C12 1.391(9) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.377(11) . ?
C13 C14 1.391(10) . ?
C13 C19 1.517(10) . ?
C14 C15 1.397(12) . ?
C14 H14 0.9400 . ?
C15 C16 1.376(14) . ?
C15 H15 0.9400 . ?
C16 C17 1.366(14) . ?
C17 C18 1.362(13) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.520(10) . ?
C19 H19 0.9900 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.165(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 C24 1.502(11) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 H25 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 113.4(3) . . ?
O3 S1 O1 112.2(3) . . ?
O2 S1 O1 111.5(3) . . ?
O3 S1 C1 106.1(3) . . ?
O2 S1 C1 106.9(3) . . ?
O1 S1 C1 106.1(3) . . ?
N2 N1 C4 112.6(6) . . ?
N1 N2 C7 114.3(6) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C25 N5 C23 121.8(7) . . ?
C25 N5 C21 119.8(7) . . ?
C23 N5 C21 115.8(7) . . ?
C6 C1 C2 118.7(6) . . ?
C6 C1 S1 120.4(5) . . ?
C2 C1 S1 120.8(5) . . ?
C1 C2 C3 121.0(7) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.0(6) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.3(7) . . ?
C3 C4 N1 125.3(6) . . ?
C5 C4 N1 115.4(7) . . ?
C4 C5 C6 120.1(8) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.8(7) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C12 C7 C8 118.5(6) . . ?
C12 C7 N2 126.8(6) . . ?
C8 C7 N2 114.6(6) . . ?
C9 C8 C7 121.7(6) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 120.0(6) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
N3 C10 C9 121.3(6) . . ?
N3 C10 C11 120.2(6) . . ?
C9 C10 C11 118.5(6) . . ?
C12 C11 C10 120.9(6) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C7 C12 C11 120.3(6) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C18 C13 C14 118.7(7) . . ?
C18 C13 C19 121.6(7) . . ?
C14 C13 C19 119.7(6) . . ?
C13 C14 C15 120.2(8) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 118.6(8) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C15 121.3(8) . . ?
C17 C16 Cl1 120.4(8) . . ?
C15 C16 Cl1 118.3(8) . . ?
C18 C17 C16 119.7(9) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C13 121.4(9) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
N4 C19 C13 109.3(5) . . ?
N4 C19 C20 109.6(6) . . ?
C13 C19 C20 113.4(7) . . ?
N4 C19 H19 108.1 . . ?
C13 C19 H19 108.1 . . ?
C20 C19 H19 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N5 85(2) . . ?
C22 C21 H21A 114.4 . . ?
N5 C21 H21A 114.4 . . ?
C22 C21 H21B 114.4 . . ?
N5 C21 H21B 114.4 . . ?
H21A C21 H21B 111.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N5 C23 C24 111.8(8) . . ?
N5 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
N5 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 N5 126.0(8) . . ?
O4 C25 H25 117.0 . . ?
N5 C25 H25 117.0 . . ?

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
C4 N1 N2 C7 179.3(6) . . . . ?
O3 S1 C1 C6 85.6(8) . . . . ?
O2 S1 C1 C6 -35.7(8) . . . . ?
O1 S1 C1 C6 -154.8(7) . . . . ?
O3 S1 C1 C2 -92.3(6) . . . . ?
O2 S1 C1 C2 146.4(6) . . . . ?
O1 S1 C1 C2 27.2(7) . . . . ?
C6 C1 C2 C3 -0.4(12) . . . . ?
S1 C1 C2 C3 177.6(6) . . . . ?
C1 C2 C3 C4 1.5(12) . . . . ?
C2 C3 C4 C5 -1.9(13) . . . . ?
C2 C3 C4 N1 180.0(7) . . . . ?
N2 N1 C4 C3 -4.7(11) . . . . ?
N2 N1 C4 C5 177.2(8) . . . . ?
C3 C4 C5 C6 1.4(16) . . . . ?
N1 C4 C5 C6 179.7(10) . . . . ?
C2 C1 C6 C5 -0.1(15) . . . . ?
S1 C1 C6 C5 -178.1(9) . . . . ?
C4 C5 C6 C1 -0.4(18) . . . . ?
N1 N2 C7 C12 -4.9(9) . . . . ?
N1 N2 C7 C8 174.6(6) . . . . ?
C12 C7 C8 C9 0.1(10) . . . . ?
N2 C7 C8 C9 -179.5(6) . . . . ?
C7 C8 C9 C10 -0.7(10) . . . . ?
C8 C9 C10 N3 -179.8(6) . . . . ?
C8 C9 C10 C11 1.3(9) . . . . ?
N3 C10 C11 C12 179.8(6) . . . . ?
C9 C10 C11 C12 -1.3(9) . . . . ?
C8 C7 C12 C11 -0.1(9) . . . . ?
N2 C7 C12 C11 179.4(6) . . . . ?
C10 C11 C12 C7 0.7(9) . . . . ?
C18 C13 C14 C15 -1.6(12) . . . . ?
C19 C13 C14 C15 178.1(7) . . . . ?
C13 C14 C15 C16 2.1(13) . . . . ?
C14 C15 C16 C17 -1.8(14) . . . . ?
C14 C15 C16 Cl1 179.7(7) . . . . ?
C15 C16 C17 C18 0.9(17) . . . . ?
Cl1 C16 C17 C18 179.4(8) . . . . ?
C16 C17 C18 C13 -0.3(16) . . . . ?
C14 C13 C18 C17 0.6(13) . . . . ?
C19 C13 C18 C17 -179.0(9) . . . . ?
C18 C13 C19 N4 71.3(9) . . . . ?
C14 C13 C19 N4 -108.3(7) . . . . ?
C18 C13 C19 C20 -51.3(9) . . . . ?
C14 C13 C19 C20 129.1(7) . . . . ?
C25 N5 C21 C22 96.2(12) . . . . ?
C23 N5 C21 C22 -101.6(12) . . . . ?
C25 N5 C23 C24 84.3(11) . . . . ?
C21 N5 C23 C24 -77.5(11) . . . . ?
C23 N5 C25 O4 180.0(9) . . . . ?
C21 N5 C25 O4 -18.9(15) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3B O3 . . 2_547 3.051(9) 0.870 2.295 145.3 no
N4 H4A O2 . . 1_655 2.830(7) 0.900 1.943 168.4 no
N4 H4B O1 . . . 2.811(8) 0.900 1.944 161.1 no
N4 H4C O4 . . . 2.738(8) 0.900 1.846 170.7 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-(4-chlorophenyl)ethan-1-amine/N,N-diethylformamide'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/DEF'
####################################################################### 
# 
# 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_AAS
_database_code_depnum_ccdc_archive 'CCDC 1504254'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H11 N3 O3 S'
_chemical_formula_moiety         'C12 H11 N3 O3 S'
_chemical_formula_weight         277.30
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.8245(3)
_cell_length_b                   7.5038(4)
_cell_length_c                   13.8162(4)
_cell_angle_alpha                94.785(3)
_cell_angle_beta                 94.970(3)
_cell_angle_gamma                95.755(4)
_cell_volume                     595.96(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3423
_cell_measurement_theta_min      5.93
_cell_measurement_theta_max      76.57
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       column
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288.00
_exptl_absorpt_coefficient_mu    2.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.5a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  0.904

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            5827
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_theta_max         77.288
_diffrn_reflns_theta_min         5.953
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2411
_reflns_number_gt                2110
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1506
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2411
_refine_ls_number_parameters     173
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0741P)²+0.5909P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.87
_refine_diff_density_min         -0.67
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.16970(12) 0.71608(9) 0.89654(4) 0.0363(2) Uani 1 1 d . . . . .
O1 O 0.0754(6) 0.8819(3) 0.9212(2) 0.0855(11) Uani 1 1 d . . . . .
O2 O -0.0073(4) 0.5657(2) 0.89389(14) 0.0419(5) Uani 1 1 d . . . . .
O3 O 0.3758(5) 0.6803(5) 0.95411(17) 0.0852(10) Uani 1 1 d . . . . .
N1 N 0.4021(4) 0.7351(3) 0.48607(15) 0.0361(5) Uani 1 1 d . . . . .
N2 N 0.6059(4) 0.7815(3) 0.46980(15) 0.0343(5) Uani 1 1 d . . . . .
N3 N 0.7813(4) 0.7499(3) 0.07373(14) 0.0300(5) Uani 1 1 d . . . . .
H3A H 0.6478 0.7316 0.0345 0.036 Uiso 1 1 calc R U . . .
H3B H 0.8665 0.6583 0.0618 0.036 Uiso 1 1 calc R U . . .
H3C H 0.8611 0.8537 0.0621 0.036 Uiso 1 1 calc R U . . .
C1 C 0.2500(4) 0.7258(3) 0.77612(17) 0.0290(5) Uani 1 1 d . . . . .
C2 C 0.0854(5) 0.6652(3) 0.69925(18) 0.0327(5) Uani 1 1 d . . . . .
H2 H -0.0640 0.6182 0.7114 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1413(5) 0.6741(4) 0.60438(19) 0.0345(6) Uani 1 1 d . . . . .
H3 H 0.0288 0.6355 0.5519 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3629(4) 0.7398(3) 0.58659(17) 0.0310(5) Uani 1 1 d . . . . .
C5 C 0.5288(4) 0.8040(3) 0.66414(18) 0.0327(5) Uani 1 1 d . . . . .
H5 H 0.6776 0.8521 0.6518 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4726(4) 0.7964(3) 0.75907(18) 0.0327(5) Uani 1 1 d . . . . .
H6 H 0.5833 0.8383 0.8117 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6389(4) 0.7710(3) 0.36790(17) 0.0299(5) Uani 1 1 d . . . . .
C8 C 0.4694(5) 0.6949(3) 0.29476(18) 0.0324(5) Uani 1 1 d . . . . .
H8 H 0.3238 0.6476 0.3112 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5150(4) 0.6887(3) 0.19795(18) 0.0314(5) Uani 1 1 d . . . . .
H9 H 0.4016 0.6370 0.1483 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7301(4) 0.7599(3) 0.17557(16) 0.0272(5) Uani 1 1 d . . . . .
C11 C 0.9004(4) 0.8353(3) 0.24747(18) 0.0320(5) Uani 1 1 d . . . . .
H11 H 1.0454 0.8834 0.2308 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8550(5) 0.8392(3) 0.34443(18) 0.0328(5) Uani 1 1 d . . . . .
H12 H 0.9703 0.8878 0.3940 0.039 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.5a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.437(2) . ?
S1 O3 1.442(3) . ?
S1 O2 1.446(2) . ?
S1 C1 1.772(2) . ?
N1 N2 1.247(3) . ?
N1 C4 1.425(3) . ?
N2 C7 1.434(3) . ?
N3 C10 1.461(3) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N3 H3C 0.9000 . ?
C1 C2 1.382(4) . ?
C1 C6 1.398(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.398(4) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.386(3) . ?
C7 C8 1.393(4) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.383(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?

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 O3 117.6(2) . . ?
O1 S1 O2 110.25(15) . . ?
O3 S1 O2 109.79(16) . . ?
O1 S1 C1 106.21(13) . . ?
O3 S1 C1 105.40(14) . . ?
O2 S1 C1 106.93(11) . . ?
N2 N1 C4 115.1(2) . . ?
N1 N2 C7 113.3(2) . . ?
C10 N3 H3A 109.5 . . ?
C10 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C10 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 S1 118.33(19) . . ?
C6 C1 S1 120.96(19) . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 N1 114.8(2) . . ?
C5 C4 N1 124.8(2) . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C12 C7 C8 120.3(2) . . ?
C12 C7 N2 116.1(2) . . ?
C8 C7 N2 123.5(2) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 118.9(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 N3 119.1(2) . . ?
C11 C10 N3 119.2(2) . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C7 C12 C11 119.7(2) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C7 178.7(2) . . . . ?
O1 S1 C1 C2 -88.0(2) . . . . ?
O3 S1 C1 C2 146.5(2) . . . . ?
O2 S1 C1 C2 29.7(2) . . . . ?
O1 S1 C1 C6 90.6(3) . . . . ?
O3 S1 C1 C6 -34.8(3) . . . . ?
O2 S1 C1 C6 -151.6(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
S1 C1 C2 C3 178.80(19) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 -2.5(4) . . . . ?
C2 C3 C4 N1 177.4(2) . . . . ?
N2 N1 C4 C3 -174.9(2) . . . . ?
N2 N1 C4 C5 5.0(4) . . . . ?
C3 C4 C5 C6 2.0(4) . . . . ?
N1 C4 C5 C6 -177.9(2) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
S1 C1 C6 C5 -179.20(19) . . . . ?
N1 N2 C7 C12 173.2(2) . . . . ?
N1 N2 C7 C8 -7.9(4) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
N2 C7 C8 C9 -179.6(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C8 C9 C10 N3 178.5(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
N3 C10 C11 C12 -177.7(2) . . . . ?
C8 C7 C12 C11 1.5(4) . . . . ?
N2 C7 C12 C11 -179.5(2) . . . . ?
C10 C11 C12 C7 -1.3(4) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O3 . . 1_554 2.741(3) 0.900 1.842 176.7 no
N3 H3B O2 . . 2_666 2.871(3) 0.900 2.057 149.8 no
N3 H3C O1 . . 1_654 2.998(4) 0.900 2.414 122.8 no
N3 H3C O1 . . 2_676 2.798(3) 0.900 1.972 152.0 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-DMF
_database_code_depnum_ccdc_archive 'CCDC 1504255'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;
#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H28 Cl N5 O4 S'
_chemical_formula_moiety         'C23 H28 Cl N5 O4 S'
_chemical_formula_weight         506.02
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_space_group_IT_number           1
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.94757(14)
_cell_length_b                   9.5911(2)
_cell_length_c                   11.4509(3)
_cell_angle_alpha                83.8975(16)
_cell_angle_beta                 82.0150(15)
_cell_angle_gamma                71.9997(15)
_cell_volume                     613.82(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2880
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      68.13
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             266.00
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.306
_exptl_absorpt_correction_T_max  0.606

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6470
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_theta_max         68.127
_diffrn_reflns_theta_min         3.907
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3604
_reflns_number_gt                3036
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_max     0.639
_reflns_Friedel_fraction_full    0.644

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.2643
_refine_ls_wR_factor_gt          0.2281
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3604
_refine_ls_number_parameters     312
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1731P)²+0.0945P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.010(5)
_refine_ls_abs_structure_details 
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.09(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.1771(6) 0.5178(3) 0.8285(3) 0.0733(10) Uani 1 1 d . . . . .
S1 S 0.9651(3) 0.5835(2) 0.24803(18) 0.0391(6) Uani 1 1 d . . . . .
O1 O 1.2161(13) 0.5706(8) 0.2394(6) 0.0470(16) Uani 1 1 d . . . . .
O2 O 0.8989(15) 0.5406(8) 0.1453(6) 0.0553(19) Uani 1 1 d . . . . .
O3 O 0.8198(12) 0.7301(7) 0.2813(6) 0.0478(16) Uani 1 1 d . . . . .
O4 O 0.1069(18) 1.0603(11) 0.1273(8) 0.081(3) Uani 1 1 d . . . . .
N1 N 0.7764(15) 0.1831(8) 0.6613(6) 0.0408(18) Uani 1 1 d . . . . .
N2 N 0.5982(15) 0.1398(8) 0.6648(6) 0.0397(18) Uani 1 1 d . . . . .
N3 N 0.4803(16) -0.2836(9) 1.0236(7) 0.0495(19) Uani 1 1 d . . . . .
H3A H 0.5770 -0.3135 1.0778 0.059 Uiso 1 1 calc R U . . .
H3B H 0.3643 -0.3210 1.0238 0.059 Uiso 1 1 calc R U . . .
N4 N 0.3175(16) 0.8299(8) 0.2752(6) 0.0434(18) Uani 1 1 d . . . . .
H4A H 0.2655 0.7516 0.2733 0.052 Uiso 1 1 calc R U . . .
H4B H 0.4765 0.7997 0.2759 0.052 Uiso 1 1 calc R U . . .
H4C H 0.2799 0.8911 0.2109 0.052 Uiso 1 1 calc R U . . .
N5 N -0.2286(19) 1.2110(9) 0.0589(8) 0.056(2) Uani 1 1 d . . . . .
C1 C 0.9119(18) 0.4606(10) 0.3665(8) 0.039(2) Uani 1 1 d . . . . .
C2 C 1.0369(17) 0.4375(9) 0.4647(7) 0.0367(19) Uani 1 1 d . . . . .
H2 H 1.1553 0.4832 0.4662 0.044 Uiso 1 1 calc R U . . .
C3 C 0.9846(16) 0.3459(10) 0.5605(8) 0.038(2) Uani 1 1 d . . . . .
H3 H 1.0687 0.3300 0.6268 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8097(17) 0.2775(9) 0.5596(9) 0.039(2) Uani 1 1 d . . . . .
C5 C 0.6878(18) 0.2990(10) 0.4587(9) 0.044(2) Uani 1 1 d . . . . .
H5 H 0.5726 0.2511 0.4562 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7374(17) 0.3898(10) 0.3642(8) 0.041(2) Uani 1 1 d . . . . .
H6 H 0.6545 0.4048 0.2976 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5713(17) 0.0398(9) 0.7631(8) 0.040(2) Uani 1 1 d . . . . .
C8 C 0.7261(17) -0.0090(10) 0.8495(7) 0.041(2) Uani 1 1 d . . . . .
H8 H 0.8518 0.0310 0.8493 0.049 Uiso 1 1 calc R U . . .
C9 C 0.6958(19) -0.1161(11) 0.9354(8) 0.046(2) Uani 1 1 d . . . . .
H9 H 0.8014 -0.1481 0.9934 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5112(17) -0.1773(10) 0.9374(7) 0.039(2) Uani 1 1 d . . . . .
C11 C 0.3523(17) -0.1243(10) 0.8525(8) 0.042(2) Uani 1 1 d . . . . .
H11 H 0.2235 -0.1620 0.8544 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3807(16) -0.0173(10) 0.7656(8) 0.041(2) Uani 1 1 d . . . . .
H12 H 0.2728 0.0167 0.7087 0.049 Uiso 1 1 calc R U . . .
C13 C 0.2011(18) 0.8051(10) 0.4927(8) 0.040(2) Uani 1 1 d . . . . .
C14 C 0.4103(18) 0.7108(11) 0.5320(8) 0.045(2) Uani 1 1 d . . . . .
H14 H 0.5578 0.7084 0.4888 0.054 Uiso 1 1 calc R U . . .
C15 C 0.4023(19) 0.6210(11) 0.6339(9) 0.047(2) Uani 1 1 d . . . . .
H15 H 0.5431 0.5567 0.6601 0.057 Uiso 1 1 calc R U . . .
C16 C 0.184(2) 0.6271(11) 0.6968(8) 0.052(3) Uani 1 1 d . . . . .
C17 C -0.026(2) 0.7196(11) 0.6616(9) 0.050(2) Uani 1 1 d . . . . .
H17 H -0.1727 0.7230 0.7063 0.060 Uiso 1 1 calc R U . . .
C18 C -0.015(2) 0.8067(11) 0.5591(9) 0.050(2) Uani 1 1 d . . . . .
H18 H -0.1571 0.8694 0.5329 0.060 Uiso 1 1 calc R U . . .
C19 C 0.2000(18) 0.9103(11) 0.3864(8) 0.044(2) Uani 1 1 d . . . . .
H19 H 0.0321 0.9630 0.3748 0.053 Uiso 1 1 calc R U . . .
C20 C 0.325(2) 1.0247(12) 0.3972(11) 0.058(3) Uani 1 1 d . . . . .
H20A H 0.2612 1.0732 0.4700 0.070 Uiso 1 1 calc R U . . .
H20B H 0.2987 1.0968 0.3305 0.070 Uiso 1 1 calc R U . . .
H20C H 0.4942 0.9767 0.3980 0.070 Uiso 1 1 calc R U . . .
C21 C -0.094(7) 1.114(3) 0.111(3) 0.24(3) Uani 1 1 d . . . . .
H21 H -0.1835 1.0591 0.1575 0.292 Uiso 1 1 calc R U . . .
C22 C -0.122(6) 1.290(2) -0.0287(19) 0.137(10) Uani 1 1 d . . . . .
H22A H 0.0458 1.2365 -0.0447 0.165 Uiso 1 1 calc R U . . .
H22B H -0.1384 1.3854 -0.0022 0.165 Uiso 1 1 calc R U . . .
H22C H -0.1980 1.3017 -0.1002 0.165 Uiso 1 1 calc R U . . .
C23 C -0.476(6) 1.267(4) 0.059(4) 0.26(3) Uani 1 1 d . . . . .
H23A H -0.5532 1.2424 0.1351 0.317 Uiso 1 1 calc R U . . .
H23B H -0.5255 1.2250 -0.0026 0.317 Uiso 1 1 calc R U . . .
H23C H -0.5200 1.3732 0.0446 0.317 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.747(10) . ?
S1 O2 1.428(7) . ?
S1 O1 1.449(7) . ?
S1 O3 1.463(7) . ?
S1 C1 1.761(10) . ?
O4 C21 1.18(3) . ?
N1 N2 1.246(11) . ?
N1 C4 1.427(12) . ?
N2 C7 1.424(11) . ?
N3 C10 1.378(12) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N4 C19 1.528(11) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N4 H4C 0.9000 . ?
N5 C21 1.19(2) . ?
N5 C22 1.39(2) . ?
N5 C23 1.40(3) . ?
C1 C2 1.394(12) . ?
C1 C6 1.409(14) . ?
C2 C3 1.394(12) . ?
C2 H2 0.9400 . ?
C3 C4 1.392(13) . ?
C3 H3 0.9400 . ?
C4 C5 1.412(13) . ?
C5 C6 1.373(13) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.391(13) . ?
C7 C12 1.399(14) . ?
C8 C9 1.380(13) . ?
C8 H8 0.9400 . ?
C9 C10 1.393(14) . ?
C9 H9 0.9400 . ?
C10 C11 1.397(13) . ?
C11 C12 1.384(14) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.394(14) . ?
C13 C18 1.396(15) . ?
C13 C19 1.495(14) . ?
C14 C15 1.379(14) . ?
C14 H14 0.9400 . ?
C15 C16 1.382(15) . ?
C15 H15 0.9400 . ?
C16 C17 1.375(16) . ?
C17 C18 1.373(15) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.526(15) . ?
C19 H19 0.9900 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21 0.9400 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

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 113.2(5) . . ?
O2 S1 O3 113.1(4) . . ?
O1 S1 O3 110.7(4) . . ?
O2 S1 C1 107.0(4) . . ?
O1 S1 C1 106.2(4) . . ?
O3 S1 C1 106.1(4) . . ?
N2 N1 C4 114.1(7) . . ?
N1 N2 C7 114.2(7) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C21 N5 C22 115(3) . . ?
C21 N5 C23 137(3) . . ?
C22 N5 C23 108(3) . . ?
C2 C1 C6 120.0(9) . . ?
C2 C1 S1 119.8(8) . . ?
C6 C1 S1 120.2(7) . . ?
C3 C2 C1 119.2(9) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 121.1(8) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.2(9) . . ?
C3 C4 N1 116.0(7) . . ?
C5 C4 N1 124.7(8) . . ?
C6 C5 C4 120.0(9) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.4(8) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C12 119.6(8) . . ?
C8 C7 N2 124.8(8) . . ?
C12 C7 N2 115.5(8) . . ?
C9 C8 C7 120.2(9) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.0(9) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
N3 C10 C9 121.0(8) . . ?
N3 C10 C11 120.7(9) . . ?
C9 C10 C11 118.3(8) . . ?
C12 C11 C10 121.3(9) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C7 119.4(8) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C14 C13 C18 118.5(9) . . ?
C14 C13 C19 122.6(9) . . ?
C18 C13 C19 118.8(9) . . ?
C15 C14 C13 120.4(10) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.0(9) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 122.5(10) . . ?
C17 C16 Cl1 119.0(9) . . ?
C15 C16 Cl1 118.5(9) . . ?
C18 C17 C16 117.8(10) . . ?
C18 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
C17 C18 C13 122.0(10) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
C13 C19 C20 113.9(9) . . ?
C13 C19 N4 111.4(7) . . ?
C20 C19 N4 107.5(9) . . ?
C13 C19 H19 107.9 . . ?
C20 C19 H19 107.9 . . ?
N4 C19 H19 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 O4 145(5) . . ?
N5 C21 H21 107.5 . . ?
O4 C21 H21 107.5 . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N5 C23 H23A 109.5 . . ?
N5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C4 N1 N2 C7 177.0(7) . . . . ?
O2 S1 C1 C2 155.7(7) . . . . ?
O1 S1 C1 C2 34.6(8) . . . . ?
O3 S1 C1 C2 -83.3(8) . . . . ?
O2 S1 C1 C6 -26.6(9) . . . . ?
O1 S1 C1 C6 -147.7(7) . . . . ?
O3 S1 C1 C6 94.5(8) . . . . ?
C6 C1 C2 C3 -1.0(13) . . . . ?
S1 C1 C2 C3 176.7(7) . . . . ?
C1 C2 C3 C4 -0.1(13) . . . . ?
C2 C3 C4 C5 1.5(13) . . . . ?
C2 C3 C4 N1 178.4(7) . . . . ?
N2 N1 C4 C3 170.8(8) . . . . ?
N2 N1 C4 C5 -12.5(12) . . . . ?
C3 C4 C5 C6 -1.8(13) . . . . ?
N1 C4 C5 C6 -178.5(8) . . . . ?
C4 C5 C6 C1 0.8(14) . . . . ?
C2 C1 C6 C5 0.6(14) . . . . ?
S1 C1 C6 C5 -177.1(7) . . . . ?
N1 N2 C7 C8 -0.3(12) . . . . ?
N1 N2 C7 C12 -176.4(8) . . . . ?
C12 C7 C8 C9 1.7(14) . . . . ?
N2 C7 C8 C9 -174.2(8) . . . . ?
C7 C8 C9 C10 0.1(14) . . . . ?
C8 C9 C10 N3 -179.7(8) . . . . ?
C8 C9 C10 C11 -2.1(14) . . . . ?
N3 C10 C11 C12 179.9(8) . . . . ?
C9 C10 C11 C12 2.2(14) . . . . ?
C10 C11 C12 C7 -0.4(14) . . . . ?
C8 C7 C12 C11 -1.6(14) . . . . ?
N2 C7 C12 C11 174.8(8) . . . . ?
C18 C13 C14 C15 0.3(13) . . . . ?
C19 C13 C14 C15 176.8(9) . . . . ?
C13 C14 C15 C16 -0.6(14) . . . . ?
C14 C15 C16 C17 0.0(15) . . . . ?
C14 C15 C16 Cl1 -177.7(7) . . . . ?
C15 C16 C17 C18 0.9(15) . . . . ?
Cl1 C16 C17 C18 178.5(7) . . . . ?
C16 C17 C18 C13 -1.1(14) . . . . ?
C14 C13 C18 C17 0.6(14) . . . . ?
C19 C13 C18 C17 -176.0(9) . . . . ?
C14 C13 C19 C20 -61.7(11) . . . . ?
C18 C13 C19 C20 114.7(10) . . . . ?
C14 C13 C19 N4 60.2(12) . . . . ?
C18 C13 C19 N4 -123.4(9) . . . . ?
C22 N5 C21 O4 10(4) . . . . ?
C23 N5 C21 O4 -173(3) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O2 . . 1_546 2.975(12) 0.870 2.179 152.0 no
N4 H4A O1 . . 1_455 2.816(12) 0.900 1.934 166.2 no
N4 H4B O3 . . . 2.850(11) 0.900 1.950 178.3 no
N4 H4C O4 . . . 2.721(11) 0.900 1.876 155.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-(4-chlorophenyl)ethan-1-amine/N,N-dimethylformamide'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/DMF'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-DMA
_database_code_depnum_ccdc_archive 'CCDC 1504256'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H30 Cl N5 O4 S'
_chemical_formula_moiety         'C24 H30 Cl N5 O4 S'
_chemical_formula_weight         520.05
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.11235(13)
_cell_length_b                   28.1898(6)
_cell_length_c                   7.71338(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.9285(13)
_cell_angle_gamma                90.0000
_cell_volume                     1327.33(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10693
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548.00
_exptl_absorpt_coefficient_mu    2.331
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.478
_exptl_absorpt_correction_T_max  0.627

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.000
_diffrn_reflns_number            13867
_diffrn_reflns_av_R_equivalents  0.1683
_diffrn_reflns_theta_max         68.212
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4695
_reflns_number_gt                2537
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.945

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.1118
_refine_ls_wR_factor_ref         0.3381
_refine_ls_wR_factor_gt          0.2752
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4695
_refine_ls_number_parameters     322
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1561P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.99
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.020(5)
_refine_ls_abs_structure_details 
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.00(6)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.7297(11) 0.40686(16) 0.2501(7) 0.130(2) Uani 1 1 d . . . . .
S1 S 0.0868(5) 0.58563(10) 0.7075(4) 0.0641(9) Uani 1 1 d . . . . .
O1 O -0.0382(17) 0.6042(3) 0.8449(11) 0.081(3) Uani 1 1 d . . . . .
O2 O -0.0167(15) 0.5913(3) 0.5380(10) 0.073(2) Uani 1 1 d . . . . .
O3 O 0.3124(14) 0.6030(3) 0.7181(12) 0.075(2) Uani 1 1 d . . . . .
O4 O 0.5606(19) 0.7275(4) 0.4249(15) 0.096(3) Uani 1 1 d . . . . .
N1 N 0.109(2) 0.3765(4) 0.8512(16) 0.083(3) Uani 1 1 d . . . . .
N2 N 0.2912(19) 0.3616(4) 0.9140(16) 0.077(3) Uani 1 1 d . . . . .
N3 N 0.3786(18) 0.1740(4) 1.1327(14) 0.074(3) Uani 1 1 d . . . . .
H3A H 0.2704 0.1540 1.1236 0.089 Uiso 1 1 calc R U . . .
H3B H 0.5052 0.1650 1.1778 0.089 Uiso 1 1 calc R U . . .
N4 N 0.5724(17) 0.6311(3) 0.4445(13) 0.066(3) Uani 1 1 d . . . . .
H4A H 0.4703 0.6198 0.5137 0.079 Uiso 1 1 calc R U . . .
H4B H 0.5721 0.6630 0.4482 0.079 Uiso 1 1 calc R U . . .
H4C H 0.7052 0.6203 0.4815 0.079 Uiso 1 1 calc R U . . .
N5 N 0.709(3) 0.7968(7) 0.501(2) 0.132(7) Uani 1 1 d . . . . .
C1 C 0.1047(19) 0.5233(4) 0.7422(14) 0.057(3) Uani 1 1 d . . . . .
C2 C -0.069(2) 0.4948(4) 0.6936(18) 0.071(3) Uani 1 1 d . . . . .
H2 H -0.1935 0.5078 0.6352 0.085 Uiso 1 1 calc R U . . .
C3 C -0.061(3) 0.4462(5) 0.7309(19) 0.084(4) Uani 1 1 d . . . . .
H3 H -0.1803 0.4266 0.6974 0.101 Uiso 1 1 calc R U . . .
C4 C 0.120(2) 0.4273(5) 0.8159(19) 0.075(3) Uani 1 1 d . . . . .
C5 C 0.299(2) 0.4557(5) 0.8621(19) 0.078(4) Uani 1 1 d . . . . .
H5 H 0.4255 0.4425 0.9169 0.094 Uiso 1 1 calc R U . . .
C6 C 0.288(2) 0.5041(5) 0.8262(18) 0.075(3) Uani 1 1 d . . . . .
H6 H 0.4075 0.5238 0.8595 0.090 Uiso 1 1 calc R U . . .
C7 C 0.297(2) 0.3133(4) 0.9627(16) 0.067(3) Uani 1 1 d . . . . .
C8 C 0.122(2) 0.2808(5) 0.9462(17) 0.071(3) Uani 1 1 d . . . . .
H8 H -0.0138 0.2903 0.8956 0.085 Uiso 1 1 calc R U . . .
C9 C 0.151(2) 0.2353(4) 1.0039(17) 0.068(3) Uani 1 1 d . . . . .
H9 H 0.0320 0.2141 0.9940 0.082 Uiso 1 1 calc R U . . .
C10 C 0.350(2) 0.2192(4) 1.0768(16) 0.066(3) Uani 1 1 d . . . . .
C11 C 0.526(2) 0.2517(5) 1.0855(17) 0.072(3) Uani 1 1 d . . . . .
H11 H 0.6643 0.2420 1.1306 0.087 Uiso 1 1 calc R U . . .
C12 C 0.495(2) 0.2973(5) 1.0286(19) 0.076(3) Uani 1 1 d . . . . .
H12 H 0.6147 0.3184 1.0350 0.092 Uiso 1 1 calc R U . . .
C13 C 0.566(2) 0.5626(4) 0.2509(16) 0.065(3) Uani 1 1 d . . . . .
C14 C 0.427(2) 0.5296(5) 0.3252(18) 0.077(4) Uani 1 1 d . . . . .
H14 H 0.2991 0.5401 0.3754 0.092 Uiso 1 1 calc R U . . .
C15 C 0.477(3) 0.4814(6) 0.326(2) 0.095(5) Uani 1 1 d . . . . .
H15 H 0.3863 0.4591 0.3774 0.114 Uiso 1 1 calc R U . . .
C16 C 0.662(3) 0.4677(6) 0.2481(18) 0.087(4) Uani 1 1 d . . . . .
C17 C 0.801(3) 0.4987(5) 0.1732(19) 0.082(4) Uani 1 1 d . . . . .
H17 H 0.9281 0.4875 0.1231 0.098 Uiso 1 1 calc R U . . .
C18 C 0.754(2) 0.5460(5) 0.1715(17) 0.074(3) Uani 1 1 d . . . . .
H18 H 0.8462 0.5675 0.1175 0.089 Uiso 1 1 calc R U . . .
C19 C 0.522(2) 0.6150(4) 0.2625(15) 0.066(3) Uani 1 1 d . . . . .
H19 H 0.6268 0.6311 0.1885 0.079 Uiso 1 1 calc R U . . .
C20 C 0.298(2) 0.6311(5) 0.2033(18) 0.078(4) Uani 1 1 d . . . . .
H20A H 0.1906 0.6160 0.2733 0.094 Uiso 1 1 calc R U . . .
H20B H 0.2700 0.6225 0.0824 0.094 Uiso 1 1 calc R U . . .
H20C H 0.2884 0.6653 0.2155 0.094 Uiso 1 1 calc R U . . .
C21 C 0.723(5) 0.7562(7) 0.482(2) 0.134(10) Uani 1 1 d . . . . .
C22 C 0.950(3) 0.7295(7) 0.512(3) 0.102(5) Uani 1 1 d . . . . .
H22A H 1.0010 0.7326 0.6325 0.122 Uiso 1 1 calc R U . . .
H22B H 1.0567 0.7435 0.4381 0.122 Uiso 1 1 calc R U . . .
H22C H 0.9314 0.6962 0.4833 0.122 Uiso 1 1 calc R U . . .
C23 C 0.882(3) 0.8269(7) 0.577(2) 0.117(7) Uani 1 1 d . . . . .
H23A H 1.0132 0.8081 0.6006 0.140 Uiso 1 1 calc R U . . .
H23B H 0.8353 0.8407 0.6837 0.140 Uiso 1 1 calc R U . . .
H23C H 0.9139 0.8521 0.4956 0.140 Uiso 1 1 calc R U . . .
C24 C 0.477(3) 0.8174(6) 0.457(3) 0.103(5) Uani 1 1 d . . . . .
H24A H 0.4054 0.8239 0.5632 0.123 Uiso 1 1 calc R U . . .
H24B H 0.3918 0.7946 0.3878 0.123 Uiso 1 1 calc R U . . .
H24C H 0.4907 0.8466 0.3913 0.123 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.764(16) . ?
S1 O2 1.432(8) . ?
S1 O1 1.437(8) . ?
S1 O3 1.462(9) . ?
S1 C1 1.780(12) . ?
O4 C21 1.34(3) . ?
N1 N2 1.263(15) . ?
N1 C4 1.461(16) . ?
N2 C7 1.412(16) . ?
N3 C10 1.352(15) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N4 C19 1.493(15) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N4 H4C 0.9000 . ?
N5 C21 1.16(2) . ?
N5 C23 1.46(2) . ?
N5 C24 1.55(3) . ?
C1 C2 1.369(17) . ?
C1 C6 1.378(17) . ?
C2 C3 1.400(18) . ?
C2 H2 0.9400 . ?
C3 C4 1.37(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.387(19) . ?
C5 C6 1.391(19) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.367(18) . ?
C7 C8 1.407(18) . ?
C8 C9 1.366(17) . ?
C8 H8 0.9400 . ?
C9 C10 1.390(18) . ?
C9 H9 0.9400 . ?
C10 C11 1.411(18) . ?
C11 C12 1.369(18) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.401(18) . ?
C13 C18 1.406(19) . ?
C13 C19 1.506(17) . ?
C14 C15 1.39(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.36(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.37(2) . ?
C17 C18 1.364(19) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.492(18) . ?
C19 H19 0.9900 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.59(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?

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 114.0(6) . . ?
O2 S1 O3 112.7(6) . . ?
O1 S1 O3 111.8(6) . . ?
O2 S1 C1 105.5(5) . . ?
O1 S1 C1 106.3(5) . . ?
O3 S1 C1 105.8(6) . . ?
N2 N1 C4 110.6(13) . . ?
N1 N2 C7 115.6(12) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C21 N5 C23 125(3) . . ?
C21 N5 C24 114(2) . . ?
C23 N5 C24 120(2) . . ?
C2 C1 C6 120.0(11) . . ?
C2 C1 S1 119.9(10) . . ?
C6 C1 S1 120.1(9) . . ?
C1 C2 C3 120.1(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.8(14) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.5(12) . . ?
C3 C4 N1 115.3(13) . . ?
C5 C4 N1 124.2(13) . . ?
C4 C5 C6 119.1(12) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.4(12) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C12 C7 C8 118.3(11) . . ?
C12 C7 N2 115.2(11) . . ?
C8 C7 N2 126.6(12) . . ?
C9 C8 C7 119.8(12) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 122.3(12) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
N3 C10 C9 122.2(12) . . ?
N3 C10 C11 120.7(13) . . ?
C9 C10 C11 117.1(11) . . ?
C12 C11 C10 120.3(14) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C7 C12 C11 122.1(13) . . ?
C7 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C14 C13 C18 118.8(12) . . ?
C14 C13 C19 120.8(13) . . ?
C18 C13 C19 120.3(12) . . ?
C15 C14 C13 120.8(14) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 117.5(14) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C17 123.5(15) . . ?
C15 C16 Cl1 118.0(13) . . ?
C17 C16 Cl1 118.4(13) . . ?
C18 C17 C16 119.6(14) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 119.8(13) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C20 C19 N4 109.7(11) . . ?
C20 C19 C13 116.5(11) . . ?
N4 C19 C13 109.0(10) . . ?
C20 C19 H19 107.1 . . ?
N4 C19 H19 107.1 . . ?
C13 C19 H19 107.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 O4 126(3) . . ?
N5 C21 C22 121(3) . . ?
O4 C21 C22 113.1(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N5 C23 H23A 109.5 . . ?
N5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N5 C24 H24A 109.5 . . ?
N5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C4 N1 N2 C7 176.5(11) . . . . ?
O2 S1 C1 C2 -42.2(12) . . . . ?
O1 S1 C1 C2 79.1(11) . . . . ?
O3 S1 C1 C2 -161.9(10) . . . . ?
O2 S1 C1 C6 141.2(11) . . . . ?
O1 S1 C1 C6 -97.4(12) . . . . ?
O3 S1 C1 C6 21.6(12) . . . . ?
C6 C1 C2 C3 1(2) . . . . ?
S1 C1 C2 C3 -175.8(10) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C2 C3 C4 N1 178.9(13) . . . . ?
N2 N1 C4 C3 173.4(13) . . . . ?
N2 N1 C4 C5 -6(2) . . . . ?
C3 C4 C5 C6 2(2) . . . . ?
N1 C4 C5 C6 -178.2(13) . . . . ?
C2 C1 C6 C5 0(2) . . . . ?
S1 C1 C6 C5 176.6(11) . . . . ?
C4 C5 C6 C1 -2(2) . . . . ?
N1 N2 C7 C12 179.2(12) . . . . ?
N1 N2 C7 C8 0.7(19) . . . . ?
C12 C7 C8 C9 3.4(19) . . . . ?
N2 C7 C8 C9 -178.1(12) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
C8 C9 C10 N3 -179.5(12) . . . . ?
C8 C9 C10 C11 -1.5(19) . . . . ?
N3 C10 C11 C12 180.0(11) . . . . ?
C9 C10 C11 C12 1.9(19) . . . . ?
C8 C7 C12 C11 -3(2) . . . . ?
N2 C7 C12 C11 178.3(12) . . . . ?
C10 C11 C12 C7 0(2) . . . . ?
C18 C13 C14 C15 2(2) . . . . ?
C19 C13 C14 C15 -175.2(14) . . . . ?
C13 C14 C15 C16 -1(2) . . . . ?
C14 C15 C16 C17 1(3) . . . . ?
C14 C15 C16 Cl1 179.1(12) . . . . ?
C15 C16 C17 C18 -1(2) . . . . ?
Cl1 C16 C17 C18 -179.3(11) . . . . ?
C16 C17 C18 C13 2(2) . . . . ?
C14 C13 C18 C17 -2(2) . . . . ?
C19 C13 C18 C17 175.1(12) . . . . ?
C14 C13 C19 C20 -52.6(17) . . . . ?
C18 C13 C19 C20 130.2(13) . . . . ?
C14 C13 C19 N4 72.1(15) . . . . ?
C18 C13 C19 N4 -105.1(13) . . . . ?
C23 N5 C21 O4 174.7(15) . . . . ?
C24 N5 C21 O4 1(3) . . . . ?
C23 N5 C21 C22 -9(3) . . . . ?
C24 N5 C21 C22 176.9(14) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-(4-chlorophenyl)ethan-1-amine/N,N-dimethylacetamide '
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/DMA'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-DMSO
_database_code_depnum_ccdc_archive 'CCDC 1504257'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H27 Cl N4 O4 S2'
_chemical_formula_moiety         'C22 H27 Cl N4 O4 S2'
_chemical_formula_weight         511.05
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.99452(11)
_cell_length_b                   23.7139(4)
_cell_length_c                   9.33438(17)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.5280(11)
_cell_angle_gamma                90.0000
_cell_volume                     1258.14(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10363
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536.00
_exptl_absorpt_coefficient_mu    3.193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_T_max  0.727

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12525
_diffrn_reflns_av_R_equivalents  0.1336
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_min         3.728
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4386
_reflns_number_gt                2616
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_max     0.926
_reflns_Friedel_fraction_full    0.933

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0789
_refine_ls_wR_factor_ref         0.2167
_refine_ls_wR_factor_gt          0.1667
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4386
_refine_ls_number_parameters     302
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0679P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.2943(9) 0.63661(15) 0.5729(5) 0.1109(15) Uani 1 1 d . . . . .
S1 S 0.9398(5) 0.35748(9) 0.5746(3) 0.0540(7) Uani 1 1 d . . . . .
S2 S -0.0670(7) 0.25401(16) 0.0633(4) 0.0897(12) Uani 1 1 d . . . . .
O1 O 1.1928(11) 0.3530(3) 0.5967(8) 0.0554(16) Uani 1 1 d . . . . .
O2 O 0.8405(15) 0.3087(3) 0.6239(9) 0.074(2) Uani 1 1 d . . . . .
O3 O 0.8096(13) 0.3742(3) 0.4185(7) 0.063(2) Uani 1 1 d . . . . .
O4 O 0.1449(16) 0.2888(4) 0.1218(11) 0.091(3) Uani 1 1 d . . . . .
N1 N 0.8189(16) 0.5581(3) 0.9272(9) 0.051(2) Uani 1 1 d . . . . .
N2 N 0.6414(17) 0.5580(3) 0.9763(9) 0.054(2) Uani 1 1 d . . . . .
N3 N 0.5535(17) 0.7440(4) 1.3210(11) 0.074(3) Uani 1 1 d . . . . .
H3A H 0.4379 0.7460 1.3584 0.089 Uiso 1 1 calc R U . . .
H3B H 0.6565 0.7711 1.3376 0.089 Uiso 1 1 calc R U . . .
N4 N 0.3116(16) 0.3702(3) 0.3273(9) 0.060(2) Uani 1 1 d . . . . .
H4A H 0.2576 0.3697 0.4069 0.072 Uiso 1 1 calc R U . . .
H4B H 0.4696 0.3726 0.3604 0.072 Uiso 1 1 calc R U . . .
H4C H 0.2677 0.3384 0.2733 0.072 Uiso 1 1 calc R U . . .
C1 C 0.9074(16) 0.4146(4) 0.6848(10) 0.046(2) Uani 1 1 d . . . . .
C2 C 1.0437(18) 0.4624(4) 0.6971(12) 0.055(3) Uani 1 1 d . . . . .
H2 H 1.1607 0.4632 0.6499 0.066 Uiso 1 1 calc R U . . .
C3 C 1.0119(19) 0.5094(4) 0.7780(12) 0.057(3) Uani 1 1 d . . . . .
H3 H 1.1077 0.5415 0.7863 0.068 Uiso 1 1 calc R U . . .
C4 C 0.8355(17) 0.5085(4) 0.8469(10) 0.046(2) Uani 1 1 d . . . . .
C5 C 0.6999(19) 0.4601(4) 0.8381(12) 0.055(2) Uani 1 1 d . . . . .
H5 H 0.5859 0.4589 0.8877 0.066 Uiso 1 1 calc R U . . .
C6 C 0.7324(19) 0.4136(4) 0.7563(12) 0.058(3) Uani 1 1 d . . . . .
H6 H 0.6376 0.3814 0.7486 0.069 Uiso 1 1 calc R U . . .
C7 C 0.6261(17) 0.6076(4) 1.0625(11) 0.050(2) Uani 1 1 d . . . . .
C8 C 0.783(2) 0.6515(4) 1.0890(12) 0.059(3) Uani 1 1 d . . . . .
H8 H 0.9048 0.6510 1.0454 0.070 Uiso 1 1 calc R U . . .
C9 C 0.765(2) 0.6964(4) 1.1785(14) 0.065(3) Uani 1 1 d . . . . .
H9 H 0.8790 0.7252 1.2008 0.078 Uiso 1 1 calc R U . . .
C10 C 0.5729(19) 0.6988(4) 1.2370(13) 0.057(3) Uani 1 1 d . . . . .
C11 C 0.4154(19) 0.6540(4) 1.2058(12) 0.054(2) Uani 1 1 d . . . . .
H11 H 0.2894 0.6545 1.2453 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4387(18) 0.6091(4) 1.1189(12) 0.057(3) Uani 1 1 d . . . . .
H12 H 0.3283 0.5796 1.0978 0.068 Uiso 1 1 calc R U . . .
C13 C 0.2309(18) 0.4735(4) 0.3189(11) 0.051(2) Uani 1 1 d . . . . .
C14 C 0.452(2) 0.4922(4) 0.4123(11) 0.057(3) Uani 1 1 d . . . . .
H14 H 0.5882 0.4707 0.4221 0.068 Uiso 1 1 calc R U . . .
C15 C 0.467(3) 0.5427(5) 0.4895(14) 0.076(4) Uani 1 1 d . . . . .
H15 H 0.6144 0.5556 0.5520 0.091 Uiso 1 1 calc R U . . .
C16 C 0.270(3) 0.5739(5) 0.4755(14) 0.076(4) Uani 1 1 d . . . . .
C17 C 0.050(3) 0.5554(5) 0.3853(15) 0.075(4) Uani 1 1 d . . . . .
H17 H -0.0863 0.5765 0.3770 0.090 Uiso 1 1 calc R U . . .
C18 C 0.038(2) 0.5050(5) 0.3082(13) 0.063(3) Uani 1 1 d . . . . .
H18 H -0.1099 0.4922 0.2463 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2112(19) 0.4203(4) 0.2295(12) 0.057(3) Uani 1 1 d . . . . .
H19 H 0.0420 0.4129 0.1782 0.068 Uiso 1 1 calc R U . . .
C20 C 0.333(2) 0.4233(5) 0.1078(12) 0.072(3) Uani 1 1 d . . . . .
H20A H 0.2991 0.3893 0.0471 0.086 Uiso 1 1 calc R U . . .
H20B H 0.5016 0.4267 0.1558 0.086 Uiso 1 1 calc R U . . .
H20C H 0.2753 0.4558 0.0437 0.086 Uiso 1 1 calc R U . . .
C21 C -0.030(6) 0.2058(10) 0.211(3) 0.247(17) Uani 1 1 d . . . . .
H21A H -0.1593 0.2098 0.2526 0.296 Uiso 1 1 calc R U . . .
H21B H 0.1172 0.2133 0.2901 0.296 Uiso 1 1 calc R U . . .
H21C H -0.0292 0.1678 0.1737 0.296 Uiso 1 1 calc R U . . .
C22 C -0.305(3) 0.2966(9) 0.074(2) 0.170(11) Uani 1 1 d . . . . .
H22A H -0.3039 0.2987 0.1780 0.204 Uiso 1 1 calc R U . . .
H22B H -0.4526 0.2801 0.0121 0.204 Uiso 1 1 calc R U . . .
H22C H -0.2896 0.3342 0.0375 0.204 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.726(13) . ?
S1 O2 1.441(7) . ?
S1 O1 1.468(6) . ?
S1 O3 1.471(7) . ?
S1 C1 1.748(10) . ?
S2 O4 1.467(8) . ?
S2 C21 1.75(2) . ?
S2 C22 1.778(17) . ?
N1 N2 1.285(11) . ?
N1 C4 1.415(11) . ?
N2 C7 1.445(12) . ?
N3 C10 1.356(12) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N4 C19 1.502(12) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N4 H4C 0.9000 . ?
C1 C2 1.381(12) . ?
C1 C6 1.411(14) . ?
C2 C3 1.394(14) . ?
C2 H2 0.9400 . ?
C3 C4 1.401(14) . ?
C3 H3 0.9400 . ?
C4 C5 1.394(13) . ?
C5 C6 1.390(14) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.373(13) . ?
C7 C12 1.384(14) . ?
C8 C9 1.377(14) . ?
C8 H8 0.9400 . ?
C9 C10 1.425(15) . ?
C9 H9 0.9400 . ?
C10 C11 1.389(12) . ?
C11 C12 1.373(14) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.355(13) . ?
C13 C14 1.408(14) . ?
C13 C19 1.497(14) . ?
C14 C15 1.387(15) . ?
C14 H14 0.9400 . ?
C15 C16 1.364(18) . ?
C15 H15 0.9400 . ?
C16 C17 1.392(18) . ?
C17 C18 1.385(15) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.534(14) . ?
C19 H19 0.9900 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?

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 114.2(4) . . ?
O2 S1 O3 112.9(5) . . ?
O1 S1 O3 111.0(4) . . ?
O2 S1 C1 107.4(5) . . ?
O1 S1 C1 106.0(4) . . ?
O3 S1 C1 104.5(4) . . ?
O4 S2 C21 101.3(10) . . ?
O4 S2 C22 106.0(7) . . ?
C21 S2 C22 103.1(13) . . ?
N2 N1 C4 113.1(8) . . ?
N1 N2 C7 113.8(8) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C2 C1 C6 118.9(9) . . ?
C2 C1 S1 120.8(8) . . ?
C6 C1 S1 120.2(7) . . ?
C1 C2 C3 121.6(10) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 119.2(9) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.8(9) . . ?
C5 C4 N1 125.3(9) . . ?
C3 C4 N1 114.8(8) . . ?
C6 C5 C4 120.3(10) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.1(9) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C8 C7 C12 120.4(9) . . ?
C8 C7 N2 123.8(9) . . ?
C12 C7 N2 115.8(9) . . ?
C7 C8 C9 120.9(10) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 119.5(10) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C11 123.2(10) . . ?
N3 C10 C9 118.9(9) . . ?
C11 C10 C9 117.9(9) . . ?
C12 C11 C10 121.8(10) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C7 119.4(10) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C18 C13 C14 119.3(10) . . ?
C18 C13 C19 120.6(10) . . ?
C14 C13 C19 120.1(9) . . ?
C15 C14 C13 119.1(11) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 120.5(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.9(13) . . ?
C15 C16 Cl1 119.5(12) . . ?
C17 C16 Cl1 119.6(11) . . ?
C18 C17 C16 118.0(12) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C13 C18 C17 122.3(11) . . ?
C13 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C13 C19 N4 112.4(8) . . ?
C13 C19 C20 113.7(9) . . ?
N4 C19 C20 107.1(9) . . ?
C13 C19 H19 107.8 . . ?
N4 C19 H19 107.8 . . ?
C20 C19 H19 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S2 C21 H21A 109.5 . . ?
S2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S2 C22 H22A 109.5 . . ?
S2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C4 N1 N2 C7 178.2(7) . . . . ?
O2 S1 C1 C2 160.5(7) . . . . ?
O1 S1 C1 C2 37.9(8) . . . . ?
O3 S1 C1 C2 -79.4(8) . . . . ?
O2 S1 C1 C6 -22.9(9) . . . . ?
O1 S1 C1 C6 -145.4(8) . . . . ?
O3 S1 C1 C6 97.3(8) . . . . ?
C6 C1 C2 C3 -0.1(14) . . . . ?
S1 C1 C2 C3 176.6(8) . . . . ?
C1 C2 C3 C4 -0.8(15) . . . . ?
C2 C3 C4 C5 2.1(15) . . . . ?
C2 C3 C4 N1 179.5(9) . . . . ?
N2 N1 C4 C5 -9.2(13) . . . . ?
N2 N1 C4 C3 173.6(9) . . . . ?
C3 C4 C5 C6 -2.6(15) . . . . ?
N1 C4 C5 C6 -179.6(9) . . . . ?
C4 C5 C6 C1 1.6(15) . . . . ?
C2 C1 C6 C5 -0.3(14) . . . . ?
S1 C1 C6 C5 -177.0(7) . . . . ?
N1 N2 C7 C8 0.8(14) . . . . ?
N1 N2 C7 C12 -179.4(9) . . . . ?
C12 C7 C8 C9 3.5(17) . . . . ?
N2 C7 C8 C9 -176.7(10) . . . . ?
C7 C8 C9 C10 -3.7(18) . . . . ?
C8 C9 C10 N3 -178.0(10) . . . . ?
C8 C9 C10 C11 2.7(17) . . . . ?
N3 C10 C11 C12 179.3(11) . . . . ?
C9 C10 C11 C12 -1.4(17) . . . . ?
C10 C11 C12 C7 1.1(16) . . . . ?
C8 C7 C12 C11 -2.1(16) . . . . ?
N2 C7 C12 C11 178.1(9) . . . . ?
C18 C13 C14 C15 -0.8(15) . . . . ?
C19 C13 C14 C15 177.5(10) . . . . ?
C13 C14 C15 C16 0.2(17) . . . . ?
C14 C15 C16 C17 0.8(19) . . . . ?
C14 C15 C16 Cl1 -180.0(9) . . . . ?
C15 C16 C17 C18 -1.1(19) . . . . ?
Cl1 C16 C17 C18 179.7(8) . . . . ?
C14 C13 C18 C17 0.5(16) . . . . ?
C19 C13 C18 C17 -177.9(10) . . . . ?
C16 C17 C18 C13 0.5(17) . . . . ?
C18 C13 C19 N4 -124.8(11) . . . . ?
C14 C13 C19 N4 56.9(12) . . . . ?
C18 C13 C19 C20 113.3(12) . . . . ?
C14 C13 C19 C20 -65.0(12) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O2 . . 2_657 2.995(14) 0.870 2.281 139.2 no
N3 H3B O1 . . 2_757 2.974(11) 0.870 2.149 158.2 no
N4 H4A O1 . . 1_455 2.852(12) 0.900 1.970 166.0 no
N4 H4B O3 . . . 2.834(12) 0.900 1.936 175.6 no
N4 H4C O4 . . . 2.681(11) 0.900 1.805 163.5 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-(4-chlorophenyl)ethan-1-amine/dimethyl sulfoxide'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/DMSO'
####################################################################### 
# 
# 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_2-DMA
_database_code_depnum_ccdc_archive 'CCDC 1504258'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H31 N5 O4 S'
_chemical_formula_moiety         'C24 H31 N5 O4 S'
_chemical_formula_weight         485.60
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.19100(11)
_cell_length_b                   26.0113(5)
_cell_length_c                   8.06978(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.6890(10)
_cell_angle_gamma                90.0000
_cell_volume                     1267.79(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11578
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516.00
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.864

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            14197
_diffrn_reflns_av_R_equivalents  0.1410
_diffrn_reflns_theta_max         68.196
_diffrn_reflns_theta_min         3.398
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4506
_reflns_number_gt                2695
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.964

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1153
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_ref         0.2091
_refine_ls_wR_factor_gt          0.1583
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4506
_refine_ls_number_parameters     311
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0670P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 758 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(17)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.4982(3) 0.39946(7) 0.6835(3) 0.0530(6) Uani 1 1 d . . . . .
O1 O 0.4397(10) 0.3619(2) 0.7955(8) 0.0726(19) Uani 1 1 d . . . . .
O2 O 0.3666(8) 0.3961(2) 0.5099(7) 0.0694(17) Uani 1 1 d . . . . .
O3 O 0.7369(8) 0.3997(2) 0.6858(6) 0.0523(13) Uani 1 1 d . . . . .
O4 O 0.7953(15) 0.2822(3) 0.3088(10) 0.094(2) Uani 1 1 d . . . . .
N1 N 0.3225(12) 0.6065(2) 0.9424(10) 0.0573(19) Uani 1 1 d . . . . .
N2 N 0.1395(12) 0.6124(2) 0.9865(9) 0.0541(18) Uani 1 1 d . . . . .
N3 N -0.0161(11) 0.8066(2) 1.2320(10) 0.065(2) Uani 1 1 d . . . . .
H3A H -0.1381 0.8124 1.2631 0.078 Uiso 1 1 calc R U . . .
H3B H 0.0810 0.8306 1.2388 0.078 Uiso 1 1 calc R U . . .
N4 N 0.9007(11) 0.3822(2) 0.3986(8) 0.0567(18) Uani 1 1 d . . . . .
H4A H 0.8683 0.3497 0.3681 0.068 Uiso 1 1 calc R U . . .
H4B H 0.8387 0.3904 0.4847 0.068 Uiso 1 1 calc R U . . .
H4C H 1.0469 0.3858 0.4306 0.068 Uiso 1 1 calc R U . . .
N6 N 0.539(3) 0.2282(6) 0.3428(17) 0.151(6) Uani 1 1 d . . . . .
C1 C 0.4427(14) 0.4603(3) 0.7602(11) 0.050(2) Uani 1 1 d . . . . .
C2 C 0.2548(14) 0.4669(3) 0.8246(11) 0.057(2) Uani 1 1 d . . . . .
H2 H 0.1593 0.4394 0.8267 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2090(14) 0.5149(3) 0.8862(11) 0.058(2) Uani 1 1 d . . . . .
H3 H 0.0846 0.5192 0.9317 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3492(14) 0.5560(3) 0.8797(12) 0.052(2) Uani 1 1 d . . . . .
C5 C 0.5359(15) 0.5487(3) 0.8156(11) 0.058(2) Uani 1 1 d . . . . .
H5 H 0.6322 0.5760 0.8140 0.069 Uiso 1 1 calc R U . . .
C6 C 0.5824(13) 0.5010(3) 0.7533(11) 0.055(2) Uani 1 1 d . . . . .
H6 H 0.7065 0.4968 0.7074 0.066 Uiso 1 1 calc R U . . .
C7 C 0.1096(15) 0.6625(3) 1.0493(11) 0.056(2) Uani 1 1 d . . . . .
C8 C -0.0897(14) 0.6722(3) 1.0980(11) 0.057(2) Uani 1 1 d . . . . .
H8 H -0.1957 0.6464 1.0885 0.069 Uiso 1 1 calc R U . . .
C9 C -0.1290(15) 0.7189(3) 1.1586(11) 0.058(2) Uani 1 1 d . . . . .
H9 H -0.2614 0.7244 1.1924 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0236(15) 0.7592(3) 1.1720(10) 0.053(2) Uani 1 1 d . . . . .
C11 C 0.2227(14) 0.7490(3) 1.1209(12) 0.060(2) Uani 1 1 d . . . . .
H11 H 0.3278 0.7749 1.1278 0.072 Uiso 1 1 calc R U . . .
C12 C 0.2633(15) 0.7023(3) 1.0621(12) 0.060(2) Uani 1 1 d . . . . .
H12 H 0.3963 0.6966 1.0294 0.072 Uiso 1 1 calc R U . . .
C13 C 0.8206(17) 0.4726(3) 0.3093(11) 0.064(2) Uani 1 1 d . . . . .
C14 C 0.6248(17) 0.5010(4) 0.2820(13) 0.080(3) Uani 1 1 d . . . . .
H14 H 0.4912 0.4859 0.2296 0.096 Uiso 1 1 calc R U . . .
C15 C 0.630(2) 0.5522(5) 0.3334(16) 0.095(4) Uani 1 1 d . . . . .
H15 H 0.4982 0.5705 0.3184 0.114 Uiso 1 1 calc R U . . .
C16 C 0.822(2) 0.5757(4) 0.4044(16) 0.092(4) Uani 1 1 d . . . . .
H16 H 0.8243 0.6102 0.4341 0.110 Uiso 1 1 calc R U . . .
C17 C 1.015(2) 0.5476(4) 0.4321(15) 0.091(4) Uani 1 1 d . . . . .
H17 H 1.1477 0.5635 0.4830 0.109 Uiso 1 1 calc R U . . .
C18 C 1.0170(15) 0.4968(4) 0.3865(12) 0.069(3) Uani 1 1 d . . . . .
H18 H 1.1496 0.4786 0.4072 0.082 Uiso 1 1 calc R U . . .
C19 C 0.8133(15) 0.4170(3) 0.2510(11) 0.057(2) Uani 1 1 d . . . . .
H19 H 0.6586 0.4077 0.2033 0.068 Uiso 1 1 calc R U . . .
C20 C 0.9463(15) 0.4064(4) 0.1187(11) 0.077(3) Uani 1 1 d . . . . .
H20A H 0.9225 0.3716 0.0799 0.092 Uiso 1 1 calc R U . . .
H20B H 1.1007 0.4116 0.1674 0.092 Uiso 1 1 calc R U . . .
H20C H 0.9002 0.4294 0.0245 0.092 Uiso 1 1 calc R U . . .
C21 C 0.600(4) 0.2647(7) 0.301(2) 0.143(8) Uani 1 1 d . . . . .
C22 C 0.3959(19) 0.3027(4) 0.2164(16) 0.099(4) Uani 1 1 d . . . . .
H22A H 0.4537 0.3341 0.1809 0.119 Uiso 1 1 calc R U . . .
H22B H 0.3041 0.2861 0.1198 0.119 Uiso 1 1 calc R U . . .
H22C H 0.3096 0.3102 0.2987 0.119 Uiso 1 1 calc R U . . .
C23 C 0.323(2) 0.2077(6) 0.3527(17) 0.122(5) Uani 1 1 d . . . . .
H23A H 0.2787 0.1822 0.2659 0.146 Uiso 1 1 calc R U . . .
H23B H 0.2166 0.2351 0.3366 0.146 Uiso 1 1 calc R U . . .
H23C H 0.3326 0.1924 0.4622 0.146 Uiso 1 1 calc R U . . .
C24 C 0.751(2) 0.1901(4) 0.4268(16) 0.096(4) Uani 1 1 d . . . . .
H24A H 0.7519 0.1608 0.3546 0.115 Uiso 1 1 calc R U . . .
H24B H 0.7368 0.1788 0.5371 0.115 Uiso 1 1 calc R U . . .
H24C H 0.8873 0.2087 0.4371 0.115 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.430(5) . ?
S1 O2 1.460(5) . ?
S1 O3 1.474(5) . ?
S1 C1 1.759(8) . ?
O4 C21 1.278(18) . ?
N1 N2 1.270(8) . ?
N1 C4 1.428(10) . ?
N2 C7 1.425(9) . ?
N3 C10 1.366(9) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C19 1.499(9) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
N6 C21 1.103(17) . ?
N6 C23 1.455(14) . ?
N6 C24 1.668(19) . ?
C1 C6 1.377(10) . ?
C1 C2 1.385(11) . ?
C2 C3 1.395(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(11) . ?
C5 C6 1.392(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.396(11) . ?
C7 C8 1.397(11) . ?
C8 C9 1.351(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.409(10) . ?
C11 C12 1.346(11) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.390(12) . ?
C13 C14 1.397(12) . ?
C13 C19 1.518(12) . ?
C14 C15 1.392(14) . ?
C14 H14 0.9300 . ?
C15 C16 1.349(16) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(16) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(13) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.510(11) . ?
C19 H19 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.63(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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 113.6(4) . . ?
O1 S1 O3 112.8(4) . . ?
O2 S1 O3 111.0(3) . . ?
O1 S1 C1 107.2(4) . . ?
O2 S1 C1 106.3(4) . . ?
O3 S1 C1 105.3(4) . . ?
N2 N1 C4 113.0(7) . . ?
N1 N2 C7 113.9(7) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C21 N6 C23 136(2) . . ?
C21 N6 C24 110.0(18) . . ?
C23 N6 C24 114.2(14) . . ?
C6 C1 C2 120.4(7) . . ?
C6 C1 S1 120.4(6) . . ?
C2 C1 S1 119.3(6) . . ?
C1 C2 C3 119.9(7) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.9(8) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.4(7) . . ?
C5 C4 N1 115.6(7) . . ?
C3 C4 N1 125.0(8) . . ?
C4 C5 C6 121.0(7) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.3(8) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C12 C7 C8 118.3(8) . . ?
C12 C7 N2 124.5(8) . . ?
C8 C7 N2 117.2(7) . . ?
C9 C8 C7 120.3(8) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 122.0(9) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
N3 C10 C9 122.2(8) . . ?
N3 C10 C11 120.8(8) . . ?
C9 C10 C11 117.0(8) . . ?
C12 C11 C10 121.2(8) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 121.2(9) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C18 C13 C14 118.3(9) . . ?
C18 C13 C19 122.3(8) . . ?
C14 C13 C19 119.4(9) . . ?
C15 C14 C13 119.8(11) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 121.3(11) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 118.9(12) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 121.7(12) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 119.9(10) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
N4 C19 C20 107.1(7) . . ?
N4 C19 C13 110.4(7) . . ?
C20 C19 C13 114.1(8) . . ?
N4 C19 H19 108.4 . . ?
C20 C19 H19 108.4 . . ?
C13 C19 H19 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 O4 133(2) . . ?
N6 C21 C22 111(2) . . ?
O4 C21 C22 116.3(15) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N6 C23 H23A 109.5 . . ?
N6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N6 C24 H24A 109.5 . . ?
N6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C4 N1 N2 C7 -180.0(7) . . . . ?
O1 S1 C1 C6 142.1(7) . . . . ?
O2 S1 C1 C6 -96.1(7) . . . . ?
O3 S1 C1 C6 21.7(8) . . . . ?
O1 S1 C1 C2 -39.1(8) . . . . ?
O2 S1 C1 C2 82.6(7) . . . . ?
O3 S1 C1 C2 -159.5(7) . . . . ?
C6 C1 C2 C3 -1.4(13) . . . . ?
S1 C1 C2 C3 179.8(7) . . . . ?
C1 C2 C3 C4 1.3(13) . . . . ?
C2 C3 C4 C5 -1.5(14) . . . . ?
C2 C3 C4 N1 -178.4(8) . . . . ?
N2 N1 C4 C5 174.4(8) . . . . ?
N2 N1 C4 C3 -8.6(12) . . . . ?
C3 C4 C5 C6 1.7(13) . . . . ?
N1 C4 C5 C6 179.0(8) . . . . ?
C2 C1 C6 C5 1.6(12) . . . . ?
S1 C1 C6 C5 -179.6(6) . . . . ?
C4 C5 C6 C1 -1.8(13) . . . . ?
N1 N2 C7 C12 0.3(12) . . . . ?
N1 N2 C7 C8 179.0(7) . . . . ?
C12 C7 C8 C9 -1.2(13) . . . . ?
N2 C7 C8 C9 -180.0(8) . . . . ?
C7 C8 C9 C10 1.3(13) . . . . ?
C8 C9 C10 N3 179.5(8) . . . . ?
C8 C9 C10 C11 -0.6(13) . . . . ?
N3 C10 C11 C12 179.8(8) . . . . ?
C9 C10 C11 C12 -0.1(13) . . . . ?
C10 C11 C12 C7 0.1(14) . . . . ?
C8 C7 C12 C11 0.5(13) . . . . ?
N2 C7 C12 C11 179.2(8) . . . . ?
C18 C13 C14 C15 -0.6(15) . . . . ?
C19 C13 C14 C15 -179.4(9) . . . . ?
C13 C14 C15 C16 2.3(18) . . . . ?
C14 C15 C16 C17 -2.6(19) . . . . ?
C15 C16 C17 C18 1.2(19) . . . . ?
C16 C17 C18 C13 0.4(17) . . . . ?
C14 C13 C18 C17 -0.7(15) . . . . ?
C19 C13 C18 C17 178.0(9) . . . . ?
C18 C13 C19 N4 60.0(11) . . . . ?
C14 C13 C19 N4 -121.3(9) . . . . ?
C18 C13 C19 C20 -60.6(11) . . . . ?
C14 C13 C19 C20 118.0(9) . . . . ?
C23 N6 C21 O4 172.9(13) . . . . ?
C24 N6 C21 O4 -2(2) . . . . ?
C23 N6 C21 C22 -6(2) . . . . ?
C24 N6 C21 C22 179.5(9) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O1 . . 2_557 2.957(9) 0.860 2.231 142.0 no
N3 H3B O3 . . 2_657 2.963(8) 0.860 2.137 161.0 no
N4 H4A O4 . . . 2.741(9) 0.890 1.851 178.3 no
N4 H4B O3 . . . 2.764(9) 0.890 1.881 171.0 no
N4 H4C O2 . . 1_655 2.850(8) 0.890 1.961 177.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-phenylethan-1-amine/N,N-dimethylacetamide '
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/DMA'
####################################################################### 
# 
# 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_2-Dioxane
_database_code_depnum_ccdc_archive 'CCDC 1504259'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H30 N4 O5 S'
_chemical_formula_moiety         'C24 H30 N4 O5 S'
_chemical_formula_weight         486.58
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.06973(12)
_cell_length_b                   23.5497(5)
_cell_length_c                   9.2011(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.6090(12)
_cell_angle_gamma                90.0000
_cell_volume                     1246.44(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10931
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516.00
_exptl_absorpt_coefficient_mu    1.503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_T_max  0.860

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13460
_diffrn_reflns_av_R_equivalents  0.2100
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         3.754
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4359
_reflns_number_gt                2231
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_max     0.924
_reflns_Friedel_fraction_full    0.933

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.1953
_refine_ls_wR_factor_gt          0.1545
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4359
_refine_ls_number_parameters     310
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[σ²(Fo²)]'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.75
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(2)
_refine_ls_abs_structure_details 
;
 Flack x determined using 545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.4885(4) 0.39047(9) 0.5996(3) 0.0588(6) Uani 1 1 d . . . . .
O1 O 0.7378(8) 0.3899(3) 0.6203(6) 0.0613(14) Uani 1 1 d . . . . .
O2 O 0.3496(9) 0.4017(3) 0.4381(7) 0.0682(17) Uani 1 1 d . . . . .
O3 O 0.4166(12) 0.3405(2) 0.6618(8) 0.077(2) Uani 1 1 d . . . . .
O4 O 0.6689(12) 0.2821(3) 0.2522(8) 0.079(2) Uani 1 1 d . . . . .
O5 O 0.3496(14) 0.2110(4) 0.3326(11) 0.106(3) Uani 1 1 d . . . . .
N1 N 0.3104(13) 0.5937(3) 0.9284(9) 0.0620(19) Uani 1 1 d . . . . .
N2 N 0.1448(12) 0.5916(3) 0.9847(9) 0.062(2) Uani 1 1 d . . . . .
N3 N -0.0303(13) 0.7882(3) 1.2667(10) 0.087(3) Uani 1 1 d . . . . .
H3A H -0.1473 0.7890 1.3019 0.104 Uiso 1 1 calc R U . . .
H3B H 0.0562 0.8182 1.2736 0.104 Uiso 1 1 calc R U . . .
N4 N 0.8602(11) 0.3901(3) 0.3548(8) 0.0618(18) Uani 1 1 d . . . . .
H4A H 0.8106 0.3929 0.4368 0.074 Uiso 1 1 calc R U . . .
H4B H 1.0153 0.3950 0.3845 0.074 Uiso 1 1 calc R U . . .
H4C H 0.8240 0.3556 0.3118 0.074 Uiso 1 1 calc R U . . .
C1 C 0.4444(14) 0.4482(3) 0.7056(11) 0.054(2) Uani 1 1 d . . . . .
C2 C 0.5650(14) 0.4988(4) 0.7112(11) 0.061(2) Uani 1 1 d . . . . .
H2 H 0.6802 0.5011 0.6632 0.073 Uiso 1 1 calc R U . . .
C3 C 0.5179(15) 0.5456(4) 0.7863(10) 0.059(2) Uani 1 1 d . . . . .
H3 H 0.6016 0.5794 0.7893 0.071 Uiso 1 1 calc R U . . .
C4 C 0.3477(15) 0.5433(4) 0.8574(10) 0.056(2) Uani 1 1 d . . . . .
C5 C 0.2280(15) 0.4929(4) 0.8541(12) 0.063(2) Uani 1 1 d . . . . .
H5 H 0.1149 0.4908 0.9038 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2732(15) 0.4461(4) 0.7790(11) 0.064(2) Uani 1 1 d . . . . .
H6 H 0.1891 0.4124 0.7765 0.077 Uiso 1 1 calc R U . . .
C7 C 0.1084(14) 0.6418(4) 1.0554(11) 0.056(2) Uani 1 1 d . . . . .
C8 C 0.2477(15) 0.6903(4) 1.0722(11) 0.062(2) Uani 1 1 d . . . . .
H8 H 0.3738 0.6897 1.0339 0.075 Uiso 1 1 calc R U . . .
C9 C 0.2066(15) 0.7385(4) 1.1426(11) 0.068(3) Uani 1 1 d . . . . .
H9 H 0.3033 0.7704 1.1522 0.081 Uiso 1 1 calc R U . . .
C10 C 0.0177(15) 0.7399(4) 1.2005(11) 0.062(2) Uani 1 1 d . . . . .
C11 C -0.1208(15) 0.6911(4) 1.1886(11) 0.064(2) Uani 1 1 d . . . . .
H11 H -0.2437 0.6910 1.2300 0.077 Uiso 1 1 calc R U . . .
C12 C -0.0749(16) 0.6430(4) 1.1152(11) 0.062(2) Uani 1 1 d . . . . .
H12 H -0.1696 0.6107 1.1059 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7524(15) 0.4915(4) 0.3149(11) 0.062(2) Uani 1 1 d . . . . .
C14 C 0.9622(16) 0.5158(4) 0.4041(11) 0.069(3) Uani 1 1 d . . . . .
H14 H 1.1024 0.4968 0.4144 0.083 Uiso 1 1 calc R U . . .
C15 C 0.9677(17) 0.5671(4) 0.4772(12) 0.070(3) Uani 1 1 d . . . . .
H15 H 1.1097 0.5815 0.5418 0.084 Uiso 1 1 calc R U . . .
C16 C 0.7660(18) 0.5972(4) 0.4558(12) 0.072(3) Uani 1 1 d . . . . .
H16 H 0.7687 0.6328 0.5029 0.086 Uiso 1 1 calc R U . . .
C17 C 0.5615(18) 0.5745(4) 0.3647(13) 0.072(3) Uani 1 1 d . . . . .
H17 H 0.4230 0.5949 0.3502 0.086 Uiso 1 1 calc R U . . .
C18 C 0.5516(17) 0.5237(4) 0.2946(12) 0.072(3) Uani 1 1 d . . . . .
H18 H 0.4076 0.5099 0.2313 0.086 Uiso 1 1 calc R U . . .
C19 C 0.7436(15) 0.4353(4) 0.2391(11) 0.069(3) Uani 1 1 d . . . . .
H19 H 0.5778 0.4247 0.1944 0.082 Uiso 1 1 calc R U . . .
C20 C 0.8508(18) 0.4337(5) 0.1094(11) 0.088(3) Uani 1 1 d . . . . .
H20A H 1.0163 0.4412 0.1509 0.105 Uiso 1 1 calc R U . . .
H20B H 0.7780 0.4624 0.0337 0.105 Uiso 1 1 calc R U . . .
H20C H 0.8259 0.3966 0.0615 0.105 Uiso 1 1 calc R U . . .
C21 C 0.7351(19) 0.2309(5) 0.3406(14) 0.087(3) Uani 1 1 d . . . . .
H21A H 0.8946 0.2349 0.4101 0.104 Uiso 1 1 calc R U . . .
H21B H 0.7325 0.1992 0.2712 0.104 Uiso 1 1 calc R U . . .
C22 C 0.579(2) 0.2177(6) 0.4318(17) 0.108(4) Uani 1 1 d . . . . .
H22A H 0.6304 0.1828 0.4905 0.130 Uiso 1 1 calc R U . . .
H22B H 0.5847 0.2486 0.5042 0.130 Uiso 1 1 calc R U . . .
C23 C 0.2737(19) 0.2612(6) 0.2502(15) 0.097(4) Uani 1 1 d . . . . .
H23A H 0.2728 0.2920 0.3217 0.117 Uiso 1 1 calc R U . . .
H23B H 0.1145 0.2562 0.1812 0.117 Uiso 1 1 calc R U . . .
C24 C 0.4302(18) 0.2771(5) 0.1580(15) 0.100(4) Uani 1 1 d . . . . .
H24A H 0.4176 0.2482 0.0792 0.120 Uiso 1 1 calc R U . . .
H24B H 0.3782 0.3134 0.1060 0.120 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.436(6) . ?
S1 O1 1.464(5) . ?
S1 O2 1.480(6) . ?
S1 C1 1.743(9) . ?
O4 C24 1.436(11) . ?
O4 C21 1.439(11) . ?
O5 C23 1.402(14) . ?
O5 C22 1.408(13) . ?
N1 N2 1.270(8) . ?
N1 C4 1.408(10) . ?
N2 C7 1.401(10) . ?
N3 C10 1.366(10) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N4 C19 1.512(11) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N4 H4C 0.9000 . ?
C1 C2 1.390(11) . ?
C1 C6 1.409(11) . ?
C2 C3 1.379(11) . ?
C2 H2 0.9400 . ?
C3 C4 1.389(10) . ?
C3 H3 0.9400 . ?
C4 C5 1.386(10) . ?
C5 C6 1.376(11) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.390(12) . ?
C7 C8 1.401(11) . ?
C8 C9 1.370(11) . ?
C8 H8 0.9400 . ?
C9 C10 1.410(12) . ?
C9 H9 0.9400 . ?
C10 C11 1.408(12) . ?
C11 C12 1.391(11) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.397(12) . ?
C13 C14 1.399(12) . ?
C13 C19 1.488(12) . ?
C14 C15 1.376(12) . ?
C14 H14 0.9400 . ?
C15 C16 1.374(12) . ?
C15 H15 0.9400 . ?
C16 C17 1.366(13) . ?
C16 H16 0.9400 . ?
C17 C18 1.351(12) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.531(12) . ?
C19 H19 0.9900 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.486(14) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.509(15) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 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
O3 S1 O1 111.9(4) . . ?
O3 S1 O2 113.5(4) . . ?
O1 S1 O2 111.5(3) . . ?
O3 S1 C1 107.2(4) . . ?
O1 S1 C1 105.7(4) . . ?
O2 S1 C1 106.4(4) . . ?
C24 O4 C21 108.6(8) . . ?
C23 O5 C22 110.0(9) . . ?
N2 N1 C4 114.8(7) . . ?
N1 N2 C7 114.7(7) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C2 C1 C6 118.3(8) . . ?
C2 C1 S1 121.0(7) . . ?
C6 C1 S1 120.6(7) . . ?
C3 C2 C1 120.8(9) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.5(9) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.2(8) . . ?
C5 C4 N1 124.8(8) . . ?
C3 C4 N1 116.0(8) . . ?
C6 C5 C4 120.7(8) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.5(8) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C12 C7 C8 118.1(8) . . ?
C12 C7 N2 117.8(8) . . ?
C8 C7 N2 124.1(8) . . ?
C9 C8 C7 122.3(9) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C8 C9 C10 119.3(8) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C11 120.6(9) . . ?
N3 C10 C9 120.1(9) . . ?
C11 C10 C9 119.3(8) . . ?
C12 C11 C10 119.7(8) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C7 C12 C11 121.2(9) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C18 C13 C14 116.5(9) . . ?
C18 C13 C19 121.4(8) . . ?
C14 C13 C19 122.0(8) . . ?
C15 C14 C13 121.5(9) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 120.1(9) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 118.6(10) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C18 C17 C16 122.2(9) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C13 120.9(10) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C13 C19 N4 110.9(8) . . ?
C13 C19 C20 115.3(8) . . ?
N4 C19 C20 108.2(8) . . ?
C13 C19 H19 107.4 . . ?
N4 C19 H19 107.4 . . ?
C20 C19 H19 107.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C22 112.4(9) . . ?
O4 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
O4 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
O5 C22 C21 109.5(12) . . ?
O5 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
O5 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
O5 C23 C24 110.9(10) . . ?
O5 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
O4 C24 C23 112.1(11) . . ?
O4 C24 H24A 109.2 . . ?
C23 C24 H24A 109.2 . . ?
O4 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C7 179.9(7) . . . . ?
O3 S1 C1 C2 157.8(8) . . . . ?
O1 S1 C1 C2 38.3(8) . . . . ?
O2 S1 C1 C2 -80.4(8) . . . . ?
O3 S1 C1 C6 -26.7(8) . . . . ?
O1 S1 C1 C6 -146.2(7) . . . . ?
O2 S1 C1 C6 95.1(8) . . . . ?
C6 C1 C2 C3 -0.2(14) . . . . ?
S1 C1 C2 C3 175.4(7) . . . . ?
C1 C2 C3 C4 -0.3(13) . . . . ?
C2 C3 C4 C5 1.0(13) . . . . ?
C2 C3 C4 N1 -178.9(8) . . . . ?
N2 N1 C4 C5 -3.9(12) . . . . ?
N2 N1 C4 C3 176.0(8) . . . . ?
C3 C4 C5 C6 -1.3(13) . . . . ?
N1 C4 C5 C6 178.6(8) . . . . ?
C4 C5 C6 C1 0.9(13) . . . . ?
C2 C1 C6 C5 -0.1(14) . . . . ?
S1 C1 C6 C5 -175.7(7) . . . . ?
N1 N2 C7 C12 178.0(8) . . . . ?
N1 N2 C7 C8 -3.3(13) . . . . ?
C12 C7 C8 C9 -1.1(14) . . . . ?
N2 C7 C8 C9 -179.8(8) . . . . ?
C7 C8 C9 C10 -0.1(14) . . . . ?
C8 C9 C10 N3 -177.9(9) . . . . ?
C8 C9 C10 C11 1.8(14) . . . . ?
N3 C10 C11 C12 177.4(8) . . . . ?
C9 C10 C11 C12 -2.3(13) . . . . ?
C8 C7 C12 C11 0.6(14) . . . . ?
N2 C7 C12 C11 179.3(8) . . . . ?
C10 C11 C12 C7 1.1(14) . . . . ?
C18 C13 C14 C15 4.6(14) . . . . ?
C19 C13 C14 C15 -178.2(9) . . . . ?
C13 C14 C15 C16 -4.1(14) . . . . ?
C14 C15 C16 C17 1.8(14) . . . . ?
C15 C16 C17 C18 -0.4(15) . . . . ?
C16 C17 C18 C13 1.1(15) . . . . ?
C14 C13 C18 C17 -3.2(14) . . . . ?
C19 C13 C18 C17 179.6(9) . . . . ?
C18 C13 C19 N4 -127.3(9) . . . . ?
C14 C13 C19 N4 55.7(11) . . . . ?
C18 C13 C19 C20 109.4(10) . . . . ?
C14 C13 C19 C20 -67.6(12) . . . . ?
C24 O4 C21 C22 -55.1(12) . . . . ?
C23 O5 C22 C21 -60.4(14) . . . . ?
O4 C21 C22 O5 59.7(13) . . . . ?
C22 O5 C23 C24 58.9(13) . . . . ?
C21 O4 C24 C23 52.6(12) . . . . ?
O5 C23 C24 O4 -55.9(12) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O3 . . 2_557 2.903(12) 0.870 2.145 145.4 no
N3 H3B O1 . . 2_657 2.965(10) 0.870 2.142 157.5 no
N4 H4A O1 . . . 2.771(10) 0.900 1.878 171.6 no
N4 H4B O2 . . 1_655 2.835(8) 0.900 1.936 176.1 no
N4 H4C O4 . . . 2.830(9) 0.900 1.963 161.3 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-phenylethan-1-amine/dioxane'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/dioxane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-Dioxane
_database_code_depnum_ccdc_archive 'CCDC 1504260'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H29 Cl N4 O5 S'
_chemical_formula_moiety         'C24 H29 Cl N4 O5 S'
_chemical_formula_weight         521.03
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.00155(11)
_cell_length_b                   26.1427(5)
_cell_length_c                   8.40735(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.2470(9)
_cell_angle_gamma                90.0000
_cell_volume                     1272.66(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12456
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      68.17
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548.00
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.577
_exptl_absorpt_correction_T_max  0.783

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13914
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_theta_max         68.170
_diffrn_reflns_theta_min         3.381
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4492
_reflns_number_gt                3930
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.957

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1047
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4492
_refine_ls_number_parameters     318
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(10)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.1871(3) 0.61243(5) 0.44698(18) 0.0740(5) Uani 1 1 d . . . . .
S1 S 0.48882(18) 0.37781(4) 0.29134(13) 0.0378(3) Uani 1 1 d . . . . .
O1 O 0.2450(5) 0.37887(11) 0.2898(3) 0.0421(7) Uani 1 1 d . . . . .
O2 O 0.6335(5) 0.37549(12) 0.4593(4) 0.0525(8) Uani 1 1 d . . . . .
O3 O 0.5420(6) 0.33923(11) 0.1849(4) 0.0559(9) Uani 1 1 d . . . . .
O4 O 0.3174(6) 0.26903(12) 0.7273(4) 0.0497(8) Uani 1 1 d . . . . .
O5 O 0.6842(6) 0.22115(16) 0.6318(5) 0.0723(11) Uani 1 1 d . . . . .
N1 N 0.6735(7) 0.58154(14) 0.0336(5) 0.0442(9) Uani 1 1 d . . . . .
N2 N 0.8475(7) 0.58558(14) -0.0233(5) 0.0445(9) Uani 1 1 d . . . . .
N3 N 1.0314(7) 0.77941(14) -0.2358(5) 0.0546(11) Uani 1 1 d . . . . .
H3A H 1.1449 0.7833 -0.2793 0.066 Uiso 1 1 calc R U . . .
H3B H 0.9467 0.8052 -0.2262 0.066 Uiso 1 1 calc R U . . .
N4 N 0.1212(6) 0.36202(13) 0.5817(4) 0.0439(9) Uani 1 1 d . . . . .
H4A H 0.1832 0.3693 0.4991 0.053 Uiso 1 1 calc R U . . .
H4B H -0.0319 0.3643 0.5465 0.053 Uiso 1 1 calc R U . . .
H4C H 0.1606 0.3304 0.6173 0.053 Uiso 1 1 calc R U . . .
C1 C 0.5444(8) 0.43797(16) 0.2100(5) 0.0366(10) Uani 1 1 d . . . . .
C2 C 0.4073(8) 0.47931(15) 0.2199(5) 0.0405(11) Uani 1 1 d . . . . .
H2 H 0.2838 0.4759 0.2667 0.049 Uiso 1 1 calc R U . . .
C3 C 0.4555(8) 0.52633(16) 0.1590(6) 0.0431(11) Uani 1 1 d . . . . .
H3 H 0.3641 0.5546 0.1655 0.052 Uiso 1 1 calc R U . . .
C4 C 0.6381(8) 0.53131(16) 0.0891(5) 0.0403(10) Uani 1 1 d . . . . .
C5 C 0.7768(8) 0.48900(17) 0.0805(5) 0.0429(11) Uani 1 1 d . . . . .
H5 H 0.9007 0.4924 0.0341 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7304(8) 0.44227(16) 0.1408(5) 0.0408(10) Uani 1 1 d . . . . .
H6 H 0.8221 0.4140 0.1353 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8836(8) 0.63543(16) -0.0759(5) 0.0411(11) Uani 1 1 d . . . . .
C8 C 0.7490(8) 0.67772(16) -0.0603(5) 0.0417(10) Uani 1 1 d . . . . .
H8 H 0.6247 0.6738 -0.0147 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7994(8) 0.72483(17) -0.1119(5) 0.0429(11) Uani 1 1 d . . . . .
H9 H 0.7087 0.7527 -0.1007 0.052 Uiso 1 1 calc R U . . .
C10 C 0.9852(8) 0.73191(16) -0.1813(6) 0.0420(11) Uani 1 1 d . . . . .
C11 C 1.1210(8) 0.68980(16) -0.1960(6) 0.0467(11) Uani 1 1 d . . . . .
H11 H 1.2450 0.6937 -0.2420 0.056 Uiso 1 1 calc R U . . .
C12 C 1.0718(9) 0.64247(16) -0.1425(6) 0.0459(11) Uani 1 1 d . . . . .
H12 H 1.1651 0.6147 -0.1507 0.055 Uiso 1 1 calc R U . . .
C13 C 0.2001(8) 0.45297(18) 0.6557(6) 0.0471(11) Uani 1 1 d . . . . .
C14 C -0.0057(9) 0.47573(17) 0.5719(6) 0.0528(13) Uani 1 1 d . . . . .
H14 H -0.1430 0.4576 0.5573 0.063 Uiso 1 1 calc R U . . .
C15 C -0.0116(10) 0.52464(18) 0.5095(6) 0.0537(12) Uani 1 1 d . . . . .
H15 H -0.1512 0.5392 0.4524 0.064 Uiso 1 1 calc R U . . .
C16 C 0.1907(10) 0.55178(19) 0.5325(6) 0.0536(13) Uani 1 1 d . . . . .
C17 C 0.3968(10) 0.5305(2) 0.6179(7) 0.0626(15) Uani 1 1 d . . . . .
H17 H 0.5331 0.5490 0.6347 0.075 Uiso 1 1 calc R U . . .
C18 C 0.4004(9) 0.48177(19) 0.6780(6) 0.0531(13) Uani 1 1 d . . . . .
H18 H 0.5406 0.4676 0.7353 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2092(8) 0.39952(18) 0.7213(5) 0.0471(11) Uani 1 1 d . . . . .
H19 H 0.3713 0.3913 0.7733 0.057 Uiso 1 1 calc R U . . .
C20 C 0.0743(9) 0.39134(19) 0.8479(6) 0.0586(14) Uani 1 1 d . . . . .
H20A H 0.1375 0.4125 0.9424 0.070 Uiso 1 1 calc R U . . .
H20B H 0.0844 0.3561 0.8808 0.070 Uiso 1 1 calc R U . . .
H20C H -0.0845 0.4003 0.8010 0.070 Uiso 1 1 calc R U . . .
C21 C 0.5494(9) 0.26959(18) 0.8315(6) 0.0506(12) Uani 1 1 d . . . . .
H21A H 0.5710 0.2412 0.9083 0.061 Uiso 1 1 calc R U . . .
H21B H 0.5762 0.3011 0.8945 0.061 Uiso 1 1 calc R U . . .
C22 C 0.7184(9) 0.2654(2) 0.7288(7) 0.0603(14) Uani 1 1 d . . . . .
H22A H 0.7032 0.2952 0.6577 0.072 Uiso 1 1 calc R U . . .
H22B H 0.8741 0.2652 0.8007 0.072 Uiso 1 1 calc R U . . .
C23 C 0.4505(10) 0.2208(2) 0.5273(7) 0.0710(17) Uani 1 1 d . . . . .
H23A H 0.4251 0.1898 0.4614 0.085 Uiso 1 1 calc R U . . .
H23B H 0.4281 0.2498 0.4529 0.085 Uiso 1 1 calc R U . . .
C24 C 0.2798(10) 0.2233(2) 0.6298(6) 0.0588(14) Uani 1 1 d . . . . .
H24A H 0.1238 0.2232 0.5584 0.071 Uiso 1 1 calc R U . . .
H24B H 0.2978 0.1936 0.7012 0.071 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.739(5) . ?
S1 O3 1.439(3) . ?
S1 O2 1.451(3) . ?
S1 O1 1.460(3) . ?
S1 C1 1.781(4) . ?
O4 C24 1.434(6) . ?
O4 C21 1.437(6) . ?
O5 C22 1.400(6) . ?
O5 C23 1.446(6) . ?
N1 N2 1.262(5) . ?
N1 C4 1.428(5) . ?
N2 C7 1.411(5) . ?
N3 C10 1.377(5) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 C19 1.514(5) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
C1 C2 1.374(6) . ?
C1 C6 1.393(5) . ?
C2 C3 1.391(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(6) . ?
C5 C6 1.379(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.395(6) . ?
C7 C12 1.399(6) . ?
C8 C9 1.366(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.400(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(6) . ?
C11 C12 1.375(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.385(7) . ?
C13 C18 1.389(7) . ?
C13 C19 1.498(6) . ?
C14 C15 1.379(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(7) . ?
C17 C18 1.367(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.513(6) . ?
C19 H19 0.9800 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.499(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.504(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 113.7(2) . . ?
O3 S1 O1 113.18(19) . . ?
O2 S1 O1 110.55(18) . . ?
O3 S1 C1 106.6(2) . . ?
O2 S1 C1 106.61(19) . . ?
O1 S1 C1 105.56(18) . . ?
C24 O4 C21 109.8(4) . . ?
C22 O5 C23 109.3(4) . . ?
N2 N1 C4 114.2(4) . . ?
N1 N2 C7 114.0(4) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C2 C1 C6 121.4(4) . . ?
C2 C1 S1 119.7(3) . . ?
C6 C1 S1 118.9(3) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 N1 115.4(4) . . ?
C5 C4 N1 124.7(4) . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.1(4) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 C12 118.8(4) . . ?
C8 C7 N2 124.2(4) . . ?
C12 C7 N2 117.0(4) . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
N3 C10 C11 120.6(4) . . ?
N3 C10 C9 120.7(4) . . ?
C11 C10 C9 118.7(4) . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C14 C13 C18 117.4(5) . . ?
C14 C13 C19 122.0(4) . . ?
C18 C13 C19 120.6(5) . . ?
C15 C14 C13 121.5(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 119.4(5) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.3(5) . . ?
C17 C16 Cl1 119.8(4) . . ?
C15 C16 Cl1 119.9(5) . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 121.7(5) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
C13 C19 C20 114.6(4) . . ?
C13 C19 N4 110.3(4) . . ?
C20 C19 N4 108.2(4) . . ?
C13 C19 H19 107.8 . . ?
C20 C19 H19 107.8 . . ?
N4 C19 H19 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C22 110.0(4) . . ?
O4 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
O4 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O5 C22 C21 112.2(4) . . ?
O5 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
O5 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
O5 C23 C24 110.5(5) . . ?
O5 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
O5 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
O4 C24 C23 109.6(4) . . ?
O4 C24 H24A 109.7 . . ?
C23 C24 H24A 109.7 . . ?
O4 C24 H24B 109.7 . . ?
C23 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?

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
C4 N1 N2 C7 -179.2(4) . . . . ?
O3 S1 C1 C2 145.0(4) . . . . ?
O2 S1 C1 C2 -93.2(4) . . . . ?
O1 S1 C1 C2 24.4(4) . . . . ?
O3 S1 C1 C6 -36.4(4) . . . . ?
O2 S1 C1 C6 85.3(4) . . . . ?
O1 S1 C1 C6 -157.1(3) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
S1 C1 C2 C3 178.7(3) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C2 C3 C4 C5 -0.6(7) . . . . ?
C2 C3 C4 N1 -178.9(4) . . . . ?
N2 N1 C4 C3 177.1(4) . . . . ?
N2 N1 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
N1 C4 C5 C6 178.7(4) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
S1 C1 C6 C5 -178.8(3) . . . . ?
N1 N2 C7 C8 3.1(6) . . . . ?
N1 N2 C7 C12 -179.1(4) . . . . ?
C12 C7 C8 C9 1.0(6) . . . . ?
N2 C7 C8 C9 178.7(4) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 N3 178.7(4) . . . . ?
C8 C9 C10 C11 -0.6(7) . . . . ?
N3 C10 C11 C12 -179.4(4) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C10 C11 C12 C7 1.3(7) . . . . ?
C8 C7 C12 C11 -1.7(7) . . . . ?
N2 C7 C12 C11 -179.6(4) . . . . ?
C18 C13 C14 C15 1.5(7) . . . . ?
C19 C13 C14 C15 -178.8(4) . . . . ?
C13 C14 C15 C16 -0.8(8) . . . . ?
C14 C15 C16 C17 -0.5(8) . . . . ?
C14 C15 C16 Cl1 177.3(4) . . . . ?
C15 C16 C17 C18 1.0(8) . . . . ?
Cl1 C16 C17 C18 -176.8(4) . . . . ?
C16 C17 C18 C13 -0.2(8) . . . . ?
C14 C13 C18 C17 -1.0(7) . . . . ?
C19 C13 C18 C17 179.3(5) . . . . ?
C14 C13 C19 C20 -61.1(6) . . . . ?
C18 C13 C19 C20 118.5(5) . . . . ?
C14 C13 C19 N4 61.2(6) . . . . ?
C18 C13 C19 N4 -119.1(5) . . . . ?
C24 O4 C21 C22 57.3(5) . . . . ?
C23 O5 C22 C21 57.5(6) . . . . ?
O4 C21 C22 O5 -57.9(5) . . . . ?
C22 O5 C23 C24 -58.1(6) . . . . ?
C21 O4 C24 C23 -58.6(5) . . . . ?
O5 C23 C24 O4 59.2(6) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O3 . . 2_755 2.934(5) 0.860 2.348 125.7 no
N3 H3B O1 . . 2_655 3.053(5) 0.860 2.236 158.8 no
N4 H4A O1 . . . 2.779(5) 0.890 1.908 165.9 no
N4 H4B O2 . . 1_455 2.858(5) 0.890 1.971 174.6 no
N4 H4C O4 . . . 2.835(5) 0.890 1.964 165.8 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-(4-chlorophenyl)ethan-1-amine/dioxane'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/dioxane'
####################################################################### 
# 
# 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_2-DEF
_database_code_depnum_ccdc_archive 'CCDC 1504261'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H33 N5 O4 S'
_chemical_formula_moiety         'C25 H33 N5 O4 S'
_chemical_formula_weight         499.63
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.21672(11)
_cell_length_b                   26.5810(5)
_cell_length_c                   7.98985(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.5040(7)
_cell_angle_gamma                90.0000
_cell_volume                     1302.17(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12359
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532.00
_exptl_absorpt_coefficient_mu    1.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.370
_exptl_absorpt_correction_T_max  0.867

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13515
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         3.325
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4617
_reflns_number_gt                3833
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    0.939

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1175
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4617
_refine_ls_number_parameters     321
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0405P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.29
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0066(10)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(13)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.44229(18) 0.41581(4) 0.26473(14) 0.0403(3) Uani 1 1 d . . . . .
O1 O 0.5464(5) 0.41218(14) 0.4422(4) 0.0546(9) Uani 1 1 d . . . . .
O2 O 0.2052(4) 0.41582(13) 0.2494(4) 0.0419(7) Uani 1 1 d . . . . .
O3 O 0.5213(6) 0.37909(13) 0.1572(5) 0.0604(11) Uani 1 1 d . . . . .
O4 O -0.0119(6) 0.29090(15) 0.5934(6) 0.0678(11) Uani 1 1 d . . . . .
N1 N 0.6701(7) 0.62026(15) 0.0407(5) 0.0480(10) Uani 1 1 d . . . . .
N2 N 0.8612(7) 0.62771(14) 0.0113(5) 0.0460(10) Uani 1 1 d . . . . .
N3 N 1.0604(7) 0.82263(14) -0.1718(5) 0.0501(10) Uani 1 1 d . . . . .
H3A H 1.1876 0.8289 -0.1991 0.060 Uiso 1 1 calc R U . . .
H3B H 0.9659 0.8468 -0.1721 0.060 Uiso 1 1 calc R U . . .
N4 N 0.0006(7) 0.39460(14) 0.5284(5) 0.0442(10) Uani 1 1 d . . . . .
H4A H 0.0190 0.3614 0.5472 0.053 Uiso 1 1 calc R U . . .
H4B H 0.0615 0.4035 0.4381 0.053 Uiso 1 1 calc R U . . .
H4C H -0.1428 0.4018 0.5078 0.053 Uiso 1 1 calc R U . . .
N5 N 0.3014(8) 0.24733(17) 0.5922(6) 0.0606(12) Uani 1 1 d . . . . .
C1 C 0.5131(8) 0.47583(16) 0.1932(6) 0.0396(11) Uani 1 1 d . . . . .
C2 C 0.3801(8) 0.51708(18) 0.2081(6) 0.0474(12) Uani 1 1 d . . . . .
H2 H 0.2513 0.5130 0.2539 0.057 Uiso 1 1 calc R U . . .
C3 C 0.4366(8) 0.56364(19) 0.1560(6) 0.0489(12) Uani 1 1 d . . . . .
H3 H 0.3453 0.5914 0.1650 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6289(8) 0.57021(17) 0.0896(6) 0.0422(11) Uani 1 1 d . . . . .
C5 C 0.7615(8) 0.52893(18) 0.0743(6) 0.0445(11) Uani 1 1 d . . . . .
H5 H 0.8910 0.5329 0.0294 0.053 Uiso 1 1 calc R U . . .
C6 C 0.7022(8) 0.48185(17) 0.1254(6) 0.0431(11) Uani 1 1 d . . . . .
H6 H 0.7909 0.4538 0.1139 0.052 Uiso 1 1 calc R U . . .
C7 C 0.9026(8) 0.67753(16) -0.0348(6) 0.0412(11) Uani 1 1 d . . . . .
C8 C 0.7546(8) 0.71742(18) -0.0399(6) 0.0464(12) Uani 1 1 d . . . . .
H8 H 0.6160 0.7112 -0.0118 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8049(8) 0.76470(17) -0.0842(6) 0.0460(12) Uani 1 1 d . . . . .
H9 H 0.7019 0.7906 -0.0851 0.055 Uiso 1 1 calc R U . . .
C10 C 1.0094(8) 0.77521(17) -0.1286(6) 0.0404(11) Uani 1 1 d . . . . .
C11 C 1.1554(8) 0.73521(18) -0.1262(6) 0.0469(12) Uani 1 1 d . . . . .
H11 H 1.2924 0.7410 -0.1578 0.056 Uiso 1 1 calc R U . . .
C12 C 1.1043(9) 0.68800(18) -0.0794(6) 0.0477(12) Uani 1 1 d . . . . .
H12 H 1.2075 0.6621 -0.0772 0.057 Uiso 1 1 calc R U . . .
C13 C 0.0988(8) 0.4790(2) 0.6485(6) 0.0470(12) Uani 1 1 d . . . . .
C14 C -0.0937(9) 0.5036(2) 0.5813(7) 0.0634(15) Uani 1 1 d . . . . .
H14 H -0.2218 0.4847 0.5489 0.076 Uiso 1 1 calc R U . . .
C15 C -0.0998(11) 0.5546(2) 0.5615(9) 0.0758(19) Uani 1 1 d . . . . .
H15 H -0.2317 0.5703 0.5156 0.091 Uiso 1 1 calc R U . . .
C16 C 0.0854(13) 0.5833(2) 0.6082(9) 0.0760(19) Uani 1 1 d . . . . .
H16 H 0.0811 0.6183 0.5932 0.091 Uiso 1 1 calc R U . . .
C17 C 0.2765(11) 0.5595(3) 0.6770(8) 0.0783(19) Uani 1 1 d . . . . .
H17 H 0.4032 0.5787 0.7115 0.094 Uiso 1 1 calc R U . . .
C18 C 0.2839(10) 0.5081(2) 0.6960(7) 0.0638(16) Uani 1 1 d . . . . .
H18 H 0.4162 0.4925 0.7417 0.077 Uiso 1 1 calc R U . . .
C19 C 0.1070(8) 0.4231(2) 0.6811(6) 0.0476(12) Uani 1 1 d . . . . .
H19 H 0.2621 0.4129 0.7061 0.057 Uiso 1 1 calc R U . . .
C20 C -0.0007(10) 0.4082(2) 0.8318(6) 0.0639(16) Uani 1 1 d . . . . .
H20A H -0.1543 0.4169 0.8084 0.077 Uiso 1 1 calc R U . . .
H20B H 0.0688 0.4260 0.9323 0.077 Uiso 1 1 calc R U . . .
H20C H 0.0148 0.3723 0.8507 0.077 Uiso 1 1 calc R U . . .
C21 C 0.0913(11) 0.2519(2) 0.6059(8) 0.0635(16) Uani 1 1 d . . . . .
H21 H 0.0168 0.2224 0.6271 0.076 Uiso 1 1 calc R U . . .
C22 C 0.4298(9) 0.2921(2) 0.5711(8) 0.0590(15) Uani 1 1 d . . . . .
H22A H 0.3389 0.3163 0.4986 0.071 Uiso 1 1 calc R U . . .
H22B H 0.5525 0.2829 0.5145 0.071 Uiso 1 1 calc R U . . .
C23 C 0.5160(10) 0.3166(2) 0.7398(8) 0.0685(17) Uani 1 1 d . . . . .
H23A H 0.5922 0.3473 0.7208 0.082 Uiso 1 1 calc R U . . .
H23B H 0.6157 0.2937 0.8083 0.082 Uiso 1 1 calc R U . . .
H23C H 0.3953 0.3243 0.7985 0.082 Uiso 1 1 calc R U . . .
C24 C 0.4180(14) 0.1987(3) 0.6277(9) 0.087(2) Uani 1 1 d . . . . .
H24A H 0.5477 0.2040 0.7139 0.104 Uiso 1 1 calc R U . . .
H24B H 0.3227 0.1749 0.6737 0.104 Uiso 1 1 calc R U . . .
C25 C 0.4835(17) 0.1774(3) 0.4765(12) 0.113(3) Uani 1 1 d . . . . .
H25A H 0.5768 0.2011 0.4301 0.136 Uiso 1 1 calc R U . . .
H25B H 0.3550 0.1706 0.3929 0.136 Uiso 1 1 calc R U . . .
H25C H 0.5624 0.1463 0.5057 0.136 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.439(4) . ?
S1 O2 1.459(3) . ?
S1 O1 1.461(3) . ?
S1 C1 1.774(5) . ?
O4 C21 1.214(7) . ?
N1 N2 1.264(5) . ?
N1 C4 1.422(6) . ?
N2 C7 1.409(5) . ?
N3 C10 1.358(6) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N4 C19 1.495(6) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N4 H4C 0.9000 . ?
N5 C21 1.334(7) . ?
N5 C22 1.459(7) . ?
N5 C24 1.485(8) . ?
C1 C6 1.383(7) . ?
C1 C2 1.390(6) . ?
C2 C3 1.370(7) . ?
C2 H2 0.9400 . ?
C3 C4 1.397(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.390(6) . ?
C5 C6 1.385(6) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.387(6) . ?
C7 C8 1.400(6) . ?
C8 C9 1.356(6) . ?
C8 H8 0.9400 . ?
C9 C10 1.403(6) . ?
C9 H9 0.9400 . ?
C10 C11 1.396(6) . ?
C11 C12 1.362(7) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.387(7) . ?
C13 C14 1.391(7) . ?
C13 C19 1.508(7) . ?
C14 C15 1.365(8) . ?
C14 H14 0.9400 . ?
C15 C16 1.380(9) . ?
C15 H15 0.9400 . ?
C16 C17 1.377(9) . ?
C16 H16 0.9400 . ?
C17 C18 1.375(9) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.523(7) . ?
C19 H19 0.9900 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21 0.9400 . ?
C22 C23 1.512(8) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 C25 1.452(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 112.9(2) . . ?
O3 S1 O1 113.2(2) . . ?
O2 S1 O1 111.16(18) . . ?
O3 S1 C1 106.9(2) . . ?
O2 S1 C1 105.9(2) . . ?
O1 S1 C1 106.1(2) . . ?
N2 N1 C4 114.5(4) . . ?
N1 N2 C7 114.4(4) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C21 N5 C22 119.8(5) . . ?
C21 N5 C24 121.2(5) . . ?
C22 N5 C24 118.2(5) . . ?
C6 C1 C2 119.9(4) . . ?
C6 C1 S1 120.2(3) . . ?
C2 C1 S1 120.0(4) . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 N1 125.3(4) . . ?
C3 C4 N1 115.2(4) . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 C5 120.3(4) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C12 C7 C8 117.3(4) . . ?
C12 C7 N2 117.8(4) . . ?
C8 C7 N2 124.9(4) . . ?
C9 C8 C7 122.1(5) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 120.5(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N3 C10 C11 122.1(4) . . ?
N3 C10 C9 120.5(4) . . ?
C11 C10 C9 117.3(4) . . ?
C12 C11 C10 121.6(5) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C7 121.2(4) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C18 C13 C14 117.7(5) . . ?
C18 C13 C19 120.0(5) . . ?
C14 C13 C19 122.1(5) . . ?
C15 C14 C13 121.1(6) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.8(6) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 118.7(6) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 120.7(6) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C13 120.9(6) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
N4 C19 C13 111.1(4) . . ?
N4 C19 C20 108.7(4) . . ?
C13 C19 C20 112.7(5) . . ?
N4 C19 H19 108.1 . . ?
C13 C19 H19 108.1 . . ?
C20 C19 H19 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 N5 125.7(5) . . ?
O4 C21 H21 117.2 . . ?
N5 C21 H21 117.2 . . ?
N5 C22 C23 111.6(5) . . ?
N5 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
N5 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 N5 112.1(6) . . ?
C25 C24 H24A 109.2 . . ?
N5 C24 H24A 109.2 . . ?
C25 C24 H24B 109.2 . . ?
N5 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C4 N1 N2 C7 -179.1(4) . . . . ?
O3 S1 C1 C6 -32.5(5) . . . . ?
O2 S1 C1 C6 -153.2(4) . . . . ?
O1 S1 C1 C6 88.6(4) . . . . ?
O3 S1 C1 C2 148.5(4) . . . . ?
O2 S1 C1 C2 27.9(4) . . . . ?
O1 S1 C1 C2 -90.3(4) . . . . ?
C6 C1 C2 C3 -0.2(7) . . . . ?
S1 C1 C2 C3 178.7(4) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C2 C3 C4 C5 0.9(8) . . . . ?
C2 C3 C4 N1 -179.8(5) . . . . ?
N2 N1 C4 C5 -13.4(7) . . . . ?
N2 N1 C4 C3 167.3(4) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
N1 C4 C5 C6 -179.4(4) . . . . ?
C2 C1 C6 C5 0.9(7) . . . . ?
S1 C1 C6 C5 -178.0(4) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
N1 N2 C7 C12 -176.1(5) . . . . ?
N1 N2 C7 C8 3.6(7) . . . . ?
C12 C7 C8 C9 -0.8(8) . . . . ?
N2 C7 C8 C9 179.5(5) . . . . ?
C7 C8 C9 C10 0.6(8) . . . . ?
C8 C9 C10 N3 -179.5(5) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
N3 C10 C11 C12 178.6(4) . . . . ?
C9 C10 C11 C12 -1.4(7) . . . . ?
C10 C11 C12 C7 1.2(8) . . . . ?
C8 C7 C12 C11 -0.1(7) . . . . ?
N2 C7 C12 C11 179.6(4) . . . . ?
C18 C13 C14 C15 0.5(9) . . . . ?
C19 C13 C14 C15 176.3(5) . . . . ?
C13 C14 C15 C16 -0.1(10) . . . . ?
C14 C15 C16 C17 -0.8(11) . . . . ?
C15 C16 C17 C18 1.3(11) . . . . ?
C16 C17 C18 C13 -0.9(10) . . . . ?
C14 C13 C18 C17 0.0(9) . . . . ?
C19 C13 C18 C17 -175.9(5) . . . . ?
C18 C13 C19 N4 -134.0(5) . . . . ?
C14 C13 C19 N4 50.2(7) . . . . ?
C18 C13 C19 C20 103.7(6) . . . . ?
C14 C13 C19 C20 -72.1(6) . . . . ?
C22 N5 C21 O4 4.2(9) . . . . ?
C24 N5 C21 O4 173.5(7) . . . . ?
C21 N5 C22 C23 83.8(6) . . . . ?
C24 N5 C22 C23 -85.8(6) . . . . ?
C21 N5 C24 C25 114.0(8) . . . . ?
C22 N5 C24 C25 -76.6(8) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O3 . . 2_755 2.988(6) 0.870 2.230 145.6 no
N3 H3B O2 . . 2_655 2.985(5) 0.870 2.159 158.2 no
N4 H4A O4 . . . 2.808(5) 0.900 1.925 166.6 no
N4 H4B O2 . . . 2.800(5) 0.900 1.903 174.1 no
N4 H4C O1 . . 1_455 2.832(5) 0.900 1.936 173.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-phenylethan-1-amine/N,N-diethylformamide'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/DEF'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-GF
_database_code_depnum_ccdc_archive 'CCDC 1504262'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2016-10-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H21 Cl N4 O3 S'
_chemical_formula_moiety         'C20 H21 Cl N4 O3 S'
_chemical_formula_weight         432.92
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.3493(2)
_cell_length_b                   6.04446(19)
_cell_length_c                   23.3114(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.6950(17)
_cell_angle_gamma                90.0000
_cell_volume                     1032.07(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4622
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452.00
_exptl_absorpt_coefficient_mu    2.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.516
_exptl_absorpt_correction_T_max  0.753

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.000
_diffrn_reflns_number            11000
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         3.805
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3640
_reflns_number_gt                2419
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.936
_reflns_Friedel_fraction_full    0.939

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2025
_refine_ls_wR_factor_gt          0.1559
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3640
_refine_ls_number_parameters     264
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0853P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.59
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.1866(4) 0.9195(5) 0.33303(11) 0.0799(9) Uani 1 1 d . . . . .
S1 S 0.5878(3) 0.6274(4) 0.10003(9) 0.0479(5) Uani 1 1 d . . . . .
O1 O 0.6064(7) 0.8686(9) 0.0996(3) 0.0529(16) Uani 1 1 d . . . . .
O2 O 0.4033(7) 0.5592(10) 0.0830(3) 0.0556(16) Uani 1 1 d . . . . .
O3 O 0.7229(8) 0.5188(10) 0.0673(3) 0.069(2) Uani 1 1 d . . . . .
N1 N 0.6825(10) 0.3632(13) 0.3462(3) 0.056(2) Uani 1 1 d . . . . .
N2 N 0.7340(9) 0.1678(13) 0.3584(3) 0.0562(19) Uani 1 1 d . . . . .
N3 N 0.7842(13) -0.0865(17) 0.5889(4) 0.093(3) Uani 1 1 d . . . . .
H3A H 0.7476 0.0007 0.6153 0.112 Uiso 1 1 calc R U . . .
H3B H 0.8322 -0.2143 0.5984 0.112 Uiso 1 1 calc R U . . .
N4 N 0.3156(7) 1.1080(12) 0.0540(3) 0.0458(16) Uani 1 1 d . . . . .
H4A H 0.4161 1.0352 0.0683 0.055 Uiso 1 1 calc R U . . .
H4B H 0.3218 1.2498 0.0657 0.055 Uiso 1 1 calc R U . . .
H4C H 0.3086 1.1030 0.0152 0.055 Uiso 1 1 calc R U . . .
C1 C 0.6346(11) 0.5474(13) 0.1722(3) 0.0427(19) Uani 1 1 d . . . . .
C2 C 0.5833(11) 0.6865(15) 0.2150(4) 0.055(2) Uani 1 1 d . . . . .
H2 H 0.5325 0.8256 0.2053 0.066 Uiso 1 1 calc R U . . .
C3 C 0.6063(11) 0.6224(17) 0.2722(4) 0.057(2) Uani 1 1 d . . . . .
H3 H 0.5743 0.7200 0.3011 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6755(11) 0.4168(16) 0.2870(4) 0.048(2) Uani 1 1 d . . . . .
C5 C 0.7309(11) 0.2718(15) 0.2445(4) 0.050(2) Uani 1 1 d . . . . .
H5 H 0.7817 0.1328 0.2544 0.060 Uiso 1 1 calc R U . . .
C6 C 0.7080(11) 0.3411(14) 0.1871(4) 0.050(2) Uani 1 1 d . . . . .
H6 H 0.7429 0.2462 0.1580 0.060 Uiso 1 1 calc R U . . .
C7 C 0.7389(11) 0.1111(17) 0.4172(4) 0.053(2) Uani 1 1 d . . . . .
C8 C 0.6777(12) 0.2481(19) 0.4597(4) 0.062(2) Uani 1 1 d . . . . .
H8 H 0.6277 0.3873 0.4497 0.074 Uiso 1 1 calc R U . . .
C9 C 0.6902(13) 0.1804(17) 0.5169(4) 0.066(3) Uani 1 1 d . . . . .
H9 H 0.6466 0.2732 0.5450 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7665(14) -0.0232(18) 0.5328(4) 0.062(3) Uani 1 1 d . . . . .
C11 C 0.8260(13) -0.1595(17) 0.4899(4) 0.065(3) Uani 1 1 d . . . . .
H11 H 0.8767 -0.2984 0.4999 0.078 Uiso 1 1 calc R U . . .
C12 C 0.8120(12) -0.0946(17) 0.4333(4) 0.062(2) Uani 1 1 d . . . . .
H12 H 0.8522 -0.1899 0.4051 0.075 Uiso 1 1 calc R U . . .
C13 C 0.1600(10) 0.9893(13) 0.1398(3) 0.043(2) Uani 1 1 d . . . . .
C14 C 0.2282(10) 1.1605(15) 0.1757(4) 0.049(2) Uani 1 1 d . . . . .
H14 H 0.2689 1.2917 0.1593 0.058 Uiso 1 1 calc R U . . .
C15 C 0.2366(10) 1.1402(18) 0.2347(4) 0.055(2) Uani 1 1 d . . . . .
H15 H 0.2873 1.2542 0.2584 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1701(11) 0.9515(17) 0.2589(4) 0.053(2) Uani 1 1 d . . . . .
C17 C 0.0953(12) 0.7807(15) 0.2240(4) 0.054(2) Uani 1 1 d . . . . .
H17 H 0.0479 0.6536 0.2407 0.065 Uiso 1 1 calc R U . . .
C18 C 0.0918(11) 0.8005(15) 0.1653(4) 0.051(2) Uani 1 1 d . . . . .
H18 H 0.0426 0.6852 0.1418 0.061 Uiso 1 1 calc R U . . .
C19 C 0.1491(10) 1.0010(13) 0.0751(4) 0.044(2) Uani 1 1 d . . . . .
H19 H 0.1434 0.8474 0.0603 0.053 Uiso 1 1 calc R U . . .
C20 C -0.0183(10) 1.123(2) 0.0485(4) 0.060(2) Uani 1 1 d . . . . .
H20A H -0.1277 1.0444 0.0573 0.072 Uiso 1 1 calc R U . . .
H20B H -0.0133 1.1306 0.0071 0.072 Uiso 1 1 calc R U . . .
H20C H -0.0207 1.2715 0.0641 0.072 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.733(9) . ?
S1 O2 1.441(6) . ?
S1 O3 1.458(6) . ?
S1 O1 1.464(6) . ?
S1 C1 1.757(8) . ?
N1 N2 1.266(9) . ?
N1 C4 1.413(10) . ?
N2 C7 1.410(10) . ?
N3 C10 1.358(12) . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N4 C19 1.502(9) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N4 H4C 0.9000 . ?
C1 C2 1.382(11) . ?
C1 C6 1.391(11) . ?
C2 C3 1.386(12) . ?
C2 H2 0.9400 . ?
C3 C4 1.376(13) . ?
C3 H3 0.9400 . ?
C4 C5 1.408(12) . ?
C5 C6 1.399(12) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C12 1.394(13) . ?
C7 C8 1.394(13) . ?
C8 C9 1.389(13) . ?
C8 H8 0.9400 . ?
C9 C10 1.390(13) . ?
C9 H9 0.9400 . ?
C10 C11 1.394(13) . ?
C11 C12 1.373(12) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C18 1.399(11) . ?
C13 C14 1.398(10) . ?
C13 C19 1.505(11) . ?
C14 C15 1.377(11) . ?
C14 H14 0.9400 . ?
C15 C16 1.379(13) . ?
C15 H15 0.9400 . ?
C16 C17 1.398(13) . ?
C17 C18 1.374(12) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.522(11) . ?
C19 H19 0.9900 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?

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 O3 113.1(4) . . ?
O2 S1 O1 111.7(3) . . ?
O3 S1 O1 112.1(4) . . ?
O2 S1 C1 106.9(4) . . ?
O3 S1 C1 106.8(4) . . ?
O1 S1 C1 105.7(4) . . ?
N2 N1 C4 114.9(8) . . ?
N1 N2 C7 115.4(8) . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C2 C1 C6 119.2(8) . . ?
C2 C1 S1 118.7(7) . . ?
C6 C1 S1 121.9(6) . . ?
C1 C2 C3 120.4(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.5(9) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.6(8) . . ?
C3 C4 N1 115.8(8) . . ?
C5 C4 N1 123.6(9) . . ?
C6 C5 C4 117.9(8) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C1 C6 C5 121.5(8) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C12 C7 C8 118.6(9) . . ?
C12 C7 N2 117.2(8) . . ?
C8 C7 N2 124.2(9) . . ?
C9 C8 C7 120.4(10) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.8(10) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N3 C10 C9 120.8(10) . . ?
N3 C10 C11 120.9(10) . . ?
C9 C10 C11 118.3(9) . . ?
C12 C11 C10 121.2(10) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 120.7(10) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 C14 118.2(8) . . ?
C18 C13 C19 118.2(7) . . ?
C14 C13 C19 123.6(7) . . ?
C15 C14 C13 121.2(8) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 119.5(9) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C17 120.6(8) . . ?
C15 C16 Cl1 120.1(7) . . ?
C17 C16 Cl1 119.3(8) . . ?
C18 C17 C16 119.3(9) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C13 121.1(8) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
N4 C19 C13 111.8(6) . . ?
N4 C19 C20 108.1(7) . . ?
C13 C19 C20 114.0(6) . . ?
N4 C19 H19 107.6 . . ?
C13 C19 H19 107.6 . . ?
C20 C19 H19 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 N1 N2 C7 -179.1(7) . . . . ?
O2 S1 C1 C2 -85.0(7) . . . . ?
O3 S1 C1 C2 153.6(7) . . . . ?
O1 S1 C1 C2 34.1(7) . . . . ?
O2 S1 C1 C6 89.7(7) . . . . ?
O3 S1 C1 C6 -31.7(8) . . . . ?
O1 S1 C1 C6 -151.3(7) . . . . ?
C6 C1 C2 C3 0.6(12) . . . . ?
S1 C1 C2 C3 175.5(6) . . . . ?
C1 C2 C3 C4 -1.9(12) . . . . ?
C2 C3 C4 C5 2.6(12) . . . . ?
C2 C3 C4 N1 -176.2(7) . . . . ?
N2 N1 C4 C3 175.1(7) . . . . ?
N2 N1 C4 C5 -3.6(12) . . . . ?
C3 C4 C5 C6 -1.9(12) . . . . ?
N1 C4 C5 C6 176.7(7) . . . . ?
C2 C1 C6 C5 0.0(12) . . . . ?
S1 C1 C6 C5 -174.7(6) . . . . ?
C4 C5 C6 C1 0.7(12) . . . . ?
N1 N2 C7 C12 -173.7(8) . . . . ?
N1 N2 C7 C8 5.4(12) . . . . ?
C12 C7 C8 C9 0.2(14) . . . . ?
N2 C7 C8 C9 -179.0(8) . . . . ?
C7 C8 C9 C10 1.1(14) . . . . ?
C8 C9 C10 N3 177.9(9) . . . . ?
C8 C9 C10 C11 -1.5(14) . . . . ?
N3 C10 C11 C12 -178.6(9) . . . . ?
C9 C10 C11 C12 0.7(15) . . . . ?
C10 C11 C12 C7 0.5(15) . . . . ?
C8 C7 C12 C11 -0.9(14) . . . . ?
N2 C7 C12 C11 178.3(8) . . . . ?
C18 C13 C14 C15 3.2(12) . . . . ?
C19 C13 C14 C15 -179.4(7) . . . . ?
C13 C14 C15 C16 -2.6(12) . . . . ?
C14 C15 C16 C17 0.3(13) . . . . ?
C14 C15 C16 Cl1 177.9(6) . . . . ?
C15 C16 C17 C18 1.3(13) . . . . ?
Cl1 C16 C17 C18 -176.3(6) . . . . ?
C16 C17 C18 C13 -0.6(13) . . . . ?
C14 C13 C18 C17 -1.5(12) . . . . ?
C19 C13 C18 C17 -179.1(7) . . . . ?
C18 C13 C19 N4 -142.1(7) . . . . ?
C14 C13 C19 N4 40.5(10) . . . . ?
C18 C13 C19 C20 95.0(9) . . . . ?
C14 C13 C19 C20 -82.4(10) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N4 H4A O1 . . . 2.724(8) 0.900 1.826 174.9 no
N4 H4B O2 . . 1_565 2.871(9) 0.900 1.995 164.1 no
N4 H4C O3 . . 2_655 2.867(9) 0.900 1.985 166.6 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
'(E)-4-((4-aminophenyl)diazenyl)benzenesulfonic acid/(R)-1-(4-chlorophenyl)ethan-1-amine'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
