# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_KB1306_0m
_database_code_depnum_ccdc_archive 'CCDC 2361366'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-06-08 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Azathioprine
_chemical_name_common            Azathioprine
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 N7 O2 S'
_chemical_formula_sum            'C9 H7 N7 O2 S'
_chemical_formula_weight         277.28

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

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

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

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

_cell_length_a                   10.3738(7)
_cell_length_b                   8.3050(5)
_cell_length_c                   13.8405(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.676(2)
_cell_angle_gamma                90
_cell_volume                     1158.61(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5250
_cell_measurement_theta_min      3.88
_cell_measurement_theta_max      29.22

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.291
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14246
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.883
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3468
_reflns_number_gt                2328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.3207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3468
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33505(17) 0.7018(2) 0.13397(13) 0.0414(4) Uani 1 1 d . . . . .
H1 H 0.247019 0.732150 0.109824 0.050 Uiso 1 1 calc R U . . .
C2 C 0.52974(15) 0.6009(2) 0.13694(11) 0.0327(4) Uani 1 1 d . . . . .
C3 C 0.52352(15) 0.6606(2) 0.22977(11) 0.0320(4) Uani 1 1 d . . . . .
C4 C 0.63840(15) 0.6447(2) 0.30540(11) 0.0320(3) Uani 1 1 d . . . . .
C5 C 0.73962(17) 0.5267(3) 0.19393(12) 0.0435(5) Uani 1 1 d . . . . .
H5 H 0.816479 0.480255 0.182971 0.052 Uiso 1 1 calc R U . . .
C6 C 0.79257(16) 0.6801(2) 0.49336(11) 0.0345(4) Uani 1 1 d . . . . .
C7 C 0.91537(18) 0.7381(2) 0.49096(13) 0.0421(4) Uani 1 1 d . . . . .
C8 C 0.9498(2) 0.5866(3) 0.61452(16) 0.0583(6) Uani 1 1 d . . . . .
H8 H 0.991357 0.530219 0.671420 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7229(2) 0.4855(3) 0.61369(16) 0.0638(6) Uani 1 1 d . . . . .
H9A H 0.666123 0.427583 0.560125 0.096 Uiso 1 1 calc R U . . .
H9B H 0.670227 0.555555 0.644063 0.096 Uiso 1 1 calc R U . . .
H9C H 0.769917 0.410671 0.662260 0.096 Uiso 1 1 calc R U . . .
N1 N 0.39996(14) 0.7245(2) 0.22700(11) 0.0409(4) Uani 1 1 d . . . . .
N2 N 0.40813(14) 0.6300(2) 0.07633(11) 0.0391(4) Uani 1 1 d . . . . .
H2N H 0.384(2) 0.592(3) 0.0153(17) 0.054(6) Uiso 1 1 d . . . . .
N3 N 0.63637(14) 0.5323(2) 0.11546(10) 0.0408(4) Uani 1 1 d . . . . .
N4 N 0.74681(13) 0.57954(19) 0.28658(10) 0.0382(4) Uani 1 1 d . . . . .
N5 N 0.81786(15) 0.5813(2) 0.57504(11) 0.0430(4) Uani 1 1 d . . . . .
N6 N 1.01287(16) 0.6783(3) 0.56521(14) 0.0584(5) Uani 1 1 d . . . . .
N7 N 0.9476(2) 0.8440(2) 0.41920(14) 0.0571(5) Uani 1 1 d . . . . .
O1 O 0.8577(2) 0.9057(2) 0.35719(13) 0.0728(5) Uani 1 1 d . . . . .
O2 O 1.0658(2) 0.8698(3) 0.42513(17) 0.1058(8) Uani 1 1 d . . . . .
S1 S 0.63196(4) 0.71350(7) 0.42440(3) 0.04402(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.318(2) . ?
C1 N2 1.361(2) . ?
C1 H1 0.9300 . ?
C2 N3 1.339(2) . ?
C2 N2 1.3613(19) . ?
C2 C3 1.393(2) . ?
C3 N1 1.379(2) . ?
C3 C4 1.394(2) . ?
C4 N4 1.328(2) . ?
C4 S1 1.7595(16) . ?
C5 N3 1.334(2) . ?
C5 N4 1.340(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(2) . ?
C6 N5 1.372(2) . ?
C6 S1 1.7354(16) . ?
C7 N6 1.354(2) . ?
C7 N7 1.424(3) . ?
C8 N6 1.298(3) . ?
C8 N5 1.349(2) . ?
C8 H8 0.9300 . ?
C9 N5 1.462(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N2 H2N 0.88(2) . ?
N7 O1 1.222(3) . ?
N7 O2 1.228(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 114.12(15) . . ?
N1 C1 H1 122.9 . . ?
N2 C1 H1 122.9 . . ?
N3 C2 N2 129.24(15) . . ?
N3 C2 C3 125.26(14) . . ?
N2 C2 C3 105.49(14) . . ?
N1 C3 C2 110.90(13) . . ?
N1 C3 C4 132.93(15) . . ?
C2 C3 C4 116.17(14) . . ?
N4 C4 C3 120.30(14) . . ?
N4 C4 S1 122.50(11) . . ?
C3 C4 S1 117.21(12) . . ?
N3 C5 N4 128.32(16) . . ?
N3 C5 H5 115.8 . . ?
N4 C5 H5 115.8 . . ?
C7 C6 N5 103.46(15) . . ?
C7 C6 S1 135.08(15) . . ?
N5 C6 S1 121.37(13) . . ?
N6 C7 C6 112.61(18) . . ?
N6 C7 N7 119.94(17) . . ?
C6 C7 N7 127.39(17) . . ?
N6 C8 N5 113.31(18) . . ?
N6 C8 H8 123.3 . . ?
N5 C8 H8 123.3 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 C3 103.23(14) . . ?
C2 N2 C1 106.26(13) . . ?
C2 N2 H2N 122.8(14) . . ?
C1 N2 H2N 130.2(14) . . ?
C5 N3 C2 112.36(14) . . ?
C4 N4 C5 117.57(14) . . ?
C8 N5 C6 106.99(16) . . ?
C8 N5 C9 125.20(18) . . ?
C6 N5 C9 127.80(16) . . ?
C8 N6 C7 103.60(16) . . ?
O1 N7 O2 124.0(2) . . ?
O1 N7 C7 118.85(18) . . ?
O2 N7 C7 117.2(2) . . ?
C6 S1 C4 102.64(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C2 C3 N1 179.60(17) . . . . ?
N2 C2 C3 N1 0.5(2) . . . . ?
N3 C2 C3 C4 -0.7(3) . . . . ?
N2 C2 C3 C4 -179.85(16) . . . . ?
N1 C3 C4 N4 -178.69(19) . . . . ?
C2 C3 C4 N4 1.7(3) . . . . ?
N1 C3 C4 S1 1.5(3) . . . . ?
C2 C3 C4 S1 -178.11(13) . . . . ?
N5 C6 C7 N6 0.9(2) . . . . ?
S1 C6 C7 N6 177.35(16) . . . . ?
N5 C6 C7 N7 178.28(19) . . . . ?
S1 C6 C7 N7 -5.3(3) . . . . ?
N2 C1 N1 C3 -0.8(2) . . . . ?
C2 C3 N1 C1 0.2(2) . . . . ?
C4 C3 N1 C1 -179.4(2) . . . . ?
N3 C2 N2 C1 179.98(19) . . . . ?
C3 C2 N2 C1 -0.9(2) . . . . ?
N1 C1 N2 C2 1.2(2) . . . . ?
N4 C5 N3 C2 0.1(3) . . . . ?
N2 C2 N3 C5 178.77(19) . . . . ?
C3 C2 N3 C5 -0.2(3) . . . . ?
C3 C4 N4 C5 -1.8(3) . . . . ?
S1 C4 N4 C5 178.03(15) . . . . ?
N3 C5 N4 C4 0.9(3) . . . . ?
N6 C8 N5 C6 -0.9(3) . . . . ?
N6 C8 N5 C9 178.7(2) . . . . ?
C7 C6 N5 C8 -0.1(2) . . . . ?
S1 C6 N5 C8 -177.10(15) . . . . ?
C7 C6 N5 C9 -179.6(2) . . . . ?
S1 C6 N5 C9 3.4(3) . . . . ?
N5 C8 N6 C7 1.4(3) . . . . ?
C6 C7 N6 C8 -1.4(3) . . . . ?
N7 C7 N6 C8 -179.0(2) . . . . ?
N6 C7 N7 O1 -174.8(2) . . . . ?
C6 C7 N7 O1 8.1(3) . . . . ?
N6 C7 N7 O2 3.9(3) . . . . ?
C6 C7 N7 O2 -173.3(2) . . . . ?
C7 C6 S1 C4 63.7(2) . . . . ?
N5 C6 S1 C4 -120.36(15) . . . . ?
N4 C4 S1 C6 2.52(18) . . . . ?
C3 C4 S1 C6 -177.68(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 N6 0.93 2.48 3.401(2) 173.5 4_475 yes
C5 H5 O2 0.93 2.33 3.172(2) 150.2 2_745 yes
N2 H2N N3 0.88(2) 2.05(2) 2.915(2) 167(2) 3_665 yes

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: cyclohexanol + acetone'
####################################################################### 
# 
# 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_KB1325_0m
_database_code_depnum_ccdc_archive 'CCDC 2361367'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-06-08 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Azathioprine monohydrate'
_chemical_name_common            'Azathioprine monohydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 N7 O2 S, O'
_chemical_formula_sum            'C9 H7 N7 O3 S'
_chemical_formula_weight         293.28

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

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

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

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

_cell_length_a                   4.5053(3)
_cell_length_b                   25.0747(13)
_cell_length_c                   24.4596(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.789(2)
_cell_angle_gamma                90
_cell_volume                     2761.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4567
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      21.62

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.253
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6661
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            25692
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4865
_reflns_number_gt                3056
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1268P)²+1.2499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4865
_refine_ls_number_parameters     378
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.2204
_refine_ls_wR_factor_gt          0.1855
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.9287(12) 0.93729(19) 0.4167(2) 0.0665(14) Uani 1 1 d . . . . .
H1A H 1.032943 0.955297 0.390193 0.080 Uiso 1 1 calc R U . . .
C2A C 0.6347(10) 0.92361(16) 0.48341(17) 0.0483(10) Uani 1 1 d . . . . .
C3A C 0.7545(9) 0.87592(16) 0.46549(16) 0.0462(10) Uani 1 1 d . . . . .
C4A C 0.6669(9) 0.83001(15) 0.49259(16) 0.0429(10) Uani 1 1 d . . . . .
C5A C 0.3777(10) 0.88214(15) 0.54606(16) 0.0472(10) Uani 1 1 d . . . . .
H5A H 0.244719 0.883261 0.574355 0.057 Uiso 1 1 calc R U . . .
C6A C 0.6678(9) 0.72596(15) 0.52150(16) 0.0441(10) Uani 1 1 d . . . . .
C7A C 0.9660(10) 0.76236(17) 0.60349(18) 0.0545(11) Uani 1 1 d . . . . .
H7AA H 1.126206 0.770591 0.579932 0.082 Uiso 1 1 calc R U . . .
H7AB H 1.043914 0.746174 0.636483 0.082 Uiso 1 1 calc R U . . .
H7AC H 0.862650 0.794555 0.612328 0.082 Uiso 1 1 calc R U . . .
C8A C 0.6200(10) 0.68514(17) 0.60031(19) 0.0552(11) Uani 1 1 d . . . . .
H8A H 0.646464 0.677005 0.637239 0.066 Uiso 1 1 calc R U . . .
C9A C 0.4749(9) 0.68341(16) 0.51846(18) 0.0495(11) Uani 1 1 d . . . . .
N1A N 0.9436(9) 0.88493(15) 0.42305(15) 0.0612(10) Uani 1 1 d . . . . .
N2A N 0.7508(9) 0.96257(16) 0.45177(17) 0.0595(10) Uani 1 1 d D . . . .
H1N H 0.713(11) 0.9972(9) 0.453(2) 0.078(17) Uiso 1 1 d D . . . .
N3A N 0.4425(8) 0.92917(13) 0.52380(14) 0.0501(9) Uani 1 1 d . . . . .
N4A N 0.4773(7) 0.83387(12) 0.53333(13) 0.0450(8) Uani 1 1 d . . . . .
N5A N 0.7610(7) 0.72549(12) 0.57569(14) 0.0455(8) Uani 1 1 d . . . . .
N6A N 0.4412(9) 0.65844(14) 0.56683(17) 0.0607(10) Uani 1 1 d . . . . .
N7A N 0.3114(10) 0.66464(16) 0.47124(18) 0.0639(11) Uani 1 1 d . . . . .
O1A O 0.3736(9) 0.68272(15) 0.42704(17) 0.0874(12) Uani 1 1 d . . . . .
O2A O 0.1160(9) 0.63114(16) 0.47788(18) 0.0958(13) Uani 1 1 d . . . . .
S1A S 0.8082(3) 0.76792(4) 0.47259(4) 0.0566(4) Uani 1 1 d . . . . .
C1B C 0.0430(10) 0.43957(16) 0.41438(18) 0.0533(11) Uani 1 1 d . . . . .
H1B H -0.075410 0.411322 0.425166 0.064 Uiso 1 1 calc R U . . .
C2B C 0.3691(9) 0.50380(15) 0.41939(15) 0.0393(9) Uani 1 1 d . . . . .
C3B C 0.2484(9) 0.49835(14) 0.36617(15) 0.0402(9) Uani 1 1 d . . . . .
C4B C 0.3507(9) 0.53400(15) 0.32802(15) 0.0403(9) Uani 1 1 d . . . . .
C5B C 0.6555(9) 0.57044(16) 0.39441(15) 0.0440(10) Uani 1 1 d . . . . .
H5B H 0.799092 0.595929 0.403214 0.053 Uiso 1 1 calc R U . . .
C6B C 0.3602(9) 0.58705(17) 0.23174(15) 0.0449(10) Uani 1 1 d . . . . .
C7B C 0.0983(11) 0.65510(19) 0.29049(19) 0.0664(13) Uani 1 1 d . . . . .
H7BA H 0.019905 0.689898 0.282331 0.100 Uiso 1 1 calc R U . . .
H7BB H 0.210791 0.656250 0.324452 0.100 Uiso 1 1 calc R U . . .
H7BC H -0.062376 0.630211 0.293452 0.100 Uiso 1 1 calc R U . . .
C8B C 0.4424(12) 0.6710(2) 0.2129(2) 0.0684(14) Uani 1 1 d . . . . .
H8B H 0.434875 0.707962 0.215009 0.082 Uiso 1 1 calc R U . . .
C9B C 0.5487(10) 0.59340(19) 0.18909(16) 0.0544(12) Uani 1 1 d . . . . .
N1B N 0.2333(8) 0.46580(13) 0.44976(14) 0.0466(9) Uani 1 1 d D . . . .
H2N H 0.282(7) 0.4618(14) 0.4850(8) 0.032(10) Uiso 1 1 d D . . . .
N2B N 0.0412(8) 0.45761(13) 0.36367(14) 0.0511(9) Uani 1 1 d . . . . .
N3B N 0.5750(7) 0.53933(13) 0.43530(12) 0.0442(8) Uani 1 1 d . . . . .
N4B N 0.5576(7) 0.56997(12) 0.34231(12) 0.0424(8) Uani 1 1 d . . . . .
N5B N 0.2921(8) 0.63812(14) 0.24641(13) 0.0506(9) Uani 1 1 d . . . . .
N6B N 0.5997(10) 0.64502(17) 0.17726(16) 0.0682(11) Uani 1 1 d . . . . .
N7B N 0.6834(9) 0.5518(2) 0.15812(14) 0.0636(11) Uani 1 1 d . . . . .
O1B O 0.8929(8) 0.56346(18) 0.12948(15) 0.0917(12) Uani 1 1 d . . . . .
O2B O 0.5805(9) 0.50690(17) 0.16167(15) 0.0874(12) Uani 1 1 d . . . . .
S1B S 0.2089(3) 0.53049(5) 0.26018(4) 0.0530(4) Uani 1 1 d . . . . .
O1W O -0.275(4) 0.3974(4) 0.2817(5) 0.239(6) Uani 0.566(6) 1 d . . P A 1
O2W O 1.244(4) 0.8061(7) 0.3499(6) 0.272(7) Uani 0.566(6) 1 d . . P A 1
O1WD O -0.304(6) 0.2994(6) 0.2654(7) 0.239(6) Uani 0.434(6) 1 d . . P A 2
O2WD O 1.650(6) 0.7749(9) 0.3209(9) 0.272(7) Uani 0.434(6) 1 d . . P A 2


_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
C1A N1A 1.323(6) . ?
C1A N2A 1.349(6) . ?
C1A H1A 0.9300 . ?
C2A N3A 1.341(5) . ?
C2A N2A 1.361(5) . ?
C2A C3A 1.388(6) . ?
C3A N1A 1.382(5) . ?
C3A C4A 1.391(5) . ?
C4A N4A 1.336(5) . ?
C4A S1A 1.757(4) . ?
C5A N4A 1.331(5) . ?
C5A N3A 1.335(5) . ?
C5A H5A 0.9300 . ?
C6A C9A 1.377(6) . ?
C6A N5A 1.378(5) . ?
C6A S1A 1.728(4) . ?
C7A N5A 1.460(5) . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C8A N6A 1.314(6) . ?
C8A N5A 1.347(5) . ?
C8A H8A 0.9300 . ?
C9A N6A 1.351(6) . ?
C9A N7A 1.430(6) . ?
N2A H1N 0.886(19) . ?
N7A O1A 1.213(5) . ?
N7A O2A 1.231(5) . ?
C1B N2B 1.320(5) . ?
C1B N1B 1.367(5) . ?
C1B H1B 0.9300 . ?
C2B N3B 1.335(5) . ?
C2B N1B 1.365(5) . ?
C2B C3B 1.402(5) . ?
C3B C4B 1.382(5) . ?
C3B N2B 1.384(5) . ?
C4B N4B 1.336(5) . ?
C4B S1B 1.761(4) . ?
C5B N3B 1.328(5) . ?
C5B N4B 1.335(5) . ?
C5B H5B 0.9300 . ?
C6B N5B 1.367(5) . ?
C6B C9B 1.375(6) . ?
C6B S1B 1.729(4) . ?
C7B N5B 1.471(6) . ?
C7B H7BA 0.9600 . ?
C7B H7BB 0.9600 . ?
C7B H7BC 0.9600 . ?
C8B N6B 1.313(7) . ?
C8B N5B 1.357(6) . ?
C8B H8B 0.9300 . ?
C9B N6B 1.347(6) . ?
C9B N7B 1.435(6) . ?
N1B H2N 0.888(18) . ?
N7B O2B 1.222(5) . ?
N7B O1B 1.228(5) . ?

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
N1A C1A N2A 114.9(4) . . ?
N1A C1A H1A 122.6 . . ?
N2A C1A H1A 122.6 . . ?
N3A C2A N2A 127.8(4) . . ?
N3A C2A C3A 126.0(4) . . ?
N2A C2A C3A 106.2(4) . . ?
N1A C3A C2A 110.5(4) . . ?
N1A C3A C4A 133.1(4) . . ?
C2A C3A C4A 116.3(4) . . ?
N4A C4A C3A 119.5(4) . . ?
N4A C4A S1A 121.1(3) . . ?
C3A C4A S1A 119.3(3) . . ?
N4A C5A N3A 128.9(4) . . ?
N4A C5A H5A 115.5 . . ?
N3A C5A H5A 115.5 . . ?
C9A C6A N5A 102.6(3) . . ?
C9A C6A S1A 132.7(3) . . ?
N5A C6A S1A 124.4(3) . . ?
N5A C7A H7AA 109.5 . . ?
N5A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
N5A C7A H7AC 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
N6A C8A N5A 113.1(4) . . ?
N6A C8A H8A 123.4 . . ?
N5A C8A H8A 123.4 . . ?
N6A C9A C6A 113.6(4) . . ?
N6A C9A N7A 119.1(4) . . ?
C6A C9A N7A 127.4(4) . . ?
C1A N1A C3A 102.7(4) . . ?
C1A N2A C2A 105.7(4) . . ?
C1A N2A H1N 127(3) . . ?
C2A N2A H1N 127(3) . . ?
C5A N3A C2A 111.3(3) . . ?
C5A N4A C4A 117.9(3) . . ?
C8A N5A C6A 107.6(3) . . ?
C8A N5A C7A 124.6(4) . . ?
C6A N5A C7A 127.7(3) . . ?
C8A N6A C9A 103.1(4) . . ?
O1A N7A O2A 124.0(5) . . ?
O1A N7A C9A 118.0(4) . . ?
O2A N7A C9A 118.0(5) . . ?
C6A S1A C4A 101.72(19) . . ?
N2B C1B N1B 114.5(4) . . ?
N2B C1B H1B 122.7 . . ?
N1B C1B H1B 122.7 . . ?
N3B C2B N1B 128.8(3) . . ?
N3B C2B C3B 125.6(3) . . ?
N1B C2B C3B 105.7(3) . . ?
C4B C3B N2B 133.4(4) . . ?
C4B C3B C2B 115.9(3) . . ?
N2B C3B C2B 110.8(3) . . ?
N4B C4B C3B 120.3(3) . . ?
N4B C4B S1B 120.7(3) . . ?
C3B C4B S1B 119.0(3) . . ?
N3B C5B N4B 128.6(4) . . ?
N3B C5B H5B 115.7 . . ?
N4B C5B H5B 115.7 . . ?
N5B C6B C9B 103.9(4) . . ?
N5B C6B S1B 124.6(3) . . ?
C9B C6B S1B 131.4(4) . . ?
N5B C7B H7BA 109.5 . . ?
N5B C7B H7BB 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
N5B C7B H7BC 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
N6B C8B N5B 113.0(4) . . ?
N6B C8B H8B 123.5 . . ?
N5B C8B H8B 123.5 . . ?
N6B C9B C6B 112.8(4) . . ?
N6B C9B N7B 120.5(4) . . ?
C6B C9B N7B 126.7(4) . . ?
C2B N1B C1B 105.9(3) . . ?
C2B N1B H2N 120(2) . . ?
C1B N1B H2N 134(2) . . ?
C1B N2B C3B 103.1(4) . . ?
C5B N3B C2B 112.1(3) . . ?
C5B N4B C4B 117.6(3) . . ?
C8B N5B C6B 106.8(4) . . ?
C8B N5B C7B 125.8(4) . . ?
C6B N5B C7B 127.3(4) . . ?
C8B N6B C9B 103.5(4) . . ?
O2B N7B O1B 124.0(5) . . ?
O2B N7B C9B 117.7(4) . . ?
O1B N7B C9B 118.3(5) . . ?
C6B S1B C4B 101.67(18) . . ?

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
N3A C2A C3A N1A 179.8(4) . . . . ?
N2A C2A C3A N1A 0.0(5) . . . . ?
N3A C2A C3A C4A -0.5(6) . . . . ?
N2A C2A C3A C4A 179.7(4) . . . . ?
N1A C3A C4A N4A 179.6(4) . . . . ?
C2A C3A C4A N4A 0.0(6) . . . . ?
N1A C3A C4A S1A -0.3(6) . . . . ?
C2A C3A C4A S1A -179.9(3) . . . . ?
N5A C6A C9A N6A 1.4(5) . . . . ?
S1A C6A C9A N6A 174.9(3) . . . . ?
N5A C6A C9A N7A -179.6(4) . . . . ?
S1A C6A C9A N7A -6.1(7) . . . . ?
N2A C1A N1A C3A 0.9(6) . . . . ?
C2A C3A N1A C1A -0.5(5) . . . . ?
C4A C3A N1A C1A 179.9(5) . . . . ?
N1A C1A N2A C2A -0.9(6) . . . . ?
N3A C2A N2A C1A -179.3(4) . . . . ?
C3A C2A N2A C1A 0.5(5) . . . . ?
N4A C5A N3A C2A 0.2(6) . . . . ?
N2A C2A N3A C5A -179.8(4) . . . . ?
C3A C2A N3A C5A 0.4(6) . . . . ?
N3A C5A N4A C4A -0.6(6) . . . . ?
C3A C4A N4A C5A 0.5(6) . . . . ?
S1A C4A N4A C5A -179.6(3) . . . . ?
N6A C8A N5A C6A 0.3(5) . . . . ?
N6A C8A N5A C7A 178.3(4) . . . . ?
C9A C6A N5A C8A -1.0(4) . . . . ?
S1A C6A N5A C8A -175.3(3) . . . . ?
C9A C6A N5A C7A -178.9(4) . . . . ?
S1A C6A N5A C7A 6.8(6) . . . . ?
N5A C8A N6A C9A 0.5(5) . . . . ?
C6A C9A N6A C8A -1.2(5) . . . . ?
N7A C9A N6A C8A 179.7(4) . . . . ?
N6A C9A N7A O1A -170.3(4) . . . . ?
C6A C9A N7A O1A 10.8(7) . . . . ?
N6A C9A N7A O2A 9.7(6) . . . . ?
C6A C9A N7A O2A -169.2(4) . . . . ?
C9A C6A S1A C4A 117.3(4) . . . . ?
N5A C6A S1A C4A -70.3(4) . . . . ?
N4A C4A S1A C6A -5.7(4) . . . . ?
C3A C4A S1A C6A 174.2(3) . . . . ?
N3B C2B C3B C4B -1.4(6) . . . . ?
N1B C2B C3B C4B 178.8(3) . . . . ?
N3B C2B C3B N2B 179.8(4) . . . . ?
N1B C2B C3B N2B 0.0(4) . . . . ?
N2B C3B C4B N4B -180.0(4) . . . . ?
C2B C3B C4B N4B 1.6(5) . . . . ?
N2B C3B C4B S1B -1.0(6) . . . . ?
C2B C3B C4B S1B -179.5(3) . . . . ?
N5B C6B C9B N6B 0.3(5) . . . . ?
S1B C6B C9B N6B 175.9(3) . . . . ?
N5B C6B C9B N7B -179.1(4) . . . . ?
S1B C6B C9B N7B -3.5(7) . . . . ?
N3B C2B N1B C1B -179.4(4) . . . . ?
C3B C2B N1B C1B 0.4(4) . . . . ?
N2B C1B N1B C2B -0.6(5) . . . . ?
N1B C1B N2B C3B 0.6(5) . . . . ?
C4B C3B N2B C1B -178.9(4) . . . . ?
C2B C3B N2B C1B -0.4(5) . . . . ?
N4B C5B N3B C2B 0.1(6) . . . . ?
N1B C2B N3B C5B -179.7(4) . . . . ?
C3B C2B N3B C5B 0.6(6) . . . . ?
N3B C5B N4B C4B 0.1(6) . . . . ?
C3B C4B N4B C5B -1.1(5) . . . . ?
S1B C4B N4B C5B -180.0(3) . . . . ?
N6B C8B N5B C6B 0.8(5) . . . . ?
N6B C8B N5B C7B 179.8(4) . . . . ?
C9B C6B N5B C8B -0.6(4) . . . . ?
S1B C6B N5B C8B -176.6(3) . . . . ?
C9B C6B N5B C7B -179.6(4) . . . . ?
S1B C6B N5B C7B 4.4(6) . . . . ?
N5B C8B N6B C9B -0.6(5) . . . . ?
C6B C9B N6B C8B 0.2(5) . . . . ?
N7B C9B N6B C8B 179.6(4) . . . . ?
N6B C9B N7B O2B -163.7(4) . . . . ?
C6B C9B N7B O2B 15.7(6) . . . . ?
N6B C9B N7B O1B 15.9(6) . . . . ?
C6B C9B N7B O1B -164.8(4) . . . . ?
N5B C6B S1B C4B -65.8(4) . . . . ?
C9B C6B S1B C4B 119.4(4) . . . . ?
N4B C4B S1B C6B -9.0(4) . . . . ?
C3B C4B S1B C6B 172.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2A H1N N3A 0.886(19) 2.06(2) 2.919(5) 164(5) 3_676 yes
N1B H2N N3B 0.888(18) 2.034(19) 2.918(5) 173(3) 3_666 yes

_refine_diff_density_max         0.588
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.075


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_KB1331_0m
_database_code_depnum_ccdc_archive 'CCDC 2361369'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-06-08 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Azathioprine-hemidioxane solvate'
_chemical_name_common            'Azathioprine-hemidioxane solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 N7 O2 S, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C11 H11 N7 O3 S'
_chemical_formula_weight         321.33

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

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

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

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

_cell_length_a                   4.4622(8)
_cell_length_b                   15.295(2)
_cell_length_c                   19.852(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.035(11)
_cell_angle_gamma                90
_cell_volume                     1354.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2886
_cell_measurement_theta_min      2.663
_cell_measurement_theta_max      27.987

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.266
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5357
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            12611
_diffrn_reflns_av_unetI/netI     0.1101
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.447
_diffrn_reflns_theta_max         28.631
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3385
_reflns_number_gt                2075
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0758P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3385
_refine_ls_number_parameters     223
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0263(6) 0.66322(16) 0.50899(12) 0.0217(6) Uani 1 1 d . . . . .
H1 H -0.090467 0.672829 0.547388 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2205(6) 0.67776(15) 0.41366(11) 0.0178(6) Uani 1 1 d . . . . .
C3 C 0.3482(6) 0.60245(16) 0.44300(11) 0.0183(6) Uani 1 1 d . . . . .
C4 C 0.6257(6) 0.57850(15) 0.35432(12) 0.0196(6) Uani 1 1 d . . . . .
H4 H 0.771358 0.544731 0.332200 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3147(6) 0.69818(16) 0.34973(12) 0.0202(6) Uani 1 1 d . . . . .
C6 C 0.3123(6) 0.77659(16) 0.22819(12) 0.0214(6) Uani 1 1 d . . . . .
C7 C 0.0265(7) 0.63654(17) 0.19777(13) 0.0252(6) Uani 1 1 d . . . . .
H7A H -0.066695 0.616479 0.155078 0.038 Uiso 1 1 calc R U . . .
H7B H -0.129638 0.655612 0.227989 0.038 Uiso 1 1 calc R U . . .
H7C H 0.141066 0.588512 0.218834 0.038 Uiso 1 1 calc R U . . .
C8 C 0.3794(7) 0.72154(18) 0.12748(13) 0.0278(7) Uani 1 1 d . . . . .
H8 H 0.362206 0.683416 0.089765 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5089(7) 0.82461(17) 0.19176(13) 0.0248(6) Uani 1 1 d . . . . .
N1 N 0.0168(5) 0.71536(13) 0.45624(10) 0.0209(5) Uani 1 1 d . . . . .
N2 N 0.2190(5) 0.59386(14) 0.50393(10) 0.0202(5) Uani 1 1 d . . . . .
H2 H 0.260(7) 0.554(2) 0.5334(14) 0.038(9) Uiso 1 1 d . . . . .
N3 N 0.5536(5) 0.55072(13) 0.41546(9) 0.0191(5) Uani 1 1 d . . . . .
N4 N 0.5177(5) 0.64827(13) 0.32020(10) 0.0205(5) Uani 1 1 d . . . . .
N5 N 0.2281(5) 0.70977(13) 0.18492(10) 0.0214(5) Uani 1 1 d . . . . .
N6 N 0.5517(5) 0.79108(15) 0.12949(11) 0.0309(6) Uani 1 1 d . . . . .
N7 N 0.6618(6) 0.90373(15) 0.21243(14) 0.0352(6) Uani 1 1 d . . . . .
O1 O 0.5744(5) 0.94186(13) 0.26286(11) 0.0438(6) Uani 1 1 d . . . . .
O2 O 0.8715(5) 0.92838(14) 0.17874(12) 0.0506(7) Uani 1 1 d . . . . .
S1 S 0.16798(17) 0.79175(4) 0.30769(3) 0.0237(2) Uani 1 1 d . . . . .
O3 O 0.6556(6) 0.55958(13) 0.04286(10) 0.0488(7) Uani 1 1 d . . . . .
C10 C 0.5254(19) 0.5869(4) -0.0216(3) 0.0420(17) Uani 0.668(11) 1 d . U P A 1
H10A H 0.640627 0.636511 -0.039567 0.050 Uiso 0.668(11) 1 calc R U P A 1
H10B H 0.315714 0.606191 -0.016256 0.050 Uiso 0.668(11) 1 calc R U P A 1
C11 C 0.4662(19) 0.4896(4) 0.0693(3) 0.0430(17) Uani 0.668(11) 1 d . U P A 1
H11A H 0.257571 0.510649 0.072996 0.052 Uiso 0.668(11) 1 calc R U P A 1
H11B H 0.542216 0.471761 0.114741 0.052 Uiso 0.668(11) 1 calc R U P A 1
C10D C 0.670(4) 0.5628(8) -0.0326(6) 0.038(3) Uani 0.332(11) 1 d . U P A 2
H10C H 0.717207 0.622532 -0.048202 0.046 Uiso 0.332(11) 1 calc R U P A 2
H10D H 0.823165 0.521793 -0.048870 0.046 Uiso 0.332(11) 1 calc R U P A 2
C11D C 0.636(4) 0.4640(7) 0.0565(5) 0.040(3) Uani 0.332(11) 1 d . U P A 2
H11C H 0.665946 0.452140 0.105305 0.048 Uiso 0.332(11) 1 calc R U P A 2
H11D H 0.790286 0.431855 0.031822 0.048 Uiso 0.332(11) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.316(3) . ?
C1 N2 1.371(3) . ?
C1 H1 0.9500 . ?
C2 C5 1.387(3) . ?
C2 N1 1.388(3) . ?
C2 C3 1.403(3) . ?
C3 N3 1.342(3) . ?
C3 N2 1.365(3) . ?
C4 N3 1.336(3) . ?
C4 N4 1.344(3) . ?
C4 H4 0.9500 . ?
C5 N4 1.336(3) . ?
C5 S1 1.770(3) . ?
C6 C9 1.370(4) . ?
C6 N5 1.379(3) . ?
C6 S1 1.741(3) . ?
C7 N5 1.465(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N6 1.312(4) . ?
C8 N5 1.357(3) . ?
C8 H8 0.9500 . ?
C9 N6 1.358(3) . ?
C9 N7 1.442(4) . ?
N2 H2 0.86(3) . ?
N7 O2 1.229(3) . ?
N7 O1 1.234(3) . ?
O3 C10 1.448(6) . ?
O3 C11 1.472(6) . ?
O3 C11D 1.489(11) . ?
O3 C10D 1.503(12) . ?
C10 C11 1.508(10) 3_665 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10D C11D 1.49(2) 3_665 ?
C10D H10C 0.9900 . ?
C10D H10D 0.9900 . ?
C11D H11C 0.9900 . ?
C11D H11D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 114.4(2) . . ?
N1 C1 H1 122.8 . . ?
N2 C1 H1 122.8 . . ?
C5 C2 N1 133.7(2) . . ?
C5 C2 C3 115.7(2) . . ?
N1 C2 C3 110.7(2) . . ?
N3 C3 N2 128.4(2) . . ?
N3 C3 C2 126.0(2) . . ?
N2 C3 C2 105.6(2) . . ?
N3 C4 N4 128.1(2) . . ?
N3 C4 H4 116.0 . . ?
N4 C4 H4 116.0 . . ?
N4 C5 C2 120.3(2) . . ?
N4 C5 S1 120.01(18) . . ?
C2 C5 S1 119.6(2) . . ?
C9 C6 N5 103.5(2) . . ?
C9 C6 S1 132.2(2) . . ?
N5 C6 S1 124.2(2) . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N6 C8 N5 113.0(2) . . ?
N6 C8 H8 123.5 . . ?
N5 C8 H8 123.5 . . ?
N6 C9 C6 113.0(2) . . ?
N6 C9 N7 119.7(2) . . ?
C6 C9 N7 127.2(3) . . ?
C1 N1 C2 103.3(2) . . ?
C3 N2 C1 106.0(2) . . ?
C3 N2 H2 126(2) . . ?
C1 N2 H2 128(2) . . ?
C4 N3 C3 111.9(2) . . ?
C5 N4 C4 118.0(2) . . ?
C8 N5 C6 107.0(2) . . ?
C8 N5 C7 125.1(2) . . ?
C6 N5 C7 127.9(2) . . ?
C8 N6 C9 103.4(2) . . ?
O2 N7 O1 124.4(3) . . ?
O2 N7 C9 117.7(3) . . ?
O1 N7 C9 117.9(3) . . ?
C6 S1 C5 100.20(12) . . ?
C10 O3 C11 107.9(4) . . ?
C11D O3 C10D 102.6(7) . . ?
O3 C10 C11 108.2(5) . 3_665 ?
O3 C10 H10A 110.0 . . ?
C11 C10 H10A 110.1 3_665 . ?
O3 C10 H10B 110.1 . . ?
C11 C10 H10B 110.0 3_665 . ?
H10A C10 H10B 108.4 . . ?
O3 C11 C10 108.2(6) . 3_665 ?
O3 C11 H11A 110.1 . . ?
C10 C11 H11A 110.1 3_665 . ?
O3 C11 H11B 110.1 . . ?
C10 C11 H11B 110.1 3_665 . ?
H11A C11 H11B 108.4 . . ?
C11D C10D O3 103.8(10) 3_665 . ?
C11D C10D H10C 111.0 3_665 . ?
O3 C10D H10C 111.0 . . ?
C11D C10D H10D 111.0 3_665 . ?
O3 C10D H10D 111.0 . . ?
H10C C10D H10D 109.0 . . ?
O3 C11D C10D 105.8(12) . 3_665 ?
O3 C11D H11C 110.6 . . ?
C10D C11D H11C 110.6 3_665 . ?
O3 C11D H11D 110.6 . . ?
C10D C11D H11D 110.6 3_665 . ?
H11C C11D H11D 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C2 C3 N3 1.4(4) . . . . ?
N1 C2 C3 N3 -179.8(2) . . . . ?
C5 C2 C3 N2 -178.4(2) . . . . ?
N1 C2 C3 N2 0.4(3) . . . . ?
N1 C2 C5 N4 -179.4(3) . . . . ?
C3 C2 C5 N4 -0.9(4) . . . . ?
N1 C2 C5 S1 1.4(4) . . . . ?
C3 C2 C5 S1 179.89(19) . . . . ?
N5 C6 C9 N6 -0.5(3) . . . . ?
S1 C6 C9 N6 -177.1(2) . . . . ?
N5 C6 C9 N7 178.6(3) . . . . ?
S1 C6 C9 N7 2.0(5) . . . . ?
N2 C1 N1 C2 -0.6(3) . . . . ?
C5 C2 N1 C1 178.6(3) . . . . ?
C3 C2 N1 C1 0.1(3) . . . . ?
N3 C3 N2 C1 179.5(3) . . . . ?
C2 C3 N2 C1 -0.7(3) . . . . ?
N1 C1 N2 C3 0.8(3) . . . . ?
N4 C4 N3 C3 -0.4(4) . . . . ?
N2 C3 N3 C4 179.0(2) . . . . ?
C2 C3 N3 C4 -0.7(4) . . . . ?
C2 C5 N4 C4 0.0(4) . . . . ?
S1 C5 N4 C4 179.20(19) . . . . ?
N3 C4 N4 C5 0.7(4) . . . . ?
N6 C8 N5 C6 -0.9(3) . . . . ?
N6 C8 N5 C7 -178.2(2) . . . . ?
C9 C6 N5 C8 0.8(3) . . . . ?
S1 C6 N5 C8 177.72(19) . . . . ?
C9 C6 N5 C7 178.0(3) . . . . ?
S1 C6 N5 C7 -5.1(4) . . . . ?
N5 C8 N6 C9 0.5(3) . . . . ?
C6 C9 N6 C8 0.0(3) . . . . ?
N7 C9 N6 C8 -179.2(2) . . . . ?
N6 C9 N7 O2 -14.6(4) . . . . ?
C6 C9 N7 O2 166.3(3) . . . . ?
N6 C9 N7 O1 165.7(2) . . . . ?
C6 C9 N7 O1 -13.3(4) . . . . ?
C9 C6 S1 C5 -116.9(3) . . . . ?
N5 C6 S1 C5 67.1(3) . . . . ?
N4 C5 S1 C6 9.4(2) . . . . ?
C2 C5 S1 C6 -171.4(2) . . . . ?
C11 O3 C10 C11 -63.1(10) . . . 3_665 ?
C10 O3 C11 C10 63.1(9) . . . 3_665 ?
C11D O3 C10D C11D 70.0(16) . . . 3_665 ?
C10D O3 C11D C10D -71.6(15) . . . 3_665 ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.094


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,4-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_KB1287_0m
_database_code_depnum_ccdc_archive 'CCDC 2361368'
loop_
_audit_author_name
_audit_author_address
'Sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-06-08 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Azathioprine-2-methoxyethanol hydrate'
_chemical_name_common            'Azathioprine-2-methoxyethanol hydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H7 N7 O2 S), C3 H8 O2, H2 O'
_chemical_formula_sum            'C21 H24 N14 O7 S2'
_chemical_formula_weight         648.66

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

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

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

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

_cell_length_a                   4.3790(4)
_cell_length_b                   25.0168(19)
_cell_length_c                   24.5692(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.152(6)
_cell_angle_gamma                90
_cell_volume                     2691.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4525
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.26

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6018
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            35022
_diffrn_reflns_av_unetI/netI     0.1498
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         29.123
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6784
_reflns_number_gt                3547
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0812P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6784
_refine_ls_number_parameters     420
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0703
_refine_ls_wR_factor_ref         0.1768
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C -1.4533(9) 0.43884(15) 1.08347(14) 0.0261(9) Uani 1 1 d . . . . .
H1A H -1.563071 0.457391 1.110562 0.031 Uiso 1 1 calc R U . . .
C2A C -1.1448(9) 0.42500(13) 1.01575(13) 0.0214(8) Uani 1 1 d . . . . .
C3A C -1.2766(8) 0.37702(14) 1.03380(13) 0.0210(8) Uani 1 1 d . . . . .
C4A C -1.1902(8) 0.33131(13) 1.00679(13) 0.0201(8) Uani 1 1 d . . . . .
C5A C -0.8831(8) 0.38273(14) 0.95320(13) 0.0221(8) Uani 1 1 d . . . . .
H5A H -0.744503 0.383534 0.923950 0.027 Uiso 1 1 calc R U . . .
C6A C -1.1846(8) 0.22690(13) 0.97856(13) 0.0191(8) Uani 1 1 d . . . . .
C7A C -0.9835(8) 0.18483(13) 0.98246(13) 0.0202(8) Uani 1 1 d . . . . .
C8A C -1.1156(8) 0.18707(13) 0.89988(13) 0.0212(8) Uani 1 1 d . . . . .
H8A H -1.133824 0.179411 0.862079 0.025 Uiso 1 1 calc R U . . .
C9A C -1.4768(9) 0.26500(13) 0.89676(13) 0.0233(8) Uani 1 1 d . . . . .
H9AA H -1.551579 0.249338 0.862447 0.035 Uiso 1 1 calc R U . . .
H9AB H -1.367485 0.298292 0.889220 0.035 Uiso 1 1 calc R U . . .
H9AC H -1.649989 0.272578 0.920191 0.035 Uiso 1 1 calc R U . . .
N1A N -1.4706(7) 0.38623(12) 1.07695(11) 0.0259(7) Uani 1 1 d . . . . .
N2A N -1.2640(7) 0.46425(12) 1.04794(12) 0.0252(7) Uani 1 1 d D . . . .
H1N H -1.212(12) 0.5006(9) 1.0499(18) 0.079(17) Uiso 1 1 d D . . . .
N3A N -0.9451(7) 0.42983(11) 0.97570(11) 0.0216(7) Uani 1 1 d . . . . .
N4A N -0.9908(7) 0.33417(11) 0.96642(10) 0.0206(7) Uani 1 1 d . . . . .
N5A N -1.2686(7) 0.22719(10) 0.92438(11) 0.0186(7) Uani 1 1 d . . . . .
N6A N -0.9395(7) 0.15981(11) 0.93378(11) 0.0224(7) Uani 1 1 d . . . . .
N7A N -0.8252(7) 0.16556(11) 1.03037(11) 0.0247(7) Uani 1 1 d . . . . .
O1A O -0.6224(6) 0.13233(10) 1.02439(10) 0.0328(7) Uani 1 1 d . . . . .
O2A O -0.9001(7) 0.18376(10) 1.07484(9) 0.0328(7) Uani 1 1 d . . . . .
S1A S -1.3365(2) 0.26891(4) 1.02731(3) 0.0237(2) Uani 1 1 d . . . . .
C1B C 0.4638(8) 0.56263(13) 0.58272(13) 0.0212(8) Uani 1 1 d . . . . .
H1B H 0.581591 0.592250 0.571113 0.025 Uiso 1 1 calc R U . . .
C2B C 0.1398(8) 0.49642(13) 0.57983(13) 0.0186(8) Uani 1 1 d . . . . .
C3B C 0.2696(8) 0.50195(13) 0.63209(12) 0.0180(8) Uani 1 1 d . . . . .
C4B C 0.1773(8) 0.46435(12) 0.67040(12) 0.0170(7) Uani 1 1 d . . . . .
C5B C -0.1423(8) 0.42699(13) 0.60539(12) 0.0186(8) Uani 1 1 d . . . . .
H5B H -0.289513 0.400215 0.596923 0.022 Uiso 1 1 calc R U . . .
C6B C 0.1758(8) 0.40990(13) 0.76588(13) 0.0200(8) Uani 1 1 d . . . . .
C7B C -0.0184(9) 0.40355(15) 0.80899(13) 0.0237(9) Uani 1 1 d . . . . .
C8B C 0.0904(9) 0.32606(15) 0.78571(14) 0.0273(9) Uani 1 1 d . . . . .
H8B H 0.100804 0.288161 0.784123 0.033 Uiso 1 1 calc R U . . .
C9B C 0.4374(9) 0.34096(14) 0.70734(13) 0.0256(9) Uani 1 1 d . . . . .
H9BA H 0.317887 0.339945 0.673209 0.038 Uiso 1 1 calc R U . . .
H9BB H 0.517359 0.305191 0.715481 0.038 Uiso 1 1 calc R U . . .
H9BC H 0.607832 0.366022 0.703713 0.038 Uiso 1 1 calc R U . . .
N1B N 0.4740(7) 0.54400(11) 0.63344(10) 0.0209(7) Uani 1 1 d . . . . .
N2B N 0.2697(7) 0.53541(11) 0.54912(11) 0.0220(7) Uani 1 1 d D . . . .
H2N H 0.214(8) 0.5379(13) 0.5146(8) 0.029(10) Uiso 1 1 d D . . . .
N3B N -0.0697(7) 0.45994(10) 0.56471(10) 0.0184(7) Uani 1 1 d . . . . .
N4B N -0.0313(7) 0.42733(10) 0.65682(10) 0.0197(7) Uani 1 1 d . . . . .
N5B N 0.2427(7) 0.35843(11) 0.75148(10) 0.0214(7) Uani 1 1 d . . . . .
N6B N -0.0731(7) 0.35198(12) 0.82137(11) 0.0278(8) Uani 1 1 d . . . . .
N7B N -0.1541(8) 0.44581(14) 0.84014(11) 0.0285(8) Uani 1 1 d . . . . .
O1B O -0.0469(6) 0.49140(10) 0.83676(10) 0.0329(7) Uani 1 1 d . . . . .
O2B O -0.3733(6) 0.43460(11) 0.86893(10) 0.0356(7) Uani 1 1 d . . . . .
S1B S 0.3338(2) 0.46685(3) 0.73702(3) 0.0213(2) Uani 1 1 d . . . . .
C1 C 0.8904(13) 0.70622(17) 0.84487(15) 0.0596(16) Uani 1 1 d . . . . .
H1C H 0.993324 0.741003 0.844757 0.089 Uiso 1 1 calc R U . . .
H1D H 0.950311 0.686526 0.877875 0.089 Uiso 1 1 calc R U . . .
H1E H 0.668698 0.711603 0.844117 0.089 Uiso 1 1 calc R U . . .
C2 C 0.8596(12) 0.62264(17) 0.79926(16) 0.0470(12) Uani 1 1 d . . . . .
H2C H 0.637748 0.623271 0.806201 0.056 Uiso 1 1 calc R U . . .
H2D H 0.962426 0.602275 0.828917 0.056 Uiso 1 1 calc R U . . .
C3 C 0.9174(12) 0.59626(17) 0.74518(16) 0.0474(12) Uani 1 1 d . . . . .
H3A H 1.139122 0.596683 0.738052 0.057 Uiso 1 1 calc R U . . .
H3B H 0.850035 0.558514 0.746474 0.057 Uiso 1 1 calc R U . . .
O1 O 0.9766(8) 0.67624(12) 0.79784(11) 0.0526(9) Uani 1 1 d . . . . .
O2 O 0.7592(8) 0.62294(12) 0.70270(11) 0.0479(9) Uani 1 1 d D . . . .
H2O H 0.679(15) 0.5955(17) 0.685(2) 0.13(3) Uiso 1 1 d D . . . .
O1W O 1.4020(10) 0.71652(14) 0.72623(14) 0.0542(9) Uani 1 1 d D . . . .
H1W H 1.232(9) 0.706(2) 0.743(2) 0.13(3) Uiso 1 1 d D . . . .
H2W H 1.568(9) 0.6933(18) 0.728(2) 0.09(2) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A N1A 1.328(4) . ?
C1A N2A 1.372(5) . ?
C1A H1A 0.9500 . ?
C2A N3A 1.335(5) . ?
C2A N2A 1.371(4) . ?
C2A C3A 1.407(5) . ?
C3A C4A 1.379(5) . ?
C3A N1A 1.391(4) . ?
C4A N4A 1.337(4) . ?
C4A S1A 1.765(4) . ?
C5A N3A 1.332(4) . ?
C5A N4A 1.345(4) . ?
C5A H5A 0.9500 . ?
C6A N5A 1.374(4) . ?
C6A C7A 1.374(5) . ?
C6A S1A 1.736(3) . ?
C7A N6A 1.367(4) . ?
C7A N7A 1.437(4) . ?
C8A N6A 1.314(4) . ?
C8A N5A 1.355(4) . ?
C8A H8A 0.9500 . ?
C9A N5A 1.470(4) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
N2A H1N 0.938(19) . ?
N7A O1A 1.227(4) . ?
N7A O2A 1.234(3) . ?
C1B N1B 1.330(4) . ?
C1B N2B 1.356(4) . ?
C1B H1B 0.9500 . ?
C2B N3B 1.341(4) . ?
C2B N2B 1.364(4) . ?
C2B C3B 1.401(4) . ?
C3B N1B 1.381(4) . ?
C3B C4B 1.396(4) . ?
C4B N4B 1.338(4) . ?
C4B S1B 1.763(3) . ?
C5B N3B 1.339(4) . ?
C5B N4B 1.345(4) . ?
C5B H5B 0.9500 . ?
C6B N5B 1.369(4) . ?
C6B C7B 1.381(5) . ?
C6B S1B 1.741(4) . ?
C7B N6B 1.348(4) . ?
C7B N7B 1.440(4) . ?
C8B N6B 1.314(5) . ?
C8B N5B 1.353(4) . ?
C8B H8B 0.9500 . ?
C9B N5B 1.460(4) . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
N2B H2N 0.880(18) . ?
N7B O2B 1.236(4) . ?
N7B O1B 1.237(4) . ?
C1 O1 1.435(4) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C2 O1 1.436(5) . ?
C2 C3 1.509(6) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 O2 1.409(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O2 H2O 0.88(2) . ?
O1W H1W 0.91(2) . ?
O1W H2W 0.93(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A C1A N2A 114.6(3) . . ?
N1A C1A H1A 122.7 . . ?
N2A C1A H1A 122.7 . . ?
N3A C2A N2A 128.5(3) . . ?
N3A C2A C3A 126.0(3) . . ?
N2A C2A C3A 105.4(3) . . ?
C4A C3A N1A 133.0(3) . . ?
C4A C3A C2A 115.9(3) . . ?
N1A C3A C2A 111.1(3) . . ?
N4A C4A C3A 120.2(3) . . ?
N4A C4A S1A 120.4(3) . . ?
C3A C4A S1A 119.4(3) . . ?
N3A C5A N4A 128.6(3) . . ?
N3A C5A H5A 115.7 . . ?
N4A C5A H5A 115.7 . . ?
N5A C6A C7A 103.3(3) . . ?
N5A C6A S1A 124.5(3) . . ?
C7A C6A S1A 132.0(3) . . ?
N6A C7A C6A 113.0(3) . . ?
N6A C7A N7A 119.3(3) . . ?
C6A C7A N7A 127.7(3) . . ?
N6A C8A N5A 113.1(3) . . ?
N6A C8A H8A 123.5 . . ?
N5A C8A H8A 123.5 . . ?
N5A C9A H9AA 109.5 . . ?
N5A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
N5A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C1A N1A C3A 102.8(3) . . ?
C2A N2A C1A 106.1(3) . . ?
C2A N2A H1N 129(3) . . ?
C1A N2A H1N 125(3) . . ?
C5A N3A C2A 111.6(3) . . ?
C4A N4A C5A 117.7(3) . . ?
C8A N5A C6A 107.6(3) . . ?
C8A N5A C9A 125.4(3) . . ?
C6A N5A C9A 127.0(3) . . ?
C8A N6A C7A 103.0(3) . . ?
O1A N7A O2A 124.2(3) . . ?
O1A N7A C7A 117.9(3) . . ?
O2A N7A C7A 118.0(3) . . ?
C6A S1A C4A 101.08(17) . . ?
N1B C1B N2B 113.8(3) . . ?
N1B C1B H1B 123.1 . . ?
N2B C1B H1B 123.1 . . ?
N3B C2B N2B 128.6(3) . . ?
N3B C2B C3B 125.7(3) . . ?
N2B C2B C3B 105.7(3) . . ?
N1B C3B C4B 133.9(3) . . ?
N1B C3B C2B 110.4(3) . . ?
C4B C3B C2B 115.7(3) . . ?
N4B C4B C3B 120.2(3) . . ?
N4B C4B S1B 120.5(2) . . ?
C3B C4B S1B 119.3(3) . . ?
N3B C5B N4B 127.7(3) . . ?
N3B C5B H5B 116.2 . . ?
N4B C5B H5B 116.2 . . ?
N5B C6B C7B 103.2(3) . . ?
N5B C6B S1B 125.2(3) . . ?
C7B C6B S1B 131.5(3) . . ?
N6B C7B C6B 113.5(3) . . ?
N6B C7B N7B 120.4(3) . . ?
C6B C7B N7B 126.2(3) . . ?
N6B C8B N5B 113.6(3) . . ?
N6B C8B H8B 123.2 . . ?
N5B C8B H8B 123.2 . . ?
N5B C9B H9BA 109.5 . . ?
N5B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
N5B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C1B N1B C3B 103.6(3) . . ?
C1B N2B C2B 106.6(3) . . ?
C1B N2B H2N 135(2) . . ?
C2B N2B H2N 118(2) . . ?
C5B N3B C2B 112.5(3) . . ?
C4B N4B C5B 118.1(3) . . ?
C8B N5B C6B 107.0(3) . . ?
C8B N5B C9B 125.8(3) . . ?
C6B N5B C9B 127.2(3) . . ?
C8B N6B C7B 102.7(3) . . ?
O2B N7B O1B 123.2(3) . . ?
O2B N7B C7B 118.1(3) . . ?
O1B N7B C7B 118.7(3) . . ?
C6B S1B C4B 101.47(16) . . ?
O1 C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
O1 C2 C3 108.7(4) . . ?
O1 C2 H2C 109.9 . . ?
C3 C2 H2C 109.9 . . ?
O1 C2 H2D 109.9 . . ?
C3 C2 H2D 109.9 . . ?
H2C C2 H2D 108.3 . . ?
O2 C3 C2 110.9(4) . . ?
O2 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C1 O1 C2 111.6(4) . . ?
C3 O2 H2O 100(4) . . ?
H1W O1W H2W 116(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
N3A C2A C3A C4A -0.6(5) . . . . ?
N2A C2A C3A C4A 179.7(3) . . . . ?
N3A C2A C3A N1A 178.8(3) . . . . ?
N2A C2A C3A N1A -0.8(4) . . . . ?
N1A C3A C4A N4A -178.7(3) . . . . ?
C2A C3A C4A N4A 0.5(5) . . . . ?
N1A C3A C4A S1A -0.6(5) . . . . ?
C2A C3A C4A S1A 178.7(2) . . . . ?
N5A C6A C7A N6A 0.3(4) . . . . ?
S1A C6A C7A N6A 175.7(3) . . . . ?
N5A C6A C7A N7A -179.3(3) . . . . ?
S1A C6A C7A N7A -4.0(6) . . . . ?
N2A C1A N1A C3A 0.1(4) . . . . ?
C4A C3A N1A C1A 179.8(4) . . . . ?
C2A C3A N1A C1A 0.5(4) . . . . ?
N3A C2A N2A C1A -178.8(3) . . . . ?
C3A C2A N2A C1A 0.8(4) . . . . ?
N1A C1A N2A C2A -0.6(4) . . . . ?
N4A C5A N3A C2A -1.0(5) . . . . ?
N2A C2A N3A C5A -179.6(3) . . . . ?
C3A C2A N3A C5A 0.7(5) . . . . ?
C3A C4A N4A C5A -0.7(5) . . . . ?
S1A C4A N4A C5A -178.9(2) . . . . ?
N3A C5A N4A C4A 1.0(5) . . . . ?
N6A C8A N5A C6A 0.8(4) . . . . ?
N6A C8A N5A C9A 178.7(3) . . . . ?
C7A C6A N5A C8A -0.6(4) . . . . ?
S1A C6A N5A C8A -176.4(3) . . . . ?
C7A C6A N5A C9A -178.5(3) . . . . ?
S1A C6A N5A C9A 5.7(5) . . . . ?
N5A C8A N6A C7A -0.5(4) . . . . ?
C6A C7A N6A C8A 0.1(4) . . . . ?
N7A C7A N6A C8A 179.8(3) . . . . ?
N6A C7A N7A O1A 10.5(5) . . . . ?
C6A C7A N7A O1A -169.9(3) . . . . ?
N6A C7A N7A O2A -170.1(3) . . . . ?
C6A C7A N7A O2A 9.6(5) . . . . ?
N5A C6A S1A C4A -68.3(3) . . . . ?
C7A C6A S1A C4A 117.2(4) . . . . ?
N4A C4A S1A C6A -6.1(3) . . . . ?
C3A C4A S1A C6A 175.8(3) . . . . ?
N3B C2B C3B N1B -179.2(3) . . . . ?
N2B C2B C3B N1B 0.5(4) . . . . ?
N3B C2B C3B C4B 2.6(5) . . . . ?
N2B C2B C3B C4B -177.7(3) . . . . ?
N1B C3B C4B N4B 179.9(3) . . . . ?
C2B C3B C4B N4B -2.4(5) . . . . ?
N1B C3B C4B S1B 1.0(6) . . . . ?
C2B C3B C4B S1B 178.6(2) . . . . ?
N5B C6B C7B N6B -0.1(4) . . . . ?
S1B C6B C7B N6B -175.7(3) . . . . ?
N5B C6B C7B N7B 178.9(3) . . . . ?
S1B C6B C7B N7B 3.4(5) . . . . ?
N2B C1B N1B C3B -0.4(4) . . . . ?
C4B C3B N1B C1B 177.6(4) . . . . ?
C2B C3B N1B C1B -0.1(4) . . . . ?
N1B C1B N2B C2B 0.7(4) . . . . ?
N3B C2B N2B C1B 179.0(3) . . . . ?
C3B C2B N2B C1B -0.7(4) . . . . ?
N4B C5B N3B C2B 0.2(5) . . . . ?
N2B C2B N3B C5B 178.8(3) . . . . ?
C3B C2B N3B C5B -1.5(5) . . . . ?
C3B C4B N4B C5B 1.4(5) . . . . ?
S1B C4B N4B C5B -179.7(2) . . . . ?
N3B C5B N4B C4B -0.2(5) . . . . ?
N6B C8B N5B C6B 0.4(4) . . . . ?
N6B C8B N5B C9B -178.9(3) . . . . ?
C7B C6B N5B C8B -0.2(3) . . . . ?
S1B C6B N5B C8B 175.8(2) . . . . ?
C7B C6B N5B C9B 179.2(3) . . . . ?
S1B C6B N5B C9B -4.9(5) . . . . ?
N5B C8B N6B C7B -0.4(4) . . . . ?
C6B C7B N6B C8B 0.3(4) . . . . ?
N7B C7B N6B C8B -178.8(3) . . . . ?
N6B C7B N7B O2B -17.0(5) . . . . ?
C6B C7B N7B O2B 164.0(3) . . . . ?
N6B C7B N7B O1B 163.2(3) . . . . ?
C6B C7B N7B O1B -15.8(5) . . . . ?
N5B C6B S1B C4B 67.5(3) . . . . ?
C7B C6B S1B C4B -117.8(3) . . . . ?
N4B C4B S1B C6B 6.0(3) . . . . ?
C3B C4B S1B C6B -175.0(3) . . . . ?
O1 C2 C3 O2 -62.8(5) . . . . ?
C3 C2 O1 C1 171.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2A H1N N3A 0.938(19) 1.98(3) 2.867(4) 157(4) 3_367 yes
O1W H2W O1 0.93(2) 2.49(4) 3.204(5) 134(4) 1_655 yes
O1W H2W O2 0.93(2) 2.05(3) 2.881(5) 147(5) 1_655 yes
N2B H2N N3B 0.880(18) 2.037(18) 2.916(4) 177(3) 3_566 yes
O2 H2O N1B 0.88(2) 2.01(2) 2.876(4) 168(6) . yes
O1W H1W O1 0.91(2) 1.91(3) 2.777(5) 160(6) . yes
C5A H5A O2B 0.95 2.49 3.337(5) 148.9 . yes

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.091


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2-methoxyethanol+formamide'
