# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_SY_BAAT_OTS_0m
_database_code_depnum_ccdc_archive 'CCDC 2118464'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Department of Chemistry, Purdue University
United States of America
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        '4-benzyloxy-1,5-diaminotetrazolium tosylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H11 N6 O, C7 H7 O3 S'
_chemical_formula_sum            'C15 H18 N6 O4 S'
_chemical_formula_weight         378.41

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 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.6351(2)
_cell_length_b                   8.2212(3)
_cell_length_c                   16.2653(5)
_cell_angle_alpha                98.0291(14)
_cell_angle_beta                 98.6583(13)
_cell_angle_gamma                113.9202(13)
_cell_volume                     899.60(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8561
_cell_measurement_theta_min      5.6437
_cell_measurement_theta_max      79.2039

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.908
_shelx_estimated_absorpt_T_min   0.487
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5478
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            17324
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.644
_diffrn_reflns_theta_max         79.743
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3764
_reflns_number_gt                3233
_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 v2019.11-0 (Bruker, 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1183 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.3805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3764
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50519(6) 0.67444(5) 0.38935(2) 0.02461(13) Uani 1 1 d . . . . .
O1 O 0.80158(17) 0.33304(16) 0.25779(7) 0.0281(3) Uani 1 1 d . . . . .
O2 O 0.5971(2) 0.5787(2) 0.34344(9) 0.0485(4) Uani 1 1 d . . . . .
O3 O 0.6367(2) 0.79840(18) 0.46808(8) 0.0398(3) Uani 1 1 d . . . . .
O4 O 0.31665(17) 0.55230(16) 0.40240(7) 0.0300(3) Uani 1 1 d . . . . .
N1 N 0.8633(2) 0.26483(19) 0.32179(9) 0.0262(3) Uani 1 1 d . . . . .
N2 N 0.9464(2) 0.1483(2) 0.30806(10) 0.0306(3) Uani 1 1 d . . . . .
N3 N 0.9817(2) 0.1043(2) 0.37887(9) 0.0291(3) Uani 1 1 d . . . . .
N4 N 0.9224(2) 0.19424(18) 0.43789(9) 0.0243(3) Uani 1 1 d . . . . .
N5 N 0.9336(2) 0.1771(2) 0.52192(9) 0.0277(3) Uani 1 1 d . . . . .
H5A H 1.060(3) 0.204(3) 0.5433(13) 0.033 Uiso 1 1 d . U . . .
H5B H 0.862(3) 0.063(3) 0.5218(13) 0.033 Uiso 1 1 d . U . . .
N6 N 0.7703(2) 0.39810(19) 0.43701(10) 0.0256(3) Uani 1 1 d . . . . .
H6A H 0.712(3) 0.441(3) 0.4040(13) 0.031 Uiso 1 1 d . U . . .
H6B H 0.748(3) 0.395(3) 0.4898(14) 0.031 Uiso 1 1 d . U . . .
C1 C 0.8447(2) 0.2956(2) 0.40247(10) 0.0228(3) Uani 1 1 d . . . . .
C2 C 0.9678(3) 0.4985(3) 0.24954(12) 0.0350(4) Uani 1 1 d . . . . .
H2A H 1.078822 0.471006 0.239846 0.042 Uiso 1 1 calc R U . . .
H2B H 1.014070 0.595606 0.301982 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8920(3) 0.5579(3) 0.17487(11) 0.0316(4) Uani 1 1 d . . . . .
C4 C 0.8474(5) 0.4572(4) 0.09332(14) 0.0629(7) Uani 1 1 d . . . . .
H4 H 0.861512 0.346916 0.083904 0.075 Uiso 1 1 calc R U . . .
C5 C 0.7818(6) 0.5174(5) 0.02487(17) 0.0895(11) Uani 1 1 d . . . . .
H5 H 0.750547 0.447939 -0.031561 0.107 Uiso 1 1 calc R U . . .
C6 C 0.7618(4) 0.6779(5) 0.03842(18) 0.0720(8) Uani 1 1 d . . . . .
H6 H 0.715447 0.718087 -0.008581 0.086 Uiso 1 1 calc R U . . .
C7 C 0.8082(4) 0.7781(4) 0.11871(18) 0.0568(6) Uani 1 1 d . . . . .
H7 H 0.796919 0.889768 0.127965 0.068 Uiso 1 1 calc R U . . .
C8 C 0.8721(3) 0.7180(3) 0.18716(14) 0.0407(5) Uani 1 1 d . . . . .
H8 H 0.902634 0.787969 0.243405 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4560(2) 0.8119(2) 0.32288(10) 0.0248(3) Uani 1 1 d . . . . .
C10 C 0.4520(3) 0.7768(3) 0.23668(11) 0.0316(4) Uani 1 1 d . . . . .
H10 H 0.478221 0.679796 0.211980 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4088(3) 0.8863(3) 0.18675(12) 0.0398(5) Uani 1 1 d . . . . .
H11 H 0.406846 0.863102 0.127663 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3686(3) 1.0278(3) 0.22087(13) 0.0382(5) Uani 1 1 d . . . . .
C13 C 0.3727(3) 1.0600(3) 0.30737(13) 0.0345(4) Uani 1 1 d . . . . .
H13 H 0.344595 1.155991 0.331856 0.041 Uiso 1 1 calc R U . . .
C14 C 0.4172(2) 0.9542(2) 0.35857(11) 0.0282(4) Uani 1 1 d . . . . .
H14 H 0.421223 0.978822 0.417826 0.034 Uiso 1 1 calc R U . . .
C15 C 0.3228(4) 1.1466(4) 0.16634(17) 0.0572(7) Uani 1 1 d . . . . .
H15A H 0.400990 1.275317 0.195153 0.086 Uiso 1 1 calc R U . . .
H15B H 0.182501 1.117030 0.157438 0.086 Uiso 1 1 calc R U . . .
H15C H 0.355381 1.124488 0.111095 0.086 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.4508(13) . ?
S1 O3 1.4510(13) . ?
S1 O2 1.4527(14) . ?
S1 C9 1.7747(16) . ?
O1 N1 1.3601(17) . ?
O1 C2 1.477(2) . ?
N1 C1 1.341(2) . ?
N1 N2 1.3588(19) . ?
N2 N3 1.278(2) . ?
N3 N4 1.370(2) . ?
N4 C1 1.3456(19) . ?
N4 N5 1.3868(19) . ?
N5 H5A 0.90(2) . ?
N5 H5B 0.87(2) . ?
N6 C1 1.304(2) . ?
N6 H6A 0.85(2) . ?
N6 H6B 0.90(2) . ?
C2 C3 1.494(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.375(3) . ?
C3 C8 1.376(3) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.354(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 C14 1.392(2) . ?
C10 C11 1.393(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 C15 1.513(3) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O4 S1 O3 112.30(8) . . ?
O4 S1 O2 112.83(9) . . ?
O3 S1 O2 112.25(10) . . ?
O4 S1 C9 106.33(7) . . ?
O3 S1 C9 106.42(8) . . ?
O2 S1 C9 106.11(8) . . ?
N1 O1 C2 109.59(12) . . ?
C1 N1 N2 112.34(13) . . ?
C1 N1 O1 125.98(13) . . ?
N2 N1 O1 121.63(13) . . ?
N3 N2 N1 106.75(14) . . ?
N2 N3 N4 107.88(13) . . ?
C1 N4 N3 110.88(13) . . ?
C1 N4 N5 124.59(14) . . ?
N3 N4 N5 124.48(13) . . ?
N4 N5 H5A 105.7(13) . . ?
N4 N5 H5B 108.0(14) . . ?
H5A N5 H5B 108(2) . . ?
C1 N6 H6A 117.5(13) . . ?
C1 N6 H6B 120.6(13) . . ?
H6A N6 H6B 119.2(18) . . ?
N6 C1 N1 128.48(15) . . ?
N6 C1 N4 129.39(15) . . ?
N1 C1 N4 102.14(13) . . ?
O1 C2 C3 106.34(13) . . ?
O1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
O1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C8 119.30(19) . . ?
C4 C3 C2 120.72(19) . . ?
C8 C3 C2 119.95(18) . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C3 C8 C7 120.8(2) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C14 120.19(15) . . ?
C10 C9 S1 121.01(13) . . ?
C14 C9 S1 118.79(13) . . ?
C9 C10 C11 118.91(17) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 121.82(18) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 118.28(16) . . ?
C11 C12 C15 121.5(2) . . ?
C13 C12 C15 120.2(2) . . ?
C14 C13 C12 120.99(18) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C9 119.80(17) . . ?
C13 C14 H14 120.1 . . ?
C9 C14 H14 120.1 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C2 O1 N1 C1 96.53(18) . . . . ?
C2 O1 N1 N2 -86.17(18) . . . . ?
C1 N1 N2 N3 -0.14(19) . . . . ?
O1 N1 N2 N3 -177.78(14) . . . . ?
N1 N2 N3 N4 -0.48(18) . . . . ?
N2 N3 N4 C1 0.96(18) . . . . ?
N2 N3 N4 N5 178.52(15) . . . . ?
N2 N1 C1 N6 -179.36(16) . . . . ?
O1 N1 C1 N6 -1.8(3) . . . . ?
N2 N1 C1 N4 0.69(18) . . . . ?
O1 N1 C1 N4 178.21(14) . . . . ?
N3 N4 C1 N6 179.07(16) . . . . ?
N5 N4 C1 N6 1.5(3) . . . . ?
N3 N4 C1 N1 -0.98(17) . . . . ?
N5 N4 C1 N1 -178.53(15) . . . . ?
N1 O1 C2 C3 176.46(14) . . . . ?
O1 C2 C3 C4 -69.9(2) . . . . ?
O1 C2 C3 C8 112.16(19) . . . . ?
C8 C3 C4 C5 -0.5(4) . . . . ?
C2 C3 C4 C5 -178.4(3) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C5 C6 C7 C8 -1.2(4) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C2 C3 C8 C7 177.90(18) . . . . ?
C6 C7 C8 C3 0.9(3) . . . . ?
O4 S1 C9 C10 -102.06(15) . . . . ?
O3 S1 C9 C10 138.04(15) . . . . ?
O2 S1 C9 C10 18.31(17) . . . . ?
O4 S1 C9 C14 76.66(14) . . . . ?
O3 S1 C9 C14 -43.25(15) . . . . ?
O2 S1 C9 C14 -162.98(14) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
S1 C9 C10 C11 178.73(14) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C10 C11 C12 C15 179.70(19) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C15 C12 C13 C14 -179.06(17) . . . . ?
C12 C13 C14 C9 -0.9(3) . . . . ?
C10 C9 C14 C13 0.6(2) . . . . ?
S1 C9 C14 C13 -178.13(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5A O3 0.90(2) 2.36(2) 3.181(2) 152.6(18) 2_766 yes
N5 H5B O3 0.87(2) 2.11(2) 2.918(2) 154.5(19) 1_545 yes
N6 H6A O2 0.85(2) 1.97(2) 2.8088(19) 170.0(19) . yes
N6 H6B O4 0.90(2) 1.93(2) 2.8061(19) 163.2(19) 2_666 yes

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.049


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

data_DATO_Isopropanol_0m
_database_code_depnum_ccdc_archive 'CCDC 2118466'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Department of Chemistry, Purdue University
United States of America
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        1,5-diaminotetrazole-4N-oxide
_chemical_name_common            SYX-9
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H4 N6 O'
_chemical_formula_weight         116.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

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

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

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

_cell_length_a                   6.0034(4)
_cell_length_b                   14.4146(9)
_cell_length_c                   5.2071(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.186(2)
_cell_angle_gamma                90
_cell_volume                     417.24(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5818
_cell_measurement_theta_min      2.8263
_cell_measurement_theta_max      32.5738

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            15906
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.826
_diffrn_reflns_theta_max         33.183
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1592
_reflns_number_gt                1265
_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       'Apex4 v2021.4-0 (Bruker, 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1275(Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.2235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1592
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
O1 O 0.73319(14) 0.54789(6) 0.86341(17) 0.01807(18) Uani 1 1 d . . . . .
N1 N 0.58612(16) 0.59637(6) 0.65316(19) 0.01403(18) Uani 1 1 d . . . . .
N2 N 0.66466(17) 0.64359(7) 0.4768(2) 0.01685(19) Uani 1 1 d . . . . .
N3 N 0.48180(17) 0.68267(7) 0.2895(2) 0.01662(19) Uani 1 1 d . . . . .
N4 N 0.28578(16) 0.65973(6) 0.34495(19) 0.01341(18) Uani 1 1 d . . . . .
N5 N 0.05909(17) 0.69131(7) 0.1766(2) 0.01603(19) Uani 1 1 d . . . . .
H5B H 0.004(3) 0.7244(12) 0.286(4) 0.024 Uiso 1 1 d . U . . .
H5A H -0.039(3) 0.6418(12) 0.105(3) 0.024 Uiso 1 1 d . U . . .
N6 N 0.20714(18) 0.56986(7) 0.6904(2) 0.01744(19) Uani 1 1 d . . . . .
H6B H 0.057(3) 0.5827(12) 0.626(4) 0.026 Uiso 1 1 d . U . . .
H6A H 0.270(3) 0.5349(12) 0.841(4) 0.026 Uiso 1 1 d . U . . .
C1 C 0.34800(18) 0.60618(7) 0.5729(2) 0.01298(19) 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
O1 N1 1.3178(12) . ?
N1 C1 1.3368(13) . ?
N1 N2 1.3626(13) . ?
N2 N3 1.2902(13) . ?
N3 N4 1.3543(13) . ?
N4 C1 1.3452(14) . ?
N4 N5 1.3880(13) . ?
N5 H5B 0.897(17) . ?
N5 H5A 0.911(17) . ?
N6 C1 1.3244(14) . ?
N6 H6B 0.856(18) . ?
N6 H6A 0.887(18) . ?

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 N1 C1 128.15(9) . . ?
O1 N1 N2 122.08(9) . . ?
C1 N1 N2 109.75(9) . . ?
N3 N2 N1 108.38(9) . . ?
N2 N3 N4 106.99(9) . . ?
C1 N4 N3 110.74(9) . . ?
C1 N4 N5 128.66(9) . . ?
N3 N4 N5 120.60(9) . . ?
N4 N5 H5B 106.2(11) . . ?
N4 N5 H5A 109.3(10) . . ?
H5B N5 H5A 110.1(15) . . ?
C1 N6 H6B 119.6(12) . . ?
C1 N6 H6A 120.1(11) . . ?
H6B N6 H6A 120.2(16) . . ?
N6 C1 N1 127.43(10) . . ?
N6 C1 N4 128.42(10) . . ?
N1 C1 N4 104.14(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
O1 N1 N2 N3 178.68(9) . . . . ?
C1 N1 N2 N3 0.15(12) . . . . ?
N1 N2 N3 N4 -0.50(12) . . . . ?
N2 N3 N4 C1 0.69(12) . . . . ?
N2 N3 N4 N5 -179.60(9) . . . . ?
O1 N1 C1 N6 0.88(18) . . . . ?
N2 N1 C1 N6 179.29(11) . . . . ?
O1 N1 C1 N4 -178.15(10) . . . . ?
N2 N1 C1 N4 0.26(11) . . . . ?
N3 N4 C1 N6 -179.60(11) . . . . ?
N5 N4 C1 N6 0.73(19) . . . . ?
N3 N4 C1 N1 -0.58(12) . . . . ?
N5 N4 C1 N1 179.74(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5B N5 0.897(17) 2.282(17) 3.1051(11) 152.5(15) 4_576 yes
N5 H5A O1 0.911(17) 1.996(17) 2.8899(13) 166.7(15) 1_454 yes
N5 H5A N1 0.911(17) 2.651(17) 3.3941(13) 139.3(13) 1_454 yes
N6 H6B N2 0.856(18) 2.352(18) 3.1996(14) 170.2(16) 1_455 yes
N6 H6A O1 0.887(18) 1.954(18) 2.7890(13) 156.4(16) 3_667 yes

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.064


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: 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_SY_DATO_EtOH_0m
_database_code_depnum_ccdc_archive 'CCDC 2118465'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Department of Chemistry, Purdue University
United States of America
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        '1,5-diamino-4-hydroxytetrazolium bromide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C H4.50 N6 O), Br'
_chemical_formula_sum            'C2 H9 Br N12 O2'
_chemical_formula_weight         313.12

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

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

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

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

_cell_length_a                   8.3967(5)
_cell_length_b                   5.6497(4)
_cell_length_c                   11.8522(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.990(3)
_cell_angle_gamma                90
_cell_volume                     551.94(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4815
_cell_measurement_theta_min      3.5023
_cell_measurement_theta_max      32.9523

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    3.743
_shelx_estimated_absorpt_T_min   0.309
_shelx_estimated_absorpt_T_max   0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5540
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            15296
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.471
_diffrn_reflns_theta_max         33.172
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2113
_reflns_number_gt                1563
_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 v2019.11-0 (Bruker, 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1275(Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The proton at O1 is half occupied due to a short contact with its 
symmetry counterpart across an inversion center. It is charge 
balanced by a half bromide located on an inversion center. 

The O-H distance was restrained to a target value of 0.84(2) 
Angstrom.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0181P)²+0.2398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2113
_refine_ls_number_parameters     94
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0550
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.000000 0.500000 0.000000 0.01855(6) Uani 1 2 d S . P . .
O1 O 0.47961(15) 0.8175(2) 0.44411(11) 0.0268(3) Uani 1 1 d D . . . .
H1 H 0.504(6) 0.931(6) 0.487(4) 0.040 Uiso 0.5 1 d D U P . .
N1 N 0.59005(15) 0.8084(2) 0.37625(11) 0.0174(2) Uani 1 1 d . . . . .
N2 N 0.58958(17) 0.9618(2) 0.28854(12) 0.0231(3) Uani 1 1 d . . . . .
N3 N 0.70207(18) 0.8975(2) 0.23548(11) 0.0245(3) Uani 1 1 d . . . . .
N4 N 0.76957(15) 0.6966(2) 0.28798(10) 0.0181(2) Uani 1 1 d . . . . .
N5 N 0.9000(2) 0.5764(3) 0.25834(16) 0.0303(3) Uani 1 1 d . . . . .
H5A H 0.875(3) 0.561(4) 0.183(2) 0.045 Uiso 1 1 d . U . . .
H5B H 0.977(3) 0.663(5) 0.275(2) 0.045 Uiso 1 1 d . U . . .
N6 N 0.73580(18) 0.4624(2) 0.44939(13) 0.0223(3) Uani 1 1 d . . . . .
H6A H 0.809(3) 0.377(4) 0.4471(18) 0.033 Uiso 1 1 d . U . . .
H6B H 0.674(3) 0.439(4) 0.4952(19) 0.033 Uiso 1 1 d . U . . .
C1 C 0.70180(17) 0.6396(2) 0.37741(12) 0.0154(3) 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
O1 N1 1.3393(16) . ?
O1 H1 0.821(19) . ?
N1 C1 1.3364(18) . ?
N1 N2 1.3528(18) . ?
N2 N3 1.283(2) . ?
N3 N4 1.3646(18) . ?
N4 C1 1.3347(18) . ?
N4 N5 1.3892(19) . ?
N5 H5A 0.88(3) . ?
N5 H5B 0.81(3) . ?
N6 C1 1.3110(19) . ?
N6 H6A 0.79(2) . ?
N6 H6B 0.83(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 O1 H1 106(4) . . ?
C1 N1 O1 125.90(12) . . ?
C1 N1 N2 111.36(12) . . ?
O1 N1 N2 122.41(12) . . ?
N3 N2 N1 107.50(12) . . ?
N2 N3 N4 107.02(12) . . ?
C1 N4 N3 111.10(12) . . ?
C1 N4 N5 123.98(13) . . ?
N3 N4 N5 124.75(13) . . ?
N4 N5 H5A 105.0(16) . . ?
N4 N5 H5B 105.8(17) . . ?
H5A N5 H5B 110(2) . . ?
C1 N6 H6A 121.4(15) . . ?
C1 N6 H6B 117.4(15) . . ?
H6A N6 H6B 121(2) . . ?
N6 C1 N4 128.92(13) . . ?
N6 C1 N1 128.12(13) . . ?
N4 C1 N1 102.97(12) . . ?

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
C1 N1 N2 N3 -1.70(17) . . . . ?
O1 N1 N2 N3 -175.55(13) . . . . ?
N1 N2 N3 N4 2.24(16) . . . . ?
N2 N3 N4 C1 -2.14(17) . . . . ?
N2 N3 N4 N5 -177.52(15) . . . . ?
N3 N4 C1 N6 -178.80(15) . . . . ?
N5 N4 C1 N6 -3.4(2) . . . . ?
N3 N4 C1 N1 1.05(16) . . . . ?
N5 N4 C1 N1 176.48(14) . . . . ?
O1 N1 C1 N6 -6.2(2) . . . . ?
N2 N1 C1 N6 -179.79(15) . . . . ?
O1 N1 C1 N4 173.95(13) . . . . ?
N2 N1 C1 N4 0.36(16) . . . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.083

