# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_exp_3525_auto
_database_code_depnum_ccdc_archive 'CCDC 2168450'
loop_
_audit_author_name
_audit_author_address
'Ivica Dilovic'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-04-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H6 N6'
_chemical_formula_sum            'C5 H6 N6'
_chemical_formula_weight         150.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   18.8845(7)
_cell_length_b                   18.8845(7)
_cell_length_c                   10.7786(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3328.9(3)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3531
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      76.6470
_cell_measurement_theta_min      4.6810
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             1404
_exptl_crystal_recrystallization_method Butan-1-ol
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3452
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        65.997
_diffrn_reflns_theta_max         65.997
_diffrn_reflns_theta_min         4.914
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 119.00   0.50    0.80    --  111.75  45.00 -30.00   54
  2  ω     99.00 149.00   0.50    0.80    --  111.75 125.00 -90.00  100
  3  ω     73.00 121.00   0.50    0.40    --   42.29 178.00 -90.00   96
  4  ω    139.00 167.00   0.50    0.80    --  111.75  45.00 -30.00   56
  5  ω    114.00 142.00   0.50    0.80    --  111.75 157.00 167.00   56
  6  ω     80.00 106.00   0.50    0.80    --  111.75 157.00 167.00   52
  7  ω    -26.00  36.00   0.50    0.40    --  -42.29  24.00 164.00  124
  8  ω    -76.00 -22.00   0.50    0.80    --  -90.25 110.00  -1.00  108
  9  ω     38.00  69.00   0.50    0.80    --  111.75 -61.00  60.00   62
 10  ω     42.00  68.00   0.50    0.80    --  111.75 -61.00 -30.00   52
 11  ω     57.00  98.00   0.50    0.80    --  111.75 -77.00-150.00   82
 12  ω     38.00  63.00   0.50    0.80    --  111.75 -61.00-120.00   50
 13  ω     41.00 109.00   0.50    0.80    --  111.75-125.00 -30.00  136
 14  ω     43.00 105.00   0.50    0.80    --  111.75-125.00-150.00  124
 15  ω     45.00 108.00   0.50    0.80    --  111.75-123.00 148.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0926134000
_diffrn_orient_matrix_UB_12      0.0610264000
_diffrn_orient_matrix_UB_13      0.0053907000
_diffrn_orient_matrix_UB_21      0.0149877000
_diffrn_orient_matrix_UB_22      -0.0689678000
_diffrn_orient_matrix_UB_23      0.0444376000
_diffrn_orient_matrix_UB_31      0.0087634000
_diffrn_orient_matrix_UB_32      -0.0201547000
_diffrn_orient_matrix_UB_33      -0.1355913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1227
_reflns_number_total             1293
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00055(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1045P)²+4.3184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1564
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N5 N 0.19480(9) 0.42627(9) 0.67274(13) 0.0263(4) Uani 1 1 d . . . . .
H5A H 0.222670 0.416866 0.729363 0.032 Uiso 1 1 calc R U . . .
H5B H 0.154268 0.433870 0.695060 0.032 Uiso 1 1 calc R U . . .
N1 N 0.27659(9) 0.41706(8) 0.52193(13) 0.0241(4) Uani 1 1 d . . . . .
N4 N 0.10817(9) 0.46011(10) 0.45909(14) 0.0294(5) Uani 1 1 d . . . . .
N2 N 0.26636(10) 0.44177(10) 0.30367(14) 0.0296(5) Uani 1 1 d . . . . .
N3 N 0.15591(10) 0.47114(10) 0.26601(14) 0.0319(5) Uani 1 1 d . . . . .
H3 H 0.160276 0.479499 0.185354 0.038 Uiso 1 1 calc R U . . .
N6 N 0.36142(11) 0.40980(11) 0.37788(16) 0.0349(5) Uani 1 1 d . . . . .
C1 C 0.21401(10) 0.42900(10) 0.55304(16) 0.0226(5) Uani 1 1 d . . . . .
C4 C 0.17291(11) 0.44428(10) 0.45769(16) 0.0254(5) Uani 1 1 d . . . . .
C2 C 0.29804(11) 0.42243(11) 0.40086(16) 0.0259(5) Uani 1 1 d . . . . .
C3 C 0.20294(11) 0.45095(11) 0.33875(16) 0.0267(5) Uani 1 1 d . . . . .
C5 C 0.10115(12) 0.47570(13) 0.34321(17) 0.0321(5) Uani 1 1 d . . . . .
H5 H 0.061511 0.489007 0.315233 0.039 Uiso 1 1 calc R U . . .
H6A H 0.3817(15) 0.3919(15) 0.439(2) 0.039(6) Uiso 1 1 d . . . . .
H6B H 0.3701(14) 0.4034(14) 0.302(3) 0.034(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C1 1.334(2) . ?
N1 C1 1.351(2) . ?
N1 C2 1.355(2) . ?
N4 C4 1.396(2) . ?
N4 C5 1.305(2) . ?
N2 C2 1.344(2) . ?
N2 C3 1.347(2) . ?
N3 H3 0.8800 . ?
N3 C3 1.374(2) . ?
N3 C5 1.363(2) . ?
N6 C2 1.355(2) . ?
N6 H6A 0.91(3) . ?
N6 H6B 0.86(3) . ?
C1 C4 1.402(2) . ?
C4 C3 1.382(2) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H5A N5 H5B 120.0 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
C1 N1 C2 118.70(15) . . ?
C5 N4 C4 103.68(14) . . ?
C2 N2 C3 111.18(15) . . ?
C3 N3 H3 126.7 . . ?
C5 N3 H3 126.7 . . ?
C5 N3 C3 106.57(15) . . ?
C2 N6 H6A 120.3(15) . . ?
C2 N6 H6B 116.7(16) . . ?
H6A N6 H6B 120(2) . . ?
N5 C1 N1 118.50(15) . . ?
N5 C1 C4 123.29(16) . . ?
N1 C1 C4 118.21(15) . . ?
N4 C4 C1 132.08(16) . . ?
C3 C4 N4 110.73(15) . . ?
C3 C4 C1 117.03(16) . . ?
N1 C2 N6 114.85(16) . . ?
N2 C2 N1 127.86(17) . . ?
N2 C2 N6 117.23(17) . . ?
N2 C3 N3 127.96(16) . . ?
N2 C3 C4 126.83(16) . . ?
N3 C3 C4 105.18(16) . . ?
N4 C5 N3 113.84(16) . . ?
N4 C5 H5 123.1 . . ?
N3 C5 H5 123.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C1 C4 N4 0.7(3) . . . . ?
N5 C1 C4 C3 175.65(16) . . . . ?
N1 C1 C4 N4 -178.80(17) . . . . ?
N1 C1 C4 C3 -3.8(2) . . . . ?
N4 C4 C3 N2 178.25(17) . . . . ?
N4 C4 C3 N3 0.0(2) . . . . ?
C1 N1 C2 N2 2.8(3) . . . . ?
C1 N1 C2 N6 179.88(15) . . . . ?
C1 C4 C3 N2 2.2(3) . . . . ?
C1 C4 C3 N3 -176.03(15) . . . . ?
C4 N4 C5 N3 0.2(2) . . . . ?
C2 N1 C1 N5 -177.87(15) . . . . ?
C2 N1 C1 C4 1.6(2) . . . . ?
C2 N2 C3 N3 179.48(18) . . . . ?
C2 N2 C3 C4 1.6(3) . . . . ?
C3 N2 C2 N1 -4.3(3) . . . . ?
C3 N2 C2 N6 178.70(16) . . . . ?
C3 N3 C5 N4 -0.2(2) . . . . ?
C5 N4 C4 C1 175.12(19) . . . . ?
C5 N4 C4 C3 -0.1(2) . . . . ?
C5 N3 C3 N2 -178.12(19) . . . . ?
C5 N3 C3 C4 0.1(2) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.764 197.3 54.3 '1.998 H2O'
2 0.333 0.667 -0.888 197.3 54.3 '1.998 H2O'
3 0.667 0.333 -0.221 197.3 54.3 '1.998 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'Mounted in cryo loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.472
_oxdiff_exptl_absorpt_empirical_full_min 0.656
####################################################################### 
# 
# 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_exp_3525_auto_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2168451'
loop_
_audit_author_name
_audit_author_address
'Ivica Dilovic'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-04-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.333(O1), C5 H6 N6'
_chemical_formula_sum            'C5 H6 N6 O0.33'
_chemical_formula_weight         155.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   18.8845(7)
_cell_length_b                   18.8845(7)
_cell_length_c                   10.7786(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3328.9(3)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3531
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      76.6470
_cell_measurement_theta_min      4.6810
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             1452
_exptl_crystal_recrystallization_method Butan-1-ol
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3511
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.808
_diffrn_reflns_theta_min         4.914
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 119.00   0.50    0.80    --  111.75  45.00 -30.00   54
  2  ω     99.00 149.00   0.50    0.80    --  111.75 125.00 -90.00  100
  3  ω     73.00 121.00   0.50    0.40    --   42.29 178.00 -90.00   96
  4  ω    139.00 167.00   0.50    0.80    --  111.75  45.00 -30.00   56
  5  ω    114.00 142.00   0.50    0.80    --  111.75 157.00 167.00   56
  6  ω     80.00 106.00   0.50    0.80    --  111.75 157.00 167.00   52
  7  ω    -26.00  36.00   0.50    0.40    --  -42.29  24.00 164.00  124
  8  ω    -76.00 -22.00   0.50    0.80    --  -90.25 110.00  -1.00  108
  9  ω     38.00  69.00   0.50    0.80    --  111.75 -61.00  60.00   62
 10  ω     42.00  68.00   0.50    0.80    --  111.75 -61.00 -30.00   52
 11  ω     57.00  98.00   0.50    0.80    --  111.75 -77.00-150.00   82
 12  ω     38.00  63.00   0.50    0.80    --  111.75 -61.00-120.00   50
 13  ω     41.00 109.00   0.50    0.80    --  111.75-125.00 -30.00  136
 14  ω     43.00 105.00   0.50    0.80    --  111.75-125.00-150.00  124
 15  ω     45.00 108.00   0.50    0.80    --  111.75-123.00 148.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0926134000
_diffrn_orient_matrix_UB_12      0.0610264000
_diffrn_orient_matrix_UB_13      0.0053907000
_diffrn_orient_matrix_UB_21      0.0149877000
_diffrn_orient_matrix_UB_22      -0.0689678000
_diffrn_orient_matrix_UB_23      0.0444376000
_diffrn_orient_matrix_UB_31      0.0087634000
_diffrn_orient_matrix_UB_32      -0.0201547000
_diffrn_orient_matrix_UB_33      -0.1355913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1256
_reflns_number_total             1326
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1326
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0754
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1382P)²+9.6866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2189
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Rigid body (RIGU) restrains
 O3, O1, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 1*[Sof(O1)]+1*[Sof(O2)]+1*[Sof(O3)]=1 with esd of 0.001
 Fixed Uiso: O1(0.1) O2(0.1) O3(0.1)
 Fixed X: O1(0.33333) O2(0.33333) O3(0.33333)
 Fixed Y: O1(0.66667) O2(0.66667) O3(0.66667)
 Fixed Z: O1(0.486329) O2(0.66667) O3(0.357821)
4.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5)
4.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.333330 0.666670 0.486329 0.100 Uiso 0.505(10) 3 d S U P A 1
O2 O 0.333330 0.666670 0.666670 0.100 Uiso 0.515(18) 6 d S U P B 2
O3 O 0.333330 0.666670 0.357821 0.100 Uiso 0.237(11) 3 d S U P C 3
N1 N 0.27664(12) 0.41698(12) 0.52201(19) 0.0227(6) Uani 1 1 d . . . . .
N2 N 0.26641(13) 0.44186(14) 0.30366(19) 0.0280(6) Uani 1 1 d . . . . .
N3 N 0.15612(14) 0.47114(15) 0.2661(2) 0.0311(6) Uani 1 1 d . . . . .
H3 H 0.160607 0.479676 0.185449 0.037 Uiso 1 1 calc R U . . .
N4 N 0.10820(13) 0.46019(14) 0.4592(2) 0.0282(6) Uani 1 1 d . . . . .
N5 N 0.19495(13) 0.42649(13) 0.67271(19) 0.0248(6) Uani 1 1 d . . . . .
H5A H 0.222777 0.417045 0.729350 0.030 Uiso 1 1 calc R U . . .
H5B H 0.154479 0.434201 0.695022 0.030 Uiso 1 1 calc R U . . .
N6 N 0.36135(15) 0.40986(16) 0.3778(2) 0.0336(7) Uani 1 1 d . . . . .
C1 C 0.21406(14) 0.42910(14) 0.5533(2) 0.0213(6) Uani 1 1 d . . . . .
C2 C 0.29817(15) 0.42242(15) 0.4007(2) 0.0240(6) Uani 1 1 d . . . . .
C3 C 0.20296(16) 0.45098(16) 0.3386(2) 0.0253(6) Uani 1 1 d . . . . .
C4 C 0.17292(15) 0.44453(15) 0.4574(2) 0.0240(6) Uani 1 1 d . . . . .
C5 C 0.10104(17) 0.47541(18) 0.3434(2) 0.0313(7) Uani 1 1 d . . . . .
H5 H 0.061136 0.488309 0.315243 0.038 Uiso 1 1 calc R U . . .
H6A H 0.384(2) 0.398(2) 0.438(4) 0.039(9) Uiso 1 1 d . . . . .
H6B H 0.373(2) 0.407(2) 0.299(4) 0.034(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.354(3) . ?
N1 C2 1.358(3) . ?
N2 C2 1.345(3) . ?
N2 C3 1.347(3) . ?
N3 H3 0.8800 . ?
N3 C3 1.369(3) . ?
N3 C5 1.366(3) . ?
N4 C4 1.394(3) . ?
N4 C5 1.303(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C1 1.331(3) . ?
N6 C2 1.350(3) . ?
N6 H6A 0.87(4) . ?
N6 H6B 0.89(4) . ?
C1 C4 1.409(3) . ?
C3 C4 1.381(3) . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 118.7(2) . . ?
C2 N2 C3 111.4(2) . . ?
C3 N3 H3 126.7 . . ?
C5 N3 H3 126.7 . . ?
C5 N3 C3 106.6(2) . . ?
C5 N4 C4 103.4(2) . . ?
H5A N5 H5B 120.0 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
C2 N6 H6A 120(2) . . ?
C2 N6 H6B 117(2) . . ?
H6A N6 H6B 122(3) . . ?
N1 C1 C4 118.1(2) . . ?
N5 C1 N1 118.6(2) . . ?
N5 C1 C4 123.4(2) . . ?
N2 C2 N1 127.7(2) . . ?
N2 C2 N6 117.4(2) . . ?
N6 C2 N1 114.8(2) . . ?
N2 C3 N3 128.0(2) . . ?
N2 C3 C4 126.9(2) . . ?
N3 C3 C4 105.1(2) . . ?
N4 C4 C1 131.8(2) . . ?
C3 C4 N4 111.0(2) . . ?
C3 C4 C1 117.0(2) . . ?
N3 C5 H5 123.1 . . ?
N4 C5 N3 113.9(2) . . ?
N4 C5 H5 123.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C4 N4 -179.1(2) . . . . ?
N1 C1 C4 C3 -3.8(3) . . . . ?
N2 C3 C4 N4 178.2(2) . . . . ?
N2 C3 C4 C1 2.0(4) . . . . ?
N3 C3 C4 N4 0.1(3) . . . . ?
N3 C3 C4 C1 -176.1(2) . . . . ?
N5 C1 C4 N4 0.4(4) . . . . ?
N5 C1 C4 C3 175.7(2) . . . . ?
C1 N1 C2 N2 2.7(4) . . . . ?
C1 N1 C2 N6 179.7(2) . . . . ?
C2 N1 C1 N5 -177.7(2) . . . . ?
C2 N1 C1 C4 1.7(3) . . . . ?
C2 N2 C3 N3 179.5(3) . . . . ?
C2 N2 C3 C4 1.9(4) . . . . ?
C3 N2 C2 N1 -4.4(4) . . . . ?
C3 N2 C2 N6 178.7(2) . . . . ?
C3 N3 C5 N4 0.3(3) . . . . ?
C4 N4 C5 N3 -0.2(3) . . . . ?
C5 N3 C3 N2 -178.3(3) . . . . ?
C5 N3 C3 C4 -0.2(3) . . . . ?
C5 N4 C4 C1 175.5(3) . . . . ?
C5 N4 C4 C3 0.0(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'Mounted in cryo loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.472
_oxdiff_exptl_absorpt_empirical_full_min 0.656
####################################################################### 
# 
# 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_manu_2_comp_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2168452'
loop_
_audit_author_name
_audit_author_address
'Ivica Dilovic'
;University of Zagreb, Faculty of Science, Department of Chemistry
Croatia
;
_audit_update_record             
;
2022-04-23 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;
_audit_creation_date             2022-04-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C5 H6 N6)'
_chemical_formula_sum            'C15 H18 N18'
_chemical_formula_weight         450.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         '(C5 H6 N6)3 OH2'
_chemical_oxdiff_usercomment     'C5 H6 N6'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.7265(5)
_cell_length_b                   11.3448(2)
_cell_length_c                   11.6327(4)
_cell_angle_alpha                109.619(3)
_cell_angle_beta                 108.625(3)
_cell_angle_gamma                107.919(3)
_cell_volume                     1118.77(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16920
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      76.9580
_cell_measurement_theta_min      4.5660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.92a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_recrystallization_method isopropanol
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7318
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        65.995
_diffrn_reflns_theta_max         65.995
_diffrn_reflns_theta_min         4.674
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -40.00   0.50    0.20    --  -46.91 -64.00-162.00  138
  2  ω    -57.00  11.00   0.50    0.20    --  -46.91  64.00 -26.00  136
  3  ω     64.00 101.00   0.50    0.20    --   46.91  64.00 -26.00   74
  4  ω     -2.00  62.00   0.50    0.20    --   46.91 -64.00-162.00  128
  5  ω   -154.00-108.00   0.50    0.80    --  -86.25 -64.00-162.00   92
  6  ω    -69.00 -44.00   0.50    0.80    --  -86.25  64.00 -26.00   50
  7  ω     35.00  75.00   0.50    0.80    --  107.75 -64.00-162.00   80
  8  ω     98.00 167.00   0.50    0.80    --  107.75  64.00 -26.00  138
  9  ω   -110.00 -75.00   0.50    0.20    --  -46.91-125.00  30.00   70
 10  ω   -116.00 -74.00   0.50    0.20    --  -46.91-125.00-150.00   84
 11  ω    -27.00  29.00   0.50    0.20    --  -46.91  19.00 -90.00  112
 12  ω    -25.00  27.00   0.50    0.20    --   46.91 -19.00  90.00  104
 13  ω     35.00  94.00   0.50    0.20    --   46.91-125.00  60.00  118
 14  ω    -47.00 -16.00   0.50    0.80    --  -86.25  45.00-180.00   62
 15  ω    -51.00 -14.00   0.50    0.80    --  -86.25  45.00 150.00   74
 16  ω     79.00 108.00   0.50    0.80    --  107.75-111.00 -58.68   58
 17  ω     36.00  62.00   0.50    0.80    --  107.75-111.00 -58.68   52
 18  ω     35.00 100.00   0.50    0.80    --  107.75 -95.00  90.00  130
 19  ω     35.00  71.00   0.50    0.80    --  107.75 -61.00 150.00   72
 20  ω     40.00  69.00   0.50    0.80    --  107.75-125.00   0.00   58
 21  ω     74.00 111.00   0.50    0.80    --  107.75-125.00   0.00   74
 22  ω     78.00 103.00   0.50    0.80    --  107.75 -95.00-150.00   50
 23  ω    117.00 176.00   0.50    0.80    --  107.75  38.00 -84.84  118
 24  ω     95.00 140.00   0.50    0.80    --  107.75 125.00 -90.00   90
 25  ω     42.00  97.00   0.50    0.80    --  107.75 -95.00   0.00  110
 26  ω     39.00  64.00   0.50    0.80    --  107.75-125.00-180.00   50
 27  ω     87.00 112.00   0.50    0.80    --  107.75-125.00-180.00   50
 28  ω    145.00 174.00   0.50    0.80    --  107.75 125.00 -90.00   58
 29  ω    105.00 177.00   0.50    0.80    --  107.75  26.00-119.12  144
 30  ω     37.00  63.00   0.50    0.80    --  107.75 -61.00 -90.00   52
 31  ω     95.00 178.00   0.50    0.80    --  107.75  45.00  90.00  166
 32  ω     39.00  80.00   0.50    0.80    --  107.75 -77.00-120.00   82
 33  ω     40.00 102.00   0.50    0.80    --  107.75 -95.00  60.00  124
 34  ω    117.00 174.00   0.50    0.80    --  107.75  30.00-180.00  114
 35  ω     41.00  66.00   0.50    0.80    --  107.75 -95.00 120.00   50
 36  ω     37.00  68.00   0.50    0.80    --  107.75 -95.00 -30.00   62
 37  ω     77.00 103.00   0.50    0.80    --  107.75 -95.00  30.00   52
 38  ω     98.00 127.00   0.50    0.80    --  107.75 125.00  60.00   58
 39  ω     36.00 103.00   0.50    0.80    --  107.75 -95.00 150.00  134
 40  ω    123.00 176.00   0.50    0.80    --  107.75  77.00-180.00  106
 41  ω     76.00 108.00   0.50    0.80    --  107.75-109.00  50.89   64
 42  ω     35.00  60.00   0.50    0.80    --  107.75 -95.00  30.00   50
 43  ω     63.00 112.00   0.50    0.80    --  107.75-125.00-150.00   98
 44  ω     39.00  90.00   0.50    0.80    --  107.75-125.00  30.00  102
 45  ω     61.00 107.00   0.50    0.80    --  107.75-106.00-110.40   92
 46  ω    150.00 175.00   0.50    0.80    --  107.75 125.00  60.00   50
 47  ω     35.00  62.00   0.50    0.80    --  107.75 -61.00  90.00   54
 48  ω     52.00  78.00   0.50    0.80    --  107.75-125.00 150.00   52
 49  ω     86.00 112.00   0.50    0.80    --  107.75-125.00 150.00   52
 50  ω     43.00  69.00   0.50    0.80    --  107.75 -77.00 120.00   52
 51  ω     38.00  64.00   0.50    0.80    --  107.75 -77.00 150.00   52
 52  ω     43.00  70.00   0.50    0.80    --  107.75 -95.00 -90.00   54
 53  ω     64.00 112.00   0.50    0.80    --  107.75-125.00  60.00   96
 54  ω    104.00 129.00   0.50    0.80    --  107.75  91.00  39.20   50
 55  ω    137.00 178.00   0.50    0.80    --  107.75  91.00  39.20   82
 56  ω    105.00 172.00   0.50    0.80    --  107.75  30.00  30.00  134
 57  ω    126.00 158.00   0.50    0.80    --  107.75  -3.00  94.12   64
 58  ω     75.00 111.00   0.50    0.80    --  107.75-124.00 -45.82   72
 59  ω     42.00 112.00   0.50    0.80    --  107.75-125.00-120.00  140
 60  ω     36.00  67.00   0.50    0.80    --  107.75 -61.00   0.00   62
 61  ω     44.00  83.00   0.50    0.80    --  107.75-141.00 109.00   78
 62  ω    -79.00 -35.00   0.50    0.20    --  -46.91 130.00  -5.00   88
 63  ω    -13.00  15.00   0.50    0.20    --   46.91 -19.00 -30.00   56
 64  ω    145.00 171.00   0.50    0.80    --  107.75  15.00 -30.00   52
 65  ω     61.00  87.00   0.50    0.80    --  107.75-135.00  17.98   52
 66  ω     38.00  65.00   0.50    0.80    --  107.75 -77.00   0.00   54
 67  ω     67.00  93.00   0.50    0.80    --  107.75 -77.00   0.00   52
 68  ω     80.00 105.00   0.50    0.80    --  107.75 -95.00  60.00   50
 69  ω     43.00  69.00   0.50    0.80    --  107.75 -61.00-180.00   52
 70  ω     37.00  75.00   0.50    0.80    --  107.75 -77.00-180.00   76
 71  ω     94.00 119.00   0.50    0.80    --  107.75-135.00  17.98   50
 72  ω    116.00 173.00   0.50    0.80    --  107.75  45.00 150.00  114
 73  ω     94.00 147.00   0.50    0.80    --  107.75  77.00  60.00  106
 74  ω     47.00  73.00   0.50    0.80    --  107.75 -77.00 -60.00   52
 75  ω     80.00 105.00   0.50    0.80    --  107.75 -77.00 -60.00   50
 76  ω     50.00  88.00   0.50    0.80    --  107.75-125.00 150.00   76
 77  ω    146.00 172.00   0.50    0.80    --  107.75 125.00  90.00   52
 78  ω    107.00 139.00   0.50    0.80    --  107.75  15.00 -30.00   64
 79  ω     96.00 122.00   0.50    0.80    --  107.75-141.00 109.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0299184000
_diffrn_orient_matrix_UB_12      -0.1219036000
_diffrn_orient_matrix_UB_13      0.0088048000
_diffrn_orient_matrix_UB_21      0.1587386000
_diffrn_orient_matrix_UB_22      0.1076000000
_diffrn_orient_matrix_UB_23      0.1176734000
_diffrn_orient_matrix_UB_31      -0.0566252000
_diffrn_orient_matrix_UB_32      0.0084621000
_diffrn_orient_matrix_UB_33      0.1072286000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6644
_reflns_number_total             7318
_reflns_special_details          
;
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.92a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         7318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0804
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1757P)²+0.4101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2401
_refine_ls_wR_factor_ref         0.2466
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7487(18)
 0.2513(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
3.a Rotating group:
 N36(H36A), N26(H26A)
3.b Aromatic/amide H refined with riding coordinates:
 N33(H33), N13(H13), N23(H23), C35(H35), C25(H25), C15(H15)
3.c X=CH2 refined with riding coordinates:
 N35(H35A,H35B), N15(H15A,H15B), N25(H25A,H25B), N16(H16A,H16B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N31 N 1.1084(2) 0.8092(2) 0.9483(2) 0.0236(5) Uani 1 1 d . . . . .
N21 N 1.3327(2) 0.9356(2) 0.6344(2) 0.0238(5) Uani 1 1 d . . . . .
N35 N 1.2490(3) 0.8763(2) 0.8451(2) 0.0252(5) Uani 1 1 d . . . . .
H35A H 1.315352 0.857479 0.892153 0.030 Uiso 1 1 calc R U . . .
H35B H 1.262864 0.907496 0.788219 0.030 Uiso 1 1 calc R U . . .
N11 N 1.2015(2) 0.3622(2) 0.8057(2) 0.0238(5) Uani 1 1 d . . . . .
N32 N 0.8673(3) 0.8028(3) 0.8915(3) 0.0294(6) Uani 1 1 d . . . . .
N15 N 1.1351(3) 0.5365(2) 0.8867(2) 0.0262(5) Uani 1 1 d . . . . .
H15A H 1.048835 0.471020 0.864974 0.031 Uiso 1 1 calc R U . . .
H15B H 1.155529 0.626051 0.923981 0.031 Uiso 1 1 calc R U . . .
N24 N 1.1907(3) 0.6911(3) 0.2634(2) 0.0302(6) Uani 1 1 d . . . . .
N25 N 1.0909(3) 0.8349(2) 0.4650(2) 0.0258(5) Uani 1 1 d . . . . .
H25A H 1.069465 0.879076 0.528167 0.031 Uiso 1 1 calc R U . . .
H25B H 1.021370 0.780050 0.378228 0.031 Uiso 1 1 calc R U . . .
N34 N 1.0023(3) 0.9330(2) 0.6914(3) 0.0287(5) Uani 1 1 d . . . . .
N14 N 1.4409(3) 0.7446(2) 0.9491(3) 0.0294(5) Uani 1 1 d . . . . .
N33 N 0.8005(3) 0.8830(3) 0.7211(3) 0.0323(6) Uani 1 1 d . . . . .
H33 H 0.712324 0.873680 0.710279 0.039 Uiso 1 1 calc R U . . .
N22 N 1.5213(3) 0.8839(2) 0.5909(2) 0.0287(5) Uani 1 1 d . . . . .
N36 N 0.9712(3) 0.7355(3) 1.0483(3) 0.0360(6) Uani 1 1 d . . . . .
H36A H 0.893594 0.734397 1.060075 0.043 Uiso 1 1 d R U . . .
N16 N 1.2565(3) 0.1836(3) 0.7183(3) 0.0329(6) Uani 1 1 d . . . . .
H16A H 1.313583 0.150945 0.693706 0.039 Uiso 1 1 calc R U . . .
H16B H 1.170708 0.124798 0.704652 0.039 Uiso 1 1 calc R U . . .
N12 N 1.4325(3) 0.4088(2) 0.7954(3) 0.0286(5) Uani 1 1 d . . . . .
N13 N 1.5858(3) 0.6613(2) 0.8878(3) 0.0331(6) Uani 1 1 d . . . . .
H13 H 1.662741 0.661722 0.875634 0.040 Uiso 1 1 calc R U . . .
N23 N 1.4232(3) 0.7211(3) 0.3460(3) 0.0320(6) Uani 1 1 d . . . . .
H23 H 1.501822 0.711619 0.346708 0.038 Uiso 1 1 calc R U . . .
N26 N 1.5693(3) 1.0360(3) 0.8084(3) 0.0348(6) Uani 1 1 d . . . . .
H26A H 1.661547 1.061733 0.821729 0.042 Uiso 1 1 d R U . . .
C34 C 1.0169(3) 0.8860(3) 0.7890(3) 0.0247(6) Uani 1 1 d . . . . .
C31 C 1.1268(3) 0.8573(3) 0.8602(3) 0.0220(6) Uani 1 1 d . . . . .
C33 C 0.8923(3) 0.8546(3) 0.8082(3) 0.0267(6) Uani 1 1 d . . . . .
C21 C 1.2289(3) 0.8511(3) 0.5010(3) 0.0228(6) Uani 1 1 d . . . . .
C11 C 1.2358(3) 0.4999(3) 0.8629(3) 0.0222(6) Uani 1 1 d . . . . .
C32 C 0.9820(3) 0.7857(3) 0.9600(3) 0.0254(6) Uani 1 1 d . . . . .
C22 C 1.4724(3) 0.9496(3) 0.6722(3) 0.0254(6) Uani 1 1 d . . . . .
C14 C 1.3751(3) 0.5986(3) 0.8942(3) 0.0252(6) Uani 1 1 d . . . . .
C12 C 1.3004(3) 0.3238(3) 0.7769(3) 0.0250(6) Uani 1 1 d . . . . .
C24 C 1.2704(3) 0.7832(3) 0.4046(3) 0.0246(6) Uani 1 1 d . . . . .
C13 C 1.4640(3) 0.5451(3) 0.8555(3) 0.0260(6) Uani 1 1 d . . . . .
C23 C 1.4147(3) 0.8034(3) 0.4577(3) 0.0264(6) Uani 1 1 d . . . . .
C35 C 0.8713(3) 0.9284(3) 0.6545(3) 0.0319(6) Uani 1 1 d . . . . .
H35 H 0.829863 0.954237 0.587633 0.038 Uiso 1 1 calc R U . . .
C25 C 1.2875(3) 0.6570(3) 0.2343(3) 0.0326(7) Uani 1 1 d . . . . .
H25 H 1.264773 0.593664 0.143846 0.039 Uiso 1 1 calc R U . . .
C15 C 1.5651(3) 0.7760(3) 0.9422(3) 0.0330(7) Uani 1 1 d . . . . .
H15 H 1.634382 0.869642 0.972251 0.040 Uiso 1 1 calc R U . . .
H36B H 1.049(5) 0.733(4) 1.106(4) 0.040(9) Uiso 1 1 d . . . . .
H26B H 1.553(4) 1.094(4) 0.862(4) 0.039(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N31 C31 1.351(3) . ?
N31 C32 1.359(4) . ?
N21 C21 1.344(4) . ?
N21 C22 1.360(4) . ?
N35 H35A 0.8800 . ?
N35 H35B 0.8800 . ?
N35 C31 1.339(4) . ?
N11 C11 1.345(3) . ?
N11 C12 1.357(3) . ?
N32 C33 1.344(4) . ?
N32 C32 1.345(4) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
N15 C11 1.344(3) . ?
N24 C24 1.386(4) . ?
N24 C25 1.314(4) . ?
N25 H25A 0.8800 . ?
N25 H25B 0.8800 . ?
N25 C21 1.337(4) . ?
N34 C34 1.394(3) . ?
N34 C35 1.310(4) . ?
N14 C14 1.390(3) . ?
N14 C15 1.306(4) . ?
N33 H33 0.8800 . ?
N33 C33 1.371(4) . ?
N33 C35 1.358(4) . ?
N22 C22 1.344(4) . ?
N22 C23 1.348(4) . ?
N36 H36A 0.8831 . ?
N36 C32 1.350(4) . ?
N36 H36B 0.91(4) . ?
N16 H16A 0.8800 . ?
N16 H16B 0.8800 . ?
N16 C12 1.350(4) . ?
N12 C12 1.345(4) . ?
N12 C13 1.340(4) . ?
N13 H13 0.8800 . ?
N13 C13 1.371(4) . ?
N13 C15 1.363(4) . ?
N23 H23 0.8800 . ?
N23 C23 1.373(4) . ?
N23 C25 1.357(4) . ?
N26 H26A 0.8840 . ?
N26 C22 1.353(4) . ?
N26 H26B 0.85(4) . ?
C34 C31 1.405(4) . ?
C34 C33 1.383(4) . ?
C21 C24 1.414(4) . ?
C11 C14 1.403(4) . ?
C14 C13 1.388(4) . ?
C24 C23 1.380(4) . ?
C35 H35 0.9500 . ?
C25 H25 0.9500 . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C31 N31 C32 118.6(2) . . ?
C21 N21 C22 118.9(2) . . ?
H35A N35 H35B 120.0 . . ?
C31 N35 H35A 120.0 . . ?
C31 N35 H35B 120.0 . . ?
C11 N11 C12 119.1(2) . . ?
C33 N32 C32 111.8(2) . . ?
H15A N15 H15B 120.0 . . ?
C11 N15 H15A 120.0 . . ?
C11 N15 H15B 120.0 . . ?
C25 N24 C24 103.5(2) . . ?
H25A N25 H25B 120.0 . . ?
C21 N25 H25A 120.0 . . ?
C21 N25 H25B 120.0 . . ?
C35 N34 C34 103.7(2) . . ?
C15 N14 C14 103.9(2) . . ?
C33 N33 H33 126.5 . . ?
C35 N33 H33 126.5 . . ?
C35 N33 C33 107.0(2) . . ?
C22 N22 C23 111.6(2) . . ?
H36A N36 H36B 125.8 . . ?
C32 N36 H36A 109.9 . . ?
C32 N36 H36B 121(3) . . ?
H16A N16 H16B 120.0 . . ?
C12 N16 H16A 120.0 . . ?
C12 N16 H16B 120.0 . . ?
C13 N12 C12 111.8(2) . . ?
C13 N13 H13 126.5 . . ?
C15 N13 H13 126.5 . . ?
C15 N13 C13 107.1(2) . . ?
C23 N23 H23 126.5 . . ?
C25 N23 H23 126.5 . . ?
C25 N23 C23 107.1(2) . . ?
H26A N26 H26B 118.0 . . ?
C22 N26 H26A 110.0 . . ?
C22 N26 H26B 123(3) . . ?
N34 C34 C31 132.0(2) . . ?
C33 C34 N34 110.7(2) . . ?
C33 C34 C31 117.2(2) . . ?
N31 C31 C34 118.3(2) . . ?
N35 C31 N31 118.7(2) . . ?
N35 C31 C34 123.0(2) . . ?
N32 C33 N33 128.5(2) . . ?
N32 C33 C34 126.4(2) . . ?
N33 C33 C34 105.1(2) . . ?
N21 C21 C24 118.6(2) . . ?
N25 C21 N21 118.7(2) . . ?
N25 C21 C24 122.8(2) . . ?
N11 C11 C14 118.3(2) . . ?
N15 C11 N11 118.7(2) . . ?
N15 C11 C14 123.0(2) . . ?
N32 C32 N31 127.6(2) . . ?
N32 C32 N36 117.6(2) . . ?
N36 C32 N31 114.8(2) . . ?
N22 C22 N21 127.3(3) . . ?
N22 C22 N26 117.8(2) . . ?
N26 C22 N21 114.9(2) . . ?
N14 C14 C11 132.1(2) . . ?
C13 C14 N14 110.9(2) . . ?
C13 C14 C11 116.9(2) . . ?
N16 C12 N11 115.2(2) . . ?
N12 C12 N11 127.2(2) . . ?
N12 C12 N16 117.5(2) . . ?
N24 C24 C21 132.2(2) . . ?
C23 C24 N24 111.3(2) . . ?
C23 C24 C21 116.4(2) . . ?
N12 C13 N13 128.6(2) . . ?
N12 C13 C14 126.6(3) . . ?
N13 C13 C14 104.7(2) . . ?
N22 C23 N23 128.2(2) . . ?
N22 C23 C24 127.0(2) . . ?
N23 C23 C24 104.7(2) . . ?
N34 C35 N33 113.6(3) . . ?
N34 C35 H35 123.2 . . ?
N33 C35 H35 123.2 . . ?
N24 C25 N23 113.4(3) . . ?
N24 C25 H25 123.3 . . ?
N23 C25 H25 123.3 . . ?
N14 C15 N13 113.5(2) . . ?
N14 C15 H15 123.3 . . ?
N13 C15 H15 123.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N21 C21 C24 N24 179.5(3) . . . . ?
N21 C21 C24 C23 3.5(4) . . . . ?
N11 C11 C14 N14 178.1(3) . . . . ?
N11 C11 C14 C13 3.9(4) . . . . ?
N15 C11 C14 N14 -1.5(5) . . . . ?
N15 C11 C14 C13 -175.8(2) . . . . ?
N24 C24 C23 N22 -178.7(3) . . . . ?
N24 C24 C23 N23 -0.2(3) . . . . ?
N25 C21 C24 N24 -0.6(5) . . . . ?
N25 C21 C24 C23 -176.5(2) . . . . ?
N34 C34 C31 N31 -178.6(2) . . . . ?
N34 C34 C31 N35 1.8(5) . . . . ?
N34 C34 C33 N32 177.9(3) . . . . ?
N34 C34 C33 N33 0.0(3) . . . . ?
N14 C14 C13 N12 -177.8(3) . . . . ?
N14 C14 C13 N13 0.0(3) . . . . ?
C34 N34 C35 N33 0.4(3) . . . . ?
C31 N31 C32 N32 1.0(4) . . . . ?
C31 N31 C32 N36 178.9(2) . . . . ?
C31 C34 C33 N32 2.0(4) . . . . ?
C31 C34 C33 N33 -175.9(2) . . . . ?
C33 N32 C32 N31 -2.8(4) . . . . ?
C33 N32 C32 N36 179.4(2) . . . . ?
C33 N33 C35 N34 -0.4(4) . . . . ?
C33 C34 C31 N31 -3.8(4) . . . . ?
C33 C34 C31 N35 176.6(2) . . . . ?
C21 N21 C22 N22 -2.2(4) . . . . ?
C21 N21 C22 N26 -179.7(2) . . . . ?
C21 C24 C23 N22 -1.9(4) . . . . ?
C21 C24 C23 N23 176.6(2) . . . . ?
C11 N11 C12 N16 -179.3(2) . . . . ?
C11 N11 C12 N12 -2.1(4) . . . . ?
C11 C14 C13 N12 -2.4(4) . . . . ?
C11 C14 C13 N13 175.4(2) . . . . ?
C32 N31 C31 N35 -177.9(2) . . . . ?
C32 N31 C31 C34 2.5(4) . . . . ?
C32 N32 C33 N33 178.6(3) . . . . ?
C32 N32 C33 C34 1.2(4) . . . . ?
C22 N21 C21 N25 178.3(2) . . . . ?
C22 N21 C21 C24 -1.7(4) . . . . ?
C22 N22 C23 N23 -179.6(3) . . . . ?
C22 N22 C23 C24 -1.5(4) . . . . ?
C14 N14 C15 N13 -0.5(3) . . . . ?
C12 N11 C11 N15 177.8(2) . . . . ?
C12 N11 C11 C14 -1.9(4) . . . . ?
C12 N12 C13 N13 -178.4(3) . . . . ?
C12 N12 C13 C14 -1.1(4) . . . . ?
C24 N24 C25 N23 -0.4(3) . . . . ?
C13 N12 C12 N11 3.5(4) . . . . ?
C13 N12 C12 N16 -179.4(2) . . . . ?
C13 N13 C15 N14 0.5(4) . . . . ?
C23 N22 C22 N21 3.7(4) . . . . ?
C23 N22 C22 N26 -178.8(2) . . . . ?
C23 N23 C25 N24 0.3(4) . . . . ?
C35 N34 C34 C31 174.9(3) . . . . ?
C35 N34 C34 C33 -0.2(3) . . . . ?
C35 N33 C33 N32 -177.6(3) . . . . ?
C35 N33 C33 C34 0.3(3) . . . . ?
C25 N24 C24 C21 -175.7(3) . . . . ?
C25 N24 C24 C23 0.4(3) . . . . ?
C25 N23 C23 N22 178.4(3) . . . . ?
C25 N23 C23 C24 -0.1(3) . . . . ?
C15 N14 C14 C11 -174.2(3) . . . . ?
C15 N14 C14 C13 0.3(3) . . . . ?
C15 N13 C13 N12 177.5(3) . . . . ?
C15 N13 C13 C14 -0.2(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.268 0.500 0.500 208.7 53.1 '2 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'Mounted in cryo mesh'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.603
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7487(18) 19106 4559 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2513(18) 18590 4559 nmt 0.9958 -0.0133 -0.0026 -0.9838 -0.9523 -0.9847
0.0056 1.0290 0.0108

_twin_special_details            
;
Component 2 rotated by 118.3424° 
around [0.90 -0.30 -0.31] (reciprocal) or [1.00 -0.01 0.00] (direct)
;
####################################################################### 
# 
# 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_DAP_anhydrate
_database_code_depnum_ccdc_archive 'CCDC 2164594'
loop_
_audit_author_name
_audit_author_address
'Tomislav Stolar'
;Ruder Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-07-11 deposited with the CCDC.	2022-08-15 downloaded from the CCDC.
;

_chemical_formula_weight         150.16
_chemical_formula_moiety         'C5 H6 N6'
_cell_formula_units_Z            8
_chemical_formula_sum            'C5 H6 N6'

_cell_length_a                   14.97434(81)
_cell_length_b                   12.37809(44)
_cell_length_c                   6.76487(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1253.894(88)
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_diffrn_measurement_device_type  
;
Laboratory powder diffractometer equiped with Mo KÎ+- source. 
;

_diffrn_ambient_temperature      295
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_exptl_crystal_density_diffrn    1.590
_refine_ls_hydrogen_treatment    refall
_refine_ls_shift/su_max          <0.01
_refine_ls_number_parameters     50
_pd_proc_ls_prof_R_factor        0.054
_pd_proc_ls_prof_wR_factor       0.071
_refine_ls_R_Fsqd_factor         0.023
_refine_ls_goodness_of_fit_all   1.97
_cell_measurement_temperature    295
_exptl_crystal_colour            white

_computing_cell_refinement       Topas
_computing_structure_solution    Topas
_computing_structure_refinement  Topas

_refine_special_details          
;
Structure refined with rigid bodies and additional rotational degrees of freedom for the protons from the amino groups. 
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N3 N 8 -0.09168743 0.4543357 0.3681001 1 2.385(64)
N4 N 8 -0.2073546 0.3334227 0.3812718 1 2.385(64)
N5 N 8 -0.3459621 0.2338304 0.4073628 1 2.385(64)
H10 H 8 -0.3263694 0.1685673 0.4027686 1 2.385(64)
N6 N 8 -0.4426944 0.3700709 0.4282542 1 2.385(64)
N7 N 8 -0.2324158 0.5267704 0.3861209 1 2.385(64)
N8 N 8 -0.3730942 0.6029317 0.3999651 1 2.385(64)
C5 C 8 -0.1803206 0.4370937 0.3772062 1 2.385(64)
C6 C 8 -0.2964381 0.3257791 0.398202 1 2.385(64)
C7 C 8 -0.4328542 0.2652354 0.4250752 1 2.385(64)
H9 H 8 -0.4802636 0.2169664 0.434066 1 2.385(64)
C8 C 8 -0.3564733 0.4101865 0.4121444 1 2.385(64)
C9 C 8 -0.3211296 0.5153504 0.4057823 1 2.385(64)
H6 H 8 -0.06137699 0.4290942 0.2699045 1 2.385(64)
H5 H 8 -0.06292466 0.4724165 0.4771022 1 2.385(64)
H7 H 8 -0.4270556 0.599339 0.4464748 1 2.385(64)
H8 H 8 -0.3537165 0.6671716 0.3854548 1 2.385(64)

# start Validation Reply Form
_vrf_GEOM001_DAP_anhydrate       
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: Can be calculated from atomic coordinates
;
_vrf_GEOM002_DAP_anhydrate       
;
PROBLEM: _geom_bond_atom_site_label_2 is missing
RESPONSE: Can be calculated from atomic coordinates
;
_vrf_GEOM003_DAP_anhydrate       
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: Can be calculated from atomic coordinates
;
_vrf_GEOM006_DAP_anhydrate       
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: Can be calculated from atomic coordinates
;
_vrf_GEOM007_DAP_anhydrate       
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: Can be calculated from atomic coordinates
;
_vrf_GEOM008_DAP_anhydrate       
;
PROBLEM: _geom_angle is missing
RESPONSE: Can be calculated from atomic coordinates
;

loop_
_pd_meas_2theta_corrected
_pd_meas_intensity_total
_pd_calc_intensity_total
2.00029 349.69000 337.29043
2.00429 424.36000 339.65180
2.00829 372.49000 341.98700
2.01229 380.25000 344.29625
2.01629 404.01000 346.57976
2.02029 400.00000 348.83773
2.02429 376.36000 351.07038
2.02829 396.01000 353.27792
2.03229 376.36000 355.46054
2.03629 368.64000 357.61847
2.04029 368.64000 359.75191
2.04429 372.49000 361.86105
2.04829 380.25000 363.94609
2.05229 376.36000 366.00726
2.05629 408.04000 368.04473
2.06029 436.81000 370.05871
2.06429 420.25000 372.04939
2.06829 368.64000 374.01698
2.07229 396.01000 375.96167
2.07629 338.56000 377.88365
2.08029 396.01000 379.78311
2.08429 408.04000 381.66024
2.08829 376.36000 383.51525
2.09229 408.04000 385.34830
2.09629 400.00000 387.15960
2.10029 408.04000 388.94933
2.10429 396.01000 390.71767
2.10829 416.16000 392.46481
2.11229 404.01000 394.19093
2.11629 392.04000 395.89622
2.12029 388.09000 397.58085
2.12429 384.16000 399.24500
2.12829 380.25000 400.88886
2.13229 424.36000 402.51260
2.13629 412.09000 404.11639
2.14029 416.16000 405.70042
2.14429 384.16000 407.26486
2.14829 388.09000 408.80987
2.15229 420.25000 410.33564
2.15629 404.01000 411.84233
2.16029 392.04000 413.33011
2.16429 392.04000 414.79915
2.16829 376.36000 416.24962
2.17229 420.25000 417.68169
2.17629 408.04000 419.09552
2.18029 376.36000 420.49127
2.18429 380.25000 421.86911
2.18829 404.01000 423.22920
2.19229 400.00000 424.57171
2.19629 416.16000 425.89679
2.20029 432.64000 427.20460
2.20429 400.00000 428.49530
2.20829 412.09000 429.76904
2.21229 400.00000 431.02600
2.21629 441.00000 432.26631
2.22029 420.25000 433.49013
2.22429 408.04000 434.69762
2.22829 416.16000 435.88893
2.23229 441.00000 437.06420
2.23629 428.49000 438.22360
2.24029 416.16000 439.36726
2.24429 424.36000 440.49535
2.24829 424.36000 441.60799
2.25229 420.25000 442.70535
2.25629 424.36000 443.78756
2.26029 453.69000 444.85477
2.26429 424.36000 445.90713
2.26829 453.69000 446.94477
2.27229 475.24000 447.96784
2.27629 396.01000 448.97648
2.28029 424.36000 449.97082
2.28429 424.36000 450.95101
2.28829 412.09000 451.91719
2.29229 416.16000 452.86948
2.29629 436.81000 453.80804
2.30029 420.25000 454.73298
2.30429 424.36000 455.64445
2.30829 432.64000 456.54258
2.31229 441.00000 457.42750
2.31629 457.96000 458.29934
2.32029 449.44000 459.15823
2.32429 453.69000 460.00431
2.32829 436.81000 460.83770
2.33229 441.00000 461.65853
2.33629 445.21000 462.46692
2.34029 445.21000 463.26301
2.34429 449.44000 464.04691
2.34829 466.56000 464.81876
2.35229 449.44000 465.57867
2.35629 466.56000 466.32677
2.36029 445.21000 467.06318
2.36429 449.44000 467.78802
2.36829 457.96000 468.50141
2.37229 445.21000 469.20347
2.37629 484.00000 469.89432
2.38029 470.89000 470.57408
2.38429 436.81000 471.24286
2.38829 470.89000 471.90078
2.39229 475.24000 472.54796
2.39629 457.96000 473.18450
2.40029 449.44000 473.81052
2.40429 484.00000 474.42615
2.40829 436.81000 475.03147
2.41229 462.25000 475.62662
2.41629 492.84000 476.21170
2.42029 466.56000 476.78681
2.42429 475.24000 477.35207
2.42829 492.84000 477.90759
2.43229 479.61000 478.45347
2.43629 484.00000 478.98981
2.44029 492.84000 479.51674
2.44429 457.96000 480.03434
2.44829 484.00000 480.54273
2.45229 432.64000 481.04200
2.45629 466.56000 481.53227
2.46029 484.00000 482.01363
2.46429 510.76000 482.48618
2.46829 470.89000 482.95003
2.47229 457.96000 483.40527
2.47629 445.21000 483.85200
2.48029 470.89000 484.29033
2.48429 492.84000 484.72034
2.48829 462.25000 485.14214
2.49229 470.89000 485.55582
2.49629 479.61000 485.96148
2.50029 462.25000 486.35922
2.50429 488.41000 486.74911
2.50829 445.21000 487.13127
2.51229 462.25000 487.50578
2.51629 510.76000 487.87274
2.52029 492.84000 488.23223
2.52429 488.41000 488.58435
2.52829 466.56000 488.92918
2.53229 470.89000 489.26682
2.53629 479.61000 489.59736
2.54029 497.29000 489.92088
2.54429 484.00000 490.23746
2.54829 492.84000 490.54720
2.55229 506.25000 490.85019
2.55629 510.76000 491.14650
2.56029 492.84000 491.43622
2.56429 479.61000 491.71944
2.56829 470.89000 491.99624
2.57229 484.00000 492.26670
2.57629 484.00000 492.53090
2.58029 497.29000 492.78893
2.58429 515.29000 493.04086
2.58829 475.24000 493.28678
2.59229 510.76000 493.52677
2.59629 484.00000 493.76090
2.60029 479.61000 493.98925
2.60429 492.84000 494.21191
2.60829 488.41000 494.42894
2.61229 492.84000 494.64043
2.61629 479.61000 494.84644
2.62029 475.24000 495.04707
2.62429 501.76000 495.24237
2.62829 519.84000 495.43242
2.63229 538.24000 495.61731
2.63629 510.76000 495.79709
2.64029 492.84000 495.97185
2.64429 533.61000 496.14165
2.64829 492.84000 496.30657
2.65229 501.76000 496.46667
2.65629 506.25000 496.62203
2.66029 515.29000 496.77271
2.66429 497.29000 496.91879
2.66829 519.84000 497.06033
2.67229 510.76000 497.19741
2.67629 519.84000 497.33008
2.68029 524.41000 497.45841
2.68429 538.24000 497.58248
2.68829 519.84000 497.70234
2.69229 552.25000 497.81806
2.69629 542.89000 497.92971
2.70029 538.24000 498.03735
2.70429 529.00000 498.14104
2.70829 524.41000 498.24085
2.71229 510.76000 498.33683
2.71629 524.41000 498.42906
2.72029 510.76000 498.51758
2.72429 519.84000 498.60247
2.72829 524.41000 498.68378
2.73229 542.89000 498.76158
2.73629 538.24000 498.83591
2.74029 529.00000 498.90685
2.74429 510.76000 498.97444
2.74829 538.24000 499.03875
2.75229 484.00000 499.09983
2.75629 492.84000 499.15774
2.76029 475.24000 499.21254
2.76429 466.56000 499.26428
2.76829 479.61000 499.31302
2.77229 510.76000 499.35881
2.77629 524.41000 499.40171
2.78029 470.89000 499.44177
2.78429 484.00000 499.47904
2.78829 510.76000 499.51357
2.79229 475.24000 499.54543
2.79629 492.84000 499.57466
2.80029 506.25000 499.60131
2.80429 492.84000 499.62543
2.80829 538.24000 499.64708
2.81229 492.84000 499.66630
2.81629 484.00000 499.68314
2.82029 462.25000 499.69766
2.82429 492.84000 499.70990
2.82829 484.00000 499.71991
2.83229 492.84000 499.72773
2.83629 497.29000 499.73342
2.84029 492.84000 499.73703
2.84429 510.76000 499.73859
2.84829 524.41000 499.73816
2.85229 501.76000 499.73578
2.85629 501.76000 499.73149
2.86029 488.41000 499.72535
2.86429 488.41000 499.71739
2.86829 479.61000 499.70766
2.87229 488.41000 499.69620
2.87629 488.41000 499.68306
2.88029 510.76000 499.66827
2.88429 501.76000 499.65189
2.88829 484.00000 499.63395
2.89229 492.84000 499.61449
2.89629 501.76000 499.59356
2.90029 501.76000 499.57120
2.90429 470.89000 499.54744
2.90829 506.25000 499.52233
2.91229 488.41000 499.49591
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49.73229 282.24000 273.05270
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49.75229 278.89000 272.99323
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49.76029 289.00000 272.92942
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49.81629 289.00000 272.49124
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49.82429 275.56000 272.49952
49.82829 278.89000 272.51596
49.83229 295.84000 272.54151
49.83629 278.89000 272.57679
49.84029 275.56000 272.62241
49.84429 289.00000 272.67884
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49.85629 272.25000 272.92079
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49.87629 265.69000 273.59476
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49.88829 282.24000 274.17436
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49.90429 262.44000 275.15113
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49.91229 285.61000 275.72152
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49.94029 272.25000 278.08391
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49.97229 256.00000 281.28541
49.97629 278.89000 281.70911
49.98029 292.41000 282.13618
49.98429 252.81000 282.56594
49.98829 259.21000 282.99758
49.99229 262.44000 283.43030
_chemical_name_systematic        2,6-diaminopurine
_chemical_name_common            2-aminoadenine
_chemical_melting_point          574
