# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_r20191127a
_audit_block_doi                 10.5517/ccdc.csd.cc242dxk
_database_code_depnum_ccdc_archive 'CCDC 1968528'
_audit_update_record             
;
2019-11-29 deposited with the CCDC.	2020-07-03 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 N6 O3'
_chemical_formula_sum            'C15 H14 N6 O3'
_chemical_formula_weight         326.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H16N6O3
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.3096(6)
_cell_length_b                   29.084(2)
_cell_length_c                   7.5539(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.450(9)
_cell_angle_gamma                90
_cell_volume                     1385.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3907
_cell_measurement_temperature    133.15
_cell_measurement_theta_max      32.9400
_cell_measurement_theta_min      2.7720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12221
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.787
_diffrn_ambient_temperature      133.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0453820000
_diffrn_orient_matrix_UB_12      -0.0221941000
_diffrn_orient_matrix_UB_13      -0.0101425000
_diffrn_orient_matrix_UB_21      -0.1022811000
_diffrn_orient_matrix_UB_22      0.0099801000
_diffrn_orient_matrix_UB_23      -0.0081381000
_diffrn_orient_matrix_UB_31      0.0108910000
_diffrn_orient_matrix_UB_32      0.0015120000
_diffrn_orient_matrix_UB_33      -0.0930743000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2159
_reflns_number_total             2826
_reflns_odcompleteness_completeness 92.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.80
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear (Rigaku, 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.301
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.016(3)
_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   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.130
_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)+(0.0637P)²+1.2721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1686
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C4(H4), C2(H2), C1(H1), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_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 0.8287(3) 0.29620(6) 0.7132(3) 0.0316(5) Uani 1 1 d . . . . .
O3 O 0.3896(3) 0.14051(6) 0.4821(3) 0.0354(5) Uani 1 1 d . . . . .
O2 O 0.6733(3) 0.15963(7) 0.6345(3) 0.0373(5) Uani 1 1 d . . . . .
N3 N 0.2865(3) 0.35648(7) 0.4385(3) 0.0227(5) Uani 1 1 d . . . . .
N6 N 0.5120(4) 0.16964(8) 0.5462(3) 0.0280(5) Uani 1 1 d . . . . .
N4 N 0.6828(4) 0.32588(8) 0.6398(3) 0.0280(5) Uani 1 1 d . . . . .
N5 N 0.7771(4) 0.25024(8) 0.6815(3) 0.0282(5) Uani 1 1 d . . . . .
N2 N 0.1745(4) 0.44842(8) 0.3287(3) 0.0282(5) Uani 1 1 d . . . . .
N1 N 0.2891(4) 0.51920(8) 0.2252(3) 0.0316(6) Uani 1 1 d . . . . .
C5 C 0.1251(4) 0.49095(8) 0.2618(4) 0.0245(6) Uani 1 1 d . . . . .
C10 C 0.3453(4) 0.31279(9) 0.4653(3) 0.0224(6) Uani 1 1 d . . . . .
C11 C 0.5381(4) 0.29946(9) 0.5615(3) 0.0228(6) Uani 1 1 d . . . . .
C12 C 0.5969(4) 0.25209(9) 0.5883(3) 0.0228(6) Uani 1 1 d . . . . .
C13 C 0.4638(4) 0.21692(9) 0.5193(3) 0.0235(6) Uani 1 1 d . . . . .
C14 C 0.2814(4) 0.22999(9) 0.4299(3) 0.0243(6) Uani 1 1 d . . . . .
H14 H 0.190353 0.206578 0.384325 0.029 Uiso 1 1 calc R U . . .
C15 C 0.2223(4) 0.27555(9) 0.4024(4) 0.0238(6) Uani 1 1 d . . . . .
H15 H 0.093859 0.281798 0.338579 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0844(4) 0.36640(8) 0.3449(4) 0.0243(6) Uani 1 1 d . . . . .
H7A H -0.025533 0.344923 0.386244 0.029 Uiso 1 1 calc R U . . .
H7B H 0.101071 0.361319 0.216381 0.029 Uiso 1 1 calc R U . . .
C6 C 0.0121(4) 0.41556(9) 0.3756(4) 0.0260(6) Uani 1 1 d . . . . .
H6A H -0.118279 0.421588 0.303656 0.031 Uiso 1 1 calc R U . . .
H6B H -0.022277 0.419548 0.501817 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4116(4) 0.39668(9) 0.4952(4) 0.0295(6) Uani 1 1 d . . . . .
H8A H 0.562201 0.387677 0.510886 0.035 Uiso 1 1 calc R U . . .
H8B H 0.361137 0.407660 0.610838 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0845(4) 0.50406(9) 0.2305(4) 0.0277(6) Uani 1 1 d . . . . .
H4 H -0.197855 0.484384 0.261505 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3935(4) 0.43522(9) 0.3610(4) 0.0293(6) Uani 1 1 d . . . . .
H9A H 0.474957 0.462161 0.405086 0.035 Uiso 1 1 calc R U . . .
H9B H 0.455864 0.425150 0.248475 0.035 Uiso 1 1 calc R U . . .
C2 C 0.0402(5) 0.57558(10) 0.1160(4) 0.0333(7) Uani 1 1 d . . . . .
H2 H 0.013933 0.604993 0.065394 0.040 Uiso 1 1 calc R U . . .
C1 C 0.2420(5) 0.56091(9) 0.1541(4) 0.0309(7) Uani 1 1 d . . . . .
H1 H 0.355948 0.581076 0.129253 0.037 Uiso 1 1 calc R U . . .
C3 C -0.1237(5) 0.54615(10) 0.1538(4) 0.0351(7) Uani 1 1 d . . . . .
H3 H -0.265591 0.555074 0.126385 0.042 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
O1 N4 1.369(3) . ?
O1 N5 1.395(3) . ?
O3 N6 1.237(3) . ?
O2 N6 1.237(3) . ?
N3 C10 1.338(3) . ?
N3 C7 1.471(3) . ?
N3 C8 1.468(3) . ?
N6 C13 1.422(3) . ?
N4 C11 1.322(3) . ?
N5 C12 1.323(3) . ?
N2 C5 1.369(3) . ?
N2 C6 1.452(3) . ?
N2 C9 1.449(3) . ?
N1 C5 1.355(3) . ?
N1 C1 1.356(3) . ?
C5 C4 1.390(4) . ?
C10 C11 1.454(4) . ?
C10 C15 1.408(4) . ?
C11 C12 1.440(4) . ?
C12 C13 1.415(4) . ?
C13 C14 1.373(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(4) . ?
C15 H15 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.520(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.514(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.374(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C1 1.367(4) . ?
C2 C3 1.378(4) . ?
C1 H1 0.9500 . ?
C3 H3 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
N4 O1 N5 112.54(19) . . ?
C10 N3 C7 119.5(2) . . ?
C10 N3 C8 124.6(2) . . ?
C8 N3 C7 115.9(2) . . ?
O3 N6 O2 123.1(2) . . ?
O3 N6 C13 118.5(2) . . ?
O2 N6 C13 118.3(2) . . ?
C11 N4 O1 105.3(2) . . ?
C12 N5 O1 104.2(2) . . ?
C5 N2 C6 122.0(2) . . ?
C5 N2 C9 120.6(2) . . ?
C9 N2 C6 117.4(2) . . ?
C5 N1 C1 117.5(2) . . ?
N2 C5 C4 121.1(2) . . ?
N1 C5 N2 117.1(2) . . ?
N1 C5 C4 121.8(2) . . ?
N3 C10 C11 123.7(2) . . ?
N3 C10 C15 122.1(2) . . ?
C15 C10 C11 114.3(2) . . ?
N4 C11 C10 129.0(2) . . ?
N4 C11 C12 108.7(2) . . ?
C12 C11 C10 122.3(2) . . ?
N5 C12 C11 109.2(2) . . ?
N5 C12 C13 131.4(2) . . ?
C13 C12 C11 119.4(2) . . ?
C12 C13 N6 121.6(2) . . ?
C14 C13 N6 120.8(2) . . ?
C14 C13 C12 117.6(2) . . ?
C13 C14 H14 118.1 . . ?
C13 C14 C15 123.8(2) . . ?
C15 C14 H14 118.1 . . ?
C10 C15 H15 118.7 . . ?
C14 C15 C10 122.6(2) . . ?
C14 C15 H15 118.7 . . ?
N3 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
N3 C7 C6 111.8(2) . . ?
H7A C7 H7B 107.9 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
N2 C6 C7 111.4(2) . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N3 C8 H8A 109.4 . . ?
N3 C8 H8B 109.4 . . ?
N3 C8 C9 111.3(2) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
N2 C9 C8 111.4(2) . . ?
N2 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.6(3) . . ?
C3 C2 H2 121.2 . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N4 C11 C10 178.9(3) . . . . ?
O1 N4 C11 C12 0.2(3) . . . . ?
O1 N5 C12 C11 0.3(3) . . . . ?
O1 N5 C12 C13 -178.7(3) . . . . ?
O3 N6 C13 C12 -179.8(2) . . . . ?
O3 N6 C13 C14 2.4(4) . . . . ?
O2 N6 C13 C12 1.0(4) . . . . ?
O2 N6 C13 C14 -176.7(2) . . . . ?
N3 C10 C11 N4 1.4(4) . . . . ?
N3 C10 C11 C12 179.9(2) . . . . ?
N3 C10 C15 C14 -179.8(2) . . . . ?
N3 C7 C6 N2 54.9(3) . . . . ?
N3 C8 C9 N2 56.9(3) . . . . ?
N6 C13 C14 C15 178.5(2) . . . . ?
N4 O1 N5 C12 -0.2(3) . . . . ?
N4 C11 C12 N5 -0.4(3) . . . . ?
N4 C11 C12 C13 178.8(2) . . . . ?
N5 O1 N4 C11 0.0(3) . . . . ?
N5 C12 C13 N6 0.6(4) . . . . ?
N5 C12 C13 C14 178.5(3) . . . . ?
N2 C5 C4 C3 -176.3(2) . . . . ?
N1 C5 C4 C3 2.7(4) . . . . ?
C5 N2 C6 C7 147.5(2) . . . . ?
C5 N2 C9 C8 158.0(2) . . . . ?
C5 N1 C1 C2 -0.7(4) . . . . ?
C5 C4 C3 C2 -2.9(4) . . . . ?
C10 N3 C7 C6 162.5(2) . . . . ?
C10 N3 C8 C9 143.2(3) . . . . ?
C10 C11 C12 N5 -179.2(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C10 C15 C14 -0.2(4) . . . . ?
C11 C12 C13 N6 -178.3(2) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 0.7(4) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C15 C10 C11 N4 -178.2(3) . . . . ?
C15 C10 C11 C12 0.3(4) . . . . ?
C7 N3 C10 C11 -177.8(2) . . . . ?
C7 N3 C10 C15 1.7(4) . . . . ?
C7 N3 C8 C9 -36.2(3) . . . . ?
C6 N2 C5 N1 179.0(2) . . . . ?
C6 N2 C5 C4 -2.0(4) . . . . ?
C6 N2 C9 C8 -19.9(3) . . . . ?
C8 N3 C10 C11 2.8(4) . . . . ?
C8 N3 C10 C15 -177.7(3) . . . . ?
C8 N3 C7 C6 -18.1(3) . . . . ?
C9 N2 C5 N1 1.1(4) . . . . ?
C9 N2 C5 C4 -179.9(3) . . . . ?
C9 N2 C6 C7 -34.6(3) . . . . ?
C1 N1 C5 N2 178.1(2) . . . . ?
C1 N1 C5 C4 -0.9(4) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C3 C2 C1 N1 0.5(4) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.261
_oxdiff_exptl_absorpt_empirical_full_min 0.646
####################################################################### 
# 
# 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_r20191211d_tw
_database_code_depnum_ccdc_archive 'CCDC 1973453'
loop_
_audit_author_name
_audit_author_address
'Haibin Song'
;Nankai University
China
;
_audit_update_record             
;
2019-12-23 deposited with the CCDC.	2020-07-03 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:19:11 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N6 O3, I'
_chemical_formula_sum            'C16 H17 I N6 O3'
_chemical_formula_weight         468.25
_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 0.0033 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'
I I -0.4742 1.8119 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   19.9828(7)
_cell_length_b                   12.5986(5)
_cell_length_c                   14.2705(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.853(3)
_cell_angle_gamma                90
_cell_volume                     3516.1(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14630
_cell_measurement_temperature    133.15
_cell_measurement_theta_max      31.4120
_cell_measurement_theta_min      2.0810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.852
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.32673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.923
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6571
_reflns_number_total             7186
_reflns_special_details          
;
 _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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear(Rigaku, 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.937
_refine_diff_density_min         -2.912
_refine_diff_density_rms         0.200
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         7186
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.1022
_refine_ls_restrained_S_all      1.199
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0070P)²+97.0031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2203
_refine_ls_wR_factor_ref         0.2243
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.836(4)
 0.164(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(N10) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C22(H22A,H22B), C23(H23A,
 H23B), C24(H24A,H24B), C25(H25A,H25B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C30(H30), C31(H31)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.0972(4) 0.6156(8) 0.8805(6) 0.035(2) Uani 1 1 d . . . . .
O2 O -0.1108(5) 0.6017(8) 0.7768(6) 0.038(2) Uani 1 1 d . . . . .
O3 O -0.1534(4) 0.6107(8) 0.6254(7) 0.040(2) Uani 1 1 d . . . . .
N1 N 0.3959(6) 0.5384(10) 0.5757(8) 0.042(3) Uani 1 1 d . . . . .
N2 N 0.2939(6) 0.6283(11) 0.5683(7) 0.043(3) Uani 1 1 d . . . . .
N3 N 0.1609(5) 0.6131(9) 0.6118(6) 0.033(2) Uani 1 1 d . . . . .
N4 N 0.1345(5) 0.6145(9) 0.8102(7) 0.033(2) Uani 1 1 d . . . . .
N5 N 0.0279(6) 0.6146(9) 0.8444(7) 0.033(2) Uani 1 1 d . . . . .
N6 N -0.1045(6) 0.6087(9) 0.6919(8) 0.035(2) Uani 1 1 d . . . . .
C1 C 0.4329(9) 0.4579(14) 0.5471(12) 0.057(4) Uani 1 1 d . . . . .
H1 H 0.477392 0.442554 0.583083 0.069 Uiso 1 1 calc R U . . .
C2 C 0.4068(10) 0.3988(13) 0.4672(12) 0.056(4) Uani 1 1 d . . . . .
H2 H 0.432183 0.341414 0.448885 0.067 Uiso 1 1 calc R U . . .
C3 C 0.3428(9) 0.4243(14) 0.4137(12) 0.056(4) Uani 1 1 d . . . . .
H3 H 0.325338 0.388340 0.355274 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3052(8) 0.5012(15) 0.4454(11) 0.056(4) Uani 1 1 d . . . . .
H4 H 0.261065 0.518144 0.409196 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3309(7) 0.5559(13) 0.5312(9) 0.043(3) Uani 1 1 d . . . . .
C6 C 0.2859(6) 0.6232(15) 0.6676(9) 0.048(4) Uani 1 1 d . . . . .
H6A H 0.283697 0.695931 0.693016 0.057 Uiso 1 1 calc R U . . .
H6B H 0.325794 0.586710 0.707048 0.057 Uiso 1 1 calc R U . . .
C7 C 0.2218(6) 0.5643(12) 0.6732(10) 0.041(3) Uani 1 1 d . . . . .
H7A H 0.226032 0.489806 0.652912 0.049 Uiso 1 1 calc R U . . .
H7B H 0.215915 0.563522 0.740349 0.049 Uiso 1 1 calc R U . . .
C8 C 0.1687(6) 0.6258(13) 0.5111(8) 0.038(3) Uani 1 1 d . . . . .
H8A H 0.130015 0.667893 0.474958 0.046 Uiso 1 1 calc R U . . .
H8B H 0.168024 0.555274 0.480414 0.046 Uiso 1 1 calc R U . . .
C9 C 0.2343(6) 0.6805(12) 0.5087(9) 0.039(3) Uani 1 1 d . . . . .
H9A H 0.240593 0.683002 0.441680 0.047 Uiso 1 1 calc R U . . .
H9B H 0.231726 0.754560 0.530910 0.047 Uiso 1 1 calc R U . . .
C10 C 0.0993(6) 0.6097(11) 0.6319(9) 0.034(3) Uani 1 1 d . . . . .
C11 C 0.0884(7) 0.6105(10) 0.7294(9) 0.033(3) Uani 1 1 d . . . . .
C12 C 0.0220(6) 0.6107(9) 0.7509(8) 0.028(2) Uani 1 1 d . . . . .
C13 C -0.0370(6) 0.6121(9) 0.6751(8) 0.026(2) Uani 1 1 d . . . . .
C14 C -0.0263(6) 0.6109(10) 0.5825(8) 0.030(3) Uani 1 1 d . . . . .
H14 H -0.064904 0.609527 0.531079 0.036 Uiso 1 1 calc R U . . .
C15 C 0.0381(6) 0.6114(10) 0.5614(9) 0.031(3) Uani 1 1 d . . . . .
H15 H 0.041457 0.613098 0.496031 0.037 Uiso 1 1 calc R U . . .
C16 C 0.4324(7) 0.6091(14) 0.6532(10) 0.047(4) Uani 1 1 d . . . . .
H16A H 0.426835 0.581703 0.715397 0.071 Uiso 1 1 calc R U . . .
H16B H 0.413185 0.680849 0.643910 0.071 Uiso 1 1 calc R U . . .
H16C H 0.481073 0.611297 0.651193 0.071 Uiso 1 1 calc R U . . .
O4 O 0.0597(4) 0.3550(7) -0.3404(6) 0.034(2) Uani 1 1 d . . . . .
O5 O -0.1384(5) 0.3712(8) -0.2970(6) 0.041(2) Uani 1 1 d . . . . .
O6 O -0.1591(4) 0.3635(8) -0.1540(7) 0.043(2) Uani 1 1 d . . . . .
N7 N 0.4030(5) 0.4568(8) 0.0908(7) 0.030(2) Uani 1 1 d . . . . .
N8 N 0.2865(5) 0.4222(9) 0.0595(7) 0.030(2) Uani 1 1 d . . . . .
N9 N 0.1634(5) 0.3366(9) -0.0445(7) 0.031(2) Uani 1 1 d . . . . .
N10 N 0.1087(5) 0.3490(9) -0.2573(7) 0.032(2) Uani 1 1 d . U . . .
N11 N -0.0071(5) 0.3614(9) -0.3244(7) 0.033(2) Uani 1 1 d . . . . .
N12 N -0.1194(6) 0.3692(9) -0.2104(7) 0.035(2) Uani 1 1 d . . . . .
C17 C 0.4581(6) 0.5135(11) 0.1359(9) 0.037(3) Uani 1 1 d . . . . .
H17 H 0.500991 0.501454 0.118823 0.044 Uiso 1 1 calc R U . . .
C18 C 0.4544(7) 0.5860(12) 0.2040(10) 0.040(3) Uani 1 1 d . . . . .
H18 H 0.493866 0.624237 0.234256 0.048 Uiso 1 1 calc R U . . .
C19 C 0.3914(7) 0.6040(11) 0.2292(9) 0.041(3) Uani 1 1 d . . . . .
H19 H 0.388236 0.652201 0.279302 0.049 Uiso 1 1 calc R U . . .
C20 C 0.3342(7) 0.5517(11) 0.1815(9) 0.036(3) Uani 1 1 d . . . . .
H20 H 0.290985 0.564980 0.197138 0.043 Uiso 1 1 calc R U . . .
C21 C 0.3399(6) 0.4796(11) 0.1105(8) 0.031(3) Uani 1 1 d . . . . .
C22 C 0.2275(6) 0.4030(12) 0.1063(8) 0.036(3) Uani 1 1 d . . . . .
H22A H 0.243993 0.385839 0.174854 0.043 Uiso 1 1 calc R U . . .
H22B H 0.198456 0.467224 0.101655 0.043 Uiso 1 1 calc R U . . .
C23 C 0.1877(6) 0.3133(11) 0.0568(8) 0.032(3) Uani 1 1 d . . . . .
H23A H 0.216648 0.248874 0.063767 0.038 Uiso 1 1 calc R U . . .
H23B H 0.148089 0.298923 0.086795 0.038 Uiso 1 1 calc R U . . .
C24 C 0.2221(6) 0.3541(12) -0.0911(8) 0.037(3) Uani 1 1 d . . . . .
H24A H 0.205584 0.369502 -0.160011 0.044 Uiso 1 1 calc R U . . .
H24B H 0.250934 0.289512 -0.085283 0.044 Uiso 1 1 calc R U . . .
C25 C 0.2627(6) 0.4447(11) -0.0438(8) 0.033(3) Uani 1 1 d . . . . .
H25A H 0.234245 0.509732 -0.052104 0.040 Uiso 1 1 calc R U . . .
H25B H 0.302519 0.456982 -0.073768 0.040 Uiso 1 1 calc R U . . .
C26 C 0.0980(6) 0.3535(10) -0.0841(7) 0.026(2) Uani 1 1 d . . . . .
C27 C 0.0724(6) 0.3577(10) -0.1884(8) 0.029(3) Uani 1 1 d . . . . .
C28 C 0.0017(7) 0.3628(10) -0.2305(8) 0.032(3) Uani 1 1 d . . . . .
C29 C -0.0484(6) 0.3685(10) -0.1717(8) 0.030(3) Uani 1 1 d . . . . .
C30 C -0.0224(6) 0.3710(10) -0.0736(8) 0.030(3) Uani 1 1 d . . . . .
H30 H -0.054206 0.376435 -0.032687 0.036 Uiso 1 1 calc R U . . .
C31 C 0.0458(6) 0.3664(10) -0.0312(8) 0.029(3) Uani 1 1 d . . . . .
H31 H 0.058561 0.372021 0.036530 0.035 Uiso 1 1 calc R U . . .
C32 C 0.4123(7) 0.3723(12) 0.0271(10) 0.045(3) Uani 1 1 d . . . . .
H32A H 0.394225 0.394101 -0.039224 0.067 Uiso 1 1 calc R U . . .
H32B H 0.387933 0.308958 0.041741 0.067 Uiso 1 1 calc R U . . .
H32C H 0.461166 0.356221 0.035184 0.067 Uiso 1 1 calc R U . . .
I1 I 0.39053(5) 0.81278(8) 0.42652(6) 0.0421(3) Uani 1 1 d . . . . .
I2 I 0.35245(5) 0.18066(9) 0.23723(6) 0.0490(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 N4 1.368(12) . ?
O1 N5 1.373(13) . ?
O2 N6 1.247(13) . ?
O3 N6 1.215(13) . ?
N1 C1 1.37(2) . ?
N1 C5 1.341(17) . ?
N1 C16 1.489(18) . ?
N2 C5 1.349(19) . ?
N2 C6 1.459(15) . ?
N2 C9 1.469(17) . ?
N3 C7 1.480(16) . ?
N3 C8 1.484(13) . ?
N3 C10 1.321(16) . ?
N4 C11 1.321(16) . ?
N5 C12 1.317(15) . ?
N6 C13 1.418(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.37(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.39(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.36(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.41(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.496(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.488(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.452(16) . ?
C10 C15 1.416(17) . ?
C11 C12 1.422(17) . ?
C12 C13 1.426(16) . ?
C13 C14 1.382(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(17) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O4 N10 1.377(13) . ?
O4 N11 1.401(13) . ?
O5 N12 1.217(13) . ?
O6 N12 1.241(13) . ?
N7 C17 1.358(16) . ?
N7 C21 1.378(14) . ?
N7 C32 1.437(17) . ?
N8 C21 1.368(15) . ?
N8 C22 1.490(14) . ?
N8 C25 1.481(14) . ?
N9 C23 1.458(14) . ?
N9 C24 1.479(14) . ?
N9 C26 1.330(15) . ?
N10 C27 1.342(15) . ?
N11 C28 1.316(15) . ?
N12 C29 1.414(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.35(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.40(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.374(18) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.475(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.480(18) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.471(15) . ?
C26 C31 1.417(14) . ?
C27 C28 1.417(17) . ?
C28 C29 1.434(16) . ?
C29 C30 1.390(16) . ?
C30 H30 0.9500 . ?
C30 C31 1.374(17) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
N4 O1 N5 112.6(8) . . ?
C1 N1 C16 116.9(13) . . ?
C5 N1 C1 120.8(14) . . ?
C5 N1 C16 122.1(13) . . ?
C5 N2 C6 122.0(12) . . ?
C5 N2 C9 121.3(11) . . ?
C6 N2 C9 110.2(11) . . ?
C7 N3 C8 112.4(10) . . ?
C10 N3 C7 123.2(10) . . ?
C10 N3 C8 120.1(10) . . ?
C11 N4 O1 104.6(10) . . ?
C12 N5 O1 104.7(9) . . ?
O2 N6 C13 117.1(10) . . ?
O3 N6 O2 122.3(11) . . ?
O3 N6 C13 120.5(10) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 120.9(16) . . ?
C2 C1 H1 119.5 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.9(16) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(16) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(16) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 N2 118.7(13) . . ?
N1 C5 C4 118.4(14) . . ?
N2 C5 C4 122.8(14) . . ?
N2 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
N2 C6 C7 109.8(11) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
N3 C7 C6 111.7(11) . . ?
N3 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N3 C8 H8A 109.7 . . ?
N3 C8 H8B 109.7 . . ?
N3 C8 C9 109.9(10) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
N2 C9 C8 113.1(11) . . ?
N2 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N3 C10 C11 122.6(11) . . ?
N3 C10 C15 123.6(11) . . ?
C15 C10 C11 113.7(11) . . ?
N4 C11 C10 128.4(12) . . ?
N4 C11 C12 109.1(10) . . ?
C12 C11 C10 122.4(11) . . ?
N5 C12 C11 108.9(11) . . ?
N5 C12 C13 131.0(11) . . ?
C11 C12 C13 120.0(11) . . ?
N6 C13 C12 122.6(10) . . ?
C14 C13 N6 120.0(11) . . ?
C14 C13 C12 117.3(11) . . ?
C13 C14 H14 118.6 . . ?
C15 C14 C13 122.9(11) . . ?
C15 C14 H14 118.6 . . ?
C10 C15 H15 118.2 . . ?
C14 C15 C10 123.6(11) . . ?
C14 C15 H15 118.2 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N10 O4 N11 113.3(8) . . ?
C17 N7 C21 118.7(11) . . ?
C17 N7 C32 119.5(11) . . ?
C21 N7 C32 121.8(11) . . ?
C21 N8 C22 116.8(9) . . ?
C21 N8 C25 118.9(10) . . ?
C25 N8 C22 110.8(9) . . ?
C23 N9 C24 110.1(9) . . ?
C26 N9 C23 123.4(9) . . ?
C26 N9 C24 125.9(10) . . ?
C27 N10 O4 103.3(9) . . ?
C28 N11 O4 103.5(10) . . ?
O5 N12 O6 123.6(11) . . ?
O5 N12 C29 118.3(11) . . ?
O6 N12 C29 118.0(10) . . ?
N7 C17 H17 118.7 . . ?
C18 C17 N7 122.6(12) . . ?
C18 C17 H17 118.7 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.9(13) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(13) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.5(12) . . ?
C21 C20 H20 120.2 . . ?
N7 C21 C20 120.2(11) . . ?
N8 C21 N7 115.3(11) . . ?
N8 C21 C20 124.4(11) . . ?
N8 C22 H22A 110.1 . . ?
N8 C22 H22B 110.1 . . ?
H22A C22 H22B 108.4 . . ?
C23 C22 N8 108.0(10) . . ?
C23 C22 H22A 110.1 . . ?
C23 C22 H22B 110.1 . . ?
N9 C23 C22 110.9(10) . . ?
N9 C23 H23A 109.5 . . ?
N9 C23 H23B 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.0 . . ?
N9 C24 H24A 110.0 . . ?
N9 C24 H24B 110.0 . . ?
N9 C24 C25 108.7(10) . . ?
H24A C24 H24B 108.3 . . ?
C25 C24 H24A 110.0 . . ?
C25 C24 H24B 110.0 . . ?
N8 C25 H25A 109.7 . . ?
N8 C25 H25B 109.7 . . ?
C24 C25 N8 109.9(10) . . ?
C24 C25 H25A 109.7 . . ?
C24 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
N9 C26 C27 122.9(10) . . ?
N9 C26 C31 123.9(10) . . ?
C31 C26 C27 113.2(10) . . ?
N10 C27 C26 127.6(11) . . ?
N10 C27 C28 109.6(10) . . ?
C28 C27 C26 122.7(10) . . ?
N11 C28 C27 110.1(11) . . ?
N11 C28 C29 129.3(12) . . ?
C27 C28 C29 120.6(11) . . ?
N12 C29 C28 122.5(11) . . ?
C30 C29 N12 122.1(11) . . ?
C30 C29 C28 115.4(11) . . ?
C29 C30 H30 117.5 . . ?
C31 C30 C29 125.1(11) . . ?
C31 C30 H30 117.5 . . ?
C26 C31 H31 118.6 . . ?
C30 C31 C26 122.8(10) . . ?
C30 C31 H31 118.6 . . ?
N7 C32 H32A 109.5 . . ?
N7 C32 H32B 109.5 . . ?
N7 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N4 C11 C10 178.7(13) . . . . ?
O1 N4 C11 C12 0.9(14) . . . . ?
O1 N5 C12 C11 -0.7(13) . . . . ?
O1 N5 C12 C13 -177.3(12) . . . . ?
O2 N6 C13 C12 -1.7(17) . . . . ?
O2 N6 C13 C14 174.6(11) . . . . ?
O3 N6 C13 C12 179.5(11) . . . . ?
O3 N6 C13 C14 -4.2(18) . . . . ?
N1 C1 C2 C3 2(2) . . . . ?
N2 C6 C7 N3 -56.8(17) . . . . ?
N3 C8 C9 N2 53.9(16) . . . . ?
N3 C10 C11 N4 0(2) . . . . ?
N3 C10 C11 C12 177.6(12) . . . . ?
N3 C10 C15 C14 -178.1(13) . . . . ?
N4 O1 N5 C12 1.3(13) . . . . ?
N4 C11 C12 N5 -0.1(15) . . . . ?
N4 C11 C12 C13 176.9(11) . . . . ?
N5 O1 N4 C11 -1.4(13) . . . . ?
N5 C12 C13 N6 -6(2) . . . . ?
N5 C12 C13 C14 177.6(13) . . . . ?
N6 C13 C14 C15 -178.4(11) . . . . ?
C1 N1 C5 N2 172.6(12) . . . . ?
C1 N1 C5 C4 -10.0(19) . . . . ?
C1 C2 C3 C4 -5(2) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 N1 7(2) . . . . ?
C3 C4 C5 N2 -176.0(13) . . . . ?
C5 N1 C1 C2 6(2) . . . . ?
C5 N2 C6 C7 -93.6(15) . . . . ?
C5 N2 C9 C8 93.6(14) . . . . ?
C6 N2 C5 N1 -54.4(18) . . . . ?
C6 N2 C5 C4 128.4(15) . . . . ?
C6 N2 C9 C8 -58.5(16) . . . . ?
C7 N3 C8 C9 -51.2(16) . . . . ?
C7 N3 C10 C11 33(2) . . . . ?
C7 N3 C10 C15 -151.1(13) . . . . ?
C8 N3 C7 C6 53.8(16) . . . . ?
C8 N3 C10 C11 -172.3(13) . . . . ?
C8 N3 C10 C15 4(2) . . . . ?
C9 N2 C5 N1 156.8(12) . . . . ?
C9 N2 C5 C4 -20(2) . . . . ?
C9 N2 C6 C7 58.3(17) . . . . ?
C10 N3 C7 C6 -149.6(13) . . . . ?
C10 N3 C8 C9 151.4(13) . . . . ?
C10 C11 C12 N5 -178.2(12) . . . . ?
C10 C11 C12 C13 -1.1(19) . . . . ?
C11 C10 C15 C14 -1.8(19) . . . . ?
C11 C12 C13 N6 177.7(11) . . . . ?
C11 C12 C13 C14 1.4(17) . . . . ?
C12 C13 C14 C15 -1.9(18) . . . . ?
C13 C14 C15 C10 2(2) . . . . ?
C15 C10 C11 N4 -176.4(13) . . . . ?
C15 C10 C11 C12 1.2(19) . . . . ?
C16 N1 C1 C2 -170.3(13) . . . . ?
C16 N1 C5 N2 -11.6(19) . . . . ?
C16 N1 C5 C4 165.8(13) . . . . ?
O4 N10 C27 C26 178.1(11) . . . . ?
O4 N10 C27 C28 3.2(13) . . . . ?
O4 N11 C28 C27 0.2(14) . . . . ?
O4 N11 C28 C29 -179.8(12) . . . . ?
O5 N12 C29 C28 -4.3(19) . . . . ?
O5 N12 C29 C30 177.0(12) . . . . ?
O6 N12 C29 C28 173.0(12) . . . . ?
O6 N12 C29 C30 -5.7(18) . . . . ?
N7 C17 C18 C19 -0.1(19) . . . . ?
N8 C22 C23 N9 -59.2(13) . . . . ?
N9 C24 C25 N8 58.8(13) . . . . ?
N9 C26 C27 N10 -2(2) . . . . ?
N9 C26 C27 C28 172.2(12) . . . . ?
N9 C26 C31 C30 -172.0(12) . . . . ?
N10 O4 N11 C28 1.9(13) . . . . ?
N10 C27 C28 N11 -2.2(15) . . . . ?
N10 C27 C28 C29 177.7(11) . . . . ?
N11 O4 N10 C27 -3.2(13) . . . . ?
N11 C28 C29 N12 3(2) . . . . ?
N11 C28 C29 C30 -178.6(13) . . . . ?
N12 C29 C30 C31 177.3(12) . . . . ?
C17 N7 C21 N8 177.5(10) . . . . ?
C17 N7 C21 C20 -6.1(17) . . . . ?
C17 C18 C19 C20 -3(2) . . . . ?
C18 C19 C20 C21 2(2) . . . . ?
C19 C20 C21 N7 3.0(19) . . . . ?
C19 C20 C21 N8 179.0(12) . . . . ?
C21 N7 C17 C18 4.7(18) . . . . ?
C21 N8 C22 C23 -161.5(11) . . . . ?
C21 N8 C25 C24 161.4(11) . . . . ?
C22 N8 C21 N7 151.2(11) . . . . ?
C22 N8 C21 C20 -25.0(18) . . . . ?
C22 N8 C25 C24 -59.1(14) . . . . ?
C23 N9 C24 C25 -59.9(14) . . . . ?
C23 N9 C26 C27 -168.5(11) . . . . ?
C23 N9 C26 C31 10(2) . . . . ?
C24 N9 C23 C22 61.4(13) . . . . ?
C24 N9 C26 C27 21(2) . . . . ?
C24 N9 C26 C31 -160.6(12) . . . . ?
C25 N8 C21 N7 -71.7(15) . . . . ?
C25 N8 C21 C20 112.2(14) . . . . ?
C25 N8 C22 C23 58.1(14) . . . . ?
C26 N9 C23 C22 -110.3(13) . . . . ?
C26 N9 C24 C25 111.4(13) . . . . ?
C26 C27 C28 N11 -177.5(11) . . . . ?
C26 C27 C28 C29 2.5(19) . . . . ?
C27 C26 C31 C30 6.4(18) . . . . ?
C27 C28 C29 N12 -177.2(12) . . . . ?
C27 C28 C29 C30 1.5(18) . . . . ?
C28 C29 C30 C31 -1.4(19) . . . . ?
C29 C30 C31 C26 -3(2) . . . . ?
C31 C26 C27 N10 179.4(12) . . . . ?
C31 C26 C27 C28 -6.2(17) . . . . ?
C32 N7 C17 C18 -172.8(12) . . . . ?
C32 N7 C21 N8 -5.0(17) . . . . ?
C32 N7 C21 C20 171.4(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.836(4)
2 0.164(4)

