# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_pyrimethanilhemicocrystal_10k_sxd
_database_code_depnum_ccdc_archive 'CCDC 2385127'
loop_
_audit_author_name
_audit_author_address
'Claire Wilson'
;University of Glasgow
United Kingdom
;
_audit_update_record             
;
2024-09-19 deposited with the CCDC.	2025-11-06 downloaded from the CCDC.
;
_audit_creation_date             2024-06-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C28 H32 N6 O6)'
_chemical_formula_sum            'C112 H128 N24 O24'
_chemical_formula_weight         2194.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
H H 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
N N 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
C C 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'

_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   18.791(3)
_cell_length_b                   16.407(2)
_cell_length_c                   8.6453(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2665.4(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    283.15
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.045
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1388
_diffrn_reflns_Laue_measured_fraction_full 0.667
_diffrn_reflns_Laue_measured_fraction_max 0.160
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18634
_diffrn_reflns_point_group_measured_fraction_full 0.634
_diffrn_reflns_point_group_measured_fraction_max 0.133
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         88.133
_diffrn_reflns_theta_min         8.926
_diffrn_ambient_temperature      283.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.667
_diffrn_measured_fraction_theta_max 0.160
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           neutrons
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.553
_reflns_Friedel_fraction_full    0.590
_reflns_Friedel_fraction_max     0.102
_reflns_number_gt                17642
_reflns_number_total             18634
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         3.904
_refine_diff_density_min         -1.944
_refine_diff_density_rms         0.446
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       0.00013(2)
_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   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         18634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0957
_refine_ls_restrained_S_all      1.045
_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)+(0.1688P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2279
_refine_ls_wR_factor_ref         0.2343
_refine_special_details          ?
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: -37.2(4)
 3.45(11) 0.76(4) 2.84(9) 0.72(3) 2.59(9) 0.95(4) 3.15(10) 1.08(4) 3.25(11)
 4.71(15) 3.24(11) 2.42(8) 4.16(13) 4.89(16)
2. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O2A)
Uanis(O1B) = Uanis(O2B)
Uiso(O3A) = Uiso(O3AB)
Uiso(H3AA) = Uiso(H3AB)
Uiso(H14A) = Uiso(H14B)
Uanis(C13A) = Uanis(C14A)
Uanis(C13B) = Uanis(C14B)
Uanis(N1A) = Uanis(N2A) = Uanis(N3A)
Uanis(N1B) = Uanis(N2B) = Uanis(N3B)
Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A) = Uanis(C6A)
Uanis(C1B) = Uanis(C2B) = Uanis(C3B) = Uanis(C4B) = Uanis(C5B) = Uanis(C6B)
Uanis(C7A) = Uanis(C8A) = Uanis(C9A) = Uanis(C10A) = Uanis(C11A) = Uanis(C12A)
Uanis(C7B) = Uanis(C8B) = Uanis(C9B) = Uanis(C10B) = Uanis(C11B) = Uanis(C12B)
3. Others
 Sof(O3AB)=Sof(H3AB)=Sof(H14B)=1-FVAR(1)
 Sof(O3A)=Sof(H3AA)=Sof(H14A)=FVAR(1)
 Sof(H2B)=1-FVAR(2)
 Sof(H1B)=FVAR(2)
 Fixed Sof: H2A(0.5) H2AA(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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
O1A O 0.4200(6) 0.8853(6) 0.5798(16) 0.0121(18) Uani 1 1 d . . . . .
O2A O 0.4415(6) 0.8606(6) 0.8293(17) 0.0121(18) Uani 1 1 d . . . . .
O3A O 0.5523(11) 0.9622(13) 0.851(3) 0.004(3) Uiso 0.51(2) 1 d . . P . .
H3AA H 0.542(3) 0.915(4) 0.915(9) 0.020(7) Uiso 0.51(2) 1 d . . P . .
O3AB O 0.5710(10) 0.9319(12) 0.796(3) 0.004(3) Uiso 0.49(2) 1 d . . P . .
H3AB H 0.550(4) 0.925(5) 0.899(10) 0.020(7) Uiso 0.49(2) 1 d . . P . .
N1A N 0.3766(3) 0.7216(4) 0.5762(10) 0.0075(9) Uani 1 1 d . . . . .
H1A H 0.3905(10) 0.7817(11) 0.576(3) 0.016(5) Uani 1 1 d . . . . .
N2A N 0.3398(4) 0.7528(4) 0.8202(11) 0.0075(9) Uani 1 1 d . . . . .
N3A N 0.3062(4) 0.6260(4) 0.7088(10) 0.0075(9) Uani 1 1 d . . . . .
C1A C 0.4224(5) 0.7248(5) 0.3200(14) 0.0075(8) Uani 1 1 d . . . . .
H1AA H 0.4240(12) 0.7905(11) 0.330(3) 0.021(5) Uani 1 1 d . . . . .
C2A C 0.4450(5) 0.6888(5) 0.1841(14) 0.0075(8) Uani 1 1 d . . . . .
H2AB H 0.4637(11) 0.7258(12) 0.091(3) 0.020(5) Uani 1 1 d . . . . .
C3A C 0.4433(5) 0.6035(5) 0.1682(15) 0.0075(8) Uani 1 1 d . . . . .
H3A H 0.4610(13) 0.5756(13) 0.063(3) 0.023(5) Uani 1 1 d . . . . .
C4A C 0.4185(5) 0.5567(5) 0.2921(14) 0.0075(8) Uani 1 1 d . . . . .
H4A H 0.4165(14) 0.4901(13) 0.281(3) 0.024(6) Uani 1 1 d . . . . .
C5A C 0.3945(5) 0.5928(5) 0.4286(15) 0.0075(8) Uani 1 1 d . . . . .
H5A H 0.3739(14) 0.5560(14) 0.522(3) 0.026(6) Uani 1 1 d . . . . .
C6A C 0.3968(5) 0.6777(5) 0.4425(14) 0.0075(8) Uani 1 1 d . . . . .
C7A C 0.3400(5) 0.6972(5) 0.7035(13) 0.0065(8) Uani 1 1 d . . . . .
C8A C 0.2678(5) 0.6102(5) 0.8360(14) 0.0065(8) Uani 1 1 d . . . . .
C9A C 0.2624(5) 0.6653(5) 0.9597(15) 0.0065(8) Uani 1 1 d . . . . .
H9A H 0.2316(12) 0.6522(12) 1.058(3) 0.022(5) Uani 1 1 d . . . . .
C10A C 0.3003(5) 0.7384(5) 0.9477(14) 0.0065(8) Uani 1 1 d . . . . .
C11A C 0.2292(5) 0.5303(5) 0.8404(15) 0.0065(8) Uani 1 1 d . . . . .
H11A H 0.1823(16) 0.5351(17) 0.772(6) 0.062(14) Uani 1 1 d . . . . .
H11B H 0.214(3) 0.513(2) 0.952(5) 0.095(18) Uani 1 1 d . . . . .
H11C H 0.2600(16) 0.4838(14) 0.796(5) 0.048(10) Uani 1 1 d . . . . .
C12A C 0.2978(5) 0.8045(5) 1.0667(15) 0.0065(8) Uani 1 1 d . . . . .
H12A H 0.3456(12) 0.8414(15) 1.063(4) 0.033(7) Uani 1 1 d . . . . .
H12B H 0.2913(17) 0.7777(15) 1.183(4) 0.038(7) Uani 1 1 d . . . . .
H12C H 0.2543(14) 0.8415(17) 1.045(4) 0.044(9) Uani 1 1 d . . . . .
C13A C 0.4539(5) 0.8965(6) 0.6996(15) 0.0104(16) Uani 1 1 d . . . . .
C14A C 0.5156(5) 0.9568(6) 0.7004(15) 0.0104(16) Uani 1 1 d . . . . .
H14A H 0.542(3) 0.949(4) 0.574(8) 0.016(6) Uiso 0.51(2) 1 d . . P . .
H14B H 0.547(4) 0.948(4) 0.605(8) 0.016(6) Uiso 0.49(2) 1 d . . P . .
O1B O 0.5761(5) 0.8761(6) 0.3498(15) 0.0059(15) Uani 1 1 d . . . . .
H1B H 0.610(3) 0.827(4) 0.334(5) 0.011(14) Uani 0.51(18) 1 d . . P . .
O2B O 0.5485(5) 0.8601(6) 0.1009(14) 0.0059(15) Uani 1 1 d . . . . .
O3B O 0.4294(5) 0.9505(6) 0.1308(17) 0.007(2) Uani 1 1 d . . . . .
H3B H 0.4479(14) 0.936(3) 0.041(4) 0.064(11) Uani 1 1 d . . . . .
N1B N 0.6172(3) 0.7098(4) 0.0901(9) 0.0050(8) Uani 1 1 d . . . . .
H1BA H 0.5949(12) 0.7684(11) 0.095(3) 0.022(5) Uani 1 1 d . . . . .
N2B N 0.6569(4) 0.7440(4) 0.3312(10) 0.0050(8) Uani 1 1 d . . . . .
N3B N 0.6907(4) 0.6173(4) 0.2200(9) 0.0050(8) Uani 1 1 d . . . . .
C1B C 0.5690(5) 0.7127(5) -0.1644(14) 0.0065(8) Uani 1 1 d . . . . .
H1BB H 0.5613(12) 0.7780(11) -0.148(3) 0.022(5) Uani 1 1 d . . . . .
C2B C 0.5483(5) 0.6758(5) -0.3028(14) 0.0065(8) Uani 1 1 d . . . . .
H2BA H 0.5240(13) 0.7131(13) -0.394(3) 0.026(6) Uani 1 1 d . . . . .
C3B C 0.5574(5) 0.5916(5) -0.3225(15) 0.0065(8) Uani 1 1 d . . . . .
H3BA H 0.5391(13) 0.5633(12) -0.428(3) 0.026(6) Uani 1 1 d . . . . .
C4B C 0.5871(5) 0.5457(5) -0.2043(13) 0.0065(8) Uani 1 1 d . . . . .
H4B H 0.5936(15) 0.4817(13) -0.219(3) 0.026(6) Uani 1 1 d . . . . .
C5B C 0.6087(5) 0.5820(5) -0.0655(14) 0.0065(8) Uani 1 1 d . . . . .
H5B H 0.6325(13) 0.5461(13) 0.025(3) 0.025(6) Uani 1 1 d . . . . .
C6B C 0.6000(5) 0.6664(5) -0.0453(14) 0.0065(8) Uani 1 1 d . . . . .
C7B C 0.6558(5) 0.6877(5) 0.2153(14) 0.0073(9) Uani 1 1 d . . . . .
C8B C 0.7292(5) 0.6009(5) 0.3472(15) 0.0073(9) Uani 1 1 d . . . . .
C9B C 0.7325(5) 0.6555(5) 0.4699(15) 0.0073(9) Uani 1 1 d . . . . .
H9B H 0.7640(12) 0.6421(12) 0.572(3) 0.022(5) Uani 1 1 d . . . . .
C10B C 0.6956(5) 0.7282(5) 0.4573(14) 0.0073(9) Uani 1 1 d . . . . .
C11B C 0.7686(6) 0.5215(5) 0.3480(15) 0.0073(9) Uani 1 1 d . . . . .
H11D H 0.7345(14) 0.4727(14) 0.312(5) 0.043(9) Uani 1 1 d . . . . .
H11E H 0.7941(17) 0.5090(17) 0.458(4) 0.046(8) Uani 1 1 d . . . . .
H11F H 0.8125(16) 0.5224(17) 0.264(4) 0.044(9) Uani 1 1 d . . . . .
C12B C 0.6977(5) 0.7929(5) 0.5795(15) 0.0073(9) Uani 1 1 d . . . . .
H12D H 0.7440(16) 0.827(2) 0.568(5) 0.055(11) Uani 1 1 d . . . . .
H12E H 0.699(2) 0.7678(16) 0.692(4) 0.044(8) Uani 1 1 d . . . . .
H12F H 0.6526(17) 0.8330(16) 0.575(4) 0.044(8) Uani 1 1 d . . . . .
C13B C 0.5396(5) 0.8931(5) 0.2280(13) 0.0050(14) Uani 1 1 d . . . . .
C14B C 0.4821(5) 0.9583(6) 0.2476(13) 0.0050(14) Uani 1 1 d . . . . .
H14C H 0.4562(10) 0.9480(12) 0.358(3) 0.016(5) Uani 1 1 d . . . . .
H2B H 0.625(4) 0.800(6) 0.331(8) 0.023(16) Uiso 0.49(18) 1 d . . P . .
H2A H 0.401(2) 0.817(2) 0.812(6) 0.011(8) Uiso 0.5 1 d . . P A 2
H2AA H 0.377(3) 0.804(3) 0.825(7) 0.014(9) Uiso 0.5 1 d . . P . .


_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
O1A C13A 1.230(17) . ?
O2A C13A 1.288(18) . ?
O2A H2A 1.06(4) . ?
O3A H3AA 0.97(6) . ?
O3A O3AB 0.77(3) . ?
O3A H3AB 0.75(9) . ?
O3A C14A 1.47(3) . ?
H3AA O3AB 1.20(7) . ?
O3AB H3AA 1.20(7) . ?
O3AB H3AB 0.98(9) . ?
O3AB C14A 1.39(2) . ?
N1A H1A 1.02(2) . ?
N1A C6A 1.414(14) . ?
N1A C7A 1.358(14) . ?
N2A C7A 1.360(13) . ?
N2A C10A 1.349(14) . ?
N2A H2AA 1.09(5) . ?
N3A C7A 1.330(12) . ?
N3A C8A 1.340(14) . ?
C1A H1AA 1.08(2) . ?
C1A C2A 1.382(16) . ?
C1A C6A 1.397(16) . ?
C2A H2AB 1.07(3) . ?
C2A C3A 1.406(13) . ?
C3A H3A 1.07(3) . ?
C3A C4A 1.398(15) . ?
C4A H4A 1.10(2) . ?
C4A C5A 1.395(16) . ?
C5A H5A 1.08(3) . ?
C5A C6A 1.398(13) . ?
C8A C9A 1.405(16) . ?
C8A C11A 1.498(13) . ?
C9A H9A 1.05(3) . ?
C9A C10A 1.399(13) . ?
C10A C12A 1.495(15) . ?
C11A H11A 1.07(3) . ?
C11A H11B 1.04(4) . ?
C11A H11C 1.03(3) . ?
C12A H12A 1.08(2) . ?
C12A H12B 1.11(4) . ?
C12A H12C 1.03(3) . ?
C13A C14A 1.525(13) . ?
C14A C14A 1.53(2) 2_675 ?
C14A H14A 1.21(7) . ?
C14A H14B 1.03(8) . ?
O1B H1B 1.03(8) . ?
O1B C13B 1.286(16) . ?
H1B H2B 0.53(6) . ?
O2B C13B 1.236(15) . ?
O3B H3B 0.88(4) . ?
O3B C14B 1.421(16) . ?
N1B H1BA 1.05(2) . ?
N1B C6B 1.408(14) . ?
N1B C7B 1.351(14) . ?
N2B C7B 1.363(13) . ?
N2B C10B 1.336(14) . ?
N2B H2B 1.10(11) . ?
N3B C7B 1.329(12) . ?
N3B C8B 1.343(14) . ?
C1B H1BB 1.09(2) . ?
C1B C2B 1.396(16) . ?
C1B C6B 1.407(15) . ?
C2B H2BA 1.10(3) . ?
C2B C3B 1.402(12) . ?
C3B H3BA 1.08(3) . ?
C3B C4B 1.387(15) . ?
C4B H4B 1.06(2) . ?
C4B C5B 1.400(16) . ?
C5B H5B 1.08(3) . ?
C5B C6B 1.404(13) . ?
C8B C9B 1.389(16) . ?
C8B C11B 1.499(13) . ?
C9B H9B 1.09(3) . ?
C9B C10B 1.384(13) . ?
C10B C12B 1.499(16) . ?
C11B H11D 1.07(3) . ?
C11B H11E 1.09(4) . ?
C11B H11F 1.10(3) . ?
C12B H12D 1.04(3) . ?
C12B H12E 1.05(4) . ?
C12B H12F 1.07(3) . ?
C13B C14B 1.529(13) . ?
C14B C14B 1.525(19) 2_675 ?
C14B H14C 1.09(3) . ?
H2B H1B 0.53(6) . ?
H2A H2AA 0.51(5) . ?
H2AA H2A 0.51(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H2A O2A C13A 109(3) . . ?
H3AA O3A C14A 111(5) . . ?
O3AB O3A H3AA 86(5) . . ?
O3AB O3A C14A 68(3) . . ?
H3AB O3A H3AA 8(9) . . ?
H3AB O3A O3AB 81(7) . . ?
H3AB O3A C14A 114(7) . . ?
O3A H3AA O3AB 40(3) . . ?
O3A O3AB H3AA 54(4) . . ?
O3A O3AB H3AB 48(6) . . ?
O3A O3AB C14A 80(3) . . ?
H3AA O3AB C14A 104(4) . . ?
H3AB O3AB H3AA 7(7) . . ?
H3AB O3AB C14A 106(5) . . ?
O3A H3AB O3AB 51(5) . . ?
H1A N1A C6A 114.9(16) . . ?
H1A N1A C7A 114.7(15) . . ?
C7A N1A C6A 130.4(7) . . ?
C10A N2A C7A 119.4(8) . . ?
H2AA N2A C7A 123(3) . . ?
H2AA N2A C10A 117(3) . . ?
C7A N3A C8A 117.1(9) . . ?
H1AA C1A C2A 119.0(17) . . ?
H1AA C1A C6A 120.1(17) . . ?
C2A C1A C6A 120.9(9) . . ?
C1A C2A C3A 120.1(10) . . ?
H2AB C2A C1A 119.9(15) . . ?
H2AB C2A C3A 120.0(16) . . ?
H3A C3A C2A 120.0(15) . . ?
H3A C3A C4A 121.3(15) . . ?
C4A C3A C2A 118.6(11) . . ?
H4A C4A C3A 119.4(17) . . ?
H4A C4A C5A 119.1(17) . . ?
C5A C4A C3A 121.5(9) . . ?
C4A C5A C6A 119.1(10) . . ?
H5A C5A C4A 120.8(15) . . ?
H5A C5A C6A 120.1(16) . . ?
C1A C6A N1A 115.5(8) . . ?
C1A C6A C5A 119.8(11) . . ?
C5A C6A N1A 124.7(10) . . ?
N1A C7A N2A 113.9(8) . . ?
N3A C7A N1A 121.9(9) . . ?
N3A C7A N2A 124.2(10) . . ?
N3A C8A C9A 122.6(8) . . ?
N3A C8A C11A 116.8(9) . . ?
C9A C8A C11A 120.6(10) . . ?
H9A C9A C8A 121.6(14) . . ?
H9A C9A C10A 121.1(16) . . ?
C10A C9A C8A 117.3(11) . . ?
N2A C10A C9A 119.4(10) . . ?
N2A C10A C12A 116.9(8) . . ?
C9A C10A C12A 123.7(11) . . ?
H11A C11A C8A 108.8(17) . . ?
H11B C11A C8A 113(2) . . ?
H11B C11A H11A 108(4) . . ?
H11C C11A C8A 111.5(18) . . ?
H11C C11A H11A 108(3) . . ?
H11C C11A H11B 107(4) . . ?
H12A C12A C10A 111.0(18) . . ?
H12A C12A H12B 110(3) . . ?
H12B C12A C10A 110.0(15) . . ?
H12C C12A C10A 109.0(19) . . ?
H12C C12A H12A 109(2) . . ?
H12C C12A H12B 108(3) . . ?
O1A C13A O2A 124.8(11) . . ?
O1A C13A C14A 119.7(11) . . ?
O2A C13A C14A 115.6(11) . . ?
O3A C14A C13A 113.5(12) . . ?
O3A C14A C14A 97.1(10) . 2_675 ?
O3AB C14A O3A 31.2(12) . . ?
O3AB C14A C13A 112.4(11) . . ?
O3AB C14A C14A 124.0(12) . 2_675 ?
C13A C14A C14A 108.0(10) . 2_675 ?
H14A C14A O3A 128(3) . . ?
H14A C14A O3AB 101(3) . . ?
H14A C14A C13A 104(3) . . ?
H14A C14A C14A 105(3) . 2_675 ?
H14B C14A O3A 117(4) . . ?
H14B C14A O3AB 90(4) . . ?
H14B C14A C13A 110(4) . . ?
H14B C14A C14A 111(4) . 2_675 ?
H14B C14A H14A 11(6) . . ?
H1B O1B C13B 113(3) . . ?
H2B H1B O1B 173(10) . . ?
H3B O3B C14B 111.9(19) . . ?
H1BA N1B C6B 114.0(16) . . ?
H1BA N1B C7B 115.2(17) . . ?
C7B N1B C6B 130.7(7) . . ?
C10B N2B C7B 118.5(8) . . ?
H2B N2B C7B 124(4) . . ?
H2B N2B C10B 117(4) . . ?
C7B N3B C8B 117.8(8) . . ?
H1BB C1B C2B 120.2(17) . . ?
H1BB C1B C6B 119.3(17) . . ?
C2B C1B C6B 120.5(8) . . ?
C1B C2B C3B 119.8(10) . . ?
H2BA C2B C1B 119.3(15) . . ?
H2BA C2B C3B 120.8(16) . . ?
H3BA C3B C2B 119.1(14) . . ?
H3BA C3B C4B 121.2(13) . . ?
C4B C3B C2B 119.6(11) . . ?
C3B C4B C5B 121.2(9) . . ?
H4B C4B C3B 119.7(19) . . ?
H4B C4B C5B 119.1(18) . . ?
C4B C5B C6B 119.5(10) . . ?
H5B C5B C4B 120.7(15) . . ?
H5B C5B C6B 119.8(17) . . ?
C1B C6B N1B 115.5(7) . . ?
C5B C6B N1B 125.1(10) . . ?
C5B C6B C1B 119.4(10) . . ?
N1B C7B N2B 114.5(8) . . ?
N3B C7B N1B 121.6(9) . . ?
N3B C7B N2B 123.9(10) . . ?
N3B C8B C9B 121.3(8) . . ?
N3B C8B C11B 116.3(10) . . ?
C9B C8B C11B 122.3(10) . . ?
H9B C9B C8B 121.0(14) . . ?
H9B C9B C10B 120.8(15) . . ?
C10B C9B C8B 118.2(11) . . ?
N2B C10B C9B 120.3(10) . . ?
N2B C10B C12B 116.9(8) . . ?
C9B C10B C12B 122.8(10) . . ?
H11D C11B C8B 110.6(16) . . ?
H11D C11B H11E 112(3) . . ?
H11D C11B H11F 106(3) . . ?
H11E C11B C8B 112.7(18) . . ?
H11E C11B H11F 104(3) . . ?
H11F C11B C8B 110.9(17) . . ?
H12D C12B C10B 110(2) . . ?
H12D C12B H12E 107(3) . . ?
H12D C12B H12F 109(3) . . ?
H12E C12B C10B 111.9(17) . . ?
H12E C12B H12F 107(3) . . ?
H12F C12B C10B 112.8(18) . . ?
O1B C13B C14B 116.0(9) . . ?
O2B C13B O1B 124.1(10) . . ?
O2B C13B C14B 120.0(10) . . ?
O3B C14B C13B 110.6(9) . . ?
O3B C14B C14B 112.8(8) . 2_675 ?
C14B C14B C13B 108.4(9) 2_675 . ?
H14C C14B O3B 107.4(14) . . ?
H14C C14B C13B 107.8(13) . . ?
H14C C14B C14B 109.7(12) . 2_675 ?
H1B H2B N2B 178(10) . . ?
H2AA H2A O2A 153(10) . . ?
H2A H2AA N2A 151(10) . . ?

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
O1A C13A C14A O3A -178.5(14) . . . . ?
O1A C13A C14A O3AB -144.6(15) . . . . ?
O1A C13A C14A C14A 75.0(11) . . . 2_675 ?
O1A C13A C14A H14A -36(3) . . . . ?
O1A C13A C14A H14B -46(4) . . . . ?
O2A C13A C14A O3A 1.6(16) . . . . ?
O2A C13A C14A O3AB 35.5(18) . . . . ?
O2A C13A C14A C14A -104.8(9) . . . 2_675 ?
O2A C13A C14A H14A 144(3) . . . . ?
O2A C13A C14A H14B 134(4) . . . . ?
O2A H2A H2AA N2A -161(9) . . . . ?
O3A H3AA O3AB H3AB 39(57) . . . . ?
O3A H3AA O3AB C14A -67(4) . . . . ?
O3A O3AB C14A C13A -99(2) . . . . ?
O3A O3AB C14A C14A 34(3) . . . 2_675 ?
O3A O3AB C14A H14A 151(4) . . . . ?
O3A O3AB C14A H14B 149(4) . . . . ?
H3AA O3A O3AB H3AB -6(10) . . . . ?
H3AA O3A O3AB C14A 115(4) . . . . ?
H3AA O3A H3AB O3AB 131(75) . . . . ?
H3AA O3A C14A O3AB -77(5) . . . . ?
H3AA O3A C14A C13A 18(5) . . . . ?
H3AA O3A C14A C14A 132(5) . . . 2_675 ?
H3AA O3A C14A H14A -113(6) . . . . ?
H3AA O3A C14A H14B -111(6) . . . . ?
H3AA O3AB H3AB O3A -137(62) . . . . ?
H3AA O3AB C14A O3A 49(4) . . . . ?
H3AA O3AB C14A C13A -50(4) . . . . ?
H3AA O3AB C14A C14A 83(4) . . . 2_675 ?
H3AA O3AB C14A H14A -160(5) . . . . ?
H3AA O3AB C14A H14B -162(5) . . . . ?
O3AB O3A C14A C13A 95(2) . . . . ?
O3AB O3A C14A C14A -152(2) . . . 2_675 ?
O3AB O3A C14A H14A -37(5) . . . . ?
O3AB O3A C14A H14B -35(5) . . . . ?
H3AB O3A H3AA O3AB -48(74) . . . . ?
H3AB O3A O3AB H3AA 6(10) . . . . ?
H3AB O3A O3AB C14A 121(6) . . . . ?
H3AB O3A C14A O3AB -68(7) . . . . ?
H3AB O3A C14A C13A 27(7) . . . . ?
H3AB O3A C14A C14A 140(6) . . . 2_675 ?
H3AB O3A C14A H14A -105(7) . . . . ?
H3AB O3A C14A H14B -103(8) . . . . ?
H3AB O3AB C14A O3A 42(6) . . . . ?
H3AB O3AB C14A C13A -57(5) . . . . ?
H3AB O3AB C14A C14A 76(5) . . . 2_675 ?
H3AB O3AB C14A H14A -167(6) . . . . ?
H3AB O3AB C14A H14B -169(6) . . . . ?
H1A N1A C6A C1A -9.7(18) . . . . ?
H1A N1A C6A C5A 168.5(16) . . . . ?
H1A N1A C7A N2A -11.5(18) . . . . ?
H1A N1A C7A N3A 166.5(15) . . . . ?
N2A C10A C12A H12A -27(2) . . . . ?
N2A C10A C12A H12B -149(2) . . . . ?
N2A C10A C12A H12C 92(2) . . . . ?
N3A C8A C9A H9A 179.4(18) . . . . ?
N3A C8A C9A C10A -1.4(14) . . . . ?
N3A C8A C11A H11A -78(3) . . . . ?
N3A C8A C11A H11B 161(4) . . . . ?
N3A C8A C11A H11C 41(3) . . . . ?
C1A C2A C3A H3A -179.8(18) . . . . ?
C1A C2A C3A C4A 0.0(15) . . . . ?
H1AA C1A C2A H2AB 0(2) . . . . ?
H1AA C1A C2A C3A -179.8(17) . . . . ?
H1AA C1A C6A N1A -2(2) . . . . ?
H1AA C1A C6A C5A 179.6(17) . . . . ?
C2A C1A C6A N1A 178.9(9) . . . . ?
C2A C1A C6A C5A 0.6(15) . . . . ?
C2A C3A C4A H4A 179.6(19) . . . . ?
C2A C3A C4A C5A 1.1(16) . . . . ?
H2AB C2A C3A H3A 0(3) . . . . ?
H2AB C2A C3A C4A -179.9(17) . . . . ?
C3A C4A C5A H5A 178.1(19) . . . . ?
C3A C4A C5A C6A -1.3(16) . . . . ?
H3A C3A C4A H4A -1(3) . . . . ?
H3A C3A C4A C5A -179.1(18) . . . . ?
C4A C5A C6A N1A -177.7(9) . . . . ?
C4A C5A C6A C1A 0.5(15) . . . . ?
H4A C4A C5A H5A 0(3) . . . . ?
H4A C4A C5A C6A -179.8(19) . . . . ?
H5A C5A C6A N1A 3(2) . . . . ?
H5A C5A C6A C1A -179.0(18) . . . . ?
C6A N1A C7A N2A 170.4(9) . . . . ?
C6A N1A C7A N3A -11.6(16) . . . . ?
C6A C1A C2A H2AB 179.1(17) . . . . ?
C6A C1A C2A C3A -0.8(15) . . . . ?
C7A N1A C6A C1A 168.4(9) . . . . ?
C7A N1A C6A C5A -13.4(17) . . . . ?
C7A N2A C10A C9A 2.1(13) . . . . ?
C7A N2A C10A C12A -175.6(8) . . . . ?
C7A N2A H2AA H2A -29(25) . . . . ?
C7A N3A C8A C9A 0.3(14) . . . . ?
C7A N3A C8A C11A 179.3(8) . . . . ?
C8A N3A C7A N1A -175.6(9) . . . . ?
C8A N3A C7A N2A 2.2(14) . . . . ?
C8A C9A C10A N2A 0.1(14) . . . . ?
C8A C9A C10A C12A 177.7(9) . . . . ?
C9A C8A C11A H11A 101(3) . . . . ?
C9A C8A C11A H11B -20(4) . . . . ?
C9A C8A C11A H11C -140(3) . . . . ?
C9A C10A C12A H12A 155(2) . . . . ?
C9A C10A C12A H12B 33(2) . . . . ?
C9A C10A C12A H12C -85(3) . . . . ?
H9A C9A C10A N2A 179.4(18) . . . . ?
H9A C9A C10A C12A -3(2) . . . . ?
C10A N2A C7A N1A 174.5(8) . . . . ?
C10A N2A C7A N3A -3.4(14) . . . . ?
C10A N2A H2AA H2A 141(23) . . . . ?
C11A C8A C9A H9A 0(2) . . . . ?
C11A C8A C9A C10A 179.6(9) . . . . ?
C13A O2A H2A H2AA -125(22) . . . . ?
C14A O3A H3AA O3AB 65(3) . . . . ?
C14A O3A O3AB H3AA -115(5) . . . . ?
C14A O3A O3AB H3AB -121(6) . . . . ?
C14A O3A H3AB O3AB 61(4) . . . . ?
C14A O3AB H3AB O3A -61(5) . . . . ?
O1B C13B C14B O3B -157.8(10) . . . . ?
O1B C13B C14B C14B 78.0(9) . . . 2_675 ?
O1B C13B C14B H14C -40.7(17) . . . . ?
H1B O1B C13B O2B -7(3) . . . . ?
H1B O1B C13B C14B 173(3) . . . . ?
O2B C13B C14B O3B 21.9(13) . . . . ?
O2B C13B C14B C14B -102.3(9) . . . 2_675 ?
O2B C13B C14B H14C 139.0(15) . . . . ?
H3B O3B C14B C13B -37(3) . . . . ?
H3B O3B C14B C14B 85(3) . . . 2_675 ?
H3B O3B C14B H14C -154(3) . . . . ?
H1BA N1B C6B C1B 12.7(18) . . . . ?
H1BA N1B C6B C5B -164.6(15) . . . . ?
H1BA N1B C7B N2B 2.6(18) . . . . ?
H1BA N1B C7B N3B -175.7(15) . . . . ?
N2B C10B C12B H12D -98(3) . . . . ?
N2B C10B C12B H12E 144(2) . . . . ?
N2B C10B C12B H12F 24(3) . . . . ?
N3B C8B C9B H9B -179.5(18) . . . . ?
N3B C8B C9B C10B -0.7(15) . . . . ?
N3B C8B C11B H11D -48(3) . . . . ?
N3B C8B C11B H11E -174(2) . . . . ?
N3B C8B C11B H11F 69(2) . . . . ?
C1B C2B C3B H3BA 177.4(17) . . . . ?
C1B C2B C3B C4B -0.3(14) . . . . ?
H1BB C1B C2B H2BA 0(3) . . . . ?
H1BB C1B C2B C3B -179.1(17) . . . . ?
H1BB C1B C6B N1B 1(2) . . . . ?
H1BB C1B C6B C5B 178.9(17) . . . . ?
C2B C1B C6B N1B -178.7(8) . . . . ?
C2B C1B C6B C5B -1.3(14) . . . . ?
C2B C3B C4B H4B 179(2) . . . . ?
C2B C3B C4B C5B -0.3(15) . . . . ?
H2BA C2B C3B H3BA -1(3) . . . . ?
H2BA C2B C3B C4B -178.9(18) . . . . ?
C3B C4B C5B H5B -179.0(18) . . . . ?
C3B C4B C5B C6B 0.1(15) . . . . ?
H3BA C3B C4B H4B 2(3) . . . . ?
H3BA C3B C4B C5B -177.9(18) . . . . ?
C4B C5B C6B N1B 177.8(9) . . . . ?
C4B C5B C6B C1B 0.7(15) . . . . ?
H4B C4B C5B H5B 1(3) . . . . ?
H4B C4B C5B C6B -180(2) . . . . ?
H5B C5B C6B N1B -3(2) . . . . ?
H5B C5B C6B C1B 179.8(18) . . . . ?
C6B N1B C7B N2B -175.2(9) . . . . ?
C6B N1B C7B N3B 6.6(16) . . . . ?
C6B C1B C2B H2BA 179.7(17) . . . . ?
C6B C1B C2B C3B 1.1(14) . . . . ?
C7B N1B C6B C1B -169.5(9) . . . . ?
C7B N1B C6B C5B 13.2(16) . . . . ?
C7B N2B C10B C9B -1.0(14) . . . . ?
C7B N2B C10B C12B 177.7(9) . . . . ?
C7B N3B C8B C9B 0.0(14) . . . . ?
C7B N3B C8B C11B -179.3(9) . . . . ?
C8B N3B C7B N1B 178.4(9) . . . . ?
C8B N3B C7B N2B 0.2(15) . . . . ?
C8B C9B C10B N2B 1.2(15) . . . . ?
C8B C9B C10B C12B -177.5(9) . . . . ?
C9B C8B C11B H11D 133(3) . . . . ?
C9B C8B C11B H11E 7(2) . . . . ?
C9B C8B C11B H11F -110(2) . . . . ?
C9B C10B C12B H12D 81(3) . . . . ?
C9B C10B C12B H12E -37(3) . . . . ?
C9B C10B C12B H12F -158(2) . . . . ?
H9B C9B C10B N2B 180.0(18) . . . . ?
H9B C9B C10B C12B 1(2) . . . . ?
C10B N2B C7B N1B -178.0(8) . . . . ?
C10B N2B C7B N3B 0.3(15) . . . . ?
C11B C8B C9B H9B 0(2) . . . . ?
C11B C8B C9B C10B 178.5(9) . . . . ?
H2B N2B C7B N1B 7(4) . . . . ?
H2B N2B C7B N3B -175(4) . . . . ?
H2B N2B C10B C9B 175(4) . . . . ?
H2B N2B C10B C12B -6(4) . . . . ?
H2A O2A C13A O1A 5(3) . . . . ?
H2A O2A C13A C14A -175(2) . . . . ?
H2AA N2A C7A N1A -16(3) . . . . ?
H2AA N2A C7A N3A 166(3) . . . . ?
H2AA N2A C10A C9A -168(3) . . . . ?
H2AA N2A C10A C12A 14(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 -37.2(4)
2 3.45(11)
3 0.76(4)
4 2.84(9)
5 0.72(3)
6 2.59(9)
7 0.95(4)
8 3.15(10)
9 1.08(4)
10 3.25(11)
11 4.71(15)
12 3.24(11)
13 2.42(8)
14 4.16(13)
15 4.89(16)

####################################################################### 
# 
# 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_cu_2021gu0033_150k
_database_code_depnum_ccdc_archive 'CCDC 2385128'
loop_
_audit_author_name
_audit_author_address
'Claire Wilson'
;University of Glasgow
United Kingdom
;
_audit_update_record             
;
2024-09-19 deposited with the CCDC.	2025-11-06 downloaded from the CCDC.
;
_audit_creation_date             2024-06-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT353_cu_2021gu0033_150k  
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.24 Ang.  
RESPONSE: this is refined position consistent with hydrogen positions
determined from single crystal neutron diffraction data suggesting
an asymmetric N...H...O hydrogen bond.
;
_vrf_PLAT355_cu_2021gu0033_150k  
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O6T      - H3A      .       1.22 Ang.  
RESPONSE: this is refined position consistent with hydrogen positions
determined from single crystal neutron diffraction data suggesting
an asymmetric N...H...O hydrogen bond.
;

_vrf_PLAT771_cu_2021gu0033_150k  
;
PROBLEM: Check   N-H Bond in CIF: N3A      --H3A       ..       1.43 Ang.  
RESPONSE: this is refined position consistent with hydrogen positions
determined from single crystal neutron diffraction data suggesting
an asymmetric N...H...O hydrogen bond.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '(C12 H13 N3)2, (C4 H6 O6)'
_chemical_formula_sum            'C28 H32 N6 O6'
_chemical_formula_weight         548.59
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   16.6004(7)
_cell_length_b                   18.6805(8)
_cell_length_c                   8.7346(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2708.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.191
_cell_measurement_theta_min      3.562
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0738 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.8668.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            23878
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         3.562
_diffrn_ambient_temperature      150
_diffrn_detector                 'charge integrating pixel array detector'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'INCOATEC I\ms 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4827
_reflns_number_total             4929
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.9-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         4929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.073
_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)+(0.0457P)²+0.3438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0782
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.97(18)
 0.03(18)
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, All C(H,H,H,H,H,H) groups, All O(H) groups
3. Others
 Sof(H4TA)=Sof(O1A)=Sof(H1A)=1-FVAR(1)
 Sof(O1)=Sof(H1)=Sof(H4T)=FVAR(1)
 Fixed Sof: H14A(0.5) H14B(0.5) H14C(0.5) H14D(0.5) H14E(0.5) H14F(0.5)
 H15A(0.5) H15B(0.5) H15C(0.5) H15D(0.5) H15E(0.5) H15F(0.5) H14G(0.5)
 H14H(0.5) H14I(0.5) H15G(0.5) H15H(0.5) H15I(0.5) H15J(0.5) H15K(0.5)
 H15L(0.5) H14J(0.5) H14K(0.5) H14L(0.5)
4.a Ternary CH refined with riding coordinates:
 C8T(H8T), C4T(H4T), C4T(H4TA)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C5A(H5A), C9A(H9A),
 C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A)
4.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14(H14D,H14E,H14F), C15(H15A,H15B,H15C), C15(H15D,H15E,
 H15F), C14A(H14G,H14H,H14I), C15A(H15G,H15H,H15I), C15A(H15J,H15K,H15L)
4.d Idealised tetrahedral OH refined as rotating group:
 O9T(H9T), O1(H1), O1A(H1A)
;
_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
C2 C 0.19808(10) 0.15774(9) 0.2168(2) 0.0249(3) Uani 1 1 d . . . . .
C4 C 0.24223(11) 0.20180(9) 0.4519(2) 0.0283(4) Uani 1 1 d . . . . .
C5 C 0.17124(12) 0.23971(10) 0.4644(2) 0.0316(4) Uani 1 1 d . . . . .
H5 H 0.161568 0.270169 0.549541 0.038 Uiso 1 1 calc R U . . .
C6 C 0.11406(11) 0.23206(9) 0.3486(2) 0.0302(4) Uani 1 1 d . . . . .
C8 C 0.17673(11) 0.10184(9) -0.0411(2) 0.0273(4) Uani 1 1 d . . . . .
C9 C 0.09328(11) 0.10403(10) -0.0540(2) 0.0333(4) Uani 1 1 d . . . . .
H9 H 0.061173 0.119836 0.029494 0.040 Uiso 1 1 calc R U . . .
C10 C 0.05740(13) 0.08282(11) -0.1904(3) 0.0407(5) Uani 1 1 d . . . . .
H10 H 0.000357 0.083874 -0.198929 0.049 Uiso 1 1 calc R U . . .
C11 C 0.10273(14) 0.06024(11) -0.3141(3) 0.0408(5) Uani 1 1 d . . . . .
H11 H 0.077242 0.046459 -0.406928 0.049 Uiso 1 1 calc R U . . .
C12 C 0.18600(13) 0.05797(11) -0.3007(2) 0.0375(4) Uani 1 1 d . . . . .
H12 H 0.217837 0.042454 -0.384798 0.045 Uiso 1 1 calc R U . . .
C13 C 0.22279(11) 0.07824(10) -0.1654(2) 0.0316(4) Uani 1 1 d . . . . .
H13 H 0.279787 0.076122 -0.156743 0.038 Uiso 1 1 calc R U . . .
C14 C 0.30932(12) 0.20567(11) 0.5661(2) 0.0357(4) Uani 1 1 d . . . . .
H14A H 0.342888 0.247629 0.544454 0.054 Uiso 0.5 1 calc R U P A 1
H14B H 0.342223 0.162238 0.559137 0.054 Uiso 0.5 1 calc R U P A 1
H14C H 0.286776 0.209698 0.669416 0.054 Uiso 0.5 1 calc R U P A 1
H14D H 0.299129 0.245022 0.637716 0.054 Uiso 0.5 1 calc R U P B 2
H14E H 0.360352 0.214082 0.512611 0.054 Uiso 0.5 1 calc R U P B 2
H14F H 0.312407 0.160461 0.622680 0.054 Uiso 0.5 1 calc R U P B 2
C15 C 0.03505(12) 0.27038(11) 0.3560(3) 0.0424(5) Uani 1 1 d . . . . .
H15A H 0.041537 0.319154 0.316550 0.064 Uiso 0.5 1 calc R U P C 1
H15B H 0.016578 0.272334 0.462468 0.064 Uiso 0.5 1 calc R U P C 1
H15C H -0.004745 0.244760 0.293800 0.064 Uiso 0.5 1 calc R U P C 1
H15D H 0.037064 0.306783 0.436684 0.064 Uiso 0.5 1 calc R U P D 2
H15E H -0.007909 0.236009 0.378783 0.064 Uiso 0.5 1 calc R U P D 2
H15F H 0.024215 0.293457 0.257351 0.064 Uiso 0.5 1 calc R U P D 2
C2A C 0.30986(10) 0.34583(9) 0.2716(2) 0.0267(4) Uani 1 1 d . . . . .
C4A C 0.26627(11) 0.30162(10) 0.0364(2) 0.0298(4) Uani 1 1 d . . . . .
C5A C 0.33798(12) 0.26491(10) 0.0231(2) 0.0341(4) Uani 1 1 d . . . . .
H5A H 0.348676 0.236033 -0.064123 0.041 Uiso 1 1 calc R U . . .
C6A C 0.39426(11) 0.27115(10) 0.1401(2) 0.0329(4) Uani 1 1 d . . . . .
C8A C 0.33253(10) 0.40110(9) 0.5302(2) 0.0264(4) Uani 1 1 d . . . . .
C9A C 0.41550(11) 0.39298(10) 0.5484(2) 0.0327(4) Uani 1 1 d . . . . .
H9A H 0.447464 0.374186 0.467607 0.039 Uiso 1 1 calc R U . . .
C10A C 0.45074(13) 0.41280(11) 0.6865(3) 0.0404(5) Uani 1 1 d . . . . .
H10A H 0.507256 0.407420 0.699190 0.048 Uiso 1 1 calc R U . . .
C11A C 0.40568(14) 0.44002(11) 0.8053(3) 0.0415(5) Uani 1 1 d . . . . .
H11A H 0.430713 0.452960 0.899063 0.050 Uiso 1 1 calc R U . . .
C12A C 0.32337(13) 0.44830(11) 0.7863(2) 0.0380(4) Uani 1 1 d . . . . .
H12A H 0.291696 0.467128 0.867472 0.046 Uiso 1 1 calc R U . . .
C13A C 0.28716(11) 0.42928(10) 0.6498(2) 0.0325(4) Uani 1 1 d . . . . .
H13A H 0.230738 0.435504 0.637541 0.039 Uiso 1 1 calc R U . . .
C14A C 0.19993(13) 0.29762(12) -0.0793(2) 0.0368(4) Uani 1 1 d . . . . .
H14G H 0.151569 0.320760 -0.038132 0.055 Uiso 0.5 1 calc R U P E 1
H14H H 0.188103 0.247358 -0.102191 0.055 Uiso 0.5 1 calc R U P E 1
H14I H 0.216682 0.322134 -0.173209 0.055 Uiso 0.5 1 calc R U P E 1
C15A C 0.47339(12) 0.23244(12) 0.1355(3) 0.0448(5) Uani 1 1 d . . . . .
H15G H 0.477083 0.204618 0.040600 0.067 Uiso 0.5 1 calc R U P F 1
H15H H 0.477291 0.200151 0.223568 0.067 Uiso 0.5 1 calc R U P F 1
H15I H 0.517492 0.267273 0.139166 0.067 Uiso 0.5 1 calc R U P F 1
H15J H 0.503309 0.246878 0.043796 0.067 Uiso 0.5 1 calc R U P G 2
H15K H 0.463766 0.180701 0.132618 0.067 Uiso 0.5 1 calc R U P G 2
H15L H 0.504791 0.244464 0.226919 0.067 Uiso 0.5 1 calc R U P G 2
N1A N 0.38042(9) 0.31134(8) 0.26472(19) 0.0303(3) Uani 1 1 d . . . . .
N3A N 0.25248(9) 0.34286(8) 0.16046(17) 0.0267(3) Uani 1 1 d . . . . .
N7A N 0.28950(9) 0.38523(8) 0.39486(18) 0.0278(3) Uani 1 1 d . . . . .
C7T C 0.10644(10) 0.46121(9) 0.26074(19) 0.0245(3) Uani 1 1 d . . . . .
C8T C 0.04145(10) 0.51830(9) 0.24218(19) 0.0245(4) Uani 1 1 d . . . . .
H8T H 0.049220 0.541996 0.140584 0.029 Uiso 1 1 calc R U . . .
O5T O 0.14094(8) 0.45480(8) 0.38473(15) 0.0349(3) Uani 1 1 d . . . . .
O6T O 0.12099(7) 0.42272(7) 0.14188(14) 0.0313(3) Uani 1 1 d . . . . .
O9T O 0.04757(9) 0.57094(7) 0.35671(17) 0.0394(3) Uani 1 1 d . . . . .
H9T H 0.063888 0.552068 0.438301 0.067(9) Uiso 1 1 calc R . . . .
N1 N 0.12740(9) 0.19190(8) 0.22408(18) 0.0287(3) Uani 1 1 d . . . . .
N3 N 0.25453(9) 0.15973(8) 0.32951(18) 0.0267(3) Uani 1 1 d . . . . .
N7 N 0.22011(9) 0.11957(8) 0.09190(18) 0.0286(3) Uani 1 1 d . . . . .
O1 O 0.4396(7) -0.0707(4) 0.3164(13) 0.0326(19) Uani 0.63(4) 1 d . . P H 1
H1 H 0.422971 -0.052209 0.398176 0.049 Uiso 0.63(4) 1 calc R U P H 1
C3T C 0.39646(10) 0.04465(10) 0.2104(2) 0.0273(4) Uani 1 1 d . . . . .
C4T C 0.45784(10) -0.01647(10) 0.2107(2) 0.0284(4) Uani 1 1 d . . . . .
H4T H 0.452235 -0.039576 0.107947 0.034 Uiso 0.63(4) 1 calc R U P H 1
H4TA H 0.449547 -0.050537 0.123773 0.034 Uiso 0.37(4) 1 calc R U P H 2
O1T O 0.38294(7) 0.07675(7) 0.09051(14) 0.0313(3) Uani 1 1 d . . . . .
O2T O 0.36313(8) 0.05874(7) 0.33981(15) 0.0353(3) Uani 1 1 d . . . . .
O1A O 0.4622(9) -0.0535(9) 0.362(2) 0.030(3) Uani 0.37(4) 1 d . . P H 2
H1A H 0.430452 -0.033780 0.423303 0.044 Uiso 0.37(4) 1 calc R U P H 2
H14J H 0.151(3) 0.274(2) -0.033(5) 0.023(9) Uiso 0.5 1 d . . P I 2
H14K H 0.182(3) 0.346(2) -0.109(5) 0.019(9) Uiso 0.5 1 d . . P J 2
H14L H 0.212(3) 0.265(3) -0.165(6) 0.034(11) Uiso 0.5 1 d . . P K 2
H7A H 0.2400(15) 0.4034(12) 0.391(3) 0.035(6) Uiso 1 1 d . . . . .
H7 H 0.2761(16) 0.1077(13) 0.087(3) 0.045(7) Uiso 1 1 d . . . . .
H3 H 0.311(3) 0.116(2) 0.325(5) 0.112(14) Uiso 1 1 d . . . . .
H3A H 0.181(2) 0.386(2) 0.160(5) 0.100(13) 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
C2 N1 1.337(2) . ?
C2 N3 1.360(2) . ?
C2 N7 1.353(2) . ?
C4 C5 1.379(3) . ?
C4 C14 1.497(3) . ?
C4 N3 1.342(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(3) . ?
C6 C15 1.496(2) . ?
C6 N1 1.339(2) . ?
C8 C9 1.390(3) . ?
C8 C13 1.399(3) . ?
C8 N7 1.406(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 H14D 0.9800 . ?
C14 H14E 0.9800 . ?
C14 H14F 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 0.9800 . ?
C2A N1A 1.338(2) . ?
C2A N3A 1.361(2) . ?
C2A N7A 1.348(2) . ?
C4A C5A 1.379(3) . ?
C4A C14A 1.496(3) . ?
C4A N3A 1.349(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.390(3) . ?
C6A C15A 1.500(3) . ?
C6A N1A 1.342(3) . ?
C8A C9A 1.395(3) . ?
C8A C13A 1.391(3) . ?
C8A N7A 1.413(2) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.391(3) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.376(3) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.385(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.382(3) . ?
C13A H13A 0.9500 . ?
C14A H14G 0.9800 . ?
C14A H14H 0.9800 . ?
C14A H14I 0.9800 . ?
C14A H14J 1.01(4) . ?
C14A H14K 0.99(4) . ?
C14A H14L 0.98(5) . ?
C15A H15G 0.9800 . ?
C15A H15H 0.9800 . ?
C15A H15I 0.9800 . ?
C15A H15J 0.9800 . ?
C15A H15K 0.9800 . ?
C15A H15L 0.9800 . ?
N3A H3A 1.43(4) . ?
N7A H7A 0.89(3) . ?
C7T C8T 1.526(2) . ?
C7T O5T 1.231(2) . ?
C7T O6T 1.286(2) . ?
C8T C8T 1.537(3) 2_565 ?
C8T H8T 1.0000 . ?
C8T O9T 1.406(2) . ?
O6T H3A 1.22(4) . ?
O9T H9T 0.8400 . ?
N3 H3 1.25(4) . ?
N7 H7 0.96(3) . ?
O1 H1 0.8400 . ?
O1 C4T 1.404(4) . ?
C3T C4T 1.530(2) . ?
C3T O1T 1.228(2) . ?
C3T O2T 1.286(2) . ?
C4T C4T 1.529(4) 2_655 ?
C4T H4T 1.0000 . ?
C4T H4TA 1.0000 . ?
C4T O1A 1.490(10) . ?
O2T H3 1.38(4) . ?
O1A H1A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 N3 123.85(16) . . ?
N1 C2 N7 121.80(16) . . ?
N7 C2 N3 114.31(15) . . ?
C5 C4 C14 123.92(17) . . ?
N3 C4 C5 119.58(17) . . ?
N3 C4 C14 116.48(15) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.12(17) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C15 121.08(17) . . ?
N1 C6 C5 122.27(16) . . ?
N1 C6 C15 116.63(17) . . ?
C9 C8 C13 119.40(18) . . ?
C9 C8 N7 124.76(18) . . ?
C13 C8 N7 115.80(16) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.20(19) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.59(19) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.06(19) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.21(19) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.54(18) . . ?
C12 C13 H13 119.7 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
C4 C14 H14D 109.5 . . ?
C4 C14 H14E 109.5 . . ?
C4 C14 H14F 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
C6 C15 H15D 109.5 . . ?
C6 C15 H15E 109.5 . . ?
C6 C15 H15F 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
N1A C2A N3A 124.14(17) . . ?
N1A C2A N7A 121.21(16) . . ?
N7A C2A N3A 114.62(15) . . ?
C5A C4A C14A 123.60(17) . . ?
N3A C4A C5A 119.90(17) . . ?
N3A C4A C14A 116.49(16) . . ?
C4A C5A H5A 120.8 . . ?
C4A C5A C6A 118.45(17) . . ?
C6A C5A H5A 120.8 . . ?
C5A C6A C15A 121.90(18) . . ?
N1A C6A C5A 121.89(17) . . ?
N1A C6A C15A 116.20(18) . . ?
C9A C8A N7A 124.85(18) . . ?
C13A C8A C9A 119.37(18) . . ?
C13A C8A N7A 115.74(15) . . ?
C8A C9A H9A 120.5 . . ?
C10A C9A C8A 119.00(19) . . ?
C10A C9A H9A 120.5 . . ?
C9A C10A H10A 119.2 . . ?
C11A C10A C9A 121.56(18) . . ?
C11A C10A H10A 119.2 . . ?
C10A C11A H11A 120.4 . . ?
C10A C11A C12A 119.18(19) . . ?
C12A C11A H11A 120.4 . . ?
C11A C12A H12A 119.9 . . ?
C13A C12A C11A 120.2(2) . . ?
C13A C12A H12A 119.9 . . ?
C8A C13A H13A 119.7 . . ?
C12A C13A C8A 120.65(18) . . ?
C12A C13A H13A 119.7 . . ?
C4A C14A H14G 109.5 . . ?
C4A C14A H14H 109.5 . . ?
C4A C14A H14I 109.5 . . ?
C4A C14A H14J 110(2) . . ?
C4A C14A H14K 111(2) . . ?
C4A C14A H14L 114(3) . . ?
H14G C14A H14H 109.5 . . ?
H14G C14A H14I 109.5 . . ?
H14H C14A H14I 109.5 . . ?
H14J C14A H14K 105(3) . . ?
H14J C14A H14L 101(3) . . ?
H14K C14A H14L 115(4) . . ?
C6A C15A H15G 109.5 . . ?
C6A C15A H15H 109.5 . . ?
C6A C15A H15I 109.5 . . ?
C6A C15A H15J 109.5 . . ?
C6A C15A H15K 109.5 . . ?
C6A C15A H15L 109.5 . . ?
H15G C15A H15H 109.5 . . ?
H15G C15A H15I 109.5 . . ?
H15H C15A H15I 109.5 . . ?
H15J C15A H15K 109.5 . . ?
H15J C15A H15L 109.5 . . ?
H15K C15A H15L 109.5 . . ?
C2A N1A C6A 117.09(16) . . ?
C2A N3A H3A 124.2(17) . . ?
C4A N3A C2A 118.51(15) . . ?
C4A N3A H3A 117.0(17) . . ?
C2A N7A C8A 131.05(15) . . ?
C2A N7A H7A 114.4(16) . . ?
C8A N7A H7A 114.5(16) . . ?
O5T C7T C8T 119.37(15) . . ?
O5T C7T O6T 124.65(16) . . ?
O6T C7T C8T 115.97(14) . . ?
C7T C8T C8T 108.79(17) . 2_565 ?
C7T C8T H8T 108.2 . . ?
C8T C8T H8T 108.2 2_565 . ?
O9T C8T C7T 111.23(14) . . ?
O9T C8T C8T 112.08(13) . 2_565 ?
O9T C8T H8T 108.2 . . ?
C7T O6T H3A 112(2) . . ?
C8T O9T H9T 109.5 . . ?
C2 N1 C6 116.81(16) . . ?
C2 N3 H3 119(2) . . ?
C4 N3 C2 119.20(15) . . ?
C4 N3 H3 121(2) . . ?
C2 N7 C8 130.64(15) . . ?
C2 N7 H7 115.0(16) . . ?
C8 N7 H7 113.8(16) . . ?
C4T O1 H1 109.5 . . ?
O1T C3T C4T 119.17(15) . . ?
O1T C3T O2T 124.85(16) . . ?
O2T C3T C4T 115.98(15) . . ?
O1 C4T C3T 113.3(2) . . ?
O1 C4T C4T 119.2(7) . 2_655 ?
O1 C4T H4T 105.0 . . ?
C3T C4T H4T 105.0 . . ?
C3T C4T H4TA 112.5 . . ?
C4T C4T C3T 108.01(18) 2_655 . ?
C4T C4T H4T 105.0 2_655 . ?
C4T C4T H4TA 112.5 2_655 . ?
O1A C4T C3T 112.4(3) . . ?
O1A C4T C4T 98.2(8) . 2_655 ?
O1A C4T H4TA 112.5 . . ?
C3T O2T H3 110.2(19) . . ?
C4T O1A H1A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9 N1 0.95 2.43 2.985(3) 117.0 . yes
C15 H15A O9T 0.98 2.55 3.266(2) 129.4 2_565 yes
C9A H9A N1A 0.95 2.40 2.967(3) 118.0 . yes
C15A H15K O1T 0.98 2.39 3.297(3) 153.8 . yes
C8T H8T O1T 1.00 2.40 3.348(2) 157.9 3 yes
O9T H9T O5T 0.84 2.27 2.6776(18) 110.0 . yes
O9T H9T O2T 0.84 2.29 3.046(2) 150.0 3_556 yes
O9T H9T O1A 0.84 2.43 2.86(2) 112.4 4_456 yes
O1 H1 O5T 0.84 2.18 2.971(6) 157.7 3_546 yes
C4T H4T O6T 1.00 2.60 3.533(2) 156.2 3_545 yes
O1A H1A O5T 0.84 2.06 2.805(8) 146.8 3_546 yes
O1A H1A O2T 0.84 2.18 2.672(6) 117.0 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C5 C6 C15 178.79(18) . . . . ?
C4 C5 C6 N1 -2.9(3) . . . . ?
C5 C4 N3 C2 2.8(2) . . . . ?
C5 C6 N1 C2 1.4(2) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C8 C13 C12 0.7(3) . . . . ?
C9 C8 N7 C2 -18.6(3) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C13 C8 N7 C2 163.64(17) . . . . ?
C14 C4 C5 C6 179.02(17) . . . . ?
C14 C4 N3 C2 -175.63(16) . . . . ?
C15 C6 N1 C2 179.79(16) . . . . ?
C4A C5A C6A C15A 179.36(18) . . . . ?
C4A C5A C6A N1A 0.3(3) . . . . ?
C5A C4A N3A C2A -1.4(2) . . . . ?
C5A C6A N1A C2A -0.4(3) . . . . ?
C8A C9A C10A C11A 0.1(3) . . . . ?
C9A C8A C13A C12A -0.8(3) . . . . ?
C9A C8A N7A C2A 17.1(3) . . . . ?
C9A C10A C11A C12A -0.4(3) . . . . ?
C10A C11A C12A C13A 0.1(3) . . . . ?
C11A C12A C13A C8A 0.5(3) . . . . ?
C13A C8A C9A C10A 0.5(3) . . . . ?
C13A C8A N7A C2A -165.40(18) . . . . ?
C14A C4A C5A C6A -178.12(18) . . . . ?
C14A C4A N3A C2A 177.44(16) . . . . ?
C15A C6A N1A C2A -179.47(17) . . . . ?
N1A C2A N3A C4A 1.3(3) . . . . ?
N1A C2A N7A C8A 2.5(3) . . . . ?
N3A C2A N1A C6A -0.5(3) . . . . ?
N3A C2A N7A C8A -179.43(17) . . . . ?
N3A C4A C5A C6A 0.6(3) . . . . ?
N7A C2A N1A C6A 177.47(16) . . . . ?
N7A C2A N3A C4A -176.72(15) . . . . ?
N7A C8A C9A C10A 177.96(17) . . . . ?
N7A C8A C13A C12A -178.50(17) . . . . ?
O5T C7T C8T C8T -105.13(15) . . . 2_565 ?
O5T C7T C8T O9T 18.8(2) . . . . ?
O6T C7T C8T C8T 74.89(14) . . . 2_565 ?
O6T C7T C8T O9T -161.18(15) . . . . ?
N1 C2 N3 C4 -4.6(2) . . . . ?
N1 C2 N7 C8 -6.4(3) . . . . ?
N3 C2 N1 C6 2.4(2) . . . . ?
N3 C2 N7 C8 175.44(17) . . . . ?
N3 C4 C5 C6 0.7(3) . . . . ?
N7 C2 N1 C6 -175.55(16) . . . . ?
N7 C2 N3 C4 173.50(15) . . . . ?
N7 C8 C9 C10 -177.83(17) . . . . ?
N7 C8 C13 C12 178.62(16) . . . . ?
O1T C3T C4T O1 -148.2(8) . . . . ?
O1T C3T C4T C4T 77.48(17) . . . 2_655 ?
O1T C3T C4T O1A -175.3(11) . . . . ?
O2T C3T C4T O1 32.4(8) . . . . ?
O2T C3T C4T C4T -101.89(14) . . . 2_655 ?
O2T C3T C4T O1A 5.3(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.97(18)
2 0.03(18)

