# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_gu287_a
_database_code_depnum_ccdc_archive 'CCDC 1503996'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'THY: 2,4 DAP'
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H6 N2 O2, C4 H6 N4'
_chemical_formula_sum            'C9 H12 N6 O2'
_chemical_formula_weight         236.25

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

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

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

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

_cell_length_a                   7.3027(14)
_cell_length_b                   7.7089(15)
_cell_length_c                   10.368(2)
_cell_angle_alpha                93.184(3)
_cell_angle_beta                 98.654(3)
_cell_angle_gamma                107.390(3)
_cell_volume                     547.52(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4443
_cell_measurement_theta_min      5.569
_cell_measurement_theta_max      56.025

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Siemens SMART, Bruker APEXII CCD'
_diffrn_measurement_method       omega-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7616
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         28.049
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2649
_reflns_number_gt                2269
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX, Bruker-AXS'
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_structure_solution    'SHELXS-97, G. Sheldrick (1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'X-SEED, L.Barbour (1999);http://x-seed.net/'
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0770P)²+0.0595P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2649
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60833(12) -0.19879(10) 0.58735(8) 0.0428(2) Uani 1 1 d . . . . .
O2 O 0.94239(13) 0.28802(9) 0.40194(8) 0.0434(2) Uani 1 1 d . . . . .
N1 N 0.77700(12) 0.04596(10) 0.49810(8) 0.0309(2) Uani 1 1 d . . . . .
H1A H 0.7810 -0.0267 0.4333 0.037 Uiso 1 1 calc R U . . .
N2 N 0.85153(13) 0.33910(11) 0.59659(8) 0.0337(2) Uani 1 1 d . . . . .
H2A H 0.8999 0.4555 0.5971 0.040 Uiso 1 1 calc R U . . .
C1 C 0.68483(14) -0.03224(13) 0.59761(10) 0.0303(2) Uani 1 1 d . . . . .
C2 C 0.86217(14) 0.22881(12) 0.49406(10) 0.0308(2) Uani 1 1 d . . . . .
C3 C 0.76604(15) 0.27152(14) 0.69998(10) 0.0346(2) Uani 1 1 d . . . . .
H3A H 0.7648 0.3537 0.7687 0.042 Uiso 1 1 calc R U . . .
C4 C 0.68414(14) 0.09242(14) 0.70660(10) 0.0327(2) Uani 1 1 d . . . . .
C5 C 0.59492(18) 0.01670(17) 0.82021(11) 0.0447(3) Uani 1 1 d . . . . .
H5A H 0.4603 -0.0518 0.7903 0.067 Uiso 1 1 calc R U . . .
H5B H 0.6044 0.1153 0.8843 0.067 Uiso 1 1 calc R U . . .
H5C H 0.6627 -0.0620 0.8590 0.067 Uiso 1 1 calc R U . . .
N3 N 0.13272(15) 0.22413(13) 0.94733(9) 0.0434(3) Uani 1 1 d . . . . .
N4 N 0.06561(15) -0.05649(12) 0.83404(9) 0.0422(2) Uani 1 1 d . . . . .
H4A H 0.0156 -0.1044 0.8987 0.051 Uiso 1 1 calc R U . . .
H4B H 0.0674 -0.1254 0.7664 0.051 Uiso 1 1 calc R U . . .
N5 N 0.21776(12) 0.19239(11) 0.73451(8) 0.0312(2) Uani 1 1 d . . . . .
N6 N 0.37544(16) 0.44229(12) 0.63915(10) 0.0473(3) Uani 1 1 d . . . . .
H6A H 0.3748 0.3700 0.5728 0.057 Uiso 1 1 calc R U . . .
H6B H 0.4270 0.5584 0.6401 0.057 Uiso 1 1 calc R U . . .
C6 C 0.14056(14) 0.12516(13) 0.83869(9) 0.0316(2) Uani 1 1 d . . . . .
C7 C 0.29613(15) 0.37420(13) 0.74098(10) 0.0339(2) Uani 1 1 d . . . . .
C8 C 0.2924(2) 0.48909(15) 0.84936(12) 0.0488(3) Uani 1 1 d . . . . .
H8A H 0.3440 0.6156 0.8539 0.059 Uiso 1 1 calc R U . . .
C9 C 0.2088(2) 0.40496(17) 0.94782(12) 0.0535(3) Uani 1 1 d . . . . .
H9A H 0.2043 0.4788 1.0206 0.064 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 C1 1.2288(12) . ?
O2 C2 1.2331(12) . ?
N1 C2 1.3659(12) . ?
N1 C1 1.3844(12) . ?
N1 H1A 0.8600 . ?
N2 C2 1.3502(13) . ?
N2 C3 1.3708(13) . ?
N2 H2A 0.8600 . ?
C1 C4 1.4437(14) . ?
C3 C4 1.3409(14) . ?
C3 H3A 0.9300 . ?
C4 C5 1.4942(14) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
N3 C9 1.3369(15) . ?
N3 C6 1.3432(13) . ?
N4 C6 1.3376(13) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 C7 1.3398(12) . ?
N5 C6 1.3505(12) . ?
N6 C7 1.3377(13) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C7 C8 1.4003(16) . ?
C8 C9 1.3638(17) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?

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
C2 N1 C1 125.53(8) . . ?
C2 N1 H1A 117.2 . . ?
C1 N1 H1A 117.2 . . ?
C2 N2 C3 122.12(8) . . ?
C2 N2 H2A 118.9 . . ?
C3 N2 H2A 118.9 . . ?
O1 C1 N1 119.10(9) . . ?
O1 C1 C4 124.76(9) . . ?
N1 C1 C4 116.13(8) . . ?
O2 C2 N2 122.63(9) . . ?
O2 C2 N1 121.69(9) . . ?
N2 C2 N1 115.68(8) . . ?
C4 C3 N2 123.06(9) . . ?
C4 C3 H3A 118.5 . . ?
N2 C3 H3A 118.5 . . ?
C3 C4 C1 117.43(9) . . ?
C3 C4 C5 123.59(10) . . ?
C1 C4 C5 118.98(9) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C9 N3 C6 114.80(9) . . ?
C6 N4 H4A 120.0 . . ?
C6 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C7 N5 C6 117.00(9) . . ?
C7 N6 H6A 120.0 . . ?
C7 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N4 C6 N3 116.75(9) . . ?
N4 C6 N5 117.32(9) . . ?
N3 C6 N5 125.94(9) . . ?
N6 C7 N5 117.56(9) . . ?
N6 C7 C8 121.17(10) . . ?
N5 C7 C8 121.26(9) . . ?
C9 C8 C7 116.21(10) . . ?
C9 C8 H8A 121.9 . . ?
C7 C8 H8A 121.9 . . ?
N3 C9 C8 124.76(10) . . ?
N3 C9 H9A 117.6 . . ?
C8 C9 H9A 117.6 . . ?

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
N4 H4A N3 0.86 2.16 3.0168(13) 175.3 2_557

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_twin4a
_database_code_depnum_ccdc_archive 'CCDC 1503998'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_audit_creation_date             2016-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            
'thymine:2,4-diamino-6-hydroxypyrimidine trihydrate'
_chemical_name_systematic        T:DAHP.3H2O
_chemical_formula_moiety         '3(H2 O), C5 H6 N2 O2, C4 H6 N4 O'
_chemical_formula_sum            'C9 H18 N6 O6'
_chemical_formula_weight         306.29
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.9654(5)
_cell_length_b                   6.9947(5)
_cell_length_c                   15.4852(10)
_cell_angle_alpha                83.219(2)
_cell_angle_beta                 87.719(2)
_cell_angle_gamma                73.739(2)
_cell_volume                     719.19(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.65
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1476 before and 0.0523 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1499 before and 0.0610 after correction.
 The Ratio of minimum to maximum transmission is 0.91.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 38876 reflections, Rint = 0.1130
 (19048 with I > 3sig(I), Rint = 0.0581)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3426
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.65
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2765
_reflns_number_total             3426
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.6283P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1223
_refine_special_details          
;Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger., Twin
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.3817(2) 0.8704(2) 0.08246(10) 0.0207(3) Uani 1 d . . .
O2 O 0.3155(2) 0.1672(2) 0.42883(9) 0.0185(3) Uani 1 d . . .
O3 O 0.9736(2) -0.1112(2) 0.37087(9) 0.0178(3) Uani 1 d . . .
N4 N 0.6450(2) 0.0289(2) 0.39786(11) 0.0147(3) Uani 1 d . . .
O5 O 0.7613(2) 0.7406(2) 0.00240(10) 0.0209(3) Uani 1 d . . .
O6 O 1.0862(2) 0.4812(2) 0.23857(9) 0.0194(3) Uani 1 d . . .
N7 N 0.3905(3) 0.7670(3) 0.27691(12) 0.0173(4) Uani 1 d . . .
N8 N 0.4351(2) 0.2354(2) 0.29365(11) 0.0149(4) Uani 1 d . . .
N9 N 0.9275(2) 0.4285(2) 0.36624(11) 0.0142(4) Uani 1 d . . .
N10 N 0.5824(2) 0.5702(2) 0.38895(11) 0.0143(3) Uani 1 d . . .
O11 O 0.1441(2) 0.6120(2) 0.07402(10) 0.0198(3) Uani 1 d . . .
C12 C 0.7378(3) 0.6295(3) 0.24939(13) 0.0143(4) Uani 1 d . . .
C13 C 0.4569(3) 0.1454(3) 0.37605(13) 0.0146(4) Uani 1 d . . .
C14 C 0.8114(3) -0.0038(3) 0.34287(13) 0.0135(4) Uani 1 d . . .
N15 N 0.7786(3) 0.3725(3) 0.49889(12) 0.0182(4) Uani 1 d . . .
C16 C 0.5908(3) 0.2098(3) 0.23507(13) 0.0164(4) Uani 1 d . . .
C17 C 0.7608(3) 0.4589(3) 0.41732(12) 0.0134(4) Uani 1 d . . .
C18 C 0.5714(3) 0.6546(3) 0.30465(12) 0.0125(4) Uani 1 d . . .
C19 C 0.7762(3) 0.0948(3) 0.25494(13) 0.0150(4) Uani 1 d . . .
C20 C 0.9223(3) 0.5149(3) 0.28086(13) 0.0150(4) Uani 1 d . . .
C21 C 0.9467(3) 0.0642(4) 0.19123(15) 0.0212(5) Uani 1 d . . .
H16 H 0.555(3) 0.282(4) 0.1785(16) 0.020(6) Uiso 1 d . . .
H12 H 0.727(3) 0.687(3) 0.1906(16) 0.017(6) Uiso 1 d . . .
H15A H 0.894(4) 0.288(4) 0.5198(17) 0.030(7) Uiso 1 d . . .
H8 H 0.321(4) 0.314(4) 0.2797(15) 0.017(6) Uiso 1 d . . .
H21A H 1.005(4) -0.081(4) 0.1835(17) 0.033(7) Uiso 1 d . . .
H9 H 1.037(4) 0.354(4) 0.3867(17) 0.026(7) Uiso 1 d . . .
H21B H 0.899(4) 0.138(4) 0.1357(18) 0.032(7) Uiso 1 d . . .
H11A H 0.125(4) 0.574(4) 0.129(2) 0.038(8) Uiso 1 d . . .
H11B H 0.216(4) 0.691(4) 0.0749(18) 0.033(8) Uiso 1 d . . .
H4 H 0.664(4) -0.034(4) 0.4523(18) 0.030(7) Uiso 1 d . . .
H1A H 0.500(5) 0.829(4) 0.058(2) 0.043(8) Uiso 1 d . . .
H5A H 0.881(5) 0.718(5) 0.026(2) 0.051(9) Uiso 1 d . . .
H7A H 0.285(4) 0.784(4) 0.3089(18) 0.032(7) Uiso 1 d . . .
H7B H 0.378(4) 0.819(4) 0.220(2) 0.037(8) Uiso 1 d . . .
H21C H 1.057(4) 0.110(4) 0.2113(17) 0.031(7) Uiso 1 d . . .
H15B H 0.674(4) 0.396(4) 0.5311(18) 0.031(7) Uiso 1 d . . .
H5B H 0.772(5) 0.633(5) -0.023(2) 0.053(10) Uiso 1 d . . .
H1B H 0.341(5) 0.986(5) 0.059(2) 0.046(9) Uiso 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 H1A 0.88(3) . ?
O1 H1B 0.82(3) . ?
O2 C13 1.242(2) . ?
O3 C14 1.231(2) . ?
N4 C13 1.366(2) . ?
N4 C14 1.393(2) . ?
N4 H4 0.90(3) . ?
O5 H5A 0.88(3) . ?
O5 H5B 0.87(3) . ?
O6 C20 1.271(2) . ?
N7 C18 1.341(2) . ?
N7 H7A 0.86(3) . ?
N7 H7B 0.91(3) . ?
N8 C13 1.349(3) . ?
N8 C16 1.372(3) . ?
N8 H8 0.85(2) . ?
N9 C17 1.359(2) . ?
N9 C20 1.385(2) . ?
N9 H9 0.84(3) . ?
N10 C17 1.328(2) . ?
N10 C18 1.364(2) . ?
O11 H11A 0.87(3) . ?
O11 H11B 0.85(3) . ?
C12 C18 1.396(3) . ?
C12 C20 1.383(3) . ?
C12 H12 0.95(2) . ?
C14 C19 1.449(3) . ?
N15 C17 1.329(3) . ?
N15 H15A 0.90(3) . ?
N15 H15B 0.86(3) . ?
C16 C19 1.342(3) . ?
C16 H16 0.96(2) . ?
C19 C21 1.498(3) . ?
C21 H21A 1.00(3) . ?
C21 H21B 0.97(3) . ?
C21 H21C 0.99(3) . ?

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
H1A O1 H1B 102(3) . . ?
C13 N4 C14 125.79(17) . . ?
C13 N4 H4 117.9(17) . . ?
C14 N4 H4 116.3(17) . . ?
H5A O5 H5B 103(3) . . ?
C18 N7 H7A 123.2(18) . . ?
C18 N7 H7B 118.1(18) . . ?
H7A N7 H7B 119(3) . . ?
C13 N8 C16 122.31(18) . . ?
C13 N8 H8 117.0(16) . . ?
C16 N8 H8 120.6(16) . . ?
C17 N9 C20 121.76(17) . . ?
C17 N9 H9 119.5(17) . . ?
C20 N9 H9 118.8(17) . . ?
C17 N10 C18 116.97(17) . . ?
H11A O11 H11B 105(3) . . ?
C18 C12 H12 121.8(14) . . ?
C20 C12 C18 119.12(18) . . ?
C20 C12 H12 119.1(14) . . ?
O2 C13 N4 122.06(18) . . ?
O2 C13 N8 122.29(18) . . ?
N8 C13 N4 115.65(17) . . ?
O3 C14 N4 119.39(18) . . ?
O3 C14 C19 125.07(18) . . ?
N4 C14 C19 115.53(17) . . ?
C17 N15 H15A 122.4(17) . . ?
C17 N15 H15B 117.4(18) . . ?
H15A N15 H15B 120(2) . . ?
N8 C16 H16 113.9(14) . . ?
C19 C16 N8 122.99(19) . . ?
C19 C16 H16 123.1(14) . . ?
N10 C17 N9 122.76(18) . . ?
N10 C17 N15 119.12(18) . . ?
N15 C17 N9 118.13(18) . . ?
N7 C18 N10 116.36(17) . . ?
N7 C18 C12 120.89(18) . . ?
N10 C18 C12 122.75(18) . . ?
C14 C19 C21 118.86(17) . . ?
C16 C19 C14 117.72(18) . . ?
C16 C19 C21 123.43(19) . . ?
O6 C20 N9 117.35(17) . . ?
O6 C20 C12 126.02(18) . . ?
C12 C20 N9 116.63(17) . . ?
C19 C21 H21A 111.6(15) . . ?
C19 C21 H21B 108.8(16) . . ?
C19 C21 H21C 111.4(15) . . ?
H21A C21 H21B 109(2) . . ?
H21A C21 H21C 106(2) . . ?
H21B C21 H21C 110(2) . . ?

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
O3 C14 C19 C16 -178.9(2) . . . . ?
O3 C14 C19 C21 1.0(3) . . . . ?
N4 C14 C19 C16 1.2(3) . . . . ?
N4 C14 C19 C21 -178.91(18) . . . . ?
N8 C16 C19 C14 -0.8(3) . . . . ?
N8 C16 C19 C21 179.4(2) . . . . ?
C13 N4 C14 O3 179.36(18) . . . . ?
C13 N4 C14 C19 -0.7(3) . . . . ?
C13 N8 C16 C19 -0.3(3) . . . . ?
C14 N4 C13 O2 179.91(19) . . . . ?
C14 N4 C13 N8 -0.3(3) . . . . ?
C16 N8 C13 O2 -179.36(19) . . . . ?
C16 N8 C13 N4 0.8(3) . . . . ?
C17 N9 C20 O6 178.67(18) . . . . ?
C17 N9 C20 C12 -1.7(3) . . . . ?
C17 N10 C18 N7 -179.83(18) . . . . ?
C17 N10 C18 C12 -0.6(3) . . . . ?
C18 N10 C17 N9 0.2(3) . . . . ?
C18 N10 C17 N15 -179.60(18) . . . . ?
C18 C12 C20 O6 -179.12(19) . . . . ?
C18 C12 C20 N9 1.3(3) . . . . ?
C20 N9 C17 N10 1.0(3) . . . . ?
C20 N9 C17 N15 -179.24(18) . . . . ?
C20 C12 C18 N7 179.04(19) . . . . ?
C20 C12 C18 N10 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_twin5c
_database_code_depnum_ccdc_archive 'CCDC 1503997'
_audit_update_record             
;
2016-09-12 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_audit_creation_date             2016-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            Thymine:2,4,6-triaminopyrimidine
_chemical_name_systematic        T:246TAPM
_chemical_formula_moiety         'C5 H6 N2 O2, C4 H7 N5, O H2'
_chemical_formula_sum            'C9 H15 N7 O3'
_chemical_formula_weight         269.28
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7793(2)
_cell_length_b                   12.3197(4)
_cell_length_c                   14.8694(4)
_cell_angle_alpha                104.7164(14)
_cell_angle_beta                 96.7763(13)
_cell_angle_gamma                90.5177(14)
_cell_volume                     1191.76(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4566
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      0.754
_cell_measurement_theta_min      0.829
_shelx_estimated_absorpt_T_max   40.0205
_shelx_estimated_absorpt_T_min   3.098
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  0.753622
_exptl_absorpt_correction_T_min  0.308952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1546 before and 0.0514 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1674 before and 0.0755 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4424
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.715
_diffrn_reflns_theta_min         3.097
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4217
_reflns_number_total             4424
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         4424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      1.066
_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)+(0.1074P)²+0.4075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1546
_refine_special_details          
;Refined as a 2-component twin...

 The initial cell appeared to be C-centered monoclinic. Cell_Now revealed a 
 weak centering for P-lattice. Weak reflections from the second individual
 were apparently doubling the long axis to ~29 ang. The long axis limit was
 used to find a pair of individuals with the current unit cell and an
 approximated twin law: 1 0 0 -0.03090 -1 0 -0.51812  0.0 -1.0. Final
 integrated data came from SAINT whereby box sizes were fixed, unit cells
 were fixed, and final cell came from global refinement. Ratio of twin
 individuals is approximately 90:10 based on HKLF5 data for space group P-1., Twin
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.903(2) 0.097(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1A(H1AA), N2A(H2AA), C3A(H3AA), C8A(H8AA), N1B(H1BA), N2B(H2BA), C3B(H3BA),
 C8B(H8BA)
3.b Idealised Me refined as rotating group:
 C5A(H5AA,H5AB,H5AC), C5B(H5BA,H5BB,H5BC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.4408(2) 0.25447(13) 0.15126(10) 0.0116(3) Uani 1 1 d . . . . .
O1A O 0.41018(18) 0.16811(9) 0.08664(7) 0.0166(3) Uani 1 1 d . . . . .
N1A N 0.4942(2) 0.24497(10) 0.24192(9) 0.0111(3) Uani 1 1 d . . . . .
H1AA H 0.4990 0.1767 0.2502 0.013 Uiso 1 1 calc R . . . .
C2A C 0.5400(2) 0.33259(13) 0.31941(10) 0.0113(3) Uani 1 1 d . . . . .
O2A O 0.59237(17) 0.31656(9) 0.39787(7) 0.0143(3) Uani 1 1 d . . . . .
N2A N 0.5271(2) 0.43692(10) 0.30544(9) 0.0123(3) Uani 1 1 d . . . . .
H2AA H 0.5551 0.4957 0.3535 0.015 Uiso 1 1 calc R . . . .
C3A C 0.4711(2) 0.45328(12) 0.21766(11) 0.0122(3) Uani 1 1 d . . . . .
H3AA H 0.4626 0.5280 0.2114 0.015 Uiso 1 1 calc R . . . .
C4A C 0.4279(2) 0.36747(13) 0.14056(10) 0.0121(3) Uani 1 1 d . . . . .
C5A C 0.3733(3) 0.38413(13) 0.04422(11) 0.0165(3) Uani 1 1 d . . . . .
H5AA H 0.3575 0.4643 0.0487 0.025 Uiso 1 1 calc GR . . . .
H5AB H 0.2480 0.3425 0.0157 0.025 Uiso 1 1 calc GR . . . .
H5AC H 0.4786 0.3565 0.0054 0.025 Uiso 1 1 calc GR . . . .
N3A N 0.9272(2) 0.59217(11) 0.62895(9) 0.0126(3) Uani 1 1 d . . . . .
C6A C 0.9160(2) 0.49077(12) 0.64707(10) 0.0116(3) Uani 1 1 d . . . . .
N4A N 0.8466(2) 0.40353(11) 0.57549(9) 0.0173(3) Uani 1 1 d . . . . .
H4AA H 0.810(3) 0.4129(17) 0.5180(16) 0.021 Uiso 1 1 d R . . . .
H4AB H 0.843(3) 0.3332(19) 0.5839(15) 0.021 Uiso 1 1 d R . . . .
N5A N 0.9663(2) 0.46779(10) 0.73119(9) 0.0109(3) Uani 1 1 d . . . . .
C7A C 1.0349(2) 0.55621(12) 0.80288(10) 0.0109(3) Uani 1 1 d . . . . .
N6A N 1.0880(2) 0.53197(11) 0.88700(9) 0.0143(3) Uani 1 1 d . . . . .
H6AA H 1.034(3) 0.4687(18) 0.8954(14) 0.017 Uiso 1 1 d R . . . .
H6AB H 1.119(3) 0.5865(18) 0.9373(15) 0.017 Uiso 1 1 d R . . . .
C8A C 1.0552(2) 0.66440(12) 0.79212(10) 0.0124(3) Uani 1 1 d . . . . .
H8AA H 1.1063 0.7255 0.8429 0.015 Uiso 1 1 calc R . . . .
C9A C 0.9962(2) 0.67862(12) 0.70234(11) 0.0118(3) Uani 1 1 d . . . . .
N7A N 1.0005(2) 0.78231(11) 0.68570(10) 0.0159(3) Uani 1 1 d . . . . .
H7AA H 0.973(3) 0.7832(17) 0.6252(16) 0.019 Uiso 1 1 d R . . . .
H7AB H 1.085(4) 0.8280(18) 0.7199(15) 0.019 Uiso 1 1 d R . . . .
C1B C 0.8549(2) 0.24371(13) 0.85215(10) 0.0111(3) Uani 1 1 d . . . . .
O1B O 0.86543(18) 0.33108(9) 0.91610(7) 0.0164(3) Uani 1 1 d . . . . .
N1B N 0.8489(2) 0.25114(10) 0.76024(9) 0.0110(3) Uani 1 1 d . . . . .
H1BA H 0.8474 0.3188 0.7508 0.013 Uiso 1 1 calc R . . . .
C2B C 0.8451(2) 0.16204(12) 0.68309(10) 0.0112(3) Uani 1 1 d . . . . .
O2B O 0.84147(18) 0.17592(9) 0.60319(7) 0.0145(3) Uani 1 1 d . . . . .
N2B N 0.8460(2) 0.05857(10) 0.69971(9) 0.0120(3) Uani 1 1 d . . . . .
H2BA H 0.8464 -0.0011 0.6523 0.014 Uiso 1 1 calc R . . . .
C3B C 0.8463(2) 0.04449(12) 0.78891(11) 0.0115(3) Uani 1 1 d . . . . .
H3BA H 0.8444 -0.0296 0.7968 0.014 Uiso 1 1 calc R . . . .
C4B C 0.8493(2) 0.13152(13) 0.86500(10) 0.0116(3) Uani 1 1 d . . . . .
C5B C 0.8540(3) 0.11732(13) 0.96274(11) 0.0160(3) Uani 1 1 d . . . . .
H5BA H 0.8390 0.0373 0.9601 0.024 Uiso 1 1 calc GR . . . .
H5BB H 0.7449 0.1576 0.9924 0.024 Uiso 1 1 calc GR . . . .
H5BC H 0.9812 0.1478 0.9994 0.024 Uiso 1 1 calc GR . . . .
N3B N 0.6400(2) -0.09893(11) 0.36794(9) 0.0125(3) Uani 1 1 d . . . . .
C6B C 0.6140(2) 0.00242(12) 0.35080(10) 0.0112(3) Uani 1 1 d . . . . .
N4B N 0.5794(2) 0.08789(11) 0.42355(9) 0.0157(3) Uani 1 1 d . . . . .
H4BA H 0.616(3) 0.0831(17) 0.4824(16) 0.019 Uiso 1 1 d R . . . .
H4BB H 0.585(3) 0.1584(18) 0.4182(15) 0.019 Uiso 1 1 d R . . . .
N5B N 0.6149(2) 0.02732(10) 0.26730(9) 0.0112(3) Uani 1 1 d . . . . .
C7B C 0.6438(2) -0.05952(12) 0.19409(10) 0.0104(3) Uani 1 1 d . . . . .
N6B N 0.6467(2) -0.03376(11) 0.11048(9) 0.0143(3) Uani 1 1 d . . . . .
H6BA H 0.592(3) 0.0310(18) 0.1071(14) 0.017 Uiso 1 1 d R . . . .
H6BB H 0.643(3) -0.0883(18) 0.0592(15) 0.017 Uiso 1 1 d R . . . .
C8B C 0.6734(2) -0.16796(12) 0.20366(10) 0.0122(3) Uani 1 1 d . . . . .
H8BA H 0.6946 -0.2282 0.1519 0.015 Uiso 1 1 calc R . . . .
C9B C 0.6703(2) -0.18363(12) 0.29348(11) 0.0110(3) Uani 1 1 d . . . . .
N7B N 0.6935(2) -0.28678(11) 0.30986(10) 0.0156(3) Uani 1 1 d . . . . .
H7BA H 0.706(3) -0.2857(17) 0.3731(15) 0.019 Uiso 1 1 d R . . . .
H7BB H 0.751(3) -0.3361(18) 0.2718(15) 0.019 Uiso 1 1 d R . . . .
O3A O 0.66660(19) 0.60951(9) 0.46616(8) 0.0152(3) Uani 1 1 d . . . . .
H3AB H 0.764(4) 0.6096(18) 0.5055(16) 0.018 Uiso 1 1 d R . . . .
H3AC H 0.571(3) 0.6317(17) 0.4980(16) 0.018 Uiso 1 1 d R . . . .
O3B O 0.8931(2) -0.10791(9) 0.53365(8) 0.0161(3) Uani 1 1 d . . . . .
H3BC H 0.995(4) -0.1078(17) 0.5052(16) 0.019 Uiso 1 1 d R . . . .
H3BB H 0.798(4) -0.1153(18) 0.4909(17) 0.019 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A O1A 1.2361(19) . ?
C1A N1A 1.3884(19) . ?
C1A C4A 1.443(2) . ?
N1A H1AA 0.8800 . ?
N1A C2A 1.3663(19) . ?
C2A O2A 1.2436(19) . ?
C2A N2A 1.3551(19) . ?
N2A H2AA 0.8800 . ?
N2A C3A 1.3808(19) . ?
C3A H3AA 0.9500 . ?
C3A C4A 1.348(2) . ?
C4A C5A 1.502(2) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
N3A C6A 1.3465(19) . ?
N3A C9A 1.350(2) . ?
C6A N4A 1.342(2) . ?
C6A N5A 1.3572(19) . ?
N4A H4AA 0.90(2) . ?
N4A H4AB 0.91(2) . ?
N5A C7A 1.3501(19) . ?
C7A N6A 1.3671(19) . ?
C7A C8A 1.390(2) . ?
N6A H6AA 0.90(2) . ?
N6A H6AB 0.87(2) . ?
C8A H8AA 0.9500 . ?
C8A C9A 1.402(2) . ?
C9A N7A 1.362(2) . ?
N7A H7AA 0.90(2) . ?
N7A H7AB 0.83(2) . ?
C1B O1B 1.2372(19) . ?
C1B N1B 1.3886(19) . ?
C1B C4B 1.443(2) . ?
N1B H1BA 0.8800 . ?
N1B C2B 1.3691(19) . ?
C2B O2B 1.2401(19) . ?
C2B N2B 1.3586(19) . ?
N2B H2BA 0.8800 . ?
N2B C3B 1.3804(19) . ?
C3B H3BA 0.9500 . ?
C3B C4B 1.345(2) . ?
C4B C5B 1.504(2) . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?
N3B C6B 1.3455(19) . ?
N3B C9B 1.3518(19) . ?
C6B N4B 1.349(2) . ?
C6B N5B 1.3531(18) . ?
N4B H4BA 0.90(2) . ?
N4B H4BB 0.89(2) . ?
N5B C7B 1.3530(19) . ?
C7B N6B 1.3613(19) . ?
C7B C8B 1.393(2) . ?
N6B H6BA 0.89(2) . ?
N6B H6BB 0.88(2) . ?
C8B H8BA 0.9500 . ?
C8B C9B 1.400(2) . ?
C9B N7B 1.3606(19) . ?
N7B H7BA 0.93(2) . ?
N7B H7BB 0.85(2) . ?
O3A H3AB 0.83(2) . ?
O3A H3AC 0.86(2) . ?
O3B H3BC 0.85(3) . ?
O3B H3BB 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A C1A N1A 119.03(13) . . ?
O1A C1A C4A 125.09(14) . . ?
N1A C1A C4A 115.88(13) . . ?
C1A N1A H1AA 117.2 . . ?
C2A N1A C1A 125.52(13) . . ?
C2A N1A H1AA 117.2 . . ?
O2A C2A N1A 121.40(14) . . ?
O2A C2A N2A 122.36(13) . . ?
N2A C2A N1A 116.23(13) . . ?
C2A N2A H2AA 119.2 . . ?
C2A N2A C3A 121.66(13) . . ?
C3A N2A H2AA 119.2 . . ?
N2A C3A H3AA 118.7 . . ?
C4A C3A N2A 122.61(13) . . ?
C4A C3A H3AA 118.7 . . ?
C1A C4A C5A 118.79(13) . . ?
C3A C4A C1A 118.07(14) . . ?
C3A C4A C5A 123.12(14) . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C6A N3A C9A 116.02(13) . . ?
N3A C6A N5A 126.43(14) . . ?
N4A C6A N3A 117.23(13) . . ?
N4A C6A N5A 116.34(13) . . ?
C6A N4A H4AA 121.0(14) . . ?
C6A N4A H4AB 120.1(14) . . ?
H4AA N4A H4AB 118.9(19) . . ?
C7A N5A C6A 115.89(12) . . ?
N5A C7A N6A 115.47(13) . . ?
N5A C7A C8A 122.68(13) . . ?
N6A C7A C8A 121.83(14) . . ?
C7A N6A H6AA 117.3(13) . . ?
C7A N6A H6AB 119.6(13) . . ?
H6AA N6A H6AB 116.2(19) . . ?
C7A C8A H8AA 121.7 . . ?
C7A C8A C9A 116.51(13) . . ?
C9A C8A H8AA 121.7 . . ?
N3A C9A C8A 122.45(13) . . ?
N3A C9A N7A 116.52(14) . . ?
N7A C9A C8A 121.00(14) . . ?
C9A N7A H7AA 115.2(13) . . ?
C9A N7A H7AB 115.7(14) . . ?
H7AA N7A H7AB 119(2) . . ?
O1B C1B N1B 119.11(13) . . ?
O1B C1B C4B 124.96(14) . . ?
N1B C1B C4B 115.92(13) . . ?
C1B N1B H1BA 117.3 . . ?
C2B N1B C1B 125.50(13) . . ?
C2B N1B H1BA 117.3 . . ?
O2B C2B N1B 121.51(13) . . ?
O2B C2B N2B 122.53(13) . . ?
N2B C2B N1B 115.96(13) . . ?
C2B N2B H2BA 119.1 . . ?
C2B N2B C3B 121.80(12) . . ?
C3B N2B H2BA 119.1 . . ?
N2B C3B H3BA 118.7 . . ?
C4B C3B N2B 122.59(13) . . ?
C4B C3B H3BA 118.7 . . ?
C1B C4B C5B 118.73(13) . . ?
C3B C4B C1B 118.17(13) . . ?
C3B C4B C5B 123.07(13) . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
C4B C5B H5BC 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
C6B N3B C9B 115.88(13) . . ?
N3B C6B N4B 117.04(13) . . ?
N3B C6B N5B 126.66(13) . . ?
N4B C6B N5B 116.28(13) . . ?
C6B N4B H4BA 119.7(13) . . ?
C6B N4B H4BB 119.7(14) . . ?
H4BA N4B H4BB 112.7(19) . . ?
C7B N5B C6B 115.95(12) . . ?
N5B C7B N6B 115.70(13) . . ?
N5B C7B C8B 122.40(13) . . ?
N6B C7B C8B 121.89(13) . . ?
C7B N6B H6BA 114.9(13) . . ?
C7B N6B H6BB 119.2(13) . . ?
H6BA N6B H6BB 118.9(18) . . ?
C7B C8B H8BA 121.7 . . ?
C7B C8B C9B 116.60(13) . . ?
C9B C8B H8BA 121.7 . . ?
N3B C9B C8B 122.52(13) . . ?
N3B C9B N7B 116.28(13) . . ?
N7B C9B C8B 121.19(13) . . ?
C9B N7B H7BA 113.7(13) . . ?
C9B N7B H7BB 118.7(14) . . ?
H7BA N7B H7BB 120.0(18) . . ?
H3AB O3A H3AC 105(2) . . ?
H3BC O3B H3BB 103(2) . . ?

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
N1A H1AA N5B 0.88 2.07 2.9125(18) 159.8 .
N2A H2AA O3A 0.88 1.96 2.8240(17) 168.1 .
N4A H4AA O2A 0.90(2) 2.25(2) 2.9239(17) 132.0(18) .
N4A H4AB O2B 0.91(2) 2.03(2) 2.9362(17) 179(2) .
N6A H6AA O1B 0.90(2) 2.14(2) 3.0363(18) 171.5(19) .
N6A H6AB O1B 0.87(2) 2.15(2) 2.9632(17) 155.6(18) 2_767
N7A H7AA O3B 0.90(2) 2.17(2) 2.9418(18) 143.3(18) 1_565
N1B H1BA N5A 0.88 2.10 2.9279(18) 156.8 .
N2B H2BA O3B 0.88 1.98 2.8336(16) 164.5 .
N4B H4BA O2B 0.90(2) 2.27(2) 2.9734(17) 135.0(18) .
N4B H4BB O2A 0.89(2) 2.05(2) 2.9393(17) 177(2) .
N6B H6BA O1A 0.89(2) 2.16(2) 3.0443(17) 169.0(19) .
N6B H6BB O1A 0.88(2) 2.13(2) 2.9556(17) 157.4(18) 2_655
N7B H7BA O3A 0.93(2) 2.15(2) 2.9446(17) 142.0(17) 1_545
N7B H7BB N5A 0.85(2) 2.52(2) 3.2245(18) 141.1(18) 2_756
O3A H3AB N3A 0.83(2) 2.09(2) 2.8788(18) 159(2) .
O3A H3AC O2A 0.86(2) 1.99(2) 2.8161(16) 164(2) 2_666
O3B H3BC O2B 0.85(3) 2.07(2) 2.8471(16) 152(2) 2_756
O3B H3BB N3B 0.84(2) 2.06(2) 2.8586(18) 158(2) .

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
C1A N1A C2A O2A -177.78(14) . . . . ?
C1A N1A C2A N2A 1.5(2) . . . . ?
O1A C1A N1A C2A 177.30(15) . . . . ?
O1A C1A C4A C3A -178.17(15) . . . . ?
O1A C1A C4A C5A 0.0(2) . . . . ?
N1A C1A C4A C3A 1.0(2) . . . . ?
N1A C1A C4A C5A 179.26(13) . . . . ?
N1A C2A N2A C3A -0.1(2) . . . . ?
C2A N2A C3A C4A -0.7(2) . . . . ?
O2A C2A N2A C3A 179.18(15) . . . . ?
N2A C3A C4A C1A 0.2(2) . . . . ?
N2A C3A C4A C5A -177.94(14) . . . . ?
C4A C1A N1A C2A -2.0(2) . . . . ?
N3A C6A N5A C7A -0.3(2) . . . . ?
C6A N3A C9A C8A 0.7(2) . . . . ?
C6A N3A C9A N7A -177.42(14) . . . . ?
C6A N5A C7A N6A -179.05(13) . . . . ?
C6A N5A C7A C8A -0.5(2) . . . . ?
N4A C6A N5A C7A -179.62(14) . . . . ?
N5A C7A C8A C9A 1.4(2) . . . . ?
C7A C8A C9A N3A -1.5(2) . . . . ?
C7A C8A C9A N7A 176.58(14) . . . . ?
N6A C7A C8A C9A 179.79(14) . . . . ?
C9A N3A C6A N4A 179.52(15) . . . . ?
C9A N3A C6A N5A 0.2(2) . . . . ?
C1B N1B C2B O2B -179.40(14) . . . . ?
C1B N1B C2B N2B 0.5(2) . . . . ?
O1B C1B N1B C2B 177.29(15) . . . . ?
O1B C1B C4B C3B -177.20(15) . . . . ?
O1B C1B C4B C5B 0.7(2) . . . . ?
N1B C1B C4B C3B 2.4(2) . . . . ?
N1B C1B C4B C5B -179.63(13) . . . . ?
N1B C2B N2B C3B 1.4(2) . . . . ?
C2B N2B C3B C4B -1.2(2) . . . . ?
O2B C2B N2B C3B -178.75(14) . . . . ?
N2B C3B C4B C1B -0.8(2) . . . . ?
N2B C3B C4B C5B -178.66(14) . . . . ?
C4B C1B N1B C2B -2.4(2) . . . . ?
N3B C6B N5B C7B 0.4(2) . . . . ?
C6B N3B C9B C8B -0.4(2) . . . . ?
C6B N3B C9B N7B -178.98(14) . . . . ?
C6B N5B C7B N6B -179.32(13) . . . . ?
C6B N5B C7B C8B -0.8(2) . . . . ?
N4B C6B N5B C7B -178.11(14) . . . . ?
N5B C7B C8B C9B 0.5(2) . . . . ?
C7B C8B C9B N3B 0.1(2) . . . . ?
C7B C8B C9B N7B 178.61(14) . . . . ?
N6B C7B C8B C9B 178.99(14) . . . . ?
C9B N3B C6B N4B 178.66(14) . . . . ?
C9B N3B C6B N5B 0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.903(2)
2 0.097(2)

