# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_KA1171_0m
_database_code_depnum_ccdc_archive 'CCDC 2512924'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-12-03 deposited with the CCDC.	2026-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Favipiravir Theophylline Cocrystal Form I'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N4 O2, C5 H4 F N3 O2'
_chemical_formula_sum            'C12 H12 F N7 O4'
_chemical_formula_weight         337.29

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.346(13)
_cell_length_b                   7.489(6)
_cell_length_c                   14.808(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.83(2)
_cell_angle_gamma                90
_cell_volume                     1409(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2704
_cell_measurement_theta_min      2.463
_cell_measurement_theta_max      23.516

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11242
_diffrn_reflns_av_unetI/netI     0.1198
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.465
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2881
_reflns_number_gt                1423
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+0.9124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0064(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2881
_refine_ls_number_parameters     235
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1697
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.022
_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
F1 F 0.45956(16) 0.1228(3) 0.23793(15) 0.0698(7) Uani 1 1 d . . . . .
O1 O 0.09686(19) 0.4101(3) -0.04738(16) 0.0516(7) Uani 1 1 d . . . . .
O2 O 0.2270(2) 0.2497(4) -0.11615(19) 0.0657(8) Uani 1 1 d D . . . .
H2O H 0.172(2) 0.309(5) -0.107(3) 0.079 Uiso 1 1 d D U . . .
N1 N 0.1156(3) 0.3907(4) 0.1092(2) 0.0424(8) Uani 1 1 d D . . . .
H1N H 0.0553(19) 0.439(5) 0.097(3) 0.079(16) Uiso 1 1 d D . . . .
H2N H 0.152(3) 0.353(5) 0.1631(17) 0.065(14) Uiso 1 1 d D . . . .
N2 N 0.3754(3) 0.1333(4) -0.0142(2) 0.0533(9) Uani 1 1 d . . . . .
N3 N 0.3097(2) 0.2352(3) 0.13996(19) 0.0378(7) Uani 1 1 d . . . . .
C1 C 0.1477(3) 0.3615(4) 0.0348(2) 0.0385(9) Uani 1 1 d . . . . .
C2 C 0.2502(3) 0.2697(4) 0.0504(2) 0.0335(8) Uani 1 1 d . . . . .
C3 C 0.2838(3) 0.2182(5) -0.0266(3) 0.0453(10) Uani 1 1 d . . . . .
C4 C 0.4328(3) 0.1016(5) 0.0746(3) 0.0507(10) Uani 1 1 d . . . . .
H4 H 0.496929 0.042619 0.086897 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3980(3) 0.1555(5) 0.1485(3) 0.0440(9) Uani 1 1 d . . . . .
O3 O 0.11262(17) 0.1098(3) 0.59941(15) 0.0467(7) Uani 1 1 d . . . . .
O4 O 0.41362(18) 0.3889(3) 0.58869(15) 0.0487(7) Uani 1 1 d . . . . .
N4 N 0.2620(2) 0.2518(3) 0.59248(17) 0.0356(7) Uani 1 1 d . . . . .
N5 N 0.29693(19) 0.3110(3) 0.44785(17) 0.0286(6) Uani 1 1 d . . . . .
N6 N 0.1595(2) 0.2107(3) 0.30712(17) 0.0357(7) Uani 1 1 d . . . . .
N7 N 0.0533(2) 0.0954(4) 0.38275(19) 0.0356(7) Uani 1 1 d . . . . .
H7N H 0.002(2) 0.042(4) 0.393(2) 0.035(10) Uiso 1 1 d . . . . .
C6 C 0.1656(2) 0.1678(4) 0.5508(2) 0.0329(8) Uani 1 1 d . . . . .
C7 C 0.2981(3) 0.2668(6) 0.6959(2) 0.0712(14) Uani 1 1 d . . . . .
H7A H 0.311988 0.389846 0.713597 0.107 Uiso 1 1 calc R U . . .
H7B H 0.361280 0.198319 0.721117 0.107 Uiso 1 1 calc R U . . .
H7C H 0.244553 0.222267 0.721021 0.107 Uiso 1 1 calc R U . . .
C8 C 0.3297(3) 0.3211(4) 0.5452(2) 0.0333(8) Uani 1 1 d . . . . .
C9 C 0.3662(2) 0.3752(5) 0.3948(2) 0.0421(9) Uani 1 1 d . . . . .
H9A H 0.324421 0.421085 0.334535 0.063 Uiso 1 1 calc R U . . .
H9B H 0.408869 0.278275 0.385071 0.063 Uiso 1 1 calc R U . . .
H9C H 0.410787 0.468164 0.430127 0.063 Uiso 1 1 calc R U . . .
C10 C 0.2025(2) 0.2312(4) 0.4024(2) 0.0283(8) Uani 1 1 d . . . . .
C11 C 0.1401(2) 0.1628(4) 0.4513(2) 0.0278(8) Uani 1 1 d . . . . .
C12 C 0.0690(2) 0.1266(5) 0.2997(2) 0.0387(9) Uani 1 1 d . . . . .
H12 H 0.021528 0.093125 0.241940 0.046 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
F1 C5 1.349(4) . ?
O1 C1 1.252(4) . ?
O2 C3 1.332(4) . ?
O2 H2O 0.909(18) . ?
N1 C1 1.317(4) . ?
N1 H1N 0.850(18) . ?
N1 H2N 0.846(18) . ?
N2 C4 1.325(4) . ?
N2 C3 1.340(4) . ?
N3 C5 1.293(4) . ?
N3 C2 1.345(4) . ?
C1 C2 1.484(5) . ?
C2 C3 1.401(5) . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
O3 C6 1.232(3) . ?
O4 C8 1.219(4) . ?
N4 C6 1.395(4) . ?
N4 C8 1.401(4) . ?
N4 C7 1.463(4) . ?
N5 C10 1.371(4) . ?
N5 C8 1.374(4) . ?
N5 C9 1.465(4) . ?
N6 C12 1.336(4) . ?
N6 C10 1.360(4) . ?
N7 C12 1.330(4) . ?
N7 C11 1.381(4) . ?
N7 H7N 0.85(3) . ?
C6 C11 1.407(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.360(4) . ?
C12 H12 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
C3 O2 H2O 100(3) . . ?
C1 N1 H1N 115(3) . . ?
C1 N1 H2N 120(3) . . ?
H1N N1 H2N 125(4) . . ?
C4 N2 C3 116.6(3) . . ?
C5 N3 C2 115.5(3) . . ?
O1 C1 N1 123.1(3) . . ?
O1 C1 C2 119.1(3) . . ?
N1 C1 C2 117.8(3) . . ?
N3 C2 C3 120.7(3) . . ?
N3 C2 C1 118.7(3) . . ?
C3 C2 C1 120.6(3) . . ?
O2 C3 N2 115.9(3) . . ?
O2 C3 C2 122.4(4) . . ?
N2 C3 C2 121.7(3) . . ?
N2 C4 C5 120.3(4) . . ?
N2 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N3 C5 F1 116.3(3) . . ?
N3 C5 C4 125.3(4) . . ?
F1 C5 C4 118.4(4) . . ?
C6 N4 C8 126.5(3) . . ?
C6 N4 C7 117.5(3) . . ?
C8 N4 C7 116.1(3) . . ?
C10 N5 C8 119.2(3) . . ?
C10 N5 C9 121.1(3) . . ?
C8 N5 C9 119.6(3) . . ?
C12 N6 C10 102.9(3) . . ?
C12 N7 C11 106.3(3) . . ?
C12 N7 H7N 128(2) . . ?
C11 N7 H7N 125(2) . . ?
O3 C6 N4 121.1(3) . . ?
O3 C6 C11 127.2(3) . . ?
N4 C6 C11 111.7(3) . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 N5 121.5(3) . . ?
O4 C8 N4 121.3(3) . . ?
N5 C8 N4 117.2(3) . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N6 C10 C11 112.2(3) . . ?
N6 C10 N5 126.3(3) . . ?
C11 C10 N5 121.6(3) . . ?
C10 C11 N7 105.0(3) . . ?
C10 C11 C6 123.8(3) . . ?
N7 C11 C6 131.2(3) . . ?
N7 C12 N6 113.7(3) . . ?
N7 C12 H12 123.2 . . ?
N6 C12 H12 123.2 . . ?

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
C5 N3 C2 C3 0.8(4) . . . . ?
C5 N3 C2 C1 -179.8(3) . . . . ?
O1 C1 C2 N3 172.9(3) . . . . ?
N1 C1 C2 N3 -6.0(4) . . . . ?
O1 C1 C2 C3 -7.8(5) . . . . ?
N1 C1 C2 C3 173.4(3) . . . . ?
C4 N2 C3 O2 179.8(3) . . . . ?
C4 N2 C3 C2 -0.4(5) . . . . ?
N3 C2 C3 O2 179.9(3) . . . . ?
C1 C2 C3 O2 0.6(5) . . . . ?
N3 C2 C3 N2 0.1(5) . . . . ?
C1 C2 C3 N2 -179.2(3) . . . . ?
C3 N2 C4 C5 -0.2(5) . . . . ?
C2 N3 C5 F1 178.9(3) . . . . ?
C2 N3 C5 C4 -1.6(5) . . . . ?
N2 C4 C5 N3 1.3(6) . . . . ?
N2 C4 C5 F1 -179.1(3) . . . . ?
C8 N4 C6 O3 179.3(3) . . . . ?
C7 N4 C6 O3 0.5(5) . . . . ?
C8 N4 C6 C11 -1.5(4) . . . . ?
C7 N4 C6 C11 179.7(3) . . . . ?
C10 N5 C8 O4 179.1(3) . . . . ?
C9 N5 C8 O4 3.0(4) . . . . ?
C10 N5 C8 N4 -1.6(4) . . . . ?
C9 N5 C8 N4 -177.7(3) . . . . ?
C6 N4 C8 O4 -178.4(3) . . . . ?
C7 N4 C8 O4 0.3(5) . . . . ?
C6 N4 C8 N5 2.2(5) . . . . ?
C7 N4 C8 N5 -179.0(3) . . . . ?
C12 N6 C10 C11 -0.3(3) . . . . ?
C12 N6 C10 N5 -180.0(3) . . . . ?
C8 N5 C10 N6 -179.9(3) . . . . ?
C9 N5 C10 N6 -3.8(5) . . . . ?
C8 N5 C10 C11 0.5(4) . . . . ?
C9 N5 C10 C11 176.5(3) . . . . ?
N6 C10 C11 N7 0.1(4) . . . . ?
N5 C10 C11 N7 179.8(3) . . . . ?
N6 C10 C11 C6 -179.5(3) . . . . ?
N5 C10 C11 C6 0.2(5) . . . . ?
C12 N7 C11 C10 0.1(3) . . . . ?
C12 N7 C11 C6 179.7(3) . . . . ?
O3 C6 C11 C10 179.4(3) . . . . ?
N4 C6 C11 C10 0.3(4) . . . . ?
O3 C6 C11 N7 -0.1(6) . . . . ?
N4 C6 C11 N7 -179.2(3) . . . . ?
C11 N7 C12 N6 -0.3(4) . . . . ?
C10 N6 C12 N7 0.4(4) . . . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_ka996_0m-auto_pl
_database_code_depnum_ccdc_archive 'CCDC 2512925'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-12-03 deposited with the CCDC.	2026-04-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'Favipiravir Theophylline Cocrystal Form II'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N4 O2, C5 H4 F N3 O2'
_chemical_formula_sum            'C12 H12 F N7 O4'
_chemical_formula_weight         337.29

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.228(5)
_cell_length_b                   13.950(10)
_cell_length_c                   14.273(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.548(19)
_cell_angle_gamma                90
_cell_volume                     1432.4(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.195
_cell_measurement_theta_max      30.581

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7129
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28742
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.831
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3284
_reflns_number_gt                2699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.7101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3284
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.008
_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
F1 F 0.1131(2) 0.56717(10) 0.28803(9) 0.0710(4) Uani 1 1 d . . . . .
O1 O 0.4462(2) 0.82923(10) 0.56894(9) 0.0497(4) Uani 1 1 d . . . . .
O2 O 0.3301(2) 0.91107(10) 0.41331(11) 0.0574(4) Uani 1 1 d . . . . .
H2O H 0.377(4) 0.9003(18) 0.4739(19) 0.068(7) Uiso 1 1 d . . . . .
N1 N 0.4085(2) 0.66989(13) 0.58755(11) 0.0446(4) Uani 1 1 d . . . . .
H1N H 0.471(3) 0.6702(17) 0.6468(18) 0.065(7) Uiso 1 1 d . . . . .
H2N H 0.366(3) 0.6127(17) 0.5656(16) 0.053(6) Uiso 1 1 d . . . . .
N2 N 0.1977(2) 0.81860(13) 0.29503(11) 0.0493(4) Uani 1 1 d . . . . .
N3 N 0.2428(2) 0.65571(11) 0.40831(10) 0.0390(3) Uani 1 1 d . . . . .
C1 C 0.3896(2) 0.74906(13) 0.53858(11) 0.0363(4) Uani 1 1 d . . . . .
C2 C 0.2984(2) 0.74229(12) 0.44045(11) 0.0326(4) Uani 1 1 d . . . . .
C3 C 0.2757(3) 0.82383(14) 0.38378(12) 0.0395(4) Uani 1 1 d . . . . .
C4 C 0.1442(3) 0.73252(16) 0.26389(12) 0.0484(5) Uani 1 1 d . . . . .
H4 H 0.089738 0.725535 0.202522 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1683(3) 0.65299(15) 0.32154(12) 0.0431(4) Uani 1 1 d . . . . .
O3 O 0.65147(19) 0.65658(9) 0.75943(9) 0.0446(3) Uani 1 1 d . . . . .
O4 O 0.9321(2) 0.69996(11) 1.05685(10) 0.0584(4) Uani 1 1 d . . . . .
N4 N 0.7893(2) 0.67913(10) 0.90894(10) 0.0356(3) Uani 1 1 d . . . . .
N5 N 0.8139(2) 0.83228(11) 0.98135(9) 0.0361(3) Uani 1 1 d . . . . .
N6 N 0.6910(2) 0.96381(11) 0.88080(11) 0.0449(4) Uani 1 1 d . . . . .
N7 N 0.6089(2) 0.87533(11) 0.75301(10) 0.0399(4) Uani 1 1 d . . . . .
H7N H 0.566(3) 0.8604(18) 0.6917(18) 0.065(7) Uiso 1 1 d . . . . .
C6 C 0.7024(2) 0.71255(12) 0.82323(11) 0.0311(3) Uani 1 1 d . . . . .
C7 C 0.8210(3) 0.57527(14) 0.91786(15) 0.0534(5) Uani 1 1 d . . . . .
H7A H 0.844276 0.558641 0.983202 0.080 Uiso 1 1 calc R U . . .
H7B H 0.926490 0.557773 0.885513 0.080 Uiso 1 1 calc R U . . .
H7C H 0.713085 0.541597 0.890676 0.080 Uiso 1 1 calc R U . . .
C8 C 0.8504(2) 0.73572(13) 0.98718(11) 0.0378(4) Uani 1 1 d . . . . .
C9 C 0.8703(3) 0.89473(15) 1.06183(13) 0.0499(5) Uani 1 1 d . . . . .
H9A H 0.839330 0.864650 1.118771 0.075 Uiso 1 1 calc R U . . .
H9B H 0.806390 0.954951 1.053923 0.075 Uiso 1 1 calc R U . . .
H9C H 1.001966 0.905433 1.065454 0.075 Uiso 1 1 calc R U . . .
C10 C 0.7316(2) 0.87033(12) 0.89834(11) 0.0325(4) Uani 1 1 d . . . . .
C11 C 0.6827(2) 0.81334(12) 0.82209(11) 0.0316(3) Uani 1 1 d . . . . .
C12 C 0.6188(3) 0.96260(14) 0.79136(13) 0.0488(5) Uani 1 1 d . . . . .
H12 H 0.578994 1.017630 0.758591 0.059 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
F1 C5 1.336(2) . ?
O1 C1 1.254(2) . ?
O2 C3 1.335(2) . ?
O2 H2O 0.91(3) . ?
N1 C1 1.307(2) . ?
N1 H1N 0.92(3) . ?
N1 H2N 0.90(2) . ?
N2 C4 1.325(3) . ?
N2 C3 1.338(2) . ?
N3 C5 1.303(2) . ?
N3 C2 1.340(2) . ?
C1 C2 1.492(2) . ?
C2 C3 1.396(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
O3 C6 1.229(2) . ?
O4 C8 1.214(2) . ?
N4 C6 1.400(2) . ?
N4 C8 1.403(2) . ?
N4 C7 1.470(3) . ?
N5 C8 1.374(3) . ?
N5 C10 1.380(2) . ?
N5 C9 1.468(2) . ?
N6 C12 1.332(3) . ?
N6 C10 1.355(2) . ?
N7 C12 1.334(3) . ?
N7 C11 1.379(2) . ?
N7 H7N 0.92(3) . ?
C6 C11 1.413(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.366(2) . ?
C12 H12 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
C3 O2 H2O 102.7(16) . . ?
C1 N1 H1N 120.4(15) . . ?
C1 N1 H2N 123.2(15) . . ?
H1N N1 H2N 116(2) . . ?
C4 N2 C3 116.72(17) . . ?
C5 N3 C2 115.76(16) . . ?
O1 C1 N1 123.73(17) . . ?
O1 C1 C2 118.72(16) . . ?
N1 C1 C2 117.54(16) . . ?
N3 C2 C3 121.44(16) . . ?
N3 C2 C1 117.97(15) . . ?
C3 C2 C1 120.58(16) . . ?
O2 C3 N2 115.67(17) . . ?
O2 C3 C2 123.05(16) . . ?
N2 C3 C2 121.29(18) . . ?
N2 C4 C5 120.79(17) . . ?
N2 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
N3 C5 F1 116.63(18) . . ?
N3 C5 C4 124.01(19) . . ?
F1 C5 C4 119.36(17) . . ?
C6 N4 C8 126.02(15) . . ?
C6 N4 C7 117.18(15) . . ?
C8 N4 C7 116.81(15) . . ?
C8 N5 C10 119.58(14) . . ?
C8 N5 C9 119.84(15) . . ?
C10 N5 C9 120.53(16) . . ?
C12 N6 C10 102.87(15) . . ?
C12 N7 C11 106.09(15) . . ?
C12 N7 H7N 126.4(15) . . ?
C11 N7 H7N 127.4(15) . . ?
O3 C6 N4 120.86(16) . . ?
O3 C6 C11 126.96(15) . . ?
N4 C6 C11 112.17(14) . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 N5 121.87(16) . . ?
O4 C8 N4 120.76(18) . . ?
N5 C8 N4 117.37(14) . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N6 C10 C11 112.22(15) . . ?
N6 C10 N5 126.64(15) . . ?
C11 C10 N5 121.14(16) . . ?
C10 C11 N7 104.89(16) . . ?
C10 C11 C6 123.49(15) . . ?
N7 C11 C6 131.56(15) . . ?
N6 C12 N7 113.92(16) . . ?
N6 C12 H12 123.0 . . ?
N7 C12 H12 123.0 . . ?

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
C5 N3 C2 C3 0.4(2) . . . . ?
C5 N3 C2 C1 -178.32(16) . . . . ?
O1 C1 C2 N3 178.41(16) . . . . ?
N1 C1 C2 N3 -0.5(2) . . . . ?
O1 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C3 -179.22(17) . . . . ?
C4 N2 C3 O2 179.39(18) . . . . ?
C4 N2 C3 C2 -0.3(3) . . . . ?
N3 C2 C3 O2 -179.71(17) . . . . ?
C1 C2 C3 O2 -1.0(3) . . . . ?
N3 C2 C3 N2 -0.1(3) . . . . ?
C1 C2 C3 N2 178.61(16) . . . . ?
C3 N2 C4 C5 0.3(3) . . . . ?
C2 N3 C5 F1 179.55(16) . . . . ?
C2 N3 C5 C4 -0.4(3) . . . . ?
N2 C4 C5 N3 0.1(3) . . . . ?
N2 C4 C5 F1 -179.89(19) . . . . ?
C8 N4 C6 O3 -178.83(16) . . . . ?
C7 N4 C6 O3 1.6(2) . . . . ?
C8 N4 C6 C11 0.8(2) . . . . ?
C7 N4 C6 C11 -178.77(16) . . . . ?
C10 N5 C8 O4 175.68(18) . . . . ?
C9 N5 C8 O4 -1.5(3) . . . . ?
C10 N5 C8 N4 -4.3(2) . . . . ?
C9 N5 C8 N4 178.50(16) . . . . ?
C6 N4 C8 O4 -176.56(17) . . . . ?
C7 N4 C8 O4 3.0(3) . . . . ?
C6 N4 C8 N5 3.4(3) . . . . ?
C7 N4 C8 N5 -177.06(17) . . . . ?
C12 N6 C10 C11 -1.0(2) . . . . ?
C12 N6 C10 N5 178.48(18) . . . . ?
C8 N5 C10 N6 -178.32(17) . . . . ?
C9 N5 C10 N6 -1.1(3) . . . . ?
C8 N5 C10 C11 1.1(2) . . . . ?
C9 N5 C10 C11 178.32(17) . . . . ?
N6 C10 C11 N7 0.5(2) . . . . ?
N5 C10 C11 N7 -178.98(15) . . . . ?
N6 C10 C11 C6 -177.00(16) . . . . ?
N5 C10 C11 C6 3.5(3) . . . . ?
C12 N7 C11 C10 0.2(2) . . . . ?
C12 N7 C11 C6 177.41(19) . . . . ?
O3 C6 C11 C10 175.34(17) . . . . ?
N4 C6 C11 C10 -4.2(2) . . . . ?
O3 C6 C11 N7 -1.5(3) . . . . ?
N4 C6 C11 N7 178.97(17) . . . . ?
C10 N6 C12 N7 1.1(2) . . . . ?
C11 N7 C12 N6 -0.8(2) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
