# Electronic Supplementary Material (ESI) for RSC Mechanochemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_tp_ma_triclinic
_database_code_depnum_ccdc_archive 'CCDC 2305331'
loop_
_audit_author_name
_audit_author_address
'Laura Macchietti'
;University of Bologna
Italy
;
_audit_update_record             
;
2023-11-02 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;
_audit_creation_date             2023-10-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'Theophylline, Malonic acid'
_chemical_formula_moiety         'C3 H4 O4, C7 H8 N4 O2'
_chemical_formula_sum            'C10 H12 N4 O6'
_chemical_formula_weight         284.24
_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'

_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                   8.1438(6)
_cell_length_b                   12.4857(10)
_cell_length_c                   12.9437(10)
_cell_angle_alpha                92.848(6)
_cell_angle_beta                 103.379(6)
_cell_angle_gamma                102.355(7)
_cell_volume                     1243.92(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3307
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      26.6660
_cell_measurement_theta_min      2.6450
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.85a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_preparation       
'Slow evaporation from chloroform/ethanol solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.807
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10235
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.607
_diffrn_reflns_theta_min         2.212
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1385
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.807
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  31.00   1.00   14.97    --  -16.68  77.00-150.00   75
  2  ω      3.00  86.00   1.00   14.97    --   17.62  57.00  90.00   83
  3  ω    -31.00  -2.00   1.00   14.97    --   17.62 -77.00-180.00   29
  4  ω     -9.00  28.00   1.00   14.97    --   17.62  77.00  60.00   37
  5  ω     -6.00  30.00   1.00   14.97    --   17.62  77.00-180.00   36
  6  ω    -51.00  36.00   1.00   14.97    --   17.62 -57.00 -60.00   87
  7  ω     -9.00  17.00   1.00   14.97    --   17.62  77.00 -30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0079354000
_diffrn_orient_matrix_UB_12      0.0576978000
_diffrn_orient_matrix_UB_13      0.0077472000
_diffrn_orient_matrix_UB_21      0.0722592000
_diffrn_orient_matrix_UB_22      0.0043430000
_diffrn_orient_matrix_UB_23      0.0441199000
_diffrn_orient_matrix_UB_31      0.0564507000
_diffrn_orient_matrix_UB_32      0.0084526000
_diffrn_orient_matrix_UB_33      -0.0346575000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3998
_reflns_number_total             5652
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0687
_refine_ls_restrained_S_all      1.104
_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)+(0.0584P)²+0.3826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1524
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N1(H1), C14(H14), C4(H4)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C9(H9A,H9B,H9C), C20(H20A,H20B,H20C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O10(H10), O7(H7), O3(H3), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_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
O10 O 0.5328(3) 0.21579(14) 0.41372(15) 0.0575(6) Uani 1 1 d . . . . .
H10 H 0.510541 0.241219 0.467132 0.086 Uiso 1 1 calc R U . . .
O12 O 0.6724(3) 0.67447(15) 0.08130(14) 0.0525(5) Uani 1 1 d . . . . .
O7 O 0.7701(3) 0.28458(15) 0.12794(16) 0.0584(6) Uani 1 1 d . . . . .
H7 H 0.779075 0.321820 0.078236 0.088 Uiso 1 1 calc R U . . .
N8 N 0.5181(3) 0.86505(15) 0.28904(15) 0.0353(5) Uani 1 1 d . . . . .
O11 O 0.5192(3) 0.99096(15) 0.16967(15) 0.0600(6) Uani 1 1 d . . . . .
O1 O 0.8341(3) 0.95618(18) -0.44392(18) 0.0627(6) Uani 1 1 d . . . . .
O3 O 0.9055(3) 0.73441(16) -0.34625(16) 0.0618(6) Uani 1 1 d . . . . .
H3 H 0.882750 0.668211 -0.339937 0.093 Uiso 1 1 calc R U . . .
N6 N 0.5926(3) 0.60010(15) 0.29102(16) 0.0381(5) Uani 1 1 d . . . . .
H6 H 0.618091 0.542171 0.266380 0.046 Uiso 1 1 calc R U . . .
O5 O 0.8874(3) 0.52468(16) -0.35517(15) 0.0595(6) Uani 1 1 d . . . . .
O6 O 0.9900(3) 0.18787(16) -0.28231(16) 0.0607(6) Uani 1 1 d . . . . .
N7 N 0.5965(3) 0.83313(16) 0.12749(15) 0.0386(5) Uani 1 1 d . . . . .
N5 N 0.5197(3) 0.71385(15) 0.39998(16) 0.0396(5) Uani 1 1 d . . . . .
N2 N 0.8047(3) 0.39561(16) -0.03909(16) 0.0400(5) Uani 1 1 d . . . . .
N4 N 0.9042(3) 0.28059(16) -0.15717(17) 0.0408(5) Uani 1 1 d . . . . .
O4 O 0.8081(3) 0.74751(16) -0.19988(16) 0.0611(6) Uani 1 1 d . . . . .
N3 N 0.9387(3) 0.35658(18) -0.31733(16) 0.0450(5) Uani 1 1 d . . . . .
N1 N 0.7925(3) 0.53391(17) -0.13864(16) 0.0435(5) Uani 1 1 d . . . . .
H1 H 0.776425 0.596097 -0.159317 0.052 Uiso 1 1 calc R U . . .
O8 O 0.6697(3) 0.42094(16) 0.18274(16) 0.0695(7) Uani 1 1 d . . . . .
O9 O 0.5849(4) 0.38892(15) 0.38303(17) 0.0735(7) Uani 1 1 d . . . . .
O2 O 1.1144(3) 0.9712(2) -0.37536(18) 0.0720(7) Uani 1 1 d . . . . .
H2 H 1.119683 0.988095 -0.435121 0.108 Uiso 1 1 calc R U . . .
C16 C 0.5406(3) 0.76180(18) 0.31112(18) 0.0315(5) Uani 1 1 d . . . . .
C15 C 0.5859(3) 0.69507(17) 0.24221(18) 0.0316(5) Uani 1 1 d . . . . .
C17 C 0.6229(3) 0.72731(19) 0.14496(18) 0.0354(5) Uani 1 1 d . . . . .
C6 C 0.8562(3) 0.37403(19) -0.12883(19) 0.0355(5) Uani 1 1 d . . . . .
C13 C 0.5832(3) 0.29535(18) 0.35919(18) 0.0363(6) Uani 1 1 d . . . . .
C18 C 0.5434(3) 0.90225(19) 0.19483(19) 0.0389(6) Uani 1 1 d . . . . .
C8 C 0.9474(3) 0.2693(2) -0.2536(2) 0.0439(6) Uani 1 1 d . . . . .
C11 C 0.6938(4) 0.3303(2) 0.1909(2) 0.0402(6) Uani 1 1 d . . . . .
C5 C 0.8505(3) 0.4570(2) -0.19189(19) 0.0394(6) Uani 1 1 d . . . . .
C14 C 0.5523(4) 0.6152(2) 0.3834(2) 0.0427(6) Uani 1 1 d . . . . .
H14 H 0.547277 0.562442 0.431539 0.051 Uiso 1 1 calc R U . . .
C7 C 0.8925(3) 0.4540(2) -0.2925(2) 0.0421(6) Uani 1 1 d . . . . .
C4 C 0.7662(4) 0.4935(2) -0.0492(2) 0.0430(6) Uani 1 1 d . . . . .
H4 H 0.725462 0.529679 0.000696 0.052 Uiso 1 1 calc R U . . .
C1 C 0.9576(4) 0.9487(2) -0.3702(2) 0.0517(7) Uani 1 1 d . . . . .
C3 C 0.8720(4) 0.7884(2) -0.2675(2) 0.0471(7) Uani 1 1 d . . . . .
C19 C 0.4655(4) 0.9345(2) 0.3636(2) 0.0465(7) Uani 1 1 d . . . . .
H19A H 0.342597 0.911406 0.355518 0.070 Uiso 1 1 calc R U . . .
H19B H 0.494431 1.009948 0.348985 0.070 Uiso 1 1 calc R U . . .
H19C H 0.525113 0.927889 0.435408 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6428(4) 0.2535(2) 0.2682(2) 0.0524(8) Uani 1 1 d . . . . .
H12A H 0.550805 0.192905 0.228137 0.063 Uiso 1 1 calc R U . . .
H12B H 0.741439 0.222856 0.297678 0.063 Uiso 1 1 calc R U . . .
C9 C 0.9158(4) 0.1944(2) -0.0857(2) 0.0563(8) Uani 1 1 d . . . . .
H9A H 0.803942 0.165691 -0.072960 0.084 Uiso 1 1 calc R U . . .
H9B H 0.997608 0.224615 -0.019205 0.084 Uiso 1 1 calc R U . . .
H9C H 0.953579 0.136162 -0.117867 0.084 Uiso 1 1 calc R U . . .
C20 C 0.6271(4) 0.8769(2) 0.0285(2) 0.0581(8) Uani 1 1 d . . . . .
H20A H 0.666619 0.824674 -0.010878 0.087 Uiso 1 1 calc R U . . .
H20B H 0.713579 0.945059 0.045750 0.087 Uiso 1 1 calc R U . . .
H20C H 0.521031 0.889638 -0.014057 0.087 Uiso 1 1 calc R U . . .
C2 C 0.9241(5) 0.9112(2) -0.2671(2) 0.0640(9) Uani 1 1 d . . . . .
H2A H 1.028262 0.939464 -0.210444 0.077 Uiso 1 1 calc R U . . .
H2B H 0.833026 0.942964 -0.250933 0.077 Uiso 1 1 calc R U . . .
C10 C 0.9770(4) 0.3411(3) -0.4223(2) 0.0670(9) Uani 1 1 d . . . . .
H10A H 0.870783 0.311309 -0.475435 0.101 Uiso 1 1 calc R U . . .
H10B H 1.052276 0.291156 -0.419163 0.101 Uiso 1 1 calc R U . . .
H10C H 1.032856 0.410869 -0.440522 0.101 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
O10 H10 0.8200 . ?
O10 C13 1.297(3) . ?
O12 C17 1.220(3) . ?
O7 H7 0.8200 . ?
O7 C11 1.310(3) . ?
N8 C16 1.375(3) . ?
N8 C18 1.370(3) . ?
N8 C19 1.461(3) . ?
O11 C18 1.213(3) . ?
O1 C1 1.239(4) . ?
O3 H3 0.8200 . ?
O3 C3 1.307(3) . ?
N6 H6 0.8600 . ?
N6 C15 1.376(3) . ?
N6 C14 1.326(3) . ?
O5 C7 1.229(3) . ?
O6 C8 1.211(3) . ?
N7 C17 1.404(3) . ?
N7 C18 1.397(3) . ?
N7 C20 1.471(3) . ?
N5 C16 1.351(3) . ?
N5 C14 1.332(3) . ?
N2 C6 1.357(3) . ?
N2 C4 1.331(3) . ?
N4 C6 1.367(3) . ?
N4 C8 1.382(3) . ?
N4 C9 1.458(3) . ?
O4 C3 1.200(3) . ?
N3 C8 1.403(3) . ?
N3 C7 1.392(3) . ?
N3 C10 1.475(3) . ?
N1 H1 0.8600 . ?
N1 C5 1.379(3) . ?
N1 C4 1.329(3) . ?
O8 C11 1.194(3) . ?
O9 C13 1.190(3) . ?
O2 H2 0.8200 . ?
O2 C1 1.266(3) . ?
C16 C15 1.355(3) . ?
C15 C17 1.418(3) . ?
C6 C5 1.352(3) . ?
C13 C12 1.486(3) . ?
C11 C12 1.487(3) . ?
C5 C7 1.421(3) . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?
C1 C2 1.500(4) . ?
C3 C2 1.499(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
C13 O10 H10 109.5 . . ?
C11 O7 H7 109.5 . . ?
C16 N8 C19 121.06(19) . . ?
C18 N8 C16 119.12(18) . . ?
C18 N8 C19 119.81(19) . . ?
C3 O3 H3 109.5 . . ?
C15 N6 H6 126.6 . . ?
C14 N6 H6 126.6 . . ?
C14 N6 C15 106.73(18) . . ?
C17 N7 C20 117.5(2) . . ?
C18 N7 C17 126.68(19) . . ?
C18 N7 C20 115.8(2) . . ?
C14 N5 C16 103.47(18) . . ?
C4 N2 C6 104.1(2) . . ?
C6 N4 C8 119.4(2) . . ?
C6 N4 C9 121.0(2) . . ?
C8 N4 C9 119.6(2) . . ?
C8 N3 C10 116.2(2) . . ?
C7 N3 C8 126.4(2) . . ?
C7 N3 C10 117.3(2) . . ?
C5 N1 H1 126.6 . . ?
C4 N1 H1 126.6 . . ?
C4 N1 C5 106.8(2) . . ?
C1 O2 H2 109.5 . . ?
N5 C16 N8 125.92(19) . . ?
N5 C16 C15 111.99(19) . . ?
C15 C16 N8 122.1(2) . . ?
N6 C15 C17 131.7(2) . . ?
C16 C15 N6 104.89(19) . . ?
C16 C15 C17 123.3(2) . . ?
O12 C17 N7 121.3(2) . . ?
O12 C17 C15 127.4(2) . . ?
N7 C17 C15 111.35(19) . . ?
N2 C6 N4 126.4(2) . . ?
C5 C6 N2 111.4(2) . . ?
C5 C6 N4 122.2(2) . . ?
O10 C13 C12 110.81(19) . . ?
O9 C13 O10 123.0(2) . . ?
O9 C13 C12 126.1(2) . . ?
N8 C18 N7 117.31(19) . . ?
O11 C18 N8 121.8(2) . . ?
O11 C18 N7 120.9(2) . . ?
O6 C8 N4 121.8(3) . . ?
O6 C8 N3 121.4(2) . . ?
N4 C8 N3 116.8(2) . . ?
O7 C11 C12 110.5(2) . . ?
O8 C11 O7 122.3(2) . . ?
O8 C11 C12 127.3(2) . . ?
N1 C5 C7 131.6(2) . . ?
C6 C5 N1 105.2(2) . . ?
C6 C5 C7 123.1(2) . . ?
N6 C14 N5 112.9(2) . . ?
N6 C14 H14 123.5 . . ?
N5 C14 H14 123.5 . . ?
O5 C7 N3 120.8(2) . . ?
O5 C7 C5 127.1(2) . . ?
N3 C7 C5 112.1(2) . . ?
N2 C4 H4 123.8 . . ?
N1 C4 N2 112.4(2) . . ?
N1 C4 H4 123.8 . . ?
O1 C1 O2 124.1(3) . . ?
O1 C1 C2 119.5(3) . . ?
O2 C1 C2 116.4(3) . . ?
O3 C3 C2 113.2(2) . . ?
O4 C3 O3 125.4(3) . . ?
O4 C3 C2 121.3(3) . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12A 107.5 . . ?
C13 C12 H12B 107.5 . . ?
C11 C12 H12A 107.5 . . ?
C11 C12 H12B 107.5 . . ?
H12A C12 H12B 107.0 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N7 C20 H20A 109.5 . . ?
N7 C20 H20B 109.5 . . ?
N7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C3 C2 C1 114.3(2) . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O10 H10 N5 0.82 1.87 2.683(2) 171.4 2_666
O7 H7 N2 0.82 1.84 2.662(3) 175.0 .
O3 H3 O5 0.82 1.80 2.586(3) 159.4 .
O2 H2 O1 0.82 1.83 2.640(3) 169.9 2_774

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
O10 C13 C12 C11 175.5(3) . . . . ?
O7 C11 C12 C13 169.1(3) . . . . ?
N8 C16 C15 N6 -179.0(2) . . . . ?
N8 C16 C15 C17 3.5(4) . . . . ?
O1 C1 C2 C3 83.1(4) . . . . ?
O3 C3 C2 C1 16.0(4) . . . . ?
N6 C15 C17 O12 -0.5(5) . . . . ?
N6 C15 C17 N7 179.7(2) . . . . ?
N5 C16 C15 N6 0.3(3) . . . . ?
N5 C16 C15 C17 -177.2(2) . . . . ?
N2 C6 C5 N1 0.0(3) . . . . ?
N2 C6 C5 C7 -177.9(2) . . . . ?
N4 C6 C5 N1 178.3(2) . . . . ?
N4 C6 C5 C7 0.4(4) . . . . ?
O4 C3 C2 C1 -164.8(3) . . . . ?
N1 C5 C7 O5 1.2(5) . . . . ?
N1 C5 C7 N3 -177.1(3) . . . . ?
O8 C11 C12 C13 -11.9(5) . . . . ?
O9 C13 C12 C11 -6.7(5) . . . . ?
O2 C1 C2 C3 -97.1(3) . . . . ?
C16 N8 C18 O11 177.3(2) . . . . ?
C16 N8 C18 N7 -1.9(3) . . . . ?
C16 N5 C14 N6 0.4(3) . . . . ?
C16 C15 C17 O12 176.2(3) . . . . ?
C16 C15 C17 N7 -3.5(3) . . . . ?
C15 N6 C14 N5 -0.3(3) . . . . ?
C17 N7 C18 N8 1.7(4) . . . . ?
C17 N7 C18 O11 -177.5(3) . . . . ?
C6 N2 C4 N1 -0.7(3) . . . . ?
C6 N4 C8 O6 -179.7(2) . . . . ?
C6 N4 C8 N3 0.0(3) . . . . ?
C6 C5 C7 O5 178.5(3) . . . . ?
C6 C5 C7 N3 0.2(4) . . . . ?
C18 N8 C16 N5 -179.7(2) . . . . ?
C18 N8 C16 C15 -0.5(4) . . . . ?
C18 N7 C17 O12 -178.8(2) . . . . ?
C18 N7 C17 C15 0.9(3) . . . . ?
C8 N4 C6 N2 177.6(2) . . . . ?
C8 N4 C6 C5 -0.5(4) . . . . ?
C8 N3 C7 O5 -179.2(3) . . . . ?
C8 N3 C7 C5 -0.8(4) . . . . ?
C5 N1 C4 N2 0.7(3) . . . . ?
C14 N6 C15 C16 0.0(3) . . . . ?
C14 N6 C15 C17 177.2(3) . . . . ?
C14 N5 C16 N8 178.8(2) . . . . ?
C14 N5 C16 C15 -0.4(3) . . . . ?
C7 N3 C8 O6 -179.6(2) . . . . ?
C7 N3 C8 N4 0.7(4) . . . . ?
C4 N2 C6 N4 -177.8(2) . . . . ?
C4 N2 C6 C5 0.4(3) . . . . ?
C4 N1 C5 C6 -0.4(3) . . . . ?
C4 N1 C5 C7 177.3(3) . . . . ?
C19 N8 C16 N5 -0.5(4) . . . . ?
C19 N8 C16 C15 178.7(2) . . . . ?
C19 N8 C18 O11 -1.9(4) . . . . ?
C19 N8 C18 N7 178.9(2) . . . . ?
C9 N4 C6 N2 -4.4(4) . . . . ?
C9 N4 C6 C5 177.6(3) . . . . ?
C9 N4 C8 O6 2.2(4) . . . . ?
C9 N4 C8 N3 -178.1(2) . . . . ?
C20 N7 C17 O12 1.3(4) . . . . ?
C20 N7 C17 C15 -179.0(2) . . . . ?
C20 N7 C18 N8 -178.4(2) . . . . ?
C20 N7 C18 O11 2.4(4) . . . . ?
C10 N3 C8 O6 2.5(4) . . . . ?
C10 N3 C8 N4 -177.2(2) . . . . ?
C10 N3 C7 O5 -1.3(4) . . . . ?
C10 N3 C7 C5 177.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.074
_oxdiff_exptl_absorpt_empirical_full_min 0.960
####################################################################### 
# 
# 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_tp_ma_monoclinic
_database_code_depnum_ccdc_archive 'CCDC 2305332'
loop_
_audit_author_name
_audit_author_address
'Laura Macchietti'
;University of Bologna
Italy
;
_audit_update_record             
;
2023-11-02 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;
_audit_creation_date             2023-10-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        'Theophylline, Malonic acid'
_chemical_formula_moiety         'C7 H8 N4 O2, C3 H4 O4'
_chemical_formula_sum            'C10 H12 N4 O6'
_chemical_formula_weight         284.24
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.2266(11)
_cell_length_b                   8.3825(4)
_cell_length_c                   17.7760(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.365(7)
_cell_angle_gamma                90
_cell_volume                     2486.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1625
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      25.8830
_cell_measurement_theta_min      2.3700
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.85a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5467
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.317
_diffrn_reflns_theta_min         2.365
_diffrn_ambient_temperature      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1385
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  39.00   1.00  110.00    --   17.46  77.00  60.00   48
  2  ω     -7.00  19.00   1.00  110.00    --   17.46  77.00 -90.00   26
  3  ω     39.00  64.00   1.00  110.00    --   17.46 178.00 120.00   25
  4  ω    -55.00  55.00   1.00  110.00    --   17.46 -19.00-120.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0417298000
_diffrn_orient_matrix_UB_12      0.0142378000
_diffrn_orient_matrix_UB_13      0.0134879000
_diffrn_orient_matrix_UB_21      -0.0064831000
_diffrn_orient_matrix_UB_22      0.0362735000
_diffrn_orient_matrix_UB_23      0.0339976000
_diffrn_orient_matrix_UB_31      0.0047886000
_diffrn_orient_matrix_UB_32      -0.0750582000
_diffrn_orient_matrix_UB_33      0.0189821000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1919
_reflns_number_total             2856
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.063
_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)+(0.0629P)²+1.4821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1514
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_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
O5 O 0.48654(11) 0.9084(2) 0.35839(11) 0.0513(5) Uani 1 1 d . . . . .
O1 O 0.29861(12) 0.1085(2) 0.73128(12) 0.0538(5) Uani 1 1 d . . . . .
O6 O 0.31767(13) 1.2678(2) 0.42667(12) 0.0590(6) Uani 1 1 d . . . . .
O3 O 0.30063(12) 0.5436(2) 0.67224(12) 0.0592(6) Uani 1 1 d . . . . .
N4 N 0.40236(12) 1.0872(2) 0.39341(11) 0.0365(5) Uani 1 1 d . . . . .
N3 N 0.42910(12) 0.8354(2) 0.45465(11) 0.0380(5) Uani 1 1 d . . . . .
O4 O 0.40290(13) 0.5063(2) 0.62150(14) 0.0700(7) Uani 1 1 d . . . . .
H4A H 0.388490 0.593053 0.601584 0.105 Uiso 1 1 calc R U . . .
N2 N 0.29289(13) 1.0162(2) 0.54406(12) 0.0425(5) Uani 1 1 d . . . . .
H2 H 0.261992 1.091020 0.552548 0.051 Uiso 1 1 calc R U . . .
O2 O 0.30913(14) 0.3259(2) 0.80388(13) 0.0699(7) Uani 1 1 d . . . . .
N1 N 0.35724(13) 0.7853(2) 0.55427(12) 0.0430(5) Uani 1 1 d . . . . .
C5 C 0.37701(14) 0.8758(3) 0.49875(13) 0.0329(5) Uani 1 1 d . . . . .
C7 C 0.34946(15) 1.1361(3) 0.43699(14) 0.0371(6) Uani 1 1 d . . . . .
C3 C 0.35707(14) 0.4654(3) 0.66617(14) 0.0373(6) Uani 1 1 d . . . . .
C8 C 0.44239(14) 0.9403(3) 0.39959(14) 0.0361(6) Uani 1 1 d . . . . .
C6 C 0.33888(14) 1.0189(3) 0.49061(13) 0.0358(5) Uani 1 1 d . . . . .
C1 C 0.32576(15) 0.2520(3) 0.75254(16) 0.0438(6) Uani 1 1 d . . . . .
C4 C 0.30539(16) 0.8764(3) 0.57981(15) 0.0456(7) Uani 1 1 d . . . . .
H4 H 0.280786 0.845067 0.618452 0.055 Uiso 1 1 calc R U . . .
C10 C 0.41639(18) 1.1956(3) 0.33328(16) 0.0508(7) Uani 1 1 d . . . . .
H10A H 0.390799 1.153892 0.282930 0.076 Uiso 1 1 calc R U . . .
H10B H 0.472947 1.204945 0.338044 0.076 Uiso 1 1 calc R U . . .
H10C H 0.394604 1.298717 0.339528 0.076 Uiso 1 1 calc R U . . .
C9 C 0.46429(18) 0.6757(3) 0.46002(17) 0.0518(7) Uani 1 1 d . . . . .
H9A H 0.488218 0.650778 0.513450 0.078 Uiso 1 1 calc R U . . .
H9B H 0.504536 0.672544 0.431132 0.078 Uiso 1 1 calc R U . . .
H9C H 0.423222 0.599121 0.438993 0.078 Uiso 1 1 calc R U . . .
C2 C 0.38298(17) 0.3116(3) 0.70783(18) 0.0546(8) Uani 1 1 d . . . . .
H2A H 0.388478 0.231303 0.670197 0.066 Uiso 1 1 calc R U . . .
H2B H 0.435183 0.326558 0.743314 0.066 Uiso 1 1 calc R U . . .
H1 H 0.265(2) 0.079(4) 0.761(2) 0.097(12) 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
O5 C8 1.209(3) . ?
O1 C1 1.311(3) . ?
O1 H1 0.91(4) . ?
O6 C7 1.226(3) . ?
O3 C3 1.199(3) . ?
N4 C7 1.396(3) . ?
N4 C8 1.402(3) . ?
N4 C10 1.468(3) . ?
N3 C5 1.372(3) . ?
N3 C8 1.376(3) . ?
N3 C9 1.463(3) . ?
O4 H4A 0.8200 . ?
O4 C3 1.297(3) . ?
N2 H2 0.8600 . ?
N2 C6 1.380(3) . ?
N2 C4 1.325(3) . ?
O2 C1 1.195(3) . ?
N1 C5 1.354(3) . ?
N1 C4 1.337(3) . ?
C5 C6 1.358(3) . ?
C7 C6 1.412(3) . ?
C3 C2 1.499(3) . ?
C1 C2 1.497(3) . ?
C4 H4 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109(2) . . ?
C7 N4 C8 126.18(19) . . ?
C7 N4 C10 118.08(19) . . ?
C8 N4 C10 115.71(19) . . ?
C5 N3 C8 119.77(18) . . ?
C5 N3 C9 120.50(19) . . ?
C8 N3 C9 119.4(2) . . ?
C3 O4 H4A 109.5 . . ?
C6 N2 H2 126.5 . . ?
C4 N2 H2 126.5 . . ?
C4 N2 C6 106.99(19) . . ?
C4 N1 C5 103.75(19) . . ?
N1 C5 N3 126.65(19) . . ?
N1 C5 C6 111.7(2) . . ?
C6 C5 N3 121.6(2) . . ?
O6 C7 N4 120.7(2) . . ?
O6 C7 C6 126.9(2) . . ?
N4 C7 C6 112.46(19) . . ?
O3 C3 O4 122.8(2) . . ?
O3 C3 C2 125.0(2) . . ?
O4 C3 C2 112.2(2) . . ?
O5 C8 N4 121.2(2) . . ?
O5 C8 N3 122.0(2) . . ?
N3 C8 N4 116.82(19) . . ?
N2 C6 C7 132.0(2) . . ?
C5 C6 N2 104.9(2) . . ?
C5 C6 C7 123.1(2) . . ?
O1 C1 C2 112.8(2) . . ?
O2 C1 O1 124.0(2) . . ?
O2 C1 C2 123.1(3) . . ?
N2 C4 N1 112.6(2) . . ?
N2 C4 H4 123.7 . . ?
N1 C4 H4 123.7 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 C3 113.3(2) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 122.3(3) . . . . ?
O6 C7 C6 N2 0.0(5) . . . . ?
O6 C7 C6 C5 -179.5(3) . . . . ?
O3 C3 C2 C1 6.4(4) . . . . ?
N4 C7 C6 N2 -179.8(2) . . . . ?
N4 C7 C6 C5 0.6(3) . . . . ?
N3 C5 C6 N2 -179.7(2) . . . . ?
N3 C5 C6 C7 0.0(4) . . . . ?
O4 C3 C2 C1 -173.3(3) . . . . ?
O2 C1 C2 C3 -60.2(4) . . . . ?
N1 C5 C6 N2 -0.1(3) . . . . ?
N1 C5 C6 C7 179.5(2) . . . . ?
C5 N3 C8 O5 -178.5(2) . . . . ?
C5 N3 C8 N4 1.7(3) . . . . ?
C5 N1 C4 N2 -0.5(3) . . . . ?
C7 N4 C8 O5 179.2(2) . . . . ?
C7 N4 C8 N3 -1.0(4) . . . . ?
C8 N4 C7 O6 -180.0(2) . . . . ?
C8 N4 C7 C6 -0.1(3) . . . . ?
C8 N3 C5 N1 179.3(2) . . . . ?
C8 N3 C5 C6 -1.2(4) . . . . ?
C6 N2 C4 N1 0.4(3) . . . . ?
C4 N2 C6 C5 -0.2(3) . . . . ?
C4 N2 C6 C7 -179.8(3) . . . . ?
C4 N1 C5 N3 179.9(2) . . . . ?
C4 N1 C5 C6 0.4(3) . . . . ?
C10 N4 C7 O6 -2.1(4) . . . . ?
C10 N4 C7 C6 177.7(2) . . . . ?
C10 N4 C8 O5 1.3(3) . . . . ?
C10 N4 C8 N3 -178.9(2) . . . . ?
C9 N3 C5 N1 5.6(4) . . . . ?
C9 N3 C5 C6 -174.9(2) . . . . ?
C9 N3 C8 O5 -4.7(4) . . . . ?
C9 N3 C8 N4 175.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.060
_oxdiff_exptl_absorpt_empirical_full_min 0.945
