# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_car_293k
_audit_block_doi                 10.5517/ccdc.csd.cc2fr0cl
_database_code_depnum_ccdc_archive 'CCDC 2256439'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2023-04-14 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_audit_creation_date             2022-05-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H2 N4 O3, C10 H8 N2'
_chemical_formula_sum            'C12 H10 N6 O3'
_chemical_formula_weight         286.26
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.9440(7)
_cell_length_b                   5.7979(5)
_cell_length_c                   27.874(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.810(3)
_cell_angle_gamma                90
_cell_volume                     1277.22(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0898 before and 0.0379 after correction.
The Ratio of minimum to maximum transmission is 0.9332.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            27388
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.389
_diffrn_reflns_theta_min         2.607
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2387
_reflns_number_total             2576
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.105
_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)+(0.0650P)²+0.3026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1242
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, H9 of C9, H12 of C12, H11 of C11, H4 of C4, H10 of C10, H7
  of C7, H6 of C6, H3 of C3
 At 1.5 times of:
  H1 of C7
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C9(H9), C4(H4), C10(H10), C12(H12), C11(H11), C3(H3), C6(H6), C7(H7)
;
_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
O1 O 0.49256(15) 0.76318(19) 0.37594(4) 0.0527(3) Uani 1 1 d . . . . .
N1 N 0.64218(15) 0.4156(2) 0.38003(4) 0.0383(3) Uani 1 1 d . . . . .
O2 O 0.83627(16) 0.0366(2) 0.39580(5) 0.0653(4) Uani 1 1 d . . . . .
N5 N 0.60812(15) 0.3235(2) 0.30218(4) 0.0414(3) Uani 1 1 d . . . . .
O3 O 0.79467(17) -0.0633(2) 0.32033(5) 0.0670(4) Uani 1 1 d . . . . .
N2 N 0.52851(16) 0.5251(2) 0.31025(4) 0.0423(3) Uani 1 1 d . . . . .
H2 H 0.472221 0.603308 0.287823 0.051 Uiso 1 1 calc R U . . .
N4 N 0.89691(17) 0.7525(2) 0.72442(4) 0.0471(3) Uani 1 1 d . . . . .
N6 N 0.77461(16) 0.0644(2) 0.35402(5) 0.0476(3) Uani 1 1 d . . . . .
N3 N 0.73885(17) 0.4604(3) 0.47680(4) 0.0506(3) Uani 1 1 d . . . . .
C8 C 0.83361(15) 0.6352(2) 0.62675(4) 0.0332(3) Uani 1 1 d . . . . .
C5 C 0.80115(16) 0.5741(2) 0.57473(4) 0.0349(3) Uani 1 1 d . . . . .
C2 C 0.67254(17) 0.2670(2) 0.34476(5) 0.0368(3) Uani 1 1 d . . . . .
C1 C 0.54684(17) 0.5913(2) 0.35762(5) 0.0381(3) Uani 1 1 d . . . . .
C9 C 0.76949(18) 0.8354(3) 0.64492(5) 0.0419(3) Uani 1 1 d . . . . .
H9 H 0.703814 0.935078 0.624685 0.050 Uiso 1 1 calc R U . . .
C4 C 0.8596(2) 0.3710(3) 0.55631(5) 0.0484(4) Uani 1 1 d . . . . .
H4 H 0.921422 0.267479 0.576609 0.058 Uiso 1 1 calc R U . . .
C10 C 0.8038(2) 0.8859(3) 0.69333(5) 0.0470(4) Uani 1 1 d . . . . .
H10 H 0.759225 1.021001 0.704837 0.056 Uiso 1 1 calc R U . . .
C12 C 0.93050(19) 0.4949(3) 0.65916(5) 0.0418(3) Uani 1 1 d . . . . .
H12 H 0.976015 0.358174 0.648718 0.050 Uiso 1 1 calc R U . . .
C11 C 0.9588(2) 0.5595(3) 0.70693(5) 0.0473(4) Uani 1 1 d . . . . .
H11 H 1.024465 0.463600 0.728029 0.057 Uiso 1 1 calc R U . . .
C3 C 0.8263(2) 0.3219(3) 0.50792(5) 0.0534(4) Uani 1 1 d . . . . .
H3 H 0.867257 0.184368 0.496482 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7098(2) 0.7187(3) 0.54197(5) 0.0541(4) Uani 1 1 d . . . . .
H6 H 0.667511 0.857855 0.552214 0.065 Uiso 1 1 calc R U . . .
C7 C 0.6821(2) 0.6548(3) 0.49414(6) 0.0606(5) Uani 1 1 d . . . . .
H7 H 0.620086 0.753952 0.472885 0.073 Uiso 1 1 calc R U . . .
H1 H 0.686(3) 0.405(4) 0.4139(9) 0.091 Uiso 1 1 d . 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 1.2183(17) . ?
N1 C2 1.3472(17) . ?
N1 C1 1.3809(17) . ?
N1 H1 0.97(3) . ?
O2 N6 1.2273(18) . ?
N5 N2 1.3584(17) . ?
N5 C2 1.2864(18) . ?
O3 N6 1.2188(18) . ?
N2 H2 0.8600 . ?
N2 C1 1.3686(17) . ?
N4 C10 1.329(2) . ?
N4 C11 1.334(2) . ?
N6 C2 1.4359(18) . ?
N3 C3 1.326(2) . ?
N3 C7 1.324(2) . ?
C8 C5 1.4893(17) . ?
C8 C9 1.3841(19) . ?
C8 C12 1.3890(18) . ?
C5 C4 1.384(2) . ?
C5 C6 1.3890(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.378(2) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.3797(19) . ?
C11 H11 0.9300 . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.380(2) . ?
C7 H7 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 105.80(11) . . ?
C2 N1 H1 126.5(14) . . ?
C1 N1 H1 127.5(15) . . ?
C2 N5 N2 102.42(11) . . ?
N5 N2 H2 123.4 . . ?
N5 N2 C1 113.28(11) . . ?
C1 N2 H2 123.4 . . ?
C10 N4 C11 116.81(12) . . ?
O2 N6 C2 116.21(13) . . ?
O3 N6 O2 125.51(14) . . ?
O3 N6 C2 118.28(13) . . ?
C7 N3 C3 116.87(13) . . ?
C9 C8 C5 121.44(11) . . ?
C9 C8 C12 116.96(12) . . ?
C12 C8 C5 121.60(12) . . ?
C4 C5 C8 122.13(12) . . ?
C4 C5 C6 116.25(13) . . ?
C6 C5 C8 121.62(13) . . ?
N1 C2 N6 122.10(12) . . ?
N5 C2 N1 115.24(12) . . ?
N5 C2 N6 122.62(13) . . ?
O1 C1 N1 127.96(13) . . ?
O1 C1 N2 128.79(13) . . ?
N2 C1 N1 103.25(11) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.47(13) . . ?
C10 C9 H9 120.3 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.03(14) . . ?
C3 C4 H4 120.0 . . ?
N4 C10 C9 123.75(14) . . ?
N4 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C8 C12 H12 120.2 . . ?
C11 C12 C8 119.61(13) . . ?
C11 C12 H12 120.2 . . ?
N4 C11 C12 123.39(14) . . ?
N4 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
N3 C3 C4 123.50(15) . . ?
N3 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.67(15) . . ?
C7 C6 H6 120.2 . . ?
N3 C7 C6 123.68(15) . . ?
N3 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?

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
O2 N6 C2 N1 -1.7(2) . . . . ?
O2 N6 C2 N5 176.09(14) . . . . ?
N5 N2 C1 O1 179.11(14) . . . . ?
N5 N2 C1 N1 -0.96(16) . . . . ?
O3 N6 C2 N1 179.13(13) . . . . ?
O3 N6 C2 N5 -3.1(2) . . . . ?
N2 N5 C2 N1 -0.25(16) . . . . ?
N2 N5 C2 N6 -178.15(12) . . . . ?
C8 C5 C4 C3 179.94(14) . . . . ?
C8 C5 C6 C7 -179.72(15) . . . . ?
C8 C9 C10 N4 0.2(2) . . . . ?
C8 C12 C11 N4 0.3(2) . . . . ?
C5 C8 C9 C10 -179.53(13) . . . . ?
C5 C8 C12 C11 179.29(13) . . . . ?
C5 C4 C3 N3 -0.1(3) . . . . ?
C5 C6 C7 N3 -0.3(3) . . . . ?
C2 N1 C1 O1 -179.33(14) . . . . ?
C2 N1 C1 N2 0.74(15) . . . . ?
C2 N5 N2 C1 0.77(15) . . . . ?
C1 N1 C2 N5 -0.33(16) . . . . ?
C1 N1 C2 N6 177.59(12) . . . . ?
C9 C8 C5 C4 -177.81(14) . . . . ?
C9 C8 C5 C6 2.1(2) . . . . ?
C9 C8 C12 C11 -0.3(2) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C10 N4 C11 C12 -0.1(2) . . . . ?
C12 C8 C5 C4 2.7(2) . . . . ?
C12 C8 C5 C6 -177.46(15) . . . . ?
C12 C8 C9 C10 0.0(2) . . . . ?
C11 N4 C10 C9 -0.2(2) . . . . ?
C3 N3 C7 C6 0.3(3) . . . . ?
C6 C5 C4 C3 0.1(2) . . . . ?
C7 N3 C3 C4 0.0(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
