# 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_p02
_audit_block_doi                 10.5517/ccdc.csd.cc2bvm3y
_database_code_depnum_ccdc_archive 'CCDC 2170530'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_car_p02             
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.366 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
_vrf_PLAT430_car_p02             
;
PROBLEM: Short Inter D...A Contact  O3       ..N1       .       2.83 Ang.
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:23 PM
# end Validation Reply Form

_audit_creation_date             2022-05-03
_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                   7.6908(13)
_cell_length_b                   5.7271(4)
_cell_length_c                   27.006(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.719(9)
_cell_angle_gamma                90
_cell_volume                     1189.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2691
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      25.63
_cell_measurement_theta_min      3.86
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0975 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.8547.
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    1.599
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.366
_diffrn_reflns_Laue_measured_fraction_max 0.339
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6652
_diffrn_reflns_point_group_measured_fraction_full 0.366
_diffrn_reflns_point_group_measured_fraction_max 0.339
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         3.865
_diffrn_ambient_temperature      296.1
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.366
_diffrn_measured_fraction_theta_max 0.339
_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                667
_reflns_number_total             826
_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         0.123
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         826
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.017
_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)+(0.0559P)²+1.1862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C5: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
3. 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
4.a Aromatic/amide H refined with riding coordinates:
 N3(H3A), C11(H11), C4(H4), C12(H12), C8(H8), C6(H6), C9(H9), C7(H7), C3(H3)
;
_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
O2 O 0.1711(10) 0.0008(5) 0.60990(12) 0.055(5) Uani 1 1 d . . . . .
O3 O 0.5151(10) 0.7397(4) 0.62723(11) 0.044(4) Uani 1 1 d . . . . .
O1 O 0.2060(10) -0.1053(5) 0.68665(12) 0.056(4) Uani 1 1 d . . . . .
N6 N 0.1084(11) 0.7768(5) 0.27946(12) 0.039(5) Uani 1 1 d . . . . .
N4 N 0.3935(11) 0.2856(5) 0.70388(12) 0.028(4) Uani 1 1 d . . . . .
N3 N 0.4753(11) 0.4932(5) 0.69488(13) 0.035(4) Uani 1 1 d . . . . .
H3A H 0.530834 0.571186 0.717214 0.042 Uiso 1 1 calc R U . . .
N1 N 0.2305(11) 0.0271(5) 0.65210(13) 0.038(4) Uani 1 1 d . . . . .
N2 N 0.3649(11) 0.3874(5) 0.62473(13) 0.026(4) Uani 1 1 d . . . . .
N5 N 0.2646(12) 0.4461(6) 0.52911(13) 0.046(6) Uani 1 1 d . . . . .
C11 C 0.2296(14) 0.8529(6) 0.35965(15) 0.031(5) Uani 1 1 d . . . . .
H11 H 0.292275 0.953806 0.380104 0.037 Uiso 1 1 calc R U . . .
C1 C 0.3329(14) 0.2318(6) 0.66078(15) 0.028(4) Uani 1 1 d . . . . .
C10 C 0.1677(13) 0.6461(6) 0.37799(15) 0.023(5) Uani 1 1 d . . . . .
C2 C 0.4595(13) 0.5635(6) 0.64688(15) 0.031(4) Uani 1 1 d . . . . .
C4 C 0.2888(14) 0.7199(7) 0.46317(16) 0.035(6) Uani 1 1 d . . . . .
H4 H 0.327948 0.864926 0.452555 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2003(13) 0.5757(6) 0.43079(14) 0.020(5) Uani 1 1 d . . . . .
C12 C 0.1982(14) 0.9112(7) 0.31042(16) 0.037(6) Uani 1 1 d . . . . .
H12 H 0.242407 1.051471 0.298618 0.044 Uiso 1 1 calc R U . . .
C8 C 0.0453(14) 0.5762(7) 0.29751(16) 0.041(5) Uani 1 1 d . . . . .
H8 H -0.019552 0.480415 0.276482 0.049 Uiso 1 1 calc R U . . .
C6 C 0.1439(14) 0.3649(6) 0.44927(15) 0.028(5) Uani 1 1 d . . . . .
H6 H 0.081862 0.262237 0.429045 0.033 Uiso 1 1 calc R U . . .
C9 C 0.0721(14) 0.5056(6) 0.34583(15) 0.028(5) Uani 1 1 d . . . . .
H9 H 0.026443 0.364663 0.356788 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1799(14) 0.3070(7) 0.49788(16) 0.039(6) Uani 1 1 d . . . . .
H7 H 0.142732 0.162542 0.509378 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3194(15) 0.6495(7) 0.51141(16) 0.046(6) Uani 1 1 d . . . . .
H3 H 0.381171 0.748738 0.532450 0.055 Uiso 1 1 calc R U . . .
H2 H 0.333(14) 0.378(7) 0.5920(19) 0.059(16) 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
O2 N1 1.232(4) . ?
O3 C2 1.220(7) . ?
O1 N1 1.219(5) . ?
N6 C12 1.325(7) . ?
N6 C8 1.341(7) . ?
N4 N3 1.368(7) . ?
N4 C1 1.286(5) . ?
N3 H3A 0.8600 . ?
N3 C2 1.361(5) . ?
N1 C1 1.430(8) . ?
N2 C1 1.345(6) . ?
N2 C2 1.376(7) . ?
N2 H2 0.92(5) . ?
N5 C7 1.325(7) . ?
N5 C3 1.330(8) . ?
C11 H11 0.9300 . ?
C11 C10 1.371(8) . ?
C11 C12 1.389(5) . ?
C10 C5 1.500(5) . ?
C10 C9 1.388(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(7) . ?
C4 C3 1.381(5) . ?
C5 C6 1.379(7) . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.379(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(5) . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 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
C12 N6 C8 117.2(4) . . ?
C1 N4 N3 102.1(4) . . ?
N4 N3 H3A 123.5 . . ?
C2 N3 N4 113.0(4) . . ?
C2 N3 H3A 123.5 . . ?
O2 N1 C1 116.7(4) . . ?
O1 N1 O2 125.0(5) . . ?
O1 N1 C1 118.3(4) . . ?
C1 N2 C2 105.7(4) . . ?
C1 N2 H2 127(4) . . ?
C2 N2 H2 127(4) . . ?
C7 N5 C3 117.0(4) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
N4 C1 N1 122.5(4) . . ?
N4 C1 N2 115.4(5) . . ?
N2 C1 N1 122.0(4) . . ?
C11 C10 C5 121.4(4) . . ?
C11 C10 C9 117.3(3) . . ?
C9 C10 C5 121.3(5) . . ?
O3 C2 N3 129.1(5) . . ?
O3 C2 N2 127.1(3) . . ?
N3 C2 N2 103.7(4) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.1(5) . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C10 121.2(5) . . ?
C4 C5 C6 116.8(4) . . ?
C6 C5 C10 122.0(4) . . ?
N6 C12 C11 123.2(5) . . ?
N6 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
N6 C8 H8 118.5 . . ?
N6 C8 C9 123.0(5) . . ?
C9 C8 H8 118.5 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.7(5) . . ?
C7 C6 H6 120.2 . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
N5 C7 C6 123.5(5) . . ?
N5 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
N5 C3 C4 122.9(5) . . ?
N5 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?

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 N1 C1 N4 175.9(8) . . . . ?
O2 N1 C1 N2 -0.7(12) . . . . ?
O1 N1 C1 N4 -2.9(12) . . . . ?
O1 N1 C1 N2 -179.5(8) . . . . ?
N6 C8 C9 C10 0.3(14) . . . . ?
N4 N3 C2 O3 179.2(9) . . . . ?
N4 N3 C2 N2 -1.0(9) . . . . ?
N3 N4 C1 N1 -178.0(8) . . . . ?
N3 N4 C1 N2 -1.2(10) . . . . ?
C11 C10 C5 C4 2.2(14) . . . . ?
C11 C10 C5 C6 -177.8(9) . . . . ?
C11 C10 C9 C8 0.8(13) . . . . ?
C1 N4 N3 C2 1.3(10) . . . . ?
C1 N2 C2 O3 -179.9(9) . . . . ?
C1 N2 C2 N3 0.2(9) . . . . ?
C10 C11 C12 N6 0.7(15) . . . . ?
C10 C5 C6 C7 178.9(8) . . . . ?
C2 N2 C1 N4 0.6(11) . . . . ?
C2 N2 C1 N1 177.5(8) . . . . ?
C4 C5 C6 C7 -1.1(14) . . . . ?
C5 C10 C9 C8 -179.8(9) . . . . ?
C5 C4 C3 N5 -1.1(15) . . . . ?
C5 C6 C7 N5 1.3(15) . . . . ?
C12 N6 C8 C9 -0.9(14) . . . . ?
C12 C11 C10 C5 179.4(9) . . . . ?
C12 C11 C10 C9 -1.3(13) . . . . ?
C8 N6 C12 C11 0.4(14) . . . . ?
C9 C10 C5 C4 -177.2(9) . . . . ?
C9 C10 C5 C6 2.8(14) . . . . ?
C7 N5 C3 C4 1.2(14) . . . . ?
C3 N5 C7 C6 -1.4(14) . . . . ?
C3 C4 C5 C10 -179.0(9) . . . . ?
C3 C4 C5 C6 0.9(14) . . . . ?


_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_2car_p07
_audit_block_doi                 10.5517/ccdc.csd.cc2bvm50
_database_code_depnum_ccdc_archive 'CCDC 2170532'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_2car_p07            
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is due to the limitation of the high pressure data. intensity is not enough to determine anisotropic atomic displacement.
;
_vrf_PLAT029_2car_p07            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.385 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
_vrf_PLAT201_2car_p07            
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         12 Report
RESPONSE: high pressure data
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:23 PM
# end Validation Reply Form

_audit_creation_date             2022-05-04
_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         '2(C2 H2 N4 O3), 2(C10 H8 N2)'
_chemical_formula_sum            'C24 H20 N12 O6'
_chemical_formula_weight         572.52
_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                   7.2224(11)
_cell_length_b                   5.6283(4)
_cell_length_c                   26.087(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.048(7)
_cell_angle_gamma                90
_cell_volume                     1057.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    292.9
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      3.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1150 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.8307.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.797
_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  0.0427
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.385
_diffrn_reflns_Laue_measured_fraction_max 0.354
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5833
_diffrn_reflns_point_group_measured_fraction_full 0.385
_diffrn_reflns_point_group_measured_fraction_max 0.354
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.405
_diffrn_reflns_theta_min         3.546
_diffrn_ambient_temperature      292.9
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.385
_diffrn_measured_fraction_theta_max 0.354
_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                630
_reflns_number_total             766
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.267
_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)+(0.0706P)²+1.4757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1632
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
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), C11(H11), C8(H8), C3(H3), C6(H6), C4(H4), C12(H12), 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 0.1893(11) 1.1481(5) 0.31160(15) 0.0273(9) Uiso 1 1 d . . . . .
O3 O 0.5215(11) 0.2802(5) 0.36933(15) 0.0276(9) Uiso 1 1 d . . . . .
O2 O 0.1751(11) 1.0331(5) 0.39093(14) 0.0253(9) Uiso 1 1 d . . . . .
N2 N 0.3684(13) 0.6407(6) 0.37316(17) 0.0176(10) Uiso 1 1 d . . . . .
H2 H 0.341014 0.645771 0.404688 0.021 Uiso 1 1 calc R U . . .
N6 N 0.1194(13) 0.1922(6) 0.71875(17) 0.0209(10) Uiso 1 1 d . . . . .
N4 N 0.3872(13) 0.7564(6) 0.29247(17) 0.0208(10) Uiso 1 1 d . . . . .
N5 N 0.2676(14) 0.5659(7) 0.46637(18) 0.0261(11) Uiso 1 1 d . . . . .
N1 N 0.2239(13) 1.0108(6) 0.34655(17) 0.0211(10) Uiso 1 1 d . . . . .
N3 N 0.4701(14) 0.5420(6) 0.30024(17) 0.0206(10) Uiso 1 1 d . . . . .
C5 C 0.2050(17) 0.4175(7) 0.5654(2) 0.0191(11) Uiso 1 1 d . . . . .
C10 C 0.1672(16) 0.3361(7) 0.6179(2) 0.0168(11) Uiso 1 1 d . . . . .
C9 C 0.0754(16) 0.4789(8) 0.6514(2) 0.0200(11) Uiso 1 1 d . . . . .
H9 H 0.029638 0.626459 0.640605 0.024 Uiso 1 1 calc R U . . .
C1 C 0.3273(16) 0.8042(7) 0.3368(2) 0.0177(11) Uiso 1 1 d . . . . .
C11 C 0.2325(17) 0.1204(8) 0.6362(2) 0.0202(11) Uiso 1 1 d . . . . .
H11 H 0.294299 0.019036 0.615004 0.024 Uiso 1 1 calc R U . . .
C8 C 0.0524(17) 0.4015(8) 0.7004(2) 0.0203(11) Uiso 1 1 d . . . . .
H8 H -0.012287 0.497751 0.721929 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3243(18) 0.3547(8) 0.4834(2) 0.0259(12) Uiso 1 1 d . . . . .
H3 H 0.386779 0.256668 0.461743 0.031 Uiso 1 1 calc R U . . .
C6 C 0.1432(17) 0.6399(7) 0.5469(2) 0.0197(11) Uiso 1 1 d . . . . .
H6 H 0.078216 0.740894 0.567395 0.024 Uiso 1 1 calc R U . . .
C2 C 0.4631(16) 0.4634(7) 0.3500(2) 0.0190(11) Uiso 1 1 d . . . . .
C4 C 0.2945(16) 0.2742(8) 0.5321(2) 0.0204(12) Uiso 1 1 d . . . . .
H4 H 0.334604 0.123536 0.542417 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2057(17) 0.0546(8) 0.6865(2) 0.0207(12) Uiso 1 1 d . . . . .
H12 H 0.250067 -0.092252 0.698158 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1803(17) 0.7061(8) 0.4979(2) 0.0223(12) Uiso 1 1 d . . . . .
H7 H 0.142482 0.855801 0.486236 0.027 Uiso 1 1 calc R U . . .
H3A H 0.51(2) 0.455(10) 0.269(3) 0.06(2) 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
O1 N1 1.208(7) . ?
O3 C2 1.211(8) . ?
O2 N1 1.240(5) . ?
N2 H2 0.8600 . ?
N2 C1 1.339(8) . ?
N2 C2 1.373(7) . ?
N6 C8 1.349(9) . ?
N6 C12 1.330(7) . ?
N4 N3 1.356(8) . ?
N4 C1 1.292(5) . ?
N5 C3 1.324(9) . ?
N5 C7 1.330(7) . ?
N1 C1 1.415(9) . ?
N3 C2 1.376(6) . ?
N3 H3A 1.00(6) . ?
C5 C10 1.488(5) . ?
C5 C6 1.403(9) . ?
C5 C4 1.379(7) . ?
C10 C9 1.389(8) . ?
C10 C11 1.375(9) . ?
C9 H9 0.9300 . ?
C9 C8 1.371(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(6) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.378(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(6) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
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
C1 N2 H2 126.9 . . ?
C1 N2 C2 106.3(4) . . ?
C2 N2 H2 126.9 . . ?
C12 N6 C8 117.1(4) . . ?
C1 N4 N3 102.9(4) . . ?
C3 N5 C7 118.2(4) . . ?
O1 N1 O2 125.7(5) . . ?
O1 N1 C1 118.3(4) . . ?
O2 N1 C1 116.1(5) . . ?
N4 N3 C2 112.4(4) . . ?
N4 N3 H3A 117(5) . . ?
C2 N3 H3A 130(4) . . ?
C6 C5 C10 121.1(5) . . ?
C4 C5 C10 121.7(5) . . ?
C4 C5 C6 117.1(4) . . ?
C9 C10 C5 121.8(5) . . ?
C11 C10 C5 120.7(5) . . ?
C11 C10 C9 117.4(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.8(6) . . ?
C8 C9 H9 120.1 . . ?
N2 C1 N1 122.1(4) . . ?
N4 C1 N2 114.8(6) . . ?
N4 C1 N1 123.1(5) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(5) . . ?
C12 C11 H11 120.2 . . ?
N6 C8 C9 123.0(5) . . ?
N6 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
N5 C3 H3 118.7 . . ?
N5 C3 C4 122.7(5) . . ?
C4 C3 H3 118.7 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6 120.5 . . ?
O3 C2 N2 127.3(4) . . ?
O3 C2 N3 129.2(5) . . ?
N2 C2 N3 103.5(5) . . ?
C5 C4 C3 119.9(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N6 C12 C11 123.0(6) . . ?
N6 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
N5 C7 C6 123.1(6) . . ?
N5 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?

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 N1 C1 N2 -178.7(9) . . . . ?
O1 N1 C1 N4 0.4(15) . . . . ?
O2 N1 C1 N2 0.8(14) . . . . ?
O2 N1 C1 N4 179.8(9) . . . . ?
N4 N3 C2 O3 179.1(11) . . . . ?
N4 N3 C2 N2 0.6(11) . . . . ?
N5 C3 C4 C5 -1.1(18) . . . . ?
N3 N4 C1 N2 1.5(11) . . . . ?
N3 N4 C1 N1 -177.6(9) . . . . ?
C5 C10 C9 C8 -176.5(10) . . . . ?
C5 C10 C11 C12 175.9(11) . . . . ?
C5 C6 C7 N5 2.1(18) . . . . ?
C10 C5 C6 C7 -179.4(11) . . . . ?
C10 C5 C4 C3 179.0(11) . . . . ?
C10 C9 C8 N6 1.7(17) . . . . ?
C10 C11 C12 N6 -0.4(17) . . . . ?
C9 C10 C11 C12 -0.3(16) . . . . ?
C1 N2 C2 O3 -178.3(11) . . . . ?
C1 N2 C2 N3 0.3(11) . . . . ?
C1 N4 N3 C2 -1.3(11) . . . . ?
C11 C10 C9 C8 -0.3(16) . . . . ?
C8 N6 C12 C11 1.6(16) . . . . ?
C3 N5 C7 C6 -1.3(17) . . . . ?
C6 C5 C10 C9 -2.3(17) . . . . ?
C6 C5 C10 C11 -178.3(10) . . . . ?
C6 C5 C4 C3 1.8(16) . . . . ?
C2 N2 C1 N4 -1.2(12) . . . . ?
C2 N2 C1 N1 178.0(9) . . . . ?
C4 C5 C10 C9 -179.3(11) . . . . ?
C4 C5 C10 C11 4.6(16) . . . . ?
C4 C5 C6 C7 -2.3(16) . . . . ?
C12 N6 C8 C9 -2.3(15) . . . . ?
C7 N5 C3 C4 0.8(17) . . . . ?


_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_3car_p04
_audit_block_doi                 10.5517/ccdc.csd.cc2bvm61
_database_code_depnum_ccdc_archive 'CCDC 2170533'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_3car_p04            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.348 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:23 PM
# end Validation Reply Form

_audit_creation_date             2022-05-04
_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                   7.1952(4)
_cell_length_b                   5.6211(3)
_cell_length_c                   26.010(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.452(6)
_cell_angle_gamma                90
_cell_volume                     1048.79(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2516
_cell_measurement_temperature    300.8
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.813
_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  0.0286
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.348
_diffrn_reflns_Laue_measured_fraction_max 0.328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5605
_diffrn_reflns_point_group_measured_fraction_full 0.348
_diffrn_reflns_point_group_measured_fraction_max 0.328
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_min         2.887
_diffrn_ambient_temperature      300.8
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.348
_diffrn_measured_fraction_theta_max 0.328
_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                591
_reflns_number_total             700
_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         0.090
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.021
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         700
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      0.972
_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)+(0.0393P)²+0.2262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0670
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
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:
 N3(H3A), C12(H12), C9(H9), C8(H8), C6(H6), C7(H7), C3(H3), C11(H11), C4(H4)
;
_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 0.8130(2) 1.1519(3) 0.68859(18) 0.028(3) Uani 1 1 d . . . . .
O2 O 0.8246(3) 1.0355(3) 0.6086(3) 0.028(3) Uani 1 1 d . . . . .
O3 O 0.47555(19) 0.2810(2) 0.63026(15) 0.030(2) Uani 1 1 d . . . . .
N4 N 0.6306(3) 0.6433(3) 0.6260(2) 0.019(2) Uani 1 1 d . . . . .
N1 N 0.7765(4) 1.0146(4) 0.6532(3) 0.019(3) Uani 1 1 d . . . . .
N6 N 0.8805(2) 0.1894(3) 0.2808(2) 0.024(3) Uani 1 1 d . . . . .
N2 N 0.6138(3) 0.7607(3) 0.7083(3) 0.023(3) Uani 1 1 d . . . . .
N3 N 0.5296(3) 0.5433(4) 0.6995(3) 0.022(3) Uani 1 1 d . . . . .
H3A H 0.476840 0.464489 0.722730 0.027 Uiso 1 1 calc R U . . .
N5 N 0.7342(3) 0.5679(3) 0.5343(2) 0.025(3) Uani 1 1 d . . . . .
C12 C 0.7940(3) 0.0537(4) 0.3145(3) 0.024(3) Uani 1 1 d . . . . .
H12 H 0.748799 -0.093629 0.303140 0.029 Uiso 1 1 calc R U . . .
C2 C 0.5389(3) 0.4664(4) 0.6504(3) 0.018(3) Uani 1 1 d . . . . .
C1 C 0.6706(3) 0.8046(4) 0.6637(3) 0.018(3) Uani 1 1 d . . . . .
C9 C 0.9240(3) 0.4778(4) 0.3479(3) 0.023(3) Uani 1 1 d . . . . .
H9 H 0.969091 0.627110 0.357933 0.027 Uiso 1 1 calc R U . . .
C8 C 0.9463(3) 0.3995(4) 0.3001(3) 0.024(3) Uani 1 1 d . . . . .
H8 H 1.011486 0.496082 0.278721 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7036(3) 0.2751(4) 0.4686(3) 0.023(3) Uani 1 1 d . . . . .
H6 H 0.660638 0.125152 0.458343 0.027 Uiso 1 1 calc R U . . .
C10 C 0.8328(3) 0.3367(3) 0.3832(3) 0.019(2) Uani 1 1 d . . . . .
C7 C 0.6747(3) 0.3535(4) 0.5164(3) 0.027(3) Uani 1 1 d . . . . .
H7 H 0.610983 0.255659 0.537882 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8234(3) 0.7061(4) 0.5016(3) 0.024(3) Uani 1 1 d . . . . .
H3 H 0.863172 0.855819 0.513043 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7681(4) 0.1169(4) 0.3641(3) 0.024(3) Uani 1 1 d . . . . .
H11 H 0.707466 0.013755 0.385188 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7980(3) 0.4160(4) 0.4338(3) 0.021(2) Uani 1 1 d . . . . .
C4 C 0.8584(3) 0.6404(4) 0.4535(3) 0.022(3) Uani 1 1 d . . . . .
H4 H 0.922539 0.742840 0.433045 0.026 Uiso 1 1 calc R U . . .
H4A H 0.679(4) 0.626(4) 0.589(3) 0.016(10) 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
O1 N1 1.214(7) . ?
O2 N1 1.242(11) . ?
O3 C2 1.238(4) . ?
N4 C2 1.375(5) . ?
N4 C1 1.349(8) . ?
N4 H4A 1.06(7) . ?
N1 C1 1.443(4) . ?
N6 C12 1.351(7) . ?
N6 C8 1.354(4) . ?
N2 N3 1.375(4) . ?
N2 C1 1.285(9) . ?
N3 H3A 0.8600 . ?
N3 C2 1.356(11) . ?
N5 C7 1.349(5) . ?
N5 C3 1.349(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.364(12) . ?
C9 H9 0.9300 . ?
C9 C8 1.340(10) . ?
C9 C10 1.413(7) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.349(10) . ?
C6 C5 1.415(7) . ?
C10 C11 1.398(5) . ?
C10 C5 1.431(10) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.348(11) . ?
C11 H11 0.9300 . ?
C5 C4 1.416(5) . ?
C4 H4 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 N4 H4A 123.9(14) . . ?
C1 N4 C2 103.6(5) . . ?
C1 N4 H4A 131.3(15) . . ?
O1 N1 O2 126.1(3) . . ?
O1 N1 C1 117.6(6) . . ?
O2 N1 C1 116.3(6) . . ?
C12 N6 C8 114.6(5) . . ?
C1 N2 N3 100.8(6) . . ?
N2 N3 H3A 123.6 . . ?
C2 N3 N2 112.8(5) . . ?
C2 N3 H3A 123.6 . . ?
C7 N5 C3 116.8(5) . . ?
N6 C12 H12 117.6 . . ?
N6 C12 C11 124.8(3) . . ?
C11 C12 H12 117.6 . . ?
O3 C2 N4 126.0(7) . . ?
O3 C2 N3 128.6(5) . . ?
N3 C2 N4 105.3(3) . . ?
N4 C1 N1 119.9(6) . . ?
N2 C1 N4 117.5(3) . . ?
N2 C1 N1 122.5(6) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
N6 C8 H8 117.7 . . ?
C9 C8 N6 124.6(4) . . ?
C9 C8 H8 117.7 . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C5 121.5(3) . . ?
C5 C6 H6 119.3 . . ?
C9 C10 C5 123.1(3) . . ?
C11 C10 C9 115.1(5) . . ?
C11 C10 C5 121.7(4) . . ?
N5 C7 H7 118.6 . . ?
C6 C7 N5 122.8(5) . . ?
C6 C7 H7 118.6 . . ?
N5 C3 H3 118.0 . . ?
C4 C3 N5 124.0(3) . . ?
C4 C3 H3 118.0 . . ?
C12 C11 C10 120.0(5) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C6 C5 C10 122.8(3) . . ?
C6 C5 C4 114.6(6) . . ?
C4 C5 C10 122.6(4) . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?

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 N1 C1 N4 -178.2(3) . . . . ?
O1 N1 C1 N2 0.6(5) . . . . ?
O2 N1 C1 N4 0.6(5) . . . . ?
O2 N1 C1 N2 179.4(4) . . . . ?
N6 C12 C11 C10 0.2(7) . . . . ?
N2 N3 C2 O3 -179.2(3) . . . . ?
N2 N3 C2 N4 -0.9(4) . . . . ?
N3 N2 C1 N4 1.2(4) . . . . ?
N3 N2 C1 N1 -177.6(3) . . . . ?
N5 C3 C4 C5 1.1(7) . . . . ?
C12 N6 C8 C9 -2.6(5) . . . . ?
C2 N4 C1 N1 177.1(3) . . . . ?
C2 N4 C1 N2 -1.8(4) . . . . ?
C1 N4 C2 O3 179.8(3) . . . . ?
C1 N4 C2 N3 1.5(4) . . . . ?
C1 N2 N3 C2 -0.1(4) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C9 C10 C5 C6 178.8(3) . . . . ?
C9 C10 C5 C4 -2.4(6) . . . . ?
C8 N6 C12 C11 1.3(6) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C8 C9 C10 C5 -177.1(4) . . . . ?
C6 C5 C4 C3 -0.6(6) . . . . ?
C10 C9 C8 N6 2.5(6) . . . . ?
C10 C5 C4 C3 -179.5(4) . . . . ?
C7 N5 C3 C4 -1.3(6) . . . . ?
C7 C6 C5 C10 179.2(4) . . . . ?
C7 C6 C5 C4 0.3(6) . . . . ?
C3 N5 C7 C6 1.0(6) . . . . ?
C11 C10 C5 C6 2.8(6) . . . . ?
C11 C10 C5 C4 -178.5(3) . . . . ?
C5 C6 C7 N5 -0.6(7) . . . . ?
C5 C10 C11 C12 175.9(4) . . . . ?


_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_3car_p02
_audit_block_doi                 10.5517/ccdc.csd.cc2bvm4z
_database_code_depnum_ccdc_archive 'CCDC 2170531'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_3car_p02            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.411 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:23 PM
# end Validation Reply Form

_audit_creation_date             2022-05-04
_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                   7.2334(6)
_cell_length_b                   5.6302(4)
_cell_length_c                   26.082(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.001(8)
_cell_angle_gamma                90
_cell_volume                     1059.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1916
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      2.88
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1664 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.8068.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.794
_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  0.0428
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.411
_diffrn_reflns_Laue_measured_fraction_max 0.381
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4897
_diffrn_reflns_point_group_measured_fraction_full 0.411
_diffrn_reflns_point_group_measured_fraction_max 0.381
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.385
_diffrn_reflns_theta_min         2.876
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.411
_diffrn_measured_fraction_theta_max 0.381
_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                665
_reflns_number_total             823
_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         0.112
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         823
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      0.986
_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)+(0.0437P)²+0.2005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
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), N3(H3A), C9(H9), C11(H11), C4(H4), C3(H3), C12(H12), C7(H7), C6(H6),
 C8(H8)
;
_atom_sites_solution_hydrogens   geom
_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
O3 O 0.52398(19) 0.2792(2) 0.36979(13) 0.0285(17) Uani 1 1 d . . . . .
O2 O 0.1754(3) 1.0326(3) 0.3910(2) 0.029(2) Uani 1 1 d . . . . .
O1 O 0.1891(2) 1.1478(3) 0.31113(16) 0.029(2) Uani 1 1 d . . . . .
N2 N 0.3688(2) 0.6398(3) 0.37343(17) 0.019(2) Uani 1 1 d . . . . .
H2 H 0.341665 0.645787 0.404984 0.023 Uiso 1 1 calc R U . . .
N6 N 0.1180(2) 0.1926(3) 0.71916(17) 0.0206(19) Uani 1 1 d . . . . .
N5 N 0.2659(3) 0.5662(3) 0.46561(18) 0.027(2) Uani 1 1 d . . . . .
N4 N 0.3872(3) 0.7560(3) 0.2923(2) 0.022(2) Uani 1 1 d . . . . .
N3 N 0.4710(3) 0.5400(4) 0.3007(2) 0.024(2) Uani 1 1 d . . . . .
H3A H 0.524013 0.461938 0.277510 0.029 Uiso 1 1 calc R U . . .
C1 C 0.3300(3) 0.8017(4) 0.3365(3) 0.019(2) Uani 1 1 d . . . . .
C2 C 0.4613(3) 0.4628(4) 0.3497(3) 0.020(2) Uani 1 1 d . . . . .
C9 C 0.0754(3) 0.4795(4) 0.6524(3) 0.021(2) Uani 1 1 d . . . . .
H9 H 0.030405 0.628215 0.642257 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2314(3) 0.1194(4) 0.6365(3) 0.018(2) Uani 1 1 d . . . . .
H11 H 0.292370 0.016265 0.615501 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2014(3) 0.4171(4) 0.5661(2) 0.0182(18) Uani 1 1 d . . . . .
C10 C 0.1670(3) 0.3385(4) 0.6172(2) 0.0165(18) Uani 1 1 d . . . . .
C4 C 0.1423(3) 0.6401(4) 0.5465(3) 0.021(2) Uani 1 1 d . . . . .
H4 H 0.078751 0.742962 0.566973 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1771(3) 0.7056(4) 0.4984(3) 0.024(2) Uani 1 1 d . . . . .
H3 H 0.137862 0.855083 0.487023 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2048(3) 0.0572(4) 0.6858(3) 0.018(2) Uani 1 1 d . . . . .
H12 H 0.249925 -0.089548 0.697325 0.022 Uiso 1 1 calc R U . . .
C7 C 0.3242(3) 0.3535(4) 0.4840(3) 0.025(2) Uani 1 1 d . . . . .
H7 H 0.387679 0.254854 0.462636 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2955(3) 0.2758(4) 0.5317(3) 0.022(2) Uani 1 1 d . . . . .
H6 H 0.338499 0.126432 0.542076 0.027 Uiso 1 1 calc R U . . .
N1 N 0.2247(4) 1.0109(4) 0.3471(3) 0.023(2) Uani 1 1 d . . . . .
C8 C 0.0524(3) 0.4019(4) 0.7001(3) 0.025(2) Uani 1 1 d . . . . .
H8 H -0.012915 0.498244 0.721459 0.030 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
O3 C2 1.231(4) . ?
O2 N1 1.230(8) . ?
O1 N1 1.226(6) . ?
N2 H2 0.8600 . ?
N2 C1 1.342(6) . ?
N2 C2 1.372(5) . ?
N6 C12 1.345(6) . ?
N6 C8 1.352(4) . ?
N5 C3 1.355(6) . ?
N5 C7 1.347(4) . ?
N4 N3 1.370(3) . ?
N4 C1 1.278(8) . ?
N3 H3A 0.8600 . ?
N3 C2 1.356(9) . ?
C1 N1 1.440(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.412(6) . ?
C9 C8 1.340(9) . ?
C11 H11 0.9300 . ?
C11 C10 1.399(4) . ?
C11 C12 1.361(9) . ?
C5 C10 1.442(8) . ?
C5 C4 1.411(4) . ?
C5 C6 1.410(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.349(9) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.349(9) . ?
C6 H6 0.9300 . ?
C8 H8 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
C1 N2 H2 127.6 . . ?
C1 N2 C2 104.7(4) . . ?
C2 N2 H2 127.6 . . ?
C12 N6 C8 115.1(4) . . ?
C7 N5 C3 116.2(5) . . ?
C1 N4 N3 101.6(5) . . ?
N4 N3 H3A 123.7 . . ?
C2 N3 N4 112.7(4) . . ?
C2 N3 H3A 123.7 . . ?
N2 C1 N1 120.3(5) . . ?
N4 C1 N2 116.5(3) . . ?
N4 C1 N1 123.2(5) . . ?
O3 C2 N2 126.5(6) . . ?
O3 C2 N3 128.9(5) . . ?
N3 C2 N2 104.5(3) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.9(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.1(4) . . ?
C4 C5 C10 122.7(4) . . ?
C6 C5 C10 122.5(3) . . ?
C6 C5 C4 114.8(5) . . ?
C9 C10 C5 123.1(3) . . ?
C11 C10 C9 115.0(5) . . ?
C11 C10 C5 121.8(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
N5 C3 H3 118.1 . . ?
C4 C3 N5 123.8(3) . . ?
C4 C3 H3 118.1 . . ?
N6 C12 C11 124.7(3) . . ?
N6 C12 H12 117.7 . . ?
C11 C12 H12 117.7 . . ?
N5 C7 H7 118.2 . . ?
N5 C7 C6 123.5(4) . . ?
C6 C7 H7 118.2 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
O2 N1 C1 116.8(5) . . ?
O1 N1 O2 126.2(3) . . ?
O1 N1 C1 116.9(5) . . ?
N6 C8 H8 117.9 . . ?
C9 C8 N6 124.2(4) . . ?
C9 C8 H8 117.9 . . ?

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
N2 C1 N1 O2 0.7(5) . . . . ?
N2 C1 N1 O1 -177.7(3) . . . . ?
N5 C7 C6 C5 -0.4(6) . . . . ?
N4 N3 C2 O3 -179.0(3) . . . . ?
N4 N3 C2 N2 -0.7(4) . . . . ?
N4 C1 N1 O2 178.9(4) . . . . ?
N4 C1 N1 O1 0.5(5) . . . . ?
N3 N4 C1 N2 0.7(4) . . . . ?
N3 N4 C1 N1 -177.7(3) . . . . ?
C1 N2 C2 O3 179.4(3) . . . . ?
C1 N2 C2 N3 1.0(3) . . . . ?
C1 N4 N3 C2 0.1(4) . . . . ?
C2 N2 C1 N4 -1.1(4) . . . . ?
C2 N2 C1 N1 177.3(3) . . . . ?
C5 C4 C3 N5 1.1(6) . . . . ?
C10 C9 C8 N6 2.4(6) . . . . ?
C10 C11 C12 N6 0.3(6) . . . . ?
C10 C5 C4 C3 -179.8(4) . . . . ?
C10 C5 C6 C7 179.5(4) . . . . ?
C4 C5 C10 C9 -1.5(6) . . . . ?
C4 C5 C10 C11 -178.2(3) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C3 N5 C7 C6 1.1(5) . . . . ?
C12 N6 C8 C9 -2.5(5) . . . . ?
C12 C11 C10 C9 -0.5(5) . . . . ?
C12 C11 C10 C5 176.4(4) . . . . ?
C7 N5 C3 C4 -1.5(5) . . . . ?
C6 C5 C10 C9 179.0(3) . . . . ?
C6 C5 C10 C11 2.4(5) . . . . ?
C6 C5 C4 C3 -0.3(5) . . . . ?
C8 N6 C12 C11 1.2(5) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C8 C9 C10 C5 -177.6(4) . . . . ?


_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_3car_p08
_audit_block_doi                 10.5517/ccdc.csd.cc2bvm72
_database_code_depnum_ccdc_archive 'CCDC 2170534'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_3car_p08            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.363 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:23 PM
# end Validation Reply Form

_audit_creation_date             2022-05-04
_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                   7.1472(12)
_cell_length_b                   5.6110(4)
_cell_length_c                   25.939(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.766(8)
_cell_angle_gamma                90
_cell_volume                     1036.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2739
_cell_measurement_temperature    298.4
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      3.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0687 before and 0.0451 after correction.
The Ratio of minimum to maximum transmission is 0.8913.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.834
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.363
_diffrn_reflns_Laue_measured_fraction_max 0.333
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5518
_diffrn_reflns_point_group_measured_fraction_full 0.363
_diffrn_reflns_point_group_measured_fraction_max 0.333
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.152
_diffrn_ambient_temperature      298.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.363
_diffrn_measured_fraction_theta_max 0.333
_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                615
_reflns_number_total             704
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         704
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.010
_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)+(0.0559P)²+1.5315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
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:
 C4(H4), C7(H7), C6(H6), C11(H11), C9(H9), C3(H3), C12(H12), C8(H8)
;
_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 0.1850(11) -0.1542(4) 0.31137(14) 0.031(4) Uani 1 1 d . . . . .
O2 O 0.1752(11) -0.0374(4) 0.39132(13) 0.037(5) Uani 1 1 d . . . . .
O3 O 0.5236(11) 0.7177(4) 0.36895(14) 0.036(4) Uani 1 1 d . . . . .
N2 N 0.3681(13) 0.3557(5) 0.37300(16) 0.026(4) Uani 1 1 d . . . . .
N4 N 0.3861(13) 0.2378(5) 0.29174(15) 0.021(5) Uani 1 1 d . . . . .
N5 N 0.2687(13) 0.4329(6) 0.46591(17) 0.024(6) Uani 1 1 d . . . . .
N3 N 0.4701(13) 0.4536(5) 0.30002(17) 0.036(5) Uani 1 1 d . . . . .
N1 N 0.2220(13) -0.0165(5) 0.34654(15) 0.020(4) Uani 1 1 d . . . . .
N6 N 0.1223(12) 0.8120(5) 0.71895(15) 0.027(5) Uani 1 1 d . . . . .
C1 C 0.3293(15) 0.1906(6) 0.33710(19) 0.023(5) Uani 1 1 d . . . . .
C10 C 0.1685(15) 0.6655(6) 0.61768(19) 0.020(5) Uani 1 1 d . . . . .
C4 C 0.1438(16) 0.3596(6) 0.54653(19) 0.017(6) Uani 1 1 d . . . . .
H4 H 0.080607 0.257281 0.567322 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4647(15) 0.5331(6) 0.34972(19) 0.018(5) Uani 1 1 d . . . . .
C7 C 0.3234(17) 0.6453(7) 0.4826(2) 0.025(7) Uani 1 1 d . . . . .
H7 H 0.382222 0.745209 0.460351 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2022(16) 0.5832(6) 0.56469(19) 0.021(6) Uani 1 1 d . . . . .
C6 C 0.2972(16) 0.7264(7) 0.53185(19) 0.032(6) Uani 1 1 d . . . . .
H6 H 0.342606 0.874879 0.542821 0.039 Uiso 1 1 calc R U . . .
C11 C 0.2307(16) 0.8841(6) 0.6354(2) 0.015(6) Uani 1 1 d . . . . .
H11 H 0.286776 0.988312 0.613479 0.018 Uiso 1 1 calc R U . . .
C9 C 0.0721(16) 0.5220(6) 0.65058(19) 0.024(6) Uani 1 1 d . . . . .
H9 H 0.021184 0.376793 0.639292 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1807(16) 0.2920(6) 0.4975(2) 0.025(6) Uani 1 1 d . . . . .
H3 H 0.142706 0.141512 0.485889 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2099(16) 0.9498(6) 0.68639(19) 0.029(6) Uani 1 1 d . . . . .
H12 H 0.258783 1.095262 0.698277 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0544(16) 0.6017(6) 0.7005(2) 0.020(6) Uani 1 1 d . . . . .
H8 H -0.007981 0.504564 0.722490 0.024 Uiso 1 1 calc R U . . .
H3A H 0.51(2) 0.532(9) 0.276(3) 0.06(2) Uiso 1 1 d . . . . .
H2 H 0.311(18) 0.365(9) 0.406(3) 0.061(19) 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
O1 N1 1.208(6) . ?
O2 N1 1.241(4) . ?
O3 C2 1.210(7) . ?
N2 C1 1.326(7) . ?
N2 C2 1.379(7) . ?
N2 H2 0.99(6) . ?
N4 N3 1.361(7) . ?
N4 C1 1.304(5) . ?
N5 C7 1.316(8) . ?
N5 C3 1.334(7) . ?
N3 C2 1.368(6) . ?
N3 H3A 0.84(6) . ?
N1 C1 1.424(8) . ?
N6 C12 1.339(6) . ?
N6 C8 1.349(8) . ?
C10 C5 1.488(5) . ?
C10 C11 1.371(8) . ?
C10 C9 1.396(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(8) . ?
C4 C3 1.372(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.383(5) . ?
C5 C6 1.389(7) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.392(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.385(6) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C8 H8 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
C1 N2 C2 106.3(3) . . ?
C1 N2 H2 125(5) . . ?
C2 N2 H2 127(4) . . ?
C1 N4 N3 101.8(4) . . ?
C7 N5 C3 118.4(4) . . ?
N4 N3 C2 113.1(4) . . ?
N4 N3 H3A 122(5) . . ?
C2 N3 H3A 125(5) . . ?
O1 N1 O2 126.0(5) . . ?
O1 N1 C1 118.6(3) . . ?
O2 N1 C1 115.4(4) . . ?
C12 N6 C8 117.0(3) . . ?
N2 C1 N1 122.2(3) . . ?
N4 C1 N2 115.4(5) . . ?
N4 C1 N1 122.2(5) . . ?
C11 C10 C5 121.0(4) . . ?
C11 C10 C9 118.2(4) . . ?
C9 C10 C5 120.8(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(5) . . ?
O3 C2 N2 127.4(3) . . ?
O3 C2 N3 129.2(4) . . ?
N3 C2 N2 103.4(5) . . ?
N5 C7 H7 118.6 . . ?
N5 C7 C6 122.9(5) . . ?
C6 C7 H7 118.6 . . ?
C4 C5 C10 121.7(4) . . ?
C6 C5 C10 120.8(5) . . ?
C6 C5 C4 117.5(3) . . ?
C7 C6 C5 119.1(5) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C9 H9 120.9 . . ?
C8 C9 C10 118.3(5) . . ?
C8 C9 H9 120.9 . . ?
N5 C3 C4 122.9(5) . . ?
N5 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
N6 C12 C11 122.6(5) . . ?
N6 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N6 C8 C9 123.8(4) . . ?
N6 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?

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 N1 C1 N2 176.8(9) . . . . ?
O1 N1 C1 N4 1.0(14) . . . . ?
O2 N1 C1 N2 -3.3(14) . . . . ?
O2 N1 C1 N4 -179.1(9) . . . . ?
N4 N3 C2 O3 -178.7(10) . . . . ?
N4 N3 C2 N2 -1.1(11) . . . . ?
N5 C7 C6 C5 -2.8(17) . . . . ?
N3 N4 C1 N2 0.4(11) . . . . ?
N3 N4 C1 N1 176.4(9) . . . . ?
C1 N2 C2 O3 178.9(10) . . . . ?
C1 N2 C2 N3 1.2(10) . . . . ?
C1 N4 N3 C2 0.5(11) . . . . ?
C10 C5 C6 C7 -179.1(10) . . . . ?
C10 C11 C12 N6 -3.3(16) . . . . ?
C10 C9 C8 N6 1.1(16) . . . . ?
C4 C5 C6 C7 2.3(15) . . . . ?
C2 N2 C1 N4 -1.1(12) . . . . ?
C2 N2 C1 N1 -177.1(9) . . . . ?
C7 N5 C3 C4 0.4(16) . . . . ?
C5 C10 C11 C12 -175.3(10) . . . . ?
C5 C10 C9 C8 176.3(10) . . . . ?
C5 C4 C3 N5 -0.8(17) . . . . ?
C11 C10 C5 C4 178.5(9) . . . . ?
C11 C10 C5 C6 -0.1(15) . . . . ?
C11 C10 C9 C8 -3.9(15) . . . . ?
C9 C10 C5 C4 -1.7(16) . . . . ?
C9 C10 C5 C6 179.7(9) . . . . ?
C9 C10 C11 C12 4.9(14) . . . . ?
C3 N5 C7 C6 1.5(16) . . . . ?
C3 C4 C5 C10 -179.2(10) . . . . ?
C3 C4 C5 C6 -0.5(15) . . . . ?
C12 N6 C8 C9 0.6(15) . . . . ?
C8 N6 C12 C11 0.4(15) . . . . ?


_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_3CAR_P01
_audit_block_doi                 10.5517/ccdc.csd.cc2bvm94
_database_code_depnum_ccdc_archive 'CCDC 2170536'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_3CAR_P01            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.331 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
_vrf_PLAT088_3CAR_P01            
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.81 Note
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:23 PM
# end Validation Reply Form

_audit_creation_date             2022-05-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
loop_
_audit_author_email
?
_chemical_formula_moiety         'C2 H2 N4 O3, C10 H8 N2'
_chemical_formula_sum            'C12 H10 N6 O3'
_chemical_formula_weight         286.252
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.6129(13)
_cell_length_b                   5.7121(10)
_cell_length_c                   26.809(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.448(18)
_cell_angle_gamma                90
_cell_volume                     1165.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    275.6
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.78
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6627
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0921 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.8891.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_description       block
_exptl_crystal_F_000             592.284
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.3314
_diffrn_reflns_Laue_measured_fraction_max 0.3051
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6538
_diffrn_reflns_point_group_measured_fraction_full 0.3314
_diffrn_reflns_point_group_measured_fraction_max 0.3051
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.34
_diffrn_reflns_theta_min         2.78
_diffrn_ambient_temperature      275.6
_diffrn_measured_fraction_theta_full 0.3314
_diffrn_measured_fraction_theta_max 0.3051
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -9
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -6
_reflns_number_gt                590
_reflns_number_total             723
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_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  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.0874
_refine_diff_density_min         -0.1003
_refine_diff_density_rms         0.0257
_refine_ls_d_res_high            0.8010
_refine_ls_d_res_low             7.3382
_refine_ls_goodness_of_fit_ref   1.1857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     190
_refine_ls_number_reflns         723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.1857
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.1506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0691
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
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), C12(H12), N3(H3a), C7(H7), C4(H4), C8(H8), C3(H3), C6(H6), C9(H9),
 C11(H11)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
_atom_site_refinement_flags_adp
O3 O 0.51823(18) 0.7360(2) 0.37224(17) 0.044(3) Uani 1.000000 . U
O1 O 0.2021(2) -0.1147(3) 0.3122(2) 0.048(4) Uani 1.000000 . U
O2 O 0.1729(3) -0.0067(5) 0.3899(3) 0.050(5) Uani 1.000000 . U
N2 N 0.3661(2) 0.3809(3) 0.3747(2) 0.033(4) Uani 1.000000 . U
H2 H 0.3361(2) 0.3725(3) 0.4055(2) 0.039(5) Uiso 1.000000 R .
N4 N 0.3935(3) 0.2759(4) 0.2948(3) 0.034(5) Uani 1.000000 . U
N6 N 0.1092(2) 0.7836(3) 0.7210(2) 0.035(4) Uani 1.000000 . U
C12 C 0.1994(4) 0.9180(5) 0.6880(4) 0.031(4) Uani 1.000000 . U
H12 H 0.2425(4) 1.0611(5) 0.6992(4) 0.037(5) Uiso 1.000000 R .
N5 N 0.2646(2) 0.4420(4) 0.4693(2) 0.038(5) Uani 1.000000 . U
C10 C 0.1662(3) 0.6486(4) 0.6202(4) 0.019(6) Uani 1.000000 . U
N3 N 0.4762(4) 0.4867(5) 0.3046(4) 0.046(5) Uani 1.000000 . U
H3a H 0.5326(4) 0.5646(5) 0.2825(4) 0.055(6) Uiso 1.000000 R .
C5 C 0.2001(3) 0.5786(5) 0.5694(4) 0.024(6) Uani 1.000000 . U
N1 N 0.2292(4) 0.0180(5) 0.3475(4) 0.043(5) Uani 1.000000 . U
C2 C 0.4600(4) 0.5575(6) 0.3517(4) 0.039(7) Uani 1.000000 . U
C7 C 0.1770(4) 0.3043(6) 0.5020(4) 0.052(6) Uani 1.000000 . U
H7 H 0.1397(4) 0.1582(6) 0.4909(4) 0.062(7) Uiso 1.000000 R .
C1 C 0.3324(4) 0.2258(4) 0.3384(4) 0.023(6) Uani 1.000000 . U
C4 C 0.2908(4) 0.7207(6) 0.5348(4) 0.044(5) Uani 1.000000 . U
H4 H 0.3302(4) 0.8677(6) 0.5447(4) 0.053(6) Uiso 1.000000 R .
C8 C 0.0456(4) 0.5811(5) 0.7006(4) 0.045(5) Uani 1.000000 . U
H8 H -0.0228(4) 0.4859(5) 0.7208(4) 0.055(6) Uiso 1.000000 R .
C3 C 0.3210(4) 0.6485(6) 0.4886(4) 0.049(6) Uani 1.000000 . U
H3 H 0.3853(4) 0.7466(6) 0.4679(4) 0.059(7) Uiso 1.000000 R .
C6 C 0.1407(4) 0.3629(5) 0.5488(4) 0.049(5) Uani 1.000000 . U
H6 H 0.0754(4) 0.2611(5) 0.5684(4) 0.059(6) Uiso 1.000000 R .
C9 C 0.0734(4) 0.5096(5) 0.6543(4) 0.032(4) Uani 1.000000 . U
H9 H 0.0307(4) 0.3645(5) 0.6442(4) 0.039(5) Uiso 1.000000 R .
C11 C 0.2308(4) 0.8588(5) 0.6401(4) 0.041(5) Uani 1.000000 . U
H11 H 0.2962(4) 0.9587(5) 0.6201(4) 0.049(6) Uiso 1.000000 R .


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
O3 C2 1.239(6) . ?
O1 N1 1.229(10) . ?
O2 N1 1.227(13) . ?
N2 H2 0.8600 . ?
N2 C2 1.384(7) . ?
N2 C1 1.339(9) . ?
N4 N3 1.383(5) . ?
N4 C1 1.294(12) . ?
N6 C12 1.362(8) . ?
N6 C8 1.367(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.350(16) . ?
N5 C7 1.356(9) . ?
N5 C3 1.356(6) . ?
C10 C5 1.446(13) . ?
C10 C9 1.406(9) . ?
C10 C11 1.402(7) . ?
N3 H3a 0.8600 . ?
N3 C2 1.332(16) . ?
C5 C4 1.416(10) . ?
C5 C6 1.422(7) . ?
N1 C1 1.445(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.330(17) . ?
C4 H4 0.9300 . ?
C4 C3 1.328(16) . ?
C8 H8 0.9300 . ?
C8 C9 1.323(14) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C11 H11 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 N2 H2 127.6(4) . . ?
C1 N2 H2 127.6(3) . . ?
C1 N2 C2 104.8(6) . . ?
C1 N4 N3 100.7(7) . . ?
C8 N6 C12 113.3(6) . . ?
H12 C12 N6 117.6(4) . . ?
C11 C12 N6 124.8(4) . . ?
C11 C12 H12 117.6(2) . . ?
C3 N5 C7 114.5(7) . . ?
C9 C10 C5 123.5(4) . . ?
C11 C10 C5 122.1(6) . . ?
C11 C10 C9 114.4(8) . . ?
H3a N3 N4 123.2(5) . . ?
C2 N3 N4 113.6(7) . . ?
C2 N3 H3a 123.2(3) . . ?
C4 C5 C10 123.4(4) . . ?
C6 C5 C10 123.2(6) . . ?
C6 C5 C4 113.4(8) . . ?
O2 N1 O1 125.8(3) . . ?
C1 N1 O1 117.7(8) . . ?
C1 N1 O2 116.4(8) . . ?
N2 C2 O3 125.9(9) . . ?
N3 C2 O3 129.5(7) . . ?
N3 C2 N2 104.6(4) . . ?
H7 C7 N5 117.6(4) . . ?
C6 C7 N5 124.8(4) . . ?
C6 C7 H7 117.6(3) . . ?
N4 C1 N2 116.3(3) . . ?
N1 C1 N2 121.5(8) . . ?
N1 C1 N4 122.3(8) . . ?
H4 C4 C5 119.3(4) . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.3(3) . . ?
H8 C8 N6 117.4(4) . . ?
C9 C8 N6 125.3(6) . . ?
C9 C8 H8 117.4(2) . . ?
C4 C3 N5 124.6(6) . . ?
H3 C3 N5 117.7(5) . . ?
H3 C3 C4 117.7(3) . . ?
C7 C6 C5 121.1(6) . . ?
H6 C6 C5 119.5(5) . . ?
H6 C6 C7 119.5(2) . . ?
C8 C9 C10 121.3(4) . . ?
H9 C9 C10 119.3(4) . . ?
H9 C9 C8 119.3(2) . . ?
C10 C11 C12 120.8(7) . . ?
H11 C11 C12 119.6(2) . . ?
H11 C11 C10 119.6(5) . . ?

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 C2 N2 C1 -179.6(4) . . . . ?
O3 C2 N3 N4 179.8(6) . . . . ?
O1 N1 C1 N2 179.2(3) . . . . ?
O1 N1 C1 N4 0.9(4) . . . . ?
O2 N1 C1 N2 0.9(5) . . . . ?
O2 N1 C1 N4 -177.4(4) . . . . ?
N2 C2 N3 N4 1.8(3) . . . . ?
N2 C1 N4 N3 0.2(3) . . . . ?
N6 C12 C11 C10 1.6(5) . . . . ?
N6 C8 C9 C10 -3.9(6) . . . . ?
C12 C11 C10 C5 -179.0(6) . . . . ?
C12 C11 C10 C9 -1.6(7) . . . . ?
N5 C7 C6 C5 -2.9(6) . . . . ?
N5 C3 C4 C5 2.5(6) . . . . ?
C10 C5 C4 C3 179.2(6) . . . . ?
C10 C5 C6 C7 -179.1(7) . . . . ?


_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_3car_p09_h
_audit_block_doi                 10.5517/ccdc.csd.cc2bvm83
_database_code_depnum_ccdc_archive 'CCDC 2170535'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_3car_p09_h          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: This is due to the limitation of the high pressure data. intensity is not enough to determine anisotropic atomic displacement.
;
_vrf_PLAT029_3car_p09_h          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.355 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
_vrf_PLAT201_3car_p09_h          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         12 Report
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:23 PM
# end Validation Reply Form

_audit_creation_date             2022-05-03
_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                   7.0225(10)
_cell_length_b                   5.5811(4)
_cell_length_c                   25.7121(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.797(7)
_cell_angle_gamma                90
_cell_volume                     1002.59(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2747
_cell_measurement_temperature    298.4
_cell_measurement_theta_max      25.15
_cell_measurement_theta_min      3.74
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.896
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.355
_diffrn_reflns_Laue_measured_fraction_max 0.353
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5470
_diffrn_reflns_point_group_measured_fraction_full 0.355
_diffrn_reflns_point_group_measured_fraction_max 0.353
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.318
_diffrn_reflns_theta_min         1.592
_diffrn_ambient_temperature      298.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.355
_diffrn_measured_fraction_theta_max 0.353
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                560
_reflns_number_total             646
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.081
_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)+(0.0601P)²+2.5480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1361
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. 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
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3A), C4(H4), C6(H6), C11(H11), C8(H8), C7(H7), C9(H9), C12(H12),
 C3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
O2 O 0.1746(12) -0.0430(5) 0.39195(15) 0.0205(8) Uiso 1 1 d . . . . .
O1 O 0.1799(13) -0.1625(5) 0.31162(15) 0.0230(9) Uiso 1 1 d . . . . .
O3 O 0.5232(13) 0.7145(5) 0.36804(16) 0.0239(9) Uiso 1 1 d . . . . .
N2 N 0.3658(14) 0.3517(5) 0.37260(18) 0.0163(9) Uiso 1 1 d . . . . .
H2 H 0.336145 0.350583 0.404241 0.020 Uiso 1 1 calc R U . . .
N4 N 0.3793(14) 0.2289(6) 0.29085(18) 0.0176(9) Uiso 1 1 d . . . . .
N1 N 0.2181(14) -0.0226(6) 0.34670(18) 0.0171(9) Uiso 1 1 d . . . . .
N3 N 0.4655(15) 0.4470(6) 0.29878(19) 0.0178(9) Uiso 1 1 d . . . . .
H3A H 0.515704 0.525147 0.274769 0.021 Uiso 1 1 calc R U . . .
N5 N 0.2669(16) 0.4305(6) 0.46478(19) 0.0235(10) Uiso 1 1 d . . . . .
N6 N 0.1243(14) 0.8180(6) 0.71861(18) 0.0195(10) Uiso 1 1 d . . . . .
C1 C 0.3274(18) 0.1846(7) 0.3365(2) 0.0160(10) Uiso 1 1 d . . . . .
C5 C 0.2031(18) 0.5836(7) 0.5638(2) 0.0177(11) Uiso 1 1 d . . . . .
C2 C 0.4635(18) 0.5279(7) 0.3487(2) 0.0169(11) Uiso 1 1 d . . . . .
C4 C 0.1433(19) 0.3578(7) 0.5457(2) 0.0185(11) Uiso 1 1 d . . . . .
H4 H 0.080896 0.255027 0.566849 0.022 Uiso 1 1 calc R U . . .
C10 C 0.1696(17) 0.6688(7) 0.6168(2) 0.0159(11) Uiso 1 1 d . . . . .
C6 C 0.3002(19) 0.7271(7) 0.5310(2) 0.0197(11) Uiso 1 1 d . . . . .
H6 H 0.346620 0.876580 0.542106 0.024 Uiso 1 1 calc R U . . .
C11 C 0.2329(18) 0.8889(7) 0.6350(2) 0.0174(11) Uiso 1 1 d . . . . .
H11 H 0.290677 0.992906 0.613083 0.021 Uiso 1 1 calc R U . . .
C8 C 0.0563(18) 0.6051(7) 0.7003(2) 0.0188(11) Uiso 1 1 d . . . . .
H8 H -0.007502 0.508156 0.722299 0.023 Uiso 1 1 calc R U . . .
C7 C 0.327(2) 0.6445(8) 0.4818(2) 0.0242(12) Uiso 1 1 d . . . . .
H7 H 0.388543 0.742681 0.459572 0.029 Uiso 1 1 calc R U . . .
C9 C 0.0769(18) 0.5244(7) 0.6507(2) 0.0184(11) Uiso 1 1 d . . . . .
H9 H 0.029406 0.375096 0.639785 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2112(18) 0.9565(7) 0.6858(2) 0.0191(11) Uiso 1 1 d . . . . .
H12 H 0.258941 1.104393 0.697609 0.023 Uiso 1 1 calc R U . . .
C3 C 0.1776(19) 0.2891(8) 0.4964(2) 0.0210(11) Uiso 1 1 d . . . . .
H3 H 0.137105 0.138327 0.484507 0.025 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
O2 N1 1.238(5) . ?
O1 N1 1.203(7) . ?
O3 C2 1.211(8) . ?
N2 H2 0.8600 . ?
N2 C1 1.325(7) . ?
N2 C2 1.379(8) . ?
N4 N3 1.366(8) . ?
N4 C1 1.287(6) . ?
N1 C1 1.427(9) . ?
N3 H3A 0.8600 . ?
N3 C2 1.361(6) . ?
N5 C7 1.325(9) . ?
N5 C3 1.334(8) . ?
N6 C8 1.347(9) . ?
N6 C12 1.336(7) . ?
C5 C4 1.394(9) . ?
C5 C10 1.485(6) . ?
C5 C6 1.391(8) . ?
C4 H4 0.9300 . ?
C4 C3 1.368(6) . ?
C10 C11 1.373(9) . ?
C10 C9 1.395(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.377(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(6) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C3 H3 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
C1 N2 H2 127.3 . . ?
C1 N2 C2 105.3(4) . . ?
C2 N2 H2 127.3 . . ?
C1 N4 N3 101.4(5) . . ?
O2 N1 C1 115.9(5) . . ?
O1 N1 O2 126.0(5) . . ?
O1 N1 C1 118.1(4) . . ?
N4 N3 H3A 123.5 . . ?
C2 N3 N4 112.9(4) . . ?
C2 N3 H3A 123.5 . . ?
C7 N5 C3 119.0(4) . . ?
C12 N6 C8 117.3(4) . . ?
N2 C1 N1 121.1(4) . . ?
N4 C1 N2 116.6(5) . . ?
N4 C1 N1 122.1(6) . . ?
C4 C5 C10 121.7(5) . . ?
C6 C5 C4 117.9(4) . . ?
C6 C5 C10 120.4(6) . . ?
O3 C2 N2 126.7(4) . . ?
O3 C2 N3 129.5(5) . . ?
N3 C2 N2 103.7(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C11 C10 C5 121.6(5) . . ?
C11 C10 C9 117.4(4) . . ?
C9 C10 C5 121.0(5) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(6) . . ?
C7 C6 H6 120.5 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(5) . . ?
C12 C11 H11 119.9 . . ?
N6 C8 H8 118.4 . . ?
N6 C8 C9 123.1(5) . . ?
C9 C8 H8 118.4 . . ?
N5 C7 C6 122.5(6) . . ?
N5 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C10 C9 H9 120.3 . . ?
C8 C9 C10 119.3(6) . . ?
C8 C9 H9 120.3 . . ?
N6 C12 C11 122.6(6) . . ?
N6 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
N5 C3 C4 122.4(6) . . ?
N5 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?

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 N1 C1 N2 -4.9(15) . . . . ?
O2 N1 C1 N4 -178.9(9) . . . . ?
O1 N1 C1 N2 176.4(10) . . . . ?
O1 N1 C1 N4 2.5(16) . . . . ?
N4 N3 C2 O3 -178.2(11) . . . . ?
N4 N3 C2 N2 -1.6(12) . . . . ?
N3 N4 C1 N2 1.7(13) . . . . ?
N3 N4 C1 N1 175.9(9) . . . . ?
N6 C8 C9 C10 -1.0(18) . . . . ?
C1 N2 C2 O3 179.2(11) . . . . ?
C1 N2 C2 N3 2.4(11) . . . . ?
C1 N4 N3 C2 0.1(12) . . . . ?
C5 C4 C3 N5 0(2) . . . . ?
C5 C10 C11 C12 -175.6(12) . . . . ?
C5 C10 C9 C8 177.0(11) . . . . ?
C5 C6 C7 N5 -1.7(19) . . . . ?
C2 N2 C1 N4 -2.7(13) . . . . ?
C2 N2 C1 N1 -177.0(10) . . . . ?
C4 C5 C10 C11 178.3(11) . . . . ?
C4 C5 C10 C9 0.2(19) . . . . ?
C4 C5 C6 C7 2.4(17) . . . . ?
C10 C5 C4 C3 179.8(12) . . . . ?
C10 C5 C6 C7 -179.0(11) . . . . ?
C10 C11 C12 N6 -2.1(18) . . . . ?
C6 C5 C4 C3 -1.7(18) . . . . ?
C6 C5 C10 C11 -0.2(17) . . . . ?
C6 C5 C10 C9 -178.3(11) . . . . ?
C11 C10 C9 C8 -1.2(17) . . . . ?
C8 N6 C12 C11 -0.1(17) . . . . ?
C7 N5 C3 C4 0.7(18) . . . . ?
C9 C10 C11 C12 2.7(17) . . . . ?
C12 N6 C8 C9 1.7(16) . . . . ?
C3 N5 C7 C6 0.1(18) . . . . ?


_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_2car_p03_p
_audit_block_doi                 10.5517/ccdc.csd.cc2bvmb5
_database_code_depnum_ccdc_archive 'CCDC 2170537'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2car_p03_p          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.355 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:24 PM
# end Validation Reply Form

_audit_creation_date             2022-05-03
_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         '2(C2 H2 N4 O3), 2(C10 H8 N2)'
_chemical_formula_sum            'C24 H20 N12 O6'
_chemical_formula_weight         572.52
_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                   7.6153(11)
_cell_length_b                   5.7099(4)
_cell_length_c                   26.8265(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.275(7)
_cell_angle_gamma                90
_cell_volume                     1166.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2997
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      3.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0872 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.8301.
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    1.630
_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  0.0499
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.355
_diffrn_reflns_Laue_measured_fraction_max 0.290
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6348
_diffrn_reflns_point_group_measured_fraction_full 0.355
_diffrn_reflns_point_group_measured_fraction_max 0.290
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.895
_diffrn_reflns_theta_min         4.235
_diffrn_ambient_temperature      296.1
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.355
_diffrn_measured_fraction_theta_max 0.290
_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                662
_reflns_number_total             813
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         813
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.025
_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)+(0.0716P)²+1.7831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1509
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 N3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 O3, C2, N2, N3, C1, N4, H3A, N1, O2, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N6, C8, C12, C9, H8, C11, H12, C10, H9, H11, C5, C6, C4, H6, C7, H4, N5, H7,
 H3, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3A), C6(H6), C11(H11), C4(H4), C9(H9), C8(H8), C12(H12), C7(H7),
 C3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
O3 O 0.5192(12) 0.2644(5) 0.37235(13) 0.053(5) Uani 1 1 d . . . . .
O2 O 0.1725(12) 1.0062(6) 0.39000(13) 0.064(6) Uani 1 1 d . . . . .
N4 N 0.3942(14) 0.7217(6) 0.29544(14) 0.050(6) Uani 1 1 d . . . . .
N2 N 0.3648(13) 0.6193(6) 0.37456(14) 0.032(5) Uani 1 1 d . . . . .
H2 H 0.332437 0.627572 0.405173 0.039 Uiso 1 1 calc R U . . .
N6 N 0.1099(14) 0.2170(6) 0.72005(14) 0.041(5) Uani 1 1 d . . . . .
O1 O 0.2029(13) 1.1143(5) 0.31265(14) 0.074(5) Uani 1 1 d . . . . .
N1 N 0.2295(14) 0.9805(6) 0.34735(15) 0.029(5) Uani 1 1 d . . . . .
N5 N 0.2655(14) 0.5568(7) 0.46999(14) 0.046(7) Uani 1 1 d . . . . .
N3 N 0.4726(14) 0.5138(6) 0.30417(14) 0.054(6) Uani 1 1 d . . . . .
H3A H 0.524815 0.434219 0.281416 0.065 Uiso 1 1 calc R U . . .
C10 C 0.1693(16) 0.3507(7) 0.62119(16) 0.035(6) Uani 1 1 d . . . . .
C5 C 0.2008(17) 0.4231(7) 0.56825(17) 0.059(7) Uani 1 1 d . . . . .
C6 C 0.1464(18) 0.6376(7) 0.54997(18) 0.050(7) Uani 1 1 d . . . . .
H6 H 0.087376 0.742044 0.570537 0.060 Uiso 1 1 calc R U . . .
C11 C 0.2318(17) 0.1413(8) 0.63966(18) 0.044(7) Uani 1 1 d . . . . .
H11 H 0.293176 0.039848 0.618960 0.052 Uiso 1 1 calc R U . . .
C1 C 0.3319(16) 0.7750(7) 0.33879(17) 0.036(5) Uani 1 1 d . . . . .
C4 C 0.2900(18) 0.2783(8) 0.53598(17) 0.061(8) Uani 1 1 d . . . . .
H4 H 0.331096 0.133371 0.546711 0.073 Uiso 1 1 calc R U . . .
C9 C 0.0747(17) 0.4920(7) 0.65325(17) 0.030(7) Uani 1 1 d . . . . .
H9 H 0.029821 0.634421 0.642226 0.036 Uiso 1 1 calc R U . . .
C8 C 0.0471(18) 0.4192(8) 0.70219(18) 0.047(7) Uani 1 1 d . . . . .
H8 H -0.017556 0.515174 0.723268 0.056 Uiso 1 1 calc R U . . .
C2 C 0.4612(17) 0.4416(7) 0.35284(17) 0.034(6) Uani 1 1 d . . . . .
C12 C 0.2034(17) 0.0821(7) 0.68876(18) 0.042(7) Uani 1 1 d . . . . .
H12 H 0.250896 -0.056968 0.700798 0.050 Uiso 1 1 calc R U . . .
C7 C 0.1800(18) 0.6956(8) 0.50121(17) 0.048(8) Uani 1 1 d . . . . .
H7 H 0.140803 0.839814 0.489508 0.058 Uiso 1 1 calc R U . . .
C3 C 0.3176(18) 0.3512(8) 0.48729(19) 0.036(8) Uani 1 1 d . . . . .
H3 H 0.375850 0.250325 0.465736 0.043 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
O3 C2 1.221(8) . ?
O2 N1 1.234(5) . ?
N4 N3 1.349(8) . ?
N4 C1 1.294(6) . ?
N2 H2 0.8600 . ?
N2 C1 1.331(7) . ?
N2 C2 1.383(9) . ?
N6 C8 1.337(9) . ?
N6 C12 1.346(9) . ?
O1 N1 1.221(6) . ?
N1 C1 1.428(10) . ?
N5 C7 1.326(8) . ?
N5 C3 1.323(9) . ?
N3 H3A 0.8600 . ?
N3 C2 1.373(6) . ?
C10 C5 1.499(5) . ?
C10 C11 1.378(9) . ?
C10 C9 1.384(8) . ?
C5 C6 1.382(9) . ?
C5 C4 1.379(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.388(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.394(5) . ?
C8 H8 0.9300 . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 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
C1 N4 N3 102.4(4) . . ?
C1 N2 H2 126.7 . . ?
C1 N2 C2 106.6(4) . . ?
C2 N2 H2 126.7 . . ?
C8 N6 C12 117.4(4) . . ?
O2 N1 C1 116.2(5) . . ?
O1 N1 O2 125.1(6) . . ?
O1 N1 C1 118.7(4) . . ?
C3 N5 C7 117.2(4) . . ?
N4 N3 H3A 123.2 . . ?
N4 N3 C2 113.6(5) . . ?
C2 N3 H3A 123.2 . . ?
C11 C10 C5 121.6(5) . . ?
C11 C10 C9 117.5(4) . . ?
C9 C10 C5 120.9(6) . . ?
C6 C5 C10 122.1(5) . . ?
C4 C5 C10 120.7(6) . . ?
C4 C5 C6 117.1(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.7(6) . . ?
C7 C6 H6 120.2 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.1(6) . . ?
C12 C11 H11 120.0 . . ?
N4 C1 N2 115.0(6) . . ?
N4 C1 N1 122.7(5) . . ?
N2 C1 N1 122.3(4) . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.3(6) . . ?
C3 C4 H4 120.4 . . ?
C10 C9 H9 120.2 . . ?
C10 C9 C8 119.5(6) . . ?
C8 C9 H9 120.2 . . ?
N6 C8 C9 122.6(6) . . ?
N6 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
O3 C2 N2 128.3(4) . . ?
O3 C2 N3 129.2(6) . . ?
N3 C2 N2 102.5(5) . . ?
N6 C12 C11 122.8(6) . . ?
N6 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
N5 C7 C6 123.4(6) . . ?
N5 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
N5 C3 C4 123.3(6) . . ?
N5 C3 H3 118.3 . . ?
C4 C3 H3 118.3 . . ?

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 N1 C1 N4 177.3(10) . . . . ?
O2 N1 C1 N2 0.0(15) . . . . ?
N4 N3 C2 O3 -179.5(11) . . . . ?
N4 N3 C2 N2 1.3(12) . . . . ?
O1 N1 C1 N4 -1.8(15) . . . . ?
O1 N1 C1 N2 -179.1(10) . . . . ?
N3 N4 C1 N2 0.3(12) . . . . ?
N3 N4 C1 N1 -177.2(9) . . . . ?
C10 C5 C6 C7 179.5(12) . . . . ?
C10 C5 C4 C3 -179.7(12) . . . . ?
C10 C11 C12 N6 2.6(18) . . . . ?
C10 C9 C8 N6 0.5(18) . . . . ?
C5 C10 C11 C12 178.8(12) . . . . ?
C5 C10 C9 C8 179.7(11) . . . . ?
C5 C6 C7 N5 -1(2) . . . . ?
C5 C4 C3 N5 1.3(19) . . . . ?
C6 C5 C4 C3 -1.2(18) . . . . ?
C11 C10 C5 C6 -176.7(11) . . . . ?
C11 C10 C5 C4 1.7(18) . . . . ?
C11 C10 C9 C8 0.3(16) . . . . ?
C1 N4 N3 C2 -1.0(12) . . . . ?
C1 N2 C2 O3 179.8(11) . . . . ?
C1 N2 C2 N3 -1.0(11) . . . . ?
C4 C5 C6 C7 1.0(18) . . . . ?
C9 C10 C5 C6 3.8(18) . . . . ?
C9 C10 C5 C4 -177.8(11) . . . . ?
C9 C10 C11 C12 -1.8(17) . . . . ?
C8 N6 C12 C11 -1.8(17) . . . . ?
C2 N2 C1 N4 0.4(13) . . . . ?
C2 N2 C1 N1 178.0(10) . . . . ?
C12 N6 C8 C9 0.2(16) . . . . ?
C7 N5 C3 C4 -1.2(18) . . . . ?
C3 N5 C7 C6 1.0(18) . . . . ?


_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_2car_p01
_audit_block_doi                 10.5517/ccdc.csd.cc2bvmg9
_database_code_depnum_ccdc_archive 'CCDC 2170541'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2car_p01            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.551 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 02:12 PM
# end Validation Reply Form

_audit_creation_date             2022-05-04
_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                   7.9306(12)
_cell_length_b                   5.7908(7)
_cell_length_c                   27.809(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.349(10)
_cell_angle_gamma                90
_cell_volume                     1271.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1996
_cell_measurement_temperature    289.5
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.62
_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  0.6540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0879 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.8774.
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    1.495
_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  0.0472
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.551
_diffrn_reflns_Laue_measured_fraction_max 0.551
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7300
_diffrn_reflns_point_group_measured_fraction_full 0.551
_diffrn_reflns_point_group_measured_fraction_max 0.551
_diffrn_reflns_theta_full        24.977
_diffrn_reflns_theta_max         24.977
_diffrn_reflns_theta_min         2.616
_diffrn_ambient_temperature      289.5
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.551
_diffrn_measured_fraction_theta_max 0.551
_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                832
_reflns_number_total             1231
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1231
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.038
_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)+(0.0664P)²+0.2001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
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:
 N3(H3A), N2(H2), C8(H8), C9(H9), C11(H11), C12(H12), C4(H4), C6(H6), C7(H7),
 C3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
O3 O 0.4917(4) 0.7625(4) 0.37554(10) 0.0574(10) Uani 1 1 d . . . . .
O2 O 0.8356(5) 0.0334(5) 0.39529(13) 0.0710(13) Uani 1 1 d . . . . .
O1 O 0.7944(4) -0.0657(4) 0.31941(10) 0.0691(11) Uani 1 1 d . . . . .
N4 N 0.6095(4) 0.3212(5) 0.30179(12) 0.0457(11) Uani 1 1 d . . . . .
N3 N 0.5285(4) 0.5231(4) 0.30994(12) 0.0475(11) Uani 1 1 d . . . . .
H3A H 0.472081 0.600790 0.287513 0.057 Uiso 1 1 calc R U . . .
N2 N 0.6423(4) 0.4148(4) 0.37944(10) 0.0390(11) Uani 1 1 d . . . . .
H2 H 0.676361 0.403824 0.409632 0.047 Uiso 1 1 calc R U . . .
N1 N 0.7754(5) 0.0631(5) 0.35406(16) 0.0531(13) Uani 1 1 d . . . . .
N6 N 0.8975(5) 0.7529(5) 0.72446(13) 0.0509(12) Uani 1 1 d . . . . .
C1 C 0.6721(5) 0.2652(6) 0.34416(16) 0.0447(14) Uani 1 1 d . . . . .
C10 C 0.8338(5) 0.6348(5) 0.62611(14) 0.0371(11) Uani 1 1 d . . . . .
N5 N 0.7380(5) 0.4591(5) 0.47587(13) 0.0529(12) Uani 1 1 d . . . . .
C2 C 0.5458(5) 0.5897(6) 0.35715(15) 0.0423(13) Uani 1 1 d . . . . .
C8 C 0.9575(6) 0.5594(6) 0.70575(14) 0.0539(13) Uani 1 1 d . . . . .
H8 H 1.022771 0.461872 0.726535 0.065 Uiso 1 1 calc R U . . .
C9 C 0.9299(6) 0.4950(6) 0.65849(15) 0.0432(13) Uani 1 1 d . . . . .
H9 H 0.975441 0.357903 0.648045 0.052 Uiso 1 1 calc R U . . .
C11 C 0.7697(5) 0.8353(5) 0.64468(14) 0.0468(12) Uani 1 1 d . . . . .
H11 H 0.704047 0.935521 0.624606 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8014(5) 0.5745(5) 0.57464(14) 0.0388(11) Uani 1 1 d . . . . .
C12 C 0.8034(6) 0.8847(6) 0.69247(17) 0.0510(13) Uani 1 1 d . . . . .
H12 H 0.757944 1.019961 0.703849 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7093(6) 0.7166(6) 0.54161(16) 0.0529(14) Uani 1 1 d . . . . .
H4 H 0.666004 0.855460 0.551902 0.063 Uiso 1 1 calc R U . . .
C6 C 0.8588(5) 0.3702(5) 0.55527(14) 0.0514(13) Uani 1 1 d . . . . .
H6 H 0.920110 0.265145 0.575270 0.062 Uiso 1 1 calc R U . . .
C7 C 0.8259(6) 0.3228(7) 0.50720(18) 0.0572(14) Uani 1 1 d . . . . .
H7 H 0.868106 0.185633 0.495691 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6817(6) 0.6540(7) 0.49392(15) 0.0647(15) Uani 1 1 d . . . . .
H3 H 0.619684 0.754099 0.472936 0.078 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
O3 C2 1.220(4) . ?
O2 N1 1.212(5) . ?
O1 N1 1.239(4) . ?
N4 N3 1.363(4) . ?
N4 C1 1.277(6) . ?
N3 H3A 0.8600 . ?
N3 C2 1.363(5) . ?
N2 H2 0.8600 . ?
N2 C1 1.346(4) . ?
N2 C2 1.381(5) . ?
N1 C1 1.440(5) . ?
N6 C8 1.341(4) . ?
N6 C12 1.344(6) . ?
C10 C9 1.385(6) . ?
C10 C11 1.386(4) . ?
C10 C5 1.472(6) . ?
N5 C7 1.325(6) . ?
N5 C3 1.329(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.364(6) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.361(6) . ?
C5 C4 1.389(6) . ?
C5 C6 1.394(4) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.373(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.366(6) . ?
C7 H7 0.9300 . ?
C3 H3 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
C1 N4 N3 102.3(3) . . ?
N4 N3 H3A 123.3 . . ?
C2 N3 N4 113.3(3) . . ?
C2 N3 H3A 123.3 . . ?
C1 N2 H2 127.1 . . ?
C1 N2 C2 105.8(4) . . ?
C2 N2 H2 127.1 . . ?
O2 N1 O1 125.8(3) . . ?
O2 N1 C1 117.6(3) . . ?
O1 N1 C1 116.7(4) . . ?
C8 N6 C12 114.4(4) . . ?
N4 C1 N2 115.4(3) . . ?
N4 C1 N1 123.2(3) . . ?
N2 C1 N1 121.3(4) . . ?
C9 C10 C11 116.5(4) . . ?
C9 C10 C5 121.9(3) . . ?
C11 C10 C5 121.6(3) . . ?
C7 N5 C3 115.6(4) . . ?
O3 C2 N3 128.9(4) . . ?
O3 C2 N2 128.0(4) . . ?
N3 C2 N2 103.1(3) . . ?
N6 C8 H8 117.6 . . ?
N6 C8 C9 124.8(4) . . ?
C9 C8 H8 117.6 . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C4 C5 C10 122.4(3) . . ?
C4 C5 C6 114.7(4) . . ?
C6 C5 C10 122.9(4) . . ?
N6 C12 C11 125.0(4) . . ?
N6 C12 H12 117.5 . . ?
C11 C12 H12 117.5 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H6 119.7 . . ?
N5 C7 C6 124.4(4) . . ?
N5 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
N5 C3 C4 124.1(4) . . ?
N5 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?

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
O2 N1 C1 N4 176.1(4) . . . . ?
O2 N1 C1 N2 -0.5(6) . . . . ?
O1 N1 C1 N4 -4.0(6) . . . . ?
O1 N1 C1 N2 179.4(3) . . . . ?
N4 N3 C2 O3 178.4(3) . . . . ?
N4 N3 C2 N2 -0.7(4) . . . . ?
N3 N4 C1 N2 -1.3(4) . . . . ?
N3 N4 C1 N1 -178.1(3) . . . . ?
N6 C8 C9 C10 0.1(6) . . . . ?
C1 N4 N3 C2 1.2(4) . . . . ?
C1 N2 C2 O3 -179.2(3) . . . . ?
C1 N2 C2 N3 0.0(4) . . . . ?
C10 C11 C12 N6 0.4(6) . . . . ?
C10 C5 C4 C3 -179.9(3) . . . . ?
C10 C5 C6 C7 -179.7(3) . . . . ?
C2 N2 C1 N4 0.9(5) . . . . ?
C2 N2 C1 N1 177.8(3) . . . . ?
C8 N6 C12 C11 -0.7(6) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C9 C10 C5 C4 -178.1(4) . . . . ?
C9 C10 C5 C6 2.6(5) . . . . ?
C11 C10 C9 C8 -0.4(6) . . . . ?
C11 C10 C5 C4 1.8(5) . . . . ?
C11 C10 C5 C6 -177.6(3) . . . . ?
C5 C10 C9 C8 179.5(3) . . . . ?
C5 C10 C11 C12 -179.7(3) . . . . ?
C5 C4 C3 N5 0.2(7) . . . . ?
C5 C6 C7 N5 -1.0(7) . . . . ?
C12 N6 C8 C9 0.4(5) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C6 C5 C4 C3 -0.5(6) . . . . ?
C7 N5 C3 C4 -0.2(6) . . . . ?
C3 N5 C7 C6 0.6(7) . . . . ?


_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_2car_p05
_audit_block_doi                 10.5517/ccdc.csd.cc2bvmf8
_database_code_depnum_ccdc_archive 'CCDC 2170540'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2car_p05            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.340 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:24 PM
# end Validation Reply Form

_audit_creation_date             2022-05-03
_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                   7.3848(11)
_cell_length_b                   5.6634(4)
_cell_length_c                   26.3751(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.598(7)
_cell_angle_gamma                90
_cell_volume                     1102.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3002
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.68
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0827 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.8245.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.725
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.340
_diffrn_reflns_Laue_measured_fraction_max 0.318
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6162
_diffrn_reflns_point_group_measured_fraction_full 0.340
_diffrn_reflns_point_group_measured_fraction_max 0.318
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.291
_diffrn_reflns_theta_min         3.680
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.340
_diffrn_measured_fraction_theta_max 0.318
_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                607
_reflns_number_total             711
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         711
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      0.986
_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)+(0.0548P)²+1.1743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
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:
 N3(H3A), C8(H8), C11(H11), C7(H7), C6(H6), C4(H4), C3(H3), C12(H12), C9(H9)
;
_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
O3 O 0.5200(11) 0.7247(4) 0.37042(12) 0.034(4) Uani 1 1 d . . . . .
O2 O 0.1749(10) -0.0239(4) 0.39012(11) 0.042(5) Uani 1 1 d . . . . .
O1 O 0.1972(11) -0.1359(4) 0.31180(12) 0.036(4) Uani 1 1 d . . . . .
N4 N 0.3913(12) 0.2566(5) 0.29359(13) 0.023(5) Uani 1 1 d . . . . .
N5 N 0.2665(14) 0.4373(5) 0.46749(14) 0.033(6) Uani 1 1 d . . . . .
N3 N 0.4721(12) 0.4683(5) 0.30192(13) 0.030(5) Uani 1 1 d . . . . .
H3A H 0.524164 0.546909 0.278786 0.036 Uiso 1 1 calc R U . . .
N6 N 0.1126(12) 0.7988(5) 0.71896(13) 0.031(5) Uani 1 1 d . . . . .
N2 N 0.3678(12) 0.3670(5) 0.37381(13) 0.028(5) Uani 1 1 d . . . . .
N1 N 0.2284(12) 0.0004(5) 0.34671(13) 0.021(5) Uani 1 1 d . . . . .
C1 C 0.3332(15) 0.2061(6) 0.33764(16) 0.018(5) Uani 1 1 d . . . . .
C2 C 0.4624(14) 0.5445(6) 0.35113(16) 0.019(5) Uani 1 1 d . . . . .
C10 C 0.1693(15) 0.6580(6) 0.61918(16) 0.026(6) Uani 1 1 d . . . . .
C5 C 0.2007(16) 0.5798(6) 0.56629(16) 0.032(6) Uani 1 1 d . . . . .
C8 C 0.0499(16) 0.5925(6) 0.70081(17) 0.030(6) Uani 1 1 d . . . . .
H8 H -0.012323 0.494962 0.722411 0.037 Uiso 1 1 calc R U . . .
C11 C 0.2276(15) 0.8722(6) 0.63720(17) 0.030(6) Uani 1 1 d . . . . .
H11 H 0.285068 0.976384 0.615919 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3226(17) 0.6462(7) 0.48487(17) 0.034(7) Uani 1 1 d . . . . .
H7 H 0.385327 0.744030 0.463432 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2921(16) 0.7248(6) 0.53341(16) 0.038(7) Uani 1 1 d . . . . .
H6 H 0.332289 0.873290 0.543959 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1446(16) 0.3614(6) 0.54821(17) 0.030(7) Uani 1 1 d . . . . .
H4 H 0.085131 0.257597 0.569120 0.037 Uiso 1 1 calc R U . . .
C3 C 0.1776(16) 0.2984(6) 0.49881(16) 0.031(7) Uani 1 1 d . . . . .
H3 H 0.135949 0.152747 0.486888 0.037 Uiso 1 1 calc R U . . .
C12 C 0.2013(15) 0.9346(6) 0.68699(16) 0.024(6) Uani 1 1 d . . . . .
H12 H 0.247605 1.078075 0.698783 0.029 Uiso 1 1 calc R U . . .
C9 C 0.0726(15) 0.5164(6) 0.65179(16) 0.031(6) Uani 1 1 d . . . . .
H9 H 0.024093 0.372944 0.640656 0.038 Uiso 1 1 calc R U . . .
H2 H 0.350(15) 0.359(7) 0.408(2) 0.047(15) 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
O3 C2 1.209(7) . ?
O2 N1 1.236(4) . ?
O1 N1 1.215(5) . ?
N4 N3 1.352(7) . ?
N4 C1 1.289(5) . ?
N5 C7 1.328(8) . ?
N5 C3 1.334(7) . ?
N3 H3A 0.8600 . ?
N3 C2 1.373(5) . ?
N6 C8 1.337(7) . ?
N6 C12 1.335(7) . ?
N2 C1 1.336(6) . ?
N2 C2 1.376(7) . ?
N2 H2 0.93(4) . ?
N1 C1 1.425(8) . ?
C10 C5 1.492(5) . ?
C10 C11 1.366(8) . ?
C10 C9 1.396(7) . ?
C5 C6 1.391(7) . ?
C5 C4 1.382(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.384(5) . ?
C6 H6 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.383(5) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?
C9 H9 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
C1 N4 N3 102.3(4) . . ?
C7 N5 C3 117.8(3) . . ?
N4 N3 H3A 123.5 . . ?
N4 N3 C2 113.0(4) . . ?
C2 N3 H3A 123.5 . . ?
C12 N6 C8 116.7(3) . . ?
C1 N2 C2 105.8(3) . . ?
C1 N2 H2 130(4) . . ?
C2 N2 H2 124(4) . . ?
O2 N1 C1 116.5(4) . . ?
O1 N1 O2 125.0(5) . . ?
O1 N1 C1 118.5(3) . . ?
N4 C1 N2 115.6(5) . . ?
N4 C1 N1 122.6(5) . . ?
N2 C1 N1 121.7(3) . . ?
O3 C2 N3 129.1(4) . . ?
O3 C2 N2 127.5(3) . . ?
N3 C2 N2 103.3(4) . . ?
C11 C10 C5 121.9(4) . . ?
C11 C10 C9 117.3(3) . . ?
C9 C10 C5 120.8(5) . . ?
C6 C5 C10 120.6(5) . . ?
C4 C5 C10 122.1(4) . . ?
C4 C5 C6 117.3(3) . . ?
N6 C8 H8 118.2 . . ?
N6 C8 C9 123.6(5) . . ?
C9 C8 H8 118.2 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(4) . . ?
C12 C11 H11 119.9 . . ?
N5 C7 H7 118.5 . . ?
N5 C7 C6 123.0(5) . . ?
C6 C7 H7 118.5 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(5) . . ?
C7 C6 H6 120.3 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
N5 C3 C4 122.9(5) . . ?
N5 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
N6 C12 C11 123.2(5) . . ?
N6 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C10 C9 H9 120.5 . . ?
C8 C9 C10 119.0(5) . . ?
C8 C9 H9 120.5 . . ?

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 N1 C1 N4 -177.4(9) . . . . ?
O2 N1 C1 N2 -1.6(13) . . . . ?
O1 N1 C1 N4 2.1(13) . . . . ?
O1 N1 C1 N2 177.9(9) . . . . ?
N4 N3 C2 O3 -179.6(9) . . . . ?
N4 N3 C2 N2 -0.5(10) . . . . ?
N5 C7 C6 C5 0.9(18) . . . . ?
N3 N4 C1 N2 0.5(11) . . . . ?
N3 N4 C1 N1 176.5(8) . . . . ?
N6 C8 C9 C10 1.5(16) . . . . ?
C1 N4 N3 C2 0.1(10) . . . . ?
C1 N2 C2 O3 179.9(10) . . . . ?
C1 N2 C2 N3 0.8(10) . . . . ?
C2 N2 C1 N4 -0.8(12) . . . . ?
C2 N2 C1 N1 -176.9(8) . . . . ?
C10 C5 C6 C7 178.7(10) . . . . ?
C10 C5 C4 C3 -180.0(10) . . . . ?
C10 C11 C12 N6 -3.2(15) . . . . ?
C5 C10 C11 C12 -177.7(10) . . . . ?
C5 C10 C9 C8 178.5(9) . . . . ?
C5 C4 C3 N5 1.8(18) . . . . ?
C8 N6 C12 C11 0.8(14) . . . . ?
C11 C10 C5 C6 0.2(16) . . . . ?
C11 C10 C5 C4 178.9(10) . . . . ?
C11 C10 C9 C8 -3.6(15) . . . . ?
C7 N5 C3 C4 -1.0(16) . . . . ?
C6 C5 C4 C3 -1.2(17) . . . . ?
C4 C5 C6 C7 0.0(17) . . . . ?
C3 N5 C7 C6 -0.4(16) . . . . ?
C12 N6 C8 C9 0.0(15) . . . . ?
C9 C10 C5 C6 177.9(10) . . . . ?
C9 C10 C5 C4 -3.4(16) . . . . ?
C9 C10 C11 C12 4.5(14) . . . . ?


_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_2car_p06
_audit_block_doi                 10.5517/ccdc.csd.cc2bvmc6
_database_code_depnum_ccdc_archive 'CCDC 2170538'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2car_p06            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.332 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:24 PM
# end Validation Reply Form

_audit_creation_date             2022-05-03
_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         'C4 H4 N8 O6, C20 H16 N4'
_chemical_formula_sum            'C24 H20 N12 O6'
_chemical_formula_weight         572.52
_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                   7.2747(16)
_cell_length_b                   5.6382(6)
_cell_length_c                   26.176(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.556(12)
_cell_angle_gamma                90
_cell_volume                     1071.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1871
_cell_measurement_temperature    292.9
_cell_measurement_theta_max      23.82
_cell_measurement_theta_min      3.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1453 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.8251.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.774
_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  0.0511
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.332
_diffrn_reflns_Laue_measured_fraction_max 0.332
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5495
_diffrn_reflns_point_group_measured_fraction_full 0.332
_diffrn_reflns_point_group_measured_fraction_max 0.332
_diffrn_reflns_theta_full        24.963
_diffrn_reflns_theta_max         24.963
_diffrn_reflns_theta_min         3.697
_diffrn_ambient_temperature      292.9
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.332
_diffrn_measured_fraction_theta_max 0.332
_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                510
_reflns_number_total             624
_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         0.264
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         624
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      0.951
_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)+(0.0771P)²+5.0730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1728
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
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:
 N3(H3A), C11(H11), C12(H12), C8(H8), C9(H9), C4(H4), C3(H3), C7(H7), C6(H6)
3.b Fitted hexagon refined as free rotating group:
 C11(C12,N6,C8,C9,C10), C4(C3,N5,C7,C6,C5)
;
_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
O2 O 0.1754(19) -0.0305(8) 0.3906(2) 0.023(9) Uani 1 1 d . . . . .
O3 O 0.521(2) 0.7217(8) 0.3697(2) 0.037(8) Uani 1 1 d . . . . .
O1 O 0.192(2) -0.1449(8) 0.3115(2) 0.043(8) Uani 1 1 d . . . . .
N2 N 0.363(2) 0.3610(9) 0.3731(3) 0.034(8) Uani 1 1 d . . . . .
N4 N 0.391(2) 0.2481(9) 0.2928(3) 0.027(8) Uani 1 1 d . . . . .
N3 N 0.472(2) 0.4610(9) 0.3009(3) 0.034(8) Uani 1 1 d . . . . .
H3A H 0.523049 0.539784 0.277566 0.041 Uiso 1 1 calc R U . . .
N1 N 0.222(2) -0.0078(9) 0.3463(3) 0.031(8) Uani 1 1 d . . . . .
C11 C 0.2417(14) 0.8760(7) 0.63720(19) 0.024(10) Uani 1 1 d G . . . .
H11 H 0.308597 0.971219 0.616055 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2155(14) 0.9471(7) 0.68707(17) 0.025(10) Uani 1 1 d G . . . .
H12 H 0.264843 1.089800 0.699300 0.030 Uiso 1 1 calc R U . . .
N6 N 0.1154(15) 0.8048(7) 0.71867(15) 0.021(9) Uani 1 1 d G . . . .
C8 C 0.0416(14) 0.5914(7) 0.70040(18) 0.022(10) Uani 1 1 d G . . . .
H8 H -0.025338 0.496250 0.721545 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0678(15) 0.5204(7) 0.65053(17) 0.032(10) Uani 1 1 d G . . . .
H9 H 0.018414 0.377667 0.638300 0.038 Uiso 1 1 calc R U . . .
C10 C 0.1678(16) 0.6627(7) 0.61892(15) 0.026(9) Uani 1 1 d G . . . .
C1 C 0.327(3) 0.1984(11) 0.3369(3) 0.030(8) Uani 1 1 d . . . . .
C2 C 0.463(3) 0.5395(11) 0.3505(3) 0.030(8) Uani 1 1 d . . . . .
C4 C 0.1359(16) 0.3628(8) 0.5471(2) 0.020(10) Uani 1 1 d G . . . .
H4 H 0.069330 0.266173 0.568028 0.024 Uiso 1 1 calc R U . . .
C3 C 0.1679(16) 0.2903(8) 0.49765(18) 0.053(12) Uani 1 1 d G . . . .
H3 H 0.122734 0.145189 0.485539 0.063 Uiso 1 1 calc R U . . .
N5 N 0.2674(17) 0.4347(8) 0.46634(16) 0.047(11) Uani 1 1 d G . . . .
C7 C 0.3348(16) 0.6516(8) 0.4844(2) 0.039(12) Uani 1 1 d G . . . .
H7 H 0.401403 0.748197 0.463489 0.046 Uiso 1 1 calc R U . . .
C6 C 0.3029(16) 0.7241(8) 0.53386(18) 0.018(10) Uani 1 1 d G . . . .
H6 H 0.348001 0.869185 0.545977 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2034(18) 0.5797(7) 0.56518(17) 0.020(9) Uani 1 1 d G . . . .
H2 H 0.31(3) 0.359(13) 0.404(4) 0.04(3) 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
O2 N1 1.235(7) . ?
O3 C2 1.207(13) . ?
O1 N1 1.204(10) . ?
N2 C1 1.333(12) . ?
N2 C2 1.394(13) . ?
N2 H2 0.93(9) . ?
N4 N3 1.347(13) . ?
N4 C1 1.303(9) . ?
N3 H3A 0.8600 . ?
N3 C2 1.376(9) . ?
N1 C1 1.420(15) . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C11 C10 1.3900 . ?
C12 H12 0.9300 . ?
C12 N6 1.3900 . ?
N6 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 C5 1.520(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.3900 . ?
C4 C5 1.3900 . ?
C3 H3 0.9300 . ?
C3 N5 1.3900 . ?
N5 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?

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 N2 C2 106.3(6) . . ?
C1 N2 H2 122(8) . . ?
C2 N2 H2 130(6) . . ?
C1 N4 N3 103.2(7) . . ?
N4 N3 H3A 123.5 . . ?
N4 N3 C2 113.0(7) . . ?
C2 N3 H3A 123.5 . . ?
O2 N1 C1 115.4(8) . . ?
O1 N1 O2 126.7(9) . . ?
O1 N1 C1 117.9(6) . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 N6 120.0 . . ?
N6 C12 H12 120.0 . . ?
C12 N6 C8 120.0 . . ?
N6 C8 H8 120.0 . . ?
C9 C8 N6 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C5 120.0(4) . . ?
C9 C10 C11 120.0 . . ?
C9 C10 C5 119.9(4) . . ?
N2 C1 N1 121.7(6) . . ?
N4 C1 N2 114.5(10) . . ?
N4 C1 N1 123.8(9) . . ?
O3 C2 N2 127.8(6) . . ?
O3 C2 N3 129.2(8) . . ?
N3 C2 N2 102.9(8) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C3 H3 120.0 . . ?
N5 C3 C4 120.0 . . ?
N5 C3 H3 120.0 . . ?
C3 N5 C7 120.0 . . ?
N5 C7 H7 120.0 . . ?
N5 C7 C6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C4 C5 C10 120.6(4) . . ?
C6 C5 C10 119.4(4) . . ?
C6 C5 C4 120.0 . . ?

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
O2 N1 C1 N2 -3(3) . . . . ?
O2 N1 C1 N4 178.3(17) . . . . ?
O1 N1 C1 N2 178.9(17) . . . . ?
O1 N1 C1 N4 0(3) . . . . ?
N4 N3 C2 O3 -179.4(19) . . . . ?
N4 N3 C2 N2 -2(2) . . . . ?
N3 N4 C1 N2 -1(2) . . . . ?
N3 N4 C1 N1 177.2(16) . . . . ?
C11 C12 N6 C8 0.0 . . . . ?
C11 C10 C5 C4 177.7(5) . . . . ?
C11 C10 C5 C6 -2.9(10) . . . . ?
C12 C11 C10 C9 0.0 . . . . ?
C12 C11 C10 C5 -177.4(10) . . . . ?
C12 N6 C8 C9 0.0 . . . . ?
N6 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C8 C9 C10 C5 177.4(10) . . . . ?
C9 C10 C5 C4 0.3(11) . . . . ?
C9 C10 C5 C6 179.7(5) . . . . ?
C10 C11 C12 N6 0.0 . . . . ?
C1 N2 C2 O3 178.5(19) . . . . ?
C1 N2 C2 N3 1.3(19) . . . . ?
C1 N4 N3 C2 2(2) . . . . ?
C2 N2 C1 N4 0(2) . . . . ?
C2 N2 C1 N1 -178.5(16) . . . . ?
C4 C3 N5 C7 0.0 . . . . ?
C3 C4 C5 C10 179.3(10) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 N5 C7 C6 0.0 . . . . ?
N5 C7 C6 C5 0.0 . . . . ?
C7 C6 C5 C10 -179.4(10) . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C5 C4 C3 N5 0.0 . . . . ?


_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_2car_p04
_audit_block_doi                 10.5517/ccdc.csd.cc2bvmd7
_database_code_depnum_ccdc_archive 'CCDC 2170539'
loop_
_audit_author_name
_audit_author_address
'Xiaojiao Liu'
;The University of Edinburgh
United Kingdom
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_2car_p04            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.344 Why?
RESPONSE: This is due to the limitation of the high pressure data.
;
# Added during the CSD deposition process: Wednesday 04 May 2022 01:24 PM
# end Validation Reply Form

_audit_creation_date             2022-05-03
_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                   7.4571(13)
_cell_length_b                   5.6784(5)
_cell_length_c                   26.508(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.931(9)
_cell_angle_gamma                90
_cell_volume                     1121.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2934
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      26.17
_cell_measurement_theta_min      3.67
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1346 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.8141.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.695
_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  0.0385
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.344
_diffrn_reflns_Laue_measured_fraction_max 0.325
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6195
_diffrn_reflns_point_group_measured_fraction_full 0.344
_diffrn_reflns_point_group_measured_fraction_max 0.325
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.277
_diffrn_reflns_theta_min         3.670
_diffrn_ambient_temperature      296.1
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.344
_diffrn_measured_fraction_theta_max 0.325
_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                605
_reflns_number_total             736
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         736
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.009
_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)+(0.0516P)²+1.1736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1117
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 O2, N1, O1, C1, N2, H2, C2, N3, O3, N5, H3A, C7, C3, C6, H7, C4, H3, C5, H6,
 H4, C10, C11, C9, H11, C12, C8, H9, N6, H12, H8, N4
 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), N3(H3A), C11(H11), C4(H4), C8(H8), C9(H9), C12(H12), C6(H6), C7(H7),
 C3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
O2 O 0.8262(10) 1.0190(4) 0.61010(12) 0.045(5) Uani 1 1 d . . . . .
O3 O 0.4794(11) 0.2727(4) 0.62886(12) 0.041(4) Uani 1 1 d . . . . .
O1 O 0.7998(10) 1.1295(4) 0.68815(12) 0.042(5) Uani 1 1 d . . . . .
N2 N 0.6347(12) 0.6294(5) 0.62616(13) 0.030(5) Uani 1 1 d . . . . .
H2 H 0.667711 0.635348 0.595415 0.036 Uiso 1 1 calc R U . . .
N4 N 0.6098(12) 0.7372(5) 0.70623(13) 0.026(5) Uani 1 1 d . . . . .
N3 N 0.5267(12) 0.5268(5) 0.69728(14) 0.033(5) Uani 1 1 d . . . . .
H3A H 0.473007 0.448801 0.720113 0.040 Uiso 1 1 calc R U . . .
N6 N 0.8867(12) 0.2060(5) 0.28062(13) 0.038(5) Uani 1 1 d . . . . .
N1 N 0.7696(12) 0.9940(5) 0.65309(14) 0.027(5) Uani 1 1 d . . . . .
N5 N 0.7343(13) 0.5608(6) 0.53168(14) 0.049(6) Uani 1 1 d . . . . .
C1 C 0.6666(14) 0.7882(6) 0.66193(16) 0.021(5) Uani 1 1 d . . . . .
C2 C 0.5372(15) 0.4518(6) 0.64834(17) 0.024(5) Uani 1 1 d . . . . .
C10 C 0.8319(14) 0.3448(6) 0.38029(16) 0.026(5) Uani 1 1 d . . . . .
C5 C 0.7969(14) 0.4208(6) 0.43289(16) 0.022(6) Uani 1 1 d . . . . .
C11 C 0.7705(15) 0.1318(6) 0.36205(17) 0.032(6) Uani 1 1 d . . . . .
H11 H 0.709121 0.029919 0.382826 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7038(16) 0.2773(6) 0.46541(17) 0.033(6) Uani 1 1 d . . . . .
H4 H 0.660809 0.131507 0.454560 0.039 Uiso 1 1 calc R U . . .
C8 C 0.9523(16) 0.4115(6) 0.29924(17) 0.040(6) Uani 1 1 d . . . . .
H8 H 1.018237 0.506857 0.278184 0.049 Uiso 1 1 calc R U . . .
C9 C 0.9265(15) 0.4862(6) 0.34774(17) 0.036(6) Uani 1 1 d . . . . .
H9 H 0.972014 0.630539 0.358707 0.043 Uiso 1 1 calc R U . . .
C12 C 0.8007(15) 0.0703(6) 0.31263(17) 0.034(6) Uani 1 1 d . . . . .
H12 H 0.758381 -0.074771 0.301123 0.041 Uiso 1 1 calc R U . . .
C6 C 0.8553(15) 0.6375(6) 0.45118(17) 0.026(6) Uani 1 1 d . . . . .
H6 H 0.916087 0.740351 0.430464 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8222(16) 0.6994(6) 0.50041(17) 0.049(7) Uani 1 1 d . . . . .
H7 H 0.863276 0.844579 0.512245 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6757(17) 0.3535(7) 0.51422(17) 0.048(8) Uani 1 1 d . . . . .
H3 H 0.613246 0.255939 0.535673 0.057 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
O2 N1 1.237(4) . ?
O3 C2 1.213(7) . ?
O1 N1 1.221(6) . ?
N2 H2 0.8600 . ?
N2 C1 1.324(6) . ?
N2 C2 1.386(7) . ?
N4 N3 1.363(7) . ?
N4 C1 1.295(5) . ?
N3 H3A 0.8600 . ?
N3 C2 1.370(5) . ?
N6 C8 1.352(8) . ?
N6 C12 1.327(7) . ?
N1 C1 1.423(8) . ?
N5 C7 1.331(7) . ?
N5 C3 1.333(8) . ?
C10 C5 1.491(5) . ?
C10 C11 1.375(8) . ?
C10 C9 1.389(7) . ?
C5 C4 1.389(7) . ?
C5 C6 1.387(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.387(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(5) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.382(5) . ?
C7 H7 0.9300 . ?
C3 H3 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
C1 N2 H2 127.0 . . ?
C1 N2 C2 106.0(3) . . ?
C2 N2 H2 127.0 . . ?
C1 N4 N3 101.5(4) . . ?
N4 N3 H3A 123.3 . . ?
N4 N3 C2 113.4(4) . . ?
C2 N3 H3A 123.3 . . ?
C12 N6 C8 116.4(3) . . ?
O2 N1 C1 116.7(4) . . ?
O1 N1 O2 124.7(5) . . ?
O1 N1 C1 118.6(3) . . ?
C7 N5 C3 117.9(4) . . ?
N2 C1 N1 121.8(3) . . ?
N4 C1 N2 116.1(5) . . ?
N4 C1 N1 121.9(5) . . ?
O3 C2 N2 127.9(3) . . ?
O3 C2 N3 129.3(4) . . ?
N3 C2 N2 102.9(5) . . ?
C11 C10 C5 121.1(4) . . ?
C11 C10 C9 117.4(4) . . ?
C9 C10 C5 121.5(5) . . ?
C4 C5 C10 121.2(5) . . ?
C6 C5 C10 121.4(5) . . ?
C6 C5 C4 117.4(3) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(5) . . ?
C12 C11 H11 120.2 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
N6 C8 H8 118.4 . . ?
N6 C8 C9 123.2(5) . . ?
C9 C8 H8 118.4 . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.5(5) . . ?
C8 C9 H9 120.2 . . ?
N6 C12 C11 123.9(5) . . ?
N6 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.5(5) . . ?
C7 C6 H6 120.3 . . ?
N5 C7 C6 123.0(5) . . ?
N5 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
N5 C3 C4 122.7(5) . . ?
N5 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?

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 N1 C1 N2 0.9(13) . . . . ?
O2 N1 C1 N4 175.8(9) . . . . ?
O1 N1 C1 N2 -177.4(9) . . . . ?
O1 N1 C1 N4 -2.4(13) . . . . ?
N4 N3 C2 O3 179.0(10) . . . . ?
N4 N3 C2 N2 0.3(10) . . . . ?
N3 N4 C1 N2 -2.4(11) . . . . ?
N3 N4 C1 N1 -177.6(8) . . . . ?
N6 C8 C9 C10 1.4(16) . . . . ?
C1 N2 C2 O3 179.6(10) . . . . ?
C1 N2 C2 N3 -1.7(10) . . . . ?
C1 N4 N3 C2 1.2(10) . . . . ?
C2 N2 C1 N4 2.8(12) . . . . ?
C2 N2 C1 N1 178.0(8) . . . . ?
C10 C5 C4 C3 179.4(10) . . . . ?
C10 C5 C6 C7 -179.1(9) . . . . ?
C10 C11 C12 N6 -0.2(16) . . . . ?
C5 C10 C11 C12 178.1(9) . . . . ?
C5 C10 C9 C8 -178.6(9) . . . . ?
C5 C4 C3 N5 0.0(17) . . . . ?
C5 C6 C7 N5 -0.7(17) . . . . ?
C11 C10 C5 C4 1.1(15) . . . . ?
C11 C10 C5 C6 -178.6(9) . . . . ?
C11 C10 C9 C8 1.0(15) . . . . ?
C4 C5 C6 C7 1.2(16) . . . . ?
C8 N6 C12 C11 2.5(15) . . . . ?
C9 C10 C5 C4 -179.3(10) . . . . ?
C9 C10 C5 C6 1.0(15) . . . . ?
C9 C10 C11 C12 -1.6(14) . . . . ?
C12 N6 C8 C9 -3.1(14) . . . . ?
C6 C5 C4 C3 -0.9(16) . . . . ?
C7 N5 C3 C4 0.5(16) . . . . ?
C3 N5 C7 C6 -0.2(16) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
