# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_rav10738_E-4iz-4iz
_database_code_depnum_ccdc_archive 'CCDC 2463597'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2025-06-11 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;

_audit_creation_method           
;
FinalCif 2024.9-0 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C10 H12 N4 O2'
_chemical_formula_moiety         'C10 H12 N4 O2'
_chemical_formula_weight         220.24
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.1319(2)
_cell_length_b                   15.3888(7)
_cell_length_c                   8.5819(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.967(2)
_cell_angle_gamma                90
_cell_volume                     533.82(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9656
_cell_measurement_theta_min      5.7503
_cell_measurement_theta_max      68.3688
_cell_measurement_wavelength     1.54178
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method 'cyclohexane / DCM'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   
;Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_exptl_bruker_absorpt_correction_T_ratio 0.874
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.965
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N2
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'
_bruker_diffrn_measurement_temperature_device 'Oxford Cryostream 1000'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\mS Diamant II'
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_source_current           1.0
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.391
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support loop
_diffrn_measurement_details      
;<Phi   scan: start=   0.0; len= 180.0; end= 180.0 at [Counterclockwise Eulerian 
angles: dx= 42.20 mm theta=  27.500 deg omega= 360.000 deg chi=  54.740 deg] 
measure for 3.0 seconds; frame angle 1.00 degrees, wavelength=1.54184>
<Phi   scan: start= 180.0; len= 180.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 42.20 mm theta=  27.500 deg omega= 360.000 deg chi=  54.740 deg] 
measure for 3.0 seconds; frame angle 1.00 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.313 deg phi= 256.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start=   0.0; len= 360.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg omega= 113.272 deg chi= -38.000 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start=  44.0; len= 183.0; end= 227.0 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg omega=   3.914 deg chi=  38.000 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -24.312 deg omega=  60.605 deg chi= -46.500 deg] 
measure for 15.3 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start=  95.4; len=  79.5; end= 174.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  46.812 deg phi=  90.000 deg chi= -46.500 deg] 
measure for 30.2 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 314.4; len= 103.5; end= 417.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -23.464 deg phi=  40.000 deg chi= -57.500 deg] 
measure for 15.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi= 160.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  46.812 deg omega=  95.354 deg chi= -46.500 deg] 
measure for 30.2 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi=  64.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi= 320.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start=   3.6; len= 160.5; end= 164.1 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -23.464 deg omega= 308.424 deg chi=  38.000 deg] 
measure for 15.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start=  95.4; len=  79.5; end= 174.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  46.812 deg phi=   0.000 deg chi= -46.500 deg] 
measure for 30.2 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  39.312 deg omega=  80.354 deg chi= -46.500 deg] 
measure for 23.1 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 314.4; len= 103.5; end= 417.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -23.464 deg phi=   0.000 deg chi= -57.500 deg] 
measure for 15.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi= 128.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi=  32.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start=  95.4; len=  79.5; end= 174.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  46.812 deg phi= 270.000 deg chi= -46.500 deg] 
measure for 30.2 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg omega= 110.354 deg chi= -46.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start=   3.6; len= 160.5; end= 164.1 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -23.464 deg omega= 308.424 deg chi=  38.000 deg] 
measure for 15.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi=  96.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Phi   scan: start= 360.0; len=   1.5; end= 361.5 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta= -31.812 deg omega=  45.605 deg chi= -46.500 deg] 
measure for 18.3 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start=  80.4; len=  94.5; end= 174.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  39.312 deg phi=   0.000 deg chi= -46.500 deg] 
measure for 23.1 seconds; frame angle 1.50 degrees, wavelength=1.54184>
<Omega scan: start= 354.1; len= 112.5; end= 466.6 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=  54.312 deg phi= 360.000 deg chi=  57.500 deg] 
measure for 40.0 seconds; frame angle 1.50 degrees, wavelength=1.54184>
;
_diffrn_measurement_bruker_total_exposure_time 81553.09999999999
_diffrn_reflns_number            14141
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_theta_min         5.75
_diffrn_reflns_theta_max         68.505
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_reduction_process narrow-frame
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_bruker_av_norm_I  22086.176
_diffrn_reflns_bruker_number_gt  12764
_reflns_number_total             973
_reflns_number_gt                889
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker Instrument Service v8.5.5.6'
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  ?
_computing_bruker_data_scaling   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.1787P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Intrinsic Phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         973
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_geom_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.
;
_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_
_bruker_diffrn_runs_axis
_bruker_diffrn_runs_distance
_bruker_diffrn_runs_theta
_bruker_diffrn_runs_omega
_bruker_diffrn_runs_phi
_bruker_diffrn_runs_chi
_bruker_diffrn_runs_width
_bruker_diffrn_runs_images
_bruker_diffrn_runs_time
_bruker_diffrn_runs_wavelength
_bruker_diffrn_runs_voltage
_bruker_diffrn_runs_current
_bruker_diffrn_runs_temperature
Phi 42.2 27.5 0.0 0.0 54.74 1.0 180 3.0 1.54184 50.0 1.0 100.14999999999998
Phi 42.2 27.5 0.0 180.0 54.74 1.0 180 3.0 1.54184 50.0 1.0 100.14999999999998
Omega 42.0 54.3125 -5.874 -104.0 57.5 1.5 75 40.0 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 54.3125 113.27249143656935 0.0 -38.0 1.5 240 40.0 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 54.3125 3.914408563430653 44.0 38.0 1.5 122 40.0 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 -24.3125 60.60488168836829 0.0 -46.5 1.5 240 15.3 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 46.8125 95.354 90.0 -46.5 1.5 53 30.2 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 -23.464 -45.567 40.0 -57.5 1.5 69 15.0 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 54.3125 -5.874 160.0 57.5 1.5 75 40.0 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 46.8125 95.35428168836827 0.0 -46.5 1.5 240 30.2 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 54.3125 -5.874 64.0 57.5 1.5 75 40.0 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 54.3125 -5.874 -40.0 57.5 1.5 75 40.0 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 -23.464 -51.57619143656933 3.577 38.0 1.5 107 15.0 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 46.8125 95.354 0.0 -46.5 1.5 53 30.2 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 39.3125 80.35428168836827 0.0 -46.5 1.5 240 23.1 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 -23.464 -45.567 0.0 -57.5 1.5 69 15.0 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 54.3125 -5.874 128.0 57.5 1.5 75 40.0 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 54.3125 -5.874 32.0 57.5 1.5 75 40.0 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 46.8125 95.354 270.0 -46.5 1.5 53 30.2 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 54.3125 110.35428168836827 0.0 -46.5 1.5 240 40.0 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 -23.464 -51.57619143656933 3.577 38.0 1.5 107 15.0 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 54.3125 -5.874 96.0 57.5 1.5 75 40.0 1.54184 50.0 1.0
100.14999999999998
Phi 42.0 -31.8125 45.6048816883683 0.0 -46.5 1.5 240 18.3 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 39.3125 80.354 0.0 -46.5 1.5 63 23.1 1.54184 50.0 1.0
100.14999999999998
Omega 42.0 54.3125 -5.874 0.0 57.5 1.5 75 40.0 1.54184 50.0 1.0
100.14999999999998

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
N1 N 0.4581(2) 0.46043(7) 0.48931(12) 0.0215(3) Uani 1 1 d . . . . .
N2 N 0.0772(3) 0.40465(7) 0.82079(12) 0.0257(3) Uani 1 1 d . . . . .
O1 O 0.0606(2) 0.32677(6) 0.72837(10) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.3056(3) 0.42662(8) 0.60730(14) 0.0216(3) Uani 1 1 d . . . . .
C2 C 0.2004(3) 0.34234(8) 0.60339(14) 0.0243(3) Uani 1 1 d . . . . .
C3 C 0.2239(3) 0.46286(8) 0.74783(15) 0.0233(3) Uani 1 1 d . . . . .
C4 C 0.2804(3) 0.55158(8) 0.81678(15) 0.0277(3) Uani 1 1 d . . . . .
H4A H 0.191905 0.555039 0.914069 0.041 Uiso 1 1 calc R U . . .
H4B H 0.168337 0.594314 0.739406 0.041 Uiso 1 1 calc R U . . .
H4C H 0.518309 0.563850 0.842303 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2225(4) 0.26969(9) 0.49338(17) 0.0318(3) Uani 1 1 d . . . . .
H5A H 0.386734 0.227517 0.546317 0.048 Uiso 1 1 calc R U . . .
H5B H 0.289089 0.292108 0.397847 0.048 Uiso 1 1 calc R U . . .
H5C H 0.006277 0.241291 0.463031 0.048 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0216(5) 0.0237(5) 0.0203(5) 0.0019(4) 0.0066(4) 0.0015(4)
N2 0.0293(6) 0.0275(6) 0.0223(5) -0.0002(4) 0.0098(4) -0.0004(4)
O1 0.0347(5) 0.0271(5) 0.0272(5) 0.0024(4) 0.0120(4) -0.0019(4)
C1 0.0211(6) 0.0242(6) 0.0203(6) 0.0022(5) 0.0062(5) 0.0023(5)
C2 0.0236(6) 0.0266(7) 0.0237(6) 0.0026(5) 0.0074(5) 0.0019(5)
C3 0.0213(6) 0.0278(7) 0.0211(6) 0.0020(5) 0.0048(5) 0.0023(5)
C4 0.0335(7) 0.0281(7) 0.0233(6) -0.0023(5) 0.0104(5) 0.0000(5)
C5 0.0388(8) 0.0247(7) 0.0343(7) -0.0026(5) 0.0134(6) -0.0019(5)

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
N1 N1 1.269(2) 3_666 ?
N1 C1 1.3991(15) . ?
N2 C3 1.3112(17) . ?
N2 O1 1.4308(14) . ?
O1 C2 1.3410(15) . ?
C1 C2 1.3661(18) . ?
C1 C3 1.4312(17) . ?
C2 C5 1.4783(18) . ?
C3 C4 1.4871(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?

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
N1 N1 C1 113.74(12) 3_666 . ?
C3 N2 O1 106.34(9) . . ?
C2 O1 N2 108.34(9) . . ?
C2 C1 N1 121.61(11) . . ?
C2 C1 C3 105.13(11) . . ?
N1 C1 C3 133.26(12) . . ?
O1 C2 C1 109.73(11) . . ?
O1 C2 C5 118.01(11) . . ?
C1 C2 C5 132.23(12) . . ?
N2 C3 C1 110.45(11) . . ?
N2 C3 C4 119.16(11) . . ?
C1 C3 C4 130.39(11) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

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
C3 N2 O1 C2 0.12(12) . . . . ?
N1 N1 C1 C2 -179.79(12) 3_666 . . . ?
N1 N1 C1 C3 0.0(2) 3_666 . . . ?
N2 O1 C2 C1 -0.60(13) . . . . ?
N2 O1 C2 C5 177.85(10) . . . . ?
N1 C1 C2 O1 -179.33(10) . . . . ?
C3 C1 C2 O1 0.81(14) . . . . ?
N1 C1 C2 C5 2.5(2) . . . . ?
C3 C1 C2 C5 -177.34(13) . . . . ?
O1 N2 C3 C1 0.39(13) . . . . ?
O1 N2 C3 C4 -179.53(10) . . . . ?
C2 C1 C3 N2 -0.74(14) . . . . ?
N1 C1 C3 N2 179.42(12) . . . . ?
C2 C1 C3 C4 179.16(12) . . . . ?
N1 C1 C3 C4 -0.7(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 1 3 0.062
0 -4 1 0.015
0 4 -1 0.021
0 -1 -1 0.007
0 3 4 0.026
4 -1 -3 0.053

_shelx_res_file                  
;
TITL rav10738.res in P2(1)/n
    rav10738.res
    created by SHELXL-2019/3 at 10:01:37 on 13-Dec-2024
REM Old TITL rav10738 in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.093, Rweak 0.002, Alpha 0.012
REM <I/s>   0.632 for   47 systematic absences,  Orientation as input
REM Formula found by SHELXT:  C5 N2 O

CELL  1.54178   4.1319  15.3888   8.5819   90.000  101.967   90.000
ZERR    2.000   0.0002   0.0007   0.0004    0.000    0.002    0.000
LATT  1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C H N O
UNIT 20 24 8 4
SIZE 0.043 0.054 0.129
TEMP -173.150

ACTA
CONF

L.S. 40
BOND $H

LIST 4

FMAP 2
PLAN 10

HTAB

WGHT    0.044200    0.178700
FVAR       1.10879
N1    3    0.458091    0.460432    0.489307    11.00000    0.02156    0.02366 =
         0.02027    0.00191    0.00662    0.00145
N2    3    0.077193    0.404648    0.820786    11.00000    0.02929    0.02747 =
         0.02232   -0.00016    0.00975   -0.00042
O1    4    0.060582    0.326774    0.728368    11.00000    0.03472    0.02713 =
         0.02716    0.00244    0.01197   -0.00190
C1    1    0.305630    0.426620    0.607301    11.00000    0.02106    0.02422 =
         0.02033    0.00217    0.00623    0.00234
C2    1    0.200367    0.342340    0.603389    11.00000    0.02357    0.02663 =
         0.02374    0.00257    0.00742    0.00188
C3    1    0.223912    0.462857    0.747826    11.00000    0.02128    0.02780 =
         0.02109    0.00202    0.00482    0.00233
C4    1    0.280435    0.551578    0.816779    11.00000    0.03348    0.02812 =
         0.02333   -0.00225    0.01041    0.00005
AFIX 137
H4A   2    0.191905    0.555039    0.914069    11.00000   -1.50000
H4B   2    0.168337    0.594314    0.739406    11.00000   -1.50000
H4C   2    0.518309    0.563850    0.842303    11.00000   -1.50000
AFIX   0
C5    1    0.222480    0.269692    0.493375    11.00000    0.03877    0.02466 =
         0.03435   -0.00263    0.01337   -0.00187
AFIX 137
H5A   2    0.386734    0.227517    0.546317    11.00000   -1.50000
H5B   2    0.289089    0.292108    0.397847    11.00000   -1.50000
H5C   2    0.006277    0.241291    0.463031    11.00000   -1.50000
AFIX   0
HKLF 4




REM  rav10738.res in P2(1)/n
REM wR2 = 0.0887, GooF = S = 1.095, Restrained GooF = 1.095 for all data
REM R1 = 0.0317 for 889 Fo > 4sig(Fo) and 0.0342 for all 973 data
REM 75 parameters refined using 0 restraints

END

WGHT      0.0442      0.1787

REM Instructions for potential hydrogen bonds
EQIV $2 x-1/2, -y+1/2, z-1/2
HTAB C5 O1_$2

REM Highest difference peak  0.206,  deepest hole -0.191,  1-sigma level  0.038
Q1    1   0.2402  0.4557  0.6616  11.00000  0.05    0.21
Q2    1   0.3448  0.3795  0.6214  11.00000  0.05    0.20
Q3    1   0.1741  0.3948  0.5708  11.00000  0.05    0.18
Q4    1   0.2851  0.5024  0.7858  11.00000  0.05    0.17
Q5    1   0.3525  0.4441  0.5595  11.00000  0.05    0.14
Q6    1   0.2289  0.3060  0.5643  11.00000  0.05    0.14
Q7    1   0.1763  0.2152  0.5287  11.00000  0.05    0.12
Q8    1   0.4836  0.4342  0.3967  11.00000  0.05    0.12
Q9    1   0.2550  0.4207  0.8316  11.00000  0.05    0.11
Q10   1   0.2879  0.6050  0.7444  11.00000  0.05    0.11
;
_shelx_res_checksum              16900
####################################################################### 
# 
# 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_rav10796_E-3iz-4iz
_database_code_depnum_ccdc_archive 'CCDC 2463598'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2025-06-11 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;

_audit_creation_method           
;
FinalCif 2024.9-0 by Daniel Kratzert, Freiburg 2025, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C9 H10 N4 O2'
_chemical_formula_moiety         'C9 H10 N4 O2'
_chemical_formula_weight         206.21
_chemical_melting_point          ?
_chemical_absolute_configuration .
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.9217(13)
_cell_length_b                   4.4554(2)
_cell_length_c                   10.4846(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     977.32(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5772
_cell_measurement_theta_min      2.7505
_cell_measurement_theta_max      27.4755
_cell_measurement_wavelength     0.71073
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method 
'The crystals were crystallised from acetonitrile.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for single-crystal
 structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_exptl_bruker_absorpt_correction_T_ratio 0.9443
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.996
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N2
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'
_bruker_diffrn_measurement_temperature_device 'Oxford Cryostream 1000'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\mS Diamant II'
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_diffrn_source_current           1.6
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.391
_diffrn_measurement_device       'KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_measurement_details      
;<Phi   scan: start=   0.0; len= 180.0; end= 180.0 at [Counterclockwise Eulerian 
angles: dx= 42.20 mm theta=   0.000 deg omega= 359.849 deg chi=  54.740 deg] 
measure for 2.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 180.0; len= 180.0; end= 360.0 at [Counterclockwise Eulerian 
angles: dx= 42.20 mm theta=   0.000 deg omega= 359.849 deg chi=  54.740 deg] 
measure for 2.0 seconds; frame angle 1.00 degrees, wavelength=0.71073>
<Phi   scan: start= 312.5; len= 142.8; end= 455.3 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=   3.062 deg omega=   7.853 deg chi= -46.500 deg] 
measure for 25.0 seconds; frame angle 0.60 degrees, wavelength=0.71073>
<Omega scan: start=   8.9; len= 105.0; end= 113.9 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=   3.062 deg phi= 360.000 deg chi= -46.500 deg] 
measure for 25.0 seconds; frame angle 0.60 degrees, wavelength=0.71073>
<Phi   scan: start=  40.5; len= 142.8; end= 183.3 at [Counterclockwise Eulerian 
angles: dx= 42.00 mm theta=   3.062 deg omega=  10.771 deg chi= -38.000 deg] 
measure for 25.0 seconds; frame angle 0.60 degrees, wavelength=0.71073>
;
_diffrn_measurement_bruker_total_exposure_time 16995.0
_diffrn_reflns_number            13266
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_theta_min         1.947
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_reduction_process narrow-frame
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_bruker_av_norm_I  442.943
_diffrn_reflns_bruker_number_gt  14566
_reflns_number_total             2232
_reflns_number_gt                2112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.998
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker Instrument Service v8.5.5.6'
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  ?
_computing_bruker_data_scaling   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.1637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Intrinsic Phasing'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2232
_refine_ls_number_parameters     139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_abs_structure_details 
;
 Flack x determined using 950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_geom_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.
;
_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_
_bruker_diffrn_runs_axis
_bruker_diffrn_runs_distance
_bruker_diffrn_runs_theta
_bruker_diffrn_runs_omega
_bruker_diffrn_runs_phi
_bruker_diffrn_runs_chi
_bruker_diffrn_runs_width
_bruker_diffrn_runs_images
_bruker_diffrn_runs_time
_bruker_diffrn_runs_wavelength
_bruker_diffrn_runs_voltage
_bruker_diffrn_runs_current
_bruker_diffrn_runs_temperature
Phi 42.2 0.0 -0.1507498302674508 0.0 54.74 1.0 180 2.0 0.71073 50.0 1.6
100.14999999999998
Phi 42.2 0.0 -0.1507498302674508 180.0 54.74 1.0 180 2.0 0.71073 50.0 1.6
100.14999999999998
Phi 42.0 3.0615 7.853 -47.485 -46.5 0.6 238 25.0 0.71073 50.0 1.6
100.14999999999998
Omega 42.0 3.0615 8.853 0.0 -46.5 0.6 175 25.0 0.71073 50.0 1.6
100.14999999999998
Phi 42.0 3.0615 10.771 40.515 -38.0 0.6 238 25.0 0.71073 50.0 1.6
100.14999999999998

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
N1 N 0.33833(8) 0.2269(4) 0.59568(16) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.35205(7) 0.3536(4) 0.49086(16) 0.0176(3) Uani 1 1 d . . . . .
N3 N 0.27005(8) -0.1265(4) 0.68240(17) 0.0208(4) Uani 1 1 d . . . . .
N4 N 0.48127(8) 0.8663(4) 0.56270(16) 0.0218(4) Uani 1 1 d . . . . .
O1 O 0.21768(6) -0.3005(3) 0.64201(13) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.46929(7) 0.9034(3) 0.42863(14) 0.0227(3) Uani 1 1 d . . . . .
C1 C 0.20555(9) -0.2419(4) 0.51671(18) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.24791(9) -0.0376(4) 0.47246(18) 0.0186(4) Uani 1 1 d . . . . .
H2 H 0.251069 0.043759 0.388948 0.022 Uiso 1 1 calc R U . . .
C3 C 0.28658(9) 0.0263(4) 0.58057(18) 0.0168(4) Uani 1 1 d . . . . .
C4 C 0.14932(10) -0.3967(4) 0.46046(18) 0.0214(4) Uani 1 1 d . . . . .
H4A H 0.109986 -0.306918 0.493937 0.032 Uiso 1 1 calc R U . . .
H4B H 0.150617 -0.610134 0.482893 0.032 Uiso 1 1 calc R U . . .
H4C H 0.150273 -0.375121 0.367464 0.032 Uiso 1 1 calc R U . . .
C11 C 0.40176(8) 0.5602(4) 0.49933(19) 0.0173(4) Uani 1 1 d . . . . .
C12 C 0.42192(9) 0.7194(4) 0.39479(18) 0.0190(4) Uani 1 1 d . . . . .
C13 C 0.44066(9) 0.6639(4) 0.60215(19) 0.0191(4) Uani 1 1 d . . . . .
C14 C 0.39943(10) 0.7269(5) 0.2611(2) 0.0274(5) Uani 1 1 d . . . . .
H14A H 0.365168 0.875517 0.252632 0.041 Uiso 1 1 calc R U . . .
H14B H 0.383218 0.528399 0.237064 0.041 Uiso 1 1 calc R U . . .
H14C H 0.435022 0.781619 0.204926 0.041 Uiso 1 1 calc R U . . .
C15 C 0.43891(10) 0.5804(5) 0.73947(19) 0.0233(4) Uani 1 1 d . . . . .
H15A H 0.471040 0.696985 0.786086 0.035 Uiso 1 1 calc R U . . .
H15B H 0.448133 0.365849 0.748568 0.035 Uiso 1 1 calc R U . . .
H15C H 0.396404 0.623468 0.774226 0.035 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0185(8) 0.0166(8) 0.0190(8) 0.0004(6) 0.0006(6) 0.0004(6)
N2 0.0176(7) 0.0159(7) 0.0194(7) 0.0000(6) 0.0012(6) 0.0005(6)
N3 0.0204(8) 0.0221(8) 0.0200(7) 0.0006(7) -0.0012(6) -0.0038(7)
N4 0.0211(8) 0.0210(9) 0.0232(9) -0.0009(7) 0.0003(6) -0.0019(6)
O1 0.0206(7) 0.0223(7) 0.0179(7) 0.0025(6) -0.0014(6) -0.0051(5)
O2 0.0228(7) 0.0213(7) 0.0239(7) 0.0023(6) 0.0015(6) -0.0036(5)
C1 0.0186(9) 0.0185(9) 0.0168(9) 0.0000(7) 0.0009(7) 0.0033(7)
C2 0.0198(9) 0.0195(8) 0.0164(8) 0.0016(7) 0.0007(7) -0.0001(7)
C3 0.0166(8) 0.0167(9) 0.0170(8) -0.0006(7) 0.0006(7) 0.0016(7)
C4 0.0202(9) 0.0228(9) 0.0213(10) -0.0013(8) -0.0009(7) -0.0022(7)
C11 0.0164(8) 0.0157(8) 0.0197(8) 0.0001(8) 0.0008(7) 0.0019(6)
C12 0.0162(9) 0.0185(9) 0.0224(10) -0.0006(8) 0.0015(7) 0.0010(7)
C13 0.0183(9) 0.0168(9) 0.0223(10) -0.0029(7) 0.0010(7) 0.0018(7)
C14 0.0268(11) 0.0324(11) 0.0229(10) 0.0066(9) -0.0007(8) -0.0045(8)
C15 0.0253(10) 0.0246(10) 0.0201(9) -0.0008(8) -0.0020(8) -0.0033(8)

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
N1 N2 1.268(2) . ?
N1 C3 1.413(2) . ?
N2 C11 1.392(2) . ?
N3 C3 1.313(3) . ?
N3 O1 1.407(2) . ?
N4 C13 1.306(3) . ?
N4 O2 1.437(2) . ?
O1 C1 1.363(2) . ?
O2 C12 1.334(2) . ?
C1 C2 1.352(3) . ?
C1 C4 1.486(3) . ?
C2 C3 1.422(3) . ?
C2 H2 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C11 C12 1.372(3) . ?
C11 C13 1.428(3) . ?
C12 C14 1.479(3) . ?
C13 C15 1.487(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
N2 N1 C3 110.97(16) . . ?
N1 N2 C11 114.10(16) . . ?
C3 N3 O1 104.25(15) . . ?
C13 N4 O2 106.00(16) . . ?
C1 O1 N3 109.23(14) . . ?
C12 O2 N4 108.60(15) . . ?
C2 C1 O1 109.73(16) . . ?
C2 C1 C4 134.03(18) . . ?
O1 C1 C4 116.17(17) . . ?
C1 C2 C3 103.55(17) . . ?
C1 C2 H2 128.2 . . ?
C3 C2 H2 128.2 . . ?
N3 C3 N1 116.03(17) . . ?
N3 C3 C2 113.24(17) . . ?
N1 C3 C2 130.73(18) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C12 C11 N2 121.38(18) . . ?
C12 C11 C13 105.11(16) . . ?
N2 C11 C13 133.49(18) . . ?
O2 C12 C11 109.48(17) . . ?
O2 C12 C14 118.33(18) . . ?
C11 C12 C14 132.15(19) . . ?
N4 C13 C11 110.80(18) . . ?
N4 C13 C15 119.68(18) . . ?
C11 C13 C15 129.49(18) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C3 N1 N2 C11 178.54(15) . . . . ?
C3 N3 O1 C1 0.0(2) . . . . ?
C13 N4 O2 C12 -0.1(2) . . . . ?
N3 O1 C1 C2 0.3(2) . . . . ?
N3 O1 C1 C4 -177.04(15) . . . . ?
O1 C1 C2 C3 -0.5(2) . . . . ?
C4 C1 C2 C3 176.2(2) . . . . ?
O1 N3 C3 N1 178.90(14) . . . . ?
O1 N3 C3 C2 -0.3(2) . . . . ?
N2 N1 C3 N3 177.33(16) . . . . ?
N2 N1 C3 C2 -3.6(3) . . . . ?
C1 C2 C3 N3 0.5(2) . . . . ?
C1 C2 C3 N1 -178.58(19) . . . . ?
N1 N2 C11 C12 -179.17(17) . . . . ?
N1 N2 C11 C13 -0.8(3) . . . . ?
N4 O2 C12 C11 -0.2(2) . . . . ?
N4 O2 C12 C14 177.71(17) . . . . ?
N2 C11 C12 O2 179.25(15) . . . . ?
C13 C11 C12 O2 0.5(2) . . . . ?
N2 C11 C12 C14 1.7(3) . . . . ?
C13 C11 C12 C14 -177.1(2) . . . . ?
O2 N4 C13 C11 0.5(2) . . . . ?
O2 N4 C13 C15 -177.82(17) . . . . ?
C12 C11 C13 N4 -0.6(2) . . . . ?
N2 C11 C13 N4 -179.14(19) . . . . ?
C12 C11 C13 C15 177.5(2) . . . . ?
N2 C11 C13 C15 -1.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 N3 0.95 2.65 3.570(3) 162.1 4_554 yes

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -1 2 0.146
0 -4 -1 0.02
0 4 1 0.025
0 0 1 0.017
0 0 -1 0.009
1 1 0 0.118
4 1 -2 0.129

_shelx_res_file                  
;
TITL rav10796.res in Pna2(1)
    rav10796.res
    created by SHELXL-2019/3 at 15:11:26 on 13-Feb-2025
REM Old TITL rav10796 in Pna2(1)
REM SHELXT solution in Pna2(1): R1 0.065, Rweak 0.003, Alpha 0.001
REM <I/s>   0.556 for  174 systematic absences,  Orientation as input
REM Flack x = -0.111 ( 0.409 ) from   884 Parsons' quotients
REM Formula found by SHELXT:  C9 N4 O2
CELL  0.71073  20.9217   4.4554  10.4846   90.000   90.000   90.000
ZERR    4.000   0.0013   0.0002   0.0006    0.000    0.000    0.000
LATT -1
SYMM -X, -Y, 1/2+Z
SYMM 1/2+X, 1/2-Y, Z
SYMM 1/2-X, 1/2+Y, 1/2+Z
SFAC C H N O
UNIT 36 40 16 8
SIZE 0.041 0.068 0.30
TEMP -173.150

ACTA
CONF

L.S. 40
BOND $H

LIST 4

FMAP 2
PLAN 10

HTAB

EQIV $1 -x+1/2, y+1/2, z-1/2
HTAB C2 N3_$1

OMIT 12   3   0

WGHT    0.049100    0.163700
FVAR       0.77847
N1    3    0.338327    0.226890    0.595681    11.00000    0.01846    0.01658 =
         0.01901    0.00044    0.00056    0.00040
N2    3    0.352051    0.353626    0.490860    11.00000    0.01758    0.01591 =
         0.01937    0.00003    0.00123    0.00050
N3    3    0.270054   -0.126473    0.682395    11.00000    0.02038    0.02209 =
         0.01995    0.00060   -0.00124   -0.00376
N4    3    0.481271    0.866263    0.562700    11.00000    0.02109    0.02099 =
         0.02318   -0.00092    0.00031   -0.00192
O1    4    0.217684   -0.300475    0.642007    11.00000    0.02057    0.02235 =
         0.01787    0.00247   -0.00140   -0.00512
O2    4    0.469288    0.903398    0.428631    11.00000    0.02278    0.02134 =
         0.02388    0.00234    0.00155   -0.00359
C1    1    0.205554   -0.241883    0.516714    11.00000    0.01865    0.01849 =
         0.01683   -0.00004    0.00085    0.00325
C2    1    0.247909   -0.037640    0.472457    11.00000    0.01980    0.01954 =
         0.01640    0.00157    0.00066   -0.00010
AFIX  43
H2    2    0.251069    0.043759    0.388948    11.00000   -1.20000
AFIX   0
C3    1    0.286583    0.026338    0.580574    11.00000    0.01660    0.01673 =
         0.01696   -0.00064    0.00062    0.00156
C4    1    0.149322   -0.396689    0.460465    11.00000    0.02018    0.02281 =
         0.02134   -0.00132   -0.00095   -0.00222
AFIX 137
H4A   2    0.109986   -0.306918    0.493937    11.00000   -1.50000
H4B   2    0.150617   -0.610134    0.482893    11.00000   -1.50000
H4C   2    0.150273   -0.375121    0.367464    11.00000   -1.50000
AFIX   0
C11   1    0.401762    0.560213    0.499326    11.00000    0.01639    0.01568 =
         0.01972    0.00009    0.00084    0.00187
C12   1    0.421915    0.719435    0.394790    11.00000    0.01615    0.01854 =
         0.02243   -0.00059    0.00154    0.00097
C13   1    0.440661    0.663924    0.602149    11.00000    0.01830    0.01685 =
         0.02229   -0.00293    0.00101    0.00182
C14   1    0.399434    0.726870    0.261072    11.00000    0.02678    0.03243 =
         0.02286    0.00665   -0.00065   -0.00453
AFIX 137
H14A  2    0.365168    0.875517    0.252632    11.00000   -1.50000
H14B  2    0.383218    0.528399    0.237064    11.00000   -1.50000
H14C  2    0.435022    0.781619    0.204926    11.00000   -1.50000
AFIX   0
C15   1    0.438910    0.580436    0.739470    11.00000    0.02528    0.02458 =
         0.02013   -0.00081   -0.00204   -0.00326
AFIX 137
H15A  2    0.471040    0.696985    0.786086    11.00000   -1.50000
H15B  2    0.448133    0.365849    0.748568    11.00000   -1.50000
H15C  2    0.396404    0.623468    0.774226    11.00000   -1.50000
AFIX   0
HKLF 4




REM  rav10796.res in Pna2(1)
REM wR2 = 0.0801, GooF = S = 1.035, Restrained GooF = 1.034 for all data
REM R1 = 0.0306 for 2112 Fo > 4sig(Fo) and 0.0332 for all 2232 data
REM 139 parameters refined using 1 restraints

END

WGHT      0.0491      0.1637

REM Instructions for potential hydrogen bonds
HTAB C2 N3_$1
EQIV $2 -x+1/2, y+3/2, z-1/2
HTAB C14 O1_$2
EQIV $3 -x+1, -y+2, z+1/2
HTAB C15 O2_$3

REM Highest difference peak  0.195,  deepest hole -0.195,  1-sigma level  0.039
Q1    1   0.3561  0.6476  0.2527  11.00000  0.05    0.19
Q2    1   0.4261  0.5552  0.5524  11.00000  0.05    0.17
Q3    1   0.2368 -0.2106  0.4818  11.00000  0.05    0.17
Q4    1   0.2122 -0.0776  0.4992  11.00000  0.05    0.16
Q5    1   0.2719 -0.0094  0.5189  11.00000  0.05    0.15
Q6    1   0.4155  0.5738  0.4355  11.00000  0.05    0.14
Q7    1   0.4713  0.7229  0.5783  11.00000  0.05    0.13
Q8    1   0.3267  0.3586  0.4290  11.00000  0.05    0.13
Q9    1   0.4267  0.5951  0.2170  11.00000  0.05    0.12
Q10   1   0.5160  0.8518  0.5883  11.00000  0.05    0.12
;
_shelx_res_checksum              58666
