# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_cocrystal
_database_code_depnum_ccdc_archive 'CCDC 2211429'
loop_
_audit_author_name
_audit_author_address
'Toshiyuki Sasaki'
;Yokohama City University
Japan
;
_audit_update_record             
;
2022-10-06 deposited with the CCDC.	2022-12-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_cocrystal           
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: R(int) increases with the multiplicity of the dataset.
This is pointed out in Diederichs & Karplus,
Nat. Struct. Biol., 1997 for the case of a related metric R(merge).
;
_vrf_PLAT020_cocrystal           
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.330 Report
RESPONSE: R(int) increases with the multiplicity of the dataset.
This is pointed out in Diederichs & Karplus,
Nat. Struct. Biol., 1997 for the case of a related metric R(merge).
;
# Added during the CSD deposition process: Thursday 06 October 2022 01:22 PM
# end Validation Reply Form

_audit_creation_date             2022-07-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 N3, C2 H3 O2'
_chemical_formula_sum            'C6 H8 N3 O2'
_chemical_formula_weight         154.15
_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 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.759
_cell_length_b                   5.200
_cell_length_c                   12.760
_cell_angle_alpha                90
_cell_angle_beta                 90.67
_cell_angle_gamma                90
_cell_volume                     713.8
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    79
_cell_measurement_theta_max      1.02465176988461
_cell_measurement_theta_min      0.14661895733917485
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             117
_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  0.3296
_diffrn_reflns_av_unetI/netI     0.2018
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38658
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        0.862
_diffrn_reflns_theta_max         1.026
_diffrn_reflns_theta_min         0.149
_diffrn_ambient_temperature      79
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  
;
Talos Arctica G2
;
_diffrn_measurement_method       ?
_diffrn_radiation_type           electrons
_diffrn_radiation_wavelength     0.02508
_diffrn_source                   electrons
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                964
_reflns_number_total             2172
_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       
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection       
'Verlox (Thermo Fisher Scientific) and SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       19793(20)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.1822
_refine_ls_R_factor_gt           0.1120
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1583P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2990
_refine_ls_wR_factor_ref         0.3195
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.01
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
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
N2 N 0.2498(3) 0.1835(7) 0.3317(3) 0.0171(9) Uani 1 1 d . U . . .
O1 O 0.4300(4) 0.5489(7) 0.3607(3) 0.0244(9) Uani 1 1 d . U . . .
O2 O 0.3228(3) 0.6879(7) 0.4994(3) 0.0219(9) Uani 1 1 d . U . . .
N1 N 0.1321(4) 0.2683(7) 0.4785(4) 0.0223(10) Uani 1 1 d . U . . .
C3 C 0.1555(4) 0.1184(8) 0.3964(4) 0.0164(10) Uani 1 1 d . U . . .
C4 C 0.2675(4) 0.0334(8) 0.2476(3) 0.0177(10) Uani 1 1 d . U . . .
C1 C 0.4115(4) 0.7042(8) 0.4406(4) 0.0166(10) Uani 1 1 d . U . . .
C5 C 0.1930(4) -0.1828(8) 0.2252(4) 0.0200(10) Uani 1 1 d . U . . .
C6 C 0.1015(4) -0.2359(8) 0.2978(4) 0.0202(11) Uani 1 1 d . U . . .
N3 N 0.0794(3) -0.0882(7) 0.3817(3) 0.0182(9) Uani 1 1 d . U . . .
C2 C 0.5110(4) 0.9127(8) 0.4523(4) 0.0191(11) Uani 1 1 d . U . . .
H2A H 0.603(2) 0.806(4) 0.4624(17) 0.020(5) Uiso 1 1 d . . . . .
H2B H 0.521(3) 1.028(5) 0.374(2) 0.045(7) Uiso 1 1 d . . . . .
H1A H 0.187(2) 0.422(5) 0.4904(19) 0.028(6) Uiso 1 1 d . . . . .
H4 H 0.350(3) 0.091(5) 0.192(2) 0.049(8) Uiso 1 1 d . . . . .
H1 H 0.358(3) 0.429(5) 0.346(2) 0.038(6) Uiso 1 1 d . . . . .
H1B H 0.054(2) 0.209(4) 0.5258(19) 0.025(5) Uiso 1 1 d . . . . .
H6 H 0.052(3) -0.429(7) 0.292(3) 0.071(10) Uiso 1 1 d . . . . .
H5 H 0.212(3) -0.291(6) 0.157(3) 0.057(8) Uiso 1 1 d . . . . .

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
N2 0.0160(19) 0.0170(17) 0.018(2) -0.0007(17) 0.0025(16) 0.0002(15)
O1 0.022(2) 0.0242(18) 0.027(2) 0.0009(17) 0.0088(17) -0.0049(16)
O2 0.0168(17) 0.0257(18) 0.023(2) -0.0012(17) 0.0070(16) -0.0044(15)
N1 0.022(2) 0.020(2) 0.025(2) -0.0034(17) 0.0067(18) -0.0048(16)
C3 0.017(2) 0.017(2) 0.015(2) -0.0006(18) 0.0046(17) -0.0052(16)
C4 0.018(2) 0.022(2) 0.013(2) 0.0038(19) 0.0085(18) -0.0051(17)
C1 0.010(2) 0.021(2) 0.019(2) -0.0044(19) 0.0030(17) -0.0063(17)
C5 0.022(2) 0.020(2) 0.018(3) 0.000(2) 0.0029(19) -0.0015(18)
C6 0.021(2) 0.019(2) 0.021(3) 0.0005(19) 0.0026(19) -0.0004(17)
N3 0.0152(19) 0.0196(18) 0.020(2) -0.0008(17) 0.0041(16) -0.0042(14)
C2 0.013(2) 0.019(2) 0.026(3) -0.001(2) 0.0064(19) -0.0009(16)

_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
N2 C3 1.359(5) . ?
N2 C4 1.342(6) . ?
O1 C1 1.317(6) . ?
O1 H1 1.01(3) . ?
O2 C1 1.223(5) . ?
N1 C3 1.332(6) . ?
N1 H1A 1.00(2) . ?
N1 H1B 1.09(2) . ?
C3 N3 1.362(5) . ?
C4 C5 1.408(6) . ?
C4 H4 1.18(3) . ?
C1 C2 1.529(6) . ?
C5 C6 1.387(6) . ?
C5 H5 1.06(3) . ?
C6 N3 1.342(6) . ?
C6 H6 1.14(4) . ?
C2 C2 1.538(9) 3_676 ?
C2 H2A 1.14(2) . ?
C2 H2B 1.17(3) . ?

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
C4 N2 C3 117.0(4) . . ?
C1 O1 H1 113.8(15) . . ?
C3 N1 H1A 117.9(14) . . ?
C3 N1 H1B 115.1(13) . . ?
H1A N1 H1B 127.0(19) . . ?
N2 C3 N3 124.4(4) . . ?
N1 C3 N2 118.8(4) . . ?
N1 C3 N3 116.8(4) . . ?
N2 C4 C5 122.8(4) . . ?
N2 C4 H4 116.5(14) . . ?
C5 C4 H4 120.8(14) . . ?
O1 C1 C2 113.5(4) . . ?
O2 C1 O1 123.9(4) . . ?
O2 C1 C2 122.6(4) . . ?
C4 C5 H5 118.4(18) . . ?
C6 C5 C4 115.5(4) . . ?
C6 C5 H5 126.1(18) . . ?
C5 C6 H6 118.2(18) . . ?
N3 C6 C5 123.5(4) . . ?
N3 C6 H6 117.7(18) . . ?
C6 N3 C3 116.7(4) . . ?
C1 C2 C2 112.4(4) . 3_676 ?
C1 C2 H2A 105.8(11) . . ?
C1 C2 H2B 110.5(14) . . ?
C2 C2 H2A 109.9(12) 3_676 . ?
C2 C2 H2B 112.9(14) 3_676 . ?
H2A C2 H2B 104.8(18) . . ?

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 C3 N3 C6 0.7(7) . . . . ?
N2 C4 C5 C6 -1.8(7) . . . . ?
O1 C1 C2 C2 -178.6(5) . . . 3_676 ?
O2 C1 C2 C2 2.4(8) . . . 3_676 ?
N1 C3 N3 C6 178.7(4) . . . . ?
C3 N2 C4 C5 0.2(7) . . . . ?
C4 N2 C3 N1 -177.5(4) . . . . ?
C4 N2 C3 N3 0.4(7) . . . . ?
C4 C5 C6 N3 3.1(7) . . . . ?
C5 C6 N3 C3 -2.5(7) . . . . ?

_shelx_res_file                  
;
TITL
    cocrystal.res
    created by SHELXL-2018/3 at 11:02:52 on 25-Jul-2022
CELL 0.02508 10.759 5.1996 12.7601 90 90.672 90
ZERR 4 0 0 0 0 0 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC  C 0.731 36.995 1.195 11.297 0.456 2.814 0.125 0.346 0 0 0 0 0.77 12.011
SFAC  H 0.375 15.495 0.141 4.126 0.022 0.025 -0.101 46.884 0 0 0 0 0.32 1.008
SFAC  N 0.572 28.846 1.042 9.054 0.465 2.421 0.131 0.317 0 0 0 0 0.75 14.007
SFAC  O 0.455 23.78 0.917 7.622 0.472 2.144 0.138 0.296 0 0 0 0 0.73 15.999
UNIT 24 32 12 8

ISOR 0.01 0.01
RIGU

L.S. 100
PLAN  20
CONF
MORE -1
BOND $H
fmap 2
acta
SHEL 10 0.7
REM <olex2.extras>
REM <HklSrc "%.\\cocrystal.hkl">
REM </olex2.extras>

WGHT    0.158300
EXTI19792.935547
FVAR       0.37382
N2    3    0.249833    0.183533    0.331655    11.00000    0.01602    0.01698 =
         0.01844   -0.00072    0.00251    0.00017
O1    4    0.430032    0.548944    0.360734    11.00000    0.02218    0.02423 =
         0.02690    0.00092    0.00877   -0.00490
O2    4    0.322849    0.687941    0.499350    11.00000    0.01684    0.02570 =
         0.02321   -0.00120    0.00699   -0.00439
N1    3    0.132146    0.268328    0.478525    11.00000    0.02242    0.01974 =
         0.02500   -0.00342    0.00672   -0.00480
C3    1    0.155545    0.118391    0.396418    11.00000    0.01693    0.01722 =
         0.01507   -0.00062    0.00456   -0.00521
C4    1    0.267507    0.033376    0.247633    11.00000    0.01800    0.02180 =
         0.01350    0.00380    0.00848   -0.00511
C1    1    0.411549    0.704230    0.440612    11.00000    0.00999    0.02054 =
         0.01932   -0.00441    0.00297   -0.00634
C5    1    0.193003   -0.182776    0.225207    11.00000    0.02238    0.01990 =
         0.01773    0.00010    0.00288   -0.00146
C6    1    0.101524   -0.235943    0.297772    11.00000    0.02059    0.01852 =
         0.02144    0.00050    0.00260   -0.00039
N3    3    0.079415   -0.088188    0.381702    11.00000    0.01519    0.01958 =
         0.01982   -0.00081    0.00408   -0.00419
C2    1    0.510994    0.912710    0.452344    11.00000    0.01258    0.01906 =
         0.02579   -0.00135    0.00636   -0.00086
H2A   2    0.603258    0.805847    0.462351    11.00000    0.01993
H2B   2    0.520944    1.027856    0.374233    11.00000    0.04488
H1A   2    0.186916    0.421635    0.490405    11.00000    0.02774
H4    2    0.350379    0.090809    0.192230    11.00000    0.04852
H1    2    0.357973    0.428809    0.345515    11.00000    0.03751
H1B   2    0.053892    0.208575    0.525845    11.00000    0.02519
H6    2    0.051771   -0.428911    0.292448    11.00000    0.07150
H5    2    0.212363   -0.291309    0.156994    11.00000    0.05728
HKLF 4




REM
REM wR2 = 0.3195, GooF = S = 1.026, Restrained GooF = 0.999 for all data
REM R1 = 0.1120 for 964 Fo > 4sig(Fo) and 0.1822 for all 2172 data
REM 133 parameters refined using 129 restraints

END

WGHT      0.1537      0.0000

REM Highest difference peak  0.157,  deepest hole -0.176,  1-sigma level  0.041
Q1    1   0.2902  0.1527  0.2748  11.00000  0.05    0.16
Q2    1   0.2266 -0.0030  0.2580  11.00000  0.05    0.15
Q3    1   0.2384  0.1121  0.2213  11.00000  0.05    0.13
Q4    1   0.4424  0.7614  0.3820  11.00000  0.05    0.11
Q5    1   0.2011  0.0758  0.4135  11.00000  0.05    0.11
Q6    1   0.2383 -0.0802  0.1651  11.00000  0.05    0.11
Q7    1  -0.0256 -0.2289  0.3398  11.00000  0.05    0.11
Q8    1   0.4058  0.5040  0.4487  11.00000  0.05    0.10
Q9    1   0.4425  0.2629  0.3720  11.00000  0.05    0.10
Q10   1   0.4592  0.6107  0.3855  11.00000  0.05    0.10
Q11   1   0.1444  0.0862  0.4228  11.00000  0.05    0.10
Q12   1   0.3547  0.5937  0.5186  11.00000  0.05    0.10
Q13   1   0.4790  0.5720  0.3966  11.00000  0.05    0.10
Q14   1   0.2339  0.2451  0.1534  11.00000  0.05    0.09
Q15   1   0.3122 -0.0814  0.2470  11.00000  0.05    0.09
Q16   1   0.3152  0.4626  0.5005  11.00000  0.05    0.09
Q17   1   0.1602  0.1814  0.4052  11.00000  0.05    0.09
Q18   1   0.2822 -0.1804  0.2886  11.00000  0.05    0.09
Q19   1   0.2244 -0.0317  0.1226  11.00000  0.05    0.09
Q20   1   0.3789  0.6262  0.5090  11.00000  0.05    0.09
;
_shelx_res_checksum              4552
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method Co-grinding
