# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 2040625'
loop_
_audit_author_name
_audit_author_address
'Zhihan Liang'
;Guangxi University for Nationalities
China
;
_audit_update_record             
;
2020-10-26 deposited with the CCDC.	2022-03-01 downloaded from the CCDC.
;
_audit_creation_date             2020-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H5 N3 O, C4 H6 O4'
_chemical_formula_sum            'C9 H11 N3 O5'
_chemical_formula_weight         241.21
_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/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                   9.7596(9)
_cell_length_b                   6.3491(6)
_cell_length_c                   18.2303(18)
_cell_angle_alpha                90
_cell_angle_beta                 102.170(3)
_cell_angle_gamma                90
_cell_volume                     1104.25(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4509
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.305
_cell_measurement_theta_min      3.406
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0631 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.9445.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16548
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         3.406
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1647
_reflns_number_total             2526
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.016
_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)+(0.0551P)²+0.2673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1209
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.29623(13) 0.5264(2) 0.67702(7) 0.0431(4) Uani 1 1 d . . . . .
O5 O 0.41212(13) 0.2299(2) 0.28527(9) 0.0536(4) Uani 1 1 d . . . . .
H5A H 0.369731 0.161377 0.249480 0.080 Uiso 1 1 calc GR . . . .
O4 O 0.20255(13) 0.3658(2) 0.27940(8) 0.0535(4) Uani 1 1 d . . . . .
O2 O 0.23784(18) 0.5305(2) 0.46082(9) 0.0653(5) Uani 1 1 d . . . . .
O3 O 0.37461(17) 0.2503(2) 0.46768(9) 0.0607(4) Uani 1 1 d . . . . .
H3A H 0.333288 0.215011 0.500495 0.091 Uiso 1 1 calc GR . . . .
N2 N 0.02327(16) 0.9003(3) 0.63094(9) 0.0429(4) Uani 1 1 d . . . . .
N1 N 0.08030(16) 0.5281(3) 0.70261(9) 0.0447(4) Uani 1 1 d . . . . .
H1A H 0.094224 0.411467 0.727062 0.054 Uiso 1 1 calc R . . . .
H1B H 0.001233 0.592038 0.697775 0.054 Uiso 1 1 calc R . . . .
N3 N 0.22194(19) 1.0911(3) 0.56338(9) 0.0480(4) Uani 1 1 d . . . . .
C8 C 0.32560(17) 0.3579(3) 0.30812(9) 0.0320(4) Uani 1 1 d . . . . .
C1 C 0.18002(18) 0.6086(3) 0.67258(10) 0.0342(4) Uani 1 1 d . . . . .
C7 C 0.39116(18) 0.4946(3) 0.37402(10) 0.0343(4) Uani 1 1 d . . . . .
H7 H 0.492082 0.466380 0.387361 0.041 Uiso 1 1 calc R . . . .
C2 C 0.14792(18) 0.8131(3) 0.63211(9) 0.0338(4) Uani 1 1 d . . . . .
C6 C 0.32524(19) 0.4315(3) 0.43909(10) 0.0373(4) Uani 1 1 d . . . . .
C3 C 0.2465(2) 0.9072(3) 0.59846(11) 0.0427(5) Uani 1 1 d . . . . .
H3 H 0.331949 0.840334 0.600407 0.051 Uiso 1 1 calc R . . . .
C5 C 0.0009(2) 1.0853(3) 0.59638(12) 0.0503(5) Uani 1 1 d . . . . .
H5 H -0.084103 1.153277 0.594667 0.060 Uiso 1 1 calc R . . . .
C4 C 0.0988(2) 1.1798(3) 0.56312(11) 0.0488(5) Uani 1 1 d . . . . .
H4 H 0.078190 1.309584 0.539760 0.059 Uiso 1 1 calc R . . . .
C9 C 0.3680(2) 0.7266(3) 0.35481(12) 0.0489(5) Uani 1 1 d . . . . .
H9A H 0.416549 0.763397 0.315956 0.073 Uiso 1 1 calc GR . . . .
H9B H 0.403359 0.810091 0.398626 0.073 Uiso 1 1 calc GR . . . .
H9C H 0.269618 0.752955 0.337704 0.073 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.236(2) . ?
O5 H5A 0.8200 . ?
O5 C8 1.302(2) . ?
O4 C8 1.206(2) . ?
O2 C6 1.193(2) . ?
O3 H3A 0.8200 . ?
O3 C6 1.312(2) . ?
N2 C2 1.333(2) . ?
N2 C5 1.329(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.316(2) . ?
N3 C3 1.329(2) . ?
N3 C4 1.326(3) . ?
C8 C7 1.511(2) . ?
C1 C2 1.494(3) . ?
C7 H7 0.9800 . ?
C7 C6 1.518(2) . ?
C7 C9 1.520(3) . ?
C2 C3 1.381(3) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C4 H4 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O5 H5A 109.5 . . ?
C6 O3 H3A 109.5 . . ?
C5 N2 C2 115.63(18) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C4 N3 C3 116.48(18) . . ?
O5 C8 C7 114.74(15) . . ?
O4 C8 O5 122.74(17) . . ?
O4 C8 C7 122.51(16) . . ?
O1 C1 N1 123.90(17) . . ?
O1 C1 C2 119.57(16) . . ?
N1 C1 C2 116.53(16) . . ?
C8 C7 H7 109.1 . . ?
C8 C7 C6 106.95(14) . . ?
C8 C7 C9 110.87(15) . . ?
C6 C7 H7 109.1 . . ?
C6 C7 C9 111.68(15) . . ?
C9 C7 H7 109.1 . . ?
N2 C2 C1 117.69(16) . . ?
N2 C2 C3 122.15(17) . . ?
C3 C2 C1 120.15(16) . . ?
O2 C6 O3 123.96(18) . . ?
O2 C6 C7 124.83(17) . . ?
O3 C6 C7 111.19(16) . . ?
N3 C3 C2 121.48(18) . . ?
N3 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
N2 C5 H5 118.8 . . ?
N2 C5 C4 122.39(19) . . ?
C4 C5 H5 118.8 . . ?
N3 C4 C5 121.84(19) . . ?
N3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 C1 C2 N2 -177.60(16) . . . . ?
O1 C1 C2 C3 1.4(3) . . . . ?
O5 C8 C7 C6 -115.46(17) . . . . ?
O5 C8 C7 C9 122.57(18) . . . . ?
O4 C8 C7 C6 64.0(2) . . . . ?
O4 C8 C7 C9 -58.0(2) . . . . ?
N2 C2 C3 N3 0.4(3) . . . . ?
N2 C5 C4 N3 0.2(3) . . . . ?
N1 C1 C2 N2 1.5(2) . . . . ?
N1 C1 C2 C3 -179.44(17) . . . . ?
C8 C7 C6 O2 -103.8(2) . . . . ?
C8 C7 C6 O3 74.74(18) . . . . ?
C1 C2 C3 N3 -178.63(16) . . . . ?
C2 N2 C5 C4 0.8(3) . . . . ?
C3 N3 C4 C5 -0.9(3) . . . . ?
C5 N2 C2 C1 177.94(16) . . . . ?
C5 N2 C2 C3 -1.1(3) . . . . ?
C4 N3 C3 C2 0.7(3) . . . . ?
C9 C7 C6 O2 17.6(3) . . . . ?
C9 C7 C6 O3 -163.81(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
