# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_aa5no2
_database_code_depnum_ccdc_archive 'CCDC 2143162'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 N2 O5, 0.167(H2 O)'
_chemical_formula_sum            'C11 H10.33 N2 O5.17'
_chemical_formula_weight         253.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   20.0082(4)
_cell_length_b                   9.9146(2)
_cell_length_c                   11.4233(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.317(2)
_cell_angle_gamma                90
_cell_volume                     2242.24(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9087
_cell_measurement_theta_min      4.4570
_cell_measurement_theta_max      76.5290

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             1053
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.039
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_T_min  0.61476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_reflns_number            15099
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.467
_diffrn_reflns_theta_max         76.759
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2362
_reflns_number_gt                2165
_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       
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2021)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0588P)²+2.3065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2362
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.70939(6) 0.55524(11) 0.63796(9) 0.0186(2) Uani 1 1 d . . . . .
H1 H 0.7202(10) 0.5647(19) 0.7149(18) 0.029(5) Uiso 1 1 d . . . . .
N2 N 0.60629(7) 0.91100(12) 0.28115(11) 0.0274(3) Uani 1 1 d . . . . .
O1 O 0.57143(5) 0.42782(10) 0.57080(9) 0.0254(2) Uani 1 1 d . . . . .
O2 O 0.73752(5) 0.42969(10) 0.38583(8) 0.0174(2) Uani 1 1 d . . . . .
H2 H 0.7512(11) 0.348(2) 0.3962(19) 0.043(6) Uiso 1 1 d . . . . .
O3 O 0.73118(5) 0.32910(10) 0.62997(8) 0.0231(2) Uani 1 1 d . . . . .
O4 O 0.59375(10) 0.86485(13) 0.18158(11) 0.0587(5) Uani 1 1 d . . . . .
O5 O 0.60115(7) 1.03132(11) 0.30244(11) 0.0398(3) Uani 1 1 d . . . . .
C1 C 0.50756(8) 0.27110(17) 0.44177(16) 0.0337(4) Uani 1 1 d . . . . .
H1A H 0.477118 0.271302 0.501710 0.050 Uiso 1 1 calc R U . . .
H1B H 0.522853 0.178778 0.430263 0.050 Uiso 1 1 calc R U . . .
H1C H 0.483574 0.305743 0.366936 0.050 Uiso 1 1 calc R U . . .
C2 C 0.56745(7) 0.35907(13) 0.48220(12) 0.0214(3) Uani 1 1 d . . . . .
C3 C 0.62441(7) 0.35670(13) 0.40840(12) 0.0199(3) Uani 1 1 d . . . . .
H3A H 0.605859 0.379638 0.325717 0.024 Uiso 1 1 calc R U . . .
H3B H 0.642564 0.263804 0.408532 0.024 Uiso 1 1 calc R U . . .
C4 C 0.68250(6) 0.45312(13) 0.45044(10) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.70981(6) 0.43460(13) 0.58332(11) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.68193(6) 0.65579(13) 0.55982(11) 0.0170(3) Uani 1 1 d . . . . .
C7 C 0.67245(7) 0.79031(14) 0.58489(11) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.683471 0.824670 0.662927 0.024 Uiso 1 1 calc R U . . .
C8 C 0.64613(7) 0.87327(13) 0.49129(12) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.638735 0.966331 0.504512 0.024 Uiso 1 1 calc R U . . .
C9 C 0.63076(7) 0.81948(13) 0.37862(11) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.63895(7) 0.68273(13) 0.35288(11) 0.0181(3) Uani 1 1 d . . . . .
H10 H 0.627160 0.647946 0.275139 0.022 Uiso 1 1 calc R U . . .
C11 C 0.66490(6) 0.60169(13) 0.44598(11) 0.0165(3) Uani 1 1 d . . . . .
O6 O 0.500000 0.5020(5) 0.250000 0.0268(9) Uani 0.3333 2 d S T P . .
H6 H 0.515(3) 0.553(6) 0.196(5) 0.033(15) Uiso 0.3333 1 d . . P . .


_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
N1 C5 1.3497(17) . yes
N1 C6 1.3967(17) . yes
N1 H1 0.88(2) . ?
N2 O4 1.2180(17) . yes
N2 O5 1.2247(17) . yes
N2 C9 1.4647(17) . yes
O1 C2 1.2132(18) . yes
O2 C4 1.4304(15) . yes
O2 H2 0.86(2) . ?
O3 C5 1.2227(17) . yes
C1 C2 1.500(2) . yes
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5126(18) . ?
C3 C4 1.5277(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.5136(17) . ?
C4 C5 1.5480(17) . ?
C6 C7 1.3829(18) . ?
C6 C11 1.4024(17) . ?
C7 C8 1.3907(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3860(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.4020(19) . ?
C10 C11 1.3735(18) . ?
C10 H10 0.9500 . ?
O6 H6 0.88(6) . ?
O6 H6 0.88(6) 2_655 ?

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
C5 N1 C6 111.42(10) . . ?
C5 N1 H1 122.7(12) . . ?
C6 N1 H1 125.4(12) . . ?
O4 N2 O5 122.65(13) . . ?
O4 N2 C9 118.57(12) . . ?
O5 N2 C9 118.74(12) . . ?
C4 O2 H2 109.6(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 122.45(13) . . ?
O1 C2 C3 120.65(12) . . ?
C1 C2 C3 116.88(12) . . ?
C2 C3 C4 114.54(11) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
O2 C4 C11 109.47(10) . . ?
O2 C4 C3 110.09(10) . . ?
C11 C4 C3 115.83(11) . . ?
O2 C4 C5 107.32(10) . . ?
C11 C4 C5 101.30(10) . . ?
C3 C4 C5 112.25(10) . . ?
O3 C5 N1 125.57(12) . . ?
O3 C5 C4 125.48(12) . . ?
N1 C5 C4 108.87(11) . . ?
C7 C6 N1 127.52(12) . . ?
C7 C6 C11 122.60(12) . . ?
N1 C6 C11 109.88(11) . . ?
C6 C7 C8 117.33(12) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C9 C8 C7 119.66(12) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 123.36(12) . . ?
C8 C9 N2 118.19(12) . . ?
C10 C9 N2 118.42(12) . . ?
C11 C10 C9 116.48(12) . . ?
C11 C10 H10 121.8 . . ?
C9 C10 H10 121.8 . . ?
C10 C11 C6 120.54(12) . . ?
C10 C11 C4 130.95(11) . . ?
C6 C11 C4 108.47(11) . . ?
H6 O6 H6 111(8) . 2_655 ?

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 C2 C3 C4 -3.95(18) . . . . ?
C1 C2 C3 C4 177.26(12) . . . . ?
C2 C3 C4 O2 171.84(10) . . . . ?
C2 C3 C4 C11 -63.32(14) . . . . ?
C2 C3 C4 C5 52.35(14) . . . . ?
C6 N1 C5 O3 179.67(12) . . . . ?
C6 N1 C5 C4 2.77(14) . . . . ?
O2 C4 C5 O3 -64.59(16) . . . . ?
C11 C4 C5 O3 -179.32(13) . . . . ?
C3 C4 C5 O3 56.50(17) . . . . ?
O2 C4 C5 N1 112.32(11) . . . . ?
C11 C4 C5 N1 -2.41(13) . . . . ?
C3 C4 C5 N1 -126.59(12) . . . . ?
C5 N1 C6 C7 178.85(12) . . . . ?
C5 N1 C6 C11 -1.96(15) . . . . ?
N1 C6 C7 C8 177.82(12) . . . . ?
C11 C6 C7 C8 -1.28(19) . . . . ?
C6 C7 C8 C9 -0.09(19) . . . . ?
C7 C8 C9 C10 1.4(2) . . . . ?
C7 C8 C9 N2 -177.03(12) . . . . ?
O4 N2 C9 C8 178.79(16) . . . . ?
O5 N2 C9 C8 0.9(2) . . . . ?
O4 N2 C9 C10 0.3(2) . . . . ?
O5 N2 C9 C10 -177.62(14) . . . . ?
C8 C9 C10 C11 -1.3(2) . . . . ?
N2 C9 C10 C11 177.13(12) . . . . ?
C9 C10 C11 C6 -0.07(19) . . . . ?
C9 C10 C11 C4 -177.70(12) . . . . ?
C7 C6 C11 C10 1.4(2) . . . . ?
N1 C6 C11 C10 -177.86(11) . . . . ?
C7 C6 C11 C4 179.49(11) . . . . ?
N1 C6 C11 C4 0.25(14) . . . . ?
O2 C4 C11 C10 65.97(17) . . . . ?
C3 C4 C11 C10 -59.19(18) . . . . ?
C5 C4 C11 C10 179.09(13) . . . . ?
O2 C4 C11 C6 -111.87(11) . . . . ?
C3 C4 C11 C6 122.97(12) . . . . ?
C5 C4 C11 C6 1.25(13) . . . . ?

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
N1 H1 O2 0.88(2) 1.93(2) 2.8098(14) 174.0(18) 6_566 yes
O2 H2 O3 0.86(2) 1.82(2) 2.6534(14) 162(2) 7_656 yes
C1 H1C O6 0.98 2.41 3.157(4) 132.7 . yes
C3 H3A O6 0.99 2.49 3.200(3) 128.8 . yes
C10 H10 O1 0.95 2.55 3.4856(16) 168.3 6_565 yes
O6 H6 O1 0.88(6) 1.95(6) 2.7503(16) 150(6) 6_565 yes

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.052

