# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_29
_database_code_depnum_ccdc_archive 'CCDC 2038360'
loop_
_audit_author_name
_audit_author_address
'Louise Male'
;University of Birmingham
United Kingdom
;
_audit_update_record             
;
2020-10-14 deposited with the CCDC.	2021-03-25 downloaded from the CCDC.
;
_audit_creation_date             2019-09-10
_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         'C8 H7 N O6'
_chemical_formula_sum            'C8 H7 N O6'
_chemical_formula_weight         213.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H7 N1 O6'
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'

_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                   8.9555(7)
_cell_length_b                   10.1597(6)
_cell_length_c                   9.9607(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.056(9)
_cell_angle_gamma                90
_cell_volume                     851.32(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1703
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.6780
_cell_measurement_theta_min      4.7750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.278
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 0 0 0.0719
0 5 4 0.0795
-2 5 4 0.0821
1 -5 -4 0.0635
0 3 -5 0.0217
-6 1 0 0.0687
1 -2 -6 0.0375
4 1 3 0.0767
-1 2 6 0.0812
-3 2 6 0.0786
0 -7 0 0.0771
0 7 -1 0.0656
-3 5 0 0.0742
-6 0 1 0.0669
-1 -6 3 0.0798
5 -3 1 0.0845
-3 -3 6 0.0920
-3 0 6 0.0835
5 0 1 0.0665

_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.119
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.9926 0.0051 0.0276 -0.0453 -0.1421 -1.0890
-0.0241 4.9945 4.0102 0.2434 -0.9676 -0.1117
-2.0216 4.9928 4.0010 0.2585 -0.9202 0.2514
1.0228 -4.9936 -4.0056 -0.2509 0.9439 -0.0698
0.0357 2.9987 -5.0045 0.8316 0.3890 0.1949
-5.9920 0.9940 -0.0267 0.1681 0.0534 1.0950
1.0382 -1.9958 -6.0057 0.3027 0.9398 0.0189
3.9754 1.0017 3.0236 -0.1854 -0.5765 -0.8262
-1.0382 1.9958 6.0057 -0.3027 -0.9398 -0.0189
-3.0357 1.9940 5.9965 -0.2876 -0.8924 0.3441
-0.0042 -6.9937 -0.0062 -0.8595 0.6209 -0.0419
0.0110 6.9940 -0.9952 0.9521 -0.4899 0.0773
-2.9933 4.9930 -0.0093 0.6366 -0.3725 0.5744
-5.9994 -0.0054 0.9738 -0.0473 0.0111 1.0536
-1.0227 -5.9963 2.9943 -1.0071 0.1629 0.0394
4.9852 -2.9933 1.0218 -0.4988 0.0167 -0.9609
-3.0387 -3.0015 5.9921 -0.9015 -0.4489 0.3142
-3.0369 -0.0042 5.9948 -0.5332 -0.7150 0.3321
4.9871 0.0040 1.0244 -0.1304 -0.2494 -0.9429

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3177
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.979
_diffrn_reflns_theta_min         5.258
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -11.00   1.00    1.00    --  -42.06 -77.00 -90.00  102
  2  ω      1.00  28.00   1.00    1.00    --  -42.06  57.00 150.00   27
  3  ω    -20.00  67.00   1.00    1.00    --   42.06 -57.00  60.00   87
  4  ω     56.00 118.00   1.00    1.00    --  107.88-125.00-180.00   62
  5  ω     35.00 127.00   1.00    1.00    --  107.88 -30.00-180.00   92
  6  ω    118.00 159.00   1.00    1.00    --  107.88  45.00-150.00   41
  7  ω     28.00  92.00   1.00    1.00    --  107.88 -94.00  90.00   64
  8  ω     33.00 127.00   1.00    1.00    --  107.88 -30.00 -90.00   94
  9  ω     34.00  88.00   1.00    1.00    --  107.88 -77.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0072451000
_diffrn_orient_matrix_UB_12      0.1229835000
_diffrn_orient_matrix_UB_13      -0.0925241000
_diffrn_orient_matrix_UB_21      -0.0230349000
_diffrn_orient_matrix_UB_22      -0.0886528000
_diffrn_orient_matrix_UB_23      -0.1310083000
_diffrn_orient_matrix_UB_31      -0.1815670000
_diffrn_orient_matrix_UB_32      0.0061328000
_diffrn_orient_matrix_UB_33      -0.0365710000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1441
_reflns_number_total             1687
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1687
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.045
_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)+(0.0452P)²+0.3825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29058(17) 0.51073(15) 0.62281(15) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.38747(18) 0.61442(15) 0.61519(15) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.39368(18) 0.65369(15) 0.48175(16) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.455233 0.725796 0.476106 0.023 Uiso 1 1 calc R . . . .
C4 C 0.30960(18) 0.58637(16) 0.36000(16) 0.0197(3) Uani 1 1 d . . . . .
H4 H 0.314630 0.614251 0.272726 0.024 Uiso 1 1 calc R . . . .
C5 C 0.21628(18) 0.47664(15) 0.36364(16) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.20484(17) 0.44217(15) 0.49660(15) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.29269(17) 0.46977(15) 0.76869(15) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.2214(2) 0.52957(17) 0.96721(16) 0.0227(4) Uani 1 1 d . . . . .
H8A H 0.159312 0.452292 0.966096 0.034 Uiso 1 1 calc GR . . . .
H8B H 0.177010 0.603172 1.000933 0.034 Uiso 1 1 calc GR . . . .
H8C H 0.328812 0.515468 1.029546 0.034 Uiso 1 1 calc GR . . . .
N1 N 0.09272(15) 0.34208(13) 0.50299(13) 0.0185(3) Uani 1 1 d . . . . .
O1 O 0.36064(13) 0.37230(11) 0.83084(11) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.22002(13) 0.55658(11) 0.82311(11) 0.0194(3) Uani 1 1 d . . . . .
O3 O 0.47714(14) 0.67309(12) 0.73961(11) 0.0220(3) Uani 1 1 d . . . . .
O4 O 0.14091(14) 0.41650(12) 0.23856(11) 0.0231(3) Uani 1 1 d . . . . .
O5 O 0.03703(13) 0.26633(12) 0.40030(11) 0.0240(3) Uani 1 1 d . . . . .
O6 O 0.05366(13) 0.33743(11) 0.61030(11) 0.0226(3) Uani 1 1 d . . . . .
H4A H 0.091(3) 0.346(2) 0.260(2) 0.043(6) Uiso 1 1 d . . . . .
H3A H 0.532(3) 0.737(3) 0.722(2) 0.052(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(2) . ?
C1 C6 1.412(2) . ?
C1 C7 1.5054(19) . ?
C2 C3 1.407(2) . ?
C2 O3 1.3614(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(2) . ?
C5 C6 1.407(2) . ?
C5 O4 1.3433(18) . ?
C6 N1 1.446(2) . ?
C7 O1 1.2148(19) . ?
C7 O2 1.3180(18) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 O2 1.4573(17) . ?
N1 O5 1.2399(17) . ?
N1 O6 1.2343(16) . ?
O3 H3A 0.87(3) . ?
O4 H4A 0.91(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.13(13) . . ?
C2 C1 C7 117.58(13) . . ?
C6 C1 C7 123.10(14) . . ?
C1 C2 C3 119.77(14) . . ?
O3 C2 C1 117.95(13) . . ?
O3 C2 C3 122.26(14) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.43(14) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.72(14) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 117.32(14) . . ?
O4 C5 C4 116.90(13) . . ?
O4 C5 C6 125.74(14) . . ?
C1 C6 N1 118.79(13) . . ?
C5 C6 C1 121.49(14) . . ?
C5 C6 N1 119.49(13) . . ?
O1 C7 C1 123.74(14) . . ?
O1 C7 O2 124.59(13) . . ?
O2 C7 C1 111.56(12) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
O5 N1 C6 119.29(12) . . ?
O6 N1 C6 118.19(13) . . ?
O6 N1 O5 122.50(13) . . ?
C7 O2 C8 116.13(12) . . ?
C2 O3 H3A 110.0(15) . . ?
C5 O4 H4A 105.9(14) . . ?

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
O4 H4A N1 0.91(2) 2.42(2) 2.9112(17) 114.3(17) . yes
O4 H4A O5 0.91(2) 1.82(2) 2.6108(16) 144(2) . yes
O4 H4A O6 0.91(2) 2.34(2) 2.8659(17) 117.3(17) 4_565 yes
O3 H3A O1 0.87(3) 1.85(3) 2.7200(17) 175(2) 2_656 yes

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
C1 C2 C3 C4 -2.8(2) . . . . ?
C1 C6 N1 O5 -167.87(13) . . . . ?
C1 C6 N1 O6 13.6(2) . . . . ?
C1 C7 O2 C8 -177.30(12) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C2 C1 C6 N1 -174.33(13) . . . . ?
C2 C1 C7 O1 -103.94(18) . . . . ?
C2 C1 C7 O2 72.37(17) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 3.5(2) . . . . ?
C3 C4 C5 O4 -178.89(14) . . . . ?
C4 C5 C6 C1 -3.4(2) . . . . ?
C4 C5 C6 N1 171.19(13) . . . . ?
C5 C6 N1 O5 17.4(2) . . . . ?
C5 C6 N1 O6 -161.07(13) . . . . ?
C6 C1 C2 C3 2.8(2) . . . . ?
C6 C1 C2 O3 -175.60(13) . . . . ?
C6 C1 C7 O1 70.9(2) . . . . ?
C6 C1 C7 O2 -112.74(16) . . . . ?
C7 C1 C2 C3 177.94(13) . . . . ?
C7 C1 C2 O3 -0.5(2) . . . . ?
C7 C1 C6 C5 -174.56(14) . . . . ?
C7 C1 C6 N1 10.9(2) . . . . ?
O1 C7 O2 C8 -1.0(2) . . . . ?
O3 C2 C3 C4 175.59(14) . . . . ?
O4 C5 C6 C1 179.23(14) . . . . ?
O4 C5 C6 N1 -6.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.545
_oxdiff_exptl_absorpt_empirical_full_min 0.742
