# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_audit_block_doi                 10.5517/cc1jpx48
_database_code_depnum_ccdc_archive 'CCDC 1421230'
_audit_update_record             
;
2015-08-29 deposited with the CCDC.
2015-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N O5'
_chemical_formula_sum            'C12 H9 N O5'
_chemical_formula_weight         247.20

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   7.201(3)
_cell_length_b                   10.323(4)
_cell_length_c                   7.211(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.096(7)
_cell_angle_gamma                90
_cell_volume                     533.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    625
_cell_measurement_theta_min      28.60
_cell_measurement_theta_max      77.80

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.042
_shelx_estimated_absorpt_T_min   0.681
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            11331
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.172
_diffrn_reflns_theta_max         77.372
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             2085
_reflns_number_gt                1995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_max     0.844
_reflns_Friedel_fraction_full    0.861

_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       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.0050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0078(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 832 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2085
_refine_ls_number_parameters     164
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.000
_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
O1 O 0.53829(18) 0.37900(14) 0.26942(17) 0.0283(3) Uani 1 1 d . . . . .
O2 O 0.83478(18) 0.36313(16) 0.40371(19) 0.0352(3) Uani 1 1 d . . . . .
O3 O 0.37874(15) 0.05265(13) 0.19362(17) 0.0253(3) Uani 1 1 d . . . . .
O4 O 0.9888(2) 0.18655(17) 0.0270(2) 0.0415(4) Uani 1 1 d . . . . .
O5 O 0.9009(3) -0.01243(19) -0.0065(2) 0.0507(5) Uani 1 1 d . . . . .
N1 N 0.95286(18) 0.08043(17) 0.0893(2) 0.0269(3) Uani 1 1 d . . . . .
C1 C 0.6935(2) 0.3088(2) 0.3368(2) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.6538(2) 0.17086(19) 0.3133(2) 0.0225(4) Uani 1 1 d . . . . .
C3 C 0.4760(2) 0.16145(19) 0.2357(2) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.3893(2) 0.29141(19) 0.2016(2) 0.0246(4) Uani 1 1 d . . . . .
H4A H 0.3507 0.3053 0.0671 0.030 Uiso 1 1 calc R U . . .
H4B H 0.2793 0.3022 0.2717 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7750(2) 0.0566(2) 0.3693(2) 0.0231(4) Uani 1 1 d . . . . .
H5 H 0.7963 0.0568 0.5086 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6652(2) -0.0665(2) 0.3119(2) 0.0217(4) Uani 1 1 d . . . . .
C7 C 0.4779(2) -0.06343(19) 0.2340(2) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.3752(2) -0.1756(2) 0.1904(2) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.2487 -0.1701 0.1379 0.031 Uiso 1 1 calc R U . . .
C9 C 0.4589(3) -0.2956(2) 0.2241(2) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.3896 -0.3728 0.1965 0.035 Uiso 1 1 calc R U . . .
C10 C 0.6472(3) -0.3024(2) 0.2995(3) 0.0297(4) Uani 1 1 d . . . . .
H10 H 0.7062 -0.3842 0.3211 0.036 Uiso 1 1 calc R U . . .
C11 C 0.7458(3) -0.1895(2) 0.3419(2) 0.0274(4) Uani 1 1 d . . . . .
H11 H 0.8727 -0.1953 0.3931 0.033 Uiso 1 1 calc R U . . .
C12 C 0.9693(2) 0.0647(2) 0.2965(2) 0.0267(4) Uani 1 1 d . . . . .
H12A H 1.0392 0.1391 0.3559 0.032 Uiso 1 1 calc R U . . .
H12B H 1.0407 -0.0151 0.3318 0.032 Uiso 1 1 calc R U . . .


_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 1.377(2) . ?
O1 C4 1.448(2) . ?
O2 C1 1.216(2) . ?
O3 C3 1.341(2) . ?
O3 C7 1.410(2) . ?
O4 N1 1.222(2) . ?
O5 N1 1.217(2) . ?
N1 C12 1.495(2) . ?
C1 C2 1.459(3) . ?
C2 C3 1.345(3) . ?
C2 C5 1.497(3) . ?
C3 C4 1.489(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.530(3) . ?
C5 C12 1.549(2) . ?
C5 H5 1.0000 . ?
C6 C11 1.403(3) . ?
C6 C7 1.405(2) . ?
C7 C8 1.392(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.408(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C1 O1 C4 109.59(15) . . ?
C3 O3 C7 115.08(12) . . ?
O5 N1 O4 124.18(16) . . ?
O5 N1 C12 117.95(16) . . ?
O4 N1 C12 117.85(16) . . ?
O2 C1 O1 120.74(19) . . ?
O2 C1 C2 129.93(18) . . ?
O1 C1 C2 109.33(15) . . ?
C3 C2 C1 106.56(17) . . ?
C3 C2 C5 123.85(18) . . ?
C1 C2 C5 129.52(15) . . ?
O3 C3 C2 127.29(18) . . ?
O3 C3 C4 121.12(14) . . ?
C2 C3 C4 111.58(17) . . ?
O1 C4 C3 102.93(14) . . ?
O1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
O1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C2 C5 C6 108.18(13) . . ?
C2 C5 C12 112.81(15) . . ?
C6 C5 C12 114.36(14) . . ?
C2 C5 H5 107.0 . . ?
C6 C5 H5 107.0 . . ?
C12 C5 H5 107.0 . . ?
C11 C6 C7 116.48(17) . . ?
C11 C6 C5 121.10(14) . . ?
C7 C6 C5 122.37(17) . . ?
C8 C7 C6 122.41(18) . . ?
C8 C7 O3 114.52(14) . . ?
C6 C7 O3 123.08(16) . . ?
C9 C8 C7 119.49(16) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 119.67(18) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.62(19) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C6 122.32(17) . . ?
C10 C11 H11 118.8 . . ?
C6 C11 H11 118.8 . . ?
N1 C12 C5 111.47(12) . . ?
N1 C12 H12A 109.3 . . ?
C5 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
C5 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?

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
C4 O1 C1 O2 -178.82(15) . . . . ?
C4 O1 C1 C2 0.90(17) . . . . ?
O2 C1 C2 C3 178.69(17) . . . . ?
O1 C1 C2 C3 -1.00(17) . . . . ?
O2 C1 C2 C5 1.7(3) . . . . ?
O1 C1 C2 C5 -178.03(14) . . . . ?
C7 O3 C3 C2 -1.0(2) . . . . ?
C7 O3 C3 C4 -179.73(13) . . . . ?
C1 C2 C3 O3 -178.13(14) . . . . ?
C5 C2 C3 O3 -0.9(3) . . . . ?
C1 C2 C3 C4 0.71(18) . . . . ?
C5 C2 C3 C4 177.95(13) . . . . ?
C1 O1 C4 C3 -0.46(17) . . . . ?
O3 C3 C4 O1 178.74(12) . . . . ?
C2 C3 C4 O1 -0.18(18) . . . . ?
C3 C2 C5 C6 3.4(2) . . . . ?
C1 C2 C5 C6 179.99(15) . . . . ?
C3 C2 C5 C12 130.94(16) . . . . ?
C1 C2 C5 C12 -52.5(2) . . . . ?
C2 C5 C6 C11 178.10(13) . . . . ?
C12 C5 C6 C11 51.46(19) . . . . ?
C2 C5 C6 C7 -4.50(19) . . . . ?
C12 C5 C6 C7 -131.14(15) . . . . ?
C11 C6 C7 C8 0.8(2) . . . . ?
C5 C6 C7 C8 -176.71(13) . . . . ?
C11 C6 C7 O3 -179.16(13) . . . . ?
C5 C6 C7 O3 3.3(2) . . . . ?
C3 O3 C7 C8 179.75(13) . . . . ?
C3 O3 C7 C6 -0.28(19) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
O3 C7 C8 C9 179.93(13) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C7 C6 C11 C10 -0.7(2) . . . . ?
C5 C6 C11 C10 176.88(15) . . . . ?
O5 N1 C12 C5 -71.9(2) . . . . ?
O4 N1 C12 C5 106.71(18) . . . . ?
C2 C5 C12 N1 -56.0(2) . . . . ?
C6 C5 C12 N1 68.17(19) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.047



