# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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#######################################################################

data_rj_ah421_0m
_database_code_depnum_ccdc_archive 'CCDC 1498919'
_audit_update_record             
;
2016-08-12 deposited with the CCDC.
2016-09-14 downloaded from the CCDC.
;
_audit_creation_date             2016-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H9 N O5'
_chemical_formula_sum            'C13 H9 N O5'
_chemical_formula_weight         259.21
_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                   10.7430(9)
_cell_length_b                   16.6008(14)
_cell_length_c                   6.9203(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.069(5)
_cell_angle_gamma                90
_cell_volume                     1215.17(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    250
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.9
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.8789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11534
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         1.925
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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                1702
_reflns_number_total             2674
_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       'SMART APEX II'
_computing_data_collection       'SMART APEX II (BRUKER,2010)'
_computing_data_reduction        'SAINT (BRUKER,2000)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.052
_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)+(0.0596P)²+0.1778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1364
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.23910(11) 0.44958(7) 0.5945(2) 0.0688(4) Uani 1 1 d . . . . .
N1 N 0.28180(16) 0.15210(9) 0.6052(2) 0.0642(4) Uani 1 1 d . . . . .
C1 C 0.18083(16) 0.52644(10) 0.5814(3) 0.0635(5) Uani 1 1 d . . . . .
O2 O 0.43085(12) 0.50269(7) 0.6993(2) 0.0787(4) Uani 1 1 d . . . . .
C2 C 0.1720(2) 0.56763(13) 0.7502(4) 0.0902(7) Uani 1 1 d . . . . .
H2 H 0.2094 0.5477 0.8722 0.108 Uiso 1 1 calc R . . . .
O3 O 0.62155(11) 0.40311(8) 0.8076(2) 0.0771(4) Uani 1 1 d . . . . .
H3 H 0.5868 0.4471 0.7900 0.116 Uiso 1 1 calc GR . . . .
C3 C 0.1065(2) 0.63918(15) 0.7345(5) 0.1124(10) Uani 1 1 d . . . . .
H3A H 0.0995 0.6680 0.8474 0.135 Uiso 1 1 calc R . . . .
O4 O 0.17139(15) 0.16714(9) 0.5447(3) 0.1027(6) Uani 1 1 d . . . . .
C4 C 0.0524(2) 0.66804(15) 0.5582(6) 0.1089(11) Uani 1 1 d . . . . .
H4 H 0.0088 0.7166 0.5501 0.131 Uiso 1 1 calc R . . . .
O5 O 0.32145(15) 0.08333(8) 0.6213(3) 0.0951(5) Uani 1 1 d . . . . .
C5 C 0.0613(2) 0.62645(17) 0.3914(5) 0.1062(9) Uani 1 1 d . . . . .
H5 H 0.0230 0.6467 0.2702 0.127 Uiso 1 1 calc R . . . .
C6 C 0.12812(19) 0.55302(13) 0.4011(4) 0.0824(7) Uani 1 1 d . . . . .
H6 H 0.1356 0.5242 0.2884 0.099 Uiso 1 1 calc R . . . .
C7 C 0.36347(16) 0.44456(10) 0.6601(3) 0.0557(4) Uani 1 1 d . . . . .
C8 C 0.40844(15) 0.36038(9) 0.6801(2) 0.0501(4) Uani 1 1 d . . . . .
C9 C 0.32579(16) 0.29618(9) 0.6314(2) 0.0506(4) Uani 1 1 d . . . . .
H9 H 0.2407 0.3056 0.5833 0.061 Uiso 1 1 calc R . . . .
C10 C 0.37078(16) 0.21851(9) 0.6548(2) 0.0515(4) Uani 1 1 d . . . . .
C11 C 0.49739(17) 0.20207(10) 0.7250(3) 0.0576(5) Uani 1 1 d . . . . .
H11 H 0.5260 0.1492 0.7388 0.069 Uiso 1 1 calc R . . . .
C12 C 0.57972(16) 0.26504(11) 0.7737(3) 0.0608(5) Uani 1 1 d . . . . .
H12 H 0.6647 0.2547 0.8207 0.073 Uiso 1 1 calc R . . . .
C13 C 0.53675(16) 0.34474(10) 0.7530(3) 0.0555(5) Uani 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
O1 C1 1.417(2) . ?
O1 C7 1.336(2) . ?
N1 O4 1.213(2) . ?
N1 O5 1.2167(18) . ?
N1 C10 1.460(2) . ?
C1 C2 1.371(3) . ?
C1 C6 1.351(3) . ?
O2 C7 1.2084(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
O3 H3 0.8200 . ?
O3 C13 1.338(2) . ?
C3 H3A 0.9300 . ?
C3 C4 1.344(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.410(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.477(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.407(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(2) . ?
C10 C11 1.389(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.400(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
C7 O1 C1 118.82(12) . . ?
O4 N1 O5 122.04(16) . . ?
O4 N1 C10 119.09(14) . . ?
O5 N1 C10 118.85(16) . . ?
C2 C1 O1 119.33(18) . . ?
C6 C1 O1 117.54(19) . . ?
C6 C1 C2 122.94(19) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.3(2) . . ?
C3 C2 H2 120.8 . . ?
C13 O3 H3 109.5 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
O1 C7 C8 112.46(13) . . ?
O2 C7 O1 123.40(15) . . ?
O2 C7 C8 124.14(15) . . ?
C9 C8 C7 121.19(14) . . ?
C9 C8 C13 119.32(15) . . ?
C13 C8 C7 119.48(14) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.55(15) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 N1 118.53(15) . . ?
C9 C10 C11 121.83(15) . . ?
C11 C10 N1 119.65(14) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.06(15) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.51(15) . . ?
C13 C12 H12 119.7 . . ?
O3 C13 C8 122.93(15) . . ?
O3 C13 C12 117.34(15) . . ?
C12 C13 C8 119.72(15) . . ?

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 C3 -175.0(2) . . . . ?
O1 C1 C6 C5 174.85(18) . . . . ?
O1 C7 C8 C9 0.7(2) . . . . ?
O1 C7 C8 C13 -178.19(16) . . . . ?
N1 C10 C11 C12 -179.11(16) . . . . ?
C1 O1 C7 O2 -4.1(3) . . . . ?
C1 O1 C7 C8 175.50(16) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
O2 C7 C8 C9 -179.67(18) . . . . ?
O2 C7 C8 C13 1.4(3) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
O4 N1 C10 C9 0.1(3) . . . . ?
O4 N1 C10 C11 179.72(18) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
O5 N1 C10 C9 178.35(17) . . . . ?
O5 N1 C10 C11 -2.0(3) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C7 O1 C1 C2 -68.4(2) . . . . ?
C7 O1 C1 C6 116.3(2) . . . . ?
C7 C8 C9 C10 -179.02(16) . . . . ?
C7 C8 C13 O3 0.6(3) . . . . ?
C7 C8 C13 C12 179.53(16) . . . . ?
C8 C9 C10 N1 179.17(15) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C8 C13 O3 -178.35(16) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 O3 178.45(17) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
