# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_18053003
_database_code_depnum_ccdc_archive 'CCDC 1858401'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N O5'
_chemical_formula_weight         265.26

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.12044(5)
_cell_length_b                   14.66642(14)
_cell_length_c                   16.34735(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1227.66(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6653
_cell_measurement_theta_min      4.0250
_cell_measurement_theta_max      73.4570

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6836
_exptl_absorpt_correction_T_max  0.9122
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7388
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         73.58
_reflns_number_total             2415
_reflns_number_gt                2374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0524P)²+0.1681P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_number_reflns         2415
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.005

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.89285(19) 0.31396(6) 0.42513(5) 0.0164(2) Uani 1 1 d . . .
O3 O 0.25272(18) 0.23962(6) 0.17900(5) 0.0152(2) Uani 1 1 d . . .
H3 H 0.1501 0.1963 0.1887 0.023 Uiso 1 1 calc R . .
O2 O 0.12676(19) 0.35326(6) 0.03079(5) 0.0166(2) Uani 1 1 d . . .
C11 C 1.0727(3) 0.36370(9) 0.47534(8) 0.0162(3) Uani 1 1 d . . .
H11A H 1.1805 0.4033 0.4408 0.024 Uiso 1 1 calc R . .
H11B H 1.1851 0.3208 0.5049 0.024 Uiso 1 1 calc R . .
H11C H 0.9754 0.4010 0.5146 0.024 Uiso 1 1 calc R . .
C6 C 0.7108(2) 0.45832(9) 0.37679(7) 0.0136(3) Uani 1 1 d . . .
H6 H 0.8232 0.4928 0.4112 0.016 Uiso 1 1 calc R . .
C5 C 0.7227(2) 0.36318(9) 0.37811(7) 0.0129(3) Uani 1 1 d . . .
C3 C 0.3816(2) 0.35635(8) 0.27872(7) 0.0114(2) Uani 1 1 d . . .
C1 C 0.1048(2) 0.40052(8) 0.16764(7) 0.0119(2) Uani 1 1 d . . .
H1 H -0.0868 0.4024 0.1558 0.014 Uiso 1 1 calc R . .
C7 C 0.5346(3) 0.50336(8) 0.32518(7) 0.0129(2) Uani 1 1 d . . .
H7 H 0.5279 0.5681 0.3234 0.015 Uiso 1 1 calc R . .
C4 C 0.5559(2) 0.31138(8) 0.32843(7) 0.0125(2) Uani 1 1 d . . .
H4 H 0.5631 0.2467 0.3291 0.015 Uiso 1 1 calc R . .
C9 C 0.2620(3) 0.39607(8) 0.08848(7) 0.0126(2) Uani 1 1 d . . .
C8 C 0.3709(2) 0.45130(8) 0.27689(7) 0.0114(2) Uani 1 1 d . . .
O1 O 0.47796(18) 0.42666(7) 0.08038(6) 0.0195(2) Uani 1 1 d . . .
C2 C 0.1736(2) 0.31715(8) 0.22347(7) 0.0117(2) Uani 1 1 d . . .
H2 H 0.0173 0.3011 0.2572 0.014 Uiso 1 1 calc R . .
C10 C 0.2649(3) 0.33768(9) -0.04550(7) 0.0208(3) Uani 1 1 d . . .
H10A H 0.1547 0.3018 -0.0824 0.031 Uiso 1 1 calc R . .
H10B H 0.4270 0.3044 -0.0345 0.031 Uiso 1 1 calc R . .
H10C H 0.3063 0.3964 -0.0711 0.031 Uiso 1 1 calc R . .
N1 N 0.1841(2) 0.47960(7) 0.21739(6) 0.0116(2) Uani 1 1 d . . .
O5 O 0.12906(19) 0.62304(6) 0.26373(5) 0.0175(2) Uani 1 1 d . . .
C13 C -0.1047(3) 0.58244(9) 0.14185(8) 0.0165(3) Uani 1 1 d . . .
H13A H -0.0350 0.5542 0.0921 0.025 Uiso 1 1 calc R . .
H13B H -0.1202 0.6484 0.1337 0.025 Uiso 1 1 calc R . .
H13C H -0.2772 0.5568 0.1539 0.025 Uiso 1 1 calc R . .
C12 C 0.0774(2) 0.56375(8) 0.21249(7) 0.0132(2) 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
O4 C5 1.3679(15) . ?
O4 C11 1.4330(15) . ?
O3 C2 1.4091(14) . ?
O3 H3 0.8400 . ?
O2 C9 1.3280(15) . ?
O2 C10 1.4519(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C6 C5 1.3969(17) . ?
C6 C7 1.4008(17) . ?
C6 H6 0.9500 . ?
C5 C4 1.4023(17) . ?
C3 C4 1.3754(17) . ?
C3 C8 1.3939(17) . ?
C3 C2 1.5100(16) . ?
C1 N1 1.4736(15) . ?
C1 C9 1.5255(16) . ?
C1 C2 1.5661(16) . ?
C1 H1 1.0000 . ?
C7 C8 1.3817(17) . ?
C7 H7 0.9500 . ?
C4 H4 0.9500 . ?
C9 O1 1.2005(16) . ?
C8 N1 1.4259(15) . ?
C2 H2 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N1 C12 1.3521(16) . ?
O5 C12 1.2360(15) . ?
C13 C12 1.5095(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 O4 C11 117.54(9) . . ?
C2 O3 H3 109.5 . . ?
C9 O2 C10 115.49(10) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C6 C7 120.56(12) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
O4 C5 C6 124.30(11) . . ?
O4 C5 C4 115.31(11) . . ?
C6 C5 C4 120.38(11) . . ?
C4 C3 C8 121.14(11) . . ?
C4 C3 C2 128.93(11) . . ?
C8 C3 C2 109.87(10) . . ?
N1 C1 C9 110.87(10) . . ?
N1 C1 C2 103.34(9) . . ?
C9 C1 C2 110.00(10) . . ?
N1 C1 H1 110.8 . . ?
C9 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
C8 C7 C6 118.31(11) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C3 C4 C5 118.54(11) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
O1 C9 O2 125.36(12) . . ?
O1 C9 C1 124.31(11) . . ?
O2 C9 C1 110.32(11) . . ?
C7 C8 C3 121.06(11) . . ?
C7 C8 N1 129.49(11) . . ?
C3 C8 N1 109.38(10) . . ?
O3 C2 C3 114.40(10) . . ?
O3 C2 C1 113.21(9) . . ?
C3 C2 C1 102.13(9) . . ?
O3 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 N1 C8 125.25(10) . . ?
C12 N1 C1 125.05(10) . . ?
C8 N1 C1 109.41(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C12 N1 121.04(11) . . ?
O5 C12 C13 121.53(11) . . ?
N1 C12 C13 117.44(11) . . ?

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
C11 O4 C5 C6 -0.91(18) . . . . ?
C11 O4 C5 C4 178.29(10) . . . . ?
C7 C6 C5 O4 178.38(11) . . . . ?
C7 C6 C5 C4 -0.78(19) . . . . ?
C5 C6 C7 C8 1.04(18) . . . . ?
C8 C3 C4 C5 0.47(18) . . . . ?
C2 C3 C4 C5 -176.42(11) . . . . ?
O4 C5 C4 C3 -179.22(10) . . . . ?
C6 C5 C4 C3 0.01(18) . . . . ?
C10 O2 C9 O1 4.69(17) . . . . ?
C10 O2 C9 C1 -174.87(10) . . . . ?
N1 C1 C9 O1 26.94(16) . . . . ?
C2 C1 C9 O1 -86.74(14) . . . . ?
N1 C1 C9 O2 -153.50(10) . . . . ?
C2 C1 C9 O2 92.83(12) . . . . ?
C6 C7 C8 C3 -0.56(18) . . . . ?
C6 C7 C8 N1 -177.08(12) . . . . ?
C4 C3 C8 C7 -0.20(19) . . . . ?
C2 C3 C8 C7 177.23(10) . . . . ?
C4 C3 C8 N1 176.96(10) . . . . ?
C2 C3 C8 N1 -5.62(14) . . . . ?
C4 C3 C2 O3 -41.80(17) . . . . ?
C8 C3 C2 O3 141.03(10) . . . . ?
C4 C3 C2 C1 -164.49(12) . . . . ?
C8 C3 C2 C1 18.34(13) . . . . ?
N1 C1 C2 O3 -146.96(10) . . . . ?
C9 C1 C2 O3 -28.54(14) . . . . ?
N1 C1 C2 C3 -23.46(11) . . . . ?
C9 C1 C2 C3 94.96(11) . . . . ?
C7 C8 N1 C12 -19.9(2) . . . . ?
C3 C8 N1 C12 163.21(11) . . . . ?
C7 C8 N1 C1 165.98(12) . . . . ?
C3 C8 N1 C1 -10.86(13) . . . . ?
C9 C1 N1 C12 89.82(14) . . . . ?
C2 C1 N1 C12 -152.37(11) . . . . ?
C9 C1 N1 C8 -96.09(11) . . . . ?
C2 C1 N1 C8 21.72(12) . . . . ?
C8 N1 C12 O5 -3.26(19) . . . . ?
C1 N1 C12 O5 169.91(11) . . . . ?
C8 N1 C12 C13 176.27(11) . . . . ?
C1 N1 C12 C13 -10.56(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        73.58
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050
_chemical_absolute_configuration ad
