# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1511246'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N O4'
_chemical_formula_weight         261.27

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   14.388(3)
_cell_length_b                   6.6658(13)
_cell_length_c                   14.112(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1353.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4287
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      31.06

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14228
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         32.13
_reflns_number_total             2437
_reflns_number_gt                1580
_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)+(0.1349P)²+0.3183P] 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_number_reflns         2437
_refine_ls_number_parameters     122
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2460
_refine_ls_wR_factor_gt          0.2062
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.032
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.79144(14) 0.7500 0.38498(15) 0.0738(6) Uani 1 2 d S . .
O2 O 0.38732(11) 0.7500 0.56548(11) 0.0465(4) Uani 1 2 d S A .
O3 O 0.21090(14) 0.7500 0.52067(15) 0.0779(7) Uani 1 2 d SU . .
O4 O 0.16479(15) 0.7500 0.67208(17) 0.0822(7) Uani 1 2 d S . .
N1 N 0.35957(16) 0.7500 0.72020(15) 0.0587(6) Uani 1 2 d S A .
C1 C 0.8785(3) 0.7500 0.2417(4) 0.1089(15) Uani 1 2 d S . .
H1A H 0.9142 0.8571 0.2690 0.163 Uiso 0.50 1 calc PR . .
H1B H 0.8744 0.7687 0.1744 0.163 Uiso 0.50 1 calc PR . .
H1C H 0.9083 0.6242 0.2549 0.163 Uiso 0.50 1 calc PR . .
C2 C 0.7833(3) 0.7500 0.2833(2) 0.0772(9) Uani 1 2 d S . .
H2A H 0.7495 0.8680 0.2625 0.093 Uiso 0.50 1 calc PR . .
H2B H 0.7495 0.6320 0.2625 0.093 Uiso 0.50 1 calc PR . .
C3 C 0.71048(18) 0.7500 0.43543(18) 0.0537(6) Uani 1 2 d S . .
C4 C 0.62331(18) 0.7500 0.39504(17) 0.0534(6) Uani 1 2 d S . .
H4 H 0.6165 0.7500 0.3295 0.064 Uiso 1 2 calc SR . .
C5 C 0.54575(17) 0.7500 0.45360(16) 0.0497(5) Uani 1 2 d S . .
H5 H 0.4869 0.7500 0.4264 0.060 Uiso 1 2 calc SR . .
C6 C 0.55373(15) 0.7500 0.55086(15) 0.0433(5) Uani 1 2 d S . .
C7 C 0.64251(16) 0.7500 0.59036(17) 0.0531(6) Uani 1 2 d S . .
H7 H 0.6495 0.7500 0.6559 0.064 Uiso 1 2 calc SR . .
C8 C 0.71946(18) 0.7500 0.5333(2) 0.0594(6) Uani 1 2 d S . .
H8 H 0.7784 0.7500 0.5605 0.071 Uiso 1 2 calc SR . .
C9 C 0.47173(14) 0.7500 0.60963(15) 0.0439(5) Uani 1 2 d S . .
C10 C 0.45398(18) 0.7500 0.70503(17) 0.0553(6) Uani 1 2 d S . .
H10 H 0.4990 0.7500 0.7524 0.066 Uiso 1 2 calc SR . .
C11 C 0.32406(16) 0.7500 0.63625(17) 0.0501(5) Uani 1 2 d S . .
C12 C 0.22490(17) 0.7500 0.6128(2) 0.0584(6) Uani 1 2 d S A .
C13 C 0.1135(3) 0.8038(11) 0.4929(4) 0.100(2) Uani 0.50 1 d PU A -1
H13A H 0.0701 0.7774 0.5440 0.120 Uiso 0.50 1 calc PR A -1
H13B H 0.1089 0.9437 0.4745 0.120 Uiso 0.50 1 calc PR A -1
C14 C 0.0973(5) 0.6731(16) 0.4137(6) 0.190(5) Uani 0.50 1 d PU A -1
H14A H 0.0346 0.6898 0.3917 0.285 Uiso 0.50 1 calc PR A -1
H14B H 0.1067 0.5364 0.4329 0.285 Uiso 0.50 1 calc PR A -1
H14C H 0.1398 0.7056 0.3635 0.285 Uiso 0.50 1 calc PR A -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0566(11) 0.0889(15) 0.0759(13) 0.000 0.0247(10) 0.000
O2 0.0428(8) 0.0532(9) 0.0437(8) 0.000 0.0030(6) 0.000
O3 0.0495(10) 0.1167(18) 0.0674(12) 0.000 -0.0042(9) 0.000
O4 0.0546(11) 0.1087(18) 0.0833(15) 0.000 0.0240(10) 0.000
N1 0.0593(12) 0.0683(13) 0.0486(11) 0.000 0.0093(9) 0.000
C1 0.100(3) 0.107(3) 0.120(3) 0.000 0.066(3) 0.000
C2 0.087(2) 0.0757(19) 0.0693(17) 0.000 0.0346(16) 0.000
C3 0.0508(12) 0.0518(13) 0.0586(13) 0.000 0.0127(10) 0.000
C4 0.0581(13) 0.0577(13) 0.0443(11) 0.000 0.0049(9) 0.000
C5 0.0474(12) 0.0579(13) 0.0439(10) 0.000 -0.0017(8) 0.000
C6 0.0439(11) 0.0427(11) 0.0433(10) 0.000 0.0015(8) 0.000
C7 0.0467(12) 0.0669(15) 0.0458(11) 0.000 -0.0022(9) 0.000
C8 0.0438(12) 0.0721(16) 0.0623(14) 0.000 -0.0025(10) 0.000
C9 0.0452(10) 0.0432(11) 0.0433(10) 0.000 0.0015(8) 0.000
C10 0.0552(13) 0.0663(15) 0.0445(11) 0.000 0.0004(9) 0.000
C11 0.0481(11) 0.0506(12) 0.0518(11) 0.000 0.0094(9) 0.000
C12 0.0486(12) 0.0622(15) 0.0645(14) 0.000 0.0068(11) 0.000
C13 0.063(2) 0.134(7) 0.102(3) 0.002(3) -0.019(2) -0.003(3)
C14 0.136(6) 0.228(13) 0.206(8) -0.088(7) -0.093(6) 0.036(6)

_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 C3 1.365(3) . ?
O1 C2 1.440(4) . ?
O2 C11 1.351(3) . ?
O2 C9 1.365(3) . ?
O3 C12 1.315(3) . ?
O3 C13 1.499(5) . ?
O3 C13 1.499(5) 8_575 ?
O4 C12 1.203(3) . ?
N1 C11 1.290(3) . ?
N1 C10 1.375(3) . ?
C1 C2 1.490(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.378(4) . ?
C3 C8 1.388(4) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(3) . ?
C6 C9 1.442(3) . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.465(4) . ?
C13 C14 1.436(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C3 O1 C2 116.8(2) . . ?
C11 O2 C9 105.18(17) . . ?
C12 O3 C13 113.7(3) . . ?
C12 O3 C13 113.7(3) . 8_575 ?
C13 O3 C13 27.7(5) . 8_575 ?
C11 N1 C10 104.4(2) . . ?
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 108.5(3) . . ?
O1 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
O1 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O1 C3 C4 124.1(2) . . ?
O1 C3 C8 116.1(2) . . ?
C4 C3 C8 119.8(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 118.4(2) . . ?
C5 C6 C9 120.3(2) . . ?
C7 C6 C9 121.32(19) . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C3 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
O2 C9 C10 106.42(19) . . ?
O2 C9 C6 117.74(18) . . ?
C10 C9 C6 135.8(2) . . ?
N1 C10 C9 109.7(2) . . ?
N1 C10 H10 125.2 . . ?
C9 C10 H10 125.2 . . ?
N1 C11 O2 114.3(2) . . ?
N1 C11 C12 126.4(2) . . ?
O2 C11 C12 119.3(2) . . ?
O4 C12 O3 125.2(3) . . ?
O4 C12 C11 122.9(3) . . ?
O3 C12 C11 111.9(2) . . ?
C14 C13 O3 102.1(5) . . ?
C14 C13 H13A 111.3 . . ?
O3 C13 H13A 111.3 . . ?
C14 C13 H13B 111.3 . . ?
O3 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
C3 O1 C2 C1 180.0 . . . . ?
C2 O1 C3 C4 0.000(1) . . . . ?
C2 O1 C3 C8 180.0 . . . . ?
O1 C3 C4 C5 180.0 . . . . ?
C8 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C6 C9 180.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C9 C6 C7 C8 180.0 . . . . ?
C6 C7 C8 C3 0.0 . . . . ?
O1 C3 C8 C7 180.0 . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
C11 O2 C9 C10 0.0 . . . . ?
C11 O2 C9 C6 180.0 . . . . ?
C5 C6 C9 O2 0.000(1) . . . . ?
C7 C6 C9 O2 180.0 . . . . ?
C5 C6 C9 C10 180.0 . . . . ?
C7 C6 C9 C10 0.000(1) . . . . ?
C11 N1 C10 C9 0.0 . . . . ?
O2 C9 C10 N1 0.0 . . . . ?
C6 C9 C10 N1 180.0 . . . . ?
C10 N1 C11 O2 0.0 . . . . ?
C10 N1 C11 C12 180.0 . . . . ?
C9 O2 C11 N1 0.000(1) . . . . ?
C9 O2 C11 C12 180.0 . . . . ?
C13 O3 C12 O4 15.2(3) . . . . ?
C13 O3 C12 O4 -15.2(3) 8_575 . . . ?
C13 O3 C12 C11 -164.8(3) . . . . ?
C13 O3 C12 C11 164.8(3) 8_575 . . . ?
N1 C11 C12 O4 0.0 . . . . ?
O2 C11 C12 O4 180.0 . . . . ?
N1 C11 C12 O3 180.0 . . . . ?
O2 C11 C12 O3 0.0 . . . . ?
C12 O3 C13 C14 -142.4(5) . . . . ?
C13 O3 C13 C14 -46.2(6) 8_575 . . . ?

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        32.13
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.193
