# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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 1557654'
_audit_update_record             
;
2017-06-21 deposited with the CCDC.
2018-02-06 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 0.0181 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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0788(3)
_cell_length_b                   10.0610(7)
_cell_length_c                   12.9069(8)
_cell_angle_alpha                76.261(5)
_cell_angle_beta                 80.914(5)
_cell_angle_gamma                81.176(5)
_cell_volume                     627.97(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2286
_cell_measurement_theta_min      3.5460
_cell_measurement_theta_max      71.4080

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7560
_exptl_absorpt_correction_T_max  0.7853
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11054
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.56
_diffrn_reflns_theta_max         66.04
_reflns_number_total             2176
_reflns_number_gt                1447
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1051P)²+0.0216P] 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         2176
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1811
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
N1 N 0.7318(4) 0.1848(2) 0.72403(15) 0.0617(5) Uani 1 1 d . . .
O1 O -0.0140(3) 0.51980(16) 0.63744(10) 0.0587(5) Uani 1 1 d . . .
O2 O -0.3462(4) 0.6755(2) 0.58624(12) 0.0792(6) Uani 1 1 d . . .
O3 O -0.7134(4) 0.7654(2) 0.72525(14) 0.0803(6) Uani 1 1 d . . .
H3 H -0.6308 0.7538 0.6675 0.120 Uiso 1 1 calc R . .
O4 O -0.6755(4) 0.68623(19) 0.89710(13) 0.0747(6) Uani 1 1 d . . .
C1 C -0.2409(5) 0.6032(2) 0.66205(16) 0.0566(6) Uani 1 1 d . . .
C2 C -0.3375(4) 0.5987(2) 0.77421(16) 0.0506(5) Uani 1 1 d . . .
C3 C -0.2012(4) 0.5132(2) 0.85099(15) 0.0517(6) Uani 1 1 d . . .
H3A H -0.2657 0.5098 0.9230 0.062 Uiso 1 1 calc R . .
C4 C 0.0356(4) 0.4293(2) 0.82428(15) 0.0491(5) Uani 1 1 d . . .
C5 C 0.1260(4) 0.4332(2) 0.71520(15) 0.0492(5) Uani 1 1 d . . .
C6 C 0.3517(4) 0.3536(2) 0.67996(15) 0.0515(5) Uani 1 1 d . . .
H6 H 0.4020 0.3589 0.6068 0.062 Uiso 1 1 calc R . .
C7 C 0.5060(5) 0.2641(2) 0.75517(16) 0.0526(5) Uani 1 1 d . . .
C8 C 0.4185(5) 0.2617(2) 0.86611(17) 0.0573(6) Uani 1 1 d . . .
H8 H 0.5192 0.2052 0.9176 0.069 Uiso 1 1 calc R . .
C9 C 0.1920(5) 0.3397(2) 0.89833(15) 0.0553(6) Uani 1 1 d . . .
H9 H 0.1390 0.3336 0.9715 0.066 Uiso 1 1 calc R . .
C10 C -0.5878(5) 0.6859(2) 0.80504(18) 0.0588(6) Uani 1 1 d . . .
C11 C 0.8217(5) 0.1842(3) 0.6109(2) 0.0726(7) Uani 1 1 d . . .
H11A H 1.0157 0.1631 0.6012 0.087 Uiso 1 1 calc R . .
H11B H 0.7767 0.2758 0.5680 0.087 Uiso 1 1 calc R . .
C12 C 0.7008(7) 0.0826(4) 0.5702(3) 0.0903(9) Uani 1 1 d . . .
H12A H 0.7472 -0.0086 0.6113 0.135 Uiso 1 1 calc R . .
H12B H 0.7689 0.0871 0.4959 0.135 Uiso 1 1 calc R . .
H12C H 0.5090 0.1044 0.5774 0.135 Uiso 1 1 calc R . .
C13 C 0.8803(6) 0.0856(3) 0.8014(2) 0.0759(7) Uani 1 1 d . . .
H13A H 0.9032 0.1293 0.8583 0.091 Uiso 1 1 calc R . .
H13B H 1.0576 0.0597 0.7661 0.091 Uiso 1 1 calc R . .
C14 C 0.7506(8) -0.0413(3) 0.8504(3) 0.0962(10) Uani 1 1 d . . .
H14A H 0.5667 -0.0164 0.8771 0.144 Uiso 1 1 calc R . .
H14B H 0.8438 -0.0951 0.9085 0.144 Uiso 1 1 calc R . .
H14C H 0.7573 -0.0943 0.7970 0.144 Uiso 1 1 calc R . .


_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
N1 C7 1.356(3) . ?
N1 C13 1.448(3) . ?
N1 C11 1.460(3) . ?
O1 C1 1.359(3) . ?
O1 C5 1.375(3) . ?
O2 C1 1.217(3) . ?
O3 C10 1.329(3) . ?
O3 H3 0.8200 . ?
O4 C10 1.202(3) . ?
C1 C2 1.446(3) . ?
C2 C3 1.353(3) . ?
C2 C10 1.486(3) . ?
C3 C4 1.404(3) . ?
C3 H3A 0.9300 . ?
C4 C9 1.403(3) . ?
C4 C5 1.403(3) . ?
C5 C6 1.374(3) . ?
C6 C7 1.406(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.426(3) . ?
C8 C9 1.356(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C11 C12 1.499(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.485(5) . ?
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
C7 N1 C13 121.68(19) . . ?
C7 N1 C11 121.8(2) . . ?
C13 N1 C11 116.2(2) . . ?
C1 O1 C5 122.29(15) . . ?
C10 O3 H3 109.5 . . ?
O2 C1 O1 116.19(18) . . ?
O2 C1 C2 125.6(2) . . ?
O1 C1 C2 118.2(2) . . ?
C3 C2 C1 119.70(19) . . ?
C3 C2 C10 120.15(18) . . ?
C1 C2 C10 120.1(2) . . ?
C2 C3 C4 121.42(17) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C9 C4 C5 116.27(19) . . ?
C9 C4 C3 125.28(17) . . ?
C5 C4 C3 118.4(2) . . ?
C6 C5 O1 116.70(17) . . ?
C6 C5 C4 123.4(2) . . ?
O1 C5 C4 119.90(19) . . ?
C5 C6 C7 119.63(18) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
N1 C7 C6 121.66(18) . . ?
N1 C7 C8 121.0(2) . . ?
C6 C7 C8 117.3(2) . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 121.78(18) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
O4 C10 O3 120.7(2) . . ?
O4 C10 C2 122.6(2) . . ?
O3 C10 C2 116.74(18) . . ?
N1 C11 C12 113.7(2) . . ?
N1 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 114.1(3) . . ?
N1 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
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
C5 O1 C1 O2 179.7(2) . . . . ?
C5 O1 C1 C2 -0.6(3) . . . . ?
O2 C1 C2 C3 179.9(2) . . . . ?
O1 C1 C2 C3 0.2(3) . . . . ?
O2 C1 C2 C10 0.9(4) . . . . ?
O1 C1 C2 C10 -178.78(19) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C10 C2 C3 C4 179.89(19) . . . . ?
C2 C3 C4 C9 178.8(2) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C1 O1 C5 C6 179.69(19) . . . . ?
C1 O1 C5 C4 -0.1(3) . . . . ?
C9 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C6 -178.6(2) . . . . ?
C9 C4 C5 O1 -179.15(19) . . . . ?
C3 C4 C5 O1 1.2(3) . . . . ?
O1 C5 C6 C7 179.21(18) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C13 N1 C7 C6 -175.6(2) . . . . ?
C11 N1 C7 C6 -2.3(4) . . . . ?
C13 N1 C7 C8 5.6(4) . . . . ?
C11 N1 C7 C8 178.9(2) . . . . ?
C5 C6 C7 N1 -179.2(2) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
N1 C7 C8 C9 -179.5(2) . . . . ?
C6 C7 C8 C9 1.6(3) . . . . ?
C7 C8 C9 C4 -1.6(4) . . . . ?
C5 C4 C9 C8 0.3(3) . . . . ?
C3 C4 C9 C8 179.8(2) . . . . ?
C3 C2 C10 O4 1.3(4) . . . . ?
C1 C2 C10 O4 -179.7(2) . . . . ?
C3 C2 C10 O3 -178.8(2) . . . . ?
C1 C2 C10 O3 0.2(3) . . . . ?
C7 N1 C11 C12 -87.4(3) . . . . ?
C13 N1 C11 C12 86.3(3) . . . . ?
C7 N1 C13 C14 74.8(3) . . . . ?
C11 N1 C13 C14 -98.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.04
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.043
