# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_l13_08
_database_code_depnum_ccdc_archive 'CCDC 1014398'
_audit_update_record             
;
2014-07-17 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O5'
_chemical_formula_weight         325.31

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   Pbca

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

_cell_length_a                   12.291(3)
_cell_length_b                   7.4147(15)
_cell_length_c                   34.667(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3159.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_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            28515
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3606
_reflns_number_gt                1860
_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)+(0.0681P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3606
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_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
C5 C 0.87349(15) 0.0922(3) 0.16699(5) 0.0456(5) Uani 1 1 d . . .
C2 C 0.88400(16) 0.0843(3) 0.24673(5) 0.0486(5) Uani 1 1 d . . .
C6 C 0.79657(16) 0.1833(3) 0.18846(6) 0.0555(5) Uani 1 1 d . . .
H6 H 0.7418 0.2480 0.1762 0.067 Uiso 1 1 calc R . .
C4 C 0.95367(16) -0.0047(3) 0.18520(5) 0.0512(5) Uani 1 1 d . . .
H4 H 1.0041 -0.0687 0.1706 0.061 Uiso 1 1 calc R . .
C7 C 0.80129(17) 0.1782(3) 0.22803(6) 0.0589(6) Uani 1 1 d . . .
H7 H 0.7487 0.2380 0.2425 0.071 Uiso 1 1 calc R . .
C8 C 0.95468(16) 0.1772(3) 0.10290(5) 0.0498(5) Uani 1 1 d . . .
C3 C 0.96003(16) -0.0078(3) 0.22501(5) 0.0527(5) Uani 1 1 d . . .
H3 H 1.0154 -0.0718 0.2371 0.063 Uiso 1 1 calc R . .
C9 C 0.91346(16) 0.1668(3) 0.06351(5) 0.0500(5) Uani 1 1 d . . .
C1 C 0.96880(19) 0.0047(3) 0.30628(6) 0.0705(7) Uani 1 1 d . . .
H1A H 0.9657 -0.1224 0.3011 0.106 Uiso 1 1 calc R . .
H1B H 0.9606 0.0251 0.3335 0.106 Uiso 1 1 calc R . .
H1C H 1.0377 0.0515 0.2979 0.106 Uiso 1 1 calc R . .
N1 N 0.87254(12) 0.1013(2) 0.12545(4) 0.0487(4) Uani 1 1 d . . .
O1 O 0.88327(12) 0.0937(2) 0.28600(4) 0.0633(4) Uani 1 1 d . . .
O2 O 1.03957(11) 0.2385(2) 0.11470(4) 0.0639(4) Uani 1 1 d . . .
O4 O 0.81003(11) 0.0890(2) 0.06511(3) 0.0577(4) Uani 1 1 d . . .
O3 O 0.70036(12) -0.0116(2) 0.11261(4) 0.0727(5) Uani 1 1 d . . .
C15 C 0.88053(15) 0.1996(3) -0.08724(5) 0.0499(5) Uani 1 1 d . . .
C17 C 0.83709(17) 0.1263(3) -0.02176(6) 0.0587(6) Uani 1 1 d . . .
H17 H 0.7906 0.0725 -0.0040 0.070 Uiso 1 1 calc R . .
C16 C 0.81176(17) 0.1190(3) -0.06053(5) 0.0577(6) Uani 1 1 d . . .
H16 H 0.7490 0.0603 -0.0687 0.069 Uiso 1 1 calc R . .
C10 C 0.78496(17) 0.0528(3) 0.10286(5) 0.0544(5) Uani 1 1 d . . .
C14 C 0.97365(16) 0.2874(3) -0.07485(6) 0.0581(6) Uani 1 1 d . . .
H14 H 1.0195 0.3425 -0.0926 0.070 Uiso 1 1 calc R . .
C12 C 0.93076(16) 0.2126(3) -0.00863(5) 0.0510(5) Uani 1 1 d . . .
C11 C 0.96395(17) 0.2195(3) 0.03172(5) 0.0550(5) Uani 1 1 d . . .
H11 H 1.0323 0.2696 0.0358 0.066 Uiso 1 1 calc R . .
C13 C 0.99821(17) 0.2928(3) -0.03622(6) 0.0570(6) Uani 1 1 d . . .
H13 H 1.0612 0.3512 -0.0282 0.068 Uiso 1 1 calc R . .
C18 C 0.77767(17) 0.0932(3) -0.14179(6) 0.0672(6) Uani 1 1 d . . .
H18A H 0.7891 -0.0310 -0.1351 0.101 Uiso 1 1 calc R . .
H18B H 0.7765 0.1055 -0.1694 0.101 Uiso 1 1 calc R . .
H18C H 0.7095 0.1333 -0.1313 0.101 Uiso 1 1 calc R . .
O5 O 0.86415(11) 0.2004(2) -0.12625(4) 0.0592(4) 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
C5 C4 1.373(3) . ?
C5 C6 1.380(3) . ?
C5 N1 1.442(2) . ?
C2 O1 1.363(2) . ?
C2 C3 1.381(3) . ?
C2 C7 1.392(3) . ?
C6 C7 1.373(3) . ?
C4 C3 1.383(2) . ?
C8 O2 1.210(2) . ?
C8 N1 1.395(2) . ?
C8 C9 1.459(3) . ?
C9 C11 1.324(3) . ?
C9 O4 1.397(2) . ?
C1 O1 1.426(2) . ?
N1 C10 1.379(2) . ?
O4 C10 1.371(2) . ?
O3 C10 1.193(2) . ?
C15 O5 1.367(2) . ?
C15 C14 1.385(3) . ?
C15 C16 1.389(3) . ?
C17 C16 1.381(3) . ?
C17 C12 1.393(3) . ?
C14 C13 1.373(3) . ?
C12 C13 1.398(3) . ?
C12 C11 1.458(3) . ?
C18 O5 1.432(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
C4 C5 C6 119.99(18) . . ?
C4 C5 N1 119.31(17) . . ?
C6 C5 N1 120.68(17) . . ?
O1 C2 C3 125.04(18) . . ?
O1 C2 C7 115.77(17) . . ?
C3 C2 C7 119.18(18) . . ?
C7 C6 C5 119.74(19) . . ?
C5 C4 C3 120.54(18) . . ?
C6 C7 C2 120.65(18) . . ?
O2 C8 N1 125.90(17) . . ?
O2 C8 C9 129.50(18) . . ?
N1 C8 C9 104.60(17) . . ?
C2 C3 C4 119.85(18) . . ?
C11 C9 O4 125.56(17) . . ?
C11 C9 C8 126.95(19) . . ?
O4 C9 C8 107.49(15) . . ?
C10 N1 C8 110.60(16) . . ?
C10 N1 C5 124.15(16) . . ?
C8 N1 C5 124.94(15) . . ?
C2 O1 C1 117.63(15) . . ?
C10 O4 C9 108.86(14) . . ?
O5 C15 C14 115.24(17) . . ?
O5 C15 C16 124.86(18) . . ?
C14 C15 C16 119.90(18) . . ?
C16 C17 C12 121.49(19) . . ?
C17 C16 C15 119.65(19) . . ?
O3 C10 O4 123.00(18) . . ?
O3 C10 N1 128.60(19) . . ?
O4 C10 N1 108.40(17) . . ?
C13 C14 C15 119.86(19) . . ?
C17 C12 C13 117.49(18) . . ?
C17 C12 C11 124.11(18) . . ?
C13 C12 C11 118.38(19) . . ?
C9 C11 C12 131.1(2) . . ?
C14 C13 C12 121.6(2) . . ?
C15 O5 C18 118.62(16) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.042
