# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1831464'
_audit_update_record             
;
2018-03-21 deposited with the CCDC.
2018-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O6'
_chemical_formula_sum            'C18 H21 N O6'
_chemical_formula_weight         347.36

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   8.9121(4)
_cell_length_b                   10.6028(6)
_cell_length_c                   10.6070(6)
_cell_angle_alpha                107.362(2)
_cell_angle_beta                 95.433(2)
_cell_angle_gamma                110.176(2)
_cell_volume                     875.81(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      28.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      1.317
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.099
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18241
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4328
_reflns_number_gt                3436
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXP-97

_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)+(0.0518P)²+0.3127P] 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         4328
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
C1 C 0.12295(16) 0.70464(14) 0.65118(13) 0.0322(3) Uani 1 1 d . . .
C2 C 0.16426(19) 0.62038(16) 0.71621(15) 0.0398(3) Uani 1 1 d . . .
H2 H 0.2738 0.6354 0.7404 0.048 Uiso 1 1 calc R . .
C3 C 0.0460(2) 0.51565(17) 0.74512(18) 0.0483(4) Uani 1 1 d . . .
C4 C -0.1194(2) 0.49245(16) 0.70961(17) 0.0461(4) Uani 1 1 d . . .
C5 C -0.16110(19) 0.57278(17) 0.64303(17) 0.0454(4) Uani 1 1 d . . .
H5 H -0.2709 0.5559 0.6167 0.055 Uiso 1 1 calc R . .
C6 C -0.04095(18) 0.67906(17) 0.61456(15) 0.0398(3) Uani 1 1 d . . .
H6 H -0.0712 0.7333 0.5705 0.048 Uiso 1 1 calc R . .
C7 C 0.25547(16) 0.81601(15) 0.62277(13) 0.0301(3) Uani 1 1 d . . .
C8 C 0.23625(15) 0.94763(15) 0.60560(13) 0.0294(3) Uani 1 1 d . . .
H8 H 0.3456 1.0243 0.6289 0.035 Uiso 1 1 calc R . .
C9 C 0.15783(17) 0.91805(16) 0.46111(13) 0.0330(3) Uani 1 1 d . . .
H9A H 0.2038 0.8624 0.3985 0.040 Uiso 1 1 calc R . .
H9B H 0.0408 0.8633 0.4432 0.040 Uiso 1 1 calc R . .
C10 C 0.21180(16) 1.06446(14) 0.82905(13) 0.0306(3) Uani 1 1 d . . .
C11 C 0.11597(18) 1.11814(15) 0.91032(14) 0.0342(3) Uani 1 1 d . . .
C12 C 0.1757(2) 1.18491(17) 1.04858(15) 0.0468(4) Uani 1 1 d . . .
H12 H 0.1127 1.2202 1.1028 0.056 Uiso 1 1 calc R . .
C13 C 0.3299(2) 1.19938(19) 1.10669(16) 0.0538(4) Uani 1 1 d . . .
H13 H 0.3694 1.2438 1.1999 0.065 Uiso 1 1 calc R . .
C14 C 0.4243(2) 1.14866(18) 1.02753(17) 0.0500(4) Uani 1 1 d . . .
H14 H 0.5278 1.1596 1.0671 0.060 Uiso 1 1 calc R . .
C15 C 0.36572(18) 1.08072(16) 0.88787(15) 0.0395(3) Uani 1 1 d . . .
H15 H 0.4300 1.0464 0.8344 0.047 Uiso 1 1 calc R . .
C16 C -0.1282(2) 1.1648(2) 0.91604(18) 0.0523(4) Uani 1 1 d . . .
H16A H -0.1552 1.1261 0.9859 0.078 Uiso 1 1 calc R . .
H16B H -0.2271 1.1459 0.8558 0.078 Uiso 1 1 calc R . .
H16C H -0.0665 1.2666 0.9562 0.078 Uiso 1 1 calc R . .
C17 C 0.2417(4) 0.4485(4) 0.8432(5) 0.1519(19) Uani 1 1 d . . .
H17A H 0.2843 0.4312 0.7627 0.228 Uiso 1 1 calc R . .
H17B H 0.2481 0.3820 0.8860 0.228 Uiso 1 1 calc R . .
H17C H 0.3049 0.5449 0.9044 0.228 Uiso 1 1 calc R . .
C18 C -0.3925(3) 0.3751(2) 0.7285(3) 0.0816(7) Uani 1 1 d . . .
H18A H -0.3969 0.4652 0.7782 0.122 Uiso 1 1 calc R . .
H18B H -0.4544 0.3026 0.7614 0.122 Uiso 1 1 calc R . .
H18C H -0.4382 0.3483 0.6341 0.122 Uiso 1 1 calc R . .
N1 N 0.38988(14) 0.79744(14) 0.61571(13) 0.0382(3) Uani 1 1 d . . .
O1 O 0.07738(19) 0.43006(17) 0.8087(2) 0.0847(5) Uani 1 1 d . . .
O2 O -0.22727(17) 0.38880(14) 0.74581(16) 0.0695(4) Uani 1 1 d . . .
O3 O 0.50757(13) 0.91306(13) 0.59480(14) 0.0515(3) Uani 1 1 d . . .
H3 H 0.5923 0.8992 0.5905 0.077 Uiso 1 1 calc R . .
O4 O 0.18820(12) 1.05233(11) 0.44275(10) 0.0381(2) Uani 1 1 d . . .
H4 H 0.1203 1.0404 0.3779 0.057 Uiso 1 1 calc R . .
O5 O 0.13996(11) 0.99897(11) 0.69318(9) 0.0329(2) Uani 1 1 d . . .
O6 O -0.03233(13) 1.09871(12) 0.84183(10) 0.0423(3) 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
C1 C6 1.384(2) . ?
C1 C2 1.399(2) . ?
C1 C7 1.4825(18) . ?
C2 C3 1.377(2) . ?
C3 O1 1.364(2) . ?
C3 C4 1.401(3) . ?
C4 O2 1.3685(19) . ?
C4 C5 1.375(3) . ?
C5 C6 1.393(2) . ?
C7 N1 1.2846(17) . ?
C7 C8 1.5234(19) . ?
C8 O5 1.4377(15) . ?
C8 C9 1.5149(18) . ?
C9 O4 1.4310(17) . ?
C10 O5 1.3749(16) . ?
C10 C15 1.382(2) . ?
C10 C11 1.4066(19) . ?
C11 O6 1.3631(18) . ?
C11 C12 1.381(2) . ?
C12 C13 1.389(3) . ?
C13 C14 1.370(3) . ?
C14 C15 1.394(2) . ?
C16 O6 1.4319(18) . ?
C17 O1 1.405(3) . ?
C18 O2 1.417(3) . ?
N1 O3 1.4041(16) . ?

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
C6 C1 C2 118.31(13) . . ?
C6 C1 C7 122.72(13) . . ?
C2 C1 C7 118.96(12) . . ?
C3 C2 C1 121.29(15) . . ?
O1 C3 C2 124.44(17) . . ?
O1 C3 C4 115.71(15) . . ?
C2 C3 C4 119.85(15) . . ?
O2 C4 C5 125.33(16) . . ?
O2 C4 C3 115.54(16) . . ?
C5 C4 C3 119.14(14) . . ?
C4 C5 C6 120.78(15) . . ?
C1 C6 C5 120.59(15) . . ?
N1 C7 C1 116.45(12) . . ?
N1 C7 C8 121.23(12) . . ?
C1 C7 C8 122.30(11) . . ?
O5 C8 C9 108.29(10) . . ?
O5 C8 C7 112.15(10) . . ?
C9 C8 C7 111.97(11) . . ?
O4 C9 C8 108.68(11) . . ?
O5 C10 C15 125.44(13) . . ?
O5 C10 C11 114.78(12) . . ?
C15 C10 C11 119.78(13) . . ?
O6 C11 C12 125.41(14) . . ?
O6 C11 C10 114.98(12) . . ?
C12 C11 C10 119.61(14) . . ?
C11 C12 C13 120.08(15) . . ?
C14 C13 C12 120.41(15) . . ?
C13 C14 C15 120.27(16) . . ?
C10 C15 C14 119.84(15) . . ?
C7 N1 O3 110.89(11) . . ?
C3 O1 C17 117.16(16) . . ?
C4 O2 C18 117.37(17) . . ?
C10 O5 C8 116.66(10) . . ?
C11 O6 C16 117.83(12) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
