# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1043546'
_audit_update_record             
;
2015-01-14 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N O6'
_chemical_formula_weight         367.35

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.8241(16)
_cell_length_b                   24.301(5)
_cell_length_c                   9.1574(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.76(3)
_cell_angle_gamma                90.00
_cell_volume                     1737.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4679
_cell_measurement_theta_min      1.6760
_cell_measurement_theta_max      27.9424

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15793
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         27.99
_reflns_number_total             4064
_reflns_number_gt                3051
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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)+(0.0703P)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    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.035(3)
_refine_ls_extinction_expression 
;
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
;
_refine_ls_number_reflns         4064
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_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 0.36790(13) 0.32914(4) 0.47376(12) 0.0232(3) Uani 1 1 d . . .
O2 O 0.43698(15) 0.21836(4) 0.46808(13) 0.0298(3) Uani 1 1 d . . .
O3 O 0.53670(13) 0.36573(4) 0.78554(12) 0.0240(3) Uani 1 1 d . . .
H3 H 0.5158 0.3443 0.8541 0.036 Uiso 1 1 calc R . .
O4 O 0.80668(14) 0.43409(4) 0.42412(12) 0.0284(3) Uani 1 1 d . . .
O5 O 0.85056(13) 0.41408(4) 0.66418(12) 0.0228(3) Uani 1 1 d . . .
O6 O 0.21452(15) 0.49222(4) -0.04028(13) 0.0313(3) Uani 1 1 d . . .
N1 N 0.44723(16) 0.30059(5) 0.59738(14) 0.0216(3) Uani 1 1 d . . .
C1 C 0.5087(2) 0.24823(6) 0.55961(18) 0.0237(4) Uani 1 1 d . . .
C2 C 0.6677(2) 0.24022(6) 0.65323(18) 0.0243(4) Uani 1 1 d . . .
C3 C 0.7595(2) 0.19240(6) 0.6838(2) 0.0317(4) Uani 1 1 d . . .
H3A H 0.7214 0.1579 0.6449 0.038 Uiso 1 1 calc R . .
C4 C 0.9088(2) 0.19665(7) 0.7731(2) 0.0369(5) Uani 1 1 d . . .
H4 H 0.9751 0.1646 0.7954 0.044 Uiso 1 1 calc R . .
C5 C 0.9632(2) 0.24728(7) 0.8307(2) 0.0367(4) Uani 1 1 d . . .
H5 H 1.0664 0.2492 0.8912 0.044 Uiso 1 1 calc R . .
C6 C 0.8686(2) 0.29515(7) 0.8009(2) 0.0304(4) Uani 1 1 d . . .
H6 H 0.9049 0.3295 0.8415 0.036 Uiso 1 1 calc R . .
C7 C 0.7201(2) 0.29107(6) 0.71021(18) 0.0236(4) Uani 1 1 d . . .
C8 C 0.58838(18) 0.33507(6) 0.66610(17) 0.0212(3) Uani 1 1 d . . .
C9 C 0.61680(18) 0.37358(6) 0.54005(17) 0.0208(3) Uani 1 1 d . . .
C10 C 0.48216(19) 0.37021(6) 0.44192(17) 0.0211(3) Uani 1 1 d . . .
C11 C 0.42114(18) 0.40280(6) 0.31392(17) 0.0208(3) Uani 1 1 d . . .
C12 C 0.44794(18) 0.45953(6) 0.30879(17) 0.0218(3) Uani 1 1 d . . .
H12 H 0.5132 0.4769 0.3870 0.026 Uiso 1 1 calc R . .
C13 C 0.38193(18) 0.49119(6) 0.19270(17) 0.0214(3) Uani 1 1 d . . .
H13 H 0.4013 0.5298 0.1911 0.026 Uiso 1 1 calc R . .
C14 C 0.28704(19) 0.46557(6) 0.07877(17) 0.0232(3) Uani 1 1 d . . .
C15 C 0.2605(2) 0.40853(6) 0.08052(18) 0.0268(4) Uani 1 1 d . . .
H15 H 0.1980 0.3911 0.0009 0.032 Uiso 1 1 calc R . .
C16 C 0.32554(18) 0.37763(6) 0.19841(17) 0.0240(4) Uani 1 1 d . . .
H16 H 0.3050 0.3391 0.2007 0.029 Uiso 1 1 calc R . .
C17 C 0.2295(2) 0.55092(6) -0.04678(18) 0.0283(4) Uani 1 1 d . . .
H17A H 0.1788 0.5673 0.0381 0.042 Uiso 1 1 calc R . .
H17B H 0.1692 0.5645 -0.1369 0.042 Uiso 1 1 calc R . .
H17C H 0.3507 0.5611 -0.0460 0.042 Uiso 1 1 calc R . .
C18 C 0.76533(19) 0.41018(6) 0.53282(17) 0.0210(3) Uani 1 1 d . . .
C19 C 0.99558(19) 0.45206(6) 0.67515(19) 0.0257(4) Uani 1 1 d . . .
H19A H 1.0160 0.4644 0.7778 0.031 Uiso 1 1 calc R . .
H19B H 0.9684 0.4849 0.6139 0.031 Uiso 1 1 calc R . .
C20 C 1.1548(2) 0.42504(7) 0.6257(2) 0.0366(4) Uani 1 1 d . . .
H20A H 1.1747 0.3904 0.6789 0.055 Uiso 1 1 calc R . .
H20B H 1.2530 0.4496 0.6455 0.055 Uiso 1 1 calc R . .
H20C H 1.1404 0.4175 0.5205 0.055 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
O1 C10 1.3835(17) . ?
O1 N1 1.4338(16) . ?
O2 C1 1.2178(19) . ?
O3 C8 1.4046(17) . ?
O4 C18 1.2147(18) . ?
O5 C18 1.3399(18) . ?
O5 C19 1.4610(17) . ?
O6 C14 1.3597(19) . ?
O6 C17 1.4328(19) . ?
N1 C1 1.4114(18) . ?
N1 C8 1.4921(19) . ?
C1 C2 1.477(2) . ?
C2 C3 1.385(2) . ?
C2 C7 1.393(2) . ?
C3 C4 1.386(3) . ?
C4 C5 1.394(2) . ?
C5 C6 1.396(2) . ?
C6 C7 1.387(2) . ?
C7 C8 1.521(2) . ?
C8 C9 1.514(2) . ?
C9 C10 1.342(2) . ?
C9 C18 1.468(2) . ?
C10 C11 1.468(2) . ?
C11 C12 1.396(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.384(2) . ?
C13 C14 1.388(2) . ?
C14 C15 1.402(2) . ?
C15 C16 1.384(2) . ?
C19 C20 1.504(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
C10 O1 N1 105.26(11) . . ?
C18 O5 C19 116.42(12) . . ?
C14 O6 C17 118.46(12) . . ?
C1 N1 O1 112.31(12) . . ?
C1 N1 C8 110.78(12) . . ?
O1 N1 C8 109.35(10) . . ?
O2 C1 N1 123.84(15) . . ?
O2 C1 C2 130.83(14) . . ?
N1 C1 C2 105.33(13) . . ?
C3 C2 C7 122.21(16) . . ?
C3 C2 C1 129.32(15) . . ?
C7 C2 C1 108.46(13) . . ?
C2 C3 C4 117.56(16) . . ?
C3 C4 C5 120.90(16) . . ?
C4 C5 C6 121.12(17) . . ?
C7 C6 C5 118.04(16) . . ?
C6 C7 C2 120.15(14) . . ?
C6 C7 C8 129.45(14) . . ?
C2 C7 C8 110.28(13) . . ?
O3 C8 N1 112.54(11) . . ?
O3 C8 C9 109.27(12) . . ?
N1 C8 C9 99.62(12) . . ?
O3 C8 C7 113.00(13) . . ?
N1 C8 C7 100.79(11) . . ?
C9 C8 C7 120.41(12) . . ?
C10 C9 C18 126.58(14) . . ?
C10 C9 C8 108.95(13) . . ?
C18 C9 C8 124.41(14) . . ?
C9 C10 O1 113.13(13) . . ?
C9 C10 C11 134.56(14) . . ?
O1 C10 C11 112.12(13) . . ?
C12 C11 C16 118.79(14) . . ?
C12 C11 C10 121.20(13) . . ?
C16 C11 C10 119.90(13) . . ?
C13 C12 C11 121.70(14) . . ?
C12 C13 C14 118.84(14) . . ?
O6 C14 C13 124.31(14) . . ?
O6 C14 C15 115.20(14) . . ?
C13 C14 C15 120.48(14) . . ?
C16 C15 C14 119.88(15) . . ?
C15 C16 C11 120.29(14) . . ?
O4 C18 O5 123.93(14) . . ?
O4 C18 C9 125.50(15) . . ?
O5 C18 C9 110.56(13) . . ?
O5 C19 C20 111.00(13) . . ?

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
C10 O1 N1 C1 -107.16(12) . . . . ?
C10 O1 N1 C8 16.24(13) . . . . ?
O1 N1 C1 O2 -35.89(19) . . . . ?
C8 N1 C1 O2 -158.49(14) . . . . ?
O1 N1 C1 C2 144.50(11) . . . . ?
C8 N1 C1 C2 21.90(16) . . . . ?
O2 C1 C2 C3 -14.7(3) . . . . ?
N1 C1 C2 C3 164.83(16) . . . . ?
O2 C1 C2 C7 164.30(16) . . . . ?
N1 C1 C2 C7 -16.13(16) . . . . ?
C7 C2 C3 C4 -0.7(2) . . . . ?
C1 C2 C3 C4 178.23(15) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C5 C6 C7 C2 0.9(2) . . . . ?
C5 C6 C7 C8 176.31(15) . . . . ?
C3 C2 C7 C6 0.0(2) . . . . ?
C1 C2 C7 C6 -179.12(14) . . . . ?
C3 C2 C7 C8 -176.25(14) . . . . ?
C1 C2 C7 C8 4.63(17) . . . . ?
C1 N1 C8 O3 -139.15(12) . . . . ?
O1 N1 C8 O3 96.54(14) . . . . ?
C1 N1 C8 C9 105.20(13) . . . . ?
O1 N1 C8 C9 -19.10(13) . . . . ?
C1 N1 C8 C7 -18.51(15) . . . . ?
O1 N1 C8 C7 -142.81(11) . . . . ?
C6 C7 C8 O3 -47.6(2) . . . . ?
C2 C7 C8 O3 128.24(13) . . . . ?
C6 C7 C8 N1 -167.89(16) . . . . ?
C2 C7 C8 N1 7.92(16) . . . . ?
C6 C7 C8 C9 84.1(2) . . . . ?
C2 C7 C8 C9 -100.09(16) . . . . ?
O3 C8 C9 C10 -102.50(14) . . . . ?
N1 C8 C9 C10 15.61(15) . . . . ?
C7 C8 C9 C10 124.26(14) . . . . ?
O3 C8 C9 C18 74.85(17) . . . . ?
N1 C8 C9 C18 -167.04(13) . . . . ?
C7 C8 C9 C18 -58.4(2) . . . . ?
C18 C9 C10 O1 175.82(13) . . . . ?
C8 C9 C10 O1 -6.90(17) . . . . ?
C18 C9 C10 C11 -9.7(3) . . . . ?
C8 C9 C10 C11 167.56(15) . . . . ?
N1 O1 C10 C9 -5.69(15) . . . . ?
N1 O1 C10 C11 178.56(11) . . . . ?
C9 C10 C11 C12 -32.4(3) . . . . ?
O1 C10 C11 C12 142.07(13) . . . . ?
C9 C10 C11 C16 151.48(17) . . . . ?
O1 C10 C11 C16 -34.02(18) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C13 -175.97(13) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C17 O6 C14 C13 -3.0(2) . . . . ?
C17 O6 C14 C15 177.24(13) . . . . ?
C12 C13 C14 O6 179.40(14) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
O6 C14 C15 C16 -178.51(13) . . . . ?
C13 C14 C15 C16 1.7(2) . . . . ?
C14 C15 C16 C11 -1.6(2) . . . . ?
C12 C11 C16 C15 0.7(2) . . . . ?
C10 C11 C16 C15 176.89(14) . . . . ?
C19 O5 C18 O4 3.5(2) . . . . ?
C19 O5 C18 C9 -176.24(11) . . . . ?
C10 C9 C18 O4 -16.7(2) . . . . ?
C8 C9 C18 O4 166.42(14) . . . . ?
C10 C9 C18 O5 163.01(14) . . . . ?
C8 C9 C18 O5 -13.87(19) . . . . ?
C18 O5 C19 C20 -84.01(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.84 1.97 2.7838(15) 163.6 4_566

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.059
