# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 1031306'
_audit_update_record             
;
2014-11-11 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N O10'
_chemical_formula_weight         373.31

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   'P 21 21 21'

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

_cell_length_a                   9.809(3)
_cell_length_b                   10.419(3)
_cell_length_c                   16.505(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1686.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2976
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      31.30

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_process_details   'NUMBAS (Rigaku, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            12759
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2950
_reflns_number_gt                2731
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b23 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b23 (Rigaku, 2012)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b23 (Rigaku, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1267P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2950
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_restrained_S_all      0.738
_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
O5 O 0.50026(15) 0.35126(14) 0.58845(9) 0.0187(3) Uani 1 1 d . . .
O7 O 0.38247(15) 0.15269(15) 0.45530(8) 0.0192(4) Uani 1 1 d . . .
O9 O 0.40067(16) -0.10852(14) 0.51817(9) 0.0216(4) Uani 1 1 d . . .
O1 O 0.50239(16) 0.07856(14) 0.65646(9) 0.0215(4) Uani 1 1 d . . .
O2 O 0.35466(18) 0.06433(15) 0.76707(9) 0.0262(4) Uani 1 1 d . . .
O4 O 0.24823(18) 0.47321(15) 0.72513(10) 0.0260(4) Uani 1 1 d . . .
O8 O 0.54725(17) 0.24204(18) 0.37868(10) 0.0282(4) Uani 1 1 d . . .
O10 O 0.52423(18) -0.23176(16) 0.60399(10) 0.0300(4) Uani 1 1 d . . .
O6 O 0.35086(17) 0.45583(17) 0.50706(10) 0.0269(4) Uani 1 1 d . . .
O3 O 0.14855(19) 0.10903(19) 0.81886(11) 0.0358(5) Uani 1 1 d . . .
N1 N 0.2802(2) 0.26594(17) 0.75535(11) 0.0202(4) Uani 1 1 d . . .
C3 C 0.3924(2) 0.2722(2) 0.61999(12) 0.0177(5) Uani 1 1 d . . .
H3A H 0.3021 0.3036 0.6041 0.021 Uiso 1 1 calc R . .
C14 C 0.2046(2) 0.3803(2) 0.76100(13) 0.0226(5) Uani 1 1 d . . .
C4 C 0.4144(2) 0.1324(2) 0.59560(12) 0.0181(4) Uani 1 1 d . . .
H4A H 0.3267 0.0874 0.5966 0.022 Uiso 1 1 calc R . .
C9 C 0.4297(2) 0.2172(2) 0.38894(12) 0.0203(5) Uani 1 1 d . . .
C6 C 0.5185(2) -0.0300(2) 0.49893(13) 0.0221(5) Uani 1 1 d . . .
H6A H 0.5439 -0.0422 0.4427 0.026 Uiso 1 1 calc R . .
H6B H 0.5951 -0.0549 0.5326 0.026 Uiso 1 1 calc R . .
C10 C 0.3138(2) 0.2501(2) 0.33394(14) 0.0248(5) Uani 1 1 d . . .
H10A H 0.3478 0.2956 0.2876 0.037 Uiso 1 1 calc R . .
H10B H 0.2497 0.3031 0.3624 0.037 Uiso 1 1 calc R . .
H10C H 0.2695 0.1727 0.3165 0.037 Uiso 1 1 calc R . .
C1 C 0.4668(3) 0.1338(2) 0.73021(12) 0.0217(5) Uani 1 1 d . . .
H1A H 0.5454 0.1381 0.7668 0.026 Uiso 1 1 calc R . .
C2 C 0.4099(2) 0.2678(2) 0.71268(12) 0.0184(5) Uani 1 1 d . . .
H2A H 0.4702 0.3359 0.7325 0.022 Uiso 1 1 calc R . .
C12 C 0.5889(3) 0.5107(2) 0.50394(14) 0.0256(5) Uani 1 1 d . . .
H12A H 0.5636 0.5730 0.4638 0.038 Uiso 1 1 calc R . .
H12B H 0.6531 0.4514 0.4810 0.038 Uiso 1 1 calc R . .
H12C H 0.6298 0.5535 0.5494 0.038 Uiso 1 1 calc R . .
C13 C 0.2499(2) 0.1455(2) 0.78460(13) 0.0247(5) Uani 1 1 d . . .
C15 C 0.0805(3) 0.3805(3) 0.81286(16) 0.0346(6) Uani 1 1 d . . .
H15A H 0.0389 0.4639 0.8113 0.052 Uiso 1 1 calc R . .
H15B H 0.1053 0.3601 0.8676 0.052 Uiso 1 1 calc R . .
H15C H 0.0171 0.3177 0.7931 0.052 Uiso 1 1 calc R . .
C7 C 0.4156(2) -0.2019(2) 0.57452(13) 0.0219(5) Uani 1 1 d . . .
C5 C 0.4832(2) 0.1096(2) 0.51388(12) 0.0195(5) Uani 1 1 d . . .
H5A H 0.5655 0.1624 0.5097 0.023 Uiso 1 1 calc R . .
C8 C 0.2818(3) -0.2597(2) 0.59545(16) 0.0306(6) Uani 1 1 d . . .
H8A H 0.2946 -0.3254 0.6355 0.046 Uiso 1 1 calc R . .
H8B H 0.2417 -0.2965 0.5477 0.046 Uiso 1 1 calc R . .
H8C H 0.2225 -0.1945 0.6166 0.046 Uiso 1 1 calc R . .
C11 C 0.4657(2) 0.4400(2) 0.53122(13) 0.0197(5) 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
O5 C11 1.365(3) . ?
O5 C3 1.439(2) . ?
O7 C9 1.366(3) . ?
O7 C5 1.453(2) . ?
O9 C7 1.354(3) . ?
O9 C6 1.451(3) . ?
O1 C1 1.391(3) . ?
O1 C4 1.438(3) . ?
O2 C13 1.362(3) . ?
O2 C1 1.451(3) . ?
O4 C14 1.213(3) . ?
O8 C9 1.193(3) . ?
O10 C7 1.211(3) . ?
O6 C11 1.206(3) . ?
O3 C13 1.206(3) . ?
N1 C13 1.377(3) . ?
N1 C14 1.407(3) . ?
N1 C2 1.454(3) . ?
C3 C4 1.526(3) . ?
C3 C2 1.540(3) . ?
C3 H3A 0.9800 . ?
C14 C15 1.489(3) . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9800 . ?
C9 C10 1.495(3) . ?
C6 C5 1.515(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C1 C2 1.531(3) . ?
C1 H1A 0.9800 . ?
C2 H2A 0.9800 . ?
C12 C11 1.485(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C7 C8 1.485(3) . ?
C5 H5A 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C11 O5 C3 117.11(17) . . ?
C9 O7 C5 117.04(17) . . ?
C7 O9 C6 117.99(17) . . ?
C1 O1 C4 107.43(16) . . ?
C13 O2 C1 110.57(17) . . ?
C13 N1 C14 129.4(2) . . ?
C13 N1 C2 111.75(18) . . ?
C14 N1 C2 118.83(18) . . ?
O5 C3 C4 110.30(17) . . ?
O5 C3 C2 107.12(17) . . ?
C4 C3 C2 102.58(17) . . ?
O5 C3 H3A 112.1 . . ?
C4 C3 H3A 112.1 . . ?
C2 C3 H3A 112.1 . . ?
O4 C14 N1 117.3(2) . . ?
O4 C14 C15 124.6(2) . . ?
N1 C14 C15 118.1(2) . . ?
O1 C4 C5 106.91(17) . . ?
O1 C4 C3 105.83(17) . . ?
C5 C4 C3 116.36(18) . . ?
O1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
O8 C9 O7 123.2(2) . . ?
O8 C9 C10 126.8(2) . . ?
O7 C9 C10 110.0(2) . . ?
O9 C6 C5 108.89(18) . . ?
O9 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
O9 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C1 O2 110.55(18) . . ?
O1 C1 C2 107.65(16) . . ?
O2 C1 C2 104.90(18) . . ?
O1 C1 H1A 111.2 . . ?
O2 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
N1 C2 C1 102.46(17) . . ?
N1 C2 C3 112.58(18) . . ?
C1 C2 C3 104.80(17) . . ?
N1 C2 H2A 112.1 . . ?
C1 C2 H2A 112.1 . . ?
C3 C2 H2A 112.1 . . ?
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 . . ?
O3 C13 O2 121.7(2) . . ?
O3 C13 N1 129.1(2) . . ?
O2 C13 N1 109.20(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O10 C7 O9 123.7(2) . . ?
O10 C7 C8 125.5(2) . . ?
O9 C7 C8 110.80(19) . . ?
O7 C5 C6 110.09(18) . . ?
O7 C5 C4 103.83(16) . . ?
C6 C5 C4 113.22(18) . . ?
O7 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C11 O5 123.6(2) . . ?
O6 C11 C12 126.3(2) . . ?
O5 C11 C12 110.1(2) . . ?

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
C11 O5 C3 C4 114.12(19) . . . . ?
C11 O5 C3 C2 -134.97(19) . . . . ?
C13 N1 C14 O4 -174.9(2) . . . . ?
C2 N1 C14 O4 4.6(3) . . . . ?
C13 N1 C14 C15 7.5(3) . . . . ?
C2 N1 C14 C15 -173.02(19) . . . . ?
C1 O1 C4 C5 160.65(18) . . . . ?
C1 O1 C4 C3 36.0(2) . . . . ?
O5 C3 C4 O1 86.18(19) . . . . ?
C2 C3 C4 O1 -27.7(2) . . . . ?
O5 C3 C4 C5 -32.4(2) . . . . ?
C2 C3 C4 C5 -146.22(18) . . . . ?
C5 O7 C9 O8 -2.1(3) . . . . ?
C5 O7 C9 C10 177.97(18) . . . . ?
C7 O9 C6 C5 -122.66(19) . . . . ?
C4 O1 C1 O2 85.3(2) . . . . ?
C4 O1 C1 C2 -28.7(2) . . . . ?
C13 O2 C1 O1 -125.47(18) . . . . ?
C13 O2 C1 C2 -9.7(2) . . . . ?
C13 N1 C2 C1 -7.9(2) . . . . ?
C14 N1 C2 C1 172.51(17) . . . . ?
C13 N1 C2 C3 104.1(2) . . . . ?
C14 N1 C2 C3 -75.4(2) . . . . ?
O1 C1 C2 N1 127.97(18) . . . . ?
O2 C1 C2 N1 10.21(19) . . . . ?
O1 C1 C2 C3 10.2(2) . . . . ?
O2 C1 C2 C3 -107.51(17) . . . . ?
O5 C3 C2 N1 143.92(17) . . . . ?
C4 C3 C2 N1 -99.9(2) . . . . ?
O5 C3 C2 C1 -105.50(19) . . . . ?
C4 C3 C2 C1 10.7(2) . . . . ?
C1 O2 C13 O3 -176.7(2) . . . . ?
C1 O2 C13 N1 5.0(2) . . . . ?
C14 N1 C13 O3 3.6(4) . . . . ?
C2 N1 C13 O3 -175.9(2) . . . . ?
C14 N1 C13 O2 -178.21(19) . . . . ?
C2 N1 C13 O2 2.3(2) . . . . ?
C6 O9 C7 O10 -7.4(3) . . . . ?
C6 O9 C7 C8 171.68(19) . . . . ?
C9 O7 C5 C6 -97.4(2) . . . . ?
C9 O7 C5 C4 141.08(18) . . . . ?
O9 C6 C5 O7 -68.0(2) . . . . ?
O9 C6 C5 C4 47.7(2) . . . . ?
O1 C4 C5 O7 173.73(15) . . . . ?
C3 C4 C5 O7 -68.3(2) . . . . ?
O1 C4 C5 C6 54.4(2) . . . . ?
C3 C4 C5 C6 172.33(19) . . . . ?
C3 O5 C11 O6 0.9(3) . . . . ?
C3 O5 C11 C12 -178.61(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.101
