# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_cad4
_database_code_depnum_ccdc_archive 'CCDC 1423098'
_audit_update_record             
;
2015-09-08 deposited with the CCDC.
2015-10-02 downloaded from the CCDC.
;
_audit_creation_date             2015-09-07
_audit_creation_method           'WinGX-Routine XCAD4'
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H23 N O9'
_chemical_formula_sum            'C17 H23 N O9'
_chemical_formula_weight         385.36
_chemical_absolute_configuration syn
_chemical_melting_point          ?
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   9.1230(18)
_cell_length_b                   14.399(3)
_cell_length_c                   15.260(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2004.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297
_cell_measurement_theta_max      21.641
_cell_measurement_theta_min      20.258
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2187
_diffrn_reflns_theta_full        72.87
_diffrn_reflns_theta_max         72.87
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_temperature      297
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_dtime           1.195
_diffrn_detector_type            'scintillation LiI'
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius MACH3'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.030338
_diffrn_orient_matrix_UB_12      -0.028088
_diffrn_orient_matrix_UB_13      0.057126
_diffrn_orient_matrix_UB_21      0.015348
_diffrn_orient_matrix_UB_22      0.061149
_diffrn_orient_matrix_UB_23      0.029663
_diffrn_orient_matrix_UB_31      -0.104224
_diffrn_orient_matrix_UB_32      0.017164
_diffrn_orient_matrix_UB_33      -0.012284
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Cuk\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Cu
_diffrn_source_type              'fine-focus sealed tube'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
4 -2 2
4 2 -2

_diffrn_standards_decay_%        3
_diffrn_standards_decay_corr_max 1.077
_diffrn_standards_decay_corr_min 1.000
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_reflns_number_gt                1583
_reflns_number_total             2187
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0645P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1160
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O2 O 0.4404(2) 0.38079(15) 0.33884(16) 0.0492(6) Uani 1 1 d . . .
O6 O 0.0416(3) 0.27858(15) 0.20112(16) 0.0497(6) Uani 1 1 d . . .
O4 O 0.1123(2) 0.17008(15) 0.34975(16) 0.0474(6) Uani 1 1 d . . .
O1 O 0.2642(3) 0.40840(14) 0.23067(16) 0.0484(6) Uani 1 1 d . . .
O8 O 0.3684(3) 0.41656(16) 0.05635(17) 0.0569(7) Uani 1 1 d . . .
C1 C 0.2918(4) 0.4009(2) 0.3211(2) 0.0452(8) Uani 1 1 d . . .
H1 H 0.2668 0.4601 0.3490 0.054 Uiso 1 1 calc R . .
N1 N 0.2382(3) 0.3121(2) 0.45441(18) 0.0494(7) Uani 1 1 d . . .
H1A H 0.3293 0.3113 0.4690 0.059 Uiso 1 1 calc R . .
C3 C 0.2183(4) 0.2331(2) 0.3129(2) 0.0423(8) Uani 1 1 d . . .
H3 H 0.3173 0.2086 0.3219 0.051 Uiso 1 1 calc R . .
C4 C 0.1906(4) 0.2472(2) 0.2157(2) 0.0452(8) Uani 1 1 d . . .
H4 H 0.2088 0.1894 0.1836 0.054 Uiso 1 1 calc R . .
O3 O 0.0039(3) 0.3068(2) 0.50339(18) 0.0650(8) Uani 1 1 d . . .
C2 C 0.2004(4) 0.3242(2) 0.3635(2) 0.0431(8) Uani 1 1 d . . .
H2 H 0.0971 0.3425 0.3605 0.052 Uiso 1 1 calc R . .
C8 C 0.5242(4) 0.5381(2) 0.3618(3) 0.0543(9) Uani 1 1 d . . .
C6 C 0.2670(4) 0.3467(3) 0.0871(2) 0.0549(9) Uani 1 1 d . . .
H6A H 0.2787 0.2908 0.0524 0.066 Uiso 1 1 calc R . .
H6B H 0.1675 0.3689 0.0793 0.066 Uiso 1 1 calc R . .
O9 O 0.5292(3) 0.30724(17) 0.0176(2) 0.0690(8) Uani 1 1 d . . .
C5 C 0.2919(4) 0.3241(2) 0.1823(2) 0.0471(8) Uani 1 1 d . . .
H5 H 0.3942 0.3053 0.1908 0.056 Uiso 1 1 calc R . .
O5 O 0.2482(4) 0.04886(18) 0.3085(2) 0.0853(10) Uani 1 1 d . . .
C16 C 0.4954(4) 0.3885(2) 0.0225(2) 0.0519(9) Uani 1 1 d . . .
C12 C 0.1404(5) 0.0781(2) 0.3417(3) 0.0566(10) Uani 1 1 d . . .
C13 C 0.0181(5) 0.0224(3) 0.3789(3) 0.0750(13) Uani 1 1 d . . .
H13A H -0.0025 0.0433 0.4374 0.113 Uiso 1 1 calc R . .
H13B H 0.0454 -0.0420 0.3803 0.113 Uiso 1 1 calc R . .
H13C H -0.0677 0.0299 0.3432 0.113 Uiso 1 1 calc R . .
C10 C 0.1359(5) 0.3021(3) 0.5177(3) 0.0552(10) Uani 1 1 d . . .
O7 O -0.0391(4) 0.1325(2) 0.1815(2) 0.0800(9) Uani 1 1 d . . .
C7 C 0.5394(4) 0.4529(2) 0.3111(3) 0.0594(10) Uani 1 1 d . . .
H7A H 0.5216 0.4666 0.2498 0.071 Uiso 1 1 calc R . .
H7B H 0.6393 0.4305 0.3164 0.071 Uiso 1 1 calc R . .
C14 C -0.0623(5) 0.2150(3) 0.1827(3) 0.0597(10) Uani 1 1 d . . .
C9 C 0.5134(5) 0.6068(3) 0.4020(3) 0.0653(11) Uani 1 1 d . . .
H9 H 0.5047 0.6615 0.4340 0.078 Uiso 1 1 calc R . .
C17 C 0.5879(5) 0.4670(3) -0.0073(3) 0.0748(13) Uani 1 1 d . . .
H17A H 0.5463 0.4937 -0.0593 0.112 Uiso 1 1 calc R . .
H17B H 0.6850 0.4449 -0.0198 0.112 Uiso 1 1 calc R . .
H17C H 0.5924 0.5133 0.0379 0.112 Uiso 1 1 calc R . .
C15 C -0.2056(5) 0.2614(4) 0.1662(3) 0.0810(14) Uani 1 1 d . . .
H15A H -0.2106 0.3181 0.1991 0.122 Uiso 1 1 calc R . .
H15B H -0.2839 0.2210 0.1839 0.122 Uiso 1 1 calc R . .
H15C H -0.2148 0.2750 0.1048 0.122 Uiso 1 1 calc R . .
C11 C 0.1948(6) 0.2868(4) 0.6083(3) 0.0895(17) Uani 1 1 d . . .
H11A H 0.2978 0.2736 0.6051 0.134 Uiso 1 1 calc R . .
H11B H 0.1448 0.2353 0.6349 0.134 Uiso 1 1 calc R . .
H11C H 0.1794 0.3416 0.6429 0.134 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
O2 C1 1.413(4) . ?
O2 C7 1.440(4) . ?
O6 C4 1.450(4) . ?
O6 C14 1.348(4) . ?
O4 C3 1.440(4) . ?
O4 C12 1.355(4) . ?
O1 C1 1.407(4) . ?
O1 C5 1.443(4) . ?
O8 C6 1.444(4) . ?
O8 C16 1.331(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.528(4) . ?
N1 H1A 0.8600 . ?
N1 C2 1.439(4) . ?
N1 C10 1.350(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.518(5) . ?
C3 C2 1.530(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.530(4) . ?
O3 C10 1.225(4) . ?
C2 H2 0.9800 . ?
C8 C7 1.457(5) . ?
C8 C9 1.169(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.506(5) . ?
O9 C16 1.212(4) . ?
C5 H5 0.9800 . ?
O5 C12 1.183(5) . ?
C16 C17 1.483(5) . ?
C12 C13 1.487(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 C11 1.500(6) . ?
O7 C14 1.207(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C15 1.490(6) . ?
C9 H9 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C1 O2 C7 113.4(3) . . ?
C14 O6 C4 118.7(3) . . ?
C12 O4 C3 117.0(3) . . ?
C1 O1 C5 113.9(2) . . ?
C16 O8 C6 118.1(3) . . ?
O2 C1 H1 108.5 . . ?
O2 C1 C2 107.1(3) . . ?
O1 C1 O2 112.1(3) . . ?
O1 C1 H1 108.5 . . ?
O1 C1 C2 112.0(3) . . ?
C2 C1 H1 108.5 . . ?
C2 N1 H1A 118.8 . . ?
C10 N1 H1A 118.8 . . ?
C10 N1 C2 122.4(3) . . ?
O4 C3 H3 109.7 . . ?
O4 C3 C4 110.7(3) . . ?
O4 C3 C2 105.8(3) . . ?
C4 C3 H3 109.7 . . ?
C4 C3 C2 111.2(3) . . ?
C2 C3 H3 109.7 . . ?
O6 C4 C3 110.3(3) . . ?
O6 C4 H4 110.3 . . ?
O6 C4 C5 106.8(3) . . ?
C3 C4 H4 110.3 . . ?
C3 C4 C5 108.8(3) . . ?
C5 C4 H4 110.3 . . ?
C1 C2 C3 110.3(3) . . ?
C1 C2 H2 108.0 . . ?
N1 C2 C1 111.4(3) . . ?
N1 C2 C3 110.9(3) . . ?
N1 C2 H2 108.0 . . ?
C3 C2 H2 108.0 . . ?
C9 C8 C7 179.3(5) . . ?
O8 C6 H6A 109.3 . . ?
O8 C6 H6B 109.3 . . ?
O8 C6 C5 111.6(3) . . ?
H6A C6 H6B 108.0 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
O1 C5 C4 109.4(3) . . ?
O1 C5 C6 106.6(3) . . ?
O1 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C6 C5 C4 112.8(3) . . ?
C6 C5 H5 109.3 . . ?
O8 C16 C17 112.5(3) . . ?
O9 C16 O8 122.6(4) . . ?
O9 C16 C17 124.9(4) . . ?
O4 C12 C13 110.5(3) . . ?
O5 C12 O4 122.9(4) . . ?
O5 C12 C13 126.6(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C10 C11 115.3(4) . . ?
O3 C10 N1 123.1(4) . . ?
O3 C10 C11 121.6(4) . . ?
O2 C7 C8 113.0(3) . . ?
O2 C7 H7A 109.0 . . ?
O2 C7 H7B 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O6 C14 C15 110.4(4) . . ?
O7 C14 O6 123.3(4) . . ?
O7 C14 C15 126.3(4) . . ?
C8 C9 H9 180.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
N1 H1A O3 0.86 2.37 3.037(4) 134.9 3_556

