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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O8'
_chemical_formula_weight         363.32

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           ?
_symmetry_space_group_name_H-M   'P 21/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                   8.6190(3)
_cell_length_b                   27.0157(10)
_cell_length_c                   7.3823(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.789(2)
_cell_angle_gamma                90.00
_cell_volume                     1712.95(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   ?
_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            13894
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3361
_reflns_number_gt                2729
_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)+(0.1000P)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_number_reflns         3361
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001

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
N1 N 0.35285(13) 0.96169(4) 0.36331(16) 0.0371(3) Uani 1 1 d . . .
O2 O 0.16106(13) 1.13249(4) 0.40055(15) 0.0479(3) Uani 1 1 d . . .
O6 O 0.28092(13) 0.80401(4) 0.42648(16) 0.0499(3) Uani 1 1 d . . .
O8 O 0.53466(13) 0.85259(4) 0.19422(15) 0.0507(3) Uani 1 1 d . . .
O4 O 0.13465(14) 0.93336(4) 0.83944(16) 0.0524(3) Uani 1 1 d . . .
C7 C 0.36076(16) 0.88542(5) 0.48081(18) 0.0362(3) Uani 1 1 d . . .
C5 C 0.27425(15) 0.96341(5) 0.52097(19) 0.0358(3) Uani 1 1 d . . .
O3 O 0.22601(15) 0.85623(4) 0.81615(17) 0.0583(4) Uani 1 1 d . . .
C6 C 0.27931(16) 0.91531(5) 0.59475(19) 0.0371(3) Uani 1 1 d . . .
C3 C 0.22448(16) 1.04974(5) 0.4654(2) 0.0394(3) Uani 1 1 d . . .
C4 C 0.21023(17) 1.00875(5) 0.57056(19) 0.0398(3) Uani 1 1 d . . .
H4 H 0.1579 1.0108 0.6755 0.048 Uiso 1 1 calc R . .
O7 O 0.52516(16) 0.92751(4) 0.06466(17) 0.0638(4) Uani 1 1 d . . .
C8 C 0.40655(17) 0.91380(5) 0.33871(19) 0.0378(3) Uani 1 1 d . . .
C14 C 0.39462(16) 0.83132(5) 0.50917(19) 0.0377(3) Uani 1 1 d . . .
C1 C 0.36870(19) 1.00351(5) 0.2581(2) 0.0436(4) Uani 1 1 d . . .
H1 H 0.4225 1.0018 0.1543 0.052 Uiso 1 1 calc R . .
C2 C 0.30571(18) 1.04666(5) 0.3070(2) 0.0440(4) Uani 1 1 d . . .
H2 H 0.3157 1.0747 0.2358 0.053 Uiso 1 1 calc R . .
C9 C 0.15597(18) 1.09727(6) 0.5251(2) 0.0436(4) Uani 1 1 d . . .
O5 O 0.50686(14) 0.81506(4) 0.59362(17) 0.0578(3) Uani 1 1 d . . .
O1 O 0.10477(17) 1.10288(5) 0.66950(17) 0.0683(4) Uani 1 1 d . . .
C16 C 0.49359(18) 0.90017(5) 0.1848(2) 0.0418(4) Uani 1 1 d . . .
C12 C 0.21289(16) 0.89791(5) 0.7594(2) 0.0395(3) Uani 1 1 d . . .
C10 C 0.1111(2) 1.18154(6) 0.4532(3) 0.0562(5) Uani 1 1 d . . .
H10A H 0.1799 1.1941 0.5535 0.067 Uiso 1 1 calc R . .
H10B H 0.0062 1.1802 0.4913 0.067 Uiso 1 1 calc R . .
C13 C 0.0596(2) 0.91908(7) 0.9988(3) 0.0597(5) Uani 1 1 d . . .
H13A H -0.0197 0.8950 0.9659 0.090 Uiso 1 1 calc R . .
H13B H 0.0133 0.9477 1.0497 0.090 Uiso 1 1 calc R . .
H13C H 0.1353 0.9051 1.0870 0.090 Uiso 1 1 calc R . .
C11 C 0.1162(2) 1.21424(6) 0.2925(3) 0.0635(5) Uani 1 1 d . . .
H11A H 0.2209 1.2159 0.2577 0.095 Uiso 1 1 calc R . .
H11B H 0.0818 1.2468 0.3221 0.095 Uiso 1 1 calc R . .
H11C H 0.0492 1.2012 0.1935 0.095 Uiso 1 1 calc R . .
C17 C 0.6243(2) 0.83519(7) 0.0504(3) 0.0577(5) Uani 1 1 d . . .
H17A H 0.5679 0.8414 -0.0651 0.086 Uiso 1 1 calc R . .
H17B H 0.6425 0.8003 0.0644 0.086 Uiso 1 1 calc R . .
H17C H 0.7222 0.8523 0.0561 0.086 Uiso 1 1 calc R . .
C15 C 0.3002(3) 0.75112(6) 0.4413(3) 0.0742(6) Uani 1 1 d . . .
H15A H 0.3974 0.7417 0.3965 0.111 Uiso 1 1 calc R . .
H15B H 0.2162 0.7349 0.3709 0.111 Uiso 1 1 calc R . .
H15C H 0.2997 0.7414 0.5664 0.111 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
N1 C1 1.3840(18) . ?
N1 C8 1.3909(18) . ?
N1 C5 1.3955(17) . ?
O2 C9 1.3263(18) . ?
O2 C10 1.4562(17) . ?
O6 C14 1.3332(18) . ?
O6 C15 1.442(2) . ?
O8 C16 1.3334(18) . ?
O8 C17 1.4434(18) . ?
O4 C12 1.3371(18) . ?
O4 C13 1.4415(18) . ?
C7 C6 1.3968(19) . ?
C7 C8 1.3832(19) . ?
C7 C14 1.5016(19) . ?
C5 C4 1.4045(19) . ?
C5 C6 1.4083(19) . ?
O3 C12 1.2035(18) . ?
C6 C12 1.4637(19) . ?
C3 C4 1.3639(19) . ?
C3 C2 1.415(2) . ?
C3 C9 1.495(2) . ?
O7 C16 1.2026(18) . ?
C8 C16 1.460(2) . ?
C14 O5 1.1902(18) . ?
C1 C2 1.348(2) . ?
C9 O1 1.1969(18) . ?
C10 C11 1.483(3) . ?

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 N1 C8 129.53(12) . . ?
C1 N1 C5 121.21(12) . . ?
C8 N1 C5 109.26(11) . . ?
C9 O2 C10 116.12(12) . . ?
C14 O6 C15 115.99(14) . . ?
C16 O8 C17 115.58(12) . . ?
C12 O4 C13 116.50(12) . . ?
C6 C7 C8 109.01(12) . . ?
C6 C7 C14 125.47(12) . . ?
C8 C7 C14 125.52(12) . . ?
C4 C5 C6 134.76(13) . . ?
C4 C5 N1 118.36(12) . . ?
C6 C5 N1 106.88(12) . . ?
C7 C6 C5 107.54(12) . . ?
C7 C6 C12 124.44(13) . . ?
C5 C6 C12 128.01(13) . . ?
C4 C3 C2 119.81(13) . . ?
C4 C3 C9 118.23(13) . . ?
C2 C3 C9 121.94(13) . . ?
C5 C4 C3 120.25(13) . . ?
N1 C8 C7 107.31(12) . . ?
N1 C8 C16 122.30(12) . . ?
C7 C8 C16 130.39(13) . . ?
O6 C14 O5 124.74(14) . . ?
O6 C14 C7 110.36(12) . . ?
O5 C14 C7 124.90(14) . . ?
C2 C1 N1 119.68(13) . . ?
C1 C2 C3 120.68(14) . . ?
O1 C9 O2 124.23(14) . . ?
O1 C9 C3 123.74(14) . . ?
O2 C9 C3 112.02(12) . . ?
O7 C16 O8 123.71(14) . . ?
O7 C16 C8 125.56(14) . . ?
O8 C16 C8 110.73(12) . . ?
O3 C12 O4 123.54(13) . . ?
O3 C12 C6 123.89(14) . . ?
O4 C12 C6 112.56(12) . . ?
O2 C10 C11 107.43(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 1000659'
