# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1569990'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N2 O8'
_chemical_formula_weight         428.39

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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.7697(4)
_cell_length_b                   4.89380(10)
_cell_length_c                   22.9053(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.860(2)
_cell_angle_gamma                90
_cell_volume                     2101.35(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4891
_cell_measurement_theta_min      4.9890
_cell_measurement_theta_max      70.9990

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.890
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_T_min  0.67115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            8010
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.865
_diffrn_reflns_theta_max         71.361
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.935
_reflns_number_total             3710
_reflns_number_gt                3531
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_max     0.831
_reflns_Friedel_fraction_full    0.858

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0802P)²+0.5587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1352 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3710
_refine_ls_number_parameters     291
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.041
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.28225(10) 0.2204(5) 0.65346(9) 0.0559(5) Uani 1 1 d . . . . .
O3 O 0.47827(9) 0.5893(5) 0.60288(9) 0.0549(5) Uani 1 1 d . . . . .
H3 H 0.5097 0.5144 0.6232 0.082 Uiso 1 1 calc R U . . .
O4 O 0.42829(11) 0.0860(5) 0.65212(9) 0.0627(6) Uani 1 1 d . . . . .
H4 H 0.4446 -0.0592 0.6409 0.094 Uiso 1 1 calc R U . . .
O1 O 0.09779(11) 0.8120(7) 0.63371(10) 0.0758(8) Uani 1 1 d . . . . .
N1 N 0.22543(12) 0.3640(6) 0.67788(11) 0.0539(6) Uani 1 1 d . . . . .
N2 N 0.13715(12) 0.7782(6) 0.72792(11) 0.0609(7) Uani 1 1 d . . . . .
O6 O 0.23228(13) 0.5123(8) 0.86023(11) 0.0968(12) Uani 1 1 d . . . . .
C9 C 0.33381(12) 0.3977(6) 0.62815(11) 0.0415(5) Uani 1 1 d . . . . .
H9 H 0.3547 0.5198 0.6583 0.050 Uiso 1 1 calc R U . . .
C2 C 0.20483(12) 0.5768(7) 0.64901(11) 0.0464(6) Uani 1 1 d . . . . .
C1 C 0.14257(13) 0.7342(7) 0.67081(13) 0.0531(7) Uani 1 1 d . . . . .
C4 C 0.29650(12) 0.5633(6) 0.58086(10) 0.0425(5) Uani 1 1 d . . . . .
C3 C 0.23199(13) 0.6543(6) 0.59354(11) 0.0475(6) Uani 1 1 d . . . . .
H3A H 0.2054 0.7641 0.5674 0.057 Uiso 1 1 calc R U . . .
C8 C 0.39130(13) 0.2181(6) 0.60482(12) 0.0461(6) Uani 1 1 d . . . . .
H8 H 0.3686 0.0786 0.5795 0.055 Uiso 1 1 calc R U . . .
C7 C 0.44037(13) 0.3897(6) 0.56848(12) 0.0492(6) Uani 1 1 d . . . . .
H7 H 0.4749 0.2685 0.5508 0.059 Uiso 1 1 calc R U . . .
O5 O 0.12113(15) 0.4588(10) 0.82756(14) 0.1098(14) Uani 1 1 d . . . . .
C2' C 0.19402(14) 0.7310(8) 0.77073(13) 0.0562(7) Uani 1 1 d . . . . .
C4' C 0.31646(15) 0.7631(8) 0.80656(12) 0.0595(8) Uani 1 1 d . . . . .
C5 C 0.33217(14) 0.6191(7) 0.52767(11) 0.0477(6) Uani 1 1 d . . . . .
H5 H 0.3078 0.7132 0.4976 0.057 Uiso 1 1 calc R U . . .
C6 C 0.39914(15) 0.5389(7) 0.52074(12) 0.0539(7) Uani 1 1 d . . . . .
H6 H 0.4205 0.5762 0.4858 0.065 Uiso 1 1 calc R U . . .
C3' C 0.25982(15) 0.8339(7) 0.76582(14) 0.0581(7) Uani 1 1 d . . . . .
H12 H 0.2684 0.9532 0.7354 0.070 Uiso 1 1 calc R U . . .
C1' C 0.17785(17) 0.5591(11) 0.81944(15) 0.0761(11) Uani 1 1 d . . . . .
C9' C 0.30083(17) 0.6014(10) 0.85349(14) 0.0720(10) Uani 1 1 d . . . . .
C5' C 0.38740(17) 0.8460(11) 0.80133(15) 0.0758(11) Uani 1 1 d . . . . .
H16 H 0.3991 0.9543 0.7698 0.091 Uiso 1 1 calc R U . . .
O8 O 0.46984(17) 0.5333(15) 0.93196(14) 0.160(3) Uani 1 1 d . . . . .
C6' C 0.43972(18) 0.7698(13) 0.84191(15) 0.0865(14) Uani 1 1 d . . . . .
H17 H 0.4866 0.8262 0.8380 0.104 Uiso 1 1 calc R U . . .
C8' C 0.3522(2) 0.5256(13) 0.89574(17) 0.1024(19) Uani 1 1 d D . . . .
C7' C 0.4224(2) 0.6076(15) 0.88904(15) 0.0984(17) Uani 1 1 d . . . . .
C10' C 0.07270(19) 0.9196(12) 0.74598(19) 0.0907(14) Uani 1 1 d . . . . .
H10A H 0.0749 1.1088 0.7351 0.136 Uiso 1 1 calc R U . . .
H10B H 0.0698 0.9052 0.7876 0.136 Uiso 1 1 calc R U . . .
H10C H 0.0313 0.8371 0.7270 0.136 Uiso 1 1 calc R U . . .
C12' C 0.5421(3) 0.617(3) 0.9283(3) 0.201(6) Uani 1 1 d . . . . .
H20A H 0.5583 0.5711 0.8904 0.302 Uiso 1 1 calc R U . . .
H20B H 0.5712 0.5246 0.9578 0.302 Uiso 1 1 calc R U . . .
H20C H 0.5456 0.8105 0.9341 0.302 Uiso 1 1 calc R U . . .
O7 O 0.3306(2) 0.4535(12) 0.95054(16) 0.0878(13) Uani 0.709(6) 1 d . . P A 2
C11' C 0.3260(11) 0.182(3) 0.9548(6) 0.180(6) Uani 0.709(6) 1 d . . P A 2
H11A H 0.3111 0.1339 0.9930 0.270 Uiso 0.709(6) 1 calc R U P A 2
H11B H 0.3718 0.1022 0.9489 0.270 Uiso 0.709(6) 1 calc R U P A 2
H11C H 0.2919 0.1147 0.9257 0.270 Uiso 0.709(6) 1 calc R U P A 2
O7' O 0.3478(6) 0.2687(15) 0.9248(4) 0.0878(13) Uani 0.291(6) 1 d D . P A 1
C11 C 0.310(3) 0.326(8) 0.9734(17) 0.180(6) Uani 0.291(6) 1 d . . P A 1
H11D H 0.3048 0.1614 0.9956 0.270 Uiso 0.291(6) 1 calc R U P A 1
H11E H 0.2643 0.3971 0.9615 0.270 Uiso 0.291(6) 1 calc R U P A 1
H11F H 0.3361 0.4584 0.9971 0.270 Uiso 0.291(6) 1 calc R U P A 1


_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 N1 1.415(3) . ?
O2 C9 1.443(3) . ?
O3 C7 1.423(4) . ?
O3 H3 0.8200 . ?
O4 C8 1.414(3) . ?
O4 H4 0.8200 . ?
O1 C1 1.226(4) . ?
N1 C2 1.283(4) . ?
N2 C1 1.335(4) . ?
N2 C2' 1.432(4) . ?
N2 C10' 1.471(4) . ?
O6 C1' 1.369(4) . ?
O6 C9' 1.375(4) . ?
C9 C4 1.498(3) . ?
C9 C8 1.510(3) . ?
C9 H9 0.9800 . ?
C2 C3 1.443(4) . ?
C2 C1 1.506(3) . ?
C4 C3 1.336(3) . ?
C4 C5 1.445(4) . ?
C3 H3A 0.9300 . ?
C8 C7 1.524(4) . ?
C8 H8 0.9800 . ?
C7 C6 1.498(4) . ?
C7 H7 0.9800 . ?
O5 C1' 1.195(4) . ?
C2' C3' 1.344(4) . ?
C2' C1' 1.442(5) . ?
C4' C9' 1.378(5) . ?
C4' C5' 1.403(4) . ?
C4' C3' 1.422(4) . ?
C5 C6 1.334(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C3' H12 0.9300 . ?
C9' C8' 1.382(5) . ?
C5' C6' 1.370(5) . ?
C5' H16 0.9300 . ?
O8 C7' 1.343(5) . ?
O8 C12' 1.423(7) . ?
C6' C7' 1.391(6) . ?
C6' H17 0.9300 . ?
C8' O7 1.384(5) . ?
C8' C7' 1.395(6) . ?
C8' O7' 1.427(3) . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
C12' H20A 0.9600 . ?
C12' H20B 0.9600 . ?
C12' H20C 0.9600 . ?
O7 C11' 1.335(15) . ?
C11' H11A 0.9600 . ?
C11' H11B 0.9600 . ?
C11' H11C 0.9600 . ?
O7' C11 1.37(5) . ?
C11 H11D 0.9600 . ?
C11 H11E 0.9600 . ?
C11 H11F 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
N1 O2 C9 113.2(2) . . ?
C7 O3 H3 109.5 . . ?
C8 O4 H4 109.5 . . ?
C2 N1 O2 114.4(2) . . ?
C1 N2 C2' 123.7(2) . . ?
C1 N2 C10' 117.1(3) . . ?
C2' N2 C10' 118.6(3) . . ?
C1' O6 C9' 122.8(3) . . ?
O2 C9 C4 108.5(2) . . ?
O2 C9 C8 107.3(2) . . ?
C4 C9 C8 112.1(2) . . ?
O2 C9 H9 109.6 . . ?
C4 C9 H9 109.6 . . ?
C8 C9 H9 109.6 . . ?
N1 C2 C3 123.8(2) . . ?
N1 C2 C1 117.6(2) . . ?
C3 C2 C1 118.2(2) . . ?
O1 C1 N2 123.1(3) . . ?
O1 C1 C2 116.5(3) . . ?
N2 C1 C2 120.4(2) . . ?
C3 C4 C5 125.7(2) . . ?
C3 C4 C9 114.8(2) . . ?
C5 C4 C9 119.5(2) . . ?
C4 C3 C2 117.9(2) . . ?
C4 C3 H3A 121.1 . . ?
C2 C3 H3A 121.1 . . ?
O4 C8 C9 109.1(2) . . ?
O4 C8 C7 112.5(2) . . ?
C9 C8 C7 109.6(2) . . ?
O4 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
O3 C7 C6 107.2(2) . . ?
O3 C7 C8 112.0(2) . . ?
C6 C7 C8 111.3(2) . . ?
O3 C7 H7 108.8 . . ?
C6 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C3' C2' N2 122.6(3) . . ?
C3' C2' C1' 120.9(3) . . ?
N2 C2' C1' 116.5(3) . . ?
C9' C4' C5' 118.2(3) . . ?
C9' C4' C3' 118.1(3) . . ?
C5' C4' C3' 123.7(3) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2' C3' C4' 120.9(3) . . ?
C2' C3' H12 119.5 . . ?
C4' C3' H12 119.5 . . ?
O5 C1' O6 117.7(3) . . ?
O5 C1' C2' 125.7(3) . . ?
O6 C1' C2' 116.6(3) . . ?
O6 C9' C4' 120.4(3) . . ?
O6 C9' C8' 117.4(3) . . ?
C4' C9' C8' 122.2(3) . . ?
C6' C5' C4' 121.0(3) . . ?
C6' C5' H16 119.5 . . ?
C4' C5' H16 119.5 . . ?
C7' O8 C12' 118.5(5) . . ?
C5' C6' C7' 119.7(3) . . ?
C5' C6' H17 120.2 . . ?
C7' C6' H17 120.2 . . ?
C9' C8' O7 118.6(4) . . ?
C9' C8' C7' 118.4(3) . . ?
O7 C8' C7' 119.6(4) . . ?
C9' C8' O7' 120.6(6) . . ?
C7' C8' O7' 112.4(6) . . ?
O8 C7' C6' 123.4(4) . . ?
O8 C7' C8' 115.9(4) . . ?
C6' C7' C8' 120.5(3) . . ?
N2 C10' H10A 109.5 . . ?
N2 C10' H10B 109.5 . . ?
H10A C10' H10B 109.5 . . ?
N2 C10' H10C 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
O8 C12' H20A 109.5 . . ?
O8 C12' H20B 109.5 . . ?
H20A C12' H20B 109.5 . . ?
O8 C12' H20C 109.5 . . ?
H20A C12' H20C 109.5 . . ?
H20B C12' H20C 109.5 . . ?
C11' O7 C8' 110.1(8) . . ?
O7 C11' H11A 109.5 . . ?
O7 C11' H11B 109.5 . . ?
H11A C11' H11B 109.5 . . ?
O7 C11' H11C 109.5 . . ?
H11A C11' H11C 109.5 . . ?
H11B C11' H11C 109.5 . . ?
C11 O7' C8' 104.0(17) . . ?
O7' C11 H11D 109.5 . . ?
O7' C11 H11E 109.5 . . ?
H11D C11 H11E 109.5 . . ?
O7' C11 H11F 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 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
O3 H3 O1 0.82 1.93 2.686(3) 152.6 3_545
O4 H4 O3 0.82 2.04 2.858(3) 172.6 1_545

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

