# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1861590'
_audit_update_record             
;
2018-08-26 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N4 O10, 2(H2 O)'
_chemical_formula_sum            'C19 H24 N4 O12'
_chemical_formula_weight         500.42

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_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.9557(8)
_cell_length_b                   7.4897(8)
_cell_length_c                   41.571(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2165.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6931
_cell_measurement_theta_min      6.00
_cell_measurement_theta_max      68.40

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.120
_shelx_estimated_absorpt_T_min   0.759
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6540
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8332
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         6.003
_diffrn_reflns_theta_max         68.395
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             3742
_reflns_number_gt                3457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_max     0.902
_reflns_Friedel_fraction_full    0.910

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0573P)²+0.4318P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3742
_refine_ls_number_parameters     344
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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_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
O1 O 0.5556(3) 0.2695(3) 0.37170(5) 0.0287(5) Uani 1 1 d D . . . .
H1O H 0.554(5) 0.255(5) 0.3918(3) 0.043 Uiso 1 1 d D U . . .
O2 O 0.4011(3) 0.6788(3) 0.41196(5) 0.0298(5) Uani 1 1 d D . . . .
H2O H 0.451(5) 0.742(4) 0.3976(7) 0.045 Uiso 1 1 d D U . . .
O3 O 0.6697(3) 0.4962(3) 0.41957(4) 0.0248(5) Uani 1 1 d . . . . .
O4 O 0.2028(3) 0.3120(3) 0.41988(5) 0.0300(5) Uani 1 1 d . . . . .
O5 O 0.2854(3) 0.3819(3) 0.52454(5) 0.0266(5) Uani 1 1 d . . . . .
O6 O 0.4785(3) 0.5192(3) 0.55945(4) 0.0225(4) Uani 1 1 d . . . . .
O7 O 0.0912(3) 0.6216(3) 0.63311(5) 0.0236(5) Uani 1 1 d . . . . .
O8 O 0.7690(3) 0.3736(3) 0.66517(5) 0.0287(5) Uani 1 1 d . . . . .
O9 O 0.3028(3) 0.5130(4) 0.75090(5) 0.0386(6) Uani 1 1 d . . . . .
O10 O 0.5360(3) 0.9125(3) 0.69188(5) 0.0327(5) Uani 1 1 d D . . . .
H10O H 0.588(5) 0.935(6) 0.7096(6) 0.049 Uiso 1 1 d D U . . .
O1W O 0.8031(4) 0.2901(4) 0.31948(6) 0.0450(6) Uani 1 1 d D . . . .
H1W1 H 0.748(6) 0.296(7) 0.3379(6) 0.068 Uiso 1 1 d D U . . .
H1W2 H 0.879(5) 0.378(4) 0.3177(11) 0.068 Uiso 1 1 d D U . . .
O2W O 0.5121(3) 0.5143(4) 0.29173(7) 0.0502(7) Uani 1 1 d D . . . .
H2W1 H 0.431(5) 0.480(7) 0.2776(9) 0.075 Uiso 1 1 d D U . . .
H2W2 H 0.571(6) 0.425(4) 0.3003(11) 0.075 Uiso 1 1 d D U . . .
N1 N 0.3871(3) 0.3948(3) 0.46189(6) 0.0221(5) Uani 1 1 d D . . . .
H1 H 0.309(4) 0.347(4) 0.4764(6) 0.026 Uiso 1 1 d D U . . .
N2 N 0.5723(3) 0.4679(3) 0.62508(5) 0.0242(5) Uani 1 1 d D . . . .
H2 H 0.620(4) 0.392(4) 0.6111(6) 0.029 Uiso 1 1 d D U . . .
N3 N 0.3301(3) 0.6133(3) 0.66913(5) 0.0189(5) Uani 1 1 d . . . . .
N4 N 0.5254(3) 0.5432(4) 0.71083(5) 0.0223(5) Uani 1 1 d . . . . .
C1 C 0.4744(4) 0.4434(4) 0.37434(7) 0.0273(7) Uani 1 1 d . . . . .
H1A H 0.3410 0.4420 0.3660 0.033 Uiso 1 1 calc R U . . .
H1B H 0.5499 0.5284 0.3612 0.033 Uiso 1 1 calc R U . . .
C2 C 0.4741(4) 0.5039(4) 0.40892(7) 0.0246(6) Uani 1 1 d . . . . .
C3 C 0.3430(4) 0.3895(4) 0.43047(7) 0.0219(6) Uani 1 1 d . . . . .
C4 C 0.5573(4) 0.4690(4) 0.47395(6) 0.0192(6) Uani 1 1 d . . . . .
C5 C 0.7000(4) 0.5170(4) 0.45198(6) 0.0208(6) Uani 1 1 d . . . . .
C6 C 0.8769(4) 0.5746(4) 0.46227(7) 0.0232(6) Uani 1 1 d . . . . .
H6 H 0.9739 0.6037 0.4470 0.028 Uiso 1 1 calc R U . . .
C7 C 0.9140(4) 0.5904(4) 0.49499(7) 0.0249(6) Uani 1 1 d . . . . .
H7 H 1.0370 0.6283 0.5022 0.030 Uiso 1 1 calc R U . . .
C8 C 0.7724(4) 0.5509(4) 0.51688(7) 0.0228(6) Uani 1 1 d . . . . .
H8 H 0.7974 0.5650 0.5392 0.027 Uiso 1 1 calc R U . . .
C9 C 0.5922(4) 0.4905(4) 0.50684(6) 0.0191(6) Uani 1 1 d . . . . .
C10 C 0.4369(4) 0.4542(4) 0.53025(6) 0.0195(6) Uani 1 1 d . . . . .
C11 C 0.3297(4) 0.4995(4) 0.58336(6) 0.0246(6) Uani 1 1 d . . . . .
H11A H 0.2984 0.3720 0.5868 0.030 Uiso 1 1 calc R U . . .
H11B H 0.2115 0.5635 0.5768 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4148(4) 0.5810(4) 0.61319(7) 0.0219(6) Uani 1 1 d . . . . .
H12 H 0.4690 0.7005 0.6075 0.026 Uiso 1 1 calc R U . . .
C13 C 0.2631(4) 0.6069(4) 0.63919(6) 0.0183(6) Uani 1 1 d . . . . .
C14 C 0.2073(4) 0.6020(4) 0.69733(6) 0.0223(6) Uani 1 1 d . . . . .
H14A H 0.1044 0.5121 0.6944 0.027 Uiso 1 1 calc R U . . .
H14B H 0.1485 0.7190 0.7024 0.027 Uiso 1 1 calc R U . . .
C15 C 0.3455(4) 0.5462(4) 0.72264(7) 0.0256(7) Uani 1 1 d . . . . .
C16 C 0.5357(4) 0.6007(4) 0.67749(6) 0.0197(6) Uani 1 1 d . . . . .
C17 C 0.6362(4) 0.4663(4) 0.65531(7) 0.0208(6) Uani 1 1 d . . . . .
C18 C 0.6359(4) 0.7821(4) 0.67419(7) 0.0249(6) Uani 1 1 d . . . . .
H18A H 0.7696 0.7730 0.6822 0.030 Uiso 1 1 calc R U . . .
H18B H 0.6406 0.8171 0.6512 0.030 Uiso 1 1 calc R U . . .
C19 C 0.6939(4) 0.5155(5) 0.73111(7) 0.0337(8) Uani 1 1 d . . . . .
H19A H 0.6586 0.5335 0.7537 0.051 Uiso 1 1 calc R U . . .
H19B H 0.7944 0.6009 0.7251 0.051 Uiso 1 1 calc R U . . .
H19C H 0.7418 0.3936 0.7281 0.051 Uiso 1 1 calc R U . . .


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 C1 1.425(4) . ?
O2 C2 1.410(4) . ?
O3 C5 1.373(3) . ?
O3 C2 1.432(3) . ?
O4 C3 1.217(3) . ?
O5 C10 1.208(3) . ?
O6 C10 1.339(3) . ?
O6 C11 1.443(3) . ?
O7 C13 1.227(3) . ?
O8 C17 1.226(3) . ?
O9 C15 1.237(3) . ?
O10 C18 1.407(4) . ?
N1 C3 1.342(4) . ?
N1 C4 1.401(3) . ?
N2 C17 1.333(4) . ?
N2 C12 1.470(4) . ?
N3 C13 1.330(3) . ?
N3 C14 1.453(3) . ?
N3 C16 1.475(3) . ?
N4 C15 1.345(3) . ?
N4 C16 1.453(3) . ?
N4 C19 1.458(3) . ?
C1 C2 1.507(4) . ?
C2 C3 1.539(4) . ?
C4 C5 1.396(4) . ?
C4 C9 1.398(4) . ?
C5 C6 1.373(4) . ?
C6 C7 1.389(4) . ?
C7 C8 1.373(4) . ?
C8 C9 1.397(4) . ?
C9 C10 1.479(4) . ?
C11 C12 1.504(4) . ?
C12 C13 1.523(4) . ?
C14 C15 1.485(4) . ?
C16 C18 1.533(4) . ?
C16 C17 1.533(4) . ?

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
C5 O3 C2 116.4(2) . . ?
C10 O6 C11 115.6(2) . . ?
C3 N1 C4 123.6(2) . . ?
C17 N2 C12 124.8(2) . . ?
C13 N3 C14 123.2(2) . . ?
C13 N3 C16 123.9(2) . . ?
C14 N3 C16 112.1(2) . . ?
C15 N4 C16 112.9(2) . . ?
C15 N4 C19 122.6(2) . . ?
C16 N4 C19 123.6(2) . . ?
O1 C1 C2 110.4(2) . . ?
O2 C2 O3 110.6(2) . . ?
O2 C2 C1 111.4(2) . . ?
O3 C2 C1 106.3(2) . . ?
O2 C2 C3 104.6(2) . . ?
O3 C2 C3 111.1(2) . . ?
C1 C2 C3 112.9(2) . . ?
O4 C3 N1 123.3(3) . . ?
O4 C3 C2 122.0(3) . . ?
N1 C3 C2 114.5(2) . . ?
C5 C4 C9 119.1(2) . . ?
C5 C4 N1 118.0(2) . . ?
C9 C4 N1 122.8(2) . . ?
C6 C5 O3 118.6(2) . . ?
C6 C5 C4 121.0(3) . . ?
O3 C5 C4 120.3(2) . . ?
C5 C6 C7 119.9(3) . . ?
C8 C7 C6 119.8(3) . . ?
C7 C8 C9 121.0(3) . . ?
C8 C9 C4 119.0(2) . . ?
C8 C9 C10 121.2(2) . . ?
C4 C9 C10 119.7(2) . . ?
O5 C10 O6 122.0(2) . . ?
O5 C10 C9 126.1(2) . . ?
O6 C10 C9 111.8(2) . . ?
O6 C11 C12 104.1(2) . . ?
N2 C12 C11 109.7(2) . . ?
N2 C12 C13 110.5(2) . . ?
C11 C12 C13 111.3(2) . . ?
O7 C13 N3 122.1(2) . . ?
O7 C13 C12 122.7(3) . . ?
N3 C13 C12 115.2(2) . . ?
N3 C14 C15 102.0(2) . . ?
O9 C15 N4 124.5(3) . . ?
O9 C15 C14 125.1(3) . . ?
N4 C15 C14 110.4(2) . . ?
N4 C16 N3 101.3(2) . . ?
N4 C16 C18 111.7(2) . . ?
N3 C16 C18 111.3(2) . . ?
N4 C16 C17 113.7(2) . . ?
N3 C16 C17 110.0(2) . . ?
C18 C16 C17 108.7(2) . . ?
O8 C17 N2 124.8(3) . . ?
O8 C17 C16 120.9(2) . . ?
N2 C17 C16 114.1(2) . . ?
O10 C18 C16 110.1(2) . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055

