# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
# 
#######################################################################

data_AB_B1_0008
_database_code_depnum_ccdc_archive 'CCDC 1528414'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-02-14 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2014/7

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Maria Tsanakopoulou'
_cambridge_user_email            mtsanak@mrc-lmb.cam.ac.uk
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_email adb29@cam.ac.uk
_cambridge_sample_id             MT-484
_cambridge_data_id               AB_B1_0008
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N4 O5, H2 O'
_chemical_formula_sum            'C10 H14 N4 O6'
_chemical_formula_weight         286.25
_chemical_absolute_configuration ad

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'

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

_cell_length_a                   7.4674(2)
_cell_length_b                   10.9703(3)
_cell_length_c                   13.9309(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1141.21(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9923
_cell_measurement_theta_min      4.03
_cell_measurement_theta_max      66.77

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.200
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6490
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13491
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.132
_diffrn_reflns_theta_max         66.780
_diffrn_reflns_theta_full        66.781
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1996
_reflns_number_gt                1920
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.987

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0370P)²+0.3485P] 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     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_extinction_coef       0.0047(7)
_refine_ls_abs_structure_Flack   -0.09(8)
_refine_ls_abs_structure_details 
;
Flack x determined using 773 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_number_reflns         1996
_refine_ls_number_parameters     210
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.037

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 0.5115(2) 0.95472(13) 0.25324(13) 0.0199(4) Uani 1 1 d . . . . .
O2 O 0.8020(2) 0.69995(14) 0.25944(11) 0.0187(4) Uani 1 1 d . . . . .
O3 O 0.4490(2) 0.81467(14) 0.13934(12) 0.0215(4) Uani 1 1 d . . . . .
O4 O 0.6826(2) 0.61960(13) 0.45202(13) 0.0204(4) Uani 1 1 d . . . . .
O5 O 0.9360(3) 0.53896(16) 0.11299(14) 0.0335(5) Uani 1 1 d . . . . .
H5 H 0.918(7) 0.483(4) 0.061(4) 0.085(15) Uiso 1 1 d . . . . .
N6 N 0.2107(3) 0.91743(18) 0.20397(17) 0.0234(5) Uani 1 1 d . . . . .
H61 H 0.227(4) 0.977(3) 0.161(2) 0.025(7) Uiso 1 1 d . . . . .
H62 H 0.166(4) 0.947(3) 0.253(3) 0.026(8) Uiso 1 1 d . . . . .
N7 N 0.5315(2) 0.73899(15) 0.34543(13) 0.0151(4) Uani 1 1 d . . . . .
N8 N 0.3804(3) 0.60797(16) 0.45495(14) 0.0191(4) Uani 1 1 d . . . . .
N9 N 0.0753(3) 0.59463(19) 0.45264(18) 0.0241(5) Uani 1 1 d . . . . .
H91 H 0.093(3) 0.545(2) 0.4973(19) 0.007(6) Uiso 1 1 d . . . . .
H92 H -0.030(4) 0.618(2) 0.430(2) 0.018(7) Uiso 1 1 d . . . . .
C10 C 0.3699(3) 0.77285(18) 0.30496(16) 0.0156(5) Uani 1 1 d . . . . .
C11 C 0.7040(3) 0.78765(19) 0.31203(17) 0.0170(5) Uani 1 1 d . . . . .
H11A H 0.7762 0.8182 0.3675 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5345(3) 0.65266(19) 0.41961(16) 0.0157(4) Uani 1 1 d . . . . .
C13 C 0.2242(3) 0.64177(19) 0.41586(17) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.6422(3) 0.81832(19) 0.14567(17) 0.0202(5) Uani 1 1 d . . . . .
H14A H 0.6977 0.8592 0.0888 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3784(3) 0.86749(19) 0.22540(17) 0.0179(5) Uani 1 1 d . . . . .
C16 C 0.6730(3) 0.89010(19) 0.23874(18) 0.0184(5) Uani 1 1 d . . . . .
H16A H 0.7784 0.9459 0.2339 0.022 Uiso 1 1 calc R U . . .
C17 C 0.7227(3) 0.69194(19) 0.16422(16) 0.0197(5) Uani 1 1 d . . . . .
H17A H 0.6256 0.6291 0.1640 0.024 Uiso 1 1 calc R U . . .
C18 C 0.2148(3) 0.7253(2) 0.33703(17) 0.0196(5) Uani 1 1 d . . . . .
H18A H 0.1035 0.7464 0.3085 0.023 Uiso 1 1 calc R U . . .
C19 C 0.8648(4) 0.6578(2) 0.0929(2) 0.0303(6) Uani 1 1 d . . . . .
H19A H 0.8132 0.6586 0.0274 0.036 Uiso 1 1 calc R U . . .
H19B H 0.9626 0.7186 0.0951 0.036 Uiso 1 1 calc R U . . .
O1W O 0.1981(3) 0.41073(19) 0.57705(17) 0.0405(5) Uani 1 1 d D . . . .
H1W H 0.311(3) 0.440(4) 0.590(4) 0.089(16) Uiso 1 1 d D . . . .
H2W H 0.170(5) 0.337(2) 0.605(3) 0.063(12) Uiso 1 1 d 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
O1 C16 1.413(3) . ?
O1 C15 1.433(3) . ?
O2 C11 1.413(3) . ?
O2 C17 1.455(3) . ?
O3 C15 1.432(3) . ?
O3 C14 1.446(3) . ?
O4 C12 1.248(3) . ?
O5 C19 1.435(3) . ?
O5 H5 0.96(5) . ?
N6 C15 1.399(3) . ?
N6 H61 0.90(3) . ?
N6 H62 0.83(3) . ?
N7 C10 1.383(3) . ?
N7 C12 1.402(3) . ?
N7 C11 1.470(3) . ?
N8 C13 1.340(3) . ?
N8 C12 1.345(3) . ?
N9 C13 1.329(3) . ?
N9 H91 0.84(3) . ?
N9 H92 0.88(3) . ?
C10 C18 1.347(3) . ?
C10 C15 1.520(3) . ?
C11 C16 1.536(3) . ?
C11 H11A 1.0000 . ?
C13 C18 1.432(3) . ?
C14 C17 1.533(3) . ?
C14 C16 1.534(3) . ?
C14 H14A 1.0000 . ?
C16 H16A 1.0000 . ?
C17 C19 1.501(3) . ?
C17 H17A 1.0000 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
O1W H1W 0.922(14) . ?
O1W H2W 0.920(14) . ?

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
C16 O1 C15 102.60(15) . . ?
C11 O2 C17 107.65(16) . . ?
C15 O3 C14 107.77(17) . . ?
C19 O5 H5 112(3) . . ?
C15 N6 H61 107.9(18) . . ?
C15 N6 H62 110(2) . . ?
H61 N6 H62 109(3) . . ?
C10 N7 C12 119.74(18) . . ?
C10 N7 C11 122.56(17) . . ?
C12 N7 C11 117.69(18) . . ?
C13 N8 C12 119.72(19) . . ?
C13 N9 H91 114.1(17) . . ?
C13 N9 H92 120.0(17) . . ?
H91 N9 H92 126(2) . . ?
C18 C10 N7 120.76(19) . . ?
C18 C10 C15 122.8(2) . . ?
N7 C10 C15 116.39(19) . . ?
O2 C11 N7 111.74(17) . . ?
O2 C11 C16 103.39(18) . . ?
N7 C11 C16 110.12(17) . . ?
O2 C11 H11A 110.5 . . ?
N7 C11 H11A 110.5 . . ?
C16 C11 H11A 110.5 . . ?
O4 C12 N8 121.3(2) . . ?
O4 C12 N7 118.5(2) . . ?
N8 C12 N7 120.2(2) . . ?
N9 C13 N8 117.6(2) . . ?
N9 C13 C18 120.3(2) . . ?
N8 C13 C18 122.1(2) . . ?
O3 C14 C17 112.11(18) . . ?
O3 C14 C16 102.41(18) . . ?
C17 C14 C16 105.25(19) . . ?
O3 C14 H14A 112.2 . . ?
C17 C14 H14A 112.2 . . ?
C16 C14 H14A 112.2 . . ?
N6 C15 O3 108.02(19) . . ?
N6 C15 O1 114.65(18) . . ?
O3 C15 O1 103.96(17) . . ?
N6 C15 C10 112.7(2) . . ?
O3 C15 C10 110.44(17) . . ?
O1 C15 C10 106.71(18) . . ?
O1 C16 C14 104.52(18) . . ?
O1 C16 C11 113.63(18) . . ?
C14 C16 C11 102.05(17) . . ?
O1 C16 H16A 112.0 . . ?
C14 C16 H16A 112.0 . . ?
C11 C16 H16A 112.0 . . ?
O2 C17 C19 109.3(2) . . ?
O2 C17 C14 104.98(17) . . ?
C19 C17 C14 113.03(19) . . ?
O2 C17 H17A 109.8 . . ?
C19 C17 H17A 109.8 . . ?
C14 C17 H17A 109.8 . . ?
C10 C18 C13 117.4(2) . . ?
C10 C18 H18A 121.3 . . ?
C13 C18 H18A 121.3 . . ?
O5 C19 C17 111.1(2) . . ?
O5 C19 H19A 109.4 . . ?
C17 C19 H19A 109.4 . . ?
O5 C19 H19B 109.4 . . ?
C17 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
H1W O1W H2W 115(4) . . ?

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
O5 H5 O4 0.96(5) 2.03(5) 2.973(3) 166(4) 2_664
O5 H5 N8 0.96(5) 2.34(5) 3.054(3) 131(4) 2_664
N6 H61 O4 0.90(3) 2.32(3) 3.206(3) 171(2) 3_655
N6 H62 O5 0.83(3) 2.25(4) 3.079(3) 175(3) 3_655
N9 H91 O1W 0.84(3) 2.01(3) 2.813(3) 162(2) .
N9 H92 O4 0.88(3) 2.17(3) 2.945(3) 147(2) 1_455
O1W H1W O5 0.922(14) 1.927(18) 2.832(3) 167(4) 2_665
O1W H2W O3 0.920(14) 1.949(18) 2.841(3) 163(4) 2_565



