# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_prophe
_database_code_depnum_ccdc_archive 'CCDC 1991811'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 N4 O7'
_chemical_formula_weight         366.33
_chemical_oxdiff_usercomment     'Joses (UW) JN_3-2PFI_A1-1-F33'

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   4.7625(2)
_cell_length_b                   13.0451(8)
_cell_length_c                   13.8262(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.126(5)
_cell_angle_gamma                90
_cell_volume                     855.55(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    130.0(1)
_cell_measurement_reflns_used    1313
_cell_measurement_theta_min      4.6330
_cell_measurement_theta_max      74.2030

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.508
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.977
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.83605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.752
_oxdiff_exptl_absorpt_empirical_full_max 1.424
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4959
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.669
_diffrn_reflns_theta_max         74.735
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.776
_diffrn_reflns_point_group_measured_fraction_full 0.814
_reflns_number_total             2723
_reflns_number_gt                2335
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.537
_reflns_Friedel_fraction_max     0.567
_reflns_Friedel_fraction_full    0.614

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0542P)²] 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 705 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2723
_refine_ls_number_parameters     239
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
C1 C 0.8720(9) 0.5595(5) 0.4117(3) 0.0543(14) Uani 1 1 d . . . . .
H1A H 1.065885 0.538508 0.427934 0.065 Uiso 1 1 calc R U . . .
H1B H 0.850152 0.583646 0.345131 0.065 Uiso 1 1 calc R U . . .
C2 C 0.6686(9) 0.4734(4) 0.4279(3) 0.0461(10) Uani 1 1 d . . . . .
H2A H 0.750255 0.407299 0.414788 0.055 Uiso 1 1 calc R U . . .
H2B H 0.493728 0.481613 0.386956 0.055 Uiso 1 1 calc R U . . .
C3 C 0.6199(11) 0.4842(3) 0.5358(3) 0.0465(10) Uani 1 1 d . . . . .
H3A H 0.763395 0.447268 0.576081 0.056 Uiso 1 1 calc R U . . .
H3B H 0.436315 0.457415 0.547993 0.056 Uiso 1 1 calc R U . . .
C4 C 0.6371(7) 0.5999(3) 0.5576(2) 0.0281(7) Uani 1 1 d . . . . .
H4 H 0.448838 0.630531 0.556041 0.034 Uiso 1 1 calc R U . . .
C5 C 0.8051(6) 0.6182(3) 0.6551(2) 0.0246(6) Uani 1 1 d . . . . .
C6 C 0.7871(6) 0.6318(3) 0.8304(2) 0.0252(7) Uani 1 1 d . . . . .
H6 H 0.636364 0.638873 0.873728 0.030 Uiso 1 1 calc R U . . .
C7 C 0.9658(7) 0.5384(3) 0.8647(3) 0.0284(7) Uani 1 1 d . . . . .
H7A H 1.117896 0.530303 0.823130 0.034 Uiso 1 1 calc R U . . .
H7B H 1.049478 0.550893 0.930213 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7979(7) 0.4406(3) 0.8636(3) 0.0281(7) Uani 1 1 d . . . . .
C9 C 0.8257(8) 0.3673(3) 0.7916(3) 0.0327(8) Uani 1 1 d . . . . .
H9 H 0.942676 0.380481 0.742639 0.039 Uiso 1 1 calc R U . . .
C10 C 0.6812(8) 0.2748(3) 0.7920(3) 0.0365(8) Uani 1 1 d . . . . .
H10 H 0.699528 0.225901 0.744097 0.044 Uiso 1 1 calc R U . . .
C11 C 0.5086(8) 0.2577(3) 0.8661(3) 0.0316(8) Uani 1 1 d . . . . .
C12 C 0.4721(8) 0.3297(3) 0.9376(3) 0.0338(8) Uani 1 1 d . . . . .
H12 H 0.352573 0.316786 0.985863 0.041 Uiso 1 1 calc R U . . .
C13 C 0.6188(8) 0.4214(3) 0.9354(3) 0.0307(7) Uani 1 1 d . . . . .
H13 H 0.596876 0.470771 0.982714 0.037 Uiso 1 1 calc R U . . .
C14 C 0.9671(7) 0.7286(3) 0.8407(3) 0.0280(7) Uani 1 1 d . . . . .
C15 C 0.9831(10) 0.9054(3) 0.8097(4) 0.0472(10) Uani 1 1 d . . . . .
H15A H 1.020914 0.922952 0.877031 0.071 Uiso 1 1 calc R U . . .
H15B H 0.871975 0.958544 0.776963 0.071 Uiso 1 1 calc R U . . .
H15C H 1.157819 0.898466 0.780665 0.071 Uiso 1 1 calc R U . . .
N1 N 0.7871(7) 0.6367(3) 0.4782(2) 0.0384(7) Uani 1 1 d . . . . .
N2 N 0.6543(5) 0.6210(2) 0.7318(2) 0.0237(5) Uani 1 1 d D . . . .
N3 N 0.8710(9) 0.7331(4) 0.4750(3) 0.0553(11) Uani 1 1 d . . . . .
N4 N 0.3638(8) 0.1592(3) 0.8704(3) 0.0455(9) Uani 1 1 d . . . . .
O1 O 1.0659(5) 0.6234(2) 0.66136(18) 0.0347(6) Uani 1 1 d . . . . .
O2 O 1.0238(13) 0.7566(5) 0.4105(3) 0.112(2) Uani 1 1 d . . . . .
O3 O 0.7884(8) 0.7933(2) 0.5357(3) 0.0618(10) Uani 1 1 d . . . . .
O4 O 0.8295(5) 0.8092(2) 0.8012(2) 0.0352(6) Uani 1 1 d . . . . .
O5 O 1.1988(5) 0.7326(2) 0.8831(2) 0.0387(6) Uani 1 1 d . . . . .
O6 O 0.4184(9) 0.0920(3) 0.8122(3) 0.0632(10) Uani 1 1 d . . . . .
O7 O 0.1975(8) 0.1466(3) 0.9330(3) 0.0580(9) Uani 1 1 d . . . . .
H2 H 0.484(4) 0.632(6) 0.725(5) 0.070 Uiso 1 1 d D U . . .


_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
C1 N1 1.444(6) . ?
C1 C2 1.513(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.537(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.540(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.444(4) . ?
C4 C5 1.524(5) . ?
C4 H4 0.9800 . ?
C5 O1 1.239(4) . ?
C5 N2 1.333(4) . ?
C6 N2 1.458(4) . ?
C6 C14 1.526(5) . ?
C6 C7 1.537(5) . ?
C6 H6 0.9800 . ?
C7 C8 1.505(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.388(5) . ?
C8 C9 1.395(5) . ?
C9 C10 1.389(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(6) . ?
C11 N4 1.461(5) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O5 1.203(5) . ?
C14 O4 1.330(5) . ?
C15 O4 1.452(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 N3 1.322(6) . ?
N2 H2 0.822(13) . ?
N3 O3 1.239(6) . ?
N3 O2 1.239(6) . ?
N4 O6 1.234(6) . ?
N4 O7 1.235(5) . ?

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 C1 C2 101.8(3) . . ?
N1 C1 H1A 111.4 . . ?
C2 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
C2 C1 H1B 111.4 . . ?
H1A C1 H1B 109.3 . . ?
C1 C2 C3 103.3(4) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 105.6(4) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
N1 C4 C5 111.4(3) . . ?
N1 C4 C3 101.4(3) . . ?
C5 C4 C3 109.9(3) . . ?
N1 C4 H4 111.2 . . ?
C5 C4 H4 111.2 . . ?
C3 C4 H4 111.2 . . ?
O1 C5 N2 123.4(3) . . ?
O1 C5 C4 120.9(3) . . ?
N2 C5 C4 115.5(3) . . ?
N2 C6 C14 111.2(3) . . ?
N2 C6 C7 113.2(3) . . ?
C14 C6 C7 109.6(3) . . ?
N2 C6 H6 107.5 . . ?
C14 C6 H6 107.5 . . ?
C7 C6 H6 107.5 . . ?
C8 C7 C6 112.9(3) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 119.4(3) . . ?
C13 C8 C7 120.3(3) . . ?
C9 C8 C7 120.3(3) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 118.1(4) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C12 C11 C10 122.5(3) . . ?
C12 C11 N4 118.4(3) . . ?
C10 C11 N4 119.0(4) . . ?
C11 C12 C13 118.2(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C8 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
O5 C14 O4 124.3(4) . . ?
O5 C14 C6 124.3(4) . . ?
O4 C14 C6 111.3(3) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 N1 C4 120.8(4) . . ?
N3 N1 C1 122.7(4) . . ?
C4 N1 C1 116.0(4) . . ?
C5 N2 C6 121.8(2) . . ?
C5 N2 H2 120(5) . . ?
C6 N2 H2 116(5) . . ?
O3 N3 O2 125.0(5) . . ?
O3 N3 N1 117.8(4) . . ?
O2 N3 N1 117.2(5) . . ?
O6 N4 O7 123.2(4) . . ?
O6 N4 C11 118.1(4) . . ?
O7 N4 C11 118.7(4) . . ?
C14 O4 C15 115.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -32.6(5) . . . . ?
C1 C2 C3 C4 33.2(5) . . . . ?
C2 C3 C4 N1 -19.7(4) . . . . ?
C2 C3 C4 C5 -137.6(3) . . . . ?
N1 C4 C5 O1 -26.8(5) . . . . ?
C3 C4 C5 O1 84.9(4) . . . . ?
N1 C4 C5 N2 157.6(3) . . . . ?
C3 C4 C5 N2 -90.8(4) . . . . ?
N2 C6 C7 C8 -59.3(4) . . . . ?
C14 C6 C7 C8 175.8(3) . . . . ?
C6 C7 C8 C13 -76.1(4) . . . . ?
C6 C7 C8 C9 105.4(4) . . . . ?
C13 C8 C9 C10 -1.3(5) . . . . ?
C7 C8 C9 C10 177.3(3) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C9 C10 C11 N4 -177.4(4) . . . . ?
C10 C11 C12 C13 -1.2(6) . . . . ?
N4 C11 C12 C13 177.5(3) . . . . ?
C11 C12 C13 C8 -0.2(5) . . . . ?
C9 C8 C13 C12 1.3(5) . . . . ?
C7 C8 C13 C12 -177.2(3) . . . . ?
N2 C6 C14 O5 -136.4(4) . . . . ?
C7 C6 C14 O5 -10.5(5) . . . . ?
N2 C6 C14 O4 46.7(4) . . . . ?
C7 C6 C14 O4 172.7(3) . . . . ?
C5 C4 N1 N3 -56.4(5) . . . . ?
C3 C4 N1 N3 -173.2(4) . . . . ?
C5 C4 N1 C1 115.2(4) . . . . ?
C3 C4 N1 C1 -1.6(4) . . . . ?
C2 C1 N1 N3 -166.3(4) . . . . ?
C2 C1 N1 C4 22.2(5) . . . . ?
O1 C5 N2 C6 0.8(5) . . . . ?
C4 C5 N2 C6 176.4(3) . . . . ?
C14 C6 N2 C5 57.0(4) . . . . ?
C7 C6 N2 C5 -67.0(4) . . . . ?
C4 N1 N3 O3 -8.4(6) . . . . ?
C1 N1 N3 O3 -179.4(4) . . . . ?
C4 N1 N3 O2 172.6(5) . . . . ?
C1 N1 N3 O2 1.5(7) . . . . ?
C12 C11 N4 O6 -173.1(4) . . . . ?
C10 C11 N4 O6 5.6(6) . . . . ?
C12 C11 N4 O7 5.5(6) . . . . ?
C10 C11 N4 O7 -175.8(4) . . . . ?
O5 C14 O4 C15 1.8(5) . . . . ?
C6 C14 O4 C15 178.7(3) . . . . ?

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
C1 H1B O6 0.97 2.43 3.304(7) 150.4 2_656
C3 H3B O3 0.97 2.62 3.258(6) 123.9 2_646
C4 H4 O1 0.98 2.44 3.202(4) 134.8 1_455
C6 H6 O5 0.98 2.43 3.236(4) 139.3 1_455
C7 H7A O1 0.97 2.54 3.099(4) 116.8 .
C7 H7B O7 0.97 2.63 3.287(5) 125.3 2_657
C10 H10 O2 0.93 2.64 3.252(6) 123.9 2_746
N2 H2 O1 0.822(13) 2.11(3) 2.883(3) 158(6) 1_455

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046

