# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_pan11_2_5_2019_3_tw
_database_code_depnum_ccdc_archive 'CCDC 1923238'
loop_
_audit_author_name
_audit_author_address
'Adi Azoulay'
;Ben Gurion university of the Negev
Israel
;
_audit_update_record             
;
2019-06-16 deposited with the CCDC.	2020-04-16 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(H2 O4 P), C3 H8 N6'
_chemical_formula_sum            'C3 H12 N6 O8 P2'
_chemical_formula_weight         322.13
_chemical_melting_point          ?
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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   4.57630(10)
_cell_length_b                   8.0571(2)
_cell_length_c                   16.5465(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.331(2)
_cell_angle_gamma                90
_cell_volume                     607.46(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1918
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.1090
_cell_measurement_theta_min      5.298
_shelx_estimated_absorpt_T_max   0.703
_shelx_estimated_absorpt_T_min   0.703
_exptl_absorpt_coefficient_mu    3.789
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1113
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.368
_diffrn_reflns_theta_min         5.370
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_detector_type            HyPix
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1034
_reflns_number_total             1113
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1113
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0854P)²+0.1209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.774(4)
 0.226(4)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
3. Restrained distances
 H4-P1
 2.2 with sigma of 0.001
4. Others
 Fixed Sof: H1A(0.5) H1B(0.5) O3(0.8) O4(0.8) O5(0.2) O3A(0.2)
5.a Aromatic/amide H refined with riding coordinates:
 N2(H2)
5.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
P1 P 0.37085(13) 0.70107(8) 0.56180(4) 0.0421(3) Uani 1 1 d D . . . .
O1 O 0.4902(4) 0.5425(2) 0.60142(10) 0.0446(5) Uani 1 1 d . . . . .
O2 O 0.1518(4) 0.7874(2) 0.60910(11) 0.0467(5) Uani 1 1 d . . . . .
N1 N 0.000000 0.6296(4) 0.750000 0.0462(7) Uani 1 2 d S T P . .
H1A H -0.088958 0.682990 0.785476 0.055 Uiso 0.5 1 calc R . . . .
H1B H 0.088958 0.682990 0.714524 0.055 Uiso 0.5 1 calc R . . . .
N2 N 0.1376(5) 0.3814(3) 0.69512(12) 0.0440(5) Uani 1 1 d . . . . .
H2 H 0.232084 0.432632 0.660106 0.053 Uiso 1 1 calc R . . . .
O3 O 0.1940(8) 0.6589(6) 0.4770(3) 0.0551(9) Uani 0.8 1 d . . . A 1
N3 N 0.000000 0.1255(4) 0.750000 0.0457(7) Uani 1 2 d S T P . .
N4 N 0.2593(6) 0.1346(3) 0.63868(14) 0.0523(6) Uani 1 1 d . . . . .
H4A H 0.262577 0.027926 0.637643 0.063 Uiso 1 1 calc R . . . .
H4B H 0.342340 0.190494 0.602878 0.063 Uiso 1 1 calc R . . . .
C1 C 0.000000 0.4696(4) 0.750000 0.0402(7) Uani 1 2 d S T P . .
C2 C 0.1283(6) 0.2119(3) 0.69467(16) 0.0431(6) Uani 1 1 d . . . . .
O4 O 0.6179(7) 0.8131(5) 0.5387(2) 0.0572(9) Uani 0.8 1 d . . . A 1
O5 O 0.626(3) 0.8495(15) 0.5792(11) 0.053(3) Uani 0.2 1 d . . . A 2
O3A O 0.313(4) 0.6974(19) 0.4740(11) 0.053(4) Uani 0.2 1 d . . . A 2
H3 H 0.287(9) 0.596(5) 0.451(2) 0.057(9) Uiso 1 1 d . . . . .
H4 H 0.803(5) 0.822(5) 0.568(4) 0.13(2) Uiso 1 1 d D . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0377(4) 0.0437(4) 0.0458(4) 0.0025(2) 0.0083(3) 0.0042(2)
O1 0.0435(8) 0.0438(10) 0.0470(9) 0.0010(7) 0.0068(7) 0.0037(7)
O2 0.0473(10) 0.0445(9) 0.0496(10) -0.0006(7) 0.0120(8) 0.0029(7)
N1 0.0557(17) 0.0404(16) 0.0433(14) 0.000 0.0098(12) 0.000
N2 0.0506(11) 0.0412(11) 0.0414(10) 0.0034(8) 0.0102(9) 0.0011(9)
O3 0.0509(19) 0.063(2) 0.0502(16) -0.0079(16) -0.0016(17) 0.0175(17)
N3 0.0531(16) 0.0410(16) 0.0439(14) 0.000 0.0083(12) 0.000
N4 0.0662(13) 0.0418(11) 0.0518(12) 0.0002(9) 0.0210(10) 0.0033(10)
C1 0.0419(15) 0.0415(17) 0.0368(15) 0.000 0.0011(12) 0.000
C2 0.0443(12) 0.0413(13) 0.0438(13) -0.0012(9) 0.0040(10) 0.0007(9)
O4 0.0386(15) 0.062(2) 0.072(2) 0.0226(16) 0.0070(17) 0.0011(14)
O5 0.035(5) 0.033(5) 0.088(9) -0.004(6) -0.004(6) -0.009(4)
O3A 0.065(9) 0.040(7) 0.058(7) 0.002(5) 0.021(9) 0.016(6)

_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
P1 O1 1.5148(18) . ?
P1 O2 1.4992(18) . ?
P1 O3 1.589(4) . ?
P1 O4 1.523(4) . ?
P1 O5 1.677(12) . ?
P1 O3A 1.453(19) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.289(5) . ?
N2 H2 0.8600 . ?
N2 C1 1.354(3) . ?
N2 C2 1.366(3) . ?
O3 H3 0.81(4) . ?
N3 C2 1.329(3) 2_556 ?
N3 C2 1.329(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C2 1.307(3) . ?
O4 H4 0.94(3) . ?
O5 H4 0.88(4) . ?
O3A H3 0.90(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
O1 P1 O3 109.59(19) . . ?
O1 P1 O4 111.24(15) . . ?
O1 P1 O5 108.1(5) . . ?
O2 P1 O1 113.41(10) . . ?
O2 P1 O3 104.44(17) . . ?
O2 P1 O4 113.83(19) . . ?
O2 P1 O5 93.8(5) . . ?
O4 P1 O3 103.6(2) . . ?
O3A P1 O1 116.2(6) . . ?
O3A P1 O2 117.5(6) . . ?
O3A P1 O5 104.3(8) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C1 N2 H2 119.6 . . ?
C1 N2 C2 120.8(2) . . ?
C2 N2 H2 119.6 . . ?
P1 O3 H3 110(3) . . ?
C2 N3 C2 116.9(3) . 2_556 ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
N1 C1 N2 121.67(15) . . ?
N1 C1 N2 121.67(15) . 2_556 ?
N2 C1 N2 116.7(3) 2_556 . ?
N3 C2 N2 122.3(2) . . ?
N4 C2 N2 117.6(2) . . ?
N4 C2 N3 120.0(2) . . ?
P1 O4 H4 125(3) . . ?
P1 O5 H4 115(3) . . ?
P1 O3A H3 116(2) . . ?

_iucr_refine_instructions_details 
;
TITL pan11_2_5_2019_3_b.res in P2/c
    pan11_2_5_2019_3_tw.res
    created by SHELXL-2018/3 at 15:03:30 on 13-Jun-2019
REM Old TITL
REM SHELXT solution in P2/c: R1 0.211, Rweak 0.059, Alpha 0.054
REM <I/s> 0.727 for 87 systematic absences, Orientation as input
REM Formula found by SHELXT: C15 O2 P2
CELL 1.54184 4.5763 8.0571 16.5465 90 95.331 90
ZERR 2 0.0001 0.0002 0.0004 0 0.002 0
LATT 1
SYMM -X,+Y,0.5-Z
SFAC C H N O P
UNIT 6 24 12 16 4
DFIX 2.2 0.001 H4 P1

L.S. 10
PLAN  20
SIZE 0.1 0.1 0.1
BOND
bond $H
LIST 4
fmap 2
acta
OMIT 1 1 0
OMIT -1 0 2
OMIT -4 6 2
OMIT 1 2 0
OMIT 0 1 1
OMIT 1 1 1
REM <olex2.extras>
REM <HklSrc "%.\\pan11_2_5_2019_3_tw.hkl">
REM </olex2.extras>

WGHT    0.085400    0.120900
BASF   0.22645
FVAR      10.66606
P1    5    0.370848    0.701070    0.561797    11.00000    0.03773    0.04367 =
         0.04576    0.00251    0.00835    0.00423
O1    4    0.490235    0.542476    0.601418    11.00000    0.04352    0.04382 =
         0.04698    0.00100    0.00683    0.00367
O2    4    0.151768    0.787432    0.609097    11.00000    0.04732    0.04449 =
         0.04963   -0.00062    0.01199    0.00292
N1    3    0.000000    0.629621    0.750000    10.50000    0.05574    0.04044 =
         0.04334    0.00000    0.00981    0.00000
AFIX  93
H1A   2   -0.088958    0.682990    0.785476    10.50000   -1.20000
H1B   2    0.088958    0.682990    0.714524    10.50000   -1.20000
AFIX   0
N2    3    0.137624    0.381362    0.695115    11.00000    0.05065    0.04121 =
         0.04135    0.00339    0.01023    0.00106
AFIX  43
H2    2    0.232084    0.432632    0.660106    11.00000   -1.20000
AFIX   0

PART 1
O3    4    0.193976    0.658915    0.477045    10.80000    0.05090    0.06302 =
         0.05016   -0.00786   -0.00160    0.01745

PART 0
N3    3    0.000000    0.125533    0.750000    10.50000    0.05314    0.04096 =
         0.04387    0.00000    0.00834    0.00000
N4    3    0.259345    0.134624    0.638678    11.00000    0.06618    0.04183 =
         0.05183    0.00023    0.02097    0.00334
AFIX  93
H4A   2    0.262577    0.027926    0.637643    11.00000   -1.20000
H4B   2    0.342340    0.190494    0.602878    11.00000   -1.20000
AFIX   0
C1    1    0.000000    0.469599    0.750000    10.50000    0.04187    0.04153 =
         0.03681    0.00000    0.00113    0.00000
C2    1    0.128283    0.211878    0.694665    11.00000    0.04433    0.04126 =
         0.04384   -0.00117    0.00404    0.00068

PART 1
O4    4    0.617943    0.813121    0.538699    10.80000    0.03855    0.06198 =
         0.07157    0.02262    0.00703    0.00111
PART 0
PART 2
O5    4    0.625645    0.849511    0.579247    10.20000    0.03544    0.03336 =
         0.08781   -0.00409   -0.00380   -0.00917
O3A   4    0.312543    0.697425    0.473995    10.20000    0.06512    0.03990 =
         0.05768    0.00155    0.02137    0.01599
PART 0
H3    2    0.287470    0.595982    0.451306    11.00000    0.05691
H4    2    0.803178    0.822187    0.567835    11.00000    0.13227
HKLF 5




REM  pan11_2_5_2019_3_b.res in P2/c
REM wR2 = 0.1292, GooF = S = 1.113, Restrained GooF = 1.112 for all data
REM R1 = 0.0487 for 1034 Fo > 4sig(Fo) and 0.0505 for all 1113 data
REM 115 parameters refined using 1 restraints

END  
     
WGHT      0.0854      0.1210 

REM Highest difference peak  0.511,  deepest hole -0.311,  1-sigma level  0.092
Q1    1   0.3531  0.5886  0.5871  11.00000  0.05    0.51
Q2    1   0.3131  0.7856  0.5966  11.00000  0.05    0.46
Q3    1   0.0587  0.4144  0.7081  11.00000  0.05    0.32
Q4    1   0.5633  0.7114  0.5644  11.00000  0.05    0.30
Q5    1   0.4435  0.8076  0.5401  11.00000  0.05    0.29
Q6    1   0.4842  0.5224  0.6328  11.00000  0.05    0.29
Q7    1   0.0124  0.5416  0.7156  11.00000  0.05    0.29
Q8    1   0.5382  0.4714  0.5753  11.00000  0.05    0.28
Q9    1   0.1890  0.8137  0.6508  11.00000  0.05    0.28
Q10   1   0.3128  0.6494  0.5094  11.00000  0.05    0.28
Q11   1   0.3519  0.6205  0.5182  11.00000  0.05    0.27
Q12   1   0.1359  0.3165  0.7228  11.00000  0.05    0.25
Q13   1   0.0027  0.0869  0.7127  11.00000  0.05    0.25
Q14   1   0.2524  0.1791  0.6840  11.00000  0.05    0.24
Q15   1   0.0348  0.1808  0.7140  11.00000  0.05    0.23
Q16   1   0.6015  0.9171  0.5652  11.00000  0.05    0.23
Q17   1   0.1598  0.5936  0.5182  11.00000  0.05    0.23
Q18   1   0.1549  0.2965  0.6648  11.00000  0.05    0.22
Q19   1   0.1804  0.7195  0.5746  11.00000  0.05    0.21
Q20   1   0.2827  0.1683  0.5945  11.00000  0.05    0.21

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0487 for 1034 Fo > 4sig(Fo) and 0.0505 for all 1119 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.51, deepest hole -0.31
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0505
  REM R1_gt = 0.0487
  REM wR_ref = 0.1292
  REM GOOF = 1.113
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 1119
  REM Reflections_gt = 1034
  REM Parameters = n/a
  REM Hole = -0.31
  REM Peak = 0.51
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.774(4)
2 0.226(4)

