# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_x11
_database_code_depnum_ccdc_archive 'CCDC 2173858'
loop_
_audit_author_name
_audit_author_address
'Duanliang Wang'
;NO
China
;
_audit_update_record             
;
2022-05-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;
_audit_creation_date             2022-05-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        C6H12N2O4P
_chemical_formula_moiety         'H2 O4 P, C6 H9 N2'
_chemical_formula_sum            'C6 H11 N2 O4 P'
_chemical_formula_weight         206.14
_chemical_absolute_configuration ?
_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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   16.313(2)
_cell_length_b                   6.9761(10)
_cell_length_c                   7.9052(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     899.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3138
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0600 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.8781.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9515
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.615
_diffrn_reflns_theta_min         2.497
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                1957
_reflns_number_total             2494
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.048
_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)+(0.0377P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0818
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_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 0.54197(4) 0.82487(9) 0.58922(10) 0.02667(17) Uani 1 1 d . . . . .
O4 O 0.51148(13) 0.6509(3) 0.6819(3) 0.0346(5) Uani 1 1 d . . . . .
O1 O 0.63690(13) 0.8444(3) 0.6148(3) 0.0451(6) Uani 1 1 d . . . . .
H1 H 0.660245 0.755779 0.566536 0.068 Uiso 1 1 calc R U . . .
O2 O 0.50475(15) 1.0118(3) 0.6403(3) 0.0440(6) Uani 1 1 d . . . . .
N2 N 0.93864(13) 0.6521(3) 0.5128(3) 0.0283(5) Uani 1 1 d . . . . .
H2A H 0.951145 0.637345 0.404009 0.034 Uiso 1 1 calc R U . . .
H2B H 0.953606 0.547905 0.569976 0.034 Uiso 1 1 calc R U . . .
H2C H 0.964977 0.753721 0.553805 0.034 Uiso 1 1 calc R U . . .
O3 O 0.52859(14) 0.7812(3) 0.3964(3) 0.0417(6) Uani 1 1 d . . . . .
H3A H 0.520914 0.881872 0.345243 0.063 Uiso 1 1 calc R U . . .
N1 N 0.71780(14) 0.5437(4) 0.4783(4) 0.0374(6) Uani 1 1 d . . . . .
C2 C 0.79888(16) 0.5189(4) 0.4602(3) 0.0289(6) Uani 1 1 d . . . . .
C3 C 0.8308(2) 0.3584(5) 0.3813(5) 0.0385(7) Uani 1 1 d . . . . .
H3 H 0.887211 0.344532 0.369054 0.046 Uiso 1 1 calc R U . . .
C1 C 0.84930(17) 0.6809(4) 0.5305(4) 0.0338(7) Uani 1 1 d . . . . .
H1A H 0.834100 0.798481 0.473070 0.041 Uiso 1 1 calc R U . . .
H1B H 0.836303 0.696400 0.649491 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7782(2) 0.2186(5) 0.3206(4) 0.0416(8) Uani 1 1 d . . . . .
H4 H 0.798756 0.109690 0.267696 0.050 Uiso 1 1 calc R U . . .
C5 C 0.6951(2) 0.2432(5) 0.3398(5) 0.0448(8) Uani 1 1 d . . . . .
H5 H 0.658248 0.151922 0.300380 0.054 Uiso 1 1 calc R U . . .
C6 C 0.6684(2) 0.4059(5) 0.4185(5) 0.0485(9) Uani 1 1 d . . . . .
H6 H 0.612193 0.422228 0.431470 0.058 Uiso 1 1 calc R U . . .

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 0.0345(3) 0.0235(3) 0.0220(3) -0.0011(3) -0.0003(3) 0.0038(3)
O4 0.0424(12) 0.0337(12) 0.0278(11) 0.0036(9) -0.0016(9) -0.0060(9)
O1 0.0346(11) 0.0384(12) 0.0622(19) -0.0136(13) -0.0009(11) -0.0053(9)
O2 0.0688(14) 0.0350(12) 0.0282(10) -0.0017(8) 0.0038(9) 0.0217(10)
N2 0.0304(12) 0.0288(13) 0.0258(11) -0.0003(10) -0.0002(10) -0.0020(10)
O3 0.0670(16) 0.0337(12) 0.0243(10) -0.0013(9) -0.0026(10) 0.0110(11)
N1 0.0267(12) 0.0378(14) 0.0478(16) -0.0020(12) 0.0031(12) 0.0030(11)
C2 0.0264(13) 0.0326(15) 0.0277(15) 0.0031(11) 0.0003(11) 0.0023(12)
C3 0.0311(16) 0.0403(19) 0.0440(18) -0.0079(15) 0.0029(14) 0.0036(13)
C1 0.0308(14) 0.0332(16) 0.0375(16) -0.0038(12) 0.0024(12) 0.0004(13)
C4 0.046(2) 0.0320(18) 0.046(2) -0.0075(14) -0.0034(16) 0.0023(14)
C5 0.0423(19) 0.0389(19) 0.053(2) -0.0029(16) -0.0043(16) -0.0089(18)
C6 0.0295(16) 0.046(2) 0.070(3) -0.0017(19) 0.0026(16) -0.0032(15)

_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 O4 1.502(2) . ?
P1 O1 1.568(2) . ?
P1 O2 1.494(2) . ?
P1 O3 1.570(2) . ?
O1 H1 0.8200 . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C1 1.478(3) . ?
O3 H3A 0.8200 . ?
N1 C2 1.342(3) . ?
N1 C6 1.340(4) . ?
C2 C3 1.384(4) . ?
C2 C1 1.504(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.374(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.366(5) . ?
C6 H6 0.9300 . ?

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
O4 P1 O1 109.53(13) . . ?
O4 P1 O3 105.70(12) . . ?
O1 P1 O3 106.22(13) . . ?
O2 P1 O4 116.03(14) . . ?
O2 P1 O1 106.92(13) . . ?
O2 P1 O3 112.04(13) . . ?
P1 O1 H1 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C1 N2 H2A 109.5 . . ?
C1 N2 H2B 109.5 . . ?
C1 N2 H2C 109.5 . . ?
P1 O3 H3A 109.5 . . ?
C6 N1 C2 117.6(3) . . ?
N1 C2 C3 121.6(3) . . ?
N1 C2 C1 113.8(3) . . ?
C3 C2 C1 124.7(3) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
N2 C1 C2 113.7(2) . . ?
N2 C1 H1A 108.8 . . ?
N2 C1 H1B 108.8 . . ?
C2 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C5 124.4(3) . . ?
N1 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?

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
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.89 2.703(3) 173.9 . yes
N2 H2A O4 0.89 1.86 2.740(3) 168.8 4_654 yes
N2 H2B O4 0.89 1.90 2.769(3) 166.1 3_565 yes
N2 H2C O2 0.89 1.89 2.771(3) 171.1 3_575 yes
O3 H3A O2 0.82 1.83 2.546(3) 144.9 2_674 yes

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 C2 C3 C4 -0.6(5) . . . . ?
N1 C2 C1 N2 179.1(2) . . . . ?
C2 N1 C6 C5 -0.4(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C2 C1 N2 -1.7(4) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C1 C2 C3 C4 -179.7(3) . . . . ?
C4 C5 C6 N1 0.1(6) . . . . ?
C6 N1 C2 C3 0.7(5) . . . . ?
C6 N1 C2 C1 179.8(3) . . . . ?

_shelx_res_file                  
;
TITL x11_a.res in Pca2(1)
    x11.res
    created by SHELXL-2018/3 at 11:29:02 on 06-May-2022
REM Old TITL x11 in Pca2(1)
REM SHELXT solution in Pca2(1): R1 0.093, Rweak 0.011, Alpha 0.002
REM <I/s> 0.758 for 119 systematic absences, Orientation as input
REM Flack x = 0.024 ( 0.046 ) from 653 Parsons' quotients
REM Formula found by SHELXT: C6 N O5 P
CELL 0.71073 16.313 6.9761 7.9052 90 90 90
ZERR 4 0.0021 0.001 0.0009 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,-Y,+Z
SYMM 0.5-X,+Y,0.5+Z
SFAC C H N O P
UNIT 24 44 8 16 4
EQIV $1 0.5+X,1-Y,+Z
EQIV $2 1.5-X,+Y,-0.5+Z
EQIV $3 0.5+X,2-Y,+Z
EQIV $4 1-X,2-Y,-0.5+Z

L.S. 25
PLAN  5
SIZE 0.1 0.11 0.12
TEMP 19.85
CONF
HTAB O1 N1
HTAB N2 O4_$1
HTAB N2 O4_$2
HTAB N2 O2_$3
HTAB O3 O2_$4
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\x11.hkl">
REM </olex2.extras>

WGHT    0.037700
FVAR       0.98323
P1    5    0.541965    0.824871    0.589220    11.00000    0.03451    0.02348 =
         0.02202   -0.00107   -0.00034    0.00378
O4    4    0.511480    0.650900    0.681867    11.00000    0.04236    0.03367 =
         0.02782    0.00365   -0.00158   -0.00599
O1    4    0.636905    0.844364    0.614793    11.00000    0.03464    0.03844 =
         0.06217   -0.01360   -0.00089   -0.00531
AFIX 147
H1    2    0.660245    0.755779    0.566536    11.00000   -1.50000
AFIX   0
O2    4    0.504746    1.011763    0.640273    11.00000    0.06884    0.03496 =
         0.02821   -0.00171    0.00385    0.02175

N2    3    0.938641    0.652101    0.512820    11.00000    0.03043    0.02877 =
         0.02581   -0.00026   -0.00024   -0.00205
AFIX 137
H2A   2    0.951145    0.637345    0.404009    11.00000   -1.20000
H2B   2    0.953606    0.547905    0.569976    11.00000   -1.20000
H2C   2    0.964977    0.753721    0.553805    11.00000   -1.20000
AFIX   0

O3    4    0.528587    0.781172    0.396351    11.00000    0.06697    0.03372 =
         0.02433   -0.00133   -0.00264    0.01098
AFIX 147
H3A   2    0.520914    0.881872    0.345243    11.00000   -1.50000
AFIX   0

N1    3    0.717795    0.543656    0.478309    11.00000    0.02667    0.03781 =
         0.04784   -0.00196    0.00306    0.00303
C2    1    0.798884    0.518926    0.460242    11.00000    0.02638    0.03262 =
         0.02769    0.00306    0.00035    0.00228
C3    1    0.830823    0.358426    0.381291    11.00000    0.03110    0.04026 =
         0.04401   -0.00787    0.00290    0.00356
AFIX  43
H3    2    0.887211    0.344532    0.369054    11.00000   -1.20000
AFIX   0
C1    1    0.849298    0.680880    0.530539    11.00000    0.03075    0.03317 =
         0.03755   -0.00384    0.00239    0.00040
AFIX  23
H1A   2    0.834100    0.798481    0.473070    11.00000   -1.20000
H1B   2    0.836303    0.696400    0.649491    11.00000   -1.20000
AFIX   0
C4    1    0.778190    0.218606    0.320618    11.00000    0.04630    0.03205 =
         0.04636   -0.00754   -0.00337    0.00225
AFIX  43
H4    2    0.798756    0.109690    0.267696    11.00000   -1.20000
AFIX   0
C5    1    0.695135    0.243230    0.339790    11.00000    0.04228    0.03888 =
         0.05336   -0.00293   -0.00426   -0.00885
AFIX  43
H5    2    0.658248    0.151922    0.300380    11.00000   -1.20000
AFIX   0
C6    1    0.668426    0.405938    0.418509    11.00000    0.02946    0.04640 =
         0.06972   -0.00166    0.00257   -0.00317
AFIX  43
H6    2    0.612193    0.422228    0.431470    11.00000   -1.20000
AFIX   0
HKLF 4




REM  x11_a.res in Pca2(1)
REM wR2 = 0.0818, GooF = S = 1.048, Restrained GooF = 1.048 for all data
REM R1 = 0.0371 for 1957 Fo > 4sig(Fo) and 0.0604 for all 2494 data
REM 121 parameters refined using 1 restraints

END

WGHT      0.0377      0.0000

REM Highest difference peak  0.230,  deepest hole -0.252,  1-sigma level  0.054
Q1    1   0.5405  0.5360  0.5876  11.00000  0.05    0.23
Q2    1   0.7400  0.8769  0.3866  11.00000  0.05    0.20
Q3    1   0.5985  0.4972  0.5921  11.00000  0.05    0.20
Q4    1   0.6030  0.2393  0.5889  11.00000  0.05    0.20
Q5    1   0.6197  0.1833  0.0916  11.00000  0.05    0.19
;
_shelx_res_checksum              97684
_olex2_submission_special_instructions 'No special instructions were received'
