# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_xq
_database_code_depnum_ccdc_archive 'CCDC 2252377'
loop_
_audit_author_name
_audit_author_address
'qiao xia'
;Tongji University
China
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2023-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'imidazolium phosphate'
_chemical_formula_moiety         'H2 O4 P, C3 H5 N2'
_chemical_formula_sum            'C3 H7 N2 O4 P'
_chemical_formula_weight         166.08
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.3021(6)
_cell_length_b                   17.5648(12)
_cell_length_c                   4.7203(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     688.34(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2787
_cell_measurement_temperature    279.0
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0468 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.9022.
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    1.603
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.076
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4216
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.859
_diffrn_reflns_theta_min         2.714
_diffrn_ambient_temperature      279.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.991
_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         0.697
_reflns_Friedel_fraction_full    0.891
_reflns_Friedel_fraction_max     0.878
_reflns_number_gt                1443
_reflns_number_total             1549
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 554 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   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1549
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.082
_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)+(0.0403P)²+0.0314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0697
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C2(H2A), C3(H3)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2B), O4(H4)
;
_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 0.67283(6) 0.57721(3) 0.71814(14) 0.02511(16) Uani 1 1 d . . . . .
O1 O 0.7530(2) 0.65324(8) 0.6778(4) 0.0355(4) Uani 1 1 d . . . . .
O2 O 0.7669(2) 0.53048(9) 0.9463(4) 0.0329(4) Uani 1 1 d . . . . .
H2B H 0.722738 0.535435 1.100634 0.049 Uiso 1 1 calc R U . . .
O3 O 0.6635(2) 0.52869(10) 0.4556(4) 0.0382(4) Uani 1 1 d . . . . .
O4 O 0.5000(2) 0.59364(9) 0.8408(4) 0.0355(4) Uani 1 1 d . . . . .
H4 H 0.458148 0.553496 0.890221 0.053 Uiso 1 1 calc R U . . .
N1 N 0.4980(2) 0.82396(11) 0.0490(5) 0.0339(5) Uani 1 1 d . . . . .
H1 H 0.429906 0.831806 -0.085194 0.041 Uiso 1 1 calc R U . . .
N2 N 0.6441(2) 0.76682(12) 0.3591(5) 0.0364(5) Uani 1 1 d . . . . .
H2 H 0.686566 0.731383 0.460216 0.044 Uiso 1 1 calc R U . . .
C1 C 0.5351(3) 0.75704(14) 0.1587(5) 0.0339(6) Uani 1 1 d . . . . .
H1A H 0.491528 0.710558 0.103606 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5861(3) 0.87871(14) 0.1852(7) 0.0399(6) Uani 1 1 d . . . . .
H2A H 0.582885 0.930790 0.150226 0.048 Uiso 1 1 calc R U . . .
C3 C 0.6782(3) 0.84328(14) 0.3787(6) 0.0398(6) Uani 1 1 d . . . . .
H3 H 0.750975 0.866069 0.502194 0.048 Uiso 1 1 calc R 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
P1 O1 1.5043(15) . ?
P1 O2 1.5630(17) . ?
P1 O3 1.5059(19) . ?
P1 O4 1.5739(18) . ?
O2 H2B 0.8200 . ?
O4 H4 0.8200 . ?
N1 H1 0.8600 . ?
N1 C1 1.321(3) . ?
N1 C2 1.369(3) . ?
N2 H2 0.8600 . ?
N2 C1 1.320(3) . ?
N2 C3 1.376(3) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.344(4) . ?
C3 H3 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
O1 P1 O2 109.42(10) . . ?
O1 P1 O3 114.90(10) . . ?
O1 P1 O4 106.69(9) . . ?
O2 P1 O4 107.35(10) . . ?
O3 P1 O2 107.19(10) . . ?
O3 P1 O4 111.05(11) . . ?
P1 O2 H2B 109.5 . . ?
P1 O4 H4 109.5 . . ?
C1 N1 H1 125.8 . . ?
C1 N1 C2 108.4(2) . . ?
C2 N1 H1 125.8 . . ?
C1 N2 H2 125.8 . . ?
C1 N2 C3 108.4(2) . . ?
C3 N2 H2 125.8 . . ?
N1 C1 H1A 125.5 . . ?
N2 C1 N1 109.0(2) . . ?
N2 C1 H1A 125.5 . . ?
N1 C2 H2A 126.3 . . ?
C3 C2 N1 107.3(2) . . ?
C3 C2 H2A 126.3 . . ?
N2 C3 H3 126.6 . . ?
C2 C3 N2 106.8(2) . . ?
C2 C3 H3 126.6 . . ?

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
O2 H2B O3 0.82 1.75 2.553(3) 165.7 1_556 yes
O4 H4 O3 0.82 1.79 2.598(2) 169.2 2_665 yes
N1 H1 O1 0.86 1.86 2.714(3) 169.1 3_464 yes
N2 H2 O1 0.86 1.80 2.657(3) 173.6 . 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 N2 -0.3(3) . . . . ?
C1 N1 C2 C3 0.4(3) . . . . ?
C1 N2 C3 C2 0.2(3) . . . . ?
C2 N1 C1 N2 -0.2(3) . . . . ?
C3 N2 C1 N1 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_xq_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2252378'
loop_
_audit_author_name
_audit_author_address
'qiao xia'
;Tongji University
China
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2024-10-21 downloaded from the CCDC.
;
_audit_creation_date             2023-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '1-methylimidazolium phosphate'
_chemical_formula_moiety         'H2 O4 P, C4 H7 N2'
_chemical_formula_sum            'C4 H9 N2 O4 P'
_chemical_formula_weight         180.10
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1708(5)
_cell_length_b                   9.9677(6)
_cell_length_c                   9.8120(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.695(2)
_cell_angle_gamma                90
_cell_volume                     795.18(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2728
_cell_measurement_temperature    297.0
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.92
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0630 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.9321.
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    1.504
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.036
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9014
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         2.920
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1280
_reflns_number_total             1758
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1758
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.046
_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)+(0.0350P)²+0.5997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1111
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.25442(8) 0.52146(7) 0.03648(7) 0.0399(2) Uani 1 1 d . . . . .
O1 O 0.3885(2) 0.6136(2) 0.1053(2) 0.0534(5) Uani 1 1 d . . . . .
O4 O 0.1419(2) 0.4734(2) 0.13967(17) 0.0521(5) Uani 1 1 d . . . . .
O2 O 0.1546(2) 0.6120(2) -0.0725(2) 0.0584(6) Uani 1 1 d . . . . .
H2B H 0.066408 0.575929 -0.097329 0.088 Uiso 1 1 calc R U . . .
O3 O 0.3275(2) 0.4047(2) -0.0355(2) 0.0583(6) Uani 1 1 d . . . . .
N1 N 0.3499(3) 0.6053(2) 0.5911(2) 0.0445(5) Uani 1 1 d . . . . .
N2 N 0.2361(3) 0.5241(2) 0.4028(2) 0.0491(6) Uani 1 1 d . . . . .
H2 H 0.201415 0.515889 0.317518 0.059 Uiso 1 1 calc R U . . .
C1 C 0.4369(4) 0.6960(3) 0.6907(3) 0.0577(8) Uani 1 1 d . . . . .
H1A H 0.529401 0.650241 0.737564 0.087 Uiso 1 1 calc R U . . .
H1B H 0.363795 0.724381 0.755868 0.087 Uiso 1 1 calc R U . . .
H1C H 0.474740 0.773024 0.644067 0.087 Uiso 1 1 calc R U . . .
C2 C 0.3168(4) 0.6271(3) 0.4584(3) 0.0496(7) Uani 1 1 d . . . . .
H2A H 0.345994 0.703433 0.411878 0.060 Uiso 1 1 calc R U . . .
C3 C 0.2163(4) 0.4322(3) 0.5021(3) 0.0599(8) Uani 1 1 d . . . . .
H3 H 0.163438 0.349830 0.490449 0.072 Uiso 1 1 calc R U . . .
C4 C 0.2871(4) 0.4825(3) 0.6197(3) 0.0599(8) Uani 1 1 d . . . . .
H4 H 0.292578 0.441589 0.705185 0.072 Uiso 1 1 calc R U . . .
H1 H 0.506(6) 0.606(4) 0.071(4) 0.129(16) Uiso 1 1 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
P1 O1 1.5339(18) . ?
P1 O4 1.5115(18) . ?
P1 O2 1.5653(19) . ?
P1 O3 1.515(2) . ?
O1 H1 1.05(5) . ?
O2 H2B 0.8200 . ?
N1 C1 1.463(3) . ?
N1 C2 1.321(3) . ?
N1 C4 1.367(4) . ?
N2 H2 0.8600 . ?
N2 C2 1.310(3) . ?
N2 C3 1.358(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.336(4) . ?
C4 H4 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
O1 P1 O2 104.90(11) . . ?
O4 P1 O1 110.49(11) . . ?
O4 P1 O2 109.26(11) . . ?
O4 P1 O3 111.28(12) . . ?
O3 P1 O1 111.57(11) . . ?
O3 P1 O2 109.12(12) . . ?
P1 O1 H1 117(2) . . ?
P1 O2 H2B 109.5 . . ?
C2 N1 C1 126.5(2) . . ?
C2 N1 C4 107.8(2) . . ?
C4 N1 C1 125.7(2) . . ?
C2 N2 H2 125.7 . . ?
C2 N2 C3 108.7(2) . . ?
C3 N2 H2 125.7 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 125.5 . . ?
N2 C2 N1 109.1(2) . . ?
N2 C2 H2A 125.5 . . ?
N2 C3 H3 126.4 . . ?
C4 C3 N2 107.1(3) . . ?
C4 C3 H3 126.4 . . ?
N1 C4 H4 126.3 . . ?
C3 C4 N1 107.3(2) . . ?
C3 C4 H4 126.3 . . ?

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
N2 C3 C4 N1 0.0(4) . . . . ?
C1 N1 C2 N2 -179.4(2) . . . . ?
C1 N1 C4 C3 179.5(3) . . . . ?
C2 N1 C4 C3 0.0(3) . . . . ?
C2 N2 C3 C4 0.1(4) . . . . ?
C3 N2 C2 N1 -0.1(3) . . . . ?
C4 N1 C2 N2 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Moisture-sensitive
