# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_EF184
_database_code_depnum_ccdc_archive 'CCDC 2076831'
loop_
_audit_author_name
_audit_author_address
'Jose Goicoechea'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
 PH2C(O)NHNH2
;
_contact_author_fax              '+44 1865 272690'
_chemical_name_common            .
_chemical_melting_point          .
_chemical_formula_moiety         'C H5 N2 O P'
_chemical_formula_sum            'C H5 N2 O P'
_chemical_formula_weight         92.04

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   25.025(2)
_cell_length_b                   4.8946(4)
_cell_length_c                   6.9706(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.901(10)
_cell_angle_gamma                90
_cell_volume                     851.85(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1271
_cell_measurement_theta_min      7.0990
_cell_measurement_theta_max      76.0820

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    4.342
_shelx_estimated_absorpt_T_min   0.509
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   .

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5035
_diffrn_reflns_number            5153
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.540
_diffrn_reflns_theta_max         66.470
_diffrn_reflns_theta_full        66.470
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1500
_reflns_number_gt                1033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 1.171.38.43b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0798P)²+4.9532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1500
_refine_ls_number_parameters     130
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0788
_refine_ls_wR_factor_ref         0.2203
_refine_ls_wR_factor_gt          0.2102
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.125
_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
P1 P 0.18909(7) 0.0269(4) 0.1512(3) 0.0367(6) Uani 1 1 d D . . . .
C1 C 0.1204(2) -0.0852(13) 0.2009(10) 0.0239(14) Uani 1 1 d . . . . .
O1 O 0.10865(19) -0.3270(9) 0.1920(7) 0.0315(12) Uani 1 1 d . . . . .
N1 N 0.0873(2) 0.1104(10) 0.2559(8) 0.0237(12) Uani 1 1 d . . . . .
N2 N 0.0364(2) 0.0451(12) 0.3266(10) 0.0266(13) Uani 1 1 d . . . . .
P21 P 0.31089(8) 0.5159(4) 0.0557(3) 0.0392(6) Uani 1 1 d D . . . .
C21 C 0.3804(3) 0.4126(13) 0.1407(10) 0.0239(13) Uani 1 1 d . . . . .
O21 O 0.39190(19) 0.1686(9) 0.1394(8) 0.0318(11) Uani 1 1 d . . . . .
N21 N 0.4125(2) 0.6083(11) 0.2121(9) 0.0264(12) Uani 1 1 d . . . . .
N22 N 0.4632(2) 0.5458(12) 0.3088(10) 0.0301(14) Uani 1 1 d . . . . .
H2 H 0.186(4) -0.036(17) -0.041(4) 0.05(2) Uiso 1 1 d D . . . .
H4 H 0.053(4) -0.047(18) 0.442(12) 0.04(2) Uiso 1 1 d . . . . .
H5 H 0.022(3) -0.055(15) 0.261(10) 0.010(17) Uiso 1 1 d . . . . .
H21 H 0.314(4) 0.447(18) -0.136(4) 0.05(3) Uiso 1 1 d D . . . .
H22 H 0.323(4) 0.785(8) 0.016(14) 0.06(3) Uiso 1 1 d D . . . .
H23 H 0.402(2) 0.792(14) 0.207(8) 0.007(14) Uiso 1 1 d . . . . .
H24 H 0.473(3) 0.428(16) 0.251(10) 0.015(18) Uiso 1 1 d . . . . .
H25 H 0.449(4) 0.450(19) 0.409(13) 0.04(2) Uiso 1 1 d . . . . .
H1 H 0.180(4) 0.299(6) 0.106(12) 0.05(2) Uiso 1 1 d D . . . .
H3 H 0.098(3) 0.303(18) 0.242(11) 0.033 Uiso 1 1 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
P1 C1 1.859(6) . ?
P1 H2 1.37(2) . ?
P1 H1 1.38(2) . ?
C1 O1 1.220(8) . ?
C1 N1 1.339(8) . ?
N1 N2 1.432(7) . ?
N1 H3 0.99(9) . ?
N2 H4 0.98(9) . ?
N2 H5 0.75(7) . ?
P21 C21 1.868(7) . ?
P21 H21 1.38(2) . ?
P21 H22 1.38(2) . ?
C21 O21 1.229(8) . ?
C21 N21 1.326(8) . ?
N21 N22 1.429(8) . ?
N21 H23 0.93(7) . ?
N22 H24 0.75(8) . ?
N22 H25 0.94(9) . ?

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
C1 P1 H2 97(4) . . ?
C1 P1 H1 100(4) . . ?
H2 P1 H1 90(5) . . ?
O1 C1 N1 123.8(6) . . ?
O1 C1 P1 120.0(5) . . ?
N1 C1 P1 116.1(5) . . ?
C1 N1 N2 121.4(5) . . ?
C1 N1 H3 118(5) . . ?
N2 N1 H3 121(5) . . ?
N1 N2 H4 93(5) . . ?
N1 N2 H5 110(5) . . ?
H4 N2 H5 111(7) . . ?
C21 P21 H21 97(4) . . ?
C21 P21 H22 96(4) . . ?
H21 P21 H22 91(5) . . ?
O21 C21 N21 124.6(6) . . ?
O21 C21 P21 118.4(5) . . ?
N21 C21 P21 116.8(5) . . ?
C21 N21 N22 121.3(5) . . ?
C21 N21 H23 122(4) . . ?
N22 N21 H23 117(4) . . ?
N21 N22 H24 103(6) . . ?
N21 N22 H25 95(5) . . ?
H24 N22 H25 100(8) . . ?

_refine_diff_density_max         1.097
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_EF360B
_database_code_depnum_ccdc_archive 'CCDC 2076832'
loop_
_audit_author_name
_audit_author_address
'Jose Goicoechea'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
 PH2C(O)NHNH2*0.5(18-crown-6)
;
_contact_author_fax              '+44 1865 272690'
_chemical_name_common            .
_chemical_melting_point          .
_chemical_formula_moiety         'C H5 N2 O P, 0.5(C12 H24 O6)'
_chemical_formula_sum            'C7 H17 N2 O4 P'
_chemical_formula_weight         224.19

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.9885(2)
_cell_length_b                   11.78140(10)
_cell_length_c                   14.7581(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.5020(10)
_cell_angle_gamma                90
_cell_volume                     2292.66(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15106
_cell_measurement_theta_min      4.8930
_cell_measurement_theta_max      76.1570

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.122
_shelx_estimated_absorpt_T_min   0.652
_shelx_estimated_absorpt_T_max   0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4102
_diffrn_reflns_number            22090
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.919
_diffrn_reflns_theta_max         76.017
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4757
_reflns_number_gt                4570
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 1.171.38.43b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0535P)²+3.5724P] 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_number_reflns         4757
_refine_ls_number_parameters     293
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.040
_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
P1 P 0.05981(5) 0.41861(6) 0.22724(5) 0.03939(18) Uani 1 1 d D . . . .
H1 H -0.0359(9) 0.407(3) 0.187(2) 0.080(12) Uiso 1 1 d D . . . .
H2 H 0.052(2) 0.465(3) 0.1454(13) 0.064(10) Uiso 1 1 d D . . . .
C1 C 0.05157(16) 0.5608(2) 0.28123(15) 0.0272(4) Uani 1 1 d . . . . .
O1 O 0.09201(17) 0.64500(17) 0.26181(14) 0.0497(5) Uani 1 1 d . . . . .
N1 N 0.00548(14) 0.56012(16) 0.34766(12) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.009(2) 0.621(3) 0.383(2) 0.037(7) Uiso 1 1 d . . . . .
N2 N -0.02043(15) 0.45499(17) 0.37790(13) 0.0264(4) Uani 1 1 d . . . . .
H4 H 0.025(2) 0.438(2) 0.432(2) 0.033(7) Uiso 1 1 d . . . . .
H5 H -0.076(2) 0.460(3) 0.390(2) 0.041(8) Uiso 1 1 d . . . . .
P21 P 0.31014(4) 0.48330(6) 0.20519(4) 0.03787(18) Uani 1 1 d D . . . .
H21 H 0.293(2) 0.5875(11) 0.1859(19) 0.057(9) Uiso 1 1 d D . . . .
H22 H 0.314(2) 0.509(2) 0.2916(10) 0.050(9) Uiso 1 1 d D . . . .
C21 C 0.44979(16) 0.49607(18) 0.23339(15) 0.0250(4) Uani 1 1 d . . . . .
O21 O 0.51005(13) 0.48473(17) 0.31455(12) 0.0401(4) Uani 1 1 d . . . . .
N21 N 0.47760(14) 0.51295(18) 0.15614(13) 0.0297(4) Uani 1 1 d . . . . .
H23 H 0.542(2) 0.513(2) 0.163(2) 0.037(7) Uiso 1 1 d . . . . .
N22 N 0.40260(15) 0.51414(19) 0.06452(13) 0.0302(4) Uani 1 1 d . . . . .
H24 H 0.411(2) 0.576(3) 0.033(2) 0.043(8) Uiso 1 1 d . . . . .
H25 H 0.410(2) 0.451(3) 0.032(2) 0.036(7) Uiso 1 1 d . . . . .
O101 O 0.18987(11) 0.61884(12) 0.55453(11) 0.0253(3) Uani 1 1 d . . . . .
O102 O 0.17328(11) 0.37953(12) 0.52639(11) 0.0273(3) Uani 1 1 d . . . . .
O103 O -0.00521(11) 0.25283(12) 0.51846(10) 0.0243(3) Uani 1 1 d . . . . .
C101 C 0.18358(16) 0.73075(18) 0.51655(16) 0.0269(4) Uani 1 1 d . . . . .
H10A H 0.168790 0.727490 0.446154 0.032 Uiso 1 1 calc R U . . .
H10B H 0.248977 0.770612 0.545773 0.032 Uiso 1 1 calc R U . . .
C102 C 0.26389(15) 0.5517(2) 0.53293(16) 0.0274(4) Uani 1 1 d . . . . .
H10C H 0.331423 0.587842 0.559634 0.033 Uiso 1 1 calc R U . . .
H10D H 0.246856 0.545168 0.462422 0.033 Uiso 1 1 calc R U . . .
C103 C 0.26576(15) 0.43631(19) 0.57629(16) 0.0279(5) Uani 1 1 d . . . . .
H10E H 0.323899 0.392151 0.571034 0.033 Uiso 1 1 calc R U . . .
H10F H 0.273527 0.443524 0.645219 0.033 Uiso 1 1 calc R U . . .
C104 C 0.17354(16) 0.26413(18) 0.55485(16) 0.0268(4) Uani 1 1 d . . . . .
H10G H 0.178550 0.260049 0.623285 0.032 Uiso 1 1 calc R U . . .
H10H H 0.232765 0.224283 0.547364 0.032 Uiso 1 1 calc R U . . .
C105 C 0.07727(17) 0.20838(18) 0.49328(15) 0.0264(4) Uani 1 1 d . . . . .
H10I H 0.066452 0.223479 0.424575 0.032 Uiso 1 1 calc R U . . .
H10J H 0.081886 0.125235 0.503542 0.032 Uiso 1 1 calc R U . . .
C106 C -0.10043(16) 0.20637(18) 0.46135(16) 0.0276(4) Uani 1 1 d . . . . .
H10K H -0.103253 0.124693 0.476015 0.033 Uiso 1 1 calc R U . . .
H10L H -0.109011 0.214117 0.392281 0.033 Uiso 1 1 calc R U . . .
O201 O 0.60251(11) 0.30225(14) 0.07847(11) 0.0306(3) Uani 1 1 d . . . . .
O202 O 0.69016(11) 0.51344(13) 0.16082(11) 0.0273(3) Uani 1 1 d . . . . .
O203 O 0.60616(11) 0.70730(13) 0.04512(11) 0.0305(3) Uani 1 1 d . . . . .
C201 C 0.53704(18) 0.2082(2) 0.07165(19) 0.0357(5) Uani 1 1 d . . . . .
H20A H 0.499966 0.217503 0.117774 0.043 Uiso 1 1 calc R U . . .
H20B H 0.577349 0.137438 0.087937 0.043 Uiso 1 1 calc R U . . .
C202 C 0.67761(17) 0.3122(2) 0.17126(16) 0.0333(5) Uani 1 1 d . . . . .
H20C H 0.717785 0.241367 0.187606 0.040 Uiso 1 1 calc R U . . .
H20D H 0.644688 0.324946 0.220273 0.040 Uiso 1 1 calc R U . . .
C203 C 0.74535(16) 0.4098(2) 0.17039(16) 0.0316(5) Uani 1 1 d . . . . .
H20E H 0.803959 0.410726 0.230862 0.038 Uiso 1 1 calc R U . . .
H20F H 0.771447 0.401525 0.116097 0.038 Uiso 1 1 calc R U . . .
C204 C 0.74786(16) 0.6093(2) 0.15141(17) 0.0328(5) Uani 1 1 d . . . . .
H20G H 0.771675 0.598740 0.095891 0.039 Uiso 1 1 calc R U . . .
H20H H 0.807980 0.617860 0.210032 0.039 Uiso 1 1 calc R U . . .
C205 C 0.68317(18) 0.7131(2) 0.13688(17) 0.0360(5) Uani 1 1 d . . . . .
H20I H 0.651896 0.718094 0.187845 0.043 Uiso 1 1 calc R U . . .
H20J H 0.725230 0.781684 0.140669 0.043 Uiso 1 1 calc R U . . .
C206 C 0.53684(18) 0.7994(2) 0.02857(19) 0.0350(5) Uani 1 1 d . . . . .
H20K H 0.574169 0.872237 0.037156 0.042 Uiso 1 1 calc R U . . .
H20L H 0.500058 0.796736 0.075372 0.042 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 C1 1.875(2) . ?
P1 H1 1.278(10) . ?
P1 H2 1.298(10) . ?
C1 O1 1.223(3) . ?
C1 N1 1.341(3) . ?
N1 N2 1.405(3) . ?
N1 H3 0.88(3) . ?
N2 H4 0.87(3) . ?
N2 H5 0.85(3) . ?
P21 C21 1.863(2) . ?
P21 H21 1.265(10) . ?
P21 H22 1.293(10) . ?
C21 O21 1.220(3) . ?
C21 N21 1.337(3) . ?
N21 N22 1.408(3) . ?
N21 H23 0.87(3) . ?
N22 H24 0.90(3) . ?
N22 H25 0.91(3) . ?
O101 C102 1.421(3) . ?
O101 C101 1.424(3) . ?
O102 C104 1.423(2) . ?
O102 C103 1.424(3) . ?
O103 C105 1.425(2) . ?
O103 C106 1.426(2) . ?
C101 C106 1.504(3) 3_566 ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C102 C103 1.499(3) . ?
C102 H10C 0.9900 . ?
C102 H10D 0.9900 . ?
C103 H10E 0.9900 . ?
C103 H10F 0.9900 . ?
C104 C105 1.501(3) . ?
C104 H10G 0.9900 . ?
C104 H10H 0.9900 . ?
C105 H10I 0.9900 . ?
C105 H10J 0.9900 . ?
C106 H10K 0.9900 . ?
C106 H10L 0.9900 . ?
O201 C201 1.420(3) . ?
O201 C202 1.426(3) . ?
O202 C204 1.422(3) . ?
O202 C203 1.426(3) . ?
O203 C206 1.421(3) . ?
O203 C205 1.423(3) . ?
C201 C206 1.498(4) 3_665 ?
C201 H20A 0.9900 . ?
C201 H20B 0.9900 . ?
C202 C203 1.493(3) . ?
C202 H20C 0.9900 . ?
C202 H20D 0.9900 . ?
C203 H20E 0.9900 . ?
C203 H20F 0.9900 . ?
C204 C205 1.493(3) . ?
C204 H20G 0.9900 . ?
C204 H20H 0.9900 . ?
C205 H20I 0.9900 . ?
C205 H20J 0.9900 . ?
C206 H20K 0.9900 . ?
C206 H20L 0.9900 . ?

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
C1 P1 H1 95.3(18) . . ?
C1 P1 H2 91.3(16) . . ?
H1 P1 H2 82.1(11) . . ?
O1 C1 N1 123.3(2) . . ?
O1 C1 P1 121.77(17) . . ?
N1 C1 P1 114.73(16) . . ?
C1 N1 N2 118.38(18) . . ?
C1 N1 H3 119.2(19) . . ?
N2 N1 H3 119.8(19) . . ?
N1 N2 H4 107.9(19) . . ?
N1 N2 H5 111(2) . . ?
H4 N2 H5 106(3) . . ?
C21 P21 H21 94.6(15) . . ?
C21 P21 H22 93.6(14) . . ?
H21 P21 H22 86.6(11) . . ?
O21 C21 N21 123.4(2) . . ?
O21 C21 P21 122.68(17) . . ?
N21 C21 P21 113.80(16) . . ?
C21 N21 N22 119.00(18) . . ?
C21 N21 H23 119.0(19) . . ?
N22 N21 H23 121.4(19) . . ?
N21 N22 H24 109(2) . . ?
N21 N22 H25 108.9(18) . . ?
H24 N22 H25 109(3) . . ?
C102 O101 C101 112.39(16) . . ?
C104 O102 C103 112.58(16) . . ?
C105 O103 C106 112.49(16) . . ?
O101 C101 C106 108.75(17) . 3_566 ?
O101 C101 H10A 109.9 . . ?
C106 C101 H10A 109.9 3_566 . ?
O101 C101 H10B 109.9 . . ?
C106 C101 H10B 109.9 3_566 . ?
H10A C101 H10B 108.3 . . ?
O101 C102 C103 108.61(16) . . ?
O101 C102 H10C 110.0 . . ?
C103 C102 H10C 110.0 . . ?
O101 C102 H10D 110.0 . . ?
C103 C102 H10D 110.0 . . ?
H10C C102 H10D 108.3 . . ?
O102 C103 C102 108.78(16) . . ?
O102 C103 H10E 109.9 . . ?
C102 C103 H10E 109.9 . . ?
O102 C103 H10F 109.9 . . ?
C102 C103 H10F 109.9 . . ?
H10E C103 H10F 108.3 . . ?
O102 C104 C105 109.03(17) . . ?
O102 C104 H10G 109.9 . . ?
C105 C104 H10G 109.9 . . ?
O102 C104 H10H 109.9 . . ?
C105 C104 H10H 109.9 . . ?
H10G C104 H10H 108.3 . . ?
O103 C105 C104 108.79(16) . . ?
O103 C105 H10I 109.9 . . ?
C104 C105 H10I 109.9 . . ?
O103 C105 H10J 109.9 . . ?
C104 C105 H10J 109.9 . . ?
H10I C105 H10J 108.3 . . ?
O103 C106 C101 108.67(16) . 3_566 ?
O103 C106 H10K 110.0 . . ?
C101 C106 H10K 110.0 3_566 . ?
O103 C106 H10L 110.0 . . ?
C101 C106 H10L 110.0 3_566 . ?
H10K C106 H10L 108.3 . . ?
C201 O201 C202 112.54(17) . . ?
C204 O202 C203 112.56(16) . . ?
C206 O203 C205 112.52(18) . . ?
O201 C201 C206 109.45(19) . 3_665 ?
O201 C201 H20A 109.8 . . ?
C206 C201 H20A 109.8 3_665 . ?
O201 C201 H20B 109.8 . . ?
C206 C201 H20B 109.8 3_665 . ?
H20A C201 H20B 108.2 . . ?
O201 C202 C203 108.75(18) . . ?
O201 C202 H20C 109.9 . . ?
C203 C202 H20C 109.9 . . ?
O201 C202 H20D 109.9 . . ?
C203 C202 H20D 109.9 . . ?
H20C C202 H20D 108.3 . . ?
O202 C203 C202 109.63(17) . . ?
O202 C203 H20E 109.7 . . ?
C202 C203 H20E 109.7 . . ?
O202 C203 H20F 109.7 . . ?
C202 C203 H20F 109.7 . . ?
H20E C203 H20F 108.2 . . ?
O202 C204 C205 109.14(18) . . ?
O202 C204 H20G 109.9 . . ?
C205 C204 H20G 109.9 . . ?
O202 C204 H20H 109.9 . . ?
C205 C204 H20H 109.9 . . ?
H20G C204 H20H 108.3 . . ?
O203 C205 C204 109.09(18) . . ?
O203 C205 H20I 109.9 . . ?
C204 C205 H20I 109.9 . . ?
O203 C205 H20J 109.9 . . ?
C204 C205 H20J 109.9 . . ?
H20I C205 H20J 108.3 . . ?
O203 C206 C201 109.27(19) . 3_665 ?
O203 C206 H20K 109.8 . . ?
C201 C206 H20K 109.8 3_665 . ?
O203 C206 H20L 109.8 . . ?
C201 C206 H20L 109.8 3_665 . ?
H20K C206 H20L 108.3 . . ?

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
_geom_hbond_publ_flag
N2 H4 O102 0.87(3) 2.18(3) 2.995(2) 156(3) . yes
N2 H4 O103 0.87(3) 2.63(3) 3.119(2) 117(2) . yes
N21 H23 O202 0.87(3) 2.08(3) 2.951(2) 173(3) . yes
N1 H3 O103 0.88(3) 2.09(3) 2.961(2) 170(3) 3_566 yes
N2 H5 O101 0.85(3) 2.23(3) 2.991(2) 149(3) 3_566 yes
N22 H24 O201 0.90(3) 2.14(3) 3.006(3) 162(3) 3_665 yes
N22 H25 O203 0.91(3) 2.15(3) 3.051(3) 167(3) 3_665 yes
C102 H10C O21 0.99 2.52 3.240(3) 129.5 3_666 yes
C106 H10L O1 0.99 2.50 3.412(3) 153.0 2_545 yes

_refine_diff_density_max         2.062
_refine_diff_density_min         -1.113
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_EF392
_database_code_depnum_ccdc_archive 'CCDC 2076834'
loop_
_audit_author_name
_audit_author_address
'Jose Goicoechea'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
 [K(18-crown-6)][PHC(O)NHNH2]
;
_contact_author_fax              '+44 1865 272690'
_chemical_name_common            .
_chemical_melting_point          .
_chemical_formula_moiety         'C H4 N2 O P, C12 H24 K O6'
_chemical_formula_sum            'C13 H28 K N2 O7 P'
_chemical_formula_weight         394.44

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   16.5692(3)
_cell_length_b                   8.8974(2)
_cell_length_c                   12.9189(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1904.54(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9351
_cell_measurement_theta_min      2.4660
_cell_measurement_theta_max      28.5360

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.398
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5035
_diffrn_reflns_number            25455
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.458
_diffrn_reflns_theta_max         28.860
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4693
_reflns_number_gt                4322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.916
_reflns_Friedel_fraction_full    1.000

_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0232P)²+0.4223P] 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 1871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4693
_refine_ls_number_parameters     233
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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
P1 P 0.60601(4) 0.43742(8) 1.08420(6) 0.03342(16) Uani 1 1 d . . . A 1
C1 C 0.70642(14) 0.3728(3) 1.11039(18) 0.0239(5) Uani 1 1 d . . . A 1
O1 O 0.77154(10) 0.4349(2) 1.08755(16) 0.0400(5) Uani 1 1 d . . . A 1
N1 N 0.71141(14) 0.2365(3) 1.16144(19) 0.0324(5) Uani 1 1 d . . . A 1
N2 N 0.64654(16) 0.1733(3) 1.2145(3) 0.0441(6) Uani 1 1 d . . . A 1
K1 K 0.77359(3) 0.59127(5) 0.91037(4) 0.02201(11) Uani 1 1 d . . . A 1
O101 O 0.89268(10) 0.77367(17) 1.00529(14) 0.0259(4) Uani 1 1 d . . . A 1
O102 O 0.93810(9) 0.49233(17) 0.92506(14) 0.0256(4) Uani 1 1 d . . . A 1
O103 O 0.81383(10) 0.31565(18) 0.82881(14) 0.0279(4) Uani 1 1 d . . . A 1
O104 O 0.67199(10) 0.46361(18) 0.74987(14) 0.0275(4) Uani 1 1 d . . . A 1
O105 O 0.63270(10) 0.74135(18) 0.83282(14) 0.0267(4) Uani 1 1 d . . . A 1
O106 O 0.76042(9) 0.91609(16) 0.90908(17) 0.0252(3) Uani 1 1 d . . . A 1
C101 C 0.97120(14) 0.7129(3) 1.0182(2) 0.0282(5) Uani 1 1 d . . . A 1
H10A H 0.995814 0.751842 1.082627 0.034 Uiso 1 1 calc R U . A 1
H10B H 1.005950 0.742113 0.959185 0.034 Uiso 1 1 calc R U . A 1
C102 C 0.96407(14) 0.5447(3) 1.0235(2) 0.0279(5) Uani 1 1 d . . . A 1
H10C H 1.016925 0.499702 1.041327 0.033 Uiso 1 1 calc R U . A 1
H10D H 0.924553 0.515679 1.077392 0.033 Uiso 1 1 calc R U . A 1
C103 C 0.93783(15) 0.3322(3) 0.9190(3) 0.0328(6) Uani 1 1 d . . . A 1
H10E H 0.908213 0.289482 0.978719 0.039 Uiso 1 1 calc R U . A 1
H10F H 0.993854 0.293607 0.920600 0.039 Uiso 1 1 calc R U . A 1
C104 C 0.89761(16) 0.2875(3) 0.8200(2) 0.0339(6) Uani 1 1 d . . . A 1
H10G H 0.920334 0.345954 0.761708 0.041 Uiso 1 1 calc R U . A 1
H10H H 0.907025 0.179403 0.806321 0.041 Uiso 1 1 calc R U . A 1
C105 C 0.76912(17) 0.2662(3) 0.7407(2) 0.0357(6) Uani 1 1 d . . . A 1
H10I H 0.775182 0.156155 0.732196 0.043 Uiso 1 1 calc R U . A 1
H10J H 0.789888 0.315735 0.677436 0.043 Uiso 1 1 calc R U . A 1
C106 C 0.68246(17) 0.3048(3) 0.7557(2) 0.0360(6) Uani 1 1 d . . . A 1
H10K H 0.649485 0.255172 0.701713 0.043 Uiso 1 1 calc R U . A 1
H10L H 0.664075 0.268034 0.824118 0.043 Uiso 1 1 calc R U . A 1
C107 C 0.59007(14) 0.5063(3) 0.7680(2) 0.0319(6) Uani 1 1 d . . . A 1
H10M H 0.573564 0.476930 0.838788 0.038 Uiso 1 1 calc R U . A 1
H10N H 0.554067 0.455311 0.717922 0.038 Uiso 1 1 calc R U . A 1
C108 C 0.58393(15) 0.6733(3) 0.7554(2) 0.0308(6) Uani 1 1 d . . . A 1
H10O H 0.602929 0.703324 0.685778 0.037 Uiso 1 1 calc R U . A 1
H10P H 0.527131 0.705935 0.763276 0.037 Uiso 1 1 calc R U . A 1
C109 C 0.63164(15) 0.9018(3) 0.8293(2) 0.0275(5) Uani 1 1 d . . . A 1
H10Q H 0.575380 0.939139 0.831640 0.033 Uiso 1 1 calc R U . A 1
H10R H 0.657016 0.937881 0.764484 0.033 Uiso 1 1 calc R U . A 1
C110 C 0.67792(13) 0.9576(3) 0.9213(2) 0.0270(5) Uani 1 1 d . . . A 1
H11A H 0.673152 1.068280 0.926494 0.032 Uiso 1 1 calc R U . A 1
H11B H 0.655890 0.912741 0.985493 0.032 Uiso 1 1 calc R U . A 1
C111 C 0.80992(14) 0.9887(3) 0.9847(2) 0.0259(5) Uani 1 1 d . . . A 1
H11C H 0.788365 0.969474 1.054985 0.031 Uiso 1 1 calc R U . A 1
H11D H 0.810177 1.098562 0.972783 0.031 Uiso 1 1 calc R U . A 1
C112 C 0.89364(15) 0.9279(3) 0.9761(2) 0.0269(5) Uani 1 1 d . . . A 1
H11E H 0.913209 0.938167 0.904002 0.032 Uiso 1 1 calc R U . A 1
H11F H 0.930420 0.984913 1.021984 0.032 Uiso 1 1 calc R U . A 1
H2 H 0.756(2) 0.208(4) 1.180(3) 0.042(9) Uiso 1 1 d . . . B 1
H3 H 0.6225(16) 0.133(3) 1.166(2) 0.019(7) Uiso 1 1 d . . . C 1
H4 H 0.6166(19) 0.250(4) 1.241(3) 0.050(10) Uiso 1 1 d . . . D 1
H1 H 0.6317(18) 0.565(4) 1.043(2) 0.047(9) 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 C1 1.792(2) . ?
P1 K1 3.8244(9) . ?
P1 H1 1.32(3) . ?
C1 O1 1.248(3) . ?
C1 N1 1.383(3) . ?
C1 K1 3.420(2) . ?
O1 K1 2.679(2) . ?
N1 N2 1.393(3) . ?
N1 H2 0.82(3) . ?
N2 K1 2.948(3) 4_645 ?
N2 H3 0.82(3) . ?
N2 H4 0.91(3) . ?
K1 O103 2.7511(17) . ?
K1 O101 2.8340(17) . ?
K1 O105 2.8698(17) . ?
K1 O102 2.8707(16) . ?
K1 O106 2.8983(15) . ?
K1 O104 2.9023(18) . ?
K1 C102 3.503(2) . ?
K1 H1 2.92(3) . ?
O101 C101 1.419(3) . ?
O101 C112 1.424(3) . ?
O102 C102 1.421(3) . ?
O102 C103 1.427(3) . ?
O103 C104 1.415(3) . ?
O103 C105 1.428(3) . ?
O104 C106 1.426(3) . ?
O104 C107 1.429(3) . ?
O105 C108 1.421(3) . ?
O105 C109 1.429(3) . ?
O106 C110 1.425(3) . ?
O106 C111 1.430(3) . ?
C101 C102 1.503(3) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C102 H10C 0.9900 . ?
C102 H10D 0.9900 . ?
C103 C104 1.496(4) . ?
C103 H10E 0.9900 . ?
C103 H10F 0.9900 . ?
C104 H10G 0.9900 . ?
C104 H10H 0.9900 . ?
C105 C106 1.489(4) . ?
C105 H10I 0.9900 . ?
C105 H10J 0.9900 . ?
C106 H10K 0.9900 . ?
C106 H10L 0.9900 . ?
C107 C108 1.498(4) . ?
C107 H10M 0.9900 . ?
C107 H10N 0.9900 . ?
C108 H10O 0.9900 . ?
C108 H10P 0.9900 . ?
C109 C110 1.500(4) . ?
C109 H10Q 0.9900 . ?
C109 H10R 0.9900 . ?
C110 H11A 0.9900 . ?
C110 H11B 0.9900 . ?
C111 C112 1.493(3) . ?
C111 H11C 0.9900 . ?
C111 H11D 0.9900 . ?
C112 H11E 0.9900 . ?
C112 H11F 0.9900 . ?

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
C1 P1 K1 63.37(8) . . ?
C1 P1 H1 93.0(13) . . ?
K1 P1 H1 39.2(13) . . ?
O1 C1 N1 116.7(2) . . ?
O1 C1 P1 128.0(2) . . ?
N1 C1 P1 115.26(18) . . ?
O1 C1 K1 44.61(12) . . ?
N1 C1 K1 147.07(16) . . ?
P1 C1 K1 88.69(9) . . ?
C1 O1 K1 116.30(15) . . ?
C1 N1 N2 122.8(2) . . ?
C1 N1 H2 118(2) . . ?
N2 N1 H2 115(2) . . ?
N1 N2 K1 100.12(17) . 4_645 ?
N1 N2 H3 99.9(19) . . ?
K1 N2 H3 139.8(19) 4_645 . ?
N1 N2 H4 108(2) . . ?
K1 N2 H4 96(2) 4_645 . ?
H3 N2 H4 110(3) . . ?
O1 K1 O103 82.38(6) . . ?
O1 K1 O101 86.36(6) . . ?
O103 K1 O101 120.49(5) . . ?
O1 K1 O105 121.98(5) . . ?
O103 K1 O105 118.57(5) . . ?
O101 K1 O105 116.81(5) . . ?
O1 K1 O102 78.25(5) . . ?
O103 K1 O102 61.43(5) . . ?
O101 K1 O102 59.06(5) . . ?
O105 K1 O102 159.74(5) . . ?
O1 K1 O106 121.45(7) . . ?
O103 K1 O106 154.81(6) . . ?
O101 K1 O106 58.93(5) . . ?
O105 K1 O106 58.19(5) . . ?
O102 K1 O106 112.19(4) . . ?
O1 K1 O104 113.57(6) . . ?
O103 K1 O104 61.19(5) . . ?
O101 K1 O104 159.57(5) . . ?
O105 K1 O104 57.38(5) . . ?
O102 K1 O104 118.55(5) . . ?
O106 K1 O104 110.03(5) . . ?
O1 K1 N2 150.22(7) . 4_654 ?
O103 K1 N2 77.47(7) . 4_654 ?
O101 K1 N2 85.25(7) . 4_654 ?
O105 K1 N2 87.15(6) . 4_654 ?
O102 K1 N2 72.93(6) . 4_654 ?
O106 K1 N2 77.41(8) . 4_654 ?
O104 K1 N2 75.16(7) . 4_654 ?
O1 K1 C1 19.09(5) . . ?
O103 K1 C1 82.05(6) . . ?
O101 K1 C1 103.01(6) . . ?
O105 K1 C1 105.28(6) . . ?
O102 K1 C1 94.86(5) . . ?
O106 K1 C1 123.13(6) . . ?
O104 K1 C1 97.39(5) . . ?
N2 K1 C1 159.33(8) 4_654 . ?
O1 K1 C102 66.01(5) . . ?
O103 K1 C102 80.56(6) . . ?
O101 K1 C102 42.25(5) . . ?
O105 K1 C102 159.01(5) . . ?
O102 K1 C102 23.15(6) . . ?
O106 K1 C102 100.85(5) . . ?
O104 K1 C102 140.75(6) . . ?
N2 K1 C102 89.03(7) 4_654 . ?
C1 K1 C102 84.87(6) . . ?
O1 K1 P1 45.83(4) . . ?
O103 K1 P1 94.69(4) . . ?
O101 K1 P1 117.15(4) . . ?
O105 K1 P1 77.35(4) . . ?
O102 K1 P1 122.74(4) . . ?
O106 K1 P1 107.80(4) . . ?
O104 K1 P1 81.86(4) . . ?
N2 K1 P1 156.74(6) 4_654 . ?
C1 K1 P1 27.94(4) . . ?
C102 K1 P1 111.52(5) . . ?
O1 K1 H1 56.4(6) . . ?
O103 K1 H1 110.4(6) . . ?
O101 K1 H1 110.6(6) . . ?
O105 K1 H1 65.6(6) . . ?
O102 K1 H1 134.5(6) . . ?
O106 K1 H1 91.3(6) . . ?
O104 K1 H1 85.5(6) . . ?
N2 K1 H1 152.3(6) 4_654 . ?
C1 K1 H1 41.3(6) . . ?
C102 K1 H1 118.1(6) . . ?
P1 K1 H1 16.6(6) . . ?
C101 O101 C112 112.86(18) . . ?
C101 O101 K1 118.09(13) . . ?
C112 O101 K1 116.44(14) . . ?
C102 O102 C103 112.2(2) . . ?
C102 O102 K1 104.26(13) . . ?
C103 O102 K1 107.44(12) . . ?
C104 O103 C105 113.0(2) . . ?
C104 O103 K1 115.24(14) . . ?
C105 O103 K1 117.03(14) . . ?
C106 O104 C107 111.75(19) . . ?
C106 O104 K1 106.22(14) . . ?
C107 O104 K1 109.26(14) . . ?
C108 O105 C109 113.33(19) . . ?
C108 O105 K1 120.67(13) . . ?
C109 O105 K1 119.10(13) . . ?
C110 O106 C111 110.94(19) . . ?
C110 O106 K1 109.28(12) . . ?
C111 O106 K1 113.78(14) . . ?
O101 C101 C102 108.25(19) . . ?
O101 C101 H10A 110.0 . . ?
C102 C101 H10A 110.0 . . ?
O101 C101 H10B 110.0 . . ?
C102 C101 H10B 110.0 . . ?
H10A C101 H10B 108.4 . . ?
O102 C102 C101 108.0(2) . . ?
O102 C102 K1 52.59(10) . . ?
C101 C102 K1 86.21(14) . . ?
O102 C102 H10C 110.1 . . ?
C101 C102 H10C 110.1 . . ?
K1 C102 H10C 160.4 . . ?
O102 C102 H10D 110.1 . . ?
C101 C102 H10D 110.1 . . ?
K1 C102 H10D 74.2 . . ?
H10C C102 H10D 108.4 . . ?
O102 C103 C104 108.3(2) . . ?
O102 C103 H10E 110.0 . . ?
C104 C103 H10E 110.0 . . ?
O102 C103 H10F 110.0 . . ?
C104 C103 H10F 110.0 . . ?
H10E C103 H10F 108.4 . . ?
O103 C104 C103 108.7(2) . . ?
O103 C104 H10G 109.9 . . ?
C103 C104 H10G 109.9 . . ?
O103 C104 H10H 109.9 . . ?
C103 C104 H10H 109.9 . . ?
H10G C104 H10H 108.3 . . ?
O103 C105 C106 109.0(2) . . ?
O103 C105 H10I 109.9 . . ?
C106 C105 H10I 109.9 . . ?
O103 C105 H10J 109.9 . . ?
C106 C105 H10J 109.9 . . ?
H10I C105 H10J 108.3 . . ?
O104 C106 C105 109.8(2) . . ?
O104 C106 H10K 109.7 . . ?
C105 C106 H10K 109.7 . . ?
O104 C106 H10L 109.7 . . ?
C105 C106 H10L 109.7 . . ?
H10K C106 H10L 108.2 . . ?
O104 C107 C108 108.10(19) . . ?
O104 C107 H10M 110.1 . . ?
C108 C107 H10M 110.1 . . ?
O104 C107 H10N 110.1 . . ?
C108 C107 H10N 110.1 . . ?
H10M C107 H10N 108.4 . . ?
O105 C108 C107 107.92(19) . . ?
O105 C108 H10O 110.1 . . ?
C107 C108 H10O 110.1 . . ?
O105 C108 H10P 110.1 . . ?
C107 C108 H10P 110.1 . . ?
H10O C108 H10P 108.4 . . ?
O105 C109 C110 107.40(19) . . ?
O105 C109 H10Q 110.2 . . ?
C110 C109 H10Q 110.2 . . ?
O105 C109 H10R 110.2 . . ?
C110 C109 H10R 110.2 . . ?
H10Q C109 H10R 108.5 . . ?
O106 C110 C109 108.5(2) . . ?
O106 C110 H11A 110.0 . . ?
C109 C110 H11A 110.0 . . ?
O106 C110 H11B 110.0 . . ?
C109 C110 H11B 110.0 . . ?
H11A C110 H11B 108.4 . . ?
O106 C111 C112 108.6(2) . . ?
O106 C111 H11C 110.0 . . ?
C112 C111 H11C 110.0 . . ?
O106 C111 H11D 110.0 . . ?
C112 C111 H11D 110.0 . . ?
H11C C111 H11D 108.4 . . ?
O101 C112 C111 108.57(19) . . ?
O101 C112 H11E 110.0 . . ?
C111 C112 H11E 110.0 . . ?
O101 C112 H11F 110.0 . . ?
C111 C112 H11F 110.0 . . ?
H11E C112 H11F 108.4 . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2076833'
loop_
_audit_author_name
_audit_author_address
'Jose Goicoechea'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-04-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 PH2C(O)NHCH2CH2NHC(O)PH2
;
_contact_author_fax              '+44 1865 272690'
_chemical_name_common            .
_chemical_melting_point          .
_chemical_formula_moiety         'C4 H10 N2 O2 P2'
_chemical_formula_sum            'C4 H10 N2 O2 P2'
_chemical_formula_weight         180.08

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.1091(2)
_cell_length_b                   4.91330(10)
_cell_length_c                   12.5171(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.067(2)
_cell_angle_gamma                90
_cell_volume                     436.927(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2925
_cell_measurement_theta_min      3.5304
_cell_measurement_theta_max      75.7343

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             188
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    4.156
_shelx_estimated_absorpt_T_min   0.594
_shelx_estimated_absorpt_T_max   0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4102
_diffrn_reflns_number            3760
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         7.056
_diffrn_reflns_theta_max         75.915
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             896
_reflns_number_gt                869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'WinGX (Farrugia, 2005)'
_computing_publication_material  'XCIF (Sheldrick, 2001)'

_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)+(0.0327P)²+0.1084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   .
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         896
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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
P1 P -0.00084(4) -0.03564(7) 0.14289(2) 0.03227(14) Uani 1 1 d . . . . .
C1 C -0.02904(15) -0.1275(2) 0.28584(9) 0.0248(2) Uani 1 1 d . . . . .
O1 O -0.03026(15) -0.36949(18) 0.31022(8) 0.0439(3) Uani 1 1 d . . . . .
N1 N -0.05620(15) 0.0707(2) 0.35547(8) 0.0252(2) Uani 1 1 d . . . . .
C2 C -0.09135(17) 0.0157(3) 0.46721(10) 0.0286(3) Uani 1 1 d . . . . .
H1 H 0.169(3) -0.112(4) 0.1418(17) 0.075(6) Uiso 1 1 d . . . . .
H2 H 0.041(2) 0.204(4) 0.1534(15) 0.057(5) Uiso 1 1 d . . . . .
H3 H -0.047(2) 0.228(4) 0.3368(13) 0.032(4) Uiso 1 1 d . . . . .
H4 H -0.165(2) 0.166(4) 0.4976(13) 0.047(4) Uiso 1 1 d . . . . .
H5 H -0.164(2) -0.142(4) 0.4703(13) 0.045(4) 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 C1 1.8633(12) . ?
P1 H1 1.26(2) . ?
P1 H2 1.22(2) . ?
C1 O1 1.2275(15) . ?
C1 N1 1.3256(15) . ?
N1 C2 1.4549(15) . ?
N1 H3 0.813(17) . ?
C2 C2 1.519(2) 3_556 ?
C2 H4 0.989(18) . ?
C2 H5 0.934(18) . ?

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
C1 P1 H1 94.3(10) . . ?
C1 P1 H2 99.5(9) . . ?
H1 P1 H2 93.5(12) . . ?
O1 C1 N1 123.06(11) . . ?
O1 C1 P1 118.38(9) . . ?
N1 C1 P1 118.47(8) . . ?
C1 N1 C2 121.99(10) . . ?
C1 N1 H3 119.8(11) . . ?
C2 N1 H3 118.2(11) . . ?
N1 C2 C2 111.42(13) . 3_556 ?
N1 C2 H4 110.0(10) . . ?
C2 C2 H4 108.7(10) 3_556 . ?
N1 C2 H5 108.0(10) . . ?
C2 C2 H5 110.9(10) 3_556 . ?
H4 C2 H5 107.7(14) . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-1

