# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_a1-wght
_database_code_depnum_ccdc_archive 'CCDC 1425902'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-methylmorpholino-4-ium phenyl phosphate'
_chemical_name_common            'N-methyl-N-oxymorpholinium phenyl phosphate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H16 N O5 P'
_chemical_formula_sum            'C11 H16 N O5 P'
_chemical_formula_weight         273.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0190 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1480 0.1500 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   11.8630(10)
_cell_length_b                   14.0900(10)
_cell_length_c                   14.4570(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2416.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.443
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.88561
_diffrn_radiation_type           synchrotron
_diffrn_source                   'BESSY BL14.2'
_diffrn_measurement_device_type  'Mar Research MX-225'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean 25.6
_diffrn_reflns_number            2366
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.303
_diffrn_reflns_theta_max         33.130
_diffrn_reflns_theta_full        32.098
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2366
_reflns_number_gt                2114
_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       'HKL2000 (Otwinowski & Minor, 2007)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0706P)²+2.4486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2366
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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 0.20723(4) 0.55175(3) 0.63294(4) 0.01677(19) Uani 1 1 d . . . . .
O1 O 0.27467(11) 0.65150(9) 0.63667(10) 0.0175(3) Uani 1 1 d . . . . .
O2 O 0.29009(11) 0.47856(9) 0.69580(10) 0.0181(3) Uani 1 1 d . . . . .
O3 O 0.21525(12) 0.50877(11) 0.54131(11) 0.0256(4) Uani 1 1 d . . . . .
O4 O 0.10158(11) 0.56828(10) 0.68373(10) 0.0220(3) Uani 1 1 d . . . . .
C1 C 0.36882(15) 0.67484(13) 0.58368(13) 0.0148(4) Uani 1 1 d . . . . .
C2 C 0.37451(15) 0.76747(12) 0.55132(13) 0.0150(4) Uani 1 1 d . . . . .
H2 H 0.3148 0.8107 0.5633 0.018 Uiso 1 1 calc R U . . .
C3 C 0.46872(16) 0.79626(13) 0.50117(14) 0.0183(4) Uani 1 1 d . . . . .
H3 H 0.4734 0.8596 0.4789 0.022 Uiso 1 1 calc R U . . .
C4 C 0.55585(15) 0.73306(14) 0.48345(14) 0.0202(4) Uani 1 1 d . . . . .
H4 H 0.6197 0.7529 0.4489 0.024 Uiso 1 1 calc R U . . .
C5 C 0.54927(16) 0.64081(14) 0.51638(15) 0.0212(4) Uani 1 1 d . . . . .
H5 H 0.6089 0.5975 0.5044 0.025 Uiso 1 1 calc R U . . .
C6 C 0.45585(16) 0.61120(13) 0.56694(15) 0.0196(4) Uani 1 1 d . . . . .
H6 H 0.4517 0.5481 0.5898 0.023 Uiso 1 1 calc R U . . .
N1 N 0.29074(13) 0.47996(11) 0.79656(12) 0.0172(4) Uani 1 1 d . . . . .
C7 C 0.31115(19) 0.57750(14) 0.83256(14) 0.0225(4) Uani 1 1 d . . . . .
H7A H 0.3111 0.5763 0.9003 0.034 Uiso 1 1 calc R U . . .
H7B H 0.3843 0.6004 0.8104 0.034 Uiso 1 1 calc R U . . .
H7C H 0.2514 0.6200 0.8107 0.034 Uiso 1 1 calc R U . . .
C8 C 0.18281(17) 0.43938(14) 0.83585(14) 0.0191(4) Uani 1 1 d . . . . .
H8A H 0.1846 0.4431 0.9042 0.023 Uiso 1 1 calc R U . . .
H8B H 0.1177 0.4770 0.8137 0.023 Uiso 1 1 calc R U . . .
C9 C 0.16952(17) 0.33752(14) 0.80621(15) 0.0232(5) Uani 1 1 d . . . . .
H9A H 0.0994 0.3113 0.8331 0.028 Uiso 1 1 calc R U . . .
H9B H 0.1628 0.3346 0.7380 0.028 Uiso 1 1 calc R U . . .
C11 C 0.38701(16) 0.41583(14) 0.82301(14) 0.0210(4) Uani 1 1 d . . . . .
H11A H 0.3978 0.4177 0.8909 0.025 Uiso 1 1 calc R U . . .
H11B H 0.4572 0.4386 0.7935 0.025 Uiso 1 1 calc R U . . .
C10 C 0.36384(18) 0.31494(14) 0.79292(15) 0.0237(4) Uani 1 1 d . . . . .
H10A H 0.3564 0.3124 0.7248 0.028 Uiso 1 1 calc R U . . .
H10B H 0.4276 0.2737 0.8111 0.028 Uiso 1 1 calc R U . . .
05 O 0.26252(13) 0.28153(10) 0.83499(11) 0.0252(4) Uani 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 O3 1.4596(17) . ?
P1 O4 1.4712(14) . ?
P1 O1 1.6181(14) . ?
P1 O2 1.6898(14) . ?
O1 C1 1.394(2) . ?
O2 N1 1.457(2) . ?
C1 C2 1.388(2) . ?
C1 C6 1.389(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N1 C7 1.489(2) . ?
N1 C11 1.506(2) . ?
N1 C8 1.513(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.506(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 05 1.419(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C10 1.512(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 05 1.427(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 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
O3 P1 O4 125.04(9) . . ?
O3 P1 O1 111.00(8) . . ?
O4 P1 O1 105.49(8) . . ?
O3 P1 O2 101.36(8) . . ?
O4 P1 O2 108.89(8) . . ?
O1 P1 O2 102.97(7) . . ?
C1 O1 P1 125.65(12) . . ?
N1 O2 P1 122.18(11) . . ?
C2 C1 C6 120.82(17) . . ?
C2 C1 O1 116.49(16) . . ?
C6 C1 O1 122.63(16) . . ?
C1 C2 C3 119.23(17) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.45(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.74(18) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.41(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.35(18) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O2 N1 C7 111.27(15) . . ?
O2 N1 C11 104.47(14) . . ?
C7 N1 C11 109.98(15) . . ?
O2 N1 C8 111.46(14) . . ?
C7 N1 C8 110.80(15) . . ?
C11 N1 C8 108.65(15) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 109.99(16) . . ?
C9 C8 H8A 109.7 . . ?
N1 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
N1 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
05 C9 C8 111.42(16) . . ?
05 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
05 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
N1 C11 C10 110.69(16) . . ?
N1 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
05 C10 C11 109.92(17) . . ?
05 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
05 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C9 05 C10 110.28(15) . . ?

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_a2-wght
_database_code_depnum_ccdc_archive 'CCDC 1425903'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'phenyl (trimethylammonio) phosphate'
_chemical_name_common            'phenyl trimethyloxyammonium phosphate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N O4 P'
_chemical_formula_sum            'C9 H14 N O4 P'
_chemical_formula_weight         231.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 '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 0.0110 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0190 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1480 0.1500 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.2080(10)
_cell_length_b                   7.2180(10)
_cell_length_c                   12.4960(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.22
_cell_angle_gamma                90
_cell_volume                     547.24(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.453
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.88561
_diffrn_radiation_type           synchrotron
_diffrn_source                   'BESSY BL14.2'
_diffrn_measurement_device_type  'Mar Research MX-225'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean 25.6
_diffrn_reflns_number            1164
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.158
_diffrn_reflns_theta_max         33.183
_diffrn_reflns_theta_full        32.098
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.536
_diffrn_reflns_point_group_measured_fraction_full 0.539
_reflns_number_total             1164
_reflns_number_gt                1133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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       'HKL2000 (Otwinowski & Minor, 2007)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0364P)²+0.2261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.15(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1164
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_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 0.38585(8) 0.79337(8) 0.17677(4) 0.00978(14) Uani 1 1 d . . . . .
O1 O 0.3902(2) 0.7854(3) 0.30656(11) 0.0112(3) Uani 1 1 d . . . . .
O2 O 0.1732(2) 0.9381(2) 0.13205(12) 0.0111(3) Uani 1 1 d . . . . .
O3 O 0.3001(3) 0.6187(2) 0.12385(13) 0.0159(4) Uani 1 1 d . . . . .
O4 O 0.5922(2) 0.8833(3) 0.16534(13) 0.0155(4) Uani 1 1 d . . . . .
C1 C 0.2509(3) 0.6705(3) 0.35090(17) 0.0093(4) Uani 1 1 d . . . . .
C2 C 0.3450(4) 0.5735(3) 0.44542(17) 0.0127(5) Uani 1 1 d . . . . .
H2 H 0.4982 0.5845 0.4759 0.015 Uiso 1 1 calc R U . . .
C3 C 0.2135(4) 0.4606(4) 0.49484(18) 0.0159(5) Uani 1 1 d . . . . .
H3 H 0.2764 0.3957 0.5601 0.019 Uiso 1 1 calc R U . . .
C4 C -0.0101(4) 0.4422(4) 0.44902(18) 0.0170(5) Uani 1 1 d . . . . .
H4 H -0.0995 0.3626 0.4818 0.020 Uiso 1 1 calc R U . . .
C5 C -0.1016(4) 0.5411(4) 0.35481(18) 0.0144(5) Uani 1 1 d . . . . .
H5 H -0.2544 0.5286 0.3237 0.017 Uiso 1 1 calc R U . . .
C6 C 0.0263(4) 0.6577(3) 0.30533(17) 0.0111(4) Uani 1 1 d . . . . .
H6 H -0.0378 0.7271 0.2420 0.013 Uiso 1 1 calc R U . . .
N1 N 0.2009(3) 1.1369(3) 0.13735(15) 0.0107(4) Uani 1 1 d . . . . .
C7 C -0.0288(4) 1.2067(4) 0.12581(19) 0.0167(5) Uani 1 1 d . . . . .
H7A H -0.0275 1.3424 0.1284 0.025 Uiso 1 1 calc R U . . .
H7B H -0.1183 1.1654 0.0556 0.025 Uiso 1 1 calc R U . . .
H7C H -0.0917 1.1582 0.1858 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3379(4) 1.2010(4) 0.24402(18) 0.0157(5) Uani 1 1 d . . . . .
H8A H 0.3514 1.3363 0.2432 0.024 Uiso 1 1 calc R U . . .
H8B H 0.2674 1.1639 0.3038 0.024 Uiso 1 1 calc R U . . .
H8C H 0.4847 1.1450 0.2549 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2941(4) 1.1968(3) 0.04190(19) 0.0159(5) Uani 1 1 d . . . . .
H9A H 0.3142 1.3315 0.0440 0.024 Uiso 1 1 calc R U . . .
H9B H 0.4367 1.1362 0.0455 0.024 Uiso 1 1 calc R U . . .
H9C H 0.1926 1.1619 -0.0263 0.024 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 O4 1.4695(17) . ?
P1 O3 1.4701(18) . ?
P1 O1 1.6174(14) . ?
P1 O2 1.6836(17) . ?
O1 C1 1.395(3) . ?
O2 N1 1.445(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N1 C7 1.490(3) . ?
N1 C8 1.495(3) . ?
N1 C9 1.496(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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 O3 125.10(10) . . ?
O4 P1 O1 106.45(9) . . ?
O3 P1 O1 110.37(10) . . ?
O4 P1 O2 109.38(9) . . ?
O3 P1 O2 101.50(9) . . ?
O1 P1 O2 101.56(8) . . ?
C1 O1 P1 122.64(14) . . ?
N1 O2 P1 121.59(13) . . ?
C2 C1 C6 121.2(2) . . ?
C2 C1 O1 116.89(19) . . ?
C6 C1 O1 121.88(18) . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
O2 N1 C7 103.23(18) . . ?
O2 N1 C8 112.84(17) . . ?
C7 N1 C8 109.50(18) . . ?
O2 N1 C9 108.22(17) . . ?
C7 N1 C9 110.44(18) . . ?
C8 N1 C9 112.24(19) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
