# Electronic Supplementary Material (ESI) for ChemComm.
# 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_20150465
_database_code_depnum_ccdc_archive 'CCDC 1411223'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_date             2015-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N2 O4 P, C2 H5 N O'
_chemical_formula_sum            'C12 H16 N3 O5 P'
_chemical_formula_weight         313.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4P1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6832(6)
_cell_length_b                   9.6923(7)
_cell_length_c                   10.0668(9)
_cell_angle_alpha                89.063(6)
_cell_angle_beta                 82.389(7)
_cell_angle_gamma                80.144(7)
_cell_volume                     732.07(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2005
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      72.1530
_cell_measurement_theta_min      4.4350
_shelx_estimated_absorpt_T_max   0.701
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    1.915
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5500
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.466
_diffrn_reflns_theta_min         4.431
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -77.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega  -63.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -69.00  -41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  8 omega   70.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
  9 omega   79.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 10 omega   -2.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -90.0000 72

#__ type_ start__ end____ width___ exp.time_
 11 omega  -15.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
 12 omega   68.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000    0.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   27.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   50.00  106.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 15 omega   69.00   95.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   68.00   94.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   45.00   98.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 18 omega   48.00  107.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
 19 omega   58.00  100.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 20 omega   49.00   84.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 21 omega   42.00   92.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 22 omega   99.00  125.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00   88.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 24 omega   60.00  132.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   90.0000 72

#__ type_ start__ end____ width___ exp.time_
 25 omega   79.00  113.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 26 omega   93.00  178.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
 27 omega   42.00   77.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 28 omega   41.00  160.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000   60.0000 119

#__ type_ start__ end____ width___ exp.time_
 29 omega  -21.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 30 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 31 omega   35.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 32 omega   26.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   77.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
 33 omega   35.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000   90.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0794568000
_diffrn_orient_matrix_UB_12      -0.0139691000
_diffrn_orient_matrix_UB_13      -0.1308512000
_diffrn_orient_matrix_UB_21      0.1882912000
_diffrn_orient_matrix_UB_22      -0.0516779000
_diffrn_orient_matrix_UB_23      -0.0736442000
_diffrn_orient_matrix_UB_31      -0.0195307000
_diffrn_orient_matrix_UB_32      -0.1521906000
_diffrn_orient_matrix_UB_33      0.0359590000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2236
_reflns_number_total             2811
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.044
_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)+(0.0572P)²+0.1247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1212
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.1732(4) 0.3260(2) 0.5858(3) 0.0529(6) Uani 1 1 d . . . . .
H1 H 0.1230 0.2935 0.6670 0.063 Uiso 1 1 calc R . . . .
C2 C 0.2154(4) 0.2386(3) 0.4770(3) 0.0585(7) Uani 1 1 d . . . . .
H2 H 0.1930 0.1472 0.4837 0.070 Uiso 1 1 calc R . . . .
C3 C 0.2923(4) 0.2872(3) 0.3556(3) 0.0565(7) Uani 1 1 d . . . . .
H3 H 0.3222 0.2271 0.2820 0.068 Uiso 1 1 calc R . . . .
C4 C 0.3246(3) 0.4215(3) 0.3431(2) 0.0490(6) Uani 1 1 d . . . . .
H4 H 0.3759 0.4527 0.2618 0.059 Uiso 1 1 calc R . . . .
C5 C 0.2794(3) 0.5111(2) 0.4541(2) 0.0404(5) Uani 1 1 d . . . . .
C6 C 0.2046(3) 0.4638(2) 0.5763(2) 0.0405(5) Uani 1 1 d . . . . .
C7 C 0.1924(3) 0.6777(2) 0.6765(2) 0.0396(5) Uani 1 1 d . . . . .
C8 C 0.2636(3) 0.7397(2) 0.5504(2) 0.0437(5) Uani 1 1 d . . . . .
C9 C -0.0359(4) 1.0340(3) 0.7775(4) 0.0812(10) Uani 1 1 d . . . . .
H9A H -0.0548 1.0480 0.6855 0.122 Uiso 1 1 calc GR . . . .
H9B H 0.0744 1.0623 0.7908 0.122 Uiso 1 1 calc GR . . . .
H9C H -0.1322 1.0891 0.8342 0.122 Uiso 1 1 calc GR . . . .
C10 C 0.1965(5) 0.5890(3) 1.0031(3) 0.0732(9) Uani 1 1 d . . . . .
H10A H 0.2566 0.5200 0.9377 0.110 Uiso 1 1 calc GR . . . .
H10B H 0.1310 0.5445 1.0743 0.110 Uiso 1 1 calc GR . . . .
H10C H 0.2826 0.6338 1.0388 0.110 Uiso 1 1 calc GR . . . .
N1 N 0.3071(3) 0.6483(2) 0.44576(19) 0.0441(5) Uani 1 1 d . . . . .
H1A H 0.356(3) 0.678(3) 0.364(3) 0.056(7) Uiso 1 1 d . . . . .
N2 N 0.1634(2) 0.54996(18) 0.68828(18) 0.0417(4) Uani 1 1 d . . . . .
O1 O 0.2823(3) 0.86318(17) 0.53984(17) 0.0583(5) Uani 1 1 d . . . . .
O2 O 0.2997(2) 0.84931(17) 0.84967(17) 0.0541(4) Uani 1 1 d . . . . .
O3 O -0.0287(2) 0.89040(18) 0.8099(2) 0.0607(5) Uani 1 1 d . . . . .
O4 O 0.0746(2) 0.69288(18) 0.94029(16) 0.0531(4) Uani 1 1 d . . . . .
P1 P 0.14647(8) 0.78706(6) 0.82531(6) 0.04338(19) Uani 1 1 d . . . . .
C11 C 0.5328(3) 0.8227(2) 0.1800(2) 0.0449(5) Uani 1 1 d . . . . .
C12 C 0.6383(4) 0.8345(3) 0.0457(3) 0.0587(7) Uani 1 1 d . . . . .
H12A H 0.7458 0.7664 0.0383 0.088 Uiso 1 1 calc GR . . . .
H12B H 0.6679 0.9267 0.0358 0.088 Uiso 1 1 calc GR . . . .
H12C H 0.5690 0.8178 -0.0232 0.088 Uiso 1 1 calc GR . . . .
N3 N 0.5208(3) 0.9250(2) 0.2679(2) 0.0549(5) Uani 1 1 d . . . . .
H3A H 0.577(4) 0.994(3) 0.249(3) 0.064(8) Uiso 1 1 d . . . . .
H3B H 0.466(4) 0.917(3) 0.351(3) 0.077(10) Uiso 1 1 d . . . . .
O5 O 0.4609(3) 0.71927(19) 0.20483(17) 0.0619(5) 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
C1 H1 0.9300 . ?
C1 C2 1.366(3) . ?
C1 C6 1.397(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(3) . ?
C5 C6 1.393(3) . ?
C5 N1 1.382(3) . ?
C6 N2 1.383(3) . ?
C7 C8 1.475(3) . ?
C7 N2 1.296(3) . ?
C7 P1 1.810(2) . ?
C8 N1 1.357(3) . ?
C8 O1 1.231(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 O3 1.418(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 O4 1.450(3) . ?
N1 H1A 0.92(3) . ?
O2 P1 1.4614(16) . ?
O3 P1 1.5581(18) . ?
O4 P1 1.5642(17) . ?
C11 C12 1.495(3) . ?
C11 N3 1.323(3) . ?
C11 O5 1.232(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N3 H3A 0.86(3) . ?
N3 H3B 0.89(3) . ?

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
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.4(2) . . ?
N1 C5 C4 121.2(2) . . ?
N1 C5 C6 118.4(2) . . ?
C5 C6 C1 119.1(2) . . ?
N2 C6 C1 119.7(2) . . ?
N2 C6 C5 121.2(2) . . ?
C8 C7 P1 117.56(16) . . ?
N2 C7 C8 124.5(2) . . ?
N2 C7 P1 117.94(17) . . ?
N1 C8 C7 114.02(19) . . ?
O1 C8 C7 123.5(2) . . ?
O1 C8 N1 122.5(2) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
C5 N1 H1A 117.3(16) . . ?
C8 N1 C5 123.3(2) . . ?
C8 N1 H1A 119.4(16) . . ?
C7 N2 C6 118.45(19) . . ?
C9 O3 P1 124.12(18) . . ?
C10 O4 P1 120.48(17) . . ?
O2 P1 C7 112.44(10) . . ?
O2 P1 O3 116.65(10) . . ?
O2 P1 O4 115.60(10) . . ?
O3 P1 C7 105.66(10) . . ?
O3 P1 O4 99.66(10) . . ?
O4 P1 C7 105.38(10) . . ?
N3 C11 C12 118.1(2) . . ?
O5 C11 C12 119.3(2) . . ?
O5 C11 N3 122.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 N3 H3A 120.5(19) . . ?
C11 N3 H3B 119.7(19) . . ?
H3A N3 H3B 119(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
N1 H1A O5 0.92(3) 1.77(3) 2.686(3) 175(2) .
N3 H3A O1 0.86(3) 2.97(3) 3.496(3) 121(2) 2_676
N3 H3A O2 0.86(3) 2.09(3) 2.933(3) 164(3) 2_676
N3 H3B O1 0.89(3) 2.33(3) 3.195(3) 166(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
C1 C2 C3 C4 -0.7(4) . . . . ?
C1 C6 N2 C7 -179.4(2) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C1 C6 N2 -179.0(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 N1 -179.1(2) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 N2 178.2(2) . . . . ?
C4 C5 N1 C8 179.3(2) . . . . ?
C5 C6 N2 C7 1.5(3) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C5 N1 C8 -0.7(3) . . . . ?
C7 C8 N1 C5 3.1(3) . . . . ?
C8 C7 N2 C6 1.2(3) . . . . ?
C8 C7 P1 O2 -53.0(2) . . . . ?
C8 C7 P1 O3 75.33(18) . . . . ?
C8 C7 P1 O4 -179.73(16) . . . . ?
C9 O3 P1 C7 -105.8(2) . . . . ?
C9 O3 P1 O2 20.0(3) . . . . ?
C9 O3 P1 O4 145.2(2) . . . . ?
C10 O4 P1 C7 78.6(2) . . . . ?
C10 O4 P1 O2 -46.2(2) . . . . ?
C10 O4 P1 O3 -172.05(18) . . . . ?
N1 C5 C6 C1 179.0(2) . . . . ?
N1 C5 C6 N2 -1.9(3) . . . . ?
N2 C7 C8 N1 -3.5(3) . . . . ?
N2 C7 C8 O1 176.5(2) . . . . ?
N2 C7 P1 O2 125.87(17) . . . . ?
N2 C7 P1 O3 -105.83(18) . . . . ?
N2 C7 P1 O4 -0.9(2) . . . . ?
O1 C8 N1 C5 -176.9(2) . . . . ?
P1 C7 C8 N1 175.29(16) . . . . ?
P1 C7 C8 O1 -4.8(3) . . . . ?
P1 C7 N2 C6 -177.51(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
