# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1536105'
_audit_update_record             
;
2017-03-06 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H24 N O4 P'
_chemical_formula_weight         253.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   17.6894(18)
_cell_length_b                   6.6145(7)
_cell_length_c                   23.997(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.392(11)
_cell_angle_gamma                90
_cell_volume                     2761.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2440
_cell_measurement_theta_min      2.341\%
_cell_measurement_theta_max      24.996\%

_exptl_crystal_description       Needles
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71423
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9844
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2440
_reflns_number_gt                1852
_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       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_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)+(0.0652P)²+3.5248P] 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         2440
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1361
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
C1 C 0.7045(2) 0.5289(5) 0.12418(15) 0.0511(9) Uani 1 1 d . . . . .
C2 C 0.7883(2) 0.5380(7) 0.15378(19) 0.0774(13) Uani 1 1 d . . . . .
H2A H 0.7967 0.6588 0.1762 0.116 Uiso 1 1 calc R U . . .
H2B H 0.8210 0.5391 0.1259 0.116 Uiso 1 1 calc R U . . .
H2C H 0.8000 0.4220 0.1778 0.116 Uiso 1 1 calc R U . . .
C3 C 0.6868(3) 0.3343(8) 0.0946(2) 0.116(2) Uani 1 1 d . . . . .
H3A H 0.6980 0.2254 0.1212 0.174 Uiso 1 1 calc R U . . .
H3B H 0.7176 0.3202 0.0657 0.174 Uiso 1 1 calc R U . . .
H3C H 0.6334 0.3307 0.0775 0.174 Uiso 1 1 calc R U . . .
C4 C 0.6878(3) 0.7081(8) 0.0854(2) 0.118(2) Uani 1 1 d . . . . .
H4A H 0.6350 0.7046 0.0669 0.177 Uiso 1 1 calc R U . . .
H4B H 0.7204 0.7037 0.0574 0.177 Uiso 1 1 calc R U . . .
H4C H 0.6974 0.8304 0.1070 0.177 Uiso 1 1 calc R U . . .
C5 C 0.51049(18) 0.9366(4) 0.14579(13) 0.0399(7) Uani 1 1 d . . . . .
H5 H 0.5543 0.9191 0.1264 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4546(2) 0.7642(5) 0.12882(14) 0.0531(9) Uani 1 1 d . . . . .
H6A H 0.4124 0.7744 0.1495 0.064 Uiso 1 1 calc R U . . .
H6B H 0.4805 0.6363 0.1386 0.064 Uiso 1 1 calc R U . . .
C7 C 0.4231(2) 0.7698(5) 0.06544(16) 0.0671(11) Uani 1 1 d . . . . .
H7A H 0.4645 0.7441 0.0448 0.080 Uiso 1 1 calc R U . . .
H7B H 0.3850 0.6639 0.0559 0.080 Uiso 1 1 calc R U . . .
C8 C 0.3868(3) 0.9725(6) 0.04758(17) 0.0732(12) Uani 1 1 d . . . . .
H8A H 0.3414 0.9905 0.0645 0.088 Uiso 1 1 calc R U . . .
H8B H 0.3708 0.9748 0.0067 0.088 Uiso 1 1 calc R U . . .
C9 C 0.4425(3) 1.1455(6) 0.06559(17) 0.0706(12) Uani 1 1 d . . . . .
H9A H 0.4849 1.1369 0.0451 0.085 Uiso 1 1 calc R U . . .
H9B H 0.4164 1.2732 0.0560 0.085 Uiso 1 1 calc R U . . .
C10 C 0.4737(2) 1.1391(5) 0.12890(15) 0.0528(9) Uani 1 1 d . . . . .
H10A H 0.5114 1.2457 0.1388 0.063 Uiso 1 1 calc R U . . .
H10B H 0.4321 1.1625 0.1495 0.063 Uiso 1 1 calc R U . . .
N1 N 0.53917(14) 0.9315(4) 0.20778(11) 0.0400(6) Uani 1 1 d . . . . .
H1A H 0.5763 1.0229 0.2168 0.048 Uiso 1 1 calc R U . . .
H1B H 0.5577 0.8091 0.2178 0.048 Uiso 1 1 calc R U . . .
H1C H 0.5008 0.9595 0.2259 0.048 Uiso 1 1 calc R U . . .
O2 O 0.58275(12) 0.5334(3) 0.24157(9) 0.0472(6) Uani 1 1 d . . . . .
O3 O 0.72449(13) 0.5151(3) 0.26642(10) 0.0498(6) Uani 1 1 d . . . . .
H3 H 0.7566 0.4242 0.2707 0.075 Uiso 1 1 calc R U . . .
O4 O 0.65455(11) 0.2207(3) 0.21593(10) 0.0461(6) Uani 1 1 d . . . . .
O1 O 0.65393(12) 0.5586(3) 0.16549(9) 0.0468(6) Uani 1 1 d . . . . .
P1 P 0.65233(4) 0.44578(11) 0.22338(3) 0.0357(3) 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 O1 1.463(4) . ?
C1 C3 1.476(5) . ?
C1 C4 1.504(5) . ?
C1 C2 1.525(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N1 1.483(4) . ?
C5 C10 1.513(4) . ?
C5 C6 1.517(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.523(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.515(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.521(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.520(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O2 P1 1.495(2) . ?
O3 P1 1.559(2) . ?
O3 H3 0.8200 . ?
O4 P1 1.501(2) . ?
O1 P1 1.582(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C3 109.9(3) . . ?
O1 C1 C4 103.8(3) . . ?
C3 C1 C4 112.9(4) . . ?
O1 C1 C2 109.9(3) . . ?
C3 C1 C2 111.3(4) . . ?
C4 C1 C2 108.8(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C10 110.0(2) . . ?
N1 C5 C6 109.9(2) . . ?
C10 C5 C6 111.4(3) . . ?
N1 C5 H5 108.5 . . ?
C10 C5 H5 108.5 . . ?
C6 C5 H5 108.5 . . ?
C5 C6 C7 110.7(3) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 111.4(3) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 111.4(3) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 111.3(3) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C5 C10 C9 110.7(3) . . ?
C5 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C5 N1 H1A 109.5 . . ?
C5 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C5 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
P1 O3 H3 109.5 . . ?
C1 O1 P1 129.89(19) . . ?
O2 P1 O4 117.37(13) . . ?
O2 P1 O3 108.14(13) . . ?
O4 P1 O3 109.56(12) . . ?
O2 P1 O1 102.69(12) . . ?
O4 P1 O1 111.02(13) . . ?
O3 P1 O1 107.50(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C6 C7 178.7(3) . . . . ?
C10 C5 C6 C7 56.5(4) . . . . ?
C5 C6 C7 C8 -55.4(5) . . . . ?
C6 C7 C8 C9 54.8(5) . . . . ?
C7 C8 C9 C10 -54.9(5) . . . . ?
N1 C5 C10 C9 -178.9(3) . . . . ?
C6 C5 C10 C9 -56.7(4) . . . . ?
C8 C9 C10 C5 55.6(5) . . . . ?
C3 C1 O1 P1 70.3(4) . . . . ?
C4 C1 O1 P1 -168.8(3) . . . . ?
C2 C1 O1 P1 -52.5(4) . . . . ?
C1 O1 P1 O2 -174.6(3) . . . . ?
C1 O1 P1 O4 -48.3(3) . . . . ?
C1 O1 P1 O3 71.5(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
C2 H2A O3 0.96 2.62 3.551(5) 163.1 7_665
C3 H3A O4 0.96 2.53 3.158(6) 123.3 .
N1 H1A O4 0.89 1.91 2.778(3) 165.4 1_565
N1 H1B O2 0.89 1.94 2.822(3) 171.5 .
N1 H1C O2 0.89 1.86 2.744(3) 174.8 4
C2 H2A O3 0.96 2.62 3.551(5) 163.1 7_665
C3 H3A O4 0.96 2.53 3.158(6) 123.3 .
N1 H1A O4 0.89 1.91 2.778(3) 165.4 1_565
N1 H1B O2 0.89 1.94 2.822(3) 171.5 .
N1 H1C O2 0.89 1.86 2.744(3) 174.8 4
O3 H3 O4 0.82 1.82 2.620(3) 164.6 7_655

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1536103'
_audit_update_record             
;
2017-03-06 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 N O4 P'
_chemical_formula_weight         225.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   22.8176(10)
_cell_length_b                   5.9912(3)
_cell_length_c                   18.3149(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.199(4)
_cell_angle_gamma                90
_cell_volume                     2489.09(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5071
_cell_measurement_theta_min      2.6590
_cell_measurement_theta_max      30.6460

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8941
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.713
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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             2187
_reflns_number_gt                1815
_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       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_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)+(0.0534P)²+3.8950P] 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         2187
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.90064(13) 1.1415(5) 0.64038(18) 0.0604(8) Uani 1 1 d . . . . .
H1D H 0.9131 1.2627 0.6096 0.091 Uiso 1 1 calc R U . . .
H1E H 0.9345 1.0456 0.6560 0.091 Uiso 1 1 calc R U . . .
H1F H 0.8850 1.2046 0.6837 0.091 Uiso 1 1 calc R U . . .
C2 C 0.85377(12) 1.0068(5) 0.59740(15) 0.0458(7) Uani 1 1 d . . . . .
H2A H 0.8202 1.1040 0.5795 0.055 Uiso 1 1 calc R U . . .
H2B H 0.8696 0.9387 0.5543 0.055 Uiso 1 1 calc R U . . .
C3 C 0.63782(10) 0.2237(4) 0.66694(12) 0.0337(6) Uani 1 1 d . . . . .
H3A H 0.6300 0.3414 0.7034 0.040 Uiso 1 1 calc R U . . .
C4 C 0.59922(14) 0.0281(6) 0.6779(2) 0.0823(12) Uani 1 1 d . . . . .
H4A H 0.6065 -0.0240 0.7294 0.099 Uiso 1 1 calc R U . . .
H4B H 0.6088 -0.0956 0.6454 0.099 Uiso 1 1 calc R U . . .
C5 C 0.53366(15) 0.0923(8) 0.6605(3) 0.0994(15) Uani 1 1 d . . . . .
H5A H 0.5088 -0.0413 0.6652 0.119 Uiso 1 1 calc R U . . .
H5B H 0.5231 0.2047 0.6965 0.119 Uiso 1 1 calc R U . . .
C6 C 0.52156(14) 0.1851(7) 0.5846(2) 0.0783(12) Uani 1 1 d . . . . .
H6A H 0.4796 0.2299 0.5756 0.094 Uiso 1 1 calc R U . . .
H6B H 0.5289 0.0686 0.5483 0.094 Uiso 1 1 calc R U . . .
C7 C 0.56031(13) 0.3843(7) 0.57482(19) 0.0744(11) Uani 1 1 d . . . . .
H7A H 0.5507 0.5052 0.6084 0.089 Uiso 1 1 calc R U . . .
H7B H 0.5526 0.4401 0.5238 0.089 Uiso 1 1 calc R U . . .
C8 C 0.62605(12) 0.3218(6) 0.59112(16) 0.0564(8) Uani 1 1 d . . . . .
H8A H 0.6368 0.2122 0.5544 0.068 Uiso 1 1 calc R U . . .
H8B H 0.6507 0.4566 0.5874 0.068 Uiso 1 1 calc R U . . .
N1 N 0.70096(8) 0.1557(3) 0.68129(9) 0.0271(4) Uani 1 1 d . . . . .
H1A H 0.7087 0.0460 0.6493 0.032 Uiso 1 1 calc R U . . .
H1B H 0.7083 0.1043 0.7281 0.032 Uiso 1 1 calc R U . . .
H1C H 0.7245 0.2755 0.6752 0.032 Uiso 1 1 calc R U . . .
O1 O 0.83419(7) 0.8336(3) 0.64440(8) 0.0338(4) Uani 1 1 d . . . . .
O2 O 0.77375(7) 0.5169(3) 0.67352(8) 0.0343(4) Uani 1 1 d . . . . .
O3 O 0.80490(8) 0.5444(3) 0.54656(8) 0.0398(5) Uani 1 1 d . . . . .
H3 H 0.7900 0.5992 0.5066 0.060 Uiso 1 1 calc R U . . .
O4 O 0.72909(6) 0.8158(3) 0.58427(7) 0.0295(4) Uani 1 1 d . . . . .
P1 P 0.78168(3) 0.67418(10) 0.61192(3) 0.0261(2) 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 C2 1.494(4) . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C2 O1 1.449(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.492(4) . ?
C3 N1 1.493(3) . ?
C3 C8 1.505(3) . ?
C3 H3A 1.0000 . ?
C4 C5 1.544(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.495(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.507(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.543(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
O1 P1 1.5963(16) . ?
O2 P1 1.4960(15) . ?
O3 P1 1.5668(16) . ?
O3 H3 0.8400 . ?
O4 P1 1.5115(15) . ?

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 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
O1 C2 C1 108.8(2) . . ?
O1 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
O1 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 N1 109.6(2) . . ?
C4 C3 C8 112.4(2) . . ?
N1 C3 C8 109.97(19) . . ?
C4 C3 H3A 108.3 . . ?
N1 C3 H3A 108.3 . . ?
C8 C3 H3A 108.3 . . ?
C3 C4 C5 110.5(3) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 111.2(3) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 110.7(3) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 110.8(3) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C3 C8 C7 110.2(2) . . ?
C3 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C3 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C3 N1 H1A 109.5 . . ?
C3 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C3 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 O1 P1 118.31(15) . . ?
P1 O3 H3 109.5 . . ?
O2 P1 O4 116.74(9) . . ?
O2 P1 O3 110.01(9) . . ?
O4 P1 O3 110.14(8) . . ?
O2 P1 O1 104.06(8) . . ?
O4 P1 O1 109.01(9) . . ?
O3 P1 O1 106.23(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 C5 -177.9(3) . . . . ?
C8 C3 C4 C5 -55.3(4) . . . . ?
C3 C4 C5 C6 55.8(5) . . . . ?
C4 C5 C6 C7 -57.1(5) . . . . ?
C5 C6 C7 C8 57.2(4) . . . . ?
C4 C3 C8 C7 55.5(4) . . . . ?
N1 C3 C8 C7 177.9(3) . . . . ?
C6 C7 C8 C3 -55.8(4) . . . . ?
C1 C2 O1 P1 177.02(18) . . . . ?
C2 O1 P1 O2 179.21(17) . . . . ?
C2 O1 P1 O4 -55.57(19) . . . . ?
C2 O1 P1 O3 63.09(19) . . . . ?

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 O4 0.91 1.91 2.822(2) 177.0 1_545
N1 H1B O2 0.91 1.88 2.786(2) 175.9 4_646
N1 H1C O2 0.91 1.83 2.741(2) 173.9 .
O3 H3 O4 0.84 1.75 2.577(2) 168.0 7_666

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1536102'
_audit_update_record             
;
2017-03-06 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H37 N2 O7 P'
_chemical_formula_weight         364.41

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'

_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                   12.6511(5)
_cell_length_b                   6.4515(2)
_cell_length_c                   24.2892(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.918(3)
_cell_angle_gamma                90
_cell_volume                     1958.48(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3447
_cell_measurement_theta_min      2.3480
_cell_measurement_theta_max      28.8810

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14283
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.529
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_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             3446
_reflns_number_gt                2816
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    Sir92
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ' Diamond'
_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)+(0.1345P)²+3.0445P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3446
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.2375
_refine_ls_wR_factor_gt          0.2217
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.41407(7) 0.84549(13) 0.63048(3) 0.0309(3) Uani 1 1 d . . . . .
O2 O 0.4274(2) 0.6156(4) 0.64043(12) 0.0476(7) Uani 1 1 d . . . . .
O3 O 0.4846(3) 0.9787(5) 0.67108(12) 0.0590(9) Uani 1 1 d . . . . .
O6 O 0.4169(3) 0.6787(5) 0.38213(14) 0.0561(8) Uani 1 1 d G . . . .
H6C H 0.4440 0.7928 0.3738 0.084 Uiso 1 1 d G U . . .
H6D H 0.4606 0.5807 0.3794 0.084 Uiso 1 1 d G U . . .
N2 N 0.4122(2) 0.3374(4) 0.72548(12) 0.0357(7) Uani 1 1 d . . . . .
H2A H 0.4235 0.4372 0.7018 0.043 Uiso 1 1 calc R U . . .
H2B H 0.4305 0.2156 0.7125 0.043 Uiso 1 1 calc R U . . .
H2C H 0.4516 0.3615 0.7585 0.043 Uiso 1 1 calc R U . . .
O4 O 0.4110(3) 0.9010(5) 0.57044(11) 0.0608(9) Uani 1 1 d . . . . .
N1 N 0.3368(3) 0.6185(5) 0.48275(13) 0.0428(8) Uani 1 1 d . . . . .
H1A H 0.3640 0.6585 0.4528 0.051 Uiso 1 1 calc R U . . .
H1B H 0.3565 0.4886 0.4913 0.051 Uiso 1 1 calc R U . . .
H1C H 0.3610 0.7012 0.5113 0.051 Uiso 1 1 calc R U . . .
O5 O 0.5869(3) 0.7959(6) 0.51389(17) 0.0725(10) Uani 1 1 d G . . . .
H5C H 0.5596 0.8513 0.5402 0.109 Uiso 1 1 d G U . . .
H5D H 0.5670 0.8621 0.4838 0.109 Uiso 1 1 d G U . . .
O1 O 0.2980(3) 0.9155(5) 0.64783(15) 0.0649(9) Uani 1 1 d . . . . .
O7 O 0.2774(3) 0.3385(5) 0.58041(17) 0.0750(11) Uani 1 1 d G . . . .
H7A H 0.2977 0.2130 0.5843 0.113 Uiso 1 1 d G U . . .
H7B H 0.3224 0.4159 0.6004 0.113 Uiso 1 1 d G U . . .
C7 C 0.2963(3) 0.3336(5) 0.73159(14) 0.0333(8) Uani 1 1 d . . . . .
H7 H 0.2544 0.3123 0.6946 0.040 Uiso 1 1 calc R U . . .
C1 C 0.2177(3) 0.6308(6) 0.47089(16) 0.0383(8) Uani 1 1 d . . . . .
H1 H 0.1895 0.6002 0.5054 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2641(3) 0.5401(6) 0.75354(17) 0.0455(10) Uani 1 1 d . . . . .
H8A H 0.2789 0.6501 0.7286 0.055 Uiso 1 1 calc R U . . .
H8B H 0.3057 0.5662 0.7899 0.055 Uiso 1 1 calc R U . . .
C6 C 0.1749(3) 0.4703(6) 0.42789(18) 0.0489(10) Uani 1 1 d . . . . .
H6A H 0.1955 0.3330 0.4419 0.059 Uiso 1 1 calc R U . . .
H6B H 0.2055 0.4927 0.3942 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2723(3) 0.1563(5) 0.76871(16) 0.0429(9) Uani 1 1 d . . . . .
H12A H 0.3139 0.1721 0.8055 0.051 Uiso 1 1 calc R U . . .
H12B H 0.2919 0.0257 0.7533 0.051 Uiso 1 1 calc R U . . .
C2 C 0.1836(3) 0.8469(6) 0.45247(19) 0.0492(10) Uani 1 1 d . . . . .
H2D H 0.2146 0.8835 0.4197 0.059 Uiso 1 1 calc R U . . .
H2E H 0.2096 0.9447 0.4818 0.059 Uiso 1 1 calc R U . . .
C4 C 0.0159(4) 0.7003(7) 0.3965(2) 0.0556(11) Uani 1 1 d . . . . .
H4A H 0.0378 0.7318 0.3609 0.067 Uiso 1 1 calc R U . . .
H4B H -0.0616 0.7060 0.3918 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1445(4) 0.5396(7) 0.7582(2) 0.0578(11) Uani 1 1 d . . . . .
H9A H 0.1255 0.6701 0.7739 0.069 Uiso 1 1 calc R U . . .
H9B H 0.1027 0.5257 0.7214 0.069 Uiso 1 1 calc R U . . .
C11 C 0.1539(4) 0.1554(7) 0.77303(19) 0.0540(11) Uani 1 1 d . . . . .
H11A H 0.1393 0.0440 0.7976 0.065 Uiso 1 1 calc R U . . .
H11B H 0.1130 0.1289 0.7365 0.065 Uiso 1 1 calc R U . . .
C3 C 0.0623(4) 0.8605(7) 0.4391(2) 0.0601(12) Uani 1 1 d . . . . .
H3A H 0.0321 0.8404 0.4731 0.072 Uiso 1 1 calc R U . . .
H3B H 0.0422 0.9978 0.4250 0.072 Uiso 1 1 calc R U . . .
C5 C 0.0531(3) 0.4842(7) 0.4146(2) 0.0535(11) Uani 1 1 d . . . . .
H5A H 0.0274 0.3866 0.3852 0.064 Uiso 1 1 calc R U . . .
H5B H 0.0226 0.4455 0.4474 0.064 Uiso 1 1 calc R U . . .
C10 C 0.1179(4) 0.3604(7) 0.7952(2) 0.0565(12) Uani 1 1 d . . . . .
H10A H 0.1537 0.3817 0.8331 0.068 Uiso 1 1 calc R U . . .
H10B H 0.0414 0.3567 0.7957 0.068 Uiso 1 1 calc R U . . .
C13 C 0.2022(4) 0.8359(8) 0.6202(2) 0.0580(12) Uani 1 1 d . . . . .
H13A H 0.1913 0.8824 0.5822 0.087 Uiso 1 1 calc R U . . .
H13B H 0.1442 0.8832 0.6382 0.087 Uiso 1 1 calc R U . . .
H13C H 0.2048 0.6872 0.6211 0.087 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 O3 1.495(3) . ?
P1 O4 1.496(3) . ?
P1 O2 1.508(3) . ?
P1 O1 1.653(3) . ?
O6 H6C 0.8501 . ?
O6 H6D 0.8499 . ?
N2 C7 1.497(5) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N1 C1 1.492(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O5 H5C 0.8503 . ?
O5 H5D 0.8499 . ?
O1 C13 1.389(5) . ?
O7 H7A 0.8498 . ?
O7 H7B 0.8503 . ?
C7 C8 1.514(5) . ?
C7 C12 1.516(5) . ?
C7 H7 0.9800 . ?
C1 C2 1.507(5) . ?
C1 C6 1.510(5) . ?
C1 H1 0.9800 . ?
C8 C9 1.535(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 C5 1.526(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C12 C11 1.517(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 C3 1.521(6) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C4 C3 1.515(7) . ?
C4 C5 1.515(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C9 C10 1.533(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C10 1.525(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 115.34(19) . . ?
O3 P1 O2 114.78(17) . . ?
O4 P1 O2 112.16(18) . . ?
O3 P1 O1 97.93(18) . . ?
O4 P1 O1 107.05(19) . . ?
O2 P1 O1 108.03(17) . . ?
H6C O6 H6D 109.5 . . ?
C7 N2 H2A 109.5 . . ?
C7 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C7 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
H5C O5 H5D 109.5 . . ?
C13 O1 P1 121.3(3) . . ?
H7A O7 H7B 109.5 . . ?
N2 C7 C8 110.0(3) . . ?
N2 C7 C12 111.2(3) . . ?
C8 C7 C12 111.4(3) . . ?
N2 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
C12 C7 H7 108.1 . . ?
N1 C1 C2 109.9(3) . . ?
N1 C1 C6 109.9(3) . . ?
C2 C1 C6 111.9(3) . . ?
N1 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
C6 C1 H1 108.3 . . ?
C7 C8 C9 110.3(3) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C1 C6 C5 110.3(3) . . ?
C1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C7 C12 C11 109.6(3) . . ?
C7 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C7 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C1 C2 C3 110.4(3) . . ?
C1 C2 H2D 109.6 . . ?
C3 C2 H2D 109.6 . . ?
C1 C2 H2E 109.6 . . ?
C3 C2 H2E 109.6 . . ?
H2D C2 H2E 108.1 . . ?
C3 C4 C5 111.0(4) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C10 C9 C8 110.7(4) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C12 C11 C10 111.9(4) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C4 C3 C2 112.2(4) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C5 C6 111.9(4) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C11 C10 C9 110.0(4) . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O3 P1 O1 C13 178.4(4) . . . . ?
O4 P1 O1 C13 58.8(4) . . . . ?
O2 P1 O1 C13 -62.2(4) . . . . ?
N2 C7 C8 C9 178.3(3) . . . . ?
C12 C7 C8 C9 -58.0(4) . . . . ?
N1 C1 C6 C5 -178.9(3) . . . . ?
C2 C1 C6 C5 -56.5(5) . . . . ?
N2 C7 C12 C11 -179.0(3) . . . . ?
C8 C7 C12 C11 57.9(4) . . . . ?
N1 C1 C2 C3 178.9(3) . . . . ?
C6 C1 C2 C3 56.5(5) . . . . ?
C7 C8 C9 C10 56.5(5) . . . . ?
C7 C12 C11 C10 -57.4(5) . . . . ?
C5 C4 C3 C2 54.0(5) . . . . ?
C1 C2 C3 C4 -55.0(5) . . . . ?
C3 C4 C5 C6 -53.9(5) . . . . ?
C1 C6 C5 C4 55.1(5) . . . . ?
C12 C11 C10 C9 56.6(5) . . . . ?
C8 C9 C10 C11 -55.6(5) . . . . ?

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
O6 H6C O3 0.85 2.12 2.934(4) 161.2 3_676
O6 H6D O2 0.85 2.01 2.850(4) 167.9 3_666
N2 H2A O2 0.89 1.89 2.766(4) 167.8 .
N2 H2B O3 0.89 2.01 2.884(4) 167.6 1_545
N2 H2C O3 0.89 1.93 2.798(4) 165.2 2_646
N1 H1A O6 0.89 1.94 2.814(4) 166.6 .
N1 H1B O5 0.89 1.98 2.839(5) 161.6 3_666
N1 H1C O4 0.89 1.96 2.850(4) 175.7 .
O5 H5C O4 0.85 2.15 2.872(5) 143.0 .
O5 H5D O4 0.85 2.06 2.835(5) 150.4 3_676
O7 H7A O4 0.85 2.52 3.317(5) 155.9 1_545
O7 H7A O1 0.85 2.46 3.173(5) 141.5 1_545
O7 H7B O2 0.85 1.99 2.840(5) 174.3 .
C1 H1 O7 0.98 2.60 3.253(5) 123.8 .
C8 H8A O1 0.97 2.64 3.603(5) 170.5 .

_refine_diff_density_max         1.629
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1536106'
_audit_update_record             
;
2017-03-06 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H9 O4 P'
_chemical_formula_sum            'C3 H9 O4 P'
_chemical_formula_weight         140.07

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'
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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'

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

_cell_length_a                   14.6655(2)
_cell_length_b                   14.6655(2)
_cell_length_c                   5.88520(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1265.77(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2077
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.367
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9065
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.778
_diffrn_reflns_theta_max         24.972
_diffrn_reflns_theta_full        24.972
_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             1110
_reflns_number_gt                1076
_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       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    Sir92
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3.2'
_computing_publication_material  'WinGX v2014. 1'
_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)+(0.0525P)²+0.7472P] 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         1110
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.19656(3) 0.08586(3) 0.97494(7) 0.01719(19) Uani 1 1 d . . . . .
O1 O 0.19728(7) -0.01373(8) 1.0667(2) 0.0204(3) Uani 1 1 d . . . . .
O4 O 0.17690(8) 0.07694(8) 0.7180(2) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.1772 0.1289 0.6581 0.034 Uiso 1 1 calc R U . . .
O3 O 0.11383(8) 0.13788(8) 1.0741(2) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.1180 0.1395 1.2164 0.034 Uiso 1 1 calc R U . . .
O2 O 0.28643(8) 0.12816(8) 1.03081(19) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.11418(11) -0.07053(11) 1.0558(3) 0.0219(4) Uani 1 1 d . . . . .
H1 H 0.0676 -0.0396 0.9585 0.026 Uiso 1 1 calc R U . . .
C3 C 0.14077(14) -0.15958(14) 0.9494(4) 0.0373(5) Uani 1 1 d . . . . .
H3A H 0.0871 -0.1992 0.9393 0.056 Uiso 1 1 calc R U . . .
H3B H 0.1650 -0.1485 0.7967 0.056 Uiso 1 1 calc R U . . .
H3C H 0.1875 -0.1892 1.0427 0.056 Uiso 1 1 calc R U . . .
C2 C 0.07792(13) -0.08000(15) 1.2933(4) 0.0368(5) Uani 1 1 d . . . . .
H2A H 0.0226 -0.1175 1.2912 0.055 Uiso 1 1 calc R U . . .
H2B H 0.1240 -0.1092 1.3894 0.055 Uiso 1 1 calc R U . . .
H2C H 0.0635 -0.0195 1.3542 0.055 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 O2 1.4933(12) . ?
P1 O4 1.5447(13) . ?
P1 O3 1.5475(12) . ?
P1 O1 1.5573(12) . ?
O1 C1 1.478(2) . ?
O4 H4 0.8400 . ?
O3 H3 0.8400 . ?
C1 C3 1.500(3) . ?
C1 C2 1.502(3) . ?
C1 H1 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
O2 P1 O4 114.55(7) . . ?
O2 P1 O3 113.83(7) . . ?
O4 P1 O3 105.33(7) . . ?
O2 P1 O1 107.90(7) . . ?
O4 P1 O1 105.15(6) . . ?
O3 P1 O1 109.68(7) . . ?
C1 O1 P1 120.54(10) . . ?
P1 O4 H4 109.5 . . ?
P1 O3 H3 109.5 . . ?
O1 C1 C3 107.14(14) . . ?
O1 C1 C2 107.67(14) . . ?
C3 C1 C2 113.59(16) . . ?
O1 C1 H1 109.5 . . ?
C3 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

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
O2 P1 O1 C1 174.32(11) . . . . ?
O4 P1 O1 C1 -63.01(12) . . . . ?
O3 P1 O1 C1 49.81(13) . . . . ?
P1 O1 C1 C3 129.52(14) . . . . ?
P1 O1 C1 C2 -107.95(15) . . . . ?

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
O4 H4 O2 0.84 1.82 2.5828(16) 151.1 7_567
O3 H3 O2 0.84 1.85 2.5852(16) 145.6 7_568
O4 H4 O2 0.84 1.82 2.5828(16) 151.1 7_567
O3 H3 O2 0.84 1.85 2.5852(16) 145.6 7_568

_refine_diff_density_max         0.363
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1536104'
_audit_update_record             
;
2017-03-06 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H22 N O4 P'
_chemical_formula_weight         239.24

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'

_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                   13.4545(12)
_cell_length_b                   6.1394(4)
_cell_length_c                   16.6944(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.778(8)
_cell_angle_gamma                90
_cell_volume                     1313.15(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2309
_cell_measurement_theta_min      3.180
_cell_measurement_theta_max      24.999

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'OXFORD DIFFRACTIOM X CALIBUR-S'
_diffrn_measurement_method       'omega(w)-q scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8427
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.180
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2309
_reflns_number_gt                1822
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        'ShelXT (Sheldrick, 2015)'
_computing_structure_solution    ?
_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)+(0.0800P)²+13.9616P] 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         2309
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0935
_refine_ls_wR_factor_ref         0.2919
_refine_ls_wR_factor_gt          0.2879
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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 0.06299(14) 1.0335(3) 0.13261(10) 0.0257(5) Uani 1 1 d . . . . .
O4 O 0.0631(4) 0.8341(7) 0.0804(3) 0.0275(11) Uani 1 1 d . . . . .
O2 O 0.1675(4) 1.1286(8) 0.1780(3) 0.0334(12) Uani 1 1 d . . . . .
O3 O -0.0117(4) 1.2090(8) 0.0786(3) 0.0365(13) Uani 1 1 d . . . . .
H3 H -0.0284 1.1736 0.0276 0.055 Uiso 1 1 calc R U . . .
O1 O 0.0143(4) 0.9760(8) 0.2056(3) 0.0337(12) Uani 1 1 d . . . . .
N1 N 0.2753(4) 1.0437(9) 0.3442(3) 0.0270(13) Uani 1 1 d . . . . .
H1A H 0.2435 1.0869 0.2903 0.032 Uiso 1 1 calc R U . . .
H1B H 0.2993 0.9050 0.3443 0.032 Uiso 1 1 calc R U . . .
H1C H 0.3297 1.1341 0.3685 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2501(6) 0.9657(14) 0.4821(5) 0.0386(18) Uani 1 1 d . . . . .
H5A H 0.2717 0.8122 0.4798 0.046 Uiso 1 1 calc R U . . .
H5B H 0.3130 1.0527 0.5102 0.046 Uiso 1 1 calc R U . . .
C4 C 0.1991(5) 1.0516(11) 0.3926(4) 0.0293(15) Uani 1 1 d . . . . .
H4 H 0.1390 0.9548 0.3641 0.035 Uiso 1 1 calc R U . . .
C9 C 0.1585(6) 1.2821(13) 0.3921(5) 0.0401(19) Uani 1 1 d . . . . .
H9A H 0.1227 1.3276 0.3335 0.048 Uiso 1 1 calc R U . . .
H9B H 0.2178 1.3825 0.4159 0.048 Uiso 1 1 calc R U . . .
C2 C -0.0842(6) 0.8589(13) 0.1867(5) 0.0390(18) Uani 1 1 d . . . . .
H2A H -0.1167 0.8523 0.1243 0.047 Uiso 1 1 calc R U . . .
C3 C -0.1529(7) 0.9888(15) 0.2241(6) 0.051(2) Uani 1 1 d . . . . .
H3A H -0.1227 0.9917 0.2855 0.077 Uiso 1 1 calc R U . . .
H3B H -0.2223 0.9219 0.2091 0.077 Uiso 1 1 calc R U . . .
H3C H -0.1589 1.1379 0.2022 0.077 Uiso 1 1 calc R U . . .
C6 C 0.1724(7) 0.9810(17) 0.5317(5) 0.052(2) Uani 1 1 d . . . . .
H6A H 0.1126 0.8832 0.5061 0.063 Uiso 1 1 calc R U . . .
H6B H 0.2064 0.9317 0.5901 0.063 Uiso 1 1 calc R U . . .
C1 C -0.0626(7) 0.6297(15) 0.2207(7) 0.058(3) Uani 1 1 d . . . . .
H1D H -0.0217 0.5518 0.1903 0.088 Uiso 1 1 calc R U . . .
H1E H -0.1288 0.5536 0.2132 0.088 Uiso 1 1 calc R U . . .
H1F H -0.0233 0.6352 0.2807 0.088 Uiso 1 1 calc R U . . .
C8 C 0.0822(7) 1.2958(16) 0.4439(5) 0.052(2) Uani 1 1 d . . . . .
H8A H 0.0602 1.4490 0.4461 0.062 Uiso 1 1 calc R U . . .
H8B H 0.0193 1.2082 0.4164 0.062 Uiso 1 1 calc R U . . .
C7 C 0.1329(7) 1.2122(19) 0.5329(5) 0.058(3) Uani 1 1 d . . . . .
H7A H 0.1919 1.3084 0.5622 0.070 Uiso 1 1 calc R U . . .
H7B H 0.0814 1.2158 0.5644 0.070 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 O2 1.497(5) . ?
P1 O4 1.503(5) . ?
P1 O3 1.559(5) . ?
P1 O1 1.590(5) . ?
O3 H3 0.8400 . ?
O1 C2 1.455(9) . ?
N1 C4 1.486(9) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C5 C6 1.521(11) . ?
C5 C4 1.535(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 C9 1.516(10) . ?
C4 H4 1.0000 . ?
C9 C8 1.533(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C2 C3 1.494(11) . ?
C2 C1 1.511(12) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C6 C7 1.518(14) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C8 C7 1.522(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 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
O2 P1 O4 116.4(3) . . ?
O2 P1 O3 111.3(3) . . ?
O4 P1 O3 110.0(3) . . ?
O2 P1 O1 104.0(3) . . ?
O4 P1 O1 109.7(3) . . ?
O3 P1 O1 104.7(3) . . ?
P1 O3 H3 109.5 . . ?
C2 O1 P1 120.3(4) . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 C5 C4 109.4(6) . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
N1 C4 C9 109.6(6) . . ?
N1 C4 C5 109.9(5) . . ?
C9 C4 C5 112.3(6) . . ?
N1 C4 H4 108.3 . . ?
C9 C4 H4 108.3 . . ?
C5 C4 H4 108.3 . . ?
C4 C9 C8 110.5(7) . . ?
C4 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O1 C2 C3 106.5(6) . . ?
O1 C2 C1 108.7(6) . . ?
C3 C2 C1 114.4(7) . . ?
O1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C7 C6 C5 111.5(7) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C7 C8 C9 110.8(7) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C6 C7 C8 110.9(8) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?

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
O2 P1 O1 C2 -173.8(5) . . . . ?
O4 P1 O1 C2 -48.7(6) . . . . ?
O3 P1 O1 C2 69.3(6) . . . . ?
C6 C5 C4 N1 178.3(7) . . . . ?
C6 C5 C4 C9 56.1(9) . . . . ?
N1 C4 C9 C8 -178.3(6) . . . . ?
C5 C4 C9 C8 -55.9(8) . . . . ?
P1 O1 C2 C3 -128.1(6) . . . . ?
P1 O1 C2 C1 108.2(7) . . . . ?
C4 C5 C6 C7 -56.5(9) . . . . ?
C4 C9 C8 C7 55.4(10) . . . . ?
C5 C6 C7 C8 57.7(10) . . . . ?
C9 C8 C7 C6 -56.4(10) . . . . ?

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
O3 H3 O4 0.84 1.72 2.544(6) 166.6 3_575
N1 H1A O2 0.91 1.86 2.761(7) 170.1 .
N1 H1B O3 0.91 3.00 3.674(8) 131.7 2_545
N1 H1C O4 0.91 1.89 2.797(7) 176.6 2

_refine_diff_density_max         0.820
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.125

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1536107'
_audit_update_record             
;
2017-03-06 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H8 O4 P, C3 H9 O4 P, C6 H14 N'
_chemical_formula_sum            'C12 H31 N O8 P2'
_chemical_formula_weight         379.32

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'
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'
N N 0.0061 0.0033 '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                   13.596(7)
_cell_length_b                   10.066(5)
_cell_length_c                   15.921(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.966(9)
_cell_angle_gamma                90
_cell_volume                     2020.7(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4419
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      31.40

_exptl_crystal_description       Needles
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.249
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13969
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.589
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3526
_reflns_number_gt                3378
_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       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_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)+(0.0717P)²+1.1115P] 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         3526
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_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 0.48682(5) 0.08725(6) 0.37629(4) 0.0265(2) Uani 1 1 d . . . . .
P2 P 0.38870(5) 0.63387(7) 0.28644(4) 0.0289(2) Uani 1 1 d . . . . .
O1 O 0.55163(14) 0.09741(18) 0.31272(12) 0.0340(5) Uani 1 1 d . . . . .
O2 O 0.46708(14) -0.05645(18) 0.39186(11) 0.0326(4) Uani 1 1 d . . . . .
O3 O 0.56148(13) 0.15099(18) 0.46759(11) 0.0322(4) Uani 1 1 d . . . . .
H3 H 0.5484 0.1177 0.5107 0.039 Uiso 1 1 calc R U . . .
O4 O 0.39006(13) 0.17103(17) 0.33399(11) 0.0315(4) Uani 1 1 d . . . . .
O5 O 0.40821(15) 0.57372(18) 0.20345(12) 0.0358(4) Uani 1 1 d . . . . .
O6 O 0.47021(14) 0.59501(18) 0.37533(12) 0.0350(5) Uani 1 1 d . . . . .
O7 O 0.28036(14) 0.58472(19) 0.28433(12) 0.0378(5) Uani 1 1 d . . . . .
H7 H 0.2328 0.6055 0.2346 0.045 Uiso 1 1 calc R U . . .
O8 O 0.38317(16) 0.78240(19) 0.26261(12) 0.0409(5) Uani 1 1 d . . . . .
H8 H 0.3693 0.8264 0.3017 0.049 Uiso 1 1 calc R U . . .
N1 N 0.11453(15) 0.8822(2) 0.05254(14) 0.0284(5) Uani 1 1 d . . . . .
H1A H 0.1092 0.8105 0.0854 0.034 Uiso 1 1 calc R U . . .
H1B H 0.1022 0.9576 0.0785 0.034 Uiso 1 1 calc R U . . .
H1C H 0.0659 0.8752 -0.0050 0.034 Uiso 1 1 calc R U . . .
C1 C 0.6543(2) 0.0309(3) 0.33951(19) 0.0389(7) Uani 1 1 d . . . . .
H1 H 0.6718 -0.0109 0.4004 0.047 Uiso 1 1 calc R U . . .
C2 C 0.7353(3) 0.1367(4) 0.3457(3) 0.0571(9) Uani 1 1 d . . . . .
H2A H 0.8056 0.0960 0.3636 0.069 Uiso 1 1 calc R U . . .
H2B H 0.7170 0.1797 0.2866 0.069 Uiso 1 1 calc R U . . .
H2C H 0.7358 0.2030 0.3909 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6461(3) -0.0752(3) 0.2709(3) 0.0585(9) Uani 1 1 d . . . . .
H3A H 0.7143 -0.1212 0.2877 0.070 Uiso 1 1 calc R U . . .
H3B H 0.5911 -0.1391 0.2694 0.070 Uiso 1 1 calc R U . . .
H3C H 0.6276 -0.0346 0.2110 0.070 Uiso 1 1 calc R U . . .
C4 C 0.4218(2) 0.4299(3) 0.19771(19) 0.0387(6) Uani 1 1 d . . . . .
H4 H 0.4259 0.3877 0.2558 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3277(3) 0.3769(4) 0.1224(3) 0.0731(11) Uani 1 1 d . . . . .
H5A H 0.3353 0.2807 0.1174 0.088 Uiso 1 1 calc R U . . .
H5B H 0.2635 0.3955 0.1345 0.088 Uiso 1 1 calc R U . . .
H5C H 0.3221 0.4196 0.0655 0.088 Uiso 1 1 calc R U . . .
C6 C 0.5244(3) 0.4085(4) 0.1856(3) 0.0793(13) Uani 1 1 d . . . . .
H6A H 0.5361 0.3131 0.1814 0.095 Uiso 1 1 calc R U . . .
H6B H 0.5218 0.4525 0.1298 0.095 Uiso 1 1 calc R U . . .
H6C H 0.5825 0.4460 0.2374 0.095 Uiso 1 1 calc R U . . .
C7 C 0.22327(19) 0.8874(3) 0.05041(17) 0.0286(5) Uani 1 1 d . . . . .
H7A H 0.2761 0.8963 0.1138 0.034 Uiso 1 1 calc R U . . .
C8 C 0.2433(2) 0.7580(3) 0.01080(19) 0.0371(6) Uani 1 1 d . . . . .
H8A H 0.1885 0.7454 -0.0505 0.044 Uiso 1 1 calc R U . . .
H8B H 0.2383 0.6829 0.0492 0.044 Uiso 1 1 calc R U . . .
C9 C 0.3529(2) 0.7592(3) 0.0054(2) 0.0506(8) Uani 1 1 d . . . . .
H9A H 0.4079 0.7625 0.0673 0.061 Uiso 1 1 calc R U . . .
H9B H 0.3632 0.6766 -0.0241 0.061 Uiso 1 1 calc R U . . .
C10 C 0.3648(3) 0.8790(4) -0.0485(3) 0.0575(9) Uani 1 1 d . . . . .
H10A H 0.4377 0.8811 -0.0483 0.069 Uiso 1 1 calc R U . . .
H10B H 0.3147 0.8708 -0.1121 0.069 Uiso 1 1 calc R U . . .
C11 C 0.3431(3) 1.0075(4) -0.0086(2) 0.0548(9) Uani 1 1 d . . . . .
H11A H 0.3484 1.0833 -0.0464 0.066 Uiso 1 1 calc R U . . .
H11B H 0.3972 1.0198 0.0530 0.066 Uiso 1 1 calc R U . . .
C12 C 0.2330(2) 1.0063(3) -0.0040(2) 0.0394(7) Uani 1 1 d . . . . .
H12A H 0.2218 1.0890 0.0248 0.047 Uiso 1 1 calc R U . . .
H12B H 0.1782 1.0016 -0.0659 0.047 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 1.4941(19) . ?
P1 O2 1.508(2) . ?
P1 O3 1.5656(19) . ?
P1 O1 1.5742(18) . ?
P2 O6 1.4868(19) . ?
P2 O8 1.537(2) . ?
P2 O7 1.542(2) . ?
P2 O5 1.564(2) . ?
O1 C1 1.461(3) . ?
O3 H3 0.8400 . ?
O5 C4 1.467(3) . ?
O7 H7 0.8400 . ?
O8 H8 0.8400 . ?
N1 C7 1.492(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C1 C3 1.501(4) . ?
C1 C2 1.508(4) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.488(5) . ?
C4 C6 1.493(5) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.512(4) . ?
C7 C8 1.516(4) . ?
C7 H7A 1.0000 . ?
C8 C9 1.525(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.523(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.526(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 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
O4 P1 O2 115.75(11) . . ?
O4 P1 O3 110.06(11) . . ?
O2 P1 O3 109.50(10) . . ?
O4 P1 O1 106.49(10) . . ?
O2 P1 O1 110.16(10) . . ?
O3 P1 O1 104.23(11) . . ?
O6 P2 O8 116.17(11) . . ?
O6 P2 O7 107.58(11) . . ?
O8 P2 O7 110.39(11) . . ?
O6 P2 O5 113.63(12) . . ?
O8 P2 O5 100.15(11) . . ?
O7 P2 O5 108.66(11) . . ?
C1 O1 P1 119.09(16) . . ?
P1 O3 H3 109.5 . . ?
C4 O5 P2 120.01(16) . . ?
P2 O7 H7 109.5 . . ?
P2 O8 H8 109.5 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O1 C1 C3 108.1(2) . . ?
O1 C1 C2 106.9(2) . . ?
C3 C1 C2 113.8(3) . . ?
O1 C1 H1 109.3 . . ?
C3 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O5 C4 C5 108.3(2) . . ?
O5 C4 C6 107.2(3) . . ?
C5 C4 C6 114.1(3) . . ?
O5 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C6 C4 H4 109.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C12 109.9(2) . . ?
N1 C7 C8 108.2(2) . . ?
C12 C7 C8 112.0(2) . . ?
N1 C7 H7A 108.9 . . ?
C12 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C7 C8 C9 110.4(2) . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 110.5(3) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 111.2(3) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 111.2(3) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C7 C12 C11 109.4(2) . . ?
C7 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C7 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?

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
O4 P1 O1 C1 176.66(19) . . . . ?
O2 P1 O1 C1 -57.1(2) . . . . ?
O3 P1 O1 C1 60.3(2) . . . . ?
O6 P2 O5 C4 53.9(2) . . . . ?
O8 P2 O5 C4 178.47(19) . . . . ?
O7 P2 O5 C4 -65.8(2) . . . . ?
P1 O1 C1 C3 115.9(2) . . . . ?
P1 O1 C1 C2 -121.2(2) . . . . ?
P2 O5 C4 C5 111.1(3) . . . . ?
P2 O5 C4 C6 -125.4(3) . . . . ?
N1 C7 C8 C9 178.9(2) . . . . ?
C12 C7 C8 C9 57.6(3) . . . . ?
C7 C8 C9 C10 -55.7(4) . . . . ?
C8 C9 C10 C11 55.8(4) . . . . ?
C9 C10 C11 C12 -56.7(4) . . . . ?
N1 C7 C12 C11 -177.9(2) . . . . ?
C8 C7 C12 C11 -57.6(3) . . . . ?
C10 C11 C12 C7 56.8(4) . . . . ?

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
O3 H3 O2 0.84 1.75 2.591(3) 174.1 3_656
O7 H7 O4 0.84 1.75 2.531(3) 154.5 2
O8 H8 O2 0.84 1.95 2.532(3) 125.8 1_565
N1 H1A O4 0.91 1.90 2.805(3) 173.2 2
N1 H1B O6 0.91 1.99 2.868(3) 161.5 2
N1 H1B O7 0.91 2.52 3.189(3) 130.8 2
N1 H1C O6 0.91 1.89 2.779(3) 166.3 4_575
C4 H4 O4 1.00 2.65 3.519(4) 146.0 .
C7 H7A O8 1.00 2.54 3.430(3) 147.6 .
O3 H3 O2 0.84 1.75 2.591(3) 174.1 3_656
O7 H7 O4 0.84 1.75 2.531(3) 154.5 2
O8 H8 O2 0.84 1.95 2.532(3) 125.8 1_565
N1 H1A O4 0.91 1.90 2.805(3) 173.2 2
N1 H1B O6 0.91 1.99 2.868(3) 161.5 2
N1 H1B O7 0.91 2.52 3.189(3) 130.8 2
N1 H1C O6 0.91 1.89 2.779(3) 166.3 4_575
C4 H4 O4 1.00 2.65 3.519(4) 146.0 .
C7 H7A O8 1.00 2.54 3.430(3) 147.6 .

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.067

