# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Christian Stevens'
_publ_contact_author_email       CHRIS.STEVENS@UGENT.BE

_publ_section_title              
;
One-Pot Tandem 1,4-1,2-Addition of Phosphites to Quinolines
;
loop_
_publ_author_name
'Christian Stevens'
'Ann De Blieck'
'Frederic Dhaene'
'Kurt Masschelein'

data_I
_database_code_depnum_ccdc_archive 'CCDC 747372'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2,6-Bis(dimethoxyphosphoryl)-1,2,3,4-tetrahydroquinoline
;
_chemical_name_common            
2,6-Bis(dimethoxyphosphoryl)-1,2,3,4-tetrahydroquinoline
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 N2 O8 P2'
_chemical_formula_sum            'C13 H20 N2 O8 P2'
_chemical_formula_weight         394.25

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_symmetry_cell_setting
triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0124(4)
_cell_length_b                   10.3614(5)
_cell_length_c                   10.4335(4)
_cell_angle_alpha                63.537(4)
_cell_angle_beta                 80.792(3)
_cell_angle_gamma                67.351(4)
_cell_volume                     894.17(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    19124
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      25.68

_exptl_crystal_description       columnar
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_min  0.96596
_exptl_absorpt_correction_T_max  0.98000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur3\\^TM\\^ CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19124
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.68
_reflns_number_total             3389
_reflns_number_gt                2307
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.0536P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3389
_refine_ls_number_parameters     278
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.19466(8) 0.40484(10) 0.21682(9) 0.0455(3) Uani 1 1 d . A .
O3 O 0.2174(2) 0.4785(3) 0.0639(2) 0.0555(6) Uani 1 1 d . . .
O5 O 0.0767(3) 0.5157(4) 0.2745(3) 0.0862(9) Uani 1 1 d . . .
N2 N 0.3228(4) 0.7684(4) 0.4154(3) 0.0598(8) Uani 1 1 d . . .
C1 C 0.3964(3) 0.6616(4) 0.3513(3) 0.0466(8) Uani 1 1 d . A .
C2 C 0.5187(4) 0.6733(4) 0.2702(3) 0.0492(8) Uani 1 1 d . . .
H2A H 0.5543 0.7489 0.2572 0.059 Uiso 1 1 calc R A .
C3 C 0.5857(3) 0.5722(4) 0.2098(3) 0.0480(8) Uani 1 1 d . A .
H3A H 0.6686 0.5787 0.1565 0.058 Uiso 1 1 calc R . .
C9 C 0.3439(3) 0.5493(4) 0.3720(3) 0.0460(8) Uani 1 1 d . . .
H9A H 0.2630 0.5421 0.4286 0.055 Uiso 1 1 calc R A .
O2 O 0.3726(4) 0.8666(3) 0.3976(3) 0.0881(9) Uani 1 1 d . A .
O1 O 0.2158(13) 0.752(2) 0.493(3) 0.075(3) Uani 0.79(7) 1 d P A 1
O1A O 0.202(5) 0.788(6) 0.444(6) 0.075(3) Uani 0.21(7) 1 d P A 2
C11 C -0.0079(13) 0.6586(13) 0.1999(12) 0.093(3) Uani 0.464(8) 1 d P B 1
H11A H 0.0500 0.7175 0.1391 0.139 Uiso 0.464(8) 1 calc PR B 1
H11B H -0.0615 0.7035 0.2640 0.139 Uiso 0.464(8) 1 calc PR B 1
H11C H -0.0739 0.6590 0.1423 0.139 Uiso 0.464(8) 1 calc PR B 1
C11A C -0.0152(18) 0.5271(18) 0.3718(19) 0.093(3) Uani 0.312(8) 1 d P B 2
H11D H -0.0573 0.6327 0.3583 0.139 Uiso 0.312(8) 1 calc PR B 2
H11E H 0.0322 0.4643 0.4639 0.139 Uiso 0.312(8) 1 calc PR B 2
H11F H -0.0898 0.4927 0.3668 0.139 Uiso 0.312(8) 1 calc PR B 2
C11B C -0.061(3) 0.574(3) 0.267(3) 0.093(3) Uani 0.223(9) 1 d P B 3
H11G H -0.0916 0.6259 0.1685 0.139 Uiso 0.223(9) 1 calc PR B 3
H11H H -0.0949 0.6455 0.3098 0.139 Uiso 0.223(9) 1 calc PR B 3
H11I H -0.0998 0.4928 0.3173 0.139 Uiso 0.223(9) 1 calc PR B 3
C4 C 0.5329(3) 0.4584(3) 0.2261(3) 0.0396(7) Uani 1 1 d . . .
C7 C 0.3516(3) 0.3238(4) 0.3306(3) 0.0435(8) Uani 1 1 d . . .
H7A H 0.317(4) 0.292(4) 0.419(4) 0.065 Uiso 1 1 d . . .
C8 C 0.4097(3) 0.4465(3) 0.3099(3) 0.0408(7) Uani 1 1 d . A .
C5 C 0.5523(3) 0.2437(4) 0.1702(3) 0.0417(7) Uani 1 1 d . . .
H5A H 0.496(4) 0.282(4) 0.088(3) 0.063 Uiso 1 1 d . . .
C6 C 0.4707(4) 0.1881(4) 0.3085(4) 0.0473(8) Uani 1 1 d . A .
H6A H 0.534(4) 0.139(4) 0.385(4) 0.071 Uiso 1 1 d . . .
H6B H 0.430(4) 0.118(4) 0.307(3) 0.071 Uiso 1 1 d . . .
N1 N 0.6037(3) 0.3598(3) 0.1637(3) 0.0508(7) Uani 1 1 d . A .
H1 H 0.662(4) 0.387(4) 0.100(4) 0.061 Uiso 1 1 d . . .
P2 P 0.70208(10) 0.08803(11) 0.14929(11) 0.0550(3) Uani 1 1 d . A .
O6 O 0.8178(7) 0.1365(8) 0.0559(7) 0.0680(14) Uani 0.512(3) 1 d P A 1
O7 O 0.6279(10) 0.0100(10) 0.0943(9) 0.086(2) Uani 0.512(3) 1 d P A 1
C13 C 0.6887(11) -0.0629(11) -0.0138(10) 0.108(2) Uani 0.512(3) 1 d P A 1
H13A H 0.7468 -0.0094 -0.0827 0.161 Uiso 0.512(3) 1 calc PR A 1
H13B H 0.6100 -0.0549 -0.0620 0.161 Uiso 0.512(3) 1 calc PR A 1
H13C H 0.7471 -0.1695 0.0364 0.161 Uiso 0.512(3) 1 calc PR A 1
O8 O 0.7624(5) -0.0470(5) 0.2955(6) 0.0701(10) Uani 0.512(3) 1 d P A 1
C12 C 0.8615(6) -0.0533(5) 0.3813(5) 0.0950(14) Uani 1 1 d . A 1
H12A H 0.9490 -0.0488 0.3292 0.142 Uiso 0.512(3) 1 calc PR A 1
H12B H 0.8829 -0.1479 0.4667 0.142 Uiso 0.512(3) 1 calc PR A 1
H12C H 0.8204 0.0324 0.4067 0.142 Uiso 0.512(3) 1 calc PR A 1
H12D H 0.8192 -0.0608 0.4725 0.142 Uiso 0.488(3) 1 calc PR A 1
H12E H 0.8853 0.0384 0.3350 0.142 Uiso 0.488(3) 1 calc PR A 1
H12F H 0.9478 -0.1419 0.3951 0.142 Uiso 0.488(3) 1 calc PR A 1
O6A O 0.7538(7) 0.1802(9) -0.0017(8) 0.0680(14) Uani 0.488(3) 1 d P A 2
O7A O 0.6645(10) -0.0432(10) 0.1803(9) 0.086(2) Uani 0.488(3) 1 d P A 2
C13A C 0.8696(12) 0.1060(11) -0.0589(11) 0.108(2) Uani 0.488(3) 1 d P A 2
H13D H 0.9518 0.0587 0.0038 0.161 Uiso 0.488(3) 1 calc PR A 2
H13E H 0.8891 0.1781 -0.1501 0.161 Uiso 0.488(3) 1 calc PR A 2
H13F H 0.8508 0.0281 -0.0713 0.161 Uiso 0.488(3) 1 calc PR A 2
O8A O 0.8261(5) 0.0565(6) 0.2475(6) 0.0701(10) Uani 0.488(3) 1 d P A 2
O4 O 0.1466(3) 0.2635(3) 0.2670(3) 0.0717(8) Uani 1 1 d . . .
C10 C 0.0278(7) 0.2640(7) 0.2075(6) 0.089(2) Uani 0.837(8) 1 d P A 1
H10A H 0.0517 0.1662 0.2048 0.134 Uiso 0.837(8) 1 calc PR A 1
H10B H 0.0078 0.3444 0.1120 0.134 Uiso 0.837(8) 1 calc PR A 1
H10C H -0.0560 0.2817 0.2655 0.134 Uiso 0.837(8) 1 calc PR A 1
C10A C 0.136(4) 0.218(4) 0.151(3) 0.089(2) Uani 0.163(8) 1 d P A 2
H10D H 0.0453 0.2035 0.1585 0.134 Uiso 0.163(8) 1 calc PR A 2
H10E H 0.2141 0.1244 0.1613 0.134 Uiso 0.163(8) 1 calc PR A 2
H10F H 0.1405 0.2988 0.0587 0.134 Uiso 0.163(8) 1 calc PR A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0337(5) 0.0509(6) 0.0484(5) -0.0180(4) 0.0085(4) -0.0180(4)
O3 0.0443(13) 0.0627(15) 0.0448(13) -0.0106(11) 0.0022(10) -0.0192(12)
O5 0.0397(15) 0.119(3) 0.105(2) -0.071(2) 0.0226(15) -0.0150(17)
N2 0.064(2) 0.052(2) 0.0543(19) -0.0245(16) -0.0066(17) -0.0059(17)
C1 0.0478(19) 0.0421(19) 0.0432(18) -0.0191(15) -0.0054(15) -0.0058(16)
C2 0.054(2) 0.044(2) 0.0492(19) -0.0165(16) -0.0060(16) -0.0179(17)
C3 0.0395(18) 0.053(2) 0.0506(19) -0.0196(16) 0.0052(15) -0.0203(16)
C9 0.0386(17) 0.051(2) 0.0399(18) -0.0177(16) 0.0025(14) -0.0101(16)
O2 0.123(3) 0.0652(19) 0.088(2) -0.0463(16) 0.0137(18) -0.0338(19)
O1 0.068(3) 0.083(6) 0.070(9) -0.047(6) 0.012(4) -0.010(3)
O1A 0.068(3) 0.083(6) 0.070(9) -0.047(6) 0.012(4) -0.010(3)
C11 0.086(6) 0.078(7) 0.084(7) -0.034(6) 0.015(5) -0.004(5)
C11A 0.086(6) 0.078(7) 0.084(7) -0.034(6) 0.015(5) -0.004(5)
C11B 0.086(6) 0.078(7) 0.084(7) -0.034(6) 0.015(5) -0.004(5)
C4 0.0365(16) 0.0425(18) 0.0390(16) -0.0167(14) 0.0019(13) -0.0144(15)
C7 0.0422(18) 0.050(2) 0.0365(17) -0.0156(15) 0.0110(14) -0.0220(16)
C8 0.0358(16) 0.0420(18) 0.0363(16) -0.0119(14) -0.0004(13) -0.0106(14)
C5 0.0354(17) 0.0424(19) 0.0486(19) -0.0207(15) 0.0021(14) -0.0140(15)
C6 0.0427(19) 0.043(2) 0.048(2) -0.0127(16) 0.0004(15) -0.0152(16)
N1 0.0484(17) 0.0565(18) 0.0581(18) -0.0321(15) 0.0214(13) -0.0279(15)
P2 0.0444(5) 0.0487(6) 0.0722(7) -0.0305(5) 0.0025(5) -0.0113(4)
O6 0.060(4) 0.062(4) 0.070(4) -0.030(3) 0.019(3) -0.014(3)
O7 0.065(4) 0.072(5) 0.139(7) -0.065(5) 0.016(5) -0.023(4)
C13 0.110(6) 0.078(5) 0.092(5) -0.021(4) 0.029(4) -0.018(4)
O8 0.051(2) 0.051(2) 0.090(3) -0.015(2) -0.0065(19) -0.0147(17)
C12 0.111(4) 0.075(3) 0.072(3) -0.017(2) -0.009(3) -0.018(3)
O6A 0.060(4) 0.062(4) 0.070(4) -0.030(3) 0.019(3) -0.014(3)
O7A 0.065(4) 0.072(5) 0.139(7) -0.065(5) 0.016(5) -0.023(4)
C13A 0.110(6) 0.078(5) 0.092(5) -0.021(4) 0.029(4) -0.018(4)
O8A 0.051(2) 0.051(2) 0.090(3) -0.015(2) -0.0065(19) -0.0147(17)
O4 0.0651(16) 0.0732(18) 0.0740(17) -0.0082(14) -0.0104(13) -0.0445(15)
C10 0.096(5) 0.107(5) 0.096(4) -0.043(3) -0.008(3) -0.064(4)
C10A 0.096(5) 0.107(5) 0.096(4) -0.043(3) -0.008(3) -0.064(4)

_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 1.454(2) . ?
P1 O5 1.556(3) . ?
P1 O4 1.558(2) . ?
P1 C7 1.810(3) . ?
O5 C11A 1.270(15) . ?
O5 C11B 1.27(2) . ?
O5 C11 1.316(11) . ?
N2 O1A 1.16(4) . ?
N2 O2 1.228(4) . ?
N2 O1 1.255(15) . ?
N2 C1 1.446(4) . ?
C1 C9 1.373(4) . ?
C1 C2 1.386(4) . ?
C2 C3 1.362(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.404(4) . ?
C3 H3A 0.9300 . ?
C9 C8 1.389(4) . ?
C9 H9A 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C11B H11G 0.9600 . ?
C11B H11H 0.9600 . ?
C11B H11I 0.9600 . ?
C4 N1 1.363(4) . ?
C4 C8 1.406(4) . ?
C7 C8 1.512(4) . ?
C7 C6 1.538(4) . ?
C7 H7A 0.89(3) . ?
C5 N1 1.452(4) . ?
C5 C6 1.525(4) . ?
C5 P2 1.801(3) . ?
C5 H5A 0.94(3) . ?
C6 H6A 0.92(4) . ?
C6 H6B 0.96(4) . ?
N1 H1 0.83(3) . ?
P2 O7A 1.435(10) . ?
P2 O6 1.481(7) . ?
P2 O8 1.546(5) . ?
P2 O6A 1.563(8) . ?
P2 O8A 1.579(5) . ?
P2 O7 1.596(8) . ?
O7 C13 1.548(13) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O8 C12 1.404(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12D 0.9600 . ?
C12 H12E 0.9600 . ?
C12 H12F 0.9600 . ?
O6A C13A 1.338(12) . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 0.9600 . ?
O4 C10 1.425(5) . ?
O4 C10A 1.51(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 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 O5 113.13(16) . . ?
O3 P1 O4 115.40(13) . . ?
O5 P1 O4 104.69(16) . . ?
O3 P1 C7 115.83(13) . . ?
O5 P1 C7 104.80(15) . . ?
O4 P1 C7 101.56(14) . . ?
C11A O5 C11B 50.1(12) . . ?
C11A O5 C11 82.9(9) . . ?
C11B O5 C11 50.9(12) . . ?
C11A O5 P1 146.2(8) . . ?
C11B O5 P1 134.6(12) . . ?
C11 O5 P1 127.5(5) . . ?
O1A N2 O2 120(2) . . ?
O2 N2 O1 122.8(5) . . ?
O1A N2 C1 118.0(19) . . ?
O2 N2 C1 118.4(3) . . ?
O1 N2 C1 118.6(5) . . ?
C9 C1 C2 120.9(3) . . ?
C9 C1 N2 119.3(3) . . ?
C2 C1 N2 119.8(3) . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C1 C9 C8 121.1(3) . . ?
C1 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
O5 C11A H11D 109.5 . . ?
O5 C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
O5 C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
O5 C11B H11G 109.5 . . ?
O5 C11B H11H 109.5 . . ?
O5 C11B H11I 109.5 . . ?
N1 C4 C3 119.6(3) . . ?
N1 C4 C8 121.4(3) . . ?
C3 C4 C8 119.0(3) . . ?
C8 C7 C6 111.0(2) . . ?
C8 C7 P1 111.0(2) . . ?
C6 C7 P1 112.3(2) . . ?
C8 C7 H7A 108(2) . . ?
C6 C7 H7A 110(2) . . ?
P1 C7 H7A 104(2) . . ?
C9 C8 C4 118.5(3) . . ?
C9 C8 C7 121.5(3) . . ?
C4 C8 C7 120.1(3) . . ?
N1 C5 C6 110.8(3) . . ?
N1 C5 P2 109.7(2) . . ?
C6 C5 P2 112.3(2) . . ?
N1 C5 H5A 111(2) . . ?
C6 C5 H5A 112(2) . . ?
P2 C5 H5A 101(2) . . ?
C5 C6 C7 111.5(3) . . ?
C5 C6 H6A 109(2) . . ?
C7 C6 H6A 106(2) . . ?
C5 C6 H6B 110(2) . . ?
C7 C6 H6B 111(2) . . ?
H6A C6 H6B 110(3) . . ?
C4 N1 C5 122.9(3) . . ?
C4 N1 H1 116(2) . . ?
C5 N1 H1 119(2) . . ?
O7A P2 O6 128.8(5) . . ?
O7A P2 O8 66.9(4) . . ?
O6 P2 O8 112.0(3) . . ?
O7A P2 O6A 122.3(5) . . ?
O8 P2 O6A 141.0(3) . . ?
O7A P2 O8A 115.0(4) . . ?
O6 P2 O8A 71.6(3) . . ?
O8 P2 O8A 50.1(2) . . ?
O6A P2 O8A 100.6(3) . . ?
O6 P2 O7 114.5(4) . . ?
O8 P2 O7 99.6(4) . . ?
O6A P2 O7 95.1(4) . . ?
O8A P2 O7 144.8(3) . . ?
O7A P2 C5 112.7(4) . . ?
O6 P2 C5 114.1(3) . . ?
O8 P2 C5 111.7(2) . . ?
O6A P2 C5 99.3(3) . . ?
O8A P2 C5 104.3(2) . . ?
O7 P2 C5 103.9(3) . . ?
C13 O7 P2 127.7(7) . . ?
C12 O8 P2 124.6(4) . . ?
O8 C12 H12A 109.5 . . ?
O8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O8 C12 H12D 109.5 . . ?
H12A C12 H12D 141.1 . . ?
H12B C12 H12D 56.3 . . ?
H12C C12 H12D 56.3 . . ?
O8 C12 H12E 109.5 . . ?
H12A C12 H12E 56.3 . . ?
H12B C12 H12E 141.1 . . ?
H12C C12 H12E 56.3 . . ?
H12D C12 H12E 109.5 . . ?
O8 C12 H12F 109.5 . . ?
H12A C12 H12F 56.3 . . ?
H12B C12 H12F 56.3 . . ?
H12C C12 H12F 141.1 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
C13A O6A P2 119.3(6) . . ?
O6A C13A H13D 109.5 . . ?
O6A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
O6A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C10 O4 C10A 47.2(13) . . ?
C10 O4 P1 124.7(3) . . ?
C10A O4 P1 115.5(12) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
O4 C10A H10D 109.5 . . ?
O4 C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
O4 C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 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 O5 C11A 156.1(16) . . . . ?
O4 P1 O5 C11A 29.6(16) . . . . ?
C7 P1 O5 C11A -76.8(16) . . . . ?
O3 P1 O5 C11B 74.6(19) . . . . ?
O4 P1 O5 C11B -51.8(19) . . . . ?
C7 P1 O5 C11B -158.3(19) . . . . ?
O3 P1 O5 C11 5.7(8) . . . . ?
O4 P1 O5 C11 -120.8(8) . . . . ?
C7 P1 O5 C11 132.7(8) . . . . ?
O1A N2 C1 C9 -23(3) . . . . ?
O2 N2 C1 C9 178.9(3) . . . . ?
O1 N2 C1 C9 2.7(15) . . . . ?
O1A N2 C1 C2 157(3) . . . . ?
O2 N2 C1 C2 -1.0(4) . . . . ?
O1 N2 C1 C2 -177.2(14) . . . . ?
C9 C1 C2 C3 0.6(5) . . . . ?
N2 C1 C2 C3 -179.5(3) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C1 C9 C8 -1.4(4) . . . . ?
N2 C1 C9 C8 178.7(3) . . . . ?
C2 C3 C4 N1 180.0(3) . . . . ?
C2 C3 C4 C8 -1.6(5) . . . . ?
O3 P1 C7 C8 59.4(3) . . . . ?
O5 P1 C7 C8 -66.0(2) . . . . ?
O4 P1 C7 C8 -174.7(2) . . . . ?
O3 P1 C7 C6 -65.5(3) . . . . ?
O5 P1 C7 C6 169.1(2) . . . . ?
O4 P1 C7 C6 60.4(2) . . . . ?
C1 C9 C8 C4 0.7(4) . . . . ?
C1 C9 C8 C7 -179.2(3) . . . . ?
N1 C4 C8 C9 179.1(3) . . . . ?
C3 C4 C8 C9 0.7(4) . . . . ?
N1 C4 C8 C7 -0.9(4) . . . . ?
C3 C4 C8 C7 -179.3(3) . . . . ?
C6 C7 C8 C9 -156.3(3) . . . . ?
P1 C7 C8 C9 78.1(3) . . . . ?
C6 C7 C8 C4 23.8(4) . . . . ?
P1 C7 C8 C4 -101.9(3) . . . . ?
N1 C5 C6 C7 52.2(4) . . . . ?
P2 C5 C6 C7 175.2(2) . . . . ?
C8 C7 C6 C5 -48.9(3) . . . . ?
P1 C7 C6 C5 76.0(3) . . . . ?
C3 C4 N1 C5 -177.1(3) . . . . ?
C8 C4 N1 C5 4.5(5) . . . . ?
C6 C5 N1 C4 -30.6(4) . . . . ?
P2 C5 N1 C4 -155.0(3) . . . . ?
N1 C5 P2 O7A 169.4(4) . . . . ?
C6 C5 P2 O7A 45.8(4) . . . . ?
N1 C5 P2 O6 -32.1(4) . . . . ?
C6 C5 P2 O6 -155.7(3) . . . . ?
N1 C5 P2 O8 96.2(3) . . . . ?
C6 C5 P2 O8 -27.4(3) . . . . ?
N1 C5 P2 O6A -59.7(4) . . . . ?
C6 C5 P2 O6A 176.7(4) . . . . ?
N1 C5 P2 O8A 43.9(3) . . . . ?
C6 C5 P2 O8A -79.7(3) . . . . ?
N1 C5 P2 O7 -157.4(4) . . . . ?
C6 C5 P2 O7 79.1(4) . . . . ?
O7A P2 O7 C13 -104.9(15) . . . . ?
O6 P2 O7 C13 19.6(9) . . . . ?
O8 P2 O7 C13 -100.1(7) . . . . ?
O6A P2 O7 C13 43.7(8) . . . . ?
O8A P2 O7 C13 -73.0(10) . . . . ?
C5 P2 O7 C13 144.6(7) . . . . ?
O7A P2 O8 C12 170.8(7) . . . . ?
O6 P2 O8 C12 46.6(6) . . . . ?
O6A P2 O8 C12 57.4(8) . . . . ?
O8A P2 O8 C12 8.0(4) . . . . ?
O7 P2 O8 C12 168.0(5) . . . . ?
C5 P2 O8 C12 -82.8(5) . . . . ?
O7A P2 O6A C13A -57.1(9) . . . . ?
O6 P2 O6A C13A 55.7(10) . . . . ?
O8 P2 O6A C13A 35.5(11) . . . . ?
O8A P2 O6A C13A 71.8(8) . . . . ?
O7 P2 O6A C13A -76.6(8) . . . . ?
C5 P2 O6A C13A 178.5(8) . . . . ?
O3 P1 O4 C10 -52.0(4) . . . . ?
O5 P1 O4 C10 73.1(4) . . . . ?
C7 P1 O4 C10 -178.1(4) . . . . ?
O3 P1 O4 C10A 2.2(16) . . . . ?
O5 P1 O4 C10A 127.2(16) . . . . ?
C7 P1 O4 C10A -123.9(16) . . . . ?

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 H1 O3 0.84(4) 2.20(4) 3.010(4) 164(4) 2_665
C6 H6A O2 0.92(4) 2.56(4) 3.390(5) 150(3) 2_666
C12 H12B O4 0.96 2.51 3.337(5) 145 2_656
C13 H13B O7 0.96 2.31 3.187(16) 154 2_655

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048