# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_C26H20FN6O4P
_database_code_depnum_ccdc_archive 'CCDC 1044179'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            '[TPP][FDNTz]'
_chemical_formula_moiety         'C24 H20 P, C2 F N6 O4'
_chemical_formula_sum            'C26 H20 F N6 O4 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         530.45
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.8077(14)
_cell_length_b                   7.1276(8)
_cell_length_c                   14.7721(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.585(2)
_cell_angle_gamma                90
_cell_volume                     1237.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    26729
_cell_measurement_theta_min      1.73
_cell_measurement_theta_max      30.54
_cell_measurement_temperature    101.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548

_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2014/4'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      101.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            26729
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_full        30.54
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             7495
_reflns_number_gt                5985
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1005
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         7495
_refine_ls_number_parameters     343
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.2111P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 2380 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)

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'
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'
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XL 2014/6 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XL 2014/6 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2895(2) 0.7197(4) 0.27514(17) 0.0206(5) Uani d . . . 1 . .
C C2 0.2976(3) 0.6241(4) 0.36416(19) 0.0270(6) Uani d . . . 1 . .
C C3 0.6647(2) 0.3444(3) 0.24807(16) 0.0147(5) Uani d . . . 1 . .
C C4 0.7107(2) 0.2030(4) 0.30569(17) 0.0187(5) Uani d . . . 1 . .
H H4 0.7909 0.1888 0.3164 0.022 Uiso calc U . R 1 . .
C C5 0.6394(2) 0.0831(4) 0.34731(17) 0.0200(5) Uani d . . . 1 . .
H H5 0.6707 -0.0116 0.3875 0.024 Uiso calc U . R 1 . .
C C6 0.5218(2) 0.1014(4) 0.33023(17) 0.0201(5) Uani d . . . 1 . .
H H6 0.4729 0.0194 0.359 0.024 Uiso calc U . R 1 . .
C C7 0.4762(2) 0.2392(4) 0.27128(17) 0.0193(5) Uani d . . . 1 . .
H H7 0.396 0.2494 0.2587 0.023 Uiso calc U . R 1 . .
C C8 0.5468(2) 0.3625(4) 0.23034(16) 0.0162(5) Uani d . . . 1 . .
H H8 0.5153 0.4581 0.1907 0.019 Uiso calc U . R 1 . .
C C9 0.8637(2) 0.3581(4) 0.14949(17) 0.0162(5) Uani d . . . 1 . .
C C10 0.8234(2) 0.2380(4) 0.07869(17) 0.0197(5) Uani d . . . 1 . .
H H10 0.7456 0.2414 0.0552 0.024 Uiso calc U . R 1 . .
C C11 0.8979(2) 0.1136(4) 0.04293(19) 0.0235(6) Uani d . . . 1 . .
H H11 0.8714 0.0335 -0.006 0.028 Uiso calc U . R 1 . .
C C12 1.0110(2) 0.1061(4) 0.0785(2) 0.0260(6) Uani d . . . 1 . .
H H12 1.0612 0.019 0.0546 0.031 Uiso calc U . R 1 . .
C C13 1.0513(2) 0.2252(4) 0.1489(2) 0.0259(6) Uani d . . . 1 . .
H H13 1.1288 0.2195 0.1729 0.031 Uiso calc U . R 1 . .
C C14 0.9781(2) 0.3526(4) 0.18422(18) 0.0214(6) Uani d . . . 1 . .
H H14 1.0057 0.4356 0.2317 0.026 Uiso calc U . R 1 . .
C C15 0.8323(2) 0.6430(4) 0.28911(16) 0.0163(5) Uani d . . . 1 . .
C C16 0.8047(2) 0.6279(4) 0.37887(17) 0.0194(5) Uani d . . . 1 . .
H H16 0.75 0.5386 0.3943 0.023 Uiso calc U . R 1 . .
C C17 0.8582(3) 0.7451(4) 0.44523(18) 0.0261(6) Uani d . . . 1 . .
H H17 0.8399 0.7357 0.5063 0.031 Uiso calc U . R 1 . .
C C18 0.9381(2) 0.8756(4) 0.4229(2) 0.0277(6) Uani d . . . 1 . .
H H18 0.9744 0.9548 0.4687 0.033 Uiso calc U . R 1 . .
C C19 0.9654(2) 0.8909(4) 0.3335(2) 0.0276(6) Uani d . . . 1 . .
H H19 1.0206 0.9796 0.3185 0.033 Uiso calc U . R 1 . .
C C20 0.9118(2) 0.7763(4) 0.26629(19) 0.0228(6) Uani d . . . 1 . .
H H20 0.9291 0.7884 0.2051 0.027 Uiso calc U . R 1 . .
C C21 0.6892(2) 0.6579(3) 0.11995(16) 0.0150(5) Uani d . . . 1 . .
C C22 0.7097(2) 0.6637(4) 0.02829(17) 0.0178(5) Uani d . . . 1 . .
H H22 0.7596 0.5752 0.005 0.021 Uiso calc U . R 1 . .
C C23 0.6567(2) 0.7992(4) -0.02822(17) 0.0208(6) Uani d . . . 1 . .
H H23 0.6712 0.8046 -0.0903 0.025 Uiso calc U . R 1 . .
C C24 0.5825(2) 0.9272(4) 0.00530(18) 0.0202(5) Uani d . . . 1 . .
H H24 0.5472 1.0205 -0.0338 0.024 Uiso calc U . R 1 . .
C C25 0.5596(2) 0.9192(4) 0.09604(17) 0.0194(5) Uani d . . . 1 . .
H H25 0.5072 1.0047 0.1183 0.023 Uiso calc U . R 1 . .
C C26 0.6132(2) 0.7868(4) 0.15342(17) 0.0174(5) Uani d . . . 1 . .
H H26 0.5988 0.7826 0.2155 0.021 Uiso calc U . R 1 . .
F F1 0.23655(19) 0.4658(3) 0.36487(13) 0.0455(6) Uani d . . . 1 . .
N N1 0.3149(2) 0.6265(4) 0.20131(17) 0.0315(6) Uani d . . . 1 . .
N N2 0.2939(2) 0.7541(4) 0.13452(15) 0.0290(6) Uani d . . . 1 . .
N N3 0.2579(2) 0.9110(4) 0.16813(16) 0.0264(5) Uani d . . . 1 . .
N N4 0.2544(2) 0.8930(4) 0.25860(16) 0.0264(5) Uani d . . . 1 . .
N N5 0.4195(2) 0.5704(4) 0.40249(15) 0.0281(6) Uani d . . . 1 . .
N N6 0.2590(2) 0.7542(4) 0.43795(16) 0.0299(6) Uani d . . . 1 . .
O O1 0.49759(19) 0.6562(3) 0.37486(15) 0.0331(5) Uani d . . . 1 . .
O O2 0.4252(2) 0.4430(4) 0.45776(15) 0.0465(7) Uani d . . . 1 . .
O O3 0.32180(19) 0.8856(4) 0.45835(15) 0.0365(5) Uani d . . . 1 . .
O O4 0.17022(19) 0.7144(4) 0.46911(16) 0.0399(6) Uani d . . . 1 . .
P P1 0.76191(5) 0.50104(9) 0.20038(4) 0.01387(13) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N4 . 1.319(4) ?
C1 N1 . 1.335(4) ?
C1 C2 . 1.476(4) ?
C2 F1 . 1.339(4) ?
C2 N6 . 1.534(4) ?
C2 N5 . 1.543(4) ?
C3 C4 . 1.395(3) ?
C3 C8 . 1.398(4) ?
C3 P1 . 1.793(3) ?
C4 C5 . 1.385(4) ?
C4 H4 . 0.95 ?
C5 C6 . 1.394(4) ?
C5 H5 . 0.95 ?
C6 C7 . 1.386(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.390(3) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C9 C14 . 1.398(4) ?
C9 C10 . 1.399(4) ?
C9 P1 . 1.796(3) ?
C10 C11 . 1.389(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.388(4) ?
C11 H11 . 0.95 ?
C12 C13 . 1.390(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.389(4) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 C16 . 1.400(3) ?
C15 C20 . 1.400(4) ?
C15 P1 . 1.794(3) ?
C16 C17 . 1.392(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.387(5) ?
C17 H17 . 0.95 ?
C18 C19 . 1.394(4) ?
C18 H18 . 0.95 ?
C19 C20 . 1.390(4) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 C22 . 1.399(3) ?
C21 C26 . 1.407(3) ?
C21 P1 . 1.789(3) ?
C22 C23 . 1.385(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.389(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.394(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.381(4) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
N1 N2 . 1.347(4) ?
N2 N3 . 1.311(4) ?
N3 N4 . 1.347(3) ?
N5 O1 . 1.210(3) ?
N5 O2 . 1.218(3) ?
N6 O3 . 1.214(4) ?
N6 O4 . 1.219(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N4 C1 N1 . . 113.9(2) ?
N4 C1 C2 . . 126.1(3) ?
N1 C1 C2 . . 119.9(3) ?
F1 C2 C1 . . 114.1(2) ?
F1 C2 N6 . . 107.8(2) ?
C1 C2 N6 . . 110.9(2) ?
F1 C2 N5 . . 105.8(2) ?
C1 C2 N5 . . 114.7(2) ?
N6 C2 N5 . . 102.7(2) ?
C4 C3 C8 . . 120.2(2) ?
C4 C3 P1 . . 117.6(2) ?
C8 C3 P1 . . 122.20(19) ?
C5 C4 C3 . . 120.0(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.0(2) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C7 C6 C5 . . 119.9(2) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C6 C7 C8 . . 120.6(2) ?
C6 C7 H7 . . 119.7 ?
C8 C7 H7 . . 119.7 ?
C7 C8 C3 . . 119.3(2) ?
C7 C8 H8 . . 120.4 ?
C3 C8 H8 . . 120.4 ?
C14 C9 C10 . . 120.2(2) ?
C14 C9 P1 . . 121.6(2) ?
C10 C9 P1 . . 117.9(2) ?
C11 C10 C9 . . 119.6(3) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.1(3) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 120.4(3) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.0(3) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C9 . . 119.6(3) ?
C13 C14 H14 . . 120.2 ?
C9 C14 H14 . . 120.2 ?
C16 C15 C20 . . 120.2(2) ?
C16 C15 P1 . . 121.0(2) ?
C20 C15 P1 . . 118.71(19) ?
C17 C16 C15 . . 119.3(3) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C18 C17 C16 . . 120.5(3) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C17 C18 C19 . . 120.2(3) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C20 C19 C18 . . 120.0(3) ?
C20 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?
C19 C20 C15 . . 119.7(3) ?
C19 C20 H20 . . 120.1 ?
C15 C20 H20 . . 120.1 ?
C22 C21 C26 . . 119.8(2) ?
C22 C21 P1 . . 123.0(2) ?
C26 C21 P1 . . 117.12(18) ?
C23 C22 C21 . . 119.6(2) ?
C23 C22 H22 . . 120.2 ?
C21 C22 H22 . . 120.2 ?
C22 C23 C24 . . 120.4(2) ?
C22 C23 H23 . . 119.8 ?
C24 C23 H23 . . 119.8 ?
C23 C24 C25 . . 120.3(2) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C26 C25 C24 . . 119.8(2) ?
C26 C25 H25 . . 120.1 ?
C24 C25 H25 . . 120.1 ?
C25 C26 C21 . . 120.0(2) ?
C25 C26 H26 . . 120.0 ?
C21 C26 H26 . . 120.0 ?
C1 N1 N2 . . 102.9(2) ?
N3 N2 N1 . . 110.0(2) ?
N2 N3 N4 . . 109.7(2) ?
C1 N4 N3 . . 103.5(2) ?
O1 N5 O2 . . 127.5(3) ?
O1 N5 C2 . . 117.7(2) ?
O2 N5 C2 . . 114.8(3) ?
O3 N6 O4 . . 127.8(3) ?
O3 N6 C2 . . 115.2(2) ?
O4 N6 C2 . . 117.0(3) ?
C21 P1 C3 . . 111.48(12) ?
C21 P1 C15 . . 106.91(12) ?
C3 P1 C15 . . 109.41(12) ?
C21 P1 C9 . . 111.97(11) ?
C3 P1 C9 . . 106.93(12) ?
C15 P1 C9 . . 110.15(13) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_CH6N4O4
_database_code_depnum_ccdc_archive 'CCDC 1044180'
_audit_update_record             
;
2015-01-21 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;
_chemical_name_systematic        'hydrazinium dinitrocyanomethide'
_chemical_name_common            '[N2H5][(NO2)2CN]'
_chemical_formula_moiety         'C H N2 O4, H5 N2'
_chemical_formula_sum            'C H6 N4 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         138.10

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   3.6434(4)
_cell_length_b                   13.7827(13)
_cell_length_c                   10.6457(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.230(2)
_cell_angle_gamma                90
_cell_volume                     529.08(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12436
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      30.61
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.098
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288

_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2014/4'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            12436
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         30.61
_diffrn_reflns_theta_full        30.61
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             1614
_reflns_number_gt                1465
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0769
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_number_reflns         1614
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.1095P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XL 2014/6 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XL 2014/6 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3641(2) 0.50613(5) 0.15481(7) 0.01206(15) Uani d . . . 1 . .
H H1 0.213(3) 0.4675(9) 0.1007(11) 0.014 Uiso d U . . 1 . .
N N1 0.39509(17) 0.60208(5) 0.12520(6) 0.01096(14) Uani d . . . 1 . .
N N2 0.54237(17) 0.46290(5) 0.26182(6) 0.01089(14) Uani d . . . 1 . .
N N3 -0.13535(18) 0.30543(5) 0.57358(6) 0.01195(14) Uani d . . . 1 . .
H H2 -0.087(3) 0.2425(9) 0.5933(11) 0.014 Uiso d U . . 1 . .
H H3 -0.041(3) 0.3378(9) 0.6405(11) 0.014 Uiso d U . . 1 . .
N N4 0.09230(18) 0.33019(5) 0.47678(6) 0.01092(14) Uani d . . . 1 . .
H H4 0.333(3) 0.3256(9) 0.5055(11) 0.013 Uiso d U . . 1 . .
H H5 0.039(3) 0.2903(9) 0.4140(11) 0.013 Uiso d U . . 1 . .
H H6 0.032(3) 0.3895(9) 0.4477(11) 0.013 Uiso d U . . 1 . .
O O1 0.58787(16) 0.66234(4) 0.19448(5) 0.01541(14) Uani d . . . 1 . .
O O2 0.21327(17) 0.62862(4) 0.02069(5) 0.01605(14) Uani d . . . 1 . .
O O3 0.75790(16) 0.50676(4) 0.34655(5) 0.01505(14) Uani d . . . 1 . .
O O4 0.47962(17) 0.37323(4) 0.27230(6) 0.01509(14) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.3647(9) ?
C1 N1 . 1.3680(10) ?
C1 H1 . 0.910(12) ?
N1 O1 . 1.2565(8) ?
N1 O2 . 1.2647(8) ?
N2 O3 . 1.2621(8) ?
N2 O4 . 1.2648(8) ?
N3 N4 . 1.4529(9) ?
N3 H2 . 0.904(12) ?
N3 H3 . 0.869(12) ?
N4 H4 . 0.890(12) ?
N4 H5 . 0.866(12) ?
N4 H6 . 0.890(12) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 . . 124.70(7) ?
N2 C1 H1 . . 116.5(8) ?
N1 C1 H1 . . 118.8(8) ?
O1 N1 O2 . . 120.24(6) ?
O1 N1 C1 . . 124.15(6) ?
O2 N1 C1 . . 115.61(6) ?
O3 N2 O4 . . 120.45(6) ?
O3 N2 C1 . . 124.09(6) ?
O4 N2 C1 . . 115.46(6) ?
N4 N3 H2 . . 106.2(7) ?
N4 N3 H3 . . 105.2(8) ?
H2 N3 H3 . . 105.2(11) ?
N3 N4 H4 . . 112.0(7) ?
N3 N4 H5 . . 108.1(8) ?
H4 N4 H5 . . 108.8(11) ?
N3 N4 H6 . . 109.0(7) ?
H4 N4 H6 . . 111.5(11) ?
H5 N4 H6 . . 107.4(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C1 N1 O1 . . . . -1.20(12) ?
N2 C1 N1 O2 . . . . 178.87(7) ?
N1 C1 N2 O3 . . . . 0.05(12) ?
N1 C1 N2 O4 . . . . -179.77(7) ?



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# 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_C26H20N3O4P
_database_code_depnum_ccdc_archive 'CCDC 1044181'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            '[PPh4][FDNTz]'
_chemical_formula_moiety         'C24 H20 P, C2 N3 O4'
_chemical_formula_sum            'C26 H20 N3 O4 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         469.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.6601(8)
_cell_length_b                   14.2600(9)
_cell_length_c                   13.4402(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.0990(10)
_cell_angle_gamma                90
_cell_volume                     2234.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    125
_cell_measurement_theta_min      3.7627
_cell_measurement_theta_max      25.9237
_cell_measurement_temperature    104.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.142
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976

_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2014/4'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      104.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            55116
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             6814
_reflns_number_gt                5611
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0988
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_number_reflns         6814
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+1.0542P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XL 2014/6 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XL 2014/6 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.57515(10) 0.24267(8) 0.13252(9) 0.0185(2) Uani d . . . 1 . .
C C2 0.50448(11) 0.32182(9) 0.14897(9) 0.0212(2) Uani d . . . 1 . .
C C3 0.59960(9) 0.32770(8) 0.52773(8) 0.0150(2) Uani d . . . 1 . .
C C4 0.56677(10) 0.38204(8) 0.60961(9) 0.0191(2) Uani d . . . 1 . .
H H4 0.5232 0.3548 0.6618 0.023 Uiso calc U . R 1 . .
C C5 0.59821(11) 0.47605(9) 0.61419(9) 0.0213(2) Uani d . . . 1 . .
H H5 0.5763 0.513 0.6698 0.026 Uiso calc U . R 1 . .
C C6 0.66156(11) 0.51598(8) 0.53771(9) 0.0211(2) Uani d . . . 1 . .
H H6 0.6839 0.5799 0.5416 0.025 Uiso calc U . R 1 . .
C C7 0.69228(11) 0.46280(9) 0.45572(9) 0.0226(2) Uani d . . . 1 . .
H H7 0.7345 0.4908 0.4031 0.027 Uiso calc U . R 1 . .
C C8 0.66167(11) 0.36856(9) 0.45002(9) 0.0202(2) Uani d . . . 1 . .
H H8 0.6828 0.3322 0.3937 0.024 Uiso calc U . R 1 . .
C C9 0.56301(10) 0.14923(8) 0.63784(8) 0.0158(2) Uani d . . . 1 . .
C C10 0.48592(10) 0.17620(9) 0.71296(9) 0.0184(2) Uani d . . . 1 . .
H H10 0.431 0.224 0.7007 0.022 Uiso calc U . R 1 . .
C C11 0.49076(11) 0.13231(9) 0.80531(9) 0.0229(2) Uani d . . . 1 . .
H H11 0.4397 0.1511 0.8566 0.027 Uiso calc U . R 1 . .
C C12 0.56992(12) 0.06095(9) 0.82315(9) 0.0247(3) Uani d . . . 1 . .
H H12 0.5728 0.0313 0.8864 0.03 Uiso calc U . R 1 . .
C C13 0.64447(11) 0.03337(9) 0.74845(10) 0.0237(2) Uani d . . . 1 . .
H H13 0.6977 -0.0158 0.7605 0.028 Uiso calc U . R 1 . .
C C14 0.64200(10) 0.07723(8) 0.65588(9) 0.0193(2) Uani d . . . 1 . .
H H14 0.6937 0.0584 0.6052 0.023 Uiso calc U . R 1 . .
C C15 0.65965(10) 0.14884(8) 0.43770(8) 0.0156(2) Uani d . . . 1 . .
C C16 0.77744(10) 0.15898(9) 0.45652(9) 0.0215(2) Uani d . . . 1 . .
H H16 0.8034 0.1998 0.5076 0.026 Uiso calc U . R 1 . .
C C17 0.85578(11) 0.10880(10) 0.39975(10) 0.0247(3) Uani d . . . 1 . .
H H17 0.9356 0.1148 0.4127 0.03 Uiso calc U . R 1 . .
C C18 0.81795(11) 0.04993(9) 0.32415(10) 0.0232(2) Uani d . . . 1 . .
H H18 0.8719 0.0155 0.2859 0.028 Uiso calc U . R 1 . .
C C19 0.70127(11) 0.04131(8) 0.30431(9) 0.0207(2) Uani d . . . 1 . .
H H19 0.676 0.0018 0.2518 0.025 Uiso calc U . R 1 . .
C C20 0.62148(10) 0.09018(8) 0.36088(8) 0.0165(2) Uani d . . . 1 . .
H H20 0.5418 0.0839 0.3476 0.02 Uiso calc U . R 1 . .
C C21 0.41860(9) 0.19620(8) 0.46439(8) 0.0144(2) Uani d . . . 1 . .
C C22 0.33667(10) 0.13492(8) 0.50303(8) 0.0169(2) Uani d . . . 1 . .
H H22 0.3533 0.0989 0.5607 0.02 Uiso calc U . R 1 . .
C C23 0.23005(10) 0.12686(9) 0.45640(9) 0.0206(2) Uani d . . . 1 . .
H H23 0.1736 0.0858 0.4828 0.025 Uiso calc U . R 1 . .
C C24 0.20647(11) 0.17880(9) 0.37136(10) 0.0237(3) Uani d . . . 1 . .
H H24 0.1339 0.1729 0.3397 0.028 Uiso calc U . R 1 . .
C C25 0.28844(11) 0.23953(9) 0.33219(10) 0.0239(2) Uani d . . . 1 . .
H H25 0.2719 0.2745 0.2738 0.029 Uiso calc U . R 1 . .
C C26 0.39447(11) 0.24886(8) 0.37875(9) 0.0193(2) Uani d . . . 1 . .
H H26 0.4503 0.2907 0.3527 0.023 Uiso calc U . R 1 . .
N N1 0.68924(9) 0.24737(7) 0.16393(7) 0.0192(2) Uani d . . . 1 . .
N N2 0.52890(10) 0.16578(8) 0.08170(8) 0.0225(2) Uani d . . . 1 . .
N N3 0.44779(11) 0.38689(9) 0.16124(9) 0.0303(3) Uani d . . . 1 . .
O O1 0.71317(8) 0.31758(7) 0.21657(7) 0.0269(2) Uani d . . . 1 . .
O O2 0.76089(8) 0.18777(6) 0.13965(7) 0.02471(19) Uani d . . . 1 . .
O O3 0.42567(9) 0.17283(8) 0.05708(9) 0.0353(2) Uani d . . . 1 . .
O O4 0.58609(9) 0.09499(7) 0.06506(8) 0.0293(2) Uani d . . . 1 . .
P P1 0.55941(2) 0.20618(2) 0.51843(2) 0.01325(7) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3966(15) ?
C1 N2 . 1.3994(16) ?
C1 C2 . 1.4150(17) ?
C2 N3 . 1.1513(17) ?
C3 C8 . 1.3989(16) ?
C3 C4 . 1.3998(16) ?
C3 P1 . 1.7994(11) ?
C4 C5 . 1.3911(17) ?
C4 H4 . 0.95 ?
C5 C6 . 1.3890(18) ?
C5 H5 . 0.95 ?
C6 C7 . 1.3853(18) ?
C6 H6 . 0.95 ?
C7 C8 . 1.3925(17) ?
C7 H7 . 0.95 ?
C8 H8 . 0.95 ?
C9 C14 . 1.4002(16) ?
C9 C10 . 1.4065(16) ?
C9 P1 . 1.7991(11) ?
C10 C11 . 1.3912(16) ?
C10 H10 . 0.95 ?
C11 C12 . 1.3943(19) ?
C11 H11 . 0.95 ?
C12 C13 . 1.386(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.3928(17) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C15 C20 . 1.4008(15) ?
C15 C16 . 1.4035(16) ?
C15 P1 . 1.7934(11) ?
C16 C17 . 1.3896(18) ?
C16 H16 . 0.95 ?
C17 C18 . 1.3894(19) ?
C17 H17 . 0.95 ?
C18 C19 . 1.3913(18) ?
C18 H18 . 0.95 ?
C19 C20 . 1.3899(16) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 C22 . 1.3956(16) ?
C21 C26 . 1.4025(16) ?
C21 P1 . 1.7998(11) ?
C22 C23 . 1.3960(16) ?
C22 H22 . 0.95 ?
C23 C24 . 1.3890(18) ?
C23 H23 . 0.95 ?
C24 C25 . 1.3937(19) ?
C24 H24 . 0.95 ?
C25 C26 . 1.3911(17) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
N1 O2 . 1.2360(14) ?
N1 O1 . 1.2571(14) ?
N2 O4 . 1.2305(14) ?
N2 O3 . 1.2518(15) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 123.45(11) ?
N1 C1 C2 . . 117.98(11) ?
N2 C1 C2 . . 118.50(11) ?
N3 C2 C1 . . 179.00(15) ?
C8 C3 C4 . . 119.93(10) ?
C8 C3 P1 . . 118.96(9) ?
C4 C3 P1 . . 121.08(9) ?
C5 C4 C3 . . 119.73(11) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C6 C5 C4 . . 120.18(11) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C7 C6 C5 . . 120.19(11) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C8 . . 120.36(11) ?
C6 C7 H7 . . 119.8 ?
C8 C7 H7 . . 119.8 ?
C7 C8 C3 . . 119.59(11) ?
C7 C8 H8 . . 120.2 ?
C3 C8 H8 . . 120.2 ?
C14 C9 C10 . . 119.81(10) ?
C14 C9 P1 . . 119.99(9) ?
C10 C9 P1 . . 120.20(9) ?
C11 C10 C9 . . 119.50(11) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C10 C11 C12 . . 120.50(12) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.89(11) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 120.50(12) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C13 C14 C9 . . 119.78(12) ?
C13 C14 H14 . . 120.1 ?
C9 C14 H14 . . 120.1 ?
C20 C15 C16 . . 120.26(11) ?
C20 C15 P1 . . 120.77(9) ?
C16 C15 P1 . . 118.85(9) ?
C17 C16 C15 . . 119.47(11) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C18 C17 C16 . . 120.30(12) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C19 . . 120.18(11) ?
C17 C18 H18 . . 119.9 ?
C19 C18 H18 . . 119.9 ?
C20 C19 C18 . . 120.40(11) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C19 C20 C15 . . 119.37(11) ?
C19 C20 H20 . . 120.3 ?
C15 C20 H20 . . 120.3 ?
C22 C21 C26 . . 120.28(10) ?
C22 C21 P1 . . 121.59(8) ?
C26 C21 P1 . . 118.06(9) ?
C21 C22 C23 . . 119.61(11) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C24 C23 C22 . . 120.03(11) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C23 C24 C25 . . 120.48(11) ?
C23 C24 H24 . . 119.8 ?
C25 C24 H24 . . 119.8 ?
C26 C25 C24 . . 119.94(11) ?
C26 C25 H25 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C25 C26 C21 . . 119.66(11) ?
C25 C26 H26 . . 120.2 ?
C21 C26 H26 . . 120.2 ?
O2 N1 O1 . . 123.15(10) ?
O2 N1 C1 . . 122.08(10) ?
O1 N1 C1 . . 114.75(10) ?
O4 N2 O3 . . 122.62(11) ?
O4 N2 C1 . . 121.53(11) ?
O3 N2 C1 . . 115.82(11) ?
C15 P1 C9 . . 108.64(5) ?
C15 P1 C3 . . 108.13(5) ?
C9 P1 C3 . . 111.53(5) ?
C15 P1 C21 . . 108.35(5) ?
C9 P1 C21 . . 110.13(5) ?
C3 P1 C21 . . 109.97(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C3 C4 C5 . . . . -1.36(18) ?
P1 C3 C4 C5 . . . . -179.37(9) ?
C3 C4 C5 C6 . . . . 0.24(18) ?
C4 C5 C6 C7 . . . . 0.99(19) ?
C5 C6 C7 C8 . . . . -1.09(19) ?
C6 C7 C8 C3 . . . . -0.04(19) ?
C4 C3 C8 C7 . . . . 1.26(18) ?
P1 C3 C8 C7 . . . . 179.31(10) ?
C14 C9 C10 C11 . . . . 1.43(17) ?
P1 C9 C10 C11 . . . . -179.18(9) ?
C9 C10 C11 C12 . . . . -1.12(18) ?
C10 C11 C12 C13 . . . . 0.00(19) ?
C11 C12 C13 C14 . . . . 0.82(19) ?
C12 C13 C14 C9 . . . . -0.50(18) ?
C10 C9 C14 C13 . . . . -0.62(17) ?
P1 C9 C14 C13 . . . . 179.98(9) ?
C20 C15 C16 C17 . . . . -1.40(18) ?
P1 C15 C16 C17 . . . . 174.70(10) ?
C15 C16 C17 C18 . . . . 0.8(2) ?
C16 C17 C18 C19 . . . . 0.4(2) ?
C17 C18 C19 C20 . . . . -1.08(19) ?
C18 C19 C20 C15 . . . . 0.47(18) ?
C16 C15 C20 C19 . . . . 0.77(17) ?
P1 C15 C20 C19 . . . . -175.26(9) ?
C26 C21 C22 C23 . . . . -0.51(17) ?
P1 C21 C22 C23 . . . . -177.55(9) ?
C21 C22 C23 C24 . . . . 0.76(18) ?
C22 C23 C24 C25 . . . . -0.30(19) ?
C23 C24 C25 C26 . . . . -0.4(2) ?
C24 C25 C26 C21 . . . . 0.67(19) ?
C22 C21 C26 C25 . . . . -0.20(18) ?
P1 C21 C26 C25 . . . . 176.94(10) ?
N2 C1 N1 O2 . . . . 7.87(18) ?
C2 C1 N1 O2 . . . . -169.02(11) ?
N2 C1 N1 O1 . . . . -173.58(11) ?
C2 C1 N1 O1 . . . . 9.53(16) ?
N1 C1 N2 O4 . . . . 3.06(18) ?
C2 C1 N2 O4 . . . . 179.94(12) ?
N1 C1 N2 O3 . . . . -178.84(11) ?
C2 C1 N2 O3 . . . . -1.97(17) ?
C20 C15 P1 C9 . . . . 106.51(10) ?
C16 C15 P1 C9 . . . . -69.57(11) ?
C20 C15 P1 C3 . . . . -132.29(9) ?
C16 C15 P1 C3 . . . . 51.63(11) ?
C20 C15 P1 C21 . . . . -13.13(11) ?
C16 C15 P1 C21 . . . . 170.79(9) ?
C14 C9 P1 C15 . . . . 4.16(11) ?
C10 C9 P1 C15 . . . . -175.23(9) ?
C14 C9 P1 C3 . . . . -114.93(10) ?
C10 C9 P1 C3 . . . . 65.68(10) ?
C14 C9 P1 C21 . . . . 122.69(9) ?
C10 C9 P1 C21 . . . . -56.70(10) ?
C8 C3 P1 C15 . . . . 25.41(11) ?
C4 C3 P1 C15 . . . . -156.56(9) ?
C8 C3 P1 C9 . . . . 144.80(9) ?
C4 C3 P1 C9 . . . . -37.17(11) ?
C8 C3 P1 C21 . . . . -92.72(10) ?
C4 C3 P1 C21 . . . . 85.31(10) ?
C22 C21 P1 C15 . . . . 105.94(10) ?
C26 C21 P1 C15 . . . . -71.16(10) ?
C22 C21 P1 C9 . . . . -12.76(11) ?
C26 C21 P1 C9 . . . . 170.13(9) ?
C22 C21 P1 C3 . . . . -136.07(9) ?
C26 C21 P1 C3 . . . . 46.83(10) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
