# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Dietrich Gudat'
_publ_contact_author_email       GUDAT@IAC.UNI-STUTTGART.DE

_publ_section_title              
;
Benzo-1,3,2-diazaphospholide and
Benzo-1,3,2-diazaphospholium: An Isoelectronic Aromatic Anion-Cation
Pair
;
loop_
_publ_author_name
'Dietrich Gudat'
'Zoltan Benko'
'Denis Bubrin'
'Ingo Hartenbach'
'Sebastian Loscher'
'Laszlo Nyulaszi'
;
T.Schleid
;
'Dirk Schmid'

# Attachment 'CCDC696162rev.cif'

data_c:\crystal\x-red32\dsnov07
_database_code_depnum_ccdc_archive 'CCDC 696162'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
'Benzo-1,3,2H-Diazaphospholenium Trifluormethane sulfonate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 F3 N2 O3 P S'
_chemical_formula_weight         286.17

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'
P P 0.1023 0.0942 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.9377(7)
_cell_length_b                   11.2028(8)
_cell_length_c                   11.6347(8)
_cell_angle_alpha                114.374(4)
_cell_angle_beta                 112.907(4)
_cell_angle_gamma                92.534(4)
_cell_volume                     1053.91(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    10799
_cell_measurement_theta_min      1.02
_cell_measurement_theta_max      28.28

_exptl_crystal_description       lath-shaped
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7698
_exptl_absorpt_correction_T_max  0.9529
_exptl_absorpt_process_details   'HABITUS (W. Herrendorf)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'four-circle, ccd detector'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15230
_diffrn_reflns_av_R_equivalents  0.1513
_diffrn_reflns_av_sigmaI/netI    0.1427
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.44
_diffrn_reflns_theta_max         28.27
_reflns_number_total             5077
_reflns_number_gt                2912
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius Collect Software'
_computing_cell_refinement       'DENZO (W. Minor & Z. Otwinowski)'
_computing_data_reduction        'DENZO (W. Minor & Z. Otwinowski)'
_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.
The quality of the measured crystal was not too good, therefore the R(int)
value is that high.
;

_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^)+(0.0620P)^2^+0.1748P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5077
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.03365(13) 0.77066(12) 0.16846(13) 0.0203(3) Uani 1 1 d . . .
N2 N 0.0586(4) 0.8365(4) 0.0738(4) 0.0172(8) Uani 1 1 d . . .
H2A H 0.0025 0.8031 -0.0154 0.021 Uiso 1 1 calc R . .
C3 C 0.1779(5) 0.9508(4) 0.1491(5) 0.0150(9) Uani 1 1 d . . .
C4 C 0.2488(4) 0.9798(4) 0.2900(4) 0.0134(9) Uani 1 1 d . . .
N5 N 0.1771(4) 0.8860(4) 0.3098(4) 0.0172(8) Uani 1 1 d . . .
H5A H 0.2061 0.8885 0.3909 0.021 Uiso 1 1 calc R . .
C6 C 0.3723(5) 1.0884(5) 0.3886(5) 0.0203(10) Uani 1 1 d . . .
H6A H 0.4191 1.1074 0.4828 0.024 Uiso 1 1 calc R . .
C7 C 0.4239(5) 1.1683(5) 0.3413(5) 0.0230(11) Uani 1 1 d . . .
H7A H 0.5064 1.2420 0.4046 0.028 Uiso 1 1 calc R . .
C8 C 0.3524(5) 1.1379(5) 0.2000(6) 0.0250(11) Uani 1 1 d . . .
H8A H 0.3892 1.1924 0.1711 0.030 Uiso 1 1 calc R . .
C9 C 0.2282(5) 1.0299(4) 0.0999(5) 0.0157(9) Uani 1 1 d . . .
H9A H 0.1812 1.0111 0.0058 0.019 Uiso 1 1 calc R . .
S1 S 0.22643(11) 0.51630(11) -0.79935(11) 0.0139(2) Uani 1 1 d . . .
O1 O 0.2150(3) 0.6135(3) -0.6761(3) 0.0168(7) Uani 1 1 d . . .
O2 O 0.1690(3) 0.3780(3) -0.8368(3) 0.0207(7) Uani 1 1 d . . .
O3 O 0.1839(4) 0.5483(4) -0.9139(3) 0.0273(8) Uani 1 1 d . . .
C1 C 0.4289(5) 0.5321(5) -0.7370(5) 0.0196(10) Uani 1 1 d . . .
F1 F 0.4999(3) 0.6558(3) -0.6971(3) 0.0304(7) Uani 1 1 d . . .
F2 F 0.4852(3) 0.5087(3) -0.6259(3) 0.0326(7) Uani 1 1 d . . .
F3 F 0.4580(3) 0.4455(3) -0.8366(3) 0.0316(7) Uani 1 1 d . . .
P11 P 0.11381(12) 0.29664(12) -0.62425(12) 0.0153(3) Uani 1 1 d . . .
N12 N 0.1632(4) 0.4620(4) -0.5520(4) 0.0131(8) Uani 1 1 d . . .
H12A H 0.1716 0.5034 -0.5976 0.016 Uiso 1 1 calc R . .
C13 C 0.1905(4) 0.5301(4) -0.4117(4) 0.0114(9) Uani 1 1 d . . .
C14 C 0.1686(4) 0.4355(4) -0.3657(4) 0.0118(9) Uani 1 1 d . . .
N15 N 0.1273(4) 0.3055(4) -0.4751(4) 0.0135(8) Uani 1 1 d . . .
H15A H 0.1100 0.2349 -0.4658 0.016 Uiso 1 1 calc R . .
C16 C 0.1898(4) 0.4800(4) -0.2277(4) 0.0146(9) Uani 1 1 d . . .
H16A H 0.1741 0.4190 -0.1964 0.017 Uiso 1 1 calc R . .
C17 C 0.2343(5) 0.6156(5) -0.1399(5) 0.0183(10) Uani 1 1 d . . .
H17A H 0.2507 0.6467 -0.0469 0.022 Uiso 1 1 calc R . .
C18 C 0.2563(5) 0.7103(5) -0.1850(5) 0.0167(10) Uani 1 1 d . . .
H18A H 0.2862 0.8022 -0.1221 0.020 Uiso 1 1 calc R . .
C19 C 0.2337(4) 0.6677(4) -0.3230(5) 0.0148(9) Uani 1 1 d . . .
H19A H 0.2472 0.7293 -0.3543 0.018 Uiso 1 1 calc R . .
S2 S 0.81531(11) 0.98130(11) 0.32822(11) 0.0131(2) Uani 1 1 d . . .
O4 O 0.8595(3) 0.8765(3) 0.3655(3) 0.0201(7) Uani 1 1 d . . .
O5 O 0.7767(3) 1.0858(3) 0.4246(3) 0.0197(7) Uani 1 1 d . . .
O6 O 0.9074(3) 1.0297(3) 0.2792(3) 0.0207(7) Uani 1 1 d . . .
C2 C 0.6354(5) 0.8922(5) 0.1700(5) 0.0205(10) Uani 1 1 d . . .
F4 F 0.5826(3) 0.9742(3) 0.1155(3) 0.0271(7) Uani 1 1 d . . .
F5 F 0.6518(3) 0.7878(3) 0.0738(3) 0.0363(8) Uani 1 1 d . . .
F6 F 0.5328(3) 0.8498(3) 0.2002(3) 0.0355(8) Uani 1 1 d . . .

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 0.0173(6) 0.0160(6) 0.0267(7) 0.0093(5) 0.0100(5) 0.0019(5)
N2 0.0172(18) 0.016(2) 0.0120(19) 0.0041(16) 0.0032(15) 0.0021(15)
C3 0.015(2) 0.012(2) 0.016(2) 0.0031(18) 0.0077(18) 0.0083(17)
C4 0.0111(19) 0.014(2) 0.014(2) 0.0088(18) 0.0034(17) 0.0019(16)
N5 0.0203(19) 0.018(2) 0.015(2) 0.0106(17) 0.0070(16) 0.0063(16)
C6 0.020(2) 0.021(3) 0.014(2) 0.005(2) 0.0060(19) 0.0058(19)
C7 0.020(2) 0.017(2) 0.030(3) 0.007(2) 0.013(2) 0.0044(19)
C8 0.029(3) 0.021(3) 0.039(3) 0.018(2) 0.024(2) 0.008(2)
C9 0.025(2) 0.016(2) 0.016(2) 0.0108(19) 0.0137(19) 0.0113(18)
S1 0.0126(5) 0.0170(6) 0.0134(5) 0.0088(5) 0.0053(4) 0.0032(4)
O1 0.0221(16) 0.0142(16) 0.0208(17) 0.0104(14) 0.0131(14) 0.0067(13)
O2 0.0172(15) 0.0164(17) 0.0195(17) 0.0033(14) 0.0058(13) -0.0026(13)
O3 0.0276(18) 0.041(2) 0.0210(19) 0.0218(17) 0.0100(15) 0.0118(16)
C1 0.017(2) 0.020(3) 0.022(2) 0.009(2) 0.0084(19) 0.0047(19)
F1 0.0251(14) 0.0202(15) 0.0317(17) 0.0015(13) 0.0126(13) -0.0102(12)
F2 0.0190(14) 0.046(2) 0.0238(16) 0.0180(15) -0.0004(12) 0.0086(13)
F3 0.0174(13) 0.0327(17) 0.0271(17) -0.0030(14) 0.0119(12) 0.0023(12)
P11 0.0161(5) 0.0142(6) 0.0140(6) 0.0062(5) 0.0059(5) 0.0024(5)
N12 0.0141(17) 0.0163(19) 0.0131(19) 0.0098(16) 0.0071(15) 0.0021(15)
C13 0.0090(18) 0.016(2) 0.012(2) 0.0091(18) 0.0042(16) 0.0034(16)
C14 0.0082(18) 0.013(2) 0.018(2) 0.0104(18) 0.0056(17) 0.0045(16)
N15 0.0139(17) 0.0130(19) 0.0144(19) 0.0099(16) 0.0037(15) -0.0005(14)
C16 0.014(2) 0.019(2) 0.015(2) 0.0123(19) 0.0054(17) 0.0015(17)
C17 0.016(2) 0.026(3) 0.017(2) 0.012(2) 0.0087(18) 0.0054(19)
C18 0.014(2) 0.014(2) 0.018(2) 0.0069(19) 0.0039(18) -0.0006(17)
C19 0.013(2) 0.015(2) 0.019(2) 0.0131(19) 0.0043(18) 0.0044(17)
S2 0.0141(5) 0.0115(5) 0.0108(5) 0.0063(4) 0.0017(4) 0.0016(4)
O4 0.0195(15) 0.0176(17) 0.0176(17) 0.0107(14) 0.0006(13) 0.0025(13)
O5 0.0232(16) 0.0183(17) 0.0143(16) 0.0070(14) 0.0056(13) 0.0072(14)
O6 0.0205(16) 0.0193(18) 0.0226(18) 0.0107(15) 0.0093(14) 0.0023(13)
C2 0.018(2) 0.022(3) 0.016(2) 0.008(2) 0.0042(19) 0.0010(19)
F4 0.0252(14) 0.0314(16) 0.0195(15) 0.0172(13) -0.0005(12) 0.0083(12)
F5 0.0375(17) 0.0258(16) 0.0169(15) -0.0040(13) 0.0003(13) 0.0090(13)
F6 0.0188(14) 0.0417(19) 0.0377(19) 0.0225(16) 0.0021(13) -0.0071(13)

_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 N5 1.632(4) . ?
P1 N2 1.638(4) . ?
N2 C3 1.394(5) . ?
C3 C4 1.390(6) . ?
C3 C9 1.401(6) . ?
C4 C6 1.386(6) . ?
C4 N5 1.388(5) . ?
C6 C7 1.397(6) . ?
C7 C8 1.390(7) . ?
C8 C9 1.389(6) . ?
S1 O3 1.432(3) . ?
S1 O2 1.445(3) . ?
S1 O1 1.450(3) . ?
S1 C1 1.826(5) . ?
C1 F3 1.314(6) . ?
C1 F1 1.327(5) . ?
C1 F2 1.336(5) . ?
P11 N12 1.641(4) . ?
P11 N15 1.648(4) . ?
N12 C13 1.389(5) . ?
C13 C19 1.381(6) . ?
C13 C14 1.412(5) . ?
C14 N15 1.386(5) . ?
C14 C16 1.392(6) . ?
C16 C17 1.362(6) . ?
C17 C18 1.406(6) . ?
C18 C19 1.390(6) . ?
S2 O5 1.438(3) . ?
S2 O6 1.440(3) . ?
S2 O4 1.441(3) . ?
S2 C2 1.829(4) . ?
C2 F5 1.314(6) . ?
C2 F6 1.328(5) . ?
C2 F4 1.336(5) . ?

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
N5 P1 N2 90.56(18) . . ?
C3 N2 P1 114.9(3) . . ?
C4 C3 N2 109.6(4) . . ?
C4 C3 C9 121.5(4) . . ?
N2 C3 C9 128.9(4) . . ?
C6 C4 N5 128.7(4) . . ?
C6 C4 C3 121.6(4) . . ?
N5 C4 C3 109.7(4) . . ?
C4 N5 P1 115.3(3) . . ?
C4 C6 C7 117.6(4) . . ?
C8 C7 C6 120.2(4) . . ?
C9 C8 C7 122.9(4) . . ?
C8 C9 C3 116.1(4) . . ?
O3 S1 O2 116.0(2) . . ?
O3 S1 O1 115.3(2) . . ?
O2 S1 O1 112.88(18) . . ?
O3 S1 C1 103.9(2) . . ?
O2 S1 C1 103.1(2) . . ?
O1 S1 C1 103.4(2) . . ?
F3 C1 F1 108.5(4) . . ?
F3 C1 F2 108.4(4) . . ?
F1 C1 F2 107.8(4) . . ?
F3 C1 S1 110.9(3) . . ?
F1 C1 S1 110.8(3) . . ?
F2 C1 S1 110.4(3) . . ?
N12 P11 N15 90.87(18) . . ?
C13 N12 P11 115.1(3) . . ?
C19 C13 N12 128.7(4) . . ?
C19 C13 C14 121.9(4) . . ?
N12 C13 C14 109.4(4) . . ?
N15 C14 C16 130.2(4) . . ?
N15 C14 C13 109.8(4) . . ?
C16 C14 C13 120.0(4) . . ?
C14 N15 P11 114.8(3) . . ?
C17 C16 C14 118.0(4) . . ?
C16 C17 C18 122.2(4) . . ?
C19 C18 C17 120.5(4) . . ?
C13 C19 C18 117.3(4) . . ?
O5 S2 O6 114.41(19) . . ?
O5 S2 O4 115.47(19) . . ?
O6 S2 O4 115.0(2) . . ?
O5 S2 C2 103.5(2) . . ?
O6 S2 C2 103.3(2) . . ?
O4 S2 C2 102.8(2) . . ?
F5 C2 F6 109.0(4) . . ?
F5 C2 F4 108.4(4) . . ?
F6 C2 F4 107.5(4) . . ?
F5 C2 S2 110.4(3) . . ?
F6 C2 S2 110.9(3) . . ?
F4 C2 S2 110.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.123

# Attachment 'CCDC703761rev.CIF'

data_s02neu
_database_code_depnum_ccdc_archive 'CCDC 703761'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N2 Na O2 P'
_chemical_formula_sum            'C14 H20 N2 Na O2 P'
_chemical_formula_weight         302.28

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'
Na Na 0.0362 0.0249 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   15.402(4)
_cell_length_b                   8.6206(15)
_cell_length_c                   12.500(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.22(2)
_cell_angle_gamma                90.00
_cell_volume                     1646.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    51
_cell_measurement_theta_min      4
_cell_measurement_theta_max      12.5

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '\o 2\t'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2065
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1780
_reflns_number_gt                1596
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'XScans v. 2.10b'
_computing_cell_refinement       'XScans v. 2.10b'
_computing_data_reduction        'XScans v. 2.10b'
_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^)+(0.0691P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(13)
_refine_ls_number_reflns         1780
_refine_ls_number_parameters     181
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.994
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.62308(5) 0.05718(9) 0.44658(6) 0.0429(2) Uani 1 1 d . . .
Na Na 0.63498(8) 0.18074(12) 0.17442(8) 0.0398(3) Uani 1 1 d . . .
N2 N 0.68029(18) 0.0689(3) 0.3442(2) 0.0427(6) Uani 1 1 d . . .
N1 N 0.68883(16) -0.0530(3) 0.52865(19) 0.0394(6) Uani 1 1 d . . .
O30 O 0.48484(17) 0.1777(3) 0.1228(2) 0.0602(7) Uani 1 1 d . . .
C3 C 0.9000(2) -0.1938(4) 0.4521(3) 0.0520(8) Uani 1 1 d . . .
H3A H 0.9497 -0.2542 0.4785 0.062 Uiso 1 1 calc R . .
C2 C 0.8337(2) -0.1730(4) 0.5160(3) 0.0448(7) Uani 1 1 d . . .
H2A H 0.8377 -0.2189 0.5856 0.054 Uiso 1 1 calc R . .
O20 O 0.6529(2) 0.4472(3) 0.2004(2) 0.0669(9) Uani 1 1 d . . .
C1 C 0.76072(19) -0.0838(3) 0.4770(2) 0.0341(6) Uani 1 1 d . . .
C5 C 0.8236(2) -0.0395(4) 0.3081(3) 0.0494(8) Uani 1 1 d . . .
H5A H 0.8205 0.0039 0.2379 0.059 Uiso 1 1 calc R . .
C6 C 0.75543(19) -0.0154(3) 0.3718(2) 0.0363(6) Uani 1 1 d . . .
C4 C 0.8951(2) -0.1273(4) 0.3497(3) 0.0548(8) Uani 1 1 d . . .
H4A H 0.9417 -0.1428 0.3078 0.066 Uiso 1 1 calc R . .
C31 C 0.4239(3) 0.0657(5) 0.1535(4) 0.0772(13) Uani 1 1 d . . .
H31A H 0.4171 0.0751 0.2309 0.093 Uiso 1 1 calc R . .
H31B H 0.4429 -0.0411 0.1388 0.093 Uiso 1 1 calc R . .
C21 C 0.6018(4) 0.5706(5) 0.1507(4) 0.0745(14) Uani 1 1 d . . .
H21A H 0.5461 0.5300 0.1131 0.089 Uiso 1 1 calc R . .
H21B H 0.6338 0.6233 0.0972 0.089 Uiso 1 1 calc R . .
C33 C 0.3707(4) 0.1636(7) -0.0180(7) 0.114(3) Uani 1 1 d . . .
H33A H 0.3870 0.0767 -0.0633 0.136 Uiso 1 1 calc R . .
H33B H 0.3263 0.2292 -0.0606 0.136 Uiso 1 1 calc R . .
C34 C 0.4475(3) 0.2542(7) 0.0262(5) 0.0897(16) Uani 1 1 d . . .
H34A H 0.4905 0.2590 -0.0264 0.108 Uiso 1 1 calc R . .
H34B H 0.4300 0.3614 0.0424 0.108 Uiso 1 1 calc R . .
C32 C 0.3393(3) 0.1067(7) 0.0829(7) 0.118(3) Uani 1 1 d . . .
H32A H 0.3013 0.0145 0.0688 0.141 Uiso 1 1 calc R . .
H32B H 0.3067 0.1885 0.1166 0.141 Uiso 1 1 calc R . .
C24 C 0.6873(4) 0.4994(6) 0.3054(4) 0.0840(15) Uani 1 1 d . . .
H24A H 0.7441 0.5524 0.3040 0.101 Uiso 1 1 calc R . .
H24B H 0.6954 0.4115 0.3566 0.101 Uiso 1 1 calc R . .
C22 C 0.5844(5) 0.6801(7) 0.2352(6) 0.124(3) Uani 1 1 d . . .
H22A H 0.6129 0.7811 0.2254 0.149 Uiso 1 1 calc R . .
H22B H 0.5206 0.6971 0.2337 0.149 Uiso 1 1 calc R . .
C23 C 0.6207(4) 0.6084(8) 0.3359(5) 0.1046(19) Uani 1 1 d . . .
H23A H 0.5748 0.5526 0.3693 0.126 Uiso 1 1 calc R . .
H23B H 0.6477 0.6872 0.3873 0.126 Uiso 1 1 calc R . .

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
P 0.0391(4) 0.0491(4) 0.0412(4) 0.0019(3) 0.0076(3) 0.0143(4)
Na 0.0437(6) 0.0414(6) 0.0336(5) 0.0006(5) 0.0022(4) 0.0103(5)
N2 0.0449(14) 0.0454(14) 0.0378(13) 0.0033(10) 0.0046(11) 0.0104(12)
N1 0.0421(14) 0.0413(13) 0.0357(12) 0.0025(10) 0.0083(10) 0.0039(12)
O30 0.0425(13) 0.0648(17) 0.0730(16) 0.0081(13) 0.0056(11) 0.0002(12)
C3 0.0386(17) 0.0442(18) 0.072(2) -0.0119(16) 0.0011(16) 0.0103(15)
C2 0.0475(17) 0.0401(15) 0.0443(15) 0.0007(12) -0.0041(13) 0.0081(14)
O20 0.087(2) 0.0407(12) 0.0669(18) -0.0037(10) -0.0155(16) 0.0103(13)
C1 0.0378(14) 0.0307(13) 0.0340(13) -0.0035(11) 0.0052(11) -0.0008(11)
C5 0.0526(19) 0.0467(17) 0.0523(19) -0.0013(14) 0.0207(16) 0.0004(16)
C6 0.0400(15) 0.0314(13) 0.0376(14) -0.0020(11) 0.0060(12) 0.0019(12)
C4 0.0402(18) 0.0576(19) 0.069(2) -0.0144(18) 0.0180(16) -0.0004(17)
C31 0.090(3) 0.060(2) 0.084(3) -0.008(2) 0.020(3) -0.022(2)
C21 0.088(3) 0.053(2) 0.075(3) 0.0094(19) -0.018(2) 0.016(2)
C33 0.080(4) 0.074(3) 0.171(7) 0.022(4) -0.045(4) 0.007(3)
C34 0.065(3) 0.077(3) 0.119(4) 0.031(3) -0.018(3) 0.002(3)
C32 0.045(2) 0.075(3) 0.233(9) -0.031(4) 0.019(4) -0.015(2)
C24 0.103(4) 0.063(2) 0.075(3) 0.003(2) -0.030(3) -0.006(3)
C22 0.123(5) 0.077(3) 0.156(6) -0.037(4) -0.042(5) 0.051(4)
C23 0.106(4) 0.111(4) 0.099(4) -0.055(4) 0.023(4) -0.031(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
P N2 1.645(3) . ?
P N1 1.649(2) . ?
Na O30 2.322(3) . ?
Na O20 2.332(3) . ?
Na N2 2.356(3) . ?
Na N1 2.367(3) 2_554 ?
N2 C6 1.374(4) . ?
N1 C1 1.376(4) . ?
N1 Na 2.367(3) 2 ?
O30 C31 1.431(5) . ?
O30 C34 1.433(5) . ?
C3 C2 1.386(5) . ?
C3 C4 1.396(6) . ?
C2 C1 1.398(4) . ?
O20 C21 1.419(4) . ?
O20 C24 1.425(5) . ?
C1 C6 1.434(4) . ?
C5 C4 1.382(5) . ?
C5 C6 1.411(4) . ?
C31 C32 1.521(8) . ?
C21 C22 1.466(8) . ?
C33 C34 1.466(7) . ?
C33 C32 1.489(10) . ?
C24 C23 1.476(8) . ?
C22 C23 1.450(9) . ?

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
N2 P N1 99.92(13) . . ?
O30 Na O20 98.43(11) . . ?
O30 Na N2 114.68(11) . . ?
O20 Na N2 105.15(10) . . ?
O30 Na N1 102.36(10) . 2_554 ?
O20 Na N1 121.24(11) . 2_554 ?
N2 Na N1 114.24(10) . 2_554 ?
C6 N2 P 106.8(2) . . ?
C6 N2 Na 126.0(2) . . ?
P N2 Na 126.79(15) . . ?
C1 N1 P 106.66(19) . . ?
C1 N1 Na 130.7(2) . 2 ?
P N1 Na 119.99(13) . 2 ?
C31 O30 C34 109.2(3) . . ?
C31 O30 Na 126.7(3) . . ?
C34 O30 Na 120.6(3) . . ?
C2 C3 C4 121.1(3) . . ?
C3 C2 C1 119.2(3) . . ?
C21 O20 C24 106.7(3) . . ?
C21 O20 Na 128.9(2) . . ?
C24 O20 Na 117.6(2) . . ?
N1 C1 C2 127.0(3) . . ?
N1 C1 C6 113.2(3) . . ?
C2 C1 C6 119.8(3) . . ?
C4 C5 C6 118.8(3) . . ?
N2 C6 C5 126.9(3) . . ?
N2 C6 C1 113.4(3) . . ?
C5 C6 C1 119.8(3) . . ?
C5 C4 C3 121.3(3) . . ?
O30 C31 C32 103.4(4) . . ?
O20 C21 C22 108.0(4) . . ?
C34 C33 C32 100.9(6) . . ?
O30 C34 C33 106.9(4) . . ?
C33 C32 C31 102.8(4) . . ?
O20 C24 C23 104.4(4) . . ?
C23 C22 C21 105.4(4) . . ?
C22 C23 C24 104.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.040