# Supplementary Material (ESI) for Green Chemistry
# This journal is © The Royal Society of Chemistry 2007

data_global
_journal_name_full               'Green Chemistry'

_journal_coden_Cambridge         1048

_publ_contact_author_name        'Michael Watkinson'
_publ_contact_author_address     
;
School of Biological and Chemical Sciences
Queen Mary University of London
The Walter Besant Building
Mil End Road
London
E1 4NS
UNITED KINGDOM
;

_publ_contact_author_email       M.WATKINSON@QMUL.AC.UK

_publ_section_title              
;
Investigations into the efficacy of aminophosphonic
acid functionalised 1,4,7-triazacyclononane ligands in bleaching
catalysis
;
loop_
_publ_author_name
'Michael Watkinson'
'Majid Motevalli'
'John Schofield'
'K Shastri'
'Jennifer S. Wilkinson'

data_ksc2p-ii
_database_code_depnum_ccdc_archive 'CCDC 614131'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H44 N6 O12 P4, 4(H2 O)'
_chemical_formula_sum            'C18 H52 N6 O16 P4'
_chemical_formula_weight         732.54

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   20.450(4)
_cell_length_b                   7.329(2)
_cell_length_c                   10.310(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.28(2)
_cell_angle_gamma                90.00
_cell_volume                     1525.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10.0005
_cell_measurement_theta_max      13.558

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.8793
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was 3
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.

;

_diffrn_ambient_temperature      160(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  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 100
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        4
_diffrn_reflns_number            2918
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         24.97
_reflns_number_total             2673
_reflns_number_gt                1768
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 /PC (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0518P)^2^+1.0895P] 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         2673
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
C1 C 0.00953(16) 0.9070(5) 0.0268(3) 0.0255(8) Uani 1 1 d . . .
H1A H 0.0320 0.8395 -0.0366 0.031 Uiso 1 1 calc R . .
H1B H 0.0411 0.9192 0.1099 0.031 Uiso 1 1 calc R . .
C2 C -0.03043(16) 0.6594(5) 0.1518(3) 0.0200(7) Uani 1 1 d . . .
H2A H 0.0165 0.6245 0.1543 0.024 Uiso 1 1 calc R . .
H2B H -0.0583 0.5497 0.1299 0.024 Uiso 1 1 calc R . .
C3 C -0.04054(15) 0.7347(5) 0.2853(3) 0.0185(7) Uani 1 1 d . . .
H3A H -0.0404 0.6339 0.3493 0.022 Uiso 1 1 calc R . .
H3B H -0.0044 0.8205 0.3191 0.022 Uiso 1 1 calc R . .
C4 C -0.16287(15) 0.7027(4) 0.2427(3) 0.0180(7) Uani 1 1 d . . .
H4A H -0.1808 0.6835 0.3253 0.022 Uiso 1 1 calc R . .
H4B H -0.1482 0.5832 0.2130 0.022 Uiso 1 1 calc R . .
C5 C -0.21630(16) 0.7810(5) 0.1390(3) 0.0211(8) Uani 1 1 d . . .
H5A H -0.2512 0.6880 0.1143 0.025 Uiso 1 1 calc R . .
H5B H -0.2368 0.8873 0.1759 0.025 Uiso 1 1 calc R . .
C6 C -0.16058(16) 0.6888(5) -0.0449(3) 0.0207(7) Uani 1 1 d . . .
H6A H -0.1893 0.6615 -0.1295 0.025 Uiso 1 1 calc R . .
H6B H -0.1581 0.5777 0.0103 0.025 Uiso 1 1 calc R . .
C7 C -0.09164(17) 0.7378(5) -0.0705(3) 0.0227(8) Uani 1 1 d . . .
H7A H -0.0710 0.6293 -0.1043 0.027 Uiso 1 1 calc R . .
H7B H -0.0950 0.8343 -0.1384 0.027 Uiso 1 1 calc R . .
C8 C -0.11282(16) 0.9625(4) 0.3724(3) 0.0168(7) Uani 1 1 d . . .
H8A H -0.0912 0.9104 0.4571 0.020 Uiso 1 1 calc R . .
H8B H -0.1606 0.9747 0.3768 0.020 Uiso 1 1 calc R . .
C9 C -0.23930(16) 0.9450(4) -0.0673(3) 0.0203(7) Uani 1 1 d . . .
H9A H -0.2841 0.9098 -0.0514 0.024 Uiso 1 1 calc R . .
H9B H -0.2360 0.9120 -0.1591 0.024 Uiso 1 1 calc R . .
O7 O -0.41551(13) 1.0923(4) -0.1249(3) 0.0274(6) Uani 1 1 d . . .
O8 O -0.35446(15) 1.6017(4) -0.1749(3) 0.0315(7) Uani 1 1 d . . .
N1 N -0.04924(12) 0.8030(4) 0.0513(2) 0.0183(6) Uani 1 1 d . . .
H1 H -0.0751 0.8856 0.0892 0.022 Uiso 0.46(4) 1 calc PR . .
N2 N -0.10536(12) 0.8304(4) 0.2668(2) 0.0144(6) Uani 1 1 d . . .
H2 H -0.1071 0.8988 0.1904 0.017 Uiso 0.54(4) 1 calc PR . .
N3 N -0.18992(12) 0.8380(4) 0.0215(2) 0.0175(6) Uani 1 1 d . . .
O1 O -0.09896(12) 1.2958(3) 0.4669(2) 0.0277(6) Uani 1 1 d . . .
O2 O -0.10317(12) 1.2586(3) 0.2185(2) 0.0236(6) Uani 1 1 d . . .
H2C H -0.1446 1.2700 0.2065 0.035 Uiso 0.33(6) 1 calc PR . .
O3 O -0.00352(11) 1.1554(3) 0.3694(3) 0.0283(6) Uani 1 1 d . . .
H3 H 0.0155 1.2547 0.3592 0.042 Uiso 1 1 calc R . .
O4 O -0.21561(11) 1.2456(3) 0.0956(2) 0.0215(5) Uani 1 1 d . . .
H4 H -0.1746 1.2398 0.1217 0.032 Uiso 0.67(6) 1 calc PR . .
O5 O -0.29365(11) 1.2732(3) -0.1177(2) 0.0218(5) Uani 1 1 d . . .
O6 O -0.16789(11) 1.2468(3) -0.1089(2) 0.0233(6) Uani 1 1 d . . .
H6 H -0.1679 1.1920 -0.1805 0.035 Uiso 1 1 calc R . .
P1 P -0.07947(4) 1.18785(12) 0.35624(8) 0.0179(2) Uani 1 1 d . . .
P2 P -0.23074(4) 1.19038(12) -0.04955(8) 0.0167(2) Uani 1 1 d . . .
H7C H -0.4103(19) 1.007(6) -0.068(4) 0.035(12) Uiso 1 1 d . . .
H7D H -0.382(2) 1.142(7) -0.121(4) 0.044(14) Uiso 1 1 d . . .
H8D H -0.365(2) 1.652(7) -0.110(4) 0.052(15) Uiso 1 1 d . . .
H8C H -0.328(2) 1.510(7) -0.140(4) 0.054(15) Uiso 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
C1 0.0203(18) 0.029(2) 0.028(2) 0.0087(16) 0.0082(15) 0.0017(15)
C2 0.0214(17) 0.0167(18) 0.0227(17) 0.0032(14) 0.0064(14) 0.0050(14)
C3 0.0177(16) 0.0184(18) 0.0193(17) 0.0041(14) 0.0025(13) 0.0041(14)
C4 0.0208(16) 0.0143(18) 0.0205(16) 0.0015(14) 0.0081(13) -0.0023(14)
C5 0.0169(16) 0.022(2) 0.0256(18) -0.0019(15) 0.0056(14) -0.0027(14)
C6 0.0275(18) 0.0136(17) 0.0202(17) -0.0030(15) 0.0016(14) -0.0004(15)
C7 0.031(2) 0.0218(19) 0.0166(17) -0.0016(15) 0.0065(15) 0.0059(16)
C8 0.0201(16) 0.0194(18) 0.0115(15) 0.0007(13) 0.0047(13) 0.0019(14)
C9 0.0205(17) 0.0135(17) 0.0242(17) 0.0002(15) -0.0050(14) -0.0028(14)
O7 0.0202(14) 0.0240(16) 0.0380(16) 0.0136(13) 0.0045(12) 0.0020(12)
O8 0.0491(18) 0.0268(15) 0.0220(15) 0.0063(13) 0.0160(13) 0.0079(14)
N1 0.0191(14) 0.0168(15) 0.0201(14) 0.0035(12) 0.0061(11) 0.0038(12)
N2 0.0169(13) 0.0108(14) 0.0158(13) -0.0012(12) 0.0040(10) 0.0000(11)
N3 0.0165(13) 0.0169(15) 0.0178(14) -0.0034(12) -0.0004(11) 0.0000(12)
O1 0.0345(14) 0.0238(14) 0.0256(13) -0.0091(11) 0.0071(11) -0.0011(12)
O2 0.0275(13) 0.0196(13) 0.0225(13) 0.0035(10) 0.0003(10) -0.0044(11)
O3 0.0204(13) 0.0210(14) 0.0432(15) 0.0022(12) 0.0048(11) -0.0007(10)
O4 0.0207(12) 0.0254(13) 0.0189(12) -0.0030(10) 0.0044(9) 0.0017(11)
O5 0.0228(12) 0.0184(13) 0.0237(12) 0.0038(10) 0.0022(10) 0.0021(10)
O6 0.0258(13) 0.0246(13) 0.0211(12) -0.0053(11) 0.0084(10) -0.0069(10)
P1 0.0179(4) 0.0167(5) 0.0182(4) -0.0019(4) 0.0003(3) 0.0012(4)
P2 0.0174(4) 0.0162(5) 0.0165(4) 0.0003(4) 0.0031(3) 0.0002(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
C1 N1 1.479(4) . ?
C1 C1 1.498(7) 3_575 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.483(4) . ?
C2 C3 1.527(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N2 1.485(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N2 1.492(4) . ?
C4 C5 1.513(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.464(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N3 1.469(4) . ?
C6 C7 1.518(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N1 1.486(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N2 1.483(4) . ?
C8 P1 1.805(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.475(4) . ?
C9 P2 1.814(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O7 H7C 0.85(4) . ?
O7 H7D 0.78(5) . ?
O8 H8D 0.82(5) . ?
O8 H8C 0.90(5) . ?
N1 H1 0.9300 . ?
N2 H2 0.9300 . ?
O1 P1 1.494(2) . ?
O2 P1 1.517(2) . ?
O2 H2C 0.8400 . ?
O3 P1 1.556(2) . ?
O3 H3 0.8400 . ?
O4 P2 1.533(2) . ?
O4 H4 0.8400 . ?
O5 P2 1.492(2) . ?
O6 P2 1.566(2) . ?
O6 H6 0.8400 . ?

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
N1 C1 C1 111.2(3) . 3_575 ?
N1 C1 H1A 109.4 . . ?
C1 C1 H1A 109.4 3_575 . ?
N1 C1 H1B 109.4 . . ?
C1 C1 H1B 109.4 3_575 . ?
H1A C1 H1B 108.0 . . ?
N1 C2 C3 108.4(3) . . ?
N1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
N2 C3 C2 107.6(2) . . ?
N2 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
N2 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N2 C4 C5 109.9(3) . . ?
N2 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
N2 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N3 C5 C4 111.9(3) . . ?
N3 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
N3 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N3 C6 C7 111.4(3) . . ?
N3 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 C6 111.2(3) . . ?
N1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N2 C8 P1 116.4(2) . . ?
N2 C8 H8A 108.2 . . ?
P1 C8 H8A 108.2 . . ?
N2 C8 H8B 108.2 . . ?
P1 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
N3 C9 P2 114.8(2) . . ?
N3 C9 H9A 108.6 . . ?
P2 C9 H9A 108.6 . . ?
N3 C9 H9B 108.6 . . ?
P2 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
H7C O7 H7D 107(4) . . ?
H8D O8 H8C 103(4) . . ?
C1 N1 C2 111.0(2) . . ?
C1 N1 C7 113.6(2) . . ?
C2 N1 C7 114.4(3) . . ?
C1 N1 H1 105.6 . . ?
C2 N1 H1 105.6 . . ?
C7 N1 H1 105.6 . . ?
C8 N2 C3 114.2(2) . . ?
C8 N2 C4 111.1(2) . . ?
C3 N2 C4 112.9(2) . . ?
C8 N2 H2 106.0 . . ?
C3 N2 H2 106.0 . . ?
C4 N2 H2 106.0 . . ?
C5 N3 C6 114.0(3) . . ?
C5 N3 C9 111.0(3) . . ?
C6 N3 C9 113.4(2) . . ?
P1 O2 H2C 109.5 . . ?
P1 O3 H3 109.5 . . ?
P2 O4 H4 109.5 . . ?
P2 O6 H6 109.5 . . ?
O1 P1 O2 116.71(14) . . ?
O1 P1 O3 113.58(14) . . ?
O2 P1 O3 107.31(14) . . ?
O1 P1 C8 105.25(14) . . ?
O2 P1 C8 109.33(14) . . ?
O3 P1 C8 103.82(14) . . ?
O5 P2 O4 112.04(13) . . ?
O5 P2 O6 114.12(14) . . ?
O4 P2 O6 105.24(13) . . ?
O5 P2 C9 107.10(14) . . ?
O4 P2 C9 111.18(15) . . ?
O6 P2 C9 107.13(15) . . ?

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 C2 C3 N2 44.4(3) . . . . ?
N2 C4 C5 N3 50.6(3) . . . . ?
N3 C6 C7 N1 51.6(4) . . . . ?
C1 C1 N1 C2 -156.1(4) 3_575 . . . ?
C1 C1 N1 C7 73.3(5) 3_575 . . . ?
C3 C2 N1 C1 95.6(3) . . . . ?
C3 C2 N1 C7 -134.2(3) . . . . ?
C6 C7 N1 C1 -161.4(3) . . . . ?
C6 C7 N1 C2 69.7(3) . . . . ?
P1 C8 N2 C3 84.3(3) . . . . ?
P1 C8 N2 C4 -146.6(2) . . . . ?
C2 C3 N2 C8 -160.2(3) . . . . ?
C2 C3 N2 C4 71.7(3) . . . . ?
C5 C4 N2 C8 90.1(3) . . . . ?
C5 C4 N2 C3 -140.2(3) . . . . ?
C4 C5 N3 C6 61.3(3) . . . . ?
C4 C5 N3 C9 -169.2(3) . . . . ?
C7 C6 N3 C5 -129.3(3) . . . . ?
C7 C6 N3 C9 102.4(3) . . . . ?
P2 C9 N3 C5 96.2(3) . . . . ?
P2 C9 N3 C6 -134.0(2) . . . . ?
N2 C8 P1 O1 175.0(2) . . . . ?
N2 C8 P1 O2 48.8(3) . . . . ?
N2 C8 P1 O3 -65.4(2) . . . . ?
N3 C9 P2 O5 -164.9(2) . . . . ?
N3 C9 P2 O4 -42.2(3) . . . . ?
N3 C9 P2 O6 72.3(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
O3 H3 O7 0.84 1.79 2.575(3) 155.0 4_686
O6 H6 O8 0.84 1.76 2.576(3) 164.1 2_444
O7 H7C O1 0.85(4) 1.86(5) 2.703(4) 171(4) 2_445
O8 H8D O1 0.82(5) 2.05(5) 2.862(4) 171(5) 2_455
O8 H8C O5 0.90(5) 1.87(5) 2.731(4) 159(4) .
O7 H7D O5 0.78(5) 2.03(5) 2.813(4) 178(4) .
N1 H1 N2 0.93 2.07 2.667(4) 121.1 .
N2 H2 N1 0.93 2.12 2.667(4) 116.4 .
O4 H4 O2 0.84 1.64 2.442(3) 159.8 .
O2 H2C O4 0.84 1.71 2.442(3) 144.7 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.076


# Attachment 'memepbr-09-07.cif'

data_memepbr
_database_code_depnum_ccdc_archive 'CCDC 614132'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H28 Br2 N3 O5 P'
_chemical_formula_sum            'C9 H28 Br2 N3 O5 P'
_chemical_formula_weight         449.13

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6030(7)
_cell_length_b                   9.1105(9)
_cell_length_c                   13.0353(15)
_cell_angle_alpha                89.455(4)
_cell_angle_beta                 75.731(4)
_cell_angle_gamma                86.145(6)
_cell_volume                     873.06(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    52616
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    4.754
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4211
_exptl_absorpt_correction_T_max  0.7023
_exptl_absorpt_process_details   
;
Using multiple and symmetry-related data measurements via the program
SORTAV
See R.H. Blessing, Acta Crysta (1995), A51, 33-38
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean 7.73
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14229
_diffrn_reflns_av_R_equivalents  0.0966
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         27.56
_reflns_number_total             3798
_reflns_number_gt                2770
_reflns_threshold_expression     >2sigma(I)

loop_
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997'
' COLLECT (Hooft, 1998)'
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_reduction        'DENZO and COLLECT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 for Windows - Farrugia, L. J. (1997)'
_computing_publication_material  'WINGX(L.J. Farrugia, 1999'

_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^)+(0.1848P)^2^+22.9089P] 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         3798
_refine_ls_number_parameters     201
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.1243
_refine_ls_wR_factor_ref         0.3619
_refine_ls_wR_factor_gt          0.3384
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.167
_refine_ls_shift/su_mean         0.001

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
C1 C 0.1650(8) 0.2721(7) 0.5142(4) 0.0134(14) Uani 1 1 d . . .
H1A H 0.0433 0.3073 0.5058 0.016 Uiso 1 1 calc R . .
H1B H 0.1892 0.1699 0.4867 0.016 Uiso 1 1 calc R . .
C2 C 0.3189(8) 0.1918(7) 0.6544(5) 0.0156(14) Uani 1 1 d . . .
H2A H 0.3266 0.2229 0.7257 0.019 Uiso 1 1 calc R . .
H2B H 0.4313 0.2174 0.6027 0.019 Uiso 1 1 calc R . .
C3 C 0.3010(8) 0.0245(7) 0.6524(5) 0.0170(15) Uani 1 1 d . . .
H3A H 0.3313 -0.0104 0.5780 0.020 Uiso 1 1 calc R . .
H3B H 0.3892 -0.0257 0.6879 0.020 Uiso 1 1 calc R . .
C4 C 0.0935(8) -0.1745(7) 0.6941(6) 0.0184(15) Uani 1 1 d . . .
H4A H 0.1694 -0.2313 0.7332 0.028 Uiso 1 1 calc R . .
H4B H 0.1327 -0.2013 0.6188 0.028 Uiso 1 1 calc R . .
H4C H -0.0340 -0.1962 0.7217 0.028 Uiso 1 1 calc R . .
C5 C 0.0573(9) 0.0347(7) 0.8205(5) 0.0183(15) Uani 1 1 d . . .
H5A H 0.1470 0.1024 0.8324 0.022 Uiso 1 1 calc R . .
H5B H 0.0624 -0.0517 0.8666 0.022 Uiso 1 1 calc R . .
C6 C -0.1321(9) 0.1126(7) 0.8540(5) 0.0163(15) Uani 1 1 d . . .
H6A H -0.1600 0.1336 0.9309 0.020 Uiso 1 1 calc R . .
H6B H -0.2216 0.0447 0.8422 0.020 Uiso 1 1 calc R . .
C7 C -0.3497(9) 0.3163(7) 0.8366(6) 0.0207(16) Uani 1 1 d . . .
H7A H -0.3637 0.3644 0.9053 0.031 Uiso 1 1 calc R . .
H7B H -0.4312 0.2359 0.8445 0.031 Uiso 1 1 calc R . .
H7C H -0.3802 0.3882 0.7862 0.031 Uiso 1 1 calc R . .
C8 C -0.0196(9) 0.3681(7) 0.7994(5) 0.0173(15) Uani 1 1 d . . .
H8A H 0.0657 0.3287 0.8409 0.021 Uiso 1 1 calc R . .
H8B H -0.0831 0.4595 0.8345 0.021 Uiso 1 1 calc R . .
C9 C 0.0867(9) 0.4027(7) 0.6868(5) 0.0189(15) Uani 1 1 d . . .
H9A H 0.0058 0.4603 0.6501 0.023 Uiso 1 1 calc R . .
H9B H 0.1886 0.4632 0.6901 0.023 Uiso 1 1 calc R . .
Br1 Br 0.20930(10) 0.26277(9) 0.01906(6) 0.02968(19) Uani 1 1 d . . .
Br2 Br 0.77426(16) 0.07737(13) 0.61570(10) 0.0589(3) Uani 1 1 d . . .
N1 N 0.1578(7) 0.2689(6) 0.6274(4) 0.0121(12) Uani 1 1 d . . .
N2 N 0.1121(7) -0.0161(6) 0.7067(4) 0.0172(13) Uani 1 1 d . . .
H2 H 0.0330 0.0339 0.6722 0.021 Uiso 1 1 calc R . .
N3 N -0.1575(7) 0.2563(6) 0.7964(4) 0.0150(12) Uani 1 1 d . . .
H3 H -0.1432 0.2318 0.7256 0.018 Uiso 1 1 calc R . .
O1 O 0.5255(6) 0.3386(5) 0.4333(4) 0.0179(11) Uani 1 1 d . . .
O2 O 0.2929(6) 0.3731(6) 0.3190(4) 0.0217(12) Uani 1 1 d . . .
H2C H 0.3759 0.3192 0.2797 0.033 Uiso 1 1 calc R . .
O3 O 0.2738(6) 0.5463(5) 0.4645(4) 0.0205(11) Uani 1 1 d . . .
H3C H 0.3362 0.5744 0.5046 0.031 Uiso 1 1 calc R . .
O4 O -0.2151(6) 0.4005(5) 0.0795(4) 0.0340(15) Uani 1 1 d D . .
O5 O 0.5065(6) 0.2258(6) 0.1665(3) 0.0316(14) Uani 1 1 d D . .
P1 P 0.3315(2) 0.38454(18) 0.43194(13) 0.0147(4) Uani 1 1 d . . .
H41 H -0.2209(12) 0.4924(7) 0.0544(11) 0.000(14) Uiso 1 1 d D . .
H42 H -0.1019(8) 0.4082(16) 0.0877(12) 0.05(3) Uiso 1 1 d D . .
H51 H 0.5618(11) 0.1889(17) 0.1019(7) 0.06(3) Uiso 1 1 d D . .
H52 H 0.4024(8) 0.250(2) 0.1474(10) 0.18(9) Uiso 1 1 d 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
C1 0.010(2) 0.017(3) 0.012(2) 0.001(2) -0.0024(19) 0.003(2)
C2 0.009(2) 0.009(3) 0.031(3) 0.001(2) -0.010(2) 0.004(2)
C3 0.007(2) 0.011(3) 0.031(3) -0.001(2) -0.003(2) 0.004(2)
C4 0.014(3) 0.009(3) 0.034(3) 0.001(2) -0.008(2) -0.008(2)
C5 0.021(3) 0.011(3) 0.021(3) -0.001(2) -0.003(2) 0.003(2)
C6 0.020(3) 0.008(3) 0.018(3) 0.003(2) 0.000(2) 0.001(2)
C7 0.014(3) 0.013(3) 0.030(3) -0.001(3) 0.002(2) 0.008(2)
C8 0.019(3) 0.016(3) 0.018(3) 0.002(2) -0.004(2) -0.009(2)
C9 0.020(3) 0.016(3) 0.022(3) 0.001(2) -0.006(2) -0.002(2)
Br1 0.0274(3) 0.0296(4) 0.0323(3) 0.0023(3) -0.0074(3) -0.0039(3)
Br2 0.0540(6) 0.0520(6) 0.0719(7) -0.0043(5) -0.0176(5) -0.0028(5)
N1 0.011(2) 0.008(2) 0.017(2) 0.0009(18) -0.0035(17) 0.0012(18)
N2 0.016(2) 0.013(3) 0.023(2) 0.004(2) -0.0071(19) -0.001(2)
N3 0.011(2) 0.008(2) 0.027(3) 0.0011(19) -0.0053(18) 0.0018(18)
O1 0.0110(18) 0.013(2) 0.030(2) -0.0008(17) -0.0062(16) 0.0045(16)
O2 0.023(2) 0.023(2) 0.019(2) 0.0030(18) -0.0060(17) 0.0032(19)
O3 0.019(2) 0.0048(19) 0.040(2) -0.0012(17) -0.0122(18) 0.0007(16)
O4 0.026(3) 0.031(3) 0.044(3) 0.007(2) -0.007(2) -0.008(2)
O5 0.029(3) 0.034(3) 0.031(3) 0.005(2) -0.003(2) -0.009(2)
P1 0.0108(6) 0.0098(7) 0.0228(7) 0.0015(6) -0.0033(5) 0.0016(6)

_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 N1 1.464(8) . ?
C1 P1 1.813(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.486(8) . ?
C2 C3 1.540(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N2 1.505(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N2 1.474(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N2 1.507(8) . ?
C5 C6 1.525(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N3 1.527(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N3 1.493(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N3 1.518(8) . ?
C8 C9 1.532(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.449(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N2 H2 0.9300 . ?
N3 H3 0.9300 . ?
O1 P1 1.510(5) . ?
O2 P1 1.576(5) . ?
O2 H2C 0.8400 . ?
O3 P1 1.542(5) . ?
O3 H3C 0.8400 . ?
O4 H41 0.898(7) . ?
O4 H42 0.900(7) . ?
O5 H51 0.900(8) . ?
O5 H52 0.900(8) . ?

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
N1 C1 P1 116.8(4) . . ?
N1 C1 H1A 108.1 . . ?
P1 C1 H1A 108.1 . . ?
N1 C1 H1B 108.1 . . ?
P1 C1 H1B 108.1 . . ?
H1A C1 H1B 107.3 . . ?
N1 C2 C3 109.1(5) . . ?
N1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C2 111.9(5) . . ?
N2 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 114.5(6) . . ?
N2 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
N2 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 N3 115.1(5) . . ?
C5 C6 H6A 108.5 . . ?
N3 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
N3 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 110.2(5) . . ?
N3 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N3 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N1 C9 C8 111.1(5) . . ?
N1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 N1 C1 116.4(5) . . ?
C9 N1 C2 115.7(5) . . ?
C1 N1 C2 114.6(4) . . ?
C4 N2 C3 110.8(5) . . ?
C4 N2 C5 113.2(5) . . ?
C3 N2 C5 111.8(5) . . ?
C4 N2 H2 106.9 . . ?
C3 N2 H2 106.9 . . ?
C5 N2 H2 106.9 . . ?
C7 N3 C8 113.1(5) . . ?
C7 N3 C6 108.4(5) . . ?
C8 N3 C6 115.0(5) . . ?
C7 N3 H3 106.6 . . ?
C8 N3 H3 106.6 . . ?
C6 N3 H3 106.6 . . ?
P1 O2 H2C 109.5 . . ?
P1 O3 H3C 109.5 . . ?
H41 O4 H42 92.5(9) . . ?
H51 O5 H52 92.6(9) . . ?
O1 P1 O3 114.0(3) . . ?
O1 P1 O2 113.5(3) . . ?
O3 P1 O2 103.5(3) . . ?
O1 P1 C1 113.8(3) . . ?
O3 P1 C1 107.3(3) . . ?
O2 P1 C1 103.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -44.3(7) . . . . ?
N2 C5 C6 N3 -63.3(7) . . . . ?
N3 C8 C9 N1 -50.3(7) . . . . ?
C8 C9 N1 C1 145.5(5) . . . . ?
C8 C9 N1 C2 -75.6(7) . . . . ?
P1 C1 N1 C9 70.3(6) . . . . ?
P1 C1 N1 C2 -69.1(6) . . . . ?
C3 C2 N1 C9 141.0(5) . . . . ?
C3 C2 N1 C1 -79.3(6) . . . . ?
C2 C3 N2 C4 174.1(6) . . . . ?
C2 C3 N2 C5 -58.6(7) . . . . ?
C6 C5 N2 C4 -100.9(6) . . . . ?
C6 C5 N2 C3 133.1(6) . . . . ?
C9 C8 N3 C7 -115.2(6) . . . . ?
C9 C8 N3 C6 119.6(6) . . . . ?
C5 C6 N3 C7 178.9(6) . . . . ?
C5 C6 N3 C8 -53.5(7) . . . . ?
N1 C1 P1 O1 60.4(5) . . . . ?
N1 C1 P1 O3 -66.7(5) . . . . ?
N1 C1 P1 O2 -175.8(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
N2 H2 Br2 0.93 2.27 3.150(6) 156.6 1_455
N3 H3 Br2 0.93 2.24 3.043(6) 144.0 1_455
N2 H2 N1 0.93 2.41 2.797(7) 105.0 .
N3 H3 N1 0.93 2.38 2.836(7) 110.3 .
O2 H2C O5 0.84 1.75 2.561(6) 160.4 .
O3 H3C O1 0.84 1.71 2.539(7) 167.5 2_666
O4 H41 Br1 0.898(7) 2.418(7) 3.314(5) 175.3(8) 2_565
O4 H42 Br1 0.900(7) 2.591(9) 3.291(4) 135.2(13) .

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.945
_refine_diff_density_max         2.161
_refine_diff_density_min         -2.896
_refine_diff_density_rms         0.317