# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Chemical Science'

_journal_coden_Cambridge         1475
_journal_year                    ?
_publ_contact_author_email       philip.gale@soton.ac.uk
_publ_contact_author_name        'Philip Gale'
loop_
_publ_author_name
'Mark Light'
'Cally Haynes'
'Phil Gale'

data_2011sot0006
_database_code_depnum_ccdc_archive 'CCDC 862708'
#TrackingRef '- cally-final.cif'

#2011src0023

_chemical_compound_source        'Cally Haynes'
_database_code_CSD               11ST0006

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C12 H24 O6), C22 H24 N6 O2, 2(K)+, (C2 O4)2-'
_chemical_formula_sum            'C48 H72 K2 N6 O18'
_chemical_formula_weight         1099.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   22.76(3)
_cell_length_b                   7.558(9)
_cell_length_c                   31.61(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.626(19)
_cell_angle_gamma                90.00
_cell_volume                     5389(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5321
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      24.3

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2336
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.277
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.68890
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         Synchrotron
_diffrn_radiation_monochromator  Synchrotron
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13658
_diffrn_reflns_av_R_equivalents  0.2070
_diffrn_reflns_av_sigmaI/netI    0.3822
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         24.30
_reflns_number_total             8840
_reflns_number_gt                1960
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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^ > 2\s(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^)+(0.1319P)^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_number_reflns         8840
_refine_ls_number_parameters     667
_refine_ls_number_restraints     288
_refine_ls_R_factor_all          0.3426
_refine_ls_R_factor_gt           0.1183
_refine_ls_wR_factor_ref         0.4094
_refine_ls_wR_factor_gt          0.2544
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.972
_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
N1 N -0.0593(5) 0.6136(14) 0.7339(3) 0.058(3) Uani 1 1 d . . .
H901 H -0.0802 0.6128 0.7084 0.070 Uiso 1 1 calc R . .
N2 N 0.0276(4) 0.5402(13) 0.6723(3) 0.049(3) Uani 1 1 d . . .
H902 H -0.0097 0.5671 0.6637 0.059 Uiso 1 1 calc R . .
N3 N 0.0295(5) 0.5052(14) 0.6014(4) 0.064(3) Uani 1 1 d . . .
H903 H -0.0074 0.5436 0.5979 0.077 Uiso 1 1 calc R . .
N4 N 0.1838(5) 0.7825(15) 0.5057(3) 0.061(3) Uani 1 1 d . . .
H904 H 0.1627 0.7641 0.4807 0.073 Uiso 1 1 calc R . .
N5 N 0.2622(5) 0.7024(14) 0.4738(3) 0.058(3) Uani 1 1 d . . .
H905 H 0.2351 0.6931 0.4513 0.069 Uiso 1 1 calc R . .
N6 N 0.2890(5) 0.6591(14) 0.3865(3) 0.059(3) Uani 1 1 d . . .
H906 H 0.2507 0.6781 0.3853 0.070 Uiso 1 1 calc R . .
C1 C -0.0809(7) 0.6430(19) 0.7719(5) 0.071(4) Uani 1 1 d U . .
H1 H -0.1211 0.6693 0.7744 0.085 Uiso 1 1 calc R . .
C2 C -0.0381(7) 0.630(2) 0.8045(5) 0.081(5) Uani 1 1 d U . .
H2 H -0.0428 0.6453 0.8337 0.097 Uiso 1 1 calc R . .
C3 C 0.0159(6) 0.5885(17) 0.7888(4) 0.056(4) Uani 1 1 d U . .
C4 C 0.0747(6) 0.5635(16) 0.8059(5) 0.062(4) Uani 1 1 d U . .
H4 H 0.0854 0.5716 0.8359 0.074 Uiso 1 1 calc R . .
C5 C 0.1173(6) 0.5280(18) 0.7811(4) 0.060(4) Uani 1 1 d U . .
H5 H 0.1572 0.5113 0.7938 0.072 Uiso 1 1 calc R . .
C6 C 0.1027(5) 0.5159(15) 0.7364(4) 0.049(3) Uani 1 1 d U . .
H6 H 0.1328 0.4880 0.7194 0.059 Uiso 1 1 calc R . .
C7 C 0.0453(6) 0.5439(15) 0.7170(4) 0.048(3) Uani 1 1 d U . .
C8 C 0.0008(5) 0.5858(17) 0.7429(4) 0.050(3) Uani 1 1 d U . .
C9 C 0.0611(7) 0.5002(16) 0.6412(4) 0.048(3) Uani 1 1 d U . .
C10 C 0.0572(6) 0.4464(19) 0.5646(4) 0.064(4) Uani 1 1 d U . .
H10A H 0.0282 0.3755 0.5456 0.077 Uiso 1 1 calc R . .
H10B H 0.0912 0.3685 0.5747 0.077 Uiso 1 1 calc R . .
C11 C 0.0787(6) 0.5963(18) 0.5394(4) 0.065(4) Uani 1 1 d U . .
H11A H 0.0450 0.6755 0.5297 0.078 Uiso 1 1 calc R . .
H11B H 0.0936 0.5478 0.5138 0.078 Uiso 1 1 calc R . .
C12 C 0.1279(6) 0.7043(17) 0.5651(4) 0.058(4) Uani 1 1 d U . .
H12A H 0.1121 0.7567 0.5900 0.069 Uiso 1 1 calc R . .
H12B H 0.1605 0.6230 0.5762 0.069 Uiso 1 1 calc R . .
C13 C 0.1532(6) 0.8504(19) 0.5407(4) 0.060(4) Uani 1 1 d U . .
H13A H 0.1208 0.9305 0.5288 0.072 Uiso 1 1 calc R . .
H13B H 0.1816 0.9200 0.5606 0.072 Uiso 1 1 calc R . .
C14 C 0.2421(6) 0.7473(17) 0.5100(4) 0.051(3) Uani 1 1 d U . .
C15 C 0.3211(6) 0.6675(16) 0.4665(4) 0.046(3) Uani 1 1 d U . .
C16 C 0.3697(5) 0.6536(18) 0.4958(5) 0.065(4) Uani 1 1 d U . .
H16 H 0.3648 0.6628 0.5251 0.078 Uiso 1 1 calc R . .
C17 C 0.4272(6) 0.6262(18) 0.4855(5) 0.061(4) Uani 1 1 d U . .
H17 H 0.4608 0.6225 0.5068 0.074 Uiso 1 1 calc R . .
C18 C 0.4322(7) 0.6055(18) 0.4435(5) 0.073(4) Uani 1 1 d U . .
H18 H 0.4703 0.5814 0.4357 0.088 Uiso 1 1 calc R . .
C19 C 0.3854(6) 0.6173(17) 0.4117(4) 0.053(3) Uani 1 1 d U . .
C20 C 0.3763(7) 0.6052(19) 0.3640(5) 0.069(4) Uani 1 1 d U . .
H20 H 0.4057 0.5837 0.3459 0.083 Uiso 1 1 calc R . .
C21 C 0.3178(7) 0.6311(19) 0.3519(4) 0.071(4) Uani 1 1 d U . .
H21 H 0.2992 0.6299 0.3232 0.085 Uiso 1 1 calc R . .
C22 C 0.3281(5) 0.6539(18) 0.4239(4) 0.058(4) Uani 1 1 d U . .
K1 K -0.13499(14) 0.9483(4) 0.63689(9) 0.0675(10) Uani 1 1 d . . .
O1 O 0.1139(4) 0.4651(12) 0.6480(3) 0.063(3) Uani 1 1 d . . .
O2 O 0.2733(4) 0.7487(12) 0.5456(3) 0.061(2) Uani 1 1 d . . .
O3 O -0.1322(5) 1.0328(13) 0.7255(3) 0.072(3) Uani 1 1 d . . .
O4 O -0.2410(5) 0.9489(13) 0.6731(3) 0.076(3) Uani 1 1 d . . .
O5 O -0.2321(5) 0.7863(13) 0.5923(3) 0.078(3) Uani 1 1 d . . .
O6 O -0.1325(4) 0.8697(12) 0.5498(3) 0.067(3) Uani 1 1 d . . .
O7 O -0.0256(4) 0.9397(11) 0.6047(3) 0.060(2) Uani 1 1 d . . .
O8 O -0.0334(4) 1.0958(12) 0.6841(3) 0.070(3) Uani 1 1 d . . .
C23 C -0.1872(8) 1.090(2) 0.7332(5) 0.086(5) Uani 1 1 d U . .
H23A H -0.1971 1.2027 0.7178 0.103 Uiso 1 1 calc R . .
H23B H -0.1867 1.1125 0.7641 0.103 Uiso 1 1 calc R . .
C24 C -0.2332(8) 0.954(2) 0.7187(5) 0.092(6) Uani 1 1 d U . .
H24A H -0.2204 0.8367 0.7304 0.110 Uiso 1 1 calc R . .
H24B H -0.2711 0.9849 0.7290 0.110 Uiso 1 1 calc R . .
C25 C -0.2795(8) 0.820(2) 0.6549(5) 0.084(5) Uani 1 1 d U . .
H25A H -0.3184 0.8365 0.6651 0.100 Uiso 1 1 calc R . .
H25B H -0.2641 0.7026 0.6649 0.100 Uiso 1 1 calc R . .
C26 C -0.2887(6) 0.821(2) 0.6061(5) 0.072(4) Uani 1 1 d U . .
H26A H -0.3176 0.7286 0.5951 0.087 Uiso 1 1 calc R . .
H26B H -0.3040 0.9373 0.5953 0.087 Uiso 1 1 calc R . .
C27 C -0.2364(6) 0.7880(19) 0.5467(4) 0.068(4) Uani 1 1 d U . .
H27A H -0.2495 0.9062 0.5357 0.082 Uiso 1 1 calc R . .
H27B H -0.2660 0.6998 0.5345 0.082 Uiso 1 1 calc R . .
C28 C -0.1772(7) 0.745(2) 0.5338(5) 0.080(5) Uani 1 1 d U . .
H28A H -0.1650 0.6256 0.5444 0.096 Uiso 1 1 calc R . .
H28B H -0.1806 0.7427 0.5022 0.096 Uiso 1 1 calc R . .
C29 C -0.0737(7) 0.825(2) 0.5413(5) 0.073(4) Uani 1 1 d U . .
H29A H -0.0725 0.8173 0.5102 0.088 Uiso 1 1 calc R . .
H29B H -0.0614 0.7094 0.5543 0.088 Uiso 1 1 calc R . .
C30 C -0.0343(7) 0.965(2) 0.5600(4) 0.075(4) Uani 1 1 d U . .
H30A H 0.0041 0.9598 0.5486 0.090 Uiso 1 1 calc R . .
H30B H -0.0524 1.0826 0.5530 0.090 Uiso 1 1 calc R . .
C31 C 0.0154(6) 1.067(2) 0.6244(5) 0.071(4) Uani 1 1 d U . .
H31A H 0.0013 1.1879 0.6163 0.085 Uiso 1 1 calc R . .
H31B H 0.0546 1.0499 0.6146 0.085 Uiso 1 1 calc R . .
C32 C 0.0208(7) 1.046(2) 0.6712(5) 0.075(4) Uani 1 1 d U . .
H32A H 0.0299 0.9212 0.6792 0.090 Uiso 1 1 calc R . .
H32B H 0.0532 1.1215 0.6853 0.090 Uiso 1 1 calc R . .
C33 C -0.0320(7) 1.100(2) 0.7303(5) 0.076(4) Uani 1 1 d U . .
H33A H -0.0212 0.9824 0.7425 0.091 Uiso 1 1 calc R . .
H33B H -0.0017 1.1864 0.7428 0.091 Uiso 1 1 calc R . .
C34 C -0.0887(8) 1.151(2) 0.7405(4) 0.078(5) Uani 1 1 d U . .
H34A H -0.0868 1.1600 0.7719 0.094 Uiso 1 1 calc R . .
H34B H -0.0991 1.2688 0.7282 0.094 Uiso 1 1 calc R . .
K2 K 0.32564(13) 0.8536(4) 0.62025(9) 0.0619(9) Uani 1 1 d . . .
O9 O 0.2558(5) 1.1621(17) 0.6126(4) 0.098(4) Uani 1 1 d . . .
O10 O 0.2408(5) 0.923(2) 0.6786(3) 0.094(4) Uani 1 1 d . . .
O11 O 0.3097(6) 0.6178(15) 0.6860(3) 0.086(3) Uani 1 1 d . . .
O12 O 0.4198(5) 0.6362(15) 0.6551(4) 0.092(4) Uani 1 1 d . . .
O13 O 0.4351(5) 0.8591(17) 0.5881(3) 0.089(3) Uani 1 1 d . . .
O14 O 0.3644(7) 1.1640(16) 0.5785(4) 0.107(4) Uani 1 1 d . . .
C35 C 0.2247(10) 1.201(3) 0.6468(7) 0.117(7) Uani 1 1 d U . .
H35A H 0.1950 1.2938 0.6381 0.141 Uiso 1 1 calc R . .
H35B H 0.2527 1.2472 0.6709 0.141 Uiso 1 1 calc R . .
C36 C 0.1947(8) 1.046(3) 0.6611(6) 0.099(6) Uani 1 1 d U . .
H36A H 0.1697 1.0793 0.6832 0.119 Uiso 1 1 calc R . .
H36B H 0.1691 0.9908 0.6369 0.119 Uiso 1 1 calc R . .
C37 C 0.2156(9) 0.775(3) 0.6886(7) 0.118(7) Uani 1 1 d U . .
H37A H 0.1976 0.7126 0.6625 0.142 Uiso 1 1 calc R . .
H37B H 0.1842 0.7995 0.7067 0.142 Uiso 1 1 calc R . .
C38 C 0.2653(9) 0.662(3) 0.7131(6) 0.105(6) Uani 1 1 d U . .
H38A H 0.2840 0.7283 0.7384 0.126 Uiso 1 1 calc R . .
H38B H 0.2481 0.5520 0.7232 0.126 Uiso 1 1 calc R . .
C39 C 0.3595(10) 0.548(2) 0.7074(7) 0.112(7) Uani 1 1 d U . .
H39A H 0.3492 0.4413 0.7231 0.134 Uiso 1 1 calc R . .
H39B H 0.3780 0.6347 0.7285 0.134 Uiso 1 1 calc R . .
C40 C 0.4042(9) 0.497(3) 0.6772(7) 0.111(7) Uani 1 1 d U . .
H40A H 0.4400 0.4460 0.6941 0.133 Uiso 1 1 calc R . .
H40B H 0.3865 0.4050 0.6571 0.133 Uiso 1 1 calc R . .
C41 C 0.4598(9) 0.600(3) 0.6260(7) 0.114(7) Uani 1 1 d U . .
H41A H 0.4393 0.5359 0.6010 0.137 Uiso 1 1 calc R . .
H41B H 0.4926 0.5250 0.6396 0.137 Uiso 1 1 calc R . .
C42 C 0.4831(8) 0.766(3) 0.6125(7) 0.112(7) Uani 1 1 d U . .
H42A H 0.4994 0.8371 0.6377 0.135 Uiso 1 1 calc R . .
H42B H 0.5152 0.7441 0.5949 0.135 Uiso 1 1 calc R . .
C43 C 0.4536(8) 1.021(3) 0.5703(7) 0.117(7) Uani 1 1 d U . .
H43A H 0.4817 0.9953 0.5497 0.140 Uiso 1 1 calc R . .
H43B H 0.4740 1.0966 0.5933 0.140 Uiso 1 1 calc R . .
C44 C 0.4013(11) 1.113(3) 0.5486(6) 0.124(8) Uani 1 1 d U . .
H44A H 0.4139 1.2187 0.5337 0.149 Uiso 1 1 calc R . .
H44B H 0.3793 1.0338 0.5271 0.149 Uiso 1 1 calc R . .
C45 C 0.3127(11) 1.244(3) 0.5584(6) 0.114(7) Uani 1 1 d U . .
H45A H 0.2901 1.1576 0.5392 0.136 Uiso 1 1 calc R . .
H45B H 0.3236 1.3443 0.5408 0.136 Uiso 1 1 calc R . .
C46 C 0.2761(9) 1.308(2) 0.5884(7) 0.100(6) Uani 1 1 d U . .
H46A H 0.2415 1.3710 0.5731 0.120 Uiso 1 1 calc R . .
H46B H 0.2988 1.3926 0.6082 0.120 Uiso 1 1 calc R . .
O15 O -0.1728(5) 0.4354(15) 0.6657(3) 0.087(3) Uani 1 1 d . . .
O16 O -0.0968(4) 0.6031(13) 0.6487(3) 0.065(3) Uani 1 1 d . . .
O17 O -0.0889(4) 0.3907(13) 0.5793(3) 0.068(3) Uani 1 1 d . . .
O18 O -0.1728(4) 0.2542(13) 0.5930(3) 0.075(3) Uani 1 1 d . . .
C47 C -0.1350(7) 0.476(2) 0.6420(5) 0.066(4) Uani 1 1 d U . .
C48 C -0.1299(7) 0.366(2) 0.6008(5) 0.063(4) Uani 1 1 d U . .

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
N1 0.058(7) 0.078(8) 0.041(7) 0.012(6) 0.016(5) 0.010(6)
N2 0.057(7) 0.054(7) 0.036(6) 0.000(5) 0.001(5) 0.004(5)
N3 0.064(7) 0.077(8) 0.053(8) -0.001(6) 0.014(6) 0.009(6)
N4 0.048(7) 0.098(9) 0.041(7) -0.015(6) 0.023(5) -0.002(6)
N5 0.059(7) 0.089(9) 0.028(6) 0.004(6) 0.013(5) -0.001(6)
N6 0.071(8) 0.064(8) 0.042(7) 0.007(6) 0.010(6) -0.007(6)
C1 0.091(11) 0.080(10) 0.049(9) 0.015(8) 0.038(8) 0.003(8)
C2 0.086(11) 0.087(11) 0.069(11) 0.022(9) 0.005(9) 0.006(9)
C3 0.050(8) 0.055(9) 0.067(9) 0.008(7) 0.017(7) 0.020(6)
C4 0.072(9) 0.049(8) 0.062(9) -0.002(7) 0.000(8) 0.011(7)
C5 0.061(9) 0.068(10) 0.049(9) 0.006(7) 0.000(7) 0.011(7)
C6 0.058(8) 0.045(8) 0.042(8) 0.002(6) 0.002(6) 0.018(6)
C7 0.071(9) 0.034(7) 0.036(7) -0.001(6) 0.001(6) 0.006(6)
C8 0.043(7) 0.057(9) 0.048(8) 0.000(7) 0.006(6) 0.004(6)
C9 0.079(10) 0.045(8) 0.023(7) 0.007(6) 0.013(6) 0.004(7)
C10 0.079(10) 0.075(10) 0.041(8) -0.003(7) 0.016(7) -0.004(8)
C11 0.082(10) 0.061(9) 0.057(9) -0.011(8) 0.026(7) -0.009(8)
C12 0.088(10) 0.063(9) 0.025(7) -0.003(7) 0.019(6) 0.003(7)
C13 0.068(9) 0.077(10) 0.044(8) -0.008(7) 0.035(6) -0.004(7)
C14 0.061(9) 0.053(8) 0.045(9) -0.005(7) 0.026(7) -0.013(7)
C15 0.062(8) 0.046(8) 0.034(7) 0.003(6) 0.021(6) -0.003(6)
C16 0.050(8) 0.088(10) 0.056(9) -0.015(8) 0.007(7) 0.003(7)
C17 0.045(8) 0.076(10) 0.061(9) 0.002(8) 0.000(7) 0.011(7)
C18 0.078(10) 0.065(10) 0.075(11) -0.011(9) 0.009(9) 0.025(8)
C19 0.075(9) 0.058(9) 0.031(7) 0.006(7) 0.022(6) 0.005(7)
C20 0.064(9) 0.079(10) 0.073(10) 0.004(8) 0.037(8) 0.008(8)
C21 0.090(11) 0.091(11) 0.038(8) -0.004(8) 0.029(7) -0.001(9)
C22 0.047(8) 0.076(10) 0.054(9) 0.009(8) 0.017(7) 0.008(7)
K1 0.084(2) 0.079(2) 0.0398(18) 0.0063(17) 0.0092(15) 0.0002(18)
O1 0.048(6) 0.078(7) 0.065(6) -0.009(5) 0.020(5) 0.010(5)
O2 0.071(6) 0.075(6) 0.038(5) -0.009(5) 0.016(5) 0.003(5)
O3 0.068(7) 0.093(8) 0.058(7) 0.008(6) 0.019(5) -0.005(6)
O4 0.097(8) 0.082(7) 0.052(6) 0.008(6) 0.020(5) 0.004(6)
O5 0.091(8) 0.087(8) 0.053(7) 0.022(6) 0.000(6) -0.011(6)
O6 0.090(7) 0.065(6) 0.046(6) 0.010(5) 0.009(5) -0.005(6)
O7 0.083(7) 0.049(6) 0.048(6) 0.008(5) 0.013(5) 0.004(5)
O8 0.087(7) 0.072(7) 0.051(6) -0.002(5) 0.007(5) -0.007(5)
C23 0.111(13) 0.098(12) 0.051(10) 0.014(9) 0.017(9) -0.009(11)
C24 0.124(13) 0.121(14) 0.041(9) 0.034(9) 0.049(9) 0.034(11)
C25 0.104(12) 0.101(13) 0.050(10) 0.016(9) 0.025(8) -0.012(10)
C26 0.068(10) 0.084(11) 0.065(10) 0.008(8) 0.012(8) -0.002(8)
C27 0.077(10) 0.070(10) 0.054(9) 0.016(8) -0.003(7) -0.010(8)
C28 0.112(13) 0.073(11) 0.051(9) 0.001(9) -0.007(9) 0.018(10)
C29 0.079(10) 0.097(12) 0.046(9) -0.006(8) 0.019(7) 0.014(9)
C30 0.088(10) 0.095(12) 0.046(9) 0.001(9) 0.022(8) -0.007(9)
C31 0.056(9) 0.081(10) 0.077(11) -0.004(9) 0.014(7) 0.003(8)
C32 0.070(10) 0.064(10) 0.091(12) 0.003(9) 0.010(9) 0.008(8)
C33 0.094(11) 0.075(11) 0.056(10) 0.002(8) 0.005(8) -0.013(9)
C34 0.107(12) 0.096(12) 0.030(8) 0.005(8) 0.003(8) -0.022(10)
K2 0.076(2) 0.068(2) 0.0424(18) 0.0035(17) 0.0107(15) 0.0079(16)
O9 0.093(8) 0.125(11) 0.070(8) -0.018(8) -0.012(7) 0.016(7)
O10 0.072(8) 0.150(11) 0.063(7) -0.053(8) 0.021(6) -0.029(8)
O11 0.115(9) 0.097(9) 0.044(6) 0.000(6) 0.006(6) -0.016(7)
O12 0.120(10) 0.078(8) 0.077(8) 0.013(7) 0.007(7) 0.032(7)
O13 0.087(8) 0.112(9) 0.074(8) -0.033(7) 0.033(6) -0.030(7)
O14 0.166(12) 0.093(9) 0.056(8) 0.008(7) -0.009(8) -0.047(8)
C35 0.125(15) 0.127(16) 0.089(14) -0.047(13) -0.027(12) 0.050(13)
C36 0.077(12) 0.137(16) 0.084(12) -0.065(12) 0.016(10) 0.004(12)
C37 0.086(13) 0.167(18) 0.100(15) -0.057(14) 0.011(11) -0.032(14)
C38 0.148(16) 0.105(13) 0.074(12) -0.038(11) 0.054(12) -0.032(12)
C39 0.163(17) 0.078(12) 0.090(14) 0.011(11) 0.001(14) -0.033(12)
C40 0.133(15) 0.078(13) 0.112(15) 0.014(12) -0.015(12) 0.039(11)
C41 0.079(12) 0.139(17) 0.127(16) -0.050(14) 0.025(11) 0.024(12)
C42 0.062(11) 0.162(18) 0.114(15) -0.070(14) 0.017(10) -0.001(12)
C43 0.090(13) 0.158(18) 0.103(15) -0.040(14) 0.018(11) -0.038(13)
C44 0.20(2) 0.137(16) 0.043(11) -0.021(11) 0.047(13) -0.066(15)
C45 0.179(18) 0.101(14) 0.054(11) 0.021(11) -0.009(13) -0.024(13)
C46 0.122(14) 0.078(12) 0.087(13) 0.029(11) -0.030(11) -0.008(11)
O15 0.085(8) 0.128(10) 0.051(7) 0.017(6) 0.016(6) -0.018(7)
O16 0.073(6) 0.078(7) 0.045(6) 0.013(5) 0.011(5) 0.002(5)
O17 0.066(6) 0.087(7) 0.055(6) -0.006(5) 0.022(5) 0.000(5)
O18 0.078(7) 0.073(7) 0.071(7) -0.004(6) -0.002(5) -0.002(6)
C47 0.072(10) 0.067(10) 0.056(10) 0.007(8) 0.000(8) 0.000(8)
C48 0.071(10) 0.071(10) 0.044(9) 0.003(8) 0.000(7) 0.001(8)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 C1 1.373(16) . ?
N1 C8 1.374(14) . ?
N2 C9 1.356(15) . ?
N2 C7 1.416(14) . ?
N3 C9 1.364(15) . ?
N3 C10 1.465(17) . ?
N4 C14 1.343(15) . ?
N4 C13 1.477(15) . ?
N5 C14 1.333(15) . ?
N5 C15 1.415(15) . ?
N6 C21 1.365(16) . ?
N6 C22 1.382(15) . ?
C1 C2 1.325(19) . ?
C2 C3 1.421(19) . ?
C3 C4 1.388(17) . ?
C3 C8 1.446(18) . ?
C4 C5 1.352(18) . ?
C4 K2 3.421(13) 2_546 ?
C5 C6 1.409(17) . ?
C5 K2 3.475(14) 2_546 ?
C6 C7 1.385(15) . ?
C7 C8 1.420(17) . ?
C9 O1 1.222(14) . ?
C10 C11 1.504(18) . ?
C11 C12 1.529(17) . ?
C12 C13 1.504(17) . ?
C14 O2 1.248(14) . ?
C15 C16 1.350(16) . ?
C15 C22 1.381(17) . ?
C16 C17 1.406(17) . ?
C17 C18 1.357(19) . ?
C18 C19 1.367(17) . ?
C19 C22 1.434(17) . ?
C19 C20 1.497(18) . ?
C20 C21 1.349(18) . ?
K1 O5 2.747(10) . ?
K1 O16 2.759(10) . ?
K1 O18 2.774(10) 1_565 ?
K1 O4 2.804(11) . ?
K1 O8 2.812(10) . ?
K1 O7 2.812(10) . ?
K1 O6 2.824(10) . ?
K1 O3 2.866(11) . ?
K1 C48 3.364(16) 1_565 ?
O2 K2 2.620(10) . ?
O3 C34 1.369(16) . ?
O3 C23 1.377(18) . ?
O4 C25 1.384(17) . ?
O4 C24 1.430(16) . ?
O5 C27 1.431(16) . ?
O5 C26 1.436(16) . ?
O6 C28 1.429(17) . ?
O6 C29 1.441(15) . ?
O7 C30 1.414(15) . ?
O7 C31 1.425(15) . ?
O8 C32 1.401(16) . ?
O8 C33 1.456(16) . ?
C23 C24 1.50(2) . ?
C25 C26 1.53(2) . ?
C27 C28 1.495(19) . ?
C29 C30 1.461(19) . ?
C31 C32 1.48(2) . ?
C33 C34 1.424(19) . ?
K2 O11 2.798(11) . ?
K2 O12 2.807(11) . ?
K2 O13 2.814(11) . ?
K2 O9 2.815(12) . ?
K2 O14 2.887(12) . ?
K2 O10 2.890(11) . ?
K2 C4 3.421(14) 2_556 ?
K2 C5 3.475(14) 2_556 ?
K2 C45 3.53(2) . ?
O9 C35 1.40(2) . ?
O9 C46 1.45(2) . ?
O10 C37 1.32(2) . ?
O10 C36 1.45(2) . ?
O11 C39 1.35(2) . ?
O11 C38 1.448(19) . ?
O12 C40 1.34(2) . ?
O12 C41 1.40(2) . ?
O13 C43 1.43(2) . ?
O13 C42 1.43(2) . ?
O14 C44 1.40(2) . ?
O14 C45 1.40(2) . ?
C35 C36 1.46(3) . ?
C37 C38 1.54(2) . ?
C39 C40 1.53(3) . ?
C41 C42 1.45(3) . ?
C43 C44 1.47(3) . ?
C45 C46 1.43(2) . ?
O15 C47 1.253(17) . ?
O16 C47 1.291(16) . ?
O17 C48 1.239(16) . ?
O18 C48 1.290(16) . ?
O18 K1 2.774(10) 1_545 ?
C47 C48 1.56(2) . ?
C48 K1 3.364(16) 1_545 ?

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
C1 N1 C8 107.9(11) . . ?
C9 N2 C7 127.9(11) . . ?
C9 N3 C10 119.6(11) . . ?
C14 N4 C13 123.4(11) . . ?
C14 N5 C15 128.8(11) . . ?
C21 N6 C22 111.0(12) . . ?
C2 C1 N1 110.8(15) . . ?
C1 C2 C3 109.0(15) . . ?
C4 C3 C2 136.7(15) . . ?
C4 C3 C8 118.6(13) . . ?
C2 C3 C8 104.6(11) . . ?
C5 C4 C3 121.9(14) . . ?
C5 C4 K2 80.9(8) . 2_546 ?
C3 C4 K2 147.8(10) . 2_546 ?
C4 C5 C6 120.1(12) . . ?
C4 C5 K2 76.5(8) . 2_546 ?
C6 C5 K2 152.2(9) . 2_546 ?
C7 C6 C5 121.2(13) . . ?
C6 C7 N2 124.5(12) . . ?
C6 C7 C8 118.9(11) . . ?
N2 C7 C8 116.6(10) . . ?
N1 C8 C7 133.0(12) . . ?
N1 C8 C3 107.6(11) . . ?
C7 C8 C3 119.1(10) . . ?
O1 C9 N2 123.8(11) . . ?
O1 C9 N3 123.6(12) . . ?
N2 C9 N3 112.6(12) . . ?
N3 C10 C11 113.4(12) . . ?
C10 C11 C12 112.8(12) . . ?
C13 C12 C11 115.0(11) . . ?
N4 C13 C12 112.3(11) . . ?
O2 C14 N5 124.0(13) . . ?
O2 C14 N4 121.7(12) . . ?
N5 C14 N4 114.2(12) . . ?
C16 C15 C22 118.2(13) . . ?
C16 C15 N5 127.7(12) . . ?
C22 C15 N5 114.0(11) . . ?
C15 C16 C17 123.7(13) . . ?
C18 C17 C16 116.5(13) . . ?
C17 C18 C19 123.6(14) . . ?
C18 C19 C22 117.6(12) . . ?
C18 C19 C20 136.6(13) . . ?
C22 C19 C20 105.9(11) . . ?
C21 C20 C19 106.1(12) . . ?
C20 C21 N6 110.8(13) . . ?
C15 C22 N6 133.3(12) . . ?
C15 C22 C19 120.3(12) . . ?
N6 C22 C19 106.3(11) . . ?
O5 K1 O16 82.3(3) . . ?
O5 K1 O18 86.6(3) . 1_565 ?
O16 K1 O18 158.0(3) . 1_565 ?
O5 K1 O4 62.1(3) . . ?
O16 K1 O4 102.6(3) . . ?
O18 K1 O4 88.7(3) 1_565 . ?
O5 K1 O8 176.9(3) . . ?
O16 K1 O8 94.6(3) . . ?
O18 K1 O8 96.5(3) 1_565 . ?
O4 K1 O8 118.3(3) . . ?
O5 K1 O7 119.7(3) . . ?
O16 K1 O7 75.5(3) . . ?
O18 K1 O7 93.9(3) 1_565 . ?
O4 K1 O7 176.9(3) . . ?
O8 K1 O7 59.7(3) . . ?
O5 K1 O6 61.6(3) . . ?
O16 K1 O6 83.5(3) . . ?
O18 K1 O6 74.5(3) 1_565 . ?
O4 K1 O6 121.9(3) . . ?
O8 K1 O6 118.7(3) . . ?
O7 K1 O6 60.6(3) . . ?
O5 K1 O3 120.8(3) . . ?
O16 K1 O3 96.4(3) . . ?
O18 K1 O3 105.6(3) 1_565 . ?
O4 K1 O3 60.6(3) . . ?
O8 K1 O3 58.8(3) . . ?
O7 K1 O3 117.0(3) . . ?
O6 K1 O3 177.5(3) . . ?
O5 K1 C48 107.8(3) . 1_565 ?
O16 K1 C48 155.3(4) . 1_565 ?
O18 K1 C48 21.6(3) 1_565 1_565 ?
O4 K1 C48 102.0(4) . 1_565 ?
O8 K1 C48 75.2(3) . 1_565 ?
O7 K1 C48 80.0(3) . 1_565 ?
O6 K1 C48 82.0(3) . 1_565 ?
O3 K1 C48 97.2(3) . 1_565 ?
C14 O2 K2 161.9(9) . . ?
C34 O3 C23 111.4(13) . . ?
C34 O3 K1 113.9(8) . . ?
C23 O3 K1 109.9(8) . . ?
C25 O4 C24 115.2(13) . . ?
C25 O4 K1 111.2(9) . . ?
C24 O4 K1 114.4(9) . . ?
C27 O5 C26 111.1(10) . . ?
C27 O5 K1 117.1(8) . . ?
C26 O5 K1 117.1(8) . . ?
C28 O6 C29 114.5(11) . . ?
C28 O6 K1 112.3(8) . . ?
C29 O6 K1 111.8(7) . . ?
C30 O7 C31 109.9(11) . . ?
C30 O7 K1 110.2(8) . . ?
C31 O7 K1 112.7(8) . . ?
C32 O8 C33 113.3(11) . . ?
C32 O8 K1 115.6(8) . . ?
C33 O8 K1 116.7(9) . . ?
O3 C23 C24 110.1(14) . . ?
O4 C24 C23 108.4(13) . . ?
O4 C25 C26 114.2(13) . . ?
O5 C26 C25 107.3(12) . . ?
O5 C27 C28 109.3(11) . . ?
O6 C28 C27 112.6(12) . . ?
O6 C29 C30 106.8(12) . . ?
O7 C30 C29 107.5(12) . . ?
O7 C31 C32 109.1(13) . . ?
O8 C32 C31 107.6(12) . . ?
C34 C33 O8 109.6(12) . . ?
O3 C34 C33 112.5(14) . . ?
O2 K2 O11 112.8(3) . . ?
O2 K2 O12 114.1(3) . . ?
O11 K2 O12 60.2(4) . . ?
O2 K2 O13 89.9(3) . . ?
O11 K2 O13 119.1(4) . . ?
O12 K2 O13 58.9(4) . . ?
O2 K2 O9 89.4(3) . . ?
O11 K2 O9 117.7(4) . . ?
O12 K2 O9 155.8(3) . . ?
O13 K2 O9 118.3(4) . . ?
O2 K2 O14 88.0(3) . . ?
O11 K2 O14 159.2(3) . . ?
O12 K2 O14 113.0(4) . . ?
O13 K2 O14 58.9(4) . . ?
O9 K2 O14 59.4(4) . . ?
O2 K2 O10 111.5(3) . . ?
O11 K2 O10 58.5(4) . . ?
O12 K2 O10 113.3(4) . . ?
O13 K2 O10 157.9(3) . . ?
O9 K2 O10 59.1(4) . . ?
O14 K2 O10 114.5(5) . . ?
O2 K2 C4 159.3(4) . 2_556 ?
O11 K2 C4 85.9(3) . 2_556 ?
O12 K2 C4 66.5(3) . 2_556 ?
O13 K2 C4 72.6(4) . 2_556 ?
O9 K2 C4 89.4(3) . 2_556 ?
O14 K2 C4 73.7(3) . 2_556 ?
O10 K2 C4 85.3(4) . 2_556 ?
O2 K2 C5 173.6(3) . 2_556 ?
O11 K2 C5 69.2(3) . 2_556 ?
O12 K2 C5 72.3(3) . 2_556 ?
O13 K2 C5 94.3(3) . 2_556 ?
O9 K2 C5 84.4(3) . 2_556 ?
O14 K2 C5 90.1(3) . 2_556 ?
O10 K2 C5 63.9(3) . 2_556 ?
C4 K2 C5 22.6(3) 2_556 2_556 ?
O2 K2 C45 76.1(4) . . ?
O11 K2 C45 159.1(5) . . ?
O12 K2 C45 135.2(5) . . ?
O13 K2 C45 78.5(5) . . ?
O9 K2 C45 41.9(5) . . ?
O14 K2 C45 22.4(4) . . ?
O10 K2 C45 100.8(5) . . ?
C4 K2 C45 89.4(4) 2_556 . ?
C5 K2 C45 100.0(4) 2_556 . ?
C35 O9 C46 118.6(17) . . ?
C35 O9 K2 116.3(11) . . ?
C46 O9 K2 117.3(11) . . ?
C37 O10 C36 108.5(16) . . ?
C37 O10 K2 110.4(12) . . ?
C36 O10 K2 112.5(10) . . ?
C39 O11 C38 113.7(15) . . ?
C39 O11 K2 116.0(11) . . ?
C38 O11 K2 117.5(10) . . ?
C40 O12 C41 115.5(16) . . ?
C40 O12 K2 115.0(11) . . ?
C41 O12 K2 112.6(11) . . ?
C43 O13 C42 112.8(15) . . ?
C43 O13 K2 118.3(11) . . ?
C42 O13 K2 116.4(11) . . ?
C44 O14 C45 110.9(16) . . ?
C44 O14 K2 109.4(11) . . ?
C45 O14 K2 105.7(11) . . ?
O9 C35 C36 112.3(17) . . ?
O10 C36 C35 106.6(16) . . ?
O10 C37 C38 106.1(16) . . ?
O11 C38 C37 110.8(16) . . ?
O11 C39 C40 111.7(16) . . ?
O12 C40 C39 111.9(15) . . ?
O12 C41 C42 108.6(17) . . ?
O13 C42 C41 107.5(15) . . ?
O13 C43 C44 109.0(16) . . ?
O14 C44 C43 109.7(17) . . ?
O14 C45 C46 112.0(16) . . ?
O14 C45 K2 51.9(8) . . ?
C46 C45 K2 85.8(11) . . ?
C45 C46 O9 110.4(16) . . ?
C47 O16 K1 119.1(8) . . ?
C48 O18 K1 105.9(8) . 1_545 ?
O15 C47 O16 125.8(15) . . ?
O15 C47 C48 119.9(14) . . ?
O16 C47 C48 114.3(15) . . ?
O17 C48 O18 126.9(14) . . ?
O17 C48 C47 121.4(14) . . ?
O18 C48 C47 111.7(14) . . ?
O17 C48 K1 113.0(10) . 1_545 ?
O18 C48 K1 52.5(7) . 1_545 ?
C47 C48 K1 102.0(9) . 1_545 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H901 O16 0.88 1.88 2.717(14) 159.2 .
N2 H902 O16 0.88 2.00 2.871(14) 172.9 .
N3 H903 O17 0.88 2.20 2.828(15) 128.1 .
N4 H904 O18 0.88 2.37 3.108(15) 141.2 3_566
N4 H904 O17 0.88 2.63 3.471(14) 159.4 3_566
N5 H905 O18 0.88 1.90 2.750(14) 162.6 3_566
N6 H906 O18 0.88 2.05 2.882(15) 157.2 3_566
N6 H906 O15 0.88 2.39 3.012(15) 127.9 3_566

_diffrn_measured_fraction_theta_max 0.920
_diffrn_reflns_theta_full        24.30
_diffrn_measured_fraction_theta_full 0.920
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.080

#===END

data_2011sot0537
_database_code_depnum_ccdc_archive 'CCDC 862709'
#TrackingRef '- cally-final.cif'

_chemical_compound_source        'Cally Haynes'
_database_code_CSD               1SOT0537

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C24 H28 N6 O2, 2(C16 H36 N), 2(H2 O4 P)
;
_chemical_formula_sum            'C56 H104 N8 O10 P2'
_chemical_formula_weight         1111.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
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'
'-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                   19.3998(17)
_cell_length_b                   20.670(2)
_cell_length_c                   16.7096(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.026(4)
_cell_angle_gamma                90.00
_cell_volume                     6211.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    17002
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.02

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2424
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9683
_exptl_absorpt_correction_T_max  0.9746
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27258
_diffrn_reflns_av_R_equivalents  0.1733
_diffrn_reflns_av_sigmaI/netI    0.1340
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5477
_reflns_number_gt                2703
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_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^ > 2\s(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 di-hydrogen phosphate forms hydrogen bonded chains - and the hydrogen
atoms can be clearly seen in the difference map. Due to symmetry
constraints both O3 and O2 own 0.5 of a hydrogen
;

_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^)+(0.0800P)^2^+1.0849P] 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         5477
_refine_ls_number_parameters     350
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1636
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O1 O 0.19996(18) 0.26939(17) 0.1492(2) 0.0574(9) Uani 1 1 d . . .
N1 N 0.3279(2) 0.3260(2) 0.2430(2) 0.0530(11) Uani 1 1 d . . .
H1 H 0.2956 0.2948 0.2376 0.064 Uiso 1 1 calc R . .
N2 N 0.17736(19) 0.3788(2) 0.1235(2) 0.0440(10) Uani 1 1 d . . .
H2 H 0.1392 0.4047 0.0988 0.053 Uiso 1 1 calc R . .
N3 N 0.0873(2) 0.31092(19) 0.1317(2) 0.0460(10) Uani 1 1 d . . .
H3 H 0.0578 0.3449 0.1166 0.055 Uiso 1 1 calc R . .
C1 C 0.4020(3) 0.3257(3) 0.2969(4) 0.0729(17) Uani 1 1 d . . .
H1A H 0.4262 0.2909 0.3339 0.087 Uiso 1 1 calc R . .
C2 C 0.4352(3) 0.3815(3) 0.2899(3) 0.0666(16) Uani 1 1 d . . .
H2A H 0.4856 0.3927 0.3218 0.080 Uiso 1 1 calc R . .
C3 C 0.3830(3) 0.4199(3) 0.2280(3) 0.0495(13) Uani 1 1 d . . .
C4 C 0.3813(3) 0.4813(3) 0.1923(3) 0.0583(14) Uani 1 1 d . . .
H4 H 0.4257 0.5063 0.2098 0.070 Uiso 1 1 calc R . .
C5 C 0.3174(3) 0.5064(3) 0.1328(3) 0.0556(14) Uani 1 1 d . . .
H5 H 0.3184 0.5475 0.1080 0.067 Uiso 1 1 calc R . .
C6 C 0.2493(2) 0.4712(2) 0.1077(3) 0.0375(11) Uani 1 1 d . . .
H6 H 0.2045 0.4891 0.0678 0.045 Uiso 1 1 calc R . .
C7 C 0.2497(3) 0.4091(3) 0.1435(3) 0.0478(13) Uani 1 1 d . . .
C8 C 0.3138(3) 0.3835(3) 0.1994(3) 0.0523(13) Uani 1 1 d . . .
C9 C 0.1587(3) 0.3171(3) 0.1366(3) 0.0434(12) Uani 1 1 d . . .
C10 C 0.0579(3) 0.2511(2) 0.1502(3) 0.0480(12) Uani 1 1 d . . .
H10A H 0.0773 0.2146 0.1264 0.058 Uiso 1 1 calc R . .
H10B H 0.0031 0.2514 0.1209 0.058 Uiso 1 1 calc R . .
C11 C 0.0783(3) 0.2405(2) 0.2466(3) 0.0497(12) Uani 1 1 d . . .
H11A H 0.1330 0.2365 0.2748 0.060 Uiso 1 1 calc R . .
H11B H 0.0631 0.2791 0.2711 0.060 Uiso 1 1 calc R . .
C12 C 0.0425(3) 0.1809(3) 0.2681(3) 0.0615(15) Uani 1 1 d . . .
H12A H 0.0605 0.1767 0.3317 0.074 Uiso 1 1 calc R . .
H12B H 0.0597 0.1423 0.2458 0.074 Uiso 1 1 calc R . .
P1 P -0.00602(6) 0.47578(6) 0.37276(7) 0.0390(3) Uani 1 1 d . . .
O2 O -0.02281(17) 0.53292(15) 0.30992(19) 0.0491(8) Uani 1 1 d . . .
H2B H 0.0019 0.5291 0.2783 0.074 Uiso 0.50 1 calc PR . .
O3 O 0.00306(19) 0.41364(14) 0.32765(18) 0.0487(9) Uani 1 1 d . . .
H3A H -0.0079 0.4210 0.2749 0.073 Uiso 0.50 1 calc PR . .
O4 O -0.06535(16) 0.46850(16) 0.40998(18) 0.0511(9) Uani 1 1 d . . .
O5 O 0.07104(15) 0.48780(17) 0.44819(17) 0.0475(8) Uani 1 1 d . . .
H5A H 0.0640 0.5044 0.4904 0.071 Uiso 1 1 calc R . .
N4 N 0.23146(19) 0.41980(16) 0.8390(2) 0.0368(9) Uani 1 1 d . . .
C13 C 0.2227(3) 0.4911(2) 0.8127(3) 0.0406(11) Uani 1 1 d . . .
H13A H 0.2602 0.5019 0.7877 0.049 Uiso 1 1 calc R . .
H13B H 0.1730 0.4973 0.7669 0.049 Uiso 1 1 calc R . .
C14 C 0.2312(3) 0.53797(19) 0.8855(3) 0.0391(11) Uani 1 1 d . . .
H14A H 0.1943 0.5274 0.9113 0.047 Uiso 1 1 calc R . .
H14B H 0.2815 0.5332 0.9309 0.047 Uiso 1 1 calc R . .
C15 C 0.2204(3) 0.6063(2) 0.8542(3) 0.0633(15) Uani 1 1 d . . .
H15A H 0.1683 0.6118 0.8137 0.076 Uiso 1 1 calc R . .
H15B H 0.2529 0.6146 0.8215 0.076 Uiso 1 1 calc R . .
C16 C 0.2371(3) 0.6563(2) 0.9249(3) 0.0659(16) Uani 1 1 d . . .
H16A H 0.2044 0.6493 0.9569 0.099 Uiso 1 1 calc R . .
H16B H 0.2285 0.6997 0.8994 0.099 Uiso 1 1 calc R . .
H16C H 0.2891 0.6523 0.9644 0.099 Uiso 1 1 calc R . .
C17 C 0.2320(2) 0.3801(2) 0.7622(3) 0.0412(11) Uani 1 1 d . . .
H17A H 0.2681 0.4001 0.7406 0.049 Uiso 1 1 calc R . .
H17B H 0.2508 0.3363 0.7833 0.049 Uiso 1 1 calc R . .
C18 C 0.1595(2) 0.3726(2) 0.6872(3) 0.0451(12) Uani 1 1 d . . .
H18A H 0.1405 0.4157 0.6631 0.054 Uiso 1 1 calc R . .
H18B H 0.1224 0.3523 0.7069 0.054 Uiso 1 1 calc R . .
C19 C 0.1703(3) 0.3310(3) 0.6180(3) 0.0590(15) Uani 1 1 d . . .
H19A H 0.2079 0.3517 0.5994 0.071 Uiso 1 1 calc R . .
H19B H 0.1902 0.2884 0.6433 0.071 Uiso 1 1 calc R . .
C20 C 0.1007(3) 0.3205(3) 0.5403(3) 0.0631(15) Uani 1 1 d . . .
H20A H 0.0633 0.2995 0.5578 0.095 Uiso 1 1 calc R . .
H20B H 0.1115 0.2929 0.4988 0.095 Uiso 1 1 calc R . .
H20C H 0.0816 0.3623 0.5134 0.095 Uiso 1 1 calc R . .
C21 C 0.1660(2) 0.4011(2) 0.8638(3) 0.0388(11) Uani 1 1 d . . .
H21A H 0.1666 0.4291 0.9121 0.047 Uiso 1 1 calc R . .
H21B H 0.1193 0.4102 0.8141 0.047 Uiso 1 1 calc R . .
C22 C 0.1646(2) 0.3310(2) 0.8903(3) 0.0394(11) Uani 1 1 d . . .
H22A H 0.1733 0.3024 0.8475 0.047 Uiso 1 1 calc R . .
H22B H 0.2051 0.3235 0.9470 0.047 Uiso 1 1 calc R . .
C23 C 0.0908(2) 0.3144(2) 0.8962(3) 0.0456(12) Uani 1 1 d . . .
H23A H 0.0506 0.3206 0.8389 0.055 Uiso 1 1 calc R . .
H23B H 0.0815 0.3442 0.9374 0.055 Uiso 1 1 calc R . .
C24 C 0.0887(3) 0.2452(2) 0.9254(3) 0.0515(13) Uani 1 1 d . . .
H24A H 0.0943 0.2154 0.8827 0.077 Uiso 1 1 calc R . .
H24B H 0.0410 0.2371 0.9313 0.077 Uiso 1 1 calc R . .
H24C H 0.1293 0.2383 0.9813 0.077 Uiso 1 1 calc R . .
C25 C 0.3039(2) 0.4075(2) 0.9145(3) 0.0412(11) Uani 1 1 d . . .
H25A H 0.3069 0.3607 0.9283 0.049 Uiso 1 1 calc R . .
H25B H 0.3021 0.4310 0.9653 0.049 Uiso 1 1 calc R . .
C26 C 0.3750(2) 0.4270(2) 0.9018(3) 0.0435(12) Uani 1 1 d . . .
H26A H 0.3771 0.4051 0.8501 0.052 Uiso 1 1 calc R . .
H26B H 0.3749 0.4743 0.8923 0.052 Uiso 1 1 calc R . .
C27 C 0.4422(3) 0.4086(2) 0.9802(3) 0.0553(13) Uani 1 1 d . . .
H27A H 0.4380 0.3626 0.9940 0.066 Uiso 1 1 calc R . .
H27B H 0.4427 0.4349 1.0300 0.066 Uiso 1 1 calc R . .
C28 C 0.5155(3) 0.4186(3) 0.9677(4) 0.0661(16) Uani 1 1 d . . .
H28A H 0.5165 0.3910 0.9204 0.099 Uiso 1 1 calc R . .
H28B H 0.5570 0.4071 1.0210 0.099 Uiso 1 1 calc R . .
H28C H 0.5200 0.4640 0.9537 0.099 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
O1 0.051(2) 0.061(2) 0.056(2) -0.0065(18) 0.0155(17) 0.0152(19)
N1 0.040(2) 0.060(3) 0.055(3) 0.009(2) 0.014(2) 0.010(2)
N2 0.030(2) 0.056(3) 0.043(2) -0.004(2) 0.0117(18) 0.0000(19)
N3 0.036(2) 0.046(3) 0.053(2) 0.002(2) 0.0128(19) 0.0053(19)
C1 0.053(4) 0.086(5) 0.079(4) 0.006(4) 0.024(3) 0.007(3)
C2 0.041(3) 0.093(5) 0.060(4) 0.004(3) 0.012(3) -0.002(3)
C3 0.048(3) 0.061(4) 0.044(3) -0.008(3) 0.023(3) -0.014(3)
C4 0.055(3) 0.079(4) 0.041(3) -0.012(3) 0.020(3) -0.007(3)
C5 0.062(4) 0.070(4) 0.046(3) -0.003(3) 0.034(3) 0.002(3)
C6 0.038(3) 0.043(3) 0.034(2) -0.002(2) 0.017(2) -0.009(2)
C7 0.042(3) 0.073(4) 0.032(3) -0.007(3) 0.017(2) 0.016(3)
C8 0.057(3) 0.066(4) 0.036(3) 0.002(3) 0.019(3) 0.005(3)
C9 0.042(3) 0.056(4) 0.031(2) 0.000(2) 0.012(2) 0.023(3)
C10 0.049(3) 0.044(3) 0.050(3) -0.002(2) 0.017(2) 0.003(2)
C11 0.044(3) 0.049(3) 0.055(3) 0.004(3) 0.017(2) 0.004(2)
C12 0.069(3) 0.051(3) 0.063(4) 0.002(3) 0.023(3) 0.013(3)
P1 0.0451(7) 0.0415(7) 0.0331(6) -0.0048(6) 0.0179(6) -0.0018(6)
O2 0.064(2) 0.042(2) 0.0463(19) 0.0036(16) 0.0267(17) 0.0093(17)
O3 0.081(2) 0.038(2) 0.0370(17) 0.0009(14) 0.0335(19) -0.0068(17)
O4 0.0469(19) 0.074(2) 0.0362(16) -0.0138(16) 0.0198(15) -0.0184(18)
O5 0.0385(18) 0.070(2) 0.0349(17) -0.0085(16) 0.0146(15) -0.0001(16)
N4 0.044(2) 0.034(2) 0.039(2) -0.0020(17) 0.0230(19) -0.0023(17)
C13 0.050(3) 0.039(3) 0.037(2) 0.005(2) 0.022(2) 0.000(2)
C14 0.052(3) 0.030(3) 0.041(2) 0.003(2) 0.024(2) 0.005(2)
C15 0.107(5) 0.041(3) 0.047(3) 0.000(3) 0.034(3) -0.004(3)
C16 0.104(5) 0.048(3) 0.058(3) 0.005(3) 0.043(3) 0.007(3)
C17 0.051(3) 0.042(3) 0.038(3) -0.001(2) 0.025(2) 0.000(2)
C18 0.048(3) 0.050(3) 0.038(3) -0.002(2) 0.017(2) 0.001(2)
C19 0.054(3) 0.082(4) 0.048(3) -0.015(3) 0.027(3) -0.014(3)
C20 0.062(4) 0.075(4) 0.051(3) -0.007(3) 0.020(3) -0.010(3)
C21 0.042(3) 0.042(3) 0.041(2) 0.001(2) 0.025(2) 0.003(2)
C22 0.044(3) 0.033(3) 0.045(3) 0.006(2) 0.021(2) 0.002(2)
C23 0.045(3) 0.045(3) 0.048(3) 0.002(2) 0.019(2) -0.002(2)
C24 0.051(3) 0.053(3) 0.051(3) 0.001(3) 0.021(3) -0.011(3)
C25 0.045(3) 0.039(3) 0.043(3) 0.000(2) 0.021(2) 0.003(2)
C26 0.047(3) 0.038(3) 0.049(3) -0.002(2) 0.022(2) -0.001(2)
C27 0.051(3) 0.043(3) 0.070(3) -0.002(3) 0.021(3) -0.007(2)
C28 0.052(3) 0.063(4) 0.088(4) -0.025(3) 0.031(3) -0.014(3)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 C9 1.238(5) . ?
N1 C8 1.367(6) . ?
N1 C1 1.380(6) . ?
N2 C9 1.366(6) . ?
N2 C7 1.457(6) . ?
N3 C9 1.363(5) . ?
N3 C10 1.442(6) . ?
C1 C2 1.347(8) . ?
C2 C3 1.393(7) . ?
C3 C4 1.397(7) . ?
C3 C8 1.454(7) . ?
C4 C5 1.367(7) . ?
C5 C6 1.427(6) . ?
C6 C7 1.415(6) . ?
C7 C8 1.352(6) . ?
C10 C11 1.524(6) . ?
C11 C12 1.521(7) . ?
C12 C12 1.530(9) 2 ?
P1 O4 1.507(3) . ?
P1 O2 1.532(3) . ?
P1 O3 1.532(3) . ?
P1 O5 1.572(3) . ?
N4 C25 1.517(5) . ?
N4 C21 1.527(5) . ?
N4 C17 1.527(5) . ?
N4 C13 1.529(5) . ?
C13 C14 1.514(6) . ?
C14 C15 1.494(6) . ?
C15 C16 1.511(7) . ?
C17 C18 1.499(6) . ?
C18 C19 1.519(6) . ?
C19 C20 1.498(6) . ?
C21 C22 1.518(6) . ?
C22 C23 1.512(6) . ?
C23 C24 1.517(6) . ?
C25 C26 1.527(5) . ?
C26 C27 1.510(6) . ?
C27 C28 1.527(6) . ?

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
C8 N1 C1 107.6(5) . . ?
C9 N2 C7 130.9(4) . . ?
C9 N3 C10 122.8(4) . . ?
C2 C1 N1 110.8(5) . . ?
C1 C2 C3 108.3(5) . . ?
C2 C3 C4 136.8(5) . . ?
C2 C3 C8 105.8(5) . . ?
C4 C3 C8 117.3(5) . . ?
C5 C4 C3 121.6(5) . . ?
C4 C5 C6 120.6(5) . . ?
C7 C6 C5 118.7(4) . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 N2 123.3(5) . . ?
C6 C7 N2 116.1(4) . . ?
C7 C8 N1 131.0(5) . . ?
C7 C8 C3 121.4(5) . . ?
N1 C8 C3 107.4(4) . . ?
O1 C9 N3 120.9(5) . . ?
O1 C9 N2 125.3(4) . . ?
N3 C9 N2 113.8(4) . . ?
N3 C10 C11 112.5(4) . . ?
C12 C11 C10 113.9(4) . . ?
C11 C12 C12 115.2(3) . 2 ?
O4 P1 O2 111.16(18) . . ?
O4 P1 O3 111.45(18) . . ?
O2 P1 O3 110.07(16) . . ?
O4 P1 O5 109.19(16) . . ?
O2 P1 O5 108.76(19) . . ?
O3 P1 O5 106.05(19) . . ?
C25 N4 C21 109.6(3) . . ?
C25 N4 C17 108.3(3) . . ?
C21 N4 C17 111.1(3) . . ?
C25 N4 C13 111.6(3) . . ?
C21 N4 C13 108.0(3) . . ?
C17 N4 C13 108.2(3) . . ?
C14 C13 N4 114.8(3) . . ?
C15 C14 C13 111.4(4) . . ?
C14 C15 C16 114.3(4) . . ?
C18 C17 N4 117.2(3) . . ?
C17 C18 C19 109.9(4) . . ?
C20 C19 C18 113.9(4) . . ?
C22 C21 N4 115.4(3) . . ?
C23 C22 C21 110.9(3) . . ?
C22 C23 C24 112.1(4) . . ?
N4 C25 C26 116.2(3) . . ?
C27 C26 C25 110.1(4) . . ?
C26 C27 C28 113.2(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
N1 H1 O1 0.88 1.96 2.659(5) 135.2 .
N2 H2 O4 0.88 1.91 2.749(5) 158.2 2
N3 H3 O3 0.88 2.26 2.989(5) 140.1 2
N3 H3 O4 0.88 2.61 3.324(5) 139.3 2
O2 H2B O2 0.84 1.67 2.475(6) 159.3 2
O3 H3A O3 0.84 1.76 2.553(5) 157.3 2
O5 H5A O4 0.84 1.75 2.577(4) 169.1 5_566

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.058