# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_lc_190_bez_vod_acet

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H21 N6 O5 P'
_chemical_formula_sum            'C11 H21 N6 O5 P'
_chemical_formula_weight         348.31
_chemical_compound_source        'synthesized by the authors'

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 2/c'
_space_group_name_Hall           '-P 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   15.1845(4)
_cell_length_b                   13.7904(4)
_cell_length_c                   16.3311(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.6734(10)
_cell_angle_gamma                90.00
_cell_volume                     3308.20(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7799
_cell_measurement_theta_min      2.2044
_cell_measurement_theta_max      27.4926

_exptl_crystal_description       prism
_exptl_crystal_colour            red-violet
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8997
_exptl_absorpt_correction_T_max  0.9386
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30510
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         27.50
_reflns_number_total             7598
_reflns_number_gt                5611
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.1104P)²+3.5564P] where P=(Fo²+2Fc²)/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         7598
_refine_ls_number_parameters     459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.2055
_refine_ls_wR_factor_gt          0.1865
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
P1A P 0.46167(8) 0.70525(6) 0.46035(8) 0.0201(2) Uani 0.777(3) 1 d P A 1
P1C P 0.4903(3) 0.7069(3) 0.4904(3) 0.0201(2) Uani 0.223(3) 1 d P A 2
C2A C 0.79845(15) 1.03286(16) 0.77982(13) 0.0143(4) Uani 1 1 d . . .
C4A C 0.86427(15) 1.02239(17) 0.66791(13) 0.0143(4) Uani 1 1 d . . .
C5A C 0.77438(15) 1.01415(17) 0.61081(13) 0.0144(4) Uani 1 1 d . . .
C6A C 0.69868(14) 1.01896(16) 0.65056(13) 0.0135(4) Uani 1 1 d . . .
C11A C 0.53306(15) 1.01375(19) 0.63111(14) 0.0195(5) Uani 1 1 d . . .
H11A H 0.4831 1.0475 0.5903 0.023 Uiso 1 1 calc R . .
H11B H 0.5441 1.0481 0.6860 0.023 Uiso 1 1 calc R . .
C12A C 0.50543(17) 0.9106(2) 0.64190(15) 0.0251(5) Uani 1 1 d . . .
H12A H 0.5537 0.8772 0.6849 0.030 Uiso 1 1 calc R . .
H12B H 0.4486 0.9094 0.6610 0.030 Uiso 1 1 calc R . .
C13A C 0.4890(2) 0.7603(2) 0.5679(2) 0.0381(7) Uani 1 1 d . . .
H13A H 0.4419 0.7414 0.5975 0.046 Uiso 0.777(3) 1 d PR A .
H13B H 0.5484 0.7361 0.6014 0.046 Uiso 0.777(3) 1 d PR . .
H13E H 0.4334 0.7420 0.5853 0.046 Uiso 0.223(3) 1 d PR . .
H13F H 0.5419 0.7392 0.6134 0.046 Uiso 0.223(3) 1 d PR . .
C14A C 0.6249(3) 0.7379(4) 0.4354(3) 0.0462(11) Uani 0.777(3) 1 d P A 1
H14A H 0.6396 0.6734 0.4619 0.055 Uiso 0.777(3) 1 calc PR A 1
H14B H 0.6571 0.7876 0.4758 0.055 Uiso 0.777(3) 1 calc PR A 1
C15A C 0.6566(7) 0.7429(8) 0.3555(5) 0.066(2) Uani 0.777(3) 1 d P A 1
H15A H 0.6224 0.6960 0.3145 0.099 Uiso 0.777(3) 1 calc PR A 1
H15B H 0.7216 0.7275 0.3683 0.099 Uiso 0.777(3) 1 calc PR A 1
H15C H 0.6464 0.8084 0.3317 0.099 Uiso 0.777(3) 1 calc PR A 1
C16A C 0.2878(3) 0.7324(3) 0.4169(3) 0.0509(12) Uani 0.777(3) 1 d P A 1
H16A H 0.2690 0.7866 0.4484 0.061 Uiso 0.777(3) 1 d PR A 1
H16B H 0.2904 0.6725 0.4509 0.061 Uiso 0.777(3) 1 d PR A 1
C15C C 0.633(3) 0.752(4) 0.328(3) 0.066(2) Uani 0.223(3) 1 d P A 2
H15D H 0.6590 0.8075 0.3636 0.099 Uiso 0.223(3) 1 d PR A 2
H15E H 0.6278 0.7677 0.2685 0.099 Uiso 0.223(3) 1 d PR A 2
H15F H 0.6726 0.6955 0.3443 0.099 Uiso 0.223(3) 1 d PR A 2
C14C C 0.5472(8) 0.7302(9) 0.3351(7) 0.026(2) Uiso 0.223(3) 1 d P A 2
H14C H 0.5360 0.6601 0.3242 0.031 Uiso 0.223(3) 1 calc PR A 2
H14D H 0.5023 0.7662 0.2910 0.031 Uiso 0.223(3) 1 calc PR A 2
C16C C 0.3305(10) 0.7175(10) 0.3515(9) 0.036(3) Uiso 0.223(3) 1 d P A 2
H16C H 0.3476 0.6550 0.3300 0.043 Uiso 0.223(3) 1 d PR A 2
H16D H 0.3503 0.7699 0.3187 0.043 Uiso 0.223(3) 1 d PR A 2
C17A C 0.2222(3) 0.7208(3) 0.3351(3) 0.0590(10) Uani 1 1 d . . .
H17A H 0.2167 0.7816 0.3038 0.088 Uiso 0.777(3) 1 d PR A 1
H17B H 0.1622 0.7041 0.3451 0.088 Uiso 0.777(3) 1 d PR A 1
H17C H 0.2418 0.6689 0.3039 0.088 Uiso 0.777(3) 1 d PR A 1
H17D H 0.2019 0.6681 0.3662 0.088 Uiso 0.223(3) 1 d PR A 2
H17E H 0.1939 0.7137 0.2745 0.088 Uiso 0.223(3) 1 d PR A 2
H17F H 0.2046 0.7833 0.3548 0.088 Uiso 0.223(3) 1 d PR A 2
N1A N 0.71143(13) 1.02536(14) 0.73412(11) 0.0147(4) Uani 1 1 d . . .
N3A N 0.87546(12) 1.03314(15) 0.75115(11) 0.0162(4) Uani 1 1 d . . .
N7A N 0.81091(14) 1.04130(17) 0.86320(12) 0.0230(5) Uani 1 1 d . . .
H7A1 H 0.7637 1.0417 0.8853 0.028 Uiso 1 1 calc R . .
H7A2 H 0.8663 1.0465 0.8962 0.028 Uiso 1 1 calc R . .
N8A N 0.93732(13) 1.02025(17) 0.63764(12) 0.0219(5) Uani 1 1 d . . .
H8A1 H 0.9919 1.0259 0.6722 0.026 Uiso 1 1 calc R . .
H8A2 H 0.9313 1.0132 0.5829 0.026 Uiso 1 1 calc R . .
N9A N 0.77176(13) 1.00076(16) 0.52954(12) 0.0202(4) Uani 1 1 d . . .
N10A N 0.61488(13) 1.01643(16) 0.60069(12) 0.0195(4) Uani 1 1 d . . .
H10A H 0.6125 1.0156 0.5499 0.023 Uiso 1 1 d R . .
O1A O 0.69359(12) 0.99326(16) 0.47546(10) 0.0289(5) Uani 1 1 d . . .
O2A O 0.49174(13) 0.86290(13) 0.56192(11) 0.0266(4) Uani 1 1 d . A .
O3A O 0.46286(19) 0.59943(17) 0.46772(16) 0.0224(5) Uani 0.777(3) 1 d P A 1
O3C O 0.5184(9) 0.6051(7) 0.5046(7) 0.036(2) Uani 0.223(3) 1 d P A 2
O4A O 0.53215(17) 0.75359(16) 0.41809(14) 0.0427(6) Uani 1 1 d . . .
O5A O 0.3735(2) 0.7521(2) 0.40404(19) 0.0386(7) Uani 0.777(3) 1 d P A 1
O5C O 0.3823(7) 0.7273(7) 0.4501(7) 0.0386(7) Uani 0.223(3) 1 d P A 2
P1B P -0.00223(8) 0.20513(6) 0.49088(7) 0.0191(2) Uani 0.816(3) 1 d P B 1
P1D P -0.0337(4) 0.2054(3) 0.4632(3) 0.0191(2) Uani 0.184(3) 1 d P B 2
C2B C 0.29878(15) 0.52746(17) 0.77823(13) 0.0144(4) Uani 1 1 d . . .
C4B C 0.36420(15) 0.52450(16) 0.66593(13) 0.0141(4) Uani 1 1 d . . .
C5B C 0.27435(15) 0.52274(17) 0.60876(13) 0.0145(4) Uani 1 1 d . . .
C6B C 0.19864(14) 0.52883(16) 0.64809(13) 0.0130(4) Uani 1 1 d . . .
C11B C 0.03280(15) 0.52687(18) 0.62938(14) 0.0171(5) Uani 1 1 d . . .
H11C H -0.0193 0.5544 0.5865 0.021 Uiso 1 1 calc R . .
H11D H 0.0411 0.5655 0.6819 0.021 Uiso 1 1 calc R . .
C12B C 0.01260(16) 0.42365(19) 0.64689(14) 0.0220(5) Uani 1 1 d . . .
H12C H 0.0632 0.3965 0.6916 0.026 Uiso 1 1 calc R . .
H12D H -0.0438 0.4203 0.6666 0.026 Uiso 1 1 calc R . .
C13B C 0.0148(2) 0.2698(2) 0.58636(17) 0.0306(6) Uani 1 1 d . . .
H13C H -0.0285 0.2465 0.6183 0.037 Uiso 1 1 calc R B 1
H13D H 0.0774 0.2582 0.6214 0.037 Uiso 1 1 calc R B 1
C14B C 0.1400(3) 0.2492(3) 0.4404(3) 0.0531(9) Uani 1 1 d . B .
H14E H 0.1610 0.1872 0.4693 0.064 Uiso 1 1 calc R . .
H14F H 0.1719 0.3029 0.4761 0.064 Uiso 1 1 calc R . .
C15B C 0.1611(4) 0.2516(4) 0.3556(3) 0.0830(17) Uani 1 1 d . . .
H15G H 0.1267 0.2006 0.3195 0.125 Uiso 1 1 calc R . .
H15H H 0.2265 0.2410 0.3627 0.125 Uiso 1 1 calc R . .
H15I H 0.1440 0.3149 0.3290 0.125 Uiso 1 1 calc R . .
C16B C -0.1493(3) 0.2092(3) 0.3631(2) 0.0387(9) Uani 0.816(3) 1 d P B 1
H16E H -0.1295 0.1461 0.3451 0.046 Uiso 0.816(3) 1 d PR B 1
H16F H -0.1322 0.2607 0.3279 0.046 Uiso 0.816(3) 1 d PR B 1
C16D C -0.1963(14) 0.2294(15) 0.4268(13) 0.049(5) Uiso 0.184(3) 1 d P B 2
H16G H -0.1931 0.1758 0.4678 0.059 Uiso 0.184(3) 1 d PR B 2
H16H H -0.2197 0.2881 0.4491 0.059 Uiso 0.184(3) 1 d PR B 2
C17B C -0.2526(3) 0.2088(3) 0.3511(2) 0.0510(9) Uani 1 1 d . . .
H17G H -0.2699 0.1540 0.3801 0.076 Uiso 0.816(3) 1 d PR B 1
H17H H -0.2822 0.2032 0.2891 0.076 Uiso 0.816(3) 1 d PR B 1
H17I H -0.2705 0.2696 0.3715 0.076 Uiso 0.816(3) 1 d PR B 1
H17J H -0.2961 0.2618 0.3327 0.076 Uiso 0.184(3) 1 d PR B 2
H17K H -0.2857 0.1491 0.3563 0.076 Uiso 0.184(3) 1 d PR B 2
H17L H -0.2170 0.1993 0.3094 0.076 Uiso 0.184(3) 1 d PR B 2
N1B N 0.21138(12) 0.52986(14) 0.73204(11) 0.0140(4) Uani 1 1 d . . .
N3B N 0.37569(12) 0.52688(15) 0.75001(11) 0.0167(4) Uani 1 1 d . . .
N7B N 0.31136(14) 0.52700(18) 0.86188(12) 0.0248(5) Uani 1 1 d . . .
H7B1 H 0.2642 0.5282 0.8839 0.030 Uiso 1 1 calc R . .
H7B2 H 0.3669 0.5255 0.8951 0.030 Uiso 1 1 calc R . .
N8B N 0.43749(13) 0.52386(17) 0.63598(12) 0.0216(5) Uani 1 1 d . . .
H8B1 H 0.4921 0.5250 0.6711 0.026 Uiso 1 1 calc R . .
H8B2 H 0.4316 0.5223 0.5810 0.026 Uiso 1 1 calc R . .
N9B N 0.27109(13) 0.50969(16) 0.52712(12) 0.0197(4) Uani 1 1 d . . .
N10B N 0.11482(13) 0.53320(15) 0.59869(11) 0.0172(4) Uani 1 1 d . . .
H10B H 0.1133 0.5247 0.5517 0.021 Uiso 1 1 d R . .
O1B O 0.19275(11) 0.50736(15) 0.47300(10) 0.0263(4) Uani 1 1 d . . .
O2B O 0.00188(12) 0.36958(12) 0.57059(11) 0.0237(4) Uani 1 1 d . B .
O3B O 0.02431(16) 0.10314(15) 0.50578(13) 0.0209(5) Uani 0.816(3) 1 d P B 1
O3D O -0.0300(8) 0.0976(8) 0.4715(7) 0.027(2) Uiso 0.184(3) 1 d P B 2
O4B O 0.04411(16) 0.25891(14) 0.42830(13) 0.0354(5) Uani 1 1 d . . .
O5B O -0.10644(19) 0.22586(19) 0.45120(18) 0.0357(6) Uani 0.816(3) 1 d P B 1
O5D O -0.1133(9) 0.2486(9) 0.4056(9) 0.0357(6) Uani 0.184(3) 1 d P B 2


_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
P1A O3A 1.464(3) . ?
P1A O5A 1.559(3) . ?
P1A O4A 1.562(2) . ?
P1A C13A 1.862(3) . ?
P1C O3C 1.468(10) . ?
P1C C13A 1.469(5) . ?
P1C O4A 1.611(4) . ?
P1C O5C 1.629(11) . ?
C2A N7A 1.332(3) . ?
C2A N1A 1.347(3) . ?
C2A N3A 1.365(3) . ?
C4A N8A 1.324(3) . ?
C4A N3A 1.335(3) . ?
C4A C5A 1.449(3) . ?
C5A N9A 1.331(3) . ?
C5A C6A 1.458(3) . ?
C6A N10A 1.326(3) . ?
C6A N1A 1.332(3) . ?
C11A N10A 1.451(3) . ?
C11A C12A 1.506(4) . ?
C12A O2A 1.430(3) . ?
C13A O2A 1.419(3) . ?
C14A O4A 1.381(5) . ?
C14A C15A 1.502(10) . ?
C16A O5A 1.397(5) . ?
C16A C17A 1.457(6) . ?
C15C C14C 1.37(4) . ?
C14C O4A 1.466(12) . ?
C16C C17A 1.599(14) . ?
C16C O5C 1.608(17) . ?
N9A O1A 1.292(2) . ?
P1B O3B 1.466(2) . ?
P1B O4B 1.566(2) . ?
P1B O5B 1.577(3) . ?
P1B C13B 1.758(3) . ?
P1D O5D 1.459(13) . ?
P1D O3D 1.493(11) . ?
P1D O4B 1.614(5) . ?
P1D C13B 2.151(6) . ?
C2B N7B 1.331(3) . ?
C2B N1B 1.351(3) . ?
C2B N3B 1.360(3) . ?
C4B N8B 1.324(3) . ?
C4B N3B 1.340(3) . ?
C4B C5B 1.445(3) . ?
C5B N9B 1.334(3) . ?
C5B C6B 1.454(3) . ?
C6B N10B 1.324(3) . ?
C6B N1B 1.335(3) . ?
C11B N10B 1.458(3) . ?
C11B C12B 1.499(3) . ?
C12B O2B 1.426(3) . ?
C13B O2B 1.404(3) . ?
C14B O4B 1.426(4) . ?
C14B C15B 1.499(5) . ?
C16B O5B 1.439(4) . ?
C16B C17B 1.531(5) . ?
C16D C17B 1.34(2) . ?
C16D O5D 1.41(2) . ?
N9B O1B 1.290(2) . ?

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
O3A P1A O5A 116.89(16) . . ?
O3A P1A O4A 117.78(14) . . ?
O5A P1A O4A 98.31(16) . . ?
O3A P1A C13A 109.52(14) . . ?
O5A P1A C13A 109.89(16) . . ?
O4A P1A C13A 103.23(14) . . ?
O3C P1C C13A 114.2(5) . . ?
O3C P1C O4A 110.2(4) . . ?
C13A P1C O4A 121.7(3) . . ?
O3C P1C O5C 116.8(7) . . ?
C13A P1C O5C 91.7(5) . . ?
O4A P1C O5C 100.3(5) . . ?
N7A C2A N1A 116.0(2) . . ?
N7A C2A N3A 116.0(2) . . ?
N1A C2A N3A 127.98(19) . . ?
N8A C4A N3A 118.7(2) . . ?
N8A C4A C5A 119.97(19) . . ?
N3A C4A C5A 121.34(19) . . ?
N9A C5A C4A 115.97(19) . . ?
N9A C5A C6A 128.5(2) . . ?
C4A C5A C6A 115.49(18) . . ?
N10A C6A N1A 119.9(2) . . ?
N10A C6A C5A 117.88(19) . . ?
N1A C6A C5A 122.2(2) . . ?
N10A C11A C12A 110.6(2) . . ?
O2A C12A C11A 107.92(19) . . ?
O2A C13A P1C 115.7(3) . . ?
O2A C13A P1A 110.2(2) . . ?
P1C C13A P1A 14.23(17) . . ?
O4A C14A C15A 110.5(5) . . ?
O5A C16A C17A 109.3(4) . . ?
C15C C14C O4A 114(2) . . ?
C17A C16C O5C 112.7(9) . . ?
C16A C17A C16C 54.2(5) . . ?
C6A N1A C2A 116.14(19) . . ?
C4A N3A C2A 116.73(18) . . ?
O1A N9A C5A 118.89(19) . . ?
C6A N10A C11A 124.21(19) . . ?
C13A O2A C12A 113.3(2) . . ?
C14A O4A C14C 76.4(5) . . ?
C14A O4A P1A 128.3(3) . . ?
C14C O4A P1A 126.8(5) . . ?
C14A O4A P1C 111.0(3) . . ?
C14C O4A P1C 140.6(5) . . ?
P1A O4A P1C 20.53(13) . . ?
C16A O5A P1A 121.6(3) . . ?
C16C O5C P1C 125.2(9) . . ?
O3B P1B O4B 114.36(12) . . ?
O3B P1B O5B 116.56(15) . . ?
O4B P1B O5B 102.47(15) . . ?
O3B P1B C13B 111.53(14) . . ?
O4B P1B C13B 110.42(13) . . ?
O5B P1B C13B 100.33(15) . . ?
O5D P1D O3D 118.1(8) . . ?
O5D P1D O4B 98.4(6) . . ?
O3D P1D O4B 118.3(5) . . ?
O5D P1D C13B 117.8(6) . . ?
O3D P1D C13B 109.3(5) . . ?
O4B P1D C13B 92.0(3) . . ?
N7B C2B N1B 116.02(19) . . ?
N7B C2B N3B 115.8(2) . . ?
N1B C2B N3B 128.15(19) . . ?
N8B C4B N3B 118.4(2) . . ?
N8B C4B C5B 120.36(19) . . ?
N3B C4B C5B 121.27(19) . . ?
N9B C5B C4B 115.97(19) . . ?
N9B C5B C6B 128.0(2) . . ?
C4B C5B C6B 115.86(18) . . ?
N10B C6B N1B 119.46(19) . . ?
N10B C6B C5B 118.61(19) . . ?
N1B C6B C5B 121.94(19) . . ?
N10B C11B C12B 110.87(19) . . ?
O2B C12B C11B 108.27(18) . . ?
O2B C13B P1B 110.62(18) . . ?
O2B C13B P1D 103.5(2) . . ?
P1B C13B P1D 12.11(13) . . ?
O4B C14B C15B 108.7(4) . . ?
O5B C16B C17B 108.6(3) . . ?
C17B C16D O5D 102.3(14) . . ?
C16D C17B C16B 59.2(9) . . ?
C6B N1B C2B 116.06(18) . . ?
C4B N3B C2B 116.57(18) . . ?
O1B N9B C5B 118.84(19) . . ?
C6B N10B C11B 124.10(18) . . ?
C13B O2B C12B 111.86(19) . . ?
C14B O4B P1B 118.5(2) . . ?
C14B O4B P1D 136.2(3) . . ?
P1B O4B P1D 20.51(17) . . ?
C16B O5B P1B 122.3(3) . . ?
C16D O5D P1D 114.2(13) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.090
#===END
_database_code_depnum_ccdc_archive 'CCDC 1001296'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lc_190_etac_met_budes
_publcif_datablock.id            {d08afd2c-c488-49d6-9938-fd9686b8c9a8}
_audit_update_record             
;
2014-05-05 # Formatted by publCIF

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H21 N6 O5 P, H2 O'
_chemical_formula_sum            'C11 H23 N6 O6 P'
_chemical_formula_weight         366.32
_chemical_compound_source        'synthesized by the authors'

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'

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

_cell_length_a                   8.5829(2)
_cell_length_b                   10.4800(3)
_cell_length_c                   11.4529(3)
_cell_angle_alpha                113.4116(10)
_cell_angle_beta                 92.8654(11)
_cell_angle_gamma                108.2169(10)
_cell_volume                     879.87(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4983
_cell_measurement_theta_min      2.2722
_cell_measurement_theta_max      27.5332

_exptl_crystal_description       prism
_exptl_crystal_colour            'light violet'
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8789
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9450
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3951
_reflns_number_gt                3327
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0530P)²+0.6451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3951
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.47668(17) -0.14882(15) 0.32759(14) 0.0204(3) Uani 1 1 d . . .
C2 C 0.6032(2) -0.17092(18) 0.38248(16) 0.0188(3) Uani 1 1 d . . .
N3 N 0.76317(17) -0.07230(15) 0.43854(13) 0.0188(3) Uani 1 1 d . . .
C4 C 0.7984(2) 0.06301(18) 0.44264(15) 0.0170(3) Uani 1 1 d . A .
C5 C 0.6768(2) 0.10017(18) 0.38400(16) 0.0183(3) Uani 1 1 d . . .
C6 C 0.5114(2) -0.01583(18) 0.32815(15) 0.0181(3) Uani 1 1 d . A .
N7 N 0.56821(19) -0.30380(16) 0.38094(16) 0.0269(4) Uani 1 1 d . . .
H71 H 0.4663 -0.3738 0.3420 0.032 Uiso 1 1 d R . .
H72 H 0.6431 -0.3260 0.4209 0.032 Uiso 1 1 d R . .
N8 N 0.95013(17) 0.16498(15) 0.50323(14) 0.0212(3) Uani 1 1 d . . .
H81 H 1.0343 0.1383 0.5281 0.025 Uiso 1 1 d R A .
H82 H 0.9841 0.2550 0.4998 0.025 Uiso 1 1 d R . .
N9A N 0.7333(3) 0.2353(5) 0.3870(4) 0.0258(7) Uani 0.787(3) 1 d P A 1
O1A O 0.6299(2) 0.27395(18) 0.33411(18) 0.0316(4) Uani 0.787(3) 1 d P A 1
N9B N 0.6892(18) 0.226(2) 0.373(2) 0.0258(7) Uani 0.213(3) 1 d P A 2
O1B O 0.8296(8) 0.3287(7) 0.4192(7) 0.0316(4) Uani 0.213(3) 1 d P A 2
N10 N 0.39169(18) 0.01242(16) 0.27637(14) 0.0220(3) Uani 1 1 d . . .
H10 H 0.4164 0.1000 0.2792 0.026 Uiso 1 1 d R A .
C11 C 0.2218(2) -0.0953(2) 0.22002(18) 0.0251(4) Uani 1 1 d . A .
H11A H 0.1934 -0.1604 0.2651 0.030 Uiso 1 1 calc R . .
H11B H 0.2139 -0.1590 0.1272 0.030 Uiso 1 1 calc R . .
C12 C 0.1000(2) -0.0167(2) 0.23221(18) 0.0247(4) Uani 1 1 d . . .
H12A H -0.0157 -0.0904 0.1958 0.030 Uiso 1 1 calc R A .
H12B H 0.1074 0.0476 0.3247 0.030 Uiso 1 1 calc R . .
C13 C 0.0301(2) 0.14779(19) 0.16285(18) 0.0229(4) Uani 1 1 d . . .
H13A H -0.0152 0.1709 0.2435 0.028 Uiso 1 1 calc R A .
H13B H -0.0646 0.0852 0.0876 0.028 Uiso 1 1 calc R . .
C14 C 0.3895(3) 0.2996(3) 0.0152(4) 0.0657(8) Uani 1 1 d . A .
H14A H 0.4582 0.3899 0.0943 0.079 Uiso 1 1 calc R . .
H14B H 0.4075 0.3218 -0.0604 0.079 Uiso 1 1 calc R . .
C15 C 0.4450(3) 0.1775(3) 0.0021(3) 0.0580(7) Uani 1 1 d . . .
H15A H 0.4406 0.1632 0.0816 0.087 Uiso 1 1 calc R . .
H15B H 0.5602 0.2015 -0.0122 0.087 Uiso 1 1 calc R . .
H15C H 0.3716 0.0858 -0.0719 0.087 Uiso 1 1 calc R . .
C16A C -0.0237(7) 0.4872(5) 0.2205(4) 0.0542(11) Uani 0.667(6) 1 d P A 1
H16A H 0.0817 0.5722 0.2708 0.065 Uiso 0.667(6) 1 d PR A 1
H16B H -0.0775 0.4489 0.2805 0.065 Uiso 0.667(6) 1 d PR A 1
C16B C 0.0159(14) 0.5256(11) 0.1794(9) 0.0542(11) Uani 0.333(6) 1 d P A 2
H16C H 0.0627 0.5715 0.2736 0.065 Uiso 0.333(6) 1 d PR A 2
H16D H 0.0924 0.5830 0.1409 0.065 Uiso 0.333(6) 1 d PR A 2
C17 C -0.1383(3) 0.5388(3) 0.1615(3) 0.0472(6) Uani 1 1 d . . .
H17A H -0.0758 0.5976 0.1196 0.071 Uiso 0.667(6) 1 d PR A .
H17B H -0.1836 0.5995 0.2300 0.071 Uiso 0.667(6) 1 d PR . .
H17C H -0.2308 0.4513 0.0970 0.071 Uiso 0.667(6) 1 d PR . .
H17D H -0.1826 0.4991 0.0685 0.071 Uiso 0.333(6) 1 d PR . .
H17E H -0.1257 0.6441 0.2049 0.071 Uiso 0.333(6) 1 d PR . .
H17F H -0.2159 0.4822 0.1988 0.071 Uiso 0.333(6) 1 d PR . .
P1 P 0.14836(6) 0.31675(5) 0.15327(5) 0.02731(15) Uani 1 1 d . A .
O2 O 0.14140(15) 0.07177(14) 0.16249(12) 0.0245(3) Uani 1 1 d . A .
O3 O 0.2788(2) 0.42301(16) 0.26916(16) 0.0464(4) Uani 1 1 d . . .
O4 O 0.21430(19) 0.26539(19) 0.02359(16) 0.0423(4) Uani 1 1 d . . .
O5 O 0.01138(19) 0.37373(16) 0.12033(14) 0.0388(4) Uani 1 1 d . . .
O1W O 0.77264(17) 0.58270(15) 0.48895(15) 0.0341(3) Uani 1 1 d . . .
H1W H 0.7287 0.4904 0.4306 0.041 Uiso 1 1 d R . .
H2W H 0.7477 0.5784 0.5660 0.041 Uiso 1 1 d R . .


_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
N1 C6 1.328(2) . ?
N1 C2 1.354(2) . ?
C2 N7 1.322(2) . ?
C2 N3 1.365(2) . ?
N3 C4 1.335(2) . ?
C4 N8 1.330(2) . ?
C4 C5 1.444(2) . ?
C5 N9A 1.331(5) . ?
C5 N9B 1.35(2) . ?
C5 C6 1.454(2) . ?
C6 N10 1.328(2) . ?
N9A O1A 1.299(4) . ?
N9B O1B 1.249(16) . ?
N10 C11 1.454(2) . ?
C11 C12 1.501(2) . ?
C12 O2 1.426(2) . ?
C13 O2 1.422(2) . ?
C13 P1 1.7942(18) . ?
C14 O4 1.450(3) . ?
C14 C15 1.457(4) . ?
C16A O5 1.412(4) . ?
C16A C17 1.508(5) . ?
C16B C17 1.387(10) . ?
C16B O5 1.448(9) . ?
P1 O3 1.4671(14) . ?
P1 O5 1.5668(15) . ?
P1 O4 1.5669(17) . ?

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
C6 N1 C2 116.56(14) . . ?
N7 C2 N1 116.29(14) . . ?
N7 C2 N3 116.15(15) . . ?
N1 C2 N3 127.57(15) . . ?
C4 N3 C2 116.42(14) . . ?
N8 C4 N3 118.18(15) . . ?
N8 C4 C5 120.04(14) . . ?
N3 C4 C5 121.78(14) . . ?
N9A C5 N9B 15.9(6) . . ?
N9A C5 C4 115.10(16) . . ?
N9B C5 C4 130.9(6) . . ?
N9A C5 C6 129.28(17) . . ?
N9B C5 C6 113.4(6) . . ?
C4 C5 C6 115.61(14) . . ?
N10 C6 N1 119.16(15) . . ?
N10 C6 C5 118.88(15) . . ?
N1 C6 C5 121.96(15) . . ?
O1A N9A C5 117.8(2) . . ?
O1B N9B C5 115.5(12) . . ?
C6 N10 C11 123.01(14) . . ?
N10 C11 C12 110.39(15) . . ?
O2 C12 C11 107.91(14) . . ?
O2 C13 P1 106.93(11) . . ?
O4 C14 C15 112.4(2) . . ?
O5 C16A C17 109.1(3) . . ?
C17 C16B O5 114.2(8) . . ?
C16B C17 C16A 30.2(4) . . ?
O3 P1 O5 115.80(9) . . ?
O3 P1 O4 114.66(10) . . ?
O5 P1 O4 102.58(8) . . ?
O3 P1 C13 113.34(9) . . ?
O5 P1 C13 103.81(8) . . ?
O4 P1 C13 105.30(9) . . ?
C13 O2 C12 113.15(13) . . ?
C14 O4 P1 124.75(19) . . ?
C16A O5 C16B 30.9(4) . . ?
C16A O5 P1 119.6(2) . . ?
C16B O5 P1 126.4(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
N7 H71 O3 0.90 2.03 2.886(2) 158.8 1_545
N7 H72 O1W 0.91 1.98 2.878(2) 168.1 1_545
N8 H81 N3 0.92 2.13 3.048(2) 172.5 2_756
N8 H82 O1B 0.91 2.07 2.695(6) 124.3 .
N8 H82 O1W 0.91 2.20 2.9187(19) 134.8 2_766
N10 H10 O1A 0.86 1.99 2.655(2) 133.1 .
O1W H1W O1A 0.87 1.95 2.804(2) 167.0 .
O1W H1W O1B 0.87 2.10 2.670(6) 122.8 .
O1W H1W N9B 0.87 2.48 3.24(2) 146.8 .
O1W H1W N9A 0.87 2.53 3.248(5) 140.2 .
O1W H2W O3 0.93 1.92 2.848(2) 174.0 2_666

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.054
#===END

_database_code_depnum_ccdc_archive 'CCDC 1001297'
