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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_t

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 N2 O8 P2'
_chemical_formula_weight         368.21

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   P2(1)/c

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

_cell_length_a                   14.437(9)
_cell_length_b                   17.293(11)
_cell_length_c                   5.604(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.202(8)
_cell_angle_gamma                90.00
_cell_volume                     1399.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3493
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      28.32

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9187
_exptl_absorpt_correction_T_max  0.9684
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8741
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3344
_reflns_number_gt                2748
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.2000P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.070(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3344
_refine_ls_number_parameters     204
_refine_ls_number_restraints     130
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.1117
_refine_ls_wR_factor_ref         0.3306
_refine_ls_wR_factor_gt          0.3106
_refine_ls_goodness_of_fit_ref   1.378
_refine_ls_restrained_S_all      1.394
_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
C1 C 0.1372(4) 0.4034(3) 0.6224(12) 0.0221(12) Uani 1 1 d . . .
C2 C 0.2082(5) 0.3376(4) 0.5913(16) 0.0333(16) Uani 1 1 d . . .
H2A H 0.1795 0.2951 0.5092 0.050 Uiso 1 1 calc R . .
H2B H 0.2294 0.3207 0.7452 0.050 Uiso 1 1 calc R . .
H2C H 0.2598 0.3560 0.5000 0.050 Uiso 1 1 calc R . .
C3 C 0.4557(9) 0.6740(6) 0.749(3) 0.125(4) Uani 1 1 d GU . .
C4 C 0.5319(7) 0.7190(8) 0.811(3) 0.131(4) Uani 1 1 d GU . .
H4 H 0.5860 0.6955 0.8650 0.157 Uiso 1 1 calc R . .
C5 C 0.5271(7) 0.7990(8) 0.793(3) 0.124(4) Uani 1 1 d GU . .
H5 H 0.5781 0.8291 0.8351 0.149 Uiso 1 1 calc R . .
C6 C 0.4462(9) 0.8342(6) 0.713(3) 0.125(4) Uani 1 1 d GU . .
H6 H 0.4430 0.8878 0.7014 0.150 Uiso 1 1 calc R . .
C7 C 0.3700(7) 0.7892(8) 0.651(3) 0.118(3) Uani 1 1 d GDU . .
C8 C 0.3748(7) 0.7092(8) 0.669(3) 0.115(3) Uani 1 1 d GDU . .
C9 C 0.2869(14) 0.8273(11) 0.554(4) 0.120(4) Uani 1 1 d DU . .
H9 H 0.2828 0.8806 0.5362 0.144 Uiso 1 1 calc R . .
C10 C 0.2134(15) 0.7769(11) 0.490(4) 0.120(4) Uani 1 1 d DU . .
H10 H 0.1580 0.7981 0.4358 0.144 Uiso 1 1 calc R . .
C11 C 0.2209(15) 0.7016(12) 0.505(4) 0.119(4) Uani 1 1 d DU . .
H11 H 0.1700 0.6715 0.4632 0.143 Uiso 1 1 calc R . .
H2 H 0.302(18) 0.623(7) 0.65(4) 0.17(11) Uiso 1 1 d D . .
N1 N 0.1065(4) 0.4286(3) 0.3826(11) 0.0275(12) Uani 1 1 d . . .
H1A H 0.1557 0.4403 0.2946 0.041 Uiso 1 1 calc R . .
H1B H 0.0703 0.4700 0.3961 0.041 Uiso 1 1 calc R . .
H1C H 0.0749 0.3905 0.3128 0.041 Uiso 1 1 calc R . .
N2 N 0.2981(12) 0.6655(10) 0.579(4) 0.123(4) Uani 1 1 d DU . .
O1 O 0.2277(3) 0.4578(3) 1.0155(11) 0.0384(13) Uani 1 1 d . . .
O2 O 0.2650(3) 0.5143(3) 0.6071(11) 0.0399(14) Uani 1 1 d . . .
O3 O 0.1179(3) 0.5500(2) 0.7974(11) 0.0356(12) Uani 1 1 d . . .
H3A H 0.0906 0.5565 0.9301 0.053 Uiso 1 1 d R . .
O4 O -0.0343(3) 0.4306(2) 0.8001(10) 0.0291(11) Uani 1 1 d . . .
O5 O -0.0077(3) 0.3074(2) 0.5839(10) 0.0301(11) Uani 1 1 d . . .
O6 O 0.0619(4) 0.3253(3) 1.0018(9) 0.0318(11) Uani 1 1 d . . .
H6A H 0.0692 0.2774 0.9745 0.048 Uiso 1 1 d R . .
O8 O 0.4554(7) 0.5915(7) 0.729(5) 0.178(10) Uani 1 1 d . . .
H8 H 0.5088 0.5709 0.7319 0.268 Uiso 1 1 d R . .
O7 O 0.3931(5) 0.4669(6) 0.273(2) 0.096(3) Uani 1 1 d . . .
H7B H 0.3429 0.4652 0.1938 0.144 Uiso 1 1 d R . .
H7A H 0.3956 0.4910 0.4054 0.144 Uiso 1 1 d R . .
P1 P 0.03339(10) 0.36547(8) 0.7746(3) 0.0225(5) Uani 1 1 d . . .
P2 P 0.19348(11) 0.48532(9) 0.7781(4) 0.0279(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.022(3) 0.016(3) 0.028(3) -0.002(2) 0.002(2) 0.003(2)
C2 0.028(3) 0.020(3) 0.051(5) -0.001(3) 0.000(3) 0.007(2)
C3 0.102(6) 0.112(6) 0.160(7) -0.001(6) -0.009(6) 0.003(5)
C4 0.108(6) 0.125(7) 0.160(7) -0.006(6) -0.003(6) 0.001(6)
C5 0.104(6) 0.117(6) 0.152(7) 0.002(6) 0.001(6) -0.001(6)
C6 0.108(6) 0.112(6) 0.155(7) -0.003(6) -0.002(6) -0.013(6)
C7 0.094(5) 0.102(5) 0.156(6) 0.000(5) -0.001(5) -0.008(5)
C8 0.087(5) 0.102(5) 0.157(6) 0.006(5) -0.004(5) 0.000(5)
C9 0.098(6) 0.112(6) 0.150(7) 0.006(6) -0.004(6) -0.002(6)
C10 0.097(6) 0.114(6) 0.148(7) 0.003(6) 0.000(6) -0.001(6)
C11 0.092(6) 0.113(6) 0.152(7) 0.016(6) 0.000(6) -0.002(6)
N1 0.030(3) 0.018(2) 0.034(3) 0.003(2) 0.005(2) 0.000(2)
N2 0.094(6) 0.112(6) 0.163(7) 0.011(6) -0.005(6) -0.003(5)
O1 0.034(3) 0.047(3) 0.034(3) 0.003(3) 0.000(2) -0.003(2)
O2 0.031(3) 0.039(3) 0.050(4) 0.001(2) 0.011(2) -0.014(2)
O3 0.047(3) 0.020(2) 0.040(3) -0.004(2) 0.005(2) -0.0018(19)
O4 0.030(2) 0.0149(19) 0.042(3) -0.0003(18) 0.008(2) 0.0029(15)
O5 0.031(2) 0.019(2) 0.040(3) -0.0018(19) -0.007(2) 0.0003(18)
O6 0.047(3) 0.0176(19) 0.031(3) 0.0049(19) 0.002(2) -0.0011(18)
O8 0.071(6) 0.084(7) 0.38(3) -0.008(13) -0.052(14) 0.024(5)
O7 0.063(4) 0.108(7) 0.116(9) -0.029(7) -0.006(6) 0.017(4)
P1 0.0240(7) 0.0126(7) 0.0308(9) 0.0001(6) 0.0026(7) 0.0014(5)
P2 0.0282(8) 0.0222(8) 0.0335(10) -0.0023(7) 0.0023(7) -0.0064(5)

_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(9) . ?
C1 C2 1.542(8) . ?
C1 P1 1.848(6) . ?
C1 P2 1.850(7) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.3900 . ?
C3 C8 1.3900 . ?
C3 O8 1.432(15) . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 C8 1.3900 . ?
C7 C9 1.47(2) . ?
C8 N2 1.43(2) . ?
C9 C10 1.42(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.31(2) . ?
C10 H10 0.9300 . ?
C11 N2 1.34(3) . ?
C11 H11 0.9300 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 H2 0.822(10) . ?
N2 H2 0.822(10) . ?
O1 P2 1.496(6) . ?
O2 P2 1.497(5) . ?
O3 P2 1.567(5) . ?
O3 H3A 0.8503 . ?
O4 P1 1.498(4) . ?
O5 P1 1.581(5) . ?
O6 P1 1.507(5) . ?
O6 H6A 0.8500 . ?
O8 H8 0.8495 . ?
O7 H7B 0.8499 . ?
O7 H7A 0.8499 . ?

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 C2 108.2(5) . . ?
N1 C1 P1 106.4(4) . . ?
C2 C1 P1 109.3(4) . . ?
N1 C1 P2 109.5(4) . . ?
C2 C1 P2 109.1(4) . . ?
P1 C1 P2 114.2(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C8 120.0 . . ?
C4 C3 O8 125.4(10) . . ?
C8 C3 O8 114.0(11) . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.0 . . ?
C6 C7 C9 119.1(12) . . ?
C8 C7 C9 120.8(12) . . ?
C7 C8 C3 120.0 . . ?
C7 C8 N2 117.6(12) . . ?
C3 C8 N2 122.1(12) . . ?
C10 C9 C7 115.3(16) . . ?
C10 C9 H9 122.3 . . ?
C7 C9 H9 122.3 . . ?
C11 C10 C9 122(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 N2 123(3) . . ?
C10 C11 H11 118.3 . . ?
N2 C11 H11 118.3 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
H2 N2 C11 128(10) . . ?
H2 N2 C8 105(10) . . ?
C11 N2 C8 120.3(18) . . ?
H2 N2 H2 0(8) . . ?
C11 N2 H2 128(10) . . ?
C8 N2 H2 105(10) . . ?
P2 O3 H3A 118.7 . . ?
P1 O6 H6A 109.3 . . ?
C3 O8 H8 114.4 . . ?
H7B O7 H7A 120.5 . . ?
O4 P1 O6 116.2(3) . . ?
O4 P1 O5 107.4(3) . . ?
O6 P1 O5 112.3(3) . . ?
O4 P1 C1 107.9(3) . . ?
O6 P1 C1 109.5(3) . . ?
O5 P1 C1 102.5(3) . . ?
O1 P2 O2 116.7(3) . . ?
O1 P2 O3 113.2(3) . . ?
O2 P2 O3 106.6(3) . . ?
O1 P2 C1 108.6(3) . . ?
O2 P2 C1 104.9(3) . . ?
O3 P2 C1 105.9(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
C8 C3 C4 C5 0.0 . . . . ?
O8 C3 C4 C5 171.1(19) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C5 C6 C7 C9 -176.7(12) . . . . ?
C6 C7 C8 C3 0.0 . . . . ?
C9 C7 C8 C3 176.6(12) . . . . ?
C6 C7 C8 N2 -173.5(15) . . . . ?
C9 C7 C8 N2 3.1(14) . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
O8 C3 C8 C7 -172.1(16) . . . . ?
C4 C3 C8 N2 173.2(16) . . . . ?
O8 C3 C8 N2 1.1(19) . . . . ?
C6 C7 C9 C10 178.6(14) . . . . ?
C8 C7 C9 C10 1.9(17) . . . . ?
C7 C9 C10 C11 -3(3) . . . . ?
C9 C10 C11 N2 -1(4) . . . . ?
C10 C11 N2 H2 151(23) . . . . ?
C10 C11 N2 C8 6(4) . . . . ?
C7 C8 N2 H2 -159(19) . . . . ?
C3 C8 N2 H2 27(20) . . . . ?
C7 C8 N2 C11 -7(3) . . . . ?
C3 C8 N2 C11 179.3(18) . . . . ?
N1 C1 P1 O4 -63.0(5) . . . . ?
C2 C1 P1 O4 -179.5(5) . . . . ?
P2 C1 P1 O4 57.9(4) . . . . ?
N1 C1 P1 O6 169.6(4) . . . . ?
C2 C1 P1 O6 53.0(5) . . . . ?
P2 C1 P1 O6 -69.5(4) . . . . ?
N1 C1 P1 O5 50.2(4) . . . . ?
C2 C1 P1 O5 -66.4(5) . . . . ?
P2 C1 P1 O5 171.1(3) . . . . ?
N1 C1 P2 O1 -177.5(4) . . . . ?
C2 C1 P2 O1 -59.3(5) . . . . ?
P1 C1 P2 O1 63.3(4) . . . . ?
N1 C1 P2 O2 -52.0(5) . . . . ?
C2 C1 P2 O2 66.1(5) . . . . ?
P1 C1 P2 O2 -171.2(3) . . . . ?
N1 C1 P2 O3 60.6(5) . . . . ?
C2 C1 P2 O3 178.7(5) . . . . ?
P1 C1 P2 O3 -58.6(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
O7 H7A O8 0.85 2.65 3.46(2) 158.2 .
O7 H7A O2 0.85 2.24 2.760(11) 119.6 .
O7 H7B O1 0.85 1.94 2.790(11) 178.2 1_554
O8 H8 O7 0.85 1.56 2.410(12) 177.7 3_666
O3 H3A O4 0.85 1.73 2.584(8) 179.7 3_567
N1 H1C O6 0.89 2.08 2.854(8) 144.3 1_554
N1 H1B O4 0.89 2.11 2.839(7) 139.2 3_566
N1 H1A O1 0.89 1.91 2.753(8) 158.5 1_554
N2 H2 O2 0.822(10) 1.97(16) 2.662(18) 141(24) .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.183
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.217


_database_code_depnum_ccdc_archive 'CCDC 873343'