# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_G2HP #TrackingRef '19606_web_deposit_cif_file_0_XitaoLiu_1366285315.G2HP.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'H O4 P, 2(C H6 N3), H2 O' _chemical_formula_sum 'C2 H15 N6 O5 P' _chemical_formula_weight 234.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Tetragonal _symmetry_space_group_name_H-M 'P -4 21 c' _symmetry_space_group_name_Hall 'P -42n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' 'y+1/2, x+1/2, z+1/2' '-y+1/2, -x+1/2, z+1/2' '-y, x, -z' 'y, -x, -z' _cell_length_a 16.8420(2) _cell_length_b 16.8420(2) _cell_length_c 7.2490(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2056.20(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1973 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9671 _exptl_absorpt_process_details 'APEX2 Software Suite (Bruker,2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX2 CCD area-detectr diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9021 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2314 _reflns_number_gt 1973 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Software Suite (Bruker,2005)' _computing_cell_refinement 'APEX2 Software Suite (Bruker,2005)' _computing_data_reduction 'APEX2 Software Suite (Bruker,2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'WINGX (Farrugia,1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0412P)^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 0.0106(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.23(10) _refine_ls_number_reflns 2314 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0752 _refine_ls_wR_factor_gt 0.0690 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.51787(12) 0.65574(12) 0.3031(3) 0.0320(5) Uani 1 1 d . . . C2 C 0.35114(12) 0.89237(12) 0.2824(3) 0.0337(5) Uani 1 1 d . . . H4 H 0.2464(16) 0.7057(16) -0.009(4) 0.048(9) Uiso 1 1 d . . . H1A H 0.5041(18) 0.6605(16) 0.562(4) 0.053(9) Uiso 1 1 d . . . H2A H 0.4394(17) 0.6129(14) 0.151(3) 0.040(7) Uiso 1 1 d . . . H3A H 0.6170(14) 0.6880(13) 0.204(4) 0.037(6) Uiso 1 1 d . . . H4A H 0.3448(14) 0.7854(14) 0.331(3) 0.037(6) Uiso 1 1 d . . . H5A H 0.2508(14) 0.8738(16) 0.397(3) 0.041(7) Uiso 1 1 d . . . H6A H 0.4389(15) 0.9364(15) 0.189(4) 0.046(8) Uiso 1 1 d . . . H1B H 0.4277(19) 0.6430(17) 0.446(4) 0.058(9) Uiso 1 1 d . . . H2B H 0.5059(17) 0.6432(15) 0.055(4) 0.038(8) Uiso 1 1 d . . . H3B H 0.6162(16) 0.6987(15) 0.418(4) 0.051(8) Uiso 1 1 d . . . H4B H 0.4266(17) 0.8115(15) 0.262(4) 0.052(8) Uiso 1 1 d . . . H5B H 0.2600(15) 0.9527(18) 0.337(4) 0.050(8) Uiso 1 1 d . . . H6B H 0.3789(17) 0.9944(19) 0.213(4) 0.066(9) Uiso 1 1 d . . . H1C H 0.0789(17) 0.6297(15) 0.287(4) 0.049(8) Uiso 1 1 d . . . H1D H 0.058(2) 0.6503(18) 0.449(5) 0.067(10) Uiso 1 1 d . . . N1 N 0.47974(15) 0.64792(15) 0.4613(3) 0.0496(6) Uani 1 1 d . . . N2 N 0.48163(15) 0.63887(16) 0.1466(3) 0.0449(6) Uani 1 1 d . . . N3 N 0.59279(11) 0.67898(12) 0.3041(3) 0.0386(4) Uani 1 1 d . . . N4 N 0.37959(14) 0.81953(12) 0.2966(3) 0.0429(5) Uani 1 1 d . . . N5 N 0.27739(13) 0.90787(15) 0.3327(3) 0.0414(5) Uani 1 1 d . . . N6 N 0.39644(15) 0.94942(14) 0.2171(3) 0.0453(5) Uani 1 1 d . . . O1 O 0.03947(12) 0.63884(12) 0.3466(3) 0.0504(5) Uani 1 1 d . . . O2 O 0.18151(8) 0.59663(9) 0.1911(2) 0.0389(4) Uani 1 1 d . . . O3 O 0.27732(9) 0.68048(9) 0.37661(18) 0.0324(4) Uani 1 1 d . . . O4 O 0.28090(10) 0.68328(10) 0.02919(19) 0.0308(3) Uani 1 1 d . . . O5 O 0.32728(8) 0.56457(8) 0.1952(2) 0.0344(3) Uani 1 1 d . . . P1 P 0.26421(3) 0.62901(3) 0.20586(7) 0.02443(14) 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 0.0308(12) 0.0340(11) 0.0313(9) 0.0052(10) 0.0035(10) 0.0004(9) C2 0.0371(12) 0.0300(12) 0.0339(9) -0.0055(10) 0.0007(9) -0.0037(9) N1 0.0356(13) 0.0799(18) 0.0331(11) -0.0011(10) 0.0051(10) -0.0153(12) N2 0.0335(13) 0.0680(17) 0.0331(11) 0.0001(10) 0.0013(9) -0.0100(12) N3 0.0311(10) 0.0552(12) 0.0295(9) 0.0046(10) 0.0045(9) -0.0078(9) N4 0.0370(12) 0.0288(11) 0.0628(12) -0.0048(11) 0.0064(12) -0.0018(9) N5 0.0367(12) 0.0338(12) 0.0537(13) 0.0048(10) 0.0100(9) 0.0029(10) N6 0.0436(14) 0.0323(12) 0.0600(12) -0.0022(11) 0.0161(11) -0.0036(10) O1 0.0345(11) 0.0620(13) 0.0548(11) -0.0157(9) -0.0016(9) -0.0016(9) O2 0.0309(8) 0.0440(9) 0.0417(8) 0.0004(8) 0.0020(7) -0.0090(7) O3 0.0391(9) 0.0293(8) 0.0288(7) -0.0037(6) 0.0025(6) -0.0002(7) O4 0.0304(9) 0.0333(9) 0.0288(7) 0.0065(6) 0.0023(6) 0.0022(8) O5 0.0386(8) 0.0323(8) 0.0325(7) -0.0007(7) 0.0025(7) 0.0103(6) P1 0.0261(3) 0.0234(3) 0.0238(2) -0.0013(2) 0.0017(2) -0.0005(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 C1 N2 1.319(3) . ? C1 N3 1.321(3) . ? C1 N1 1.321(3) . ? C2 N6 1.315(3) . ? C2 N5 1.321(3) . ? C2 N4 1.321(3) . ? N1 H1A 0.86(3) . ? N1 H1B 0.89(3) . ? N2 H2A 0.84(3) . ? N2 H2B 0.78(3) . ? N3 H3A 0.85(2) . ? N3 H3B 0.97(3) . ? N4 H4A 0.86(2) . ? N4 H4B 0.84(3) . ? N5 H5A 0.86(3) . ? N5 H5B 0.81(3) . ? N6 H6A 0.78(3) . ? N6 H6B 0.81(3) . ? O1 H1C 0.81(3) . ? O1 H1D 0.83(4) . ? O2 P1 1.4997(15) . ? O3 P1 1.5272(14) . ? O4 P1 1.5983(16) . ? O4 H4 0.75(3) . ? O5 P1 1.5206(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N3 120.7(2) . . ? N2 C1 N1 120.0(2) . . ? N3 C1 N1 119.3(2) . . ? N6 C2 N5 120.0(2) . . ? N6 C2 N4 119.7(2) . . ? N5 C2 N4 120.2(2) . . ? C1 N1 H1A 118.5(19) . . ? C1 N1 H1B 112(2) . . ? H1A N1 H1B 127(3) . . ? C1 N2 H2A 118.4(16) . . ? C1 N2 H2B 118(2) . . ? H2A N2 H2B 122(3) . . ? C1 N3 H3A 120.6(16) . . ? C1 N3 H3B 119.6(16) . . ? H3A N3 H3B 118(2) . . ? C2 N4 H4A 113.4(16) . . ? C2 N4 H4B 117.8(18) . . ? H4A N4 H4B 128(2) . . ? C2 N5 H5A 120.4(16) . . ? C2 N5 H5B 122.3(19) . . ? H5A N5 H5B 114(3) . . ? C2 N6 H6A 115.2(19) . . ? C2 N6 H6B 119(2) . . ? H6A N6 H6B 126(3) . . ? H1C O1 H1D 102(3) . . ? P1 O4 H4 117(2) . . ? O2 P1 O5 112.68(8) . . ? O2 P1 O3 113.50(9) . . ? O5 P1 O3 110.20(9) . . ? O2 P1 O4 108.29(9) . . ? O5 P1 O4 104.17(9) . . ? O3 P1 O4 107.42(7) . . ? 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 H1A O5 0.86(3) 2.05(3) 2.901(3) 172(3) 8_566 N2 H2B O5 0.78(3) 2.12(3) 2.901(3) 171(3) 8_565 N2 H2A O5 0.84(3) 2.08(3) 2.906(3) 169(2) . N3 H3B O3 0.97(3) 1.89(3) 2.842(3) 167(3) 8_566 N3 H3A O4 0.85(2) 2.09(3) 2.936(3) 174(2) 8_565 N4 H4B O1 0.84(3) 2.22(3) 2.970(3) 148(2) 3_565 N4 H4A O3 0.86(2) 2.13(3) 2.964(3) 165(2) . N5 H5B O5 0.81(3) 2.40(3) 3.180(3) 162(3) 4 N5 H5A O4 0.86(3) 2.16(3) 3.019(3) 174(2) 5_455 N6 H6B O2 0.81(3) 2.12(3) 2.883(3) 157(3) 4 N6 H6A O1 0.78(3) 2.13(3) 2.868(3) 159(2) 3_565 O1 H1C O2 0.81(3) 1.94(3) 2.739(3) 168(3) . O1 H1D O2 0.83(4) 1.95(4) 2.771(3) 177(3) 5_455 O4 H4 O3 0.75(3) 1.84(3) 2.567(2) 166(3) 5_454 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.160 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.038 _database_code_depnum_ccdc_archive 'CCDC 934766'