# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Chick Wilson' 'Andres E. Goeta' 'Suzanne M. Harte' 'Andrew Parkin' _publ_contact_author_name 'Prof Chick Wilson' _publ_contact_author_address ; Department of Chemistry University of Glasgow Glasgow G12 8QQ UNITED KINGDOM ; _publ_contact_author_email C.C.WILSON@CHEM.GLA.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Imaging proton migration from X-rays and neutrons ; data_150k _database_code_depnum_ccdc_archive 'CCDC 231379' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1:1 co-crystal of urea:phosphoric acid' _chemical_melting_point ? _chemical_formula_moiety 'H2 O4 P, H, O C H4 N2' _chemical_formula_sum 'C H7 N2 O5 P' _chemical_formula_weight 158.06 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.4613(3) _cell_length_b 8.9753(4) _cell_length_c 17.5018(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1172.05(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 926 _cell_measurement_theta_min 10.51 _cell_measurement_theta_max 26.20 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.791 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.428 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 SMART-6000 CCD Diffractometer' _diffrn_measurement_method '\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 7798 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 30.50 _reflns_number_total 1784 _reflns_number_gt 1631 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2000)' _computing_cell_refinement 'SMART V5.625 (Bruker, 2000)' _computing_data_reduction 'SAINT V6.02A (Bruker, 2000)' _computing_structure_solution 'known coordinates' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material Encifer _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. Hydrogen atoms were all placed on the difference map and allowed to freely refine except for H1, for which the neutron coordinates and Uij's were used and constrained, as explained in the manuscript. ; _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^)+(0.0476P)^2^+0.4140P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'known coordinates' _atom_sites_solution_secondary none _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1784 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0300 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0781 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 P P 0.22047(4) 0.19045(3) 0.189004(15) 0.01367(10) Uani 1 1 d . . . O1 O 0.11413(10) 0.06264(8) 0.22265(4) 0.01616(16) Uani 1 1 d . . . O2 O 0.40880(11) 0.13832(10) 0.16006(5) 0.01978(17) Uani 1 1 d . . . H2 H 0.467(3) 0.113(3) 0.1944(12) 0.061(7) Uiso 1 1 d . . . O3 O 0.24843(13) 0.30488(9) 0.25485(5) 0.01978(18) Uani 1 1 d . . . H3 H 0.289(3) 0.383(2) 0.2438(11) 0.041(5) Uiso 1 1 d . . . O4 O 0.13162(11) 0.26264(9) 0.12033(4) 0.01921(17) Uani 1 1 d . . . O5 O -0.13636(12) 0.19046(8) 0.05182(5) 0.02013(18) Uani 1 1 d . . . N6 N -0.13369(14) -0.04352(11) 0.10258(6) 0.0226(2) Uani 1 1 d . . . H6A H -0.173(2) -0.135(2) 0.1014(9) 0.036(5) Uiso 1 1 d . . . H6B H -0.071(3) -0.015(2) 0.1400(10) 0.038(5) Uiso 1 1 d . . . N7 N -0.28380(14) 0.00763(11) -0.00913(6) 0.0203(2) Uani 1 1 d . . . H7A H -0.307(2) 0.072(2) -0.0439(9) 0.032(4) Uiso 1 1 d . . . H7B H -0.315(2) -0.079(2) -0.0122(9) 0.030(4) Uiso 1 1 d . . . C8 C -0.18349(14) 0.05171(11) 0.04890(6) 0.01600(19) Uani 1 1 d . . . H1 H -0.0099 0.2170 0.0895 0.023 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 P 0.01575(16) 0.01177(14) 0.01349(15) 0.00000(8) -0.00025(8) -0.00086(8) O1 0.0182(3) 0.0123(3) 0.0180(4) 0.0012(3) 0.0004(3) -0.0010(3) O2 0.0166(4) 0.0257(4) 0.0171(4) -0.0013(3) 0.0002(3) 0.0014(3) O3 0.0290(4) 0.0138(3) 0.0165(4) -0.0023(3) 0.0021(3) -0.0051(3) O4 0.0204(4) 0.0175(4) 0.0197(4) 0.0049(3) -0.0040(3) -0.0024(3) O5 0.0231(4) 0.0130(4) 0.0243(4) 0.0015(3) -0.0067(3) -0.0006(3) N6 0.0292(5) 0.0177(4) 0.0210(5) 0.0046(3) -0.0074(4) -0.0053(4) N7 0.0251(5) 0.0177(4) 0.0180(4) 0.0008(3) -0.0050(3) -0.0032(4) C8 0.0156(4) 0.0158(4) 0.0166(4) 0.0002(3) 0.0008(4) 0.0004(3) H1 0.025 0.020 0.023 0.003 0.001 0.001 _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 P O1 1.5140(8) . ? P O4 1.5179(8) . ? P O3 1.5576(8) . ? P O2 1.5653(8) . ? O2 H2 0.78(2) . ? O3 H3 0.79(2) . ? O4 H1 1.2541 . ? O5 C8 1.2951(12) . ? O5 H1 1.1761 . ? N6 C8 1.3233(14) . ? N6 H6A 0.875(19) . ? N6 H6B 0.843(19) . ? N7 C8 1.3222(14) . ? N7 H7A 0.859(17) . ? N7 H7B 0.812(19) . ? 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 O1 P O4 113.74(5) . . ? O1 P O3 106.38(5) . . ? O4 P O3 111.28(5) . . ? O1 P O2 111.71(5) . . ? O4 P O2 105.27(5) . . ? O3 P O2 108.44(5) . . ? P O2 H2 110.0(16) . . ? P O3 H3 117.1(14) . . ? P O4 H1 124.6 . . ? C8 O5 H1 115.8 . . ? C8 N6 H6A 120.0(11) . . ? C8 N6 H6B 120.4(13) . . ? H6A N6 H6B 119.4(17) . . ? C8 N7 H7A 117.1(12) . . ? C8 N7 H7B 119.9(12) . . ? H7A N7 H7B 122.9(16) . . ? O5 C8 N7 118.14(10) . . ? O5 C8 N6 121.13(10) . . ? N7 C8 N6 120.73(10) . . ? 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 O5 H1 O4 1.18 1.25 2.4198(12) 169.4 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.432 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.068 data_200k _database_code_depnum_ccdc_archive 'CCDC 231380' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1:1 co-crystal of urea:phosphoric acid' _chemical_melting_point ? _chemical_formula_moiety 'H2 O4 P, H, O C H4 N2' _chemical_formula_sum 'C H7 N2 O5 P' _chemical_formula_weight 158.06 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.4667(3) _cell_length_b 8.9827(3) _cell_length_c 17.5438(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1176.68(7) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 974 _cell_measurement_theta_min 10.39 _cell_measurement_theta_max 26.16 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.427 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 SMART-6000 CCD Diffractometer' _diffrn_measurement_method '\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 7841 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.51 _reflns_number_total 1791 _reflns_number_gt 1619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2000)' _computing_cell_refinement 'SMART V5.625 (Bruker, 2000)' _computing_data_reduction 'SAINT V6.02A (Bruker, 2000)' _computing_structure_solution 'known coordinates' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material Encifer _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. Hydrogen atoms were all placed on the difference map and allowed to freely refine except for H1, for which the neutron coordinates and Uij's were used and constrained, as explained in the manuscript. ; _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^)+(0.0494P)^2^+0.3598P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'known coordinates' _atom_sites_solution_secondary none _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1791 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0306 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 P P 0.22076(4) 0.19061(3) 0.189022(15) 0.01679(10) Uani 1 1 d . . . O1 O 0.11458(11) 0.06326(8) 0.22263(4) 0.01986(17) Uani 1 1 d . . . O2 O 0.40875(11) 0.13859(10) 0.16021(5) 0.02427(18) Uani 1 1 d . . . H2 H 0.468(3) 0.113(3) 0.1955(12) 0.062(6) Uiso 1 1 d . . . O3 O 0.24856(13) 0.30524(9) 0.25444(5) 0.02451(19) Uani 1 1 d . . . H3 H 0.290(3) 0.384(2) 0.2443(11) 0.043(5) Uiso 1 1 d . . . O4 O 0.13220(12) 0.26246(9) 0.12038(4) 0.02401(18) Uani 1 1 d . . . O5 O -0.13572(12) 0.19033(8) 0.05216(5) 0.0253(2) Uani 1 1 d . . . N6 N -0.13461(15) -0.04302(12) 0.10284(6) 0.0285(2) Uani 1 1 d . . . H6A H -0.175(2) -0.136(2) 0.1016(9) 0.039(5) Uiso 1 1 d . . . H6B H -0.073(3) -0.015(2) 0.1391(10) 0.041(5) Uiso 1 1 d . . . N7 N -0.28354(15) 0.00815(12) -0.00867(6) 0.0253(2) Uani 1 1 d . . . H7A H -0.304(3) 0.073(2) -0.0438(9) 0.040(5) Uiso 1 1 d . . . H7B H -0.315(3) -0.078(2) -0.0122(10) 0.041(5) Uiso 1 1 d . . . C8 C -0.18344(15) 0.05218(11) 0.04931(6) 0.0195(2) Uani 1 1 d . . . H1 H -0.0075 0.2182 0.0899 0.029 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 P 0.01927(17) 0.01444(15) 0.01665(15) 0.00005(8) -0.00024(9) -0.00106(8) O1 0.0226(4) 0.0147(3) 0.0223(4) 0.0016(3) 0.0007(3) -0.0012(3) O2 0.0201(4) 0.0319(4) 0.0208(4) -0.0014(3) 0.0003(3) 0.0017(3) O3 0.0359(5) 0.0173(4) 0.0204(4) -0.0032(3) 0.0027(3) -0.0064(3) O4 0.0257(4) 0.0219(4) 0.0244(4) 0.0065(3) -0.0051(3) -0.0033(3) O5 0.0288(4) 0.0163(4) 0.0307(4) 0.0020(3) -0.0092(3) -0.0007(3) N6 0.0369(6) 0.0221(5) 0.0264(5) 0.0064(4) -0.0100(4) -0.0071(4) N7 0.0305(5) 0.0229(5) 0.0223(5) 0.0009(4) -0.0065(4) -0.0039(4) C8 0.0191(5) 0.0193(5) 0.0200(5) 0.0003(4) 0.0005(4) 0.0003(4) H1 0.033 0.024 0.032 0.003 0.000 0.001 _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 P O1 1.5116(8) . ? P O4 1.5179(8) . ? P O3 1.5558(9) . ? P O2 1.5634(9) . ? O2 H2 0.79(2) . ? O3 H3 0.79(2) . ? O4 H1 1.2381 . ? O5 C8 1.2921(13) . ? O5 H1 1.1903 . ? N6 C8 1.3214(14) . ? N6 H6A 0.883(19) . ? N6 H6B 0.826(19) . ? N7 C8 1.3228(14) . ? N7 H7A 0.861(17) . ? N7 H7B 0.81(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 O1 P O4 113.75(5) . . ? O1 P O3 106.45(5) . . ? O4 P O3 111.22(5) . . ? O1 P O2 111.77(5) . . ? O4 P O2 105.17(5) . . ? O3 P O2 108.45(5) . . ? P O2 H2 109.4(16) . . ? P O3 H3 118.6(14) . . ? P O4 H1 125.0 . . ? C8 O5 H1 116.4 . . ? C8 N6 H6A 119.9(11) . . ? C8 N6 H6B 120.2(14) . . ? H6A N6 H6B 119.7(17) . . ? C8 N7 H7A 116.7(12) . . ? C8 N7 H7B 120.4(13) . . ? H7A N7 H7B 122.6(17) . . ? O5 C8 N6 121.20(11) . . ? O5 C8 N7 118.21(10) . . ? N6 C8 N7 120.59(10) . . ? 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 O5 H1 O4 1.19 1.24 2.4195(12) 170.2 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.358 _refine_diff_density_min -0.418 _refine_diff_density_rms 0.073 data_250k _database_code_depnum_ccdc_archive 'CCDC 231381' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1:1 co-crystal of urea:phosphoric acid' _chemical_melting_point ? _chemical_formula_moiety 'H2 O4 P, H, O C H4 N2' _chemical_formula_sum 'C H7 N2 O5 P' _chemical_formula_weight 158.06 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.4720(5) _cell_length_b 8.9926(6) _cell_length_c 17.5962(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1182.34(15) _cell_formula_units_Z 8 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 791 _cell_measurement_theta_min 10.36 _cell_measurement_theta_max 26.01 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.425 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(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 SMART-6000 CCD Diffractometer' _diffrn_measurement_method '\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 7881 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0135 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 30.51 _reflns_number_total 1801 _reflns_number_gt 1607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2000)' _computing_cell_refinement 'SMART V5.625 (Bruker, 2000)' _computing_data_reduction 'SAINT V6.02A (Bruker, 2000)' _computing_structure_solution 'known coordinates' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material Encifer _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. Hydrogen atoms were all placed on the difference map and allowed to freely refine except for H1, for which the neutron coordinates and Uij's were used and constrained, as explained in the manuscript. ; _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^)+(0.0504P)^2^+0.3491P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'known coordinates' _atom_sites_solution_secondary none _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1801 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 P P 0.22111(4) 0.19079(3) 0.189051(16) 0.02027(11) Uani 1 1 d . . . O1 O 0.11490(11) 0.06391(8) 0.22260(5) 0.02393(18) Uani 1 1 d . . . O2 O 0.40880(12) 0.13897(11) 0.16033(5) 0.0294(2) Uani 1 1 d . . . H2 H 0.465(3) 0.114(3) 0.1945(12) 0.066(7) Uiso 1 1 d . . . O3 O 0.24845(15) 0.30568(10) 0.25394(6) 0.0297(2) Uani 1 1 d . . . H3 H 0.289(3) 0.383(2) 0.2440(11) 0.047(5) Uiso 1 1 d . . . O4 O 0.13283(13) 0.26223(10) 0.12052(5) 0.0291(2) Uani 1 1 d . . . O5 O -0.13505(14) 0.19013(9) 0.05257(6) 0.0310(2) Uani 1 1 d . . . N6 N -0.13552(17) -0.04245(13) 0.10301(7) 0.0349(3) Uani 1 1 d . . . H6A H -0.176(2) -0.135(2) 0.1019(10) 0.047(5) Uiso 1 1 d . . . H6B H -0.075(3) -0.016(2) 0.1385(10) 0.044(5) Uiso 1 1 d . . . N7 N -0.28307(16) 0.00872(13) -0.00818(7) 0.0310(2) Uani 1 1 d . . . H7A H -0.306(3) 0.074(2) -0.0425(10) 0.047(5) Uiso 1 1 d . . . H7B H -0.315(3) -0.075(2) -0.0117(10) 0.043(5) Uiso 1 1 d . . . C8 C -0.18330(16) 0.05258(12) 0.04966(6) 0.0237(2) Uani 1 1 d . . . H1 H -0.0057 0.2186 0.0904 0.032 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 P 0.02335(18) 0.01741(15) 0.02005(16) 0.00000(9) -0.00035(9) -0.00136(9) O1 0.0270(4) 0.0178(4) 0.0270(4) 0.0019(3) 0.0011(3) -0.0014(3) O2 0.0241(4) 0.0387(5) 0.0254(4) -0.0016(4) 0.0006(3) 0.0022(4) O3 0.0436(5) 0.0210(4) 0.0246(4) -0.0037(3) 0.0033(4) -0.0078(3) O4 0.0312(5) 0.0264(4) 0.0298(4) 0.0081(3) -0.0068(3) -0.0040(3) O5 0.0354(5) 0.0201(4) 0.0375(5) 0.0025(3) -0.0115(4) -0.0011(3) N6 0.0455(7) 0.0273(5) 0.0320(6) 0.0076(4) -0.0122(5) -0.0089(5) N7 0.0372(6) 0.0283(5) 0.0275(5) 0.0005(4) -0.0080(4) -0.0056(4) C8 0.0234(5) 0.0236(5) 0.0242(5) 0.0004(4) 0.0003(4) 0.0003(4) H1 0.033 0.021 0.041 0.005 0.001 0.004 _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 P O1 1.5100(8) . ? P O4 1.5172(9) . ? P O3 1.5533(9) . ? P O2 1.5618(9) . ? O2 H2 0.77(2) . ? O3 H3 0.78(2) . ? O4 H1 1.2272 . ? O5 C8 1.2894(14) . ? O5 H1 1.2012 . ? N6 C8 1.3187(15) . ? N6 H6A 0.88(2) . ? N6 H6B 0.807(19) . ? N7 C8 1.3217(15) . ? N7 H7A 0.856(18) . ? N7 H7B 0.79(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 O1 P O4 113.71(5) . . ? O1 P O3 106.52(5) . . ? O4 P O3 111.09(5) . . ? O1 P O2 111.90(5) . . ? O4 P O2 105.04(5) . . ? O3 P O2 108.56(6) . . ? P O2 H2 108.9(17) . . ? P O3 H3 118.7(14) . . ? P O4 H1 125.1 . . ? C8 O5 H1 116.8 . . ? C8 N6 H6A 119.9(12) . . ? C8 N6 H6B 120.7(14) . . ? H6A N6 H6B 119.3(18) . . ? C8 N7 H7A 116.8(13) . . ? C8 N7 H7B 121.0(14) . . ? H7A N7 H7B 122.2(18) . . ? O5 C8 N6 121.17(11) . . ? O5 C8 N7 118.33(11) . . ? N6 C8 N7 120.49(11) . . ? 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 O5 H1 O4 1.20 1.23 2.4200(13) 170.5 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.278 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.085 data_300k _database_code_depnum_ccdc_archive 'CCDC 231382' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1:1 co-crystal of urea:phosphoric acid' _chemical_melting_point ? _chemical_formula_moiety 'H2 O4 P, H, O C H4 N2' _chemical_formula_sum 'C H7 N2 O5 P' _chemical_formula_weight 158.06 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.4858(4) _cell_length_b 9.0041(5) _cell_length_c 17.6597(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1190.31(11) _cell_formula_units_Z 8 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 918 _cell_measurement_theta_min 10.33 _cell_measurement_theta_max 25.97 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 SMART-6000 CCD Diffractometer' _diffrn_measurement_method '\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 7941 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0148 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 30.50 _reflns_number_total 1814 _reflns_number_gt 1579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2000)' _computing_cell_refinement 'SMART V5.625 (Bruker, 2000)' _computing_data_reduction 'SAINT V6.02A (Bruker, 2000)' _computing_structure_solution 'known coordinates' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material Encifer _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. Hydrogen atoms were all placed on the difference map and allowed to freely refine except for H1, for which the neutron coordinates and Uij's were used and constrained, as explained in the manuscript. ; _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^)+(0.0505P)^2^+0.2903P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'known coordinates' _atom_sites_solution_secondary none _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1814 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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 P P 0.22147(4) 0.19094(3) 0.189089(17) 0.02381(11) Uani 1 1 d . . . O1 O 0.11555(12) 0.06449(9) 0.22259(5) 0.0282(2) Uani 1 1 d . . . O2 O 0.40894(13) 0.13938(12) 0.16052(6) 0.0348(2) Uani 1 1 d . . . H2 H 0.463(3) 0.115(3) 0.1943(13) 0.072(7) Uiso 1 1 d . . . O3 O 0.24873(16) 0.30610(11) 0.25349(6) 0.0352(2) Uani 1 1 d . . . H3 H 0.289(3) 0.381(2) 0.2432(12) 0.053(6) Uiso 1 1 d . . . O4 O 0.13369(13) 0.26199(11) 0.12067(5) 0.0347(2) Uani 1 1 d . . . O5 O -0.13460(15) 0.18978(10) 0.05301(6) 0.0369(2) Uani 1 1 d . . . N6 N -0.13683(19) -0.04197(15) 0.10330(8) 0.0417(3) Uani 1 1 d . . . H6A H -0.176(2) -0.133(2) 0.1016(10) 0.047(5) Uiso 1 1 d . . . H6B H -0.077(3) -0.014(3) 0.1380(10) 0.054(6) Uiso 1 1 d . . . N7 N -0.28253(18) 0.00922(15) -0.00771(7) 0.0370(3) Uani 1 1 d . . . H7A H -0.307(3) 0.076(2) -0.0414(10) 0.049(5) Uiso 1 1 d . . . H7B H -0.315(3) -0.075(2) -0.0112(11) 0.050(5) Uiso 1 1 d . . . C8 C -0.18326(17) 0.05299(13) 0.05011(7) 0.0278(2) Uani 1 1 d . . . H1 H -0.0030 0.2189 0.0909 0.038 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 P 0.02751(19) 0.02009(16) 0.02383(17) 0.00012(9) -0.00029(10) -0.00171(10) O1 0.0317(4) 0.0203(4) 0.0325(4) 0.0022(3) 0.0013(3) -0.0017(3) O2 0.0283(5) 0.0460(6) 0.0300(5) -0.0016(4) 0.0010(4) 0.0024(4) O3 0.0519(6) 0.0243(4) 0.0293(5) -0.0046(4) 0.0040(4) -0.0092(4) O4 0.0375(5) 0.0312(5) 0.0356(5) 0.0098(4) -0.0084(4) -0.0049(4) O5 0.0418(6) 0.0243(5) 0.0446(6) 0.0033(4) -0.0144(4) -0.0011(4) N6 0.0549(8) 0.0326(6) 0.0378(6) 0.0092(5) -0.0142(6) -0.0114(5) N7 0.0441(7) 0.0342(6) 0.0326(6) 0.0005(5) -0.0101(5) -0.0061(5) C8 0.0276(6) 0.0273(6) 0.0286(5) 0.0002(4) 0.0003(4) -0.0001(4) H1 0.046 0.026 0.043 0.007 0.005 0.002 _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 P O1 1.5083(9) . ? P O4 1.5169(9) . ? P O3 1.5525(10) . ? P O2 1.5618(10) . ? O2 H2 0.75(2) . ? O3 H3 0.76(2) . ? O4 H1 1.2136 . ? O5 C8 1.2855(15) . ? O5 H1 1.2199 . ? N6 C8 1.3169(17) . ? N6 H6A 0.87(2) . ? N6 H6B 0.80(2) . ? N7 C8 1.3228(17) . ? N7 H7A 0.865(18) . ? N7 H7B 0.80(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 O1 P O4 113.77(5) . . ? O1 P O3 106.61(5) . . ? O4 P O3 111.02(6) . . ? O1 P O2 112.00(6) . . ? O4 P O2 104.91(6) . . ? O3 P O2 108.48(6) . . ? P O2 H2 108.3(18) . . ? P O3 H3 117.9(16) . . ? P O4 H1 125.1 . . ? C8 O5 H1 117.2 . . ? C8 N6 H6A 119.9(12) . . ? C8 N6 H6B 119.2(16) . . ? H6A N6 H6B 121(2) . . ? C8 N7 H7A 116.2(13) . . ? C8 N7 H7B 120.9(15) . . ? H7A N7 H7B 122.9(19) . . ? O5 C8 N6 121.26(12) . . ? O5 C8 N7 118.38(12) . . ? N6 C8 N7 120.36(13) . . ? 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 O5 H1 O4 1.22 1.22 2.4257(14) 170.8 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.287 _refine_diff_density_min -0.593 _refine_diff_density_rms 0.127 data_350k _database_code_depnum_ccdc_archive 'CCDC 231383' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '1:1 co-crystal of urea:phosphoric acid' _chemical_melting_point ? _chemical_formula_moiety 'H2 O4 P, H, O C H4 N2' _chemical_formula_sum 'C H7 N2 O5 P' _chemical_formula_weight 158.06 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.4904(6) _cell_length_b 9.0176(7) _cell_length_c 17.7254(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1197.27(17) _cell_formula_units_Z 8 _cell_measurement_temperature 350(2) _cell_measurement_reflns_used 925 _cell_measurement_theta_min 10.29 _cell_measurement_theta_max 25.94 _exptl_crystal_description 'irregular shape' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.419 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 350(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 SMART-6000 CCD Diffractometer' _diffrn_measurement_method '\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 7970 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 30.52 _reflns_number_total 1825 _reflns_number_gt 1548 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2000)' _computing_cell_refinement 'SMART V5.625 (Bruker, 2000)' _computing_data_reduction 'SAINT V6.02A (Bruker, 2000)' _computing_structure_solution 'known coordinates' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material Encifer _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. Hydrogen atoms were all placed on the difference map and allowed to freely refine except for H1, for which the neutron coordinates and Uij's were used and constrained, as explained in the manuscript. ; _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^)+(0.0598P)^2^+0.1712P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'known coordinates' _atom_sites_solution_secondary none _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1825 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0955 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 P P 0.22188(5) 0.19112(3) 0.189146(17) 0.02807(13) Uani 1 1 d . . . O1 O 0.11640(12) 0.06527(9) 0.22252(5) 0.0332(2) Uani 1 1 d . . . O2 O 0.40893(14) 0.13983(13) 0.16078(6) 0.0411(3) Uani 1 1 d . . . H2 H 0.462(3) 0.115(3) 0.1964(13) 0.083(8) Uiso 1 1 d . . . O3 O 0.24872(18) 0.30662(12) 0.25283(6) 0.0412(3) Uani 1 1 d . . . H3 H 0.289(3) 0.380(3) 0.2424(11) 0.052(6) Uiso 1 1 d . . . O4 O 0.13430(15) 0.26158(12) 0.12068(5) 0.0409(3) Uani 1 1 d . . . O5 O -0.13406(16) 0.18945(10) 0.05344(7) 0.0439(3) Uani 1 1 d . . . N6 N -0.1382(2) -0.04150(16) 0.10362(8) 0.0496(4) Uani 1 1 d . . . H6A H -0.184(3) -0.132(3) 0.1033(11) 0.065(6) Uiso 1 1 d . . . H6B H -0.077(3) -0.014(3) 0.1390(11) 0.062(6) Uiso 1 1 d . . . N7 N -0.28227(19) 0.00983(16) -0.00695(8) 0.0439(3) Uani 1 1 d . . . H7A H -0.302(3) 0.078(2) -0.0422(10) 0.061(6) Uiso 1 1 d . . . H7B H -0.315(3) -0.074(2) -0.0092(12) 0.062(6) Uiso 1 1 d . . . C8 C -0.18332(18) 0.05346(14) 0.05054(7) 0.0326(3) Uani 1 1 d . . . H1 H -0.0030 0.2188 0.0913 0.040 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 P 0.0324(2) 0.02341(18) 0.02842(19) 0.00018(10) -0.00051(11) -0.00192(10) O1 0.0371(5) 0.0241(4) 0.0385(5) 0.0027(3) 0.0018(4) -0.0019(3) O2 0.0335(5) 0.0534(6) 0.0364(5) -0.0019(5) 0.0016(4) 0.0026(5) O3 0.0604(7) 0.0283(5) 0.0350(5) -0.0051(4) 0.0045(4) -0.0108(4) O4 0.0444(6) 0.0364(5) 0.0420(5) 0.0114(4) -0.0102(4) -0.0060(4) O5 0.0491(7) 0.0290(5) 0.0536(6) 0.0045(4) -0.0175(5) -0.0020(4) N6 0.0650(9) 0.0386(7) 0.0453(7) 0.0116(6) -0.0168(7) -0.0134(6) N7 0.0512(8) 0.0414(7) 0.0392(7) 0.0007(5) -0.0117(5) -0.0075(6) C8 0.0316(6) 0.0328(6) 0.0336(6) 0.0005(5) -0.0003(5) 0.0000(5) H1 0.047 0.030 0.044 0.008 0.005 0.003 _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 P O1 1.5040(9) . ? P O4 1.5187(10) . ? P O3 1.5490(11) . ? P O2 1.5588(11) . ? O2 H2 0.78(2) . ? O3 H3 0.75(2) . ? O4 H1 1.2159 . ? O5 C8 1.2816(16) . ? O5 H1 1.2181 . ? N6 C8 1.3163(18) . ? N6 H6A 0.88(2) . ? N6 H6B 0.81(2) . ? N7 C8 1.3202(18) . ? N7 H7A 0.89(2) . ? N7 H7B 0.80(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 O1 P O4 113.77(6) . . ? O1 P O3 106.79(6) . . ? O4 P O3 110.92(6) . . ? O1 P O2 112.03(6) . . ? O4 P O2 104.75(6) . . ? O3 P O2 108.53(7) . . ? P O2 H2 106.6(18) . . ? P O3 H3 117.8(16) . . ? P O4 H1 125.1 . . ? C8 O5 H1 117.5 . . ? C8 N6 H6A 119.7(13) . . ? C8 N6 H6B 119.8(16) . . ? H6A N6 H6B 120(2) . . ? C8 N7 H7A 115.5(13) . . ? C8 N7 H7B 119.5(16) . . ? H7A N7 H7B 125(2) . . ? O5 C8 N6 121.33(13) . . ? O5 C8 N7 118.53(13) . . ? N6 C8 N7 120.13(14) . . ? 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 O5 H1 O4 1.22 1.22 2.4258(15) 170.6 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.283 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.146