# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Videnova-Adrabinska, Veneta' 'Zon, Jerzy' 'Janczak, Jan' 'Wilk, Magdalena' 'Gancarz, Roman' 'Samoc, Marek' _publ_contact_author_name 'Videnova-Adrabinska, Veneta' _publ_contact_author_email veneta@pwr.wroc.pl _publ_section_title ; Design, synthesis and noncentrosymmetric solid state organization of three novel pyridylphosphonic acids ; # Attachment '- Compound 1.cif' data_Compound_1 _database_code_depnum_ccdc_archive 'CCDC 810542' #TrackingRef '- Compound 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '249-253 C' _chemical_formula_moiety 'C5 H6 N O3 P' _chemical_formula_sum 'C5 H6 N O3 P' _chemical_formula_weight 159.08 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 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 7.5460(15) _cell_length_b 10.948(2) _cell_length_c 7.8040(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 644.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 837 _cell_measurement_theta_min 3.21 _cell_measurement_theta_max 29.30 _exptl_crystal_description paralellepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas 1.63 _exptl_crystal_density_diffrn 1.639 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.365 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9181 _exptl_absorpt_correction_T_max 0.9302 _exptl_absorpt_process_details ; Oxford Diffration Poland (2006). CrysAlis Red, Version 171.31.6; Wroc\/law, Poland ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with bocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8140 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0165 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 29.30 _reflns_number_total 1643 _reflns_number_gt 1466 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffration Poland (2006). CrysAlis CCD, Version 171.31.6; Wroc\/law, Poland ; _computing_cell_refinement ; Oxford Diffration Poland (2006). CrysAlis Red, Version 171.31.6; Wroc\/law, Poland ; _computing_data_reduction ; Oxford Diffration Poland (2006). CrysAlis Red, Version 171.31.6; Wroc\/law, Poland ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0380P)^2^+0.0168P] 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 0.046(3) _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 0.12(7) _refine_ls_number_reflns 1643 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0531 _refine_ls_wR_factor_gt 0.0516 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 P3 P 0.79695(4) 0.65655(3) 0.90434(5) 0.02723(10) Uani 1 1 d . . . O31 O 0.84746(14) 0.77375(10) 0.98978(12) 0.0379(2) Uani 1 1 d . . . O32 O 0.93398(11) 0.55706(8) 0.89653(17) 0.0377(2) Uani 1 1 d . . . O33 O 0.62638(13) 0.60001(8) 0.98580(12) 0.0341(2) Uani 1 1 d . . . H33 H 0.516(2) 0.6508(15) 0.974(2) 0.051 Uiso 1 1 d . . . N1 N 0.64260(16) 0.83729(11) 0.47854(14) 0.0324(3) Uani 1 1 d . . . H1 H 0.618(2) 0.9304(13) 0.458(2) 0.039 Uiso 1 1 d . . . C2 C 0.69821(17) 0.81071(13) 0.63692(16) 0.0293(3) Uani 1 1 d . . . H2 H 0.7153 0.8735 0.7155 0.035 Uiso 1 1 calc R . . C3 C 0.73055(17) 0.69191(12) 0.68549(16) 0.0269(2) Uani 1 1 d . . . C4 C 0.70423(19) 0.59990(13) 0.56434(18) 0.0362(3) Uani 1 1 d . . . H4 H 0.7258 0.5188 0.5929 0.043 Uiso 1 1 calc R . . C5 C 0.6463(2) 0.62976(13) 0.4025(3) 0.0441(3) Uani 1 1 d . . . H5 H 0.6267 0.5689 0.3215 0.053 Uiso 1 1 calc R . . C6 C 0.6176(2) 0.75050(14) 0.36130(16) 0.0393(3) Uani 1 1 d . . . H6 H 0.5808 0.7715 0.2515 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P3 0.03004(16) 0.02705(15) 0.02460(14) 0.00427(15) -0.00082(17) -0.00138(11) O31 0.0419(5) 0.0380(6) 0.0339(5) -0.0021(4) -0.0066(4) -0.0049(4) O32 0.0350(5) 0.0349(4) 0.0434(5) 0.0047(5) 0.0059(5) 0.0023(3) O33 0.0345(5) 0.0353(5) 0.0325(5) 0.0079(4) 0.0048(4) -0.0028(4) N1 0.0358(6) 0.0321(6) 0.0293(5) 0.0074(5) 0.0002(5) -0.0006(5) C2 0.0332(7) 0.0287(6) 0.0258(6) 0.0005(5) 0.0028(5) -0.0029(5) C3 0.0279(6) 0.0282(6) 0.0246(5) 0.0038(5) 0.0021(5) -0.0014(5) C4 0.0470(9) 0.0268(7) 0.0349(7) 0.0002(6) -0.0006(6) -0.0009(6) C5 0.0644(9) 0.0371(7) 0.0309(6) -0.0043(8) -0.0017(11) -0.0054(6) C6 0.0439(7) 0.0467(9) 0.0273(7) 0.0035(5) -0.0029(5) 0.0002(7) _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 P3 O31 1.4954(11) . ? P3 O32 1.5031(9) . ? P3 O33 1.5633(10) . ? P3 C3 1.8215(14) . ? O33 H33 1.003(18) . ? N1 C6 1.3325(18) . ? N1 C2 1.3373(18) . ? N1 H1 1.049(14) . ? C2 C3 1.3765(19) . ? C2 H2 0.9300 . ? C3 C4 1.3957(19) . ? C4 C5 1.376(3) . ? C4 H4 0.9300 . ? C5 C6 1.377(2) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 O31 P3 O32 117.68(6) . . ? O31 P3 O33 111.61(6) . . ? O32 P3 O33 107.22(6) . . ? O31 P3 C3 107.81(6) . . ? O32 P3 C3 107.77(7) . . ? O33 P3 C3 103.83(6) . . ? P3 O33 H33 115.1(10) . . ? C6 N1 C2 121.59(12) . . ? C6 N1 H1 124.2(9) . . ? C2 N1 H1 114.1(9) . . ? N1 C2 C3 121.05(13) . . ? N1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C2 C3 C4 118.04(13) . . ? C2 C3 P3 120.52(10) . . ? C4 C3 P3 121.39(11) . . ? C5 C4 C3 119.71(13) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 119.46(15) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? N1 C6 C5 120.13(14) . . ? N1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? 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 O33 H33 O31 1.003(18) 1.525(19) 2.5181(15) 170.0(16) 3_465 N1 H1 O32 1.049(14) 1.518(14) 2.5559(15) 169.1(15) 4_654 _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 28.80 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.162 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.034 # Attachment '- Compound 2.cif' data_Compound_2 _database_code_depnum_ccdc_archive 'CCDC 810543' #TrackingRef '- Compound 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-(dihydroxyphosphoryl)nicotinic acid ; _chemical_name_common ? _chemical_melting_point '305-310 C' _chemical_formula_moiety 'C6 H6 N O5 P' _chemical_formula_sum 'C6 H6 N O5 P' _chemical_formula_weight 203.09 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 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 19.948(3) _cell_length_b 28.534(4) _cell_length_c 5.3040(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3019.0(8) _cell_formula_units_Z 16 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 724 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 29.36 _exptl_crystal_description paralellepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 1.79 _exptl_crystal_density_diffrn 1.787 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1664 _exptl_absorpt_coefficient_mu 0.352 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9210 _exptl_absorpt_correction_T_max 0.9491 _exptl_absorpt_process_details ; Oxford Diffraction Poland (2006). CrysAlis Red, Version 171.32.6, Wroc\/law, Poland ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9629 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 29.31 _reflns_number_total 1680 _reflns_number_gt 1525 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Oxford Diffraction Poland (2006). CrysAlis CCD, Version 171.32.6, Wroc\/law, Poland ; _computing_cell_refinement ; Oxford Diffraction Poland (2006). CrysAlis CCD, Version 171.32.6, Wroc\/law, Poland ; _computing_data_reduction ; Oxford Diffraction Poland (2006). CrysAlis CCD, Version 171.32.6, Wroc\/law, Poland ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0367P)^2^+0.9858P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(8) _refine_ls_number_reflns 1680 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0576 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 P5 P 0.09215(2) 0.269555(14) -0.13655(9) 0.01866(10) Uani 1 1 d . . . O51 O 0.03172(6) 0.27898(4) 0.0222(3) 0.0274(3) Uani 1 1 d . . . O52 O 0.14885(6) 0.30445(4) -0.1044(3) 0.0238(3) Uani 1 1 d . . . O53 O 0.07687(7) 0.26504(5) -0.4251(3) 0.0286(3) Uani 1 1 d . . . H53 H 0.0354(16) 0.2585(11) -0.460(7) 0.073(10) Uiso 1 1 d . . . N1 N 0.13570(7) 0.13160(5) -0.1153(3) 0.0264(3) Uani 1 1 d . . . H1 H 0.1203(12) 0.1025(9) -0.202(5) 0.053(8) Uiso 1 1 d . . . C2 C 0.17804(9) 0.12647(6) 0.0782(4) 0.0273(4) Uani 1 1 d . . . H2 H 0.1945 0.0969 0.1185 0.033 Uiso 1 1 calc R . . C3 C 0.19742(9) 0.16522(6) 0.2189(4) 0.0236(4) Uani 1 1 d . . . C4 C 0.17104(8) 0.20853(6) 0.1546(4) 0.0228(4) Uani 1 1 d . . . H4 H 0.1830 0.2349 0.2473 0.027 Uiso 1 1 calc R . . C5 C 0.12670(8) 0.21303(5) -0.0479(4) 0.0213(4) Uani 1 1 d . . . C6 C 0.10952(9) 0.17311(6) -0.1812(4) 0.0244(4) Uani 1 1 d . . . H6 H 0.0799 0.1751 -0.3162 0.029 Uiso 1 1 calc R . . C31 C 0.24640(9) 0.15861(6) 0.4330(4) 0.0256(4) Uani 1 1 d . . . O31 O 0.26844(8) 0.12102(5) 0.4901(3) 0.0427(4) Uani 1 1 d . . . O32 O 0.26067(8) 0.19793(5) 0.5459(3) 0.0419(4) Uani 1 1 d . . . H32 H 0.2920(13) 0.1958(10) 0.659(6) 0.067(9) Uiso 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 P5 0.02057(17) 0.01568(18) 0.0197(2) -0.00085(18) 0.00110(18) -0.00162(16) O51 0.0275(6) 0.0245(6) 0.0302(8) -0.0018(5) 0.0062(5) 0.0002(5) O52 0.0238(5) 0.0187(5) 0.0288(8) -0.0057(6) 0.0049(5) -0.0040(4) O53 0.0319(6) 0.0325(7) 0.0213(7) -0.0013(6) -0.0019(6) -0.0043(6) N1 0.0287(7) 0.0174(6) 0.0330(9) -0.0078(7) 0.0020(7) -0.0023(6) C2 0.0300(9) 0.0180(8) 0.0339(11) -0.0015(7) 0.0046(8) 0.0007(6) C3 0.0231(8) 0.0204(8) 0.0274(10) -0.0014(8) 0.0018(7) -0.0001(7) C4 0.0261(8) 0.0165(7) 0.0259(11) -0.0033(7) 0.0011(7) -0.0016(6) C5 0.0234(8) 0.0154(7) 0.0250(9) -0.0017(7) 0.0038(7) -0.0011(6) C6 0.0258(8) 0.0216(8) 0.0259(11) -0.0035(7) -0.0022(7) -0.0019(6) C31 0.0234(8) 0.0242(9) 0.0290(11) 0.0028(7) 0.0022(7) -0.0008(7) O31 0.0496(9) 0.0262(7) 0.0523(11) 0.0047(7) -0.0113(8) 0.0066(6) O32 0.0481(9) 0.0261(7) 0.0516(11) -0.0023(7) -0.0282(8) 0.0016(6) _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 P5 O51 1.4949(13) . ? P5 O52 1.5164(11) . ? P5 O53 1.5660(15) . ? P5 C5 1.8158(17) . ? O53 H53 0.87(3) . ? N1 C2 1.337(3) . ? N1 C6 1.341(2) . ? N1 H1 1.00(2) . ? C2 C3 1.389(3) . ? C2 H2 0.9300 . ? C3 C4 1.386(2) . ? C3 C31 1.510(3) . ? C4 C5 1.397(3) . ? C4 H4 0.9300 . ? C5 C6 1.384(2) . ? C6 H6 0.9300 . ? C31 O31 1.198(2) . ? C31 O32 1.303(2) . ? O32 H32 0.87(3) . ? 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 O51 P5 O52 114.83(7) . . ? O51 P5 O53 114.12(8) . . ? O52 P5 O53 108.00(7) . . ? O51 P5 C5 108.67(8) . . ? O52 P5 C5 105.72(7) . . ? O53 P5 C5 104.70(8) . . ? P5 O53 H53 114(2) . . ? C2 N1 C6 122.87(16) . . ? C2 N1 H1 117.0(15) . . ? C6 N1 H1 119.8(15) . . ? N1 C2 C3 120.07(17) . . ? N1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 118.16(18) . . ? C4 C3 C31 122.83(16) . . ? C2 C3 C31 119.00(16) . . ? C3 C4 C5 120.77(16) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 118.27(15) . . ? C6 C5 P5 120.33(14) . . ? C4 C5 P5 121.40(12) . . ? N1 C6 C5 119.85(17) . . ? N1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? O31 C31 O32 125.05(19) . . ? O31 C31 C3 122.65(17) . . ? O32 C31 C3 112.29(15) . . ? C31 O32 H32 114.6(19) . . ? 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 O53 H53 O51 0.87(3) 1.72(3) 2.5195(18) 153(3) 6_554 N1 H1 O52 1.00(2) 1.64(3) 2.6325(18) 175(2) 8_544 O32 H32 O52 0.87(3) 1.72(3) 2.589(2) 175(3) 14_556 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.248 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.045 # Attachment '- Compound 3.cif' data_Compound_3 _database_code_depnum_ccdc_archive 'CCDC 810544' #TrackingRef '- Compound 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '285-292 C' _chemical_formula_moiety 'C5 H7 N O6 P2' _chemical_formula_sum 'C5 H7 N O6 P2' _chemical_formula_weight 239.06 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 'P 21 21 21' _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' _cell_length_a 7.0495(14) _cell_length_b 10.490(2) _cell_length_c 10.813(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 799.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 872 _cell_measurement_theta_min 3.45 _cell_measurement_theta_max 29.44 _exptl_crystal_description paralellepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 1.98 _exptl_crystal_density_diffrn 1.986 _exptl_crystal_density_method floatation _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.548 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8821 _exptl_absorpt_correction_T_max 0.9215 _exptl_absorpt_process_details ; Oxford Diffraction Poland (2006). CrysAlis Red, Version 171.32.6, Wroc\/law, Poland ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'KUMA KM-4 with area CCD detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10503 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 29.44 _reflns_number_total 2077 _reflns_number_gt 1814 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction Poland (2006). CrysAlis CCD, Version 171.32.6, Wroc\/law, Poland ; _computing_cell_refinement ; Oxford Diffraction Poland (2006). CrysAlis CCD, Version 171.32.6, Wroc\/law, Poland ; _computing_data_reduction ; Oxford Diffraction Poland (2006). CrysAlis CCD, Version 171.32.6, Wroc\/law, Poland ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0372P)^2^] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(8) _refine_ls_number_reflns 2077 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0220 _refine_ls_wR_factor_ref 0.0548 _refine_ls_wR_factor_gt 0.0548 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 P3 P 0.52268(6) 0.26935(4) 0.20500(4) 0.01659(10) Uani 1 1 d D . . O31 O 0.48924(16) 0.24369(11) 0.33857(10) 0.0235(3) Uani 1 1 d . . . O32 O 0.72807(16) 0.28243(13) 0.16376(11) 0.0231(3) Uani 1 1 d . . . H32 H 0.8529(8) 0.2655(19) 0.2372(18) 0.035 Uiso 1 1 d D . . O33 O 0.41644(18) 0.38843(12) 0.15945(11) 0.0262(3) Uani 1 1 d . . . H33 H 0.311(2) 0.4222(15) 0.197(2) 0.039 Uiso 1 1 d D . . P5 P -0.03498(6) -0.10088(4) 0.12659(4) 0.01623(10) Uani 1 1 d D . . O51 O -0.14070(16) -0.02030(12) 0.21696(12) 0.0234(3) Uani 1 1 d . . . O52 O 0.02647(17) -0.23133(11) 0.17364(11) 0.0224(3) Uani 1 1 d . . . O53 O -0.15183(17) -0.11738(12) 0.00671(11) 0.0208(3) Uani 1 1 d . . . H53 H -0.093(3) -0.1630(18) -0.0632(8) 0.031 Uiso 1 1 d D . . N1 N 0.4597(2) -0.01945(14) -0.03499(14) 0.0222(3) Uani 1 1 d . . . H1 H 0.540(3) -0.0517(18) -0.0893(18) 0.027 Uiso 1 1 d . . . C2 C 0.5314(3) 0.08160(16) 0.02481(15) 0.0219(4) Uani 1 1 d . . . H2 H 0.6505 0.1130 0.0040 0.026 Uiso 1 1 calc R . . C3 C 0.4273(2) 0.13837(16) 0.11704(16) 0.0166(3) Uani 1 1 d . . . C4 C 0.2484(2) 0.08740(16) 0.14516(15) 0.0184(3) Uani 1 1 d . . . H4 H 0.1741 0.1258 0.2057 0.022 Uiso 1 1 calc R . . C5 C 0.1810(2) -0.01934(15) 0.08397(16) 0.0168(4) Uani 1 1 d . . . C6 C 0.2922(3) -0.07095(17) -0.00805(16) 0.0213(4) Uani 1 1 d . . . H6 H 0.2501 -0.1420 -0.0515 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P3 0.0170(2) 0.0176(2) 0.01516(18) 0.00041(16) -0.00074(17) -0.00226(17) O31 0.0237(7) 0.0294(7) 0.0173(5) 0.0015(5) -0.0007(5) -0.0021(5) O32 0.0161(6) 0.0313(7) 0.0221(6) 0.0006(5) 0.0006(5) -0.0056(5) O33 0.0302(7) 0.0219(6) 0.0266(7) 0.0052(6) 0.0030(5) 0.0068(5) P5 0.01329(19) 0.0178(2) 0.01761(19) -0.00045(16) -0.00009(17) -0.00224(17) O51 0.0195(6) 0.0246(6) 0.0259(6) -0.0060(6) 0.0064(5) -0.0020(5) O52 0.0201(6) 0.0192(6) 0.0278(6) 0.0040(5) -0.0055(5) -0.0036(5) O53 0.0170(6) 0.0254(7) 0.0200(6) 0.0000(5) -0.0039(5) -0.0001(5) N1 0.0168(7) 0.0280(8) 0.0219(7) -0.0085(6) 0.0059(7) 0.0007(6) C2 0.0161(8) 0.0265(9) 0.0232(8) -0.0002(7) 0.0025(7) -0.0031(7) C3 0.0137(8) 0.0179(8) 0.0181(8) 0.0013(7) -0.0006(7) -0.0004(6) C4 0.0161(8) 0.0201(9) 0.0189(8) -0.0034(7) 0.0022(7) 0.0002(6) C5 0.0148(8) 0.0178(8) 0.0178(8) 0.0024(7) -0.0020(6) -0.0010(6) C6 0.0182(8) 0.0228(9) 0.0229(9) -0.0043(7) -0.0022(8) -0.0004(7) _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 P3 O31 1.4880(12) . ? P3 O32 1.5212(12) . ? P3 O33 1.5375(13) . ? P3 C3 1.8012(17) . ? O32 H32 1.199(12) . ? O33 H33 0.921(14) . ? P5 O51 1.4916(13) . ? P5 O52 1.5228(12) . ? P5 O53 1.5457(13) . ? P5 C5 1.8060(17) . ? O53 H53 0.987(14) . ? N1 C6 1.331(2) . ? N1 C2 1.341(2) . ? N1 H1 0.88(2) . ? C2 C3 1.374(2) . ? C2 H2 0.9300 . ? C3 C4 1.403(2) . ? C4 C5 1.385(2) . ? C4 H4 0.9300 . ? C5 C6 1.378(2) . ? C6 H6 0.9300 . ? 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 O31 P3 O32 116.85(7) . . ? O31 P3 O33 112.38(7) . . ? O32 P3 O33 107.24(7) . . ? O31 P3 C3 108.39(7) . . ? O32 P3 C3 105.62(7) . . ? O33 P3 C3 105.59(8) . . ? P3 O32 H32 119.4(8) . . ? P3 O33 H33 124.3(12) . . ? O51 P5 O52 115.63(7) . . ? O51 P5 O53 110.28(7) . . ? O52 P5 O53 109.34(7) . . ? O51 P5 C5 108.66(8) . . ? O52 P5 C5 105.73(7) . . ? O53 P5 C5 106.75(7) . . ? P5 O53 H53 118.1(10) . . ? C6 N1 C2 123.36(16) . . ? C6 N1 H1 124.1(13) . . ? C2 N1 H1 112.4(13) . . ? N1 C2 C3 119.46(17) . . ? N1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 118.16(16) . . ? C2 C3 P3 120.98(13) . . ? C4 C3 P3 120.78(13) . . ? C5 C4 C3 120.87(15) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C6 C5 C4 117.87(16) . . ? C6 C5 P5 118.56(13) . . ? C4 C5 P5 123.39(13) . . ? N1 C6 C5 120.24(16) . . ? N1 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? 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 O32 H32 O52 1.199(12) 1.286(13) 2.471(2) 168(2) 3_655 O33 H33 O51 0.921(14) 1.631(16) 2.546(2) 172(2) 3 O53 H53 O31 0.987(14) 1.541(16) 2.525(2) 174(2) 2_554 N1 H1 O51 0.88(2) 2.337(19) 2.999(2) 132(2) 2_554 N1 H1 O52 0.88(2) 2.45(2) 3.050(2) 125(2) 4_545 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.235 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.051