data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name _publ_author_address 'Michaela Fridrichova' ; Department of Inorganic Chemistry Faculty of Science Charles University in Prague Hlavova 2030 12843 Prague 2 Czech Republic ; 'Ivana Cisarova' ;Department of Inorganic Chemistry Faculty of Science Charles University in Prague Hlavova 2030 12843 Prague 2 Czech Republic ; 'Petr Nemec' ; Department of Inorganic Chemistry Faculty of Science Charles University in Prague Hlavova 2030 12843 Prague 2 Czech Republic ; 'Ivan Nemec' ; Department of Chemical Physics and Optics Charles University in Prague Faculty of Mathematics and Physics Ke Karlovu 3 12116 Prague 2 ; _publ_contact_author_name 'Michaela Fridrichova' _publ_contact_author_email FANTOM.AG@SEZNAM.CZ _publ_section_title ; Guanylurea(1+) hydrogen phosphite: a novel promising phase-matchable material for second harmonic generation ; _publ_contact_author 'Fridrichova, M.' # Attachment 'guhp.cif' data_guhp _database_code_depnum_ccdc_archive 'CCDC 752254' #TrackingRef 'guhp.cif' _audit_update_record ; 2009-10-22 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'guanylurea hydrogen phosphite' _chemical_melting_point 452 _chemical_formula_moiety 'C2 H7 N4 O, H2 O3 P' _chemical_formula_sum 'C2 H9 N4 O4 P' _chemical_formula_weight 184.10 _chemical_compound_source 'synthesized by the authors' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' 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 6.6990(3) _cell_length_b 6.8420(2) _cell_length_c 16.3540(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.514(3) _cell_angle_gamma 90.00 _cell_volume 744.74(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 879 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_preparation 'from water' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.348 _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 293(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 'Nonius KappaCCD area detector' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4256 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 27.53 _reflns_number_total 1637 _reflns_number_gt 1562 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'COLLECT and DENZO' _computing_data_reduction 'COLLECT and DENZO' _computing_structure_solution 'SIR92 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0318P)^2^+0.2284P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(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 0.0(3) _refine_ls_number_reflns 1637 _refine_ls_number_parameters 138 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0660 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.090 _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 P1 P 0.38935(6) 0.30842(6) 0.02427(3) 0.02872(15) Uani 1 1 d . . . C1 C 0.6435(3) 0.5165(3) 0.29518(12) 0.0283(4) Uani 1 1 d . . . C2 C 0.9071(3) 0.4481(3) 0.20798(13) 0.0316(4) Uani 1 1 d . . . N1 N 0.4481(3) 0.5173(3) 0.29902(15) 0.0404(4) Uani 1 1 d . . . N2 N 0.7688(3) 0.5658(3) 0.35947(12) 0.0375(4) Uani 1 1 d . . . N3 N 0.7065(2) 0.4613(2) 0.22281(11) 0.0306(3) Uani 1 1 d . . . N4 N 0.9347(3) 0.3695(3) 0.13587(13) 0.0393(4) Uani 1 1 d . . . O1 O 1.0441(2) 0.5058(3) 0.25826(12) 0.0461(4) Uani 1 1 d . . . O2 O 0.3764(2) 0.3773(2) 0.10988(9) 0.0372(3) Uani 1 1 d . . . O3 O 0.5948(2) 0.2643(2) 0.00032(10) 0.0404(4) Uani 1 1 d . . . O4 O 0.2873(3) 0.4575(3) -0.04066(11) 0.0534(5) Uani 1 1 d . . . H1 H 0.269(4) 0.165(3) 0.0125(15) 0.031(6) Uiso 1 1 d . . . H1A H 0.371(4) 0.490(4) 0.2619(17) 0.033(7) Uiso 1 1 d . . . H1B H 0.390(5) 0.545(5) 0.352(2) 0.066(10) Uiso 1 1 d . . . H2A H 0.722(4) 0.616(4) 0.408(2) 0.043(7) Uiso 1 1 d . . . H2B H 0.881(4) 0.556(3) 0.3525(16) 0.027(6) Uiso 1 1 d . . . H3 H 0.601(4) 0.424(4) 0.183(2) 0.053(8) Uiso 1 1 d . . . H4A H 1.063(6) 0.365(5) 0.131(2) 0.069(10) Uiso 1 1 d . . . H4B H 0.850(5) 0.338(4) 0.103(2) 0.044(7) Uiso 1 1 d . . . H4 H 0.205(6) 0.547(5) -0.025(2) 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 P1 0.0279(2) 0.0329(2) 0.0257(2) -0.0015(2) 0.00462(15) 0.00472(19) C1 0.0260(9) 0.0328(9) 0.0265(10) 0.0042(7) 0.0046(7) 0.0010(7) C2 0.0259(9) 0.0343(9) 0.0348(11) 0.0012(7) 0.0048(8) 0.0022(7) N1 0.0243(9) 0.0580(12) 0.0395(11) -0.0010(8) 0.0064(9) -0.0037(7) N2 0.0285(9) 0.0570(11) 0.0270(9) -0.0050(8) 0.0035(7) -0.0003(8) N3 0.0230(8) 0.0427(8) 0.0256(9) -0.0027(6) 0.0012(6) -0.0014(6) N4 0.0324(10) 0.0521(11) 0.0341(11) -0.0071(8) 0.0064(8) 0.0027(8) O1 0.0240(7) 0.0707(11) 0.0433(10) -0.0129(7) 0.0030(7) -0.0025(7) O2 0.0335(7) 0.0509(8) 0.0274(7) -0.0071(6) 0.0042(6) 0.0043(6) O3 0.0351(8) 0.0436(8) 0.0444(9) 0.0042(6) 0.0133(7) 0.0136(6) O4 0.0688(12) 0.0604(10) 0.0327(9) 0.0062(7) 0.0125(8) 0.0391(9) _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 P1 O2 1.4891(15) . ? P1 O3 1.5038(14) . ? P1 O4 1.5716(17) . ? P1 H1 1.27(2) . ? C1 N2 1.313(3) . ? C1 N1 1.317(3) . ? C1 N3 1.355(3) . ? C2 O1 1.226(3) . ? C2 N4 1.328(3) . ? C2 N3 1.395(2) . ? N1 H1A 0.77(3) . ? N1 H1B 1.00(4) . ? N2 H2A 0.95(3) . ? N2 H2B 0.78(3) . ? N3 H3 0.95(3) . ? N4 H4A 0.87(4) . ? N4 H4B 0.77(4) . ? O4 H4 0.88(4) . ? 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 O2 P1 O3 117.46(9) . . ? O2 P1 O4 111.26(9) . . ? O3 P1 O4 107.17(10) . . ? O2 P1 H1 106.4(11) . . ? O3 P1 H1 113.1(10) . . ? O4 P1 H1 100.2(11) . . ? N2 C1 N1 120.6(2) . . ? N2 C1 N3 122.45(19) . . ? N1 C1 N3 116.92(19) . . ? O1 C2 N4 123.85(19) . . ? O1 C2 N3 121.67(19) . . ? N4 C2 N3 114.48(19) . . ? C1 N1 H1A 122.7(19) . . ? C1 N1 H1B 122(2) . . ? H1A N1 H1B 115(3) . . ? C1 N2 H2A 121.3(18) . . ? C1 N2 H2B 113.7(19) . . ? H2A N2 H2B 125(3) . . ? C1 N3 C2 124.88(17) . . ? C1 N3 H3 113.5(18) . . ? C2 N3 H3 121.5(18) . . ? C2 N4 H4A 109(2) . . ? C2 N4 H4B 125(2) . . ? H4A N4 H4B 126(3) . . ? P1 O4 H4 119(3) . . ? 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 O1 0.77(3) 2.19(3) 2.714(3) 126(2) 1_455 N1 H1A O2 0.77(3) 2.61(3) 3.222(3) 138(2) . N1 H1B O4 1.00(4) 1.96(4) 2.951(3) 169(3) 2_565 N2 H2A O3 0.95(3) 2.00(3) 2.937(3) 173(3) 2_565 N2 H2B O1 0.78(3) 2.02(3) 2.646(3) 138(3) . N3 H3 O2 0.95(3) 1.84(3) 2.776(2) 172(3) . N4 H4A O2 0.87(4) 2.17(4) 3.037(3) 174(4) 1_655 N4 H4B O3 0.77(4) 2.31(4) 3.078(3) 176(3) . O4 H4 O3 0.88(4) 1.73(4) 2.591(2) 165(3) 3_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.172 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.042 #===END