#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013379.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013379 loop_ _publ_author_name 'Brauer, David J.' 'Kottsieper, Konstantin W.' _publ_section_title ; Hydrogen bonding in 1-carbamoylguanidinium methylphosphonate monohydrate ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o244 _journal_page_last o246 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C2 H7 N4 O 1+, C H4 O3 P 1-, H2 O' _chemical_formula_moiety 'C2 H7 N4 O 1+, C H4 O3 P 1-, H2 O' _chemical_formula_sum 'C3 H13 N4 O5 P' _chemical_formula_weight 216.14 _chemical_name_systematic ; 1-Carbamoylguanidinium methylphosphonate hydrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 111.440(16) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.9081(18) _cell_length_b 6.4458(7) _cell_length_c 13.996(3) _cell_measurement_reflns_used 50 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 14.44 _cell_measurement_theta_min 10.82 _cell_volume 1000.0(3) _computing_cell_refinement P3/PC _computing_data_collection 'P3/PC (Siemens, 1993)' _computing_data_reduction 'XDISK Version 4.20.2 (Siemens, 1991)' _computing_molecular_graphics 'XP, Version 5.03. (Siemens, 1994)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS93 (Sheldrick, 1993)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 1.00 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measurement_device_type 'Siemens P3' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0537 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2400 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.99 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_T_max 0.9264 _exptl_absorpt_correction_T_min 0.8830 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details 'North, Phillips & Mathews, 1968' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.284 _refine_diff_density_min -0.226 _refine_ls_extinction_coef 0.0119(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.832 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 171 _refine_ls_number_reflns 2293 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.832 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0369 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0403P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0791 _refine_ls_wR_factor_ref 0.0851 _reflns_number_gt 1467 _reflns_number_total 2293 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file tr1047.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 999.9(3) _cod_database_code 2013379 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_type_symbol P 0.59655(5) 0.17680(9) 0.69649(4) 0.03592(17) Uani d 1 P O2 0.59588(15) -0.0661(3) 0.68696(14) 0.0517(4) Uani d 1 O H6 0.546(2) -0.127(5) 0.698(2) 0.075(10) Uiso d 1 H O3 0.71415(13) 0.2495(2) 0.69094(12) 0.0486(4) Uani d 1 O O4 0.57926(13) 0.2387(2) 0.79384(11) 0.0472(4) Uani d 1 O C3 0.4724(3) 0.2675(6) 0.5896(2) 0.0618(7) Uani d 1 C H5A 0.481(2) 0.226(4) 0.530(2) 0.077(9) Uiso d 1 H H5B 0.402(3) 0.214(5) 0.599(2) 0.096(11) Uiso d 1 H H5C 0.472(3) 0.412(5) 0.588(2) 0.092(11) Uiso d 1 H O5 0.76682(17) -0.3379(4) 0.66069(17) 0.0680(6) Uani d 1 O H7A 0.719(3) -0.262(5) 0.681(3) 0.120(14) Uiso d 1 H H7B 0.745(3) -0.453(5) 0.672(2) 0.096(13) Uiso d 1 H O1 0.95809(14) 0.2744(2) 1.08370(10) 0.0472(4) Uani d 1 O N1 0.75668(18) 0.2823(4) 0.99593(17) 0.0558(6) Uani d 1 N H1A 0.700(2) 0.263(4) 0.936(2) 0.063(8) Uiso d 1 H H1B 0.7411(19) 0.285(3) 1.0504(18) 0.047(7) Uiso d 1 H N2 0.88367(17) 0.2597(3) 0.90780(13) 0.0416(4) Uani d 1 N H2 0.821(2) 0.262(3) 0.8512(19) 0.057(7) Uiso d 1 H N3 0.9825(2) 0.2220(3) 0.79735(16) 0.0522(5) Uani d 1 N H3A 0.914(2) 0.225(4) 0.7536(19) 0.056(8) Uiso d 1 H H3B 1.049(2) 0.209(4) 0.7864(18) 0.059(8) Uiso d 1 H N4 1.09290(17) 0.2272(3) 0.96957(16) 0.0456(5) Uani d 1 N H4A 1.159(3) 0.211(4) 0.951(2) 0.083(9) Uiso d 1 H H4B 1.0917(19) 0.243(3) 1.0289(17) 0.038(6) Uiso d 1 H C1 0.8706(2) 0.2729(3) 1.00319(16) 0.0402(5) Uani d 1 C C2 0.98832(19) 0.2359(3) 0.89232(15) 0.0374(5) Uani d 1 C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P 0.0320(3) 0.0408(3) 0.0385(3) 0.0003(3) 0.0171(2) -0.0008(3) O2 0.0547(10) 0.0416(9) 0.0764(12) -0.0050(8) 0.0449(9) -0.0063(9) O3 0.0390(8) 0.0522(10) 0.0604(10) -0.0048(7) 0.0251(7) 0.0039(7) O4 0.0479(9) 0.0570(10) 0.0396(8) 0.0105(7) 0.0193(7) -0.0013(7) C3 0.0539(16) 0.078(2) 0.0441(15) 0.0078(15) 0.0065(12) -0.0025(14) O5 0.0593(12) 0.0540(12) 0.1066(16) 0.0042(11) 0.0493(12) 0.0061(13) O1 0.0463(9) 0.0625(11) 0.0301(8) -0.0001(7) 0.0108(7) -0.0031(7) N1 0.0443(12) 0.0867(18) 0.0393(12) 0.0000(11) 0.0187(10) -0.0021(11) N2 0.0391(10) 0.0552(12) 0.0276(9) -0.0008(9) 0.0087(8) 0.0002(8) N3 0.0591(14) 0.0642(15) 0.0390(11) 0.0047(12) 0.0246(11) 0.0024(10) N4 0.0409(11) 0.0542(13) 0.0430(11) 0.0001(9) 0.0168(9) -0.0015(9) C1 0.0474(12) 0.0392(13) 0.0351(11) 0.0000(10) 0.0162(10) 0.0012(9) C2 0.0465(12) 0.0319(11) 0.0360(11) -0.0002(9) 0.0178(10) 0.0009(9) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O2 P O3 106.36(9) yes O2 P O4 110.07(9) yes O3 P O4 113.70(10) yes O2 P C3 106.26(15) yes O3 P C3 110.98(14) yes O4 P C3 109.18(12) yes P O2 H6 118(2) no P C3 H5A 109.5(17) no P C3 H5B 105.8(19) no H5A C3 H5B 114(3) no P C3 H5C 110.0(18) no H5A C3 H5C 106(2) no H5B C3 H5C 111(2) no H7A O5 H7B 99(3) no C1 N1 H1A 118.2(16) no C1 N1 H1B 119.1(15) no H1A N1 H1B 122(2) no C2 N2 C1 126.19(18) yes C2 N2 H2 112.8(16) no C1 N2 H2 121.0(16) no C2 N3 H3A 114.8(17) no C2 N3 H3B 118.4(17) no H3A N3 H3B 127(2) no C2 N4 H4A 114.8(17) no C2 N4 H4B 116.9(15) no H4A N4 H4B 128(2) no O1 C1 N1 125.0(2) yes O1 C1 N2 121.6(2) yes N1 C1 N2 113.4(2) yes N2 C2 N3 117.5(2) yes N2 C2 N4 121.60(19) yes N3 C2 N4 120.9(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag P O2 1.5714(17) yes P O3 1.5055(14) yes P O4 1.5042(15) yes P C3 1.774(3) yes O2 H6 0.78(3) no C3 H5A 0.92(3) no C3 H5B 0.96(3) no C3 H5C 0.93(3) no O5 H7A 0.88(4) no O5 H7B 0.82(3) no O1 C1 1.224(2) no N1 C1 1.324(3) no N1 H1A 0.87(3) no N1 H1B 0.85(2) no N2 C1 1.402(3) no N2 C2 1.349(3) no N2 H2 0.86(2) no N3 C2 1.309(3) no N3 H3A 0.83(2) no N3 H3B 0.87(3) no N4 C2 1.319(3) no N4 H4A 0.92(3) no N4 H4B 0.84(2) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O2 H6 O4 . . 2_646 0.78(3) 1.76(3) 2.533(2) 172(3) yes O5 H7A O2 . . . 0.88(4) 1.96(4) 2.810(3) 164(3) yes O5 H7B O3 . . 1_545 0.82(3) 1.99(3) 2.800(3) 170(3) yes N1 H1A O4 . . . 0.87(3) 1.99(3) 2.859(3) 175(2) yes N1 H1B O3 4_565 4_565 . 0.85(2) 2.12(2) 2.959(3) 172(2) yes N2 H2 O3 . . . 0.86(2) 2.14(3) 2.969(3) 161(2) yes N3 H3A O3 . . . 0.83(2) 2.22(3) 2.997(3) 158(2) yes N3 H3B O5 . . 2_756 0.87(3) 2.06(3) 2.850(3) 151(2) yes N4 H4A O5 . . 2_756 0.92(3) 2.08(3) 2.918(3) 151(2) yes N4 H4B O1 . . . 0.84(2) 2.01(2) 2.664(3) 134(2) yes N3 H3A O1 . . 4_565 0.83(2) 2.62(2) 2.897(2) 101(2) yes N3 H3B O1 . . 4_565 0.87(3) 2.64(2) 2.897(2) 98(2) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C2 N2 C1 O1 3.9(3) no C2 N2 C1 N1 -175.8(2) no C1 N2 C2 N3 178.5(2) no C1 N2 C2 N4 -1.6(3) no