#------------------------------------------------------------------------------ #$Date: 2013-12-29 13:49:26 +0200 (Sun, 29 Dec 2013) $ #$Revision: 91935 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/31/67/4316771.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4316771 loop_ _publ_author_name 'Sylvie Pailloux' 'Cornel Edicome Shirima' 'Karen Ann Smith' 'Eileen N. Duesler' 'Robert T. Paine' 'Neil J. Williams' 'Robert D. Hancock' _publ_section_title ; Synthesis and Reactivity of (Benzoxazol-2-ylmethyl)phosphonic Acid ; _journal_name_full 'Inorganic Chemistry' _journal_page_first 9369 _journal_page_last 9379 _journal_volume 49 _journal_year 2010 _chemical_formula_moiety 'C8 H9 N O5 P, N H4' _chemical_formula_sum 'C8 H13 N2 O5 P' _chemical_formula_weight 248.17 _chemical_name_systematic ; ? ; _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 geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 97.563(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 19.8602(9) _cell_length_b 7.1524(3) _cell_length_c 8.1497(3) _cell_measurement_reflns_used 9938 _cell_measurement_temperature 228(2) _cell_measurement_theta_max 30.39 _cell_measurement_theta_min 3.03 _cell_volume 1147.58(8) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 228(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 26858 _diffrn_reflns_theta_full 30.46 _diffrn_reflns_theta_max 30.46 _diffrn_reflns_theta_min 3.10 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_T_max 0.9875 _exptl_absorpt_correction_T_min 0.8711 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details Bruker,SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.533 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 3477 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0340 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.3538P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0937 _refine_ls_wR_factor_ref 0.0997 _reflns_number_gt 2963 _reflns_number_total 3477 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ic101079b_si_003_2.cif _[local]_cod_data_source_block rpec33w _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to the built-in table from CIF Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana ; _cod_database_code 4316771 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_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 0.376904(15) 0.41851(4) 0.61135(3) 0.01981(9) Uani 1 1 d . . . O1 O 0.39070(5) 0.58896(12) 0.51508(11) 0.0289(2) Uani 1 1 d . . . O2 O 0.42442(5) 0.42895(14) 0.78264(12) 0.0299(2) Uani 1 1 d . . . H2O H 0.4133(11) 0.364(3) 0.853(3) 0.057(6) Uiso 1 1 d . . . O3 O 0.38560(5) 0.23376(12) 0.52839(11) 0.02796(19) Uani 1 1 d . . . O4 O 0.22849(5) 0.45456(12) 0.39996(11) 0.0288(2) Uani 1 1 d . . . O5 O 0.23128(5) -0.16994(13) 0.47390(12) 0.0327(2) Uani 1 1 d . . . H5O H 0.2324(9) -0.280(3) 0.435(2) 0.047(5) Uiso 1 1 d . . . N1 N 0.21206(5) 0.19214(14) 0.54665(13) 0.0236(2) Uani 1 1 d . . . H1N H 0.2229(9) 0.133(3) 0.640(2) 0.037(4) Uiso 1 1 d . . . C1 C 0.29188(6) 0.42272(16) 0.66968(14) 0.0224(2) Uani 1 1 d . . . H1A H 0.2899 0.3406 0.7652 0.027 Uiso 1 1 calc R . . H1B H 0.2808 0.5500 0.7018 0.027 Uiso 1 1 calc R . . C2 C 0.24060(6) 0.35879(15) 0.52772(14) 0.0209(2) Uani 1 1 d . . . C3 C 0.16446(6) 0.10172(16) 0.42635(15) 0.0231(2) Uani 1 1 d . . . C4 C 0.17533(6) -0.08696(16) 0.39175(16) 0.0255(2) Uani 1 1 d . . . C5 C 0.12967(7) -0.1789(2) 0.27386(18) 0.0350(3) Uani 1 1 d . . . H5 H 0.1363 -0.3057 0.2500 0.042 Uiso 1 1 calc R . . C6 C 0.07457(8) -0.0834(2) 0.1920(2) 0.0412(4) Uani 1 1 d . . . H6 H 0.0442 -0.1456 0.1120 0.049 Uiso 1 1 calc R . . C7 C 0.06378(7) 0.1027(2) 0.2269(2) 0.0399(3) Uani 1 1 d . . . H7 H 0.0262 0.1664 0.1710 0.048 Uiso 1 1 calc R . . C8 C 0.10862(7) 0.1950(2) 0.34454(17) 0.0316(3) Uani 1 1 d . . . H8 H 0.1011 0.3212 0.3690 0.038 Uiso 1 1 calc R . . N2 N 0.42622(6) 0.59330(15) 0.20023(14) 0.0275(2) Uani 1 1 d . . . H2N H 0.4121(9) 0.598(2) 0.305(3) 0.043(5) Uiso 1 1 d . . . H3N H 0.4758(10) 0.587(3) 0.209(2) 0.045(5) Uiso 1 1 d . . . H4N H 0.4117(10) 0.695(3) 0.131(2) 0.048(5) Uiso 1 1 d . . . H5N H 0.4096(10) 0.491(3) 0.143(2) 0.048(5) 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 0.02590(16) 0.01882(14) 0.01529(14) -0.00076(9) 0.00491(10) -0.00174(10) O1 0.0440(5) 0.0231(4) 0.0213(4) 0.0019(3) 0.0103(4) -0.0062(4) O2 0.0283(5) 0.0433(6) 0.0178(4) 0.0018(3) 0.0024(3) -0.0088(4) O3 0.0393(5) 0.0223(4) 0.0233(4) -0.0028(3) 0.0081(3) 0.0050(3) O4 0.0418(5) 0.0198(4) 0.0233(4) 0.0032(3) -0.0014(3) -0.0021(3) O5 0.0413(5) 0.0190(4) 0.0360(5) 0.0010(4) -0.0017(4) 0.0013(4) N1 0.0282(5) 0.0205(4) 0.0213(5) 0.0021(4) 0.0005(4) -0.0023(4) C1 0.0259(5) 0.0238(5) 0.0179(5) -0.0037(4) 0.0045(4) -0.0018(4) C2 0.0249(5) 0.0177(5) 0.0206(5) -0.0019(4) 0.0045(4) 0.0024(4) C3 0.0246(5) 0.0222(5) 0.0228(5) -0.0005(4) 0.0041(4) -0.0039(4) C4 0.0290(6) 0.0224(5) 0.0255(6) 0.0013(4) 0.0053(4) -0.0040(4) C5 0.0411(7) 0.0306(7) 0.0333(7) -0.0055(5) 0.0049(5) -0.0099(5) C6 0.0357(7) 0.0508(9) 0.0352(8) -0.0080(6) -0.0018(6) -0.0128(6) C7 0.0270(6) 0.0522(9) 0.0384(8) -0.0011(6) -0.0032(5) 0.0005(6) C8 0.0285(6) 0.0324(6) 0.0334(7) -0.0007(5) 0.0025(5) 0.0027(5) N2 0.0373(6) 0.0226(5) 0.0233(5) 0.0005(4) 0.0067(4) -0.0007(4) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O3 116.15(5) . . ? O1 P1 O2 107.20(5) . . ? O3 P1 O2 110.36(5) . . ? O1 P1 C1 111.43(6) . . ? O3 P1 C1 107.35(5) . . ? O2 P1 C1 103.65(5) . . ? P1 O2 H2O 114.9(16) . . ? C4 O5 H5O 106.2(13) . . ? C2 N1 C3 125.32(10) . . ? C2 N1 H1N 118.1(12) . . ? C3 N1 H1N 116.6(12) . . ? C2 C1 P1 110.60(8) . . ? C2 C1 H1A 109.5 . . ? P1 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 108.1 . . ? O4 C2 N1 123.33(11) . . ? O4 C2 C1 120.81(10) . . ? N1 C2 C1 115.81(10) . . ? C8 C3 C4 120.06(12) . . ? C8 C3 N1 121.90(11) . . ? C4 C3 N1 118.04(11) . . ? O5 C4 C5 123.32(12) . . ? O5 C4 C3 117.38(11) . . ? C5 C4 C3 119.29(12) . . ? C6 C5 C4 119.96(13) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 120.66(13) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C8 119.81(14) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? C7 C8 C3 120.22(13) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? H2N N2 H3N 110.7(16) . . ? H2N N2 H4N 114.5(16) . . ? H3N N2 H4N 108.0(16) . . ? H2N N2 H5N 111.4(17) . . ? H3N N2 H5N 107.1(16) . . ? H4N N2 H5N 104.7(18) . . ? 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 O1 1.4944(9) . ? P1 O3 1.5046(9) . ? P1 O2 1.5805(10) . ? P1 C1 1.8137(12) . ? O2 H2O 0.79(2) . ? O4 C2 1.2430(14) . ? O5 C4 1.3564(16) . ? O5 H5O 0.85(2) . ? N1 C2 1.3375(15) . ? N1 C3 1.4244(15) . ? N1 H1N 0.871(18) . ? C1 C2 1.5082(16) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C3 C8 1.3875(17) . ? C3 C4 1.4011(17) . ? C4 C5 1.3959(18) . ? C5 C6 1.385(2) . ? C5 H5 0.9400 . ? C6 C7 1.383(2) . ? C6 H6 0.9400 . ? C7 C8 1.387(2) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? N2 H2N 0.93(2) . ? N2 H3N 0.98(2) . ? N2 H4N 0.94(2) . ? N2 H5N 0.90(2) . ? 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 H1N O4 0.871(18) 2.199(18) 3.0415(14) 162.7(16) 4_566 N2 H2N O1 0.93(2) 1.82(2) 2.7494(15) 174.4(17) . O2 H2O O3 0.79(2) 1.74(2) 2.5231(13) 168(2) 4_566 N2 H3N O2 0.98(2) 1.98(2) 2.9555(16) 177.6(17) 3_666 N2 H4N O1 0.94(2) 1.83(2) 2.7675(14) 172.8(18) 4_575 N2 H5N O3 0.90(2) 1.89(2) 2.7905(14) 173.1(19) 4_565 O5 H5O O4 0.85(2) 1.92(2) 2.7515(13) 165.4(19) 1_545 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 C1 C2 81.28(9) . . . . ? O3 P1 C1 C2 -46.93(9) . . . . ? O2 P1 C1 C2 -163.74(8) . . . . ? C3 N1 C2 O4 -0.20(18) . . . . ? C3 N1 C2 C1 -177.53(10) . . . . ? P1 C1 C2 O4 -67.60(13) . . . . ? P1 C1 C2 N1 109.81(10) . . . . ? C2 N1 C3 C8 -47.79(18) . . . . ? C2 N1 C3 C4 132.29(12) . . . . ? C8 C3 C4 O5 179.10(11) . . . . ? N1 C3 C4 O5 -0.98(17) . . . . ? C8 C3 C4 C5 0.37(18) . . . . ? N1 C3 C4 C5 -179.71(11) . . . . ? O5 C4 C5 C6 -178.35(13) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C4 C5 C6 C7 -0.6(2) . . . . ? C5 C6 C7 C8 0.2(2) . . . . ? C6 C7 C8 C3 0.5(2) . . . . ? C4 C3 C8 C7 -0.8(2) . . . . ? N1 C3 C8 C7 179.31(12) . . . . ? _journal_paper_doi 10.1021/ic101079b