#------------------------------------------------------------------------------ #$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201982 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/31/67/4316770.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_4316770 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_paper_doi 10.1021/ic101079b _journal_volume 49 _journal_year 2010 _chemical_absolute_configuration ad _chemical_formula_moiety 'C8 H8 N O4 P' _chemical_formula_sum 'C8 H8 N O4 P' _chemical_formula_weight 213.12 _chemical_name_systematic ; ? ; _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 19.883(2) _cell_length_b 5.6194(6) _cell_length_c 7.8141(10) _cell_measurement_reflns_used 9965 _cell_measurement_temperature 228(2) _cell_measurement_theta_max 63.69 _cell_measurement_theta_min 5.21 _cell_volume 873.07(17) _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, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 228(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'CCD area detector' _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 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0134 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 21435 _diffrn_reflns_theta_full 31.85 _diffrn_reflns_theta_max 31.85 _diffrn_reflns_theta_min 3.32 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details Bruker,SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.282 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.132 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 2969 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.132 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0243 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0633P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.0679 _reflns_number_gt 2916 _reflns_number_total 2969 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ic101079b_si_003_1.cif _cod_data_source_block rpec24a _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_original_cell_volume 873.07(18) _cod_database_code 4316770 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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 0.543793(11) 0.58007(4) 0.81172(4) 0.02221(6) Uani 1 1 d . . . O1 O 0.49055(5) 0.42154(15) 0.88229(12) 0.0367(2) Uani 1 1 d . . . O2 O 0.60392(4) 0.44584(14) 0.73447(12) 0.02956(16) Uani 1 1 d . . . H2 H 0.6135(12) 0.319(4) 0.764(3) 0.069(7) Uiso 1 1 d . . . O3 O 0.51810(5) 0.75119(14) 0.67258(12) 0.03367(18) Uani 1 1 d . . . H3 H 0.5092 0.6748 0.5845 0.051 Uiso 1 1 calc R . . O4 O 0.69686(4) 0.74442(13) 0.98774(12) 0.02749(15) Uani 1 1 d . . . N1 N 0.65690(4) 1.06908(14) 0.85982(12) 0.02425(16) Uani 1 1 d . . . C1 C 0.57556(5) 0.7739(2) 0.97954(15) 0.02803(19) Uani 1 1 d . . . H1A H 0.5442(9) 0.913(3) 0.991(3) 0.038(5) Uiso 1 1 d . . . H1B H 0.5783(10) 0.688(3) 1.087(3) 0.041(4) Uiso 1 1 d . . . C2 C 0.64254(5) 0.87362(18) 0.93940(13) 0.02411(17) Uani 1 1 d . . . C3 C 0.75177(5) 0.87527(17) 0.93222(14) 0.02420(17) Uani 1 1 d . . . C4 C 0.81927(5) 0.8251(2) 0.95106(16) 0.0313(2) Uani 1 1 d . . . H4 H 0.8347 0.6859 1.0050 0.038 Uiso 1 1 calc R . . C5 C 0.86279(6) 0.9953(2) 0.88439(17) 0.0347(2) Uani 1 1 d . . . H5 H 0.9094 0.9717 0.8944 0.042 Uiso 1 1 calc R . . C6 C 0.83914(5) 1.2012(2) 0.80260(19) 0.0343(2) Uani 1 1 d . . . H6 H 0.8703 1.3113 0.7589 0.041 Uiso 1 1 calc R . . C7 C 0.77068(5) 1.24656(19) 0.78455(15) 0.0298(2) Uani 1 1 d . . . H7 H 0.7547 1.3840 0.7294 0.036 Uiso 1 1 calc R . . C8 C 0.72729(5) 1.07756(16) 0.85255(13) 0.02299(18) 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 P1 0.02032(10) 0.02301(10) 0.02330(11) 0.00044(9) 0.00139(9) 0.00110(7) O1 0.0345(4) 0.0445(5) 0.0311(4) -0.0042(3) 0.0064(3) -0.0162(3) O2 0.0301(4) 0.0264(3) 0.0322(4) 0.0045(3) 0.0064(3) 0.0088(3) O3 0.0372(4) 0.0305(4) 0.0333(4) 0.0022(3) -0.0063(3) 0.0117(3) O4 0.0259(3) 0.0249(3) 0.0316(4) 0.0058(3) -0.0039(3) 0.0014(3) N1 0.0220(3) 0.0226(3) 0.0282(4) 0.0003(3) -0.0033(3) 0.0027(3) C1 0.0254(4) 0.0315(5) 0.0273(5) -0.0043(4) 0.0025(4) -0.0023(3) C2 0.0237(4) 0.0241(4) 0.0246(4) -0.0012(3) -0.0023(3) 0.0020(3) C3 0.0251(4) 0.0227(3) 0.0248(4) 0.0005(3) -0.0041(3) 0.0021(3) C4 0.0267(4) 0.0324(5) 0.0347(5) 0.0000(4) -0.0082(4) 0.0058(4) C5 0.0232(4) 0.0399(5) 0.0411(6) -0.0061(5) -0.0048(4) 0.0021(4) C6 0.0272(4) 0.0333(5) 0.0424(6) -0.0021(5) 0.0021(5) -0.0052(4) C7 0.0299(4) 0.0249(4) 0.0348(6) 0.0026(3) 0.0003(4) 0.0002(3) C8 0.0230(4) 0.0217(4) 0.0243(4) -0.0010(3) -0.0027(3) 0.0027(3) 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 O2 113.87(5) . . ? O1 P1 O3 113.54(6) . . ? O2 P1 O3 106.70(5) . . ? O1 P1 C1 109.77(5) . . ? O2 P1 C1 107.88(5) . . ? O3 P1 C1 104.52(5) . . ? P1 O2 H2 121.8(18) . . ? P1 O3 H3 109.5 . . ? C2 O4 C3 104.86(8) . . ? C2 N1 C8 105.59(8) . . ? C2 C1 P1 112.77(8) . . ? C2 C1 H1A 106.4(10) . . ? P1 C1 H1A 108.2(13) . . ? C2 C1 H1B 108.7(12) . . ? P1 C1 H1B 110.2(11) . . ? H1A C1 H1B 110.4(17) . . ? N1 C2 O4 114.38(9) . . ? N1 C2 C1 128.50(9) . . ? O4 C2 C1 117.11(9) . . ? C4 C3 C8 123.92(10) . . ? C4 C3 O4 128.65(9) . . ? C8 C3 O4 107.42(8) . . ? C3 C4 C5 115.12(10) . . ? C3 C4 H4 122.4 . . ? C5 C4 H4 122.4 . . ? C4 C5 C6 121.96(10) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C7 C6 C5 121.66(10) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C6 116.32(10) . . ? C8 C7 H7 121.8 . . ? C6 C7 H7 121.8 . . ? C3 C8 C7 121.01(9) . . ? C3 C8 N1 107.76(8) . . ? C7 C8 N1 131.23(9) . . ? 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 1.4894(9) . ? P1 O2 1.5371(8) . ? P1 O3 1.5387(9) . ? P1 C1 1.8178(11) . ? O2 H2 0.77(2) . ? O3 H3 0.8300 . ? O4 C2 1.3551(12) . ? O4 C3 1.3860(13) . ? N1 C2 1.2942(13) . ? N1 C8 1.4015(13) . ? C1 C2 1.4786(14) . ? C1 H1A 1.004(17) . ? C1 H1B 0.97(2) . ? C3 C4 1.3793(14) . ? C3 C8 1.3845(13) . ? C4 C5 1.3911(18) . ? C4 H4 0.9400 . ? C5 C6 1.4029(18) . ? C5 H5 0.9400 . ? C6 C7 1.3921(15) . ? C6 H6 0.9400 . ? C7 C8 1.3886(14) . ? C7 H7 0.9400 . ? 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 O2 H2 N1 0.77(2) 1.81(2) 2.5596(11) 163(3) 1_545 O3 H3 O1 0.83 1.67 2.4733(14) 162.1 2_664 C4 H4 O2 0.94 2.55 3.4318(14) 155.6 4_655 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 159.85(8) . . . . ? O2 P1 C1 C2 35.25(9) . . . . ? O3 P1 C1 C2 -78.05(9) . . . . ? C8 N1 C2 O4 -0.24(12) . . . . ? C8 N1 C2 C1 -178.74(10) . . . . ? C3 O4 C2 N1 0.23(12) . . . . ? C3 O4 C2 C1 178.90(9) . . . . ? P1 C1 C2 N1 89.80(12) . . . . ? P1 C1 C2 O4 -88.66(10) . . . . ? C2 O4 C3 C4 178.97(11) . . . . ? C2 O4 C3 C8 -0.11(11) . . . . ? C8 C3 C4 C5 0.42(17) . . . . ? O4 C3 C4 C5 -178.52(11) . . . . ? C3 C4 C5 C6 -0.64(18) . . . . ? C4 C5 C6 C7 0.3(2) . . . . ? C5 C6 C7 C8 0.28(18) . . . . ? C4 C3 C8 C7 0.16(17) . . . . ? O4 C3 C8 C7 179.29(10) . . . . ? C4 C3 C8 N1 -179.16(11) . . . . ? O4 C3 C8 N1 -0.03(11) . . . . ? C6 C7 C8 C3 -0.51(16) . . . . ? C6 C7 C8 N1 178.63(11) . . . . ? C2 N1 C8 C3 0.16(11) . . . . ? C2 N1 C8 C7 -179.06(11) . . . . ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 15320964