#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/38/2013851.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_2013851 loop_ _publ_author_name 'Carvalho, Carlos E. M.' 'Wardell, Solange M. S. V.' 'Wardell, James L.' 'Skakle, Janet M. S.,' 'Low, John N.' 'Glidewell, Christopher' _publ_section_title ; Three N^2^-benzoyloxybenzamidines: sheet structures built from hard and soft hydrogen bonds and aromatic \p--\p stacking interactions ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o28 _journal_page_last o32 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H12 N2 O3' _chemical_formula_moiety 'C14 H12 N2 O3' _chemical_formula_sum 'C14 H12 N2 O3' _chemical_formula_weight 256.26 _chemical_name_systematic ; N^2^-Benzoyloxy-2-hydroxybenzamidine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 99.202(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.6463(3) _cell_length_b 22.1280(13) _cell_length_c 11.9551(9) _cell_measurement_reflns_used 2549 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.52 _cell_measurement_theta_min 3.26 _cell_volume 1213.33(14) _computing_cell_refinement 'DENZO--SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO--SMN _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.917 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans, and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8910 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 3.26 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO--SMN; Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.319 _refine_diff_density_min -0.221 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2549 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.981 _refine_ls_R_factor_all 0.1248 _refine_ls_R_factor_gt 0.0556 _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^)+(0.0626P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1089 _refine_ls_wR_factor_ref 0.1331 _reflns_number_gt 1412 _reflns_number_total 2549 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1677.cif _[local]_cod_data_source_block III _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2013851 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.3688(3) 0.18366(6) 0.20049(11) 0.0294(4) Uani d . 1 . . O O5 0.2346(3) 0.15005(7) 0.02115(12) 0.0383(4) Uani d . 1 . . O O121 0.7525(3) 0.28621(7) 0.00167(11) 0.0359(4) Uani d . 1 . . O N2 0.5570(4) 0.22553(8) 0.15460(14) 0.0289(5) Uani d . 1 . . N N4 0.6513(4) 0.25484(8) 0.34554(14) 0.0301(5) Uani d . 1 . . N C3 0.6859(4) 0.25965(9) 0.23640(17) 0.0240(5) Uani d . 1 . . C C5 0.2209(4) 0.14696(9) 0.12101(18) 0.0268(5) Uani d . 1 . . C C11 0.8891(4) 0.30561(9) 0.20344(16) 0.0241(5) Uani d . 1 . . C C12 0.9117(4) 0.31623(9) 0.09000(17) 0.0252(5) Uani d . 1 . . C C13 1.1034(5) 0.35978(10) 0.06161(17) 0.0314(6) Uani d . 1 . . C C14 1.2743(4) 0.39237(9) 0.14485(18) 0.0302(5) Uani d . 1 . . C C15 1.2559(5) 0.38254(9) 0.25700(18) 0.0305(5) Uani d . 1 . . C C16 1.0651(4) 0.33982(10) 0.28583(16) 0.0289(5) Uani d . 1 . . C C21 0.0454(4) 0.10209(9) 0.17318(17) 0.0270(5) Uani d . 1 . . C C22 0.0324(5) 0.10087(10) 0.28767(18) 0.0315(6) Uani d . 1 . . C C23 -0.1280(5) 0.05619(10) 0.33122(18) 0.0356(6) Uani d . 1 . . C C24 -0.2764(5) 0.01349(10) 0.2605(2) 0.0344(6) Uani d . 1 . . C C25 -0.2657(5) 0.01489(10) 0.1465(2) 0.0397(6) Uani d . 1 . . C C26 -0.1052(5) 0.05889(10) 0.10217(17) 0.0358(6) Uani d . 1 . . C H121 0.6558 0.2587 0.0267 0.054 Uiso calc R 1 . . H H41 0.5067 0.2317 0.3590 0.045 Uiso d R 1 . . H H42 0.7089 0.2848 0.3922 0.045 Uiso d R 1 . . H H13 1.1162 0.3670 -0.0158 0.038 Uiso calc . 1 . . H H14 1.4057 0.4218 0.1248 0.036 Uiso calc . 1 . . H H15 1.3744 0.4051 0.3144 0.037 Uiso calc . 1 . . H H16 1.0528 0.3334 0.3635 0.035 Uiso calc . 1 . . H H22 0.1330 0.1305 0.3366 0.038 Uiso calc . 1 . . H H23 -0.1353 0.0551 0.4101 0.043 Uiso calc . 1 . . H H24 -0.3862 -0.0169 0.2907 0.041 Uiso calc . 1 . . H H25 -0.3689 -0.0145 0.0978 0.048 Uiso calc . 1 . . H H26 -0.0978 0.0596 0.0232 0.043 Uiso calc . 1 . . H 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 O1 0.0340(9) 0.0321(9) 0.0235(8) -0.0059(7) 0.0090(7) 0.0010(7) O5 0.0509(10) 0.0413(11) 0.0231(9) -0.0070(8) 0.0071(7) 0.0016(7) O121 0.0408(9) 0.0445(11) 0.0235(9) -0.0131(8) 0.0087(7) -0.0048(7) N2 0.0319(11) 0.0298(11) 0.0271(11) -0.0067(8) 0.0114(9) 0.0013(8) N4 0.0347(10) 0.0327(11) 0.0237(11) -0.0038(8) 0.0072(8) 0.0001(8) C3 0.0241(12) 0.0258(13) 0.0228(12) 0.0087(9) 0.0058(10) 0.0014(9) C5 0.0280(12) 0.0285(13) 0.0234(12) 0.0044(10) 0.0027(9) 0.0021(10) C11 0.0236(11) 0.0265(12) 0.0231(12) 0.0057(9) 0.0062(9) 0.0003(9) C12 0.0250(12) 0.0287(13) 0.0224(12) 0.0025(9) 0.0051(9) -0.0028(10) C13 0.0369(13) 0.0361(14) 0.0228(12) -0.0016(11) 0.0101(10) 0.0027(10) C14 0.0308(13) 0.0285(13) 0.0330(14) -0.0015(10) 0.0105(10) 0.0014(10) C15 0.0316(12) 0.0308(14) 0.0283(13) 0.0003(10) 0.0023(10) -0.0047(10) C16 0.0338(13) 0.0326(13) 0.0207(11) 0.0046(10) 0.0056(10) 0.0014(10) C21 0.0267(12) 0.0261(13) 0.0279(13) 0.0045(10) 0.0038(10) 0.0021(10) C22 0.0382(13) 0.0271(13) 0.0306(13) 0.0003(10) 0.0100(10) -0.0010(10) C23 0.0450(14) 0.0328(14) 0.0324(13) 0.0042(11) 0.0164(11) 0.0040(11) C24 0.0321(13) 0.0286(14) 0.0442(15) -0.0003(10) 0.0110(11) 0.0062(11) C25 0.0408(14) 0.0344(15) 0.0408(16) -0.0078(11) -0.0035(12) 0.0009(12) C26 0.0420(14) 0.0385(15) 0.0258(13) -0.0031(11) 0.0019(11) 0.0035(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C5 . 1.351(2) no O1 N2 . 1.442(2) no O5 C5 . 1.208(2) no O121 C12 . 1.361(2) no O121 H121 . 0.84 no N2 C3 . 1.303(2) no N4 C3 . 1.344(2) no N4 H41 . 0.88 no N4 H42 . 0.88 no C3 C11 . 1.483(3) no C5 C21 . 1.484(3) no C11 C12 . 1.397(3) no C11 C16 . 1.398(3) no C12 C13 . 1.391(3) no C13 C14 . 1.374(3) no C13 H13 . 0.95 no C14 C15 . 1.374(3) no C14 H14 . 0.95 no C15 C16 . 1.377(3) no C15 H15 . 0.95 no C16 H16 . 0.95 no C21 C22 . 1.380(3) no C21 C26 . 1.391(3) no C22 C23 . 1.388(3) no C22 H22 . 0.95 no C23 C24 . 1.377(3) no C23 H23 . 0.95 no C24 C25 . 1.373(3) no C24 H24 . 0.95 no C25 C26 . 1.382(3) no C25 H25 . 0.95 no C26 H26 . 0.95 no 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' 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 C5 O1 N2 112.95(15) no C12 O121 H121 109.5 no C3 N2 O1 108.71(16) no C3 N4 H41 115.9 no C3 N4 H42 119.0 no H41 N4 H42 119.1 no N2 C3 N4 124.81(19) no N2 C3 C11 115.69(18) no N4 C3 C11 119.48(18) no O5 C5 O1 124.06(19) no O5 C5 C21 124.93(19) no O1 C5 C21 111.00(18) no C12 C11 C16 117.83(19) no C12 C11 C3 121.54(18) no C16 C11 C3 120.63(19) no O121 C12 C13 116.01(18) no O121 C12 C11 123.73(19) no C13 C12 C11 120.26(19) no C14 C13 C12 120.36(19) no C14 C13 H13 119.8 no C12 C13 H13 119.8 no C13 C14 C15 120.3(2) no C13 C14 H14 119.8 no C15 C14 H14 119.8 no C14 C15 C16 119.72(19) no C14 C15 H15 120.1 no C16 C15 H15 120.1 no C15 C16 C11 121.52(19) no C15 C16 H16 119.2 no C11 C16 H16 119.2 no C22 C21 C26 119.6(2) no C22 C21 C5 122.96(19) no C26 C21 C5 117.39(19) no C21 C22 C23 119.8(2) no C21 C22 H22 120.1 no C23 C22 H22 120.1 no C24 C23 C22 120.3(2) no C24 C23 H23 119.8 no C22 C23 H23 119.8 no C25 C24 C23 120.0(2) no C25 C24 H24 120.0 no C23 C24 H24 120.0 no C24 C25 C26 120.3(2) no C24 C25 H25 119.9 no C26 C25 H25 119.9 no C25 C26 C21 120.0(2) no C25 C26 H26 120.0 no C21 C26 H26 120.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _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 N4 H41 O121 4_566 0.88 2.26 2.975(2) 138 y N4 H42 O5 4_666 0.88 2.10 2.954(2) 163 y O121 H121 N2 . 0.84 1.82 2.550(2) 144 y 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 C5 O1 N2 C3 178.82(16) no O1 N2 C3 N4 1.5(3) no O1 N2 C3 C11 179.97(15) no N2 O1 C5 O5 -2.7(3) no N2 O1 C5 C21 176.26(14) no N2 C3 C11 C12 7.6(3) no N4 C3 C11 C12 -173.83(17) no N2 C3 C11 C16 -172.38(18) no N4 C3 C11 C16 6.2(3) no C16 C11 C12 O121 -179.81(18) no C3 C11 C12 O121 0.2(3) no C16 C11 C12 C13 -0.3(3) no C3 C11 C12 C13 179.74(19) no O121 C12 C13 C14 -179.80(19) no C11 C12 C13 C14 0.6(3) no C12 C13 C14 C15 -0.5(3) no C13 C14 C15 C16 0.0(3) no C14 C15 C16 C11 0.4(3) no C12 C11 C16 C15 -0.2(3) no C3 C11 C16 C15 179.77(18) no O5 C5 C21 C22 -178.9(2) no O1 C5 C21 C22 2.1(3) no O5 C5 C21 C26 2.7(3) no O1 C5 C21 C26 -176.26(17) no C26 C21 C22 C23 0.7(3) no C5 C21 C22 C23 -177.65(19) no C21 C22 C23 C24 -0.6(3) no C22 C23 C24 C25 0.1(3) no C23 C24 C25 C26 0.3(3) no C24 C25 C26 C21 -0.2(3) no C22 C21 C26 C25 -0.3(3) no C5 C21 C26 C25 178.17(19) no _cod_database_fobs_code 2013851 _journal_paper_doi 10.1107/S0108270103025435