#------------------------------------------------------------------------------ #$Date: 2012-02-25 20:48:15 +0200 (Sat, 25 Feb 2012) $ #$Revision: 34491 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/50/04/4500429.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_4500429 loop_ _publ_author_name 'Hathwar, Venkatesha R.' 'Thakur, Tejender S.' 'Row, Tayur N. Guru' 'Desiraju, Gautam R.' _publ_section_title ; Transferability of Multipole Charge Density Parameters for Supramolecular Synthons: A New Tool for Quantitative Crystal Engineering ; _journal_issue 2 _journal_name_full 'Crystal Growth & Design' _journal_page_first 616 _journal_volume 11 _journal_year 2011 _chemical_compound_source 'see text' _chemical_formula_moiety 'C9 H9 N O3' _chemical_formula_sum 'C9 H9 N O3' _chemical_formula_weight 179.17 _chemical_name_common '4-(acetylamino)-benzoic acid' _chemical_name_systematic ; ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 89.254(7) _cell_angle_beta 80.804(7) _cell_angle_gamma 79.282(5) _cell_formula_units_Z 2 _cell_length_a 5.0255(13) _cell_length_b 6.8219(13) _cell_length_c 12.196(3) _cell_measurement_reflns_used 4989 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.0 _cell_volume 405.49(16) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009) ; _computing_publication_material 'PLATON (Spek, 2003)' _diffrn_ambient_temperature 100 _diffrn_detector CCD _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; scan: Number of images: 190 Slice: -70.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 190 Slice: -70.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 49.4000 2theta: 29.6000 scan: Number of images: 190 Slice: -70.0000 - 120.0000 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 49.4000 2theta: 29.6000 ; _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Fiber _diffrn_orient_matrix_type FS_PROCESS _diffrn_orient_matrix_UB_11 0.086339 _diffrn_orient_matrix_UB_12 0.001783 _diffrn_orient_matrix_UB_13 0.067100 _diffrn_orient_matrix_UB_21 0.097446 _diffrn_orient_matrix_UB_22 0.084863 _diffrn_orient_matrix_UB_23 -0.025082 _diffrn_orient_matrix_UB_31 -0.044623 _diffrn_orient_matrix_UB_32 0.077671 _diffrn_orient_matrix_UB_33 0.042068 _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_unetI/netI 0.039 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9042 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 3.0 _diffrn_source 'Sealed Tube' _diffrn_source_current 12.0 _diffrn_source_power 0.6 _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_correction_T_min 0.9463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description Platelet _exptl_crystal_F_000 188 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.356 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1850 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0407 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+0.0701P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1120 _refine_ls_wR_factor_ref 0.1177 _reflns_number_gt 1538 _reflns_number_total 1850 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file cg101540y_si_002.cif _[local]_cod_data_source_block datam _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_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 4500429 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z 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 O1 0.0222(5) 0.0139(5) 0.0209(5) -0.0028(4) -0.0070(4) 0.0002(4) O2 0.0211(5) 0.0176(5) 0.0255(6) -0.0069(4) -0.0095(4) -0.0022(4) O3 0.0156(5) 0.0203(5) 0.0220(5) -0.0036(4) -0.0039(4) -0.0029(4) N1 0.0152(6) 0.0142(6) 0.0180(6) -0.0040(4) -0.0041(5) -0.0040(5) C1 0.0164(7) 0.0130(7) 0.0133(6) -0.0008(5) -0.0014(5) -0.0040(5) C2 0.0158(7) 0.0175(7) 0.0144(6) -0.0013(5) -0.0045(5) -0.0032(5) C3 0.0160(7) 0.0138(7) 0.0176(7) -0.0018(5) -0.0037(5) -0.0010(5) C4 0.0154(7) 0.0137(6) 0.0144(6) -0.0025(5) 0.0001(5) -0.0043(5) C5 0.0171(7) 0.0173(7) 0.0167(7) -0.0017(5) -0.0058(5) -0.0039(5) C6 0.0171(7) 0.0148(7) 0.0184(7) -0.0004(5) -0.0048(5) -0.0015(5) C7 0.0165(7) 0.0151(7) 0.0139(7) 0.0003(5) -0.0024(5) -0.0051(5) C8 0.0184(7) 0.0137(6) 0.0131(6) 0.0013(5) -0.0031(5) -0.0030(5) C9 0.0231(8) 0.0148(7) 0.0209(7) -0.0046(6) -0.0027(6) -0.0039(6) loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv O1 O Uani 0.6508(2) -0.39766(14) 0.09189(8) 1.000 0.0190(3) O2 O Uani 0.2638(2) -0.27172(16) 0.02601(9) 1.000 0.0209(3) O3 O Uani -0.1350(2) 0.54525(15) 0.36840(8) 1.000 0.0192(3) N1 N Uani 0.3307(3) 0.46316(17) 0.32932(10) 1.000 0.0154(3) C1 C Uani 0.4178(3) -0.0702(2) 0.14845(11) 1.000 0.0142(4) C2 C Uani 0.2085(3) 0.0885(2) 0.13415(12) 1.000 0.0156(4) C3 C Uani 0.1758(3) 0.2666(2) 0.19328(12) 1.000 0.0159(4) C4 C Uani 0.3528(3) 0.2839(2) 0.26812(11) 1.000 0.0146(4) C5 C Uani 0.5638(3) 0.1260(2) 0.28220(12) 1.000 0.0166(4) C6 C Uani 0.5970(3) -0.0501(2) 0.22197(12) 1.000 0.0167(4) C7 C Uani 0.4535(3) -0.2605(2) 0.08587(11) 1.000 0.0149(4) C8 C Uani 0.0926(3) 0.5829(2) 0.37390(11) 1.000 0.0150(4) C9 C Uani 0.1242(3) 0.7696(2) 0.43089(13) 1.000 0.0196(4) H1N H Uiso 0.487(4) 0.492(3) 0.3442(16) 1.000 0.029(5) H2 H Uiso 0.091(4) 0.078(3) 0.0816(15) 1.000 0.023(4) H2O H Uiso 0.308(5) -0.388(4) -0.014(2) 1.000 0.067(8) H3 H Uiso 0.034(4) 0.377(3) 0.1808(15) 1.000 0.024(4) H5 H Uiso 0.693(4) 0.135(3) 0.3344(16) 1.000 0.028(5) H6 H Uiso 0.739(4) -0.158(3) 0.2312(15) 1.000 0.026(5) H9A H Uiso 0.307(4) 0.761(3) 0.4478(16) 1.000 0.034(5) H9B H Uiso -0.021(4) 0.801(3) 0.4975(18) 1.000 0.037(5) H9C H Uiso 0.093(4) 0.881(3) 0.3787(16) 1.000 0.031(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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 C7 O2 H2O 109.7(16) no C4 N1 C8 125.40(14) yes C8 N1 H1N 118.1(13) no C4 N1 H1N 116.3(13) no C2 C1 C6 119.80(13) no C6 C1 C7 119.43(13) no C2 C1 C7 120.77(13) no C1 C2 C3 120.49(14) no C2 C3 C4 119.27(13) no N1 C4 C3 121.51(13) yes N1 C4 C5 117.99(13) yes C3 C4 C5 120.47(13) no C4 C5 C6 119.88(14) no C1 C6 C5 120.07(13) no O2 C7 C1 115.18(12) yes O1 C7 O2 123.53(13) yes O1 C7 C1 121.29(13) yes O3 C8 N1 123.38(13) yes O3 C8 C9 121.47(13) yes N1 C8 C9 115.15(13) yes C1 C2 H2 120.2(12) no C3 C2 H2 119.3(12) no C2 C3 H3 119.7(12) no C4 C3 H3 121.0(12) no C4 C5 H5 122.0(12) no C6 C5 H5 118.1(12) no C1 C6 H6 119.5(12) no C5 C6 H6 120.4(12) no C8 C9 H9A 111.9(12) no C8 C9 H9B 109.9(12) no C8 C9 H9C 107.5(12) no H9A C9 H9B 113.0(17) no H9A C9 H9C 107.3(17) no H9B C9 H9C 107.0(17) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 1.2411(18) yes O2 C7 1.3034(18) yes O3 C8 1.2300(19) yes O2 H2O 0.91(3) no N1 C8 1.355(2) yes N1 C4 1.4183(18) yes N1 H1N 0.89(2) no C1 C2 1.393(2) no C1 C7 1.4817(19) no C1 C6 1.393(2) no C2 C3 1.391(2) no C3 C4 1.393(2) no C4 C5 1.394(2) no C5 C6 1.386(2) no C8 C9 1.505(2) no C2 H2 0.950(19) no C3 H3 0.97(2) no C5 H5 0.99(2) no C6 H6 0.94(2) no C9 H9A 0.96(2) no C9 H9B 1.00(2) no C9 H9C 0.99(2) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C4 3.4119(19) 1_545 no O1 C7 3.3708(19) 2_645 no O1 O2 2.6203(16) 2_645 no O2 C2 3.365(2) 2_555 no O2 O1 2.6203(16) 2_645 no O3 C9 3.236(2) 2_566 no O3 C3 2.9240(19) . no O3 C8 3.2804(19) 2_566 no O3 N1 2.954(2) 1_455 no O1 H3 2.60(2) 1_645 no O1 H2O 1.72(3) 2_645 no O1 H6 2.518(19) . no O2 H2 2.45(2) . no O2 H2 2.55(2) 2_555 no O2 H2O 2.84(3) 2_645 no O3 H6 2.660(19) 1_465 no O3 H1N 2.07(2) 1_455 no O3 H3 2.522(18) . no O3 H9B 2.91(2) 2_566 no N1 O3 2.954(2) 1_655 no C2 O2 3.365(2) 2_555 no C2 C5 3.414(2) 1_455 no C2 C6 3.389(2) 1_455 no C2 C7 3.266(2) 2_655 no C3 C5 3.400(2) 1_455 no C3 O3 2.9240(19) . no C4 O1 3.4119(19) 1_565 no C5 C2 3.414(2) 1_655 no C5 C3 3.400(2) 1_655 no C6 C9 3.567(2) 1_545 no C6 C2 3.389(2) 1_655 no C7 C2 3.266(2) 2_655 no C7 O1 3.3708(19) 2_645 no C8 C9 3.555(2) 2_566 no C8 C8 3.316(2) 2_566 no C8 O3 3.2804(19) 2_566 no C9 O3 3.236(2) 2_566 no C9 C6 3.567(2) 1_565 no C9 C8 3.555(2) 2_566 no C9 C9 3.505(2) 2_576 no C1 H9C 3.06(2) 1_545 no C3 H5 3.02(2) 1_455 no C6 H9C 3.03(2) 1_545 no C6 H2 3.04(2) 1_655 no C7 H2O 2.57(3) 2_645 no C8 H9B 3.08(2) 2_566 no C8 H3 2.840(19) . no C8 H6 3.01(2) 1_465 no C9 H9B 3.00(2) 2_576 no H1N O3 2.07(2) 1_655 no H1N H5 2.46(3) . no H1N H9A 2.21(3) . no H2 O2 2.45(2) . no H2 C6 3.04(2) 1_455 no H2 O2 2.55(2) 2_555 no H2O O1 1.72(3) 2_645 no H2O O2 2.84(3) 2_645 no H2O C7 2.57(3) 2_645 no H2O H2O 2.30(4) 2_645 no H3 O1 2.60(2) 1_465 no H3 O3 2.522(18) . no H3 C8 2.840(19) . no H5 C3 3.02(2) 1_655 no H5 H1N 2.46(3) . no H5 H9C 2.52(3) 1_645 no H6 O1 2.518(19) . no H6 O3 2.660(19) 1_645 no H6 C8 3.01(2) 1_645 no H9A H1N 2.21(3) . no H9B O3 2.91(2) 2_566 no H9B C8 3.08(2) 2_566 no H9B C9 3.00(2) 2_576 no H9B H9C 2.60(3) 2_576 no H9C C1 3.06(2) 1_565 no H9C C6 3.03(2) 1_565 no H9C H5 2.52(3) 1_465 no H9C H9B 2.60(3) 2_576 no 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 _geom_hbond_publ_flag N1 H1N O3 0.89(2) 2.07(2) 2.954(2) 176(2) 1_655 yes O2 H2O O1 0.91(3) 1.72(3) 2.6203(16) 173(3) 2_645 yes C2 H2 O2 0.950(19) 2.55(2) 3.365(2) 144.8(16) 2_555 yes C3 H3 O3 0.97(2) 2.522(18) 2.9240(19) 105.0(13) . 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 C4 N1 C8 O3 2.0(2) no C4 N1 C8 C9 -177.45(12) no C8 N1 C4 C3 38.9(2) no C8 N1 C4 C5 -143.18(14) no C6 C1 C2 C3 -0.4(2) no C7 C1 C6 C5 -179.11(13) no C6 C1 C7 O1 -4.9(2) no C6 C1 C7 O2 174.66(13) no C2 C1 C7 O1 174.75(13) no C7 C1 C2 C3 179.89(13) no C2 C1 C6 C5 1.2(2) no C2 C1 C7 O2 -5.7(2) no C1 C2 C3 C4 -0.8(2) no C2 C3 C4 N1 179.10(13) no C2 C3 C4 C5 1.2(2) no N1 C4 C5 C6 -178.41(13) no C3 C4 C5 C6 -0.4(2) no C4 C5 C6 C1 -0.8(2) no