#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013900.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_2013900 loop_ _publ_author_name 'Doriguetto, Antonio C.' 'de Paula Silva, Carlos H. T.' 'Rando, Daniela G.' 'Ferreira, Elizabeth I.' 'Ellena, Javier' _publ_section_title ; A new monoclinic polymorph of methyl p-aminobenzoate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o69 _journal_page_last o71 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C8 H9 N O2' _chemical_formula_moiety 'C8 H9 N O2' _chemical_formula_sum 'C8 H9 N O2' _chemical_formula_weight 151.16 _chemical_name_systematic ; methyl-p-aminobenzoate ; _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' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 96.172(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.5969(4) _cell_length_b 5.6053(2) _cell_length_c 15.5397(7) _cell_measurement_reflns_used 13722 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.485 _cell_measurement_theta_min 3.395 _cell_volume 744.49(6) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_collection 'Collect (Nonius, 1998)' _computing_data_reduction 'HKL Denzo (Otwinowski & Minor, 1997) and Scalepack' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.070 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 15706 _diffrn_reflns_theta_full 25 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 3.74 _diffrn_standards_decay_% none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.167 _refine_diff_density_min -0.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 108 _refine_ls_number_reflns 1313 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_gt 0.040 _refine_ls_shift/su_max 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.0853P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.104 _reflns_number_gt 1040 _reflns_number_total 1313 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ty1003.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_bond_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times). '_geom_angle_publ_flag' value 'YES' changed to 'yes' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2013900 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.80614(17) 0.3526(3) 0.17141(9) 0.0281(4) Uani d . 1 . . C C2 0.67864(17) 0.2148(3) 0.19080(9) 0.0286(4) Uani d . 1 . . C H2 0.6962 0.0692 0.2216 0.034 Uiso calc R 1 . . H C3 0.52753(17) 0.2893(3) 0.16547(9) 0.0292(4) Uani d . 1 . . C H3 0.4421 0.1937 0.1788 0.035 Uiso calc R 1 . . H C4 0.49877(16) 0.5026(2) 0.12064(9) 0.0271(4) Uani d . 1 . . C C5 0.62569(17) 0.6391(3) 0.10085(9) 0.0288(4) Uani d . 1 . . C H5 0.6077 0.7844 0.0699 0.035 Uiso calc R 1 . . H C6 0.77676(17) 0.5658(3) 0.12551(9) 0.0299(4) Uani d . 1 . . C H6 0.8619 0.6608 0.1113 0.036 Uiso calc R 1 . . H C7 0.33586(17) 0.5786(3) 0.09731(9) 0.0283(4) Uani d . 1 . . C C8 0.16864(18) 0.8875(3) 0.04241(11) 0.0386(4) Uani d . 1 . . C H8A 0.1727 1.0473 0.0172 0.058 Uiso calc R 1 . . H H8B 0.1172 0.8957 0.0956 0.058 Uiso calc R 1 . . H H8C 0.1095 0.7808 0.001 0.058 Uiso calc R 1 . . H N1 0.95806(15) 0.2844(3) 0.19940(9) 0.0326(4) Uani d . 1 . . N O1 0.22084(12) 0.46162(19) 0.10881(7) 0.0352(3) Uani d . 1 . . O O2 0.32538(11) 0.79740(18) 0.06218(7) 0.0338(3) Uani d . 1 . . O H11 1.032(2) 0.342(3) 0.1705(11) 0.038(5) Uiso d . 1 . . H H12 0.970(2) 0.131(4) 0.2187(11) 0.048(5) Uiso d . 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 C1 0.0277(8) 0.0310(8) 0.0254(7) -0.0001(6) 0.0021(6) -0.0032(6) C2 0.0318(8) 0.0264(8) 0.0276(8) -0.0005(6) 0.0031(6) 0.0004(6) C3 0.0291(8) 0.0301(8) 0.0290(8) -0.0049(6) 0.0057(6) -0.0012(6) C4 0.0264(8) 0.0297(8) 0.0253(7) -0.0018(6) 0.0034(6) -0.0027(6) C5 0.0311(8) 0.0276(8) 0.0279(8) -0.0013(6) 0.0034(6) -0.0001(6) C6 0.0258(8) 0.0308(8) 0.0333(8) -0.0048(6) 0.0042(6) 0.0004(6) C7 0.0302(8) 0.0296(8) 0.0257(7) -0.0021(6) 0.0054(6) -0.0029(6) C8 0.0268(9) 0.0389(9) 0.0498(10) 0.0059(7) 0.0030(7) 0.0031(8) N1 0.0258(7) 0.0350(8) 0.0373(8) 0.0013(6) 0.0044(6) 0.0055(6) O1 0.0266(6) 0.0400(7) 0.0396(6) -0.0038(5) 0.0056(5) 0.0017(5) O2 0.0250(6) 0.0335(6) 0.0427(6) 0.0025(4) 0.0023(5) 0.0030(5) 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 C1 N1 . 1.385(2) yes C1 C2 . 1.400(2) ? C1 C6 . 1.401(2) ? C2 C3 . 1.381(2) ? C2 H2 . 0.95 ? C3 C4 . 1.393(2) ? C3 H3 . 0.95 ? C4 C5 . 1.394(2) ? C4 C7 . 1.472(2) yes C5 C6 . 1.377(2) ? C5 H5 . 0.95 ? C6 H6 . 0.95 ? C7 O1 . 1.216(2) yes C7 O2 . 1.341(2) yes C8 O2 . 1.441(2) yes C8 H8A . 0.98 ? C8 H8B . 0.98 ? C8 H8C . 0.98 ? N1 H11 . 0.88(2) ? N1 H12 . 0.91(2) ? 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 0 '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 0.006 '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 N1 C1 C2 120.90(10) yes N1 C1 C6 120.50(10) yes C2 C1 C6 118.60(10) ? C3 C2 C1 120.40(10) ? C3 C2 H2 119.8 ? C1 C2 H2 119.8 ? C2 C3 C4 120.90(10) ? C2 C3 H3 119.6 ? C4 C3 H3 119.6 ? C3 C4 C5 118.70(10) ? C3 C4 C7 119.00(10) yes C5 C4 C7 122.30(10) yes C6 C5 C4 120.80(10) ? C6 C5 H5 119.6 ? C4 C5 H5 119.6 ? C5 C6 C1 120.60(10) ? C5 C6 H6 119.7 ? C1 C6 H6 119.7 ? O1 C7 O2 122.20(10) yes O1 C7 C4 125.10(10) yes O2 C7 C4 112.70(10) yes O2 C8 H8A 109.5 ? O2 C8 H8B 109.5 ? H8A C8 H8B 109.5 ? O2 C8 H8C 109.5 ? H8A C8 H8C 109.5 ? H8B C8 H8C 109.5 ? C1 N1 H11 117.0(10) ? C1 N1 H12 115.0(10) ? H11 N1 H12 117(2) ? C7 O2 C8 115.30(10) yes 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 N1 H11 O1 1_655 0.88(2) 2.08(2) 2.959(2) 175.1(16) yes N1 H12 N1 2_745 0.91(2) 2.37(2) 3.256(2) 164.4(16) yes _cod_database_fobs_code 2013900 _journal_paper_doi 10.1107/S0108270103027422