#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2218141.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_2218141 loop_ _publ_author_name 'Li, Xiang' 'Yuan, Lian-Shan' 'Wang, Dan' 'Liu, Shan' 'Yao, Cheng' _publ_section_title ; Methyl 4-amino-3-methylbenzoate ; _journal_coeditor_code HK2431 _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o886 _journal_volume 64 _journal_year 2008 _chemical_formula_iupac 'C9 H11 N O2' _chemical_formula_moiety 'C9 H11 N O2' _chemical_formula_sum 'C9 H11 N O2' _chemical_formula_weight 165.19 _chemical_melting_point 391(2) _chemical_name_systematic ; Methyl 4-amino-3-methylbenzoate ; _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 98.14(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.5670(15) _cell_length_b 6.1080(12) _cell_length_c 18.127(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 9 _cell_volume 829.4(3) _computing_cell_refinement 'CAD-4 Software (Enraf--Nonius, 1985)' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1985)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w/2\q _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 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1747 _diffrn_reflns_theta_full 25.96 _diffrn_reflns_theta_max 25.96 _diffrn_reflns_theta_min 2.27 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_correction_T_min 0.9634 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.253 _refine_diff_density_min -0.272 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1620 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0528 _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^)+(0.06P)^2^+1.3P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1209 _refine_ls_wR_factor_ref 0.1884 _reflns_number_gt 1079 _reflns_number_total 1620 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hk2431.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' 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_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_ _atom_site_type_symbol _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 N N 0.8206(4) 0.4908(5) 0.17914(15) 0.0570(8) Uani d . 1 H H0A 0.8716 0.6166 0.1792 0.068 Uiso calc R 1 H H0B 0.7811 0.4279 0.1376 0.068 Uiso calc R 1 O O1 0.6922(3) -0.1169(4) 0.44629(12) 0.0549(7) Uani d . 1 O O2 0.8163(4) 0.1644(4) 0.51362(13) 0.0621(8) Uani d . 1 C C1 0.6852(5) -0.2393(6) 0.51341(18) 0.0561(10) Uani d . 1 H H1A 0.6303 -0.3788 0.5012 0.084 Uiso calc R 1 H H1B 0.6164 -0.1599 0.5451 0.084 Uiso calc R 1 H H1C 0.8041 -0.2610 0.5388 0.084 Uiso calc R 1 C C2 0.7641(4) 0.0832(5) 0.45389(18) 0.0440(8) Uani d . 1 C C3 0.7726(4) 0.1877(5) 0.38130(17) 0.0404(7) Uani d . 1 C C4 0.7052(4) 0.0892(5) 0.31364(17) 0.0423(8) Uani d . 1 H H4A 0.6496 -0.0464 0.3145 0.051 Uiso calc R 1 C C5 0.7176(4) 0.1847(5) 0.24532(17) 0.0405(8) Uani d . 1 C C6 0.8021(4) 0.3903(5) 0.24530(17) 0.0414(7) Uani d . 1 C C7 0.8662(4) 0.4927(5) 0.31251(18) 0.0450(8) Uani d . 1 H H7A 0.9196 0.6297 0.3120 0.054 Uiso calc R 1 C C8 0.8517(4) 0.3940(5) 0.37935(18) 0.0427(8) Uani d . 1 H H8A 0.8947 0.4649 0.4237 0.051 Uiso calc R 1 C C9 0.6433(5) 0.0725(6) 0.17397(18) 0.0525(9) Uani d . 1 H H9A 0.5906 -0.0644 0.1851 0.079 Uiso calc R 1 H H9B 0.7377 0.0463 0.1448 0.079 Uiso calc R 1 H H9C 0.5541 0.1639 0.1464 0.079 Uiso calc R 1 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 N 0.076(2) 0.0464(17) 0.0479(17) -0.0106(16) 0.0050(15) 0.0071(14) O1 0.0748(17) 0.0429(13) 0.0455(13) -0.0097(13) 0.0031(11) 0.0032(11) O2 0.090(2) 0.0538(16) 0.0409(13) -0.0084(14) 0.0053(13) -0.0040(12) C1 0.076(3) 0.048(2) 0.0449(19) -0.0029(19) 0.0100(17) 0.0037(16) C2 0.0489(19) 0.0416(18) 0.0418(17) 0.0019(16) 0.0079(14) -0.0005(15) C3 0.0425(17) 0.0373(17) 0.0414(17) 0.0040(14) 0.0058(13) -0.0029(14) C4 0.0430(18) 0.0349(17) 0.0479(18) -0.0003(14) 0.0021(14) -0.0008(14) C5 0.0419(18) 0.0344(16) 0.0435(17) 0.0038(14) 0.0003(13) -0.0020(14) C6 0.0448(18) 0.0325(16) 0.0468(17) 0.0050(14) 0.0065(14) 0.0022(14) C7 0.0458(19) 0.0327(16) 0.056(2) -0.0036(14) 0.0061(15) -0.0014(15) C8 0.0477(18) 0.0372(17) 0.0434(17) 0.0030(15) 0.0071(13) -0.0067(14) C9 0.057(2) 0.051(2) 0.0469(19) -0.0055(17) -0.0031(16) -0.0022(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N C6 1.372(4) N H0A 0.8600 N H0B 0.8600 O1 C2 1.336(4) O1 C1 1.435(4) C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600 O2 C2 1.206(4) C2 C3 1.472(4) C3 C4 1.396(4) C3 C8 1.398(4) C4 C5 1.384(4) C4 H4A 0.9300 C5 C6 1.410(4) C5 C9 1.501(4) C6 C7 1.394(4) C7 C8 1.372(4) C7 H7A 0.9300 C8 H8A 0.9300 C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 N H0A 120.0 C6 N H0B 120.0 H0A N H0B 120.0 C2 O1 C1 116.9(3) O1 C1 H1A 109.5 O1 C1 H1B 109.5 H1A C1 H1B 109.5 O1 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 O2 C2 O1 123.1(3) O2 C2 C3 125.0(3) O1 C2 C3 111.9(3) C4 C3 C8 118.1(3) C4 C3 C2 122.8(3) C8 C3 C2 119.1(3) C5 C4 C3 122.8(3) C5 C4 H4A 118.6 C3 C4 H4A 118.6 C4 C5 C6 117.6(3) C4 C5 C9 120.9(3) C6 C5 C9 121.4(3) N C6 C7 119.9(3) N C6 C5 120.1(3) C7 C6 C5 120.1(3) C8 C7 C6 120.9(3) C8 C7 H7A 119.5 C6 C7 H7A 119.5 C7 C8 C3 120.4(3) C7 C8 H8A 119.8 C3 C8 H8A 119.8 C5 C9 H9A 109.5 C5 C9 H9B 109.5 H9A C9 H9B 109.5 C5 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 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 C1 O1 C2 O2 -2.4(5) C1 O1 C2 C3 177.0(3) O2 C2 C3 C4 -178.0(3) O1 C2 C3 C4 2.7(4) O2 C2 C3 C8 2.2(5) O1 C2 C3 C8 -177.2(3) C8 C3 C4 C5 1.7(5) C2 C3 C4 C5 -178.2(3) C3 C4 C5 C6 -0.1(5) C3 C4 C5 C9 180.0(3) C4 C5 C6 N 179.0(3) C9 C5 C6 N -1.1(5) C4 C5 C6 C7 -1.4(4) C9 C5 C6 C7 178.5(3) N C6 C7 C8 -179.0(3) C5 C6 C7 C8 1.3(5) C6 C7 C8 C3 0.3(5) C4 C3 C8 C7 -1.7(5) C2 C3 C8 C7 178.1(3) 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 C4 H4A O1 . 0.93 2.40 2.728(4) 100.30 yes N H0B O2 4_565 0.86 2.37 3.142(3) 149.88 yes _cod_database_code 2218141