#------------------------------------------------------------------------------ #$Date: 2008-04-03 13:11:48 +0300 (Thu, 03 Apr 2008) $ #$Revision: 326 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2209401.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_2209401 loop_ _publ_author_name 'Hansen, Lars Kr.' 'Perlovich, German L.' 'Bauer-Brandl, Annette' _publ_section_title ; Redetermination of p-ethoxyacetanilide (phenacetin) ; _journal_coeditor_code BT2088 _journal_issue 7 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o2712 _journal_page_last o2713 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C10 H13 N O2' _chemical_formula_moiety 'C10 H13 N O2' _chemical_formula_sum 'C10 H13 N O2' _chemical_formula_weight 179.21 _chemical_name_systematic ; p-ethoxyacetanilide ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 103.992(14) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.3236(14) _cell_length_b 9.6159(15) _cell_length_c 7.7331(15) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 20 _cell_measurement_theta_min 13 _cell_volume 961.4(3) _computing_cell_refinement 'CELDIM in CAD-4-PC Software' _computing_data_collection 'CAD-4-PC Software (Enraf--Nonius, 1992)' _computing_data_reduction 'XCAD4 (McArdle & Higgins, 1995)' _computing_molecular_graphics 'ORTEX (McArdle, 1993) and ORTEPIII (Burnett & Johnson, (1996)' _computing_publication_material 'OSCAIL-X for Windows' _computing_structure_refinement 'OSCAIL-X for Windows and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL-X for Windows (McArdle, 2005) and SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 0.71069 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2299 _diffrn_reflns_theta_full 26.99 _diffrn_reflns_theta_max 26.99 _diffrn_reflns_theta_min 1.58 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.9745 _exptl_absorpt_correction_T_min 0.9581 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '[ABSCALC in OSCAIL (McArdle & Daly, 1999) and North et al. (1968)]' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.162 _refine_diff_density_min -0.140 _refine_ls_extinction_coef 0.021(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 121 _refine_ls_number_reflns 2083 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.996 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0389 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0541P)^2^+0.0361P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0970 _refine_ls_wR_factor_ref 0.1110 _reflns_number_gt 1056 _reflns_number_total 2083 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bt2088.cif 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 O O7 0.46006(8) 0.10210(14) 0.20468(17) 0.0577(4) Uani d . 1 O O13 -0.01286(10) 0.27655(13) -0.17104(19) 0.0605(4) Uani d . 1 N N10 0.05111(9) 0.06024(14) -0.18550(18) 0.0431(4) Uani d . 1 H H10 0.0356 -0.0219 -0.2274 0.056 Uiso calc R 1 C C1 0.35754(12) 0.10087(18) 0.1151(2) 0.0424(4) Uani d . 1 C C2 0.28182(13) 0.18444(18) 0.1543(3) 0.0494(5) Uani d . 1 H H2 0.2988 0.2481 0.2473 0.064 Uiso calc R 1 C C3 0.18047(13) 0.17362(18) 0.0551(2) 0.0483(5) Uani d . 1 H H3 0.1299 0.2306 0.0818 0.063 Uiso calc R 1 C C4 0.15391(12) 0.07959(16) -0.0822(2) 0.0380(4) Uani d . 1 C C5 0.23094(12) -0.00290(17) -0.1207(2) 0.0464(5) Uani d . 1 H H5 0.2142 -0.0664 -0.2140 0.060 Uiso calc R 1 C C6 0.33167(13) 0.00742(17) -0.0235(2) 0.0478(5) Uani d . 1 H H6 0.3824 -0.0487 -0.0514 0.062 Uiso calc R 1 C C8 0.49046(13) 0.1847(2) 0.3612(3) 0.0550(5) Uani d . 1 H H8A 0.4473 0.1641 0.4426 0.072 Uiso calc R 1 H H8B 0.4834 0.2827 0.3309 0.072 Uiso calc R 1 C C9 0.60192(15) 0.1503(2) 0.4464(3) 0.0678(6) Uani d . 1 H H9A 0.6095 0.0514 0.4614 0.095 Uiso calc R 1 H H9B 0.6223 0.1949 0.5607 0.095 Uiso calc R 1 H H9C 0.6449 0.1827 0.3715 0.095 Uiso calc R 1 C C11 -0.02454(13) 0.15589(18) -0.2251(2) 0.0445(5) Uani d . 1 C C12 -0.12500(14) 0.1060(2) -0.3406(3) 0.0608(6) Uani d . 1 H H12A -0.1774 0.1088 -0.2744 0.085 Uiso calc R 1 H H12B -0.1171 0.0122 -0.3779 0.085 Uiso calc R 1 H H12C -0.1449 0.1649 -0.4434 0.085 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 O7 0.0369(7) 0.0685(9) 0.0615(9) 0.0054(6) -0.0001(6) -0.0186(7) O13 0.0568(8) 0.0394(7) 0.0778(10) 0.0108(6) 0.0016(7) -0.0003(7) N10 0.0358(8) 0.0335(7) 0.0558(10) -0.0011(6) 0.0027(7) -0.0003(7) C1 0.0323(9) 0.0431(9) 0.0493(11) 0.0000(7) 0.0051(8) -0.0021(9) C2 0.0422(10) 0.0515(11) 0.0514(11) 0.0021(8) 0.0051(9) -0.0176(9) C3 0.0405(10) 0.0503(10) 0.0535(11) 0.0062(8) 0.0103(9) -0.0103(9) C4 0.0351(9) 0.0326(9) 0.0445(10) -0.0003(7) 0.0062(7) 0.0036(8) C5 0.0432(10) 0.0379(9) 0.0536(11) 0.0028(8) 0.0029(8) -0.0106(8) C6 0.0408(9) 0.0431(10) 0.0572(11) 0.0094(8) 0.0070(8) -0.0100(9) C8 0.0457(11) 0.0581(12) 0.0556(12) -0.0021(9) 0.0010(9) -0.0110(10) C9 0.0521(12) 0.0701(14) 0.0690(14) 0.0018(10) -0.0089(10) -0.0065(12) C11 0.0399(10) 0.0419(10) 0.0513(11) 0.0036(8) 0.0104(8) 0.0091(9) C12 0.0401(10) 0.0645(13) 0.0707(13) 0.0022(9) -0.0007(9) 0.0093(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O7 C1 1.3742(19) O7 C8 1.422(2) O13 C11 1.230(2) N10 C11 1.344(2) N10 C4 1.421(2) N10 H10 0.8600 C1 C6 1.377(2) C1 C2 1.380(2) C2 C3 1.386(2) C2 H2 0.9300 C3 C4 1.374(2) C3 H3 0.9300 C4 C5 1.385(2) C5 C6 1.374(2) C5 H5 0.9300 C6 H6 0.9300 C8 C9 1.509(2) C8 H8A 0.9700 C8 H8B 0.9700 C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 C11 C12 1.497(2) C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O7 C8 118.53(13) C11 N10 C4 127.32(14) C11 N10 H10 116.3 C4 N10 H10 116.3 O7 C1 C6 115.42(15) O7 C1 C2 125.09(16) C6 C1 C2 119.49(15) C1 C2 C3 120.07(17) C1 C2 H2 120.0 C3 C2 H2 120.0 C4 C3 C2 120.75(16) C4 C3 H3 119.6 C2 C3 H3 119.6 C3 C4 C5 118.49(15) C3 C4 N10 123.61(15) C5 C4 N10 117.89(15) C6 C5 C4 121.17(16) C6 C5 H5 119.4 C4 C5 H5 119.4 C5 C6 C1 120.02(16) C5 C6 H6 120.0 C1 C6 H6 120.0 O7 C8 C9 107.27(15) O7 C8 H8A 110.3 C9 C8 H8A 110.3 O7 C8 H8B 110.3 C9 C8 H8B 110.3 H8A C8 H8B 108.5 C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 O13 C11 N10 122.80(16) O13 C11 C12 121.77(16) N10 C11 C12 115.44(16) C11 C12 H12A 109.5 C11 C12 H12B 109.5 H12A C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 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 C8 O7 C1 C6 -173.23(16) C8 O7 C1 C2 6.7(3) O7 C1 C2 C3 -179.65(17) C6 C1 C2 C3 0.3(3) C1 C2 C3 C4 0.4(3) C2 C3 C4 C5 -0.8(3) C2 C3 C4 N10 178.02(17) C11 N10 C4 C3 30.5(3) C11 N10 C4 C5 -150.72(17) C3 C4 C5 C6 0.6(3) N10 C4 C5 C6 -178.31(16) C4 C5 C6 C1 0.1(3) O7 C1 C6 C5 179.43(17) C2 C1 C6 C5 -0.5(3) C1 O7 C8 C9 171.64(16) C4 N10 C11 O13 -1.2(3) C4 N10 C11 C12 178.71(17) 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 C3 H3 O13 . 0.93 2.42 2.915(2) 113.5 yes N10 H10 O13 4_555 0.86 2.09 2.9426(18) 174.5 yes