#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203629.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_2203629 loop_ _publ_author_name 'Glidewell, Christopher' 'Low, John N.' 'Skakle, Janet M. S.' 'Wardell, James L.' _publ_section_title ; 2-Methoxycarbonyl-4-nitroacetanilide: \p-stacked chains linked in pairs by C---H...O hydrogen bonds ; _journal_issue 5 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o852 _journal_page_last o854 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C10 H10 N2 O5' _chemical_formula_moiety 'C10 H10 N2 O5' _chemical_formula_sum 'C10 H10 N2 O5' _chemical_formula_weight 238.20 _chemical_name_systematic ; 2-Methoxycarbonyl-4-nitroacetanilide ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-I 2 2c' _symmetry_space_group_name_H-M 'I b a m' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 16.4482(14) _cell_length_b 19.9095(17) _cell_length_c 6.7549(6) _cell_measurement_reflns_used 1384 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 2.05 _cell_volume 2212.1(3) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'OSCAIL and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 291(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method \f-\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 7820 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.05 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2000)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.430 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 992 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.167 _refine_diff_density_min -0.226 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 105 _refine_ls_number_reflns 1384 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.008 _refine_ls_R_factor_all 0.0903 _refine_ls_R_factor_gt 0.0501 _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^)+(0.0672P)^2^+0.1650P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1176 _refine_ls_wR_factor_ref 0.1302 _reflns_number_gt 828 _reflns_number_total 1384 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh6206.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, z+1/2' '-x, y, z+1/2' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, z+1' '-x+1/2, y+1/2, z+1' '-x, -y, -z' 'x, y, -z' '-x, y, -z-1/2' 'x, -y, -z-1/2' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 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_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_type_symbol O11 0.45219(11) 0.10453(9) 0.5000 0.0744(6) Uani d S 1 O O21 0.66067(10) 0.37614(9) 0.5000 0.0692(6) Uani d S 1 O O22 0.68212(10) 0.26564(8) 0.5000 0.0616(6) Uani d S 1 O O41 0.40462(14) 0.47898(12) 0.5000 0.1634(16) Uani d S 1 O O42 0.29482(11) 0.42449(11) 0.5000 0.0958(8) Uani d S 1 O N1 0.54959(11) 0.18637(9) 0.5000 0.0489(5) Uani d S 1 N N4 0.36872(14) 0.42739(12) 0.5000 0.0729(8) Uani d S 1 N C1 0.50391(14) 0.24555(11) 0.5000 0.0416(6) Uani d S 1 C C2 0.54480(12) 0.30844(11) 0.5000 0.0408(5) Uani d S 1 C C3 0.49928(13) 0.36756(12) 0.5000 0.0470(6) Uani d S 1 C C4 0.41495(13) 0.36446(12) 0.5000 0.0490(6) Uani d S 1 C C5 0.37413(14) 0.30371(13) 0.5000 0.0507(6) Uani d S 1 C C6 0.41814(14) 0.24511(12) 0.5000 0.0504(6) Uani d S 1 C C11 0.52385(16) 0.12038(12) 0.5000 0.0512(6) Uani d S 1 C C12 0.59167(17) 0.07005(13) 0.5000 0.0689(8) Uani d S 1 C C21 0.63546(13) 0.31282(11) 0.5000 0.0450(6) Uani d S 1 C C22 0.74801(15) 0.38759(15) 0.5000 0.0832(10) Uani d S 1 C H1 0.6015 0.1919 0.5000 0.059 Uiso calc SR 1 H H3 0.5254 0.4090 0.5000 0.056 Uiso calc SR 1 H H5 0.3176 0.3026 0.5000 0.061 Uiso calc SR 1 H H6 0.3908 0.2042 0.5000 0.061 Uiso calc SR 1 H H12A 0.6364 0.0871 0.4236 0.103 Uiso calc PR 0.50 H H12B 0.5729 0.0287 0.4428 0.103 Uiso calc PR 0.50 H H12C 0.6092 0.0621 0.6335 0.103 Uiso calc PR 0.50 H H22A 0.7726 0.3620 0.6046 0.125 Uiso calc PR 0.50 H H22B 0.7587 0.4345 0.5202 0.125 Uiso calc PR 0.50 H H22C 0.7704 0.3738 0.3752 0.125 Uiso calc PR 0.50 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 O11 0.0529(12) 0.0586(11) 0.1116(18) -0.0126(8) 0.000 0.000 O21 0.0310(8) 0.0527(10) 0.1239(18) -0.0032(7) 0.000 0.000 O22 0.0367(9) 0.0546(10) 0.0936(16) 0.0063(8) 0.000 0.000 O41 0.0541(13) 0.0527(14) 0.383(5) 0.0054(10) 0.000 0.000 O42 0.0394(11) 0.0895(15) 0.158(3) 0.0176(10) 0.000 0.000 N1 0.0394(10) 0.0479(11) 0.0593(14) -0.0033(8) 0.000 0.000 N4 0.0402(12) 0.0643(15) 0.114(2) 0.0088(11) 0.000 0.000 C1 0.0381(12) 0.0490(12) 0.0376(14) -0.0013(9) 0.000 0.000 C2 0.0325(11) 0.0494(12) 0.0404(14) -0.0020(9) 0.000 0.000 C3 0.0358(12) 0.0497(12) 0.0556(16) -0.0024(10) 0.000 0.000 C4 0.0351(12) 0.0541(14) 0.0580(17) 0.0029(10) 0.000 0.000 C5 0.0314(11) 0.0679(16) 0.0527(17) -0.0019(11) 0.000 0.000 C6 0.0369(13) 0.0590(15) 0.0554(17) -0.0090(10) 0.000 0.000 C11 0.0522(15) 0.0485(14) 0.0530(16) -0.0055(11) 0.000 0.000 C12 0.0604(16) 0.0521(16) 0.094(2) 0.0014(12) 0.000 0.000 C21 0.0365(12) 0.0479(13) 0.0504(16) -0.0031(10) 0.000 0.000 C22 0.0301(13) 0.0730(18) 0.147(3) -0.0092(13) 0.000 0.000 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 N1 1.397(3) no C1 C6 1.411(3) no C1 C2 1.421(3) no N1 C11 1.380(3) no N1 H1 0.86 no C11 O11 1.220(3) no C11 C12 1.499(4) no C12 H12A 0.96 no C12 H12B 0.96 no C12 H12C 0.96 no C2 C3 1.395(3) no C2 C21 1.494(3) no C21 O22 1.213(3) no C21 O21 1.327(3) no O21 C22 1.454(3) no C22 H22A 0.96 no C22 H22B 0.96 no C22 H22C 0.96 no C3 C4 1.388(3) no C3 H3 0.93 no C4 C5 1.383(3) no C4 N4 1.466(3) no N4 O41 1.185(3) no N4 O42 1.217(3) no C5 C6 1.373(3) no C5 H5 0.93 no C6 H6 0.93 no 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 C6 122.2(2) no N1 C1 C2 119.24(19) no C6 C1 C2 118.6(2) no C1 N1 C11 129.6(2) y C11 N1 H1 115.2 no C1 N1 H1 115.2 no N1 C11 O11 122.8(2) y N1 C11 C12 114.1(2) y O11 C11 C12 123.1(2) y C11 C12 H12A 109.5 no C11 C12 H12B 109.5 no H12A C12 H12B 109.5 no C11 C12 H12C 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no C3 C2 C1 119.3(2) no C3 C2 C21 119.1(2) no C1 C2 C21 121.58(19) no C2 C21 O21 111.55(19) y C2 C21 O22 125.9(2) y O21 C21 O22 122.5(2) y C21 O21 C22 117.2(2) y O21 C22 H22A 109.5 no O21 C22 H22B 109.5 no H22A C22 H22B 109.5 no O21 C22 H22C 109.5 no H22A C22 H22C 109.5 no H22B C22 H22C 109.5 no C4 C3 C2 119.9(2) no C4 C3 H3 120.0 no C2 C3 H3 120.0 no C5 C4 C3 121.6(2) no C5 C4 N4 119.7(2) no C3 C4 N4 118.7(2) no O41 N4 O42 122.6(2) no O41 N4 C4 118.8(2) no O42 N4 C4 118.5(2) no C6 C5 C4 119.1(2) no C6 C5 H5 120.4 no C4 C5 H5 120.4 no C5 C6 C1 121.5(2) no C5 C6 H6 119.3 no C1 C6 H6 119.3 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 N1 H1 O22 . 0.86 1.98 2.691(2) 139 y C3 H3 O41 2_665 0.93 2.51 3.440(3) 180 y C3 H3 O21 . 0.93 2.32 2.660(3) 101 y C6 H6 O11 . 0.93 2.23 2.854(3) 124 y _cod_database_code 2203629