#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202434.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_2202434 loop_ _publ_author_name 'Daniel E. Lynch' 'Sanjeev Bagga' 'Simon Parsons' _publ_section_title ; 2-(2,4-Dichlorophenoxy)-N-(4,6-dimethylpyridin-2-yl)acetamide ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1299 _journal_page_last o1300 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C15 H14 Cl2 N2 O2' _chemical_formula_moiety 'C15 H14 Cl2 N2 O2' _chemical_formula_sum 'C15 H14 Cl2 N2 O2' _chemical_formula_weight 325.18 _chemical_melting_point 435 _chemical_name_systematic ; 2-(2,4-Dichlorophenoxy)-N-(4,6-dimethylpyridin-2-yl)acetamide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 89.28(4) _cell_angle_beta 87.08(5) _cell_angle_gamma 68.74(4) _cell_formula_units_Z 2 _cell_length_a 7.445(5) _cell_length_b 8.790(6) _cell_length_c 12.549(7) _cell_measurement_reflns_used 22 _cell_measurement_temperature 220(2) _cell_measurement_theta_max 16 _cell_measurement_theta_min 15 _cell_volume 764.3(9) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1990)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1990)' _computing_molecular_graphics 'PLATON97 (Spek, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.961 _diffrn_measurement_device_type 'Stoe Stadi-4' _diffrn_measurement_method \w/\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 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3678 _diffrn_reflns_theta_full 24.95 _diffrn_reflns_theta_max 24.95 _diffrn_reflns_theta_min 2.94 _diffrn_standards_decay_% 3 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.429 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.203 _refine_diff_density_min -0.295 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 196 _refine_ls_number_reflns 2570 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0393 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.062P)^2^+0.1634P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1005 _refine_ls_wR_factor_ref 0.1092 _reflns_number_gt 2032 _reflns_number_total 2570 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cf6274.cif _[local]_cod_data_source_block I _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. 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 '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. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 764.4(9) _cod_database_code 2202434 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0.7680(3) 0.4768(3) 0.02870(16) 0.0350(5) Uani d . 1 . . C C2 0.6560(3) 0.6291(3) 0.07107(16) 0.0379(5) Uani d . 1 . . C Cl2 0.64800(11) 0.65788(8) 0.20750(5) 0.0635(2) Uani d . 1 . . Cl C3 0.5510(3) 0.7546(3) 0.00706(17) 0.0400(5) Uani d . 1 . . C H3 0.4745 0.8566 0.0367 0.050 Uiso calc R 1 . . H C4 0.5601(3) 0.7281(3) -0.10125(17) 0.0383(5) Uani d . 1 . . C Cl4 0.42869(10) 0.88715(8) -0.18233(5) 0.0579(2) Uani d . 1 . . Cl C5 0.6701(3) 0.5784(3) -0.14543(17) 0.0446(6) Uani d . 1 . . C H5 0.6749 0.5620 -0.2196 0.056 Uiso calc R 1 . . H C6 0.7729(3) 0.4529(3) -0.08047(17) 0.0427(5) Uani d . 1 . . C H6 0.8469 0.3504 -0.1104 0.060(8) Uiso calc R 1 . . H O7 0.8631(2) 0.36317(18) 0.10017(11) 0.0456(4) Uani d . 1 . . O C8 0.9777(3) 0.2030(3) 0.06473(17) 0.0384(5) Uani d . 1 . . C H81 1.0773 0.2072 0.0120 0.047(6) Uiso calc R 1 . . H H82 0.8968 0.1527 0.0309 0.047(7) Uiso calc R 1 . . H C9 1.0706(3) 0.1029(3) 0.15923(17) 0.0365(5) Uani d . 1 . . C O10 1.1621(3) -0.04317(19) 0.14712(13) 0.0533(5) Uani d . 1 . . O N11 1.0458(3) 0.1869(2) 0.25137(13) 0.0365(4) Uani d . 1 . . N H11 0.9797 0.2910 0.2473 0.046 Uiso calc R 1 . . H C12 1.1110(3) 0.1314(3) 0.35346(16) 0.0338(5) Uani d . 1 . . C N13 1.0269(3) 0.2445(2) 0.42800(14) 0.0381(4) Uani d . 1 . . N C14 1.0738(3) 0.2054(3) 0.52910(17) 0.0410(5) Uani d . 1 . . C C15 1.2042(3) 0.0543(3) 0.55577(18) 0.0455(6) Uani d . 1 . . C H15 1.2326 0.0305 0.6276 0.048(7) Uiso calc R 1 . . H C16 1.2938(3) -0.0629(3) 0.47775(18) 0.0418(5) Uani d . 1 . . C C17 1.2448(3) -0.0218(3) 0.37256(17) 0.0385(5) Uani d . 1 . . C H17 1.3011 -0.0963 0.3164 0.048 Uiso calc R 1 . . H C18 0.9729(4) 0.3355(3) 0.6116(2) 0.0597(7) Uani d . 1 . . C H181 1.0043 0.2913 0.6823 0.075 Uiso calc R 1 . . H H182 0.8345 0.3720 0.6046 0.075 Uiso calc R 1 . . H H183 1.0150 0.4271 0.6008 0.075 Uiso calc R 1 . . H C19 1.4333(4) -0.2283(3) 0.5054(2) 0.0548(6) Uani d . 1 . . C H191 1.3631 -0.2927 0.5375 0.069 Uiso calc R 1 . . H H192 1.5226 -0.2169 0.5556 0.069 Uiso calc R 1 . . H H193 1.5044 -0.2826 0.4412 0.069 Uiso calc R 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 0.0377(12) 0.0342(11) 0.0317(11) -0.0107(10) -0.0064(9) 0.0035(9) C2 0.0423(12) 0.0407(12) 0.0286(11) -0.0120(10) -0.0058(9) -0.0008(9) Cl2 0.0839(5) 0.0523(4) 0.0327(3) 0.0032(3) -0.0157(3) -0.0074(3) C3 0.0392(12) 0.0355(12) 0.0400(12) -0.0068(10) -0.0069(10) 0.0019(10) C4 0.0365(12) 0.0418(12) 0.0376(11) -0.0147(10) -0.0106(9) 0.0116(10) Cl4 0.0620(4) 0.0567(4) 0.0493(4) -0.0134(3) -0.0180(3) 0.0224(3) C5 0.0527(14) 0.0517(14) 0.0292(11) -0.0184(12) -0.0046(10) 0.0042(10) C6 0.0503(14) 0.0395(12) 0.0333(11) -0.0098(11) -0.0038(10) -0.0020(10) O7 0.0599(10) 0.0331(8) 0.0318(8) -0.0011(8) -0.0127(7) 0.0004(6) C8 0.0412(12) 0.0345(11) 0.0337(11) -0.0066(10) -0.0028(9) -0.0038(9) C9 0.0348(11) 0.0374(12) 0.0345(11) -0.0093(10) -0.0047(9) -0.0023(9) O10 0.0609(11) 0.0364(9) 0.0464(9) 0.0038(8) -0.0153(8) -0.0064(7) N11 0.0429(10) 0.0301(9) 0.0319(9) -0.0073(8) -0.0051(8) 0.0014(7) C12 0.0355(11) 0.0372(11) 0.0311(10) -0.0159(10) -0.0044(9) 0.0039(9) N13 0.0440(11) 0.0389(10) 0.0338(10) -0.0177(9) -0.0051(8) 0.0010(8) C14 0.0462(13) 0.0473(13) 0.0349(11) -0.0228(11) -0.0073(10) 0.0021(10) C15 0.0486(14) 0.0593(15) 0.0343(12) -0.0255(13) -0.0098(10) 0.0073(11) C16 0.0349(12) 0.0463(13) 0.0467(13) -0.0172(11) -0.0084(10) 0.0135(11) C17 0.0367(12) 0.0399(12) 0.0370(12) -0.0115(10) -0.0031(9) 0.0029(9) C18 0.0782(19) 0.0644(17) 0.0391(13) -0.0281(16) -0.0070(13) -0.0090(12) C19 0.0472(15) 0.0581(16) 0.0546(15) -0.0128(13) -0.0153(12) 0.0198(12) 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 O7 . 1.354(3) ? C1 C6 . 1.385(3) ? C1 C2 . 1.391(3) ? C2 C3 . 1.374(3) ? C2 Cl2 . 1.729(2) ? C3 C4 . 1.376(3) ? C3 H3 . 0.94 ? C4 C5 . 1.379(3) ? C4 Cl4 . 1.738(2) ? C5 C6 . 1.377(3) ? C5 H5 . 0.94 ? C6 H6 . 0.94 ? O7 C8 . 1.419(3) ? C8 C9 . 1.508(3) ? C8 H81 . 0.98 ? C8 H82 . 0.98 ? C9 O10 . 1.223(3) ? C9 N11 . 1.348(3) ? N11 C12 . 1.411(3) ? N11 H11 . 0.87 ? C12 N13 . 1.330(3) ? C12 C17 . 1.381(3) ? N13 C14 . 1.340(3) ? C14 C15 . 1.380(3) ? C14 C18 . 1.507(3) ? C15 C16 . 1.387(3) ? C15 H15 . 0.94 ? C16 C17 . 1.396(3) ? C16 C19 . 1.497(3) ? C17 H17 . 0.94 ? C18 H181 . 0.97 ? C18 H182 . 0.97 ? C18 H183 . 0.97 ? C19 H191 . 0.97 ? C19 H192 . 0.97 ? C19 H193 . 0.97 ? 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' Cl Cl 0.1484 0.1585 '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 O7 C1 C6 125.7(2) O7 C1 C2 115.67(19) C6 C1 C2 118.7(2) C3 C2 C1 121.4(2) C3 C2 Cl2 120.06(17) C1 C2 Cl2 118.56(18) C2 C3 C4 118.8(2) C2 C3 H3 120.6 C4 C3 H3 120.6 C5 C4 C3 121.1(2) C5 C4 Cl4 120.12(18) C3 C4 Cl4 118.79(18) C6 C5 C4 119.7(2) C6 C5 H5 120.2 C4 C5 H5 120.2 C5 C6 C1 120.4(2) C5 C6 H6 119.8 C1 C6 H6 119.8 C1 O7 C8 119.76(17) O7 C8 C9 108.97(17) O7 C8 H81 109.9 C9 C8 H81 109.9 O7 C8 H82 109.9 C9 C8 H82 109.9 H81 C8 H82 108.3 O10 C9 N11 125.6(2) O10 C9 C8 119.18(19) N11 C9 C8 115.19(18) C9 N11 C12 129.69(18) C9 N11 H11 115.2 C12 N11 H11 115.2 N13 C12 C17 124.8(2) N13 C12 N11 111.47(19) C17 C12 N11 123.75(19) C12 N13 C14 117.3(2) N13 C14 C15 121.9(2) N13 C14 C18 115.8(2) C15 C14 C18 122.3(2) C14 C15 C16 120.7(2) C14 C15 H15 119.6 C16 C15 H15 119.6 C15 C16 C17 117.3(2) C15 C16 C19 121.5(2) C17 C16 C19 121.3(2) C12 C17 C16 118.0(2) C12 C17 H17 121.0 C16 C17 H17 121.0 C14 C18 H181 109.5 C14 C18 H182 109.5 H181 C18 H182 109.5 C14 C18 H183 109.5 H181 C18 H183 109.5 H182 C18 H183 109.5 C16 C19 H191 109.5 C16 C19 H192 109.5 H191 C19 H192 109.5 C16 C19 H193 109.5 H191 C19 H193 109.5 H192 C19 H193 109.5 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_publ_flag N11 H11 O7 0.87 2.07 2.552(3) 114 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 O7 C1 C2 C3 -179.43(19) C6 C1 C2 C3 0.1(3) O7 C1 C2 Cl2 -0.3(3) C6 C1 C2 Cl2 179.28(17) C1 C2 C3 C4 -0.8(3) Cl2 C2 C3 C4 -179.97(16) C2 C3 C4 C5 0.8(3) C2 C3 C4 Cl4 -179.59(16) C3 C4 C5 C6 0.0(3) Cl4 C4 C5 C6 -179.65(17) C4 C5 C6 C1 -0.7(4) O7 C1 C6 C5 -179.9(2) C2 C1 C6 C5 0.6(3) C6 C1 O7 C8 -0.9(3) C2 C1 O7 C8 178.58(19) C1 O7 C8 C9 178.64(18) O7 C8 C9 O10 173.7(2) O7 C8 C9 N11 -7.2(3) O10 C9 N11 C12 -1.7(4) C8 C9 N11 C12 179.32(19) C9 N11 C12 N13 -168.0(2) C9 N11 C12 C17 11.7(3) C17 C12 N13 C14 -1.1(3) N11 C12 N13 C14 178.64(17) C12 N13 C14 C15 0.2(3) C12 N13 C14 C18 -178.9(2) N13 C14 C15 C16 0.7(3) C18 C14 C15 C16 179.7(2) C14 C15 C16 C17 -0.7(3) C14 C15 C16 C19 -179.0(2) N13 C12 C17 C16 1.1(3) N11 C12 C17 C16 -178.60(19) C15 C16 C17 C12 -0.2(3) C19 C16 C17 C12 178.2(2)