#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204403.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_2204403 loop_ _publ_author_name 'Erdem, Talip Kaya' 'Atalay, \,Sehriman' 'Akdemir, Nesuhi' 'Agundefinedar, Erbil' 'Kantar, Cihan' _publ_section_title ; 4-(2-Methoxy-4-methylphenoxy)phthalonitrile ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1849 _journal_page_last o1850 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C16 H12 N2 O2' _chemical_formula_moiety 'C16 H12 N2 O2' _chemical_formula_sum 'C16 H12 N2 O2' _chemical_formula_weight 264.28 _chemical_name_systematic ; ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _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 8.2319(5) _cell_length_b 22.7570(15) _cell_length_c 14.6764(8) _cell_measurement_reflns_used 18160 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.17 _cell_measurement_theta_min 1.39 _cell_volume 2749.4(3) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Stoe IPDS-II' _diffrn_measurement_method '\w scans' _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 0.1095 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 18348 _diffrn_reflns_theta_full 25.99 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_min 1.79 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_correction_T_min 0.9431 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.800 _exptl_crystal_size_mid 0.480 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.180 _refine_diff_density_min -0.146 _refine_ls_extinction_coef 0.0125(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2697 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.905 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0432 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0722P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1077 _refine_ls_wR_factor_ref 0.1172 _reflns_number_gt 1818 _reflns_number_total 2697 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn6271.cif _[local]_cod_data_source_block I _cod_database_code 2204403 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, 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_type_symbol C11 -0.1308(2) 0.24270(7) 0.17069(13) 0.0687(5) Uani d . 1 C H11 -0.1746 0.2179 0.1267 0.082 Uiso calc R 1 H C10 -0.0423(2) 0.29134(7) 0.14412(13) 0.0681(5) Uani d . 1 C H10 -0.0240 0.2987 0.0826 0.082 Uiso calc R 1 H C16 -0.2426(2) 0.17525(7) 0.28957(16) 0.0803(6) Uani d . 1 C H16A -0.2488 0.1736 0.3548 0.121 Uiso calc R 1 H H16B -0.1844 0.1416 0.2674 0.121 Uiso calc R 1 H H16C -0.3503 0.1754 0.2645 0.121 Uiso calc R 1 H C12 -0.15481(18) 0.23066(6) 0.26119(13) 0.0603(4) Uani d . 1 C C9 0.01844(17) 0.32862(6) 0.20885(12) 0.0554(4) Uani d . 1 C O1 0.12490(12) 0.37367(4) 0.18365(9) 0.0644(3) Uani d . 1 O C13 -0.09449(19) 0.26892(7) 0.32545(12) 0.0622(4) Uani d . 1 C H13 -0.1115 0.2612 0.3869 0.075 Uiso calc R 1 H C6 0.18283(17) 0.46790(6) 0.13533(11) 0.0528(4) Uani d . 1 C H6 0.2921 0.4576 0.1366 0.063 Uiso calc R 1 H C14 -0.00864(18) 0.31886(6) 0.30008(12) 0.0567(4) Uani d . 1 C C7 0.06508(17) 0.42713(6) 0.15951(10) 0.0493(3) Uani d . 1 C C5 0.13720(18) 0.52356(6) 0.10950(11) 0.0537(4) Uani d . 1 C H5 0.2160 0.5510 0.0936 0.064 Uiso calc R 1 H C8 -0.09738(17) 0.44113(6) 0.15837(10) 0.0516(4) Uani d . 1 C H8 -0.1753 0.4136 0.1750 0.062 Uiso calc R 1 H O2 0.05324(16) 0.35989(6) 0.35821(9) 0.0788(4) Uani d . 1 O C4 -0.02505(18) 0.53895(6) 0.10709(10) 0.0497(4) Uani d . 1 C C3 -0.14265(17) 0.49746(6) 0.13171(10) 0.0501(4) Uani d . 1 C C1 -0.0726(2) 0.59665(7) 0.07771(11) 0.0573(4) Uani d . 1 C C15 0.0322(4) 0.35043(13) 0.45241(17) 0.1157(9) Uani d . 1 C H15A 0.0810 0.3822 0.4857 0.174 Uiso calc R 1 H H15B 0.0831 0.3141 0.4694 0.174 Uiso calc R 1 H H15C -0.0816 0.3486 0.4662 0.174 Uiso calc R 1 H C2 -0.3110(2) 0.51361(7) 0.12917(13) 0.0649(5) Uani d . 1 C N1 -0.1087(2) 0.64250(6) 0.05374(11) 0.0780(5) Uani d . 1 N N2 -0.44391(19) 0.52754(8) 0.12662(16) 0.0973(6) Uani d . 1 N 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 C11 0.0762(11) 0.0536(9) 0.0763(12) -0.0075(8) -0.0057(9) -0.0001(8) C10 0.0746(11) 0.0633(10) 0.0666(11) -0.0055(8) -0.0023(9) 0.0084(8) C16 0.0733(11) 0.0527(10) 0.1150(16) -0.0067(8) -0.0017(11) 0.0199(10) C12 0.0524(8) 0.0447(8) 0.0839(12) 0.0022(6) -0.0025(8) 0.0100(8) C9 0.0481(8) 0.0446(8) 0.0734(11) -0.0003(6) 0.0015(7) 0.0101(7) O1 0.0520(6) 0.0504(6) 0.0909(9) -0.0018(4) 0.0025(5) 0.0164(6) C13 0.0595(9) 0.0569(9) 0.0702(11) -0.0001(7) 0.0019(8) 0.0116(8) C6 0.0455(7) 0.0526(8) 0.0602(9) -0.0048(6) 0.0026(6) -0.0015(7) C14 0.0510(8) 0.0497(8) 0.0694(10) -0.0006(6) -0.0009(7) 0.0023(7) C7 0.0502(7) 0.0453(7) 0.0524(8) -0.0036(6) -0.0001(6) 0.0026(6) C5 0.0543(8) 0.0480(8) 0.0588(9) -0.0120(6) 0.0065(7) -0.0008(6) C8 0.0506(8) 0.0462(7) 0.0580(9) -0.0088(6) 0.0026(6) 0.0041(6) O2 0.0841(8) 0.0753(8) 0.0769(9) -0.0205(6) 0.0017(7) -0.0106(6) C4 0.0578(8) 0.0425(7) 0.0489(8) -0.0056(6) 0.0030(6) -0.0012(6) C3 0.0490(8) 0.0495(8) 0.0517(8) -0.0032(6) 0.0003(6) 0.0002(6) C1 0.0663(9) 0.0492(8) 0.0564(9) -0.0037(7) 0.0050(7) -0.0015(7) C15 0.142(2) 0.132(2) 0.0729(14) -0.0373(17) 0.0049(14) -0.0211(14) C2 0.0554(9) 0.0573(9) 0.0820(12) -0.0045(7) 0.0021(8) 0.0127(8) N1 0.0998(12) 0.0535(8) 0.0808(11) 0.0061(8) 0.0068(9) 0.0073(7) N2 0.0537(9) 0.0884(11) 0.1499(19) 0.0018(8) 0.0008(9) 0.0303(11) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C12 C11 C10 120.64(17) ? C12 C11 H11 119.7 ? C10 C11 H11 119.7 ? C9 C10 C11 119.57(17) ? C9 C10 H10 120.2 ? C11 C10 H10 120.2 ? C12 C16 H16A 109.5 ? C12 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? C12 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? C11 C12 C13 119.06(15) ? C11 C12 C16 120.17(17) ? C13 C12 C16 120.75(17) ? C10 C9 C14 121.11(14) ? C10 C9 O1 119.99(15) ? C14 C9 O1 118.51(14) ? C7 O1 C9 119.87(11) y C12 C13 C14 121.16(17) ? C12 C13 H13 119.4 ? C14 C13 H13 119.4 ? C5 C6 C7 119.71(14) ? C5 C6 H6 120.1 ? C7 C6 H6 120.1 ? O2 C14 C9 115.97(14) ? O2 C14 C13 125.64(16) ? C9 C14 C13 118.40(15) ? O1 C7 C8 124.26(12) ? O1 C7 C6 114.32(13) ? C8 C7 C6 121.42(13) ? C6 C5 C4 120.33(13) ? C6 C5 H5 119.8 ? C4 C5 H5 119.8 ? C7 C8 C3 118.52(13) ? C7 C8 H8 120.7 ? C3 C8 H8 120.7 ? C14 O2 C15 117.58(15) y C5 C4 C3 119.42(13) ? C5 C4 C1 120.21(13) ? C3 C4 C1 120.36(13) ? C8 C3 C4 120.59(13) ? C8 C3 C2 120.15(13) ? C4 C3 C2 119.26(13) ? N1 C1 C4 179.13(19) ? O2 C15 H15A 109.5 ? O2 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? O2 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? N2 C2 C3 178.62(18) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C11 C12 1.370(2) ? C11 C10 1.382(2) ? C11 H11 0.9300 ? C10 C9 1.368(2) ? C10 H10 0.9300 ? C16 C12 1.512(2) ? C16 H16A 0.9600 ? C16 H16B 0.9600 ? C16 H16C 0.9600 ? C12 C13 1.376(2) ? C9 C14 1.375(2) ? C9 O1 1.3985(17) y O1 C7 1.3595(17) y C13 C14 1.389(2) ? C13 H13 0.9300 ? C6 C5 1.374(2) ? C6 C7 1.388(2) ? C6 H6 0.9300 ? C14 O2 1.3636(19) y C7 C8 1.375(2) ? C5 C4 1.381(2) ? C5 H5 0.9300 ? C8 C3 1.3911(19) ? C8 H8 0.9300 ? O2 C15 1.410(3) y C4 C3 1.3997(19) ? C4 C1 1.437(2) ? C3 C2 1.434(2) ? C1 N1 1.140(2) y C15 H15A 0.9600 ? C15 H15B 0.9600 ? C15 H15C 0.9600 ? C2 N2 1.140(2) y 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 C8 H8 O2 6_556 0.93 2.59 3.4276(18) 150 C16 H16C Cg2 6_556 0.96 2.99 3.6114(18) 124 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 C12 C11 C10 C9 -1.7(3) C10 C11 C12 C13 2.4(3) C10 C11 C12 C16 -176.04(16) C11 C10 C9 C14 -0.7(2) C11 C10 C9 O1 172.00(15) C10 C9 O1 C7 89.45(18) C14 C9 O1 C7 -97.67(17) C11 C12 C13 C14 -0.8(2) C16 C12 C13 C14 177.68(15) C10 C9 C14 O2 -177.98(14) O1 C9 C14 O2 9.2(2) C10 C9 C14 C13 2.3(2) O1 C9 C14 C13 -170.52(13) C12 C13 C14 O2 178.73(15) C12 C13 C14 C9 -1.6(2) C9 O1 C7 C8 0.4(2) C9 O1 C7 C6 -179.54(14) C5 C6 C7 O1 179.93(14) C5 C6 C7 C8 -0.1(2) C7 C6 C5 C4 -0.3(2) O1 C7 C8 C3 -179.60(14) C6 C7 C8 C3 0.4(2) C9 C14 O2 C15 -178.08(19) C13 C14 O2 C15 1.6(3) C6 C5 C4 C3 0.4(2) C6 C5 C4 C1 -178.31(15) C7 C8 C3 C4 -0.3(2) C7 C8 C3 C2 179.67(15) C5 C4 C3 C8 0.0(2) C1 C4 C3 C8 178.64(14) C5 C4 C3 C2 179.96(15) C1 C4 C3 C2 -1.4(2) C5 C4 C1 N1 27(14) C3 C4 C1 N1 -152(14) C8 C3 C2 N2 18E1(10) C4 C3 C2 N2 -1(10)