#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202535.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_2202535 loop_ _publ_author_name 'K\"oysal, Yavuz' 'I\,s\?ik, \,Samil' 'Akdemir, Nasuhi' 'Ag{\~}ar, Erbil' 'McKee, Vickie' _publ_section_title ; 4-(2-Allylphenoxy)phthalonitrile ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1183 _journal_page_last o1184 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C17 H12 N2 O' _chemical_formula_moiety 'C17 H12 N2 O' _chemical_formula_sum 'C17 H12 N2 O' _chemical_formula_weight 260.29 _chemical_name_systematic ; 4-(2-Allylphenoxy)phthalonitrile ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _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 4 _cell_length_a 14.1639(14) _cell_length_b 11.2630(11) _cell_length_c 8.6098(8) _cell_measurement_reflns_used 10384 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 28.74 _cell_measurement_theta_min 2.31 _cell_volume 1373.5(2) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'WinGX (Farrugia, 1997) and PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.939 _diffrn_measured_fraction_theta_max 0.939 _diffrn_measurement_device_type 'Bruker CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0184 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 9839 _diffrn_reflns_theta_full 28.74 _diffrn_reflns_theta_max 28.74 _diffrn_reflns_theta_min 2.31 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_correction_T_min 0.975 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.716 _refine_diff_density_min -0.383 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 1777 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0578 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1037P)^2^+0.3289P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1653 _refine_ls_wR_factor_ref 0.1782 _reflns_number_gt 1468 _reflns_number_total 1777 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cm6045.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_database_code 2202535 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, 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_type_symbol O1 0.00062(19) 0.9665(3) 0.3276(3) 0.0680(10) Uani d . 1 O N1 -0.1290(2) 0.6821(3) 0.8664(4) 0.0566(9) Uani d . 1 N N2 -0.3779(2) 0.8041(3) 0.7409(4) 0.0570(8) Uani d . 1 N C1 0.0937(2) 0.9295(3) 0.3524(4) 0.0454(8) Uani d . 1 C C2 0.1312(3) 0.8451(3) 0.2547(5) 0.0562(10) Uani d . 1 C C3 0.2269(4) 0.8242(4) 0.2694(6) 0.0680(13) Uani d . 1 C H3 0.2556 0.7693 0.2038 0.082 Uiso calc R 1 H C4 0.2813(3) 0.8825(5) 0.3787(7) 0.0728(15) Uani d . 1 C H4 0.3456 0.8669 0.3852 0.087 Uiso calc R 1 H C5 0.2408(3) 0.9636(4) 0.4780(6) 0.0637(11) Uani d . 1 C H5 0.2767 1.0015 0.5536 0.076 Uiso calc R 1 H C6 0.1454(3) 0.9874(4) 0.4626(5) 0.0540(9) Uani d . 1 C H6 0.1167 1.0427 0.5273 0.065 Uiso calc R 1 H C7 -0.2278(2) 0.8753(2) 0.5997(3) 0.0337(6) Uani d . 1 C C8 -0.2348(2) 0.9579(3) 0.4795(4) 0.0394(7) Uani d . 1 C H8 -0.2927 0.9929 0.4571 0.047 Uiso calc R 1 H C9 -0.1563(2) 0.9877(3) 0.3940(4) 0.0427(7) Uani d . 1 C H9 -0.1612 1.0435 0.3147 0.051 Uiso calc R 1 H C10 -0.0702(2) 0.9355(3) 0.4253(4) 0.0402(7) Uani d . 1 C C11 -0.0599(2) 0.8561(2) 0.5487(3) 0.0345(6) Uani d . 1 C H11 -0.0013 0.8238 0.5728 0.041 Uiso calc R 1 H C12 -0.1394(2) 0.8267(2) 0.6341(4) 0.0334(6) Uani d . 1 C C13 -0.1319(2) 0.7454(3) 0.7627(4) 0.0391(7) Uani d . 1 C C14 -0.3113(2) 0.8375(3) 0.6806(4) 0.0425(7) Uani d . 1 C C15 0.0744(6) 0.7811(4) 0.1316(8) 0.100(2) Uani d . 1 C H15A 0.0214 0.8310 0.1025 0.120 Uiso calc R 1 H H15B 0.1137 0.7713 0.0403 0.120 Uiso calc R 1 H C16 0.0371(5) 0.6617(4) 0.1777(9) 0.0871(18) Uani d . 1 C H16 0.0054 0.6206 0.0999 0.104 Uiso calc R 1 H C17 0.0422(4) 0.6098(5) 0.3042(8) 0.0832(16) Uani d . 1 C H17A 0.0728 0.6457 0.3874 0.100 Uiso calc R 1 H H17B 0.0154 0.5350 0.3159 0.100 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 O1 0.0394(14) 0.108(3) 0.0566(18) 0.0083(14) 0.0076(13) 0.0453(18) N1 0.0470(17) 0.0600(17) 0.063(2) -0.0046(14) -0.0016(16) 0.0265(17) N2 0.0377(15) 0.072(2) 0.062(2) -0.0062(14) 0.0061(15) 0.0066(17) C1 0.0392(17) 0.0536(18) 0.0434(17) -0.0014(14) 0.0071(15) 0.0189(15) C2 0.082(3) 0.0440(17) 0.0430(19) 0.0031(17) -0.0030(19) 0.0125(16) C3 0.081(3) 0.063(2) 0.060(2) 0.030(2) 0.018(2) 0.024(2) C4 0.0383(19) 0.091(3) 0.089(4) 0.011(2) 0.011(2) 0.055(3) C5 0.053(2) 0.074(2) 0.064(3) -0.0108(19) -0.010(2) 0.024(2) C6 0.064(2) 0.056(2) 0.0423(19) 0.0059(17) -0.0001(17) 0.0080(17) C7 0.0343(15) 0.0351(13) 0.0318(14) -0.0032(11) -0.0010(11) -0.0041(11) C8 0.0394(17) 0.0401(14) 0.0386(16) 0.0054(12) -0.0030(14) 0.0002(13) C9 0.0429(18) 0.0491(17) 0.0359(16) 0.0018(14) -0.0032(13) 0.0076(14) C10 0.0388(16) 0.0496(16) 0.0322(14) -0.0003(13) 0.0020(13) 0.0079(13) C11 0.0330(15) 0.0398(13) 0.0309(14) -0.0004(11) -0.0027(11) 0.0045(12) C12 0.0355(15) 0.0321(13) 0.0326(13) -0.0036(11) -0.0020(11) 0.0000(11) C13 0.0319(14) 0.0421(14) 0.0431(16) -0.0022(12) -0.0003(13) 0.0071(14) C14 0.0356(17) 0.0462(16) 0.0457(18) -0.0003(12) -0.0027(15) -0.0009(15) C15 0.165(6) 0.049(2) 0.085(4) -0.002(3) -0.052(4) 0.005(2) C16 0.099(4) 0.054(2) 0.109(5) 0.008(2) -0.023(4) -0.011(3) C17 0.058(3) 0.094(4) 0.098(4) 0.004(3) -0.007(3) -0.003(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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 C10 O1 C1 121.8(3) yes C6 C1 C2 123.2(4) ? C6 C1 O1 118.1(4) ? C2 C1 O1 118.4(4) ? C1 C2 C3 116.1(4) ? C1 C2 C15 123.5(5) ? C3 C2 C15 120.3(5) ? C4 C3 C2 121.8(4) ? C4 C3 H3 119.1 ? C2 C3 H3 119.1 ? C5 C4 C3 120.4(4) ? C5 C4 H4 119.8 ? C3 C4 H4 119.8 ? C4 C5 C6 118.4(5) ? C4 C5 H5 120.8 ? C6 C5 H5 120.8 ? C1 C6 C5 119.9(4) ? C1 C6 H6 120.0 ? C5 C6 H6 120.0 ? C12 C7 C8 118.9(3) ? C12 C7 C14 121.2(3) ? C8 C7 C14 119.9(3) ? C9 C8 C7 120.1(3) ? C9 C8 H8 119.9 ? C7 C8 H8 119.9 ? C8 C9 C10 120.4(3) ? C8 C9 H9 119.8 ? C10 C9 H9 119.8 ? O1 C10 C9 115.1(3) ? O1 C10 C11 124.0(3) ? C9 C10 C11 120.9(3) ? C12 C11 C10 118.2(3) ? C12 C11 H11 120.9 ? C10 C11 H11 120.9 ? C11 C12 C7 121.4(3) ? C11 C12 C13 120.0(3) ? C7 C12 C13 118.6(3) ? N1 C13 C12 177.6(4) ? N2 C14 C7 177.4(4) ? C16 C15 C2 115.5(5) ? C16 C15 H15A 108.4 ? C2 C15 H15A 108.4 ? C16 C15 H15B 108.4 ? C2 C15 H15B 108.4 ? H15A C15 H15B 107.5 ? C17 C16 C15 129.5(6) ? C17 C16 H16 115.2 ? C15 C16 H16 115.2 ? C16 C17 H17A 120.0 ? C16 C17 H17B 120.0 ? H17A C17 H17B 120.0 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C10 1.355(4) yes O1 C1 1.399(4) yes N1 C13 1.144(5) yes N2 C14 1.141(5) yes C1 C6 1.365(6) ? C1 C2 1.377(6) ? C2 C3 1.382(7) ? C2 C15 1.513(7) ? C3 C4 1.382(8) ? C3 H3 0.9300 ? C4 C5 1.375(8) ? C4 H4 0.9300 ? C5 C6 1.383(6) ? C5 H5 0.9300 ? C6 H6 0.9300 ? C7 C12 1.397(4) ? C7 C8 1.395(4) ? C7 C14 1.437(5) ? C8 C9 1.375(5) ? C8 H8 0.9300 ? C9 C10 1.380(5) ? C9 H9 0.9300 ? C10 C11 1.397(4) ? C11 C12 1.385(4) ? C11 H11 0.9300 ? C12 C13 1.440(4) ? C15 C16 1.498(7) yes C15 H15A 0.9700 ? C15 H15B 0.9700 ? C16 C17 1.238(9) yes C16 H16 0.9300 ? C17 H17A 0.9300 ? C17 H17B 0.9300 ? 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 N1 3_454 0.93 2.53 3.325(3) 144 C15 H15A O1 . 0.97 2.49 2.884(5) 104 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 C10 O1 C1 C6 -77.8(5) C10 O1 C1 C2 108.5(4) C6 C1 C2 C3 -2.5(5) O1 C1 C2 C3 170.9(3) C6 C1 C2 C15 -179.6(4) O1 C1 C2 C15 -6.3(5) C1 C2 C3 C4 1.6(6) C15 C2 C3 C4 178.9(4) C2 C3 C4 C5 0.4(6) C3 C4 C5 C6 -1.8(6) C2 C1 C6 C5 1.2(5) O1 C1 C6 C5 -172.2(4) C4 C5 C6 C1 1.0(6) C12 C7 C8 C9 1.9(5) C14 C7 C8 C9 -175.1(3) C7 C8 C9 C10 0.6(5) C1 O1 C10 C9 174.1(4) C1 O1 C10 C11 -6.5(6) C8 C9 C10 O1 176.2(3) C8 C9 C10 C11 -3.2(5) O1 C10 C11 C12 -176.2(3) C9 C10 C11 C12 3.1(5) C10 C11 C12 C7 -0.5(4) C10 C11 C12 C13 -179.8(3) C8 C7 C12 C11 -2.0(4) C14 C7 C12 C11 175.0(3) C8 C7 C12 C13 177.3(3) C14 C7 C12 C13 -5.7(4) C11 C12 C13 N1 167(9) C7 C12 C13 N1 -13(9) C12 C7 C14 N2 -85(9) C8 C7 C14 N2 92(9) C1 C2 C15 C16 -96.5(6) C3 C2 C15 C16 86.5(7) C2 C15 C16 C17 3.7(11)