#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/36/2203613.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_2203613 loop_ _publ_author_name 'Din\,cer, Muharrem' '\"Ozdemir, Nam\?ik' 'Akdemir, Nesuhi' '\"Ozdil, Musa' 'A\(gar, Erbil' 'B\"uy\"ukg\"ung\"or, Orhan' _publ_section_title ; 4-(1-Indanyloxy)phthalonitrile ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o896 _journal_page_last o898 _journal_volume 60 _journal_year 2004 _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-(1-Indanyloxy)phthalonitrile ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 117.069(14) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.0560(16) _cell_length_b 23.950(3) _cell_length_c 7.8057(16) _cell_measurement_reflns_used 2365 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22.90 _cell_measurement_theta_min 1.70 _cell_volume 1341.1(5) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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 'plane graphite' _diffrn_radiation_source 'sealed X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.1300 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 9063 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 1.70 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.9984 _exptl_absorpt_correction_T_min 0.9785 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.119 _refine_diff_density_min -0.186 _refine_ls_extinction_coef 0.0034(3) _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 0.741 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 170 _refine_ls_number_reflns 2498 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.741 _refine_ls_R_factor_all 0.1609 _refine_ls_R_factor_gt 0.0398 _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^)+(0.0101P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.0665 _reflns_number_gt 767 _reflns_number_total 2498 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hg6038.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Integration' changed to 'integration' 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: '_exptl_absorpt_correction_type' value 'Integration' changed to 'integration' 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 1341.1(4) _cod_database_code 2203613 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_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 0.1628(3) 0.40707(8) 0.4057(3) 0.0681(6) Uani d . 1 O N1 0.3542(4) 0.13418(10) 0.5837(4) 0.1040(10) Uani d . 1 N N2 0.7112(4) 0.24887(12) 0.9371(4) 0.0879(9) Uani d . 1 N C1 0.3205(4) 0.18084(13) 0.5546(4) 0.0657(6) Uani d . 1 C C2 0.2815(4) 0.23916(13) 0.5210(4) 0.0657(6) Uani d . 1 C C3 0.1200(4) 0.25757(12) 0.3659(4) 0.0651(9) Uani d . 1 C H3 0.0353 0.2318 0.2829 0.078 Uiso calc R 1 H C4 0.0842(4) 0.31382(12) 0.3339(4) 0.0636(8) Uani d . 1 C H4 -0.0253 0.3258 0.2303 0.076 Uiso calc R 1 H C5 0.2095(4) 0.35265(12) 0.4545(4) 0.0598(8) Uani d . 1 C C6 0.3713(4) 0.33539(12) 0.6112(4) 0.0614(8) Uani d . 1 C H6 0.4550 0.3614 0.6943 0.074 Uiso calc R 1 H C7 0.4064(4) 0.27865(11) 0.6421(4) 0.0628(6) Uani d . 1 C C8 0.5773(4) 0.26110(12) 0.8064(4) 0.0628(6) Uani d . 1 C C9 0.2969(4) 0.44940(11) 0.5174(4) 0.0626(8) Uani d . 1 C H9 0.4225 0.4382 0.5410 0.075 Uiso calc R 1 H C10 0.2443(4) 0.50360(12) 0.4093(4) 0.0582(8) Uani d . 1 C C11 0.2046(4) 0.51241(12) 0.2207(4) 0.0727(9) Uani d . 1 C H11 0.2049 0.4830 0.1430 0.087 Uiso calc R 1 H C12 0.1637(4) 0.56676(14) 0.1489(5) 0.0817(10) Uani d . 1 C H12 0.1318 0.5738 0.0204 0.098 Uiso calc R 1 H C13 0.1705(4) 0.61032(13) 0.2693(6) 0.0833(11) Uani d . 1 C H13 0.1456 0.6465 0.2212 0.100 Uiso calc R 1 H C14 0.2136(4) 0.60071(13) 0.4582(5) 0.0770(10) Uani d . 1 C H14 0.2191 0.6300 0.5387 0.092 Uiso calc R 1 H C15 0.2485(4) 0.54659(14) 0.5263(4) 0.0652(9) Uani d . 1 C C16 0.2994(5) 0.52598(12) 0.7260(4) 0.0854(10) Uani d . 1 C H16A 0.2104 0.5389 0.7688 0.102 Uiso calc R 1 H H16B 0.4229 0.5387 0.8163 0.102 Uiso calc R 1 H C17 0.2939(4) 0.46255(12) 0.7077(4) 0.0798(10) Uani d . 1 C H17A 0.1816 0.4479 0.7073 0.096 Uiso calc R 1 H H17B 0.4011 0.4460 0.8144 0.096 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 0.0636(14) 0.0512(13) 0.0704(14) -0.0076(12) 0.0137(11) 0.0003(12) N1 0.133(3) 0.0666(18) 0.101(2) 0.013(2) 0.043(2) -0.0006(18) N2 0.082(2) 0.085(2) 0.0776(19) 0.0043(17) 0.0201(16) 0.0106(16) C1 0.0784(18) 0.0566(13) 0.0589(14) 0.0011(17) 0.0285(13) -0.0023(15) C2 0.0784(18) 0.0566(13) 0.0589(14) 0.0011(17) 0.0285(13) -0.0023(15) C3 0.070(2) 0.060(2) 0.065(2) -0.015(2) 0.0293(19) -0.0095(18) C4 0.060(2) 0.062(2) 0.0578(19) -0.0026(19) 0.0177(16) -0.0030(18) C5 0.064(2) 0.049(2) 0.068(2) -0.002(2) 0.0316(19) 0.0010(19) C6 0.061(2) 0.056(2) 0.062(2) -0.0059(18) 0.0234(18) -0.0036(17) C7 0.0722(18) 0.0600(15) 0.0599(16) 0.0037(15) 0.0333(13) 0.0063(14) C8 0.0722(18) 0.0600(15) 0.0599(16) 0.0037(15) 0.0333(13) 0.0063(14) C9 0.064(2) 0.053(2) 0.064(2) -0.0092(19) 0.0232(17) -0.0022(18) C10 0.058(2) 0.0512(19) 0.064(2) -0.0057(18) 0.0258(17) -0.0034(19) C11 0.080(2) 0.060(2) 0.072(2) 0.002(2) 0.0294(19) -0.0057(19) C12 0.084(3) 0.079(2) 0.069(2) -0.002(2) 0.023(2) 0.009(2) C13 0.074(3) 0.062(2) 0.111(3) 0.005(2) 0.039(2) 0.014(2) C14 0.078(3) 0.062(2) 0.095(3) 0.003(2) 0.044(2) -0.009(2) C15 0.062(2) 0.059(2) 0.072(2) -0.0034(19) 0.0284(19) -0.004(2) C16 0.099(3) 0.082(2) 0.078(2) -0.003(2) 0.043(2) -0.010(2) C17 0.090(3) 0.082(2) 0.059(2) -0.012(2) 0.0269(19) -0.0019(19) 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 C5 O1 C9 117.8(2) yes N1 C1 C2 179.0(4) yes C3 C2 C7 118.6(3) ? C3 C2 C1 120.8(3) yes C7 C2 C1 120.6(3) yes C4 C3 C2 120.4(3) ? C4 C3 H3 119.8 ? C2 C3 H3 119.8 ? C3 C4 C5 120.5(3) ? C3 C4 H4 119.7 ? C5 C4 H4 119.7 ? O1 C5 C4 115.5(3) yes O1 C5 C6 124.2(3) yes C4 C5 C6 120.3(3) ? C7 C6 C5 118.8(3) ? C7 C6 H6 120.6 ? C5 C6 H6 120.6 ? C6 C7 C2 121.4(3) ? C6 C7 C8 118.3(3) yes C2 C7 C8 120.3(3) yes N2 C8 C7 178.0(3) yes O1 C9 C10 109.0(2) yes O1 C9 C17 113.1(2) yes C10 C9 C17 104.1(2) ? O1 C9 H9 110.2 ? C10 C9 H9 110.2 ? C17 C9 H9 110.2 ? C15 C10 C11 121.6(3) ? C15 C10 C9 111.2(3) ? C11 C10 C9 127.2(3) ? C10 C11 C12 118.1(3) ? C10 C11 H11 120.9 ? C12 C11 H11 120.9 ? C13 C12 C11 120.0(3) ? C13 C12 H12 120.0 ? C11 C12 H12 120.0 ? C14 C13 C12 120.9(3) ? C14 C13 H13 119.5 ? C12 C13 H13 119.5 ? C13 C14 C15 118.6(3) ? C13 C14 H14 120.7 ? C15 C14 H14 120.7 ? C10 C15 C14 120.7(3) ? C10 C15 C16 111.0(3) ? C14 C15 C16 128.3(3) ? C15 C16 C17 104.3(2) ? C15 C16 H16A 110.9 ? C17 C16 H16A 110.9 ? C15 C16 H16B 110.9 ? C17 C16 H16B 110.9 ? H16A C16 H16B 108.9 ? C16 C17 C9 106.5(2) ? C16 C17 H17A 110.4 ? C9 C17 H17A 110.4 ? C16 C17 H17B 110.4 ? C9 C17 H17B 110.4 ? H17A C17 H17B 108.6 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C5 1.362(3) yes O1 C9 1.448(3) yes N1 C1 1.148(3) ? N2 C8 1.135(3) ? C1 C2 1.430(4) yes C2 C3 1.385(3) ? C2 C7 1.391(3) ? C3 C4 1.377(3) ? C3 H3 0.9300 ? C4 C5 1.380(3) ? C4 H4 0.9300 ? C5 C6 1.384(3) ? C6 C7 1.387(3) ? C6 H6 0.9300 ? C7 C8 1.452(3) yes C9 C10 1.500(3) ? C9 C17 1.529(3) yes C9 H9 0.9800 ? C10 C15 1.367(3) yes C10 C11 1.373(3) ? C11 C12 1.396(3) ? C11 H11 0.9300 ? C12 C13 1.388(4) ? C12 H12 0.9300 ? C13 C14 1.372(4) ? C13 H13 0.9300 ? C14 C15 1.381(4) ? C14 H14 0.9300 ? C15 C16 1.503(3) ? C16 C17 1.525(3) yes C16 H16A 0.9700 ? C16 H16B 0.9700 ? C17 H17A 0.9700 ? C17 H17B 0.9700 ? 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 C9 H9 Cg3 3_657 0.98 2.689 3.625(4) 160 C17 H17A Cg3 3_557 0.97 2.993 3.917(4) 160 _cod_database_fobs_code 2203613