#------------------------------------------------------------------------------ #$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/74/2007439.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_2007439 loop_ _publ_author_name 'Elmali, Ayhan' 'Elerman, Yal\;cin' 'Svoboda, Ingrid' 'Fuess, Hartmut' _publ_section_title ; N-(3,5-Dichlorophenyl)naphthaldimine ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 974 _journal_page_last 976 _journal_paper_doi 10.1107/S0108270198001176 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C17 H11 Cl2 N O' _chemical_formula_sum 'C17 H11 Cl2 N O' _chemical_formula_weight 316.19 _chemical_name_systematic ; ? ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.7410(9) _cell_length_b 15.293(5) _cell_length_c 19.610(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.00 _cell_measurement_theta_min 2.47 _cell_volume 1421.8(6) _computing_cell_refinement ; Nonius diffractometer control software (Nonius, 1993) ; _computing_data_collection ; Nonius diffractometer control software (Nonius, 1993) ; _computing_data_reduction 'REDU4 (Stoe & Cie, 1991)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL93 (Sheldrick, 1993)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71093 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 2326 _diffrn_reflns_theta_max 25.47 _diffrn_reflns_theta_min 1.69 _diffrn_standards_decay_% 3.7 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.453 _exptl_absorpt_correction_T_max 0.900 _exptl_absorpt_correction_T_min 0.818 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ' (North, Phillips & Mathews, 1968) ' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.525 _exptl_crystal_size_mid 0.325 _exptl_crystal_size_min 0.275 _refine_diff_density_max 0.158 _refine_diff_density_min -0.183 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.077 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_hydrogen_treatment H_atoms:_see_text_below _refine_ls_matrix_type full _refine_ls_number_parameters 194 _refine_ls_number_reflns 2240 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.077 _refine_ls_restrained_S_obs 1.084 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_obs .0358 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.2183P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1034 _refine_ls_wR_factor_obs .0954 _reflns_number_observed 1912 _reflns_number_total 2240 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ha1210.cif _cod_data_source_block ha1210 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.2183P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.2183P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2007439 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' 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 .0469(15) .0529(13) .0393(11) .0070(12) -.0017(11) .0033(9) C2 .061(2) .0543(14) .0432(12) .0060(13) -.0001(12) -.0026(11) C3 .060(2) .0557(14) .0470(12) -.0027(13) -.0058(14) .0062(11) C4 .061(2) .067(2) .0426(11) .001(2) .0001(13) .0073(11) C5 .060(2) .063(2) .0431(12) .0102(15) .0039(13) -.0019(12) C6 .057(2) .0521(14) .0513(14) .0024(13) .0027(13) -.0025(11) C7 .050(2) .0553(14) .0403(11) .0084(13) -.0036(11) -.0034(10) C8 .045(2) .0509(13) .0416(11) .0050(11) -.0056(11) .0021(10) C9 .055(2) .0545(15) .0431(12) .0035(13) -.0021(12) .0010(10) C10 .064(2) .059(2) .0457(13) .0083(14) .0055(14) -.0011(11) C11 .059(2) .072(2) .0438(12) .006(2) .0032(13) .0108(12) C12 .048(2) .058(2) .0491(13) .0019(13) -.0072(12) .0109(12) C13 .042(2) .0545(13) .0464(11) .0072(12) -.0099(12) .0021(10) C14 .056(2) .067(2) .067(2) -.001(2) -.004(2) -.0141(14) C15 .063(2) .071(2) .096(2) -.001(2) -.010(2) -.025(2) C16 .062(2) .061(2) .102(2) -.008(2) -.018(2) .001(2) C17 .054(2) .068(2) .078(2) -.004(2) -.009(2) .016(2) N1 .0518(15) .0554(12) .0437(10) .0031(11) .0034(10) -.0004(9) O1 .072(2) .0554(11) .0639(12) -.0034(11) .0151(12) -.0103(9) Cl1 .1136(8) .0681(4) .0637(4) -.0262(5) .0019(5) .0031(4) Cl2 .1143(9) .0839(6) .0733(5) .0039(6) .0361(6) -.0225(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol C1 -.3818(6) .3395(2) .16654(11) .0464(6) Uani d . 1 . C C2 -.5050(6) .2577(2) .16305(12) .0527(7) Uani d . 1 . C H2 -.4577 .2198 .1278 .055 Uiso calc . 1 . H C3 -.6964(7) .2325(2) .21142(13) .0544(7) Uani d . 1 . C C4 -.7789(7) .2867(2) .26323(12) .0568(7) Uani d . 1 . C H4 -.9120 .2692 .2953 .069 Uiso calc . 1 . H C5 -.6563(6) .3685(2) .26595(12) .0554(7) Uani d . 1 . C C6 -.4602(7) .3960(2) .21931(13) .0535(7) Uani d . 1 . C H6 -.3804 .4514 .2227 .085 Uiso calc . 1 . H C7 -.0423(6) .4320(2) .11527(12) .0486(6) Uani d . 1 . C H7 -.0804 .4734 .1488 .061 Uiso calc . 1 . H C8 .1662(6) .4514(2) .06557(12) .0458(6) Uani d . 1 . C C9 .2318(7) .3897(2) .01483(12) .0510(6) Uani d . 1 . C C10 .4432(7) .4063(2) -.03311(13) .0561(7) Uani d . 1 . C H10 .4886 .3638 -.0653 .066 Uiso calc . 1 . H C11 .5829(7) .4837(2) -.03320(13) .0581(7) Uani d . 1 . C H11 .7214 .4938 -.0658 .055 Uiso calc . 1 . H C12 .5216(6) .5494(2) .01548(13) .0516(7) Uani d . 1 . C C13 .3164(6) .5333(2) .06605(12) .0478(6) Uani d . 1 . C C14 .2687(7) .6001(2) .11445(15) .0635(7) Uani d . 1 . C H14 .1377 .5912 .1491 .062 Uiso calc . 1 . H C15 .4110(8) .6771(2) .1113(2) .0764(10) Uani d . 1 . C H15 .3737 .7203 .1434 .105 Uiso calc . 1 . H C16 .6098(8) .6925(2) .0614(2) .0751(9) Uani d . 1 . C H16 .7054 .7455 .0600 .089 Uiso calc . 1 . H C17 .6651(7) .6299(2) .0144(2) .0668(8) Uani d . 1 . C H17 .7999 .6403 -.0191 .067 Uiso calc . 1 . H N1 -.1813(5) .35947(14) .11597(10) .0503(5) Uani d . 1 . N O1 .0996(5) .31375(13) .00970(11) .0637(6) Uani d . 1 . O H1O -.017(11) .313(3) .041(2) .115(17) Uiso d . 1 . H Cl1 -.8446(2) .12860(6) .20800(4) .0818(3) Uani d . 1 . Cl Cl2 -.7513(2) .43790(6) .33210(4) .0905(4) Uani d . 1 . Cl loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0020 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 0.0040 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0080 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1320 0.1590 '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 C2 C1 C6 118.9(3) ? C2 C1 N1 116.6(2) y C6 C1 N1 124.5(2) y C3 C2 C1 120.1(2) ? C3 C2 H2 120.0(3) ? C1 C2 H2 120.0(3) ? C2 C3 C4 122.2(3) ? C2 C3 Cl1 119.9(2) y C4 C3 Cl1 117.9(2) y C3 C4 C5 117.2(3) ? C3 C4 H4 121.4(3) ? C5 C4 H4 121.4(3) ? C6 C5 C4 122.5(2) ? C6 C5 Cl2 119.2(2) y C4 C5 Cl2 118.3(2) y C5 C6 C1 119.0(3) ? C5 C6 H6 120.5(3) ? C1 C6 H6 120.5(3) ? N1 C7 C8 122.8(2) y N1 C7 H7 118.6(3) ? C8 C7 H7 118.6(3) ? C9 C8 C7 120.0(2) ? C9 C8 C13 118.6(2) ? C7 C8 C13 121.4(2) ? O1 C9 C10 116.6(2) y O1 C9 C8 122.5(3) y C10 C9 C8 120.8(3) ? C11 C10 C9 120.6(2) ? C11 C10 H10 119.7(3) ? C9 C10 H10 119.7(3) ? C10 C11 C12 121.2(3) ? C10 C11 H11 119.4(3) ? C12 C11 H11 119.4(3) ? C17 C12 C13 119.8(3) ? C17 C12 C11 120.8(3) ? C13 C12 C11 119.4(3) ? C12 C13 C14 117.2(3) ? C12 C13 C8 119.2(2) ? C14 C13 C8 123.6(2) ? C15 C14 C13 121.1(3) ? C15 C14 H14 119.5(3) ? C13 C14 H14 119.5(3) ? C14 C15 C16 121.3(3) ? C14 C15 H15 119.4(4) ? C16 C15 H15 119.4(4) ? C17 C16 C15 119.7(3) ? C17 C16 H16 120.2(4) ? C15 C16 H16 120.2(4) ? C16 C17 C12 121.0(3) ? C16 C17 H17 119.5(3) ? C12 C17 H17 119.5(3) ? C7 N1 C1 122.6(2) y C9 O1 H1O 106.(3) ? 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 C2 . 1.382(4) ? C1 C6 . 1.398(3) ? C1 N1 . 1.407(3) y C2 C3 . 1.368(4) ? C2 H2 . .930(3) ? C3 C4 . 1.369(4) ? C3 Cl1 . 1.738(3) y C4 C5 . 1.380(4) ? C4 H4 . .930(3) ? C5 C6 . 1.370(4) ? C5 Cl2 . 1.735(3) y C6 H6 . .930(3) ? C7 N1 . 1.290(3) y C7 C8 . 1.420(4) ? C7 H7 . .930(2) ? C8 C9 . 1.406(3) ? C8 C13 . 1.442(4) ? C9 O1 . 1.323(3) y C9 C10 . 1.397(4) ? C10 C11 . 1.357(4) ? C10 H10 . .930(3) ? C11 C12 . 1.416(4) ? C11 H11 . .930(3) ? C12 C17 . 1.406(4) ? C12 C13 . 1.411(4) ? C13 C14 . 1.412(4) ? C14 C15 . 1.359(4) ? C14 H14 . .930(3) ? C15 C16 . 1.379(5) ? C15 H15 . .930(3) ? C16 C17 . 1.353(5) ? C16 H16 . .930(3) ? C17 H17 . .930(3) ? O1 H1O . .83(5) ? 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 C6 C1 C2 C3 -1.2(4) N1 C1 C2 C3 178.3(2) C1 C2 C3 C4 1.8(4) C1 C2 C3 Cl1 -178.5(2) C2 C3 C4 C5 -1.3(4) Cl1 C3 C4 C5 179.0(2) C3 C4 C5 C6 0.1(4) C3 C4 C5 Cl2 -178.7(2) C4 C5 C6 C1 0.5(4) Cl2 C5 C6 C1 179.3(2) C2 C1 C6 C5 0.1(4) N1 C1 C6 C5 -179.3(3) N1 C7 C8 C9 -1.0(4) N1 C7 C8 C13 179.6(2) C7 C8 C9 O1 2.2(4) C13 C8 C9 O1 -178.3(2) C7 C8 C9 C10 -177.8(3) C13 C8 C9 C10 1.6(4) O1 C9 C10 C11 177.6(3) C8 C9 C10 C11 -2.4(4) C9 C10 C11 C12 0.7(4) C10 C11 C12 C17 -179.2(3) C10 C11 C12 C13 1.6(4) C17 C12 C13 C14 -0.9(4) C11 C12 C13 C14 178.3(3) C17 C12 C13 C8 178.5(2) C11 C12 C13 C8 -2.2(4) C9 C8 C13 C12 0.6(3) C7 C8 C13 C12 -180.0(2) C9 C8 C13 C14 -180.0(3) C7 C8 C13 C14 -0.6(4) C12 C13 C14 C15 1.3(4) C8 C13 C14 C15 -178.1(3) C13 C14 C15 C16 -0.9(5) C14 C15 C16 C17 0.1(6) C15 C16 C17 C12 0.3(5) C13 C12 C17 C16 0.1(4) C11 C12 C17 C16 -179.1(3) C8 C7 N1 C1 178.1(2) C2 C1 N1 C7 -176.9(2) C6 C1 N1 C7 2.5(4)