#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200881.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_2200881 loop_ _publ_author_name 'J. Z. Tian' 'Anwar Usman' 'Ibrahim Abdul Razak' 'Hoong-Kun Fun' 'Suchada Chantrapromma' 'Yan Zhang' 'Jian-Hua Xu' _publ_section_title ; 3-[(Diphenylmethylene)amino]phthalonitrile ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o151 _journal_page_last o153 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C21 H13 N3' _chemical_formula_moiety 'C21 H13 N3' _chemical_formula_sum 'C21 H13 N3' _chemical_formula_weight 307.34 _chemical_melting_point 415 _chemical_name_systematic ; 3-[(diphenylmethylene)amino]phthalonitrile ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/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 91.6480(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 15.3572(2) _cell_length_b 8.0212(2) _cell_length_c 26.7363(2) _cell_measurement_reflns_used 4600 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 28.34 _cell_measurement_theta_min 2.65 _cell_volume 3292.10(10) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 183(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .960 _diffrn_measured_fraction_theta_max .960 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .072 _diffrn_reflns_av_sigmaI/netI .1157 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 9550 _diffrn_reflns_theta_full 28.31 _diffrn_reflns_theta_max 28.31 _diffrn_reflns_theta_min 2.65 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .075 _exptl_absorpt_correction_T_max .991 _exptl_absorpt_correction_T_min .968 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 1280 _exptl_crystal_size_max .44 _exptl_crystal_size_mid .28 _exptl_crystal_size_min .12 _refine_diff_density_max .32 _refine_diff_density_min -.28 _refine_ls_extinction_coef .0092(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXTL _refine_ls_goodness_of_fit_ref .86 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 270 _refine_ls_number_reflns 3941 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .86 _refine_ls_R_factor_all .098 _refine_ls_R_factor_gt .058 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0427P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .121 _refine_ls_wR_factor_ref .133 _reflns_number_gt 2251 _reflns_number_total 3941 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6095.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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 2200881 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 .22150(9) .84975(19) .10963(6) .0279(4) Uani d . 1 . . N N2 .19821(13) .4134(2) .08851(7) .0509(5) Uani d . 1 . . N N3 .08426(13) .3948(2) -.04913(7) .0522(5) Uani d . 1 . . N C1 .15900(11) .6853(2) .04099(6) .0239(4) Uani d . 1 . . C C2 .11877(11) .6775(2) -.00667(7) .0270(4) Uani d . 1 . . C C3 .09587(13) .8221(3) -.03202(8) .0336(5) Uani d . 1 . . C C4 .11367(13) .9748(3) -.00990(8) .0352(5) Uani d . 1 . . C C5 .15260(12) .9842(3) .03692(8) .0307(5) Uani d . 1 . . C C6 .17479(11) .8396(2) .06354(7) .0248(4) Uani d . 1 . . C C7 .18770(11) .9144(2) .14858(7) .0239(4) Uani d . 1 . . C C8 .09427(11) .9638(2) .15342(6) .0238(4) Uani d . 1 . . C C9 .02584(11) .8638(2) .13568(7) .0267(4) Uani d . 1 . . C C10 -.05977(12) .9171(3) .14011(7) .0316(5) Uani d . 1 . . C C11 -.07742(13) 1.0700(3) .16165(7) .0343(5) Uani d . 1 . . C C12 -.00998(13) 1.1678(3) .17970(8) .0383(5) Uani d . 1 . . C C13 .07541(13) 1.1147(2) .17596(8) .0335(5) Uani d . 1 . . C C14 .24825(11) .9502(2) .19195(7) .0237(4) Uani d . 1 . . C C15 .33116(11) 1.0126(2) .18295(7) .0276(4) Uani d . 1 . . C C16 .38705(12) 1.0514(3) .22294(8) .0328(5) Uani d . 1 . . C C17 .36235(13) 1.0232(3) .27153(8) .0336(5) Uani d . 1 . . C C18 .28037(13) .9594(2) .28057(8) .0324(5) Uani d . 1 . . C C19 .22273(12) .9268(2) .24103(7) .0288(4) Uani d . 1 . . C C20 .18153(13) .5345(2) .06764(7) .0318(5) Uani d . 1 . . C C21 .10048(13) .5187(3) -.02987(7) .0340(5) Uani d . 1 . . C H9 .0388(11) .753(3) .1199(7) .036(5) Uiso d . 1 . . H H12 -.0211(12) 1.270(3) .1980(8) .050(6) Uiso d . 1 . . H H16 .4446(13) 1.096(2) .2162(7) .034(5) Uiso d . 1 . . H H5 .1656(12) 1.090(2) .0511(7) .035(5) Uiso d . 1 . . H H3 .0686(12) .815(2) -.0653(8) .041(6) Uiso d . 1 . . H H11 -.1394(13) 1.108(3) .1646(7) .045(6) Uiso d . 1 . . H H19 .1622(13) .880(3) .2479(8) .045(6) Uiso d . 1 . . H H10 -.1055(14) .843(3) .1265(8) .050(6) Uiso d . 1 . . H H13 .1243(13) 1.186(2) .1899(7) .045(6) Uiso d . 1 . . H H4 .0990(12) 1.073(3) -.0271(8) .038(6) Uiso d . 1 . . H H18 .2633(12) .943(3) .3170(8) .046(6) Uiso d . 1 . . H H17 .4025(12) 1.047(2) .3004(8) .039(6) Uiso d . 1 . . H H15 .3464(12) 1.032(2) .1471(8) .043(6) Uiso d . 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 N1 .0306(8) .0281(9) .0246(9) .0020(6) -.0041(7) -.0077(7) N2 .0834(15) .0359(11) .0328(11) .0039(10) -.0085(10) .0035(9) N3 .0747(14) .0420(12) .0396(11) -.0150(10) -.0049(10) -.0130(9) C1 .0262(9) .0251(10) .0203(9) -.0009(7) .0016(7) -.0023(7) C2 .0324(10) .0289(11) .0199(10) -.0040(8) .0006(8) -.0044(8) C3 .0419(11) .0365(12) .0221(11) -.0020(9) -.0049(9) .0009(9) C4 .0447(12) .0305(12) .0303(12) .0032(9) -.0027(9) .0042(9) C5 .0366(11) .0241(11) .0315(11) .0001(8) -.0004(9) -.0046(9) C6 .0237(9) .0292(10) .0215(10) .0008(7) .0019(7) -.0059(8) C7 .0301(9) .0182(9) .0232(10) .0001(7) -.0022(8) -.0030(7) C8 .0267(9) .0253(10) .0194(9) -.0010(7) -.0014(7) -.0021(7) C9 .0297(10) .0283(11) .0220(10) -.0029(8) -.0009(8) -.0012(8) C10 .0289(10) .0387(12) .0270(11) -.0069(8) -.0011(8) .0023(9) C11 .0287(10) .0440(13) .0304(11) .0054(9) .0033(9) .0041(9) C12 .0386(11) .0346(13) .0418(13) .0086(9) .0006(10) -.0106(10) C13 .0314(10) .0293(11) .0394(12) .0017(8) -.0031(9) -.0126(9) C14 .0263(9) .0211(10) .0236(10) .0023(7) -.0022(8) -.0044(7) C15 .0237(9) .0321(11) .0269(11) .0041(7) -.0004(8) -.0041(8) C16 .0233(10) .0371(12) .0377(12) .0031(8) -.0052(9) -.0076(9) C17 .0317(11) .0368(12) .0314(12) .0084(8) -.0146(9) -.0078(9) C18 .0381(11) .0354(12) .0233(11) .0075(9) -.0044(9) -.0012(9) C19 .0310(10) .0300(11) .0253(11) -.0016(8) -.0020(8) -.0009(8) C20 .0438(11) .0307(12) .0206(10) -.0016(9) -.0007(9) -.0075(9) C21 .0445(12) .0360(12) .0214(10) -.0060(9) -.0023(9) -.0023(9) 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 N1 C7 . 1.286(2) yes N1 C6 . 1.410(2) yes N2 C20 . 1.146(2) ? N3 C21 . 1.143(2) ? C1 C6 . 1.395(2) ? C1 C2 . 1.401(2) ? C1 C20 . 1.441(3) ? C2 C3 . 1.384(3) ? C2 C21 . 1.441(3) ? C3 C4 . 1.384(3) ? C3 H3 . .97(2) ? C4 C5 . 1.374(3) ? C4 H4 . .94(2) ? C5 C6 . 1.398(3) ? C5 H5 . .947(19) ? C7 C14 . 1.493(2) yes C7 C8 . 1.498(2) yes C8 C13 . 1.387(3) ? C8 C9 . 1.394(2) ? C9 C10 . 1.391(3) ? C9 H9 . 1.01(2) ? C10 C11 . 1.385(3) ? C10 H10 . .98(2) ? C11 C12 . 1.376(3) ? C11 H11 . 1.00(2) ? C12 C13 . 1.385(3) ? C12 H12 . .97(2) ? C13 H13 . 1.01(2) ? C14 C19 . 1.393(2) ? C14 C15 . 1.395(2) ? C15 C16 . 1.387(3) ? C15 H15 . 1.01(2) ? C16 C17 . 1.382(3) ? C16 H16 . .975(19) ? C17 C18 . 1.387(3) ? C17 H17 . .99(2) ? C18 C19 . 1.384(3) ? C18 H18 . 1.02(2) ? C19 H19 . 1.02(2) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 '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 C7 N1 C6 121.59(15) C6 C1 C2 119.96(17) C6 C1 C20 119.65(16) C2 C1 C20 120.35(16) C3 C2 C1 120.47(17) C3 C2 C21 119.11(17) C1 C2 C21 120.42(17) C2 C3 C4 119.21(19) C2 C3 H3 119.6(12) C4 C3 H3 121.2(12) C5 C4 C3 120.9(2) C5 C4 H4 119.5(12) C3 C4 H4 119.6(12) C4 C5 C6 120.79(19) C4 C5 H5 119.7(12) C6 C5 H5 119.5(12) C1 C6 C5 118.63(17) C1 C6 N1 120.44(16) C5 C6 N1 120.50(16) N1 C7 C14 116.72(16) N1 C7 C8 125.91(16) C14 C7 C8 117.30(15) C13 C8 C9 119.03(17) C13 C8 C7 118.77(16) C9 C8 C7 122.21(16) C10 C9 C8 119.95(18) C10 C9 H9 120.4(10) C8 C9 H9 119.6(10) C11 C10 C9 120.30(18) C11 C10 H10 122.9(12) C9 C10 H10 116.7(12) C12 C11 C10 119.77(19) C12 C11 H11 120.4(12) C10 C11 H11 119.8(12) C11 C12 C13 120.3(2) C11 C12 H12 121.0(12) C13 C12 H12 118.5(12) C12 C13 C8 120.66(18) C12 C13 H13 119.6(11) C8 C13 H13 119.8(11) C19 C14 C15 119.57(16) C19 C14 C7 121.32(16) C15 C14 C7 119.09(16) C16 C15 C14 119.68(18) C16 C15 H15 123.0(11) C14 C15 H15 117.3(11) C17 C16 C15 120.48(19) C17 C16 H16 120.6(12) C15 C16 H16 118.9(12) C16 C17 C18 119.95(18) C16 C17 H17 121.2(11) C18 C17 H17 118.8(11) C19 C18 C17 120.02(19) C19 C18 H18 121.7(11) C17 C18 H18 118.3(11) C18 C19 C14 120.20(18) C18 C19 H19 119.7(12) C14 C19 H19 120.0(12) N2 C20 C1 178.9(2) N3 C21 C2 178.1(2) 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 _geom_hbond_publ_flag C18 H18 N2 4_555 1.02(2) 2.59(2) 3.526(3) 152.0(10) yes C3 H3 Cg(A) 5_575 .97(2) 3.03(2) 3.901(2) 150.0(10) 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 C6 C1 C2 C3 1.1(3) C20 C1 C2 C3 179.01(17) C6 C1 C2 C21 -178.68(17) C20 C1 C2 C21 -.8(3) C1 C2 C3 C4 .4(3) C21 C2 C3 C4 -179.76(18) C2 C3 C4 C5 -.8(3) C3 C4 C5 C6 -.4(3) C2 C1 C6 C5 -2.3(2) C20 C1 C6 C5 179.84(17) C2 C1 C6 N1 -174.82(15) C20 C1 C6 N1 7.3(2) C4 C5 C6 C1 1.9(3) C4 C5 C6 N1 174.45(18) C7 N1 C6 C1 -120.53(19) C7 N1 C6 C5 67.1(2) C6 N1 C7 C14 -167.85(16) C6 N1 C7 C8 9.2(3) N1 C7 C8 C13 -136.6(2) C14 C7 C8 C13 40.4(2) N1 C7 C8 C9 42.9(3) C14 C7 C8 C9 -140.11(17) C13 C8 C9 C10 .9(3) C7 C8 C9 C10 -178.58(17) C8 C9 C10 C11 .6(3) C9 C10 C11 C12 -1.4(3) C10 C11 C12 C13 .7(3) C11 C12 C13 C8 .9(3) C9 C8 C13 C12 -1.7(3) C7 C8 C13 C12 177.83(18) N1 C7 C14 C19 -142.58(18) C8 C7 C14 C19 40.1(2) N1 C7 C14 C15 39.2(2) C8 C7 C14 C15 -138.12(17) C19 C14 C15 C16 -.3(3) C7 C14 C15 C16 177.96(16) C14 C15 C16 C17 2.3(3) C15 C16 C17 C18 -1.5(3) C16 C17 C18 C19 -1.2(3) C17 C18 C19 C14 3.1(3) C15 C14 C19 C18 -2.4(3) C7 C14 C19 C18 179.37(17)