#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/08/2200882.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_2200882 loop_ _publ_author_name 'A. Subbiah Pandi' 'D. Velmurugan' 'S. Shanmuga Sundara Raj' 'Hoong-Kun Fun' 'V. Raghukumar' _publ_section_title ; A monoclinic polymorph of 3-amino-4'-(N,N-diethylamino)-5-methylbiphenyl-2,4-dicarbonitrile ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o222 _journal_page_last o223 _journal_paper_doi 10.1107/S1600536802001745 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C19 H20 N4' _chemical_formula_sum 'C19 H20 N4' _chemical_formula_weight 304.39 _chemical_name_systematic ; 3-Amino-4'-(N,N-diethylamino)-5-methylbiphenyl-2,4-dicarbonitrile ; _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 90.367(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.2925(4) _cell_length_b 10.8655(3) _cell_length_c 16.7229(5) _cell_measurement_reflns_used 3225 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.31 _cell_measurement_theta_min 2.19 _cell_volume 1688.44(10) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'ZORTEP (Zsolnai, 1997)' _computing_publication_material 'SHELXL97 and 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 8.33 _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scans' _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 .124 _diffrn_reflns_av_sigmaI/netI .1537 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10442 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 26.50 _diffrn_reflns_theta_min 2.19 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .073 _exptl_absorpt_correction_T_max .990 _exptl_absorpt_correction_T_min .978 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_description slab _exptl_crystal_F_000 648 _exptl_crystal_size_max .26 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .10 _refine_diff_density_max .19 _refine_diff_density_min -.18 _refine_ls_extinction_coef .010(2) _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 .92 _refine_ls_hydrogen_treatment riding _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3496 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .92 _refine_ls_R_factor_all .212 _refine_ls_R_factor_gt .068 _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^)+(0.0674P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .135 _refine_ls_wR_factor_ref .185 _reflns_number_gt 1313 _reflns_number_total 3496 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6096.cif _cod_data_source_block I _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_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200882 _cod_database_fobs_code 2200882 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 1.2550(3) .1435(2) -.04938(17) .0627(10) Uani d . 1 . . N H1A 1.3355 .1044 -.0492 .075 Uiso calc R 1 . . H H1B 1.2323 .1895 -.0894 .075 Uiso calc R 1 . . H N2 .9802(4) .3249(3) -.1129(2) .0769(11) Uani d . 1 . . N N3 1.4420(4) -.0533(3) .0832(2) .0753(11) Uani d . 1 . . N N4 .4297(3) .4792(3) .10641(17) .0527(8) Uani d . 1 . . N C1' .8075(3) .2666(3) .08398(19) .0429(9) Uani d . 1 . . C C2' .8091(4) .3932(3) .07514(19) .0491(9) Uani d . 1 . . C H2' .8953 .4320 .0629 .059 Uiso calc R 1 . . H C3' .6867(4) .4634(3) .08397(19) .0493(10) Uani d . 1 . . C H3' .6927 .5485 .0788 .059 Uiso calc R 1 . . H C4' .5531(3) .4092(3) .10059(19) .0432(9) Uani d . 1 . . C C5' .5515(3) .2820(3) .1093(2) .0485(9) Uani d . 1 . . C H5' .4652 .2423 .1203 .058 Uiso calc R 1 . . H C6' .6752(3) .2137(3) .10183(19) .0487(9) Uani d . 1 . . C H6' .6702 .1289 .1090 .058 Uiso calc R 1 . . H C1 .9396(3) .1910(3) .0799(2) .0422(9) Uani d . 1 . . C C2 1.0330(3) .1983(3) .0147(2) .0417(9) Uani d . 1 . . C C3 1.1640(4) .1325(3) .0133(2) .0441(9) Uani d . 1 . . C C4 1.1961(3) .0586(3) .0799(2) .0460(9) Uani d . 1 . . C C5 1.1036(4) .0476(3) .1446(2) .0482(9) Uani d . 1 . . C C6 .9761(4) .1141(3) .1434(2) .0527(10) Uani d . 1 . . C H6 .9132 .1070 .1862 .063 Uiso calc R 1 . . H C7 .9996(3) .2700(3) -.0548(2) .0519(10) Uani d . 1 . . C C8 1.3319(4) -.0049(3) .0824(2) .0535(10) Uani d . 1 . . C C9 1.1408(4) -.0327(3) .2149(2) .0688(12) Uani d . 1 . . C H9A 1.0646 -.0291 .2534 .103 Uiso calc R 1 . . H H9B 1.2287 -.0042 .2391 .103 Uiso calc R 1 . . H H9C 1.1529 -.1161 .1972 .103 Uiso calc R 1 . . H C10 .2906(4) .4206(3) .1182(3) .0723(12) Uani d . 1 . . C H10A .2878 .3455 .0869 .087 Uiso calc R 1 . . H H10B .2164 .4748 .0973 .087 Uiso calc R 1 . . H C11 .2543(5) .3893(5) .2031(3) .1119(18) Uani d . 1 . . C H11A .3252 .3335 .2242 .168 Uiso calc R 1 . . H H11B .1612 .3512 .2048 .168 Uiso calc R 1 . . H H11C .2535 .4631 .2347 .168 Uiso calc R 1 . . H C12 .4342(4) .6127(3) .1089(2) .0602(11) Uani d . 1 . . C H12A .3396 .6443 .0952 .072 Uiso calc R 1 . . H H12B .5008 .6416 .0687 .072 Uiso calc R 1 . . H C13 .4785(6) .6639(4) .1883(2) .1050(18) Uani d . 1 . . C H13A .4118 .6376 .2284 .157 Uiso calc R 1 . . H H13B .4791 .7522 .1857 .157 Uiso calc R 1 . . H H13C .5732 .6349 .2018 .157 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 N1 .0456(19) .072(2) .070(2) .0191(16) .0188(17) .0173(16) N2 .075(3) .082(3) .074(3) .022(2) .003(2) .018(2) N3 .051(2) .077(3) .099(3) .0224(19) .013(2) .0235(19) N4 .0386(18) .0498(19) .070(2) .0088(16) .0001(15) -.0035(15) C1' .035(2) .047(2) .047(2) .0033(18) .0029(16) -.0006(17) C2' .040(2) .056(2) .052(2) .0020(19) .0009(18) -.0031(18) C3' .046(2) .045(2) .057(2) .0056(19) -.0013(19) -.0023(17) C4' .036(2) .052(2) .042(2) .0089(18) -.0029(16) -.0037(17) C5' .032(2) .052(2) .061(2) .0042(18) .0053(17) .0035(18) C6' .044(2) .042(2) .060(2) .0067(19) .0037(19) .0017(17) C1 .0278(18) .048(2) .051(2) .0044(17) .0021(17) -.0053(17) C2 .0330(19) .041(2) .051(2) .0076(16) -.0019(17) .0019(17) C3 .040(2) .042(2) .051(2) -.0004(17) .0045(18) -.0036(18) C4 .0307(19) .045(2) .063(2) .0093(17) .0026(18) -.0036(18) C5 .036(2) .053(2) .056(2) .0053(18) -.0013(18) -.0008(19) C6 .038(2) .064(2) .055(2) .0067(19) .0065(18) .008(2) C7 .033(2) .057(2) .066(3) .0119(19) .011(2) .001(2) C8 .048(2) .049(2) .063(3) .002(2) .008(2) .0069(18) C9 .053(3) .088(3) .065(3) .015(2) -.001(2) .022(2) C10 .043(2) .068(3) .105(4) .016(2) .000(2) .001(2) C11 .084(4) .117(4) .135(5) .006(3) .053(3) .007(3) C12 .058(3) .054(2) .068(3) .015(2) -.012(2) -.005(2) C13 .167(5) .071(3) .076(4) .004(3) -.015(3) -.022(3) 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 C3 N1 H1A 120.0 C3 N1 H1B 120.0 H1A N1 H1B 120.0 C4' N4 C12 122.0(3) C4' N4 C10 120.5(3) C12 N4 C10 117.3(3) C2' C1' C6' 116.3(3) C2' C1' C1 122.5(3) C6' C1' C1 121.0(3) C3' C2' C1' 122.0(3) C3' C2' H2' 119.0 C1' C2' H2' 119.0 C2' C3' C4' 121.4(3) C2' C3' H3' 119.3 C4' C3' H3' 119.3 N4 C4' C5' 122.1(3) N4 C4' C3' 121.3(3) C5' C4' C3' 116.6(3) C6' C5' C4' 121.2(3) C6' C5' H5' 119.4 C4' C5' H5' 119.4 C5' C6' C1' 122.5(3) C5' C6' H6' 118.7 C1' C6' H6' 118.7 C6 C1 C2 118.6(3) C6 C1 C1' 119.8(3) C2 C1 C1' 121.5(3) C1 C2 C3 121.5(3) C1 C2 C7 122.1(3) C3 C2 C7 116.4(3) N1 C3 C4 122.2(3) N1 C3 C2 120.7(3) C4 C3 C2 117.1(3) C5 C4 C3 122.5(3) C5 C4 C8 118.9(3) C3 C4 C8 118.6(3) C6 C5 C4 118.4(3) C6 C5 C9 120.4(3) C4 C5 C9 121.2(3) C5 C6 C1 121.8(3) C5 C6 H6 119.1 C1 C6 H6 119.1 N2 C7 C2 175.8(4) N3 C8 C4 178.3(4) C5 C9 H9A 109.5 C5 C9 H9B 109.5 H9A C9 H9B 109.5 C5 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 N4 C10 C11 115.6(4) N4 C10 H10A 108.4 C11 C10 H10A 108.4 N4 C10 H10B 108.4 C11 C10 H10B 108.4 H10A C10 H10B 107.4 C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 N4 C12 C13 113.9(3) N4 C12 H12A 108.8 C13 C12 H12A 108.8 N4 C12 H12B 108.8 C13 C12 H12B 108.8 H12A C12 H12B 107.7 C12 C13 H13A 109.5 C12 C13 H13B 109.5 H13A C13 H13B 109.5 C12 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 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 C3 . 1.356(4) ? N1 H1A . .86 ? N1 H1B . .86 ? N2 C7 . 1.153(4) ? N3 C8 . 1.150(4) ? N4 C4' . 1.380(4) ? N4 C12 . 1.451(4) ? N4 C10 . 1.456(4) ? C1' C2' . 1.383(4) ? C1' C6' . 1.392(4) ? C1' C1 . 1.479(4) ? C2' C3' . 1.379(4) ? C2' H2' . .93 ? C3' C4' . 1.403(4) ? C3' H3' . .93 ? C4' C5' . 1.390(4) ? C5' C6' . 1.374(4) ? C5' H5' . .93 ? C6' H6' . .93 ? C1 C6 . 1.391(4) ? C1 C2 . 1.400(4) ? C2 C3 . 1.411(4) ? C2 C7 . 1.432(5) ? C3 C4 . 1.404(4) ? C4 C5 . 1.390(4) ? C4 C8 . 1.439(5) ? C5 C6 . 1.388(4) ? C5 C9 . 1.503(5) ? C6 H6 . .93 ? C9 H9A . .96 ? C9 H9B . .96 ? C9 H9C . .96 ? C10 C11 . 1.500(5) ? C10 H10A . .97 ? C10 H10B . .97 ? C11 H11A . .96 ? C11 H11B . .96 ? C11 H11C . .96 ? C12 C13 . 1.496(5) ? C12 H12A . .97 ? C12 H12B . .97 ? C13 H13A . .96 ? C13 H13B . .96 ? C13 H13C . .96 ? 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 _geom_torsion_publ_flag C6' C1' C2' C3' .4(5) ? C1 C1' C2' C3' -175.9(3) ? C1' C2' C3' C4' -1.5(5) ? C12 N4 C4' C5' 170.9(3) yes C10 N4 C4' C5' -3.0(5) yes C12 N4 C4' C3' -10.3(5) yes C10 N4 C4' C3' 175.8(3) yes C2' C3' C4' N4 -177.5(3) ? C2' C3' C4' C5' 1.3(5) ? N4 C4' C5' C6' 178.8(3) ? C3' C4' C5' C6' .0(5) ? C4' C5' C6' C1' -1.2(5) ? C2' C1' C6' C5' .9(5) ? C1 C1' C6' C5' 177.3(3) ? C2' C1' C1 C6 124.0(4) ? C6' C1' C1 C6 -52.1(5) yes C2' C1' C1 C2 -53.5(5) yes C6' C1' C1 C2 130.4(3) ? C6 C1 C2 C3 -1.9(5) ? C1' C1 C2 C3 175.6(3) ? C6 C1 C2 C7 176.5(3) ? C1' C1 C2 C7 -6.0(5) ? C1 C2 C3 N1 -178.1(3) ? C7 C2 C3 N1 3.4(5) ? C1 C2 C3 C4 .6(5) ? C7 C2 C3 C4 -178.0(3) ? N1 C3 C4 C5 179.6(3) ? C2 C3 C4 C5 1.0(5) ? N1 C3 C4 C8 1.6(5) ? C2 C3 C4 C8 -177.0(3) ? C3 C4 C5 C6 -1.1(5) ? C8 C4 C5 C6 176.8(3) ? C3 C4 C5 C9 179.8(3) ? C8 C4 C5 C9 -2.3(5) ? C4 C5 C6 C1 -.3(5) ? C9 C5 C6 C1 178.8(3) ? C2 C1 C6 C5 1.8(5) ? C1' C1 C6 C5 -175.7(3) ? C4' N4 C10 C11 83.6(4) yes C12 N4 C10 C11 -90.5(4) ? C4' N4 C12 C13 -77.3(4) yes C10 N4 C12 C13 96.8(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9110839