#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013977.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_2013977 loop_ _publ_author_name 'H\"orner, Manfredo' 'Brancher, Almir Luis' 'Silva, Angela' 'Bordinhao, Jairo' 'M\"ossmer, C\"acilia M.' _publ_section_title ; 3-(4-Acetylphenyl)-1-(4-nitrophenyl)triazene ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o303 _journal_page_last o304 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H12 N4 O3' _chemical_formula_moiety 'C14 H12 N4 O3' _chemical_formula_sum 'C14 H12 N4 O3' _chemical_formula_weight 284.28 _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' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 100.35(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 14.357(6) _cell_length_b 7.1964(13) _cell_length_c 26.779(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.0 _cell_measurement_theta_min 10.2 _cell_volume 2721.8(14) _computing_cell_refinement 'CAD-4 Express (Enraf Nonius, 1994)' _computing_data_collection 'CAD-4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg, 1996)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method omega _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0147 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 3468 _diffrn_reflns_theta_full 27.97 _diffrn_reflns_theta_max 27.97 _diffrn_reflns_theta_min 3.02 _diffrn_standards_decay_% <1 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1184 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.144 _refine_diff_density_min -0.138 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 3266 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.009 _refine_ls_R_factor_gt 0.0523 _refine_ls_shift/su_max 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1423 _reflns_number_gt 1809 _reflns_number_total 3266 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1466.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_original_cell_volume 2721.7(13) _cod_database_code 2013977 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 O1 0.01964(11) 0.6804(2) 0.39769(6) 0.0771(5) Uani d . 1 . . O O11 0.76728(14) 0.2796(3) 0.75888(7) 0.1064(7) Uani d . 1 . . O O12 0.63806(14) 0.3986(3) 0.77367(6) 0.0976(7) Uani d . 1 . . O N1 0.68538(16) 0.3291(3) 0.74482(8) 0.0761(6) Uani d . 1 . . N N11 0.52677(12) 0.2366(3) 0.53903(6) 0.0566(5) Uani d . 1 . . N N12 0.44704(11) 0.3132(2) 0.52462(6) 0.0532(4) Uani d . 1 . . N N13 0.41564(12) 0.2878(3) 0.47558(7) 0.0567(5) Uani d . 1 . . N C2 0.07135(14) 0.5958(3) 0.37417(8) 0.0530(5) Uani d . 1 . . C C3 0.04492(16) 0.5816(4) 0.31830(8) 0.0720(7) Uani d . 1 . . C H3A -0.0176 0.6309 0.3076 0.108 Uiso calc R 1 . . H H3B 0.0459 0.4535 0.3084 0.108 Uiso calc R 1 . . H H3C 0.0891 0.6508 0.3027 0.108 Uiso calc R 1 . . H C11 0.56121(14) 0.2645(3) 0.59145(7) 0.0515(5) Uani d . 1 . . C C12 0.51637(15) 0.3705(3) 0.62349(8) 0.0607(6) Uani d . 1 . . C H12 0.4589 0.4281 0.611 0.073 Uiso calc R 1 . . H C13 0.55709(16) 0.3898(3) 0.67364(8) 0.0643(6) Uani d . 1 . . C H13 0.5273 0.4598 0.6954 0.077 Uiso calc R 1 . . H C14 0.64239(15) 0.3047(3) 0.69143(8) 0.0586(6) Uani d . 1 . . C C15 0.68790(16) 0.1988(3) 0.66067(8) 0.0626(6) Uani d . 1 . . C H15 0.7453 0.1416 0.6735 0.075 Uiso calc R 1 . . H C16 0.64685(14) 0.1788(3) 0.61037(8) 0.0578(6) Uani d . 1 . . C H16 0.6767 0.1075 0.589 0.069 Uiso calc R 1 . . H C21 0.32960(13) 0.3626(3) 0.45181(7) 0.0468(5) Uani d . 1 . . C C22 0.30022(14) 0.3275(3) 0.40068(7) 0.0510(5) Uani d . 1 . . C H22 0.3369 0.254 0.3832 0.061 Uiso calc R 1 . . H C23 0.21645(13) 0.4016(3) 0.37578(7) 0.0506(5) Uani d . 1 . . C H23 0.1972 0.378 0.3413 0.061 Uiso calc R 1 . . H C24 0.15986(12) 0.5111(3) 0.40088(7) 0.0463(5) Uani d . 1 . . C C25 0.18991(14) 0.5430(3) 0.45256(7) 0.0518(5) Uani d . 1 . . C H25 0.1524 0.614 0.4702 0.062 Uiso calc R 1 . . H C26 0.27378(13) 0.4716(3) 0.47791(7) 0.0526(5) Uani d . 1 . . C H26 0.2933 0.4957 0.5123 0.063 Uiso calc R 1 . . H H3 0.4492(16) 0.231(3) 0.4581(8) 0.064(7) 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 O1 0.0617(10) 0.0969(13) 0.0741(11) 0.0288(9) 0.0160(8) 0.0031(9) O11 0.0804(13) 0.154(2) 0.0741(12) 0.0106(14) -0.0147(10) 0.0004(13) O12 0.0881(13) 0.1498(19) 0.0564(10) -0.0121(13) 0.0170(10) -0.0025(11) N1 0.0706(14) 0.0978(17) 0.0571(12) -0.0151(12) 0.0042(11) 0.0136(12) N11 0.0468(10) 0.0631(11) 0.0567(10) 0.0047(9) 0.0012(8) 0.0034(9) N12 0.0477(10) 0.0593(11) 0.0518(10) -0.0020(8) 0.0070(8) 0.0054(8) N13 0.0461(10) 0.0718(13) 0.0516(11) 0.0092(9) 0.0071(8) -0.0003(9) C2 0.0424(11) 0.0556(13) 0.0613(13) 0.0007(10) 0.0102(10) 0.0024(10) C3 0.0576(14) 0.0901(18) 0.0636(14) 0.0080(13) -0.0015(11) 0.0056(13) C11 0.0476(11) 0.0535(12) 0.0526(11) -0.0052(10) 0.0066(9) 0.0063(10) C12 0.0500(12) 0.0704(15) 0.0608(14) 0.0056(11) 0.0075(10) 0.0061(11) C13 0.0630(14) 0.0727(16) 0.0585(13) -0.0013(12) 0.0144(11) 0.0033(12) C14 0.0553(13) 0.0689(15) 0.0496(12) -0.0117(11) 0.0042(10) 0.0110(11) C15 0.0500(12) 0.0703(15) 0.0641(14) 0.0007(11) 0.0013(10) 0.0142(12) C16 0.0496(12) 0.0609(14) 0.0613(13) 0.0022(11) 0.0056(10) 0.0049(11) C21 0.0412(10) 0.0496(12) 0.0500(11) -0.0010(9) 0.0087(8) 0.0030(9) C22 0.0467(11) 0.0556(12) 0.0516(11) 0.0043(10) 0.0109(9) -0.0058(10) C23 0.0455(11) 0.0593(13) 0.0460(11) -0.0018(10) 0.0054(9) -0.0056(10) C24 0.0393(10) 0.0499(12) 0.0505(11) -0.0012(9) 0.0103(8) 0.0004(9) C25 0.0470(11) 0.0601(13) 0.0508(11) 0.0040(10) 0.0152(9) -0.0027(10) C26 0.0491(12) 0.0641(14) 0.0444(11) 0.0010(10) 0.0076(9) -0.0023(10) 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 O1 C2 . 1.219(2) yes O11 N1 . 1.222(3) yes O11 N1 4_646 3.317(3) no O12 N1 . 1.223(3) yes N1 C14 . 1.462(3) no N1 O11 4_656 3.317(3) no N11 N12 . 1.267(2) yes N11 C11 . 1.416(3) no N12 N13 . 1.322(2) yes N13 C21 . 1.392(3) no C2 C24 . 1.474(3) no C2 C3 . 1.479(3) no C3 H3A . 0.96 no C3 H3B . 0.96 no C3 H3C . 0.96 no C11 C16 . 1.387(3) no C11 C12 . 1.389(3) no C12 C13 . 1.372(3) no C12 H12 . 0.93 no C13 C14 . 1.375(3) no C13 H13 . 0.93 no C14 C15 . 1.371(3) no C15 C16 . 1.377(3) no C15 H15 . 0.93 no C16 H16 . 0.93 no C21 C22 . 1.382(3) no C21 C26 . 1.395(3) no C22 C23 . 1.374(3) no C22 H22 . 0.93 no C23 C24 . 1.389(3) no C23 H23 . 0.93 no C24 C25 . 1.393(3) no C25 C26 . 1.371(3) no C25 H25 . 0.93 no C26 H26 . 0.93 no 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 0 '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 0.006 '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_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 O11 N1 4_646 117.85(18) no O11 N1 O12 . 122.5(2) no O11 N1 C14 . 118.7(2) no O12 N1 C14 . 118.8(2) no O11 N1 O11 4_656 95.94(16) no O12 N1 O11 4_656 76.10(16) no C14 N1 O11 4_656 98.11(13) no N12 N11 C11 . 112.07(17) yes N11 N12 N13 . 111.74(17) yes N12 N13 C21 . 121.09(19) yes N12 N13 O1 3_545 128.89(13) no C21 N13 O1 3_545 107.79(13) no O1 C2 C24 . 120.52(19) yes O1 C2 C3 . 119.17(19) no C24 C2 C3 . 120.30(19) yes C2 C3 H3A . 109.5 no C2 C3 H3B . 109.5 no H3A C3 H3B . 109.5 no C2 C3 H3C . 109.5 no H3A C3 H3C . 109.5 no H3B C3 H3C . 109.5 no C16 C11 C12 . 119.8(2) no C16 C11 N11 . 115.30(19) no C12 C11 N11 . 124.89(19) no C13 C12 C11 . 119.8(2) no C13 C12 H12 . 120.1 no C11 C12 H12 . 120.1 no C12 C13 C14 . 119.3(2) no C12 C13 H13 . 120.3 no C14 C13 H13 . 120.3 no C15 C14 C13 . 122.0(2) no C15 C14 N1 . 119.4(2) no C13 C14 N1 . 118.6(2) no C14 C15 C16 . 118.6(2) no C14 C15 H15 . 120.7 no C16 C15 H15 . 120.7 no C15 C16 C11 . 120.4(2) no C15 C16 H16 . 119.8 no C11 C16 H16 . 119.8 no C22 C21 N13 . 118.03(18) no C22 C21 C26 . 119.91(18) no N13 C21 C26 . 122.06(18) no C23 C22 C21 . 119.64(19) no C23 C22 H22 . 120.2 no C21 C22 H22 . 120.2 no C22 C23 C24 . 121.50(18) no C22 C23 H23 . 119.2 no C24 C23 H23 . 119.2 no C23 C24 C25 . 118.09(18) no C23 C24 C2 . 121.87(18) no C25 C24 C2 . 120.03(18) no C26 C25 C24 . 121.18(18) no C26 C25 H25 . 119.4 no C24 C25 H25 . 119.4 no C25 C26 C21 . 119.66(18) no C25 C26 H26 . 120.2 no C21 C26 H26 . 120.2 no _cod_database_fobs_code 2013977 _journal_paper_doi 10.1107/S0108270104004822