#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/12/2011239.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_2011239 loop_ _publ_author_name 'Jim\'enez-Cruz, Federico' 'P\'erez-Caballero, Guadalupe' 'Hern\'andez-Ortega, Sim\'on' 'Rubio-Arroyo, Manuel' _publ_section_title ; 2-(4-Methoxyphenylazo)-4-phenylphenol ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1028 _journal_page_last 1029 _journal_paper_doi 10.1107/S0108270100007307 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C19 H16 N2 O2' _chemical_formula_weight 304.34 _chemical_name_common PCH3ON2 _chemical_name_systematic ; 4-phenyl-2-[4-Methoxyphenyldiazenyl]phenol ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.48(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.449(2) _cell_length_b 8.638(2) _cell_length_c 28.414(17) _cell_measurement_reflns_used 49 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 24.5 _cell_measurement_theta_min 4.9 _cell_volume 1582.8(11) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXTL/PC (Sheldrick, 1990)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full .932 _diffrn_measured_fraction_theta_max .932 _diffrn_measurement_device_type 'Siemens P4/PC' _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 .71073 _diffrn_reflns_av_R_equivalents .0453 _diffrn_reflns_av_sigmaI/netI .0857 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 3062 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.46 _diffrn_standards_decay_% <2 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .084 _exptl_absorpt_correction_type none _exptl_crystal_colour Red _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method none _exptl_crystal_description Prism _exptl_crystal_F_000 640 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .20 _refine_diff_density_max .11 _refine_diff_density_min -.20 _refine_ls_extinction_coef .0102(11) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref .767 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2794 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .767 _refine_ls_R_factor_all .1232 _refine_ls_R_factor_gt .0482 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[s^2^(Fo^2^)+(0.0488P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1268 _reflns_number_gt 1126 _reflns_number_total 2794 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob1031.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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[s^2^(Fo^2^)+(0.0488P)^2^] 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^)+(0.0488P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1582.90(10) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2011239 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 .4701(4) 1.0730(3) .09940(8) .0816(8) Uani d . 1 . . O H1 .397(5) 1.027(4) .0774(10) .060 Uiso d . 1 . . H O2 -.1259(4) .5901(3) -.09131(8) .0879(8) Uani d . 1 . . O N1 .1696(4) .9116(3) .06438(8) .0623(7) Uani d . 1 . . N N2 .0578(4) .9241(3) .10099(8) .0621(7) Uani d . 1 . . N C1 .0790(5) .8262(4) .02666(9) .0564(8) Uani d . 1 . . C C2 -.1168(5) .7605(4) .02715(10) .0687(9) Uani d . 1 . . C H2 -.1991 .7703 .0537 .060 Uiso calc R 1 . . H C3 -.1895(5) .6814(4) -.01111(11) .0687(9) Uani d . 1 . . C H3 -.3212 .6376 -.0104 .060 Uiso calc R 1 . . H C4 -.0688(5) .6657(4) -.05120(10) .0668(9) Uani d . 1 . . C C5 .1256(5) .7332(4) -.05185(11) .0721(10) Uani d . 1 . . C H5 .2063 .7247 -.0787 .060 Uiso calc R 1 . . H C6 .2014(5) .8126(4) -.01349(10) .0664(9) Uani d . 1 . . C H6 .3328 .8568 -.0142 .060 Uiso calc R 1 . . H C7 -.3243(6) .5205(5) -.09392(13) .0967(13) Uani d . 1 . . C H7A -.3265 .4300 -.0743 .060 Uiso calc R 1 . . H H7B -.3540 .4915 -.1259 .060 Uiso calc R 1 . . H H7C -.4270 .5927 -.0833 .060 Uiso calc R 1 . . H C11 .3472(5) 1.0766(4) .13804(11) .0639(9) Uani d . 1 . . C C12 .1504(5) 1.0073(4) .13833(10) .0564(8) Uani d . 1 . . C C13 .0320(5) 1.0171(4) .17951(10) .0591(8) Uani d . 1 . . C H13 -.0989 .9720 .1796 .060 Uiso calc R 1 . . H C14 .1008(5) 1.0906(4) .21970(10) .0581(8) Uani d . 1 . . C C15 .3002(5) 1.1555(4) .21825(11) .0681(9) Uani d . 1 . . C H15 .3539 1.2031 .2451 .060 Uiso calc R 1 . . H C16 .4183(5) 1.1504(4) .17804(11) .0737(10) Uani d . 1 . . C H16 .5480 1.1975 .1779 .060 Uiso calc R 1 . . H C17 -.0285(5) 1.0970(4) .26296(9) .0539(7) Uani d . 1 . . C C18 -.1834(5) .9885(4) .27078(10) .0655(9) Uani d . 1 . . C H18 -.2033 .9091 .2491 .060 Uiso calc R 1 . . H C19 -.3089(5) .9953(4) .31004(11) .0731(10) Uani d . 1 . . C H19 -.4110 .9208 .3146 .060 Uiso calc R 1 . . H C20 -.2823(5) 1.1124(4) .34225(11) .0713(9) Uani d . 1 . . C H20 -.3674 1.1181 .3685 .060 Uiso calc R 1 . . H C21 -.1304(6) 1.2205(4) .33565(11) .0700(10) Uani d . 1 . . C H21 -.1110 1.2990 .3577 .060 Uiso calc R 1 . . H C22 -.0048(5) 1.2138(4) .29625(10) .0635(9) Uani d . 1 . . C H22 .0969 1.2887 .2920 .060 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 .0738(16) .105(2) .0660(14) -.0193(15) .0223(12) -.0006(14) O2 .0790(17) .105(2) .0796(16) -.0001(16) .0076(13) -.0338(16) N1 .0703(17) .0651(18) .0519(14) .0013(15) .0171(13) .0070(13) N2 .0691(17) .0682(17) .0490(14) .0015(15) .0114(13) .0041(13) C1 .066(2) .0552(19) .0479(17) .0025(17) .0133(15) .0057(14) C2 .073(2) .082(3) .0516(18) -.008(2) .0200(16) -.0001(18) C3 .066(2) .074(2) .066(2) -.0054(19) .0157(17) .0047(18) C4 .072(2) .071(2) .0570(19) .010(2) .0065(17) -.0046(18) C5 .067(2) .090(3) .060(2) .005(2) .0212(17) -.0045(19) C6 .061(2) .078(2) .0606(19) -.0022(19) .0152(16) .0025(18) C7 .100(3) .097(3) .094(3) -.003(3) -.005(2) -.021(2) C11 .066(2) .062(2) .0632(19) .0008(19) .0142(17) .0066(17) C12 .059(2) .0587(19) .0519(17) .0017(17) .0055(15) .0042(15) C13 .060(2) .059(2) .0581(18) -.0042(17) .0080(16) .0056(16) C14 .0601(19) .0564(19) .0580(17) -.0014(17) .0046(15) .0057(16) C15 .072(2) .074(2) .0582(19) -.007(2) .0004(17) -.0086(17) C16 .062(2) .087(3) .071(2) -.020(2) .0104(18) .001(2) C17 .0597(19) .0512(18) .0508(16) .0032(16) .0017(14) .0021(15) C18 .078(2) .063(2) .0563(18) -.003(2) .0091(17) -.0094(16) C19 .070(2) .078(3) .072(2) -.009(2) .0158(18) -.0007(19) C20 .076(2) .078(2) .0601(19) .004(2) .0156(17) -.0017(19) C21 .090(3) .063(2) .0572(18) .002(2) .0057(18) -.0079(16) C22 .071(2) .057(2) .0628(19) -.0008(18) .0057(17) .0015(16) 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' O O .0106 .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 C11 O1 H1 106(2) no C4 O2 C7 119.2(3) no N2 N1 C1 115.4(3) yes N1 N2 C12 114.7(3) yes C2 C1 C6 119.7(3) no C2 C1 N1 124.8(3) yes C6 C1 N1 115.4(3) yes C3 C2 C1 120.2(3) no C3 C2 H2 119.9 no C1 C2 H2 119.9 no C2 C3 C4 120.7(3) no C2 C3 H3 119.6 no C4 C3 H3 119.6 no O2 C4 C5 115.6(3) yes O2 C4 C3 125.6(3) yes C5 C4 C3 118.8(3) no C6 C5 C4 121.3(3) no C6 C5 H5 119.4 no C4 C5 H5 119.4 no C5 C6 C1 119.2(3) no C5 C6 H6 120.4 no C1 C6 H6 120.4 no O2 C7 H7A 109.5 no O2 C7 H7B 109.5 no H7A C7 H7B 109.5 no O2 C7 H7C 109.5 no H7A C7 H7C 109.5 no H7B C7 H7C 109.5 no O1 C11 C16 118.8(3) yes O1 C11 C12 121.8(3) yes C16 C11 C12 119.3(3) no C11 C12 C13 118.4(3) no C11 C12 N2 126.3(3) yes C13 C12 N2 115.3(3) yes C14 C13 C12 123.1(3) no C14 C13 H13 118.4 no C12 C13 H13 118.4 no C13 C14 C15 116.5(3) no C13 C14 C17 121.5(3) no C15 C14 C17 121.9(3) no C16 C15 C14 121.7(3) no C16 C15 H15 119.2 no C14 C15 H15 119.2 no C11 C16 C15 120.9(3) no C11 C16 H16 119.5 no C15 C16 H16 119.5 no C18 C17 C22 117.2(3) no C18 C17 C14 120.9(3) no C22 C17 C14 121.9(3) no C19 C18 C17 121.7(3) no C19 C18 H18 119.2 no C17 C18 H18 119.2 no C20 C19 C18 119.9(4) no C20 C19 H19 120.1 no C18 C19 H19 120.1 no C21 C20 C19 119.8(3) no C21 C20 H20 120.1 no C19 C20 H20 120.1 no C20 C21 C22 120.3(3) no C20 C21 H21 119.9 no C22 C21 H21 119.9 no C21 C22 C17 121.2(3) no C21 C22 H22 119.4 no C17 C22 H22 119.4 no 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 C11 . 1.361(4) yes O1 H1 . .87(3) no O2 C4 . 1.360(4) yes O2 C7 . 1.414(4) yes N1 N2 . 1.275(3) yes N1 C1 . 1.423(4) yes N2 C12 . 1.409(4) yes C1 C2 . 1.385(4) no C1 C6 . 1.398(4) no C2 C3 . 1.365(4) no C2 H2 . .9300 no C3 C4 . 1.392(4) no C3 H3 . .9300 no C4 C5 . 1.382(5) no C5 C6 . 1.373(4) no C5 H5 . .9300 no C6 H6 . .9300 no C7 H7A . .9600 no C7 H7B . .9600 no C7 H7C . .9600 no C11 C16 . 1.377(4) no C11 C12 . 1.403(4) no C12 C13 . 1.405(4) no C13 C14 . 1.377(4) no C13 H13 . .9300 no C14 C15 . 1.405(4) no C14 C17 . 1.492(4) no C15 C16 . 1.379(4) no C15 H15 . .9300 no C16 H16 . .9300 no C17 C18 . 1.389(4) no C17 C22 . 1.391(4) no C18 C19 . 1.384(4) no C18 H18 . .9300 no C19 C20 . 1.374(5) no C19 H19 . .9300 no C20 C21 . 1.369(5) no C20 H20 . .9300 no C21 C22 . 1.388(5) no C21 H21 . .9300 no C22 H22 . .9300 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1 N1 .88(3) 1.81(3) 2.581(4) 146(3) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 12554746 2 PubChem 4041039