#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/29/2002919.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_2002919 loop_ _publ_author_name 'Loehlin, J. H.' 'Franz, K. J.' 'Gist, L.' 'Moore, R. H.' _publ_section_title ; Supramolecular Alcohol--Amine Crystals and Their Hydrogen-Bond Patterns ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 695 _journal_page_last 704 _journal_paper_doi 10.1107/S0108768198003231 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C6 H8 N2 , 2C6 H6 O' _chemical_formula_structural 'C6 H4 (N H2 )2 , 2C6 H5 OH' _chemical_formula_sum 'C18 H20 N2 O2' _chemical_formula_weight 296.4 _chemical_melting_point 377.1(10) _chemical_name_common 'p-phenylenediamine.2 phenol' _chemical_name_systematic (1,4-diaminobenzene).2(hydroxybenzene) _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' _audit_creation_method from_xtal_archive_file_using_CIFIO _cell_angle_alpha 90.000 _cell_angle_beta 91.250(9) _cell_angle_gamma 90.000 _cell_formula_units_Z 2 _cell_length_a 18.2810(18) _cell_length_b 5.3790(5) _cell_length_c 8.1550(8) _cell_measurement_reflns_used 39 _cell_measurement_temperature 295 _cell_measurement_theta_max 12.4 _cell_measurement_theta_min 5.5 _cell_volume 801.72(13) _computing_cell_refinement 'XSCANS (Siemens, 1993)' _computing_data_collection 'XSCANS (Siemens, 1993)' _computing_data_reduction 'XSCANS (Siemens, 1993)' _computing_molecular_graphics 'Xtal_ORTEPIII (Hall et al., 1995)' _computing_publication_material 'Xtal_BONDLA_CIFIO (Hall et al., 1995)' _computing_structure_refinement 'Xtal_CRYLSQ (Hall et al., 1995)' _computing_structure_solution 'Xtal (Hall et al., 1995)' _diffrn_ambient_temperature 295 _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed x-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .027 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 1020 _diffrn_reflns_reduction_process 'Lp and standards decay corrections' _diffrn_reflns_theta_max 23.75 _diffrn_reflns_theta_min 2.23 _diffrn_standards_decay_% 2.7 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .087 _exptl_absorpt_process_details none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_meas ? _exptl_crystal_description 'cut from long thin plate' _exptl_crystal_F_000 316 _exptl_crystal_size_max .48 _exptl_crystal_size_mid .42 _exptl_crystal_size_min .18 _refine_diff_density_max .25 _refine_diff_density_min -.25 _refine_ls_abs_structure_details none _refine_ls_abs_structure_Flack 0 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_obs 1.118 _refine_ls_hydrogen_treatment '-NH~2~ and -OH hydrogens refined, others calculated, all isotropic' _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 112 _refine_ls_number_reflns 769 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .132 _refine_ls_R_factor_obs .040 _refine_ls_shift/esd_max .002 _refine_ls_shift/esd_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details w=1/[\s^2^(F~o~^2^)+0.0020F~o~^2^] _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .138 _refine_ls_wR_factor_obs .091 _reflns_number_observed 769 _reflns_number_total 1848 _reflns_observed_criterion refl_observed_if_Fsqd_>_3.50_sigma(Fsqd) _cod_data_source_file bk0047.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '103-105C' was changed to '377.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '103-105C' was changed to '377.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. 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 'w=1/[\s^2^(F~o~^2^)+0.0020F~o~^2^]' 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^(F~o~^2^)+0.0020F~o~^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 801.72(14) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2002919 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,1/2-z -x,-y,-z +x,1/2-y,1/2+z 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 .0334(16) .064(3) .080(2) -.0033(17) -.0033(13) .018(2) C2 .039(2) .042(3) .042(2) .005(2) .0011(18) -.002(3) C3 .048(2) .048(3) .045(3) .001(2) .002(2) .007(2) C4 .039(2) .043(3) .068(3) -.007(2) .009(2) -.002(3) C5 .036(2) .061(3) .075(3) .010(3) -.005(2) .002(3) C6 .059(3) .047(3) .055(3) .015(2) -.006(2) .004(3) C7 .048(2) .039(3) .055(3) .001(2) .008(2) .008(3) N8 .037(2) .069(4) .045(3) .001(2) .0029(17) .001(3) C9 .0250(19) .047(3) .038(2) .001(2) -.0007(16) .002(3) C10 .040(2) .045(3) .049(3) -.009(2) -.0042(19) -.010(3) C11 .040(2) .040(3) .045(3) .005(2) .0073(18) -.011(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_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 .20325(13) .5525(6) .5757(4) .059(2) Uani ? ? H1 .190(2) .703(7) .528(5) .071(17) Uiso ? ? C2 .27771(18) .5321(7) .6046(4) .041(3) Uani ? ? C3 .32654(19) .7036(8) .5451(5) .047(3) Uani ? ? H3 .30966 .84233 .48056 .04500 Uiso ? ? C4 .40059(18) .6715(8) .5804(5) .050(3) Uani ? ? H4 .43512 .78957 .53978 .04500 Uiso ? ? C5 .42513(18) .4752(8) .6715(5) .057(3) Uani ? ? H5 .47650 .45581 .69551 .04500 Uiso ? ? C6 .3761(2) .3059(8) .7287(5) .054(3) Uani ? ? H6 .39328 .16629 .79212 .04500 Uiso ? ? C7 .30200(19) .3348(8) .6960(5) .047(3) Uani ? ? H7 .26774 .21615 .73754 .04500 Uiso ? ? N8 .15165(16) -.0070(9) .4396(5) .050(3) Uani ? ? H8 .171(2) .160(8) .472(5) .098(18) Uiso ? ? H9 .1568(15) -.030(7) .341(4) .034(12) Uiso ? ? C9 .07400(16) .0005(7) .4672(4) .036(2) Uani ? ? C10 -.04473(18) -.1759(7) .4319(5) .045(2) Uani ? ? H10 -.07620 -.30041 .38400 .04500 Uiso ? ? C11 -.02911(17) .1783(7) .6008(5) .041(2) Uani ? ? H11 -.04930 .30233 .67125 .04500 Uiso ? ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? .002 .002 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 H ? 0 0 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 N ? .004 .003 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 O ? .008 .006 Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 -2 2 1 -1 2 0 0 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H1 O1 C2 . . . 113(2) yes O1 C2 C3 . . . 122.0(4) yes O1 C2 C7 . . . 117.6(3) yes C3 C2 C7 . . . 120.4(3) yes C2 C3 H3 . . . 120.7(3) yes C2 C3 C4 . . . 118.6(4) yes H3 C3 C4 . . . 120.7(4) yes C3 C4 H4 . . . 119.5(4) yes C3 C4 C5 . . . 121.2(4) yes H4 C4 C5 . . . 119.4(3) yes C4 C5 H5 . . . 120.3(4) yes C4 C5 C6 . . . 119.5(3) yes H5 C5 C6 . . . 120.2(4) yes C5 C6 H6 . . . 119.7(4) yes C5 C6 C7 . . . 120.4(4) yes H6 C6 C7 . . . 119.9(4) yes C2 C7 C6 . . . 119.8(4) yes C2 C7 H7 . . . 120.1(3) yes C6 C7 H7 . . . 120.0(4) yes H8 N8 H9 4 4 4 110(3) yes H8 N8 C9 4 4 4 106(2) yes H9 N8 C9 4 4 4 107(2) yes N8 C9 C10 4 4 2_556 120.8(3) yes N8 C9 C11 4 4 2_556 119.1(3) yes C10 C9 C11 2_556 4 2_556 119.2(3) yes C9 C10 H10 4 2_556 2_556 119.1(3) yes C9 C10 C11 4 2_556 4 121.3(3) yes H10 C10 C11 2_556 2_556 4 119.6(4) yes C9 C11 H11 4 2_556 2_556 119.6(3) yes C9 C11 C10 4 2_556 4 119.6(4) yes H11 C11 C10 2_556 2_556 4 120.8(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 H1 . . .93(4) yes O1 C2 . . 1.381(4) yes C2 C3 . . 1.379(5) yes C2 C7 . . 1.365(5) yes C3 H3 . . .9600 yes C3 C4 . . 1.389(5) yes C4 H4 . . .9600 yes C4 C5 . . 1.362(6) yes C5 H5 . . .9600 yes C5 C6 . . 1.366(6) yes C6 H6 . . .9600 yes C6 C7 . . 1.384(5) yes C7 H7 . . .9600 yes N8 H8 4 4 1.00(4) yes N8 H9 4 4 .82(3) yes N8 C9 4 4 1.443(4) yes C9 C10 4 2_556 1.369(5) yes C9 C11 4 2_556 1.373(5) yes C10 H10 2_556 2_556 .9600 yes C10 C11 2_556 4 1.382(5) yes C11 H11 2_556 2_556 .9600 yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 O1 H1 .93(4) . O1 C2 1.381(4) . O1 C3 2.414(4) . O1 H3 2.623(3) . O1 C7 2.349(5) . O1 H7 2.518(3) . O1 N8 3.144(5) 4 O1 H8 3.49(4) 4 O1 H9 2.34(3) 4 O1 H7 3.350(3) . O1 N8 3.337(6) 4 O1 N8 2.773(6) 4 O1 H8 2.34(4) 4 O1 H8 3.42(4) 4 O1 H9 3.06(3) 4 O1 C9 3.476(4) 4 O1 H10 2.716(3) 2_556 N8 O1 2.773(6) . N8 O1 3.337(6) . N8 H1 1.85(4) . N8 H3 3.012(3) . N8 H7 3.409(4) . N8 H10 3.153(4) 2_556 N8 O1 3.144(5) . N8 H7 3.134(4) . N8 H8 1.00(4) 4 N8 H9 .82(3) 4 N8 C9 1.443(4) 4 N8 C10 2.444(5) 2_556 N8 H10 2.606(4) 2_556 N8 C11 2.438(5) 2_556 N8 H11 2.602(4) 2_556 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139054109