#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/29/2002977.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_2002977 loop_ _publ_author_name 'Ferguson, George' 'Glidewell, Christopher' 'Lavender, Emma S.' _publ_section_title ; Crystal engineering using bisphenols and trisphenols. Complexes with 1,10-phenanthroline: hydrogen-bonded chains in adducts with 4,4'-biphenol (1/1) and 4,4'-sulfonyldiphenol (2/3), \p--\p stacked chains in the (1/2) adduct with 4,4'-thiodiphenol, and pairwise-interwoven nets in 1,1,1-tris(4-hydroxyphenyl)ethane--1,10-phenanthroline--methanol (1/1/1) ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 591 _journal_page_last 600 _journal_paper_doi 10.1107/S0108768199002657 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C12 H10 O2, C12 H8 N2' _chemical_formula_sum 'C24 H18 N2 O2' _chemical_formula_weight 366.40 _chemical_name_systematic ; 4,4'-Biphenol--1,10-phenanthroline (1/1) ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 105.199(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.0288(17) _cell_length_b 12.1865(10) _cell_length_c 12.0778(12) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294.0(10) _cell_measurement_theta_max 18.79 _cell_measurement_theta_min 9.82 _cell_volume 1850.6(3) _computing_cell_refinement 'SET4 & CELDIM (Enraf-Nonius, 1992)' _computing_data_collection 'CAD4 (Enraf-Nonius, 1992)' _computing_data_reduction 'DATRD2 in NRCVAX96 (Gabe et al., 1989)' _computing_molecular_graphics 'NRCVAX96, ORTEP (Johnson, 1976), PLATON (Spek, 1998)' _computing_publication_material 'NRCVAX96, SHELXL97 and WordPerfect macro PRPCIF97 (Ferguson, 1997)' _computing_structure_refinement 'NRCVAX96 and SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 294.0(10) _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1748 _diffrn_reflns_theta_full 25.19 _diffrn_reflns_theta_max 25.19 _diffrn_reflns_theta_min 2.32 _diffrn_standards_decay_% 'no decay, variation 0.5' _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_meas ? _exptl_crystal_description lath _exptl_crystal_F_000 768 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.140 _refine_diff_density_min -0.127 _refine_ls_extinction_coef 0.0049(9) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1678 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.976 _refine_ls_R_factor_all 0.0878 _refine_ls_R_factor_gt 0.0334 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0542P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0989 _reflns_number_gt 915 _reflns_number_total 1678 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file cf0005.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^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^)+(0.0542P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2002977 _cod_database_fobs_code 2002977 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 0.44259(12) 0.74375(12) 0.13717(12) 0.0563(4) Uani d . 1 . . N C2 0.47035(13) 0.84112(14) 0.19040(14) 0.0481(4) Uani d . 1 . . C C3 0.44280(14) 0.94214(16) 0.13423(16) 0.0568(5) Uani d . 1 . . C C4 0.38652(16) 0.9395(2) 0.01853(19) 0.0703(6) Uani d . 1 . . C C5 0.36177(17) 0.8425(2) -0.03565(18) 0.0744(6) Uani d . 1 . . C C6 0.39058(16) 0.74627(18) 0.02664(16) 0.0684(6) Uani d . 1 . . C C7 0.47228(17) 1.04284(16) 0.19502(17) 0.0722(6) Uani d . 1 . . C C11 0.27194(13) 0.29537(13) 0.04021(13) 0.0426(4) Uani d . 1 . . C C12 0.34504(15) 0.36973(15) 0.01837(15) 0.0558(5) Uani d . 1 . . C C13 0.38423(15) 0.45618(15) 0.09022(15) 0.0576(5) Uani d . 1 . . C C14 0.34859(13) 0.47393(13) 0.18692(14) 0.0468(4) Uani d . 1 . . C C15 0.27948(15) 0.39957(15) 0.21315(14) 0.0534(5) Uani d . 1 . . C C16 0.24227(15) 0.31224(14) 0.14145(14) 0.0526(5) Uani d . 1 . . C O14 0.37876(11) 0.56258(10) 0.25684(10) 0.0604(4) Uani d . 1 . . O H4 0.3661 1.0048 -0.0211 0.084 Uiso calc R 1 . . H H5 0.3261 0.8400 -0.1131 0.089 Uiso calc R 1 . . H H6 0.3724 0.6798 -0.0112 0.082 Uiso calc R 1 . . H H7 0.4526 1.1092 0.1575 0.087 Uiso calc R 1 . . H H12 0.3684 0.3607 -0.0475 0.067 Uiso calc R 1 . . H H13 0.4348 0.5028 0.0737 0.069 Uiso calc R 1 . . H H15 0.2575 0.4082 0.2800 0.064 Uiso calc R 1 . . H H16 0.1957 0.2629 0.1614 0.063 Uiso calc R 1 . . H H14 0.4119 0.6056 0.2270 0.091 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 0.0546(10) 0.0565(10) 0.0546(9) -0.0030(7) 0.0087(7) -0.0013(8) C2 0.0406(10) 0.0500(11) 0.0574(10) -0.0001(8) 0.0194(8) 0.0015(9) C3 0.0491(11) 0.0567(12) 0.0699(13) 0.0070(9) 0.0250(10) 0.0130(10) C4 0.0582(13) 0.0783(16) 0.0756(15) 0.0101(11) 0.0197(11) 0.0276(13) C5 0.0633(13) 0.0963(18) 0.0585(13) 0.0013(13) 0.0070(10) 0.0201(13) C6 0.0640(13) 0.0784(15) 0.0570(12) -0.0089(11) 0.0056(10) -0.0025(11) C7 0.0861(17) 0.0481(11) 0.0932(15) 0.0081(10) 0.0430(14) 0.0108(9) C11 0.0476(10) 0.0404(9) 0.0421(9) 0.0035(7) 0.0160(8) 0.0020(7) C12 0.0650(12) 0.0560(11) 0.0551(11) -0.0083(10) 0.0314(10) -0.0111(9) C13 0.0605(12) 0.0568(12) 0.0623(12) -0.0138(9) 0.0284(10) -0.0117(9) C14 0.0483(11) 0.0464(10) 0.0433(9) 0.0014(8) 0.0077(8) -0.0061(8) C15 0.0693(13) 0.0545(11) 0.0401(10) -0.0039(10) 0.0206(9) -0.0020(8) C16 0.0668(12) 0.0492(11) 0.0458(10) -0.0075(9) 0.0218(9) 0.0031(9) O14 0.0701(9) 0.0575(8) 0.0556(8) -0.0096(7) 0.0201(6) -0.0160(7) 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -5 -3 3 5 3 -3 5 -3 -3 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_3 _geom_angle C6 N1 C2 . . 117.34(16) N1 C2 C3 . . 122.42(16) N1 C2 C2 . 2_655 118.70(9) C3 C2 C2 . 2_655 118.89(11) C4 C3 C2 . . 117.59(18) C4 C3 C7 . . 122.18(18) C2 C3 C7 . . 120.23(17) C5 C4 C3 . . 120.05(19) C4 C5 C6 . . 118.7(2) N1 C6 C5 . . 123.8(2) C7 C7 C3 2_655 . 120.88(11) C12 C11 C16 . . 115.66(15) C12 C11 C11 . 7 121.83(18) C16 C11 C11 . 7 122.51(19) C13 C12 C11 . . 122.65(16) C12 C13 C14 . . 120.10(17) O14 C14 C15 . . 118.71(15) O14 C14 C13 . . 122.74(16) C15 C14 C13 . . 118.55(16) C14 C15 C16 . . 120.62(15) C15 C16 C11 . . 122.26(16) 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 C2 . 1.353(2) no N1 C6 . 1.330(2) no C2 C2 2_655 1.444(3) no C2 C3 . 1.406(2) no C3 C4 . 1.398(3) no C3 C7 . 1.430(3) no C4 C5 . 1.349(3) no C5 C6 . 1.391(3) no C7 C7 2_655 1.335(4) no C11 C11 7 1.484(3) no C11 C12 . 1.389(2) no C11 C16 . 1.391(2) no C12 C13 . 1.375(2) no C13 C14 . 1.382(2) no C14 O14 . 1.3640(19) no C14 C15 . 1.372(2) no C15 C16 . 1.377(2) no 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 O14 H14 N1 . .82 2.10 2.878(2) 159 no C12 H12 O14 6_565 .93 2.58 3.403(2) 148 no 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 N1 C2 C3 . . 2.4(2) no C6 N1 C2 C2 . 2_655 -178.21(19) no N1 C2 C3 C4 . . -1.3(2) no C2 C2 C3 C4 2_655 . 179.26(19) no N1 C2 C3 C7 . . 178.76(17) no C2 C2 C3 C7 2_655 . -.7(3) no C2 C3 C4 C5 . . -.9(3) no C7 C3 C4 C5 . . 179.1(2) no C3 C4 C5 C6 . . 1.8(3) no C2 N1 C6 C5 . . -1.3(3) no C4 C5 C6 N1 . . -.8(3) no C4 C3 C7 C7 . 2_655 -178.8(2) no C2 C3 C7 C7 . 2_655 1.1(3) no C16 C11 C12 C13 . . -1.4(3) no C11 C11 C12 C13 7 . 178.07(19) no C11 C12 C13 C14 . . -2.0(3) no C12 C13 C14 O14 . . -175.22(16) no C12 C13 C14 C15 . . 4.4(3) no O14 C14 C15 C16 . . 176.33(15) no C13 C14 C15 C16 . . -3.3(3) no C14 C15 C16 C11 . . -.3(3) no C12 C11 C16 C15 . . 2.6(3) no C11 C11 C16 C15 7 . -176.92(19) no