#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2002977.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_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 .99 _diffrn_measured_fraction_theta_max .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 .7107 _diffrn_reflns_av_R_equivalents .012 _diffrn_reflns_av_sigmaI/netI .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 .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 'not measured' _exptl_crystal_description lath _exptl_crystal_F_000 768 _exptl_crystal_size_max .42 _exptl_crystal_size_mid .31 _exptl_crystal_size_min .12 _refine_diff_density_max .140 _refine_diff_density_min -.127 _refine_ls_extinction_coef .0049(9) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref .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 .976 _refine_ls_R_factor_all .0878 _refine_ls_R_factor_gt .0334 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_ref .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_database_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_type_symbol N1 .44259(12) .74375(12) .13717(12) .0563(4) Uani d . 1 N C2 .47035(13) .84112(14) .19040(14) .0481(4) Uani d . 1 C C3 .44280(14) .94214(16) .13423(16) .0568(5) Uani d . 1 C C4 .38652(16) .9395(2) .01853(19) .0703(6) Uani d . 1 C C5 .36177(17) .8425(2) -.03565(18) .0744(6) Uani d . 1 C C6 .39058(16) .74627(18) .02664(16) .0684(6) Uani d . 1 C C7 .47228(17) 1.04284(16) .19502(17) .0722(6) Uani d . 1 C C11 .27194(13) .29537(13) .04021(13) .0426(4) Uani d . 1 C C12 .34504(15) .36973(15) .01837(15) .0558(5) Uani d . 1 C C13 .38423(15) .45618(15) .09022(15) .0576(5) Uani d . 1 C C14 .34859(13) .47393(13) .18692(14) .0468(4) Uani d . 1 C C15 .27948(15) .39957(15) .21315(14) .0534(5) Uani d . 1 C C16 .24227(15) .31224(14) .14145(14) .0526(5) Uani d . 1 C O14 .37876(11) .56258(10) .25684(10) .0604(4) Uani d . 1 O H4 .3661 1.0048 -.0211 .084 Uiso calc R 1 H H5 .3261 .8400 -.1131 .089 Uiso calc R 1 H H6 .3724 .6798 -.0112 .082 Uiso calc R 1 H H7 .4526 1.1092 .1575 .087 Uiso calc R 1 H H12 .3684 .3607 -.0475 .067 Uiso calc R 1 H H13 .4348 .5028 .0737 .069 Uiso calc R 1 H H15 .2575 .4082 .2800 .064 Uiso calc R 1 H H16 .1957 .2629 .1614 .063 Uiso calc R 1 H H14 .4119 .6056 .2270 .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 .0546(10) .0565(10) .0546(9) -.0030(7) .0087(7) -.0013(8) C2 .0406(10) .0500(11) .0574(10) -.0001(8) .0194(8) .0015(9) C3 .0491(11) .0567(12) .0699(13) .0070(9) .0250(10) .0130(10) C4 .0582(13) .0783(16) .0756(15) .0101(11) .0197(11) .0276(13) C5 .0633(13) .0963(18) .0585(13) .0013(13) .0070(10) .0201(13) C6 .0640(13) .0784(15) .0570(12) -.0089(11) .0056(10) -.0025(11) C7 .0861(17) .0481(11) .0932(15) .0081(10) .0430(14) .0108(9) C11 .0476(10) .0404(9) .0421(9) .0035(7) .0160(8) .0020(7) C12 .0650(12) .0560(11) .0551(11) -.0083(10) .0314(10) -.0111(9) C13 .0605(12) .0568(12) .0623(12) -.0138(9) .0284(10) -.0117(9) C14 .0483(11) .0464(10) .0433(9) .0014(8) .0077(8) -.0061(8) C15 .0693(13) .0545(11) .0401(10) -.0039(10) .0206(9) -.0020(8) C16 .0668(12) .0492(11) .0458(10) -.0075(9) .0218(9) .0031(9) O14 .0701(9) .0575(8) .0556(8) -.0096(7) .0201(6) -.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 .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_ _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