Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_4-phenylimidazole _audit_creation_date 01-00-03 _audit_creation_method from_xtal_archive_file_using_CIFIO _audit_update_record ? _chemical_compound_source ? #ActaC _chemical_name_systematic '4-phenylimidazole' #ActaC _chemical_name_common ? #ActaC _chemical_formula_analytical ? #ActaC _chemical_formula_moiety 'C9 H8 N2' #ActaC _chemical_formula_structural ? #ActaC _chemical_formula_sum C9_H8_N2 #ActaC _chemical_formula_weight 144.18 #ActaC _chemical_melting_point ? #ActaC _computing_data_collection 'Seifert XRD3000-S' #ActaC _computing_cell_refinement 'LSUCRE (D.E.Appleman)' #ActaC _computing_data_reduction xtal_DIFDAT_SORTRF_ADDREF #ActaC _computing_structure_solution 'SIR92 (Altomare et al., 1994)' #ActaC _computing_structure_refinement 'xtal_CRYLSQ (S.R.Hall et al)' #ActaC _computing_molecular_graphics xtal_ORTEP #ActaC _computing_publication_material xtal_BONDLA_CIFIO #ActaC _cell_length_a 20.627(2) #ActaC _cell_length_b 20.627(2) #ActaC _cell_length_c 9.7660(10) #ActaC _cell_angle_alpha 90.00000 #ActaC _cell_angle_beta 90.00000 #ActaC _cell_angle_gamma 120.0000 #ActaC _cell_volume 3598.5(8) #ActaC _cell_formula_units_Z 18 #ActaC _cell_measurement_temperature 293 #ActaC _cell_measurement_reflns_used 48 #ActaC _cell_measurement_theta_min 4.2 #ActaC _cell_measurement_theta_max 33.8 #ActaC _cell_special_details #ActaC ; ? ; _symmetry_cell_setting trigonal #ActaC _symmetry_space_group_name_H-M R_3_c:h #ActaC _symmetry_space_group_name_Hall r_3_-2"c #ActaC loop_ _symmetry_equiv_pos_as_xyz #ActaC +x,+y,+z -y,+x-y,+z -y,-x,1/2+z -x+y,-x,+z +x,+x-y,1/2+z -x+y,+y,1/2+z 2/3+x,1/3+y,1/3+z 1/3+x,2/3+y,2/3+z 2/3-y,1/3+x-y,1/3+z 1/3-y,2/3+x-y,2/3+z 2/3-y,1/3-x,5/6+z 1/3-y,2/3-x,1/6+z 2/3-x+y,1/3-x,1/3+z 1/3-x+y,2/3-x,2/3+z 2/3+x,1/3+x-y,5/6+z 1/3+x,2/3+x-y,1/6+z 2/3-x+y,1/3+y,5/6+z 1/3-x+y,2/3+y,1/6+z _exptl_crystal_description needle #ActaC _exptl_crystal_preparation ? _exptl_crystal_colour colourless #ActaC _exptl_crystal_size_max 0.57 #ActaC _exptl_crystal_size_mid 0.07 #ActaC _exptl_crystal_size_min 0.03 #ActaC _exptl_crystal_density_diffrn 1.198 #ActaC _exptl_crystal_density_meas ? #ActaC _exptl_crystal_density_method 'not measured' #ActaC _exptl_crystal_F_000 1368 #ActaC _exptl_absorpt_process_details ? _exptl_absorpt_coefficient_mu .58 #ActaC _exptl_absorpt_correction_type none #ActaC _exptl_absorpt_correction_T_min ? #ActaC _exptl_absorpt_correction_T_max ? #ActaC _exptl_special_details #ActaC ; ? ; _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293 #ActaC _diffrn_radiation_wavelength 1.5418 #ActaC _diffrn_radiation_type xray_synch #ActaC _diffrn_radiation_source 'Cu K/a' #ActaC _diffrn_radiation_monochromator graphite #ActaC _diffrn_radiation_detector ? #ActaC _diffrn_measurement_device 'Seifert XRD3000-S diffractometer' #ActaC _diffrn_measurement_method '\w/2\s' #ActaC _diffrn_standards_number 2 #ActaC _diffrn_standards_interval_count 100 #ActaC _diffrn_standards_interval_time ? #ActaC _diffrn_standards_decay_% 0 #ActaC loop_ _diffrn_standard_refln_index_h #ActaC _diffrn_standard_refln_index_k #ActaC _diffrn_standard_refln_index_l #ActaC 1 -4 2 -1 4 -2 loop_ _diffrn_attenuator_code _diffrn_attenuator_scale ? ? _diffrn_reflns_number 2489 #ActaC _diffrn_reflns_av_R_equivalents .071 #ActaC _diffrn_reflns_av_sigmaI/netI .042 #ActaC _diffrn_reflns_limit_h_min -1 #ActaC _diffrn_reflns_limit_h_max 21 #ActaC _diffrn_reflns_limit_k_min -4 #ActaC _diffrn_reflns_limit_k_max 21 #ActaC _diffrn_reflns_limit_l_min -2 #ActaC _diffrn_reflns_limit_l_max 11 #ActaC _diffrn_reflns_theta_min 4.29 #ActaC _diffrn_reflns_theta_max 66.46 #ActaC _diffrn_reflns_reduction_process equatorial_monochr_Lp #ActaC loop_ _atom_type_symbol #ActaC _atom_type_description #ActaC _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real #ActaC _atom_type_scat_dispersion_imag #ActaC _atom_type_scat_source #ActaC C ? 0 162 .017 .009 INTERNATIONAL_TABLES_FOR_X-RAY= H ? 0 144 0 0 INTERNATIONAL_TABLES_FOR_X-RAY= N ? 0 36 .029 .018 INTERNATIONAL_TABLES_FOR_X-RAY= loop_ _atom_site_label #ActaC _atom_site_fract_x #ActaC _atom_site_fract_y #ActaC _atom_site_fract_z #ActaC _atom_site_U_iso_or_equiv #ActaC _atom_site_thermal_displace_type #ActaC _atom_site_calc_flag #ActaC _atom_site_calc_attached_atom #ActaC N1 .7047(2) .2459(2) .52755 .0430(17) Uani ? ? C2 .7340(3) .2839(3) .4118(7) .045(2) Uani ? ? N3 .7096(2) .2433(2) .3009(5) .0402(16) Uani ? ? C4 .6594(2) .1722(2) .3478(6) .0343(17) Uani ? ? C5 .6562(3) .1737(3) .4881(6) .043(2) Uani ? ? C6 .6211(2) .1071(2) .2566(6) .0399(18) Uani ? ? C7 .6574(3) .0973(3) .1461(6) .049(2) Uani ? ? C8 .6224(4) .0342(3) .0652(7) .064(3) Uani ? ? C9 .5492(4) -.0206(3) .0932(7) .069(3) Uani ? ? C10 .5125(3) -.0112(3) .2011(7) .068(3) Uani ? ? C11 .5473(3) .0522(3) .2830(7) .056(2) Uani ? ? H1 .718(3) .265(3) .631(6) .030(14) Uiso ? ? H2 .767(4) .326(4) .417(7) .028(14) Uiso ? ? H5 .628(3) .140(3) .559(6) .016(11) Uiso ? ? H7 .708(4) .134(3) .125(6) .025(13) Uiso ? ? H8 .654(5) .031(4) -.008(9) .05(2) Uiso ? ? H9 .522(4) -.058(5) .029(8) .047(18) Uiso ? ? H10 .459(5) -.052(4) .221(7) .047(18) Uiso ? ? H11 .524(4) .056(4) .366(7) .042(17) Uiso ? ? loop_ _atom_site_aniso_label #ActaC _atom_site_aniso_U_11 #ActaC _atom_site_aniso_U_22 #ActaC _atom_site_aniso_U_33 #ActaC _atom_site_aniso_U_12 #ActaC _atom_site_aniso_U_13 #ActaC _atom_site_aniso_U_23 #ActaC N1 .045(2) .050(2) .037(2) .0255(18) -.0041(16) -.0030(16) C2 .037(2) .041(3) .049(2) .015(2) -.003(2) -.005(2) N3 .0421(19) .0364(17) .041(2) .0187(16) .0027(14) .0025(14) C4 .037(2) .041(2) .028(2) .0218(19) .0011(15) .0038(16) C5 .042(2) .048(2) .040(2) .024(2) .0002(19) .001(2) C6 .042(2) .039(2) .040(2) .0201(17) -.0038(17) .0019(17) C7 .053(3) .051(3) .043(2) .025(3) .001(2) -.003(2) C8 .081(4) .057(3) .051(3) .032(3) .001(3) -.007(2) C9 .086(4) .043(3) .062(3) .019(3) -.020(3) -.013(3) C10 .056(3) .048(3) .073(4) .005(3) -.010(3) -.001(3) C11 .047(2) .049(3) .058(3) .014(2) .006(2) .001(2) _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _refine_special_details sfls__F_____calc_weight______full_matrix _refine_ls_structure_factor_coef F #ActaC _refine_ls_matrix_type full #ActaC _refine_ls_weighting_scheme ; 'w = k/[(A+B Fo)^2^(C+D(sin\q)/\l)]' ; #ActaC _refine_ls_hydrogen_treatment refall #ActaC _refine_ls_extinction_method Zachariasen #ActaC _refine_ls_extinction_coef 13995(894) #ActaC _refine_ls_extinction_expression Eq22_p292_"Cryst._Comp."_Munksgaard_1970 _refine_ls_abs_structure_details none #ActaC _refine_ls_abs_structure_Flack 0 #ActaC _refine_ls_number_reflns 663 #ActaC _refine_ls_number_parameters 131 #ActaC _refine_ls_number_restraints 0 #ActaC _refine_ls_number_constraints 0 #ActaC _refine_ls_R_factor_all .068 #ActaC _refine_ls_R_factor_obs .05 #ActaC _refine_ls_wR_factor_all .06 #ActaC _refine_ls_wR_factor_obs .058 #ActaC _refine_ls_goodness_of_fit_all .905 #ActaC _refine_ls_goodness_of_fit_obs .907 #ActaC _refine_ls_shift/esd_max .004 #ActaC _refine_ls_shift/esd_mean . #ActaC _refine_diff_density_min -.484 #ActaC _refine_diff_density_max .532 #ActaC _geom_special_details ? #ActaC loop_ _geom_bond_atom_site_label_1 #ActaC _geom_bond_atom_site_label_2 #ActaC _geom_bond_distance #ActaC _geom_bond_site_symmetry_1 #ActaC _geom_bond_site_symmetry_2 #ActaC _geom_bond_publ_flag #ActaC N1 H1 1.07(6) . . ? N1 C2 1.335(6) . . ? N1 C5 1.370(6) . . ? C2 H2 .80(7) . . ? C2 N3 1.306(7) . . ? N3 C4 1.383(6) . . ? C4 C5 1.373(8) . . ? C4 C6 1.470(7) . . ? C5 H5 .95(6) . . ? C6 C7 1.384(8) . . ? C6 C11 1.394(7) . . ? C7 H7 .95(6) . . ? C7 C8 1.377(8) . . ? C8 H8 .99(9) . . ? C8 C9 1.388(9) . . ? C9 H9 .93(8) . . ? C9 C10 1.367(10) . . ? C10 H10 1.01(8) . . ? C10 C11 1.388(9) . . ? C11 H11 .97(7) . . ? loop_ _geom_contact_atom_site_label_1 #ActaC _geom_contact_atom_site_label_2 #ActaC _geom_contact_distance #ActaC _geom_contact_site_symmetry_1 #ActaC _geom_contact_site_symmetry_2 #ActaC _geom_contact_publ_flag #ActaC ? ? ? ? ? ? loop_ _geom_angle_atom_site_label_1 #ActaC _geom_angle_atom_site_label_2 #ActaC _geom_angle_atom_site_label_3 #ActaC _geom_angle #ActaC _geom_angle_site_symmetry_1 #ActaC _geom_angle_site_symmetry_2 #ActaC _geom_angle_site_symmetry_3 #ActaC _geom_angle_publ_flag #ActaC H1 N1 C2 129(3) . . . ? H1 N1 C5 126(3) . . . ? C2 N1 C5 105.6(3) . . . ? H2 C2 N3 127(5) . . . ? H2 C2 N1 118(5) . . . ? N3 C2 N1 114.2(4) . . . ? C2 N3 C4 104.4(4) . . . ? C5 C4 N3 109.0(4) . . . ? C5 C4 C6 128.0(4) . . . ? N3 C4 C6 122.9(5) . . . ? H5 C5 N1 116(3) . . . ? H5 C5 C4 137(3) . . . ? N1 C5 C4 106.8(4) . . . ? C7 C6 C11 118.5(5) . . . ? C7 C6 C4 121.5(4) . . . ? C11 C6 C4 120.0(5) . . . ? H7 C7 C8 119(4) . . . ? H7 C7 C6 120(4) . . . ? C8 C7 C6 121.2(5) . . . ? H8 C8 C7 115(4) . . . ? H8 C8 C9 125(4) . . . ? C7 C8 C9 120.1(7) . . . ? H9 C9 C10 119(5) . . . ? H9 C9 C8 120(5) . . . ? C10 C9 C8 119.3(6) . . . ? H10 C10 C9 118(5) . . . ? H10 C10 C11 121(5) . . . ? C9 C10 C11 121.0(5) . . . ? H11 C11 C10 122(4) . . . ? H11 C11 C6 118(4) . . . ? C10 C11 C6 120.0(6) . . . ? loop_ _geom_torsion_atom_site_label_1 #ActaC _geom_torsion_atom_site_label_2 #ActaC _geom_torsion_atom_site_label_3 #ActaC _geom_torsion_atom_site_label_4 #ActaC _geom_torsion #ActaC _geom_torsion_site_symmetry_1 #ActaC _geom_torsion_site_symmetry_2 #ActaC _geom_torsion_site_symmetry_3 #ActaC _geom_torsion_site_symmetry_4 #ActaC _geom_torsion_publ_flag #ActaC ? ? ? ? ? ? ? ? ? ? _reflns_limit_h_min 0 _reflns_limit_h_max 21 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 11 _reflns_number_total 705 #ActaC _reflns_number_observed 665 #ActaC _reflns_observed_criterion refl_observed_if_I____>2.000_sigma(I___) _reflns_d_resolution_high .841 _reflns_d_resolution_low 10.313 loop_ _reflns_scale_group_code _reflns_scale_meas_F ? .799904 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_meas _refln_F_squared_calc _refln_F_squared_sigma _refln_observed_status _refln_scale_group_code ? ? ? ? ? ? ? ? _publ_requested_journal ? #ActaC _publ_requested_coeditor_name ? #ActaC _publ_contact_author #ActaC ; 'Dr. Infantes' Instituto de Qu\'imica-F\'isica Rocasolano.CSIC Dpto. de Cristalograf\'ia Serrano, 119 E-28028 Madrid Spain ; _publ_contact_letter #ActaC ; ? letter to co-editor ; _publ_contact_author_phone '34-915619400' #ActaC _publ_contact_author_fax '34-915642431' #ActaC _publ_contact_author_email xlourdes@iqfr.csic.es #ActaC loop_ _publ_author_name #ActaC _publ_author_address #ActaC '? surname, initials' ; ? institute ? department ? address ? city ? country ; _publ_section_title #ActaC ; ? ; _publ_section_abstract #ActaC ; ? ; _publ_section_comment #ActaC ; ? ; _publ_section_experimental #ActaC ; ? ; _publ_section_references #ActaC ; ? ; _publ_section_figure_captions #ActaC ; ? ; _publ_section_acknowledgements #ActaC ; ? ; #============================================================================== # (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ?