# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Edwin Weber' _publ_contact_author_email EDWIN.WEBER@CHEMIE.TU-FREIBERG.DE _publ_section_title ; Competitive interactions in crystalline 9-pyridyl-9-fluorenols: Crossover from O-H...O to O-H...N hydrogen bonding to construct intra- and intermolecular, helical and linear contact modes ; loop_ _publ_author_name 'Edwin Weber' 'Rahmam Hosseinzadeh' 'Z Lasemi' 'Wilhelm Seichter' data_hoss_24a_0m _database_code_depnum_ccdc_archive 'CCDC 712757' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 N O' _chemical_formula_sum 'C18 H13 N O' _chemical_formula_weight 259.29 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.9969(3) _cell_length_b 7.6546(2) _cell_length_c 13.4691(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.859(2) _cell_angle_gamma 90.00 _cell_volume 1320.20(6) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3367 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 26.55 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9368 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 14541 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.80 _reflns_number_total 3112 _reflns_number_gt 2356 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker AXS, 2004)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.2827P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3112 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1115 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40533(7) -0.00751(11) 0.83639(8) 0.0411(3) Uani 1 1 d . . . H1 H 0.4017 -0.1096 0.8539 0.062 Uiso 1 1 calc R . . N1 N 0.39889(10) 0.63541(14) 0.88818(9) 0.0444(3) Uani 1 1 d . . . C1 C 0.27961(10) 0.01611(15) 0.95287(10) 0.0332(3) Uani 1 1 d . . . C2 C 0.33527(11) -0.00978(18) 1.04814(11) 0.0435(3) Uani 1 1 d . . . H2 H 0.4052 0.0223 1.0639 0.052 Uiso 1 1 calc R . . C3 C 0.28451(14) -0.0850(2) 1.12010(12) 0.0530(4) Uani 1 1 d . . . H3 H 0.3211 -0.1045 1.1848 0.064 Uiso 1 1 calc R . . C4 C 0.18034(13) -0.1314(2) 1.09709(12) 0.0528(4) Uani 1 1 d . . . H4 H 0.1477 -0.1814 1.1465 0.063 Uiso 1 1 calc R . . C5 C 0.12422(11) -0.10459(18) 1.00187(12) 0.0453(3) Uani 1 1 d . . . H5 H 0.0541 -0.1354 0.9868 0.054 Uiso 1 1 calc R . . C6 C 0.17440(10) -0.03063(16) 0.92872(10) 0.0354(3) Uani 1 1 d . . . C7 C 0.13779(10) 0.00557(16) 0.82152(11) 0.0372(3) Uani 1 1 d . . . C8 C 0.04017(11) -0.01501(19) 0.76171(12) 0.0490(4) Uani 1 1 d . . . H8 H -0.0156 -0.0601 0.7886 0.059 Uiso 1 1 calc R . . C9 C 0.02776(13) 0.0331(2) 0.66135(13) 0.0580(4) Uani 1 1 d . . . H9 H -0.0373 0.0215 0.6207 0.070 Uiso 1 1 calc R . . C10 C 0.11033(13) 0.0980(2) 0.62073(12) 0.0564(4) Uani 1 1 d . . . H10 H 0.1003 0.1288 0.5530 0.068 Uiso 1 1 calc R . . C11 C 0.20801(12) 0.11802(19) 0.67951(11) 0.0465(4) Uani 1 1 d . . . H11 H 0.2636 0.1619 0.6520 0.056 Uiso 1 1 calc R . . C12 C 0.22107(10) 0.07134(16) 0.77990(10) 0.0358(3) Uani 1 1 d . . . C13 C 0.31913(9) 0.08692(15) 0.86048(10) 0.0325(3) Uani 1 1 d . . . C14 C 0.35086(9) 0.27845(15) 0.87332(9) 0.0324(3) Uani 1 1 d . . . C15 C 0.28370(12) 0.39872(18) 0.90397(13) 0.0535(4) Uani 1 1 d . . . H15 H 0.2203 0.3623 0.9201 0.064 Uiso 1 1 calc R . . C16 C 0.31059(14) 0.57232(19) 0.91059(14) 0.0579(5) Uani 1 1 d . . . H16 H 0.2641 0.6503 0.9321 0.069 Uiso 1 1 calc R . . C17 C 0.46422(11) 0.51924(17) 0.86120(12) 0.0442(3) Uani 1 1 d . . . H17 H 0.5276 0.5593 0.8469 0.053 Uiso 1 1 calc R . . C18 C 0.44405(10) 0.34141(16) 0.85297(11) 0.0411(3) Uani 1 1 d . . . H18 H 0.4931 0.2656 0.8339 0.049 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0386(5) 0.0252(4) 0.0636(7) 0.0008(4) 0.0203(4) 0.0035(4) N1 0.0565(7) 0.0263(5) 0.0524(7) -0.0014(5) 0.0144(6) -0.0036(5) C1 0.0347(7) 0.0226(5) 0.0432(7) -0.0009(5) 0.0090(5) 0.0012(5) C2 0.0434(8) 0.0386(7) 0.0468(8) -0.0019(6) 0.0034(6) 0.0005(6) C3 0.0675(10) 0.0505(9) 0.0406(8) 0.0031(7) 0.0084(7) 0.0047(8) C4 0.0660(10) 0.0455(8) 0.0528(9) 0.0057(7) 0.0271(8) 0.0012(7) C5 0.0408(7) 0.0394(7) 0.0599(9) 0.0004(6) 0.0200(7) -0.0022(6) C6 0.0340(7) 0.0265(6) 0.0470(8) -0.0012(5) 0.0105(6) 0.0016(5) C7 0.0349(7) 0.0282(6) 0.0482(8) -0.0028(5) 0.0064(6) 0.0010(5) C8 0.0355(7) 0.0464(8) 0.0634(10) -0.0029(7) 0.0034(7) -0.0014(6) C9 0.0477(9) 0.0602(10) 0.0592(10) -0.0078(8) -0.0102(8) 0.0033(7) C10 0.0638(10) 0.0578(10) 0.0442(9) -0.0009(7) -0.0004(8) 0.0075(8) C11 0.0525(9) 0.0420(8) 0.0462(8) 0.0000(6) 0.0116(7) 0.0014(6) C12 0.0380(7) 0.0255(6) 0.0439(7) -0.0025(5) 0.0076(6) 0.0002(5) C13 0.0309(6) 0.0241(6) 0.0438(7) -0.0006(5) 0.0100(5) 0.0007(5) C14 0.0346(6) 0.0248(6) 0.0382(7) 0.0006(5) 0.0075(5) 0.0006(5) C15 0.0504(9) 0.0309(7) 0.0879(12) -0.0041(7) 0.0364(8) -0.0013(6) C16 0.0659(10) 0.0285(7) 0.0877(13) -0.0066(7) 0.0371(9) 0.0045(7) C17 0.0407(7) 0.0323(7) 0.0601(9) 0.0021(6) 0.0100(7) -0.0056(6) C18 0.0363(7) 0.0280(6) 0.0604(9) -0.0007(6) 0.0125(6) 0.0016(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.4168(14) . ? O1 H1 0.8200 . ? N1 C17 1.3226(18) . ? N1 C16 1.3268(19) . ? C1 C2 1.3753(19) . ? C1 C6 1.3969(18) . ? C1 C13 1.5248(18) . ? C2 C3 1.388(2) . ? C2 H2 0.9300 . ? C3 C4 1.383(2) . ? C3 H3 0.9300 . ? C4 C5 1.378(2) . ? C4 H4 0.9300 . ? C5 C6 1.3917(18) . ? C5 H5 0.9300 . ? C6 C7 1.4671(19) . ? C7 C8 1.391(2) . ? C7 C12 1.3953(18) . ? C8 C9 1.384(2) . ? C8 H8 0.9300 . ? C9 C10 1.378(2) . ? C9 H9 0.9300 . ? C10 C11 1.385(2) . ? C10 H10 0.9300 . ? C11 C12 1.381(2) . ? C11 H11 0.9300 . ? C12 C13 1.5306(18) . ? C13 C14 1.5248(16) . ? C14 C18 1.3740(17) . ? C14 C15 1.3796(18) . ? C15 C16 1.373(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.3871(18) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 H1 109.5 . . ? C17 N1 C16 116.03(12) . . ? C2 C1 C6 121.20(13) . . ? C2 C1 C13 128.01(12) . . ? C6 C1 C13 110.74(11) . . ? C1 C2 C3 118.32(14) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C4 C3 C2 120.97(15) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 120.81(14) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 118.83(14) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C1 119.87(13) . . ? C5 C6 C7 131.40(12) . . ? C1 C6 C7 108.68(11) . . ? C8 C7 C12 120.11(14) . . ? C8 C7 C6 131.20(13) . . ? C12 C7 C6 108.69(11) . . ? C9 C8 C7 118.56(15) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C10 C9 C8 121.03(15) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.85(15) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 118.58(14) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C7 120.87(13) . . ? C11 C12 C13 128.47(12) . . ? C7 C12 C13 110.62(12) . . ? O1 C13 C14 107.90(9) . . ? O1 C13 C1 113.31(10) . . ? C14 C13 C1 111.82(10) . . ? O1 C13 C12 113.14(10) . . ? C14 C13 C12 109.36(10) . . ? C1 C13 C12 101.25(10) . . ? C18 C14 C15 116.75(12) . . ? C18 C14 C13 123.04(11) . . ? C15 C14 C13 120.19(11) . . ? C16 C15 C14 119.88(13) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? N1 C16 C15 123.91(13) . . ? N1 C16 H16 118.0 . . ? C15 C16 H16 118.0 . . ? N1 C17 C18 124.07(13) . . ? N1 C17 H17 118.0 . . ? C18 C17 H17 118.0 . . ? C14 C18 C17 119.29(12) . . ? C14 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.5(2) . . . . ? C13 C1 C2 C3 -176.56(12) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 C6 0.4(2) . . . . ? C4 C5 C6 C1 -0.5(2) . . . . ? C4 C5 C6 C7 176.65(13) . . . . ? C2 C1 C6 C5 0.09(19) . . . . ? C13 C1 C6 C5 177.57(11) . . . . ? C2 C1 C6 C7 -177.66(11) . . . . ? C13 C1 C6 C7 -0.17(14) . . . . ? C5 C6 C7 C8 3.7(2) . . . . ? C1 C6 C7 C8 -178.87(13) . . . . ? C5 C6 C7 C12 -176.33(13) . . . . ? C1 C6 C7 C12 1.06(14) . . . . ? C12 C7 C8 C9 -0.8(2) . . . . ? C6 C7 C8 C9 179.09(13) . . . . ? C7 C8 C9 C10 0.8(2) . . . . ? C8 C9 C10 C11 -0.4(3) . . . . ? C9 C10 C11 C12 0.0(2) . . . . ? C10 C11 C12 C7 -0.1(2) . . . . ? C10 C11 C12 C13 -177.61(13) . . . . ? C8 C7 C12 C11 0.46(19) . . . . ? C6 C7 C12 C11 -179.48(12) . . . . ? C8 C7 C12 C13 178.41(11) . . . . ? C6 C7 C12 C13 -1.52(14) . . . . ? C2 C1 C13 O1 55.13(17) . . . . ? C6 C1 C13 O1 -122.13(11) . . . . ? C2 C1 C13 C14 -67.07(16) . . . . ? C6 C1 C13 C14 115.66(11) . . . . ? C2 C1 C13 C12 176.59(12) . . . . ? C6 C1 C13 C12 -0.67(13) . . . . ? C11 C12 C13 O1 -59.32(17) . . . . ? C7 C12 C13 O1 122.92(11) . . . . ? C11 C12 C13 C14 60.97(17) . . . . ? C7 C12 C13 C14 -116.79(11) . . . . ? C11 C12 C13 C1 179.10(13) . . . . ? C7 C12 C13 C1 1.34(12) . . . . ? O1 C13 C14 C18 6.33(17) . . . . ? C1 C13 C14 C18 131.58(13) . . . . ? C12 C13 C14 C18 -117.11(14) . . . . ? O1 C13 C14 C15 -175.54(13) . . . . ? C1 C13 C14 C15 -50.29(17) . . . . ? C12 C13 C14 C15 61.01(16) . . . . ? C18 C14 C15 C16 1.5(2) . . . . ? C13 C14 C15 C16 -176.79(15) . . . . ? C17 N1 C16 C15 -2.2(3) . . . . ? C14 C15 C16 N1 0.6(3) . . . . ? C16 N1 C17 C18 1.8(2) . . . . ? C15 C14 C18 C17 -1.8(2) . . . . ? C13 C14 C18 C17 176.36(13) . . . . ? N1 C17 C18 C14 0.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.80 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.180 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.033 data_hoss_25_0m _database_code_depnum_ccdc_archive 'CCDC 712758' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 N O' _chemical_formula_sum 'C18 H13 N O' _chemical_formula_weight 259.29 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.7369(2) _cell_length_b 7.93760(10) _cell_length_c 13.0497(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.9350(10) _cell_angle_gamma 90.00 _cell_volume 1309.68(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6165 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 30.92 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.9381 _exptl_absorpt_correction_T_max 0.9919 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1% _diffrn_reflns_number 21936 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.95 _reflns_number_total 3461 _reflns_number_gt 2509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker AXS, 2004)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0756P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3461 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1056 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.40016(6) -0.01993(10) 0.32226(7) 0.0381(2) Uani 1 1 d . . . H1 H 0.4142 0.0066 0.2647 0.057 Uiso 1 1 calc R . . N1 N 0.48548(9) 0.48267(12) 0.34626(8) 0.0409(3) Uani 1 1 d . . . C1 C 0.21818(9) 0.07664(14) 0.27479(9) 0.0324(3) Uani 1 1 d . . . C2 C 0.20230(10) 0.12871(16) 0.17318(10) 0.0426(3) Uani 1 1 d . . . H2 H 0.2570 0.1775 0.1423 0.051 Uiso 1 1 calc R . . C3 C 0.10346(11) 0.10689(19) 0.11824(11) 0.0508(4) Uani 1 1 d . . . H3 H 0.0918 0.1403 0.0495 0.061 Uiso 1 1 calc R . . C4 C 0.02179(11) 0.03618(19) 0.16413(12) 0.0518(4) Uani 1 1 d . . . H4 H -0.0444 0.0239 0.1261 0.062 Uiso 1 1 calc R . . C5 C 0.03693(10) -0.01658(17) 0.26565(11) 0.0456(3) Uani 1 1 d . . . H5 H -0.0181 -0.0653 0.2961 0.055 Uiso 1 1 calc R . . C6 C 0.13578(9) 0.00450(14) 0.32125(10) 0.0346(3) Uani 1 1 d . . . C7 C 0.17566(9) -0.03724(14) 0.42904(9) 0.0338(3) Uani 1 1 d . . . C8 C 0.12742(10) -0.11330(16) 0.50671(10) 0.0435(3) Uani 1 1 d . . . H8 H 0.0568 -0.1456 0.4950 0.052 Uiso 1 1 calc R . . C9 C 0.18542(11) -0.14057(17) 0.60164(10) 0.0469(3) Uani 1 1 d . . . H9 H 0.1537 -0.1923 0.6540 0.056 Uiso 1 1 calc R . . C10 C 0.29020(11) -0.09155(17) 0.61955(10) 0.0449(3) Uani 1 1 d . . . H10 H 0.3282 -0.1102 0.6840 0.054 Uiso 1 1 calc R . . C11 C 0.33933(10) -0.01475(15) 0.54247(10) 0.0379(3) Uani 1 1 d . . . H11 H 0.4098 0.0184 0.5547 0.046 Uiso 1 1 calc R . . C12 C 0.28174(9) 0.01131(13) 0.44756(9) 0.0310(3) Uani 1 1 d . . . C13 C 0.31889(8) 0.08639(13) 0.35074(9) 0.0296(2) Uani 1 1 d . . . C14 C 0.35677(8) 0.26798(13) 0.36661(8) 0.0293(2) Uani 1 1 d . . . C15 C 0.29771(10) 0.38527(15) 0.41339(10) 0.0414(3) Uani 1 1 d . . . H15 H 0.2337 0.3541 0.4353 0.050 Uiso 1 1 calc R . . C16 C 0.33363(12) 0.54750(16) 0.42742(11) 0.0475(3) Uani 1 1 d . . . H16 H 0.2949 0.6268 0.4596 0.057 Uiso 1 1 calc R . . C17 C 0.42797(10) 0.59092(15) 0.39309(10) 0.0418(3) Uani 1 1 d . . . H17 H 0.4524 0.7008 0.4032 0.050 Uiso 1 1 calc R . . C18 C 0.44955(9) 0.32389(15) 0.33450(9) 0.0353(3) Uani 1 1 d . . . H18 H 0.4900 0.2469 0.3026 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0410(5) 0.0296(4) 0.0463(5) 0.0017(4) 0.0165(4) 0.0079(3) N1 0.0462(6) 0.0336(5) 0.0439(6) 0.0029(4) 0.0099(5) -0.0090(4) C1 0.0355(6) 0.0287(5) 0.0338(6) -0.0032(5) 0.0077(5) 0.0008(4) C2 0.0464(7) 0.0450(7) 0.0373(7) 0.0011(6) 0.0089(5) 0.0015(5) C3 0.0565(8) 0.0596(9) 0.0348(7) -0.0009(6) -0.0008(6) 0.0090(7) C4 0.0408(7) 0.0625(9) 0.0493(8) -0.0081(7) -0.0063(6) 0.0033(6) C5 0.0354(6) 0.0498(8) 0.0514(8) -0.0016(6) 0.0046(6) -0.0027(5) C6 0.0335(6) 0.0327(6) 0.0381(7) -0.0025(5) 0.0062(5) 0.0002(4) C7 0.0339(6) 0.0301(6) 0.0385(7) -0.0002(5) 0.0092(5) -0.0005(4) C8 0.0377(6) 0.0460(7) 0.0490(8) 0.0043(6) 0.0144(5) -0.0067(5) C9 0.0557(8) 0.0470(7) 0.0417(7) 0.0086(6) 0.0211(6) -0.0010(6) C10 0.0537(8) 0.0470(7) 0.0342(7) 0.0036(6) 0.0067(5) 0.0033(6) C11 0.0378(6) 0.0369(6) 0.0390(7) -0.0006(5) 0.0041(5) -0.0011(5) C12 0.0328(6) 0.0253(5) 0.0361(6) 0.0000(5) 0.0089(4) -0.0005(4) C13 0.0299(5) 0.0265(5) 0.0337(6) -0.0007(5) 0.0094(4) 0.0012(4) C14 0.0315(5) 0.0275(5) 0.0294(5) 0.0016(4) 0.0058(4) 0.0013(4) C15 0.0411(6) 0.0363(7) 0.0499(7) -0.0028(6) 0.0186(6) 0.0018(5) C16 0.0640(9) 0.0314(6) 0.0500(8) -0.0065(6) 0.0184(7) 0.0065(6) C17 0.0603(8) 0.0279(6) 0.0367(7) 0.0000(5) 0.0033(6) -0.0053(5) C18 0.0355(6) 0.0306(6) 0.0416(7) 0.0003(5) 0.0125(5) -0.0004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.4195(13) . ? O1 H1 0.8200 . ? N1 C17 1.3253(17) . ? N1 C18 1.3433(15) . ? C1 C2 1.3803(17) . ? C1 C6 1.3966(16) . ? C1 C13 1.5254(16) . ? C2 C3 1.3823(19) . ? C2 H2 0.9300 . ? C3 C4 1.381(2) . ? C3 H3 0.9300 . ? C4 C5 1.381(2) . ? C4 H4 0.9300 . ? C5 C6 1.3854(18) . ? C5 H5 0.9300 . ? C6 C7 1.4744(17) . ? C7 C8 1.3856(17) . ? C7 C12 1.3977(16) . ? C8 C9 1.3807(18) . ? C8 H8 0.9300 . ? C9 C10 1.3826(19) . ? C9 H9 0.9300 . ? C10 C11 1.3882(18) . ? C10 H10 0.9300 . ? C11 C12 1.3768(17) . ? C11 H11 0.9300 . ? C12 C13 1.5230(16) . ? C13 C14 1.5261(15) . ? C14 C18 1.3742(15) . ? C14 C15 1.3843(15) . ? C15 C16 1.3714(18) . ? C15 H15 0.9300 . ? C16 C17 1.3760(19) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 H1 109.5 . . ? C17 N1 C18 117.47(11) . . ? C2 C1 C6 120.61(11) . . ? C2 C1 C13 128.55(10) . . ? C6 C1 C13 110.84(10) . . ? C1 C2 C3 118.64(12) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.84(13) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 120.95(12) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 118.60(13) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C5 C6 C1 120.35(12) . . ? C5 C6 C7 131.24(12) . . ? C1 C6 C7 108.42(10) . . ? C8 C7 C12 119.90(11) . . ? C8 C7 C6 131.58(11) . . ? C12 C7 C6 108.51(10) . . ? C9 C8 C7 119.22(12) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 120.57(12) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 120.76(12) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 118.69(11) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C7 120.86(11) . . ? C11 C12 C13 128.31(10) . . ? C7 C12 C13 110.80(10) . . ? O1 C13 C12 107.10(8) . . ? O1 C13 C1 112.48(9) . . ? C12 C13 C1 101.42(8) . . ? O1 C13 C14 111.62(8) . . ? C12 C13 C14 112.45(9) . . ? C1 C13 C14 111.30(9) . . ? C18 C14 C15 116.76(10) . . ? C18 C14 C13 122.21(10) . . ? C15 C14 C13 121.02(9) . . ? C16 C15 C14 120.00(11) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 118.82(12) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? N1 C17 C16 122.74(11) . . ? N1 C17 H17 118.6 . . ? C16 C17 H17 118.6 . . ? N1 C18 C14 124.19(11) . . ? N1 C18 H18 117.9 . . ? C14 C18 H18 117.9 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.45(18) . . . . ? C13 C1 C2 C3 179.82(11) . . . . ? C1 C2 C3 C4 0.7(2) . . . . ? C2 C3 C4 C5 -0.8(2) . . . . ? C3 C4 C5 C6 0.7(2) . . . . ? C4 C5 C6 C1 -0.44(19) . . . . ? C4 C5 C6 C7 179.58(12) . . . . ? C2 C1 C6 C5 0.33(17) . . . . ? C13 C1 C6 C5 -179.89(10) . . . . ? C2 C1 C6 C7 -179.68(11) . . . . ? C13 C1 C6 C7 0.09(13) . . . . ? C5 C6 C7 C8 1.6(2) . . . . ? C1 C6 C7 C8 -178.36(12) . . . . ? C5 C6 C7 C12 -179.47(12) . . . . ? C1 C6 C7 C12 0.55(13) . . . . ? C12 C7 C8 C9 -0.21(18) . . . . ? C6 C7 C8 C9 178.59(12) . . . . ? C7 C8 C9 C10 0.5(2) . . . . ? C8 C9 C10 C11 -0.3(2) . . . . ? C9 C10 C11 C12 -0.19(19) . . . . ? C10 C11 C12 C7 0.47(18) . . . . ? C10 C11 C12 C13 -177.57(11) . . . . ? C8 C7 C12 C11 -0.28(18) . . . . ? C6 C7 C12 C11 -179.33(10) . . . . ? C8 C7 C12 C13 178.08(10) . . . . ? C6 C7 C12 C13 -0.97(13) . . . . ? C11 C12 C13 O1 61.12(14) . . . . ? C7 C12 C13 O1 -117.08(10) . . . . ? C11 C12 C13 C1 179.17(11) . . . . ? C7 C12 C13 C1 0.97(11) . . . . ? C11 C12 C13 C14 -61.85(15) . . . . ? C7 C12 C13 C14 119.95(10) . . . . ? C2 C1 C13 O1 -66.78(15) . . . . ? C6 C1 C13 O1 113.47(10) . . . . ? C2 C1 C13 C12 179.13(11) . . . . ? C6 C1 C13 C12 -0.63(11) . . . . ? C2 C1 C13 C14 59.33(15) . . . . ? C6 C1 C13 C14 -120.42(10) . . . . ? O1 C13 C14 C18 13.32(15) . . . . ? C12 C13 C14 C18 133.72(11) . . . . ? C1 C13 C14 C18 -113.26(12) . . . . ? O1 C13 C14 C15 -167.49(10) . . . . ? C12 C13 C14 C15 -47.09(14) . . . . ? C1 C13 C14 C15 65.93(14) . . . . ? C18 C14 C15 C16 -1.18(18) . . . . ? C13 C14 C15 C16 179.59(12) . . . . ? C14 C15 C16 C17 0.8(2) . . . . ? C18 N1 C17 C16 -1.31(19) . . . . ? C15 C16 C17 N1 0.5(2) . . . . ? C17 N1 C18 C14 0.91(18) . . . . ? C15 C14 C18 N1 0.32(18) . . . . ? C13 C14 C18 N1 179.53(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.95 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.193 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.056