# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_MeHBIL _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N2 O' _chemical_formula_sum 'C14 H12 N2 O' _chemical_formula_weight 224.26 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.117(7) _cell_length_b 10.007(8) _cell_length_c 16.788(16) _cell_angle_alpha 73.45(4) _cell_angle_beta 85.81(4) _cell_angle_gamma 74.91(4) _cell_volume 1106.5(17) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2271 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 25.32 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9661 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details 'Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.111 _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6981 _diffrn_reflns_av_R_equivalents 0.1060 _diffrn_reflns_av_sigmaI/netI 0.1279 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 25.33 _reflns_number_total 3853 _reflns_number_gt 2445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'CrystalStructure 4.0' _computing_publication_material ? _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^)+(0.1230P)^2^+2.0264P] 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 3853 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1380 _refine_ls_R_factor_gt 0.1009 _refine_ls_wR_factor_ref 0.2949 _refine_ls_wR_factor_gt 0.2730 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.2890(5) 0.8731(4) 0.0837(2) 0.0320(9) Uani 1 1 d . . . H1 H 0.3048 0.8188 0.0525 0.038 Uiso 1 1 calc R . . C1 C 0.1010(7) 0.8979(5) 0.1111(3) 0.0241(11) Uani 1 1 d . . . C2 C 0.0483(7) 0.9851(5) 0.1641(3) 0.0255(11) Uani 1 1 d . . . H2 H 0.1426 1.0246 0.1801 0.031 Uiso 1 1 calc R . . C3 C -0.1408(8) 1.0158(6) 0.1943(3) 0.0318(13) Uani 1 1 d . . . H3 H -0.1762 1.0794 0.2285 0.038 Uiso 1 1 calc R . . C4 C -0.2785(8) 0.9534(6) 0.1745(3) 0.0317(13) Uani 1 1 d . . . H4 H -0.4057 0.9701 0.1974 0.038 Uiso 1 1 calc R . . C5 C -0.2281(7) 0.8672(6) 0.1213(3) 0.0274(12) Uani 1 1 d . . . H5 H -0.3227 0.8246 0.1087 0.033 Uiso 1 1 calc R . . C6 C -0.0420(7) 0.8396(5) 0.0848(3) 0.0211(11) Uani 1 1 d . . . C7 C 0.0174(7) 0.7570(5) 0.0250(3) 0.0241(11) Uani 1 1 d . . . N1 N -0.1069(6) 0.7278(4) -0.0242(3) 0.0260(10) Uani 1 1 d . . . C8 C -0.3199(7) 0.7807(6) -0.0350(3) 0.0282(12) Uani 1 1 d . . . H6 H -0.3614 0.8795 -0.0301 0.034 Uiso 1 1 calc R . . H7 H -0.3842 0.7186 0.0080 0.034 Uiso 1 1 calc R . . H8 H -0.3556 0.7793 -0.0900 0.034 Uiso 1 1 calc R . . C9 C 0.0123(7) 0.6522(5) -0.0762(3) 0.0209(10) Uani 1 1 d . . . C10 C -0.0345(8) 0.5971(5) -0.1378(3) 0.0293(12) Uani 1 1 d . . . H9 H -0.1654 0.6030 -0.1497 0.035 Uiso 1 1 calc R . . C11 C 0.1228(8) 0.5324(6) -0.1810(3) 0.0333(13) Uani 1 1 d . . . H10 H 0.0981 0.4950 -0.2241 0.040 Uiso 1 1 calc R . . C12 C 0.3146(8) 0.5218(6) -0.1620(3) 0.0326(13) Uani 1 1 d . . . H11 H 0.4170 0.4787 -0.1933 0.039 Uiso 1 1 calc R . . C13 C 0.3617(8) 0.5733(6) -0.0976(3) 0.0315(13) Uani 1 1 d . . . H12 H 0.4929 0.5630 -0.0840 0.038 Uiso 1 1 calc R . . C14 C 0.2058(8) 0.6400(5) -0.0550(3) 0.0259(11) Uani 1 1 d . . . N2 N 0.2050(6) 0.7059(4) 0.0086(3) 0.0224(9) Uani 1 1 d . . . O2 O 0.1995(5) 0.5508(4) 0.5863(2) 0.0314(9) Uani 1 1 d . . . H13 H 0.1825 0.6376 0.5591 0.038 Uiso 1 1 calc R . . C15 C 0.3870(7) 0.4969(5) 0.6123(3) 0.0237(11) Uani 1 1 d . . . C16 C 0.4358(7) 0.3610(6) 0.6681(3) 0.0255(11) Uani 1 1 d . . . H14 H 0.3393 0.3085 0.6852 0.031 Uiso 1 1 calc R . . C17 C 0.6238(8) 0.3004(6) 0.6993(3) 0.0294(12) Uani 1 1 d . . . H15 H 0.6556 0.2059 0.7361 0.035 Uiso 1 1 calc R . . C18 C 0.7646(8) 0.3761(6) 0.6775(3) 0.0317(13) Uani 1 1 d . . . H16 H 0.8913 0.3358 0.7009 0.038 Uiso 1 1 calc R . . C19 C 0.7204(7) 0.5119(5) 0.6209(3) 0.0269(12) Uani 1 1 d . . . H17 H 0.8185 0.5633 0.6054 0.032 Uiso 1 1 calc R . . C20 C 0.5321(7) 0.5751(5) 0.5859(3) 0.0216(11) Uani 1 1 d . . . C21 C 0.4764(7) 0.7162(5) 0.5238(3) 0.0236(11) Uani 1 1 d . . . N3 N 0.6022(6) 0.7910(4) 0.4760(3) 0.0253(10) Uani 1 1 d . . . C22 C 0.8144(7) 0.7479(5) 0.4661(3) 0.0249(11) Uani 1 1 d . . . H18 H 0.8553 0.6449 0.4698 0.030 Uiso 1 1 calc R . . H19 H 0.8782 0.7669 0.5100 0.030 Uiso 1 1 calc R . . H20 H 0.8513 0.8032 0.4117 0.030 Uiso 1 1 calc R . . C23 C 0.4827(7) 0.9190(5) 0.4253(3) 0.0211(11) Uani 1 1 d . . . C24 C 0.5329(8) 1.0341(5) 0.3665(3) 0.0277(12) Uani 1 1 d . . . H21 H 0.6643 1.0384 0.3555 0.033 Uiso 1 1 calc R . . C25 C 0.3760(8) 1.1436(6) 0.3243(3) 0.0318(13) Uani 1 1 d . . . H22 H 0.4028 1.2244 0.2836 0.038 Uiso 1 1 calc R . . C26 C 0.1812(8) 1.1376(5) 0.3403(3) 0.0305(13) Uani 1 1 d . . . H23 H 0.0795 1.2121 0.3094 0.037 Uiso 1 1 calc R . . C27 C 0.1364(8) 1.0211(6) 0.4021(3) 0.0294(12) Uani 1 1 d . . . H24 H 0.0052 1.0173 0.4146 0.035 Uiso 1 1 calc R . . C28 C 0.2908(7) 0.9115(5) 0.4446(3) 0.0240(11) Uani 1 1 d . . . N4 N 0.2919(6) 0.7836(4) 0.5065(3) 0.0239(10) Uani 1 1 d . . . 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 0.023(2) 0.042(2) 0.037(2) -0.0197(18) 0.0104(16) -0.0130(17) C1 0.021(3) 0.027(3) 0.025(3) -0.007(2) 0.005(2) -0.008(2) C2 0.026(3) 0.027(3) 0.026(3) -0.008(2) 0.008(2) -0.012(2) C3 0.034(3) 0.027(3) 0.026(3) 0.001(2) 0.008(2) -0.005(2) C4 0.030(3) 0.034(3) 0.028(3) -0.009(2) 0.014(2) -0.005(2) C5 0.019(3) 0.038(3) 0.027(3) -0.012(2) 0.009(2) -0.008(2) C6 0.020(3) 0.020(2) 0.021(2) -0.0054(19) 0.0080(19) -0.0041(19) C7 0.024(3) 0.024(3) 0.020(2) -0.001(2) 0.005(2) -0.005(2) N1 0.022(2) 0.029(2) 0.025(2) -0.0031(18) 0.0012(18) -0.0070(18) C8 0.017(3) 0.033(3) 0.032(3) -0.004(2) 0.002(2) -0.008(2) C9 0.022(3) 0.022(2) 0.017(2) -0.0019(19) 0.0012(19) -0.007(2) C10 0.026(3) 0.030(3) 0.032(3) -0.009(2) -0.005(2) -0.006(2) C11 0.038(3) 0.027(3) 0.031(3) -0.007(2) 0.006(2) -0.006(2) C12 0.031(3) 0.036(3) 0.035(3) -0.018(2) 0.015(2) -0.012(2) C13 0.027(3) 0.033(3) 0.034(3) -0.014(2) 0.013(2) -0.004(2) C14 0.026(3) 0.026(3) 0.027(3) -0.010(2) 0.003(2) -0.007(2) N2 0.020(2) 0.024(2) 0.025(2) -0.0095(17) 0.0058(17) -0.0055(17) O2 0.023(2) 0.032(2) 0.035(2) 0.0008(16) -0.0012(16) -0.0109(16) C15 0.025(3) 0.027(3) 0.022(3) -0.008(2) 0.004(2) -0.011(2) C16 0.021(3) 0.034(3) 0.024(3) -0.009(2) -0.001(2) -0.009(2) C17 0.031(3) 0.030(3) 0.027(3) -0.008(2) 0.000(2) -0.005(2) C18 0.020(3) 0.037(3) 0.032(3) -0.004(2) -0.006(2) 0.000(2) C19 0.013(2) 0.035(3) 0.032(3) -0.007(2) -0.001(2) -0.008(2) C20 0.017(2) 0.024(3) 0.023(2) -0.007(2) 0.0012(19) -0.0011(19) C21 0.023(3) 0.022(3) 0.024(2) -0.006(2) 0.002(2) -0.002(2) N3 0.025(2) 0.030(2) 0.024(2) -0.0095(18) 0.0031(18) -0.0099(19) C22 0.014(2) 0.033(3) 0.029(3) -0.008(2) 0.004(2) -0.008(2) C23 0.025(3) 0.021(2) 0.019(2) -0.010(2) 0.005(2) -0.006(2) C24 0.027(3) 0.029(3) 0.029(3) -0.009(2) 0.015(2) -0.011(2) C25 0.040(3) 0.031(3) 0.026(3) -0.008(2) 0.005(2) -0.013(2) C26 0.036(3) 0.024(3) 0.030(3) -0.008(2) -0.004(2) -0.005(2) C27 0.024(3) 0.032(3) 0.030(3) -0.006(2) -0.004(2) -0.004(2) C28 0.023(3) 0.024(3) 0.025(3) -0.007(2) 0.006(2) -0.007(2) N4 0.015(2) 0.028(2) 0.026(2) -0.0024(18) -0.0001(17) -0.0062(17) _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 C1 1.365(6) . ? C1 C2 1.386(7) . ? C1 C6 1.446(7) . ? C2 C3 1.392(7) . ? C3 C4 1.395(8) . ? C4 C5 1.378(7) . ? C5 C6 1.412(7) . ? C6 C7 1.449(7) . ? C7 N2 1.338(6) . ? C7 N1 1.389(7) . ? N1 C9 1.411(6) . ? N1 C8 1.476(6) . ? C9 C10 1.397(7) . ? C9 C14 1.413(7) . ? C10 C11 1.404(8) . ? C11 C12 1.395(8) . ? C12 C13 1.415(8) . ? C13 C14 1.399(7) . ? C14 N2 1.405(6) . ? O2 C15 1.356(6) . ? C15 C16 1.387(7) . ? C15 C20 1.425(7) . ? C16 C17 1.390(7) . ? C17 C18 1.377(8) . ? C18 C19 1.390(7) . ? C19 C20 1.416(7) . ? C20 C21 1.473(7) . ? C21 N4 1.321(6) . ? C21 N3 1.381(7) . ? N3 C23 1.416(6) . ? N3 C22 1.470(6) . ? C23 C24 1.395(7) . ? C23 C28 1.397(7) . ? C24 C25 1.409(8) . ? C25 C26 1.406(8) . ? C26 C27 1.412(8) . ? C27 C28 1.400(7) . ? C28 N4 1.399(6) . ? 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 O1 C1 C2 117.6(4) . . ? O1 C1 C6 122.3(4) . . ? C2 C1 C6 120.1(5) . . ? C1 C2 C3 120.9(5) . . ? C2 C3 C4 120.2(5) . . ? C5 C4 C3 119.3(5) . . ? C4 C5 C6 122.8(5) . . ? C5 C6 C1 116.3(4) . . ? C5 C6 C7 125.8(5) . . ? C1 C6 C7 117.9(4) . . ? N2 C7 N1 112.4(4) . . ? N2 C7 C6 121.9(5) . . ? N1 C7 C6 125.6(5) . . ? C7 N1 C9 106.6(4) . . ? C7 N1 C8 130.2(4) . . ? C9 N1 C8 122.5(4) . . ? C10 C9 N1 131.2(5) . . ? C10 C9 C14 123.1(5) . . ? N1 C9 C14 105.7(4) . . ? C9 C10 C11 116.2(5) . . ? C12 C11 C10 121.4(5) . . ? C11 C12 C13 122.2(5) . . ? C14 C13 C12 116.8(5) . . ? C13 C14 N2 130.2(5) . . ? C13 C14 C9 120.2(5) . . ? N2 C14 C9 109.6(4) . . ? C7 N2 C14 105.8(4) . . ? O2 C15 C16 117.7(4) . . ? O2 C15 C20 122.7(4) . . ? C16 C15 C20 119.6(5) . . ? C15 C16 C17 120.9(5) . . ? C18 C17 C16 120.6(5) . . ? C17 C18 C19 119.7(5) . . ? C18 C19 C20 121.2(5) . . ? C19 C20 C15 117.9(5) . . ? C19 C20 C21 124.2(5) . . ? C15 C20 C21 117.9(4) . . ? N4 C21 N3 112.4(4) . . ? N4 C21 C20 121.4(5) . . ? N3 C21 C20 126.2(5) . . ? C21 N3 C23 105.8(4) . . ? C21 N3 C22 130.6(4) . . ? C23 N3 C22 123.0(4) . . ? C24 C23 C28 123.5(5) . . ? C24 C23 N3 130.3(5) . . ? C28 C23 N3 106.2(4) . . ? C23 C24 C25 115.7(5) . . ? C26 C25 C24 122.3(5) . . ? C25 C26 C27 120.2(5) . . ? C28 C27 C26 118.1(5) . . ? C23 C28 N4 108.9(4) . . ? C23 C28 C27 120.1(5) . . ? N4 C28 C27 131.0(5) . . ? C21 N4 C28 106.7(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 O1 C1 C2 C3 179.7(4) . . . . ? C6 C1 C2 C3 1.3(7) . . . . ? C1 C2 C3 C4 2.9(8) . . . . ? C2 C3 C4 C5 -3.3(8) . . . . ? C3 C4 C5 C6 -0.6(8) . . . . ? C4 C5 C6 C1 4.6(7) . . . . ? C4 C5 C6 C7 -176.3(5) . . . . ? O1 C1 C6 C5 176.8(4) . . . . ? C2 C1 C6 C5 -4.9(7) . . . . ? O1 C1 C6 C7 -2.4(7) . . . . ? C2 C1 C6 C7 175.9(4) . . . . ? C5 C6 C7 N2 -163.4(5) . . . . ? C1 C6 C7 N2 15.7(7) . . . . ? C5 C6 C7 N1 20.1(8) . . . . ? C1 C6 C7 N1 -160.8(5) . . . . ? N2 C7 N1 C9 -0.1(5) . . . . ? C6 C7 N1 C9 176.6(4) . . . . ? N2 C7 N1 C8 -170.4(5) . . . . ? C6 C7 N1 C8 6.4(8) . . . . ? C7 N1 C9 C10 -179.7(5) . . . . ? C8 N1 C9 C10 -8.5(8) . . . . ? C7 N1 C9 C14 -0.1(5) . . . . ? C8 N1 C9 C14 171.1(4) . . . . ? N1 C9 C10 C11 177.1(5) . . . . ? C14 C9 C10 C11 -2.5(7) . . . . ? C9 C10 C11 C12 1.2(8) . . . . ? C10 C11 C12 C13 1.0(8) . . . . ? C11 C12 C13 C14 -1.9(8) . . . . ? C12 C13 C14 N2 -177.3(5) . . . . ? C12 C13 C14 C9 0.7(7) . . . . ? C10 C9 C14 C13 1.5(8) . . . . ? N1 C9 C14 C13 -178.1(5) . . . . ? C10 C9 C14 N2 179.9(4) . . . . ? N1 C9 C14 N2 0.3(5) . . . . ? N1 C7 N2 C14 0.3(5) . . . . ? C6 C7 N2 C14 -176.6(4) . . . . ? C13 C14 N2 C7 177.8(5) . . . . ? C9 C14 N2 C7 -0.3(5) . . . . ? O2 C15 C16 C17 -178.2(4) . . . . ? C20 C15 C16 C17 0.7(8) . . . . ? C15 C16 C17 C18 2.0(8) . . . . ? C16 C17 C18 C19 -2.8(8) . . . . ? C17 C18 C19 C20 0.8(8) . . . . ? C18 C19 C20 C15 1.8(7) . . . . ? C18 C19 C20 C21 -178.0(5) . . . . ? O2 C15 C20 C19 176.2(4) . . . . ? C16 C15 C20 C19 -2.6(7) . . . . ? O2 C15 C20 C21 -3.9(7) . . . . ? C16 C15 C20 C21 177.3(4) . . . . ? C19 C20 C21 N4 -165.3(5) . . . . ? C15 C20 C21 N4 14.9(7) . . . . ? C19 C20 C21 N3 16.8(8) . . . . ? C15 C20 C21 N3 -163.1(5) . . . . ? N4 C21 N3 C23 1.3(5) . . . . ? C20 C21 N3 C23 179.4(5) . . . . ? N4 C21 N3 C22 -170.3(5) . . . . ? C20 C21 N3 C22 7.8(8) . . . . ? C21 N3 C23 C24 178.9(5) . . . . ? C22 N3 C23 C24 -8.6(8) . . . . ? C21 N3 C23 C28 -1.4(5) . . . . ? C22 N3 C23 C28 171.0(4) . . . . ? C28 C23 C24 C25 -1.9(7) . . . . ? N3 C23 C24 C25 177.7(5) . . . . ? C23 C24 C25 C26 -0.1(7) . . . . ? C24 C25 C26 C27 1.9(8) . . . . ? C25 C26 C27 C28 -1.8(8) . . . . ? C24 C23 C28 N4 -179.2(5) . . . . ? N3 C23 C28 N4 1.1(5) . . . . ? C24 C23 C28 C27 2.0(7) . . . . ? N3 C23 C28 C27 -177.7(4) . . . . ? C26 C27 C28 C23 0.0(7) . . . . ? C26 C27 C28 N4 -178.5(5) . . . . ? N3 C21 N4 C28 -0.6(6) . . . . ? C20 C21 N4 C28 -178.9(4) . . . . ? C23 C28 N4 C21 -0.3(5) . . . . ? C27 C28 N4 C21 178.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.627 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.091 _database_code_depnum_ccdc_archive 'CCDC 924262' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_MeHBINL _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N2 O' _chemical_formula_sum 'C14 H12 N2 O' _chemical_formula_weight 224.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c 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 7.516(1) _cell_length_b 15.318(1) _cell_length_c 11.199(1) _cell_angle_alpha 90.00 _cell_angle_beta 114.615(2) _cell_angle_gamma 90.00 _cell_volume 1172.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 10352 _cell_measurement_theta_min 5.22 _cell_measurement_theta_max 73.20 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.654 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8396 _exptl_absorpt_correction_T_max 0.9108 _exptl_absorpt_process_details 'abscor (MacScience Co. Ltd., 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MacScience DIPLabo' _diffrn_measurement_method IP _diffrn_detector_area_resol_mean ? _diffrn_standards_number NONE _diffrn_standards_interval_count NONE _diffrn_standards_interval_time NONE _diffrn_standards_decay_% NONE _diffrn_reflns_number 10352 _diffrn_reflns_av_R_equivalents 0.066 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 5.22 _diffrn_reflns_theta_max 73.20 _reflns_number_total 2305 _reflns_number_gt 2102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MacScience Xpress' _computing_cell_refinement Scalepack _computing_data_reduction 'Denzo and Scalepack' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics maXus _computing_publication_material ? _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^)+(0.0780P)^2^+0.3870P] 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 2305 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1581 _refine_ls_wR_factor_gt 0.1520 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 0.2095(2) 0.77082(9) 0.59741(14) 0.0545(4) Uani 1 1 d . . . H1 H 0.2175 0.7967 0.6636 0.082 Uiso 1 1 calc R . . C1 C 0.3571(3) 0.79605(12) 0.56664(17) 0.0443(4) Uani 1 1 d . . . C2 C 0.4590(3) 0.87362(13) 0.6126(2) 0.0562(5) Uani 1 1 d . . . H2 H 0.4286 0.9092 0.6688 0.067 Uiso 1 1 calc R . . C3 C 0.6050(3) 0.89800(15) 0.5750(2) 0.0646(6) Uani 1 1 d . . . H3 H 0.6740 0.9494 0.6075 0.078 Uiso 1 1 calc R . . C4 C 0.6496(3) 0.84713(16) 0.4900(2) 0.0649(6) Uani 1 1 d . . . H4 H 0.7469 0.8644 0.4642 0.078 Uiso 1 1 calc R . . C5 C 0.5490(3) 0.77046(14) 0.4436(2) 0.0535(5) Uani 1 1 d . . . H5 H 0.5783 0.7363 0.3855 0.064 Uiso 1 1 calc R . . C6 C 0.4041(3) 0.74318(11) 0.48209(16) 0.0420(4) Uani 1 1 d . . . C7 C 0.3055(3) 0.65938(11) 0.43251(16) 0.0408(4) Uani 1 1 d . . . N1 N 0.3045(2) 0.59214(9) 0.51204(14) 0.0434(4) Uani 1 1 d . . . C8 C 0.4000(3) 0.58880(14) 0.65439(18) 0.0547(5) Uani 1 1 d . . . H6 H 0.3036 0.5945 0.6894 0.082 Uiso 1 1 calc R . . H7 H 0.4926 0.6357 0.6864 0.082 Uiso 1 1 calc R . . H8 H 0.4668 0.5340 0.6816 0.082 Uiso 1 1 calc R . . C9 C 0.2139(3) 0.52234(11) 0.43132(18) 0.0447(4) Uani 1 1 d . . . C10 C 0.1773(3) 0.43734(13) 0.4587(2) 0.0594(5) Uani 1 1 d . . . H9 H 0.2112 0.4181 0.5442 0.071 Uiso 1 1 calc R . . C11 C 0.0877(3) 0.38304(15) 0.3514(3) 0.0701(7) Uani 1 1 d . . . H10 H 0.0619 0.3255 0.3653 0.084 Uiso 1 1 calc R . . C12 C 0.0353(3) 0.41189(16) 0.2241(3) 0.0692(6) Uani 1 1 d . . . H11 H -0.0255 0.3733 0.1548 0.083 Uiso 1 1 calc R . . C13 C 0.0709(3) 0.49610(15) 0.1975(2) 0.0596(5) Uani 1 1 d . . . H12 H 0.0350 0.5150 0.1116 0.072 Uiso 1 1 calc R . . C14 C 0.1627(3) 0.55203(12) 0.30367(18) 0.0456(4) Uani 1 1 d . . . N2 N 0.2208(2) 0.63821(10) 0.30660(14) 0.0459(4) Uani 1 1 d . . . 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 0.0640(8) 0.0546(8) 0.0580(8) -0.0166(6) 0.0382(7) -0.0147(6) C1 0.0500(9) 0.0450(9) 0.0400(9) -0.0003(7) 0.0209(8) -0.0038(7) C2 0.0670(12) 0.0492(10) 0.0577(12) -0.0123(9) 0.0312(10) -0.0130(9) C3 0.0680(13) 0.0582(12) 0.0689(13) -0.0084(10) 0.0297(11) -0.0223(10) C4 0.0660(13) 0.0691(14) 0.0705(14) -0.0006(11) 0.0390(11) -0.0188(11) C5 0.0598(11) 0.0578(11) 0.0515(11) 0.0003(9) 0.0316(9) -0.0029(9) C6 0.0482(9) 0.0423(9) 0.0368(8) 0.0027(7) 0.0190(7) -0.0001(7) C7 0.0496(9) 0.0408(9) 0.0377(8) 0.0015(7) 0.0237(7) 0.0012(7) N1 0.0532(8) 0.0416(8) 0.0390(7) 0.0038(6) 0.0227(6) 0.0019(6) C8 0.0659(12) 0.0566(11) 0.0417(10) 0.0098(8) 0.0224(9) 0.0085(9) C9 0.0476(9) 0.0398(9) 0.0528(10) 0.0002(7) 0.0271(8) -0.0001(7) C10 0.0651(12) 0.0466(10) 0.0756(14) 0.0074(10) 0.0382(11) -0.0009(9) C11 0.0637(13) 0.0450(11) 0.105(2) -0.0078(12) 0.0387(13) -0.0089(9) C12 0.0538(12) 0.0607(13) 0.0865(17) -0.0238(12) 0.0227(11) -0.0119(10) C13 0.0553(11) 0.0637(12) 0.0555(12) -0.0136(10) 0.0187(9) -0.0020(9) C14 0.0468(9) 0.0465(9) 0.0469(10) -0.0045(7) 0.0229(8) 0.0001(7) N2 0.0573(9) 0.0446(8) 0.0389(8) 0.0002(6) 0.0233(7) -0.0005(7) _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 C1 1.348(2) . ? O1 H1 0.8200 . ? C1 C2 1.391(3) . ? C1 C6 1.398(2) . ? C2 C3 1.381(3) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.376(3) . ? C4 H4 0.9300 . ? C5 C6 1.392(3) . ? C5 H5 0.9300 . ? C6 C7 1.470(2) . ? C7 N2 1.323(2) . ? C7 N1 1.364(2) . ? N1 C9 1.383(2) . ? N1 C8 1.451(2) . ? C8 H6 0.9600 . ? C8 H7 0.9600 . ? C8 H8 0.9600 . ? C9 C10 1.391(3) . ? C9 C14 1.393(3) . ? C10 C11 1.384(3) . ? C10 H9 0.9300 . ? C11 C12 1.384(4) . ? C11 H10 0.9300 . ? C12 C13 1.375(3) . ? C12 H11 0.9300 . ? C13 C14 1.393(3) . ? C13 H12 0.9300 . ? C14 N2 1.387(2) . ? 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 C1 O1 H1 109.5 . . ? O1 C1 C2 122.35(17) . . ? O1 C1 C6 118.27(16) . . ? C2 C1 C6 119.35(17) . . ? C3 C2 C1 120.21(19) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 120.77(19) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.44(19) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C6 121.09(19) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 119.12(17) . . ? C5 C6 C7 118.77(16) . . ? C1 C6 C7 122.11(16) . . ? N2 C7 N1 112.33(15) . . ? N2 C7 C6 124.01(15) . . ? N1 C7 C6 123.48(15) . . ? C7 N1 C9 107.00(14) . . ? C7 N1 C8 127.55(16) . . ? C9 N1 C8 125.06(15) . . ? N1 C8 H6 109.5 . . ? N1 C8 H7 109.5 . . ? H6 C8 H7 109.5 . . ? N1 C8 H8 109.5 . . ? H6 C8 H8 109.5 . . ? H7 C8 H8 109.5 . . ? N1 C9 C10 131.96(18) . . ? N1 C9 C14 105.59(15) . . ? C10 C9 C14 122.43(19) . . ? C11 C10 C9 116.2(2) . . ? C11 C10 H9 121.9 . . ? C9 C10 H9 121.9 . . ? C10 C11 C12 121.9(2) . . ? C10 C11 H10 119.0 . . ? C12 C11 H10 119.0 . . ? C13 C12 C11 121.7(2) . . ? C13 C12 H11 119.1 . . ? C11 C12 H11 119.1 . . ? C12 C13 C14 117.6(2) . . ? C12 C13 H12 121.2 . . ? C14 C13 H12 121.2 . . ? N2 C14 C9 109.69(16) . . ? N2 C14 C13 130.15(18) . . ? C9 C14 C13 120.15(19) . . ? C7 N2 C14 105.40(15) . . ? 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 O1 C1 C2 C3 -177.9(2) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C1 1.7(3) . . . . ? C4 C5 C6 C7 -178.17(19) . . . . ? O1 C1 C6 C5 176.59(17) . . . . ? C2 C1 C6 C5 -1.4(3) . . . . ? O1 C1 C6 C7 -3.5(3) . . . . ? C2 C1 C6 C7 178.48(17) . . . . ? C5 C6 C7 N2 -53.2(3) . . . . ? C1 C6 C7 N2 126.9(2) . . . . ? C5 C6 C7 N1 121.4(2) . . . . ? C1 C6 C7 N1 -58.5(2) . . . . ? N2 C7 N1 C9 0.5(2) . . . . ? C6 C7 N1 C9 -174.73(15) . . . . ? N2 C7 N1 C8 173.55(16) . . . . ? C6 C7 N1 C8 -1.7(3) . . . . ? C7 N1 C9 C10 178.1(2) . . . . ? C8 N1 C9 C10 4.8(3) . . . . ? C7 N1 C9 C14 -0.23(19) . . . . ? C8 N1 C9 C14 -173.52(16) . . . . ? N1 C9 C10 C11 -177.67(19) . . . . ? C14 C9 C10 C11 0.4(3) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 C13 0.5(4) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? N1 C9 C14 N2 -0.1(2) . . . . ? C10 C9 C14 N2 -178.60(17) . . . . ? N1 C9 C14 C13 178.69(16) . . . . ? C10 C9 C14 C13 0.2(3) . . . . ? C12 C13 C14 N2 178.0(2) . . . . ? C12 C13 C14 C9 -0.4(3) . . . . ? N1 C7 N2 C14 -0.5(2) . . . . ? C6 C7 N2 C14 174.67(16) . . . . ? C9 C14 N2 C7 0.3(2) . . . . ? C13 C14 N2 C7 -178.24(19) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.214 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 924263' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tBuHBI _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H18 N2 O' _chemical_formula_sum 'C17 H18 N2 O' _chemical_formula_weight 266.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 21.216(1) _cell_length_b 21.216 _cell_length_c 17.221(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 6713.0(5) _cell_formula_units_Z 18 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 21369 _cell_measurement_theta_min 3.52 _cell_measurement_theta_max 73.52 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.186 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2556 _exptl_absorpt_coefficient_mu 0.587 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8366 _exptl_absorpt_correction_T_max 0.8902 _exptl_absorpt_process_details 'abscor (MacScience Co. Ltd., 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'MacScience DIPLabo' _diffrn_measurement_method IP _diffrn_detector_area_resol_mean ? _diffrn_standards_number NONE _diffrn_standards_interval_count NONE _diffrn_standards_interval_time NONE _diffrn_standards_decay_% NONE _diffrn_reflns_number 21369 _diffrn_reflns_av_R_equivalents 0.055 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 73.52 _reflns_number_total 2958 _reflns_number_gt 2648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MacScience Xpress' _computing_cell_refinement Scalepack _computing_data_reduction 'Denzo and Scalepack' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics maXus _computing_publication_material ? _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^)+(0.0627P)^2^+6.2483P] 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 2958 _refine_ls_number_parameters 185 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0624 _refine_ls_wR_factor_ref 0.1504 _refine_ls_wR_factor_gt 0.1459 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.38319(7) 0.44382(7) 0.16977(8) 0.0571(4) Uani 1 1 d . . . H1 H 0.4262 0.4742 0.1634 0.086 Uiso 1 1 calc R . . C1 C 0.35352(9) 0.46914(9) 0.22205(10) 0.0460(4) Uani 1 1 d . . . C2 C 0.38564(11) 0.54201(10) 0.24236(13) 0.0604(5) Uani 1 1 d . . . H2 H 0.4288 0.5761 0.2187 0.072 Uiso 1 1 calc R . . C3 C 0.35367(13) 0.56387(12) 0.29762(16) 0.0759(7) Uani 1 1 d . . . H3 H 0.3758 0.6128 0.3113 0.091 Uiso 1 1 calc R . . C4 C 0.28943(13) 0.51454(12) 0.33291(16) 0.0758(7) Uani 1 1 d . . . H4 H 0.2689 0.5295 0.3712 0.091 Uiso 1 1 calc R . . C5 C 0.25606(11) 0.44249(11) 0.31057(12) 0.0593(5) Uani 1 1 d . . . H5 H 0.2116 0.4092 0.3325 0.071 Uiso 1 1 calc R . . C6 C 0.28784(9) 0.41904(9) 0.25584(10) 0.0438(4) Uani 1 1 d . . . C7 C 0.24672(8) 0.34335(9) 0.22652(9) 0.0407(4) Uani 1 1 d . . . N1 N 0.26237(7) 0.28830(7) 0.23515(8) 0.0420(3) Uani 1 1 d . . . C8 C 0.31877(10) 0.28347(10) 0.28308(11) 0.0518(4) Uani 1 1 d . . . C9 C 0.36119(13) 0.34976(13) 0.33429(13) 0.0684(6) Uani 1 1 d . . . H6 H 0.3282 0.3554 0.3678 0.103 Uiso 1 1 calc R . . H7 H 0.3869 0.3923 0.3024 0.103 Uiso 1 1 calc R . . H8 H 0.3954 0.3435 0.3651 0.103 Uiso 1 1 calc R . . C10 C 0.37107(12) 0.27631(13) 0.22735(15) 0.0702(6) Uani 1 1 d . . . H9 H 0.3930 0.3178 0.1935 0.105 Uiso 1 1 calc R . . H10 H 0.3447 0.2328 0.1970 0.105 Uiso 1 1 calc R . . H11 H 0.4083 0.2738 0.2566 0.105 Uiso 1 1 calc R . . C11 C 0.27915(15) 0.21725(13) 0.33648(15) 0.0779(7) Uani 1 1 d . . . H12 H 0.2529 0.1741 0.3056 0.117 Uiso 1 1 calc R . . H13 H 0.2457 0.2231 0.3690 0.117 Uiso 1 1 calc R . . H14 H 0.3140 0.2130 0.3683 0.117 Uiso 1 1 calc R . . C12 C 0.21036(9) 0.23029(9) 0.19098(10) 0.0442(4) Uani 1 1 d . . . C13 C 0.19874(11) 0.16126(11) 0.17370(13) 0.0614(5) Uani 1 1 d . . . H15 H 0.2282 0.1447 0.1946 0.074 Uiso 1 1 calc R . . C14 C 0.14207(13) 0.11834(13) 0.12454(15) 0.0740(7) Uani 1 1 d . . . H16 H 0.1333 0.0719 0.1124 0.089 Uiso 1 1 calc R . . C15 C 0.09769(12) 0.14226(13) 0.09262(15) 0.0726(6) Uani 1 1 d . . . H17 H 0.0602 0.1119 0.0593 0.087 Uiso 1 1 calc R . . C16 C 0.10844(10) 0.20972(12) 0.10950(13) 0.0622(5) Uani 1 1 d . . . H18 H 0.0787 0.2258 0.0882 0.075 Uiso 1 1 calc R . . C17 C 0.16522(9) 0.25395(10) 0.15951(10) 0.0456(4) Uani 1 1 d . . . N2 N 0.18883(7) 0.32460(8) 0.18317(8) 0.0453(3) Uani 1 1 d . . . 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 0.0417(7) 0.0538(8) 0.0636(8) -0.0044(6) 0.0097(6) 0.0147(6) C1 0.0400(9) 0.0458(9) 0.0511(9) 0.0000(7) -0.0027(7) 0.0207(7) C2 0.0450(10) 0.0449(10) 0.0811(14) 0.0006(9) 0.0000(9) 0.0148(8) C3 0.0698(14) 0.0459(11) 0.1066(19) -0.0138(11) 0.0010(13) 0.0250(10) C4 0.0758(15) 0.0588(12) 0.0953(18) -0.0133(12) 0.0151(13) 0.0355(12) C5 0.0565(11) 0.0520(11) 0.0692(12) 0.0015(9) 0.0168(9) 0.0269(9) C6 0.0404(8) 0.0429(9) 0.0491(9) 0.0032(7) 0.0017(7) 0.0214(7) C7 0.0386(8) 0.0428(8) 0.0418(8) 0.0056(6) 0.0055(6) 0.0211(7) N1 0.0420(7) 0.0440(7) 0.0435(7) 0.0016(6) -0.0025(6) 0.0241(6) C8 0.0550(10) 0.0553(10) 0.0525(10) 0.0012(8) -0.0106(8) 0.0331(9) C9 0.0773(14) 0.0714(14) 0.0638(12) -0.0089(10) -0.0269(11) 0.0425(12) C10 0.0568(12) 0.0811(15) 0.0864(16) -0.0123(12) -0.0092(11) 0.0448(12) C11 0.0951(18) 0.0717(14) 0.0701(14) 0.0179(11) -0.0121(12) 0.0442(13) C12 0.0413(8) 0.0441(9) 0.0461(9) 0.0016(7) 0.0020(7) 0.0205(7) C13 0.0603(12) 0.0526(11) 0.0766(13) -0.0080(9) -0.0056(10) 0.0322(10) C14 0.0666(14) 0.0562(12) 0.0953(17) -0.0230(11) -0.0098(12) 0.0277(11) C15 0.0532(12) 0.0690(14) 0.0847(15) -0.0240(12) -0.0124(11) 0.0225(11) C16 0.0459(10) 0.0690(13) 0.0703(12) -0.0074(10) -0.0085(9) 0.0277(10) C17 0.0386(8) 0.0490(9) 0.0488(9) 0.0028(7) 0.0032(7) 0.0216(7) N2 0.0394(7) 0.0466(8) 0.0514(8) 0.0043(6) 0.0003(6) 0.0226(6) _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 C1 1.354(2) . ? O1 H1 0.8200 . ? C1 C2 1.387(3) . ? C1 C6 1.389(2) . ? C2 C3 1.377(3) . ? C2 H2 0.9300 . ? C3 C4 1.377(3) . ? C3 H3 0.9300 . ? C4 C5 1.380(3) . ? C4 H4 0.9300 . ? C5 C6 1.388(2) . ? C5 H5 0.9300 . ? C6 C7 1.481(2) . ? C7 N2 1.317(2) . ? C7 N1 1.373(2) . ? N1 C12 1.397(2) . ? N1 C8 1.499(2) . ? C8 C9 1.517(3) . ? C8 C10 1.531(3) . ? C8 C11 1.531(3) . ? C9 H6 0.9600 . ? C9 H7 0.9600 . ? C9 H8 0.9600 . ? C10 H9 0.9600 . ? C10 H10 0.9600 . ? C10 H11 0.9600 . ? C11 H12 0.9600 . ? C11 H13 0.9600 . ? C11 H14 0.9600 . ? C12 C13 1.390(3) . ? C12 C17 1.394(2) . ? C13 C14 1.377(3) . ? C13 H15 0.9300 . ? C14 C15 1.387(3) . ? C14 H16 0.9300 . ? C15 C16 1.363(3) . ? C15 H17 0.9300 . ? C16 C17 1.394(3) . ? C16 H18 0.9300 . ? C17 N2 1.383(2) . ? 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 C1 O1 H1 109.5 . . ? O1 C1 C2 122.90(16) . . ? O1 C1 C6 117.54(15) . . ? C2 C1 C6 119.55(17) . . ? C3 C2 C1 119.98(19) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 118.9(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 120.96(19) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C1 119.44(16) . . ? C5 C6 C7 119.46(15) . . ? C1 C6 C7 120.57(15) . . ? N2 C7 N1 112.96(14) . . ? N2 C7 C6 118.39(14) . . ? N1 C7 C6 128.58(14) . . ? C7 N1 C12 105.67(13) . . ? C7 N1 C8 131.22(14) . . ? C12 N1 C8 123.04(14) . . ? N1 C8 C9 112.38(15) . . ? N1 C8 C10 107.74(15) . . ? C9 C8 C10 109.45(18) . . ? N1 C8 C11 107.62(16) . . ? C9 C8 C11 107.49(18) . . ? C10 C8 C11 112.21(18) . . ? C8 C9 H6 109.5 . . ? C8 C9 H7 109.5 . . ? H6 C9 H7 109.5 . . ? C8 C9 H8 109.5 . . ? H6 C9 H8 109.5 . . ? H7 C9 H8 109.5 . . ? C8 C10 H9 109.5 . . ? C8 C10 H10 109.5 . . ? H9 C10 H10 109.5 . . ? C8 C10 H11 109.5 . . ? H9 C10 H11 109.5 . . ? H10 C10 H11 109.5 . . ? C8 C11 H12 109.5 . . ? C8 C11 H13 109.5 . . ? H12 C11 H13 109.5 . . ? C8 C11 H14 109.5 . . ? H12 C11 H14 109.5 . . ? H13 C11 H14 109.5 . . ? C13 C12 C17 120.27(17) . . ? C13 C12 N1 133.65(16) . . ? C17 C12 N1 106.05(14) . . ? C14 C13 C12 117.67(19) . . ? C14 C13 H15 121.2 . . ? C12 C13 H15 121.2 . . ? C13 C14 C15 122.0(2) . . ? C13 C14 H16 119.0 . . ? C15 C14 H16 119.0 . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H17 119.6 . . ? C14 C15 H17 119.6 . . ? C15 C16 C17 118.2(2) . . ? C15 C16 H18 120.9 . . ? C17 C16 H18 120.9 . . ? N2 C17 C12 109.51(15) . . ? N2 C17 C16 129.37(17) . . ? C12 C17 C16 121.06(17) . . ? C7 N2 C17 105.78(14) . . ? 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 O1 C1 C2 C3 -178.1(2) . . . . ? C6 C1 C2 C3 2.2(3) . . . . ? C1 C2 C3 C4 -0.7(4) . . . . ? C2 C3 C4 C5 -1.7(4) . . . . ? C3 C4 C5 C6 2.7(4) . . . . ? C4 C5 C6 C1 -1.2(3) . . . . ? C4 C5 C6 C7 -173.0(2) . . . . ? O1 C1 C6 C5 179.06(17) . . . . ? C2 C1 C6 C5 -1.2(3) . . . . ? O1 C1 C6 C7 -9.3(2) . . . . ? C2 C1 C6 C7 170.39(17) . . . . ? C5 C6 C7 N2 68.0(2) . . . . ? C1 C6 C7 N2 -103.67(19) . . . . ? C5 C6 C7 N1 -115.4(2) . . . . ? C1 C6 C7 N1 72.9(2) . . . . ? N2 C7 N1 C12 1.85(18) . . . . ? C6 C7 N1 C12 -174.90(16) . . . . ? N2 C7 N1 C8 -175.09(16) . . . . ? C6 C7 N1 C8 8.2(3) . . . . ? C7 N1 C8 C9 4.9(3) . . . . ? C12 N1 C8 C9 -171.61(17) . . . . ? C7 N1 C8 C10 -115.77(19) . . . . ? C12 N1 C8 C10 67.7(2) . . . . ? C7 N1 C8 C11 123.0(2) . . . . ? C12 N1 C8 C11 -53.5(2) . . . . ? C7 N1 C12 C13 177.0(2) . . . . ? C8 N1 C12 C13 -5.7(3) . . . . ? C7 N1 C12 C17 -1.24(17) . . . . ? C8 N1 C12 C17 176.02(15) . . . . ? C17 C12 C13 C14 0.5(3) . . . . ? N1 C12 C13 C14 -177.6(2) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C13 C14 C15 C16 -0.5(4) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C13 C12 C17 N2 -178.23(16) . . . . ? N1 C12 C17 N2 0.32(18) . . . . ? C13 C12 C17 C16 -0.9(3) . . . . ? N1 C12 C17 C16 177.64(16) . . . . ? C15 C16 C17 N2 177.3(2) . . . . ? C15 C16 C17 C12 0.6(3) . . . . ? N1 C7 N2 C17 -1.65(18) . . . . ? C6 C7 N2 C17 175.46(14) . . . . ? C12 C17 N2 C7 0.78(18) . . . . ? C16 C17 N2 C7 -176.25(18) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 67.44 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.185 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 924266'