# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 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_dcyme5 #TrackingRef '14982_web_deposit_cif_file_0_CarlosBasilioPinheiro_1351263618.dcym.cif' _audit_creation_date 2012-10-24T21:16:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_moiety 'C24 H18 N4 O3' _chemical_formula_sum 'C24 H18 N4 O3' _chemical_formula_weight 410.42 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 27.6303(10) _cell_length_b 4.10757(17) _cell_length_c 19.1097(6) _cell_angle_alpha 90.000 _cell_angle_beta 110.163(3) _cell_angle_gamma 90.000 _cell_volume 2035.91(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 12217 _cell_measurement_theta_min 2.461 _cell_measurement_theta_max 66.5071 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.2820 _exptl_crystal_size_mid 0.1998 _exptl_crystal_size_min 0.0706 _exptl_crystal_description primatic _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -2 0 1 0.1080 2 0 -1 0.1202 9 -2 4 0.1067 -7 2 -1 0.0303 1 -2 -5 0.0346 -1 2 5 0.0360 9 0 8 0.1295 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.741 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.89924 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 0.0382602 _diffrn_orient_matrix_ub_12 -0.0909093 _diffrn_orient_matrix_ub_13 -0.0394229 _diffrn_orient_matrix_ub_21 -0.0097513 _diffrn_orient_matrix_ub_22 -0.3638661 _diffrn_orient_matrix_ub_23 0.0094983 _diffrn_orient_matrix_ub_31 -0.0443734 _diffrn_orient_matrix_ub_32 0.0016268 _diffrn_orient_matrix_ub_33 -0.0757033 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_unetI/netI 0.0185 _diffrn_reflns_number 22251 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 66.61 _diffrn_reflns_theta_full 66.61 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 3559 _reflns_number_gt 3486 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0803P)^2^+0.3677P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3559 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.445 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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 0.40185(5) 0.0880(3) 0.63054(7) 0.0297(3) Uani 1 1 d . . . O4 O 0 0.5893(4) 0.25 0.0259(4) Uani 1 2 d S . . O2 O 0.09812(4) 0.4634(4) 0.23024(7) 0.0267(3) Uani 1 1 d . . . O3 O 0.5 -0.0320(5) 0.75 0.0270(4) Uani 1 2 d S . . C17 C 0.14485(6) 0.1903(4) 0.16654(10) 0.0246(4) Uani 1 1 d . . . C10 C 0.35866(7) 0.2534(5) 0.59103(11) 0.0264(4) Uani 1 1 d . . . C6 C 0.31221(7) 0.5337(5) 0.47571(12) 0.0295(4) Uani 1 1 d . . . H6 H 0.3102 0.609 0.4278 0.035 Uiso 1 1 calc R . . C12 C 0.45557(7) -0.2354(5) 0.72916(10) 0.0304(4) Uani 1 1 d . . . H12A H 0.4559 -0.3696 0.7723 0.037 Uiso 1 1 calc R . . H12B H 0.4562 -0.3838 0.6887 0.037 Uiso 1 1 calc R . . C23 C 0.09306(7) 0.5930(4) 0.29684(11) 0.0268(4) Uani 1 1 d . . . H23A H 0.1232 0.7309 0.3234 0.032 Uiso 1 1 calc R . . H23B H 0.091 0.4143 0.3304 0.032 Uiso 1 1 calc R . . C13 C 0.12789(7) 0.0073(6) -0.00078(12) 0.0339(5) Uani 1 1 d . . . C5 C 0.35634(7) 0.3655(5) 0.52004(10) 0.0265(4) Uani 1 1 d . . . C11 C 0.40747(7) -0.0331(5) 0.70327(11) 0.0296(4) Uani 1 1 d . . . H11A H 0.3772 -0.167 0.7012 0.036 Uiso 1 1 calc R . . H11B H 0.4102 0.1501 0.7381 0.036 Uiso 1 1 calc R . . C21 C 0.18386(7) 0.2632(5) 0.30144(11) 0.0293(4) Uani 1 1 d . . . H21 H 0.1818 0.3395 0.3473 0.035 Uiso 1 1 calc R . . C18 C 0.19054(7) 0.0327(5) 0.16780(12) 0.0285(4) Uani 1 1 d . . . H18 H 0.1931 -0.049 0.1227 0.034 Uiso 1 1 calc R . . C22 C 0.14248(6) 0.3072(4) 0.23498(10) 0.0234(4) Uani 1 1 d . . . C20 C 0.22779(7) 0.1076(5) 0.29991(12) 0.0346(5) Uani 1 1 d . . . H20 H 0.2559 0.077 0.3451 0.042 Uiso 1 1 calc R . . C16 C 0.10021(7) 0.2371(5) 0.10026(12) 0.0304(4) Uani 1 1 d . . . H16 H 0.0718 0.3384 0.1086 0.036 Uiso 1 1 calc R . . C2 C 0.40945(7) 0.3626(6) 0.43440(12) 0.0365(5) Uani 1 1 d . . . N3 N 0.15430(7) -0.1145(6) -0.02775(11) 0.0509(6) Uani 1 1 d . . . C1 C 0.37482(7) 0.5182(6) 0.36975(13) 0.0396(5) Uani 1 1 d . . . C9 C 0.31809(7) 0.3165(5) 0.61631(11) 0.0316(4) Uani 1 1 d . . . H9 H 0.3196 0.244 0.6642 0.038 Uiso 1 1 calc R . . C15 C 0.09216(7) 0.1611(5) 0.02843(11) 0.0331(5) Uani 1 1 d . . . C7 C 0.27177(7) 0.5914(5) 0.50061(13) 0.0351(5) Uani 1 1 d . . . H7 H 0.2418 0.7019 0.4697 0.042 Uiso 1 1 calc R . . C4 C 0.40052(7) 0.2956(5) 0.49838(12) 0.0336(5) Uani 1 1 d . . . H4 H 0.4278 0.1844 0.535 0.04 Uiso 1 1 calc R . . C19 C 0.23155(7) -0.0044(6) 0.23370(12) 0.0334(5) Uani 1 1 d . . . H19 H 0.2623 -0.1068 0.2336 0.04 Uiso 1 1 calc R . . N1 N 0.34918(7) 0.6470(7) 0.31661(12) 0.0631(7) Uani 1 1 d . . . C3 C 0.45807(9) 0.2710(8) 0.42780(13) 0.0535(7) Uani 1 1 d . . . C14 C 0.04315(8) 0.2301(7) -0.02813(13) 0.0481(6) Uani 1 1 d . . . N2 N 0.49595(9) 0.1997(8) 0.42139(13) 0.0760(9) Uani 1 1 d . . . C24 C 0.04449(6) 0.7922(4) 0.27394(11) 0.0276(4) Uani 1 1 d . . . H24A H 0.0438 0.9268 0.3166 0.033 Uiso 1 1 calc R . . H24B H 0.044 0.9407 0.2329 0.033 Uiso 1 1 calc R . . C8 C 0.27510(7) 0.4871(6) 0.57088(12) 0.0343(5) Uani 1 1 d . . . H8 H 0.2476 0.5325 0.5886 0.041 Uiso 1 1 calc R . . N4 N 0.00434(9) 0.2827(7) -0.07390(12) 0.0713(8) 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 0.0279(7) 0.0415(8) 0.0197(7) 0.0012(6) 0.0083(6) 0.0015(6) O4 0.0223(8) 0.0230(9) 0.0351(10) 0 0.0132(8) 0 O2 0.0192(6) 0.0399(7) 0.0220(7) -0.0015(5) 0.0085(5) 0.0014(5) O3 0.0303(9) 0.0253(9) 0.0220(9) 0 0.0050(8) 0 C17 0.0204(8) 0.0274(9) 0.0256(10) 0.0028(7) 0.0076(8) 0.0005(7) C10 0.0256(8) 0.0261(9) 0.0265(10) -0.0070(7) 0.0077(7) -0.0053(7) C6 0.0252(9) 0.0355(10) 0.0279(10) -0.0004(8) 0.0092(8) 0.0032(8) C12 0.0427(11) 0.0241(9) 0.0212(9) -0.0002(7) 0.0067(8) -0.0076(8) C23 0.0276(9) 0.0323(9) 0.0238(9) -0.0041(8) 0.0133(8) -0.0060(7) C13 0.0276(9) 0.0492(12) 0.0230(11) -0.0021(8) 0.0061(9) 0.0074(9) C5 0.0254(8) 0.0310(9) 0.0233(9) -0.0039(7) 0.0089(8) -0.0002(7) C11 0.0346(10) 0.0343(10) 0.0205(9) -0.0035(7) 0.0100(8) -0.0107(8) C21 0.0266(9) 0.0360(10) 0.0240(10) 0.0015(7) 0.0072(7) -0.0032(8) C18 0.0244(8) 0.0354(10) 0.0283(11) 0.0021(8) 0.0123(8) 0.0040(7) C22 0.0189(8) 0.0258(9) 0.0273(9) 0.0029(7) 0.0102(7) -0.0027(6) C20 0.0242(9) 0.0448(12) 0.0304(11) 0.0083(9) 0.0037(8) 0.0042(8) C16 0.0249(9) 0.0399(11) 0.0275(10) 0.0033(8) 0.0105(8) 0.0086(8) C2 0.0289(10) 0.0552(13) 0.0265(10) 0.0084(9) 0.0110(8) 0.0133(9) N3 0.0318(9) 0.0883(17) 0.0320(10) -0.0125(10) 0.0101(8) 0.0159(10) C1 0.0255(10) 0.0683(15) 0.0296(12) 0.0141(10) 0.0153(10) 0.0134(10) C9 0.0308(9) 0.0386(11) 0.0287(10) -0.0101(8) 0.0147(8) -0.0097(8) C15 0.0258(9) 0.0478(12) 0.0251(10) 0.0001(8) 0.0078(8) 0.0092(8) C7 0.0249(9) 0.0420(12) 0.0364(12) -0.0066(9) 0.0081(9) 0.0019(8) C4 0.0294(9) 0.0452(12) 0.0259(10) 0.0068(8) 0.0094(8) 0.0122(8) C19 0.0203(9) 0.0450(11) 0.0341(11) 0.0067(9) 0.0085(9) 0.0068(8) N1 0.0385(11) 0.114(2) 0.0400(12) 0.0364(13) 0.0183(10) 0.0293(12) C3 0.0428(12) 0.0923(19) 0.0291(12) 0.0237(12) 0.0172(11) 0.0301(12) C14 0.0385(12) 0.0800(17) 0.0270(11) -0.0039(11) 0.0130(10) 0.0227(11) N2 0.0541(13) 0.146(3) 0.0373(12) 0.0358(14) 0.0275(11) 0.0528(16) C24 0.0303(9) 0.0240(9) 0.0325(10) -0.0035(7) 0.0159(8) -0.0052(7) C8 0.0229(9) 0.0431(11) 0.0403(12) -0.0111(9) 0.0152(9) -0.0052(8) N4 0.0450(11) 0.134(2) 0.0287(11) -0.0032(12) 0.0048(10) 0.0406(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C10 1.354(2) . ? O1 C11 1.433(2) . ? O4 C24 1.4239(19) . ? O4 C24 1.4239(19) 2 ? O2 C22 1.359(2) . ? O2 C23 1.430(2) . ? O3 C12 1.423(2) 2_656 ? O3 C12 1.423(2) . ? C17 C18 1.412(2) . ? C17 C22 1.416(3) . ? C17 C16 1.444(3) . ? C10 C9 1.389(3) . ? C10 C5 1.413(3) . ? C6 C7 1.377(3) . ? C6 C5 1.404(3) . ? C6 H6 0.95 . ? C12 C11 1.500(3) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C23 C24 1.503(2) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C13 N3 1.144(3) . ? C13 C15 1.437(3) . ? C5 C4 1.447(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C21 C20 1.381(3) . ? C21 C22 1.397(3) . ? C21 H21 0.95 . ? C18 C19 1.382(3) . ? C18 H18 0.95 . ? C20 C19 1.383(3) . ? C20 H20 0.95 . ? C16 C15 1.349(3) . ? C16 H16 0.95 . ? C2 C4 1.356(3) . ? C2 C1 1.427(3) . ? C2 C3 1.442(3) . ? C1 N1 1.148(3) . ? C9 C8 1.395(3) . ? C9 H9 0.95 . ? C15 C14 1.440(3) . ? C7 C8 1.382(3) . ? C7 H7 0.95 . ? C4 H4 0.95 . ? C19 H19 0.95 . ? C3 N2 1.133(3) . ? C14 N4 1.147(3) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C8 H8 0.95 . ? 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 C10 O1 C11 119.66(14) . . ? C24 O4 C24 108.33(17) . 2 ? C22 O2 C23 118.63(14) . . ? C12 O3 C12 108.1(2) 2_656 . ? C18 C17 C22 117.76(17) . . ? C18 C17 C16 124.36(18) . . ? C22 C17 C16 117.88(16) . . ? O1 C10 C9 124.13(18) . . ? O1 C10 C5 116.01(16) . . ? C9 C10 C5 119.85(18) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? O3 C12 C11 110.37(15) . . ? O3 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? O3 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O2 C23 C24 107.15(16) . . ? O2 C23 H23A 110.3 . . ? C24 C23 H23A 110.3 . . ? O2 C23 H23B 110.3 . . ? C24 C23 H23B 110.3 . . ? H23A C23 H23B 108.5 . . ? N3 C13 C15 176.3(2) . . ? C6 C5 C10 118.85(17) . . ? C6 C5 C4 124.63(18) . . ? C10 C5 C4 116.52(17) . . ? O1 C11 C12 107.43(16) . . ? O1 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? O1 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C20 C21 C22 119.37(18) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C19 C18 C17 120.90(19) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? O2 C22 C21 123.96(17) . . ? O2 C22 C17 115.25(15) . . ? C21 C22 C17 120.79(16) . . ? C21 C20 C19 121.14(18) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C15 C16 C17 130.76(18) . . ? C15 C16 H16 114.6 . . ? C17 C16 H16 114.6 . . ? C4 C2 C1 126.54(19) . . ? C4 C2 C3 119.37(19) . . ? C1 C2 C3 114.09(19) . . ? N1 C1 C2 176.4(2) . . ? C10 C9 C8 119.57(19) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C16 C15 C13 127.05(17) . . ? C16 C15 C14 120.03(18) . . ? C13 C15 C14 112.91(18) . . ? C6 C7 C8 119.5(2) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C2 C4 C5 130.65(19) . . ? C2 C4 H4 114.7 . . ? C5 C4 H4 114.7 . . ? C18 C19 C20 120.03(18) . . ? C18 C19 H19 120 . . ? C20 C19 H19 120 . . ? N2 C3 C2 178.9(3) . . ? N4 C14 C15 179.0(2) . . ? O4 C24 C23 111.12(14) . . ? O4 C24 H24A 109.4 . . ? C23 C24 H24A 109.4 . . ? O4 C24 H24B 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108 . . ? C7 C8 C9 121.19(19) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C4 H4 N2 0.95 2.53 3.413(3) 154.2 3_656 C16 H16 N4 0.95 2.51 3.389(3) 153.1 3_565 C19 H19 N1 0.95 2.58 3.402(3) 144.5 1_545 _database_code_depnum_ccdc_archive 'CCDC 908002' ####################################################################### # # 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_dcyme12 #TrackingRef '14982_web_deposit_cif_file_0_CarlosBasilioPinheiro_1351263618.dcym.cif' _audit_creation_date 2012-10-24T21:18:40-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_moiety 'C26 H22 N4 O2' _chemical_formula_sum 'C26 H22 N4 O2' _chemical_formula_weight 422.48 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2(1)/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.3137(2) _cell_length_b 9.9807(4) _cell_length_c 25.5817(8) _cell_angle_alpha 90 _cell_angle_beta 94.618(3) _cell_angle_gamma 90 _cell_volume 1097.81(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8930 _cell_measurement_theta_min 2.0364 _cell_measurement_theta_max 29.4191 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.15 _exptl_crystal_description primatic _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 -2 0.1917 -1 0 2 0.1917 0 -1 1 0.0882 0 -1 -1 0.1008 0 1 1 0.0468 0 1 -1 0.092 0 0 -1 0.1925 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.988 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 -0.1617521 _diffrn_orient_matrix_ub_12 -0.0141448 _diffrn_orient_matrix_ub_13 -0.002063 _diffrn_orient_matrix_ub_21 0.0328151 _diffrn_orient_matrix_ub_22 -0.0688627 _diffrn_orient_matrix_ub_23 0.0045603 _diffrn_orient_matrix_ub_31 -0.0028865 _diffrn_orient_matrix_ub_32 0.010413 _diffrn_orient_matrix_ub_33 0.0273631 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_unetI/netI 0.0125 _diffrn_reflns_number 17312 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 2259 _reflns_number_gt 2078 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0437P)^2^+0.3775P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2259 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.04 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.0942 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.231 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.37879(18) 0.31482(7) 0.11944(3) 0.0242(2) Uani 1 1 d . . . C13 C 0.4188(2) 0.48412(11) 0.02460(4) 0.0204(2) Uani 1 1 d . . . H13A H 0.2599 0.5536 0.0295 0.024 Uiso 1 1 calc R . . H13B H 0.3107 0.3969 0.02 0.024 Uiso 1 1 calc R . . C12 C 0.6445(2) 0.47814(11) 0.07340(4) 0.0223(2) Uani 1 1 d . . . H12A H 0.7999 0.4071 0.0686 0.027 Uiso 1 1 calc R . . H12B H 0.7571 0.5645 0.0772 0.027 Uiso 1 1 calc R . . N2 N -0.0755(4) -0.25310(12) 0.14655(5) 0.0564(4) Uani 1 1 d . . . C11 C 0.4908(2) 0.45066(11) 0.12318(4) 0.0221(2) Uani 1 1 d . . . H11A H 0.6422 0.4612 0.1541 0.026 Uiso 1 1 calc R . . H11B H 0.3162 0.5136 0.1266 0.026 Uiso 1 1 calc R . . N1 N 0.3142(4) -0.15171(12) 0.00124(5) 0.0549(4) Uani 1 1 d . . . C10 C 0.2246(2) 0.26408(11) 0.15885(4) 0.0201(2) Uani 1 1 d . . . C4 C 0.1907(3) 0.06224(11) 0.10452(4) 0.0267(3) Uani 1 1 d . . . H4 H 0.2798 0.1169 0.0793 0.032 Uiso 1 1 calc R . . C9 C 0.1706(3) 0.33497(11) 0.20413(4) 0.0239(2) Uani 1 1 d . . . H9 H 0.2446 0.4242 0.2088 0.029 Uiso 1 1 calc R . . C7 C -0.1041(3) 0.14535(12) 0.23611(4) 0.0299(3) Uani 1 1 d . . . H7 H -0.2191 0.1058 0.2622 0.036 Uiso 1 1 calc R . . C5 C 0.1190(3) 0.13079(11) 0.15202(4) 0.0224(2) Uani 1 1 d . . . C6 C -0.0477(3) 0.07442(12) 0.19160(4) 0.0288(3) Uani 1 1 d . . . H6 H -0.1233 -0.0147 0.1876 0.035 Uiso 1 1 calc R . . C8 C 0.0082(3) 0.27465(12) 0.24236(4) 0.0269(3) Uani 1 1 d . . . H8 H -0.0265 0.3229 0.2734 0.032 Uiso 1 1 calc R . . C3 C 0.1498(3) -0.06774(12) 0.09073(4) 0.0281(3) Uani 1 1 d . . . C2 C 0.0234(3) -0.16951(12) 0.12209(5) 0.0349(3) Uani 1 1 d . . . C1 C 0.2409(4) -0.11387(12) 0.04080(5) 0.0376(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 0.0340(4) 0.0192(4) 0.0206(4) -0.0013(3) 0.0094(3) -0.0031(3) C13 0.0172(5) 0.0209(5) 0.0234(5) 0.0011(4) 0.0040(4) -0.0024(4) C12 0.0187(5) 0.0239(5) 0.0244(5) -0.0010(4) 0.0028(4) -0.0039(4) N2 0.1051(12) 0.0290(6) 0.0387(7) -0.0089(5) 0.0280(7) -0.0226(7) C11 0.0231(5) 0.0196(5) 0.0234(5) -0.0026(4) 0.0017(4) -0.0023(4) N1 0.0998(11) 0.0302(6) 0.0382(7) -0.0083(5) 0.0277(7) -0.0019(6) C10 0.0211(5) 0.0225(5) 0.0166(5) 0.0031(4) 0.0020(4) 0.0041(4) C4 0.0373(6) 0.0222(6) 0.0218(5) 0.0016(4) 0.0085(5) -0.0005(5) C9 0.0275(5) 0.0233(5) 0.0210(5) -0.0014(4) 0.0020(4) 0.0034(4) C7 0.0376(6) 0.0299(6) 0.0237(6) 0.0075(5) 0.0130(5) 0.0072(5) C5 0.0279(5) 0.0208(5) 0.0187(5) 0.0021(4) 0.0040(4) 0.0032(4) C6 0.0387(6) 0.0220(5) 0.0269(6) 0.0038(4) 0.0106(5) 0.0013(5) C8 0.0323(6) 0.0313(6) 0.0177(5) -0.0006(4) 0.0052(4) 0.0103(5) C3 0.0402(6) 0.0224(6) 0.0223(6) -0.0006(4) 0.0067(5) -0.0022(5) C2 0.0561(8) 0.0232(6) 0.0261(6) -0.0064(5) 0.0087(5) -0.0084(6) C1 0.0627(9) 0.0205(6) 0.0311(7) -0.0027(5) 0.0135(6) -0.0040(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C10 1.3502(12) . ? O1 C11 1.4399(13) . ? C13 C12 1.5213(14) . ? C13 C13 1.5225(19) 3_665 ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C12 C11 1.5075(14) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? N2 C2 1.1456(17) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? N1 C1 1.1482(17) . ? C10 C9 1.3930(14) . ? C10 C5 1.4126(15) . ? C4 C3 1.3521(16) . ? C4 C5 1.4493(15) . ? C4 H4 0.95 . ? C9 C8 1.3855(15) . ? C9 H9 0.95 . ? C7 C6 1.3789(16) . ? C7 C8 1.3832(17) . ? C7 H7 0.95 . ? C5 C6 1.4057(15) . ? C6 H6 0.95 . ? C8 H8 0.95 . ? C3 C2 1.4296(16) . ? C3 C1 1.4417(16) . ? 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 C10 O1 C11 119.10(8) . . ? C12 C13 C13 112.31(10) . 3_665 ? C12 C13 H13A 109.1 . . ? C13 C13 H13A 109.1 3_665 . ? C12 C13 H13B 109.1 . . ? C13 C13 H13B 109.1 3_665 . ? H13A C13 H13B 107.9 . . ? C11 C12 C13 113.85(8) . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? O1 C11 C12 106.46(8) . . ? O1 C11 H11A 110.4 . . ? C12 C11 H11A 110.4 . . ? O1 C11 H11B 110.4 . . ? C12 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? O1 C10 C9 123.78(10) . . ? O1 C10 C5 115.74(9) . . ? C9 C10 C5 120.48(10) . . ? C3 C4 C5 129.76(11) . . ? C3 C4 H4 115.1 . . ? C5 C4 H4 115.1 . . ? C8 C9 C10 119.61(10) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C6 C7 C8 119.41(10) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C6 C5 C10 117.81(10) . . ? C6 C5 C4 124.82(10) . . ? C10 C5 C4 117.38(9) . . ? C7 C6 C5 121.59(11) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C7 C8 C9 121.08(10) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C4 C3 C2 125.64(11) . . ? C4 C3 C1 119.91(11) . . ? C2 C3 C1 114.45(10) . . ? N2 C2 C3 178.53(14) . . ? N1 C1 C3 179.38(14) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C12 H12B N2 0.99 2.6 3.4341(16) 141.4 1_665 _database_code_depnum_ccdc_archive 'CCDC 908003' ####################################################################### # # 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_dcyme11 #TrackingRef '14982_web_deposit_cif_file_0_CarlosBasilioPinheiro_1351263618.dcym.cif' _audit_creation_date 2012-10-25T18:53:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_moiety 'C25 H20 N4 O2' _chemical_formula_sum 'C25 H20 N4 O2' _chemical_formula_weight 408.45 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 27.4458(9) _cell_length_b 4.38430(10) _cell_length_c 19.1157(7) _cell_angle_alpha 90 _cell_angle_beta 110.267(3) _cell_angle_gamma 90 _cell_volume 2157.79(12) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 13038 _cell_measurement_theta_min 1.7144 _cell_measurement_theta_max 62.226 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.6398 _exptl_crystal_size_mid 0.2095 _exptl_crystal_size_min 0.0987 _exptl_crystal_description primatic _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.257 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1 0 0 0.1034 0 -1 0 0.3302 0 1 0 0.3092 0 0 -1 0.0493 0 0 1 0.0493 1 0 0 0.1092 -37 -1 4 0.0936 27 -4 -3 0.2603 -1 0 1 0.0446 1 0 -1 0.0569 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.66 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.66888 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 -0.017881 _diffrn_orient_matrix_ub_12 -0.0658776 _diffrn_orient_matrix_ub_13 0.0665079 _diffrn_orient_matrix_ub_21 -0.0554294 _diffrn_orient_matrix_ub_22 -0.0623477 _diffrn_orient_matrix_ub_23 -0.0543025 _diffrn_orient_matrix_ub_31 0.0137173 _diffrn_orient_matrix_ub_32 -0.3394736 _diffrn_orient_matrix_ub_33 -0.0029206 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_unetI/netI 0.0375 _diffrn_reflns_number 15224 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 6.45 _diffrn_reflns_theta_max 62.38 _diffrn_reflns_theta_full 62.38 _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.962 _reflns_number_total 3272 _reflns_number_gt 2540 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0744P)^2^+0.5034P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3272 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.163 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 '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' 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 0.39771(10) 0.0812(5) 0.62820(13) 0.0653(7) Uani 1 1 d . . . C26 C 0 0.5884(9) 0.25 0.0529(11) Uani 1 2 d S . . H26A H 0.0006 0.4581 0.2093 0.063 Uiso 0.5 1 calc PR . . H26B H -0.0006 0.4582 0.2907 0.063 Uiso 0.5 1 calc PR . . O2 O 0.10202(9) 0.4639(6) 0.23306(13) 0.0610(6) Uani 1 1 d . . . C25 C 0.5 -0.0382(10) 0.75 0.0557(12) Uani 1 2 d S . . H25A H 0.5002 0.0923 0.7911 0.067 Uiso 0.5 1 calc PR . . H25B H 0.4998 0.0923 0.7089 0.067 Uiso 0.5 1 calc PR . . C17 C 0.14651(12) 0.1867(8) 0.1699(2) 0.0591(9) Uani 1 1 d . . . C10 C 0.35573(12) 0.2483(7) 0.58941(19) 0.0535(8) Uani 1 1 d . . . C6 C 0.31331(15) 0.5369(9) 0.4782(2) 0.0723(11) Uani 1 1 d . . . H6 H 0.3128 0.6127 0.4326 0.087 Uiso 1 1 calc R . . C12 C 0.45082(13) -0.2286(7) 0.72590(19) 0.0622(9) Uani 1 1 d . . . H12A H 0.4516 -0.3653 0.6864 0.075 Uiso 1 1 calc R . . H12B H 0.4506 -0.353 0.7677 0.075 Uiso 1 1 calc R . . C23 C 0.09916(13) 0.6023(7) 0.2993(2) 0.0590(9) Uani 1 1 d . . . H22A H 0.1285 0.7373 0.3213 0.071 Uiso 1 1 calc R . . H23B H 0.0992 0.4477 0.3357 0.071 Uiso 1 1 calc R . . C13 C 0.12711(16) 0.0124(12) 0.0030(3) 0.0871(14) Uani 1 1 d . . . C5 C 0.35524(13) 0.3649(8) 0.52035(19) 0.0591(9) Uani 1 1 d . . . C11 C 0.40174(14) -0.0490(8) 0.6989(2) 0.0612(9) Uani 1 1 d . . . H11A H 0.3722 -0.1803 0.6934 0.073 Uiso 1 1 calc R . . H11B H 0.4024 0.111 0.7343 0.073 Uiso 1 1 calc R . . C21 C 0.18737(13) 0.2604(8) 0.3038(2) 0.0648(10) Uani 1 1 d . . . H21 H 0.1865 0.3403 0.3485 0.078 Uiso 1 1 calc R . . C18 C 0.19066(14) 0.0229(10) 0.1721(2) 0.0737(11) Uani 1 1 d . . . H18 H 0.1924 -0.059 0.1282 0.088 Uiso 1 1 calc R . . C22 C 0.14543(12) 0.3051(7) 0.23788(19) 0.0532(8) Uani 1 1 d . . . C20 C 0.22946(15) 0.1000(10) 0.3028(3) 0.0783(12) Uani 1 1 d . . . H20 H 0.2573 0.0708 0.3469 0.094 Uiso 1 1 calc R . . C16 C 0.10183(14) 0.2388(9) 0.1037(2) 0.0731(11) Uani 1 1 d . . . H16 H 0.0744 0.3385 0.112 0.088 Uiso 1 1 calc R . . C2 C 0.40897(15) 0.3578(11) 0.4365(2) 0.0844(13) Uani 1 1 d . . . N3 N 0.15324(17) -0.1051(14) -0.0233(3) 0.137(2) Uani 1 1 d . . . C1 C 0.37476(17) 0.5119(14) 0.3729(3) 0.0987(17) Uani 1 1 d . . . C9 C 0.31515(13) 0.3120(8) 0.6137(2) 0.0660(10) Uani 1 1 d . . . H9 H 0.3154 0.2389 0.6594 0.079 Uiso 1 1 calc R . . C15 C 0.09318(14) 0.1674(10) 0.0319(2) 0.0785(12) Uani 1 1 d . . . C7 C 0.27209(16) 0.6005(10) 0.5013(3) 0.0786(12) Uani 1 1 d . . . H7 H 0.2441 0.7164 0.472 0.094 Uiso 1 1 calc R . . C4 C 0.39928(15) 0.2912(10) 0.4988(2) 0.0765(12) Uani 1 1 d . . . H4 H 0.4252 0.1793 0.5339 0.092 Uiso 1 1 calc R . . C19 C 0.23137(14) -0.0199(11) 0.2372(3) 0.0813(13) Uani 1 1 d . . . H19 H 0.2603 -0.1299 0.2371 0.098 Uiso 1 1 calc R . . N1 N 0.35003(17) 0.6386(15) 0.3212(3) 0.153(2) Uani 1 1 d . . . C3 C 0.4562(2) 0.2655(15) 0.4290(3) 0.118(2) Uani 1 1 d . . . C14 C 0.04349(18) 0.2364(14) -0.0253(3) 0.116(2) Uani 1 1 d . . . N2 N 0.4939(2) 0.1894(15) 0.4222(3) 0.176(3) Uani 1 1 d . . . C24 C 0.04876(12) 0.7803(6) 0.2755(2) 0.0599(9) Uani 1 1 d . . . H24A H 0.0482 0.906 0.3169 0.072 Uiso 1 1 calc R . . H24B H 0.0482 0.9161 0.2351 0.072 Uiso 1 1 calc R . . C8 C 0.27373(15) 0.4871(10) 0.5690(3) 0.0751(12) Uani 1 1 d . . . H8 H 0.2463 0.5285 0.5855 0.09 Uiso 1 1 calc R . . N4 N 0.00530(18) 0.2939(15) -0.0703(3) 0.160(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 0.0716(16) 0.0876(17) 0.0434(15) 0.0048(11) 0.0282(13) 0.0127(13) C26 0.057(3) 0.047(2) 0.060(3) 0 0.027(2) 0 O2 0.0500(13) 0.0842(15) 0.0523(15) 0.0001(12) 0.0223(12) 0.0106(11) C25 0.076(3) 0.054(2) 0.037(3) 0 0.018(2) 0 C17 0.0480(18) 0.077(2) 0.054(2) 0.0137(18) 0.0201(16) 0.0090(16) C10 0.0516(19) 0.0613(18) 0.050(2) -0.0109(15) 0.0204(16) -0.0011(15) C6 0.067(2) 0.097(3) 0.058(3) 0.008(2) 0.027(2) 0.018(2) C12 0.087(2) 0.0536(17) 0.046(2) -0.0006(15) 0.0228(18) -0.0068(17) C23 0.064(2) 0.0627(19) 0.054(2) -0.0037(17) 0.0242(18) -0.0049(16) C13 0.066(3) 0.141(4) 0.053(3) -0.005(2) 0.018(2) 0.027(3) C5 0.057(2) 0.075(2) 0.047(2) -0.0038(17) 0.0203(17) 0.0064(17) C11 0.079(2) 0.0626(19) 0.049(2) -0.0002(16) 0.0303(19) -0.0111(17) C21 0.053(2) 0.083(2) 0.055(2) 0.0038(17) 0.0144(18) -0.0010(17) C18 0.057(2) 0.105(3) 0.065(3) 0.006(2) 0.029(2) 0.022(2) C22 0.0459(18) 0.0650(18) 0.053(2) 0.0101(16) 0.0220(16) -0.0010(15) C20 0.053(2) 0.110(3) 0.065(3) 0.020(2) 0.012(2) 0.013(2) C16 0.062(2) 0.112(3) 0.051(2) 0.008(2) 0.027(2) 0.025(2) C2 0.070(2) 0.139(4) 0.050(3) 0.024(2) 0.027(2) 0.037(2) N3 0.105(3) 0.224(6) 0.083(3) -0.027(3) 0.033(3) 0.058(3) C1 0.073(3) 0.166(4) 0.067(4) 0.046(3) 0.036(3) 0.038(3) C9 0.067(2) 0.080(2) 0.060(2) -0.0143(18) 0.033(2) -0.0081(19) C15 0.064(2) 0.122(3) 0.051(3) 0.007(2) 0.0223(19) 0.023(2) C7 0.066(2) 0.094(3) 0.074(3) -0.002(2) 0.022(2) 0.013(2) C4 0.071(2) 0.113(3) 0.050(2) 0.018(2) 0.0261(19) 0.037(2) C19 0.048(2) 0.121(3) 0.073(3) 0.016(2) 0.020(2) 0.024(2) N1 0.099(3) 0.272(6) 0.106(4) 0.105(4) 0.058(3) 0.073(4) C3 0.100(3) 0.208(6) 0.058(3) 0.041(3) 0.044(3) 0.069(4) C14 0.084(3) 0.212(6) 0.051(3) 0.004(3) 0.024(3) 0.060(4) N2 0.141(4) 0.333(8) 0.080(3) 0.068(4) 0.070(3) 0.131(5) C24 0.070(2) 0.0508(16) 0.068(2) -0.0038(16) 0.0356(19) -0.0024(15) C8 0.057(2) 0.091(3) 0.084(3) -0.021(2) 0.033(2) -0.001(2) N4 0.095(3) 0.312(7) 0.062(3) 0.008(4) 0.014(2) 0.081(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C10 1.350(4) . ? O1 C11 1.436(4) . ? C26 C24 1.511(4) 2 ? C26 C24 1.511(4) . ? C26 H26A 0.97 . ? C26 H26B 0.97 . ? O2 C22 1.355(4) . ? O2 C23 1.431(4) . ? C25 C12 1.517(4) . ? C25 C12 1.517(4) 2_656 ? C25 H25A 0.97 . ? C25 H25B 0.97 . ? C17 C18 1.397(5) . ? C17 C22 1.409(5) . ? C17 C16 1.444(5) . ? C10 C9 1.375(4) . ? C10 C5 1.411(5) . ? C6 C7 1.378(6) . ? C6 C5 1.378(5) . ? C6 H6 0.93 . ? C12 C11 1.490(5) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C23 C24 1.514(4) . ? C23 H22A 0.97 . ? C23 H23B 0.97 . ? C13 N3 1.132(5) . ? C13 C15 1.411(6) . ? C5 C4 1.442(5) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C21 C20 1.358(5) . ? C21 C22 1.396(5) . ? C21 H21 0.93 . ? C18 C19 1.367(6) . ? C18 H18 0.93 . ? C20 C19 1.378(6) . ? C20 H20 0.93 . ? C16 C15 1.347(6) . ? C16 H16 0.93 . ? C2 C4 1.341(6) . ? C2 C3 1.411(6) . ? C2 C1 1.422(6) . ? C1 N1 1.133(6) . ? C9 C8 1.392(6) . ? C9 H9 0.93 . ? C15 C14 1.454(6) . ? C7 C8 1.372(6) . ? C7 H7 0.93 . ? C4 H4 0.93 . ? C19 H19 0.93 . ? C3 N2 1.138(6) . ? C14 N4 1.130(5) . ? C24 H24A 0.97 . ? C24 H24B 0.97 . ? C8 H8 0.93 . ? 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 C10 O1 C11 120.4(3) . . ? C24 C26 C24 112.4(3) 2 . ? C24 C26 H26A 109.1 2 . ? C24 C26 H26A 109.1 . . ? C24 C26 H26B 109.1 2 . ? C24 C26 H26B 109.1 . . ? H26A C26 H26B 107.9 . . ? C22 O2 C23 118.3(3) . . ? C12 C25 C12 113.2(4) . 2_656 ? C12 C25 H25A 108.9 . . ? C12 C25 H25A 108.9 2_656 . ? C12 C25 H25B 108.9 . . ? C12 C25 H25B 108.9 2_656 . ? H25A C25 H25B 107.7 . . ? C18 C17 C22 117.2(3) . . ? C18 C17 C16 124.9(4) . . ? C22 C17 C16 117.9(3) . . ? O1 C10 C9 124.2(3) . . ? O1 C10 C5 116.1(3) . . ? C9 C10 C5 119.7(3) . . ? C7 C6 C5 122.4(4) . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C11 C12 C25 114.7(3) . . ? C11 C12 H12A 108.6 . . ? C25 C12 H12A 108.6 . . ? C11 C12 H12B 108.6 . . ? C25 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? O2 C23 C24 106.0(3) . . ? O2 C23 H22A 110.5 . . ? C24 C23 H22A 110.5 . . ? O2 C23 H23B 110.5 . . ? C24 C23 H23B 110.5 . . ? H22A C23 H23B 108.7 . . ? N3 C13 C15 176.7(5) . . ? C6 C5 C10 118.7(3) . . ? C6 C5 C4 124.7(3) . . ? C10 C5 C4 116.6(3) . . ? O1 C11 C12 107.6(3) . . ? O1 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? O1 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C20 C21 C22 119.9(4) . . ? C20 C21 H21 120 . . ? C22 C21 H21 120 . . ? C19 C18 C17 121.7(4) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? O2 C22 C21 124.3(3) . . ? O2 C22 C17 115.2(3) . . ? C21 C22 C17 120.5(3) . . ? C21 C20 C19 120.8(4) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C15 C16 C17 130.8(3) . . ? C15 C16 H16 114.6 . . ? C17 C16 H16 114.6 . . ? C4 C2 C3 120.0(4) . . ? C4 C2 C1 126.0(4) . . ? C3 C2 C1 114.1(4) . . ? N1 C1 C2 175.9(5) . . ? C10 C9 C8 119.3(4) . . ? C10 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? C16 C15 C13 127.1(4) . . ? C16 C15 C14 120.4(4) . . ? C13 C15 C14 112.4(4) . . ? C8 C7 C6 117.8(4) . . ? C8 C7 H7 121.1 . . ? C6 C7 H7 121.1 . . ? C2 C4 C5 130.5(3) . . ? C2 C4 H4 114.8 . . ? C5 C4 H4 114.8 . . ? C18 C19 C20 119.9(4) . . ? C18 C19 H19 120 . . ? C20 C19 H19 120 . . ? N2 C3 C2 179.2(7) . . ? N4 C14 C15 178.8(7) . . ? C26 C24 C23 115.1(2) . . ? C26 C24 H24A 108.5 . . ? C23 C24 H24A 108.5 . . ? C26 C24 H24B 108.5 . . ? C23 C24 H24B 108.5 . . ? H24A C24 H24B 107.5 . . ? C7 C8 C9 122.1(4) . . ? C7 C8 H8 119 . . ? C9 C8 H8 119 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C4 H4 N2 0.93 2.64 3.500(6) 154.3 3_656 C16 H16 N4 0.93 2.61 3.457(5) 151.6 3_565 C19 H19 N1 0.93 2.63 3.436(6) 144.9 1_545 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF _database_code_depnum_ccdc_archive 'CCDC 908004' ####################################################################### # # 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_l14clo4-140kmo #TrackingRef '18566_web_deposit_cif_file_0_CarlosBasilioPinheiro_1363311846.archive.cif' _audit_creation_date 2013-01-23T23:38:51-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_sum 'C12 H9 N2 O' _chemical_formula_moiety 'C12 H8 N2 O' _chemical_formula_weight 197.21 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.1838(3) _cell_length_b 9.5677(6) _cell_length_c 12.2486(8) _cell_angle_alpha 96.676(5) _cell_angle_beta 91.076(5) _cell_angle_gamma 93.139(6) _cell_volume 486.05(7) _cell_formula_units_Z 2 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 1838 _cell_measurement_theta_min 2.1426 _cell_measurement_theta_max 29.4464 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 206 _exptl_crystal_description Prismatic _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.6111 _exptl_crystal_size_mid 0.2672 _exptl_crystal_size_min 0.0966 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0483 0 0 -1 0.0483 -5 6 8 0.1657 5 -6 -4 0.2042 0 -1 1 0.0843 0 1 -1 0.0843 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_detector_area_resol_mean 10.4186 _diffrn_reflns_number 5808 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 1985 _reflns_number_gt 1469 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0689P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1985 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.236 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.055 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 -0.2790(3) 0.14973(11) 0.67416(8) 0.0266(3) Uani 1 1 d . . . C11 C -0.3971(4) 0.00459(16) 0.65577(13) 0.0238(4) Uani 1 1 d . . . H11A H -0.5291 -0.0197 0.7179 0.029 Uiso 1 1 calc R . . H11B H -0.2168 -0.0584 0.6485 0.029 Uiso 1 1 calc R . . N1 N -0.3062(4) 0.66413(15) 0.51971(13) 0.0404(4) Uani 1 1 d . . . C12 C -0.5961(4) -0.01092(16) 0.55091(12) 0.0232(4) Uani 1 1 d . . . H12A H -0.7643 0.0582 0.5583 0.028 Uiso 1 1 calc R . . H12B H -0.7041 -0.1064 0.5404 0.028 Uiso 1 1 calc R . . C10 C -0.1074(3) 0.19597(16) 0.76740(12) 0.0212(4) Uani 1 1 d . . . C4 C -0.1270(4) 0.42556(17) 0.69948(13) 0.0243(4) Uani 1 1 d . . . H4 H -0.2643 0.3758 0.6438 0.029 Uiso 1 1 calc R . . C9 C -0.0155(4) 0.10923(17) 0.84402(13) 0.0252(4) Uani 1 1 d . . . H9 H -0.0737 0.0111 0.8331 0.030 Uiso 1 1 calc R . . C5 C -0.0215(4) 0.34188(16) 0.78268(12) 0.0220(4) Uani 1 1 d . . . C6 C 0.1537(4) 0.39551(17) 0.87811(13) 0.0285(4) Uani 1 1 d . . . H6 H 0.2116 0.4936 0.8907 0.034 Uiso 1 1 calc R . . C3 C 0.1359(4) 0.66339(17) 0.75839(13) 0.0276(4) Uani 1 1 d . . . C2 C -0.0629(4) 0.56323(16) 0.68768(12) 0.0249(4) Uani 1 1 d . . . C8 C 0.1613(4) 0.16644(18) 0.93628(13) 0.0289(4) Uani 1 1 d . . . H8 H 0.2272 0.1069 0.9883 0.035 Uiso 1 1 calc R . . N2 N 0.2955(4) 0.74727(16) 0.81147(12) 0.0401(4) Uani 1 1 d . . . C7 C 0.2439(4) 0.30954(19) 0.95399(13) 0.0319(4) Uani 1 1 d . . . H7 H 0.3625 0.3480 1.0184 0.038 Uiso 1 1 calc R . . C1 C -0.1997(4) 0.61963(17) 0.59453(14) 0.0288(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 0.0401(7) 0.0157(6) 0.0229(6) 0.0013(4) -0.0086(5) -0.0033(5) C11 0.0299(8) 0.0143(8) 0.0266(9) 0.0020(6) 0.0008(7) -0.0031(7) N1 0.0608(10) 0.0235(9) 0.0373(9) 0.0045(7) -0.0108(8) 0.0063(7) C12 0.0246(8) 0.0172(8) 0.0268(9) -0.0001(6) -0.0001(7) -0.0010(6) C10 0.0236(8) 0.0206(9) 0.0186(8) -0.0005(6) 0.0004(6) 0.0012(6) C4 0.0297(9) 0.0183(9) 0.0237(8) -0.0023(6) -0.0018(7) 0.0019(7) C9 0.0330(9) 0.0196(9) 0.0237(8) 0.0041(7) 0.0017(7) 0.0030(7) C5 0.0243(8) 0.0194(9) 0.0219(8) 0.0002(6) -0.0005(6) 0.0025(6) C6 0.0367(9) 0.0206(9) 0.0271(9) 0.0014(7) -0.0037(7) -0.0037(7) C3 0.0376(9) 0.0186(9) 0.0270(9) 0.0052(7) -0.0014(7) 0.0011(7) C2 0.0327(9) 0.0197(9) 0.0220(8) 0.0008(7) -0.0006(7) 0.0028(7) C8 0.0344(9) 0.0288(10) 0.0251(9) 0.0096(7) -0.0025(7) 0.0032(7) N2 0.0593(10) 0.0244(8) 0.0359(9) 0.0073(7) -0.0098(8) -0.0086(7) C7 0.0391(10) 0.0338(10) 0.0216(9) 0.0028(7) -0.0091(7) -0.0056(8) C1 0.0391(10) 0.0164(9) 0.0298(9) -0.0011(7) -0.0031(7) 0.0008(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C10 1.3538(18) . ? O1 C11 1.4390(18) . ? C11 C12 1.505(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? N1 C1 1.147(2) . ? C12 C12 1.525(3) 2_456 ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C10 C9 1.385(2) . ? C10 C5 1.412(2) . ? C4 C2 1.354(2) . ? C4 C5 1.444(2) . ? C4 H4 0.9500 . ? C9 C8 1.380(2) . ? C9 H9 0.9500 . ? C5 C6 1.398(2) . ? C6 C7 1.372(2) . ? C6 H6 0.9500 . ? C3 N2 1.147(2) . ? C3 C2 1.433(2) . ? C2 C1 1.440(2) . ? C8 C7 1.384(2) . ? C8 H8 0.9500 . ? C7 H7 0.9500 . ? 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 C10 O1 C11 119.19(12) . . ? O1 C11 C12 106.42(12) . . ? O1 C11 H11A 110.4 . . ? C12 C11 H11A 110.4 . . ? O1 C11 H11B 110.4 . . ? C12 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? C11 C12 C12 113.83(15) . 2_456 ? C11 C12 H12A 108.8 . . ? C12 C12 H12A 108.8 2_456 . ? C11 C12 H12B 108.8 . . ? C12 C12 H12B 108.8 2_456 . ? H12A C12 H12B 107.7 . . ? O1 C10 C9 123.87(14) . . ? O1 C10 C5 115.42(13) . . ? C9 C10 C5 120.72(14) . . ? C2 C4 C5 130.74(15) . . ? C2 C4 H4 114.6 . . ? C5 C4 H4 114.6 . . ? C8 C9 C10 119.49(15) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C6 C5 C10 117.81(14) . . ? C6 C5 C4 124.66(15) . . ? C10 C5 C4 117.52(13) . . ? C7 C6 C5 121.39(15) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? N2 C3 C2 177.06(18) . . ? C4 C2 C3 126.98(14) . . ? C4 C2 C1 118.93(14) . . ? C3 C2 C1 114.08(14) . . ? C9 C8 C7 120.86(15) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C6 C7 C8 119.73(15) . . ? C6 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? N1 C1 C2 179.34(19) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C4 H4 N1 0.95 2.64 3.545(2) 158.4 2_466 C11 H11A N2 0.99 2.70 3.491(2) 137.5 1_445 # END of CIF _database_code_depnum_ccdc_archive 'CCDC 929360'