# 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_compound_4a #TrackingRef '10967_web_deposit_cif_file_0_JorgePasan_1335518314.compound_4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N4 O2' _chemical_formula_weight 370.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n 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 5.9474(5) _cell_length_b 14.2294(17) _cell_length_c 10.5393(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.768(8) _cell_angle_gamma 90.00 _cell_volume 888.83(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2462 _cell_measurement_theta_min 3.4305 _cell_measurement_theta_max 28.4023 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_min 0.42674 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_detector_area_resol_mean 10.5953 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9784 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 27.40 _reflns_number_total 1994 _reflns_number_gt 1265 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0621P)^2^+0.2027P] 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 1994 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1012 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1315 _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 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 C1 C 0.1948(3) 0.59968(15) 0.84322(19) 0.0426(5) Uani 1 1 d . . . C2 C 0.0947(3) 0.61816(14) 0.70974(18) 0.0394(5) Uani 1 1 d . . . C3 C -0.1196(3) 0.66119(15) 0.69268(19) 0.0457(5) Uani 1 1 d . . . H3 H -0.1973 0.6774 0.7625 0.055 Uiso 1 1 calc R . . C4 C -0.2101(3) 0.67849(16) 0.57244(19) 0.0482(6) Uani 1 1 d . . . H4 H -0.3510 0.7068 0.5591 0.058 Uiso 1 1 calc R . . C5 C -0.0902(3) 0.65344(14) 0.46819(18) 0.0418(5) Uani 1 1 d . . . C6 C -0.1725(4) 0.66819(16) 0.33982(19) 0.0498(6) Uani 1 1 d . . . H6 H -0.3144 0.6947 0.3216 0.060 Uiso 1 1 calc R . . C7 C -0.0472(4) 0.64420(17) 0.2433(2) 0.0540(6) Uani 1 1 d . . . H7 H -0.1027 0.6550 0.1594 0.065 Uiso 1 1 calc R . . C8 C 0.1663(4) 0.60295(17) 0.2693(2) 0.0551(6) Uani 1 1 d . . . H8 H 0.2514 0.5869 0.2024 0.066 Uiso 1 1 calc R . . C9 C 0.2501(4) 0.58622(16) 0.39124(19) 0.0487(6) Uani 1 1 d . . . H9 H 0.3909 0.5582 0.4070 0.058 Uiso 1 1 calc R . . C10 C 0.1250(3) 0.61104(14) 0.49343(18) 0.0394(5) Uani 1 1 d . . . C11 C 0.5325(3) 0.54675(16) 0.97272(18) 0.0486(6) Uani 1 1 d . . . H11A H 0.5047 0.5964 1.0325 0.058 Uiso 1 1 calc R . . H11B H 0.6925 0.5465 0.9608 0.058 Uiso 1 1 calc R . . N1 N 0.4050(3) 0.56568(13) 0.85130(15) 0.0493(5) Uani 1 1 d . . . H1 H 0.4674 0.5545 0.7821 0.059 Uiso 1 1 calc R . . N2 N 0.2146(3) 0.59431(12) 0.61545(15) 0.0414(4) Uani 1 1 d . . . O1 O 0.0926(2) 0.61707(12) 0.93630(13) 0.0568(5) 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 C1 0.0380(11) 0.0514(13) 0.0381(11) 0.0010(9) 0.0027(9) -0.0052(9) C2 0.0337(10) 0.0463(13) 0.0377(11) 0.0017(9) 0.0001(8) -0.0043(8) C3 0.0370(11) 0.0551(14) 0.0454(12) -0.0010(10) 0.0058(9) 0.0035(9) C4 0.0357(10) 0.0552(14) 0.0527(13) 0.0000(10) -0.0024(9) 0.0075(9) C5 0.0382(10) 0.0432(12) 0.0431(11) 0.0024(9) -0.0023(8) -0.0012(9) C6 0.0463(12) 0.0522(14) 0.0487(13) 0.0068(10) -0.0084(10) -0.0001(10) C7 0.0588(14) 0.0625(16) 0.0386(12) 0.0074(10) -0.0084(10) -0.0073(11) C8 0.0603(15) 0.0647(16) 0.0409(12) -0.0024(11) 0.0073(10) -0.0013(11) C9 0.0442(12) 0.0587(15) 0.0432(12) -0.0002(10) 0.0040(9) 0.0040(10) C10 0.0372(10) 0.0439(12) 0.0365(11) 0.0011(9) -0.0014(8) -0.0024(8) C11 0.0369(11) 0.0711(16) 0.0366(11) 0.0035(10) -0.0034(8) 0.0014(10) N1 0.0366(9) 0.0771(14) 0.0339(9) 0.0044(9) 0.0007(7) 0.0055(8) N2 0.0350(9) 0.0508(11) 0.0379(9) 0.0012(7) 0.0009(7) -0.0001(7) O1 0.0465(9) 0.0842(12) 0.0400(9) 0.0012(8) 0.0063(7) 0.0050(8) _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 C1 O1 1.221(2) . ? C1 N1 1.337(3) . ? C1 C2 1.504(3) . ? C2 N2 1.315(2) . ? C2 C3 1.412(3) . ? C3 C4 1.358(3) . ? C4 C5 1.405(3) . ? C5 C6 1.416(3) . ? C5 C10 1.420(3) . ? C6 C7 1.354(3) . ? C7 C8 1.405(3) . ? C8 C9 1.360(3) . ? C9 C10 1.404(3) . ? C10 N2 1.371(2) . ? C11 N1 1.457(2) . ? C11 C11 1.512(4) 3_667 ? 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 N1 123.17(18) . . ? O1 C1 C2 122.08(18) . . ? N1 C1 C2 114.72(17) . . ? N2 C2 C3 123.80(18) . . ? N2 C2 C1 117.65(17) . . ? C3 C2 C1 118.54(17) . . ? C4 C3 C2 118.76(18) . . ? C3 C4 C5 119.76(19) . . ? C4 C5 C6 123.51(19) . . ? C4 C5 C10 118.01(17) . . ? C6 C5 C10 118.48(19) . . ? C7 C6 C5 120.8(2) . . ? C6 C7 C8 120.24(19) . . ? C9 C8 C7 120.8(2) . . ? C8 C9 C10 120.3(2) . . ? N2 C10 C9 119.09(18) . . ? N2 C10 C5 121.57(17) . . ? C9 C10 C5 119.34(18) . . ? N1 C11 C11 111.4(2) . 3_667 ? C1 N1 C11 122.59(17) . . ? C2 N2 C10 118.08(17) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.213 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 879084' ####################################################################### # # 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_compound_4b #TrackingRef '10968_web_deposit_cif_file_1_JorgePasan_1335518314.compound_4b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N4 O2' _chemical_formula_weight 398.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 7.6300(15) _cell_length_b 12.848(3) _cell_length_c 10.165(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.01(3) _cell_angle_gamma 90.00 _cell_volume 978.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.73850 _diffrn_source synchrotron _diffrn_source_type 'ESRF-CRG BM16' _diffrn_radiation_monochromator 'Si 111' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9.6 _diffrn_radiation_detector 'ADSC Q210r CCD (binned mode)' _diffrn_measurement_device_type 'Single-axis HUBER diffractometer' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16772 _diffrn_reflns_av_R_equivalents 0.0738 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 28.06 _reflns_number_total 2132 _reflns_number_gt 1964 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MxCube (ESRF, 2006)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0701P)^2^+0.2377P] 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 2132 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1286 _refine_ls_wR_factor_gt 0.1262 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 C1 C 0.42874(15) 0.20198(9) 0.05693(11) 0.0272(3) Uani 1 1 d . . . C2 C 0.33235(15) 0.10027(8) 0.01744(11) 0.0255(3) Uani 1 1 d . . . C3 C 0.33156(16) 0.02484(9) 0.11843(11) 0.0293(3) Uani 1 1 d . . . H3 H 0.3873 0.0380 0.2065 0.035 Uiso 1 1 calc R . . C4 C 0.24735(17) -0.06782(9) 0.08417(12) 0.0317(3) Uani 1 1 d . . . H4 H 0.2452 -0.1188 0.1488 0.038 Uiso 1 1 calc R . . C5 C 0.16360(15) -0.08546(9) -0.05014(12) 0.0280(3) Uani 1 1 d . . . C6 C 0.07247(16) -0.17887(9) -0.09524(14) 0.0342(3) Uani 1 1 d . . . H6 H 0.0649 -0.2318 -0.0342 0.041 Uiso 1 1 calc R . . C7 C -0.00409(16) -0.19216(9) -0.22665(14) 0.0351(3) Uani 1 1 d . . . H7 H -0.0631 -0.2539 -0.2547 0.042 Uiso 1 1 calc R . . C8 C 0.00603(16) -0.11233(10) -0.32029(13) 0.0327(3) Uani 1 1 d . . . H8 H -0.0456 -0.1222 -0.4100 0.039 Uiso 1 1 calc R . . C9 C 0.09089(15) -0.02069(9) -0.28066(12) 0.0292(3) Uani 1 1 d . . . H9 H 0.0951 0.0316 -0.3432 0.035 Uiso 1 1 calc R . . C10 C 0.17226(14) -0.00495(8) -0.14510(12) 0.0254(3) Uani 1 1 d . . . C11 C 0.56239(15) 0.35602(8) -0.02353(12) 0.0284(3) Uani 1 1 d . . . H11A H 0.6176 0.3691 -0.1003 0.034 Uiso 1 1 calc R . . H11B H 0.6570 0.3482 0.0544 0.034 Uiso 1 1 calc R . . C12 C 0.44785(14) 0.44918(8) -0.00266(11) 0.0269(3) Uani 1 1 d . . . H12A H 0.4046 0.4404 0.0804 0.032 Uiso 1 1 calc R . . H12B H 0.3451 0.4525 -0.0753 0.032 Uiso 1 1 calc R . . N1 N 0.46130(13) 0.25954(7) -0.04514(9) 0.0278(3) Uani 1 1 d . . . H1 H 0.4214 0.2390 -0.1258 0.033 Uiso 1 1 calc R . . N2 N 0.25735(12) 0.08754(7) -0.10937(9) 0.0251(2) Uani 1 1 d . . . O1 O 0.47513(13) 0.22646(7) 0.17562(8) 0.0349(2) 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 C1 0.0305(6) 0.0236(6) 0.0279(6) -0.0008(4) 0.0067(4) 0.0029(4) C2 0.0285(5) 0.0207(5) 0.0286(6) 0.0000(4) 0.0088(4) 0.0033(4) C3 0.0341(6) 0.0278(6) 0.0265(6) 0.0027(4) 0.0066(4) 0.0035(4) C4 0.0372(6) 0.0248(6) 0.0351(6) 0.0078(4) 0.0123(5) 0.0043(5) C5 0.0285(6) 0.0203(5) 0.0371(6) 0.0024(4) 0.0110(5) 0.0035(4) C6 0.0341(6) 0.0209(5) 0.0499(7) 0.0031(5) 0.0136(5) 0.0012(4) C7 0.0305(6) 0.0220(6) 0.0537(8) -0.0073(5) 0.0098(5) -0.0016(4) C8 0.0278(6) 0.0309(6) 0.0389(7) -0.0088(5) 0.0052(5) 0.0024(5) C9 0.0296(6) 0.0260(6) 0.0331(6) -0.0010(4) 0.0082(5) 0.0029(4) C10 0.0254(5) 0.0192(5) 0.0330(6) 0.0002(4) 0.0089(4) 0.0029(4) C11 0.0307(6) 0.0219(6) 0.0324(6) -0.0022(4) 0.0059(4) -0.0028(4) C12 0.0281(6) 0.0225(6) 0.0299(6) -0.0023(4) 0.0048(4) -0.0027(4) N1 0.0366(5) 0.0203(5) 0.0262(5) -0.0022(3) 0.0054(4) -0.0030(4) N2 0.0279(5) 0.0193(5) 0.0289(5) 0.0004(3) 0.0076(4) 0.0021(3) O1 0.0455(5) 0.0323(5) 0.0269(5) -0.0047(3) 0.0068(4) -0.0038(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2315(14) . ? C1 N1 1.3355(15) . ? C1 C2 1.5156(16) . ? C2 N2 1.3168(15) . ? C2 C3 1.4126(15) . ? C3 C4 1.3660(17) . ? C4 C5 1.4108(17) . ? C5 C6 1.4185(16) . ? C5 C10 1.4250(16) . ? C6 C7 1.3626(19) . ? C7 C8 1.4114(19) . ? C8 C9 1.3668(16) . ? C9 C10 1.4135(17) . ? C10 N2 1.3694(14) . ? C11 N1 1.4544(14) . ? C11 C12 1.5206(15) . ? C12 C12 1.525(2) 3_665 ? 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 N1 123.95(11) . . ? O1 C1 C2 120.92(10) . . ? N1 C1 C2 115.12(10) . . ? N2 C2 C3 124.39(10) . . ? N2 C2 C1 117.68(10) . . ? C3 C2 C1 117.92(10) . . ? C4 C3 C2 118.67(11) . . ? C3 C4 C5 119.39(10) . . ? C4 C5 C6 123.51(11) . . ? C4 C5 C10 117.90(11) . . ? C6 C5 C10 118.59(11) . . ? C7 C6 C5 120.98(11) . . ? C6 C7 C8 120.11(11) . . ? C9 C8 C7 120.73(12) . . ? C8 C9 C10 120.38(11) . . ? N2 C10 C9 118.71(10) . . ? N2 C10 C5 122.09(11) . . ? C9 C10 C5 119.20(10) . . ? N1 C11 C12 112.93(9) . . ? C11 C12 C12 111.66(11) . 3_665 ? C1 N1 C11 121.78(10) . . ? C2 N2 C10 117.57(9) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.277 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 879085' ####################################################################### # # 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_compound_4c #TrackingRef '10969_web_deposit_cif_file_2_JorgePasan_1335518314.compound_4c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H28 N4 O3' _chemical_formula_weight 444.52 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 P2/c 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 11.1425(3) _cell_length_b 15.6947(4) _cell_length_c 14.6254(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.235(4) _cell_angle_gamma 90.00 _cell_volume 2399.81(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4407 _cell_measurement_theta_min 3.2178 _cell_measurement_theta_max 70.1041 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 0.660 _exptl_absorpt_correction_T_min 0.91178 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _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) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_detector_area_resol_mean 10.5953 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13034 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0172 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 70.24 _reflns_number_total 4441 _reflns_number_gt 3218 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1024P)^2^+0.5503P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4441 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.2012 _refine_ls_wR_factor_gt 0.1827 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 C1 C 0.3426(3) 0.28866(19) 0.3257(2) 0.0897(8) Uani 1 1 d . . . C2 C 0.3461(3) 0.38491(17) 0.33192(19) 0.0766(7) Uani 1 1 d . . . C3 C 0.2322(3) 0.4311(2) 0.3032(2) 0.0978(9) Uani 1 1 d . . . H3 H 0.1536 0.4033 0.2813 0.117 Uiso 1 1 calc R . . C4 C 0.2385(3) 0.5172(2) 0.3078(2) 0.0989(10) Uani 1 1 d . . . H4 H 0.1637 0.5493 0.2891 0.119 Uiso 1 1 calc R . . C5 C 0.3589(3) 0.55843(17) 0.34111(18) 0.0795(7) Uani 1 1 d . . . C6 C 0.3752(4) 0.6476(2) 0.3473(2) 0.0999(11) Uani 1 1 d . . . H6 H 0.3039 0.6831 0.3291 0.120 Uiso 1 1 calc R . . C7 C 0.4939(5) 0.6818(2) 0.3797(3) 0.1141(13) Uani 1 1 d . . . H7 H 0.5036 0.7407 0.3821 0.137 Uiso 1 1 calc R . . C8 C 0.6025(4) 0.6295(2) 0.4098(3) 0.1106(11) Uani 1 1 d . . . H8 H 0.6835 0.6539 0.4337 0.133 Uiso 1 1 calc R . . C9 C 0.5898(3) 0.54333(18) 0.4040(2) 0.0930(9) Uani 1 1 d . . . H9 H 0.6623 0.5090 0.4231 0.112 Uiso 1 1 calc R . . C10 C 0.4688(3) 0.50618(15) 0.36970(18) 0.0695(6) Uani 1 1 d . . . C11 C 0.4698(3) 0.15806(16) 0.3614(2) 0.0845(8) Uani 1 1 d . . . H11A H 0.5466 0.1451 0.3471 0.101 Uiso 1 1 calc R . . H11B H 0.3979 0.1331 0.3103 0.101 Uiso 1 1 calc R . . C12 C 0.4801(2) 0.11794(15) 0.45632(19) 0.0708(6) Uani 1 1 d . . . H12A H 0.4055 0.1330 0.4727 0.085 Uiso 1 1 calc R . . H12B H 0.5551 0.1400 0.5071 0.085 Uiso 1 1 calc R . . C13 C 0.4897(2) 0.02142(15) 0.45234(18) 0.0687(6) Uani 1 1 d . . . H13A H 0.4117 -0.0005 0.4046 0.082 Uiso 1 1 calc R . . H13B H 0.5599 0.0069 0.4304 0.082 Uiso 1 1 calc R . . C14 C 0.8362(2) 0.19863(14) 0.52425(17) 0.0603(5) Uani 1 1 d . . . C15 C 0.83966(18) 0.10358(13) 0.50989(16) 0.0545(5) Uani 1 1 d . . . C16 C 0.8774(2) 0.05107(14) 0.59233(17) 0.0632(5) Uani 1 1 d . . . H16 H 0.9006 0.0744 0.6545 0.076 Uiso 1 1 calc R . . C17 C 0.8794(2) -0.03494(15) 0.57968(18) 0.0667(6) Uani 1 1 d . . . H17 H 0.9046 -0.0711 0.6334 0.080 Uiso 1 1 calc R . . C18 C 0.84327(19) -0.06841(13) 0.48541(16) 0.0576(5) Uani 1 1 d . . . C19 C 0.8430(3) -0.15691(14) 0.4648(2) 0.0722(6) Uani 1 1 d . . . H19 H 0.8663 -0.1960 0.5157 0.087 Uiso 1 1 calc R . . C20 C 0.8093(3) -0.18481(16) 0.3724(2) 0.0823(8) Uani 1 1 d . . . H20 H 0.8098 -0.2429 0.3602 0.099 Uiso 1 1 calc R . . C21 C 0.7737(3) -0.12762(17) 0.2947(2) 0.0856(8) Uani 1 1 d . . . H21 H 0.7503 -0.1480 0.2312 0.103 Uiso 1 1 calc R . . C22 C 0.7728(3) -0.04197(16) 0.31090(18) 0.0758(7) Uani 1 1 d . . . H22 H 0.7492 -0.0043 0.2585 0.091 Uiso 1 1 calc R . . C23 C 0.80746(19) -0.01058(13) 0.40653(16) 0.0560(5) Uani 1 1 d . . . C24 C 0.8146(2) 0.33931(13) 0.4503(2) 0.0735(7) Uani 1 1 d . . . H24A H 0.7747 0.3556 0.4970 0.088 Uiso 1 1 calc R . . H24B H 0.7615 0.3605 0.3870 0.088 Uiso 1 1 calc R . . C25 C 0.9450(2) 0.38087(13) 0.4786(2) 0.0716(6) Uani 1 1 d . . . H25A H 0.9841 0.3664 0.4309 0.086 Uiso 1 1 calc R . . H25B H 0.9992 0.3589 0.5413 0.086 Uiso 1 1 calc R . . C26 C 0.9358(2) 0.47781(14) 0.4848(2) 0.0706(6) Uani 1 1 d . . . H26A H 0.8826 0.4994 0.4216 0.085 Uiso 1 1 calc R . . H26B H 0.8940 0.4917 0.5311 0.085 Uiso 1 1 calc R . . N1 N 0.4532(2) 0.25008(13) 0.36005(17) 0.0843(7) Uani 1 1 d . . . H1 H 0.5205 0.2811 0.3834 0.101 Uiso 1 1 calc R . . N2 N 0.4607(2) 0.41962(12) 0.36456(15) 0.0706(5) Uani 1 1 d . . . N3 N 0.8198(2) 0.24672(11) 0.44645(15) 0.0689(5) Uani 1 1 d . . . H3A H 0.8121 0.2225 0.3919 0.083 Uiso 1 1 calc R . . N4 N 0.80619(17) 0.07558(10) 0.41984(13) 0.0572(4) Uani 1 1 d . . . O1 O 0.2425(3) 0.25082(17) 0.2859(3) 0.1553(13) Uani 1 1 d . . . O2 O 0.84624(19) 0.22724(11) 0.60464(13) 0.0815(5) Uani 1 1 d . . . O1W O 1.0000 0.33625(19) 0.7500 0.1083(12) Uani 1 2 d S . . O2W O 0.0000 0.2032(6) 0.2500 0.320(5) Uani 1 2 d S . . H1W H 0.954(3) 0.302(2) 0.702(2) 0.110(11) Uiso 1 1 d . . . H2W H 0.0812 0.2454 0.2695 0.442 Uiso 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 C1 0.0795(19) 0.0773(18) 0.101(2) 0.0011(15) 0.0169(15) -0.0083(15) C2 0.0752(16) 0.0723(16) 0.0756(15) 0.0079(12) 0.0176(12) 0.0094(13) C3 0.0757(18) 0.094(2) 0.108(2) 0.0006(17) 0.0115(15) 0.0168(16) C4 0.090(2) 0.103(2) 0.095(2) 0.0096(17) 0.0205(16) 0.0398(18) C5 0.103(2) 0.0713(16) 0.0702(15) 0.0138(12) 0.0380(14) 0.0276(14) C6 0.147(3) 0.0674(17) 0.100(2) 0.0140(15) 0.061(2) 0.035(2) C7 0.184(4) 0.0562(16) 0.128(3) 0.0046(17) 0.086(3) 0.009(2) C8 0.134(3) 0.0693(18) 0.148(3) 0.0009(19) 0.074(3) -0.0122(19) C9 0.096(2) 0.0652(16) 0.130(3) 0.0074(16) 0.0538(19) 0.0011(14) C10 0.0855(17) 0.0583(13) 0.0722(14) 0.0106(11) 0.0369(12) 0.0133(12) C11 0.0945(19) 0.0594(14) 0.0950(19) 0.0026(13) 0.0269(15) -0.0011(13) C12 0.0653(14) 0.0594(13) 0.0888(16) -0.0006(11) 0.0280(12) -0.0007(11) C13 0.0654(14) 0.0571(13) 0.0821(15) -0.0016(11) 0.0237(12) -0.0016(10) C14 0.0544(12) 0.0486(11) 0.0767(14) -0.0060(10) 0.0212(10) -0.0038(9) C15 0.0461(10) 0.0463(10) 0.0717(13) -0.0027(9) 0.0213(9) -0.0023(8) C16 0.0656(13) 0.0591(13) 0.0637(12) -0.0021(10) 0.0208(10) 0.0023(10) C17 0.0687(14) 0.0576(13) 0.0729(14) 0.0117(10) 0.0234(11) 0.0091(10) C18 0.0522(11) 0.0464(10) 0.0772(14) 0.0029(9) 0.0263(10) 0.0014(8) C19 0.0799(16) 0.0456(11) 0.0974(18) 0.0057(11) 0.0388(13) 0.0034(10) C20 0.0966(19) 0.0468(12) 0.112(2) -0.0131(13) 0.0469(16) -0.0073(12) C21 0.104(2) 0.0649(16) 0.0899(18) -0.0206(14) 0.0365(16) -0.0124(14) C22 0.0960(18) 0.0570(13) 0.0717(15) -0.0066(11) 0.0257(13) -0.0039(12) C23 0.0537(11) 0.0448(10) 0.0710(13) -0.0023(9) 0.0237(10) -0.0022(8) C24 0.0798(16) 0.0411(11) 0.0929(17) -0.0005(11) 0.0212(13) -0.0039(10) C25 0.0760(15) 0.0446(12) 0.0919(17) -0.0009(11) 0.0261(13) -0.0043(10) C26 0.0744(15) 0.0452(12) 0.0898(16) 0.0006(11) 0.0254(12) -0.0048(10) N1 0.0825(15) 0.0610(12) 0.0981(16) 0.0108(11) 0.0168(12) 0.0017(11) N2 0.0745(13) 0.0604(12) 0.0777(12) 0.0110(9) 0.0273(10) 0.0092(9) N3 0.0828(13) 0.0431(10) 0.0785(12) -0.0037(9) 0.0251(10) -0.0074(9) N4 0.0592(10) 0.0439(9) 0.0677(11) -0.0011(8) 0.0208(8) -0.0020(7) O1 0.0864(17) 0.0982(19) 0.240(4) -0.019(2) 0.0032(19) -0.0106(14) O2 0.1047(14) 0.0588(10) 0.0866(12) -0.0158(8) 0.0400(10) -0.0042(9) O1W 0.108(2) 0.0601(16) 0.116(2) 0.000 -0.0137(19) 0.000 O2W 0.130(5) 0.257(8) 0.540(16) 0.000 0.075(7) 0.000 _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 C1 O1 1.220(4) . ? C1 N1 1.307(4) . ? C1 C2 1.513(4) . ? C2 N2 1.317(3) . ? C2 C3 1.394(4) . ? C3 C4 1.355(5) . ? C4 C5 1.416(5) . ? C5 C6 1.410(4) . ? C5 C10 1.412(4) . ? C6 C7 1.353(5) . ? C7 C8 1.401(5) . ? C8 C9 1.360(4) . ? C9 C10 1.393(4) . ? C10 N2 1.362(3) . ? C11 N1 1.455(3) . ? C11 C12 1.492(4) . ? C12 C13 1.521(3) . ? C13 C13 1.492(5) 3_656 ? C14 O2 1.227(3) . ? C14 N3 1.324(3) . ? C14 C15 1.509(3) . ? C15 N4 1.314(3) . ? C15 C16 1.400(3) . ? C16 C17 1.364(3) . ? C17 C18 1.398(3) . ? C18 C23 1.413(3) . ? C18 C19 1.421(3) . ? C19 C20 1.344(4) . ? C20 C21 1.394(4) . ? C21 C22 1.366(4) . ? C22 C23 1.405(3) . ? C23 N4 1.367(3) . ? C24 N3 1.456(3) . ? C24 C25 1.513(3) . ? C25 C26 1.530(3) . ? C26 C26 1.514(5) 3_766 ? 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 N1 122.9(3) . . ? O1 C1 C2 121.0(3) . . ? N1 C1 C2 116.0(3) . . ? N2 C2 C3 124.2(3) . . ? N2 C2 C1 115.8(2) . . ? C3 C2 C1 120.0(3) . . ? C4 C3 C2 118.5(3) . . ? C3 C4 C5 120.0(3) . . ? C6 C5 C10 118.6(3) . . ? C6 C5 C4 124.1(3) . . ? C10 C5 C4 117.3(3) . . ? C7 C6 C5 120.3(3) . . ? C6 C7 C8 120.8(3) . . ? C9 C8 C7 120.2(4) . . ? C8 C9 C10 120.4(3) . . ? N2 C10 C9 118.4(2) . . ? N2 C10 C5 121.9(3) . . ? C9 C10 C5 119.7(3) . . ? N1 C11 C12 113.6(2) . . ? C11 C12 C13 111.6(2) . . ? C13 C13 C12 113.8(3) 3_656 . ? O2 C14 N3 123.7(2) . . ? O2 C14 C15 119.8(2) . . ? N3 C14 C15 116.5(2) . . ? N4 C15 C16 124.27(19) . . ? N4 C15 C14 117.26(19) . . ? C16 C15 C14 118.48(19) . . ? C17 C16 C15 118.7(2) . . ? C16 C17 C18 119.5(2) . . ? C17 C18 C23 117.87(19) . . ? C17 C18 C19 123.7(2) . . ? C23 C18 C19 118.4(2) . . ? C20 C19 C18 120.8(2) . . ? C19 C20 C21 120.8(2) . . ? C22 C21 C20 120.6(3) . . ? C21 C22 C23 120.1(2) . . ? N4 C23 C22 118.4(2) . . ? N4 C23 C18 122.23(19) . . ? C22 C23 C18 119.4(2) . . ? N3 C24 C25 113.2(2) . . ? C24 C25 C26 111.6(2) . . ? C26 C26 C25 113.5(3) 3_766 . ? C1 N1 C11 124.3(3) . . ? C2 N2 C10 118.0(2) . . ? C14 N3 C24 122.1(2) . . ? C15 N4 C23 117.40(18) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 70.24 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.556 _refine_diff_density_min -0.621 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 879086' ####################################################################### # # 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_compound_5a #TrackingRef '10970_web_deposit_cif_file_3_JorgePasan_1335518314.compound_5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N4 O2' _chemical_formula_weight 370.41 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 36.179(3) _cell_length_b 5.8548(5) _cell_length_c 8.3919(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.225(9) _cell_angle_gamma 90.00 _cell_volume 1737.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100.0 _cell_measurement_reflns_used 976 _cell_measurement_theta_min 4.9990 _cell_measurement_theta_max 72.9833 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.757 _exptl_absorpt_correction_T_min 0.13424 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100.0 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5953 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4914 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -44 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.00 _diffrn_reflns_theta_max 73.45 _reflns_number_total 1712 _reflns_number_gt 1344 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0000P)^2^+31.0257P] 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 1712 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1282 _refine_ls_R_factor_gt 0.0975 _refine_ls_wR_factor_ref 0.2803 _refine_ls_wR_factor_gt 0.2733 _refine_ls_goodness_of_fit_ref 1.358 _refine_ls_restrained_S_all 1.358 _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 C1 C 0.19313(17) 0.1288(11) 0.9679(7) 0.0267(14) Uani 1 1 d . . . C2 C 0.15743(16) 0.2047(11) 0.8534(7) 0.0205(12) Uani 1 1 d . . . C3 C 0.13728(15) 0.0632(11) 0.7357(7) 0.0210(12) Uani 1 1 d . . . H3 H 0.1471 -0.0787 0.7174 0.025 Uiso 1 1 calc R . . C4 C 0.10165(15) 0.1312(10) 0.6421(6) 0.0175(12) Uani 1 1 d . . . C5 C 0.07932(15) -0.0122(11) 0.5246(6) 0.0207(12) Uani 1 1 d . . . H5 H 0.0880 -0.1564 0.5037 0.025 Uiso 1 1 calc R . . C6 C 0.04498(16) 0.0630(12) 0.4421(7) 0.0244(13) Uani 1 1 d . . . H6 H 0.0299 -0.0285 0.3637 0.029 Uiso 1 1 calc R . . C7 C 0.03254(16) 0.2824(11) 0.4778(7) 0.0235(13) Uani 1 1 d . . . H7 H 0.0090 0.3316 0.4202 0.028 Uiso 1 1 calc R . . C8 C 0.08680(15) 0.3481(11) 0.6708(6) 0.0197(12) Uani 1 1 d . . . C9 C 0.10840(16) 0.4908(11) 0.7909(7) 0.0205(12) Uani 1 1 d . . . H9 H 0.0991 0.6343 0.8097 0.025 Uiso 1 1 calc R . . C10 C 0.14272(16) 0.4220(11) 0.8801(7) 0.0235(13) Uani 1 1 d . . . H10 H 0.1565 0.5186 0.9589 0.028 Uiso 1 1 calc R . . C11 C 0.2455(3) -0.1405(15) 1.0260(12) 0.063(3) Uani 1 1 d . . . H11A H 0.2668 -0.0390 1.0291 0.076 Uiso 1 1 calc R . . H11B H 0.2410 -0.1517 1.1358 0.076 Uiso 1 1 calc R . . N1 N 0.21211(16) -0.0434(11) 0.9194(7) 0.0367(15) Uani 1 1 d . . . H1 H 0.2045 -0.0985 0.8230 0.044 Uiso 1 1 calc R . . N2 N 0.05209(13) 0.4216(9) 0.5873(6) 0.0232(11) Uani 1 1 d . . . O1 O 0.20313(13) 0.2226(9) 1.1020(5) 0.0347(12) 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 C1 0.029(3) 0.020(4) 0.026(3) 0.004(3) -0.006(2) -0.002(3) C2 0.021(3) 0.020(3) 0.018(3) 0.005(2) -0.002(2) -0.002(2) C3 0.019(3) 0.021(3) 0.020(3) 0.003(2) -0.001(2) 0.001(2) C4 0.019(3) 0.016(3) 0.016(2) 0.003(2) 0.000(2) 0.000(2) C5 0.021(3) 0.020(3) 0.020(3) -0.001(2) 0.001(2) 0.001(2) C6 0.020(3) 0.030(4) 0.021(3) -0.003(3) -0.002(2) -0.003(2) C7 0.020(3) 0.025(4) 0.023(3) 0.001(2) -0.002(2) 0.005(2) C8 0.020(3) 0.021(3) 0.017(2) 0.003(2) 0.000(2) -0.002(2) C9 0.027(3) 0.013(3) 0.021(3) 0.000(2) 0.003(2) 0.000(2) C10 0.025(3) 0.024(3) 0.018(3) 0.001(2) -0.003(2) -0.007(2) C11 0.052(5) 0.040(5) 0.070(6) -0.014(4) -0.047(4) 0.020(4) N1 0.033(3) 0.035(4) 0.031(3) -0.004(3) -0.019(2) 0.011(3) N2 0.023(2) 0.021(3) 0.023(2) -0.002(2) -0.0002(19) 0.005(2) O1 0.036(2) 0.034(3) 0.025(2) -0.002(2) -0.0124(19) 0.000(2) _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 C1 O1 1.236(8) . ? C1 N1 1.331(9) . ? C1 C2 1.505(8) . ? C2 C3 1.374(8) . ? C2 C10 1.415(9) . ? C3 C4 1.417(7) . ? C4 C5 1.412(8) . ? C4 C8 1.419(8) . ? C5 C6 1.361(8) . ? C6 C7 1.414(9) . ? C7 N2 1.317(8) . ? C8 N2 1.372(7) . ? C8 C9 1.411(8) . ? C9 C10 1.368(8) . ? C11 C11 1.416(17) 7_547 ? C11 N1 1.457(8) . ? 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 N1 123.0(6) . . ? O1 C1 C2 119.8(6) . . ? N1 C1 C2 117.2(5) . . ? C3 C2 C10 119.7(5) . . ? C3 C2 C1 122.3(6) . . ? C10 C2 C1 117.7(5) . . ? C2 C3 C4 120.7(6) . . ? C5 C4 C3 122.6(6) . . ? C5 C4 C8 118.0(5) . . ? C3 C4 C8 119.3(5) . . ? C6 C5 C4 119.2(6) . . ? C5 C6 C7 118.9(6) . . ? N2 C7 C6 124.2(5) . . ? N2 C8 C9 119.2(6) . . ? N2 C8 C4 122.2(5) . . ? C9 C8 C4 118.6(5) . . ? C10 C9 C8 121.2(6) . . ? C9 C10 C2 120.4(5) . . ? C11 C11 N1 112.3(8) 7_547 . ? C1 N1 C11 121.4(6) . . ? C7 N2 C8 117.4(5) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 73.45 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.435 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 879087' ####################################################################### # # 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_compound_5b #TrackingRef '10971_web_deposit_cif_file_4_JorgePasan_1335518314.compound_5b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N4 O2' _chemical_formula_weight 398.46 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/n 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 5.2593(5) _cell_length_b 5.0366(4) _cell_length_c 35.673(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.355(8) _cell_angle_gamma 90.00 _cell_volume 944.67(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2170 _cell_measurement_theta_min 3.7152 _cell_measurement_theta_max 73.5274 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.735 _exptl_absorpt_correction_T_min 0.77376 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 100.0 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5953 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5371 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 4.96 _diffrn_reflns_theta_max 73.69 _reflns_number_total 1865 _reflns_number_gt 1656 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0535P)^2^+0.4390P] 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 SHELXL _refine_ls_extinction_coef 0.0028(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1865 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1090 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 C1 C 0.4612(2) 0.3584(3) 0.07305(4) 0.0164(3) Uani 1 1 d . . . C2 C 0.2940(2) 0.2901(3) 0.10514(4) 0.0166(3) Uani 1 1 d . . . C3 C 0.3521(3) 0.0886(3) 0.12986(4) 0.0176(3) Uani 1 1 d . . . H3 H 0.4908 -0.0209 0.1255 0.021 Uiso 1 1 calc R . . C4 C 0.2027(2) 0.0460(3) 0.16192(4) 0.0172(3) Uani 1 1 d . . . C5 C 0.2585(3) -0.1528(3) 0.18884(4) 0.0200(3) Uani 1 1 d . . . H5 H 0.3972 -0.2649 0.1860 0.024 Uiso 1 1 calc R . . C6 C 0.1057(3) -0.1777(3) 0.21909(4) 0.0217(3) Uani 1 1 d . . . H6 H 0.1373 -0.3082 0.2371 0.026 Uiso 1 1 calc R . . C7 C -0.1009(3) -0.0020(3) 0.22254(4) 0.0223(3) Uani 1 1 d . . . H7 H -0.2016 -0.0207 0.2435 0.027 Uiso 1 1 calc R . . C8 C -0.0106(2) 0.2118(3) 0.16772(4) 0.0177(3) Uani 1 1 d . . . C9 C -0.0697(3) 0.4142(3) 0.14145(4) 0.0193(3) Uani 1 1 d . . . H9 H -0.2119 0.5206 0.1447 0.023 Uiso 1 1 calc R . . C10 C 0.0805(3) 0.4544(3) 0.11128(4) 0.0179(3) Uani 1 1 d . . . H10 H 0.0422 0.5912 0.0946 0.021 Uiso 1 1 calc R . . C11 C 0.7596(3) 0.2158(3) 0.02621(4) 0.0181(3) Uani 1 1 d . . . H11A H 0.8753 0.3564 0.0340 0.022 Uiso 1 1 calc R . . H11B H 0.6643 0.2768 0.0042 0.022 Uiso 1 1 calc R . . C12 C 0.9111(2) -0.0287(3) 0.01618(3) 0.0177(3) Uani 1 1 d . . . H12A H 0.7955 -0.1711 0.0091 0.021 Uiso 1 1 calc R . . H12B H 1.0105 -0.0867 0.0379 0.021 Uiso 1 1 calc R . . N1 N 0.5836(2) 0.1604(2) 0.05642(3) 0.0177(3) Uani 1 1 d . . . H1 H 0.5589 -0.0006 0.0635 0.021 Uiso 1 1 calc R . . N2 N -0.1622(2) 0.1864(3) 0.19844(3) 0.0215(3) Uani 1 1 d . . . O1 O 0.48381(19) 0.59325(19) 0.06312(3) 0.0216(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 C1 0.0169(6) 0.0145(6) 0.0179(6) 0.0000(5) 0.0018(5) -0.0011(5) C2 0.0177(6) 0.0152(7) 0.0170(6) -0.0025(5) 0.0029(5) -0.0032(5) C3 0.0169(6) 0.0157(7) 0.0204(6) -0.0019(5) 0.0041(5) -0.0006(5) C4 0.0176(6) 0.0157(7) 0.0183(6) -0.0019(5) 0.0019(5) -0.0035(5) C5 0.0200(7) 0.0183(7) 0.0218(7) -0.0004(5) 0.0016(5) -0.0003(6) C6 0.0250(7) 0.0208(7) 0.0193(7) 0.0027(5) 0.0012(5) -0.0047(6) C7 0.0247(7) 0.0236(8) 0.0187(6) -0.0008(5) 0.0060(5) -0.0049(6) C8 0.0174(6) 0.0176(7) 0.0184(6) -0.0034(5) 0.0032(5) -0.0037(6) C9 0.0169(6) 0.0181(7) 0.0228(7) -0.0021(5) 0.0026(5) 0.0006(6) C10 0.0195(6) 0.0149(7) 0.0193(6) 0.0002(5) 0.0008(5) 0.0001(6) C11 0.0201(6) 0.0160(7) 0.0184(6) 0.0018(5) 0.0064(5) -0.0018(6) C12 0.0178(6) 0.0166(7) 0.0190(7) 0.0016(5) 0.0041(5) 0.0000(6) N1 0.0212(6) 0.0127(6) 0.0195(6) 0.0012(4) 0.0075(4) -0.0010(5) N2 0.0213(6) 0.0226(6) 0.0208(6) -0.0014(5) 0.0070(4) -0.0029(5) O1 0.0264(5) 0.0139(5) 0.0250(5) 0.0019(4) 0.0084(4) -0.0005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2410(16) . ? C1 N1 1.3336(18) . ? C1 C2 1.5001(17) . ? C2 C3 1.3738(19) . ? C2 C10 1.4162(19) . ? C3 C4 1.4192(18) . ? C4 C5 1.4134(19) . ? C4 C8 1.418(2) . ? C5 C6 1.3666(19) . ? C6 C7 1.409(2) . ? C7 N2 1.3157(19) . ? C8 N2 1.3761(17) . ? C8 C9 1.4144(19) . ? C9 C10 1.3652(18) . ? C11 N1 1.4642(16) . ? C11 C12 1.5144(19) . ? C12 C12 1.530(2) 3_755 ? 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 N1 122.37(12) . . ? O1 C1 C2 119.89(12) . . ? N1 C1 C2 117.74(12) . . ? C3 C2 C10 119.84(12) . . ? C3 C2 C1 122.26(12) . . ? C10 C2 C1 117.72(12) . . ? C2 C3 C4 120.66(13) . . ? C5 C4 C8 118.05(12) . . ? C5 C4 C3 123.01(13) . . ? C8 C4 C3 118.93(13) . . ? C6 C5 C4 119.02(13) . . ? C5 C6 C7 118.72(13) . . ? N2 C7 C6 125.00(13) . . ? N2 C8 C9 118.17(12) . . ? N2 C8 C4 122.47(13) . . ? C9 C8 C4 119.35(12) . . ? C10 C9 C8 120.47(13) . . ? C9 C10 C2 120.73(13) . . ? N1 C11 C12 111.37(11) . . ? C11 C12 C12 111.01(14) . 3_755 ? C1 N1 C11 120.33(11) . . ? C7 N2 C8 116.73(12) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 73.69 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.296 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 879088' ####################################################################### # # 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_compound_5c #TrackingRef '10972_web_deposit_cif_file_5_JorgePasan_1335518314.compound_5c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 N4 O2' _chemical_formula_weight 426.51 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 5.13820(10) _cell_length_b 7.03440(10) _cell_length_c 29.4160(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.9370(10) _cell_angle_gamma 90.00 _cell_volume 1060.71(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6048 _cell_measurement_theta_min 4.5163 _cell_measurement_theta_max 73.3616 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.689 _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 1.311 _exptl_absorpt_correction_type gaussian _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) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_detector_area_resol_mean 10.5953 _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11495 _diffrn_reflns_av_R_equivalents 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0109 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 6.03 _diffrn_reflns_theta_max 73.52 _reflns_number_total 2114 _reflns_number_gt 1889 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0613P)^2^+0.1923P] 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 SHELXL _refine_ls_extinction_coef 0.0023(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2114 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 C1 C -0.0645(2) 0.87244(17) 0.09003(4) 0.0388(3) Uani 1 1 d . . . C2 C -0.1278(2) 0.71890(17) 0.12289(4) 0.0389(3) Uani 1 1 d . . . C3 C 0.0226(2) 0.55819(18) 0.12524(4) 0.0410(3) Uani 1 1 d . . . H3 H 0.1564 0.5450 0.1057 0.049 Uiso 1 1 calc R . . C4 C -0.0214(2) 0.41202(17) 0.15668(4) 0.0398(3) Uani 1 1 d . . . C5 C 0.1302(3) 0.24453(19) 0.16066(5) 0.0498(3) Uani 1 1 d . . . H5 H 0.2648 0.2245 0.1416 0.060 Uiso 1 1 calc R . . C6 C 0.0774(3) 0.1130(2) 0.19259(5) 0.0555(4) Uani 1 1 d . . . H6 H 0.1757 0.0022 0.1958 0.067 Uiso 1 1 calc R . . C7 C -0.1273(3) 0.1472(2) 0.22047(5) 0.0547(4) Uani 1 1 d . . . H7 H -0.1625 0.0544 0.2417 0.066 Uiso 1 1 calc R . . C8 C -0.2221(2) 0.43516(18) 0.18692(4) 0.0420(3) Uani 1 1 d . . . C9 C -0.3717(3) 0.6036(2) 0.18452(5) 0.0513(3) Uani 1 1 d . . . H9 H -0.5014 0.6214 0.2046 0.062 Uiso 1 1 calc R . . C10 C -0.3287(2) 0.7402(2) 0.15313(5) 0.0471(3) Uani 1 1 d . . . H10 H -0.4324 0.8486 0.1515 0.057 Uiso 1 1 calc R . . C11 C -0.2161(3) 1.13819(19) 0.04281(5) 0.0475(3) Uani 1 1 d . . . H11A H -0.1867 1.0867 0.0130 0.057 Uiso 1 1 calc R . . H11B H -0.0593 1.2054 0.0538 0.057 Uiso 1 1 calc R . . C12 C -0.4386(2) 1.27608(19) 0.03823(5) 0.0475(3) Uani 1 1 d . . . H12A H -0.4644 1.3318 0.0678 0.057 Uiso 1 1 calc R . . H12B H -0.5969 1.2090 0.0281 0.057 Uiso 1 1 calc R . . C13 C -0.3871(2) 1.43287(19) 0.00455(5) 0.0483(3) Uani 1 1 d . . . H13A H -0.2361 1.5051 0.0162 0.058 Uiso 1 1 calc R . . H13B H -0.3451 1.3754 -0.0240 0.058 Uiso 1 1 calc R . . N1 N -0.2617(2) 0.98215(16) 0.07373(4) 0.0449(3) Uani 1 1 d . . . H1 H -0.4171 0.9603 0.0816 0.054 Uiso 1 1 calc R . . N2 N -0.2738(2) 0.30066(18) 0.21893(4) 0.0525(3) Uani 1 1 d . . . O1 O 0.16104(16) 0.89601(14) 0.07923(3) 0.0495(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 C1 0.0353(6) 0.0388(6) 0.0431(6) 0.0013(5) 0.0073(5) 0.0016(4) C2 0.0349(6) 0.0407(6) 0.0415(6) 0.0021(5) 0.0052(5) -0.0009(5) C3 0.0399(6) 0.0426(6) 0.0415(6) 0.0008(5) 0.0104(5) 0.0021(5) C4 0.0416(6) 0.0392(6) 0.0386(6) -0.0012(5) 0.0032(5) -0.0025(5) C5 0.0558(8) 0.0440(7) 0.0506(7) 0.0015(6) 0.0121(6) 0.0057(6) C6 0.0658(9) 0.0434(7) 0.0576(8) 0.0071(6) 0.0064(7) 0.0048(6) C7 0.0635(9) 0.0512(8) 0.0497(8) 0.0129(6) 0.0057(6) -0.0040(6) C8 0.0407(6) 0.0462(7) 0.0393(6) 0.0032(5) 0.0049(5) -0.0047(5) C9 0.0436(7) 0.0601(8) 0.0523(8) 0.0078(6) 0.0179(6) 0.0056(6) C10 0.0403(6) 0.0488(7) 0.0535(8) 0.0061(6) 0.0126(5) 0.0083(5) C11 0.0418(6) 0.0474(7) 0.0549(8) 0.0141(6) 0.0154(5) 0.0061(5) C12 0.0385(6) 0.0456(7) 0.0597(8) 0.0134(6) 0.0129(5) 0.0053(5) C13 0.0403(7) 0.0461(7) 0.0600(8) 0.0125(6) 0.0138(6) 0.0058(6) N1 0.0344(5) 0.0442(6) 0.0572(6) 0.0132(5) 0.0106(4) 0.0026(4) N2 0.0540(7) 0.0565(7) 0.0478(6) 0.0110(5) 0.0096(5) -0.0038(5) O1 0.0360(5) 0.0537(6) 0.0603(6) 0.0130(4) 0.0141(4) 0.0045(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.2335(14) . ? C1 N1 1.3364(15) . ? C1 C2 1.5000(16) . ? C2 C3 1.3683(17) . ? C2 C10 1.4162(17) . ? C3 C4 1.4116(17) . ? C4 C5 1.4130(17) . ? C4 C8 1.4166(17) . ? C5 C6 1.359(2) . ? C6 C7 1.398(2) . ? C7 N2 1.3151(19) . ? C8 N2 1.3736(16) . ? C8 C9 1.4113(19) . ? C9 C10 1.3610(19) . ? C11 N1 1.4548(16) . ? C11 C12 1.4981(17) . ? C12 C13 1.5180(17) . ? C13 C13 1.506(2) 3_485 ? 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 N1 122.18(11) . . ? O1 C1 C2 120.79(10) . . ? N1 C1 C2 117.03(10) . . ? C3 C2 C10 119.28(11) . . ? C3 C2 C1 118.73(11) . . ? C10 C2 C1 121.90(11) . . ? C2 C3 C4 121.30(11) . . ? C3 C4 C5 123.32(12) . . ? C3 C4 C8 118.94(11) . . ? C5 C4 C8 117.71(12) . . ? C6 C5 C4 119.32(13) . . ? C5 C6 C7 118.83(13) . . ? N2 C7 C6 124.96(13) . . ? N2 C8 C9 118.83(12) . . ? N2 C8 C4 122.32(12) . . ? C9 C8 C4 118.85(11) . . ? C10 C9 C8 120.89(12) . . ? C9 C10 C2 120.71(12) . . ? N1 C11 C12 112.95(10) . . ? C11 C12 C13 111.28(10) . . ? C13 C13 C12 113.89(13) 3_485 . ? C1 N1 C11 120.62(10) . . ? C7 N2 C8 116.85(12) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 73.52 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.201 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 879089'