# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Zhou, Li' 'Xu, Zong-Xiang' 'Zhou, Ye' 'Feng, Yan' 'Zhou, Xiangge' 'Xiang, Haifeng' V.A.L.Roy _publ_contact_author_name V.A.L.Roy _publ_contact_author_email val.roy@cityu.edu.hk _publ_section_title ; Structure-charge transport relationship of 5,15-Dialkylated porphyrins ; # Attachment '- C2-Por.cif' data_c3por _database_code_depnum_ccdc_archive 'CCDC 867177' #TrackingRef '- C2-Por.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 N4' _chemical_formula_weight 366.46 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 13.1977(4) _cell_length_b 12.7229(4) _cell_length_c 11.5658(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.008(2) _cell_angle_gamma 90.00 _cell_volume 1892.21(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7334 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.01 _exptl_crystal_description BLOCK _exptl_crystal_colour red _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4687 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SAINT ver 7.34; Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ' Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24410 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.53 _reflns_number_total 4303 _reflns_number_gt 3043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0928P)^2^+1.7888P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4303 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0871 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.2123 _refine_ls_wR_factor_gt 0.1917 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 N1 N 0.50892(10) 0.51628(11) 0.65643(11) 0.0406(3) Uani 1 1 d . . . H1B H 0.4738(16) 0.5724(18) 0.6213(19) 0.071(7) Uiso 1 1 d . . . N2 N 0.27741(10) 0.56579(11) 0.61558(11) 0.0410(3) Uani 1 1 d . . . N3 N 0.30472(11) 0.75520(11) 0.50675(11) 0.0421(3) Uani 1 1 d . . . H3B H 0.3443(16) 0.6877(19) 0.5395(19) 0.074(7) Uiso 1 1 d . . . N4 N 0.53686(10) 0.70640(11) 0.54994(11) 0.0417(3) Uani 1 1 d . . . C1 C 0.67735(12) 0.58251(15) 0.63166(14) 0.0455(4) Uani 1 1 d . . . C2 C 0.61471(12) 0.50783(14) 0.66865(13) 0.0426(4) Uani 1 1 d . . . C3 C 0.64402(14) 0.40806(16) 0.72379(15) 0.0515(5) Uani 1 1 d . . . H3A H 0.7133(16) 0.3811(16) 0.7445(18) 0.064(6) Uiso 1 1 d . . . C4 C 0.55766(15) 0.36044(15) 0.74252(15) 0.0500(5) Uani 1 1 d . . . H4A H 0.5489(14) 0.2931(16) 0.7725(16) 0.053(5) Uiso 1 1 d . . . C5 C 0.47132(13) 0.42779(13) 0.70012(13) 0.0418(4) Uani 1 1 d . . . C6 C 0.36894(14) 0.40620(14) 0.70225(14) 0.0446(4) Uani 1 1 d . . . H6A H 0.3583(14) 0.3295(15) 0.7356(16) 0.050(5) Uiso 1 1 d . . . C7 C 0.28074(12) 0.46755(13) 0.66296(13) 0.0415(4) Uani 1 1 d . . . C8 C 0.17795(14) 0.43577(15) 0.67213(16) 0.0514(4) Uani 1 1 d . . . H8A H 0.1684(15) 0.3723(16) 0.7084(17) 0.055(5) Uiso 1 1 d . . . C9 C 0.11262(14) 0.51560(17) 0.63212(16) 0.0541(5) Uani 1 1 d . . . H9A H 0.0410(17) 0.5213(18) 0.6285(19) 0.068(6) Uiso 1 1 d . . . C10 C 0.17560(12) 0.59786(14) 0.59665(14) 0.0439(4) Uani 1 1 d . . . C11 C 0.13966(13) 0.69552(15) 0.54866(15) 0.0471(4) Uani 1 1 d . . . C12 C 0.20143(13) 0.76822(14) 0.50613(14) 0.0453(4) Uani 1 1 d . . . C13 C 0.17218(15) 0.86843(17) 0.45311(17) 0.0579(5) Uani 1 1 d . . . H13A H 0.0992(15) 0.8993(16) 0.4429(18) 0.060(6) Uiso 1 1 d . . . C14 C 0.25740(17) 0.91179(17) 0.42463(17) 0.0597(6) Uani 1 1 d . . . H14A H 0.2639(17) 0.9830(18) 0.3887(19) 0.071(6) Uiso 1 1 d . . . C15 C 0.34158(14) 0.84163(14) 0.45882(14) 0.0481(4) Uani 1 1 d . . . C16 C 0.44274(15) 0.85963(15) 0.44883(15) 0.0508(5) Uani 1 1 d . . . H16A H 0.4558(16) 0.9325(17) 0.4148(18) 0.066(6) Uiso 1 1 d . . . C17 C 0.53112(13) 0.79891(14) 0.48965(14) 0.0457(4) Uani 1 1 d . . . C18 C 0.63383(15) 0.82992(17) 0.47611(17) 0.0581(5) Uani 1 1 d . . . H18A H 0.6524(15) 0.8892(17) 0.4391(18) 0.062(6) Uiso 1 1 d . . . C19 C 0.70005(14) 0.75474(17) 0.52790(17) 0.0569(5) Uani 1 1 d . . . H19A H 0.7701(15) 0.7514(16) 0.5328(17) 0.054(5) Uiso 1 1 d . . . C20 C 0.63928(12) 0.67679(14) 0.57409(14) 0.0440(4) Uani 1 1 d . . . C21 C 0.79295(14) 0.56060(18) 0.65728(17) 0.0561(5) Uani 1 1 d . . . H21A H 0.8268(17) 0.5938(18) 0.596(2) 0.075(7) Uiso 1 1 d . . . H21B H 0.8042(16) 0.4845(18) 0.6469(18) 0.064(6) Uiso 1 1 d . . . C22 C 0.84913(16) 0.5938(2) 0.7821(2) 0.0703(7) Uani 1 1 d . . . H22A H 0.9209 0.5733 0.7959 0.073(7) Uiso 1 1 calc R . . H22B H 0.8172 0.5603 0.8392 0.088 Uiso 1 1 calc R . . H22C H 0.8446 0.6687 0.7896 0.088 Uiso 1 1 calc R . . C23 C 0.02819(15) 0.72842(18) 0.5474(2) 0.0641(6) Uani 1 1 d . . . H23A H 0.0005 0.7686 0.4760 0.062(6) Uiso 1 1 calc R . . H23B H -0.0145 0.6661 0.5457 0.075 Uiso 1 1 calc R . . C24 C 0.02219(18) 0.7942(2) 0.6554(3) 0.0869(8) Uani 1 1 d . . . H24A H 0.0569 0.8601 0.6520 0.084(8) Uiso 1 1 calc R . . H24B H 0.0552 0.7573 0.7262 0.100 Uiso 1 1 calc R . . H24C H -0.0494 0.8070 0.6561 0.100 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0409(6) 0.0431(7) 0.0381(6) 0.0017(6) 0.0092(5) 0.0016(6) N2 0.0403(6) 0.0446(7) 0.0394(6) -0.0040(6) 0.0114(5) -0.0073(6) N3 0.0436(7) 0.0425(7) 0.0392(6) 0.0030(6) 0.0070(5) 0.0009(6) N4 0.0448(6) 0.0433(7) 0.0395(6) -0.0026(6) 0.0144(5) -0.0068(6) C1 0.0397(7) 0.0598(10) 0.0376(7) -0.0118(7) 0.0099(6) -0.0042(7) C2 0.0393(7) 0.0524(9) 0.0348(7) -0.0064(7) 0.0059(6) 0.0020(7) C3 0.0510(9) 0.0580(11) 0.0402(8) -0.0021(8) -0.0009(7) 0.0112(8) C4 0.0613(10) 0.0448(9) 0.0410(8) 0.0042(7) 0.0055(7) 0.0054(8) C5 0.0516(8) 0.0420(9) 0.0314(7) -0.0004(6) 0.0084(6) -0.0014(7) C6 0.0567(9) 0.0420(9) 0.0363(7) 0.0005(7) 0.0129(6) -0.0059(7) C7 0.0446(8) 0.0445(9) 0.0368(7) -0.0042(6) 0.0122(6) -0.0096(7) C8 0.0551(9) 0.0510(10) 0.0514(9) -0.0063(8) 0.0190(7) -0.0196(8) C9 0.0424(8) 0.0676(12) 0.0548(9) -0.0129(9) 0.0161(7) -0.0172(8) C10 0.0391(7) 0.0506(9) 0.0420(8) -0.0114(7) 0.0089(6) -0.0090(7) C11 0.0375(8) 0.0543(10) 0.0462(8) -0.0087(8) 0.0021(6) -0.0027(7) C12 0.0407(8) 0.0500(9) 0.0411(8) -0.0042(7) 0.0006(6) 0.0011(7) C13 0.0516(10) 0.0611(11) 0.0546(10) 0.0051(9) -0.0016(8) 0.0111(9) C14 0.0724(12) 0.0548(11) 0.0486(9) 0.0121(8) 0.0063(9) 0.0054(10) C15 0.0584(9) 0.0483(9) 0.0365(7) 0.0051(7) 0.0088(7) -0.0031(8) C16 0.0665(10) 0.0440(9) 0.0443(8) 0.0073(7) 0.0177(7) -0.0053(8) C17 0.0549(8) 0.0427(9) 0.0435(8) -0.0025(7) 0.0192(7) -0.0114(7) C18 0.0640(10) 0.0571(11) 0.0606(10) -0.0042(9) 0.0297(8) -0.0205(9) C19 0.0463(8) 0.0694(12) 0.0611(10) -0.0107(9) 0.0245(7) -0.0172(8) C20 0.0391(7) 0.0546(10) 0.0394(7) -0.0094(7) 0.0113(6) -0.0080(7) C21 0.0396(8) 0.0727(13) 0.0574(10) -0.0092(9) 0.0136(7) 0.0007(9) C22 0.0471(10) 0.0845(15) 0.0723(13) -0.0145(12) -0.0018(9) -0.0008(10) C23 0.0404(9) 0.0682(13) 0.0806(13) -0.0070(11) 0.0072(9) -0.0009(9) C24 0.0629(12) 0.0903(17) 0.1153(18) -0.0227(15) 0.0363(12) 0.0026(12) _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 N1 C5 1.372(2) . ? N1 C2 1.376(2) . ? N1 H1B 0.90(2) . ? N2 C7 1.362(2) . ? N2 C10 1.374(2) . ? N3 C15 1.369(2) . ? N3 C12 1.372(2) . ? N3 H3B 1.03(2) . ? N4 C17 1.361(2) . ? N4 C20 1.370(2) . ? C1 C2 1.389(3) . ? C1 C20 1.408(3) . ? C1 C21 1.513(2) . ? C2 C3 1.434(3) . ? C3 C4 1.351(3) . ? C3 H3A 0.96(2) . ? C4 C5 1.422(2) . ? C4 H4A 0.94(2) . ? C5 C6 1.385(2) . ? C6 C7 1.390(2) . ? C6 H6A 1.071(19) . ? C7 C8 1.442(2) . ? C8 C9 1.345(3) . ? C8 H8A 0.93(2) . ? C9 C10 1.452(3) . ? C9 H9A 0.94(2) . ? C10 C11 1.399(3) . ? C11 C12 1.394(3) . ? C11 C23 1.527(3) . ? C12 C13 1.430(3) . ? C13 C14 1.358(3) . ? C13 H13A 1.02(2) . ? C14 C15 1.411(3) . ? C14 H14A 1.01(2) . ? C15 C16 1.385(3) . ? C16 C17 1.390(3) . ? C16 H16A 1.04(2) . ? C17 C18 1.454(3) . ? C18 C19 1.342(3) . ? C18 H18A 0.93(2) . ? C19 C20 1.451(3) . ? C19 H19A 0.914(19) . ? C21 C22 1.526(3) . ? C21 H21A 1.01(2) . ? C21 H21B 0.99(2) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.520(4) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 C5 N1 C2 109.94(14) . . ? C5 N1 H1B 128.8(14) . . ? C2 N1 H1B 121.2(14) . . ? C7 N2 C10 106.18(14) . . ? C15 N3 C12 110.13(14) . . ? C15 N3 H3B 128.4(13) . . ? C12 N3 H3B 121.5(13) . . ? C17 N4 C20 106.31(14) . . ? C2 C1 C20 123.69(15) . . ? C2 C1 C21 117.22(16) . . ? C20 C1 C21 119.08(16) . . ? N1 C2 C1 125.15(16) . . ? N1 C2 C3 106.30(15) . . ? C1 C2 C3 128.53(16) . . ? C4 C3 C2 108.39(16) . . ? C4 C3 H3A 126.4(13) . . ? C2 C3 H3A 125.2(13) . . ? C3 C4 C5 108.30(16) . . ? C3 C4 H4A 130.2(12) . . ? C5 C4 H4A 121.4(11) . . ? N1 C5 C6 127.21(15) . . ? N1 C5 C4 107.06(15) . . ? C6 C5 C4 125.72(16) . . ? C5 C6 C7 129.16(16) . . ? C5 C6 H6A 113.3(10) . . ? C7 C6 H6A 117.5(10) . . ? N2 C7 C6 126.57(15) . . ? N2 C7 C8 109.96(15) . . ? C6 C7 C8 123.42(16) . . ? C9 C8 C7 107.68(16) . . ? C9 C8 H8A 131.9(12) . . ? C7 C8 H8A 120.1(12) . . ? C8 C9 C10 106.14(16) . . ? C8 C9 H9A 129.3(14) . . ? C10 C9 H9A 124.5(14) . . ? N2 C10 C11 123.98(16) . . ? N2 C10 C9 110.03(15) . . ? C11 C10 C9 125.98(16) . . ? C12 C11 C10 123.80(16) . . ? C12 C11 C23 116.98(17) . . ? C10 C11 C23 119.15(17) . . ? N3 C12 C11 125.28(16) . . ? N3 C12 C13 106.39(16) . . ? C11 C12 C13 128.33(17) . . ? C14 C13 C12 107.93(17) . . ? C14 C13 H13A 128.8(12) . . ? C12 C13 H13A 123.2(12) . . ? C13 C14 C15 108.54(18) . . ? C13 C14 H14A 128.1(13) . . ? C15 C14 H14A 123.3(13) . . ? N3 C15 C16 127.14(17) . . ? N3 C15 C14 107.01(17) . . ? C16 C15 C14 125.82(18) . . ? C15 C16 C17 129.11(17) . . ? C15 C16 H16A 115.2(12) . . ? C17 C16 H16A 115.3(12) . . ? N4 C17 C16 126.88(16) . . ? N4 C17 C18 110.12(16) . . ? C16 C17 C18 122.96(17) . . ? C19 C18 C17 106.73(17) . . ? C19 C18 H18A 125.0(13) . . ? C17 C18 H18A 128.3(13) . . ? C18 C19 C20 107.04(16) . . ? C18 C19 H19A 127.5(13) . . ? C20 C19 H19A 125.5(13) . . ? N4 C20 C1 124.13(16) . . ? N4 C20 C19 109.80(15) . . ? C1 C20 C19 126.03(16) . . ? C1 C21 C22 112.83(16) . . ? C1 C21 H21A 111.9(13) . . ? C22 C21 H21A 110.3(13) . . ? C1 C21 H21B 109.2(12) . . ? C22 C21 H21B 109.3(12) . . ? H21A C21 H21B 102.9(18) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C11 111.82(17) . . ? C24 C23 H23A 109.3 . . ? C11 C23 H23A 109.3 . . ? C24 C23 H23B 109.3 . . ? C11 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C1 178.76(15) . . . . ? C5 N1 C2 C3 -0.25(17) . . . . ? C20 C1 C2 N1 -1.3(3) . . . . ? C21 C1 C2 N1 177.73(15) . . . . ? C20 C1 C2 C3 177.52(16) . . . . ? C21 C1 C2 C3 -3.5(3) . . . . ? N1 C2 C3 C4 0.11(19) . . . . ? C1 C2 C3 C4 -178.86(17) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? C2 N1 C5 C6 -179.10(15) . . . . ? C2 N1 C5 C4 0.29(18) . . . . ? C3 C4 C5 N1 -0.22(19) . . . . ? C3 C4 C5 C6 179.19(16) . . . . ? N1 C5 C6 C7 -0.8(3) . . . . ? C4 C5 C6 C7 179.90(17) . . . . ? C10 N2 C7 C6 -176.39(16) . . . . ? C10 N2 C7 C8 1.14(17) . . . . ? C5 C6 C7 N2 -1.9(3) . . . . ? C5 C6 C7 C8 -179.09(16) . . . . ? N2 C7 C8 C9 -1.0(2) . . . . ? C6 C7 C8 C9 176.59(16) . . . . ? C7 C8 C9 C10 0.5(2) . . . . ? C7 N2 C10 C11 179.88(15) . . . . ? C7 N2 C10 C9 -0.84(18) . . . . ? C8 C9 C10 N2 0.2(2) . . . . ? C8 C9 C10 C11 179.48(17) . . . . ? N2 C10 C11 C12 5.1(3) . . . . ? C9 C10 C11 C12 -174.02(17) . . . . ? N2 C10 C11 C23 -171.70(16) . . . . ? C9 C10 C11 C23 9.1(3) . . . . ? C15 N3 C12 C11 -179.82(16) . . . . ? C15 N3 C12 C13 0.76(19) . . . . ? C10 C11 C12 N3 -0.9(3) . . . . ? C23 C11 C12 N3 175.96(16) . . . . ? C10 C11 C12 C13 178.35(17) . . . . ? C23 C11 C12 C13 -4.7(3) . . . . ? N3 C12 C13 C14 -0.3(2) . . . . ? C11 C12 C13 C14 -179.67(18) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C12 N3 C15 C16 177.03(17) . . . . ? C12 N3 C15 C14 -0.94(19) . . . . ? C13 C14 C15 N3 0.8(2) . . . . ? C13 C14 C15 C16 -177.26(18) . . . . ? N3 C15 C16 C17 -3.8(3) . . . . ? C14 C15 C16 C17 173.77(19) . . . . ? C20 N4 C17 C16 -178.56(17) . . . . ? C20 N4 C17 C18 -0.67(18) . . . . ? C15 C16 C17 N4 -0.1(3) . . . . ? C15 C16 C17 C18 -177.77(18) . . . . ? N4 C17 C18 C19 0.5(2) . . . . ? C16 C17 C18 C19 178.49(17) . . . . ? C17 C18 C19 C20 -0.1(2) . . . . ? C17 N4 C20 C1 -177.38(15) . . . . ? C17 N4 C20 C19 0.60(18) . . . . ? C2 C1 C20 N4 1.2(3) . . . . ? C21 C1 C20 N4 -177.78(15) . . . . ? C2 C1 C20 C19 -176.44(17) . . . . ? C21 C1 C20 C19 4.6(3) . . . . ? C18 C19 C20 N4 -0.3(2) . . . . ? C18 C19 C20 C1 177.63(17) . . . . ? C2 C1 C21 C22 -84.2(2) . . . . ? C20 C1 C21 C22 94.9(2) . . . . ? C12 C11 C23 C24 -82.9(2) . . . . ? C10 C11 C23 C24 94.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.267 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.066 # Attachment '- C4-Por.cif' data_c5por _database_code_depnum_ccdc_archive 'CCDC 867178' #TrackingRef '- C4-Por.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H30 N4' _chemical_formula_weight 422.56 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 9.8980(6) _cell_length_b 9.3449(6) _cell_length_c 12.9197(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.261(4) _cell_angle_gamma 90.00 _cell_volume 1141.20(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2060 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 22.21 _exptl_crystal_description PLATE _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5172 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SAINT ver 7.34; Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12012 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2312 _reflns_number_gt 1284 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEXII' _computing_cell_refinement 'Bruker APEXII' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1394P)^2^+1.0950P] 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 0.007(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2312 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1290 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2826 _refine_ls_wR_factor_gt 0.2107 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.06756(19) 0.1313(2) 0.39249(16) 0.0551(5) Uani 1 1 d . . . H1A H 1.032(2) 0.080(2) 0.4328(18) 0.060(7) Uiso 1 1 d . . . N2 N 0.80463(18) 0.0297(2) 0.39693(15) 0.0536(5) Uani 1 1 d . . . C1 C 1.2091(2) 0.1609(2) 0.41114(19) 0.0575(6) Uani 1 1 d . . . C2 C 1.2197(3) 0.2496(3) 0.3246(2) 0.0711(7) Uani 1 1 d . . . H2A H 1.315(3) 0.286(4) 0.322(2) 0.105(10) Uiso 1 1 d . . . C3 C 1.0888(3) 0.2708(3) 0.2564(2) 0.0710(7) Uani 1 1 d . . . H3A H 1.067(3) 0.316(3) 0.181(2) 0.084(9) Uiso 1 1 d . . . C4 C 0.9896(2) 0.1953(2) 0.2968(2) 0.0574(6) Uani 1 1 d . . . C5 C 0.8428(3) 0.1864(3) 0.25480(19) 0.0596(6) Uani 1 1 d . . . C6 C 0.7572(2) 0.1092(2) 0.3036(2) 0.0577(6) Uani 1 1 d . . . C7 C 0.6034(3) 0.1033(3) 0.2645(2) 0.0716(8) Uani 1 1 d . . . H7A H 0.545(3) 0.158(3) 0.190(2) 0.102(10) Uiso 1 1 d . . . C8 C 0.5611(2) 0.0201(3) 0.3318(2) 0.0686(7) Uani 1 1 d . . . H8A H 0.464(3) -0.018(3) 0.3305(19) 0.067(7) Uiso 1 1 d . . . C9 C 0.6859(2) -0.0266(3) 0.4154(2) 0.0589(6) Uani 1 1 d . . . C10 C 0.6818(2) -0.1133(3) 0.5005(2) 0.0632(7) Uani 1 1 d . . . H10A H 0.592(3) -0.152(3) 0.505(2) 0.076(8) Uiso 1 1 d . . . C11 C 0.7730(3) 0.2643(3) 0.1489(2) 0.0761(8) Uani 1 1 d . . . H11A H 0.691(3) 0.317(3) 0.164(2) 0.089(9) Uiso 1 1 d . . . H11B H 0.845(3) 0.342(3) 0.129(2) 0.092(9) Uiso 1 1 d . . . C12 C 0.7180(3) 0.1646(4) 0.0485(3) 0.0881(10) Uani 1 1 d . . . H12B H 0.649(3) 0.067(3) 0.049(2) 0.102(10) Uiso 1 1 d . . . H12A H 0.648(4) 0.218(4) -0.027(3) 0.129(13) Uiso 1 1 d . . . C13 C 0.8321(4) 0.0907(4) 0.0154(3) 0.0922(11) Uani 1 1 d . . . H13A H 0.8859 0.0306 0.0745 0.145(15) Uiso 1 1 calc R . . H13B H 0.8959 0.1616 0.0013 0.174 Uiso 1 1 calc R . . C14 C 0.7727(4) -0.0019(4) -0.0863(3) 0.1045(12) Uani 1 1 d . . . H14A H 0.7649 -0.0993 -0.0652 0.30(4) Uiso 1 1 calc R . . H14B H 0.8351 0.0028 -0.1306 0.361 Uiso 1 1 calc R . . H14C H 0.6809 0.0329 -0.1266 0.361 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0575(9) 0.0481(10) 0.0663(10) 0.0000(8) 0.0283(8) -0.0048(8) N2 0.0508(8) 0.0485(10) 0.0676(10) -0.0016(8) 0.0270(8) -0.0015(8) C1 0.0594(11) 0.0519(12) 0.0704(13) -0.0070(10) 0.0330(9) -0.0080(10) C2 0.0723(13) 0.0600(14) 0.0886(16) 0.0045(13) 0.0356(12) -0.0109(12) C3 0.0868(15) 0.0573(14) 0.0767(15) 0.0096(12) 0.0363(12) -0.0057(13) C4 0.0653(12) 0.0436(11) 0.0676(13) 0.0028(10) 0.0265(10) 0.0018(10) C5 0.0690(12) 0.0475(12) 0.0665(13) 0.0031(10) 0.0264(11) 0.0089(10) C6 0.0563(11) 0.0498(12) 0.0696(13) -0.0004(11) 0.0226(10) 0.0077(10) C7 0.0548(13) 0.0791(17) 0.0788(16) -0.0006(14) 0.0165(12) 0.0068(12) C8 0.0488(11) 0.0786(16) 0.0787(16) -0.0073(14) 0.0193(11) -0.0049(12) C9 0.0546(11) 0.0560(13) 0.0694(13) -0.0106(11) 0.0234(10) -0.0036(10) C10 0.0568(11) 0.0622(14) 0.0760(14) -0.0082(12) 0.0281(11) -0.0118(11) C11 0.0848(16) 0.0627(15) 0.0811(17) 0.0166(13) 0.0251(14) 0.0135(13) C12 0.0875(18) 0.098(2) 0.0756(17) 0.0185(16) 0.0192(15) 0.0108(17) C13 0.097(2) 0.098(2) 0.0778(18) 0.0076(17) 0.0191(16) 0.0087(18) C14 0.117(3) 0.107(3) 0.079(2) -0.004(2) 0.0123(19) -0.006(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 N1 C1 1.377(3) . ? N1 C4 1.384(3) . ? N1 H1A 0.86(2) . ? N2 C9 1.372(3) . ? N2 C6 1.374(3) . ? C1 C10 1.391(3) 3_756 ? C1 C2 1.420(4) . ? C2 C3 1.348(4) . ? C2 H2A 1.01(3) . ? C3 C4 1.427(4) . ? C3 H3A 1.02(3) . ? C4 C5 1.395(3) . ? C5 C6 1.398(4) . ? C5 C11 1.523(4) . ? C6 C7 1.456(3) . ? C7 C8 1.323(4) . ? C7 H7A 1.09(3) . ? C8 C9 1.447(3) . ? C8 H8A 1.02(3) . ? C9 C10 1.376(4) . ? C10 C1 1.391(3) 3_756 ? C10 H10A 0.98(3) . ? C11 C12 1.558(4) . ? C11 H11A 1.01(3) . ? C11 H11B 1.10(3) . ? C12 C13 1.490(5) . ? C12 H12B 1.14(3) . ? C12 H12A 1.13(4) . ? C13 C14 1.537(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 109.7(2) . . ? C1 N1 H1A 126.1(14) . . ? C4 N1 H1A 124.2(14) . . ? C9 N2 C6 105.84(18) . . ? N1 C1 C10 125.5(2) . 3_756 ? N1 C1 C2 106.8(2) . . ? C10 C1 C2 127.7(2) 3_756 . ? C3 C2 C1 108.6(2) . . ? C3 C2 H2A 130.8(17) . . ? C1 C2 H2A 120.6(17) . . ? C2 C3 C4 108.7(2) . . ? C2 C3 H3A 125.0(15) . . ? C4 C3 H3A 125.3(15) . . ? N1 C4 C5 124.2(2) . . ? N1 C4 C3 106.2(2) . . ? C5 C4 C3 129.6(2) . . ? C4 C5 C6 123.8(2) . . ? C4 C5 C11 117.6(2) . . ? C6 C5 C11 118.6(2) . . ? N2 C6 C5 125.4(2) . . ? N2 C6 C7 109.5(2) . . ? C5 C6 C7 125.1(2) . . ? C8 C7 C6 107.2(2) . . ? C8 C7 H7A 132.0(17) . . ? C6 C7 H7A 120.7(17) . . ? C7 C8 C9 107.6(2) . . ? C7 C8 H8A 132.3(13) . . ? C9 C8 H8A 120.0(14) . . ? N2 C9 C10 126.5(2) . . ? N2 C9 C8 109.9(2) . . ? C10 C9 C8 123.6(2) . . ? C9 C10 C1 130.1(2) . 3_756 ? C9 C10 H10A 120.3(15) . . ? C1 C10 H10A 109.5(15) 3_756 . ? C5 C11 C12 114.5(2) . . ? C5 C11 H11A 103.7(16) . . ? C12 C11 H11A 110.1(16) . . ? C5 C11 H11B 112.0(14) . . ? C12 C11 H11B 107.1(16) . . ? H11A C11 H11B 109(2) . . ? C13 C12 C11 114.1(3) . . ? C13 C12 H12B 97.9(17) . . ? C11 C12 H12B 122.6(16) . . ? C13 C12 H12A 106(2) . . ? C11 C12 H12A 115(2) . . ? H12B C12 H12A 98(2) . . ? C12 C13 C14 112.1(3) . . ? C12 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C10 -179.7(2) . . . 3_756 ? C4 N1 C1 C2 1.2(3) . . . . ? N1 C1 C2 C3 -0.5(3) . . . . ? C10 C1 C2 C3 -179.6(3) 3_756 . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 N1 C4 C5 -179.8(2) . . . . ? C1 N1 C4 C3 -1.4(3) . . . . ? C2 C3 C4 N1 1.0(3) . . . . ? C2 C3 C4 C5 179.4(3) . . . . ? N1 C4 C5 C6 -1.2(4) . . . . ? C3 C4 C5 C6 -179.3(3) . . . . ? N1 C4 C5 C11 179.5(2) . . . . ? C3 C4 C5 C11 1.4(4) . . . . ? C9 N2 C6 C5 179.7(2) . . . . ? C9 N2 C6 C7 1.0(3) . . . . ? C4 C5 C6 N2 -1.6(4) . . . . ? C11 C5 C6 N2 177.7(2) . . . . ? C4 C5 C6 C7 177.0(2) . . . . ? C11 C5 C6 C7 -3.8(4) . . . . ? N2 C6 C7 C8 -1.2(3) . . . . ? C5 C6 C7 C8 -180.0(3) . . . . ? C6 C7 C8 C9 0.9(3) . . . . ? C6 N2 C9 C10 -179.7(2) . . . . ? C6 N2 C9 C8 -0.5(3) . . . . ? C7 C8 C9 N2 -0.3(3) . . . . ? C7 C8 C9 C10 179.0(3) . . . . ? N2 C9 C10 C1 2.6(5) . . . 3_756 ? C8 C9 C10 C1 -176.5(3) . . . 3_756 ? C4 C5 C11 C12 106.9(3) . . . . ? C6 C5 C11 C12 -72.5(3) . . . . ? C5 C11 C12 C13 -67.8(4) . . . . ? C11 C12 C13 C14 -177.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.293 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.058