data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jerzy Lisowski' 'Janusz Gregolinski' 'Tadeusz Lis' _publ_contact_author_name 'Dr Jerzy Lisowski' _publ_contact_author_address ; Chemistry University of Wroclaw F. Joliot-Curie 14 Wroclaw 50-383 POLAND ; _publ_contact_author_email JUREKL@WCHUWR.CHEM.UNI.WROC.PL _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; New 2+2, 3+3 and 4+4 macrocycles derived from 1,2-diaminocyclohexane and 2,6-diformylpyridiner ; data_jg10dc _database_code_depnum_ccdc_archive 'CCDC 270351' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8(R),13(R),23(S),28(S)-7,14,22,29,31,32-hexaazapentacyclo [25.3.1.1^16,20^.0^8,13^.0^23,28^]-dotriconta- 1(31),2,4,6,14,16(32),17,19,21,29-decaene ; _chemical_name_common imine _chemical_melting_point 370 _chemical_formula_moiety 'C26 H30 N6' _chemical_formula_sum 'C26 H30 N6' _chemical_formula_weight 426.56 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 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 6.936(2) _cell_length_b 16.389(3) _cell_length_c 9.833(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.78(3) _cell_angle_gamma 90.00 _cell_volume 1116.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12599 _cell_measurement_theta_min 4 _cell_measurement_theta_max 38 _exptl_crystal_description columns _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'CrysAlis Red (Oxford Diffraction, 1995-2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Xcalibur PX \k-geometry diffractometer CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26717 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.33 _diffrn_reflns_theta_max 38.00 _reflns_number_total 6048 _reflns_number_gt 4041 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Red (Oxford Diffraction, 1995-2003)' _computing_cell_refinement 'CrysAlis Red (Oxford Diffraction, 1995-2003)' _computing_data_reduction 'CrysAlis Red (Oxford Diffraction, 1995-2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6048 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.1656 _refine_ls_wR_factor_gt 0.1471 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.123 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.003 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 0.46492(12) 0.58761(5) 0.09701(8) 0.01228(16) Uani 1 1 d . . . N2 N 0.90831(13) 0.64529(5) -0.03047(8) 0.01414(17) Uani 1 1 d . . . N3 N 0.84828(12) 0.54031(5) -0.27015(8) 0.01401(17) Uani 1 1 d . . . C1 C 0.38950(14) 0.55697(6) 0.20968(10) 0.01192(18) Uani 1 1 d . . . C2 C 0.48225(15) 0.56166(6) 0.33890(10) 0.01365(18) Uani 1 1 d . . . C3 C 0.66340(15) 0.59768(7) 0.35220(10) 0.01530(19) Uani 1 1 d . . . C4 C 0.74797(15) 0.62546(6) 0.23564(10) 0.01458(19) Uani 1 1 d . . . C5 C 0.64403(14) 0.61926(6) 0.11064(10) 0.01267(18) Uani 1 1 d . . . C6 C 0.72704(15) 0.64490(6) -0.01863(10) 0.01394(19) Uani 1 1 d . . . C7 C 0.98207(14) 0.66451(6) -0.16392(9) 0.01291(18) Uani 1 1 d . . . C8 C 1.16511(15) 0.71579(7) -0.14105(10) 0.01437(19) Uani 1 1 d . . . C9 C 1.26804(15) 0.73181(6) -0.27209(10) 0.01490(19) Uani 1 1 d . . . C10 C 1.31160(15) 0.65191(7) -0.34441(10) 0.0152(2) Uani 1 1 d . . . C11 C 1.12636(15) 0.60293(7) -0.37049(10) 0.01426(19) Uani 1 1 d . . . C12 C 1.02845(14) 0.58389(6) -0.23766(10) 0.01270(18) Uani 1 1 d . . . C13 C 0.79875(14) 0.48468(6) -0.18816(10) 0.01318(18) Uani 1 1 d . . . H2 H 0.4153(18) 0.5395(8) 0.4207(13) 0.012(3) Uiso 1 1 d . . . H3 H 0.730(2) 0.6016(10) 0.4428(14) 0.022(3) Uiso 1 1 d . . . H4 H 0.874(2) 0.6489(9) 0.2406(14) 0.026(4) Uiso 1 1 d . . . H6 H 0.6314(19) 0.6607(9) -0.0928(13) 0.018(3) Uiso 1 1 d . . . H7 H 0.8848(18) 0.6935(8) -0.2203(12) 0.012(3) Uiso 1 1 d . . . H8A H 1.2489(19) 0.6854(10) -0.0740(14) 0.024(4) Uiso 1 1 d . . . H8B H 1.126(2) 0.7680(10) -0.0991(14) 0.024(4) Uiso 1 1 d . . . H9A H 1.1875(19) 0.7678(9) -0.3349(13) 0.021(3) Uiso 1 1 d . . . H9B H 1.387(2) 0.7607(9) -0.2501(13) 0.017(3) Uiso 1 1 d . . . H10A H 1.4093(19) 0.6191(9) -0.2891(13) 0.017(3) Uiso 1 1 d . . . H10B H 1.3725(19) 0.6652(9) -0.4339(13) 0.018(3) Uiso 1 1 d . . . H11A H 1.0317(19) 0.6341(9) -0.4314(14) 0.020(3) Uiso 1 1 d . . . H11B H 1.148(2) 0.5506(9) -0.4172(14) 0.020(3) Uiso 1 1 d . . . H12 H 1.1171(18) 0.5506(8) -0.1773(13) 0.011(3) Uiso 1 1 d . . . H13 H 0.878(2) 0.4689(9) -0.1085(14) 0.021(3) 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 N1 0.0135(4) 0.0113(4) 0.0123(3) 0.0001(3) 0.0031(3) 0.0005(3) N2 0.0154(4) 0.0153(4) 0.0120(3) 0.0004(3) 0.0036(3) -0.0009(3) N3 0.0140(4) 0.0141(4) 0.0140(4) -0.0005(3) 0.0013(3) -0.0017(3) C1 0.0119(4) 0.0110(4) 0.0130(4) -0.0004(3) 0.0023(3) 0.0001(3) C2 0.0162(5) 0.0137(4) 0.0112(4) 0.0007(3) 0.0020(3) -0.0007(3) C3 0.0174(5) 0.0164(5) 0.0120(4) -0.0016(3) -0.0004(3) -0.0008(4) C4 0.0131(4) 0.0155(5) 0.0152(4) -0.0019(3) 0.0017(3) -0.0017(3) C5 0.0133(4) 0.0121(4) 0.0128(4) -0.0005(3) 0.0028(3) 0.0008(3) C6 0.0149(4) 0.0143(4) 0.0127(4) -0.0001(3) 0.0022(3) -0.0018(3) C7 0.0134(4) 0.0152(4) 0.0102(4) 0.0010(3) 0.0018(3) 0.0001(3) C8 0.0151(4) 0.0164(5) 0.0117(4) -0.0007(3) 0.0016(3) -0.0020(4) C9 0.0156(5) 0.0151(5) 0.0143(4) 0.0005(3) 0.0028(3) -0.0036(4) C10 0.0148(5) 0.0169(5) 0.0142(4) -0.0002(4) 0.0041(3) -0.0023(4) C11 0.0155(5) 0.0162(5) 0.0112(4) -0.0004(3) 0.0024(3) -0.0031(4) C12 0.0126(4) 0.0131(4) 0.0124(4) 0.0008(3) 0.0009(3) -0.0013(3) C13 0.0138(4) 0.0138(4) 0.0120(4) -0.0012(3) 0.0018(3) -0.0006(3) _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 1.3452(13) . ? N1 C5 1.3470(13) . ? N2 C6 1.2683(14) . ? N2 C7 1.4656(13) . ? N3 C13 1.2752(13) . ? N3 C12 1.4612(13) . ? C1 C2 1.3982(14) . ? C1 C13 1.4794(14) 3_665 ? C2 C3 1.3887(15) . ? C2 H2 1.015(12) . ? C3 C4 1.3893(15) . ? C3 H3 0.984(14) . ? C4 C5 1.3982(15) . ? C4 H4 0.951(15) . ? C5 C6 1.4814(14) . ? C6 H6 0.996(13) . ? C7 C8 1.5300(15) . ? C7 C12 1.5485(15) . ? C7 H7 0.976(13) . ? C8 C9 1.5258(15) . ? C8 H8A 0.992(15) . ? C8 H8B 0.994(15) . ? C9 C10 1.5273(15) . ? C9 H9A 1.004(14) . ? C9 H9B 0.969(14) . ? C10 C11 1.5261(15) . ? C10 H10A 1.004(14) . ? C10 H10B 1.018(13) . ? C11 C12 1.5331(14) . ? C11 H11A 1.006(14) . ? C11 H11B 0.987(15) . ? C12 H12 0.997(13) . ? C13 C1 1.4794(14) 3_665 ? C13 H13 0.970(14) . ? 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 C5 117.10(9) . . ? C6 N2 C7 118.29(9) . . ? C13 N3 C12 117.71(9) . . ? N1 C1 C2 123.21(9) . . ? N1 C1 C13 115.48(9) . 3_665 ? C2 C1 C13 121.29(9) . 3_665 ? C3 C2 C1 118.90(9) . . ? C3 C2 H2 121.6(7) . . ? C1 C2 H2 119.5(7) . . ? C2 C3 C4 118.55(9) . . ? C2 C3 H3 119.6(8) . . ? C4 C3 H3 121.9(8) . . ? C3 C4 C5 118.76(10) . . ? C3 C4 H4 120.8(8) . . ? C5 C4 H4 120.4(8) . . ? N1 C5 C4 123.31(9) . . ? N1 C5 C6 114.76(9) . . ? C4 C5 C6 121.90(9) . . ? N2 C6 C5 120.56(9) . . ? N2 C6 H6 124.0(8) . . ? C5 C6 H6 115.4(8) . . ? N2 C7 C8 108.04(8) . . ? N2 C7 C12 108.98(8) . . ? C8 C7 C12 110.35(8) . . ? N2 C7 H7 110.6(7) . . ? C8 C7 H7 111.2(8) . . ? C12 C7 H7 107.6(7) . . ? C9 C8 C7 112.91(8) . . ? C9 C8 H8A 111.4(8) . . ? C7 C8 H8A 106.1(8) . . ? C9 C8 H8B 110.6(8) . . ? C7 C8 H8B 106.8(8) . . ? H8A C8 H8B 108.7(12) . . ? C8 C9 C10 110.91(9) . . ? C8 C9 H9A 110.6(7) . . ? C10 C9 H9A 109.5(8) . . ? C8 C9 H9B 109.0(7) . . ? C10 C9 H9B 109.6(8) . . ? H9A C9 H9B 107.1(11) . . ? C11 C10 C9 110.20(9) . . ? C11 C10 H10A 110.5(8) . . ? C9 C10 H10A 110.5(8) . . ? C11 C10 H10B 110.4(8) . . ? C9 C10 H10B 108.6(8) . . ? H10A C10 H10B 106.6(10) . . ? C10 C11 C12 111.59(8) . . ? C10 C11 H11A 110.6(8) . . ? C12 C11 H11A 107.9(7) . . ? C10 C11 H11B 113.0(8) . . ? C12 C11 H11B 107.6(8) . . ? H11A C11 H11B 105.8(11) . . ? N3 C12 C11 108.82(8) . . ? N3 C12 C7 108.94(8) . . ? C11 C12 C7 109.63(8) . . ? N3 C12 H12 111.1(7) . . ? C11 C12 H12 109.4(7) . . ? C7 C12 H12 108.9(7) . . ? N3 C13 C1 120.16(9) . 3_665 ? N3 C13 H13 122.8(8) . . ? C1 C13 H13 117.1(8) 3_665 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8A N1 0.992(15) 2.720(15) 3.7074(16) 174.0(12) 1_655 C4 H4 N2 0.951(15) 2.689(14) 2.9106(16) 93.8(9) . C2 H2 N3 1.015(12) 2.643(13) 2.8905(15) 93.6(8) 3_665 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 38.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.54 _refine_diff_density_min -0.28 _refine_diff_density_rms 0.070 #======end====================================================== data_tekst _database_code_depnum_ccdc_archive 'CCDC 270352' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8(R),13(R),23(S),28(S),38(R),43(R),53(S),58(S)- 7,14,22,29,37,44,52,59,61,62,63,64-dodecaazananocyclo [55.3.1.1^16,20^.1^31,35^.1^46,50^.0^8,13^.0^23,28^.0^38,43^.0^53,58^] -tetrahexaconta- 1(61),2,4,6,14,16(62),17,19,21,29,31(63),32,34,44,46(64),47,49,51,59 -eicosaene ; _chemical_name_common imine _chemical_melting_point 340 _chemical_formula_moiety 'C52 H60 N12' _chemical_formula_sum 'C52 H60 N12' _chemical_formula_weight 853.13 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P21212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 15.577(4) _cell_length_b 30.563(9) _cell_length_c 5.460(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2599.4(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6668 _cell_measurement_theta_min 4 _cell_measurement_theta_max 76 _exptl_crystal_description pillars _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.090 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.522 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_correction_T_min 0.937 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_process_details 'CrysAlis Red (Oxford Diffraction, 1995-2003)' _exptl_special_details ; structure solved using Squeeze method ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur PX \k-geometry diffractometer CCD detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16367 _diffrn_reflns_av_R_equivalents 0.0833 _diffrn_reflns_av_sigmaI/netI 0.0923 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 4.05 _diffrn_reflns_theta_max 76.03 _reflns_number_total 4441 _reflns_number_gt 2357 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis Red (Oxford Diffraction, 1995-2003)' _computing_cell_refinement 'CrysAlis Red (Oxford Diffraction, 1995-2003)' _computing_data_reduction 'CrysAlis Red (Oxford Diffraction, 1995-2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Bruker, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0860P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment geom _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _chemical_absolute_configuration unk _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.6(9) _refine_ls_number_reflns 4441 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1073 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1754 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 0.903 _refine_ls_restrained_S_all 0.903 _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 0.37942(19) 0.35101(10) 0.3562(7) 0.0418(8) Uani 1 1 d . . . N2 N 0.5739(2) 0.31901(10) 0.0689(8) 0.0525(10) Uani 1 1 d . . . N3 N 0.7138(2) 0.33508(10) 0.3887(7) 0.0534(10) Uani 1 1 d . . . N4 N 0.7968(2) 0.43936(10) 0.5426(7) 0.0501(9) Uani 1 1 d . . . N5 N 0.8638(2) 0.53737(12) 0.8326(8) 0.0589(11) Uani 1 1 d . . . N6 N 0.8265(2) 0.60815(10) 0.5142(7) 0.0501(10) Uani 1 1 d . . . C1 C 0.3120(2) 0.37833(12) 0.3325(8) 0.0426(10) Uani 1 1 d . . . C2 C 0.3049(3) 0.40853(13) 0.1455(9) 0.0542(12) Uani 1 1 d . . . H2 H 0.2565 0.4273 0.1358 0.065 Uiso 1 1 calc R . . C3 C 0.3689(3) 0.41089(14) -0.0252(10) 0.0577(13) Uani 1 1 d . . . H3 H 0.3655 0.4315 -0.1552 0.069 Uiso 1 1 calc R . . C4 C 0.4390(2) 0.38291(13) -0.0071(10) 0.0522(12) Uani 1 1 d . . . H4 H 0.4843 0.3841 -0.1233 0.063 Uiso 1 1 calc R . . C5 C 0.4410(2) 0.35323(12) 0.1849(8) 0.0437(11) Uani 1 1 d . . . C6 C 0.5108(3) 0.32162(12) 0.2152(8) 0.0434(10) Uani 1 1 d . . . H6 H 0.5087 0.3021 0.3507 0.052 Uiso 1 1 calc R . . C7 C 0.6379(2) 0.28499(12) 0.1147(9) 0.0498(12) Uani 1 1 d . . . H7 H 0.6191 0.2667 0.2567 0.060 Uiso 1 1 calc R . . C8 C 0.6481(3) 0.25612(12) -0.1101(9) 0.0528(12) Uani 1 1 d . . . H8A H 0.6646 0.2744 -0.2521 0.063 Uiso 1 1 calc R . . H8B H 0.5924 0.2420 -0.1482 0.063 Uiso 1 1 calc R . . C9 C 0.7162(3) 0.22096(13) -0.0689(10) 0.0612(14) Uani 1 1 d . . . H9A H 0.7246 0.2042 -0.2223 0.073 Uiso 1 1 calc R . . H9B H 0.6961 0.2004 0.0588 0.073 Uiso 1 1 calc R . . C10 C 0.8017(3) 0.24124(14) 0.0104(9) 0.0607(13) Uani 1 1 d . . . H10A H 0.8423 0.2176 0.0536 0.073 Uiso 1 1 calc R . . H10B H 0.8264 0.2577 -0.1288 0.073 Uiso 1 1 calc R . . C11 C 0.7921(3) 0.27120(14) 0.2241(10) 0.0595(13) Uani 1 1 d . . . H11A H 0.8477 0.2856 0.2585 0.071 Uiso 1 1 calc R . . H11B H 0.7755 0.2541 0.3705 0.071 Uiso 1 1 calc R . . C12 C 0.7237(3) 0.30609(13) 0.1730(10) 0.0521(12) Uani 1 1 d . . . H12 H 0.7423 0.3241 0.0295 0.063 Uiso 1 1 calc R . . C13 C 0.7492(3) 0.37261(13) 0.3726(9) 0.0512(12) Uani 1 1 d . . . H13 H 0.7819 0.3794 0.2307 0.061 Uiso 1 1 calc R . . C14 C 0.7411(3) 0.40567(13) 0.5665(9) 0.0546(12) Uani 1 1 d . . . C15 C 0.6812(3) 0.40246(14) 0.7556(10) 0.0677(15) Uani 1 1 d . . . H15 H 0.6427 0.3784 0.7642 0.081 Uiso 1 1 calc R . . C16 C 0.6792(4) 0.43488(14) 0.9281(10) 0.0748(17) Uani 1 1 d . . . H16 H 0.6389 0.4335 1.0584 0.090 Uiso 1 1 calc R . . C17 C 0.7358(3) 0.46977(14) 0.9136(10) 0.0648(14) Uani 1 1 d . . . H17 H 0.7354 0.4924 1.0326 0.078 Uiso 1 1 calc R . . C18 C 0.7933(3) 0.47038(13) 0.7181(10) 0.0545(12) Uani 1 1 d . . . C19 C 0.8567(3) 0.50563(14) 0.6808(9) 0.0536(12) Uani 1 1 d . . . H19 H 0.8931 0.5048 0.5412 0.064 Uiso 1 1 calc R . . C20 C 0.9280(3) 0.57050(13) 0.7836(10) 0.0571(14) Uani 1 1 d . . . H20 H 0.9636 0.5615 0.6398 0.069 Uiso 1 1 calc R . . C21 C 0.9854(3) 0.57696(17) 1.0059(11) 0.0794(18) Uani 1 1 d . . . H21A H 0.9491 0.5842 1.1492 0.095 Uiso 1 1 calc R . . H21B H 1.0154 0.5491 1.0418 0.095 Uiso 1 1 calc R . . C22 C 1.0502(3) 0.6120(2) 0.9729(13) 0.101(2) Uani 1 1 d . . . H22A H 1.0916 0.6030 0.8448 0.121 Uiso 1 1 calc R . . H22B H 1.0823 0.6160 1.1277 0.121 Uiso 1 1 calc R . . C23 C 1.0077(3) 0.6560(2) 0.8982(12) 0.097(2) Uani 1 1 d . . . H23A H 0.9735 0.6674 1.0369 0.116 Uiso 1 1 calc R . . H23B H 1.0529 0.6777 0.8595 0.116 Uiso 1 1 calc R . . C24 C 0.9494(3) 0.64989(15) 0.6745(11) 0.0742(17) Uani 1 1 d . . . H24A H 0.9198 0.6777 0.6364 0.089 Uiso 1 1 calc R . . H24B H 0.9843 0.6415 0.5306 0.089 Uiso 1 1 calc R . . C25 C 0.8834(2) 0.61437(13) 0.7282(9) 0.0542(13) Uani 1 1 d . . . H25 H 0.8481 0.6233 0.8729 0.065 Uiso 1 1 calc R . . C26 C 0.7534(2) 0.62652(11) 0.5264(9) 0.0470(11) Uani 1 1 d . . . H26 H 0.7403 0.6440 0.6654 0.056 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 0.0266(18) 0.0322(17) 0.067(2) -0.0053(17) 0.0050(18) -0.0030(13) N2 0.042(2) 0.0315(18) 0.084(3) 0.0015(19) 0.005(2) 0.0093(14) N3 0.045(2) 0.0287(18) 0.087(3) -0.0041(19) 0.012(2) 0.0051(15) N4 0.045(2) 0.0347(19) 0.070(3) -0.0061(18) -0.0057(19) 0.0112(15) N5 0.036(2) 0.051(2) 0.090(3) -0.004(2) -0.019(2) 0.0178(17) N6 0.0277(18) 0.0387(18) 0.084(3) -0.0105(19) 0.0017(19) -0.0039(15) C1 0.023(2) 0.031(2) 0.074(3) 0.002(2) -0.003(2) 0.0015(15) C2 0.026(2) 0.046(2) 0.091(4) 0.016(2) -0.010(2) -0.0027(17) C3 0.031(3) 0.060(3) 0.082(4) 0.021(3) -0.006(2) 0.006(2) C4 0.031(2) 0.048(3) 0.078(3) 0.006(2) 0.000(2) -0.0069(19) C5 0.032(2) 0.031(2) 0.069(3) -0.006(2) -0.008(2) 0.0031(17) C6 0.038(2) 0.033(2) 0.060(3) -0.002(2) 0.002(2) -0.0033(17) C7 0.033(2) 0.031(2) 0.085(3) 0.001(2) 0.017(2) 0.0064(17) C8 0.051(3) 0.030(2) 0.078(3) 0.001(2) 0.010(2) 0.0078(18) C9 0.053(3) 0.038(2) 0.092(4) -0.003(2) 0.019(3) 0.007(2) C10 0.055(3) 0.042(2) 0.086(4) -0.003(2) 0.024(3) 0.010(2) C11 0.049(3) 0.041(2) 0.089(4) -0.003(2) 0.017(3) 0.013(2) C12 0.048(3) 0.030(2) 0.079(3) -0.001(2) 0.012(2) 0.0065(18) C13 0.039(2) 0.040(2) 0.074(3) -0.005(2) 0.006(2) 0.0064(19) C14 0.054(3) 0.027(2) 0.082(4) -0.002(2) 0.012(3) 0.0067(19) C15 0.081(3) 0.027(2) 0.096(4) 0.003(2) 0.033(3) 0.009(2) C16 0.112(4) 0.026(2) 0.087(4) 0.007(2) 0.033(3) 0.001(3) C17 0.083(4) 0.040(3) 0.071(3) -0.003(2) 0.016(3) 0.020(2) C18 0.051(3) 0.028(2) 0.084(4) -0.002(2) -0.004(3) 0.0103(19) C19 0.049(3) 0.044(3) 0.068(3) -0.017(2) -0.009(2) 0.023(2) C20 0.029(2) 0.043(2) 0.099(4) -0.025(3) -0.010(3) 0.0151(19) C21 0.037(3) 0.092(4) 0.110(5) -0.052(4) -0.029(3) 0.026(3) C22 0.037(3) 0.126(5) 0.139(6) -0.073(5) -0.017(4) 0.025(3) C23 0.040(3) 0.115(5) 0.136(6) -0.076(4) 0.007(3) -0.021(3) C24 0.035(3) 0.058(3) 0.130(5) -0.042(3) 0.014(3) -0.009(2) C25 0.025(2) 0.049(3) 0.088(4) -0.022(2) -0.006(2) -0.0047(18) C26 0.029(2) 0.0289(19) 0.084(3) -0.010(2) -0.006(2) -0.0050(16) _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 1.341(5) . ? N1 C1 1.348(4) . ? N2 C6 1.269(5) . ? N2 C7 1.462(5) . ? N3 C13 1.276(5) . ? N3 C12 1.482(6) . ? N4 C18 1.349(5) . ? N4 C14 1.353(5) . ? N5 C19 1.280(5) . ? N5 C20 1.447(5) . ? N6 C26 1.272(5) . ? N6 C25 1.478(5) . ? C1 C2 1.381(6) . ? C1 C26 1.476(6) 2_665 ? C2 C3 1.366(6) . ? C2 H2 0.9500 . ? C3 C4 1.390(5) . ? C3 H3 0.9500 . ? C4 C5 1.387(6) . ? C4 H4 0.9500 . ? C5 C6 1.464(5) . ? C6 H6 0.9500 . ? C7 C12 1.518(5) . ? C7 C8 1.520(6) . ? C7 H7 1.0000 . ? C8 C9 1.527(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.533(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.491(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.532(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12 1.0000 . ? C13 C14 1.469(6) . ? C13 H13 0.9500 . ? C14 C15 1.396(6) . ? C15 C16 1.368(6) . ? C15 H15 0.9500 . ? C16 C17 1.386(6) . ? C16 H16 0.9500 . ? C17 C18 1.393(6) . ? C17 H17 0.9500 . ? C18 C19 1.476(6) . ? C19 H19 0.9500 . ? C20 C21 1.521(6) . ? C20 C25 1.540(6) . ? C20 H20 1.0000 . ? C21 C22 1.482(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.555(8) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.533(7) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.524(6) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25 1.0000 . ? C26 C1 1.476(6) 2_665 ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 117.3(4) . . ? C6 N2 C7 117.7(4) . . ? C13 N3 C12 116.0(4) . . ? C18 N4 C14 116.1(4) . . ? C19 N5 C20 118.0(4) . . ? C26 N6 C25 116.0(4) . . ? N1 C1 C2 123.2(4) . . ? N1 C1 C26 114.0(4) . 2_665 ? C2 C1 C26 122.8(4) . 2_665 ? C3 C2 C1 118.8(4) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.5(4) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 118.3(4) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? N1 C5 C4 122.9(4) . . ? N1 C5 C6 114.8(4) . . ? C4 C5 C6 122.3(4) . . ? N2 C6 C5 123.1(4) . . ? N2 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? N2 C7 C12 109.5(3) . . ? N2 C7 C8 110.2(4) . . ? C12 C7 C8 108.9(3) . . ? N2 C7 H7 109.4 . . ? C12 C7 H7 109.4 . . ? C8 C7 H7 109.4 . . ? C7 C8 C9 111.2(4) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C8 C9 C10 111.2(3) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 C9 112.5(4) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 110.8(4) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? N3 C12 C7 109.2(3) . . ? N3 C12 C11 110.1(4) . . ? C7 C12 C11 110.8(3) . . ? N3 C12 H12 108.9 . . ? C7 C12 H12 108.9 . . ? C11 C12 H12 108.9 . . ? N3 C13 C14 122.1(4) . . ? N3 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? N4 C14 C15 123.7(4) . . ? N4 C14 C13 113.5(4) . . ? C15 C14 C13 122.8(4) . . ? C16 C15 C14 118.2(4) . . ? C16 C15 H15 120.9 . . ? C14 C15 H15 120.9 . . ? C15 C16 C17 120.3(5) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 117.6(4) . . ? C16 C17 H17 121.2 . . ? C18 C17 H17 121.2 . . ? N4 C18 C17 124.1(4) . . ? N4 C18 C19 112.8(4) . . ? C17 C18 C19 123.1(4) . . ? N5 C19 C18 121.4(4) . . ? N5 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? N5 C20 C21 110.5(5) . . ? N5 C20 C25 109.5(3) . . ? C21 C20 C25 108.0(4) . . ? N5 C20 H20 109.6 . . ? C21 C20 H20 109.6 . . ? C25 C20 H20 109.6 . . ? C22 C21 C20 113.4(5) . . ? C22 C21 H21A 108.9 . . ? C20 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C20 C21 H21B 108.9 . . ? H21A C21 H21B 107.7 . . ? C21 C22 C23 111.6(4) . . ? C21 C22 H22A 109.3 . . ? C23 C22 H22A 109.3 . . ? C21 C22 H22B 109.3 . . ? C23 C22 H22B 109.3 . . ? H22A C22 H22B 108.0 . . ? C24 C23 C22 110.8(4) . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C23 109.5(5) . . ? C25 C24 H24A 109.8 . . ? C23 C24 H24A 109.8 . . ? C25 C24 H24B 109.8 . . ? C23 C24 H24B 109.8 . . ? H24A C24 H24B 108.2 . . ? N6 C25 C24 110.1(4) . . ? N6 C25 C20 108.3(3) . . ? C24 C25 C20 110.7(3) . . ? N6 C25 H25 109.2 . . ? C24 C25 H25 109.2 . . ? C20 C25 H25 109.2 . . ? N6 C26 C1 122.4(4) . 2_665 ? N6 C26 H26 118.8 . . ? C1 C26 H26 118.8 2_665 . ? _diffrn_measured_fraction_theta_max 0.859 _diffrn_reflns_theta_full 76.03 _diffrn_measured_fraction_theta_full 0.859 _refine_diff_density_max 0.182 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.049