Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 222 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Martyn Coles' 'Peter B. Hitchcock' 'Sarah H. Oakley' _publ_contact_author_name 'Dr Martyn Coles ' _publ_contact_author_address ; Dr Martyn Coles Department of Chemistry University of Sussex Falmer Brighton BN1 9QJ UNITED KINGDOM ; _publ_contact_author_email 'M.P.COLES@SUSSEX.AC.UK ' _publ_section_title ; Poly(guanidyl)silanes as a new class of chelating, N-based ligand ; _publ_requested_category FO data_(2)-apr2203 _database_code_depnum_ccdc_archive 'CCDC 232112' _audit_creation_date 2003-04-16T09:21:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common ; '[MeSi(C7H12N3)3]' ; _chemical_formula_moiety 'C22 H39 N9 Si1' _chemical_formula_sum 'C22 H39 N9 Si1' _chemical_formula_weight 457.71 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3920(1) _cell_length_b 8.7131(1) _cell_length_c 16.3865(2) _cell_angle_alpha 103.074(1) _cell_angle_beta 91.011(1) _cell_angle_gamma 94.329(1) _cell_volume 1163.05(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13558 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.100119 _diffrn_orient_matrix_ub_12 -0.75922E-2 _diffrn_orient_matrix_ub_13 -0.323754E-1 _diffrn_orient_matrix_ub_21 0.651266E-1 _diffrn_orient_matrix_ub_22 0.39303E-1 _diffrn_orient_matrix_ub_23 0.533624E-1 _diffrn_orient_matrix_ub_31 0.58081E-2 _diffrn_orient_matrix_ub_32 -0.111235 _diffrn_orient_matrix_ub_33 0.58582E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_unetI/netI 0.0334 _diffrn_reflns_number 21882 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.7 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.98 _diffrn_measured_fraction_theta_max 0.98 _reflns_number_total 5235 _reflns_number_gt 4809 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (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 ? #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0614P)^2^+0.7553P] 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 riding _refine_ls_extinction_method none _refine_ls_number_reflns 5235 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0999 _refine_ls_goodness_of_fit_ref 0.844 _refine_ls_restrained_S_all 0.844 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.359 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si Si 0.17192(4) 0.10126(3) 0.254265(19) 0.01755(10) Uani 1 1 d . . . N1 N 0.22581(13) 0.14136(11) 0.36189(6) 0.0208(2) Uani 1 1 d . . . N2 N 0.19481(14) -0.12516(12) 0.35120(6) 0.0251(2) Uani 1 1 d . . . N3 N 0.26063(14) 0.04296(13) 0.48413(6) 0.0260(2) Uani 1 1 d . . . N4 N 0.16331(12) 0.28576(11) 0.22905(6) 0.0204(2) Uani 1 1 d . . . N5 N -0.05281(13) 0.32291(12) 0.31086(7) 0.0248(2) Uani 1 1 d . . . N6 N -0.01539(12) 0.47269(12) 0.20732(7) 0.0228(2) Uani 1 1 d . . . N7 N 0.33825(12) 0.01667(12) 0.20434(6) 0.0199(2) Uani 1 1 d . . . N8 N 0.20698(16) -0.01997(15) 0.07765(7) 0.0353(3) Uani 1 1 d . . . N9 N 0.41889(14) -0.17822(13) 0.09026(7) 0.0276(2) Uani 1 1 d . . . C1 C 0.22552(14) 0.01396(14) 0.39951(7) 0.0194(2) Uani 1 1 d . . . C2 C 0.25010(16) 0.30201(14) 0.41495(8) 0.0249(3) Uani 1 1 d . . . H2A H 0.1486 0.3333 0.4412 0.03 Uiso 1 1 calc R . . H2B H 0.2832 0.3774 0.3802 0.03 Uiso 1 1 calc R . . C3 C 0.37774(16) 0.30778(16) 0.48247(9) 0.0292(3) Uani 1 1 d . . . H3A H 0.48 0.2787 0.4564 0.035 Uiso 1 1 calc R . . H3B H 0.3948 0.4163 0.5179 0.035 Uiso 1 1 calc R . . C4 C 0.32494(16) 0.19387(16) 0.53551(8) 0.0290(3) Uani 1 1 d . . . H4A H 0.4172 0.1773 0.5701 0.035 Uiso 1 1 calc R . . H4B H 0.2423 0.2399 0.5739 0.035 Uiso 1 1 calc R . . C5 C 0.22472(19) -0.07857(17) 0.53097(8) 0.0325(3) Uani 1 1 d . . . H5A H 0.1591 -0.0357 0.5792 0.039 Uiso 1 1 calc R . . H5B H 0.3258 -0.1078 0.5532 0.039 Uiso 1 1 calc R . . C6 C 0.13605(18) -0.22404(17) 0.47688(9) 0.0334(3) Uani 1 1 d . . . H6A H 0.0213 -0.207 0.4721 0.04 Uiso 1 1 calc R . . H6B H 0.1455 -0.3154 0.5028 0.04 Uiso 1 1 calc R . . C7 C 0.20599(16) -0.25791(14) 0.39084(8) 0.0263(3) Uani 1 1 d . . . H7A H 0.3196 -0.2792 0.3958 0.032 Uiso 1 1 calc R . . H7B H 0.1479 -0.3535 0.3553 0.032 Uiso 1 1 calc R . . C8 C 0.02668(14) 0.36404(13) 0.25163(7) 0.0193(2) Uani 1 1 d . . . C9 C 0.28468(15) 0.35591(15) 0.18242(8) 0.0249(3) Uani 1 1 d . . . H9A H 0.3591 0.2761 0.1583 0.03 Uiso 1 1 calc R . . H9B H 0.3471 0.4451 0.2208 0.03 Uiso 1 1 calc R . . C10 C 0.20568(16) 0.41440(16) 0.11288(9) 0.0288(3) Uani 1 1 d . . . H10A H 0.1466 0.3249 0.0731 0.035 Uiso 1 1 calc R . . H10B H 0.2877 0.4632 0.0818 0.035 Uiso 1 1 calc R . . C11 C 0.09151(16) 0.53513(16) 0.15128(9) 0.0295(3) Uani 1 1 d . . . H11A H 0.1532 0.6323 0.183 0.035 Uiso 1 1 calc R . . H11B H 0.0277 0.5633 0.1062 0.035 Uiso 1 1 calc R . . C12 C -0.14503(15) 0.56984(15) 0.23848(8) 0.0258(3) Uani 1 1 d . . . H12A H -0.1907 0.6116 0.1926 0.031 Uiso 1 1 calc R . . H12B H -0.1032 0.6607 0.2836 0.031 Uiso 1 1 calc R . . C13 C -0.27415(15) 0.47222(15) 0.27213(8) 0.0265(3) Uani 1 1 d . . . H13A H -0.3258 0.3895 0.2257 0.032 Uiso 1 1 calc R . . H13B H -0.3569 0.5407 0.2983 0.032 Uiso 1 1 calc R . . C14 C -0.19964(16) 0.39621(15) 0.33650(9) 0.0272(3) Uani 1 1 d . . . H14A H -0.1767 0.4778 0.389 0.033 Uiso 1 1 calc R . . H14B H -0.2785 0.3148 0.3489 0.033 Uiso 1 1 calc R . . C15 C 0.31950(15) -0.06089(14) 0.12033(7) 0.0209(2) Uani 1 1 d . A . C16 C 0.49071(15) 0.00786(15) 0.24717(8) 0.0239(2) Uani 1 1 d . A . H16A H 0.4833 0.0517 0.3081 0.029 Uiso 1 1 calc R . . H16B H 0.5764 0.0714 0.226 0.029 Uiso 1 1 calc R . . C17 C 0.53072(16) -0.16270(16) 0.23175(8) 0.0272(3) Uani 1 1 d . . . H17A H 0.6321 -0.1698 0.262 0.033 Uiso 1 1 calc R A . H17B H 0.4449 -0.2269 0.2524 0.033 Uiso 1 1 calc R . . C18 C 0.54686(16) -0.22380(15) 0.13855(9) 0.0285(3) Uani 1 1 d . A . H18A H 0.651 -0.1817 0.1217 0.034 Uiso 1 1 calc R . . H18B H 0.5454 -0.3405 0.1258 0.034 Uiso 1 1 calc R . . C22 C -0.01922(15) -0.02082(14) 0.22344(8) 0.0250(3) Uani 1 1 d . . . H22A H 0.0027 -0.1266 0.1922 0.038 Uiso 1 1 calc R . . H22B H -0.0842 0.0288 0.188 0.038 Uiso 1 1 calc R . . H22C H -0.0773 -0.0293 0.2738 0.038 Uiso 1 1 calc R . . C19 C 0.4210(2) -0.24398(19) 0.00008(9) 0.0387(3) Uani 0.620(5) 1 d P A 1 H19A H 0.3809 -0.3569 -0.012 0.046 Uiso 0.620(5) 1 calc PR A 1 H19B H 0.5327 -0.2379 -0.0182 0.046 Uiso 0.620(5) 1 calc PR A 1 C20 C 0.3184(3) -0.1566(3) -0.05043(14) 0.0374(7) Uani 0.620(5) 1 d P A 1 H20A H 0.3801 -0.0597 -0.0581 0.045 Uiso 0.620(5) 1 calc PR A 1 H20B H 0.2906 -0.2252 -0.1066 0.045 Uiso 0.620(5) 1 calc PR A 1 C21 C 0.1746(2) -0.1149(3) -0.00738(10) 0.0527(5) Uani 0.620(5) 1 d P A 1 H21A H 0.1086 -0.2128 -0.0049 0.063 Uiso 0.620(5) 1 calc PR A 1 H21B H 0.1123 -0.055 -0.0396 0.063 Uiso 0.620(5) 1 calc PR A 1 C19A C 0.4210(2) -0.24398(19) 0.00008(9) 0.0387(3) Uani 0.380(5) 1 d P A 2 H19C H 0.4641 -0.3492 -0.0116 0.046 Uiso 0.380(5) 1 calc PR A 2 H19D H 0.4878 -0.1733 -0.0275 0.046 Uiso 0.380(5) 1 calc PR A 2 C20A C 0.2439(5) -0.2576(5) -0.0316(2) 0.0345(11) Uani 0.380(5) 1 d P A 2 H20C H 0.2386 -0.2917 -0.0935 0.041 Uiso 0.380(5) 1 calc PR A 2 H20D H 0.1825 -0.3393 -0.0091 0.041 Uiso 0.380(5) 1 calc PR A 2 C21A C 0.1746(2) -0.1149(3) -0.00738(10) 0.0527(5) Uani 0.380(5) 1 d P A 2 H21C H 0.0573 -0.1379 -0.0153 0.063 Uiso 0.380(5) 1 calc PR A 2 H21D H 0.2085 -0.0486 -0.0467 0.063 Uiso 0.380(5) 1 calc PR A 2 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 Si 0.02154(17) 0.01486(15) 0.01686(16) 0.00353(11) 0.00293(11) 0.00521(11) N1 0.0294(5) 0.0149(4) 0.0178(5) 0.0020(4) 0.0031(4) 0.0042(4) N2 0.0372(6) 0.0179(5) 0.0207(5) 0.0052(4) -0.0011(4) 0.0029(4) N3 0.0347(6) 0.0254(5) 0.0171(5) 0.0044(4) -0.0009(4) -0.0013(4) N4 0.0215(5) 0.0178(4) 0.0244(5) 0.0079(4) 0.0069(4) 0.0068(4) N5 0.0256(5) 0.0220(5) 0.0296(5) 0.0085(4) 0.0095(4) 0.0095(4) N6 0.0225(5) 0.0211(5) 0.0279(5) 0.0097(4) 0.0054(4) 0.0077(4) N7 0.0218(5) 0.0211(5) 0.0167(5) 0.0021(4) 0.0011(4) 0.0083(4) N8 0.0436(7) 0.0423(7) 0.0194(5) 0.0003(5) -0.0035(5) 0.0224(6) N9 0.0289(6) 0.0299(6) 0.0220(5) -0.0017(4) 0.0026(4) 0.0130(4) C1 0.0197(5) 0.0215(5) 0.0175(5) 0.0046(4) 0.0028(4) 0.0037(4) C2 0.0326(7) 0.0172(5) 0.0226(6) -0.0005(4) 0.0046(5) 0.0025(5) C3 0.0273(6) 0.0261(6) 0.0294(6) -0.0020(5) 0.0031(5) -0.0026(5) C4 0.0295(7) 0.0332(7) 0.0202(6) -0.0013(5) -0.0028(5) -0.0008(5) C5 0.0443(8) 0.0349(7) 0.0217(6) 0.0121(5) 0.0032(5) 0.0072(6) C6 0.0330(7) 0.0356(7) 0.0369(7) 0.0208(6) 0.0022(6) -0.0012(6) C7 0.0302(6) 0.0193(5) 0.0299(6) 0.0080(5) -0.0051(5) -0.0010(5) C8 0.0204(5) 0.0143(5) 0.0229(5) 0.0033(4) 0.0015(4) 0.0033(4) C9 0.0206(6) 0.0239(6) 0.0333(7) 0.0117(5) 0.0074(5) 0.0044(4) C10 0.0291(7) 0.0319(7) 0.0301(7) 0.0151(5) 0.0105(5) 0.0064(5) C11 0.0299(7) 0.0285(6) 0.0367(7) 0.0189(5) 0.0075(5) 0.0082(5) C12 0.0251(6) 0.0229(6) 0.0313(6) 0.0075(5) 0.0018(5) 0.0106(5) C13 0.0212(6) 0.0271(6) 0.0294(6) 0.0013(5) 0.0025(5) 0.0063(5) C14 0.0252(6) 0.0259(6) 0.0319(7) 0.0074(5) 0.0104(5) 0.0076(5) C15 0.0240(6) 0.0206(5) 0.0184(5) 0.0032(4) 0.0043(4) 0.0056(4) C16 0.0219(6) 0.0255(6) 0.0235(6) 0.0026(5) -0.0004(5) 0.0058(5) C17 0.0245(6) 0.0295(6) 0.0299(6) 0.0090(5) 0.0003(5) 0.0101(5) C18 0.0264(6) 0.0247(6) 0.0345(7) 0.0032(5) 0.0042(5) 0.0119(5) C22 0.0258(6) 0.0215(6) 0.0281(6) 0.0062(5) 0.0003(5) 0.0027(5) C19 0.0441(8) 0.0423(8) 0.0247(7) -0.0074(6) 0.0060(6) 0.0161(7) C20 0.0471(15) 0.0436(15) 0.0189(10) 0.0005(9) 0.0045(9) 0.0058(11) C21 0.0529(10) 0.0757(13) 0.0234(7) -0.0076(8) -0.0114(7) 0.0269(9) C19A 0.0441(8) 0.0423(8) 0.0247(7) -0.0074(6) 0.0060(6) 0.0161(7) C20A 0.040(2) 0.039(2) 0.0194(17) -0.0033(14) -0.0026(14) 0.0037(16) C21A 0.0529(10) 0.0757(13) 0.0234(7) -0.0076(8) -0.0114(7) 0.0269(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si N4 1.7542(10) . ? Si N7 1.7560(10) . ? Si N1 1.7624(10) . ? Si C22 1.8521(13) . ? N1 C1 1.3862(15) . ? N1 C2 1.4686(14) . ? N2 C1 1.2938(15) . ? N2 C7 1.4570(15) . ? N3 C1 1.3745(15) . ? N3 C4 1.4508(16) . ? N3 C5 1.4591(17) . ? N4 C8 1.3912(15) . ? N4 C9 1.4628(15) . ? N5 C8 1.2883(16) . ? N5 C14 1.4555(15) . ? N6 C8 1.3786(15) . ? N6 C12 1.4574(15) . ? N6 C11 1.4578(16) . ? N7 C15 1.3901(15) . ? N7 C16 1.4638(15) . ? N8 C15 1.2838(17) . ? N8 C21 1.4599(18) . ? N9 C15 1.3780(15) . ? N9 C18 1.4539(17) . ? N9 C19 1.4600(17) . ? C2 C3 1.5162(19) . ? C3 C4 1.508(2) . ? C5 C6 1.507(2) . ? C6 C7 1.512(2) . ? C9 C10 1.5116(18) . ? C10 C11 1.5148(18) . ? C12 C13 1.5152(18) . ? C13 C14 1.5157(18) . ? C16 C17 1.5144(17) . ? C17 C18 1.5114(19) . ? C19 C20 1.538(3) . ? C20 C21 1.438(3) . ? 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 N4 Si N7 106.67(5) . . ? N4 Si N1 106.07(5) . . ? N7 Si N1 104.20(5) . . ? N4 Si C22 110.25(5) . . ? N7 Si C22 113.77(5) . . ? N1 Si C22 115.22(5) . . ? C1 N1 C2 118.78(10) . . ? C1 N1 Si 117.43(8) . . ? C2 N1 Si 123.30(8) . . ? C1 N2 C7 115.95(10) . . ? C1 N3 C4 124.90(11) . . ? C1 N3 C5 120.86(11) . . ? C4 N3 C5 114.13(10) . . ? C8 N4 C9 119.06(9) . . ? C8 N4 Si 116.55(8) . . ? C9 N4 Si 124.30(8) . . ? C8 N5 C14 119.37(10) . . ? C8 N6 C12 117.70(10) . . ? C8 N6 C11 123.43(10) . . ? C12 N6 C11 115.35(10) . . ? C15 N7 C16 117.35(10) . . ? C15 N7 Si 117.95(8) . . ? C16 N7 Si 124.38(8) . . ? C15 N8 C21 116.61(12) . . ? C15 N9 C18 125.24(10) . . ? C15 N9 C19 119.24(11) . . ? C18 N9 C19 114.43(11) . . ? N2 C1 N3 124.70(11) . . ? N2 C1 N1 116.82(10) . . ? N3 C1 N1 118.47(10) . . ? N1 C2 C3 109.85(10) . . ? C4 C3 C2 109.14(11) . . ? N3 C4 C3 111.43(10) . . ? N3 C5 C6 111.64(11) . . ? C5 C6 C7 109.32(11) . . ? N2 C7 C6 111.18(11) . . ? N5 C8 N6 125.83(11) . . ? N5 C8 N4 116.05(10) . . ? N6 C8 N4 118.07(10) . . ? N4 C9 C10 109.98(10) . . ? C9 C10 C11 108.60(11) . . ? N6 C11 C10 110.72(10) . . ? N6 C12 C13 109.93(10) . . ? C12 C13 C14 109.14(10) . . ? N5 C14 C13 114.45(10) . . ? N8 C15 N9 125.32(11) . . ? N8 C15 N7 116.84(11) . . ? N9 C15 N7 117.81(10) . . ? N7 C16 C17 109.64(10) . . ? C18 C17 C16 108.25(11) . . ? N9 C18 C17 111.89(10) . . ? N9 C19 C20 112.47(13) . . ? C21 C20 C19 110.23(18) . . ? C20 C21 N8 112.49(16) . . ? #===END data_(3)-oct1403 _database_code_depnum_ccdc_archive 'CCDC 232113' _audit_creation_date 2003-10-16T13:21:32-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H41 N9 Si1' _chemical_formula_sum 'C27 H41 N9 Si1' _chemical_formula_weight 519.78 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 17.5198(5) _cell_length_b 15.3048(3) _cell_length_c 9.9712(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2673.65(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8612 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.35 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.976028E-1 _diffrn_orient_matrix_ub_12 -0.150166E-1 _diffrn_orient_matrix_ub_13 0.3062E-3 _diffrn_orient_matrix_ub_21 -0.8296E-3 _diffrn_orient_matrix_ub_22 0.7637E-3 _diffrn_orient_matrix_ub_23 -0.570724E-1 _diffrn_orient_matrix_ub_31 0.230403E-1 _diffrn_orient_matrix_ub_32 -0.635854E-1 _diffrn_orient_matrix_ub_33 -0.7578E-3 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_unetI/netI 0.0446 _diffrn_reflns_number 14383 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 25.34 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.966 _diffrn_measured_fraction_theta_max 0.966 _reflns_number_total 4445 _reflns_number_gt 3974 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (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)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; C17 is disordered over two sites. 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^)+(0.0394P)^2^+0.6490P] 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 riding _refine_ls_extinction_method none _refine_ls_number_reflns 4445 _refine_ls_number_parameters 344 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(12) _refine_diff_density_max 0.226 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Si Si 0.86139(3) 0.72804(4) 0.48966(6) 0.02182(15) Uani 1 1 d . A . N1 N 0.95481(10) 0.76087(11) 0.45058(18) 0.0238(4) Uani 1 1 d . . . N2 N 0.92046(10) 0.89165(12) 0.53889(19) 0.0266(4) Uani 1 1 d . . . N3 N 1.02552(10) 0.88809(12) 0.39017(19) 0.0264(4) Uani 1 1 d . . . N4 N 0.84630(10) 0.72962(13) 0.66236(19) 0.0250(4) Uani 1 1 d . . . N5 N 0.72936(11) 0.67166(14) 0.62147(19) 0.0312(5) Uani 1 1 d . . . N6 N 0.76190(11) 0.70943(13) 0.84516(19) 0.0305(5) Uani 1 1 d . . . N7 N 0.85153(10) 0.62479(12) 0.41381(19) 0.0247(4) Uani 1 1 d . . . N8 N 0.93424(11) 0.57377(12) 0.5716(2) 0.0314(5) Uani 1 1 d . . . N9 N 0.88339(11) 0.47419(12) 0.4136(2) 0.0303(5) Uani 1 1 d . . . C1 C 0.96825(12) 0.85034(13) 0.4638(2) 0.0223(5) Uani 1 1 d . . . C2 C 1.01510(13) 0.70611(15) 0.3920(3) 0.0308(6) Uani 1 1 d . . . H2A H 0.9935 0.6489 0.3653 0.037 Uiso 1 1 calc R . . H2B H 1.0555 0.6956 0.4595 0.037 Uiso 1 1 calc R . . C3 C 1.04901(15) 0.75082(16) 0.2709(3) 0.0345(6) Uani 1 1 d . . . H3A H 1.09 0.7141 0.2321 0.041 Uiso 1 1 calc R . . H3B H 1.0092 0.7594 0.2017 0.041 Uiso 1 1 calc R . . C4 C 1.08114(14) 0.83786(16) 0.3130(2) 0.0336(6) Uani 1 1 d . . . H4A H 1.1274 0.8284 0.3681 0.04 Uiso 1 1 calc R . . H4B H 1.0961 0.8715 0.2324 0.04 Uiso 1 1 calc R . . C5 C 1.04832(14) 0.97876(15) 0.4173(3) 0.0314(6) Uani 1 1 d . . . H5A H 1.0401 1.0143 0.3356 0.038 Uiso 1 1 calc R . . H5B H 1.1035 0.9803 0.4387 0.038 Uiso 1 1 calc R . . C6 C 1.00405(14) 1.01877(16) 0.5324(3) 0.0347(6) Uani 1 1 d . . . H6A H 1.0048 1.0833 0.5251 0.042 Uiso 1 1 calc R . . H6B H 1.0277 1.0022 0.6189 0.042 Uiso 1 1 calc R . . C7 C 0.92260(14) 0.98582(15) 0.5269(3) 0.0334(6) Uani 1 1 d . . . H7A H 0.8927 1.0124 0.6006 0.04 Uiso 1 1 calc R . . H7B H 0.899 1.0036 0.4409 0.04 Uiso 1 1 calc R . . C8 C 0.77653(13) 0.70007(14) 0.7098(2) 0.0227(5) Uani 1 1 d . . . C9 C 0.91046(14) 0.73961(18) 0.7559(2) 0.0331(6) Uani 1 1 d . . . H9A H 0.9495 0.7783 0.7156 0.04 Uiso 1 1 calc R . . H9B H 0.9342 0.6819 0.7721 0.04 Uiso 1 1 calc R . . C10 C 0.88449(16) 0.77746(18) 0.8864(3) 0.0406(6) Uani 1 1 d . . . H10A H 0.8651 0.8375 0.8723 0.049 Uiso 1 1 calc R . . H10B H 0.9278 0.7802 0.95 0.049 Uiso 1 1 calc R . . C11 C 0.82247(16) 0.7208(2) 0.9424(3) 0.0455(7) Uani 1 1 d . . . H11A H 0.8438 0.6631 0.9668 0.055 Uiso 1 1 calc R . . H11B H 0.8016 0.748 1.0247 0.055 Uiso 1 1 calc R . . C12 C 0.69238(14) 0.67007(18) 0.8980(3) 0.0394(6) Uani 1 1 d . . . H12A H 0.6783 0.6984 0.9838 0.047 Uiso 1 1 calc R . . H12B H 0.7008 0.6071 0.9152 0.047 Uiso 1 1 calc R . . C13 C 0.62905(15) 0.68166(18) 0.7974(3) 0.0401(6) Uani 1 1 d . . . H13A H 0.5825 0.6515 0.8292 0.048 Uiso 1 1 calc R . . H13B H 0.6171 0.7445 0.7871 0.048 Uiso 1 1 calc R . . C14 C 0.65334(13) 0.64440(19) 0.6653(3) 0.0371(6) Uani 1 1 d . . . H14A H 0.6523 0.5799 0.6715 0.045 Uiso 1 1 calc R . . H14B H 0.6158 0.662 0.5962 0.045 Uiso 1 1 calc R . . C15 C 0.89066(12) 0.55510(13) 0.4723(2) 0.0224(5) Uani 1 1 d . A . C19 C 0.92744(14) 0.40154(16) 0.4667(3) 0.0368(6) Uani 1 1 d . A . H19A H 0.9403 0.3608 0.393 0.044 Uiso 1 1 calc R . . H19B H 0.8964 0.3694 0.5333 0.044 Uiso 1 1 calc R . . C20 C 0.99989(14) 0.43317(15) 0.5322(3) 0.0344(6) Uani 1 1 d . . . H20A H 1.0352 0.4564 0.4634 0.041 Uiso 1 1 calc R A . H20B H 1.0255 0.3842 0.5788 0.041 Uiso 1 1 calc R . . C21 C 0.97979(14) 0.50425(17) 0.6318(3) 0.0339(6) Uani 1 1 d . A . H21A H 0.951 0.4782 0.7072 0.041 Uiso 1 1 calc R . . H21B H 1.0274 0.5296 0.6685 0.041 Uiso 1 1 calc R . . C22 C 0.79819(13) 0.80715(14) 0.3967(2) 0.0253(5) Uani 1 1 d . . . C23 C 0.81830(14) 0.83276(16) 0.2673(2) 0.0319(6) Uani 1 1 d . A . H23 H 0.8591 0.8036 0.2234 0.038 Uiso 1 1 calc R . . C24 C 0.78055(17) 0.89948(18) 0.2007(3) 0.0413(7) Uani 1 1 d . . . H24 H 0.7958 0.9155 0.1127 0.05 Uiso 1 1 calc R A . C25 C 0.72077(15) 0.94268(17) 0.2623(3) 0.0402(7) Uani 1 1 d . A . H25 H 0.695 0.9889 0.2176 0.048 Uiso 1 1 calc R . . C26 C 0.69913(15) 0.91768(17) 0.3895(3) 0.0431(7) Uani 1 1 d . . . H26 H 0.6578 0.9465 0.4323 0.052 Uiso 1 1 calc R A . C27 C 0.73703(13) 0.85098(15) 0.4556(3) 0.0332(6) Uani 1 1 d . A . H27 H 0.721 0.8347 0.5431 0.04 Uiso 1 1 calc R . . C16 C 0.7905(2) 0.60457(19) 0.3204(3) 0.0581(9) Uani 0.514(3) 1 d P A 1 H16A H 0.7432 0.5959 0.3733 0.07 Uiso 0.514(3) 1 calc PR A 1 H16B H 0.7824 0.6567 0.2633 0.07 Uiso 0.514(3) 1 calc PR A 1 C17 C 0.7987(3) 0.5327(3) 0.2360(5) 0.0249(11) Uani 0.514(3) 1 d P A 1 H17A H 0.8386 0.5447 0.168 0.03 Uiso 0.514(3) 1 calc PR A 1 H17B H 0.7501 0.521 0.1888 0.03 Uiso 0.514(3) 1 calc PR A 1 C18 C 0.82203(15) 0.45095(16) 0.3229(3) 0.0369(6) Uani 0.514(3) 1 d P A 1 H18A H 0.7774 0.4303 0.375 0.044 Uiso 0.514(3) 1 calc PR A 1 H18B H 0.8388 0.4029 0.2634 0.044 Uiso 0.514(3) 1 calc PR A 1 C16A C 0.7905(2) 0.60457(19) 0.3204(3) 0.0581(9) Uani 0.486(3) 1 d P A 2 H16C H 0.7477 0.6453 0.3379 0.07 Uiso 0.486(3) 1 calc PR A 2 H16D H 0.8092 0.6165 0.2286 0.07 Uiso 0.486(3) 1 calc PR A 2 C17A C 0.7623(3) 0.5214(3) 0.3233(7) 0.0372(14) Uani 0.486(3) 1 d P A 2 H17C H 0.7288 0.513 0.2444 0.045 Uiso 0.486(3) 1 calc PR A 2 H17D H 0.7305 0.5146 0.4046 0.045 Uiso 0.486(3) 1 calc PR A 2 C18A C 0.82203(15) 0.45095(16) 0.3229(3) 0.0369(6) Uani 0.486(3) 1 d P A 2 H18C H 0.7989 0.3949 0.3513 0.044 Uiso 0.486(3) 1 calc PR A 2 H18D H 0.8425 0.4435 0.2311 0.044 Uiso 0.486(3) 1 calc PR A 2 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 Si 0.0211(3) 0.0229(3) 0.0214(3) -0.0005(3) -0.0013(3) -0.0012(3) N1 0.0200(9) 0.0176(9) 0.0338(12) 0.0000(8) 0.0038(8) 0.0009(7) N2 0.0227(10) 0.0241(10) 0.0329(11) -0.0039(8) 0.0015(8) 0.0008(8) N3 0.0268(10) 0.0209(10) 0.0315(11) -0.0015(8) 0.0040(9) -0.0016(8) N4 0.0224(10) 0.0319(11) 0.0208(10) 0.0008(8) -0.0015(8) -0.0051(8) N5 0.0257(11) 0.0420(13) 0.0260(12) -0.0002(9) -0.0020(8) -0.0073(9) N6 0.0331(11) 0.0358(12) 0.0226(11) -0.0028(8) 0.0014(8) -0.0092(10) N7 0.0256(10) 0.0216(10) 0.0268(11) 0.0008(8) -0.0054(8) -0.0016(8) N8 0.0366(12) 0.0253(10) 0.0323(12) 0.0005(9) -0.0077(10) 0.0005(9) N9 0.0281(10) 0.0224(10) 0.0406(13) -0.0044(9) -0.0052(9) 0.0013(9) C1 0.0186(11) 0.0219(11) 0.0264(13) 0.0017(9) -0.0048(9) -0.0013(9) C2 0.0267(12) 0.0247(12) 0.0411(15) -0.0010(10) 0.0094(11) 0.0041(10) C3 0.0382(14) 0.0307(13) 0.0346(14) -0.0046(11) 0.0093(11) 0.0028(11) C4 0.0341(14) 0.0362(15) 0.0306(15) 0.0025(11) 0.0100(11) -0.0016(11) C5 0.0325(13) 0.0243(12) 0.0374(15) -0.0004(11) 0.0028(11) -0.0075(11) C6 0.0351(14) 0.0244(13) 0.0445(16) -0.0048(11) -0.0002(11) -0.0043(11) C7 0.0292(13) 0.0288(13) 0.0424(16) -0.0082(11) -0.0008(11) 0.0016(11) C8 0.0252(13) 0.0193(12) 0.0236(13) 0.0016(9) 0.0018(9) 0.0009(10) C9 0.0266(13) 0.0466(15) 0.0263(14) 0.0007(11) -0.0087(10) -0.0059(11) C10 0.0433(15) 0.0421(16) 0.0365(16) -0.0078(12) -0.0086(12) -0.0108(13) C11 0.0500(17) 0.067(2) 0.0198(14) -0.0054(12) -0.0024(11) -0.0208(15) C12 0.0401(15) 0.0485(16) 0.0296(15) 0.0004(13) 0.0120(12) -0.0113(13) C13 0.0312(14) 0.0436(16) 0.0454(17) 0.0017(13) 0.0100(12) -0.0004(12) C14 0.0251(13) 0.0472(17) 0.0390(15) 0.0028(12) -0.0009(11) -0.0071(11) C15 0.0233(11) 0.0199(11) 0.0242(13) 0.0015(9) 0.0035(10) -0.0012(9) C19 0.0425(15) 0.0233(12) 0.0446(17) 0.0012(11) -0.0062(12) 0.0016(11) C20 0.0317(14) 0.0290(13) 0.0425(16) 0.0035(11) -0.0027(11) 0.0025(11) C21 0.0314(14) 0.0352(14) 0.0351(15) 0.0009(11) -0.0076(11) 0.0048(12) C22 0.0255(12) 0.0227(12) 0.0277(13) -0.0036(10) -0.0038(10) -0.0023(10) C23 0.0363(14) 0.0346(14) 0.0247(13) -0.0018(11) -0.0027(10) 0.0037(11) C24 0.0521(18) 0.0372(16) 0.0345(15) 0.0086(12) -0.0088(12) 0.0020(14) C25 0.0378(15) 0.0273(14) 0.0556(18) 0.0068(12) -0.0179(13) -0.0007(12) C26 0.0296(14) 0.0314(14) 0.068(2) 0.0020(14) 0.0003(13) 0.0087(11) C27 0.0249(12) 0.0328(14) 0.0419(16) 0.0050(11) 0.0013(10) 0.0009(10) C16 0.083(2) 0.0309(16) 0.060(2) -0.0026(14) -0.0487(18) -0.0017(15) C17 0.025(3) 0.033(3) 0.016(3) -0.0011(19) -0.0015(19) 0.001(2) C18 0.0338(15) 0.0248(14) 0.0520(17) -0.0083(12) -0.0131(12) -0.0013(11) C16A 0.083(2) 0.0309(16) 0.060(2) -0.0026(14) -0.0487(18) -0.0017(15) C17A 0.027(3) 0.034(3) 0.050(4) -0.007(3) -0.015(3) 0.000(2) C18A 0.0338(15) 0.0248(14) 0.0520(17) -0.0083(12) -0.0131(12) -0.0013(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Si N4 1.742(2) . ? Si N1 1.7560(18) . ? Si N7 1.7604(19) . ? Si C22 1.884(2) . ? N1 C1 1.396(3) . ? N1 C2 1.470(3) . ? N2 C1 1.289(3) . ? N2 C7 1.447(3) . ? N3 C1 1.371(3) . ? N3 C4 1.460(3) . ? N3 C5 1.469(3) . ? N4 C8 1.386(3) . ? N4 C9 1.469(3) . ? N5 C8 1.284(3) . ? N5 C14 1.462(3) . ? N6 C8 1.382(3) . ? N6 C11 1.448(3) . ? N6 C12 1.457(3) . ? N7 C15 1.395(3) . ? N7 C16 1.451(3) . ? N8 C15 1.283(3) . ? N8 C21 1.459(3) . ? N9 C15 1.375(3) . ? N9 C18 1.449(3) . ? N9 C19 1.453(3) . ? C2 C3 1.510(3) . ? C3 C4 1.506(3) . ? C5 C6 1.514(3) . ? C6 C7 1.514(3) . ? C9 C10 1.495(4) . ? C10 C11 1.498(4) . ? C12 C13 1.506(4) . ? C13 C14 1.497(4) . ? C19 C20 1.507(3) . ? C20 C21 1.515(3) . ? C22 C23 1.394(3) . ? C22 C27 1.394(3) . ? C23 C24 1.386(4) . ? C24 C25 1.382(4) . ? C25 C26 1.378(4) . ? C26 C27 1.385(4) . ? C16 C17 1.393(5) . ? C17 C18 1.576(5) . ? 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 N4 Si N1 110.90(9) . . ? N4 Si N7 114.97(10) . . ? N1 Si N7 104.66(9) . . ? N4 Si C22 112.83(10) . . ? N1 Si C22 104.75(9) . . ? N7 Si C22 107.93(9) . . ? C1 N1 C2 118.41(18) . . ? C1 N1 Si 114.65(14) . . ? C2 N1 Si 126.51(15) . . ? C1 N2 C7 115.06(19) . . ? C1 N3 C4 123.27(18) . . ? C1 N3 C5 119.89(18) . . ? C4 N3 C5 114.39(17) . . ? C8 N4 C9 119.5(2) . . ? C8 N4 Si 117.79(15) . . ? C9 N4 Si 120.88(15) . . ? C8 N5 C14 118.6(2) . . ? C8 N6 C11 122.0(2) . . ? C8 N6 C12 117.7(2) . . ? C11 N6 C12 114.9(2) . . ? C15 N7 C16 117.85(19) . . ? C15 N7 Si 117.28(15) . . ? C16 N7 Si 122.63(16) . . ? C15 N8 C21 118.74(19) . . ? C15 N9 C18 123.71(19) . . ? C15 N9 C19 119.01(19) . . ? C18 N9 C19 115.68(18) . . ? N2 C1 N3 125.44(19) . . ? N2 C1 N1 115.24(19) . . ? N3 C1 N1 119.11(19) . . ? N1 C2 C3 110.02(19) . . ? C4 C3 C2 108.9(2) . . ? N3 C4 C3 111.31(19) . . ? N3 C5 C6 112.48(19) . . ? C5 C6 C7 108.69(19) . . ? N2 C7 C6 110.7(2) . . ? N5 C8 N6 125.9(2) . . ? N5 C8 N4 116.4(2) . . ? N6 C8 N4 117.6(2) . . ? N4 C9 C10 111.1(2) . . ? C9 C10 C11 108.7(2) . . ? N6 C11 C10 110.6(2) . . ? N6 C12 C13 109.0(2) . . ? C14 C13 C12 109.4(2) . . ? N5 C14 C13 114.4(2) . . ? N8 C15 N9 125.7(2) . . ? N8 C15 N7 116.40(19) . . ? N9 C15 N7 117.7(2) . . ? N9 C19 C20 111.0(2) . . ? C19 C20 C21 108.6(2) . . ? N8 C21 C20 112.4(2) . . ? C23 C22 C27 116.7(2) . . ? C23 C22 Si 119.18(18) . . ? C27 C22 Si 123.62(19) . . ? C24 C23 C22 122.0(2) . . ? C25 C24 C23 120.1(3) . . ? C26 C25 C24 119.0(2) . . ? C25 C26 C27 120.7(2) . . ? C26 C27 C22 121.5(3) . . ? C17 C16 N7 118.7(3) . . ? C16 C17 C18 108.8(3) . . ? N9 C18 C17 109.9(2) . . ? #===END data_(4)-mar703 _database_code_depnum_ccdc_archive 'CCDC 232114' _audit_creation_date 2003-03-12T09:41:31-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common '[CuCl{Me2Si(C7H12N3)2}]' _chemical_formula_moiety 'C16 H30 Cl1 Cu1 N6 Si1' _chemical_formula_sum 'C16 H30 Cl1 Cu1 N6 Si1' _chemical_formula_weight 433.54 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 13.2511(3) _cell_length_b 10.6399(3) _cell_length_c 14.0837(4) _cell_angle_alpha 90 _cell_angle_beta 96.377(1) _cell_angle_gamma 90 _cell_volume 1973.38(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19283 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.315 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.752 _exptl_absorpt_correction_T_max 0.8458 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_unetI/netI 0.0304 _diffrn_reflns_number 19159 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.79 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 3446 _reflns_number_gt 2964 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (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)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+2.6250P] 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 riding _refine_ls_extinction_method none _refine_ls_number_reflns 3446 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.425 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.06 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.29765(2) 0.61855(3) 0.45658(2) 0.02389(12) Uani 1 1 d . . . Cl Cl 0.35789(6) 0.79909(6) 0.37651(5) 0.03483(19) Uani 1 1 d . . . Si Si 0.19192(5) 0.39240(7) 0.53120(5) 0.02423(18) Uani 1 1 d . . . N1 N 0.35584(17) 0.4750(2) 0.40006(15) 0.0252(5) Uani 1 1 d . . . N2 N 0.31037(17) 0.3312(2) 0.51257(15) 0.0261(5) Uani 1 1 d . . . N3 N 0.42725(17) 0.2728(2) 0.40662(16) 0.0292(5) Uani 1 1 d . . . N4 N 0.20937(17) 0.6874(2) 0.54332(15) 0.0263(5) Uani 1 1 d . . . N5 N 0.19947(17) 0.4994(2) 0.62638(15) 0.0267(5) Uani 1 1 d . . . N6 N 0.14336(18) 0.6855(3) 0.69138(16) 0.0354(6) Uani 1 1 d . . . C1 C 0.36577(19) 0.3628(2) 0.43748(17) 0.0229(6) Uani 1 1 d . . . C2 C 0.4056(2) 0.4923(3) 0.31230(19) 0.0324(7) Uani 1 1 d . . . H2A H 0.4069 0.5828 0.296 0.039 Uiso 1 1 calc R . . H2B H 0.3667 0.4475 0.2585 0.039 Uiso 1 1 calc R . . C3 C 0.5125(2) 0.4420(3) 0.3273(2) 0.0382(7) Uani 1 1 d . . . H3A H 0.5471 0.4569 0.2696 0.046 Uiso 1 1 calc R . . H3B H 0.5512 0.4854 0.3819 0.046 Uiso 1 1 calc R . . C4 C 0.5077(2) 0.3035(3) 0.3471(2) 0.0367(7) Uani 1 1 d . . . H4A H 0.4955 0.2575 0.2858 0.044 Uiso 1 1 calc R . . H4B H 0.5739 0.2754 0.3798 0.044 Uiso 1 1 calc R . . C5 C 0.4320(2) 0.1414(3) 0.4388(2) 0.0388(7) Uani 1 1 d . . . H5A H 0.502 0.1226 0.4676 0.047 Uiso 1 1 calc R . . H5B H 0.4169 0.0858 0.3827 0.047 Uiso 1 1 calc R . . C6 C 0.3588(3) 0.1122(3) 0.5108(3) 0.0490(9) Uani 1 1 d . . . H6A H 0.2906 0.0931 0.4778 0.059 Uiso 1 1 calc R . . H6B H 0.3827 0.0386 0.55 0.059 Uiso 1 1 calc R . . C7 C 0.3541(2) 0.2263(3) 0.5730(2) 0.0386(7) Uani 1 1 d . . . H7A H 0.3113 0.209 0.6248 0.046 Uiso 1 1 calc R . . H7B H 0.4231 0.2488 0.6024 0.046 Uiso 1 1 calc R . . C8 C 0.18455(19) 0.6281(3) 0.61861(18) 0.0252(6) Uani 1 1 d . . . C9 C 0.1803(2) 0.8208(3) 0.5365(2) 0.0339(7) Uani 1 1 d . . . H9A H 0.1064 0.8281 0.517 0.041 Uiso 1 1 calc R . . H9B H 0.2165 0.8627 0.4873 0.041 Uiso 1 1 calc R . . C10 C 0.2068(3) 0.8840(3) 0.6314(2) 0.0450(8) Uani 1 1 d . . . H10A H 0.2805 0.8761 0.6514 0.054 Uiso 1 1 calc R . . H10B H 0.1898 0.9745 0.6262 0.054 Uiso 1 1 calc R . . C11 C 0.1483(3) 0.8234(3) 0.7034(2) 0.0511(9) Uani 1 1 d . . . H11A H 0.1808 0.8435 0.7683 0.061 Uiso 1 1 calc R . . H11B H 0.0786 0.858 0.6971 0.061 Uiso 1 1 calc R . . C12 C 0.1034(2) 0.6218(4) 0.7709(2) 0.0492(9) Uani 1 1 d . . . H12A H 0.0299 0.6403 0.7686 0.059 Uiso 1 1 calc R . . H12B H 0.1372 0.6563 0.8315 0.059 Uiso 1 1 calc R . . C13 C 0.1179(3) 0.4818(4) 0.7707(2) 0.0531(10) Uani 1 1 d . . . H13A H 0.0591 0.4408 0.7336 0.064 Uiso 1 1 calc R . . H13B H 0.1236 0.4491 0.8369 0.064 Uiso 1 1 calc R . . C14 C 0.2141(2) 0.4536(3) 0.72598(19) 0.0373(7) Uani 1 1 d . . . H14A H 0.2727 0.4966 0.7619 0.045 Uiso 1 1 calc R . . H14B H 0.2274 0.3621 0.7272 0.045 Uiso 1 1 calc R . . C15 C 0.1130(2) 0.4447(3) 0.4206(2) 0.0314(6) Uani 1 1 d . . . H15A H 0.0482 0.4777 0.4371 0.047 Uiso 1 1 calc R . . H15B H 0.1003 0.3732 0.377 0.047 Uiso 1 1 calc R . . H15C H 0.149 0.5106 0.3893 0.047 Uiso 1 1 calc R . . C16 C 0.1180(2) 0.2562(3) 0.5733(2) 0.0391(7) Uani 1 1 d . . . H16A H 0.0502 0.2849 0.5852 0.059 Uiso 1 1 calc R . . H16B H 0.1536 0.2223 0.6325 0.059 Uiso 1 1 calc R . . H16C H 0.1116 0.1906 0.5242 0.059 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 Cu 0.0271(2) 0.02141(19) 0.02390(18) -0.00044(13) 0.00600(13) 0.00296(13) Cl 0.0367(4) 0.0266(4) 0.0425(4) 0.0074(3) 0.0101(3) -0.0016(3) Si 0.0226(4) 0.0228(4) 0.0275(4) 0.0022(3) 0.0038(3) -0.0001(3) N1 0.0286(12) 0.0241(12) 0.0242(11) 0.0013(9) 0.0085(10) 0.0041(10) N2 0.0271(12) 0.0217(11) 0.0303(12) 0.0067(10) 0.0065(10) 0.0041(10) N3 0.0285(13) 0.0252(12) 0.0338(13) -0.0034(10) 0.0035(10) 0.0063(10) N4 0.0284(12) 0.0237(12) 0.0276(12) -0.0035(10) 0.0069(10) 0.0019(10) N5 0.0275(12) 0.0319(13) 0.0213(11) 0.0029(10) 0.0045(9) -0.0018(10) N6 0.0303(13) 0.0514(16) 0.0255(12) -0.0066(11) 0.0071(10) 0.0114(12) C1 0.0224(14) 0.0229(14) 0.0228(13) -0.0039(11) 0.0001(11) 0.0014(11) C2 0.0417(17) 0.0317(16) 0.0259(14) 0.0012(12) 0.0130(13) 0.0033(13) C3 0.0344(17) 0.0475(19) 0.0355(16) -0.0016(14) 0.0159(13) -0.0006(14) C4 0.0302(16) 0.0458(19) 0.0354(16) -0.0050(14) 0.0090(13) 0.0094(14) C5 0.0434(18) 0.0224(15) 0.0494(18) -0.0043(13) -0.0005(15) 0.0099(13) C6 0.050(2) 0.0219(16) 0.076(2) 0.0133(16) 0.0107(18) 0.0095(14) C7 0.0354(17) 0.0397(18) 0.0418(17) 0.0178(14) 0.0088(14) 0.0132(14) C8 0.0184(13) 0.0321(15) 0.0247(13) -0.0055(12) 0.0001(11) 0.0016(11) C9 0.0413(18) 0.0229(14) 0.0374(16) -0.0048(12) 0.0040(14) 0.0087(13) C10 0.052(2) 0.0332(17) 0.0475(19) -0.0151(15) -0.0037(16) 0.0148(15) C11 0.060(2) 0.055(2) 0.0366(17) -0.0165(16) -0.0004(16) 0.0299(18) C12 0.0310(17) 0.092(3) 0.0263(15) -0.0030(17) 0.0094(13) 0.0055(17) C13 0.047(2) 0.085(3) 0.0284(16) 0.0127(17) 0.0091(15) -0.019(2) C14 0.0391(18) 0.0473(19) 0.0248(14) 0.0093(13) 0.0001(13) -0.0043(14) C15 0.0254(15) 0.0329(16) 0.0350(15) -0.0013(13) -0.0002(12) -0.0008(12) C16 0.0344(17) 0.0338(17) 0.0501(19) 0.0047(14) 0.0087(15) -0.0065(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N1 1.923(2) . ? Cu N4 1.927(2) . ? Cu Cl 2.4081(7) . ? Si N2 1.746(2) . ? Si N5 1.753(2) . ? Si C15 1.862(3) . ? Si C16 1.881(3) . ? N1 C1 1.305(3) . ? N1 C2 1.475(3) . ? N2 C1 1.394(3) . ? N2 C7 1.482(3) . ? N3 C1 1.360(3) . ? N3 C4 1.465(4) . ? N3 C5 1.469(4) . ? N4 C8 1.307(3) . ? N4 C9 1.471(3) . ? N5 C8 1.385(3) . ? N5 C14 1.477(3) . ? N6 C8 1.359(3) . ? N6 C12 1.458(4) . ? N6 C11 1.477(4) . ? C2 C3 1.507(4) . ? C3 C4 1.503(4) . ? C5 C6 1.512(5) . ? C6 C7 1.502(5) . ? C9 C10 1.503(4) . ? C10 C11 1.489(5) . ? C12 C13 1.503(5) . ? C13 C14 1.513(5) . ? 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 N1 Cu N4 149.75(10) . . ? N1 Cu Cl 105.71(7) . . ? N4 Cu Cl 104.45(7) . . ? N2 Si N5 112.41(11) . . ? N2 Si C15 114.59(12) . . ? N5 Si C15 115.14(12) . . ? N2 Si C16 105.57(13) . . ? N5 Si C16 104.27(13) . . ? C15 Si C16 103.30(14) . . ? C1 N1 C2 114.7(2) . . ? C1 N1 Cu 125.89(18) . . ? C2 N1 Cu 118.96(17) . . ? C1 N2 C7 114.3(2) . . ? C1 N2 Si 125.59(17) . . ? C7 N2 Si 119.70(18) . . ? C1 N3 C4 121.7(2) . . ? C1 N3 C5 125.4(2) . . ? C4 N3 C5 112.3(2) . . ? C8 N4 C9 115.6(2) . . ? C8 N4 Cu 123.74(18) . . ? C9 N4 Cu 119.87(18) . . ? C8 N5 C14 113.8(2) . . ? C8 N5 Si 125.85(18) . . ? C14 N5 Si 120.1(2) . . ? C8 N6 C12 125.5(3) . . ? C8 N6 C11 121.1(3) . . ? C12 N6 C11 112.9(3) . . ? N1 C1 N3 123.5(2) . . ? N1 C1 N2 119.3(2) . . ? N3 C1 N2 117.2(2) . . ? N1 C2 C3 109.8(2) . . ? C4 C3 C2 108.4(3) . . ? N3 C4 C3 111.9(2) . . ? N3 C5 C6 113.1(2) . . ? C7 C6 C5 107.3(3) . . ? N2 C7 C6 108.2(2) . . ? N4 C8 N6 123.6(3) . . ? N4 C8 N5 119.7(2) . . ? N6 C8 N5 116.8(2) . . ? N4 C9 C10 109.9(2) . . ? C11 C10 C9 108.9(3) . . ? N6 C11 C10 111.9(2) . . ? N6 C12 C13 113.7(3) . . ? C12 C13 C14 108.1(3) . . ? N5 C14 C13 107.6(2) . . ? #===END