Supplementary Material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2003 data_global _publ_contact_author_email TAKUTA@IMD.ES.HOKUDAI.AC.JP _publ_contact_author_name 'Dr Tomoyuki Akutagawa' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name T.Akutagawa T.Hasegawa T.Nakamura G.Saito data_aku _database_code_CSD 196062 _audit_creation_date 2002-07-24 _audit_creation_method 'by CrystalStructure v3.00' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C54 H36 Cl2 N16 ' _chemical_formula_moiety 'C54 H36 Cl2 N16 ' _chemical_formula_weight 979.89 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z #------------------------------------------------------------------------------ _cell_length_a 8.135(2) _cell_length_b 12.011(3) _cell_length_c 12.048(2) _cell_angle_alpha 79.86(1) _cell_angle_beta 89.486(5) _cell_angle_gamma 78.146(6) _cell_volume 1133.6(4) _cell_formula_units_Z 1 _cell_measurement_reflns_used 6139 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 296.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506.00 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.960 _exptl_absorpt_correction_T_max 0.960 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 4663 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.8974 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.8974 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.5 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4662 _reflns_number_gt 3552 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.0920 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3552 _refine_ls_number_parameters 343 _refine_ls_goodness_of_fit_ref 0.599 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 33118.3000 46030.0000 13416.0000 ; _refine_ls_shift/su_max 0.2430 _refine_diff_density_max 0.73 _refine_diff_density_min -0.31 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.174 0.200 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Cl1 Cl 0.81126(9) 0.02073(6) 0.31735(5) 0.0527(2) Uani 1.00 1 d . . . N1 N -0.1422(3) -0.3614(2) 1.1128(2) 0.0584(7) Uani 1.00 1 d . . . N2 N 0.1484(4) -0.2439(2) 1.3511(2) 0.0640(8) Uani 1.00 1 d . . . C1 C 0.0009(3) -0.1011(2) 1.0795(2) 0.0370(6) Uani 1.00 1 d . . . C2 C 0.0795(3) -0.0118(2) 1.1059(2) 0.0404(6) Uani 1.00 1 d . . . C3 C 0.0789(3) 0.0843(2) 1.0306(2) 0.0403(6) Uani 1.00 1 d . . . C4 C 0.0016(3) -0.2003(2) 1.1552(2) 0.0404(6) Uani 1.00 1 d . . . C5 C -0.0784(3) -0.2896(2) 1.1302(2) 0.0431(6) Uani 1.00 1 d . . . C6 C 0.0818(4) -0.2222(2) 1.2646(2) 0.0485(7) Uani 1.00 1 d . . . N3 N 0.3961(3) -0.0858(2) 0.9216(2) 0.0432(6) Uani 1.00 1 d . . . N4 N 0.5057(3) -0.1328(2) 1.1029(2) 0.0444(5) Uani 1.00 1 d . . . C7 C 0.4783(3) -0.0558(2) 1.0074(2) 0.0447(7) Uani 1.00 1 d . . . C8 C 0.3713(3) -0.1957(2) 0.9641(2) 0.0425(6) Uani 1.00 1 d . . . C9 C 0.2966(4) -0.2698(3) 0.9155(2) 0.0517(8) Uani 1.00 1 d . . . C10 C 0.2940(4) -0.3753(3) 0.9802(3) 0.0516(8) Uani 1.00 1 d . . . C11 C 0.3616(4) -0.4048(3) 1.0911(3) 0.0557(8) Uani 1.00 1 d . . . C12 C 0.4325(3) -0.3297(2) 1.1381(2) 0.0497(7) Uani 1.00 1 d . . . C13 C 0.4388(3) -0.2226(2) 1.0742(2) 0.0414(6) Uani 1.00 1 d . . . N5 N 0.8027(3) -0.0848(2) 0.5718(2) 0.0435(6) Uani 1.00 1 d . . . N6 N 0.6018(3) 0.1488(2) 0.4820(2) 0.0421(5) Uani 1.00 1 d . . . N7 N 0.4908(3) 0.1559(2) 0.6467(2) 0.0411(5) Uani 1.00 1 d . . . N8 N 0.6508(3) -0.0808(2) 0.7284(2) 0.0426(5) Uani 1.00 1 d . . . C14 C 0.6827(3) -0.0245(2) 0.6286(2) 0.0390(6) Uani 1.00 1 d . . . C15 C 0.5945(3) 0.0907(2) 0.5860(2) 0.0384(6) Uani 1.00 1 d . . . C16 C 0.4990(3) 0.2569(2) 0.4741(2) 0.0396(6) Uani 1.00 1 d . . . C17 C 0.4637(4) 0.3495(2) 0.3861(2) 0.0468(7) Uani 1.00 1 d . . . C18 C 0.3528(4) 0.4449(2) 0.4063(2) 0.0573(8) Uani 1.00 1 d . . . C19 C 0.2778(4) 0.4486(3) 0.5117(3) 0.0590(8) Uani 1.00 1 d . . . C20 C 0.3131(4) 0.3580(2) 0.5991(2) 0.0500(7) Uani 1.00 1 d . . . C24 C 0.9073(4) -0.3736(2) 0.8148(2) 0.0496(7) Uani 1.00 1 d . . . C22 C 0.7609(3) -0.1857(2) 0.7380(2) 0.0403(6) Uani 1.00 1 d . . . C23 C 0.7841(4) -0.2811(2) 0.8253(2) 0.0450(7) Uani 1.00 1 d . . . C21 C 0.4275(3) 0.2608(2) 0.5791(2) 0.0408(6) Uani 1.00 1 d . . . C25 C 1.0079(4) -0.3747(2) 0.7188(3) 0.0559(8) Uani 1.00 1 d . . . C26 C 0.9839(4) -0.2834(2) 0.6294(3) 0.0552(8) Uani 1.00 1 d . . . C27 C 0.8579(3) -0.1895(2) 0.6411(2) 0.0407(6) Uani 1.00 1 d . . . H1 H 0.1328(3) -0.0196(2) 1.1894(2) 0.048(1) Uiso 1.00 1 c . . . H2 H 0.1387(3) 0.1558(2) 1.0549(2) 0.049(1) Uiso 1.00 1 c . . . H3 H 0.3875(3) -0.0467(2) 0.8421(2) 0.052(1) Uiso 1.00 1 c . . . H4 H 0.3579(4) -0.4850(3) 1.1432(3) 0.065(1) Uiso 1.00 1 c . . . H5 H 0.4679(3) -0.3469(2) 1.2324(2) 0.057(1) Uiso 1.00 1 c . . . H6 H 0.8305(3) -0.0601(2) 0.4975(2) 0.050(1) Uiso 1.00 1 c . . . H7 H 0.6631(3) 0.1236(2) 0.4261(2) 0.049(1) Uiso 1.00 1 c . . . H8 H 0.4765(3) 0.1374(2) 0.7220(2) 0.048(1) Uiso 1.00 1 c . . . H9 H 0.3347(4) 0.5163(2) 0.3452(2) 0.065(1) Uiso 1.00 1 c . . . H10 H 0.1998(4) 0.5246(3) 0.5100(3) 0.067(1) Uiso 1.00 1 c . . . H11 H 0.2700(4) 0.3601(2) 0.6767(2) 0.057(1) Uiso 1.00 1 c . . . H12 H 0.9221(4) -0.4411(2) 0.8746(2) 0.058(1) Uiso 1.00 1 c . . . H13 H 0.7048(4) -0.2740(2) 0.8987(2) 0.054(1) Uiso 1.00 1 c . . . H14 H 1.1092(4) -0.4532(2) 0.7170(3) 0.063(1) Uiso 1.00 1 c . . . H15 H 1.0574(4) -0.2892(2) 0.5622(3) 0.063(1) Uiso 1.00 1 c . . . H16 H 0.2460(4) -0.4298(3) 0.9503(3) 0.062(1) Uiso 1.00 1 c . . . H17 H 0.2486(4) -0.2481(3) 0.8413(2) 0.062(1) Uiso 1.00 1 c . . . H18 H 0.5146(4) 0.3458(2) 0.3151(2) 0.055(1) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0579(4) 0.0551(4) 0.0365(3) 0.0027(3) 0.0070(3) -0.0018(3) N1 0.063(1) 0.039(1) 0.067(2) -0.007(1) 0.002(1) 0.000(1) N2 0.070(2) 0.066(2) 0.048(1) -0.005(1) -0.005(1) 0.001(1) C1 0.040(1) 0.033(1) 0.035(1) -0.0030(9) 0.0074(9) -0.0044(9) C2 0.046(1) 0.040(1) 0.034(1) -0.007(1) -0.000(1) -0.004(1) C3 0.045(1) 0.036(1) 0.041(1) -0.010(1) 0.001(1) -0.005(1) C4 0.043(1) 0.035(1) 0.040(1) -0.0038(9) 0.004(1) -0.0021(9) C5 0.048(1) 0.033(1) 0.041(1) -0.001(1) 0.005(1) 0.003(1) C6 0.058(2) 0.036(1) 0.044(1) -0.001(1) 0.003(1) 0.001(1) N3 0.048(1) 0.047(1) 0.036(1) -0.0096(9) 0.0051(9) -0.0126(9) N4 0.045(1) 0.038(1) 0.040(1) 0.0039(9) 0.0078(9) 0.0044(9) C7 0.043(1) 0.044(1) 0.043(1) -0.005(1) 0.006(1) -0.004(1) C8 0.042(1) 0.047(1) 0.033(1) -0.000(1) 0.008(1) -0.003(1) C9 0.056(2) 0.055(2) 0.044(1) -0.009(1) 0.001(1) -0.009(1) C10 0.053(2) 0.047(1) 0.055(2) -0.011(1) -0.001(1) -0.006(1) C11 0.059(2) 0.047(2) 0.056(2) -0.011(1) 0.002(1) 0.000(1) C12 0.051(1) 0.049(2) 0.043(1) -0.007(1) -0.001(1) 0.002(1) C13 0.039(1) 0.044(1) 0.038(1) -0.003(1) 0.002(1) -0.007(1) N5 0.051(1) 0.037(1) 0.037(1) -0.0011(9) 0.0048(9) 0.0005(8) N6 0.054(1) 0.035(1) 0.032(1) -0.0004(9) 0.0026(9) -0.0036(8) N7 0.047(1) 0.036(1) 0.035(1) -0.0035(9) 0.0023(9) -0.0006(8) N8 0.052(1) 0.032(1) 0.040(1) -0.0034(9) 0.0024(9) -0.0033(8) C14 0.046(1) 0.033(1) 0.036(1) -0.006(1) -0.002(1) -0.0019(9) C15 0.044(1) 0.031(1) 0.038(1) -0.005(1) -0.001(1) -0.0021(9) C16 0.047(1) 0.035(1) 0.034(1) -0.005(1) -0.001(1) -0.0016(9) C17 0.056(1) 0.046(1) 0.035(1) -0.011(1) 0.000(1) 0.002(1) C18 0.075(2) 0.039(1) 0.047(1) 0.001(1) -0.004(1) 0.007(1) C19 0.071(2) 0.041(1) 0.055(2) 0.006(1) -0.002(1) -0.001(1) C20 0.052(1) 0.046(1) 0.044(1) 0.004(1) 0.003(1) -0.004(1) C24 0.062(2) 0.035(1) 0.047(1) -0.006(1) -0.005(1) 0.002(1) C22 0.048(1) 0.033(1) 0.038(1) -0.006(1) -0.002(1) -0.0039(9) C23 0.057(1) 0.041(1) 0.038(1) -0.014(1) -0.002(1) -0.005(1) C21 0.049(1) 0.033(1) 0.036(1) -0.004(1) -0.001(1) -0.0006(9) C25 0.067(2) 0.036(1) 0.054(2) 0.010(1) -0.000(1) -0.003(1) C26 0.062(2) 0.047(2) 0.049(2) 0.003(1) 0.012(1) -0.005(1) C27 0.045(1) 0.034(1) 0.040(1) -0.005(1) -0.001(1) -0.0027(9) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure Ver. 3.00' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C5 . 1.144(3) yes N2 . C6 . 1.142(4) yes C1 . C2 . 1.438(3) yes C1 . C4 . 1.366(3) yes C2 . C3 . 1.337(3) yes C2 . H1 . 1.080(4) no C3 . H2 . 1.150(6) no C4 . C5 . 1.439(4) yes C4 . C6 . 1.433(4) yes N3 . C7 . 1.375(3) yes N3 . C8 . 1.384(3) yes N3 . H3 . 0.986(5) no N4 . C7 . 1.333(3) yes N4 . C13 . 1.398(3) yes C8 . C9 . 1.384(4) yes C8 . C13 . 1.398(3) yes C9 . C10 . 1.370(4) yes C9 . H17 . 0.950(5) no C10 . C11 . 1.407(4) yes C10 . H16 . 0.950(5) no C11 . C12 . 1.366(4) yes C11 . H4 . 1.059(7) no C12 . C13 . 1.389(3) yes C12 . H5 . 1.146(5) no N5 . C14 . 1.349(3) yes N5 . C27 . 1.372(3) yes N5 . H6 . 0.933(4) no N6 . C15 . 1.330(3) yes N6 . C16 . 1.381(3) yes N6 . H7 . 0.893(4) no N7 . C15 . 1.333(3) yes N7 . C21 . 1.377(3) yes N7 . H8 . 0.907(3) no N8 . C14 . 1.323(3) yes N8 . C22 . 1.375(3) yes C14 . C15 . 1.429(3) yes C16 . C17 . 1.380(3) yes C16 . C21 . 1.392(3) yes C17 . C18 . 1.363(4) yes C17 . H18 . 0.950(4) no C18 . C19 . 1.407(4) yes C18 . H9 . 1.013(7) no C19 . C20 . 1.360(4) yes C19 . H10 . 0.996(5) no C20 . C21 . 1.391(3) yes C20 . H11 . 0.999(4) no C24 . C23 . 1.358(4) yes C24 . C25 . 1.411(4) yes C24 . H12 . 0.973(7) no C22 . C23 . 1.395(3) yes C22 . C27 . 1.405(3) yes C23 . H13 . 1.095(5) no C25 . C26 . 1.379(4) yes C25 . H14 . 1.120(6) no C26 . C27 . 1.386(3) yes C26 . H15 . 1.006(5) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C4 . 121.5(2) yes C1 . C2 . C3 . 120.8(2) yes C1 . C2 . H1 . 119.8(3) no C3 . C2 . H1 . 119.3(3) no C2 . C3 . H2 . 119.4(3) no C1 . C4 . C5 . 122.0(2) yes C1 . C4 . C6 . 122.4(2) yes C5 . C4 . C6 . 115.6(2) yes N1 . C5 . C4 . 178.4(3) yes N2 . C6 . C4 . 177.4(3) yes C7 . N3 . C8 . 104.7(2) yes C7 . N3 . H3 . 125.7(3) no C8 . N3 . H3 . 127.5(3) no C7 . N4 . C13 . 101.2(2) yes N3 . C7 . N4 . 116.2(2) yes N3 . C8 . C9 . 130.9(2) yes N3 . C8 . C13 . 105.6(2) yes C9 . C8 . C13 . 123.5(2) yes C8 . C9 . C10 . 116.6(3) yes C8 . C9 . H17 . 121.5(3) no C10 . C9 . H17 . 121.8(4) no C9 . C10 . C11 . 121.1(3) yes C9 . C10 . H16 . 119.9(4) no C11 . C10 . H16 . 119.0(4) no C10 . C11 . C12 . 121.4(3) yes C10 . C11 . H4 . 122.2(3) no C12 . C11 . H4 . 116.4(3) no C11 . C12 . C13 . 118.9(3) yes C11 . C12 . H5 . 121.6(3) no C13 . C12 . H5 . 118.8(3) no N4 . C13 . C8 . 112.1(2) yes N4 . C13 . C12 . 129.4(2) yes C8 . C13 . C12 . 118.5(2) yes C14 . N5 . C27 . 105.9(2) yes C14 . N5 . H6 . 124.5(3) no C27 . N5 . H6 . 129.3(3) no C15 . N6 . C16 . 108.5(2) yes C15 . N6 . H7 . 126.7(3) no C16 . N6 . H7 . 124.9(3) no C15 . N7 . C21 . 108.3(2) yes C15 . N7 . H8 . 125.1(3) no C21 . N7 . H8 . 126.1(3) no C14 . N8 . C22 . 103.7(2) yes N5 . C14 . N8 . 114.6(2) yes N5 . C14 . C15 . 123.7(2) yes N8 . C14 . C15 . 121.6(2) yes N6 . C15 . N7 . 110.0(2) yes N6 . C15 . C14 . 126.0(2) yes N7 . C15 . C14 . 124.0(2) yes N6 . C16 . C17 . 131.6(2) yes N6 . C16 . C21 . 106.44(19) yes C17 . C16 . C21 . 122.0(2) yes C16 . C17 . C18 . 116.6(2) yes C16 . C17 . H18 . 121.0(3) no C18 . C17 . H18 . 122.4(3) no C17 . C18 . C19 . 121.6(2) yes C17 . C18 . H9 . 117.4(3) no C19 . C18 . H9 . 120.7(4) no C18 . C19 . C20 . 122.1(3) yes C18 . C19 . H10 . 110.0(4) no C20 . C19 . H10 . 128.0(4) no C19 . C20 . C21 . 116.5(3) yes C19 . C20 . H11 . 124.1(3) no C21 . C20 . H11 . 119.2(3) no C23 . C24 . C25 . 121.7(2) yes C23 . C24 . H12 . 117.9(3) no C25 . C24 . H12 . 120.3(3) no N8 . C22 . C23 . 129.8(2) yes N8 . C22 . C27 . 110.1(2) yes C23 . C22 . C27 . 120.1(2) yes C24 . C23 . C22 . 117.6(2) yes C24 . C23 . H13 . 125.1(3) no C22 . C23 . H13 . 117.2(3) no N7 . C21 . C16 . 106.8(2) yes N7 . C21 . C20 . 132.0(2) yes C16 . C21 . C20 . 121.2(2) yes C24 . C25 . C26 . 121.9(3) yes C24 . C25 . H14 . 117.7(3) no C26 . C25 . H14 . 120.4(3) no C25 . C26 . C27 . 115.8(3) yes C25 . C26 . H15 . 118.8(4) no C27 . C26 . H15 . 125.3(3) no N5 . C27 . C22 . 105.6(2) yes N5 . C27 . C26 . 131.6(2) yes C22 . C27 . C26 . 122.7(2) yes #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================