# Copyright The Royal Society of Chemistry, 1999 # CCDC Number :182/1119 data_kcarb _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C32 H76 K2 N6 Si4' _chemical_formula_weight 735.55 _chemical_melting_point ? _chemical_compound_source ? 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' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'K' 'K' 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4128(12) _cell_length_b 10.937(3) _cell_length_c 12.306(2) _cell_angle_alpha 73.97(2) _cell_angle_beta 73.132(12) _cell_angle_gamma 69.426(10) _cell_volume 1113.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 130 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'Irregular Block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.097 _exptl_crystal_density_method ? _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.348 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.774504 _exptl_absorpt_correction_T_max 0.887862 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.14 _diffrn_reflns_number 11499 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5034 _reflns_number_observed 4058 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0438P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5034 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0343 _refine_ls_R_factor_obs 0.0266 _refine_ls_wR_factor_all 0.0762 _refine_ls_wR_factor_obs 0.0743 _refine_ls_goodness_of_fit_all 0.988 _refine_ls_goodness_of_fit_obs 1.077 _refine_ls_restrained_S_all 0.988 _refine_ls_restrained_S_obs 1.077 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group K1 K 0.11811(3) 0.97106(3) 0.11082(2) 0.02696(8) Uani 1 d . . Si1 Si 0.15997(4) 1.20943(4) -0.15326(3) 0.02235(9) Uani 1 d . . Si2 Si 0.15270(4) 0.70000(3) -0.01774(3) 0.02170(9) Uani 1 d . . N1 N 0.00112(12) 0.80333(10) 0.05429(9) 0.0226(2) Uani 1 d . . N2 N 0.25374(12) 0.95569(11) 0.38261(9) 0.0234(2) Uani 1 d . . N6 N 0.28142(12) 0.74025(11) 0.38040(9) 0.0231(2) Uani 1 d . . C1 C 0.23989(14) 0.86936(13) 0.32944(11) 0.0219(3) Uani 1 d . . C3 C 0.3157(2) 0.92015(14) 0.48752(13) 0.0324(3) Uani 1 d . . H3A H 0.2291(2) 0.92793(14) 0.55637(13) 0.039 Uiso 1 calc R . H3B H 0.3736(2) 0.98205(14) 0.48314(13) 0.039 Uiso 1 calc R . C4 C 0.4226(2) 0.77897(15) 0.49872(14) 0.0358(3) Uani 1 d . . H4A H 0.5186(2) 0.77468(15) 0.43753(14) 0.043 Uiso 1 calc R . H4B H 0.4521(2) 0.75011(15) 0.57485(14) 0.043 Uiso 1 calc R . C5 C 0.3411(2) 0.68798(14) 0.48748(12) 0.0305(3) Uani 1 d . . H5A H 0.4146(2) 0.59753(14) 0.48554(12) 0.037 Uiso 1 calc R . H5B H 0.2541(2) 0.68195(14) 0.55511(12) 0.037 Uiso 1 calc R . C7 C 0.2102(2) 1.09826(13) 0.32870(12) 0.0266(3) Uani 1 d . . H7A H 0.1501(2) 1.10905(13) 0.26995(12) 0.032 Uiso 1 calc R . C8 C 0.3510(2) 1.1450(2) 0.2645(2) 0.0512(5) Uani 1 d . . H8A H 0.4170(2) 1.0873(2) 0.2094(2) 0.077 Uiso 1 calc R . H8B H 0.4099(2) 1.1410(2) 0.3199(2) 0.077 Uiso 1 calc R . H8C H 0.3173(2) 1.2368(2) 0.2227(2) 0.077 Uiso 1 calc R . C9 C 0.1042(2) 1.1842(2) 0.41530(14) 0.0410(4) Uani 1 d . . H9A H 0.0144(2) 1.1514(2) 0.45527(14) 0.062 Uiso 1 calc R . H9B H 0.0684(2) 1.2765(2) 0.37472(14) 0.062 Uiso 1 calc R . H9C H 0.1610(2) 1.1806(2) 0.47196(14) 0.062 Uiso 1 calc R . C10 C 0.27172(15) 0.64107(13) 0.32456(12) 0.0249(3) Uani 1 d . . H10A H 0.21368(15) 0.69107(13) 0.26158(12) 0.030 Uiso 1 calc R . C11 C 0.1806(2) 0.5496(2) 0.40849(14) 0.0373(3) Uani 1 d . . H11A H 0.0781(2) 0.6033(2) 0.44336(14) 0.056 Uiso 1 calc R . H11B H 0.2371(2) 0.4956(2) 0.46944(14) 0.056 Uiso 1 calc R . H11C H 0.1679(2) 0.4911(2) 0.36664(14) 0.056 Uiso 1 calc R . C12 C 0.4328(2) 0.56164(15) 0.26781(13) 0.0331(3) Uani 1 d . . H12A H 0.4884(2) 0.62308(15) 0.21447(13) 0.050 Uiso 1 calc R . H12B H 0.4221(2) 0.50321(15) 0.22489(13) 0.050 Uiso 1 calc R . H12C H 0.4912(2) 0.50770(15) 0.32767(13) 0.050 Uiso 1 calc R . C13 C 0.3405(2) 1.1487(2) -0.09110(13) 0.0349(3) Uani 1 d . . H13A H 0.4300(3) 1.1609(10) -0.1532(2) 0.052 Uiso 1 calc R . H13B H 0.3592(7) 1.0541(3) -0.0555(8) 0.052 Uiso 1 calc R . H13C H 0.3256(5) 1.1997(7) -0.0325(7) 0.052 Uiso 1 calc R . C14 C 0.2035(2) 1.1024(2) -0.26326(13) 0.0354(3) Uani 1 d . . H14A H 0.2992(7) 1.1098(8) -0.3200(5) 0.053 Uiso 1 calc R . H14B H 0.1172(6) 1.1327(7) -0.3030(6) 0.053 Uiso 1 calc R . H14C H 0.2166(12) 1.0094(2) -0.2237(2) 0.053 Uiso 1 calc R . C15 C 0.1606(2) 1.38010(15) -0.24177(13) 0.0348(3) Uani 1 d . . H15A H 0.1386(2) 1.44141(15) -0.19000(13) 0.052 Uiso 1 calc R . H15B H 0.0807(2) 1.41225(15) -0.28779(13) 0.052 Uiso 1 calc R . H15C H 0.2627(2) 1.37537(15) -0.29354(13) 0.052 Uiso 1 calc R . C16 C 0.3400(2) 0.73803(15) -0.03395(13) 0.0331(3) Uani 1 d . . H16A H 0.4264(2) 0.6764(7) -0.0772(8) 0.050 Uiso 1 calc R . H16B H 0.3587(6) 0.7276(10) 0.04284(13) 0.050 Uiso 1 calc R . H16C H 0.3317(5) 0.8297(4) -0.0759(8) 0.050 Uiso 1 calc R . C17 C 0.1397(2) 0.71672(14) -0.17202(12) 0.0323(3) Uani 1 d . . H17A H 0.1185(2) 0.81059(14) -0.21048(12) 0.048 Uiso 1 calc R . H17B H 0.0556(2) 0.68344(14) -0.17185(12) 0.048 Uiso 1 calc R . H17C H 0.2383(2) 0.66478(14) -0.21365(12) 0.048 Uiso 1 calc R . C18 C 0.1934(2) 0.51677(14) 0.04708(13) 0.0326(3) Uani 1 d . . H18A H 0.2015(2) 0.50179(14) 0.12763(13) 0.049 Uiso 1 calc R . H18B H 0.2914(2) 0.46731(14) 0.00275(13) 0.049 Uiso 1 calc R . H18C H 0.1087(2) 0.48597(14) 0.04455(13) 0.049 Uiso 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 K1 0.0372(2) 0.0239(2) 0.0236(2) -0.00100(12) -0.01362(12) -0.01058(12) Si1 0.0243(2) 0.0209(2) 0.0220(2) -0.00442(14) -0.00354(14) -0.00771(14) Si2 0.0226(2) 0.0195(2) 0.0221(2) -0.00406(14) -0.00497(14) -0.00494(14) N1 0.0253(5) 0.0192(5) 0.0225(6) -0.0036(4) -0.0043(4) -0.0066(4) N2 0.0290(6) 0.0208(5) 0.0209(6) -0.0033(4) -0.0088(4) -0.0057(4) N6 0.0285(6) 0.0206(6) 0.0204(6) -0.0025(4) -0.0103(4) -0.0046(4) C1 0.0204(6) 0.0227(6) 0.0210(6) -0.0043(5) -0.0039(5) -0.0048(5) C3 0.0450(8) 0.0293(8) 0.0288(8) -0.0047(6) -0.0180(6) -0.0104(6) C4 0.0428(9) 0.0329(8) 0.0365(8) -0.0021(7) -0.0242(7) -0.0078(7) C5 0.0406(8) 0.0249(7) 0.0256(7) -0.0022(6) -0.0170(6) -0.0034(6) C7 0.0328(7) 0.0193(6) 0.0267(7) -0.0045(6) -0.0098(6) -0.0038(5) C8 0.0481(10) 0.0322(9) 0.0539(11) 0.0000(8) 0.0101(8) -0.0122(7) C9 0.0412(9) 0.0295(8) 0.0428(9) -0.0122(7) -0.0006(7) -0.0020(7) C10 0.0297(7) 0.0210(6) 0.0246(7) -0.0046(5) -0.0090(5) -0.0054(5) C11 0.0446(9) 0.0330(8) 0.0383(9) -0.0065(7) -0.0061(7) -0.0188(7) C12 0.0347(8) 0.0309(8) 0.0323(8) -0.0109(6) -0.0086(6) -0.0032(6) C13 0.0285(7) 0.0359(8) 0.0403(9) -0.0059(7) -0.0083(6) -0.0099(6) C14 0.0394(8) 0.0387(9) 0.0298(8) -0.0140(7) 0.0026(6) -0.0161(7) C15 0.0364(8) 0.0302(8) 0.0346(8) -0.0001(6) -0.0030(6) -0.0142(6) C16 0.0261(7) 0.0359(8) 0.0362(8) -0.0082(7) -0.0040(6) -0.0089(6) C17 0.0403(8) 0.0270(7) 0.0286(8) -0.0079(6) -0.0080(6) -0.0063(6) C18 0.0332(7) 0.0231(7) 0.0377(8) -0.0044(6) -0.0091(6) -0.0040(6) _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 K1 N1 2.7625(12) . ? K1 N1 2.8434(13) 2_575 ? K1 C1 3.0051(13) . ? K1 K1 3.7895(7) 2_575 ? Si1 N1 1.6689(11) 2_575 ? Si1 C15 1.885(2) . ? Si1 C14 1.894(2) . ? Si1 C13 1.8957(14) . ? Si2 N1 1.6688(12) . ? Si2 C18 1.8852(15) . ? Si2 C17 1.8924(15) . ? Si2 C16 1.8938(14) . ? N1 Si1 1.6689(11) 2_575 ? N1 K1 2.8434(13) 2_575 ? N2 C1 1.347(2) . ? N2 C3 1.469(2) . ? N2 C7 1.475(2) . ? N6 C1 1.344(2) . ? N6 C5 1.472(2) . ? N6 C10 1.475(2) . ? C3 C4 1.512(2) . ? C4 C5 1.507(2) . ? C7 C8 1.512(2) . ? C7 C9 1.514(2) . ? C10 C11 1.524(2) . ? C10 C12 1.529(2) . ? 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 K1 N1 94.95(3) . 2_575 ? N1 K1 C1 116.03(4) . . ? N1 K1 C1 146.92(4) 2_575 . ? N1 K1 K1 48.38(3) . 2_575 ? N1 K1 K1 46.57(3) 2_575 2_575 ? C1 K1 K1 161.54(3) . 2_575 ? N1 Si1 C15 117.24(6) 2_575 . ? N1 Si1 C14 110.45(6) 2_575 . ? C15 Si1 C14 104.92(7) . . ? N1 Si1 C13 113.67(6) 2_575 . ? C15 Si1 C13 104.46(7) . . ? C14 Si1 C13 105.04(7) . . ? N1 Si2 C18 116.85(6) . . ? N1 Si2 C17 113.03(6) . . ? C18 Si2 C17 105.70(7) . . ? N1 Si2 C16 111.44(6) . . ? C18 Si2 C16 104.84(7) . . ? C17 Si2 C16 103.85(7) . . ? Si2 N1 Si1 136.04(7) . 2_575 ? Si2 N1 K1 106.35(5) . . ? Si1 N1 K1 108.16(5) 2_575 . ? Si2 N1 K1 107.52(5) . 2_575 ? Si1 N1 K1 101.82(5) 2_575 2_575 ? K1 N1 K1 85.05(3) . 2_575 ? C1 N2 C3 125.73(11) . . ? C1 N2 C7 117.79(10) . . ? C3 N2 C7 116.42(11) . . ? C1 N6 C5 125.01(11) . . ? C1 N6 C10 118.55(10) . . ? C5 N6 C10 116.42(10) . . ? N6 C1 N2 116.26(11) . . ? N6 C1 K1 123.98(8) . . ? N2 C1 K1 119.76(8) . . ? N2 C3 C4 109.62(12) . . ? C5 C4 C3 109.48(12) . . ? N6 C5 C4 109.57(12) . . ? N2 C7 C8 111.99(11) . . ? N2 C7 C9 112.03(12) . . ? C8 C7 C9 111.58(13) . . ? N6 C10 C11 111.87(11) . . ? N6 C10 C12 111.44(11) . . ? C11 C10 C12 111.43(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 Si2 N1 Si1 -20.77(12) . . . 2_575 ? C17 Si2 N1 Si1 102.24(11) . . . 2_575 ? C16 Si2 N1 Si1 -141.25(10) . . . 2_575 ? C18 Si2 N1 K1 119.77(6) . . . . ? C17 Si2 N1 K1 -117.21(6) . . . . ? C16 Si2 N1 K1 -0.70(7) . . . . ? C18 Si2 N1 K1 -150.32(6) . . . 2_575 ? C17 Si2 N1 K1 -27.31(7) . . . 2_575 ? C16 Si2 N1 K1 89.20(7) . . . 2_575 ? N1 K1 N1 Si2 106.83(6) 2_575 . . . ? C1 K1 N1 Si2 -85.15(6) . . . . ? K1 K1 N1 Si2 106.83(6) 2_575 . . . ? N1 K1 N1 Si1 -100.83(6) 2_575 . . 2_575 ? C1 K1 N1 Si1 67.20(6) . . . 2_575 ? K1 K1 N1 Si1 -100.83(6) 2_575 . . 2_575 ? N1 K1 N1 K1 0.0 2_575 . . 2_575 ? C1 K1 N1 K1 168.03(3) . . . 2_575 ? K1 K1 N1 K1 0.0 2_575 . . 2_575 ? C5 N6 C1 N2 -0.6(2) . . . . ? C10 N6 C1 N2 -178.73(10) . . . . ? C5 N6 C1 K1 -179.92(9) . . . . ? C10 N6 C1 K1 1.97(15) . . . . ? C3 N2 C1 N6 2.7(2) . . . . ? C7 N2 C1 N6 179.59(11) . . . . ? C3 N2 C1 K1 -178.01(10) . . . . ? C7 N2 C1 K1 -1.08(14) . . . . ? N1 K1 C1 N6 19.79(11) . . . . ? N1 K1 C1 N6 177.54(8) 2_575 . . . ? K1 K1 C1 N6 49.1(2) 2_575 . . . ? N1 K1 C1 N2 -159.49(8) . . . . ? N1 K1 C1 N2 -1.74(13) 2_575 . . . ? K1 K1 C1 N2 -130.16(9) 2_575 . . . ? C1 N2 C3 C4 24.3(2) . . . . ? C7 N2 C3 C4 -152.68(12) . . . . ? N2 C3 C4 C5 -51.0(2) . . . . ? C1 N6 C5 C4 -28.1(2) . . . . ? C10 N6 C5 C4 150.01(12) . . . . ? C3 C4 C5 N6 52.8(2) . . . . ? C1 N2 C7 C8 -102.23(15) . . . . ? C3 N2 C7 C8 75.0(2) . . . . ? C1 N2 C7 C9 131.52(13) . . . . ? C3 N2 C7 C9 -51.3(2) . . . . ? C1 N6 C10 C11 -128.28(13) . . . . ? C5 N6 C10 C11 53.5(2) . . . . ? C1 N6 C10 C12 106.23(13) . . . . ? C5 N6 C10 C12 -72.04(15) . . . . ? _refine_diff_density_max 0.264 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.040 #=END data_jim3 _audit_creation_method shelxl _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'c10 h21 b f4 n2' _chemical_formula_weight 256.10 _chemical_melting_point ? _chemical_compound_source ? 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' 'b' 'b' 0.0013 0.0007 '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' 'f' 'f' 0.0171 0.0103 'international tables vol c tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_h-m P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.434(10) _cell_length_b 10.467(3) _cell_length_c 15.389(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1358.57(5) _cell_formula_units_z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 159 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.5 _exptl_crystal_description 'Irregular Block' _exptl_crystal_colour Colourless _exptl_crystal_size_max .4 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method ? _exptl_crystal_f_000 544 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type 'SADABS (Sheldrick, 1996)' _exptl_absorpt_correction_t_min 0.835895 _exptl_absorpt_correction_t_max 1.000000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8599 _diffrn_reflns_av_r_equivalents 0.0307 _diffrn_reflns_av_sigmai/neti 0.0419 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.53 _reflns_number_total 3095 _reflns_number_observed 2184 _reflns_observed_criterion >2sigma(i) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; refinement on f^2^ for all reflections except for 0 with very negative f^2^ or flagged by the user for potential systematic errors. weighted r-factors wr and all goodnesses 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 observed criterion of f^2^ > 2sigma(f^2^) is used only for calculating _r_factor_obs 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 w=1/[\s^2^(fo^2^)+(0.0472p)^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 ? _refine_ls_extinction_method shelxl _refine_ls_extinction_coef 0.0089(21) _refine_ls_extinction_expression 'fc^*^=kfc[1+0.001xfc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'flack h d (1983), acta cryst. a39, 876-881' _refine_ls_abs_structure_flack 1.36(124) _refine_ls_number_reflns 3095 _refine_ls_number_parameters 199 _refine_ls_number_restraints 94 _refine_ls_r_factor_all 0.0664 _refine_ls_r_factor_obs 0.0394 _refine_ls_wr_factor_all 0.0958 _refine_ls_wr_factor_obs 0.0850 _refine_ls_goodness_of_fit_all 0.977 _refine_ls_goodness_of_fit_obs 1.046 _refine_ls_restrained_s_all 1.452 _refine_ls_restrained_s_obs 1.658 _refine_ls_shift/esd_max -0.032 _refine_ls_shift/esd_mean 0.005 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group n1 n 0.2505(3) 0.5896(2) 0.36727(11) 0.0294(5) uani 1 d . . n2 n 0.2456(2) 0.8111(2) 0.35599(11) 0.0295(4) uani 1 d . . c1 c 0.2207(3) 0.7040(2) 0.39788(15) 0.0283(5) uani 1 d . . h1 h 0.1767(33) 0.7068(27) 0.4585(19) 0.050 uiso 1 d . . c2 c 0.3138(3) 0.5725(2) 0.2790(2) 0.0361(6) uani 1 d . . h2a h 0.2712(3) 0.4929(2) 0.2533(2) 0.043 uiso 1 calc r . h2b h 0.4308(3) 0.5654(2) 0.2813(2) 0.043 uiso 1 calc r . c3 c 0.2666(3) 0.6861(2) 0.2237(2) 0.0388(6) uani 1 d . . h3a h 0.1506(3) 0.6848(2) 0.2138(2) 0.047 uiso 1 calc r . h3b h 0.3198(3) 0.6806(2) 0.1665(2) 0.047 uiso 1 calc r . c4 c 0.3130(3) 0.8103(2) 0.2684(2) 0.0347(6) uani 1 d . . h4a h 0.4299(3) 0.8171(2) 0.2717(2) 0.042 uiso 1 calc r . h4b h 0.2723(3) 0.8840(2) 0.2349(2) 0.042 uiso 1 calc r . c5 c 0.2243(3) 0.4763(2) 0.4232(2) 0.0360(6) uani 1 d . . h5 h 0.2016(3) 0.5077(2) 0.4833(2) 0.043 uiso 1 calc r . c6 c 0.0808(3) 0.4011(3) 0.3928(2) 0.0465(7) uani 1 d . . h6a h 0.0597(14) 0.3313(11) 0.4337(7) 0.070 uiso 1 calc r . h6b h 0.1016(9) 0.3656(15) 0.3350(6) 0.070 uiso 1 calc r . h6c h -0.0117(6) 0.4577(5) 0.3901(12) 0.070 uiso 1 calc r . c7 c 0.3725(4) 0.3948(3) 0.4274(2) 0.0500(8) uani 1 d . . h7a h 0.3874(13) 0.3508(14) 0.3717(5) 0.075 uiso 1 calc r . h7b h 0.3614(10) 0.3315(12) 0.4739(8) 0.075 uiso 1 calc r . h7c h 0.4645(5) 0.4492(4) 0.4392(12) 0.075 uiso 1 calc r . c8 c 0.2085(3) 0.9346(2) 0.3987(2) 0.0372(6) uani 1 d . . h8 h 0.1782(3) 0.9162(2) 0.4602(2) 0.045 uiso 1 calc r . c9 c 0.0690(3) 0.9997(3) 0.3553(2) 0.0464(7) uani 1 d . . h9a h 0.0413(15) 1.0771(10) 0.3878(7) 0.070 uiso 1 calc r . h9b h -0.0219(7) 0.9414(7) 0.3546(11) 0.070 uiso 1 calc r . h9c h 0.0975(8) 1.0227(16) 0.2956(5) 0.070 uiso 1 calc r . c10 c 0.3542(4) 1.0187(3) 0.4001(2) 0.0572(9) uani 1 d . . h10a h 0.3366(10) 1.0906(12) 0.4397(11) 0.086 uiso 1 calc r . h10b h 0.3749(15) 1.0512(17) 0.3415(3) 0.086 uiso 1 calc r . h10c h 0.4455(6) 0.9688(6) 0.4201(14) 0.086 uiso 1 calc r . b1 b -0.2609(4) 0.7027(3) 0.3607(2) 0.0444(7) uani 0.53(2) d pd 1 f1 f -0.2171(19) 0.7396(8) 0.2785(5) 0.114(4) uani 0.53(2) d pd 1 f2 f -0.2880(10) 0.5746(5) 0.3557(5) 0.069(2) uani 0.53(2) d pd 1 f3 f -0.1268(7) 0.7118(7) 0.4189(3) 0.050(2) uani 0.53(2) d pd 1 f4 f -0.3370(18) 0.8012(14) 0.3912(6) 0.139(5) uani 0.53(2) d pd 1 b1' b -0.2609(4) 0.7027(3) 0.3607(2) 0.0444(7) uani 0.47(2) d pd 2 f1' f -0.2799(14) 0.7457(12) 0.2802(6) 0.104(4) uani 0.47(2) d pd 2 f2' f -0.3167(16) 0.5871(11) 0.3679(8) 0.148(6) uani 0.47(2) d pd 2 f3' f -0.1219(13) 0.7136(13) 0.3874(15) 0.175(6) uani 0.47(2) d pd 2 f4' f -0.3976(7) 0.7454(8) 0.4078(5) 0.058(2) uani 0.47(2) d pd 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 n1 0.0350(12) 0.0225(9) 0.0307(10) -0.0009(8) 0.0029(10) 0.0003(9) n2 0.0344(11) 0.0243(10) 0.0298(10) -0.0001(8) -0.0014(10) 0.0000(9) c1 0.0297(12) 0.0270(11) 0.0283(11) -0.0011(10) -0.0015(10) -0.0005(11) c2 0.042(2) 0.0330(14) 0.0334(13) -0.0047(11) 0.0042(12) -0.0006(11) c3 0.048(2) 0.0391(14) 0.0290(12) -0.0025(10) 0.0022(13) -0.0016(14) c4 0.0383(15) 0.0337(13) 0.0322(12) 0.0045(11) 0.0026(11) -0.0018(12) c5 0.051(2) 0.0236(11) 0.0338(12) 0.0012(9) 0.0041(13) -0.0037(12) c6 0.051(2) 0.035(2) 0.054(2) 0.0008(13) 0.008(2) -0.0089(13) c7 0.059(2) 0.034(2) 0.057(2) 0.0093(14) -0.010(2) 0.0039(14) c8 0.053(2) 0.0231(12) 0.0361(12) -0.0031(10) -0.0031(13) 0.0028(11) c9 0.047(2) 0.036(2) 0.057(2) -0.0007(13) -0.0023(15) 0.0088(13) c10 0.059(2) 0.036(2) 0.077(2) -0.0101(15) -0.026(2) -0.0024(14) b1 0.043(2) 0.047(2) 0.043(2) -0.0040(15) 0.002(2) 0.003(2) f1 0.221(12) 0.069(4) 0.051(3) 0.000(3) 0.056(5) -0.006(6) f2 0.083(4) 0.036(3) 0.088(4) -0.020(3) 0.008(3) 0.003(3) f3 0.030(3) 0.072(3) 0.046(3) -0.003(2) -0.003(2) -0.005(2) f4 0.159(10) 0.185(10) 0.073(4) -0.049(6) -0.022(5) 0.122(8) b1' 0.043(2) 0.047(2) 0.043(2) -0.0040(15) 0.002(2) 0.003(2) f1' 0.105(6) 0.130(7) 0.076(5) 0.065(5) 0.050(4) 0.058(5) f2' 0.145(9) 0.181(11) 0.118(7) 0.086(7) -0.061(6) -0.127(9) f3' 0.069(6) 0.142(9) 0.315(18) 0.066(11) -0.090(9) -0.044(6) f4' 0.037(3) 0.100(5) 0.038(3) -0.013(3) -0.005(2) 0.025(2) _geom_special_details ; all esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. the cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. an approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag n1 c1 1.311(3) . ? n1 c2 1.470(3) . ? n1 c5 1.481(3) . ? n2 c1 1.310(3) . ? n2 c4 1.462(3) . ? n2 c8 1.483(3) . ? c2 c3 1.516(3) . ? c3 c4 1.522(3) . ? c5 c7 1.515(4) . ? c5 c6 1.518(4) . ? c8 c10 1.512(4) . ? c8 c9 1.514(4) . ? b1 f4 1.303(8) . ? b1 f2 1.362(7) . ? b1 f1 1.374(9) . ? b1 f3 1.445(7) . ? b1' f3' 1.248(10) . ? b1' f2' 1.303(10) . ? b1' f1' 1.328(10) . ? b1' f4' 1.433(7) . ? 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 c2 120.8(2) . . ? c1 n1 c5 119.6(2) . . ? c2 n1 c5 119.5(2) . . ? c1 n2 c4 120.7(2) . . ? c1 n2 c8 119.6(2) . . ? c4 n2 c8 119.7(2) . . ? n2 c1 n1 125.1(2) . . ? n1 c2 c3 109.1(2) . . ? c2 c3 c4 110.4(2) . . ? n2 c4 c3 108.8(2) . . ? n1 c5 c7 110.7(2) . . ? n1 c5 c6 110.8(2) . . ? c7 c5 c6 112.2(2) . . ? n2 c8 c10 110.0(2) . . ? n2 c8 c9 111.2(2) . . ? c10 c8 c9 112.1(2) . . ? f4 b1 f2 135.8(10) . . ? f4 b1 f1 104.0(6) . . ? f2 b1 f1 105.7(5) . . ? f4 b1 f3 96.3(6) . . ? f2 b1 f3 103.4(5) . . ? f1 b1 f3 110.0(7) . . ? f3' b1' f2' 113.4(9) . . ? f3' b1' f1' 112.9(10) . . ? f2' b1' f1' 110.5(8) . . ? f3' b1' f4' 124.1(11) . . ? f2' b1' f4' 87.5(9) . . ? f1' b1' f4' 105.6(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag h1 c1 n1 c2 179.4(18) . . . . ? h1 c1 n2 c4 178.6(19) . . . . ? c2 n1 c1 n2 -1.2(4) . . . . ? n1 c1 n2 c4 -0.7(4) . . . . ? _refine_diff_density_max 0.157 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.032