Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Blanca Ruiz' B.J.Coe 'Reto Gianotti' 'Volker Gramlich' 'Peter Gunter' 'Mojca Jazbinsek' _publ_contact_author_name 'Blanca Ruiz' _publ_contact_author_address ; Department of Physics ETH Zurich ETH Hoenggerberg, IQE Non Linear Optics Laboratory HPF E 11, CH-8093 Zurich CH-8093 SWITZERLAND ; _publ_contact_author_email 'BLANKA@PHYS.ETHZ.CH ' _publ_section_title ; Polymorphism, crystal growth and characterization of an organic nonlinear optical material: DAPSH ; # Attachment 'dapsh_b.cifch' data_jh1b _database_code_depnum_ccdc_archive 'CCDC 642158' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 F6 N2 P' _chemical_formula_weight 446.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6313(9) _cell_length_b 10.9526(10) _cell_length_c 11.6996(12) _cell_angle_alpha 66.761(9) _cell_angle_beta 79.294(8) _cell_angle_gamma 68.581(9) _cell_volume 1054.46(18) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 12 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_absorpt_coefficient_mu 0.192 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details SHELXPREP _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ' \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 120 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8166 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.73 _diffrn_reflns_theta_max 26.05 _reflns_number_total 4140 _reflns_number_gt 2735 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SIEMENS SHELXTL Plus' _computing_cell_refinement 'SIEMENS SHELXTL Plus' _computing_data_reduction 'SIEMENS SHELXTL Plus' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXLTL-Plus _computing_publication_material SHELXL-93 _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^)+(0.2000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4140 _refine_ls_number_parameters 327 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.1080 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.2887 _refine_ls_wR_factor_gt 0.2592 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.184 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 P P 0.23644(10) 0.66311(9) 0.67538(9) 0.0836(4) Uani 1 1 d D . . N2 N 0.0708(2) 0.2688(2) 0.6260(2) 0.0632(6) Uani 1 1 d . . . C10 C 0.3973(3) 0.1399(3) 0.3642(3) 0.0714(8) Uani 1 1 d . . . H10A H 0.4539 0.1985 0.3198 0.086 Uiso 1 1 calc R . . C9 C 0.4238(3) 0.0263(3) 0.3376(3) 0.0717(8) Uani 1 1 d . . . H9A H 0.3702 -0.0334 0.3868 0.086 Uiso 1 1 calc R . . C11 C 0.2878(3) 0.1804(3) 0.4563(2) 0.0650(7) Uani 1 1 d . . . C15 C 0.2703(4) 0.3007(3) 0.4793(3) 0.0758(8) Uani 1 1 d . . . H15A H 0.3332 0.3534 0.4368 0.091 Uiso 1 1 calc R . . C6 C 0.5243(3) -0.0174(3) 0.2430(3) 0.0693(7) Uani 1 1 d . . . C14 C 0.1648(3) 0.3428(3) 0.5614(3) 0.0732(8) Uani 1 1 d . . . H14A H 0.1562 0.4240 0.5742 0.088 Uiso 1 1 calc R . . C16 C -0.0487(3) 0.3188(3) 0.7093(3) 0.0675(7) Uani 1 1 d . . . C12 C 0.1929(3) 0.1032(3) 0.5272(3) 0.0712(8) Uani 1 1 d . . . H12A H 0.2019 0.0200 0.5180 0.085 Uiso 1 1 calc R . . C5 C 0.5307(4) -0.1384(3) 0.2254(3) 0.0774(8) Uani 1 1 d . . . H5A H 0.4730 -0.1919 0.2791 0.093 Uiso 1 1 calc R . . C13 C 0.0887(4) 0.1488(3) 0.6086(3) 0.0737(8) Uani 1 1 d . . . H13A H 0.0268 0.0960 0.6543 0.088 Uiso 1 1 calc R . . C7 C 0.6174(4) 0.0567(3) 0.1610(3) 0.0768(8) Uani 1 1 d . . . H7A H 0.6189 0.1371 0.1695 0.092 Uiso 1 1 calc R . . C3 C 0.7070(3) -0.1053(3) 0.0507(3) 0.0741(8) Uani 1 1 d . . . N1 N 0.7942(4) -0.1489(3) -0.0418(3) 0.0925(9) Uani 1 1 d . . . C8 C 0.7055(4) 0.0137(4) 0.0692(3) 0.0819(9) Uani 1 1 d . . . H8A H 0.7663 0.0650 0.0175 0.098 Uiso 1 1 calc R . . C4 C 0.6172(4) -0.1820(3) 0.1337(3) 0.0776(8) Uani 1 1 d . . . H4A H 0.6168 -0.2632 0.1259 0.093 Uiso 1 1 calc R . . C17 C -0.1918(4) 0.3233(3) 0.6997(3) 0.0817(9) Uani 1 1 d . . . H17A H -0.2119 0.2957 0.6406 0.098 Uiso 1 1 calc R . . C21 C -0.0173(4) 0.3607(4) 0.7950(4) 0.0933(11) Uani 1 1 d . . . H21A H 0.0789 0.3589 0.7992 0.112 Uiso 1 1 calc R . . C2 C 0.7906(5) -0.2719(4) -0.0603(3) 0.0968(11) Uani 1 1 d . . . H2A H 0.7097 -0.3016 -0.0100 0.145 Uiso 1 1 calc R . . H2B H 0.8832 -0.3466 -0.0366 0.145 Uiso 1 1 calc R . . H2C H 0.7764 -0.2485 -0.1464 0.145 Uiso 1 1 calc R . . C18 C -0.3025(4) 0.3690(4) 0.7790(4) 0.0990(12) Uani 1 1 d . . . H18A H -0.3993 0.3727 0.7739 0.119 Uiso 1 1 calc R . . C19 C -0.2728(5) 0.4098(4) 0.8667(4) 0.1066(13) Uani 1 1 d . . . H19A H -0.3491 0.4404 0.9206 0.128 Uiso 1 1 calc R . . C20 C -0.1307(5) 0.4054(5) 0.8744(4) 0.1120(14) Uani 1 1 d . . . H20A H -0.1109 0.4328 0.9338 0.134 Uiso 1 1 calc R . . C1 C 0.8870(6) -0.0708(5) -0.1272(5) 0.138(2) Uani 1 1 d . . . H1A H 0.8799 0.0064 -0.1042 0.207 Uiso 1 1 calc R . . H1B H 0.8540 -0.0355 -0.2102 0.207 Uiso 1 1 calc R . . H1C H 0.9888 -0.1312 -0.1241 0.207 Uiso 1 1 calc R . . F1 F 0.3046(14) 0.7393(10) 0.5507(8) 0.177(6) Uani 0.50 1 d PD A 1 F2 F 0.3379(11) 0.5236(9) 0.6798(15) 0.233(8) Uani 0.50 1 d PD A 1 F6 F 0.1465(9) 0.6004(8) 0.7985(6) 0.119(2) Uani 0.50 1 d PD A 1 F4 F 0.1120(11) 0.8057(7) 0.6653(9) 0.150(3) Uani 0.50 1 d PD A 1 F5 F 0.1202(9) 0.6395(7) 0.6055(5) 0.116(2) Uani 0.50 1 d PD A 1 F3 F 0.3348(13) 0.6819(16) 0.7454(10) 0.220(7) Uani 0.50 1 d PD A 1 F1' F 0.222(2) 0.7675(14) 0.5412(9) 0.238(8) Uani 0.50 1 d PD A 2 F5' F 0.0860(10) 0.6676(17) 0.674(2) 0.323(10) Uani 0.50 1 d PD A 2 F3' F 0.3918(9) 0.6716(14) 0.6716(19) 0.236(8) Uani 0.50 1 d PD A 2 F2' F 0.3095(13) 0.5317(9) 0.6367(11) 0.196(7) Uani 0.50 1 d PD A 2 F4' F 0.1873(13) 0.7863(9) 0.7251(9) 0.149(3) Uani 0.50 1 d PD A 2 F6' F 0.253(2) 0.5568(10) 0.8026(8) 0.226(7) Uani 0.50 1 d PD 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 P 0.0903(7) 0.0705(6) 0.0993(7) -0.0312(5) 0.0065(5) -0.0408(5) N2 0.0748(14) 0.0496(12) 0.0632(12) -0.0151(10) -0.0047(10) -0.0228(10) C10 0.0784(18) 0.0676(17) 0.0680(16) -0.0178(14) -0.0001(13) -0.0320(14) C9 0.0792(18) 0.0666(17) 0.0664(16) -0.0178(14) -0.0034(13) -0.0271(14) C11 0.0735(16) 0.0577(15) 0.0606(14) -0.0123(12) -0.0072(12) -0.0255(12) C15 0.0801(18) 0.0651(17) 0.0868(19) -0.0235(15) 0.0052(14) -0.0372(14) C6 0.0708(17) 0.0666(17) 0.0678(15) -0.0182(14) -0.0014(12) -0.0264(13) C14 0.0772(18) 0.0540(15) 0.092(2) -0.0224(15) -0.0073(15) -0.0274(13) C16 0.0782(17) 0.0503(14) 0.0693(16) -0.0144(13) -0.0057(13) -0.0221(12) C12 0.093(2) 0.0552(15) 0.0691(16) -0.0216(13) 0.0034(14) -0.0323(14) C5 0.0818(19) 0.0721(18) 0.0831(19) -0.0256(16) 0.0086(14) -0.0388(15) C13 0.097(2) 0.0579(16) 0.0707(16) -0.0184(14) 0.0055(14) -0.0393(15) C7 0.0846(19) 0.0610(16) 0.088(2) -0.0236(15) -0.0020(15) -0.0310(14) C3 0.0752(18) 0.0619(17) 0.0703(16) -0.0158(14) -0.0011(13) -0.0154(13) N1 0.107(2) 0.0697(17) 0.0818(17) -0.0232(14) 0.0210(15) -0.0235(14) C8 0.0791(19) 0.0696(19) 0.086(2) -0.0175(16) 0.0157(15) -0.0327(15) C4 0.0830(19) 0.0715(19) 0.0820(19) -0.0305(16) 0.0036(15) -0.0295(15) C17 0.087(2) 0.073(2) 0.091(2) -0.0272(17) 0.0047(16) -0.0388(16) C21 0.085(2) 0.094(2) 0.112(3) -0.060(2) -0.0128(19) -0.0132(17) C2 0.118(3) 0.079(2) 0.081(2) -0.0304(18) 0.0025(18) -0.0193(19) C18 0.086(2) 0.082(2) 0.131(3) -0.039(2) 0.017(2) -0.0403(19) C19 0.108(3) 0.084(2) 0.122(3) -0.048(2) 0.027(2) -0.027(2) C20 0.114(3) 0.115(3) 0.123(3) -0.075(3) -0.005(2) -0.020(2) C1 0.163(4) 0.105(3) 0.128(4) -0.045(3) 0.074(3) -0.059(3) F1 0.266(12) 0.150(7) 0.160(9) -0.087(7) 0.140(10) -0.154(9) F2 0.155(7) 0.119(7) 0.38(2) -0.106(9) -0.060(10) 0.045(5) F6 0.157(6) 0.113(5) 0.088(4) -0.022(4) 0.025(4) -0.075(5) F4 0.182(8) 0.080(4) 0.172(8) -0.054(5) 0.036(6) -0.037(4) F5 0.153(6) 0.105(4) 0.110(3) -0.029(3) -0.039(3) -0.057(4) F3 0.191(11) 0.40(2) 0.208(9) -0.164(11) 0.008(8) -0.199(14) F1' 0.42(2) 0.196(11) 0.138(8) -0.025(7) -0.078(11) -0.149(13) F5' 0.141(8) 0.39(2) 0.53(3) -0.21(2) -0.084(13) -0.101(10) F3' 0.104(5) 0.257(12) 0.43(3) -0.198(17) 0.056(9) -0.104(6) F2' 0.312(17) 0.162(9) 0.212(9) -0.138(8) 0.085(9) -0.155(11) F4' 0.179(9) 0.113(5) 0.168(8) -0.088(6) 0.055(6) -0.049(6) F6' 0.41(2) 0.109(6) 0.111(6) 0.003(5) -0.041(11) -0.069(11) _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 P F5' 1.434(8) . ? P F2 1.469(7) . ? P F3 1.475(6) . ? P F6' 1.476(8) . ? P F3' 1.524(7) . ? P F1 1.529(6) . ? P F1' 1.530(10) . ? P F2' 1.558(7) . ? P F4 1.559(7) . ? P F4' 1.560(7) . ? P F6 1.577(6) . ? P F5 1.645(5) . ? N2 C13 1.353(4) . ? N2 C14 1.359(4) . ? N2 C16 1.455(4) . ? C10 C9 1.324(4) . ? C10 C11 1.444(4) . ? C9 C6 1.439(4) . ? C11 C15 1.391(4) . ? C11 C12 1.403(4) . ? C15 C14 1.346(4) . ? C6 C5 1.398(4) . ? C6 C7 1.407(4) . ? C16 C21 1.373(5) . ? C16 C17 1.385(4) . ? C12 C13 1.348(4) . ? C5 C4 1.362(4) . ? C7 C8 1.365(4) . ? C3 N1 1.372(4) . ? C3 C8 1.397(5) . ? C3 C4 1.404(4) . ? N1 C1 1.443(5) . ? N1 C2 1.460(5) . ? C17 C18 1.363(5) . ? C21 C20 1.374(5) . ? C18 C19 1.378(6) . ? C19 C20 1.370(6) . ? 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 F5' P F2 108.6(8) . . ? F5' P F3 142.4(8) . . ? F2 P F3 93.5(7) . . ? F5' P F6' 91.6(8) . . ? F2 P F6' 66.7(7) . . ? F3 P F6' 69.3(8) . . ? F5' P F3' 175.2(8) . . ? F2 P F3' 75.7(7) . . ? F3 P F3' 37.1(6) . . ? F6' P F3' 92.0(8) . . ? F5' P F1 115.9(9) . . ? F2 P F1 93.5(6) . . ? F3 P F1 91.7(5) . . ? F6' P F1 150.7(8) . . ? F3' P F1 61.2(7) . . ? F5' P F1' 88.4(8) . . ? F2 P F1' 110.7(8) . . ? F3 P F1' 112.2(7) . . ? F6' P F1' 177.3(6) . . ? F3' P F1' 88.2(7) . . ? F1 P F1' 28.5(8) . . ? F5' P F2' 94.8(7) . . ? F2 P F2' 21.8(8) . . ? F3 P F2' 113.6(7) . . ? F6' P F2' 83.1(5) . . ? F3' P F2' 88.7(6) . . ? F1 P F2' 84.6(5) . . ? F1' P F2' 94.1(6) . . ? F5' P F4 63.7(7) . . ? F2 P F4 172.0(6) . . ? F3 P F4 94.2(6) . . ? F6' P F4 114.3(6) . . ? F3' P F4 111.9(6) . . ? F1 P F4 88.3(5) . . ? F1' P F4 68.1(7) . . ? F2' P F4 151.4(6) . . ? F5' P F4' 93.4(7) . . ? F2 P F4' 149.3(7) . . ? F3 P F4' 57.0(6) . . ? F6' P F4' 92.2(6) . . ? F3' P F4' 83.3(5) . . ? F1 P F4' 95.8(5) . . ? F1' P F4' 90.5(6) . . ? F2' P F4' 170.6(6) . . ? F4 P F4' 37.8(4) . . ? F5' P F6 58.2(8) . . ? F2 P F6 92.8(6) . . ? F3 P F6 91.7(5) . . ? F6' P F6 36.5(6) . . ? F3' P F6 124.3(8) . . ? F1 P F6 172.6(5) . . ? F1' P F6 144.4(7) . . ? F2' P F6 100.0(5) . . ? F4 P F6 84.8(4) . . ? F4' P F6 80.6(5) . . ? F5' P F5 34.4(7) . . ? F2 P F5 87.2(6) . . ? F3 P F5 176.4(5) . . ? F6' P F5 107.8(6) . . ? F3' P F5 146.3(7) . . ? F1 P F5 91.8(5) . . ? F1' P F5 70.8(6) . . ? F2' P F5 67.7(4) . . ? F4 P F5 85.0(5) . . ? F4' P F5 121.6(5) . . ? F6 P F5 84.7(4) . . ? C13 N2 C14 118.3(2) . . ? C13 N2 C16 120.7(2) . . ? C14 N2 C16 121.1(2) . . ? C9 C10 C11 125.4(3) . . ? C10 C9 C6 128.9(3) . . ? C15 C11 C12 115.9(3) . . ? C15 C11 C10 121.1(3) . . ? C12 C11 C10 122.9(3) . . ? C14 C15 C11 121.9(3) . . ? C5 C6 C7 115.5(3) . . ? C5 C6 C9 120.2(3) . . ? C7 C6 C9 124.3(3) . . ? C15 C14 N2 121.1(3) . . ? C21 C16 C17 121.6(3) . . ? C21 C16 N2 119.4(3) . . ? C17 C16 N2 119.0(3) . . ? C13 C12 C11 120.4(3) . . ? C4 C5 C6 123.4(3) . . ? C12 C13 N2 122.3(3) . . ? C8 C7 C6 121.7(3) . . ? N1 C3 C8 122.4(3) . . ? N1 C3 C4 120.6(3) . . ? C8 C3 C4 117.0(3) . . ? C3 N1 C1 121.0(3) . . ? C3 N1 C2 121.0(3) . . ? C1 N1 C2 118.0(3) . . ? C7 C8 C3 121.9(3) . . ? C5 C4 C3 120.4(3) . . ? C18 C17 C16 118.5(3) . . ? C16 C21 C20 118.8(4) . . ? C17 C18 C19 120.8(4) . . ? C20 C19 C18 120.0(4) . . ? C19 C20 C21 120.4(4) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.398 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.059 # Attachment 'dapsh_c.cifch' data_jh1c _database_code_depnum_ccdc_archive 'CCDC 642159' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 F6 N2 O0 P' _chemical_formula_weight 446.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, -z-1/2' _cell_length_a 23.264(2) _cell_length_b 7.6256(10) _cell_length_c 35.890(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.850(9) _cell_angle_gamma 90.00 _cell_volume 6125.0(12) _cell_formula_units_Z 12 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 12 _cell_measurement_theta_min 10 _cell_measurement_theta_max 11 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2760 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details SHELXPREP _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ' \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1 _diffrn_standards_interval_count 120 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 45020 _diffrn_reflns_av_R_equivalents 0.2788 _diffrn_reflns_av_sigmaI/netI 0.2785 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 3.90 _diffrn_reflns_theta_max 26.06 _reflns_number_total 12077 _reflns_number_gt 3123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SIEMENS SHELXTL Plus' _computing_cell_refinement 'SIEMENS SHELXTL Plus' _computing_data_reduction 'SIEMENS SHELXTL Plus' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXLTL-Plus _computing_publication_material SHELXL-93 _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^)+(0.2000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12077 _refine_ls_number_parameters 811 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3874 _refine_ls_R_factor_gt 0.1553 _refine_ls_wR_factor_ref 0.4715 _refine_ls_wR_factor_gt 0.3409 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_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_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 P P -0.27333(13) 0.2167(4) 0.02745(9) 0.0703(9) Uani 1 1 d . . . F1 F -0.2388(4) 0.0882(11) 0.0066(2) 0.120(3) Uani 1 1 d . . . F2 F -0.2401(4) 0.3801(11) 0.0165(3) 0.132(3) Uani 1 1 d . . . F3 F -0.3233(4) 0.2440(11) -0.0111(2) 0.121(3) Uani 1 1 d . . . F4 F -0.3082(3) 0.3469(11) 0.0482(2) 0.118(3) Uani 1 1 d . . . F5 F -0.3077(3) 0.0573(10) 0.0390(2) 0.115(3) Uani 1 1 d . . . F6 F -0.2245(4) 0.1956(12) 0.0658(3) 0.128(3) Uani 1 1 d . . . P' P -0.10698(14) 0.0307(5) 0.19298(10) 0.0777(10) Uani 1 1 d . . . F1' F -0.0735(4) -0.1185(12) 0.1777(3) 0.149(3) Uani 1 1 d . . . F2' F -0.0728(4) 0.1745(12) 0.1755(2) 0.125(3) Uani 1 1 d . . . F3' F -0.1580(5) 0.0227(17) 0.1564(3) 0.184(5) Uani 1 1 d . . . F4' F -0.1397(3) 0.1824(11) 0.2096(2) 0.113(3) Uani 1 1 d . . . F5' F -0.1396(5) -0.1081(13) 0.2120(3) 0.167(4) Uani 1 1 d . . . F6' F -0.0566(4) 0.0461(12) 0.2316(2) 0.128(3) Uani 1 1 d . . . P" P 0.05885(14) 0.1464(4) 0.36186(9) 0.0710(9) Uani 1 1 d . . . F1" F 0.0953(4) -0.0072(10) 0.3498(2) 0.118(3) Uani 1 1 d . . . F2" F 0.0922(4) 0.2811(11) 0.3413(2) 0.125(3) Uani 1 1 d . . . F3" F 0.0091(4) 0.1213(11) 0.3235(2) 0.120(3) Uani 1 1 d . . . F4" F 0.0235(3) 0.3005(10) 0.3743(2) 0.118(3) Uani 1 1 d . . . F5" F 0.0261(3) 0.0102(10) 0.3830(2) 0.104(2) Uani 1 1 d . . . F6" F 0.1085(3) 0.1730(11) 0.4009(2) 0.111(2) Uani 1 1 d . . . N1 N 0.0104(4) -0.0888(14) -0.0802(3) 0.079(3) Uani 1 1 d . . . N2 N -0.2278(4) -0.3887(12) 0.1289(3) 0.069(2) Uani 1 1 d . . . N1' N 0.1790(4) -0.3566(13) 0.0831(3) 0.081(3) Uani 1 1 d . . . N2' N -0.0599(4) -0.4233(13) 0.3002(3) 0.072(3) Uani 1 1 d . . . N1" N 0.3415(4) -0.4279(13) 0.2499(3) 0.082(3) Uani 1 1 d . . . N2" N 0.1053(4) -0.2727(11) 0.4656(2) 0.065(2) Uani 1 1 d . . . C1 C 0.0698(5) -0.1577(17) -0.0744(4) 0.087(4) Uani 1 1 d . . . H1A H 0.0804 -0.2265 -0.0511 0.130 Uiso 1 1 calc R . . H1B H 0.0976 -0.0626 -0.0722 0.130 Uiso 1 1 calc R . . H1C H 0.0711 -0.2301 -0.0961 0.130 Uiso 1 1 calc R . . C2 C -0.0154(6) 0.0185(17) -0.1142(4) 0.091(4) Uani 1 1 d . . . H2A H -0.0550 0.0536 -0.1142 0.136 Uiso 1 1 calc R . . H2B H -0.0171 -0.0482 -0.1371 0.136 Uiso 1 1 calc R . . H2C H 0.0089 0.1207 -0.1136 0.136 Uiso 1 1 calc R . . C3 C -0.0226(5) -0.1247(12) -0.0551(3) 0.058(3) Uani 1 1 d . . . C4 C -0.0802(5) -0.0589(15) -0.0599(4) 0.077(3) Uani 1 1 d . . . H4A H -0.0978 0.0092 -0.0815 0.092 Uiso 1 1 calc R . . C5 C -0.1115(5) -0.0932(14) -0.0331(4) 0.074(3) Uani 1 1 d . . . H5A H -0.1494 -0.0452 -0.0368 0.089 Uiso 1 1 calc R . . C6 C -0.0880(5) -0.1976(13) -0.0006(3) 0.065(3) Uani 1 1 d . . . C7 C -0.0309(5) -0.2652(14) 0.0038(3) 0.068(3) Uani 1 1 d . . . H7A H -0.0144 -0.3381 0.0247 0.082 Uiso 1 1 calc R . . C8 C 0.0009(5) -0.2287(14) -0.0212(3) 0.065(3) Uani 1 1 d . . . H8A H 0.0395 -0.2724 -0.0163 0.078 Uiso 1 1 calc R . . C9 C -0.1248(4) -0.2322(13) 0.0265(3) 0.064(3) Uani 1 1 d . . . H9A H -0.1627 -0.1825 0.0196 0.077 Uiso 1 1 calc R . . C10 C -0.1108(4) -0.3246(15) 0.0592(3) 0.064(3) Uani 1 1 d . . . H10A H -0.0738 -0.3795 0.0669 0.076 Uiso 1 1 calc R . . C11 C -0.1516(5) -0.3425(12) 0.0832(3) 0.055(3) Uani 1 1 d . . . C12 C -0.2032(5) -0.2479(15) 0.0776(3) 0.076(3) Uani 1 1 d . . . H12A H -0.2134 -0.1665 0.0576 0.092 Uiso 1 1 calc R . . C13 C -0.2398(6) -0.2715(16) 0.1010(4) 0.087(4) Uani 1 1 d . . . H13A H -0.2741 -0.2032 0.0971 0.105 Uiso 1 1 calc R . . C14 C -0.1779(6) -0.4814(17) 0.1370(3) 0.086(4) Uani 1 1 d . . . H14A H -0.1692 -0.5594 0.1577 0.103 Uiso 1 1 calc R . . C15 C -0.1378(5) -0.4610(16) 0.1141(3) 0.081(4) Uani 1 1 d . . . H15A H -0.1027 -0.5258 0.1194 0.097 Uiso 1 1 calc R . . C16 C -0.2713(5) -0.4132(16) 0.1527(3) 0.073(3) Uani 1 1 d . . . C17 C -0.3291(5) -0.4298(17) 0.1342(3) 0.082(4) Uani 1 1 d . . . H17A H -0.3421 -0.4280 0.1073 0.098 Uiso 1 1 calc R . . C18 C -0.3698(6) -0.4498(17) 0.1563(4) 0.089(4) Uani 1 1 d . . . H18A H -0.4100 -0.4708 0.1441 0.107 Uiso 1 1 calc R . . C19 C -0.3512(6) -0.4389(19) 0.1948(4) 0.098(4) Uani 1 1 d . . . H19A H -0.3783 -0.4471 0.2096 0.118 Uiso 1 1 calc R . . C20 C -0.2914(6) -0.415(3) 0.2124(4) 0.136(7) Uani 1 1 d . . . H20A H -0.2788 -0.4032 0.2392 0.163 Uiso 1 1 calc R . . C21 C -0.2498(6) -0.409(2) 0.1919(4) 0.117(6) Uani 1 1 d . . . H21A H -0.2091 -0.4018 0.2041 0.140 Uiso 1 1 calc R . . C1' C 0.2350(5) -0.2641(19) 0.0946(4) 0.098(4) Uani 1 1 d . . . H1'A H 0.2450 -0.2403 0.1219 0.148 Uiso 1 1 calc R . . H1'B H 0.2316 -0.1556 0.0806 0.148 Uiso 1 1 calc R . . H1'C H 0.2657 -0.3348 0.0889 0.148 Uiso 1 1 calc R . . C2' C 0.1549(6) -0.4065(18) 0.0441(3) 0.090(4) Uani 1 1 d . . . H2'A H 0.1180 -0.4680 0.0415 0.135 Uiso 1 1 calc R . . H2'B H 0.1826 -0.4817 0.0364 0.135 Uiso 1 1 calc R . . H2'C H 0.1477 -0.3039 0.0281 0.135 Uiso 1 1 calc R . . C3' C 0.1462(4) -0.3794(12) 0.1107(3) 0.054(3) Uani 1 1 d . . . C4' C 0.0934(5) -0.4814(14) 0.1017(3) 0.063(3) Uani 1 1 d . . . H4'A H 0.0802 -0.5345 0.0776 0.076 Uiso 1 1 calc R . . C5' C 0.0620(5) -0.5021(15) 0.1280(3) 0.068(3) Uani 1 1 d . . . H5'A H 0.0281 -0.5724 0.1214 0.082 Uiso 1 1 calc R . . C6' C 0.0778(5) -0.4229(14) 0.1650(3) 0.065(3) Uani 1 1 d . . . C7' C 0.1315(5) -0.3254(16) 0.1737(3) 0.079(3) Uani 1 1 d . . . H7'A H 0.1454 -0.2748 0.1981 0.095 Uiso 1 1 calc R . . C8' C 0.1645(5) -0.3026(13) 0.1467(3) 0.064(3) Uani 1 1 d . . . H8'A H 0.1991 -0.2350 0.1532 0.077 Uiso 1 1 calc R . . C9' C 0.0443(4) -0.4437(14) 0.1928(3) 0.061(3) Uani 1 1 d . . . H9'A H 0.0111 -0.5168 0.1854 0.073 Uiso 1 1 calc R . . C10' C 0.0542(4) -0.3719(16) 0.2282(3) 0.069(3) Uani 1 1 d . . . H10B H 0.0882 -0.3029 0.2368 0.082 Uiso 1 1 calc R . . C11' C 0.0161(4) -0.3925(14) 0.2547(3) 0.064(3) Uani 1 1 d . . . C12' C -0.0268(6) -0.5197(16) 0.2474(3) 0.081(4) Uani 1 1 d . . . H12B H -0.0312 -0.5962 0.2267 0.097 Uiso 1 1 calc R . . C13' C -0.0635(6) -0.5318(17) 0.2717(4) 0.093(4) Uani 1 1 d . . . H13B H -0.0918 -0.6209 0.2675 0.111 Uiso 1 1 calc R . . C14' C -0.0170(6) -0.3091(17) 0.3084(4) 0.089(4) Uani 1 1 d . . . H14B H -0.0119 -0.2393 0.3304 0.106 Uiso 1 1 calc R . . C15' C 0.0210(5) -0.2891(14) 0.2855(3) 0.080(4) Uani 1 1 d . . . H15B H 0.0504 -0.2031 0.2915 0.096 Uiso 1 1 calc R . . C16' C -0.1043(5) -0.4198(14) 0.3233(3) 0.064(3) Uani 1 1 d . . . C17' C -0.1601(6) -0.418(2) 0.3052(4) 0.119(6) Uani 1 1 d . . . H17B H -0.1717 -0.4222 0.2783 0.143 Uiso 1 1 calc R . . C18' C -0.2034(6) -0.409(3) 0.3253(4) 0.126(6) Uani 1 1 d . . . H18B H -0.2437 -0.4057 0.3120 0.151 Uiso 1 1 calc R . . C19' C -0.1858(6) -0.4038(18) 0.3646(4) 0.090(4) Uani 1 1 d . . . H19B H -0.2142 -0.3978 0.3784 0.108 Uiso 1 1 calc R . . C20' C -0.1282(7) -0.4077(19) 0.3833(4) 0.099(4) Uani 1 1 d . . . H20B H -0.1163 -0.4048 0.4102 0.118 Uiso 1 1 calc R . . C21' C -0.0842(6) -0.4163(17) 0.3623(4) 0.088(4) Uani 1 1 d . . . H21B H -0.0435 -0.4194 0.3749 0.106 Uiso 1 1 calc R . . C1" C 0.4031(5) -0.3567(18) 0.2587(4) 0.107(5) Uani 1 1 d . . . H1"A H 0.4157 -0.3204 0.2853 0.160 Uiso 1 1 calc R . . H1"B H 0.4038 -0.2580 0.2423 0.160 Uiso 1 1 calc R . . H1"C H 0.4296 -0.4459 0.2543 0.160 Uiso 1 1 calc R . . C2" C 0.3146(6) -0.4915(19) 0.2110(4) 0.099(4) Uani 1 1 d . . . H2"A H 0.2749 -0.5326 0.2091 0.149 Uiso 1 1 calc R . . H2"B H 0.3382 -0.5859 0.2054 0.149 Uiso 1 1 calc R . . H2"C H 0.3129 -0.3980 0.1928 0.149 Uiso 1 1 calc R . . C3" C 0.3097(4) -0.4116(14) 0.2771(3) 0.058(3) Uani 1 1 d . . . C4" C 0.2536(5) -0.4844(16) 0.2693(3) 0.077(3) Uani 1 1 d . . . H4"A H 0.2378 -0.5419 0.2458 0.093 Uiso 1 1 calc R . . C5" C 0.2204(5) -0.4729(15) 0.2961(3) 0.068(3) Uani 1 1 d . . . H5"A H 0.1824 -0.5224 0.2902 0.082 Uiso 1 1 calc R . . C6" C 0.2424(4) -0.3899(14) 0.3310(3) 0.059(3) Uani 1 1 d . . . C7" C 0.2989(5) -0.3165(14) 0.3383(3) 0.067(3) Uani 1 1 d . . . H7"A H 0.3148 -0.2592 0.3617 0.081 Uiso 1 1 calc R . . C8" C 0.3320(4) -0.3254(14) 0.3124(2) 0.060(3) Uani 1 1 d . . . H8"A H 0.3697 -0.2738 0.3182 0.073 Uiso 1 1 calc R . . C9" C 0.2072(5) -0.3737(15) 0.3587(3) 0.069(3) Uani 1 1 d . . . H9"A H 0.1707 -0.4317 0.3518 0.082 Uiso 1 1 calc R . . C10" C 0.2192(5) -0.2892(15) 0.3921(3) 0.077(3) Uani 1 1 d . . . H10C H 0.2544 -0.2249 0.3996 0.093 Uiso 1 1 calc R . . C11" C 0.1797(5) -0.2911(15) 0.4183(3) 0.065(3) Uani 1 1 d . . . C12" C 0.1308(5) -0.3976(15) 0.4133(4) 0.078(3) Uani 1 1 d . . . H12C H 0.1226 -0.4794 0.3933 0.094 Uiso 1 1 calc R . . C13" C 0.0937(5) -0.3870(14) 0.4368(4) 0.074(3) Uani 1 1 d . . . H13C H 0.0604 -0.4596 0.4325 0.089 Uiso 1 1 calc R . . C14" C 0.1511(6) -0.1648(14) 0.4718(4) 0.080(4) Uani 1 1 d . . . H14C H 0.1576 -0.0830 0.4917 0.095 Uiso 1 1 calc R . . C15" C 0.1901(5) -0.1736(16) 0.4482(3) 0.083(4) Uani 1 1 d . . . H15C H 0.2230 -0.0995 0.4529 0.099 Uiso 1 1 calc R . . C16" C 0.0611(5) -0.2584(14) 0.4888(4) 0.069(3) Uani 1 1 d . . . C17" C 0.0028(6) -0.2393(19) 0.4697(4) 0.095(4) Uani 1 1 d . . . H17C H -0.0091 -0.2373 0.4428 0.114 Uiso 1 1 calc R . . C18" C -0.0396(6) -0.2227(19) 0.4904(5) 0.105(5) Uani 1 1 d . . . H18C H -0.0800 -0.2114 0.4776 0.126 Uiso 1 1 calc R . . C19" C -0.0208(6) -0.2233(17) 0.5293(5) 0.093(4) Uani 1 1 d . . . H19C H -0.0483 -0.2062 0.5435 0.112 Uiso 1 1 calc R . . C20" C 0.0394(6) -0.2493(17) 0.5489(4) 0.092(4) Uani 1 1 d . . . H20C H 0.0515 -0.2551 0.5758 0.110 Uiso 1 1 calc R . . C21" C 0.0814(6) -0.2666(18) 0.5273(3) 0.090(4) Uani 1 1 d . . . H21C H 0.1218 -0.2831 0.5395 0.108 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 P 0.0618(18) 0.083(2) 0.074(2) 0.0132(16) 0.0330(16) 0.0095(15) F1 0.140(6) 0.127(6) 0.122(6) 0.026(5) 0.085(5) 0.045(5) F2 0.154(7) 0.117(6) 0.160(7) 0.026(6) 0.102(6) -0.004(5) F3 0.130(6) 0.132(7) 0.088(5) -0.009(5) 0.007(5) 0.029(5) F4 0.124(6) 0.129(7) 0.120(6) -0.012(5) 0.065(5) 0.017(5) F5 0.120(6) 0.114(6) 0.127(6) 0.013(5) 0.060(5) -0.033(5) F6 0.102(6) 0.147(8) 0.126(7) 0.005(6) 0.019(5) 0.006(5) P' 0.070(2) 0.093(3) 0.076(2) -0.0111(18) 0.0298(18) -0.0071(17) F1' 0.164(7) 0.124(7) 0.187(9) -0.029(6) 0.096(7) 0.025(6) F2' 0.154(7) 0.140(7) 0.105(6) -0.008(5) 0.076(5) -0.032(6) F3' 0.149(8) 0.241(13) 0.133(9) -0.075(8) -0.013(7) -0.005(8) F4' 0.105(5) 0.129(6) 0.118(6) -0.031(5) 0.053(5) 0.004(5) F5' 0.197(9) 0.129(8) 0.222(11) -0.029(7) 0.135(8) -0.058(7) F6' 0.110(6) 0.156(8) 0.107(6) 0.028(5) 0.012(5) 0.009(5) P" 0.076(2) 0.082(2) 0.0612(19) -0.0225(15) 0.0298(16) -0.0110(16) F1" 0.135(6) 0.108(6) 0.136(6) -0.035(5) 0.079(5) 0.019(5) F2" 0.153(7) 0.126(7) 0.125(6) -0.017(5) 0.089(6) -0.046(5) F3" 0.126(6) 0.129(7) 0.093(6) -0.017(5) 0.007(5) -0.009(5) F4" 0.126(6) 0.115(6) 0.132(6) -0.021(5) 0.067(5) 0.023(5) F5" 0.119(5) 0.112(6) 0.103(5) 0.003(4) 0.065(5) -0.023(4) F6" 0.106(5) 0.128(6) 0.092(5) -0.018(5) 0.017(4) -0.010(5) N1 0.077(6) 0.113(8) 0.055(6) 0.013(5) 0.030(5) 0.019(6) N2 0.071(6) 0.063(6) 0.079(7) 0.010(5) 0.027(5) 0.012(5) N1' 0.087(7) 0.091(7) 0.075(7) -0.007(5) 0.038(6) -0.024(6) N2' 0.065(6) 0.090(7) 0.065(6) -0.003(5) 0.023(5) -0.025(5) N1" 0.088(7) 0.092(8) 0.070(7) -0.014(5) 0.030(6) -0.010(6) N2" 0.076(6) 0.061(6) 0.066(6) -0.023(5) 0.033(5) -0.010(5) C1 0.073(8) 0.101(10) 0.101(9) -0.018(7) 0.049(7) 0.001(7) C2 0.104(9) 0.100(10) 0.088(9) 0.015(7) 0.060(8) 0.031(8) C3 0.085(7) 0.035(6) 0.059(7) -0.008(5) 0.027(6) 0.000(5) C4 0.068(7) 0.081(9) 0.089(9) 0.003(6) 0.034(7) 0.020(6) C5 0.081(8) 0.047(7) 0.106(10) 0.001(6) 0.046(7) 0.011(6) C6 0.072(7) 0.041(6) 0.090(8) 0.005(6) 0.037(6) 0.002(5) C7 0.074(7) 0.064(7) 0.071(7) 0.000(6) 0.027(6) 0.004(6) C8 0.061(6) 0.072(8) 0.067(7) -0.004(6) 0.028(6) -0.001(5) C9 0.056(6) 0.061(7) 0.075(8) -0.021(6) 0.018(6) 0.003(5) C10 0.051(6) 0.085(8) 0.051(7) 0.005(6) 0.007(5) -0.002(5) C11 0.085(7) 0.037(6) 0.053(6) 0.007(4) 0.037(5) 0.001(5) C12 0.096(8) 0.079(9) 0.071(8) 0.020(6) 0.051(7) 0.017(7) C13 0.098(9) 0.060(8) 0.106(10) 0.003(7) 0.030(8) 0.028(7) C14 0.085(9) 0.098(10) 0.073(8) 0.036(7) 0.018(7) 0.019(7) C15 0.075(7) 0.097(9) 0.091(9) 0.019(7) 0.056(7) 0.018(6) C16 0.072(8) 0.095(9) 0.062(7) 0.013(6) 0.033(7) 0.004(6) C17 0.072(8) 0.107(10) 0.055(7) 0.001(6) -0.003(7) 0.000(7) C18 0.091(9) 0.104(10) 0.091(10) -0.024(7) 0.054(8) -0.013(7) C19 0.077(9) 0.143(13) 0.092(10) -0.024(8) 0.052(8) -0.003(8) C20 0.073(10) 0.25(2) 0.091(11) 0.000(11) 0.042(9) -0.001(11) C21 0.066(8) 0.223(18) 0.070(10) 0.005(10) 0.034(8) -0.010(9) C1' 0.090(9) 0.126(12) 0.094(9) -0.030(8) 0.051(7) -0.034(8) C2' 0.113(10) 0.120(11) 0.039(7) -0.017(6) 0.024(7) -0.016(8) C3' 0.055(6) 0.047(6) 0.066(7) -0.012(5) 0.024(5) -0.004(5) C4' 0.084(8) 0.067(7) 0.039(6) -0.012(5) 0.019(6) -0.017(6) C5' 0.073(7) 0.075(8) 0.049(7) -0.019(6) 0.005(6) -0.014(6) C6' 0.065(7) 0.062(7) 0.074(8) 0.009(6) 0.029(6) -0.006(5) C7' 0.081(8) 0.093(9) 0.066(8) 0.003(6) 0.025(7) -0.006(7) C8' 0.073(7) 0.052(7) 0.072(7) -0.023(5) 0.026(6) -0.036(5) C9' 0.045(6) 0.070(8) 0.066(7) -0.001(6) 0.012(5) -0.009(5) C10' 0.051(6) 0.087(9) 0.078(8) -0.009(6) 0.033(6) -0.007(5) C11' 0.054(6) 0.049(7) 0.087(8) -0.011(6) 0.015(6) -0.034(5) C12' 0.117(9) 0.100(10) 0.035(6) -0.024(6) 0.038(6) 0.011(8) C13' 0.109(10) 0.095(10) 0.075(9) -0.049(7) 0.027(8) -0.050(8) C14' 0.105(9) 0.101(10) 0.087(9) -0.035(7) 0.072(8) -0.012(8) C15' 0.084(8) 0.051(7) 0.097(9) -0.055(6) 0.007(7) -0.036(6) C16' 0.061(7) 0.079(8) 0.055(7) -0.009(5) 0.023(6) -0.012(6) C17' 0.076(9) 0.225(19) 0.059(8) -0.008(9) 0.023(8) -0.005(10) C18' 0.074(9) 0.23(2) 0.077(10) 0.001(11) 0.017(8) -0.014(10) C19' 0.099(10) 0.101(10) 0.082(10) -0.007(7) 0.045(8) -0.010(8) C20' 0.116(11) 0.122(12) 0.068(9) -0.002(8) 0.042(9) 0.013(9) C21' 0.091(9) 0.097(10) 0.081(10) 0.003(7) 0.029(8) 0.010(7) C1" 0.093(9) 0.102(11) 0.145(13) -0.026(9) 0.067(9) -0.047(8) C2" 0.090(9) 0.126(12) 0.094(10) -0.030(8) 0.046(8) -0.013(8) C3" 0.037(5) 0.074(8) 0.064(7) 0.014(5) 0.015(5) -0.007(5) C4" 0.075(8) 0.108(10) 0.052(7) -0.020(6) 0.022(6) -0.013(7) C5" 0.058(7) 0.097(9) 0.047(6) -0.021(6) 0.012(5) -0.017(6) C6" 0.041(6) 0.073(8) 0.070(7) 0.007(6) 0.026(5) -0.001(5) C7" 0.088(8) 0.063(7) 0.051(7) 0.007(5) 0.020(6) 0.017(6) C8" 0.057(6) 0.094(8) 0.021(5) -0.016(5) -0.005(5) -0.023(5) C9" 0.057(6) 0.066(8) 0.084(8) 0.000(6) 0.023(6) -0.002(5) C10" 0.092(8) 0.072(8) 0.079(8) -0.014(6) 0.041(7) -0.022(6) C11" 0.068(7) 0.083(8) 0.052(6) -0.013(6) 0.031(6) 0.007(6) C12" 0.083(8) 0.071(8) 0.100(9) -0.023(6) 0.058(7) -0.025(6) C13" 0.085(8) 0.051(7) 0.097(9) -0.007(6) 0.044(7) -0.017(6) C14" 0.106(9) 0.049(7) 0.088(9) -0.024(6) 0.034(8) -0.023(7) C15" 0.076(7) 0.088(9) 0.096(9) -0.043(7) 0.043(7) -0.051(6) C16" 0.065(7) 0.067(8) 0.085(9) -0.005(6) 0.037(7) 0.005(6) C17" 0.074(9) 0.143(13) 0.071(8) -0.032(8) 0.026(7) -0.015(8) C18" 0.087(9) 0.133(13) 0.116(12) -0.035(9) 0.065(9) -0.016(8) C19" 0.099(10) 0.089(10) 0.111(12) -0.007(8) 0.061(9) -0.010(8) C20" 0.109(11) 0.105(11) 0.068(8) 0.017(7) 0.034(8) 0.022(8) C21" 0.084(8) 0.143(13) 0.051(8) -0.002(7) 0.031(7) 0.018(8) _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 P F6 1.535(9) . ? P F3 1.559(8) . ? P F5 1.571(7) . ? P F2 1.572(8) . ? P F1 1.579(7) . ? P F4 1.591(8) . ? P' F3' 1.510(10) . ? P' F6' 1.556(9) . ? P' F1' 1.559(8) . ? P' F5' 1.565(9) . ? P' F2' 1.582(8) . ? P' F4' 1.588(8) . ? P" F3" 1.549(8) . ? P" F6" 1.567(8) . ? P" F4" 1.567(7) . ? P" F1" 1.575(7) . ? P" F2" 1.586(8) . ? P" F5" 1.596(7) . ? N1 C3 1.360(12) . ? N1 C1 1.439(13) . ? N1 C2 1.456(14) . ? N2 C13 1.316(14) . ? N2 C14 1.323(14) . ? N2 C16 1.503(13) . ? N1' C2' 1.408(13) . ? N1' C3' 1.417(12) . ? N1' C1' 1.440(14) . ? N2' C14' 1.297(14) . ? N2' C13' 1.302(13) . ? N2' C16' 1.489(13) . ? N1" C3" 1.382(13) . ? N1" C2" 1.448(14) . ? N1" C1" 1.484(14) . ? N2" C14" 1.317(13) . ? N2" C13" 1.323(13) . ? N2" C16" 1.492(13) . ? C3 C4 1.398(14) . ? C3 C8 1.430(14) . ? C4 C5 1.381(15) . ? C5 C6 1.393(15) . ? C6 C7 1.393(14) . ? C6 C9 1.483(14) . ? C7 C8 1.337(14) . ? C9 C10 1.333(14) . ? C10 C11 1.451(13) . ? C11 C12 1.368(14) . ? C11 C15 1.396(14) . ? C12 C13 1.361(16) . ? C14 C15 1.411(15) . ? C16 C17 1.335(15) . ? C16 C21 1.358(16) . ? C17 C18 1.400(16) . ? C18 C19 1.333(17) . ? C19 C20 1.374(17) . ? C20 C21 1.367(16) . ? C3' C8' 1.375(13) . ? C3' C4' 1.415(13) . ? C4' C5' 1.350(14) . ? C5' C6' 1.412(14) . ? C6' C7' 1.413(14) . ? C6' C9' 1.436(14) . ? C7' C8' 1.401(14) . ? C9' C10' 1.344(14) . ? C10' C11' 1.474(14) . ? C11' C15' 1.338(14) . ? C11' C12' 1.365(15) . ? C12' C13' 1.377(16) . ? C14' C15' 1.371(15) . ? C16' C17' 1.283(16) . ? C16' C21' 1.350(15) . ? C17' C18' 1.392(18) . ? C18' C19' 1.358(18) . ? C19' C20' 1.324(17) . ? C20' C21' 1.429(17) . ? C3" C4" 1.374(14) . ? C3" C8" 1.395(13) . ? C4" C5" 1.392(14) . ? C5" C6" 1.374(14) . ? C6" C7" 1.386(14) . ? C6" C9" 1.456(14) . ? C7" C8" 1.362(13) . ? C9" C10" 1.321(14) . ? C10" C11" 1.483(14) . ? C11" C15" 1.369(14) . ? C11" C12" 1.370(14) . ? C12" C13" 1.363(14) . ? C14" C15" 1.399(15) . ? C16" C21" 1.335(15) . ? C16" C17" 1.351(15) . ? C17" C18" 1.393(16) . ? C18" C19" 1.346(18) . ? C19" C20" 1.398(18) . ? C20" C21" 1.409(16) . ? 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 F6 P F3 178.2(5) . . ? F6 P F5 89.3(5) . . ? F3 P F5 91.5(5) . . ? F6 P F2 90.8(5) . . ? F3 P F2 88.3(5) . . ? F5 P F2 178.2(5) . . ? F6 P F1 90.8(5) . . ? F3 P F1 90.9(5) . . ? F5 P F1 90.4(5) . . ? F2 P F1 91.4(5) . . ? F6 P F4 89.5(5) . . ? F3 P F4 88.9(4) . . ? F5 P F4 89.9(5) . . ? F2 P F4 88.4(5) . . ? F1 P F4 179.6(5) . . ? F3' P' F6' 176.8(6) . . ? F3' P' F1' 90.9(6) . . ? F6' P' F1' 92.3(5) . . ? F3' P' F5' 89.6(7) . . ? F6' P' F5' 90.0(6) . . ? F1' P' F5' 90.5(6) . . ? F3' P' F2' 92.5(6) . . ? F6' P' F2' 87.9(5) . . ? F1' P' F2' 90.8(5) . . ? F5' P' F2' 177.6(6) . . ? F3' P' F4' 90.7(6) . . ? F6' P' F4' 86.1(5) . . ? F1' P' F4' 178.4(6) . . ? F5' P' F4' 89.3(5) . . ? F2' P' F4' 89.4(5) . . ? F3" P" F6" 179.2(5) . . ? F3" P" F4" 91.3(5) . . ? F6" P" F4" 87.9(5) . . ? F3" P" F1" 89.6(5) . . ? F6" P" F1" 91.2(5) . . ? F4" P" F1" 179.0(5) . . ? F3" P" F2" 90.4(5) . . ? F6" P" F2" 89.9(5) . . ? F4" P" F2" 90.5(5) . . ? F1" P" F2" 89.1(5) . . ? F3" P" F5" 90.2(5) . . ? F6" P" F5" 89.5(4) . . ? F4" P" F5" 89.9(4) . . ? F1" P" F5" 90.5(4) . . ? F2" P" F5" 179.3(5) . . ? C3 N1 C1 121.6(10) . . ? C3 N1 C2 119.3(9) . . ? C1 N1 C2 119.1(9) . . ? C13 N2 C14 121.4(10) . . ? C13 N2 C16 118.9(10) . . ? C14 N2 C16 119.7(10) . . ? C2' N1' C3' 121.2(9) . . ? C2' N1' C1' 120.0(9) . . ? C3' N1' C1' 118.5(9) . . ? C14' N2' C13' 119.0(10) . . ? C14' N2' C16' 118.0(9) . . ? C13' N2' C16' 123.0(10) . . ? C3" N1" C2" 122.5(9) . . ? C3" N1" C1" 119.2(10) . . ? C2" N1" C1" 117.8(10) . . ? C14" N2" C13" 121.7(9) . . ? C14" N2" C16" 120.6(9) . . ? C13" N2" C16" 117.4(9) . . ? N1 C3 C4 122.9(10) . . ? N1 C3 C8 121.4(10) . . ? C4 C3 C8 115.6(10) . . ? C5 C4 C3 121.2(11) . . ? C4 C5 C6 122.0(10) . . ? C5 C6 C7 116.7(10) . . ? C5 C6 C9 119.0(10) . . ? C7 C6 C9 124.3(10) . . ? C8 C7 C6 122.2(11) . . ? C7 C8 C3 122.3(10) . . ? C10 C9 C6 128.8(10) . . ? C9 C10 C11 122.2(10) . . ? C12 C11 C15 117.4(9) . . ? C12 C11 C10 123.5(9) . . ? C15 C11 C10 119.1(9) . . ? C13 C12 C11 120.8(11) . . ? N2 C13 C12 121.5(11) . . ? N2 C14 C15 119.6(11) . . ? C11 C15 C14 119.3(10) . . ? C17 C16 C21 123.7(11) . . ? C17 C16 N2 118.1(11) . . ? C21 C16 N2 118.1(10) . . ? C16 C17 C18 118.3(11) . . ? C19 C18 C17 120.1(12) . . ? C18 C19 C20 119.1(12) . . ? C21 C20 C19 122.4(14) . . ? C16 C21 C20 116.2(12) . . ? C8' C3' C4' 118.3(9) . . ? C8' C3' N1' 121.2(9) . . ? C4' C3' N1' 120.5(9) . . ? C5' C4' C3' 120.4(9) . . ? C4' C5' C6' 123.7(10) . . ? C5' C6' C7' 114.9(10) . . ? C5' C6' C9' 123.8(10) . . ? C7' C6' C9' 121.3(10) . . ? C8' C7' C6' 122.0(11) . . ? C3' C8' C7' 120.6(9) . . ? C10' C9' C6' 128.9(10) . . ? C9' C10' C11' 125.9(10) . . ? C15' C11' C12' 118.0(10) . . ? C15' C11' C10' 122.6(9) . . ? C12' C11' C10' 119.4(10) . . ? C11' C12' C13' 118.3(10) . . ? N2' C13' C12' 122.5(11) . . ? N2' C14' C15' 121.4(10) . . ? C11' C15' C14' 120.5(10) . . ? C17' C16' C21' 122.8(11) . . ? C17' C16' N2' 118.6(11) . . ? C21' C16' N2' 118.6(10) . . ? C16' C17' C18' 120.9(13) . . ? C19' C18' C17' 118.9(13) . . ? C20' C19' C18' 120.2(13) . . ? C19' C20' C21' 120.4(13) . . ? C16' C21' C20' 116.9(12) . . ? C4" C3" N1" 118.7(10) . . ? C4" C3" C8" 118.3(9) . . ? N1" C3" C8" 123.0(9) . . ? C3" C4" C5" 120.6(10) . . ? C6" C5" C4" 121.4(10) . . ? C5" C6" C7" 117.2(9) . . ? C5" C6" C9" 121.5(9) . . ? C7" C6" C9" 121.3(10) . . ? C8" C7" C6" 122.3(10) . . ? C7" C8" C3" 120.2(9) . . ? C10" C9" C6" 129.9(11) . . ? C9" C10" C11" 123.8(11) . . ? C15" C11" C12" 116.9(9) . . ? C15" C11" C10" 119.0(10) . . ? C12" C11" C10" 124.0(10) . . ? C13" C12" C11" 121.8(11) . . ? N2" C13" C12" 119.6(10) . . ? N2" C14" C15" 119.8(10) . . ? C11" C15" C14" 120.1(10) . . ? C21" C16" C17" 123.6(11) . . ? C21" C16" N2" 118.2(10) . . ? C17" C16" N2" 118.3(11) . . ? C16" C17" C18" 119.9(12) . . ? C19" C18" C17" 118.4(13) . . ? C18" C19" C20" 121.3(12) . . ? C19" C20" C21" 119.2(12) . . ? C16" C21" C20" 117.5(12) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.06 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.398 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.094