# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yun Chi' _publ_contact_author_email ychi@mx.nthu.edu.tw loop_ _publ_author_name 'Yun Chi' 'Pi-Tai Chou' 'Chih-Hao Chang' data_1 _database_code_depnum_ccdc_archive 'CCDC 872662' #TrackingRef '- OsOrange_X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H30 F6 N6 Os P2' _chemical_formula_weight 864.76 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' F F 0.0171 0.0103 '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' Os Os -1.2165 7.6030 '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 12.3979(2) _cell_length_b 19.2597(4) _cell_length_c 13.7144(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.1952(10) _cell_angle_gamma 90.00 _cell_volume 3265.95(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 19709 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 4.070 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.443 _exptl_absorpt_correction_T_max 0.577 _exptl_absorpt_process_details 'SORTAV, (Blessing. 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'NONIUS KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19709 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7448 _reflns_number_gt 5656 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'NONIUS COLLECT' _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0631P)^2^+3.6444P] 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 7448 _refine_ls_number_parameters 429 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Os Os 0.406140(17) 0.266115(12) 0.330952(16) 0.02992(10) Uani 1 1 d . . . P1 P 0.44356(13) 0.29242(10) 0.48989(11) 0.0361(4) Uani 1 1 d . . . P2 P 0.51357(12) 0.35693(8) 0.30370(11) 0.0322(3) Uani 1 1 d . A . N1 N 0.2971(4) 0.1831(3) 0.3592(3) 0.0340(11) Uani 1 1 d . . . N2 N 0.2589(4) 0.3166(3) 0.3279(4) 0.0409(13) Uani 1 1 d . . . N3 N 0.2270(4) 0.3821(3) 0.3186(4) 0.0415(13) Uani 1 1 d . . . N4 N 0.3773(4) 0.2358(3) 0.1803(4) 0.0318(11) Uani 1 1 d . . . N5 N 0.5271(4) 0.1946(3) 0.3109(4) 0.0391(12) Uani 1 1 d . . . N6 N 0.6136(4) 0.1728(3) 0.3676(4) 0.0390(12) Uani 1 1 d . . . C1 C 0.3258(6) 0.1157(3) 0.3720(5) 0.0463(16) Uani 1 1 d . . . H1 H 0.3996 0.1026 0.3710 0.056 Uiso 1 1 calc R . . C2 C 0.2471(7) 0.0648(4) 0.3868(5) 0.057(2) Uani 1 1 d . . . H2 H 0.2678 0.0177 0.3964 0.069 Uiso 1 1 calc R . . C3 C 0.1399(7) 0.0835(4) 0.3872(5) 0.056(2) Uani 1 1 d . . . H3 H 0.0862 0.0493 0.3959 0.068 Uiso 1 1 calc R . . C4 C 0.1117(6) 0.1511(4) 0.3751(5) 0.0487(18) Uani 1 1 d . . . H4 H 0.0383 0.1648 0.3766 0.058 Uiso 1 1 calc R . . C5 C 0.1905(5) 0.1999(3) 0.3605(4) 0.0363(14) Uani 1 1 d . . . C6 C 0.1704(5) 0.2744(3) 0.3443(5) 0.0407(15) Uani 1 1 d . . . C7 C 0.0784(5) 0.3161(4) 0.3434(5) 0.0492(18) Uani 1 1 d . . . H7 H 0.0060 0.3028 0.3526 0.059 Uiso 1 1 calc R . . C8 C 0.1189(5) 0.3823(4) 0.3257(6) 0.0541(19) Uani 1 1 d . A . C9 C 0.0561(6) 0.4484(4) 0.3120(8) 0.077(3) Uani 1 1 d D . . C10 C 0.2975(5) 0.2617(4) 0.1176(5) 0.0445(16) Uani 1 1 d . . . H10 H 0.2538 0.2985 0.1389 0.053 Uiso 1 1 calc R . . C11 C 0.2777(6) 0.2361(4) 0.0226(5) 0.0518(19) Uani 1 1 d . . . H11 H 0.2228 0.2555 -0.0210 0.062 Uiso 1 1 calc R . . C12 C 0.3402(5) 0.1820(4) -0.0055(5) 0.0509(19) Uani 1 1 d . . . H12 H 0.3266 0.1628 -0.0690 0.061 Uiso 1 1 calc R . . C13 C 0.4220(5) 0.1549(4) 0.0559(5) 0.0426(15) Uani 1 1 d . . . H13 H 0.4649 0.1174 0.0358 0.051 Uiso 1 1 calc R . . C14 C 0.4403(4) 0.1840(3) 0.1485(4) 0.0326(13) Uani 1 1 d . . . C15 C 0.5246(5) 0.1621(3) 0.2216(5) 0.0406(15) Uani 1 1 d . . . C16 C 0.6101(5) 0.1149(4) 0.2218(5) 0.0473(17) Uani 1 1 d . . . H16 H 0.6298 0.0849 0.1711 0.057 Uiso 1 1 calc R . . C17 C 0.6597(5) 0.1235(4) 0.3169(6) 0.0511(18) Uani 1 1 d . A . C18 C 0.7578(7) 0.0887(4) 0.3588(7) 0.065(2) Uani 1 1 d D . . C19 C 0.5386(5) 0.3654(3) 0.5046(4) 0.0356(14) Uani 1 1 d . . . C20 C 0.5799(5) 0.3909(4) 0.5948(5) 0.0474(17) Uani 1 1 d . . . H20 H 0.5618 0.3688 0.6533 0.057 Uiso 1 1 calc R . . C21 C 0.6473(5) 0.4487(4) 0.5996(5) 0.0513(18) Uani 1 1 d . . . H21 H 0.6760 0.4658 0.6611 0.062 Uiso 1 1 calc R . . C22 C 0.6720(6) 0.4807(4) 0.5147(6) 0.0529(19) Uani 1 1 d . . . H22 H 0.7161 0.5211 0.5179 0.063 Uiso 1 1 calc R . . C23 C 0.6338(5) 0.4552(4) 0.4249(5) 0.0473(16) Uani 1 1 d . . . H23 H 0.6538 0.4772 0.3668 0.057 Uiso 1 1 calc R . . C24 C 0.5658(5) 0.3974(3) 0.4187(5) 0.0370(14) Uani 1 1 d . . . C25 C 0.4921(6) 0.2234(4) 0.5755(5) 0.0487(18) Uani 1 1 d . . . H25A H 0.5169 0.1825 0.5395 0.058 Uiso 1 1 calc R . . H25B H 0.5527 0.2404 0.6202 0.058 Uiso 1 1 calc R . . C26 C 0.3957(6) 0.2050(5) 0.6317(6) 0.066(2) Uani 1 1 d . . . H26A H 0.3418 0.1781 0.5903 0.079 Uiso 1 1 calc R . . H26B H 0.4183 0.1772 0.6904 0.079 Uiso 1 1 calc R . . C27 C 0.3502(7) 0.2728(4) 0.6598(6) 0.063(2) Uani 1 1 d . . . H27A H 0.4009 0.2964 0.7080 0.076 Uiso 1 1 calc R . . H27B H 0.2808 0.2656 0.6897 0.076 Uiso 1 1 calc R . . C28 C 0.3319(5) 0.3180(4) 0.5649(5) 0.0511(18) Uani 1 1 d . . . H28A H 0.3357 0.3681 0.5809 0.061 Uiso 1 1 calc R . . H28B H 0.2608 0.3079 0.5303 0.061 Uiso 1 1 calc R . . C29 C 0.4657(5) 0.4278(3) 0.2211(4) 0.0425(15) Uani 1 1 d . A . H29A H 0.3860 0.4268 0.2097 0.051 Uiso 1 1 calc R . . H29B H 0.4879 0.4735 0.2487 0.051 Uiso 1 1 calc R . . C30 C 0.5199(6) 0.4139(4) 0.1251(5) 0.0500(17) Uani 1 1 d . . . H30A H 0.4634 0.4027 0.0728 0.060 Uiso 0.574(9) 1 calc PR A 1 H30B H 0.5573 0.4566 0.1057 0.060 Uiso 0.574(9) 1 calc PR A 1 H30C H 0.5181 0.4563 0.0841 0.060 Uiso 0.426(9) 1 d PR A 2 H30D H 0.4816 0.3763 0.0876 0.060 Uiso 0.426(9) 1 d PR A 2 C31 C 0.5973(10) 0.3574(8) 0.1340(9) 0.042(3) Uani 0.574(9) 1 d P A 1 H31A H 0.6606 0.3696 0.0976 0.051 Uiso 0.574(9) 1 calc PR A 1 H31B H 0.5637 0.3153 0.1035 0.051 Uiso 0.574(9) 1 calc PR A 1 C31' C 0.6416(16) 0.3921(11) 0.1547(15) 0.058(5) Uani 0.426(9) 1 d P A 2 H31C H 0.6747 0.3702 0.0988 0.069 Uiso 0.426(9) 1 calc PR A 2 H31D H 0.6853 0.4330 0.1764 0.069 Uiso 0.426(9) 1 calc PR A 2 C32 C 0.6345(5) 0.3416(4) 0.2364(5) 0.0461(16) Uani 1 1 d . . . H32A H 0.6945 0.3727 0.2598 0.055 Uiso 0.574(9) 1 calc PR A 1 H32B H 0.6590 0.2928 0.2432 0.055 Uiso 0.574(9) 1 calc PR A 1 H32C H 0.7000 0.3460 0.2818 0.055 Uiso 0.426(9) 1 d PR A 2 H32D H 0.6323 0.2937 0.2100 0.055 Uiso 0.426(9) 1 d PR A 2 F1 F -0.0447(4) 0.4380(3) 0.3207(5) 0.0911(17) Uani 1 1 d . A . F2 F 0.1010(7) 0.5028(5) 0.3442(8) 0.077(3) Uiso 0.574(9) 1 d P A 1 F3 F 0.0441(7) 0.4679(5) 0.2131(7) 0.079(3) Uiso 0.574(9) 1 d PD A 1 F2' F 0.0659(9) 0.4778(6) 0.4071(8) 0.072(4) Uiso 0.426(9) 1 d PD A 2 F3' F 0.1017(10) 0.5006(7) 0.2778(11) 0.078(4) Uiso 0.426(9) 1 d P A 2 F4 F 0.8320(6) 0.1352(4) 0.3988(7) 0.067(3) Uiso 0.574(9) 1 d PD A 1 F5 F 0.7425(8) 0.0366(6) 0.4165(8) 0.089(3) Uiso 0.574(9) 1 d P A 1 F6 F 0.8173(6) 0.0644(4) 0.2868(5) 0.058(2) Uiso 0.574(9) 1 d P A 1 F4' F 0.8498(16) 0.1186(13) 0.3484(19) 0.165(9) Uiso 0.426(9) 1 d PD A 2 F5' F 0.7620(10) 0.0708(7) 0.4507(10) 0.074(4) Uiso 0.426(9) 1 d P A 2 F6' F 0.7690(14) 0.0280(9) 0.3094(13) 0.123(6) Uiso 0.426(9) 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 Os 0.02836(14) 0.03123(15) 0.02995(14) 0.00218(10) 0.00072(9) 0.00054(10) P1 0.0320(8) 0.0468(9) 0.0293(8) 0.0037(7) 0.0012(6) -0.0085(7) P2 0.0308(8) 0.0342(8) 0.0320(8) 0.0060(7) 0.0051(6) 0.0009(6) N1 0.042(3) 0.034(3) 0.026(2) 0.003(2) 0.003(2) -0.009(2) N2 0.031(3) 0.041(3) 0.050(3) -0.008(3) -0.005(2) 0.002(2) N3 0.031(3) 0.037(3) 0.058(4) 0.002(3) 0.006(2) 0.000(2) N4 0.033(3) 0.035(3) 0.027(2) 0.000(2) -0.001(2) -0.002(2) N5 0.033(3) 0.039(3) 0.044(3) 0.002(3) -0.003(2) 0.006(2) N6 0.035(3) 0.043(3) 0.037(3) 0.000(2) -0.007(2) 0.009(2) C1 0.064(4) 0.039(4) 0.036(4) 0.002(3) 0.005(3) 0.000(3) C2 0.102(6) 0.030(4) 0.041(4) -0.006(3) 0.016(4) -0.010(4) C3 0.079(6) 0.051(5) 0.041(4) -0.006(4) 0.020(4) -0.028(4) C4 0.058(4) 0.058(5) 0.032(3) -0.007(3) 0.010(3) -0.022(4) C5 0.037(3) 0.042(4) 0.030(3) -0.009(3) 0.004(2) -0.009(3) C6 0.039(3) 0.044(4) 0.039(4) -0.004(3) 0.002(3) -0.006(3) C7 0.033(3) 0.063(5) 0.053(4) 0.002(4) 0.010(3) -0.004(3) C8 0.034(4) 0.054(5) 0.074(5) -0.003(4) 0.004(3) 0.006(3) C9 0.038(4) 0.055(5) 0.135(9) -0.024(6) -0.009(5) 0.008(4) C10 0.034(3) 0.054(4) 0.045(4) 0.013(3) -0.003(3) 0.002(3) C11 0.041(4) 0.075(5) 0.038(4) 0.012(4) -0.007(3) 0.000(4) C12 0.045(4) 0.077(6) 0.031(3) -0.012(3) 0.002(3) -0.014(4) C13 0.045(4) 0.045(4) 0.037(3) -0.008(3) 0.002(3) 0.000(3) C14 0.030(3) 0.035(3) 0.033(3) -0.007(3) 0.003(2) -0.001(2) C15 0.042(3) 0.042(4) 0.039(3) -0.002(3) 0.006(3) -0.001(3) C16 0.038(4) 0.047(4) 0.056(4) 0.001(3) 0.000(3) 0.005(3) C17 0.043(4) 0.049(4) 0.061(5) -0.001(4) 0.000(3) 0.010(3) C18 0.066(5) 0.060(5) 0.070(6) -0.003(4) 0.013(4) 0.023(4) C19 0.029(3) 0.042(4) 0.035(3) 0.000(3) 0.002(2) -0.003(3) C20 0.040(4) 0.063(5) 0.039(4) -0.006(3) 0.003(3) -0.009(3) C21 0.039(4) 0.062(5) 0.053(4) -0.013(4) -0.002(3) -0.006(3) C22 0.047(4) 0.038(4) 0.072(5) 0.005(4) -0.008(4) -0.017(3) C23 0.048(4) 0.045(4) 0.049(4) 0.000(3) 0.002(3) -0.013(3) C24 0.032(3) 0.040(4) 0.038(3) 0.004(3) 0.001(3) -0.001(3) C25 0.048(4) 0.059(5) 0.038(4) 0.014(3) -0.003(3) -0.012(3) C26 0.055(5) 0.085(6) 0.058(5) 0.015(5) 0.000(4) -0.005(5) C27 0.070(5) 0.076(6) 0.047(4) 0.005(4) 0.031(4) -0.020(4) C28 0.039(4) 0.073(5) 0.042(4) -0.009(4) 0.007(3) -0.012(3) C29 0.054(4) 0.037(4) 0.038(4) 0.006(3) 0.010(3) 0.005(3) C30 0.059(4) 0.052(4) 0.039(4) 0.007(3) 0.007(3) 0.010(4) C31 0.043(7) 0.049(8) 0.035(6) 0.007(6) 0.015(5) 0.002(6) C31' 0.064(12) 0.044(11) 0.068(13) 0.003(10) 0.022(10) -0.021(10) C32 0.038(3) 0.054(4) 0.047(4) 0.007(3) 0.012(3) 0.006(3) F1 0.051(3) 0.072(3) 0.151(5) 0.005(3) 0.019(3) 0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Os N2 2.065(5) . ? Os N5 2.070(5) . ? Os N1 2.148(5) . ? Os N4 2.152(5) . ? Os P2 2.2462(16) . ? Os P1 2.2528(16) . ? P1 C19 1.835(6) . ? P1 C25 1.845(7) . ? P1 C28 1.851(7) . ? P2 C24 1.835(6) . ? P2 C32 1.842(6) . ? P2 C29 1.844(6) . ? N1 C1 1.353(8) . ? N1 C5 1.363(8) . ? N2 N3 1.327(7) . ? N2 C6 1.397(8) . ? N3 C8 1.350(8) . ? N4 C10 1.358(8) . ? N4 C14 1.358(7) . ? N5 N6 1.344(7) . ? N5 C15 1.374(8) . ? N6 C17 1.331(8) . ? C1 C2 1.408(10) . ? C2 C3 1.377(11) . ? C3 C4 1.355(11) . ? C4 C5 1.380(9) . ? C5 C6 1.470(9) . ? C6 C7 1.394(9) . ? C7 C8 1.398(10) . ? C8 C9 1.498(11) . ? C9 F2 1.252(12) . ? C9 F3' 1.261(15) . ? C9 F1 1.279(9) . ? C9 F3 1.404(11) . ? C9 F2' 1.419(12) . ? C10 C11 1.397(10) . ? C11 C12 1.370(10) . ? C12 C13 1.373(9) . ? C13 C14 1.391(8) . ? C14 C15 1.457(8) . ? C15 C16 1.396(9) . ? C16 C17 1.411(10) . ? C17 C18 1.469(10) . ? C18 F4' 1.295(16) . ? C18 F5 1.299(13) . ? C18 F5' 1.304(14) . ? C18 F6 1.358(11) . ? C18 F6' 1.363(14) . ? C18 F4 1.369(11) . ? C19 C20 1.392(8) . ? C19 C24 1.394(8) . ? C20 C21 1.390(10) . ? C21 C22 1.372(10) . ? C22 C23 1.377(10) . ? C23 C24 1.395(9) . ? C25 C26 1.511(10) . ? C26 C27 1.484(12) . ? C27 C28 1.568(11) . ? C29 C30 1.544(9) . ? C30 C31 1.449(14) . ? C30 C31' 1.59(2) . ? C31 C32 1.477(14) . ? C31' C32 1.49(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 N2 Os N5 163.4(2) . . ? N2 Os N1 77.7(2) . . ? N5 Os N1 90.0(2) . . ? N2 Os N4 91.3(2) . . ? N5 Os N4 76.3(2) . . ? N1 Os N4 84.74(18) . . ? N2 Os P2 99.44(15) . . ? N5 Os P2 92.97(15) . . ? N1 Os P2 176.99(14) . . ? N4 Os P2 96.35(14) . . ? N2 Os P1 91.90(16) . . ? N5 Os P1 100.27(15) . . ? N1 Os P1 94.64(13) . . ? N4 Os P1 176.49(14) . . ? P2 Os P1 84.45(6) . . ? C19 P1 C25 107.7(3) . . ? C19 P1 C28 103.6(3) . . ? C25 P1 C28 93.5(3) . . ? C19 P1 Os 111.3(2) . . ? C25 P1 Os 119.2(3) . . ? C28 P1 Os 119.2(2) . . ? C24 P2 C32 104.5(3) . . ? C24 P2 C29 106.9(3) . . ? C32 P2 C29 92.7(3) . . ? C24 P2 Os 111.4(2) . . ? C32 P2 Os 118.2(3) . . ? C29 P2 Os 120.7(2) . . ? C1 N1 C5 118.2(6) . . ? C1 N1 Os 125.1(5) . . ? C5 N1 Os 116.7(4) . . ? N3 N2 C6 109.6(5) . . ? N3 N2 Os 135.0(4) . . ? C6 N2 Os 115.3(4) . . ? N2 N3 C8 106.6(5) . . ? C10 N4 C14 118.4(5) . . ? C10 N4 Os 124.8(5) . . ? C14 N4 Os 116.7(4) . . ? N6 N5 C15 109.8(5) . . ? N6 N5 Os 133.3(4) . . ? C15 N5 Os 116.9(4) . . ? C17 N6 N5 106.0(5) . . ? N1 C1 C2 120.5(7) . . ? C3 C2 C1 119.9(7) . . ? C4 C3 C2 119.4(7) . . ? C3 C4 C5 119.6(7) . . ? N1 C5 C4 122.5(6) . . ? N1 C5 C6 112.6(5) . . ? C4 C5 C6 124.9(6) . . ? C7 C6 N2 108.4(6) . . ? C7 C6 C5 133.8(6) . . ? N2 C6 C5 117.7(5) . . ? C6 C7 C8 102.8(6) . . ? N3 C8 C7 112.5(6) . . ? N3 C8 C9 120.1(7) . . ? C7 C8 C9 127.4(6) . . ? F2 C9 F3' 42.6(7) . . ? F2 C9 F1 120.7(8) . . ? F3' C9 F1 128.9(9) . . ? F2 C9 F3 97.5(9) . . ? F3' C9 F3 56.4(8) . . ? F1 C9 F3 95.5(7) . . ? F2 C9 F2' 48.4(7) . . ? F3' C9 F2' 90.8(9) . . ? F1 C9 F2' 89.7(8) . . ? F3 C9 F2' 141.1(9) . . ? F2 C9 C8 116.9(8) . . ? F3' C9 C8 118.8(9) . . ? F1 C9 C8 111.0(7) . . ? F3 C9 C8 111.5(8) . . ? F2' C9 C8 102.4(8) . . ? N4 C10 C11 122.0(7) . . ? C12 C11 C10 117.8(6) . . ? C11 C12 C13 121.6(6) . . ? C12 C13 C14 118.1(6) . . ? N4 C14 C13 122.0(5) . . ? N4 C14 C15 113.1(5) . . ? C13 C14 C15 124.9(6) . . ? N5 C15 C16 109.1(6) . . ? N5 C15 C14 116.7(5) . . ? C16 C15 C14 134.2(6) . . ? C15 C16 C17 101.8(6) . . ? N6 C17 C16 113.1(6) . . ? N6 C17 C18 119.8(7) . . ? C16 C17 C18 126.9(7) . . ? F4' C18 F5 125.4(14) . . ? F4' C18 F5' 104.5(14) . . ? F5 C18 F5' 37.4(7) . . ? F4' C18 F6 62.8(12) . . ? F5 C18 F6 106.8(8) . . ? F5' C18 F6 128.8(9) . . ? F4' C18 F6' 101.8(14) . . ? F5 C18 F6' 70.5(9) . . ? F5' C18 F6' 104.8(11) . . ? F6 C18 F6' 42.5(8) . . ? F4' C18 F4 35.1(12) . . ? F5 C18 F4 112.6(9) . . ? F5' C18 F4 78.9(9) . . ? F6 C18 F4 97.6(8) . . ? F6' C18 F4 132.1(11) . . ? F4' C18 C17 117.6(13) . . ? F5 C18 C17 115.9(8) . . ? F5' C18 C17 118.2(8) . . ? F6 C18 C17 110.5(7) . . ? F6' C18 C17 108.0(10) . . ? F4 C18 C17 111.7(7) . . ? C20 C19 C24 119.9(6) . . ? C20 C19 P1 124.0(5) . . ? C24 C19 P1 116.0(5) . . ? C21 C20 C19 120.4(7) . . ? C22 C21 C20 119.4(7) . . ? C21 C22 C23 121.0(6) . . ? C22 C23 C24 120.3(6) . . ? C19 C24 C23 119.0(6) . . ? C19 C24 P2 116.5(5) . . ? C23 C24 P2 124.4(5) . . ? C26 C25 P1 105.1(5) . . ? C27 C26 C25 104.8(7) . . ? C26 C27 C28 108.0(6) . . ? C27 C28 P1 104.1(5) . . ? C30 C29 P2 104.8(4) . . ? C31 C30 C29 112.6(7) . . ? C31 C30 C31' 33.9(8) . . ? C29 C30 C31' 107.0(9) . . ? C30 C31 C32 113.2(9) . . ? C32 C31' C30 104.9(11) . . ? C31 C32 C31' 35.2(8) . . ? C31 C32 P2 103.5(6) . . ? C31' C32 P2 111.5(9) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.248 _refine_diff_density_min -1.296 _refine_diff_density_rms 0.143 data_CzPhO _database_code_depnum_ccdc_archive 'CCDC 872663' #TrackingRef '- OsOrange_X-ray.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H20 N O P' _chemical_formula_weight 441.44 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 8.1571(4) _cell_length_b 16.5407(9) _cell_length_c 33.1095(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4467.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2600 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 20.46 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9302 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'BRUKER SMART APEXCCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32581 _diffrn_reflns_av_R_equivalents 0.0844 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5142 _reflns_number_gt 4002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0652P)^2^+1.1526P] 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 5142 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.112 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.32274(6) 0.84184(3) 0.427510(16) 0.01906(15) Uani 1 1 d . . . O1 O 0.16189(17) 0.87270(10) 0.41334(5) 0.0279(4) Uani 1 1 d . . . N1 N 0.8745(2) 0.99656(10) 0.33562(5) 0.0213(4) Uani 1 1 d . . . C1 C 0.4909(2) 0.88803(12) 0.40076(6) 0.0197(4) Uani 1 1 d . . . C2 C 0.6537(2) 0.87531(13) 0.41212(7) 0.0231(5) Uani 1 1 d . . . H2 H 0.6777 0.8413 0.4345 0.028 Uiso 1 1 calc R . . C3 C 0.7807(2) 0.91187(13) 0.39110(6) 0.0219(4) Uani 1 1 d . . . H3 H 0.8911 0.9042 0.3993 0.026 Uiso 1 1 calc R . . C4 C 0.7446(2) 0.95987(12) 0.35787(6) 0.0205(4) Uani 1 1 d . . . C5 C 0.5832(2) 0.97214(13) 0.34591(6) 0.0232(5) Uani 1 1 d . . . H5 H 0.5598 1.0047 0.3230 0.028 Uiso 1 1 calc R . . C6 C 0.4567(2) 0.93681(13) 0.36741(6) 0.0227(5) Uani 1 1 d . . . H6 H 0.3463 0.9458 0.3595 0.027 Uiso 1 1 calc R . . C7 C 0.3555(2) 0.73393(13) 0.42736(7) 0.0246(5) Uani 1 1 d . . . C8 C 0.3420(3) 0.67996(16) 0.39546(8) 0.0372(6) Uani 1 1 d . . . H8 H 0.3171 0.6986 0.3690 0.045 Uiso 1 1 calc R . . C9 C 0.3657(3) 0.59797(17) 0.40297(10) 0.0496(8) Uani 1 1 d . . . H9 H 0.3543 0.5601 0.3816 0.060 Uiso 1 1 calc R . . C10 C 0.4055(3) 0.57144(16) 0.44114(11) 0.0518(8) Uani 1 1 d . . . H10 H 0.4221 0.5153 0.4456 0.062 Uiso 1 1 calc R . . C11 C 0.4219(3) 0.62497(15) 0.47323(9) 0.0404(7) Uani 1 1 d . . . H11 H 0.4500 0.6060 0.4994 0.049 Uiso 1 1 calc R . . C12 C 0.3961(3) 0.70718(13) 0.46620(7) 0.0265(5) Uani 1 1 d . . . C13 C 0.4035(2) 0.77272(13) 0.49664(7) 0.0238(5) Uani 1 1 d . . . C14 C 0.4429(3) 0.76559(16) 0.53731(7) 0.0332(6) Uani 1 1 d . . . H14 H 0.4700 0.7144 0.5485 0.040 Uiso 1 1 calc R . . C15 C 0.4422(3) 0.83401(18) 0.56134(8) 0.0394(6) Uani 1 1 d . . . H15 H 0.4701 0.8293 0.5891 0.047 Uiso 1 1 calc R . . C16 C 0.4020(3) 0.90856(17) 0.54595(7) 0.0388(6) Uani 1 1 d . . . H16 H 0.4005 0.9545 0.5632 0.047 Uiso 1 1 calc R . . C17 C 0.3635(3) 0.91712(14) 0.50522(7) 0.0292(5) Uani 1 1 d . . . H17 H 0.3366 0.9686 0.4944 0.035 Uiso 1 1 calc R . . C18 C 0.3651(2) 0.84909(12) 0.48065(6) 0.0205(4) Uani 1 1 d . . . C19 C 1.0024(2) 0.95471(13) 0.31690(6) 0.0197(4) Uani 1 1 d . . . C20 C 1.0449(3) 0.87361(13) 0.31921(6) 0.0238(5) Uani 1 1 d . . . H20 H 0.9873 0.8374 0.3364 0.029 Uiso 1 1 calc R . . C21 C 1.1747(3) 0.84753(14) 0.29557(7) 0.0295(5) Uani 1 1 d . . . H21 H 1.2053 0.7921 0.2963 0.035 Uiso 1 1 calc R . . C22 C 1.2617(3) 0.90036(16) 0.27065(7) 0.0351(6) Uani 1 1 d . . . H22 H 1.3496 0.8805 0.2546 0.042 Uiso 1 1 calc R . . C23 C 1.2209(3) 0.98132(15) 0.26912(6) 0.0302(5) Uani 1 1 d . . . H23 H 1.2814 1.0174 0.2525 0.036 Uiso 1 1 calc R . . C24 C 1.0901(2) 1.00937(13) 0.29220(6) 0.0223(5) Uani 1 1 d . . . C25 C 1.0129(2) 1.08737(13) 0.29647(6) 0.0228(4) Uani 1 1 d . . . C26 C 1.0449(3) 1.16386(14) 0.28019(7) 0.0307(5) Uani 1 1 d . . . H26 H 1.1324 1.1717 0.2617 0.037 Uiso 1 1 calc R . . C27 C 0.9464(3) 1.22769(15) 0.29169(8) 0.0378(6) Uani 1 1 d . . . H27 H 0.9665 1.2800 0.2809 0.045 Uiso 1 1 calc R . . C28 C 0.8186(3) 1.21677(15) 0.31874(8) 0.0381(6) Uani 1 1 d . . . H28 H 0.7543 1.2621 0.3265 0.046 Uiso 1 1 calc R . . C29 C 0.7822(3) 1.14176(14) 0.33477(7) 0.0309(5) Uani 1 1 d . . . H29 H 0.6935 1.1347 0.3530 0.037 Uiso 1 1 calc R . . C30 C 0.8801(3) 1.07713(13) 0.32318(6) 0.0222(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0151(2) 0.0229(3) 0.0192(3) 0.0031(2) 0.0009(2) -0.0017(2) O1 0.0173(7) 0.0382(9) 0.0283(8) 0.0094(7) -0.0010(6) -0.0016(6) N1 0.0174(8) 0.0225(9) 0.0239(9) 0.0006(7) 0.0037(7) -0.0017(7) C1 0.0149(9) 0.0226(11) 0.0216(11) -0.0005(8) 0.0020(8) -0.0011(8) C2 0.0200(10) 0.0260(11) 0.0234(11) 0.0058(9) -0.0006(8) 0.0000(8) C3 0.0131(9) 0.0272(11) 0.0253(11) 0.0019(9) -0.0014(8) 0.0007(8) C4 0.0187(10) 0.0214(10) 0.0215(11) -0.0007(8) 0.0029(8) -0.0034(8) C5 0.0219(11) 0.0271(11) 0.0206(11) 0.0052(9) -0.0004(8) -0.0003(8) C6 0.0148(9) 0.0295(11) 0.0237(11) 0.0031(9) -0.0019(8) 0.0003(8) C7 0.0200(10) 0.0232(11) 0.0307(12) -0.0017(9) 0.0082(9) -0.0041(8) C8 0.0335(13) 0.0409(15) 0.0373(14) -0.0135(11) 0.0152(11) -0.0127(11) C9 0.0483(16) 0.0335(15) 0.067(2) -0.0245(14) 0.0324(15) -0.0140(12) C10 0.0462(16) 0.0230(13) 0.086(2) -0.0017(14) 0.0323(16) -0.0005(11) C11 0.0357(13) 0.0256(13) 0.0601(18) 0.0119(12) 0.0156(13) 0.0052(10) C12 0.0186(10) 0.0244(11) 0.0366(13) 0.0051(10) 0.0063(9) -0.0004(8) C13 0.0160(9) 0.0288(12) 0.0267(11) 0.0066(9) 0.0023(8) 0.0006(8) C14 0.0223(11) 0.0470(15) 0.0303(13) 0.0155(11) 0.0014(9) 0.0031(10) C15 0.0284(12) 0.0684(19) 0.0214(12) 0.0016(12) -0.0020(10) -0.0031(12) C16 0.0357(13) 0.0517(17) 0.0290(13) -0.0140(12) 0.0019(11) -0.0068(12) C17 0.0247(11) 0.0303(12) 0.0325(13) -0.0030(10) 0.0040(9) -0.0027(9) C18 0.0153(9) 0.0248(11) 0.0215(11) 0.0031(9) 0.0011(8) -0.0010(8) C19 0.0151(9) 0.0272(11) 0.0168(10) -0.0028(8) -0.0019(8) -0.0029(8) C20 0.0227(10) 0.0264(11) 0.0224(11) -0.0007(9) -0.0022(9) -0.0016(9) C21 0.0296(11) 0.0325(13) 0.0264(12) -0.0051(10) -0.0015(10) 0.0092(10) C22 0.0283(12) 0.0529(16) 0.0242(12) -0.0020(11) 0.0072(10) 0.0113(11) C23 0.0253(11) 0.0470(15) 0.0185(11) 0.0055(10) 0.0055(9) 0.0002(10) C24 0.0178(10) 0.0316(12) 0.0176(10) 0.0004(9) -0.0020(8) -0.0055(8) C25 0.0195(10) 0.0287(12) 0.0201(10) 0.0029(9) -0.0033(8) -0.0057(8) C26 0.0269(11) 0.0350(13) 0.0300(12) 0.0102(10) -0.0034(10) -0.0085(10) C27 0.0369(13) 0.0305(13) 0.0461(15) 0.0146(11) -0.0098(12) -0.0093(11) C28 0.0353(13) 0.0265(13) 0.0525(17) 0.0007(11) -0.0030(12) 0.0025(10) C29 0.0280(12) 0.0273(12) 0.0373(14) 0.0014(10) 0.0033(10) 0.0016(10) C30 0.0212(10) 0.0251(11) 0.0203(10) 0.0020(8) -0.0025(8) -0.0033(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 P1 O1 1.4840(15) . ? P1 C18 1.797(2) . ? P1 C1 1.803(2) . ? P1 C7 1.805(2) . ? N1 C30 1.396(3) . ? N1 C19 1.397(3) . ? N1 C4 1.426(2) . ? C1 C6 1.396(3) . ? C1 C2 1.396(3) . ? C2 C3 1.387(3) . ? C3 C4 1.388(3) . ? C4 C5 1.390(3) . ? C5 C6 1.383(3) . ? C7 C8 1.387(3) . ? C7 C12 1.400(3) . ? C8 C9 1.392(4) . ? C9 C10 1.377(5) . ? C10 C11 1.390(4) . ? C11 C12 1.396(3) . ? C12 C13 1.481(3) . ? C13 C14 1.389(3) . ? C13 C18 1.405(3) . ? C14 C15 1.383(4) . ? C15 C16 1.374(4) . ? C16 C17 1.392(3) . ? C17 C18 1.389(3) . ? C19 C20 1.388(3) . ? C19 C24 1.414(3) . ? C20 C21 1.385(3) . ? C21 C22 1.396(3) . ? C22 C23 1.381(3) . ? C23 C24 1.392(3) . ? C24 C25 1.443(3) . ? C25 C26 1.400(3) . ? C25 C30 1.409(3) . ? C26 C27 1.380(3) . ? C27 C28 1.386(4) . ? C28 C29 1.382(3) . ? C29 C30 1.388(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 O1 P1 C18 117.18(9) . . ? O1 P1 C1 111.81(9) . . ? C18 P1 C1 107.83(9) . . ? O1 P1 C7 118.04(10) . . ? C18 P1 C7 92.31(10) . . ? C1 P1 C7 107.77(9) . . ? C30 N1 C19 108.54(17) . . ? C30 N1 C4 125.67(17) . . ? C19 N1 C4 124.96(17) . . ? C6 C1 C2 119.34(18) . . ? C6 C1 P1 118.81(15) . . ? C2 C1 P1 121.84(16) . . ? C3 C2 C1 120.65(19) . . ? C2 C3 C4 119.25(18) . . ? C3 C4 C5 120.66(18) . . ? C3 C4 N1 119.71(18) . . ? C5 C4 N1 119.63(18) . . ? C6 C5 C4 119.89(19) . . ? C5 C6 C1 120.18(19) . . ? C8 C7 C12 121.0(2) . . ? C8 C7 P1 128.8(2) . . ? C12 C7 P1 110.18(16) . . ? C7 C8 C9 118.7(3) . . ? C10 C9 C8 120.5(3) . . ? C9 C10 C11 121.4(3) . . ? C10 C11 C12 118.6(3) . . ? C11 C12 C7 119.8(2) . . ? C11 C12 C13 126.4(2) . . ? C7 C12 C13 113.79(19) . . ? C14 C13 C18 119.5(2) . . ? C14 C13 C12 127.4(2) . . ? C18 C13 C12 113.11(19) . . ? C15 C14 C13 119.1(2) . . ? C16 C15 C14 121.5(2) . . ? C15 C16 C17 120.3(2) . . ? C18 C17 C16 118.9(2) . . ? C17 C18 C13 120.7(2) . . ? C17 C18 P1 128.75(17) . . ? C13 C18 P1 110.60(16) . . ? C20 C19 N1 129.89(19) . . ? C20 C19 C24 121.57(19) . . ? N1 C19 C24 108.53(18) . . ? C21 C20 C19 117.4(2) . . ? C20 C21 C22 121.8(2) . . ? C23 C22 C21 120.4(2) . . ? C22 C23 C24 119.2(2) . . ? C23 C24 C19 119.5(2) . . ? C23 C24 C25 133.4(2) . . ? C19 C24 C25 107.10(18) . . ? C26 C25 C30 119.6(2) . . ? C26 C25 C24 133.5(2) . . ? C30 C25 C24 106.86(18) . . ? C27 C26 C25 118.5(2) . . ? C26 C27 C28 121.1(2) . . ? C29 C28 C27 121.8(2) . . ? C28 C29 C30 117.5(2) . . ? C29 C30 N1 129.4(2) . . ? C29 C30 C25 121.6(2) . . ? N1 C30 C25 108.97(18) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.397 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.072