# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 # 1. SUBMISSION DETAILS _publ_contact_letter ; Please consider this CIF submission for publication in Chem Communications ; _publ_contact_author 'G. Bertrand' _publ_contact_author_address ; University of California UCR-CNRS Joint Research Lab (UMR 2282) Department of Chemistry Riverside, CA 92521 USA ; _publ_contact_author_fax 951-827-4713 _publ_contact_author_email guy.bertrand@ucr.edu #============================================================================= # 2. TITLE AND AUTHOR LIST _publ_section_title ; A Persistent P,N-Heterocyclic Carbene ; loop_ _publ_author_name _publ_author_address G.D.Frey ; University of California UCR-CNRS Joint Research Lab (UMR 2282) Department of Chemistry Riverside, CA 92521 USA ; 'Maoying Song.' ; University of California UCR-CNRS Joint Research Lab (UMR 2282) Department of Chemistry Riverside, CA 92521 USA ; 'Jean-Baptiste Bourg' ; University of California UCR-CNRS Joint Research Lab (UMR 2282) Department of Chemistry Riverside, CA 92521 USA ; 'Michele Soleilhavoup' ; University of California UCR-CNRS Joint Research Lab (UMR 2282) Department of Chemistry Riverside, CA 92521 USA ; 'Guy Bertrand' ; University of California UCR-CNRS Joint Research Lab (UMR 2282) Department of Chemistry Riverside, CA 92521 USA ; #============================================================================== _publ_section_references ; Bruker (2003). COSMO version 1.52. Bruker AXS Inc., Madison, Wisconsin, U.S.A. Bruker (2003). SAINT version V7.21A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2004). APEX 2 version 2.0-2. Bruker AXS Inc., Madison, Wisconsin, U.S.A. Bruker (2004). SADABS version 2004/1. Bruker AXS Inc., Madison, Wisconsin, USA. SADABS, version 2004/1, Bruker (2004), Bruker AXS Inc., Madison, Wisconsin, USA. SHELXTL, version 6.14, Bruker (2003), Bruker AXS Inc., Madison, Wisconsin, USA. Altomare, A., Burla, M.C., Carnalli, M. Cascarano, G. Giacovazzo, C., Guagliardi, A.; Moliterni, A.G.G.; Polidori, G. Spagan, R. SIR 97 (1999) J. Appl. Cryst. 32, 115-122. ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565 ; _publ_contact_author_name 'G. Bertrand' #**************************************************************************** data_3c _database_code_depnum_ccdc_archive 'CCDC 695385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C37 H59 Br Cl4 N P' _chemical_formula_sum 'C37 H59 Br Cl4 N P' _chemical_formula_weight 770.53 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 13.146(3) _cell_length_b 17.956(3) _cell_length_c 17.575(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.959(3) _cell_angle_gamma 90.00 _cell_volume 4126.0(14) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 5238 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 21.74 _exptl_crystal_description 'prism frag' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 1.319 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7802 _exptl_absorpt_correction_T_max 0.8483 _exptl_absorpt_process_details multi-scan _exptl_special_details ; Measurement were carried out on a Bruker X8 APEX2 (version 2.0-2) KAPPA-CCD X-Ray diffractometer system (Mo-radiation, \l = 0.71073 \%A, 50KV/30mA power) Compound was collected at T = 100 K Frames were integrated with the aid of the Bruker SAINT version 7.06A software and using a narrow-frame integration algorithm. Absorption corrections were applied to the raw intensity data using the SADABS program (version 2004/1). ; _diffrn_ambient_temperature 160(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23150 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 23.26 _reflns_number_total 5896 _reflns_number_gt 4623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ' Sir97' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _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^)+(0.0645P)^2^+8.2345P] 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 SHELXL _refine_ls_extinction_coef 0.0015(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5896 _refine_ls_number_parameters 485 _refine_ls_number_restraints 49 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1607 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.004 _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 Br1 Br 0.84356(4) 0.86352(3) 0.16223(3) 0.0517(2) Uani 1 1 d . . . P1 P 0.75591(9) 0.55555(7) 0.18942(8) 0.0422(3) Uani 1 1 d . . . N1 N 0.6691(3) 0.6102(2) 0.3092(2) 0.0381(9) Uani 1 1 d D . . C1 C 0.6979(3) 0.5505(2) 0.2752(3) 0.0353(10) Uani 1 1 d . A . H1 H 0.6875 0.5032 0.2973 0.042 Uiso 1 1 calc R . . C2A C 0.6972(7) 0.6831(4) 0.2743(6) 0.037(3) Uani 0.69 1 d PD A 1 H2A H 0.6610 0.6880 0.2216 0.045 Uiso 0.69 1 calc PR A 1 C17A C 0.6717(6) 0.7494(4) 0.3230(5) 0.056(2) Uani 0.69 1 d PD A 1 H17A H 0.6892 0.7957 0.2979 0.084 Uiso 0.69 1 calc PR A 1 H17B H 0.7111 0.7460 0.3734 0.084 Uiso 0.69 1 calc PR A 1 H17C H 0.5985 0.7491 0.3292 0.084 Uiso 0.69 1 calc PR A 1 C2B C 0.7112(11) 0.6881(5) 0.3058(12) 0.037(7) Uani 0.31 1 d PD A 2 H2B H 0.7158 0.7149 0.3560 0.044 Uiso 0.31 1 calc PR A 2 C17B C 0.6362(13) 0.7237(10) 0.2441(12) 0.067(6) Uani 0.31 1 d PD A 2 H17D H 0.5665 0.7197 0.2589 0.100 Uiso 0.31 1 calc PR A 2 H17E H 0.6401 0.6978 0.1954 0.100 Uiso 0.31 1 calc PR A 2 H17F H 0.6537 0.7763 0.2385 0.100 Uiso 0.31 1 calc PR A 2 C3 C 0.8148(4) 0.6838(3) 0.2706(3) 0.0547(14) Uani 1 1 d D . . H3A H 0.8386 0.7355 0.2645 0.066 Uiso 1 1 calc R A 1 H3B H 0.8499 0.6635 0.3188 0.066 Uiso 1 1 calc R A 1 C4 C 0.8405(4) 0.6370(3) 0.2038(3) 0.0513(13) Uani 1 1 d . A . H4A H 0.9123 0.6200 0.2130 0.062 Uiso 1 1 calc R . . H4B H 0.8339 0.6678 0.1568 0.062 Uiso 1 1 calc R . . C5 C 0.8260(3) 0.4723(2) 0.1652(3) 0.0390(11) Uani 1 1 d . . . C6 C 0.7846(3) 0.4379(3) 0.0963(3) 0.0409(11) Uani 1 1 d . . . C7 C 0.8495(3) 0.3982(3) 0.0542(3) 0.0444(12) Uani 1 1 d . . . H7 H 0.8216 0.3756 0.0078 0.053 Uiso 1 1 calc R . . C8 C 0.9524(4) 0.3897(3) 0.0760(3) 0.0437(12) Uani 1 1 d . . . C9 C 0.9882(3) 0.4163(3) 0.1471(3) 0.0444(12) Uani 1 1 d . . . H9 H 1.0580 0.4077 0.1648 0.053 Uiso 1 1 calc R . . C10 C 0.9284(3) 0.4552(2) 0.1949(3) 0.0382(11) Uani 1 1 d . . . C11 C 0.5961(3) 0.6043(2) 0.3662(3) 0.0391(11) Uani 1 1 d . A . C12 C 0.6324(4) 0.6042(2) 0.4432(3) 0.0429(12) Uani 1 1 d . . . C13 C 0.5611(4) 0.5989(3) 0.4959(3) 0.0531(13) Uani 1 1 d . A . H13 H 0.5838 0.5994 0.5490 0.064 Uiso 1 1 calc R . . C14 C 0.4585(4) 0.5929(3) 0.4728(4) 0.0559(14) Uani 1 1 d . . . H14 H 0.4109 0.5889 0.5098 0.067 Uiso 1 1 calc R A . C15 C 0.4244(4) 0.5926(3) 0.3963(3) 0.0530(14) Uani 1 1 d . A . H15 H 0.3532 0.5884 0.3810 0.064 Uiso 1 1 calc R . . C16 C 0.4919(3) 0.5984(2) 0.3405(3) 0.0447(12) Uani 1 1 d . . . C18 C 0.6702(3) 0.4406(3) 0.0634(3) 0.0505(13) Uani 1 1 d . . . C19 C 0.5964(4) 0.4369(3) 0.1249(3) 0.0609(15) Uani 1 1 d . . . H19A H 0.5932 0.4856 0.1496 0.073 Uiso 1 1 calc R . . H19B H 0.6205 0.3995 0.1632 0.073 Uiso 1 1 calc R . . H19C H 0.5282 0.4231 0.1013 0.073 Uiso 1 1 calc R . . C20 C 0.6418(5) 0.3728(4) 0.0116(5) 0.098(3) Uani 1 1 d . . . H20A H 0.5699 0.3765 -0.0093 0.118 Uiso 1 1 calc R . . H20B H 0.6522 0.3270 0.0417 0.118 Uiso 1 1 calc R . . H20C H 0.6853 0.3720 -0.0304 0.118 Uiso 1 1 calc R . . C21 C 0.6507(4) 0.5096(4) 0.0132(3) 0.0673(17) Uani 1 1 d . . . H21A H 0.5798 0.5091 -0.0105 0.081 Uiso 1 1 calc R . . H21B H 0.6974 0.5096 -0.0268 0.081 Uiso 1 1 calc R . . H21C H 0.6623 0.5545 0.0447 0.081 Uiso 1 1 calc R . . C22 C 1.0252(4) 0.3515(3) 0.0257(3) 0.0528(14) Uani 1 1 d . . . C23 C 0.9700(6) 0.3222(5) -0.0492(5) 0.104(3) Uani 1 1 d . . . H23A H 0.9180 0.2859 -0.0378 0.124 Uiso 1 1 calc R . . H23B H 1.0196 0.2981 -0.0792 0.124 Uiso 1 1 calc R . . H23C H 0.9372 0.3637 -0.0784 0.124 Uiso 1 1 calc R . . C24 C 1.0728(6) 0.2844(4) 0.0663(5) 0.104(3) Uani 1 1 d . . . H24A H 1.1155 0.3003 0.1124 0.125 Uiso 1 1 calc R . . H24B H 1.1150 0.2579 0.0323 0.125 Uiso 1 1 calc R . . H24C H 1.0187 0.2512 0.0806 0.125 Uiso 1 1 calc R . . C25 C 1.1048(5) 0.4066(4) 0.0065(4) 0.086(2) Uani 1 1 d . . . H25A H 1.0713 0.4492 -0.0204 0.103 Uiso 1 1 calc R . . H25B H 1.1511 0.3827 -0.0264 0.103 Uiso 1 1 calc R . . H25C H 1.1440 0.4238 0.0537 0.103 Uiso 1 1 calc R . . C26 C 0.9799(3) 0.4668(3) 0.2770(3) 0.0484(13) Uani 1 1 d . . . C27 C 0.9127(4) 0.4985(3) 0.3351(3) 0.0557(14) Uani 1 1 d . . . H27A H 0.9507 0.4979 0.3862 0.067 Uiso 1 1 calc R . . H27B H 0.8508 0.4681 0.3354 0.067 Uiso 1 1 calc R . . H27C H 0.8935 0.5498 0.3212 0.067 Uiso 1 1 calc R . . C28 C 1.0110(4) 0.3889(3) 0.3091(3) 0.0615(15) Uani 1 1 d . . . H28A H 1.0611 0.3667 0.2782 0.074 Uiso 1 1 calc R . . H28B H 0.9504 0.3569 0.3071 0.074 Uiso 1 1 calc R . . H28C H 1.0412 0.3937 0.3622 0.074 Uiso 1 1 calc R . . C29 C 1.0751(4) 0.5157(3) 0.2763(4) 0.0659(16) Uani 1 1 d . . . H29A H 1.1099 0.5192 0.3282 0.079 Uiso 1 1 calc R . . H29B H 1.0549 0.5655 0.2578 0.079 Uiso 1 1 calc R . . H29C H 1.1215 0.4935 0.2424 0.079 Uiso 1 1 calc R . . C30 C 0.7459(4) 0.6085(3) 0.4706(3) 0.0476(12) Uani 1 1 d . A . H30 H 0.7834 0.6187 0.4251 0.057 Uiso 1 1 calc R . . C31 C 0.7708(5) 0.6713(3) 0.5280(4) 0.0720(17) Uani 1 1 d . . . H31A H 0.7414 0.7180 0.5069 0.086 Uiso 1 1 calc R A . H31B H 0.8451 0.6765 0.5382 0.086 Uiso 1 1 calc R . . H31C H 0.7418 0.6597 0.5758 0.086 Uiso 1 1 calc R . . C32 C 0.7833(4) 0.5330(3) 0.5042(3) 0.0616(15) Uani 1 1 d . . . H32A H 0.7514 0.5232 0.5511 0.074 Uiso 1 1 calc R A . H32B H 0.8578 0.5342 0.5159 0.074 Uiso 1 1 calc R . . H32C H 0.7646 0.4935 0.4669 0.074 Uiso 1 1 calc R . . C33 C 0.4521(4) 0.5975(3) 0.2574(3) 0.0603(15) Uani 1 1 d . A . H33 H 0.5121 0.6027 0.2272 0.072 Uiso 1 1 calc R . . C34 C 0.3804(6) 0.6636(5) 0.2368(4) 0.112(3) Uani 1 1 d . . . H34A H 0.3206 0.6600 0.2655 0.135 Uiso 1 1 calc R A . H34B H 0.3581 0.6627 0.1818 0.135 Uiso 1 1 calc R . . H34C H 0.4168 0.7103 0.2499 0.135 Uiso 1 1 calc R . . C35 C 0.4002(5) 0.5236(5) 0.2351(5) 0.103(3) Uani 1 1 d . . . H35A H 0.4485 0.4827 0.2472 0.124 Uiso 1 1 calc R A . H35B H 0.3781 0.5236 0.1801 0.124 Uiso 1 1 calc R . . H35C H 0.3406 0.5171 0.2636 0.124 Uiso 1 1 calc R . . C10A C 0.6548(11) 0.8035(11) 0.0121(18) 0.138(13) Uani 0.57 1 d PD B 1 H10A H 0.7004 0.7879 -0.0264 0.166 Uiso 0.57 1 calc PR B 1 H10B H 0.6961 0.8330 0.0517 0.166 Uiso 0.57 1 calc PR B 1 Cl1A Cl 0.5592(9) 0.8592(6) -0.0316(7) 0.142(4) Uani 0.57 1 d PDU B 1 Cl2A Cl 0.6096(9) 0.7261(5) 0.0537(4) 0.137(4) Uani 0.57 1 d PDU B 1 C10B C 0.6551(9) 0.8109(8) 0.0029(15) 0.056(7) Uani 0.43 1 d PD C 2 H10C H 0.7036 0.8164 -0.0362 0.067 Uiso 0.43 1 calc PR C 2 H10D H 0.6886 0.8315 0.0515 0.067 Uiso 0.43 1 calc PR C 2 Cl1B Cl 0.5475(7) 0.8632(6) -0.0248(5) 0.068(2) Uani 0.43 1 d PDU C 2 Cl2B Cl 0.6325(9) 0.7184(5) 0.0155(6) 0.129(4) Uani 0.43 1 d PDU C 2 C10C C 0.0951(6) 0.8121(5) 0.2575(8) 0.087(3) Uani 0.70 1 d PD D 1 H10E H 0.0462 0.8154 0.2108 0.105 Uiso 0.70 1 calc PR D 1 H10F H 0.0706 0.8464 0.2957 0.105 Uiso 0.70 1 calc PR D 1 Cl3A Cl 0.0911(3) 0.7243(3) 0.2920(4) 0.163(2) Uani 0.70 1 d PDU D 1 Cl4A Cl 0.2099(2) 0.84294(18) 0.2358(2) 0.1133(11) Uani 0.70 1 d PD D 1 C10D C 0.0732(12) 0.7851(15) 0.3020(14) 0.088(7) Uani 0.30 1 d PDU E 2 H10G H 0.0120 0.8151 0.2848 0.106 Uiso 0.30 1 calc PR E 2 H10H H 0.0548 0.7514 0.3430 0.106 Uiso 0.30 1 calc PR E 2 Cl3B Cl 0.1041(8) 0.7316(6) 0.2261(8) 0.161(4) Uani 0.30 1 d PDU E 2 Cl4B Cl 0.1666(9) 0.8431(5) 0.3393(8) 0.218(8) Uani 0.30 1 d PD E 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 Br1 0.0636(4) 0.0435(3) 0.0478(4) 0.0037(2) 0.0050(2) 0.0031(2) P1 0.0384(7) 0.0407(7) 0.0480(8) 0.0045(6) 0.0064(6) 0.0061(5) N1 0.036(2) 0.030(2) 0.049(2) -0.0007(18) 0.0062(18) 0.0030(16) C1 0.031(2) 0.031(2) 0.042(3) 0.004(2) 0.000(2) 0.0047(19) C2A 0.049(6) 0.028(5) 0.034(6) -0.002(4) 0.000(4) 0.003(4) C17A 0.071(5) 0.042(5) 0.057(5) -0.002(4) 0.018(4) 0.004(4) C2B 0.028(9) 0.025(10) 0.057(18) -0.012(8) -0.004(10) -0.001(7) C17B 0.055(11) 0.046(10) 0.102(17) 0.018(11) 0.028(11) 0.015(9) C3 0.050(3) 0.034(3) 0.081(4) 0.004(3) 0.015(3) -0.001(2) C4 0.048(3) 0.043(3) 0.064(4) 0.010(3) 0.011(3) 0.000(2) C5 0.033(2) 0.035(2) 0.051(3) 0.006(2) 0.009(2) 0.0027(19) C6 0.031(2) 0.042(3) 0.050(3) 0.007(2) 0.008(2) 0.002(2) C7 0.038(3) 0.046(3) 0.049(3) 0.003(2) 0.009(2) 0.000(2) C8 0.043(3) 0.032(2) 0.058(4) 0.001(2) 0.018(2) 0.000(2) C9 0.029(2) 0.037(3) 0.067(4) 0.010(3) 0.007(2) 0.003(2) C10 0.030(2) 0.032(2) 0.053(3) 0.006(2) 0.003(2) 0.0010(19) C11 0.041(3) 0.028(2) 0.049(3) -0.002(2) 0.010(2) 0.003(2) C12 0.049(3) 0.030(2) 0.050(3) 0.007(2) 0.006(2) 0.007(2) C13 0.071(4) 0.037(3) 0.052(3) 0.005(2) 0.013(3) -0.001(2) C14 0.059(4) 0.038(3) 0.075(4) -0.001(3) 0.029(3) -0.002(2) C15 0.042(3) 0.042(3) 0.075(4) -0.011(3) 0.010(3) 0.001(2) C16 0.040(3) 0.034(3) 0.061(3) -0.007(2) 0.012(2) 0.002(2) C18 0.031(2) 0.062(3) 0.058(3) -0.004(3) 0.002(2) 0.001(2) C19 0.037(3) 0.085(4) 0.058(4) 0.008(3) -0.004(3) -0.009(3) C20 0.051(4) 0.117(6) 0.123(7) -0.060(5) -0.007(4) -0.004(4) C21 0.043(3) 0.102(5) 0.055(4) 0.025(3) -0.003(3) 0.005(3) C22 0.050(3) 0.038(3) 0.075(4) 0.002(3) 0.030(3) 0.001(2) C23 0.085(5) 0.119(6) 0.114(7) -0.047(5) 0.045(5) -0.011(4) C24 0.124(6) 0.061(4) 0.141(7) 0.010(4) 0.075(6) 0.036(4) C25 0.083(5) 0.070(4) 0.115(6) -0.009(4) 0.066(4) -0.006(3) C26 0.036(3) 0.046(3) 0.061(3) 0.001(2) -0.006(2) 0.006(2) C27 0.051(3) 0.058(3) 0.055(4) -0.001(3) -0.011(3) 0.006(3) C28 0.065(3) 0.055(3) 0.062(4) 0.006(3) -0.008(3) 0.013(3) C29 0.045(3) 0.072(4) 0.079(4) -0.004(3) -0.003(3) -0.009(3) C30 0.050(3) 0.045(3) 0.047(3) 0.007(2) 0.000(2) 0.002(2) C31 0.076(4) 0.058(4) 0.078(5) -0.005(3) -0.011(3) 0.000(3) C32 0.060(3) 0.055(3) 0.067(4) 0.015(3) -0.004(3) 0.004(3) C33 0.037(3) 0.076(4) 0.067(4) -0.019(3) -0.002(3) 0.007(3) C34 0.108(6) 0.144(7) 0.077(5) -0.026(5) -0.030(4) 0.072(5) C35 0.072(4) 0.127(7) 0.114(6) -0.064(5) 0.026(4) -0.039(4) C10A 0.14(2) 0.10(2) 0.15(2) 0.030(16) -0.090(16) -0.014(15) Cl1A 0.155(8) 0.092(6) 0.166(8) 0.007(5) -0.039(6) 0.021(5) Cl2A 0.205(9) 0.073(3) 0.118(5) 0.015(3) -0.053(5) -0.039(4) C10B 0.034(10) 0.043(11) 0.091(17) -0.007(10) 0.009(11) -0.002(8) Cl1B 0.061(3) 0.070(4) 0.070(4) -0.014(3) -0.008(3) 0.021(3) Cl2B 0.113(4) 0.056(3) 0.213(12) 0.019(6) -0.013(7) -0.008(3) C10C 0.055(5) 0.063(6) 0.141(10) 0.042(6) 0.002(6) -0.003(4) Cl3A 0.100(3) 0.134(3) 0.244(6) 0.106(4) -0.038(3) -0.039(2) Cl4A 0.0641(15) 0.112(2) 0.168(3) 0.044(2) 0.0317(18) 0.0024(14) C10D 0.084(10) 0.063(10) 0.118(11) -0.021(9) 0.015(9) 0.028(8) Cl3B 0.109(6) 0.109(7) 0.258(13) -0.028(8) -0.021(8) 0.024(5) Cl4B 0.230(12) 0.101(6) 0.280(17) -0.041(7) -0.177(13) 0.051(7) _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 C1 1.761(5) . ? P1 C5 1.829(4) . ? P1 C4 1.838(5) . ? N1 C1 1.302(6) . ? N1 C11 1.461(6) . ? N1 C2A 1.508(7) . ? N1 C2B 1.509(8) . ? C2A C17A 1.524(10) . ? C2A C3 1.555(9) . ? C2B C17B 1.528(15) . ? C2B C3 1.555(14) . ? C3 C4 1.511(8) . ? C5 C6 1.418(7) . ? C5 C10 1.427(6) . ? C6 C7 1.384(7) . ? C6 C18 1.554(6) . ? C7 C8 1.375(6) . ? C8 C9 1.375(7) . ? C8 C22 1.531(7) . ? C9 C10 1.395(7) . ? C10 C26 1.542(7) . ? C11 C12 1.388(7) . ? C11 C16 1.400(6) . ? C12 C13 1.389(7) . ? C12 C30 1.521(7) . ? C13 C14 1.372(8) . ? C14 C15 1.372(8) . ? C15 C16 1.392(7) . ? C16 C33 1.500(8) . ? C18 C19 1.526(7) . ? C18 C21 1.527(8) . ? C18 C20 1.543(8) . ? C22 C25 1.504(7) . ? C22 C24 1.504(8) . ? C22 C23 1.529(10) . ? C26 C27 1.529(7) . ? C26 C29 1.529(7) . ? C26 C28 1.549(7) . ? C30 C31 1.525(8) . ? C30 C32 1.538(7) . ? C33 C35 1.523(8) . ? C33 C34 1.536(8) . ? C10A Cl2A 1.705(10) . ? C10A Cl1A 1.723(9) . ? C10B Cl2B 1.706(10) . ? C10B Cl1B 1.725(8) . ? C10C Cl4A 1.688(8) . ? C10C Cl3A 1.693(7) . ? C10D Cl4B 1.690(11) . ? C10D Cl3B 1.726(10) . ? 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 P1 C5 115.5(2) . . ? C1 P1 C4 103.4(2) . . ? C5 P1 C4 111.7(2) . . ? C1 N1 C11 119.9(4) . . ? C1 N1 C2A 115.6(5) . . ? C11 N1 C2A 123.2(4) . . ? C1 N1 C2B 128.3(7) . . ? C11 N1 C2B 111.3(7) . . ? C2A N1 C2B 21.9(8) . . ? N1 C1 P1 121.5(3) . . ? N1 C2A C17A 111.9(7) . . ? N1 C2A C3 108.1(5) . . ? C17A C2A C3 107.2(6) . . ? N1 C2B C17B 101.7(12) . . ? N1 C2B C3 108.1(8) . . ? C17B C2B C3 105.4(13) . . ? C4 C3 C2A 109.3(5) . . ? C4 C3 C2B 127.8(7) . . ? C2A C3 C2B 21.2(8) . . ? C3 C4 P1 111.6(3) . . ? C6 C5 C10 118.9(4) . . ? C6 C5 P1 113.4(3) . . ? C10 C5 P1 124.8(4) . . ? C7 C6 C5 118.5(4) . . ? C7 C6 C18 116.4(4) . . ? C5 C6 C18 125.1(4) . . ? C8 C7 C6 123.4(5) . . ? C9 C8 C7 116.7(4) . . ? C9 C8 C22 120.3(5) . . ? C7 C8 C22 123.0(5) . . ? C8 C9 C10 124.0(4) . . ? C9 C10 C5 117.2(4) . . ? C9 C10 C26 114.3(4) . . ? C5 C10 C26 128.2(4) . . ? C12 C11 C16 122.7(4) . . ? C12 C11 N1 118.9(4) . . ? C16 C11 N1 118.3(4) . . ? C11 C12 C13 117.6(5) . . ? C11 C12 C30 122.5(4) . . ? C13 C12 C30 120.0(5) . . ? C14 C13 C12 121.3(5) . . ? C13 C14 C15 120.1(5) . . ? C14 C15 C16 121.5(5) . . ? C15 C16 C11 116.9(5) . . ? C15 C16 C33 120.1(5) . . ? C11 C16 C33 123.1(4) . . ? C19 C18 C21 111.4(4) . . ? C19 C18 C20 104.5(5) . . ? C21 C18 C20 106.5(6) . . ? C19 C18 C6 113.4(4) . . ? C21 C18 C6 109.7(4) . . ? C20 C18 C6 111.1(4) . . ? C25 C22 C24 111.7(5) . . ? C25 C22 C23 108.2(6) . . ? C24 C22 C23 105.6(6) . . ? C25 C22 C8 109.1(4) . . ? C24 C22 C8 109.8(5) . . ? C23 C22 C8 112.5(5) . . ? C27 C26 C29 108.8(4) . . ? C27 C26 C10 116.6(4) . . ? C29 C26 C10 110.5(4) . . ? C27 C26 C28 104.0(5) . . ? C29 C26 C28 109.6(4) . . ? C10 C26 C28 107.0(4) . . ? C12 C30 C31 112.5(4) . . ? C12 C30 C32 110.0(4) . . ? C31 C30 C32 111.1(5) . . ? C16 C33 C35 111.2(6) . . ? C16 C33 C34 111.4(5) . . ? C35 C33 C34 111.4(6) . . ? Cl2A C10A Cl1A 113.2(8) . . ? Cl2B C10B Cl1B 114.7(8) . . ? Cl4A C10C Cl3A 116.6(5) . . ? Cl4B C10D Cl3B 115.1(9) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.859 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.069 #====END data_3c' _database_code_depnum_ccdc_archive 'CCDC 695386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C47 H79 Br2 Li N O3 P' _chemical_formula_sum 'C47 H79 Br2 Li N O3 P' _chemical_formula_weight 903.84 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' Li Li -0.0003 0.0001 '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 10.9613(13) _cell_length_b 14.7848(18) _cell_length_c 16.2547(19) _cell_angle_alpha 99.990(2) _cell_angle_beta 108.109(2) _cell_angle_gamma 97.624(2) _cell_volume 2416.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1771 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 20.5 _exptl_crystal_description Prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 1.748 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7554 _exptl_absorpt_correction_T_max 0.9494 _exptl_absorpt_process_details multi-scan _exptl_special_details ; Measurement were carried out on a Bruker X8 APEX2 (version 2.0-2) KAPPA-CCD X-Ray diffractometer system (Mo-radiation, \l = 0.71073 \%A, 50KV/30mA power) Compound was collected at T = 100 K Frames were integrated with the aid of the Bruker SAINT version 7.06A software and using a narrow-frame integration algorithm. Absorption corrections were applied to the raw intensity data using the SADABS program (version 2004/1). ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14058 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.1100 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 23.26 _reflns_number_total 6875 _reflns_number_gt 4014 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution Sir97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _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^)+(0.0535P)^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 SHELXL _refine_ls_extinction_coef 0.0015(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6875 _refine_ls_number_parameters 555 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1264 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.002 _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 Br1A Br 0.2207(6) 0.7335(3) 1.0216(3) 0.0341(14) Uani 0.50 1 d P A 1 Br2A Br 0.2321(7) 0.6347(6) 0.7583(5) 0.0673(19) Uani 0.50 1 d P A 1 Br1B Br 0.2106(6) 0.7300(4) 1.0205(3) 0.053(2) Uani 0.50 1 d P A 2 Br2B Br 0.2149(6) 0.6385(6) 0.7547(5) 0.0406(12) Uani 0.50 1 d P A 2 P1A P 0.2484(2) 0.29168(13) 0.32885(12) 0.0213(5) Uani 0.80 1 d PD B 1 C1A C 0.1484(5) 0.1817(3) 0.2958(3) 0.0243(13) Uani 0.80 1 d P B 1 C2A C 0.1345(8) 0.3619(5) 0.2741(4) 0.0324(19) Uani 0.80 1 d PD B 1 H2A H 0.0614 0.3614 0.2987 0.039 Uiso 0.80 1 calc PR B 1 C3A C 0.0811(8) 0.3024(5) 0.1769(4) 0.034(2) Uani 0.80 1 d PD B 1 H3A1 H 0.0340 0.3404 0.1380 0.041 Uiso 0.80 1 calc PR B 1 H3A2 H 0.1568 0.2902 0.1588 0.041 Uiso 0.80 1 calc PR B 1 C4A C -0.0117(10) 0.2074(5) 0.1596(6) 0.040(3) Uani 0.80 1 d PD B 1 H4A1 H -0.0931 0.2182 0.1706 0.048 Uiso 0.80 1 calc PR B 1 H4A2 H -0.0355 0.1737 0.0969 0.048 Uiso 0.80 1 calc PR B 1 C35A C 0.1928(8) 0.4597(4) 0.2802(5) 0.047(2) Uani 0.80 1 d P B 1 H35A H 0.2586 0.4604 0.2509 0.070 Uiso 0.80 1 calc PR B 1 H35B H 0.2344 0.4923 0.3429 0.070 Uiso 0.80 1 calc PR B 1 H35C H 0.1240 0.4913 0.2509 0.070 Uiso 0.80 1 calc PR B 1 N1A N 0.0544(4) 0.1495(3) 0.2196(3) 0.0261(11) Uani 0.80 1 d PD B 1 P1B P 0.1858(10) 0.3015(4) 0.3490(4) 0.039(2) Uani 0.20 1 d PD B 2 C1B C 0.1484(5) 0.1817(3) 0.2958(3) 0.0243(13) Uani 0.20 1 d P B 2 C2B C 0.189(3) 0.358(2) 0.2569(14) 0.027(9) Uiso 0.20 1 d PD B 2 H2B1 H 0.2141 0.4272 0.2756 0.032 Uiso 0.20 1 calc PR B 2 H2B2 H 0.2446 0.3330 0.2240 0.032 Uiso 0.20 1 calc PR B 2 C3B C 0.040(3) 0.322(2) 0.206(3) 0.077(16) Uiso 0.20 1 d PD B 2 H3B1 H -0.0096 0.3252 0.2477 0.093 Uiso 0.20 1 calc PR B 2 H3B2 H 0.0062 0.3576 0.1612 0.093 Uiso 0.20 1 calc PR B 2 C4B C 0.033(3) 0.2182(17) 0.1619(17) 0.000(9) Uiso 0.20 1 d PD B 2 H4B H -0.0617 0.1967 0.1243 0.000 Uiso 0.20 1 calc PR B 2 C35B C 0.093(4) 0.214(3) 0.102(3) 0.089(13) Uiso 0.20 1 d P B 2 H35D H 0.1871 0.2361 0.1324 0.134 Uiso 0.20 1 calc PR B 2 H35E H 0.0593 0.2536 0.0612 0.134 Uiso 0.20 1 calc PR B 2 H35F H 0.0754 0.1490 0.0687 0.134 Uiso 0.20 1 calc PR B 2 N1B N 0.0544(4) 0.1495(3) 0.2196(3) 0.0261(11) Uani 0.20 1 d PD B 2 C11 C 0.3244(5) 0.3113(3) 0.4509(3) 0.0259(13) Uani 1 1 d . . . C5 C -0.0004(6) 0.0485(3) 0.1872(3) 0.0296(14) Uani 1 1 d . . . C6 C -0.1255(6) 0.0148(4) 0.1871(3) 0.0287(14) Uani 1 1 d . B . C7 C -0.1720(6) -0.0810(4) 0.1553(4) 0.0397(16) Uani 1 1 d . . . H7 H -0.2570 -0.1075 0.1532 0.048 Uiso 1 1 calc R B . C8 C -0.0969(6) -0.1384(4) 0.1265(4) 0.0388(16) Uani 1 1 d . B . H8 H -0.1309 -0.2038 0.1059 0.047 Uiso 1 1 calc R . . C9 C 0.0256(6) -0.1033(4) 0.1269(3) 0.0352(15) Uani 1 1 d . . . H9 H 0.0747 -0.1448 0.1065 0.042 Uiso 1 1 calc R B . C10 C 0.0792(5) -0.0076(4) 0.1568(3) 0.0271(14) Uani 1 1 d . B . C12 C 0.4591(6) 0.3110(3) 0.4753(3) 0.0270(13) Uani 1 1 d . B . C13 C 0.5239(5) 0.3013(3) 0.5620(3) 0.0259(13) Uani 1 1 d . . . H13 H 0.6142 0.2987 0.5784 0.031 Uiso 1 1 calc R B . C14 C 0.4637(6) 0.2954(3) 0.6244(3) 0.0256(13) Uani 1 1 d . B . C15 C 0.3331(6) 0.3023(3) 0.5996(3) 0.0303(14) Uani 1 1 d . . . H15 H 0.2914 0.3011 0.6427 0.036 Uiso 1 1 calc R B . C16 C 0.2587(5) 0.3109(3) 0.5153(3) 0.0275(13) Uani 1 1 d . B . C17 C -0.2075(6) 0.0758(4) 0.2197(4) 0.0394(16) Uani 1 1 d . . . H17 H -0.1536 0.1407 0.2436 0.047 Uiso 1 1 calc R B . C18 C -0.3311(6) 0.0802(4) 0.1437(4) 0.0472(17) Uani 1 1 d . B . H18A H -0.3053 0.1068 0.0990 0.071 Uiso 1 1 calc R . . H18B H -0.3829 0.1197 0.1676 0.071 Uiso 1 1 calc R . . H18C H -0.3837 0.0168 0.1162 0.071 Uiso 1 1 calc R . . C19 C -0.2448(6) 0.0457(4) 0.2955(4) 0.0521(18) Uani 1 1 d . B . H19A H -0.3024 -0.0163 0.2733 0.078 Uiso 1 1 calc R . . H19B H -0.2904 0.0911 0.3186 0.078 Uiso 1 1 calc R . . H19C H -0.1653 0.0430 0.3432 0.078 Uiso 1 1 calc R . . C20 C 0.2129(5) 0.0300(4) 0.1558(3) 0.0287(14) Uani 1 1 d . . . H20 H 0.2309 0.0999 0.1752 0.034 Uiso 1 1 calc R B . C21 C 0.2212(6) 0.0041(4) 0.0628(3) 0.0418(16) Uani 1 1 d . B . H21A H 0.3061 0.0353 0.0632 0.063 Uiso 1 1 calc R . . H21B H 0.1508 0.0244 0.0206 0.063 Uiso 1 1 calc R . . H21C H 0.2121 -0.0639 0.0450 0.063 Uiso 1 1 calc R . . C22 C 0.3178(6) -0.0065(4) 0.2201(4) 0.0397(16) Uani 1 1 d . B . H22A H 0.3106 0.0079 0.2794 0.060 Uiso 1 1 calc R . . H22B H 0.4045 0.0236 0.2227 0.060 Uiso 1 1 calc R . . H22C H 0.3056 -0.0745 0.1995 0.060 Uiso 1 1 calc R . . C23 C 0.1181(5) 0.3249(4) 0.5014(3) 0.0317(14) Uani 1 1 d . . . C24 C 0.0851(6) 0.3313(5) 0.5869(4) 0.066(2) Uani 1 1 d . B . H24A H 0.0866 0.2713 0.6046 0.099 Uiso 1 1 calc R . . H24B H -0.0023 0.3460 0.5765 0.099 Uiso 1 1 calc R . . H24C H 0.1499 0.3809 0.6343 0.099 Uiso 1 1 calc R . . C25 C 0.1036(7) 0.4195(4) 0.4774(4) 0.0577(19) Uani 1 1 d . B . H25A H 0.0113 0.4248 0.4608 0.087 Uiso 1 1 calc R . . H25B H 0.1340 0.4241 0.4273 0.087 Uiso 1 1 calc R . . H25C H 0.1561 0.4703 0.5287 0.087 Uiso 1 1 calc R . . C26 C 0.0140(6) 0.2450(4) 0.4302(4) 0.0574(19) Uani 1 1 d . B . H26A H 0.0312 0.1844 0.4425 0.086 Uiso 1 1 calc R . . H26B H 0.0179 0.2483 0.3713 0.086 Uiso 1 1 calc R . . H26C H -0.0733 0.2515 0.4315 0.086 Uiso 1 1 calc R . . C27 C 0.5458(6) 0.3241(4) 0.4166(3) 0.0310(14) Uani 1 1 d . . . C28 C 0.5313(5) 0.4142(4) 0.3822(3) 0.0351(15) Uani 1 1 d . B . H28A H 0.5521 0.4676 0.4327 0.053 Uiso 1 1 calc R . . H28B H 0.4411 0.4079 0.3427 0.053 Uiso 1 1 calc R . . H28C H 0.5915 0.4243 0.3495 0.053 Uiso 1 1 calc R . . C29 C 0.5227(7) 0.2381(4) 0.3422(4) 0.0516(19) Uani 1 1 d . B . H29A H 0.5874 0.2474 0.3128 0.077 Uiso 1 1 calc R . . H29B H 0.4344 0.2289 0.2988 0.077 Uiso 1 1 calc R . . H29C H 0.5314 0.1826 0.3674 0.077 Uiso 1 1 calc R . . C30 C 0.6925(6) 0.3394(4) 0.4694(4) 0.0488(18) Uani 1 1 d . B . H30A H 0.7120 0.2828 0.4901 0.073 Uiso 1 1 calc R . . H30B H 0.7162 0.3924 0.5207 0.073 Uiso 1 1 calc R . . H30C H 0.7431 0.3528 0.4312 0.073 Uiso 1 1 calc R . . C31 C 0.5354(5) 0.2845(4) 0.7172(3) 0.0289(14) Uani 1 1 d . . . C32 C 0.6760(6) 0.2724(4) 0.7298(4) 0.0416(16) Uani 1 1 d . B . H32A H 0.6751 0.2168 0.6868 0.062 Uiso 1 1 calc R . . H32B H 0.7180 0.2649 0.7902 0.062 Uiso 1 1 calc R . . H32C H 0.7249 0.3279 0.7205 0.062 Uiso 1 1 calc R . . C33 C 0.5397(6) 0.3706(4) 0.7846(3) 0.0491(18) Uani 1 1 d . B . H33A H 0.5849 0.4262 0.7731 0.074 Uiso 1 1 calc R . . H33B H 0.5867 0.3639 0.8446 0.074 Uiso 1 1 calc R . . H33C H 0.4501 0.3774 0.7798 0.074 Uiso 1 1 calc R . . C34 C 0.4656(6) 0.1973(4) 0.7351(4) 0.0507(18) Uani 1 1 d . B . H34A H 0.3783 0.2056 0.7348 0.076 Uiso 1 1 calc R . . H34B H 0.5165 0.1880 0.7933 0.076 Uiso 1 1 calc R . . H34C H 0.4574 0.1424 0.6888 0.076 Uiso 1 1 calc R . . O1 O 0.4660(4) 0.6372(3) 0.9705(2) 0.0414(11) Uani 1 1 d . A . C101 C 0.5461(6) 0.7291(4) 0.9986(4) 0.057(2) Uani 1 1 d . . . H10A H 0.6196 0.7351 1.0545 0.068 Uiso 1 1 calc R . . H10B H 0.4941 0.7773 1.0080 0.068 Uiso 1 1 calc R . . C102 C 0.5957(7) 0.7388(4) 0.9237(4) 0.0569(19) Uani 1 1 d . . . H10C H 0.5329 0.7614 0.8773 0.068 Uiso 1 1 calc R . . H10D H 0.6816 0.7824 0.9454 0.068 Uiso 1 1 calc R . . C103 C 0.6078(8) 0.6410(5) 0.8894(5) 0.067(2) Uani 1 1 d . . . H10E H 0.5759 0.6253 0.8235 0.081 Uiso 1 1 calc R . . H10F H 0.7004 0.6343 0.9112 0.081 Uiso 1 1 calc R . . C104 C 0.5268(6) 0.5785(4) 0.9227(4) 0.0532(19) Uani 1 1 d . . . H10G H 0.4597 0.5318 0.8726 0.064 Uiso 1 1 calc R . . H10H H 0.5822 0.5449 0.9624 0.064 Uiso 1 1 calc R . . O2 O 0.2113(4) 0.4924(3) 0.9099(2) 0.0484(11) Uani 1 1 d . A . C201 C 0.1886(7) 0.4172(4) 0.8349(4) 0.0537(19) Uani 1 1 d . . . H20A H 0.2439 0.3711 0.8521 0.064 Uiso 1 1 calc R . . H20B H 0.2095 0.4414 0.7868 0.064 Uiso 1 1 calc R . . C202 C 0.0510(7) 0.3740(5) 0.8057(5) 0.070(2) Uani 1 1 d . . . H20C H 0.0374 0.3052 0.7849 0.084 Uiso 1 1 calc R . . H20D H -0.0017 0.3999 0.7573 0.084 Uiso 1 1 calc R . . C203 C 0.0171(10) 0.3989(7) 0.8873(6) 0.151(6) Uani 1 1 d . . . H20E H -0.0666 0.4212 0.8728 0.181 Uiso 1 1 calc R . . H20F H 0.0065 0.3430 0.9122 0.181 Uiso 1 1 calc R . . C204 C 0.1168(7) 0.4689(5) 0.9494(4) 0.064(2) Uani 1 1 d . . . H20G H 0.1571 0.4462 1.0035 0.077 Uiso 1 1 calc R . . H20H H 0.0812 0.5246 0.9665 0.077 Uiso 1 1 calc R . . Li1 Li 0.2767(10) 0.6247(7) 0.9143(6) 0.038(2) Uani 1 1 d . . . O3 O 0.1623(5) 1.0358(3) 0.4149(3) 0.0588(13) Uani 1 1 d . . . C301 C 0.2789(7) 1.0466(5) 0.4879(4) 0.062(2) Uani 1 1 d . . . H30D H 0.2634 1.0650 0.5448 0.074 Uiso 1 1 calc R . . H30E H 0.3486 1.0951 0.4856 0.074 Uiso 1 1 calc R . . C302 C 0.3165(7) 0.9530(5) 0.4791(5) 0.062(2) Uani 1 1 d . . . H30F H 0.3703 0.9464 0.4403 0.074 Uiso 1 1 calc R . . H30G H 0.3656 0.9425 0.5379 0.074 Uiso 1 1 calc R . . C303 C 0.1881(7) 0.8875(5) 0.4382(5) 0.068(2) Uani 1 1 d . . . H30H H 0.1939 0.8322 0.3965 0.081 Uiso 1 1 calc R . . H30I H 0.1586 0.8659 0.4845 0.081 Uiso 1 1 calc R . . C304 C 0.0972(8) 0.9412(4) 0.3906(5) 0.076(3) Uani 1 1 d . . . H30J H 0.0713 0.9171 0.3256 0.092 Uiso 1 1 calc R . . H30K H 0.0172 0.9353 0.4070 0.092 Uiso 1 1 calc R . . H1 H 0.1554 0.1264 0.3320 0.092 Uiso 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 Br1A 0.032(2) 0.042(2) 0.024(2) 0.0177(17) 0.0012(16) 0.0036(16) Br2A 0.091(4) 0.073(3) 0.028(2) 0.0138(19) 0.013(3) -0.002(3) Br1B 0.071(4) 0.074(3) 0.021(2) -0.0001(19) 0.018(2) 0.048(3) Br2B 0.0265(14) 0.076(3) 0.027(2) 0.0121(16) 0.0132(12) 0.0271(16) P1A 0.0238(13) 0.0224(12) 0.0162(10) 0.0014(8) 0.0064(9) 0.0047(10) C1A 0.023(3) 0.033(3) 0.016(3) 0.005(2) 0.006(3) 0.006(3) C2A 0.035(5) 0.034(5) 0.032(4) 0.009(4) 0.011(4) 0.015(4) C3A 0.041(5) 0.039(5) 0.023(4) 0.015(3) 0.005(4) 0.008(4) C4A 0.032(7) 0.042(6) 0.030(5) 0.010(4) -0.008(5) -0.002(5) C35A 0.066(6) 0.025(5) 0.059(5) 0.017(4) 0.028(5) 0.015(4) N1A 0.027(3) 0.029(3) 0.021(3) 0.007(2) 0.006(2) 0.005(2) P1B 0.061(8) 0.022(5) 0.027(5) 0.007(4) 0.004(5) 0.011(5) C1B 0.023(3) 0.033(3) 0.016(3) 0.005(2) 0.006(3) 0.006(3) N1B 0.027(3) 0.029(3) 0.021(3) 0.007(2) 0.006(2) 0.005(2) C11 0.030(4) 0.020(3) 0.021(3) 0.001(2) 0.002(3) 0.004(3) C5 0.045(4) 0.018(3) 0.013(3) -0.006(2) -0.001(3) -0.003(3) C6 0.028(4) 0.023(3) 0.025(3) 0.002(2) 0.002(3) -0.004(3) C7 0.031(4) 0.041(4) 0.036(4) 0.000(3) 0.005(3) -0.005(3) C8 0.042(4) 0.028(4) 0.036(4) -0.007(3) 0.011(3) -0.004(3) C9 0.031(4) 0.032(4) 0.034(3) -0.004(3) 0.006(3) 0.003(3) C10 0.034(4) 0.025(3) 0.014(3) 0.000(2) 0.001(3) 0.005(3) C12 0.034(4) 0.020(3) 0.021(3) 0.003(2) 0.003(3) 0.004(3) C13 0.020(3) 0.029(3) 0.026(3) 0.004(2) 0.004(3) 0.004(3) C14 0.032(4) 0.021(3) 0.019(3) 0.001(2) 0.006(3) -0.002(3) C15 0.032(4) 0.033(3) 0.023(3) 0.001(3) 0.010(3) 0.002(3) C16 0.022(4) 0.022(3) 0.028(3) 0.002(2) -0.003(3) 0.000(3) C17 0.030(4) 0.036(4) 0.043(4) -0.003(3) 0.009(3) 0.000(3) C18 0.031(4) 0.054(4) 0.044(4) -0.003(3) 0.001(3) 0.014(3) C19 0.049(5) 0.062(5) 0.044(4) 0.003(3) 0.021(4) 0.008(4) C20 0.032(4) 0.024(3) 0.026(3) 0.000(2) 0.009(3) 0.000(3) C21 0.054(5) 0.041(4) 0.032(3) 0.005(3) 0.020(3) 0.008(3) C22 0.040(4) 0.039(4) 0.038(4) 0.004(3) 0.012(3) 0.008(3) C23 0.023(4) 0.034(4) 0.035(3) 0.004(3) 0.005(3) 0.008(3) C24 0.030(4) 0.113(6) 0.063(5) 0.020(4) 0.021(4) 0.029(4) C25 0.055(5) 0.056(5) 0.061(5) 0.008(4) 0.014(4) 0.024(4) C26 0.025(4) 0.048(4) 0.076(5) -0.011(4) 0.004(4) -0.004(3) C27 0.038(4) 0.028(3) 0.022(3) 0.001(3) 0.010(3) -0.001(3) C28 0.027(4) 0.036(4) 0.033(3) 0.009(3) 0.000(3) -0.006(3) C29 0.071(5) 0.034(4) 0.047(4) -0.003(3) 0.027(4) -0.001(4) C30 0.046(5) 0.068(5) 0.052(4) 0.030(4) 0.029(4) 0.022(4) C31 0.027(4) 0.039(4) 0.019(3) 0.008(3) 0.006(3) 0.004(3) C32 0.039(4) 0.055(4) 0.032(3) 0.015(3) 0.009(3) 0.014(3) C33 0.058(5) 0.056(4) 0.021(3) -0.001(3) -0.002(3) 0.019(4) C34 0.036(4) 0.074(5) 0.034(4) 0.025(3) -0.001(3) -0.002(4) O1 0.035(3) 0.043(3) 0.038(2) -0.003(2) 0.009(2) 0.002(2) C101 0.035(4) 0.054(5) 0.056(5) -0.020(4) 0.006(4) -0.013(4) C102 0.048(5) 0.048(5) 0.059(5) 0.020(4) 0.000(4) -0.009(4) C103 0.079(6) 0.076(6) 0.057(5) 0.016(4) 0.037(5) 0.014(5) C104 0.044(5) 0.051(4) 0.061(4) -0.005(4) 0.025(4) 0.003(4) O2 0.045(3) 0.054(3) 0.039(2) -0.003(2) 0.017(2) -0.007(2) C201 0.059(5) 0.048(4) 0.052(4) -0.003(3) 0.027(4) 0.001(4) C202 0.064(6) 0.059(5) 0.076(5) -0.012(4) 0.030(5) -0.004(4) C203 0.134(10) 0.164(10) 0.113(8) -0.079(7) 0.094(8) -0.093(8) C204 0.048(5) 0.093(6) 0.054(5) 0.017(4) 0.029(4) -0.007(4) Li1 0.041(7) 0.044(6) 0.028(5) -0.002(4) 0.012(5) 0.014(5) O3 0.078(4) 0.040(3) 0.044(3) 0.017(2) -0.001(3) 0.008(3) C301 0.075(6) 0.050(5) 0.045(4) 0.012(3) 0.005(4) 0.001(4) C302 0.066(6) 0.054(5) 0.072(5) 0.030(4) 0.023(5) 0.014(4) C303 0.069(6) 0.041(5) 0.106(6) 0.024(4) 0.040(5) 0.022(4) C304 0.091(7) 0.042(5) 0.071(5) 0.030(4) -0.003(5) -0.019(5) _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 Br1A Li1 2.441(10) . ? Br2A Li1 2.465(12) . ? Br1B Li1 2.464(9) . ? Br2B Li1 2.522(12) . ? P1A C1A 1.730(5) . ? P1A C2A 1.845(6) . ? P1A C11 1.851(5) . ? C1A N1A 1.302(6) . ? C2A C35A 1.473(9) . ? C2A C3A 1.555(6) . ? C3A C4A 1.548(6) . ? C4A N1A 1.490(7) . ? N1A C5 1.470(6) . ? P1B C11 1.835(10) . ? P1B C2B 1.845(8) . ? C2B C3B 1.553(7) . ? C3B C4B 1.552(7) . ? C4B C35B 1.33(4) . ? C11 C12 1.406(7) . ? C11 C16 1.442(7) . ? C5 C6 1.394(7) . ? C5 C10 1.418(7) . ? C6 C7 1.387(7) . ? C6 C17 1.499(7) . ? C7 C8 1.380(7) . ? C8 C9 1.371(7) . ? C9 C10 1.396(7) . ? C10 C20 1.503(7) . ? C12 C13 1.409(7) . ? C12 C27 1.559(7) . ? C13 C14 1.380(6) . ? C14 C15 1.384(7) . ? C14 C31 1.517(7) . ? C15 C16 1.398(7) . ? C16 C23 1.534(7) . ? C17 C19 1.529(7) . ? C17 C18 1.542(8) . ? C20 C22 1.523(7) . ? C20 C21 1.527(6) . ? C23 C25 1.532(8) . ? C23 C24 1.532(7) . ? C23 C26 1.545(8) . ? C27 C29 1.527(7) . ? C27 C30 1.533(8) . ? C27 C28 1.539(7) . ? C31 C33 1.514(7) . ? C31 C32 1.529(7) . ? C31 C34 1.529(7) . ? O1 C104 1.429(6) . ? O1 C101 1.430(7) . ? O1 Li1 1.958(11) . ? C101 C102 1.500(8) . ? C102 C103 1.496(8) . ? C103 C104 1.480(8) . ? O2 C204 1.416(6) . ? O2 C201 1.432(6) . ? O2 Li1 1.972(10) . ? C201 C202 1.450(9) . ? C202 C203 1.486(9) . ? C203 C204 1.391(9) . ? O3 C304 1.411(7) . ? O3 C301 1.416(8) . ? C301 C302 1.492(8) . ? C302 C303 1.481(9) . ? C303 C304 1.472(9) . ? 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 C1A P1A C2A 101.3(3) . . ? C1A P1A C11 104.9(2) . . ? C2A P1A C11 123.5(3) . . ? N1A C1A P1A 124.9(4) . . ? C35A C2A C3A 112.4(6) . . ? C35A C2A P1A 115.9(6) . . ? C3A C2A P1A 100.7(4) . . ? C4A C3A C2A 116.4(7) . . ? N1A C4A C3A 109.7(6) . . ? C1A N1A C5 120.6(4) . . ? C1A N1A C4A 125.7(5) . . ? C5 N1A C4A 113.6(5) . . ? C11 P1B C2B 125.9(10) . . ? C3B C2B P1B 93(2) . . ? C4B C3B C2B 103(3) . . ? C35B C4B C3B 111(3) . . ? C12 C11 C16 120.8(5) . . ? C12 C11 P1B 137.9(5) . . ? C16 C11 P1B 101.0(5) . . ? C12 C11 P1A 110.8(4) . . ? C16 C11 P1A 127.5(4) . . ? P1B C11 P1A 27.2(3) . . ? C6 C5 C10 124.8(5) . . ? C6 C5 N1A 118.8(5) . . ? C10 C5 N1A 116.4(5) . . ? C7 C6 C5 116.1(5) . . ? C7 C6 C17 120.3(5) . . ? C5 C6 C17 123.6(5) . . ? C8 C7 C6 121.1(6) . . ? C9 C8 C7 121.7(5) . . ? C8 C9 C10 120.9(5) . . ? C9 C10 C5 115.5(5) . . ? C9 C10 C20 120.3(5) . . ? C5 C10 C20 124.2(5) . . ? C11 C12 C13 117.4(5) . . ? C11 C12 C27 126.2(5) . . ? C13 C12 C27 116.3(5) . . ? C14 C13 C12 123.8(5) . . ? C13 C14 C15 116.9(5) . . ? C13 C14 C31 122.8(5) . . ? C15 C14 C31 120.3(5) . . ? C14 C15 C16 124.3(5) . . ? C15 C16 C11 116.5(5) . . ? C15 C16 C23 117.2(5) . . ? C11 C16 C23 126.1(5) . . ? C6 C17 C19 112.4(5) . . ? C6 C17 C18 111.8(4) . . ? C19 C17 C18 110.4(5) . . ? C10 C20 C22 110.9(4) . . ? C10 C20 C21 111.7(5) . . ? C22 C20 C21 109.2(4) . . ? C25 C23 C24 104.5(5) . . ? C25 C23 C16 109.5(5) . . ? C24 C23 C16 112.2(5) . . ? C25 C23 C26 110.4(5) . . ? C24 C23 C26 106.8(5) . . ? C16 C23 C26 113.0(4) . . ? C29 C27 C30 103.5(5) . . ? C29 C27 C28 112.8(4) . . ? C30 C27 C28 103.9(4) . . ? C29 C27 C12 113.4(4) . . ? C30 C27 C12 112.5(4) . . ? C28 C27 C12 110.2(4) . . ? C33 C31 C14 109.3(4) . . ? C33 C31 C32 108.3(5) . . ? C14 C31 C32 112.3(4) . . ? C33 C31 C34 109.8(5) . . ? C14 C31 C34 110.1(4) . . ? C32 C31 C34 106.9(5) . . ? C104 O1 C101 107.0(4) . . ? C104 O1 Li1 115.7(4) . . ? C101 O1 Li1 118.1(5) . . ? O1 C101 C102 104.4(5) . . ? C103 C102 C101 102.9(5) . . ? C104 C103 C102 106.5(5) . . ? O1 C104 C103 106.6(5) . . ? C204 O2 C201 107.1(5) . . ? C204 O2 Li1 120.3(5) . . ? C201 O2 Li1 123.7(4) . . ? O2 C201 C202 106.4(5) . . ? C201 C202 C203 102.9(6) . . ? C204 C203 C202 109.1(6) . . ? C203 C204 O2 107.7(5) . . ? O1 Li1 O2 101.9(5) . . ? O1 Li1 Br1A 103.0(4) . . ? O2 Li1 Br1A 112.6(4) . . ? O1 Li1 Br1B 105.1(4) . . ? O2 Li1 Br1B 110.7(4) . . ? Br1A Li1 Br1B 2.5(3) . . ? O1 Li1 Br2A 108.1(4) . . ? O2 Li1 Br2A 105.5(4) . . ? Br1A Li1 Br2A 123.5(4) . . ? Br1B Li1 Br2A 123.4(4) . . ? O1 Li1 Br2B 112.1(4) . . ? O2 Li1 Br2B 105.8(4) . . ? Br1A Li1 Br2B 120.1(4) . . ? Br1B Li1 Br2B 119.8(4) . . ? Br2A Li1 Br2B 4.4(2) . . ? C304 O3 C301 108.5(5) . . ? O3 C301 C302 105.3(5) . . ? C303 C302 C301 102.7(6) . . ? C304 C303 C302 105.6(6) . . ? O3 C304 C303 107.6(6) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.381 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.074 #====END data_6c _database_code_depnum_ccdc_archive 'CCDC 695387' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H54 N P' _chemical_formula_sum 'C35 H54 N P' _chemical_formula_weight 519.76 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' P P 0.1023 0.0942 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.330(13) _cell_length_b 17.35(2) _cell_length_c 15.903(19) _cell_angle_alpha 90.00 _cell_angle_beta 93.133(16) _cell_angle_gamma 90.00 _cell_volume 3122(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 235 _cell_measurement_theta_min 2.347 _cell_measurement_theta_max 15.222 _exptl_crystal_description 'prism frag' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.106 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9890 _exptl_absorpt_correction_T_max 0.9934 _exptl_absorpt_process_details multi-scan _exptl_special_details ; Measurement were carried out on a Bruker X8 APEX2 (version 2.0-2) KAPPA-CCD X-Ray diffractometer system (Mo-radiation, \l = 0.71073 \%A, 50KV/30mA power) Compound was collected at T = 100 K Frames were integrated with the aid of the Bruker SAINT version 7.06A software and using a narrow-frame integration algorithm. Absorption corrections were applied to the raw intensity data using the SADABS program (version 2004/1). Relative high value for Rint and large su's on cell axis can be explained by the weakness of data which doesn't really show significant diffraction intensity above 21 deg in theta angle. Quality of data is so average but unfortunately all attempts to crystallize better samples failed . ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14462 _diffrn_reflns_av_R_equivalents 0.2413 _diffrn_reflns_av_sigmaI/netI 0.2243 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 21.26 _reflns_number_total 3467 _reflns_number_gt 1499 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker Sir97' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _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^)+(0.0749P)^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 SHELXL _refine_ls_extinction_coef 0.0044(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3467 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2035 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_ref 0.2199 _refine_ls_wR_factor_gt 0.1635 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _refine_ls_shift/su_max 0.000 _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 0.5015(2) 0.16674(12) 0.80075(14) 0.0366(7) Uani 1 1 d . . . N1 N 0.2548(5) 0.1941(3) 0.7790(4) 0.0354(19) Uani 1 1 d . . . C1 C 0.3602(7) 0.2192(4) 0.8246(4) 0.034(2) Uani 1 1 d . . . H1 H 0.3655 0.2730 0.8429 0.041 Uiso 1 1 calc R . . C2 C 0.2326(9) 0.1145(6) 0.7975(7) 0.091(4) Uani 1 1 d . . . H2 H 0.2767 0.0868 0.7556 0.110 Uiso 1 1 calc R . . C3 C 0.2993(7) 0.0968(4) 0.8781(5) 0.039(2) Uani 1 1 d . . . H3A H 0.3338 0.0456 0.8767 0.047 Uiso 1 1 calc R . . H3B H 0.2482 0.0997 0.9250 0.047 Uiso 1 1 calc R . . C4 C 0.3954(7) 0.1582(4) 0.8859(5) 0.035(2) Uani 1 1 d . . . H4 H 0.4226 0.1744 0.9427 0.041 Uiso 1 1 calc R . . C5 C 0.6142(7) 0.2247(4) 0.8620(4) 0.031(2) Uani 1 1 d . . . C6 C 0.6872(7) 0.1863(4) 0.9251(5) 0.029(2) Uani 1 1 d . . . C7 C 0.7418(7) 0.2298(4) 0.9883(5) 0.029(2) Uani 1 1 d . . . H7 H 0.7845 0.2043 1.0315 0.035 Uiso 1 1 calc R . . C8 C 0.7367(7) 0.3090(4) 0.9910(5) 0.033(2) Uani 1 1 d . . . C9 C 0.6802(6) 0.3446(4) 0.9220(4) 0.030(2) Uani 1 1 d . . . H9 H 0.6814 0.3982 0.9201 0.036 Uiso 1 1 calc R . . C10 C 0.6218(7) 0.3057(4) 0.8553(5) 0.032(2) Uani 1 1 d . . . C11 C 0.2076(7) 0.2363(4) 0.7074(5) 0.032(2) Uani 1 1 d . . . C12 C 0.2345(7) 0.2183(4) 0.6244(5) 0.036(2) Uani 1 1 d . . . C13 C 0.1854(7) 0.2621(5) 0.5581(5) 0.038(2) Uani 1 1 d . . . H13 H 0.1997 0.2489 0.5029 0.046 Uiso 1 1 calc R . . C14 C 0.1154(7) 0.3252(5) 0.5740(5) 0.044(2) Uani 1 1 d . . . H14 H 0.0848 0.3554 0.5297 0.053 Uiso 1 1 calc R . . C15 C 0.0910(7) 0.3431(4) 0.6554(5) 0.041(2) Uani 1 1 d . . . H15 H 0.0428 0.3852 0.6650 0.049 Uiso 1 1 calc R . . C16 C 0.1364(7) 0.3000(4) 0.7244(5) 0.033(2) Uani 1 1 d . . . C17 C 0.1111(7) 0.0844(4) 0.7838(5) 0.048(3) Uani 1 1 d . . . H17A H 0.0620 0.1055 0.8254 0.072 Uiso 1 1 calc R . . H17B H 0.1121 0.0292 0.7884 0.072 Uiso 1 1 calc R . . H17C H 0.0801 0.0989 0.7287 0.072 Uiso 1 1 calc R . . C18 C 0.3146(7) 0.1510(4) 0.6020(5) 0.035(2) Uani 1 1 d . . . H18 H 0.3587 0.1354 0.6539 0.042 Uiso 1 1 calc R . . C19 C 0.4051(7) 0.1728(5) 0.5384(5) 0.049(3) Uani 1 1 d . . . H19A H 0.4593 0.1310 0.5326 0.073 Uiso 1 1 calc R . . H19B H 0.4477 0.2178 0.5579 0.073 Uiso 1 1 calc R . . H19C H 0.3651 0.1835 0.4849 0.073 Uiso 1 1 calc R . . C20 C 0.2438(7) 0.0814(4) 0.5703(5) 0.049(3) Uani 1 1 d . . . H20A H 0.2047 0.0933 0.5168 0.073 Uiso 1 1 calc R . . H20B H 0.1860 0.0686 0.6099 0.073 Uiso 1 1 calc R . . H20C H 0.2960 0.0385 0.5641 0.073 Uiso 1 1 calc R . . C21 C 0.1018(7) 0.3202(4) 0.8114(5) 0.036(2) Uani 1 1 d . . . H21 H 0.1614 0.2976 0.8510 0.044 Uiso 1 1 calc R . . C22 C 0.1011(8) 0.4062(4) 0.8279(5) 0.059(3) Uani 1 1 d . . . H22A H 0.1724 0.4286 0.8091 0.089 Uiso 1 1 calc R . . H22B H 0.0962 0.4153 0.8872 0.089 Uiso 1 1 calc R . . H22C H 0.0341 0.4291 0.7979 0.089 Uiso 1 1 calc R . . C23 C -0.0179(7) 0.2844(5) 0.8308(5) 0.058(3) Uani 1 1 d . . . H23A H -0.0787 0.3050 0.7929 0.087 Uiso 1 1 calc R . . H23B H -0.0355 0.2962 0.8878 0.087 Uiso 1 1 calc R . . H23C H -0.0142 0.2295 0.8240 0.087 Uiso 1 1 calc R . . C24 C 0.7156(7) 0.0982(4) 0.9230(5) 0.036(2) Uani 1 1 d . . . C25 C 0.6130(7) 0.0463(4) 0.9499(5) 0.046(3) Uani 1 1 d . . . H25A H 0.6390 -0.0063 0.9527 0.070 Uiso 1 1 calc R . . H25B H 0.5473 0.0509 0.9095 0.070 Uiso 1 1 calc R . . H25C H 0.5893 0.0623 1.0043 0.070 Uiso 1 1 calc R . . C26 C 0.8207(7) 0.0779(4) 0.9850(5) 0.048(3) Uani 1 1 d . . . H26A H 0.7975 0.0842 1.0418 0.072 Uiso 1 1 calc R . . H26B H 0.8860 0.1114 0.9754 0.072 Uiso 1 1 calc R . . H26C H 0.8439 0.0254 0.9764 0.072 Uiso 1 1 calc R . . C27 C 0.7529(7) 0.0745(4) 0.8364(5) 0.039(2) Uani 1 1 d . . . H27A H 0.8197 0.1047 0.8217 0.059 Uiso 1 1 calc R . . H27B H 0.6886 0.0828 0.7956 0.059 Uiso 1 1 calc R . . H27C H 0.7741 0.0209 0.8371 0.059 Uiso 1 1 calc R . . C28 C 0.7939(7) 0.3570(4) 1.0640(5) 0.035(2) Uani 1 1 d . . . C29 C 0.8418(7) 0.3077(4) 1.1371(4) 0.040(2) Uani 1 1 d . . . H29A H 0.7783 0.2791 1.1596 0.060 Uiso 1 1 calc R . . H29B H 0.8774 0.3403 1.1802 0.060 Uiso 1 1 calc R . . H29C H 0.8999 0.2727 1.1176 0.060 Uiso 1 1 calc R . . C30 C 0.8962(7) 0.4040(4) 1.0313(5) 0.042(2) Uani 1 1 d . . . H30A H 0.9550 0.3697 1.0113 0.063 Uiso 1 1 calc R . . H30B H 0.9307 0.4352 1.0760 0.063 Uiso 1 1 calc R . . H30C H 0.8671 0.4366 0.9860 0.063 Uiso 1 1 calc R . . C31 C 0.7015(7) 0.4142(4) 1.0976(4) 0.040(2) Uani 1 1 d . . . H31A H 0.6671 0.4439 1.0516 0.060 Uiso 1 1 calc R . . H31B H 0.7398 0.4481 1.1383 0.060 Uiso 1 1 calc R . . H31C H 0.6406 0.3857 1.1236 0.060 Uiso 1 1 calc R . . C32 C 0.5815(7) 0.3575(4) 0.7795(5) 0.036(2) Uani 1 1 d . . . C33 C 0.6921(7) 0.3998(4) 0.7509(5) 0.052(3) Uani 1 1 d . . . H33A H 0.7439 0.3634 0.7262 0.078 Uiso 1 1 calc R . . H33B H 0.7325 0.4239 0.7986 0.078 Uiso 1 1 calc R . . H33C H 0.6688 0.4383 0.7100 0.078 Uiso 1 1 calc R . . C34 C 0.4921(8) 0.4189(4) 0.8059(5) 0.051(3) Uani 1 1 d . . . H34A H 0.4703 0.4512 0.7586 0.076 Uiso 1 1 calc R . . H34B H 0.5274 0.4499 0.8506 0.076 Uiso 1 1 calc R . . H34C H 0.4229 0.3939 0.8251 0.076 Uiso 1 1 calc R . . C35 C 0.5305(7) 0.3164(4) 0.6997(5) 0.048(3) Uani 1 1 d . . . H35A H 0.5256 0.3522 0.6535 0.072 Uiso 1 1 calc R . . H35B H 0.4529 0.2972 0.7094 0.072 Uiso 1 1 calc R . . H35C H 0.5810 0.2743 0.6863 0.072 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 P1 0.0341(15) 0.0355(14) 0.0394(14) 0.0012(12) -0.0046(12) -0.0008(12) N1 0.035(5) 0.020(4) 0.049(5) 0.003(3) -0.022(4) 0.000(3) C1 0.032(6) 0.033(5) 0.036(5) -0.007(4) -0.004(5) 0.003(4) C2 0.062(8) 0.087(9) 0.118(10) 0.048(7) -0.059(7) -0.043(6) C3 0.040(6) 0.035(5) 0.042(6) 0.000(4) -0.002(5) 0.002(5) C4 0.047(6) 0.029(5) 0.027(5) 0.001(4) -0.001(4) 0.002(4) C5 0.031(6) 0.032(5) 0.029(5) 0.000(4) -0.002(4) -0.001(4) C6 0.027(5) 0.031(5) 0.030(5) 0.006(4) -0.001(4) -0.003(4) C7 0.029(6) 0.024(5) 0.036(5) 0.006(4) -0.001(4) -0.004(4) C8 0.024(5) 0.034(6) 0.041(5) 0.002(4) -0.008(5) -0.010(4) C9 0.033(6) 0.022(5) 0.034(5) -0.001(4) -0.004(5) 0.002(4) C10 0.022(5) 0.041(6) 0.033(5) -0.002(4) 0.003(4) 0.000(4) C11 0.029(6) 0.024(5) 0.042(6) -0.001(5) -0.008(5) 0.003(4) C12 0.035(6) 0.040(6) 0.032(6) -0.007(5) 0.008(5) -0.005(5) C13 0.041(6) 0.044(6) 0.029(5) 0.004(5) -0.007(5) 0.003(5) C14 0.042(6) 0.051(6) 0.039(6) 0.009(5) -0.006(5) 0.007(5) C15 0.044(6) 0.036(5) 0.043(6) 0.000(5) 0.001(5) 0.004(4) C16 0.027(6) 0.037(5) 0.034(6) -0.001(5) -0.003(5) -0.002(4) C17 0.034(6) 0.049(6) 0.061(6) 0.008(5) -0.005(5) -0.010(5) C18 0.038(6) 0.038(5) 0.028(5) -0.006(4) 0.000(5) 0.005(5) C19 0.027(6) 0.054(6) 0.066(6) -0.003(5) 0.003(5) 0.007(5) C20 0.057(7) 0.041(6) 0.047(6) -0.004(5) -0.010(5) 0.012(5) C21 0.033(6) 0.035(6) 0.041(6) -0.006(4) 0.001(5) 0.006(4) C22 0.082(8) 0.046(6) 0.050(6) -0.006(5) 0.006(6) 0.013(5) C23 0.043(7) 0.071(7) 0.063(7) -0.034(5) 0.025(6) -0.014(5) C24 0.045(6) 0.021(5) 0.039(6) 0.005(4) -0.007(5) -0.003(4) C25 0.049(7) 0.036(5) 0.053(6) 0.009(5) -0.013(5) 0.004(5) C26 0.046(6) 0.026(5) 0.070(6) 0.006(5) -0.022(5) -0.007(4) C27 0.037(6) 0.032(5) 0.050(6) 0.002(4) 0.003(5) 0.007(4) C28 0.029(6) 0.034(5) 0.041(5) -0.005(4) 0.002(5) -0.005(5) C29 0.048(6) 0.035(5) 0.035(5) 0.006(4) -0.008(5) -0.007(4) C30 0.043(6) 0.036(5) 0.046(6) -0.005(4) -0.013(5) 0.000(5) C31 0.044(6) 0.048(6) 0.029(5) -0.004(4) 0.007(5) 0.001(5) C32 0.039(6) 0.029(5) 0.041(5) 0.010(4) 0.004(5) 0.001(4) C33 0.052(7) 0.043(6) 0.059(6) 0.008(5) -0.001(6) -0.011(5) C34 0.062(7) 0.035(5) 0.054(6) 0.005(5) -0.013(5) 0.016(5) C35 0.062(7) 0.044(6) 0.038(5) 0.010(5) -0.003(5) -0.009(5) _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 C5 1.858(7) . ? P1 C4 1.866(8) . ? P1 C1 1.898(8) . ? N1 C1 1.430(8) . ? N1 C11 1.433(9) . ? N1 C2 1.437(10) . ? C1 C4 1.479(9) . ? C2 C17 1.478(11) . ? C2 C3 1.485(10) . ? C3 C4 1.523(10) . ? C5 C10 1.414(9) . ? C5 C6 1.429(9) . ? C6 C7 1.377(9) . ? C6 C24 1.563(10) . ? C7 C8 1.377(9) . ? C8 C9 1.385(9) . ? C8 C28 1.543(10) . ? C9 C10 1.393(9) . ? C10 C32 1.552(10) . ? C11 C16 1.402(10) . ? C11 C12 1.406(10) . ? C12 C13 1.390(10) . ? C12 C18 1.533(10) . ? C13 C14 1.384(10) . ? C14 C15 1.373(10) . ? C15 C16 1.403(10) . ? C16 C21 1.501(10) . ? C18 C20 1.520(9) . ? C18 C19 1.526(11) . ? C21 C22 1.515(10) . ? C21 C23 1.538(10) . ? C24 C27 1.519(10) . ? C24 C26 1.545(9) . ? C24 C25 1.549(11) . ? C28 C29 1.519(9) . ? C28 C30 1.532(10) . ? C28 C31 1.557(10) . ? C32 C35 1.542(10) . ? C32 C33 1.542(10) . ? C32 C34 1.544(10) . ? 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 C5 P1 C4 96.6(4) . . ? C5 P1 C1 101.5(3) . . ? C4 P1 C1 46.3(3) . . ? C1 N1 C11 120.8(6) . . ? C1 N1 C2 109.8(6) . . ? C11 N1 C2 126.3(6) . . ? N1 C1 C4 107.7(6) . . ? N1 C1 P1 116.3(5) . . ? C4 C1 P1 65.7(4) . . ? N1 C2 C17 118.8(8) . . ? N1 C2 C3 106.8(7) . . ? C17 C2 C3 118.7(8) . . ? C2 C3 C4 104.6(7) . . ? C1 C4 C3 106.4(6) . . ? C1 C4 P1 68.0(4) . . ? C3 C4 P1 118.9(6) . . ? C10 C5 C6 118.8(6) . . ? C10 C5 P1 122.8(5) . . ? C6 C5 P1 118.0(6) . . ? C7 C6 C5 118.5(7) . . ? C7 C6 C24 117.8(6) . . ? C5 C6 C24 123.6(6) . . ? C8 C7 C6 123.5(7) . . ? C7 C8 C9 116.1(7) . . ? C7 C8 C28 123.1(7) . . ? C9 C8 C28 120.8(7) . . ? C8 C9 C10 124.5(7) . . ? C9 C10 C5 117.0(7) . . ? C9 C10 C32 114.7(7) . . ? C5 C10 C32 128.2(7) . . ? C16 C11 C12 120.8(7) . . ? C16 C11 N1 116.3(7) . . ? C12 C11 N1 122.8(7) . . ? C13 C12 C11 119.5(8) . . ? C13 C12 C18 117.2(7) . . ? C11 C12 C18 123.3(7) . . ? C14 C13 C12 120.2(8) . . ? C15 C14 C13 119.9(8) . . ? C14 C15 C16 122.2(8) . . ? C11 C16 C15 117.3(8) . . ? C11 C16 C21 123.0(7) . . ? C15 C16 C21 119.6(7) . . ? C20 C18 C19 109.8(6) . . ? C20 C18 C12 112.0(7) . . ? C19 C18 C12 113.1(7) . . ? C16 C21 C22 113.2(7) . . ? C16 C21 C23 111.6(6) . . ? C22 C21 C23 110.5(7) . . ? C27 C24 C26 105.9(7) . . ? C27 C24 C25 110.1(6) . . ? C26 C24 C25 104.7(6) . . ? C27 C24 C6 110.6(6) . . ? C26 C24 C6 111.2(6) . . ? C25 C24 C6 113.8(7) . . ? C29 C28 C30 108.3(6) . . ? C29 C28 C8 112.9(6) . . ? C30 C28 C8 109.0(7) . . ? C29 C28 C31 108.4(7) . . ? C30 C28 C31 108.3(6) . . ? C8 C28 C31 109.9(6) . . ? C35 C32 C33 104.5(7) . . ? C35 C32 C34 108.7(6) . . ? C33 C32 C34 107.9(6) . . ? C35 C32 C10 116.9(6) . . ? C33 C32 C10 107.2(6) . . ? C34 C32 C10 111.0(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 21.26 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.336 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.067 #====END data_8c _database_code_depnum_ccdc_archive 'CCDC 695388' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H54 N P' _chemical_formula_sum 'C35 H54 N P' _chemical_formula_weight 519.76 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' P P 0.1023 0.0942 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.676(3) _cell_length_b 17.298(3) _cell_length_c 10.2989(16) _cell_angle_alpha 90.00 _cell_angle_beta 91.407(2) _cell_angle_gamma 90.00 _cell_volume 3148.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5040 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 25.65 _exptl_crystal_description 'prism frag' _exptl_crystal_colour clear _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.097 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details multi-scan _exptl_special_details ; Measurement were carried out on a Bruker X8 APEX2 (version 2.0-2) KAPPA-CCD X-Ray diffractometer system (Mo-radiation, \l = 0.71073 \%A, 50KV/30mA power) Compound was collected at T = 100 K Frames were integrated with the aid of the Bruker SAINT version 7.06A software and using a narrow-frame integration algorithm. Absorption corrections were applied to the raw intensity data using the SADABS program (version 2004/1). ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19438 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 24.71 _reflns_number_total 5359 _reflns_number_gt 4058 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker Sir97' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _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^)+(0.0741P)^2^+0.8112P] 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 SHELXL _refine_ls_extinction_coef 0.0002(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5359 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1340 _refine_ls_wR_factor_gt 0.1207 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _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 0.82275(3) 0.00829(3) 0.26764(6) 0.01738(17) Uani 1 1 d . . . N1 N 0.78045(10) -0.09764(9) 0.08675(17) 0.0178(4) Uani 1 1 d . . . C1 C 0.76927(12) 0.06415(11) 0.3897(2) 0.0165(5) Uani 1 1 d . . . C2 C 0.80862(12) 0.11689(11) 0.4742(2) 0.0172(5) Uani 1 1 d . . . C3 C 0.76971(12) 0.14757(11) 0.5791(2) 0.0178(5) Uani 1 1 d . . . H3 H 0.7963 0.1812 0.6371 0.021 Uiso 1 1 calc R . . C4 C 0.69457(12) 0.13160(11) 0.6031(2) 0.0174(5) Uani 1 1 d . . . C5 C 0.65594(12) 0.08630(11) 0.5123(2) 0.0189(5) Uani 1 1 d . . . H5 H 0.6035 0.0773 0.5233 0.023 Uiso 1 1 calc R . . C6 C 0.69081(12) 0.05330(11) 0.4056(2) 0.0174(5) Uani 1 1 d . . . C7 C 0.63870(12) 0.01394(12) 0.3029(2) 0.0189(5) Uani 1 1 d . . . C8 C 0.67603(12) -0.05366(11) 0.2326(2) 0.0189(5) Uani 1 1 d . . . H8A H 0.6889 -0.0942 0.2973 0.023 Uiso 1 1 calc R . . H8B H 0.6386 -0.0760 0.1701 0.023 Uiso 1 1 calc R . . C9 C 0.74681(12) -0.03340(11) 0.1600(2) 0.0179(5) Uani 1 1 d . . . H9 H 0.7323 0.0075 0.0954 0.022 Uiso 1 1 calc R . . C10 C 0.76158(12) -0.09932(11) -0.0498(2) 0.0183(5) Uani 1 1 d . . . C11 C 0.69678(12) -0.13789(11) -0.1010(2) 0.0196(5) Uani 1 1 d . . . C12 C 0.68095(13) -0.13290(12) -0.2341(2) 0.0242(5) Uani 1 1 d . . . H12 H 0.6380 -0.1592 -0.2694 0.029 Uiso 1 1 calc R . . C13 C 0.72584(13) -0.09081(12) -0.3159(2) 0.0268(5) Uani 1 1 d . . . H13 H 0.7130 -0.0870 -0.4058 0.032 Uiso 1 1 calc R . . C14 C 0.78977(13) -0.05425(12) -0.2658(2) 0.0245(5) Uani 1 1 d . . . H14 H 0.8210 -0.0258 -0.3223 0.029 Uiso 1 1 calc R . . C15 C 0.80912(12) -0.05841(11) -0.1341(2) 0.0206(5) Uani 1 1 d . . . C16 C 0.80724(13) -0.16672(12) 0.1582(2) 0.0217(5) Uani 1 1 d . . . H16 H 0.7632 -0.1913 0.2012 0.026 Uiso 1 1 calc R . . C17 C 0.86634(13) -0.14458(12) 0.2624(2) 0.0234(5) Uani 1 1 d . . . H17A H 0.9121 -0.1257 0.2190 0.028 Uiso 1 1 calc R . . H17B H 0.8807 -0.1917 0.3118 0.028 Uiso 1 1 calc R . . C18 C 0.84109(12) -0.08279(11) 0.3586(2) 0.0205(5) Uani 1 1 d . . . H18A H 0.8811 -0.0744 0.4261 0.025 Uiso 1 1 calc R . . H18B H 0.7945 -0.0998 0.4019 0.025 Uiso 1 1 calc R . . C19 C 0.84175(13) -0.22523(12) 0.0665(2) 0.0266(5) Uani 1 1 d . . . H19A H 0.8037 -0.2408 0.0008 0.040 Uiso 1 1 calc R . . H19B H 0.8587 -0.2707 0.1160 0.040 Uiso 1 1 calc R . . H19C H 0.8851 -0.2018 0.0238 0.040 Uiso 1 1 calc R . . C20 C 0.61479(13) 0.07667(12) 0.2035(2) 0.0254(5) Uani 1 1 d . . . H20A H 0.5834 0.0533 0.1343 0.038 Uiso 1 1 calc R . . H20B H 0.6600 0.0996 0.1660 0.038 Uiso 1 1 calc R . . H20C H 0.5858 0.1169 0.2471 0.038 Uiso 1 1 calc R . . C21 C 0.56636(13) -0.01940(13) 0.3617(2) 0.0283(6) Uani 1 1 d . . . H21A H 0.5387 -0.0497 0.2957 0.042 Uiso 1 1 calc R . . H21B H 0.5343 0.0230 0.3913 0.042 Uiso 1 1 calc R . . H21C H 0.5801 -0.0527 0.4356 0.042 Uiso 1 1 calc R . . C22 C 0.89130(12) 0.14456(11) 0.4539(2) 0.0184(5) Uani 1 1 d . . . C23 C 0.89820(12) 0.18304(12) 0.3200(2) 0.0226(5) Uani 1 1 d . . . H23A H 0.9506 0.1995 0.3081 0.034 Uiso 1 1 calc R . . H23B H 0.8647 0.2282 0.3147 0.034 Uiso 1 1 calc R . . H23C H 0.8836 0.1460 0.2518 0.034 Uiso 1 1 calc R . . C24 C 0.94867(12) 0.07849(12) 0.4696(2) 0.0213(5) Uani 1 1 d . . . H24A H 1.0001 0.0995 0.4676 0.032 Uiso 1 1 calc R . . H24B H 0.9413 0.0414 0.3985 0.032 Uiso 1 1 calc R . . H24C H 0.9412 0.0524 0.5527 0.032 Uiso 1 1 calc R . . C25 C 0.91630(12) 0.20614(12) 0.5543(2) 0.0239(5) Uani 1 1 d . . . H25A H 0.9162 0.1836 0.6416 0.036 Uiso 1 1 calc R . . H25B H 0.8812 0.2500 0.5499 0.036 Uiso 1 1 calc R . . H25C H 0.9674 0.2240 0.5351 0.036 Uiso 1 1 calc R . . C26 C 0.65338(12) 0.16181(12) 0.7229(2) 0.0215(5) Uani 1 1 d . . . C27 C 0.70166(13) 0.21813(13) 0.8042(2) 0.0277(6) Uani 1 1 d . . . H27A H 0.7469 0.1914 0.8380 0.041 Uiso 1 1 calc R . . H27B H 0.6722 0.2374 0.8768 0.041 Uiso 1 1 calc R . . H27C H 0.7168 0.2617 0.7498 0.041 Uiso 1 1 calc R . . C28 C 0.63326(13) 0.09245(13) 0.8091(2) 0.0273(5) Uani 1 1 d . . . H28A H 0.6012 0.0564 0.7592 0.041 Uiso 1 1 calc R . . H28B H 0.6060 0.1107 0.8849 0.041 Uiso 1 1 calc R . . H28C H 0.6798 0.0661 0.8380 0.041 Uiso 1 1 calc R . . C29 C 0.58047(12) 0.20389(13) 0.6793(2) 0.0260(5) Uani 1 1 d . . . H29A H 0.5932 0.2473 0.6226 0.039 Uiso 1 1 calc R . . H29B H 0.5545 0.2234 0.7556 0.039 Uiso 1 1 calc R . . H29C H 0.5472 0.1678 0.6317 0.039 Uiso 1 1 calc R . . C30 C 0.64237(12) -0.18359(12) -0.0184(2) 0.0226(5) Uani 1 1 d . . . H30 H 0.6615 -0.1820 0.0737 0.027 Uiso 1 1 calc R . . C31 C 0.63701(14) -0.26875(12) -0.0606(2) 0.0284(6) Uani 1 1 d . . . H31A H 0.6179 -0.2716 -0.1506 0.043 Uiso 1 1 calc R . . H31B H 0.6024 -0.2963 -0.0039 0.043 Uiso 1 1 calc R . . H31C H 0.6873 -0.2925 -0.0541 0.043 Uiso 1 1 calc R . . C32 C 0.56287(13) -0.14778(13) -0.0240(3) 0.0300(6) Uani 1 1 d . . . H32A H 0.5663 -0.0926 -0.0032 0.045 Uiso 1 1 calc R . . H32B H 0.5309 -0.1736 0.0392 0.045 Uiso 1 1 calc R . . H32C H 0.5407 -0.1543 -0.1114 0.045 Uiso 1 1 calc R . . C33 C 0.88135(12) -0.01905(12) -0.0852(2) 0.0243(5) Uani 1 1 d . . . H33 H 0.8887 -0.0323 0.0088 0.029 Uiso 1 1 calc R . . C34 C 0.87532(15) 0.06935(13) -0.0961(3) 0.0362(6) Uani 1 1 d . . . H34A H 0.9226 0.0930 -0.0642 0.054 Uiso 1 1 calc R . . H34B H 0.8333 0.0876 -0.0438 0.054 Uiso 1 1 calc R . . H34C H 0.8662 0.0838 -0.1871 0.054 Uiso 1 1 calc R . . C35 C 0.95003(14) -0.04851(16) -0.1568(3) 0.0376(6) Uani 1 1 d . . . H35A H 0.9439 -0.0370 -0.2496 0.056 Uiso 1 1 calc R . . H35B H 0.9547 -0.1045 -0.1446 0.056 Uiso 1 1 calc R . . H35C H 0.9957 -0.0230 -0.1222 0.056 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 P1 0.0227(3) 0.0124(3) 0.0172(3) -0.0015(2) 0.0029(2) 0.0001(2) N1 0.0279(10) 0.0101(8) 0.0155(10) -0.0008(7) 0.0013(8) 0.0033(7) C1 0.0246(12) 0.0096(10) 0.0154(12) 0.0028(8) 0.0007(9) 0.0019(8) C2 0.0247(12) 0.0105(10) 0.0163(12) 0.0024(8) -0.0004(9) 0.0027(8) C3 0.0267(12) 0.0096(10) 0.0169(12) -0.0006(8) -0.0017(9) 0.0012(8) C4 0.0236(11) 0.0110(10) 0.0177(12) 0.0012(8) 0.0016(9) 0.0027(8) C5 0.0215(11) 0.0133(10) 0.0219(13) 0.0022(9) 0.0023(9) -0.0006(8) C6 0.0264(12) 0.0087(10) 0.0173(12) 0.0024(8) 0.0016(9) 0.0012(8) C7 0.0231(11) 0.0153(10) 0.0184(12) -0.0025(9) 0.0008(9) 0.0002(8) C8 0.0239(12) 0.0127(10) 0.0200(13) -0.0018(9) 0.0013(9) -0.0011(8) C9 0.0252(12) 0.0103(10) 0.0184(12) -0.0014(8) 0.0018(9) 0.0026(8) C10 0.0261(12) 0.0118(10) 0.0171(12) -0.0029(9) 0.0023(9) 0.0054(8) C11 0.0259(12) 0.0131(10) 0.0199(13) -0.0036(9) 0.0026(9) 0.0039(9) C12 0.0314(13) 0.0160(11) 0.0251(14) -0.0062(9) -0.0030(10) 0.0001(9) C13 0.0419(15) 0.0203(12) 0.0182(13) -0.0010(10) 0.0005(11) 0.0054(10) C14 0.0356(13) 0.0166(11) 0.0217(14) 0.0013(9) 0.0061(10) 0.0022(9) C15 0.0286(12) 0.0144(10) 0.0190(13) -0.0004(9) 0.0044(10) 0.0046(9) C16 0.0313(13) 0.0139(10) 0.0202(13) 0.0011(9) 0.0036(10) 0.0022(9) C17 0.0331(13) 0.0153(11) 0.0218(13) 0.0011(9) 0.0013(10) 0.0068(9) C18 0.0254(12) 0.0160(11) 0.0200(13) 0.0005(9) 0.0013(9) 0.0015(9) C19 0.0341(14) 0.0189(11) 0.0269(14) -0.0043(10) 0.0002(11) 0.0054(9) C20 0.0322(13) 0.0183(11) 0.0255(14) -0.0031(10) -0.0038(10) 0.0065(9) C21 0.0267(13) 0.0264(12) 0.0319(15) -0.0121(10) 0.0052(11) -0.0050(10) C22 0.0228(11) 0.0138(10) 0.0186(12) -0.0005(9) 0.0028(9) 0.0000(8) C23 0.0249(12) 0.0168(11) 0.0263(14) 0.0028(9) 0.0027(10) -0.0017(9) C24 0.0243(12) 0.0169(11) 0.0228(13) 0.0015(9) 0.0021(10) 0.0000(9) C25 0.0264(12) 0.0199(11) 0.0257(14) -0.0059(10) 0.0039(10) -0.0042(9) C26 0.0249(12) 0.0178(11) 0.0218(13) -0.0047(9) 0.0035(10) -0.0003(9) C27 0.0279(13) 0.0303(13) 0.0250(14) -0.0108(10) 0.0049(10) 0.0000(10) C28 0.0333(14) 0.0258(12) 0.0233(14) -0.0013(10) 0.0083(11) 0.0004(10) C29 0.0288(13) 0.0209(12) 0.0285(14) -0.0073(10) 0.0054(10) 0.0030(9) C30 0.0280(12) 0.0179(11) 0.0218(13) -0.0038(9) 0.0012(10) -0.0005(9) C31 0.0396(14) 0.0181(12) 0.0274(14) -0.0024(10) 0.0012(11) -0.0042(10) C32 0.0305(13) 0.0271(13) 0.0326(15) -0.0063(11) 0.0020(11) -0.0012(10) C33 0.0298(13) 0.0225(12) 0.0207(13) 0.0022(9) 0.0039(10) -0.0036(9) C34 0.0431(15) 0.0240(13) 0.0412(17) 0.0060(11) -0.0033(12) -0.0082(11) C35 0.0327(14) 0.0508(17) 0.0296(16) 0.0027(13) 0.0065(12) -0.0007(12) _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 C18 1.858(2) . ? P1 C1 1.861(2) . ? P1 C9 1.865(2) . ? N1 C10 1.438(3) . ? N1 C16 1.475(3) . ? N1 C9 1.477(3) . ? C1 C6 1.413(3) . ? C1 C2 1.430(3) . ? C2 C3 1.400(3) . ? C2 C22 1.557(3) . ? C3 C4 1.385(3) . ? C4 C5 1.387(3) . ? C4 C26 1.539(3) . ? C5 C6 1.395(3) . ? C6 C7 1.544(3) . ? C7 C8 1.533(3) . ? C7 C21 1.540(3) . ? C7 C20 1.544(3) . ? C8 C9 1.514(3) . ? C10 C15 1.413(3) . ? C10 C11 1.416(3) . ? C11 C12 1.395(3) . ? C11 C30 1.521(3) . ? C12 C13 1.379(3) . ? C13 C14 1.384(3) . ? C14 C15 1.393(3) . ? C15 C33 1.522(3) . ? C16 C19 1.522(3) . ? C16 C17 1.528(3) . ? C17 C18 1.531(3) . ? C22 C24 1.534(3) . ? C22 C23 1.539(3) . ? C22 C25 1.542(3) . ? C26 C27 1.531(3) . ? C26 C29 1.538(3) . ? C26 C28 1.539(3) . ? C30 C32 1.535(3) . ? C30 C31 1.538(3) . ? C33 C35 1.523(3) . ? C33 C34 1.537(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 C18 P1 C1 100.66(9) . . ? C18 P1 C9 94.93(10) . . ? C1 P1 C9 103.41(9) . . ? C10 N1 C16 122.37(16) . . ? C10 N1 C9 115.38(16) . . ? C16 N1 C9 118.89(17) . . ? C6 C1 C2 118.55(19) . . ? C6 C1 P1 121.71(15) . . ? C2 C1 P1 119.67(15) . . ? C3 C2 C1 118.12(19) . . ? C3 C2 C22 117.92(18) . . ? C1 C2 C22 123.93(18) . . ? C4 C3 C2 123.61(19) . . ? C3 C4 C5 116.83(19) . . ? C3 C4 C26 123.35(19) . . ? C5 C4 C26 119.83(19) . . ? C4 C5 C6 122.9(2) . . ? C5 C6 C1 119.41(19) . . ? C5 C6 C7 116.91(18) . . ? C1 C6 C7 123.33(19) . . ? C8 C7 C21 105.73(17) . . ? C8 C7 C6 113.81(17) . . ? C21 C7 C6 112.50(18) . . ? C8 C7 C20 109.68(18) . . ? C21 C7 C20 107.91(18) . . ? C6 C7 C20 107.08(16) . . ? C9 C8 C7 115.27(17) . . ? N1 C9 C8 115.22(16) . . ? N1 C9 P1 107.56(14) . . ? C8 C9 P1 112.82(15) . . ? C15 C10 C11 119.7(2) . . ? C15 C10 N1 117.60(18) . . ? C11 C10 N1 122.67(19) . . ? C12 C11 C10 118.5(2) . . ? C12 C11 C30 117.85(19) . . ? C10 C11 C30 123.6(2) . . ? C13 C12 C11 121.9(2) . . ? C12 C13 C14 119.3(2) . . ? C13 C14 C15 121.2(2) . . ? C14 C15 C10 119.2(2) . . ? C14 C15 C33 118.9(2) . . ? C10 C15 C33 121.9(2) . . ? N1 C16 C19 110.98(18) . . ? N1 C16 C17 110.66(17) . . ? C19 C16 C17 108.97(18) . . ? C16 C17 C18 115.11(18) . . ? C17 C18 P1 108.41(15) . . ? C24 C22 C23 110.50(17) . . ? C24 C22 C25 105.44(18) . . ? C23 C22 C25 105.93(17) . . ? C24 C22 C2 112.16(16) . . ? C23 C22 C2 110.42(17) . . ? C25 C22 C2 112.12(17) . . ? C27 C26 C29 108.09(18) . . ? C27 C26 C28 108.33(19) . . ? C29 C26 C28 109.50(18) . . ? C27 C26 C4 112.70(18) . . ? C29 C26 C4 109.62(18) . . ? C28 C26 C4 108.55(17) . . ? C11 C30 C32 111.12(18) . . ? C11 C30 C31 112.04(18) . . ? C32 C30 C31 109.02(18) . . ? C15 C33 C35 111.3(2) . . ? C15 C33 C34 111.41(19) . . ? C35 C33 C34 110.6(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.653 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.056 #====END