Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'J Scott McIndoe' _publ_contact_author_address ;Department of Chemistry University of Victoria P.O. Box 3065 Victoria, BC V8W 3V6 CANADA ; _publ_contact_author_email mcindoe@uvic.ca _publ_contact_author_phone ;+1 (250) 721-7181 ; _publ_contact_author_fax ;+1 (250) 721-7147 ; loop_ _publ_author_name _publ_author_address J.S.McIndoe ;Department of Chemistry University of Victoria P.O. Box 3065 Victoria, BC V8W 3V6 CANADA ; N.Farrer ;Department of Chemistry University of Victoria P.O. Box 3065 Victoria, BC V8W 3V6 CANADA ; R.McDonald ;X-ray Crystallography Laboratory Department of Chemistry University of Alberta Edmonton AB T6G 2G2 Canada ; # Attachment '4.cif' data_vic0548 _database_code_depnum_ccdc_archive 'CCDC 611411' _audit_creation_method SHELXL-97 _chemical_name_systematic bis(1,8-bis(dimethylamino)naphth-2-yl)(phenyl)phosphine _chemical_name_common bis(1,8-bis(dimethylamino)naphth-2-yl)(phenyl)phosphine _chemical_melting_point ? _chemical_formula_moiety 'C34 H39 N4 P' _chemical_formula_sum 'C34 H39 N4 P' _chemical_formula_weight 534.66 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 Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 15.4223(12) _cell_length_b 10.8193(8) _cell_length_c 17.8969(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2986.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 7954 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 25.85 _exptl_crystal_description fragment _exptl_crystal_colour yellow _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9265 _exptl_absorpt_correction_T_max 0.9821 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22819 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.45 _reflns_number_total 6154 _reflns_number_gt 5074 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _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^)+(0.0772P)^2^+0.7419P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.14(11) _refine_ls_number_reflns 6154 _refine_ls_number_parameters 353 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 P P 0.20081(4) 0.26049(6) 0.07345(4) 0.03608(17) Uani 1 1 d . . . N1 N 0.19676(16) 0.3936(3) 0.21499(15) 0.0483(6) Uani 1 1 d . . . N2 N 0.11903(18) 0.5602(2) 0.31781(15) 0.0502(6) Uani 1 1 d . . . N3 N 0.15931(17) -0.0065(2) 0.10008(14) 0.0485(6) Uani 1 1 d . . . N4 N 0.01674(15) -0.1773(2) 0.07478(17) 0.0474(6) Uani 1 1 d . . . C1 C 0.2095(3) 0.3266(4) 0.2847(2) 0.0715(11) Uani 1 1 d . . . H1A H 0.2697 0.3361 0.3012 0.086 Uiso 1 1 calc R . . H1B H 0.1969 0.2387 0.2768 0.086 Uiso 1 1 calc R . . H1C H 0.1705 0.3597 0.3229 0.086 Uiso 1 1 calc R . . C2 C 0.2666(2) 0.4643(5) 0.1916(2) 0.0813(14) Uani 1 1 d . . . H2A H 0.3163 0.4490 0.2244 0.098 Uiso 1 1 calc R . . H2B H 0.2511 0.5520 0.1935 0.098 Uiso 1 1 calc R . . H2C H 0.2819 0.4417 0.1402 0.098 Uiso 1 1 calc R . . C3 C 0.1213(4) 0.5667(6) 0.3977(2) 0.107(2) Uani 1 1 d . . . H3A H 0.1048 0.4864 0.4187 0.128 Uiso 1 1 calc R . . H3B H 0.0806 0.6301 0.4150 0.128 Uiso 1 1 calc R . . H3C H 0.1800 0.5880 0.4141 0.128 Uiso 1 1 calc R . . C4 C 0.1452(3) 0.6747(4) 0.2856(3) 0.0890(14) Uani 1 1 d . . . H4A H 0.2008 0.7002 0.3071 0.107 Uiso 1 1 calc R . . H4B H 0.1013 0.7379 0.2960 0.107 Uiso 1 1 calc R . . H4C H 0.1514 0.6648 0.2314 0.107 Uiso 1 1 calc R . . C5 C 0.2079(2) -0.1211(3) 0.1008(2) 0.0595(9) Uani 1 1 d . . . H5A H 0.2267 -0.1392 0.1520 0.071 Uiso 1 1 calc R . . H5B H 0.2588 -0.1131 0.0684 0.071 Uiso 1 1 calc R . . H5C H 0.1710 -0.1884 0.0826 0.071 Uiso 1 1 calc R . . C6 C 0.1222(3) 0.0291(4) 0.1700(2) 0.0626(9) Uani 1 1 d . . . H6A H 0.1548 -0.0093 0.2108 0.075 Uiso 1 1 calc R . . H6B H 0.0617 0.0017 0.1720 0.075 Uiso 1 1 calc R . . H6C H 0.1246 0.1192 0.1750 0.075 Uiso 1 1 calc R . . C7 C -0.0068(3) -0.3021(3) 0.0973(2) 0.0696(11) Uani 1 1 d . . . H7A H -0.0230 -0.3024 0.1502 0.083 Uiso 1 1 calc R . . H7B H 0.0427 -0.3574 0.0895 0.083 Uiso 1 1 calc R . . H7C H -0.0560 -0.3306 0.0672 0.083 Uiso 1 1 calc R . . C8 C -0.0503(2) -0.0908(3) 0.0980(2) 0.0548(8) Uani 1 1 d . . . H8A H -0.0654 -0.1060 0.1504 0.066 Uiso 1 1 calc R . . H8B H -0.1019 -0.1022 0.0667 0.066 Uiso 1 1 calc R . . H8C H -0.0289 -0.0060 0.0924 0.066 Uiso 1 1 calc R . . C11 C 0.11361(16) 0.3940(2) 0.18186(14) 0.0308(5) Uani 1 1 d . . . C12 C 0.10476(16) 0.3361(3) 0.11424(15) 0.0376(6) Uani 1 1 d . . . C13 C 0.02267(19) 0.3262(3) 0.07972(19) 0.0557(9) Uani 1 1 d . . . H13 H 0.0183 0.2937 0.0306 0.067 Uiso 1 1 calc R . . C14 C -0.04971(18) 0.3628(3) 0.11631(18) 0.0479(7) Uani 1 1 d . . . H14 H -0.1049 0.3492 0.0941 0.057 Uiso 1 1 calc R . . C15 C -0.04471(16) 0.4206(2) 0.18671(15) 0.0354(6) Uani 1 1 d . . . C16 C -0.12154(19) 0.4567(3) 0.22365(18) 0.0457(7) Uani 1 1 d . . . H16 H -0.1761 0.4383 0.2016 0.055 Uiso 1 1 calc R . . C17 C -0.1190(2) 0.5165(4) 0.2892(2) 0.0617(9) Uani 1 1 d . . . H17 H -0.1712 0.5362 0.3148 0.074 Uiso 1 1 calc R . . C18 C -0.0388(2) 0.5494(3) 0.3194(2) 0.0569(9) Uani 1 1 d . . . H18 H -0.0378 0.5959 0.3644 0.068 Uiso 1 1 calc R . . C19 C 0.03871(19) 0.5176(3) 0.28701(17) 0.0417(6) Uani 1 1 d . . . C20 C 0.03846(16) 0.4449(2) 0.21981(14) 0.0312(5) Uani 1 1 d . . . C21 C 0.12824(17) 0.0353(3) 0.02962(15) 0.0362(6) Uani 1 1 d . . . C22 C 0.14833(17) 0.1548(2) 0.00594(15) 0.0344(6) Uani 1 1 d . . . C23 C 0.13547(17) 0.1885(3) -0.06917(16) 0.0386(6) Uani 1 1 d . . . H23 H 0.1451 0.2717 -0.0840 0.046 Uiso 1 1 calc R . . C24 C 0.10936(19) 0.1040(3) -0.12120(16) 0.0422(7) Uani 1 1 d . . . H24 H 0.1072 0.1263 -0.1725 0.051 Uiso 1 1 calc R . . C25 C 0.08546(18) -0.0167(3) -0.09882(17) 0.0403(6) Uani 1 1 d . . . C26 C 0.05960(19) -0.1050(3) -0.15337(18) 0.0494(8) Uani 1 1 d . . . H26 H 0.0606 -0.0845 -0.2050 0.059 Uiso 1 1 calc R . . C27 C 0.0335(2) -0.2185(3) -0.1310(2) 0.0568(9) Uani 1 1 d . . . H27 H 0.0230 -0.2810 -0.1671 0.068 Uiso 1 1 calc R . . C28 C 0.0219(2) -0.2447(3) -0.0547(2) 0.0523(8) Uani 1 1 d . . . H28 H -0.0004 -0.3231 -0.0406 0.063 Uiso 1 1 calc R . . C29 C 0.04183(17) -0.1606(3) -0.00031(18) 0.0415(6) Uani 1 1 d . . . C30 C 0.08552(16) -0.0478(3) -0.02206(16) 0.0377(6) Uani 1 1 d . . . C31 C 0.24032(17) 0.3835(2) 0.01109(16) 0.0374(6) Uani 1 1 d . . . C32 C 0.1972(2) 0.4936(3) -0.00486(17) 0.0473(7) Uani 1 1 d . . . H32 H 0.1416 0.5086 0.0161 0.057 Uiso 1 1 calc R . . C33 C 0.2346(3) 0.5812(3) -0.0508(2) 0.0601(9) Uani 1 1 d . . . H33 H 0.2045 0.6560 -0.0609 0.072 Uiso 1 1 calc R . . C34 C 0.3146(2) 0.5616(3) -0.0820(2) 0.0597(9) Uani 1 1 d . . . H34 H 0.3398 0.6227 -0.1133 0.072 Uiso 1 1 calc R . . C35 C 0.3581(2) 0.4535(3) -0.0678(2) 0.0592(9) Uani 1 1 d . . . H35 H 0.4130 0.4387 -0.0901 0.071 Uiso 1 1 calc R . . C36 C 0.32163(18) 0.3661(3) -0.02089(18) 0.0453(7) Uani 1 1 d . . . H36 H 0.3529 0.2925 -0.0103 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P 0.0289(3) 0.0409(4) 0.0385(3) -0.0063(3) -0.0007(3) 0.0037(3) N1 0.0326(12) 0.0580(16) 0.0542(15) -0.0048(13) -0.0095(11) -0.0074(11) N2 0.0580(16) 0.0454(14) 0.0473(15) -0.0107(11) -0.0064(12) -0.0111(12) N3 0.0525(15) 0.0481(14) 0.0449(13) 0.0041(11) -0.0008(12) -0.0017(12) N4 0.0416(12) 0.0375(12) 0.0630(15) 0.0092(13) 0.0072(13) 0.0008(10) C1 0.068(2) 0.065(2) 0.081(3) 0.009(2) -0.038(2) 0.0002(19) C2 0.0459(19) 0.144(4) 0.054(2) -0.012(2) 0.0013(16) -0.047(2) C3 0.107(4) 0.157(5) 0.056(3) -0.015(3) -0.004(2) -0.060(4) C4 0.068(3) 0.076(3) 0.123(4) 0.023(3) -0.009(3) -0.029(2) C5 0.0484(18) 0.056(2) 0.074(2) 0.0127(17) -0.0156(16) -0.0013(15) C6 0.066(2) 0.078(2) 0.0448(19) 0.0051(17) 0.0010(16) -0.0133(19) C7 0.066(2) 0.0478(19) 0.095(3) 0.0114(19) 0.008(2) -0.0051(17) C8 0.0460(17) 0.062(2) 0.0570(19) 0.0081(16) 0.0064(15) 0.0046(15) C11 0.0295(12) 0.0290(12) 0.0339(13) 0.0027(11) 0.0005(10) -0.0039(10) C12 0.0280(13) 0.0471(16) 0.0377(15) -0.0029(12) 0.0004(11) 0.0064(12) C13 0.0379(15) 0.080(2) 0.0488(18) -0.0318(17) -0.0133(14) 0.0096(15) C14 0.0299(14) 0.0539(18) 0.060(2) -0.0134(15) -0.0109(13) 0.0025(13) C15 0.0311(13) 0.0342(14) 0.0409(15) 0.0025(11) 0.0052(11) -0.0009(11) C16 0.0318(14) 0.0532(17) 0.0522(17) 0.0066(14) 0.0086(13) 0.0027(13) C17 0.0467(19) 0.081(2) 0.058(2) -0.0048(19) 0.0155(16) 0.0176(17) C18 0.061(2) 0.061(2) 0.0487(18) -0.0182(16) 0.0045(15) 0.0120(16) C19 0.0462(17) 0.0366(14) 0.0424(15) -0.0017(12) 0.0024(12) -0.0008(12) C20 0.0322(13) 0.0290(12) 0.0325(13) 0.0059(10) 0.0035(10) -0.0045(10) C21 0.0313(13) 0.0423(15) 0.0351(14) -0.0044(12) 0.0029(10) 0.0021(11) C22 0.0315(13) 0.0361(13) 0.0357(13) -0.0064(11) 0.0001(11) 0.0020(11) C23 0.0355(13) 0.0393(15) 0.0410(15) -0.0028(12) 0.0012(12) 0.0006(12) C24 0.0367(15) 0.0522(17) 0.0376(15) -0.0035(13) 0.0071(11) 0.0001(13) C25 0.0275(13) 0.0469(16) 0.0465(16) -0.0120(13) 0.0041(11) 0.0044(12) C26 0.0397(16) 0.061(2) 0.0473(17) -0.0175(15) 0.0079(13) -0.0001(14) C27 0.0412(17) 0.056(2) 0.073(2) -0.0313(18) 0.0026(15) -0.0017(15) C28 0.0375(16) 0.0424(17) 0.077(2) -0.0120(16) 0.0020(15) -0.0013(13) C29 0.0293(13) 0.0346(14) 0.0606(18) -0.0026(13) 0.0016(12) 0.0064(11) C30 0.0255(12) 0.0370(14) 0.0505(16) -0.0073(12) 0.0037(12) 0.0051(11) C31 0.0326(13) 0.0361(14) 0.0436(15) -0.0101(12) -0.0037(11) -0.0024(11) C32 0.0469(17) 0.0465(17) 0.0486(17) 0.0000(14) 0.0014(13) 0.0114(14) C33 0.068(2) 0.0488(19) 0.064(2) 0.0051(16) -0.0108(18) 0.0052(16) C34 0.054(2) 0.063(2) 0.062(2) 0.0117(17) -0.0100(17) -0.0166(17) C35 0.0366(16) 0.070(2) 0.071(2) -0.0050(18) 0.0044(16) -0.0147(16) C36 0.0327(15) 0.0441(16) 0.0590(18) -0.0080(14) 0.0053(13) -0.0019(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 P C31 1.841(3) . ? P C12 1.843(3) . ? P C22 1.850(3) . ? N1 C2 1.386(4) . ? N1 C11 1.413(3) . ? N1 C1 1.456(5) . ? N2 C4 1.425(5) . ? N2 C19 1.432(4) . ? N2 C3 1.433(5) . ? N3 C21 1.423(4) . ? N3 C6 1.428(4) . ? N3 C5 1.449(4) . ? N4 C29 1.410(4) . ? N4 C8 1.455(4) . ? N4 C7 1.456(4) . ? C11 C12 1.369(4) . ? C11 C20 1.452(4) . ? C12 C13 1.413(4) . ? C13 C14 1.353(4) . ? C14 C15 1.409(4) . ? C15 C16 1.412(4) . ? C15 C20 1.437(4) . ? C16 C17 1.340(5) . ? C17 C18 1.396(5) . ? C18 C19 1.372(4) . ? C19 C20 1.437(4) . ? C21 C22 1.395(4) . ? C21 C30 1.449(4) . ? C22 C23 1.407(4) . ? C23 C24 1.366(4) . ? C24 C25 1.415(4) . ? C25 C30 1.414(4) . ? C25 C26 1.423(4) . ? C26 C27 1.353(5) . ? C27 C28 1.405(5) . ? C28 C29 1.368(4) . ? C29 C30 1.448(4) . ? C31 C36 1.391(4) . ? C31 C32 1.394(4) . ? C32 C33 1.381(5) . ? C33 C34 1.370(5) . ? C34 C35 1.372(5) . ? C35 C36 1.384(5) . ? 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 C31 P C12 100.67(12) . . ? C31 P C22 101.30(12) . . ? C12 P C22 100.45(12) . . ? C2 N1 C11 125.3(3) . . ? C2 N1 C1 115.4(3) . . ? C11 N1 C1 118.9(3) . . ? C4 N2 C19 111.6(3) . . ? C4 N2 C3 110.8(4) . . ? C19 N2 C3 114.9(3) . . ? C21 N3 C6 123.8(3) . . ? C21 N3 C5 117.0(3) . . ? C6 N3 C5 115.4(3) . . ? C29 N4 C8 112.6(2) . . ? C29 N4 C7 116.8(3) . . ? C8 N4 C7 109.9(3) . . ? C12 C11 N1 117.4(2) . . ? C12 C11 C20 120.5(2) . . ? N1 C11 C20 122.0(2) . . ? C11 C12 C13 120.7(2) . . ? C11 C12 P 118.2(2) . . ? C13 C12 P 120.9(2) . . ? C14 C13 C12 120.4(3) . . ? C13 C14 C15 121.2(3) . . ? C14 C15 C16 119.7(3) . . ? C14 C15 C20 119.9(2) . . ? C16 C15 C20 120.4(3) . . ? C17 C16 C15 121.3(3) . . ? C16 C17 C18 119.2(3) . . ? C19 C18 C17 123.0(3) . . ? C18 C19 N2 120.7(3) . . ? C18 C19 C20 119.2(3) . . ? N2 C19 C20 120.0(3) . . ? C19 C20 C15 116.6(2) . . ? C19 C20 C11 126.7(2) . . ? C15 C20 C11 116.8(2) . . ? C22 C21 N3 119.3(2) . . ? C22 C21 C30 118.8(2) . . ? N3 C21 C30 121.4(2) . . ? C21 C22 C23 120.0(2) . . ? C21 C22 P 118.1(2) . . ? C23 C22 P 121.7(2) . . ? C24 C23 C22 121.3(3) . . ? C23 C24 C25 120.1(3) . . ? C30 C25 C24 119.6(3) . . ? C30 C25 C26 120.5(3) . . ? C24 C25 C26 119.9(3) . . ? C27 C26 C25 119.3(3) . . ? C26 C27 C28 120.6(3) . . ? C29 C28 C27 121.9(3) . . ? C28 C29 N4 122.2(3) . . ? C28 C29 C30 118.3(3) . . ? N4 C29 C30 119.5(3) . . ? C25 C30 C29 117.5(3) . . ? C25 C30 C21 118.2(3) . . ? C29 C30 C21 124.3(3) . . ? C36 C31 C32 117.5(3) . . ? C36 C31 P 116.7(2) . . ? C32 C31 P 125.8(2) . . ? C33 C32 C31 120.6(3) . . ? C34 C33 C32 120.9(3) . . ? C33 C34 C35 119.8(3) . . ? C34 C35 C36 119.7(3) . . ? C35 C36 C31 121.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C11 C12 73.7(4) . . . . ? C1 N1 C11 C12 -114.3(3) . . . . ? C2 N1 C11 C20 -110.9(4) . . . . ? C1 N1 C11 C20 61.0(4) . . . . ? N1 C11 C12 C13 176.2(3) . . . . ? C20 C11 C12 C13 0.8(4) . . . . ? N1 C11 C12 P 1.2(3) . . . . ? C20 C11 C12 P -174.21(19) . . . . ? C31 P C12 C11 -95.6(2) . . . . ? C22 P C12 C11 160.7(2) . . . . ? C31 P C12 C13 89.4(3) . . . . ? C22 P C12 C13 -14.3(3) . . . . ? C11 C12 C13 C14 -6.6(5) . . . . ? P C12 C13 C14 168.2(3) . . . . ? C12 C13 C14 C15 5.3(5) . . . . ? C13 C14 C15 C16 -179.5(3) . . . . ? C13 C14 C15 C20 1.8(5) . . . . ? C14 C15 C16 C17 -177.2(3) . . . . ? C20 C15 C16 C17 1.5(5) . . . . ? C15 C16 C17 C18 3.5(5) . . . . ? C16 C17 C18 C19 -3.6(6) . . . . ? C17 C18 C19 N2 176.1(3) . . . . ? C17 C18 C19 C20 -1.3(5) . . . . ? C4 N2 C19 C18 -90.8(4) . . . . ? C3 N2 C19 C18 36.5(5) . . . . ? C4 N2 C19 C20 86.6(4) . . . . ? C3 N2 C19 C20 -146.1(4) . . . . ? C18 C19 C20 C15 6.0(4) . . . . ? N2 C19 C20 C15 -171.4(2) . . . . ? C18 C19 C20 C11 -174.2(3) . . . . ? N2 C19 C20 C11 8.3(4) . . . . ? C14 C15 C20 C19 172.5(3) . . . . ? C16 C15 C20 C19 -6.2(4) . . . . ? C14 C15 C20 C11 -7.3(4) . . . . ? C16 C15 C20 C11 174.0(2) . . . . ? C12 C11 C20 C19 -173.8(3) . . . . ? N1 C11 C20 C19 11.0(4) . . . . ? C12 C11 C20 C15 6.0(3) . . . . ? N1 C11 C20 C15 -169.3(2) . . . . ? C6 N3 C21 C22 76.8(4) . . . . ? C5 N3 C21 C22 -126.2(3) . . . . ? C6 N3 C21 C30 -111.0(3) . . . . ? C5 N3 C21 C30 46.0(4) . . . . ? N3 C21 C22 C23 165.8(2) . . . . ? C30 C21 C22 C23 -6.7(4) . . . . ? N3 C21 C22 P -8.8(3) . . . . ? C30 C21 C22 P 178.75(19) . . . . ? C31 P C22 C21 165.0(2) . . . . ? C12 P C22 C21 -91.8(2) . . . . ? C31 P C22 C23 -9.5(2) . . . . ? C12 P C22 C23 93.7(2) . . . . ? C21 C22 C23 C24 -4.8(4) . . . . ? P C22 C23 C24 169.6(2) . . . . ? C22 C23 C24 C25 7.0(4) . . . . ? C23 C24 C25 C30 2.5(4) . . . . ? C23 C24 C25 C26 -179.0(3) . . . . ? C30 C25 C26 C27 1.2(4) . . . . ? C24 C25 C26 C27 -177.3(3) . . . . ? C25 C26 C27 C28 7.6(5) . . . . ? C26 C27 C28 C29 -4.5(5) . . . . ? C27 C28 C29 N4 168.8(3) . . . . ? C27 C28 C29 C30 -7.5(4) . . . . ? C8 N4 C29 C28 -109.9(3) . . . . ? C7 N4 C29 C28 18.6(4) . . . . ? C8 N4 C29 C30 66.3(3) . . . . ? C7 N4 C29 C30 -165.2(3) . . . . ? C24 C25 C30 C29 165.8(2) . . . . ? C26 C25 C30 C29 -12.7(4) . . . . ? C24 C25 C30 C21 -13.6(4) . . . . ? C26 C25 C30 C21 167.9(2) . . . . ? C28 C29 C30 C25 15.7(4) . . . . ? N4 C29 C30 C25 -160.7(2) . . . . ? C28 C29 C30 C21 -165.0(3) . . . . ? N4 C29 C30 C21 18.6(4) . . . . ? C22 C21 C30 C25 15.6(4) . . . . ? N3 C21 C30 C25 -156.6(2) . . . . ? C22 C21 C30 C29 -163.7(2) . . . . ? N3 C21 C30 C29 24.1(4) . . . . ? C12 P C31 C36 170.0(2) . . . . ? C22 P C31 C36 -87.0(2) . . . . ? C12 P C31 C32 -7.9(3) . . . . ? C22 P C31 C32 95.2(3) . . . . ? C36 C31 C32 C33 0.0(4) . . . . ? P C31 C32 C33 177.9(3) . . . . ? C31 C32 C33 C34 0.4(5) . . . . ? C32 C33 C34 C35 0.3(5) . . . . ? C33 C34 C35 C36 -1.3(5) . . . . ? C34 C35 C36 C31 1.7(5) . . . . ? C32 C31 C36 C35 -1.1(4) . . . . ? P C31 C36 C35 -179.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.234 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.045 data_bj0309 _database_code_depnum_ccdc_archive 'CCDC 611412' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H27 N2 P' _chemical_formula_sum 'C26 H27 N2 P' _chemical_formula_weight 398.47 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)/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 17.1220(3) _cell_length_b 10.1292(2) _cell_length_c 25.3141(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.8090(10) _cell_angle_gamma 90.00 _cell_volume 4380.58(14) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 22325 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 32696 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.0858 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.51 _reflns_number_total 10020 _reflns_number_gt 6163 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0494P)^2^+1.2637P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10020 _refine_ls_number_parameters 523 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.105 _refine_ls_shift/su_mean 0.006 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_1 P 1.13541(3) -0.08727(5) 0.29430(2) 0.03125(14) Uani 1 1 d . . . N1_1 N 1.12538(12) 0.03802(17) 0.39454(7) 0.0370(4) Uani 1 1 d . . . C1_1 C 1.10361(12) 0.13189(18) 0.35409(8) 0.0283(4) Uani 1 1 d . . . N2_1 N 1.04568(11) 0.23509(18) 0.45484(7) 0.0377(4) Uani 1 1 d . . . C2_1 C 1.11025(12) 0.08794(18) 0.30269(8) 0.0270(4) Uani 1 1 d . . . C3_1 C 1.10311(12) 0.17816(19) 0.26013(8) 0.0303(5) Uani 1 1 d . . . H3_1 H 1.1030 0.1469 0.2247 0.036 Uiso 1 1 calc R . . C4_1 C 1.09631(13) 0.31039(19) 0.26963(8) 0.0320(5) Uani 1 1 d . . . H4_1 H 1.0952 0.3705 0.2408 0.038 Uiso 1 1 calc R . . C5_1 C 1.09188(13) 0.4971(2) 0.33126(10) 0.0392(5) Uani 1 1 d . . . H5_1 H 1.0942 0.5573 0.3026 0.047 Uiso 1 1 calc R . . C6_1 C 1.08958(14) 0.5435(2) 0.38099(10) 0.0456(6) Uani 1 1 d . . . H6_1 H 1.0962 0.6352 0.3877 0.055 Uiso 1 1 calc R . . C7_1 C 1.07747(14) 0.4566(2) 0.42292(10) 0.0429(6) Uani 1 1 d . . . H7_1 H 1.0731 0.4914 0.4575 0.051 Uiso 1 1 calc R . . C8_1 C 1.07174(13) 0.3225(2) 0.41529(8) 0.0340(5) Uani 1 1 d . . . C9_1 C 1.08747(12) 0.26819(18) 0.36447(8) 0.0283(4) Uani 1 1 d . . . C10_1 C 1.09090(12) 0.35892(19) 0.32115(8) 0.0303(5) Uani 1 1 d . . . C11_1 C 1.18828(16) 0.0741(3) 0.43302(9) 0.0535(7) Uani 1 1 d . . . H11A_1 H 1.2228 0.1379 0.4172 0.080 Uiso 1 1 calc R . . H11B_1 H 1.2183 -0.0050 0.4438 0.080 Uiso 1 1 calc R . . H11C_1 H 1.1662 0.1136 0.4641 0.080 Uiso 1 1 calc R . . C12_1 C 1.06978(18) -0.0550(2) 0.41294(10) 0.0567(8) Uani 1 1 d . . . H12A_1 H 1.0298 -0.0736 0.3844 0.085 Uiso 1 1 calc R . . H12B_1 H 1.0449 -0.0176 0.4433 0.085 Uiso 1 1 calc R . . H12C_1 H 1.0968 -0.1370 0.4236 0.085 Uiso 1 1 calc R . . C13_1 C 1.06150(17) 0.2776(3) 0.50951(9) 0.0542(7) Uani 1 1 d . . . H13A_1 H 1.1173 0.2981 0.5157 0.081 Uiso 1 1 calc R . . H13B_1 H 1.0474 0.2067 0.5335 0.081 Uiso 1 1 calc R . . H13C_1 H 1.0305 0.3565 0.5161 0.081 Uiso 1 1 calc R . . C14_1 C 0.96283(15) 0.2042(3) 0.44442(9) 0.0505(6) Uani 1 1 d . . . H14A_1 H 0.9532 0.1765 0.4075 0.076 Uiso 1 1 calc R . . H14B_1 H 0.9314 0.2827 0.4509 0.076 Uiso 1 1 calc R . . H14C_1 H 0.9482 0.1326 0.4679 0.076 Uiso 1 1 calc R . . C21_1 C 1.23865(13) -0.08635(19) 0.31905(8) 0.0306(5) Uani 1 1 d . . . C22_1 C 1.28619(14) 0.0253(2) 0.32119(9) 0.0374(5) Uani 1 1 d . . . H22_1 H 1.2671 0.1054 0.3057 0.045 Uiso 1 1 calc R . . C23_1 C 1.36088(15) 0.0210(2) 0.34562(9) 0.0453(6) Uani 1 1 d . . . H23_1 H 1.3923 0.0984 0.3472 0.054 Uiso 1 1 calc R . . C24_1 C 1.39009(15) -0.0951(3) 0.36768(9) 0.0484(6) Uani 1 1 d . . . H24_1 H 1.4413 -0.0977 0.3845 0.058 Uiso 1 1 calc R . . C25_1 C 1.34429(15) -0.2076(2) 0.36512(9) 0.0463(6) Uani 1 1 d . . . H25_1 H 1.3642 -0.2880 0.3799 0.056 Uiso 1 1 calc R . . C26_1 C 1.26940(14) -0.2029(2) 0.34108(8) 0.0377(5) Uani 1 1 d . . . H26_1 H 1.2383 -0.2806 0.3396 0.045 Uiso 1 1 calc R . . C31_1 C 1.13907(13) -0.09589(18) 0.22184(8) 0.0310(5) Uani 1 1 d . . . C32_1 C 1.06762(14) -0.1162(2) 0.19265(9) 0.0404(6) Uani 1 1 d . . . H32_1 H 1.0209 -0.1250 0.2106 0.048 Uiso 1 1 calc R . . C33_1 C 1.06422(15) -0.1236(2) 0.13775(10) 0.0462(6) Uani 1 1 d . . . H33_1 H 1.0153 -0.1364 0.1184 0.055 Uiso 1 1 calc R . . C34_1 C 1.13159(16) -0.1125(2) 0.11130(9) 0.0443(6) Uani 1 1 d . . . H34_1 H 1.1292 -0.1178 0.0738 0.053 Uiso 1 1 calc R . . C35_1 C 1.20277(15) -0.0937(2) 0.13941(9) 0.0414(6) Uani 1 1 d . . . H35_1 H 1.2494 -0.0869 0.1212 0.050 Uiso 1 1 calc R . . C36_1 C 1.20598(14) -0.0848(2) 0.19431(8) 0.0364(5) Uani 1 1 d . . . H36_1 H 1.2550 -0.0707 0.2133 0.044 Uiso 1 1 calc R . . P1_2 P 0.77686(4) 0.13717(6) 0.08265(2) 0.03846(16) Uani 1 1 d . . . N1_2 N 0.68040(11) 0.01999(18) 0.16051(7) 0.0409(5) Uani 1 1 d . . . C1_2 C 0.75001(13) 0.07150(19) 0.18577(8) 0.0327(5) Uani 1 1 d . . . N2_2 N 0.63287(12) 0.06748(18) 0.26678(7) 0.0435(5) Uani 1 1 d . . . C2_2 C 0.80619(14) 0.11986(19) 0.15340(9) 0.0354(5) Uani 1 1 d . . . C3_2 C 0.88224(14) 0.1479(2) 0.17524(10) 0.0447(6) Uani 1 1 d . . . H3_2 H 0.9190 0.1892 0.1541 0.054 Uiso 1 1 calc R . . C4_2 C 0.90346(15) 0.1159(2) 0.22658(10) 0.0496(6) Uani 1 1 d . . . H4_2 H 0.9563 0.1273 0.2397 0.059 Uiso 1 1 calc R . . C5_2 C 0.87131(17) 0.0249(2) 0.31275(10) 0.0524(7) Uani 1 1 d . . . H5_2 H 0.9249 0.0279 0.3250 0.063 Uiso 1 1 calc R . . C6_2 C 0.81747(19) -0.0189(2) 0.34527(10) 0.0567(8) Uani 1 1 d . . . H6_2 H 0.8339 -0.0549 0.3788 0.068 Uiso 1 1 calc R . . C7_2 C 0.73728(17) -0.0114(2) 0.32966(9) 0.0475(6) Uani 1 1 d . . . H7_2 H 0.6999 -0.0383 0.3536 0.057 Uiso 1 1 calc R . . C8_2 C 0.71194(14) 0.0341(2) 0.28026(9) 0.0375(5) Uani 1 1 d . . . C9_2 C 0.76827(13) 0.05798(18) 0.24176(8) 0.0334(5) Uani 1 1 d . . . C10_2 C 0.84855(14) 0.0664(2) 0.26055(9) 0.0407(6) Uani 1 1 d . . . C11_2 C 0.61699(16) 0.1031(3) 0.13997(11) 0.0618(8) Uani 1 1 d . . . H11C_2 H 0.6373 0.1908 0.1320 0.093 Uiso 1 1 calc R . . H11B_2 H 0.5779 0.1111 0.1664 0.093 Uiso 1 1 calc R . . H11A_2 H 0.5926 0.0639 0.1075 0.093 Uiso 1 1 calc R . . C12_2 C 0.65712(17) -0.1132(2) 0.17380(10) 0.0548(7) Uani 1 1 d . . . H12C_2 H 0.7033 -0.1633 0.1871 0.082 Uiso 1 1 calc R . . H12B_2 H 0.6331 -0.1565 0.1421 0.082 Uiso 1 1 calc R . . H12A_2 H 0.6193 -0.1095 0.2011 0.082 Uiso 1 1 calc R . . C13_2 C 0.62220(16) 0.2100(2) 0.25954(11) 0.0553(7) Uani 1 1 d . . . H13C_2 H 0.6620 0.2440 0.2370 0.083 Uiso 1 1 calc R . . H13B_2 H 0.6274 0.2540 0.2941 0.083 Uiso 1 1 calc R . . H13A_2 H 0.5700 0.2273 0.2427 0.083 Uiso 1 1 calc R . . C14_2 C 0.57438(18) 0.0143(3) 0.30045(11) 0.0653(8) Uani 1 1 d . . . H14C_2 H 0.5826 -0.0809 0.3050 0.098 Uiso 1 1 calc R . . H14B_2 H 0.5219 0.0304 0.2838 0.098 Uiso 1 1 calc R . . H14A_2 H 0.5794 0.0578 0.3351 0.098 Uiso 1 1 calc R . . C21_2 C 0.78101(14) -0.0338(2) 0.05882(8) 0.0377(5) Uani 1 1 d . . . C22_2 C 0.75231(15) -0.0574(3) 0.00732(9) 0.0501(6) Uani 1 1 d . . . H22_2 H 0.7304 0.0133 -0.0134 0.060 Uiso 1 1 calc R . . C23_2 C 0.75505(18) -0.1823(3) -0.01451(11) 0.0657(8) Uani 1 1 d . . . H23_2 H 0.7356 -0.1967 -0.0501 0.079 Uiso 1 1 calc R . . C24_2 C 0.78582(19) -0.2852(3) 0.01520(12) 0.0682(9) Uani 1 1 d . . . H24_2 H 0.7875 -0.3712 0.0004 0.082 Uiso 1 1 calc R . . C25_2 C 0.8141(2) -0.2638(3) 0.06625(11) 0.0663(8) Uani 1 1 d . . . H25_2 H 0.8354 -0.3351 0.0868 0.080 Uiso 1 1 calc R . . C26_2 C 0.81172(17) -0.1391(2) 0.08814(10) 0.0518(7) Uani 1 1 d . . . H26_2 H 0.8314 -0.1255 0.1237 0.062 Uiso 1 1 calc R . . C31_2 C 0.86478(14) 0.2010(2) 0.05323(9) 0.0389(5) Uani 1 1 d . . . C32_2 C 0.93438(15) 0.1318(2) 0.04966(10) 0.0484(6) Uani 1 1 d . . . H32_2 H 0.9405 0.0481 0.0664 0.058 Uiso 1 1 calc R . . C33_2 C 0.99497(16) 0.1824(3) 0.02226(10) 0.0547(7) Uani 1 1 d . . . H33_2 H 1.0424 0.1343 0.0207 0.066 Uiso 1 1 calc R . . C34_2 C 0.98621(19) 0.3030(3) -0.00274(11) 0.0615(8) Uani 1 1 d . . . H34_2 H 1.0273 0.3374 -0.0221 0.074 Uiso 1 1 calc R . . C35_2 C 0.9183(2) 0.3732(3) 0.00028(11) 0.0624(8) Uani 1 1 d . . . H35_2 H 0.9126 0.4564 -0.0168 0.075 Uiso 1 1 calc R . . C36_2 C 0.85789(16) 0.3231(2) 0.02830(10) 0.0490(6) Uani 1 1 d . . . H36_2 H 0.8112 0.3729 0.0304 0.059 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_1 0.0340(3) 0.0257(3) 0.0346(3) -0.0010(2) 0.0060(2) -0.0008(2) N1_1 0.0460(12) 0.0368(10) 0.0281(9) 0.0056(7) 0.0024(9) 0.0089(9) C1_1 0.0270(12) 0.0292(10) 0.0289(11) 0.0031(8) 0.0028(9) 0.0020(9) N2_1 0.0385(12) 0.0481(11) 0.0265(9) -0.0063(8) 0.0027(8) 0.0043(9) C2_1 0.0252(11) 0.0278(10) 0.0285(10) 0.0000(8) 0.0052(9) 0.0001(8) C3_1 0.0294(12) 0.0335(11) 0.0285(11) 0.0007(8) 0.0046(9) -0.0023(9) C4_1 0.0308(13) 0.0302(11) 0.0350(11) 0.0080(9) 0.0031(10) 0.0004(9) C5_1 0.0320(13) 0.0284(11) 0.0571(15) 0.0013(10) 0.0031(11) 0.0027(9) C6_1 0.0407(15) 0.0303(12) 0.0654(17) -0.0120(11) 0.0021(13) 0.0026(10) C7_1 0.0377(14) 0.0433(13) 0.0474(14) -0.0163(11) 0.0006(11) 0.0082(11) C8_1 0.0289(13) 0.0373(12) 0.0357(12) -0.0068(9) 0.0005(10) 0.0055(9) C9_1 0.0236(11) 0.0290(10) 0.0322(11) -0.0028(8) 0.0011(9) 0.0018(8) C10_1 0.0204(11) 0.0295(10) 0.0410(12) 0.0016(9) 0.0018(9) 0.0023(8) C11_1 0.0583(18) 0.0641(16) 0.0368(13) 0.0028(12) -0.0062(13) 0.0258(14) C12_1 0.089(2) 0.0375(13) 0.0454(15) 0.0119(11) 0.0171(15) 0.0012(13) C13_1 0.0560(18) 0.0733(18) 0.0328(13) -0.0130(12) -0.0009(12) 0.0030(14) C14_1 0.0472(17) 0.0639(16) 0.0401(14) 0.0051(12) 0.0000(12) -0.0057(13) C21_1 0.0362(13) 0.0284(10) 0.0275(10) -0.0039(8) 0.0054(9) 0.0036(9) C22_1 0.0376(14) 0.0301(11) 0.0447(13) -0.0062(9) 0.0055(11) 0.0029(10) C23_1 0.0399(15) 0.0458(14) 0.0504(14) -0.0173(11) 0.0054(12) -0.0031(11) C24_1 0.0392(15) 0.0730(18) 0.0324(12) -0.0103(12) -0.0018(11) 0.0087(13) C25_1 0.0494(17) 0.0530(15) 0.0367(13) 0.0056(11) 0.0038(12) 0.0146(13) C26_1 0.0436(15) 0.0354(12) 0.0346(12) 0.0036(9) 0.0054(11) 0.0062(10) C31_1 0.0332(13) 0.0237(10) 0.0360(11) -0.0038(8) 0.0017(10) -0.0005(9) C32_1 0.0332(14) 0.0430(13) 0.0451(14) -0.0077(10) 0.0037(11) -0.0061(10) C33_1 0.0428(16) 0.0467(14) 0.0475(15) -0.0079(11) -0.0101(12) -0.0041(11) C34_1 0.0561(18) 0.0423(13) 0.0340(12) -0.0036(10) -0.0009(12) 0.0005(11) C35_1 0.0420(15) 0.0462(13) 0.0366(12) -0.0044(10) 0.0062(11) 0.0007(11) C36_1 0.0324(13) 0.0406(12) 0.0359(12) -0.0054(9) 0.0002(10) 0.0007(10) P1_2 0.0372(4) 0.0375(3) 0.0407(3) 0.0017(2) 0.0025(3) -0.0010(3) N1_2 0.0341(12) 0.0457(11) 0.0417(11) 0.0009(8) -0.0065(9) -0.0105(9) C1_2 0.0309(13) 0.0284(11) 0.0380(12) -0.0051(9) -0.0043(10) -0.0006(9) N2_2 0.0410(13) 0.0492(12) 0.0407(11) 0.0005(9) 0.0058(9) -0.0058(9) C2_2 0.0334(13) 0.0302(11) 0.0424(13) -0.0078(9) 0.0003(10) -0.0019(9) C3_2 0.0312(14) 0.0525(14) 0.0509(15) -0.0166(11) 0.0062(12) -0.0073(11) C4_2 0.0292(14) 0.0632(16) 0.0552(16) -0.0237(12) -0.0055(12) -0.0022(12) C5_2 0.0483(17) 0.0598(16) 0.0465(15) -0.0190(12) -0.0173(13) 0.0148(13) C6_2 0.079(2) 0.0526(16) 0.0362(14) -0.0028(11) -0.0145(15) 0.0204(15) C7_2 0.0639(19) 0.0430(14) 0.0352(13) -0.0031(10) -0.0004(13) 0.0007(12) C8_2 0.0448(15) 0.0312(11) 0.0359(12) -0.0049(9) -0.0027(11) -0.0033(10) C9_2 0.0380(14) 0.0248(10) 0.0364(12) -0.0063(8) -0.0038(10) 0.0015(9) C10_2 0.0393(15) 0.0402(13) 0.0412(13) -0.0151(10) -0.0074(11) 0.0069(10) C11_2 0.0357(16) 0.091(2) 0.0569(17) 0.0227(15) -0.0074(13) -0.0123(14) C12_2 0.0615(19) 0.0514(15) 0.0504(15) -0.0071(11) -0.0043(14) -0.0243(13) C13_2 0.0434(17) 0.0612(17) 0.0617(17) 0.0057(13) 0.0063(13) 0.0112(13) C14_2 0.058(2) 0.082(2) 0.0565(17) 0.0010(14) 0.0125(15) -0.0224(16) C21_2 0.0359(14) 0.0439(13) 0.0333(12) -0.0013(10) 0.0018(10) -0.0068(10) C22_2 0.0467(17) 0.0645(17) 0.0384(14) -0.0049(12) -0.0032(12) 0.0003(13) C23_2 0.062(2) 0.085(2) 0.0483(16) -0.0288(15) -0.0089(14) -0.0021(16) C24_2 0.077(2) 0.0558(18) 0.071(2) -0.0291(15) 0.0040(17) -0.0109(16) C25_2 0.097(3) 0.0400(15) 0.0620(18) -0.0013(13) 0.0056(17) -0.0002(15) C26_2 0.075(2) 0.0389(13) 0.0407(14) -0.0014(11) -0.0041(13) -0.0028(13) C31_2 0.0423(15) 0.0356(12) 0.0390(12) -0.0027(10) 0.0048(11) -0.0040(10) C32_2 0.0472(17) 0.0416(13) 0.0571(16) -0.0024(11) 0.0084(13) -0.0039(12) C33_2 0.0464(17) 0.0586(16) 0.0601(17) -0.0181(13) 0.0120(14) -0.0115(13) C34_2 0.065(2) 0.0657(18) 0.0557(17) -0.0093(14) 0.0172(15) -0.0309(16) C35_2 0.075(2) 0.0496(16) 0.0639(18) 0.0090(13) 0.0104(17) -0.0190(15) C36_2 0.0571(18) 0.0369(13) 0.0535(15) 0.0023(11) 0.0068(13) -0.0065(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_1 C21_1 1.836(2) . ? P1_1 C31_1 1.841(2) . ? P1_1 C2_1 1.842(2) . ? N1_1 C1_1 1.428(2) . ? N1_1 C12_1 1.439(3) . ? N1_1 C11_1 1.450(3) . ? C1_1 C2_1 1.387(3) . ? C1_1 C9_1 1.436(3) . ? N2_1 C8_1 1.430(3) . ? N2_1 C13_1 1.457(3) . ? N2_1 C14_1 1.459(3) . ? C2_1 C3_1 1.412(3) . ? C3_1 C4_1 1.367(3) . ? C4_1 C10_1 1.403(3) . ? C5_1 C6_1 1.347(3) . ? C5_1 C10_1 1.423(3) . ? C6_1 C7_1 1.405(3) . ? C7_1 C8_1 1.374(3) . ? C8_1 C9_1 1.441(3) . ? C9_1 C10_1 1.435(3) . ? C21_1 C22_1 1.392(3) . ? C21_1 C26_1 1.394(3) . ? C22_1 C23_1 1.384(3) . ? C23_1 C24_1 1.381(3) . ? C24_1 C25_1 1.382(3) . ? C25_1 C26_1 1.383(3) . ? C31_1 C36_1 1.384(3) . ? C31_1 C32_1 1.402(3) . ? C32_1 C33_1 1.389(3) . ? C33_1 C34_1 1.376(3) . ? C34_1 C35_1 1.383(3) . ? C35_1 C36_1 1.390(3) . ? P1_2 C2_2 1.836(2) . ? P1_2 C21_2 1.836(2) . ? P1_2 C31_2 1.841(2) . ? N1_2 C1_2 1.414(3) . ? N1_2 C11_2 1.443(3) . ? N1_2 C12_2 1.452(3) . ? C1_2 C2_2 1.393(3) . ? C1_2 C9_2 1.438(3) . ? N2_2 C8_2 1.415(3) . ? N2_2 C14_2 1.460(3) . ? N2_2 C13_2 1.465(3) . ? C2_2 C3_2 1.409(3) . ? C3_2 C4_2 1.365(3) . ? C4_2 C10_2 1.408(3) . ? C5_2 C6_2 1.351(4) . ? C5_2 C10_2 1.416(3) . ? C6_2 C7_2 1.405(4) . ? C7_2 C8_2 1.376(3) . ? C8_2 C9_2 1.437(3) . ? C9_2 C10_2 1.427(3) . ? C21_2 C22_2 1.383(3) . ? C21_2 C26_2 1.384(3) . ? C22_2 C23_2 1.382(4) . ? C23_2 C24_2 1.370(4) . ? C24_2 C25_2 1.367(4) . ? C25_2 C26_2 1.380(3) . ? C31_2 C36_2 1.389(3) . ? C31_2 C32_2 1.391(3) . ? C32_2 C33_2 1.384(3) . ? C33_2 C34_2 1.379(4) . ? C34_2 C35_2 1.369(4) . ? C35_2 C36_2 1.389(4) . ? 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 C21_1 P1_1 C31_1 104.15(10) . . ? C21_1 P1_1 C2_1 100.54(9) . . ? C31_1 P1_1 C2_1 100.62(9) . . ? C1_1 N1_1 C12_1 121.4(2) . . ? C1_1 N1_1 C11_1 117.43(18) . . ? C12_1 N1_1 C11_1 115.17(19) . . ? C2_1 C1_1 N1_1 115.15(17) . . ? C2_1 C1_1 C9_1 120.60(17) . . ? N1_1 C1_1 C9_1 123.59(17) . . ? C8_1 N2_1 C13_1 115.78(18) . . ? C8_1 N2_1 C14_1 110.56(17) . . ? C13_1 N2_1 C14_1 110.61(19) . . ? C1_1 C2_1 C3_1 119.98(17) . . ? C1_1 C2_1 P1_1 116.86(14) . . ? C3_1 C2_1 P1_1 123.01(15) . . ? C4_1 C3_1 C2_1 120.26(19) . . ? C3_1 C4_1 C10_1 121.24(18) . . ? C6_1 C5_1 C10_1 120.7(2) . . ? C5_1 C6_1 C7_1 120.2(2) . . ? C8_1 C7_1 C6_1 121.7(2) . . ? C7_1 C8_1 N2_1 122.42(19) . . ? C7_1 C8_1 C9_1 119.2(2) . . ? N2_1 C8_1 C9_1 118.29(17) . . ? C10_1 C9_1 C1_1 117.25(17) . . ? C10_1 C9_1 C8_1 117.21(17) . . ? C1_1 C9_1 C8_1 125.47(18) . . ? C4_1 C10_1 C5_1 120.75(19) . . ? C4_1 C10_1 C9_1 119.65(17) . . ? C5_1 C10_1 C9_1 119.55(19) . . ? C22_1 C21_1 C26_1 117.9(2) . . ? C22_1 C21_1 P1_1 124.38(16) . . ? C26_1 C21_1 P1_1 117.50(16) . . ? C23_1 C22_1 C21_1 120.8(2) . . ? C24_1 C23_1 C22_1 120.4(2) . . ? C23_1 C24_1 C25_1 119.6(2) . . ? C24_1 C25_1 C26_1 119.9(2) . . ? C25_1 C26_1 C21_1 121.3(2) . . ? C36_1 C31_1 C32_1 118.0(2) . . ? C36_1 C31_1 P1_1 125.57(17) . . ? C32_1 C31_1 P1_1 116.47(17) . . ? C33_1 C32_1 C31_1 120.8(2) . . ? C34_1 C33_1 C32_1 120.1(2) . . ? C33_1 C34_1 C35_1 120.0(2) . . ? C34_1 C35_1 C36_1 119.9(2) . . ? C31_1 C36_1 C35_1 121.3(2) . . ? C2_2 P1_2 C21_2 102.50(9) . . ? C2_2 P1_2 C31_2 104.49(10) . . ? C21_2 P1_2 C31_2 98.51(10) . . ? C1_2 N1_2 C11_2 122.60(19) . . ? C1_2 N1_2 C12_2 118.29(18) . . ? C11_2 N1_2 C12_2 114.4(2) . . ? C2_2 C1_2 N1_2 117.24(19) . . ? C2_2 C1_2 C9_2 120.0(2) . . ? N1_2 C1_2 C9_2 122.15(19) . . ? C8_2 N2_2 C14_2 117.0(2) . . ? C8_2 N2_2 C13_2 112.02(19) . . ? C14_2 N2_2 C13_2 110.6(2) . . ? C1_2 C2_2 C3_2 119.7(2) . . ? C1_2 C2_2 P1_2 116.90(16) . . ? C3_2 C2_2 P1_2 123.31(18) . . ? C4_2 C3_2 C2_2 120.4(2) . . ? C3_2 C4_2 C10_2 121.3(2) . . ? C6_2 C5_2 C10_2 120.6(2) . . ? C5_2 C6_2 C7_2 120.3(2) . . ? C8_2 C7_2 C6_2 121.1(2) . . ? C7_2 C8_2 N2_2 122.6(2) . . ? C7_2 C8_2 C9_2 119.2(2) . . ? N2_2 C8_2 C9_2 118.10(19) . . ? C10_2 C9_2 C8_2 117.3(2) . . ? C10_2 C9_2 C1_2 117.7(2) . . ? C8_2 C9_2 C1_2 125.0(2) . . ? C4_2 C10_2 C5_2 121.5(2) . . ? C4_2 C10_2 C9_2 119.0(2) . . ? C5_2 C10_2 C9_2 119.5(2) . . ? C22_2 C21_2 C26_2 118.1(2) . . ? C22_2 C21_2 P1_2 117.00(18) . . ? C26_2 C21_2 P1_2 124.93(17) . . ? C23_2 C22_2 C21_2 121.1(2) . . ? C24_2 C23_2 C22_2 119.9(2) . . ? C25_2 C24_2 C23_2 119.8(2) . . ? C24_2 C25_2 C26_2 120.5(3) . . ? C25_2 C26_2 C21_2 120.7(2) . . ? C36_2 C31_2 C32_2 117.8(2) . . ? C36_2 C31_2 P1_2 116.71(19) . . ? C32_2 C31_2 P1_2 125.19(18) . . ? C33_2 C32_2 C31_2 121.3(2) . . ? C34_2 C33_2 C32_2 119.7(3) . . ? C35_2 C34_2 C33_2 120.1(3) . . ? C34_2 C35_2 C36_2 120.2(3) . . ? C35_2 C36_2 C31_2 120.9(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.265 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.059 # Attachment '3HBr.cif' data_bj0310 _database_code_depnum_ccdc_archive 'CCDC 611413' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H27 N2 P, C2 H6 O, Br' _chemical_formula_sum 'C28 H33 Br N2 O P' _chemical_formula_weight 524.44 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' 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' _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 16.0283(3) _cell_length_b 7.18140(10) _cell_length_c 22.5380(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.9630(10) _cell_angle_gamma 90.00 _cell_volume 2562.57(9) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 22722 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1092 _exptl_absorpt_coefficient_mu 1.690 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 23406 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0603 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5838 _reflns_number_gt 4225 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0497P)^2^+3.7358P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5838 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1292 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 Br1 Br 0.66994(2) 0.72554(5) 0.045551(19) 0.04037(14) Uani 1 1 d . . . P1 P 0.81844(5) 0.12253(11) 0.28358(4) 0.02195(18) Uani 1 1 d . . . N1 N 0.69418(16) 0.2637(3) 0.16806(11) 0.0199(5) Uani 1 1 d . . . N2 N 0.55625(16) 0.2665(3) 0.09367(11) 0.0201(5) Uani 1 1 d . . . O1 O 0.8648(3) 0.6770(8) 0.5987(2) 0.1062(15) Uani 1 1 d . . . H1 H 0.8149 0.7169 0.5918 0.127 Uiso 1 1 calc R . . C1 C 0.66537(18) 0.1075(4) 0.20101(13) 0.0176(6) Uani 1 1 d . . . C2 C 0.71264(18) 0.0307(4) 0.25158(13) 0.0199(6) Uani 1 1 d . . . C3 C 0.6785(2) -0.1231(4) 0.27973(14) 0.0248(7) Uani 1 1 d . . . H3 H 0.7114 -0.1793 0.3137 0.030 Uiso 1 1 calc R . . C4 C 0.6004(2) -0.1916(4) 0.25956(14) 0.0224(6) Uani 1 1 d . . . H4 H 0.5794 -0.2927 0.2800 0.027 Uiso 1 1 calc R . . C5 C 0.4685(2) -0.1870(4) 0.18737(14) 0.0238(7) Uani 1 1 d . . . H5 H 0.4476 -0.2866 0.2085 0.029 Uiso 1 1 calc R . . C6 C 0.4195(2) -0.1170(4) 0.13737(14) 0.0252(7) Uani 1 1 d . . . H6 H 0.3655 -0.1691 0.1235 0.030 Uiso 1 1 calc R . . C7 C 0.4496(2) 0.0327(4) 0.10648(14) 0.0241(7) Uani 1 1 d . . . H7 H 0.4154 0.0829 0.0720 0.029 Uiso 1 1 calc R . . C8 C 0.52776(19) 0.1066(4) 0.12579(13) 0.0198(6) Uani 1 1 d . . . C9 C 0.58216(18) 0.0376(4) 0.17742(13) 0.0173(6) Uani 1 1 d . . . C10 C 0.54974(19) -0.1145(4) 0.20831(13) 0.0206(6) Uani 1 1 d . . . C11 C 0.7666(2) 0.2235(5) 0.13671(15) 0.0320(8) Uani 1 1 d . . . H11C H 0.7572 0.1046 0.1154 0.048 Uiso 1 1 calc R . . H11B H 0.8184 0.2161 0.1661 0.048 Uiso 1 1 calc R . . H11A H 0.7721 0.3232 0.1079 0.048 Uiso 1 1 calc R . . C12 C 0.7031(2) 0.4424(4) 0.20153(15) 0.0324(8) Uani 1 1 d . . . H12C H 0.6534 0.4623 0.2211 0.049 Uiso 1 1 calc R . . H12B H 0.7081 0.5449 0.1736 0.049 Uiso 1 1 calc R . . H12A H 0.7539 0.4382 0.2320 0.049 Uiso 1 1 calc R . . C13 C 0.5658(2) 0.2224(4) 0.03073(14) 0.0263(7) Uani 1 1 d . . . H13C H 0.6019 0.1124 0.0302 0.039 Uiso 1 1 calc R . . H13B H 0.5917 0.3284 0.0132 0.039 Uiso 1 1 calc R . . H13A H 0.5102 0.1971 0.0073 0.039 Uiso 1 1 calc R . . C14 C 0.5017(2) 0.4330(4) 0.09703(16) 0.0316(8) Uani 1 1 d . . . H14C H 0.4967 0.4580 0.1391 0.047 Uiso 1 1 calc R . . H14B H 0.4455 0.4095 0.0742 0.047 Uiso 1 1 calc R . . H14A H 0.5270 0.5410 0.0801 0.047 Uiso 1 1 calc R . . C21 C 0.87770(19) -0.0950(4) 0.29945(14) 0.0245(7) Uani 1 1 d . . . C22 C 0.8801(2) -0.2203(4) 0.25213(16) 0.0295(7) Uani 1 1 d . . . H22 H 0.8433 -0.2033 0.2152 0.035 Uiso 1 1 calc R . . C23 C 0.9360(2) -0.3695(5) 0.25905(18) 0.0373(9) Uani 1 1 d . . . H23 H 0.9373 -0.4539 0.2268 0.045 Uiso 1 1 calc R . . C24 C 0.9898(2) -0.3958(5) 0.31254(18) 0.0399(9) Uani 1 1 d . . . H24 H 1.0282 -0.4975 0.3170 0.048 Uiso 1 1 calc R . . C25 C 0.9875(2) -0.2733(5) 0.35951(18) 0.0378(8) Uani 1 1 d . . . H25 H 1.0243 -0.2910 0.3964 0.045 Uiso 1 1 calc R . . C26 C 0.9316(2) -0.1245(5) 0.35305(15) 0.0308(7) Uani 1 1 d . . . H26 H 0.9301 -0.0418 0.3858 0.037 Uiso 1 1 calc R . . C31 C 0.80009(19) 0.2063(4) 0.35757(14) 0.0229(6) Uani 1 1 d . . . C32 C 0.7788(2) 0.0964(5) 0.40444(14) 0.0278(7) Uani 1 1 d . . . H32 H 0.7716 -0.0341 0.3988 0.033 Uiso 1 1 calc R . . C33 C 0.7680(2) 0.1756(5) 0.45874(15) 0.0326(8) Uani 1 1 d . . . H33 H 0.7534 0.0996 0.4901 0.039 Uiso 1 1 calc R . . C34 C 0.7783(2) 0.3651(5) 0.46735(15) 0.0359(8) Uani 1 1 d . . . H34 H 0.7707 0.4193 0.5046 0.043 Uiso 1 1 calc R . . C35 C 0.7998(2) 0.4760(5) 0.42191(16) 0.0380(9) Uani 1 1 d . . . H35 H 0.8067 0.6064 0.4278 0.046 Uiso 1 1 calc R . . C36 C 0.8111(2) 0.3963(4) 0.36761(15) 0.0292(7) Uani 1 1 d . . . H36 H 0.8267 0.4730 0.3368 0.035 Uiso 1 1 calc R . . C101 C 0.9152(5) 0.7946(11) 0.5767(6) 0.159(5) Uani 1 1 d . . . H101A H 0.9546 0.8434 0.6114 0.191 Uiso 1 1 calc R . . H101B H 0.8795 0.9008 0.5602 0.191 Uiso 1 1 calc R . . C102 C 0.9624(6) 0.7483(11) 0.5348(3) 0.125(3) Uani 1 1 d . . . H102A H 0.9955 0.8565 0.5258 0.187 Uiso 1 1 calc R . . H102B H 0.9256 0.7081 0.4982 0.187 Uiso 1 1 calc R . . H102C H 1.0007 0.6466 0.5498 0.187 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 Br1 0.0343(2) 0.0318(2) 0.0534(3) 0.00699(17) 0.00177(17) -0.00148(15) P1 0.0219(4) 0.0234(4) 0.0207(4) 0.0009(3) 0.0035(3) -0.0008(3) N1 0.0238(14) 0.0180(12) 0.0182(13) 0.0008(10) 0.0043(10) -0.0041(10) N2 0.0264(14) 0.0162(12) 0.0177(13) 0.0023(9) 0.0037(11) 0.0020(10) O1 0.054(2) 0.168(5) 0.091(3) 0.034(3) -0.008(2) -0.004(3) C1 0.0207(15) 0.0146(13) 0.0188(14) -0.0034(11) 0.0076(12) -0.0020(11) C2 0.0188(16) 0.0204(14) 0.0208(15) -0.0007(12) 0.0040(12) 0.0008(11) C3 0.0292(18) 0.0236(15) 0.0215(16) 0.0039(13) 0.0037(13) 0.0009(13) C4 0.0268(17) 0.0186(15) 0.0231(16) 0.0035(12) 0.0084(13) 0.0019(12) C5 0.0286(18) 0.0171(14) 0.0276(17) -0.0028(12) 0.0099(14) -0.0052(12) C6 0.0219(17) 0.0266(16) 0.0268(17) -0.0052(13) 0.0028(13) -0.0066(12) C7 0.0258(17) 0.0263(16) 0.0192(15) -0.0025(12) 0.0008(13) 0.0018(13) C8 0.0257(16) 0.0147(13) 0.0199(15) -0.0018(11) 0.0064(12) 0.0004(11) C9 0.0174(15) 0.0164(13) 0.0193(15) -0.0020(11) 0.0062(12) 0.0017(11) C10 0.0258(17) 0.0152(13) 0.0225(15) -0.0028(11) 0.0094(13) -0.0003(11) C11 0.0280(19) 0.0435(19) 0.0264(18) 0.0075(15) 0.0106(15) -0.0011(15) C12 0.047(2) 0.0160(15) 0.0318(19) 0.0001(13) -0.0017(16) -0.0040(14) C13 0.0302(18) 0.0301(16) 0.0185(15) -0.0002(13) 0.0036(13) -0.0018(13) C14 0.037(2) 0.0215(16) 0.037(2) 0.0028(14) 0.0096(16) 0.0059(14) C21 0.0188(16) 0.0252(15) 0.0306(17) -0.0017(13) 0.0075(13) -0.0005(12) C22 0.0289(18) 0.0317(17) 0.0291(18) -0.0022(14) 0.0086(14) -0.0031(14) C23 0.038(2) 0.0292(18) 0.049(2) -0.0103(16) 0.0200(18) -0.0033(15) C24 0.032(2) 0.0333(19) 0.058(3) 0.0017(18) 0.0165(19) 0.0074(15) C25 0.0239(19) 0.043(2) 0.045(2) 0.0041(17) 0.0007(16) 0.0059(15) C26 0.0265(18) 0.0337(18) 0.0312(18) -0.0030(15) 0.0015(15) 0.0064(14) C31 0.0192(16) 0.0285(16) 0.0202(15) -0.0004(12) 0.0002(12) 0.0032(12) C32 0.0282(18) 0.0273(16) 0.0278(17) 0.0011(13) 0.0040(14) 0.0045(13) C33 0.036(2) 0.0382(19) 0.0258(18) 0.0025(14) 0.0096(15) 0.0044(15) C34 0.040(2) 0.045(2) 0.0235(17) -0.0079(15) 0.0049(15) 0.0030(16) C35 0.047(2) 0.0312(18) 0.036(2) -0.0075(15) 0.0056(17) -0.0045(16) C36 0.037(2) 0.0259(16) 0.0253(17) 0.0007(13) 0.0063(15) -0.0060(14) C101 0.090(6) 0.098(5) 0.311(14) -0.064(7) 0.102(7) -0.057(4) C102 0.153(8) 0.156(7) 0.066(4) -0.034(4) 0.022(4) -0.094(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.834(3) . ? P1 C31 1.839(3) . ? P1 C2 1.857(3) . ? N1 C1 1.459(3) . ? N1 C11 1.478(4) . ? N1 C12 1.485(4) . ? N2 C8 1.468(4) . ? N2 C13 1.485(4) . ? N2 C14 1.490(4) . ? O1 C101 1.317(8) . ? C1 C2 1.381(4) . ? C1 C9 1.447(4) . ? C2 C3 1.425(4) . ? C3 C4 1.355(4) . ? C4 C10 1.417(4) . ? C5 C6 1.365(4) . ? C5 C10 1.413(4) . ? C6 C7 1.406(4) . ? C7 C8 1.368(4) . ? C8 C9 1.430(4) . ? C9 C10 1.435(4) . ? C21 C26 1.387(5) . ? C21 C22 1.401(4) . ? C22 C23 1.390(5) . ? C23 C24 1.381(5) . ? C24 C25 1.381(5) . ? C25 C26 1.388(5) . ? C31 C36 1.390(4) . ? C31 C32 1.403(4) . ? C32 C33 1.384(5) . ? C33 C34 1.381(5) . ? C34 C35 1.382(5) . ? C35 C36 1.388(5) . ? C101 C102 1.342(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 C21 P1 C31 104.64(14) . . ? C21 P1 C2 100.79(13) . . ? C31 P1 C2 101.70(14) . . ? C1 N1 C11 115.3(2) . . ? C1 N1 C12 114.8(2) . . ? C11 N1 C12 113.0(3) . . ? C8 N2 C13 113.0(2) . . ? C8 N2 C14 111.9(2) . . ? C13 N2 C14 111.7(2) . . ? C2 C1 C9 121.4(3) . . ? C2 C1 N1 123.4(3) . . ? C9 C1 N1 115.2(2) . . ? C1 C2 C3 118.5(3) . . ? C1 C2 P1 121.9(2) . . ? C3 C2 P1 119.6(2) . . ? C4 C3 C2 122.1(3) . . ? C3 C4 C10 120.9(3) . . ? C6 C5 C10 121.5(3) . . ? C5 C6 C7 119.5(3) . . ? C8 C7 C6 120.4(3) . . ? C7 C8 C9 122.5(3) . . ? C7 C8 N2 119.1(3) . . ? C9 C8 N2 118.4(3) . . ? C8 C9 C10 115.9(3) . . ? C8 C9 C1 126.1(3) . . ? C10 C9 C1 117.9(3) . . ? C5 C10 C4 120.6(3) . . ? C5 C10 C9 120.2(3) . . ? C4 C10 C9 119.2(3) . . ? C26 C21 C22 118.5(3) . . ? C26 C21 P1 122.2(2) . . ? C22 C21 P1 118.3(3) . . ? C23 C22 C21 120.2(3) . . ? C24 C23 C22 120.5(3) . . ? C25 C24 C23 119.6(3) . . ? C24 C25 C26 120.3(4) . . ? C21 C26 C25 120.9(3) . . ? C36 C31 C32 118.0(3) . . ? C36 C31 P1 115.8(2) . . ? C32 C31 P1 126.2(2) . . ? C33 C32 C31 120.9(3) . . ? C34 C33 C32 120.0(3) . . ? C33 C34 C35 120.1(3) . . ? C34 C35 C36 119.8(3) . . ? C35 C36 C31 121.2(3) . . ? O1 C101 C102 123.5(7) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.684 _refine_diff_density_min -0.542 _refine_diff_density_rms 0.079 # Attachment '5c.cif' data_vic0535 _database_code_depnum_ccdc_archive 'CCDC 611414' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 10.5700(9) _cell_length_b 15.0412(13) _cell_length_c 17.6505(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.2580(11) _cell_angle_gamma 90.00 _cell_volume 2719.73 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z Fe Fe 0.31271(3) 0.349356(19) -0.020874(17) P P 0.40636(5) 0.21283(3) 0.00324(3) O1 O 0.50005(18) 0.42588(13) 0.11427(11) O2 O 0.3869(2) 0.36989(15) -0.16984(11) O3 O 0.06596(17) 0.26067(14) -0.01926(12) O4 O 0.1779(2) 0.52007(13) -0.04673(15) N1 N 0.34591(17) 0.23067(11) 0.15880(10) N2 N 0.29177(19) 0.13657(12) 0.29389(10) C1 C 0.4269(2) 0.39384(15) 0.06284(14) C2 C 0.3603(2) 0.35938(15) -0.11190(14) C3 C 0.1629(2) 0.29503(15) -0.01931(14) C4 C 0.2311(3) 0.45338(16) -0.03680(16) C11 C 0.30126(18) 0.14689(12) 0.12433(11) C12 C 0.32340(18) 0.13015(13) 0.05103(11) C13 C 0.2713(2) 0.05355(13) 0.00796(12) H13 H 0.2949 0.0397 -0.0393 C14 C 0.1876(2) -0.00036(13) 0.03382(12) H14 H 0.1482 -0.0490 0.0024 C15 C 0.15836(19) 0.01474(13) 0.10634(12) C16 C 0.0653(2) -0.04001(15) 0.12970(13) H16 H 0.0228 -0.0861 0.0961 C17 C 0.0370(2) -0.02680(16) 0.19974(15) H17 H -0.0317 -0.0593 0.2129 C18 C 0.1089(2) 0.03460(15) 0.25250(14) H18 H 0.0913 0.0406 0.3025 C19 C 0.2042(2) 0.08664(13) 0.23449(12) C20 C 0.22380(18) 0.08467(13) 0.15623(11) C21 C 0.4717(2) 0.23703(17) 0.21641(13) H21A H 0.4861 0.2985 0.2351 H21B H 0.5418 0.2193 0.1921 H21C H 0.4716 0.1976 0.2606 C22 C 0.2465(2) 0.28828(15) 0.17688(14) H22A H 0.2872 0.3432 0.2010 H22B H 0.2042 0.2577 0.2131 H22C H 0.1810 0.3026 0.1286 C23 C 0.4083(3) 0.08326(19) 0.32690(16) H23A H 0.4689 0.1178 0.3671 H23B H 0.4509 0.0673 0.2854 H23C H 0.3831 0.0291 0.3503 C24 C 0.2362(3) 0.1710(2) 0.35579(16) H24A H 0.1601 0.2080 0.3328 H24B H 0.3017 0.2068 0.3920 H24C H 0.2093 0.1213 0.3842 C31 C 0.57825(19) 0.20519(13) 0.05543(11) C32 C 0.6659(2) 0.27073(14) 0.04540(12) H32 H 0.6350 0.3220 0.0150 C33 C 0.7981(2) 0.26119(16) 0.07967(14) H33 H 0.8577 0.3054 0.0718 C34 C 0.8437(2) 0.18758(17) 0.12534(14) H34 H 0.9341 0.1819 0.1496 C35 C 0.7571(2) 0.12241(15) 0.13557(13) H35 H 0.7881 0.0719 0.1670 C36 C 0.6254(2) 0.13051(14) 0.10006(12) H36 H 0.5667 0.0848 0.1062 C41 C 0.4084(2) 0.16096(13) -0.09118(11) C42 C 0.2950(2) 0.16032(16) -0.15166(13) H42 H 0.2161 0.1831 -0.1426 C43 C 0.2956(2) 0.12703(17) -0.22463(13) H43 H 0.2172 0.1260 -0.2649 C44 C 0.4106(2) 0.09524(16) -0.23904(13) H44 H 0.4116 0.0735 -0.2894 C45 C 0.5230(2) 0.09541(16) -0.17996(14) H45 H 0.6019 0.0735 -0.1896 C46 C 0.5222(2) 0.12738(14) -0.10626(12) H46 H 0.6003 0.1263 -0.0657 #END