# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jason01 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H28 Cl2 N O P' _chemical_formula_weight 352.26 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' Cl Cl 0.1484 0.1585 '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 'P 21/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 10.1434(3) _cell_length_b 15.4257(4) _cell_length_c 12.2878(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.371(3) _cell_angle_gamma 90.00 _cell_volume 1902.17(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 12586 _cell_measurement_theta_min 2.4163 _cell_measurement_theta_max 28.2064 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.425 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98824 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 56111 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4318 _reflns_number_gt 3597 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. The NH hydrogen was refined freely. The methyl groups were refined as idealised rigid groups allowed to rotate but not tip. The other hydrogens were included using a riding model starting from calculated positions. ; _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^)+(0.0231P)^2^+1.0357P] 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 4318 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0693 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 N N 0.59918(11) 0.63702(7) 0.62760(9) 0.0116(2) Uani 1 1 d . . . H1 H 0.5378(16) 0.6716(11) 0.6016(13) 0.019(4) Uiso 1 1 d . . . P P 0.97410(4) 0.55819(2) 0.68597(3) 0.01755(9) Uani 1 1 d . . . Cl1 Cl 1.01523(4) 0.53598(3) 0.85557(3) 0.02836(10) Uani 1 1 d . . . Cl2 Cl 0.97099(4) 0.42877(2) 0.63616(3) 0.02746(10) Uani 1 1 d . . . C1 C 0.73133(13) 0.65038(9) 0.62054(10) 0.0119(3) Uani 1 1 d . . . C2 C 0.79980(13) 0.57927(9) 0.67159(11) 0.0135(3) Uani 1 1 d . . . C3 C 0.70248(13) 0.52365(9) 0.70981(11) 0.0139(3) Uani 1 1 d . . . H3 H 0.7204 0.4704 0.7480 0.017 Uiso 1 1 calc R . . C4 C 0.58033(13) 0.56033(9) 0.68196(10) 0.0121(3) Uani 1 1 d . . . C5 C 0.77128(13) 0.73145(9) 0.56310(11) 0.0148(3) Uani 1 1 d . . . C6 C 0.92254(14) 0.74427(10) 0.57944(13) 0.0216(3) Uani 1 1 d . . . H6A H 0.9562 0.7469 0.6583 0.032 Uiso 1 1 calc R . . H6B H 0.9438 0.7985 0.5442 0.032 Uiso 1 1 calc R . . H6C H 0.9644 0.6956 0.5463 0.032 Uiso 1 1 calc R . . C7 C 0.70780(15) 0.81188(9) 0.60903(12) 0.0204(3) Uani 1 1 d . . . H7A H 0.7364 0.8156 0.6886 0.031 Uiso 1 1 calc R . . H7B H 0.6105 0.8070 0.5942 0.031 Uiso 1 1 calc R . . H7C H 0.7362 0.8642 0.5735 0.031 Uiso 1 1 calc R . . C8 C 0.72157(16) 0.72397(10) 0.43872(12) 0.0213(3) Uani 1 1 d . . . H8A H 0.7427 0.7775 0.4018 0.032 Uiso 1 1 calc R . . H8B H 0.6249 0.7149 0.4269 0.032 Uiso 1 1 calc R . . H8C H 0.7655 0.6748 0.4084 0.032 Uiso 1 1 calc R . . C9 C 0.44346(13) 0.53201(9) 0.70310(11) 0.0136(3) Uani 1 1 d . . . C10 C 0.38647(14) 0.59837(10) 0.77718(12) 0.0206(3) Uani 1 1 d . . . H10A H 0.4451 0.6023 0.8478 0.031 Uiso 1 1 calc R . . H10B H 0.2974 0.5799 0.7896 0.031 Uiso 1 1 calc R . . H10C H 0.3806 0.6553 0.7413 0.031 Uiso 1 1 calc R . . C11 C 0.34848(14) 0.52385(10) 0.59385(11) 0.0180(3) Uani 1 1 d . . . H11A H 0.3377 0.5807 0.5580 0.027 Uiso 1 1 calc R . . H11B H 0.2615 0.5029 0.6084 0.027 Uiso 1 1 calc R . . H11C H 0.3857 0.4828 0.5456 0.027 Uiso 1 1 calc R . . C12 C 0.45501(15) 0.44386(10) 0.76115(12) 0.0209(3) Uani 1 1 d . . . H12A H 0.4921 0.4013 0.7147 0.031 Uiso 1 1 calc R . . H12B H 0.3665 0.4248 0.7743 0.031 Uiso 1 1 calc R . . H12C H 0.5138 0.4491 0.8316 0.031 Uiso 1 1 calc R . . O O 0.37993(10) 0.74649(7) 0.53889(8) 0.0221(2) Uani 1 1 d . . . C96 C 0.30464(15) 0.80954(10) 0.59149(12) 0.0234(3) Uani 1 1 d . . . H96A H 0.3650 0.8470 0.6417 0.028 Uiso 1 1 calc R . . H96B H 0.2420 0.7803 0.6342 0.028 Uiso 1 1 calc R . . C97 C 0.22921(15) 0.86261(10) 0.49864(12) 0.0207(3) Uani 1 1 d . . . H97A H 0.2842 0.9109 0.4771 0.025 Uiso 1 1 calc R . . H97B H 0.1453 0.8861 0.5190 0.025 Uiso 1 1 calc R . . C98 C 0.20193(14) 0.79514(10) 0.40717(12) 0.0198(3) Uani 1 1 d . . . H98A H 0.1242 0.7586 0.4166 0.024 Uiso 1 1 calc R . . H98B H 0.1864 0.8228 0.3337 0.024 Uiso 1 1 calc R . . C99 C 0.32975(15) 0.74296(10) 0.42275(12) 0.0211(3) Uani 1 1 d . . . H99A H 0.3121 0.6822 0.3989 0.025 Uiso 1 1 calc R . . H99B H 0.3951 0.7683 0.3793 0.025 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 N 0.0098(6) 0.0116(6) 0.0135(6) 0.0004(4) 0.0018(4) 0.0011(5) P 0.01090(18) 0.01811(19) 0.0239(2) 0.00058(15) 0.00356(14) 0.00144(14) Cl1 0.02053(19) 0.0401(2) 0.02253(19) -0.00125(17) -0.00320(14) 0.00848(17) Cl2 0.0229(2) 0.0220(2) 0.0376(2) -0.00826(16) 0.00504(16) 0.00687(15) C1 0.0117(6) 0.0123(6) 0.0123(6) -0.0037(5) 0.0040(5) -0.0022(5) C2 0.0113(6) 0.0133(7) 0.0160(7) -0.0012(5) 0.0028(5) 0.0006(5) C3 0.0141(7) 0.0121(7) 0.0155(7) 0.0009(5) 0.0021(5) -0.0002(5) C4 0.0143(7) 0.0117(6) 0.0106(6) -0.0014(5) 0.0024(5) -0.0011(5) C5 0.0143(7) 0.0131(7) 0.0175(7) -0.0005(5) 0.0043(5) -0.0024(5) C6 0.0182(8) 0.0170(7) 0.0307(8) 0.0021(6) 0.0075(6) -0.0054(6) C7 0.0235(8) 0.0135(7) 0.0252(8) -0.0003(6) 0.0068(6) -0.0008(6) C8 0.0278(8) 0.0194(8) 0.0175(7) 0.0032(6) 0.0059(6) -0.0058(6) C9 0.0123(7) 0.0144(7) 0.0146(7) -0.0009(5) 0.0035(5) -0.0018(5) C10 0.0164(7) 0.0255(8) 0.0215(7) -0.0060(6) 0.0077(6) -0.0035(6) C11 0.0146(7) 0.0207(7) 0.0183(7) -0.0009(6) 0.0014(5) -0.0042(6) C12 0.0185(7) 0.0213(8) 0.0234(8) 0.0063(6) 0.0047(6) -0.0049(6) O 0.0209(5) 0.0236(6) 0.0198(5) -0.0017(4) -0.0034(4) 0.0079(4) C96 0.0228(8) 0.0251(8) 0.0216(8) -0.0034(6) 0.0006(6) 0.0060(6) C97 0.0194(7) 0.0186(7) 0.0249(8) 0.0023(6) 0.0057(6) 0.0036(6) C98 0.0183(7) 0.0246(8) 0.0164(7) 0.0039(6) 0.0021(6) 0.0049(6) C99 0.0227(8) 0.0235(8) 0.0169(7) 0.0011(6) 0.0023(6) 0.0052(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 N C1 1.3714(17) . ? N C4 1.3855(17) . ? P C2 1.7810(14) . ? P Cl2 2.0870(5) . ? P Cl1 2.0931(5) . ? C1 C2 1.3973(19) . ? C1 C5 1.5198(18) . ? C2 C3 1.4373(19) . ? C3 C4 1.3597(19) . ? C4 C9 1.5135(18) . ? C5 C6 1.5309(19) . ? C5 C7 1.5421(19) . ? C5 C8 1.5424(19) . ? C9 C12 1.5320(19) . ? C9 C10 1.5376(19) . ? C9 C11 1.5393(18) . ? O C99 1.4448(17) . ? O C96 1.4459(18) . ? C96 C97 1.518(2) . ? C97 C98 1.527(2) . ? C98 C99 1.514(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N C4 111.32(11) . . ? C2 P Cl2 99.97(5) . . ? C2 P Cl1 100.36(5) . . ? Cl2 P Cl1 97.34(2) . . ? N C1 C2 106.27(11) . . ? N C1 C5 118.83(12) . . ? C2 C1 C5 134.90(12) . . ? C1 C2 C3 107.17(11) . . ? C1 C2 P 127.53(10) . . ? C3 C2 P 125.29(10) . . ? C4 C3 C2 108.27(12) . . ? C3 C4 N 106.97(12) . . ? C3 C4 C9 131.43(12) . . ? N C4 C9 121.58(12) . . ? C1 C5 C6 112.04(11) . . ? C1 C5 C7 109.77(11) . . ? C6 C5 C7 108.18(11) . . ? C1 C5 C8 109.14(11) . . ? C6 C5 C8 108.45(11) . . ? C7 C5 C8 109.22(12) . . ? C4 C9 C12 109.04(11) . . ? C4 C9 C10 110.04(11) . . ? C12 C9 C10 108.98(11) . . ? C4 C9 C11 110.32(11) . . ? C12 C9 C11 109.22(11) . . ? C10 C9 C11 109.22(12) . . ? C99 O C96 109.51(11) . . ? O C96 C97 105.55(12) . . ? C96 C97 C98 101.72(12) . . ? C99 C98 C97 102.07(12) . . ? O C99 C98 106.07(11) . . ? 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 C4 N C1 C2 0.44(14) . . . . ? C4 N C1 C5 179.84(11) . . . . ? N C1 C2 C3 -0.41(14) . . . . ? C5 C1 C2 C3 -179.67(14) . . . . ? N C1 C2 P 178.51(10) . . . . ? C5 C1 C2 P -0.8(2) . . . . ? Cl2 P C2 C1 -132.59(12) . . . . ? Cl1 P C2 C1 127.98(12) . . . . ? Cl2 P C2 C3 46.15(12) . . . . ? Cl1 P C2 C3 -53.29(12) . . . . ? C1 C2 C3 C4 0.25(15) . . . . ? P C2 C3 C4 -178.70(10) . . . . ? C2 C3 C4 N 0.01(15) . . . . ? C2 C3 C4 C9 -178.44(13) . . . . ? C1 N C4 C3 -0.28(15) . . . . ? C1 N C4 C9 178.35(11) . . . . ? N C1 C5 C6 170.26(12) . . . . ? C2 C1 C5 C6 -10.6(2) . . . . ? N C1 C5 C7 50.05(16) . . . . ? C2 C1 C5 C7 -130.76(16) . . . . ? N C1 C5 C8 -69.62(15) . . . . ? C2 C1 C5 C8 109.57(17) . . . . ? C3 C4 C9 C12 -3.5(2) . . . . ? N C4 C9 C12 178.25(12) . . . . ? C3 C4 C9 C10 115.99(16) . . . . ? N C4 C9 C10 -62.27(16) . . . . ? C3 C4 C9 C11 -123.43(16) . . . . ? N C4 C9 C11 58.31(16) . . . . ? C99 O C96 C97 -14.70(16) . . . . ? O C96 C97 C98 33.02(15) . . . . ? C96 C97 C98 C99 -38.16(14) . . . . ? C96 O C99 C98 -10.13(16) . . . . ? C97 C98 C99 O 30.39(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1 O 0.846(17) 2.033(17) 2.8775(15) 175.3(15) . C7 H7B O 0.98 2.52 3.4621(18) 161.6 . C11 H11A O 0.98 2.61 3.5236(18) 155.3 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.303 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.048 _iucr_refine_instructions_details ; TITL jason01 in P2(1)/n CELL 0.71073 10.143363 15.425689 12.287794 90.0000 98.3713 90.0000 ZERR 4.00 0.000300 0.000400 0.000300 0.0000 0.0030 0.0000 LATT 1 SYMM -x+1/2, y+1/2,-z+1/2 SFAC C H N P Cl O UNIT 64.00 112.00 4.00 4.00 8.00 4 TEMP -173 SIZE 0.3 0.2 0.1 MERG 2 FMAP 2 PLAN 10 SHEL 999 0.77 ACTA CONF HTAB N O HTAB C7 O HTAB C11 O L.S. 4 WGHT 0.023100 1.035700 FVAR 2.87710 N 3 0.599180 0.637021 0.627599 11.00000 0.00978 0.01158 = 0.01348 0.00040 0.00178 0.00106 H1 2 0.537802 0.671631 0.601650 11.00000 0.01949 P 4 0.974104 0.558191 0.685974 11.00000 0.01090 0.01811 = 0.02394 0.00058 0.00356 0.00144 CL1 5 1.015234 0.535980 0.855568 11.00000 0.02053 0.04013 = 0.02253 -0.00125 -0.00320 0.00848 CL2 5 0.970987 0.428771 0.636156 11.00000 0.02294 0.02203 = 0.03759 -0.00826 0.00504 0.00687 C1 1 0.731330 0.650380 0.620540 11.00000 0.01172 0.01231 = 0.01233 -0.00374 0.00401 -0.00225 C2 1 0.799802 0.579268 0.671595 11.00000 0.01129 0.01335 = 0.01601 -0.00121 0.00281 0.00064 C3 1 0.702483 0.523654 0.709806 11.00000 0.01412 0.01209 = 0.01546 0.00089 0.00210 -0.00021 AFIX 43 H3 2 0.720422 0.470416 0.747962 11.00000 -1.20000 AFIX 0 C4 1 0.580330 0.560327 0.681963 11.00000 0.01431 0.01168 = 0.01060 -0.00144 0.00241 -0.00108 C5 1 0.771282 0.731454 0.563097 11.00000 0.01435 0.01308 = 0.01745 -0.00052 0.00428 -0.00241 C6 1 0.922542 0.744269 0.579443 11.00000 0.01821 0.01704 = 0.03074 0.00208 0.00751 -0.00539 AFIX 137 H6A 2 0.956197 0.746933 0.658281 11.00000 -1.50000 H6B 2 0.943835 0.798476 0.544220 11.00000 -1.50000 H6C 2 0.964420 0.695600 0.546291 11.00000 -1.50000 AFIX 0 C7 1 0.707804 0.811884 0.609026 11.00000 0.02349 0.01354 = 0.02519 -0.00028 0.00676 -0.00077 AFIX 137 H7A 2 0.736374 0.815584 0.688583 11.00000 -1.50000 H7B 2 0.610510 0.807028 0.594207 11.00000 -1.50000 H7C 2 0.736190 0.864151 0.573475 11.00000 -1.50000 AFIX 0 C8 1 0.721568 0.723973 0.438717 11.00000 0.02781 0.01938 = 0.01754 0.00317 0.00586 -0.00575 AFIX 137 H8A 2 0.742732 0.777450 0.401826 11.00000 -1.50000 H8B 2 0.624913 0.714905 0.426888 11.00000 -1.50000 H8C 2 0.765473 0.674812 0.408411 11.00000 -1.50000 AFIX 0 C9 1 0.443462 0.532006 0.703098 11.00000 0.01230 0.01437 = 0.01456 -0.00090 0.00353 -0.00182 C10 1 0.386471 0.598373 0.777177 11.00000 0.01638 0.02546 = 0.02152 -0.00596 0.00768 -0.00349 AFIX 137 H10A 2 0.445073 0.602255 0.847831 11.00000 -1.50000 H10B 2 0.297437 0.579904 0.789630 11.00000 -1.50000 H10C 2 0.380577 0.655258 0.741287 11.00000 -1.50000 AFIX 0 C11 1 0.348476 0.523853 0.593850 11.00000 0.01458 0.02066 = 0.01835 -0.00091 0.00141 -0.00424 AFIX 137 H11A 2 0.337728 0.580686 0.558013 11.00000 -1.50000 H11B 2 0.261538 0.502870 0.608415 11.00000 -1.50000 H11C 2 0.385690 0.482814 0.545571 11.00000 -1.50000 AFIX 0 C12 1 0.455008 0.443858 0.761145 11.00000 0.01847 0.02131 = 0.02341 0.00625 0.00465 -0.00492 AFIX 137 H12A 2 0.492087 0.401300 0.714717 11.00000 -1.50000 H12B 2 0.366523 0.424796 0.774299 11.00000 -1.50000 H12C 2 0.513799 0.449093 0.831553 11.00000 -1.50000 AFIX 0 O 6 0.379927 0.746493 0.538890 11.00000 0.02089 0.02362 = 0.01985 -0.00168 -0.00339 0.00794 C96 1 0.304640 0.809544 0.591494 11.00000 0.02282 0.02508 = 0.02157 -0.00338 0.00059 0.00603 AFIX 23 H96A 2 0.365023 0.847009 0.641732 11.00000 -1.20000 H96B 2 0.242004 0.780314 0.634244 11.00000 -1.20000 AFIX 0 C97 1 0.229212 0.862609 0.498642 11.00000 0.01940 0.01855 = 0.02485 0.00229 0.00565 0.00365 AFIX 23 H97A 2 0.284197 0.910947 0.477100 11.00000 -1.20000 H97B 2 0.145327 0.886115 0.519009 11.00000 -1.20000 AFIX 0 C98 1 0.201926 0.795137 0.407172 11.00000 0.01832 0.02460 = 0.01643 0.00394 0.00207 0.00489 AFIX 23 H98A 2 0.124194 0.758563 0.416620 11.00000 -1.20000 H98B 2 0.186419 0.822847 0.333749 11.00000 -1.20000 AFIX 0 C99 1 0.329752 0.742959 0.422745 11.00000 0.02270 0.02349 = 0.01692 0.00112 0.00228 0.00516 AFIX 23 H99A 2 0.312062 0.682234 0.398911 11.00000 -1.20000 H99B 2 0.395117 0.768271 0.379300 11.00000 -1.20000 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 954344' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mk86 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H53 K N O3 P' _chemical_formula_weight 617.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 19.1507(4) _cell_length_b 10.3412(2) _cell_length_c 18.3019(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.513(2) _cell_angle_gamma 90.00 _cell_volume 3492.50(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 40147 _cell_measurement_theta_min 4.7690 _cell_measurement_theta_max 75.5940 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 2.020 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.40707 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 90655 _diffrn_reflns_av_R_equivalents 0.0596 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.79 _diffrn_reflns_theta_max 75.81 _reflns_number_total 7241 _reflns_number_gt 6540 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. One of the complexing THF molecules is disordered and was refined on two positions, the major part ANIS. ; _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^)+(0.0533P)^2^+1.3240P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7241 _refine_ls_number_parameters 406 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.036 _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 K K 0.296231(16) 0.71283(3) 0.561282(17) 0.02710(9) Uani 1 1 d . . . P P 0.117418(17) 0.50219(3) 0.568413(18) 0.02055(9) Uani 1 1 d . . . N N 0.32780(6) 0.43499(10) 0.58401(6) 0.0225(2) Uani 1 1 d . A . C1 C 0.25585(7) 0.43545(12) 0.54713(8) 0.0216(3) Uani 1 1 d . A . C2 C 0.21386(7) 0.47893(13) 0.59567(8) 0.0223(3) Uani 1 1 d . A . C3 C 0.26544(7) 0.50213(13) 0.66707(8) 0.0237(3) Uani 1 1 d . A . H3 H 0.2553 0.5306 0.7125 0.028 Uiso 1 1 calc R . . C4 C 0.33312(7) 0.47497(13) 0.65695(8) 0.0232(3) Uani 1 1 d . A . C5 C 0.23039(7) 0.39109(13) 0.46466(8) 0.0242(3) Uani 1 1 d . . . C6 C 0.17328(8) 0.28300(14) 0.45565(9) 0.0310(3) Uani 1 1 d . A . H6A H 0.1938 0.2104 0.4889 0.047 Uiso 1 1 calc R . . H6B H 0.1591 0.2535 0.4029 0.047 Uiso 1 1 calc R . . H6C H 0.1306 0.3164 0.4694 0.047 Uiso 1 1 calc R . . C7 C 0.19778(8) 0.50473(14) 0.41255(8) 0.0308(3) Uani 1 1 d . A . H7A H 0.1566 0.5404 0.4281 0.046 Uiso 1 1 calc R . . H7B H 0.1813 0.4743 0.3600 0.046 Uiso 1 1 calc R . . H7C H 0.2346 0.5720 0.4163 0.046 Uiso 1 1 calc R . . C8 C 0.29388(8) 0.33579(16) 0.43876(9) 0.0333(3) Uani 1 1 d . A . H8A H 0.3300 0.4037 0.4406 0.050 Uiso 1 1 calc R . . H8B H 0.2763 0.3035 0.3867 0.050 Uiso 1 1 calc R . . H8C H 0.3161 0.2647 0.4724 0.050 Uiso 1 1 calc R . . C9 C 0.40733(7) 0.48613(13) 0.71335(8) 0.0273(3) Uani 1 1 d . . . C10 C 0.44437(8) 0.35431(15) 0.72601(11) 0.0392(4) Uani 1 1 d . A . H10A H 0.4172 0.2964 0.7507 0.059 Uiso 1 1 calc R . . H10B H 0.4939 0.3643 0.7584 0.059 Uiso 1 1 calc R . . H10C H 0.4458 0.3176 0.6771 0.059 Uiso 1 1 calc R . . C11 C 0.40059(10) 0.5390(2) 0.78905(10) 0.0511(5) Uani 1 1 d . A . H11A H 0.3768 0.6237 0.7811 0.077 Uiso 1 1 calc R . . H11B H 0.4490 0.5479 0.8241 0.077 Uiso 1 1 calc R . . H11C H 0.3716 0.4793 0.8106 0.077 Uiso 1 1 calc R . . C12 C 0.45508(8) 0.57772(16) 0.68192(11) 0.0416(4) Uani 1 1 d . A . H12A H 0.4579 0.5467 0.6322 0.062 Uiso 1 1 calc R . . H12B H 0.5038 0.5803 0.7168 0.062 Uiso 1 1 calc R . . H12C H 0.4340 0.6647 0.6767 0.062 Uiso 1 1 calc R . . C13 C 0.08587(7) 0.42039(12) 0.64304(7) 0.0223(3) Uani 1 1 d . A . C14 C 0.12276(8) 0.31374(14) 0.68160(8) 0.0282(3) Uani 1 1 d . . . H14 H 0.1674 0.2877 0.6728 0.034 Uiso 1 1 calc R A . C15 C 0.09488(9) 0.24505(15) 0.73286(9) 0.0327(3) Uani 1 1 d . A . H15 H 0.1205 0.1723 0.7584 0.039 Uiso 1 1 calc R . . C16 C 0.03010(9) 0.28167(15) 0.74698(9) 0.0319(3) Uani 1 1 d . . . H16 H 0.0116 0.2355 0.7826 0.038 Uiso 1 1 calc R A . C17 C -0.00737(8) 0.38653(15) 0.70840(9) 0.0306(3) Uani 1 1 d . A . H17 H -0.0519 0.4121 0.7176 0.037 Uiso 1 1 calc R . . C18 C 0.01960(7) 0.45473(14) 0.65634(8) 0.0256(3) Uani 1 1 d . . . H18 H -0.0072 0.5253 0.6295 0.031 Uiso 1 1 calc R A . C19 C 0.10065(7) 0.67240(13) 0.58935(7) 0.0223(3) Uani 1 1 d . A . C20 C 0.14758(7) 0.75040(14) 0.64333(8) 0.0246(3) Uani 1 1 d . . . H20 H 0.1923 0.7160 0.6726 0.029 Uiso 1 1 calc R A . C21 C 0.12941(8) 0.87781(14) 0.65464(8) 0.0281(3) Uani 1 1 d . A . H21 H 0.1619 0.9296 0.6914 0.034 Uiso 1 1 calc R . . C22 C 0.06427(8) 0.92950(14) 0.61271(9) 0.0296(3) Uani 1 1 d . . . H22 H 0.0519 1.0163 0.6208 0.035 Uiso 1 1 calc R A . C23 C 0.01727(7) 0.85378(14) 0.55898(9) 0.0293(3) Uani 1 1 d . A . H23 H -0.0276 0.8886 0.5302 0.035 Uiso 1 1 calc R . . C24 C 0.03557(7) 0.72671(13) 0.54694(8) 0.0257(3) Uani 1 1 d . . . H24 H 0.0033 0.6761 0.5093 0.031 Uiso 1 1 calc R A . O1 O 0.34057(6) 0.91539(10) 0.65503(7) 0.0370(2) Uani 1 1 d . A . C25 C 0.33268(9) 0.93221(16) 0.73003(9) 0.0360(3) Uani 1 1 d . . . H25A H 0.3799 0.9197 0.7680 0.043 Uiso 1 1 calc R A . H25B H 0.2978 0.8685 0.7401 0.043 Uiso 1 1 calc R . . C26 C 0.30496(9) 1.06996(16) 0.73483(9) 0.0377(4) Uani 1 1 d . A . H26A H 0.2620 1.0701 0.7553 0.045 Uiso 1 1 calc R . . H26B H 0.3431 1.1250 0.7674 0.045 Uiso 1 1 calc R . . C27 C 0.28519(8) 1.11686(14) 0.65296(10) 0.0339(3) Uani 1 1 d . . . H27A H 0.2342 1.0964 0.6266 0.041 Uiso 1 1 calc R A . H27B H 0.2931 1.2111 0.6501 0.041 Uiso 1 1 calc R . . C28 C 0.33698(9) 1.04122(15) 0.62033(9) 0.0328(3) Uani 1 1 d . A . H28A H 0.3187 1.0347 0.5645 0.039 Uiso 1 1 calc R . . H28B H 0.3853 1.0826 0.6331 0.039 Uiso 1 1 calc R . . O2 O 0.22806(6) 0.88196(13) 0.45656(7) 0.0445(3) Uani 1 1 d . A . C29 C 0.15303(10) 0.8951(2) 0.45341(12) 0.0527(5) Uani 1 1 d . A . H29A H 0.1466 0.9621 0.4897 0.063 Uiso 1 1 calc R . . H29B H 0.1339 0.8122 0.4671 0.063 Uiso 1 1 calc R . . C30 C 0.11334(9) 0.93263(18) 0.37470(10) 0.0421(4) Uani 1 1 d . . . H30A H 0.1047 1.0271 0.3706 0.051 Uiso 1 1 calc R A . H30B H 0.0664 0.8869 0.3579 0.051 Uiso 1 1 calc R . . C31 C 0.16447(11) 0.8908(2) 0.32935(11) 0.0566(5) Uani 1 1 d . A . H31A H 0.1575 0.7985 0.3149 0.068 Uiso 1 1 calc R . . H31B H 0.1581 0.9439 0.2830 0.068 Uiso 1 1 calc R . . C32 C 0.23685(10) 0.9133(2) 0.38372(11) 0.0492(5) Uani 1 1 d . . . H32A H 0.2740 0.8572 0.3714 0.059 Uiso 1 1 calc R A . H32B H 0.2517 1.0047 0.3821 0.059 Uiso 1 1 calc R . . O3 O 0.40597(13) 0.7627(3) 0.50093(17) 0.0381(6) Uani 0.637(4) 1 d PDU A 1 C33 C 0.43860(16) 0.6845(5) 0.4528(2) 0.0475(8) Uani 0.637(4) 1 d PDU A 1 H33A H 0.4109 0.6928 0.3989 0.057 Uiso 0.637(4) 1 calc PR A 1 H33B H 0.4398 0.5923 0.4675 0.057 Uiso 0.637(4) 1 calc PR A 1 C34 C 0.51502(15) 0.7369(3) 0.46475(17) 0.0461(8) Uani 0.637(4) 1 d PD A 1 H34A H 0.5492 0.6672 0.4608 0.055 Uiso 0.637(4) 1 calc PR A 1 H34B H 0.5166 0.8054 0.4274 0.055 Uiso 0.637(4) 1 calc PR A 1 C35 C 0.53231(14) 0.7906(3) 0.54350(19) 0.0431(8) Uani 0.637(4) 1 d PD A 1 H35A H 0.5709 0.8569 0.5517 0.052 Uiso 0.637(4) 1 calc PR A 1 H35B H 0.5471 0.7216 0.5821 0.052 Uiso 0.637(4) 1 calc PR A 1 C36 C 0.45999(15) 0.8494(3) 0.5446(2) 0.0421(8) Uani 0.637(4) 1 d PDU A 1 H36A H 0.4558 0.8563 0.5973 0.050 Uiso 0.637(4) 1 calc PR A 1 H36B H 0.4545 0.9367 0.5216 0.050 Uiso 0.637(4) 1 calc PR A 1 O3' O 0.3957(3) 0.7324(5) 0.4814(3) 0.0417(15) Uiso 0.363(4) 1 d PDU A 2 C33' C 0.4375(3) 0.6287(6) 0.4652(4) 0.0416(16) Uiso 0.363(4) 1 d PDU A 2 H33C H 0.4270 0.6155 0.4097 0.050 Uiso 0.363(4) 1 calc PR A 2 H33D H 0.4262 0.5478 0.4886 0.050 Uiso 0.363(4) 1 calc PR A 2 C34' C 0.5164(2) 0.6649(4) 0.4979(3) 0.0305(11) Uiso 0.363(4) 1 d PD A 2 H34C H 0.5471 0.6275 0.4675 0.037 Uiso 0.363(4) 1 calc PR A 2 H34D H 0.5344 0.6353 0.5511 0.037 Uiso 0.363(4) 1 calc PR A 2 C35' C 0.5152(3) 0.8130(5) 0.4932(3) 0.0403(13) Uiso 0.363(4) 1 d PD A 2 H35C H 0.5539 0.8516 0.5344 0.048 Uiso 0.363(4) 1 calc PR A 2 H35D H 0.5207 0.8432 0.4437 0.048 Uiso 0.363(4) 1 calc PR A 2 C36' C 0.4404(3) 0.8455(5) 0.5023(4) 0.0399(13) Uiso 0.363(4) 1 d PDU A 2 H36C H 0.4439 0.8696 0.5555 0.048 Uiso 0.363(4) 1 calc PR A 2 H36D H 0.4193 0.9191 0.4691 0.048 Uiso 0.363(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K 0.02667(15) 0.02283(15) 0.03162(16) 0.00168(11) 0.00745(12) -0.00057(10) P 0.01692(15) 0.02212(17) 0.02301(17) -0.00036(12) 0.00601(12) 0.00003(11) N 0.0185(5) 0.0205(5) 0.0284(6) -0.0007(4) 0.0058(4) 0.0011(4) C1 0.0194(6) 0.0188(6) 0.0266(7) -0.0006(5) 0.0064(5) -0.0003(5) C2 0.0190(6) 0.0221(6) 0.0264(6) -0.0002(5) 0.0070(5) -0.0003(5) C3 0.0221(6) 0.0238(6) 0.0250(7) -0.0005(5) 0.0059(5) 0.0015(5) C4 0.0208(6) 0.0199(6) 0.0273(7) 0.0005(5) 0.0037(5) 0.0011(5) C5 0.0218(6) 0.0250(6) 0.0263(7) -0.0030(5) 0.0074(5) -0.0007(5) C6 0.0305(7) 0.0308(7) 0.0318(8) -0.0073(6) 0.0085(6) -0.0073(6) C7 0.0342(7) 0.0311(7) 0.0260(7) -0.0013(6) 0.0062(6) 0.0011(6) C8 0.0276(7) 0.0409(8) 0.0333(8) -0.0082(6) 0.0116(6) 0.0029(6) C9 0.0207(6) 0.0248(7) 0.0326(7) -0.0014(5) 0.0006(5) 0.0020(5) C10 0.0252(7) 0.0263(8) 0.0580(11) 0.0053(7) -0.0030(7) 0.0022(6) C11 0.0331(8) 0.0771(13) 0.0350(9) -0.0156(9) -0.0051(7) 0.0126(9) C12 0.0270(7) 0.0327(8) 0.0561(10) 0.0067(7) -0.0044(7) -0.0087(6) C13 0.0216(6) 0.0206(6) 0.0243(6) -0.0031(5) 0.0056(5) -0.0024(5) C14 0.0281(7) 0.0255(7) 0.0320(7) 0.0012(6) 0.0098(6) 0.0029(5) C15 0.0379(8) 0.0260(7) 0.0327(8) 0.0063(6) 0.0072(6) 0.0019(6) C16 0.0374(8) 0.0316(7) 0.0276(7) 0.0035(6) 0.0104(6) -0.0083(6) C17 0.0279(7) 0.0342(8) 0.0328(8) 0.0012(6) 0.0135(6) -0.0034(6) C18 0.0226(6) 0.0261(7) 0.0289(7) 0.0024(5) 0.0082(5) -0.0005(5) C19 0.0205(6) 0.0236(6) 0.0248(6) 0.0027(5) 0.0097(5) -0.0010(5) C20 0.0214(6) 0.0258(6) 0.0269(7) 0.0012(5) 0.0072(5) 0.0000(5) C21 0.0271(7) 0.0269(7) 0.0320(7) -0.0037(6) 0.0108(6) -0.0035(5) C22 0.0299(7) 0.0226(7) 0.0395(8) -0.0002(6) 0.0149(6) 0.0013(5) C23 0.0220(6) 0.0282(7) 0.0383(8) 0.0053(6) 0.0093(6) 0.0043(5) C24 0.0208(6) 0.0259(7) 0.0302(7) 0.0011(5) 0.0066(5) -0.0021(5) O1 0.0465(6) 0.0252(5) 0.0389(6) -0.0011(4) 0.0108(5) 0.0038(5) C25 0.0325(7) 0.0396(9) 0.0348(8) 0.0049(7) 0.0070(6) -0.0048(6) C26 0.0420(8) 0.0368(8) 0.0390(9) -0.0102(7) 0.0189(7) -0.0130(7) C27 0.0344(8) 0.0241(7) 0.0458(9) -0.0010(6) 0.0151(7) -0.0016(6) C28 0.0378(8) 0.0274(7) 0.0358(8) -0.0003(6) 0.0144(6) -0.0015(6) O2 0.0352(6) 0.0638(8) 0.0347(6) 0.0149(6) 0.0099(5) 0.0115(5) C29 0.0444(10) 0.0711(13) 0.0510(11) 0.0239(10) 0.0273(8) 0.0215(9) C30 0.0330(8) 0.0482(10) 0.0429(9) -0.0067(8) 0.0060(7) 0.0043(7) C31 0.0540(11) 0.0828(15) 0.0346(9) 0.0025(9) 0.0146(8) 0.0181(10) C32 0.0399(9) 0.0666(12) 0.0473(10) 0.0192(9) 0.0224(8) 0.0066(8) O3 0.0250(10) 0.0512(15) 0.0408(13) -0.0038(12) 0.0133(9) 0.0026(10) C33 0.0372(16) 0.064(3) 0.0431(17) -0.0064(17) 0.0133(12) 0.0065(15) C34 0.0383(14) 0.062(2) 0.0414(16) 0.0026(15) 0.0164(12) 0.0136(13) C35 0.0314(13) 0.0445(15) 0.057(2) -0.0099(13) 0.0185(13) 0.0001(11) C36 0.0341(14) 0.0348(14) 0.065(2) -0.0053(13) 0.0259(15) 0.0008(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K O2 2.6642(12) . ? K O3 2.673(2) . ? K O1 2.6970(11) . ? K O3' 2.701(6) . ? K N 2.9426(11) . ? K C1 2.9641(13) . ? K C4 2.9923(13) . ? K C2 3.0441(13) . ? K C3 3.0748(14) . ? K C29 3.4749(18) . ? P C2 1.7958(13) . ? P C13 1.8405(14) . ? P C19 1.8477(14) . ? N C1 1.3627(16) . ? N C4 1.3751(18) . ? C1 C2 1.4213(18) . ? C1 C5 1.5273(18) . ? C2 C3 1.4319(19) . ? C3 C4 1.3863(19) . ? C4 C9 1.5210(18) . ? C5 C8 1.5293(19) . ? C5 C7 1.537(2) . ? C5 C6 1.5415(19) . ? C9 C10 1.526(2) . ? C9 C11 1.527(2) . ? C9 C12 1.532(2) . ? C13 C14 1.3953(19) . ? C13 C18 1.4004(18) . ? C14 C15 1.392(2) . ? C15 C16 1.386(2) . ? C16 C17 1.385(2) . ? C17 C18 1.391(2) . ? C19 C24 1.3977(19) . ? C19 C20 1.3997(19) . ? C20 C21 1.392(2) . ? C21 C22 1.385(2) . ? C22 C23 1.384(2) . ? C23 C24 1.393(2) . ? O1 C25 1.431(2) . ? O1 C28 1.4415(18) . ? C25 C26 1.531(2) . ? C26 C27 1.523(2) . ? C27 C28 1.506(2) . ? O2 C32 1.425(2) . ? O2 C29 1.429(2) . ? C29 C30 1.489(3) . ? C30 C31 1.507(3) . ? C31 C32 1.493(3) . ? O3 C36 1.439(4) . ? O3 C33 1.455(4) . ? C33 C34 1.520(4) . ? C34 C35 1.496(4) . ? C35 C36 1.518(3) . ? O3' C33' 1.417(7) . ? O3' C36' 1.440(7) . ? C33' C34' 1.515(7) . ? C34' C35' 1.533(6) . ? C35' C36' 1.523(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 K O3 82.20(6) . . ? O2 K O1 87.60(4) . . ? O3 K O1 87.97(8) . . ? O2 K O3' 80.91(12) . . ? O3 K O3' 10.16(10) . . ? O1 K O3' 97.97(11) . . ? O2 K N 141.75(4) . . ? O3 K N 95.29(6) . . ? O1 K N 130.59(3) . . ? O3' K N 90.10(11) . . ? O2 K C1 120.41(4) . . ? O3 K C1 111.48(7) . . ? O1 K C1 146.89(4) . . ? O3' K C1 103.33(11) . . ? N K C1 26.67(3) . . ? O2 K C4 162.59(4) . . ? O3 K C4 108.16(6) . . ? O1 K C4 106.34(4) . . ? O3' K C4 106.74(12) . . ? N K C4 26.78(3) . . ? C1 K C4 43.19(4) . . ? O2 K C2 119.28(4) . . ? O3 K C2 138.33(7) . . ? O1 K C2 125.31(4) . . ? O3' K C2 130.61(11) . . ? N K C2 45.02(3) . . ? C1 K C2 27.33(3) . . ? C4 K C2 43.96(4) . . ? O2 K C3 141.13(4) . . ? O3 K C3 134.53(6) . . ? O1 K C3 103.33(4) . . ? O3' K C3 132.51(12) . . ? N K C3 44.43(3) . . ? C1 K C3 43.93(4) . . ? C4 K C3 26.37(4) . . ? C2 K C3 27.06(4) . . ? O2 K C29 22.30(4) . . ? O3 K C29 104.41(6) . . ? O1 K C29 90.37(5) . . ? O3' K C29 102.43(12) . . ? N K C29 135.31(5) . . ? C1 K C29 109.11(5) . . ? C4 K C29 143.64(4) . . ? C2 K C29 100.05(5) . . ? C3 K C29 119.14(4) . . ? C2 P C13 104.46(6) . . ? C2 P C19 107.03(6) . . ? C13 P C19 100.03(6) . . ? C1 N C4 106.40(11) . . ? C1 N K 77.54(7) . . ? C4 N K 78.62(7) . . ? N C1 C2 110.96(12) . . ? N C1 C5 120.11(11) . . ? C2 C1 C5 128.92(11) . . ? N C1 K 75.78(7) . . ? C2 C1 K 79.47(7) . . ? C5 C1 K 112.58(8) . . ? C1 C2 C3 104.82(11) . . ? C1 C2 P 125.48(10) . . ? C3 C2 P 129.67(10) . . ? C1 C2 K 73.20(7) . . ? C3 C2 K 77.66(8) . . ? P C2 K 112.80(6) . . ? C4 C3 C2 106.60(12) . . ? C4 C3 K 73.49(8) . . ? C2 C3 K 75.28(8) . . ? N C4 C3 111.19(11) . . ? N C4 C9 119.66(12) . . ? C3 C4 C9 129.14(13) . . ? N C4 K 74.60(7) . . ? C3 C4 K 80.14(8) . . ? C9 C4 K 111.48(8) . . ? C1 C5 C8 110.40(11) . . ? C1 C5 C7 110.66(11) . . ? C8 C5 C7 108.57(12) . . ? C1 C5 C6 110.69(11) . . ? C8 C5 C6 107.21(12) . . ? C7 C5 C6 109.22(12) . . ? C4 C9 C10 110.32(12) . . ? C4 C9 C11 110.65(12) . . ? C10 C9 C11 109.33(14) . . ? C4 C9 C12 109.60(12) . . ? C10 C9 C12 108.03(13) . . ? C11 C9 C12 108.86(15) . . ? C14 C13 C18 118.18(13) . . ? C14 C13 P 121.08(10) . . ? C18 C13 P 120.34(10) . . ? C15 C14 C13 120.71(13) . . ? C16 C15 C14 120.66(14) . . ? C17 C16 C15 119.11(13) . . ? C16 C17 C18 120.62(14) . . ? C17 C18 C13 120.68(13) . . ? C24 C19 C20 117.98(12) . . ? C24 C19 P 116.50(10) . . ? C20 C19 P 125.52(10) . . ? C21 C20 C19 120.76(13) . . ? C22 C21 C20 120.44(13) . . ? C23 C22 C21 119.56(13) . . ? C22 C23 C24 120.18(13) . . ? C23 C24 C19 121.07(13) . . ? C25 O1 C28 107.94(11) . . ? C25 O1 K 127.49(9) . . ? C28 O1 K 116.81(9) . . ? O1 C25 C26 107.18(12) . . ? C27 C26 C25 103.80(13) . . ? C28 C27 C26 102.00(13) . . ? O1 C28 C27 104.65(12) . . ? C32 O2 C29 108.04(13) . . ? C32 O2 K 131.65(11) . . ? C29 O2 K 112.67(10) . . ? O2 C29 C30 108.14(14) . . ? O2 C29 K 45.03(7) . . ? C30 C29 K 144.29(12) . . ? C29 C30 C31 102.67(14) . . ? C32 C31 C30 102.26(16) . . ? O2 C32 C31 105.50(15) . . ? C36 O3 C33 108.8(2) . . ? C36 O3 K 114.73(18) . . ? C33 O3 K 131.0(2) . . ? O3 C33 C34 105.5(3) . . ? C35 C34 C33 103.2(2) . . ? C34 C35 C36 101.2(2) . . ? O3 C36 C35 105.4(2) . . ? C33' O3' C36' 109.9(5) . . ? C33' O3' K 125.2(4) . . ? C36' O3' K 111.9(3) . . ? O3' C33' C34' 106.9(5) . . ? C33' C34' C35' 103.1(4) . . ? C36' C35' C34' 102.4(4) . . ? O3' C36' C35' 107.6(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 K N C1 -45.31(10) . . . . ? O3 K N C1 -129.41(10) . . . . ? O1 K N C1 138.73(8) . . . . ? O3' K N C1 -120.66(13) . . . . ? C4 K N C1 109.84(11) . . . . ? C2 K N C1 36.03(7) . . . . ? C3 K N C1 74.85(8) . . . . ? C29 K N C1 -12.73(10) . . . . ? O2 K N C4 -155.15(7) . . . . ? O3 K N C4 120.75(10) . . . . ? O1 K N C4 28.89(9) . . . . ? O3' K N C4 129.50(13) . . . . ? C1 K N C4 -109.84(11) . . . . ? C2 K N C4 -73.81(8) . . . . ? C3 K N C4 -34.99(7) . . . . ? C29 K N C4 -122.57(8) . . . . ? C4 N C1 C2 1.39(15) . . . . ? K N C1 C2 -72.61(10) . . . . ? C4 N C1 C5 -177.88(11) . . . . ? K N C1 C5 108.11(11) . . . . ? C4 N C1 K 74.00(9) . . . . ? O2 K C1 N 149.31(7) . . . . ? O3 K C1 N 55.77(10) . . . . ? O1 K C1 N -66.48(10) . . . . ? O3' K C1 N 62.13(14) . . . . ? C4 K C1 N -38.26(7) . . . . ? C2 K C1 N -114.99(11) . . . . ? C3 K C1 N -76.91(8) . . . . ? C29 K C1 N 170.56(7) . . . . ? O2 K C1 C2 -95.70(8) . . . . ? O3 K C1 C2 170.76(9) . . . . ? O1 K C1 C2 48.51(11) . . . . ? O3' K C1 C2 177.12(14) . . . . ? N K C1 C2 114.99(11) . . . . ? C4 K C1 C2 76.73(8) . . . . ? C3 K C1 C2 38.08(7) . . . . ? C29 K C1 C2 -74.45(8) . . . . ? O2 K C1 C5 32.24(10) . . . . ? O3 K C1 C5 -61.30(11) . . . . ? O1 K C1 C5 176.44(8) . . . . ? O3' K C1 C5 -54.94(14) . . . . ? N K C1 C5 -117.07(12) . . . . ? C4 K C1 C5 -155.33(11) . . . . ? C2 K C1 C5 127.94(12) . . . . ? C3 K C1 C5 166.02(11) . . . . ? C29 K C1 C5 53.49(9) . . . . ? N C1 C2 C3 -1.69(15) . . . . ? C5 C1 C2 C3 177.51(13) . . . . ? K C1 C2 C3 -71.90(9) . . . . ? N C1 C2 P 176.58(9) . . . . ? C5 C1 C2 P -4.2(2) . . . . ? K C1 C2 P 106.37(10) . . . . ? N C1 C2 K 70.20(9) . . . . ? C5 C1 C2 K -110.60(13) . . . . ? C13 P C2 C1 131.89(12) . . . . ? C19 P C2 C1 -122.62(12) . . . . ? C13 P C2 C3 -50.29(14) . . . . ? C19 P C2 C3 55.20(14) . . . . ? C13 P C2 K -143.01(6) . . . . ? C19 P C2 K -37.52(7) . . . . ? O2 K C2 C1 100.32(8) . . . . ? O3 K C2 C1 -12.99(13) . . . . ? O1 K C2 C1 -149.91(7) . . . . ? O3' K C2 C1 -3.69(17) . . . . ? N K C2 C1 -35.11(7) . . . . ? C4 K C2 C1 -73.67(8) . . . . ? C3 K C2 C1 -109.85(11) . . . . ? C29 K C2 C1 112.41(8) . . . . ? O2 K C2 C3 -149.82(7) . . . . ? O3 K C2 C3 96.86(12) . . . . ? O1 K C2 C3 -40.06(9) . . . . ? O3' K C2 C3 106.16(17) . . . . ? N K C2 C3 74.74(8) . . . . ? C1 K C2 C3 109.85(11) . . . . ? C4 K C2 C3 36.18(7) . . . . ? C29 K C2 C3 -137.74(8) . . . . ? O2 K C2 P -21.74(8) . . . . ? O3 K C2 P -135.05(10) . . . . ? O1 K C2 P 88.03(7) . . . . ? O3' K C2 P -125.76(16) . . . . ? N K C2 P -157.17(9) . . . . ? C1 K C2 P -122.06(11) . . . . ? C4 K C2 P 164.27(9) . . . . ? C3 K C2 P 128.09(11) . . . . ? C29 K C2 P -9.65(7) . . . . ? C1 C2 C3 C4 1.30(14) . . . . ? P C2 C3 C4 -176.87(10) . . . . ? K C2 C3 C4 -67.36(9) . . . . ? C1 C2 C3 K 68.66(9) . . . . ? P C2 C3 K -109.51(11) . . . . ? O2 K C3 C4 157.02(8) . . . . ? O3 K C3 C4 0.53(14) . . . . ? O1 K C3 C4 -99.96(8) . . . . ? O3' K C3 C4 14.28(18) . . . . ? N K C3 C4 35.56(7) . . . . ? C1 K C3 C4 74.21(8) . . . . ? C2 K C3 C4 112.70(12) . . . . ? C29 K C3 C4 162.00(8) . . . . ? O2 K C3 C2 44.32(10) . . . . ? O3 K C3 C2 -112.18(13) . . . . ? O1 K C3 C2 147.34(7) . . . . ? O3' K C3 C2 -98.42(17) . . . . ? N K C3 C2 -77.14(8) . . . . ? C1 K C3 C2 -38.49(7) . . . . ? C4 K C3 C2 -112.70(12) . . . . ? C29 K C3 C2 49.30(9) . . . . ? C1 N C4 C3 -0.52(15) . . . . ? K N C4 C3 72.70(10) . . . . ? C1 N C4 C9 -179.50(11) . . . . ? K N C4 C9 -106.27(11) . . . . ? C1 N C4 K -73.23(8) . . . . ? C2 C3 C4 N -0.52(15) . . . . ? K C3 C4 N -69.11(9) . . . . ? C2 C3 C4 C9 178.33(13) . . . . ? K C3 C4 C9 109.74(14) . . . . ? C2 C3 C4 K 68.60(9) . . . . ? O2 K C4 N 60.41(16) . . . . ? O3 K C4 N -64.24(11) . . . . ? O1 K C4 N -157.52(7) . . . . ? O3' K C4 N -53.69(13) . . . . ? C1 K C4 N 38.10(7) . . . . ? C2 K C4 N 78.16(8) . . . . ? C3 K C4 N 115.37(11) . . . . ? C29 K C4 N 88.29(10) . . . . ? O2 K C4 C3 -54.96(17) . . . . ? O3 K C4 C3 -179.61(11) . . . . ? O1 K C4 C3 87.11(8) . . . . ? O3' K C4 C3 -169.05(13) . . . . ? N K C4 C3 -115.37(11) . . . . ? C1 K C4 C3 -77.27(9) . . . . ? C2 K C4 C3 -37.20(8) . . . . ? C29 K C4 C3 -27.07(12) . . . . ? O2 K C4 C9 176.72(11) . . . . ? O3 K C4 C9 52.07(12) . . . . ? O1 K C4 C9 -41.21(10) . . . . ? O3' K C4 C9 62.62(15) . . . . ? N K C4 C9 116.31(13) . . . . ? C1 K C4 C9 154.41(12) . . . . ? C2 K C4 C9 -165.52(12) . . . . ? C3 K C4 C9 -128.32(14) . . . . ? C29 K C4 C9 -155.39(10) . . . . ? N C1 C5 C8 6.76(17) . . . . ? C2 C1 C5 C8 -172.37(13) . . . . ? K C1 C5 C8 92.96(11) . . . . ? N C1 C5 C7 -113.46(13) . . . . ? C2 C1 C5 C7 67.41(17) . . . . ? K C1 C5 C7 -27.26(13) . . . . ? N C1 C5 C6 125.31(13) . . . . ? C2 C1 C5 C6 -53.82(18) . . . . ? K C1 C5 C6 -148.49(9) . . . . ? N C4 C9 C10 -62.01(17) . . . . ? C3 C4 C9 C10 119.22(16) . . . . ? K C4 C9 C10 -146.03(11) . . . . ? N C4 C9 C11 176.87(14) . . . . ? C3 C4 C9 C11 -1.9(2) . . . . ? K C4 C9 C11 92.86(14) . . . . ? N C4 C9 C12 56.81(17) . . . . ? C3 C4 C9 C12 -121.96(16) . . . . ? K C4 C9 C12 -27.20(14) . . . . ? C2 P C13 C14 -29.85(13) . . . . ? C19 P C13 C14 -140.50(11) . . . . ? C2 P C13 C18 157.49(11) . . . . ? C19 P C13 C18 46.83(12) . . . . ? C18 C13 C14 C15 -1.1(2) . . . . ? P C13 C14 C15 -173.95(11) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C14 C15 C16 C17 1.1(2) . . . . ? C15 C16 C17 C18 -0.2(2) . . . . ? C16 C17 C18 C13 -1.3(2) . . . . ? C14 C13 C18 C17 2.0(2) . . . . ? P C13 C18 C17 174.85(11) . . . . ? C2 P C19 C24 154.99(10) . . . . ? C13 P C19 C24 -96.39(11) . . . . ? C2 P C19 C20 -24.62(13) . . . . ? C13 P C19 C20 84.00(12) . . . . ? C24 C19 C20 C21 0.55(19) . . . . ? P C19 C20 C21 -179.84(10) . . . . ? C19 C20 C21 C22 0.2(2) . . . . ? C20 C21 C22 C23 -0.3(2) . . . . ? C21 C22 C23 C24 -0.3(2) . . . . ? C22 C23 C24 C19 1.1(2) . . . . ? C20 C19 C24 C23 -1.2(2) . . . . ? P C19 C24 C23 179.14(11) . . . . ? O2 K O1 C25 127.13(12) . . . . ? O3 K O1 C25 -150.59(12) . . . . ? O3' K O1 C25 -152.39(16) . . . . ? N K O1 C25 -55.37(13) . . . . ? C1 K O1 C25 -22.54(15) . . . . ? C4 K O1 C25 -42.26(12) . . . . ? C2 K O1 C25 2.38(13) . . . . ? C3 K O1 C25 -15.13(12) . . . . ? C29 K O1 C25 105.00(12) . . . . ? O2 K O1 C28 -18.21(10) . . . . ? O3 K O1 C28 64.06(11) . . . . ? O3' K O1 C28 62.27(15) . . . . ? N K O1 C28 159.29(9) . . . . ? C1 K O1 C28 -167.89(9) . . . . ? C4 K O1 C28 172.40(10) . . . . ? C2 K O1 C28 -142.97(9) . . . . ? C3 K O1 C28 -160.48(10) . . . . ? C29 K O1 C28 -40.34(10) . . . . ? C28 O1 C25 C26 13.98(16) . . . . ? K O1 C25 C26 -133.78(10) . . . . ? O1 C25 C26 C27 10.25(16) . . . . ? C25 C26 C27 C28 -29.01(15) . . . . ? C25 O1 C28 C27 -33.12(16) . . . . ? K O1 C28 C27 118.56(11) . . . . ? C26 C27 C28 O1 38.23(15) . . . . ? O3 K O2 C32 29.72(17) . . . . ? O1 K O2 C32 118.00(16) . . . . ? O3' K O2 C32 19.53(19) . . . . ? N K O2 C32 -58.93(17) . . . . ? C1 K O2 C32 -80.65(16) . . . . ? C4 K O2 C32 -98.18(19) . . . . ? C2 K O2 C32 -112.23(16) . . . . ? C3 K O2 C32 -133.60(15) . . . . ? C29 K O2 C32 -145.1(2) . . . . ? O3 K O2 C29 174.86(15) . . . . ? O1 K O2 C29 -96.86(13) . . . . ? O3' K O2 C29 164.67(17) . . . . ? N K O2 C29 86.20(14) . . . . ? C1 K O2 C29 64.49(14) . . . . ? C4 K O2 C29 47.0(2) . . . . ? C2 K O2 C29 32.91(14) . . . . ? C3 K O2 C29 11.54(16) . . . . ? C32 O2 C29 C30 1.6(2) . . . . ? K O2 C29 C30 -151.70(13) . . . . ? C32 O2 C29 K 153.31(18) . . . . ? O3 K C29 O2 -5.26(16) . . . . ? O1 K C29 O2 82.74(13) . . . . ? O3' K C29 O2 -15.51(18) . . . . ? N K C29 O2 -118.53(13) . . . . ? C1 K C29 O2 -124.54(13) . . . . ? C4 K C29 O2 -158.35(11) . . . . ? C2 K C29 O2 -151.23(13) . . . . ? C3 K C29 O2 -171.74(12) . . . . ? O2 K C29 C30 50.5(2) . . . . ? O3 K C29 C30 45.3(3) . . . . ? O1 K C29 C30 133.3(2) . . . . ? O3' K C29 C30 35.0(3) . . . . ? N K C29 C30 -68.0(3) . . . . ? C1 K C29 C30 -74.0(2) . . . . ? C4 K C29 C30 -107.8(2) . . . . ? C2 K C29 C30 -100.7(2) . . . . ? C3 K C29 C30 -121.2(2) . . . . ? O2 C29 C30 C31 20.6(2) . . . . ? K C29 C30 C31 -14.5(3) . . . . ? C29 C30 C31 C32 -33.7(2) . . . . ? C29 O2 C32 C31 -23.6(2) . . . . ? K O2 C32 C31 122.66(15) . . . . ? C30 C31 C32 O2 35.8(2) . . . . ? O2 K O3 C36 102.1(2) . . . . ? O1 K O3 C36 14.2(2) . . . . ? O3' K O3 C36 -175.9(10) . . . . ? N K O3 C36 -116.3(2) . . . . ? C1 K O3 C36 -138.23(19) . . . . ? C4 K O3 C36 -92.3(2) . . . . ? C2 K O3 C36 -131.9(2) . . . . ? C3 K O3 C36 -92.5(2) . . . . ? C29 K O3 C36 104.1(2) . . . . ? O2 K O3 C33 -107.5(3) . . . . ? O1 K O3 C33 164.6(3) . . . . ? O3' K O3 C33 -25.5(8) . . . . ? N K O3 C33 34.0(3) . . . . ? C1 K O3 C33 12.2(3) . . . . ? C4 K O3 C33 58.1(3) . . . . ? C2 K O3 C33 18.5(3) . . . . ? C3 K O3 C33 57.8(3) . . . . ? C29 K O3 C33 -105.5(3) . . . . ? C36 O3 C33 C34 -4.7(4) . . . . ? K O3 C33 C34 -156.4(2) . . . . ? O3 C33 C34 C35 27.8(4) . . . . ? C33 C34 C35 C36 -38.7(3) . . . . ? C33 O3 C36 C35 -20.0(4) . . . . ? K O3 C36 C35 136.8(2) . . . . ? C34 C35 C36 O3 36.7(3) . . . . ? O2 K O3' C33' -141.7(5) . . . . ? O3 K O3' C33' 121.8(11) . . . . ? O1 K O3' C33' 132.0(5) . . . . ? N K O3' C33' 0.9(5) . . . . ? C1 K O3' C33' -22.4(5) . . . . ? C4 K O3' C33' 22.2(5) . . . . ? C2 K O3' C33' -20.7(5) . . . . ? C3 K O3' C33' 15.6(5) . . . . ? C29 K O3' C33' -135.8(5) . . . . ? O2 K O3' C36' 81.2(4) . . . . ? O3 K O3' C36' -15.3(6) . . . . ? O1 K O3' C36' -5.1(4) . . . . ? N K O3' C36' -136.2(4) . . . . ? C1 K O3' C36' -159.6(4) . . . . ? C4 K O3' C36' -114.9(4) . . . . ? C2 K O3' C36' -157.8(3) . . . . ? C3 K O3' C36' -121.5(4) . . . . ? C29 K O3' C36' 87.1(4) . . . . ? C36' O3' C33' C34' 16.2(7) . . . . ? K O3' C33' C34' -121.6(4) . . . . ? O3' C33' C34' C35' -29.6(6) . . . . ? C33' C34' C35' C36' 30.7(5) . . . . ? C33' O3' C36' C35' 4.2(7) . . . . ? K O3' C36' C35' 148.0(4) . . . . ? C34' C35' C36' O3' -22.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.514 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.044 _iucr_refine_instructions_details ; TITL MK86 in P2(1)/c CELL 1.54184 19.150731 10.341200 18.301925 90.0000 105.5128 90.0000 ZERR 4.00 0.000400 0.000200 0.000400 0.0000 0.0020 0.0000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N P K O UNIT 144 212 4 4 4 12 MERG 2 TEMP -173 ACTA 150 CONF FMAP 2 PLAN 10 FREE K C12 FREE K C36 FREE K C36' L.S. 4 WGHT 0.053300 1.324000 FVAR 3.29858 0.63737 K 5 0.296231 0.712831 0.561282 11.00000 0.02667 0.02283 = 0.03162 0.00168 0.00745 -0.00057 P 4 0.117418 0.502186 0.568413 11.00000 0.01692 0.02212 = 0.02301 -0.00036 0.00601 0.00003 N 3 0.327801 0.434993 0.584005 11.00000 0.01852 0.02047 = 0.02836 -0.00071 0.00579 0.00107 C1 1 0.255845 0.435453 0.547130 11.00000 0.01940 0.01882 = 0.02661 -0.00064 0.00641 -0.00030 C2 1 0.213856 0.478931 0.595671 11.00000 0.01898 0.02212 = 0.02643 -0.00024 0.00701 -0.00033 C3 1 0.265437 0.502133 0.667065 11.00000 0.02208 0.02381 = 0.02498 -0.00054 0.00590 0.00148 AFIX 43 H3 2 0.255262 0.530587 0.712494 11.00000 -1.20000 AFIX 0 C4 1 0.333124 0.474967 0.656950 11.00000 0.02079 0.01994 = 0.02733 0.00048 0.00374 0.00110 C5 1 0.230388 0.391090 0.464659 11.00000 0.02185 0.02502 = 0.02634 -0.00296 0.00742 -0.00068 C6 1 0.173280 0.283005 0.455649 11.00000 0.03052 0.03076 = 0.03185 -0.00728 0.00852 -0.00734 AFIX 137 H6A 2 0.193818 0.210449 0.488923 11.00000 -1.50000 H6B 2 0.159086 0.253455 0.402854 11.00000 -1.50000 H6C 2 0.130628 0.316395 0.469442 11.00000 -1.50000 AFIX 0 C7 1 0.197777 0.504731 0.412553 11.00000 0.03419 0.03105 = 0.02602 -0.00134 0.00619 0.00114 AFIX 137 H7A 2 0.156555 0.540440 0.428084 11.00000 -1.50000 H7B 2 0.181344 0.474260 0.360035 11.00000 -1.50000 H7C 2 0.234639 0.571958 0.416315 11.00000 -1.50000 AFIX 0 C8 1 0.293880 0.335787 0.438756 11.00000 0.02763 0.04091 = 0.03332 -0.00817 0.01158 0.00286 AFIX 137 H8A 2 0.329971 0.403744 0.440573 11.00000 -1.50000 H8B 2 0.276279 0.303512 0.386716 11.00000 -1.50000 H8C 2 0.316077 0.264664 0.472378 11.00000 -1.50000 AFIX 0 C9 1 0.407326 0.486134 0.713350 11.00000 0.02074 0.02476 = 0.03261 -0.00144 0.00057 0.00204 C10 1 0.444369 0.354307 0.726006 11.00000 0.02520 0.02634 = 0.05796 0.00530 -0.00299 0.00216 AFIX 137 H10A 2 0.417164 0.296373 0.750693 11.00000 -1.50000 H10B 2 0.493887 0.364269 0.758378 11.00000 -1.50000 H10C 2 0.445849 0.317597 0.677078 11.00000 -1.50000 AFIX 0 C11 1 0.400590 0.539001 0.789045 11.00000 0.03312 0.07707 = 0.03499 -0.01560 -0.00507 0.01261 AFIX 137 H11A 2 0.376837 0.623727 0.781058 11.00000 -1.50000 H11B 2 0.448963 0.547916 0.824103 11.00000 -1.50000 H11C 2 0.371646 0.479298 0.810569 11.00000 -1.50000 AFIX 0 C12 1 0.455079 0.577718 0.681919 11.00000 0.02700 0.03265 = 0.05614 0.00671 -0.00442 -0.00872 AFIX 137 H12A 2 0.457927 0.546685 0.632203 11.00000 -1.50000 H12B 2 0.503825 0.580346 0.716760 11.00000 -1.50000 H12C 2 0.434041 0.664724 0.676681 11.00000 -1.50000 AFIX 0 C13 1 0.085865 0.420392 0.643038 11.00000 0.02157 0.02063 = 0.02428 -0.00305 0.00556 -0.00239 C14 1 0.122756 0.313743 0.681599 11.00000 0.02810 0.02547 = 0.03204 0.00120 0.00980 0.00285 AFIX 43 H14 2 0.167378 0.287730 0.672775 11.00000 -1.20000 AFIX 0 C15 1 0.094880 0.245053 0.732859 11.00000 0.03793 0.02603 = 0.03269 0.00626 0.00717 0.00187 AFIX 43 H15 2 0.120519 0.172340 0.758422 11.00000 -1.20000 AFIX 0 C16 1 0.030102 0.281670 0.746977 11.00000 0.03738 0.03163 = 0.02756 0.00353 0.01040 -0.00831 AFIX 43 H16 2 0.011646 0.235466 0.782634 11.00000 -1.20000 AFIX 0 C17 1 -0.007370 0.386534 0.708402 11.00000 0.02786 0.03422 = 0.03276 0.00117 0.01354 -0.00339 AFIX 43 H17 2 -0.051908 0.412130 0.717584 11.00000 -1.20000 AFIX 0 C18 1 0.019599 0.454732 0.656338 11.00000 0.02262 0.02609 = 0.02894 0.00244 0.00823 -0.00049 AFIX 43 H18 2 -0.007214 0.525323 0.629532 11.00000 -1.20000 AFIX 0 C19 1 0.100651 0.672400 0.589352 11.00000 0.02052 0.02355 = 0.02484 0.00268 0.00971 -0.00098 C20 1 0.147580 0.750400 0.643326 11.00000 0.02141 0.02578 = 0.02694 0.00120 0.00715 -0.00003 AFIX 43 H20 2 0.192345 0.716011 0.672575 11.00000 -1.20000 AFIX 0 C21 1 0.129405 0.877808 0.654640 11.00000 0.02709 0.02687 = 0.03204 -0.00374 0.01081 -0.00349 AFIX 43 H21 2 0.161898 0.929639 0.691363 11.00000 -1.20000 AFIX 0 C22 1 0.064266 0.929499 0.612711 11.00000 0.02992 0.02256 = 0.03947 -0.00016 0.01488 0.00129 AFIX 43 H22 2 0.051923 1.016327 0.620769 11.00000 -1.20000 AFIX 0 C23 1 0.017268 0.853779 0.558981 11.00000 0.02203 0.02824 = 0.03833 0.00530 0.00928 0.00434 AFIX 43 H23 2 -0.027589 0.888596 0.530247 11.00000 -1.20000 AFIX 0 C24 1 0.035574 0.726708 0.546943 11.00000 0.02082 0.02591 = 0.03023 0.00108 0.00658 -0.00206 AFIX 43 H24 2 0.003307 0.676119 0.509297 11.00000 -1.20000 AFIX 0 O1 6 0.340567 0.915394 0.655032 11.00000 0.04649 0.02516 = 0.03891 -0.00105 0.01077 0.00384 C25 1 0.332682 0.932215 0.730026 11.00000 0.03255 0.03960 = 0.03482 0.00492 0.00703 -0.00476 AFIX 23 H25A 2 0.379864 0.919713 0.767990 11.00000 -1.20000 H25B 2 0.297768 0.868527 0.740050 11.00000 -1.20000 AFIX 0 C26 1 0.304963 1.069964 0.734829 11.00000 0.04197 0.03682 = 0.03897 -0.01023 0.01885 -0.01301 AFIX 23 H26A 2 0.262041 1.070061 0.755270 11.00000 -1.20000 H26B 2 0.343107 1.125021 0.767393 11.00000 -1.20000 AFIX 0 C27 1 0.285193 1.116859 0.652960 11.00000 0.03439 0.02411 = 0.04576 -0.00102 0.01508 -0.00158 AFIX 23 H27A 2 0.234173 1.096370 0.626607 11.00000 -1.20000 H27B 2 0.293075 1.211126 0.650090 11.00000 -1.20000 AFIX 0 C28 1 0.336982 1.041219 0.620331 11.00000 0.03782 0.02742 = 0.03578 -0.00025 0.01439 -0.00151 AFIX 23 H28A 2 0.318666 1.034715 0.564495 11.00000 -1.20000 H28B 2 0.385341 1.082648 0.633082 11.00000 -1.20000 AFIX 0 O2 6 0.228061 0.881960 0.456563 11.00000 0.03522 0.06379 = 0.03467 0.01491 0.00987 0.01151 C29 1 0.153029 0.895083 0.453408 11.00000 0.04440 0.07111 = 0.05101 0.02385 0.02730 0.02146 AFIX 23 H29A 2 0.146613 0.962135 0.489676 11.00000 -1.20000 H29B 2 0.133931 0.812219 0.467116 11.00000 -1.20000 AFIX 0 C30 1 0.113340 0.932626 0.374697 11.00000 0.03295 0.04816 = 0.04286 -0.00671 0.00601 0.00434 AFIX 23 H30A 2 0.104671 1.027055 0.370606 11.00000 -1.20000 H30B 2 0.066359 0.886856 0.357893 11.00000 -1.20000 AFIX 0 C31 1 0.164472 0.890788 0.329349 11.00000 0.05396 0.08276 = 0.03460 0.00253 0.01463 0.01809 AFIX 23 H31A 2 0.157506 0.798493 0.314865 11.00000 -1.20000 H31B 2 0.158140 0.943918 0.283034 11.00000 -1.20000 AFIX 0 C32 1 0.236850 0.913304 0.383721 11.00000 0.03989 0.06661 = 0.04727 0.01925 0.02236 0.00664 AFIX 23 H32A 2 0.274016 0.857231 0.371364 11.00000 -1.20000 H32B 2 0.251746 1.004698 0.382087 11.00000 -1.20000 AFIX 0 SAME O3' > C36' SIMU 0.02 0.04 0.9 PART1 21 O3 6 0.405970 0.762689 0.500933 21.00000 0.02498 0.05116 = 0.04083 -0.00379 0.01335 0.00258 C33 1 0.438605 0.684535 0.452758 21.00000 0.03716 0.06364 = 0.04305 -0.00644 0.01332 0.00646 AFIX 23 H33A 2 0.410874 0.692752 0.398924 21.00000 -1.20000 H33B 2 0.439827 0.592295 0.467527 21.00000 -1.20000 AFIX 0 C34 1 0.515018 0.736936 0.464747 21.00000 0.03831 0.06183 = 0.04139 0.00256 0.01640 0.01359 AFIX 23 H34A 2 0.549243 0.667232 0.460759 21.00000 -1.20000 H34B 2 0.516562 0.805372 0.427386 21.00000 -1.20000 AFIX 0 C35 1 0.532309 0.790564 0.543497 21.00000 0.03140 0.04448 = 0.05722 -0.00986 0.01850 0.00006 AFIX 23 H35A 2 0.570910 0.856893 0.551719 21.00000 -1.20000 H35B 2 0.547088 0.721593 0.582060 21.00000 -1.20000 AFIX 0 C36 1 0.459986 0.849418 0.544624 21.00000 0.03405 0.03482 = 0.06469 -0.00528 0.02593 0.00079 AFIX 23 H36A 2 0.455849 0.856324 0.597257 21.00000 -1.20000 H36B 2 0.454505 0.936705 0.521573 21.00000 -1.20000 AFIX 0 PART2 -21 O3' 6 0.395666 0.732406 0.481376 -21.00000 0.04165 C33' 1 0.437523 0.628724 0.465173 -21.00000 0.04159 AFIX 23 H33C 2 0.426996 0.615484 0.409716 -21.00000 -1.20000 H33D 2 0.426230 0.547807 0.488585 -21.00000 -1.20000 AFIX 0 C34' 1 0.516364 0.664941 0.497909 -21.00000 0.03045 AFIX 23 H34C 2 0.547103 0.627517 0.467546 -21.00000 -1.20000 H34D 2 0.534390 0.635279 0.551066 -21.00000 -1.20000 AFIX 0 C35' 1 0.515187 0.812965 0.493192 -21.00000 0.04035 AFIX 23 H35C 2 0.553948 0.851583 0.534413 -21.00000 -1.20000 H35D 2 0.520661 0.843183 0.443694 -21.00000 -1.20000 AFIX 0 C36' 1 0.440418 0.845454 0.502279 -21.00000 0.03986 AFIX 23 H36C 2 0.443901 0.869629 0.555475 -21.00000 -1.20000 H36D 2 0.419287 0.919096 0.469149 -21.00000 -1.20000 PART0 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 954345' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mk83 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 N P' _chemical_formula_weight 363.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 10.1466(12) _cell_length_b 10.3281(13) _cell_length_c 11.5600(16) _cell_angle_alpha 75.024(10) _cell_angle_beta 68.112(12) _cell_angle_gamma 72.514(10) _cell_volume 1057.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11608 _cell_measurement_theta_min 4.1470 _cell_measurement_theta_max 75.4270 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 1.178 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.55472 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26651 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 75.85 _reflns_number_total 4359 _reflns_number_gt 3894 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. One tert-butyl group is disordered and was refined on two positions. The hydrogen at N was found and refined freely. Methyls were refined as rigid groups allowed to rotate but not tip. Other hydrogens were included using a riding model starting from calculated positions. ; _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^)+(0.0413P)^2^+0.6575P] 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 4359 _refine_ls_number_parameters 246 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.064 _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 0.29441(4) 0.36561(4) 0.36483(4) 0.02091(11) Uani 1 1 d . . . N N 0.67865(14) 0.24624(13) 0.11147(12) 0.0189(3) Uani 1 1 d . . . H01 H 0.733(2) 0.222(2) 0.037(2) 0.030(5) Uiso 1 1 d . . . C1 C 0.52872(16) 0.27672(15) 0.15211(14) 0.0185(3) Uani 1 1 d . . . C2 C 0.48323(16) 0.31780(16) 0.26867(14) 0.0197(3) Uani 1 1 d . . . C3 C 0.61292(16) 0.30980(17) 0.29599(14) 0.0218(3) Uani 1 1 d . . . H3 H 0.6155 0.3314 0.3700 0.026 Uiso 1 1 calc R . . C4 C 0.73162(16) 0.26598(16) 0.19776(14) 0.0204(3) Uani 1 1 d . A . C5 C 0.44652(17) 0.25920(17) 0.07280(15) 0.0233(3) Uani 1 1 d . . . C6 C 0.3430(2) 0.39616(18) 0.04133(18) 0.0313(4) Uani 1 1 d . . . H6A H 0.2740 0.4273 0.1199 0.047 Uiso 1 1 calc R . . H6B H 0.2892 0.3830 -0.0081 0.047 Uiso 1 1 calc R . . H6C H 0.3997 0.4654 -0.0079 0.047 Uiso 1 1 calc R . . C7 C 0.35888(19) 0.14891(18) 0.14626(18) 0.0294(4) Uani 1 1 d . . . H7A H 0.4253 0.0620 0.1666 0.044 Uiso 1 1 calc R . . H7B H 0.3079 0.1357 0.0944 0.044 Uiso 1 1 calc R . . H7C H 0.2875 0.1786 0.2246 0.044 Uiso 1 1 calc R . . C8 C 0.5530(2) 0.2131(2) -0.05158(17) 0.0336(4) Uani 1 1 d . . . H8A H 0.6094 0.2829 -0.0999 0.050 Uiso 1 1 calc R . . H8B H 0.4982 0.2017 -0.1010 0.050 Uiso 1 1 calc R . . H8C H 0.6194 0.1254 -0.0334 0.050 Uiso 1 1 calc R . . C9 C 0.89380(16) 0.23664(17) 0.17488(15) 0.0240(3) Uani 1 1 d D . . C10 C 0.9569(4) 0.3523(4) 0.0893(3) 0.0360(9) Uiso 0.533(3) 1 d PD A 1 H10A H 1.0616 0.3310 0.0769 0.054 Uiso 0.533(3) 1 calc PR A 1 H10B H 0.9089 0.4364 0.1267 0.054 Uiso 0.533(3) 1 calc PR A 1 H10C H 0.9419 0.3662 0.0076 0.054 Uiso 0.533(3) 1 calc PR A 1 C11 C 0.9218(4) 0.2080(4) 0.3035(3) 0.0322(8) Uiso 0.533(3) 1 d PD A 1 H11A H 0.8856 0.1271 0.3565 0.048 Uiso 0.533(3) 1 calc PR A 1 H11B H 0.8708 0.2881 0.3464 0.048 Uiso 0.533(3) 1 calc PR A 1 H11C H 1.0267 0.1908 0.2887 0.048 Uiso 0.533(3) 1 calc PR A 1 C12 C 0.9749(4) 0.1012(3) 0.1172(3) 0.0310(8) Uiso 0.533(3) 1 d PD A 1 H12A H 1.0778 0.0789 0.1116 0.046 Uiso 0.533(3) 1 calc PR A 1 H12B H 0.9677 0.1145 0.0325 0.046 Uiso 0.533(3) 1 calc PR A 1 H12C H 0.9299 0.0255 0.1714 0.046 Uiso 0.533(3) 1 calc PR A 1 C10' C 0.9222(4) 0.3329(4) 0.2417(3) 0.0269(8) Uiso 0.467(3) 1 d PD A 2 H10D H 0.8646 0.3205 0.3316 0.040 Uiso 0.467(3) 1 calc PR A 2 H10E H 0.8939 0.4288 0.2029 0.040 Uiso 0.467(3) 1 calc PR A 2 H10F H 1.0261 0.3101 0.2329 0.040 Uiso 0.467(3) 1 calc PR A 2 C11' C 0.9472(4) 0.0908(4) 0.2228(4) 0.0342(9) Uiso 0.467(3) 1 d PD A 2 H11D H 0.9319 0.0324 0.1764 0.051 Uiso 0.467(3) 1 calc PR A 2 H11E H 0.8937 0.0699 0.3130 0.051 Uiso 0.467(3) 1 calc PR A 2 H11F H 1.0515 0.0731 0.2109 0.051 Uiso 0.467(3) 1 calc PR A 2 C12' C 0.9735(4) 0.2738(4) 0.0318(4) 0.0335(9) Uiso 0.467(3) 1 d PD A 2 H12D H 1.0785 0.2565 0.0170 0.050 Uiso 0.467(3) 1 calc PR A 2 H12E H 0.9364 0.3712 0.0027 0.050 Uiso 0.467(3) 1 calc PR A 2 H12F H 0.9563 0.2171 -0.0149 0.050 Uiso 0.467(3) 1 calc PR A 2 C13 C 0.30594(16) 0.28491(17) 0.52351(15) 0.0222(3) Uani 1 1 d . . . C14 C 0.26478(19) 0.35661(19) 0.62244(16) 0.0286(4) Uani 1 1 d . . . H14 H 0.2373 0.4543 0.6076 0.034 Uiso 1 1 calc R . . C15 C 0.2634(2) 0.2868(2) 0.74333(17) 0.0339(4) Uani 1 1 d . . . H15 H 0.2349 0.3373 0.8101 0.041 Uiso 1 1 calc R . . C16 C 0.30324(19) 0.1445(2) 0.76685(16) 0.0308(4) Uani 1 1 d . . . H16 H 0.3019 0.0973 0.8494 0.037 Uiso 1 1 calc R . . C17 C 0.34515(19) 0.07149(19) 0.66896(16) 0.0297(4) Uani 1 1 d . . . H17 H 0.3738 -0.0261 0.6840 0.036 Uiso 1 1 calc R . . C18 C 0.34525(18) 0.14105(18) 0.54882(16) 0.0267(3) Uani 1 1 d . . . H18 H 0.3725 0.0901 0.4826 0.032 Uiso 1 1 calc R . . C19 C 0.26235(17) 0.54924(17) 0.36949(15) 0.0240(3) Uani 1 1 d . . . C20 C 0.36364(18) 0.61305(18) 0.37374(15) 0.0262(3) Uani 1 1 d . . . H20 H 0.4581 0.5600 0.3737 0.031 Uiso 1 1 calc R . . C21 C 0.3283(2) 0.75256(19) 0.37803(17) 0.0313(4) Uani 1 1 d . . . H21 H 0.3980 0.7944 0.3815 0.038 Uiso 1 1 calc R . . C22 C 0.1908(2) 0.8313(2) 0.3772(2) 0.0414(5) Uani 1 1 d . . . H22 H 0.1667 0.9271 0.3795 0.050 Uiso 1 1 calc R . . C23 C 0.0888(2) 0.7698(2) 0.3731(2) 0.0467(5) Uani 1 1 d . . . H23 H -0.0055 0.8233 0.3732 0.056 Uiso 1 1 calc R . . C24 C 0.12460(19) 0.6301(2) 0.36895(19) 0.0350(4) Uani 1 1 d . . . H24 H 0.0544 0.5887 0.3657 0.042 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 0.01381(19) 0.0269(2) 0.0226(2) -0.00572(15) -0.00558(14) -0.00428(15) N 0.0169(6) 0.0214(6) 0.0177(6) -0.0046(5) -0.0049(5) -0.0028(5) C1 0.0173(7) 0.0183(7) 0.0206(7) -0.0020(6) -0.0081(6) -0.0034(6) C2 0.0166(7) 0.0226(7) 0.0207(7) -0.0034(6) -0.0073(6) -0.0041(6) C3 0.0164(7) 0.0313(8) 0.0199(7) -0.0074(6) -0.0064(6) -0.0052(6) C4 0.0173(7) 0.0240(8) 0.0209(7) -0.0044(6) -0.0066(6) -0.0048(6) C5 0.0234(8) 0.0248(8) 0.0266(8) -0.0072(6) -0.0133(6) -0.0031(6) C6 0.0332(9) 0.0290(9) 0.0395(10) -0.0051(7) -0.0245(8) -0.0024(7) C7 0.0260(8) 0.0281(9) 0.0419(10) -0.0097(7) -0.0164(7) -0.0066(7) C8 0.0345(10) 0.0442(11) 0.0293(9) -0.0144(8) -0.0148(7) -0.0064(8) C9 0.0144(7) 0.0302(8) 0.0265(8) -0.0076(6) -0.0053(6) -0.0030(6) C13 0.0130(7) 0.0294(8) 0.0240(8) -0.0056(6) -0.0037(6) -0.0062(6) C14 0.0265(8) 0.0309(9) 0.0286(8) -0.0075(7) -0.0102(7) -0.0028(7) C15 0.0348(10) 0.0409(10) 0.0259(9) -0.0102(8) -0.0105(7) -0.0035(8) C16 0.0252(8) 0.0413(10) 0.0231(8) 0.0000(7) -0.0066(6) -0.0094(7) C17 0.0254(8) 0.0297(9) 0.0294(9) -0.0005(7) -0.0043(7) -0.0093(7) C18 0.0242(8) 0.0295(9) 0.0249(8) -0.0063(7) -0.0028(6) -0.0090(7) C19 0.0172(7) 0.0294(8) 0.0220(8) -0.0049(6) -0.0035(6) -0.0035(6) C20 0.0205(8) 0.0324(9) 0.0253(8) -0.0067(7) -0.0056(6) -0.0058(7) C21 0.0289(9) 0.0333(9) 0.0310(9) -0.0096(7) -0.0039(7) -0.0096(7) C22 0.0336(10) 0.0291(10) 0.0540(12) -0.0138(9) -0.0042(9) -0.0029(8) C23 0.0244(9) 0.0352(11) 0.0735(15) -0.0139(10) -0.0127(9) 0.0037(8) C24 0.0194(8) 0.0330(10) 0.0497(11) -0.0079(8) -0.0101(8) -0.0022(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 P C2 1.8104(16) . ? P C19 1.8370(18) . ? P C13 1.8397(17) . ? N C1 1.3748(19) . ? N C4 1.3770(19) . ? C1 C2 1.387(2) . ? C1 C5 1.522(2) . ? C2 C3 1.438(2) . ? C3 C4 1.365(2) . ? C4 C9 1.512(2) . ? C5 C8 1.532(2) . ? C5 C7 1.535(2) . ? C5 C6 1.537(2) . ? C9 C11' 1.473(4) . ? C9 C10 1.481(4) . ? C9 C12' 1.549(4) . ? C9 C10' 1.550(4) . ? C9 C11 1.555(4) . ? C9 C12 1.569(4) . ? C13 C14 1.388(2) . ? C13 C18 1.400(2) . ? C14 C15 1.394(3) . ? C15 C16 1.384(3) . ? C16 C17 1.385(3) . ? C17 C18 1.389(2) . ? C19 C24 1.398(2) . ? C19 C20 1.398(2) . ? C20 C21 1.386(3) . ? C21 C22 1.390(3) . ? C22 C23 1.387(3) . ? C23 C24 1.387(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 C2 P C19 104.95(7) . . ? C2 P C13 100.97(7) . . ? C19 P C13 102.03(7) . . ? C1 N C4 111.47(13) . . ? N C1 C2 106.68(13) . . ? N C1 C5 120.52(13) . . ? C2 C1 C5 132.79(14) . . ? C1 C2 C3 106.75(13) . . ? C1 C2 P 124.42(11) . . ? C3 C2 P 128.80(12) . . ? C4 C3 C2 108.62(13) . . ? C3 C4 N 106.48(13) . . ? C3 C4 C9 132.35(14) . . ? N C4 C9 121.16(13) . . ? C1 C5 C8 110.63(13) . . ? C1 C5 C7 109.33(13) . . ? C8 C5 C7 108.47(14) . . ? C1 C5 C6 110.27(13) . . ? C8 C5 C6 108.32(14) . . ? C7 C5 C6 109.79(14) . . ? C11' C9 C10 137.5(2) . . ? C11' C9 C4 109.8(2) . . ? C10 C9 C4 111.24(19) . . ? C11' C9 C12' 111.3(2) . . ? C10 C9 C12' 43.1(2) . . ? C4 C9 C12' 109.39(19) . . ? C11' C9 C10' 111.2(2) . . ? C10 C9 C10' 65.1(2) . . ? C4 C9 C10' 108.69(18) . . ? C12' C9 C10' 106.5(2) . . ? C11' C9 C11 64.6(2) . . ? C10 C9 C11 110.7(2) . . ? C4 C9 C11 109.37(17) . . ? C12' C9 C11 139.7(2) . . ? C10' C9 C11 49.62(19) . . ? C11' C9 C12 43.4(2) . . ? C10 C9 C12 109.3(2) . . ? C4 C9 C12 110.89(17) . . ? C12' C9 C12 70.5(2) . . ? C10' C9 C12 138.8(2) . . ? C11 C9 C12 105.2(2) . . ? C14 C13 C18 118.13(15) . . ? C14 C13 P 124.10(13) . . ? C18 C13 P 117.47(12) . . ? C13 C14 C15 120.71(17) . . ? C16 C15 C14 120.54(17) . . ? C15 C16 C17 119.44(16) . . ? C16 C17 C18 119.99(17) . . ? C17 C18 C13 121.19(16) . . ? C24 C19 C20 118.21(16) . . ? C24 C19 P 116.39(13) . . ? C20 C19 P 125.39(13) . . ? C21 C20 C19 120.96(16) . . ? C20 C21 C22 119.99(17) . . ? C23 C22 C21 119.86(18) . . ? C24 C23 C22 119.95(18) . . ? C23 C24 C19 121.02(18) . . ? 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 C4 N C1 C2 0.09(17) . . . . ? C4 N C1 C5 -178.64(13) . . . . ? N C1 C2 C3 -0.27(17) . . . . ? C5 C1 C2 C3 178.24(16) . . . . ? N C1 C2 P -178.50(11) . . . . ? C5 C1 C2 P 0.0(3) . . . . ? C19 P C2 C1 -114.60(14) . . . . ? C13 P C2 C1 139.65(14) . . . . ? C19 P C2 C3 67.57(16) . . . . ? C13 P C2 C3 -38.18(16) . . . . ? C1 C2 C3 C4 0.36(18) . . . . ? P C2 C3 C4 178.49(12) . . . . ? C2 C3 C4 N -0.30(18) . . . . ? C2 C3 C4 C9 -178.86(16) . . . . ? C1 N C4 C3 0.14(18) . . . . ? C1 N C4 C9 178.90(13) . . . . ? N C1 C5 C8 -2.8(2) . . . . ? C2 C1 C5 C8 178.89(17) . . . . ? N C1 C5 C7 116.62(16) . . . . ? C2 C1 C5 C7 -61.7(2) . . . . ? N C1 C5 C6 -122.58(16) . . . . ? C2 C1 C5 C6 59.1(2) . . . . ? C3 C4 C9 C11' 91.0(3) . . . . ? N C4 C9 C11' -87.4(2) . . . . ? C3 C4 C9 C10 -100.6(2) . . . . ? N C4 C9 C10 81.0(2) . . . . ? C3 C4 C9 C12' -146.6(2) . . . . ? N C4 C9 C12' 35.0(2) . . . . ? C3 C4 C9 C10' -30.7(3) . . . . ? N C4 C9 C10' 150.88(19) . . . . ? C3 C4 C9 C11 22.0(3) . . . . ? N C4 C9 C11 -156.42(18) . . . . ? C3 C4 C9 C12 137.5(2) . . . . ? N C4 C9 C12 -40.9(2) . . . . ? C2 P C13 C14 120.92(14) . . . . ? C19 P C13 C14 12.86(15) . . . . ? C2 P C13 C18 -65.54(13) . . . . ? C19 P C13 C18 -173.60(12) . . . . ? C18 C13 C14 C15 0.3(2) . . . . ? P C13 C14 C15 173.75(13) . . . . ? C13 C14 C15 C16 0.1(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C15 C16 C17 C18 -0.8(3) . . . . ? C16 C17 C18 C13 1.1(3) . . . . ? C14 C13 C18 C17 -0.8(2) . . . . ? P C13 C18 C17 -174.78(13) . . . . ? C2 P C19 C24 143.90(14) . . . . ? C13 P C19 C24 -111.14(14) . . . . ? C2 P C19 C20 -36.24(16) . . . . ? C13 P C19 C20 68.72(15) . . . . ? C24 C19 C20 C21 0.4(3) . . . . ? P C19 C20 C21 -179.50(13) . . . . ? C19 C20 C21 C22 -0.5(3) . . . . ? C20 C21 C22 C23 0.5(3) . . . . ? C21 C22 C23 C24 -0.5(4) . . . . ? C22 C23 C24 C19 0.4(3) . . . . ? C20 C19 C24 C23 -0.3(3) . . . . ? P C19 C24 C23 179.56(17) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 75.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.558 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.048 _iunc_refine_instructions_details ; TITL MK83 in P-1 CELL 1.54184 10.146603 10.328123 11.559960 75.0243 68.1115 72.5139 ZERR 2.00 0.001200 0.001300 0.001600 0.0100 0.0120 0.0100 LATT 1 SFAC C H N P UNIT 48 60 2 2 MERG 2 FMAP 2 ACTA 150 CONF TEMP -173 PLAN 10 L.S. 4 WGHT 0.041300 0.657500 FVAR 8.55203 0.53303 P 4 0.294409 0.365613 0.364831 11.00000 0.01381 0.02686 = 0.02258 -0.00572 -0.00558 -0.00428 N 3 0.678652 0.246235 0.111471 11.00000 0.01686 0.02137 = 0.01773 -0.00465 -0.00491 -0.00276 H01 2 0.732572 0.222021 0.037342 11.00000 0.02976 C1 1 0.528717 0.276725 0.152111 11.00000 0.01731 0.01834 = 0.02057 -0.00203 -0.00807 -0.00339 C2 1 0.483233 0.317802 0.268670 11.00000 0.01660 0.02259 = 0.02065 -0.00342 -0.00726 -0.00410 C3 1 0.612918 0.309800 0.295992 11.00000 0.01637 0.03132 = 0.01988 -0.00740 -0.00641 -0.00519 AFIX 43 H3 2 0.615519 0.331408 0.370048 11.00000 -1.20000 AFIX 0 C4 1 0.731623 0.265979 0.197758 11.00000 0.01733 0.02399 = 0.02088 -0.00441 -0.00659 -0.00483 C5 1 0.446516 0.259198 0.072796 11.00000 0.02343 0.02481 = 0.02657 -0.00721 -0.01327 -0.00312 C6 1 0.342960 0.396162 0.041332 11.00000 0.03324 0.02900 = 0.03953 -0.00509 -0.02446 -0.00239 AFIX 137 H6A 2 0.273976 0.427331 0.119914 11.00000 -1.50000 H6B 2 0.289151 0.383027 -0.008110 11.00000 -1.50000 H6C 2 0.399736 0.465440 -0.007866 11.00000 -1.50000 AFIX 0 C7 1 0.358880 0.148914 0.146263 11.00000 0.02596 0.02807 = 0.04186 -0.00974 -0.01643 -0.00661 AFIX 137 H7A 2 0.425276 0.062021 0.166623 11.00000 -1.50000 H7B 2 0.307923 0.135687 0.094448 11.00000 -1.50000 H7C 2 0.287474 0.178608 0.224633 11.00000 -1.50000 AFIX 0 C8 1 0.553001 0.213124 -0.051580 11.00000 0.03445 0.04421 = 0.02930 -0.01439 -0.01477 -0.00638 AFIX 137 H8A 2 0.609441 0.282869 -0.099925 11.00000 -1.50000 H8B 2 0.498243 0.201674 -0.101015 11.00000 -1.50000 H8C 2 0.619429 0.125356 -0.033354 11.00000 -1.50000 AFIX 0 SAME C9 C10' > C12' SADI C9 C10 C9 C11 C9 C12 SADI C10 C11 C11 C12 C12 C10 SIMU 0.02 0.04 0.9 C10 > C12' C9 1 0.893795 0.236638 0.174876 11.00000 0.01443 0.03025 = 0.02646 -0.00755 -0.00526 -0.00305 PART1 21 C10 1 0.956895 0.352336 0.089287 21.00000 0.03598 AFIX 137 H10A 2 1.061610 0.331023 0.076949 21.00000 -1.50000 H10B 2 0.908907 0.436355 0.126722 21.00000 -1.50000 H10C 2 0.941922 0.366194 0.007551 21.00000 -1.50000 AFIX 0 C11 1 0.921810 0.208025 0.303511 21.00000 0.03223 AFIX 137 H11A 2 0.885566 0.127150 0.356503 21.00000 -1.50000 H11B 2 0.870795 0.288059 0.346405 21.00000 -1.50000 H11C 2 1.026728 0.190831 0.288713 21.00000 -1.50000 AFIX 0 C12 1 0.974921 0.101167 0.117178 21.00000 0.03098 AFIX 137 H12A 2 1.077832 0.078874 0.111583 21.00000 -1.50000 H12B 2 0.967682 0.114525 0.032497 21.00000 -1.50000 H12C 2 0.929929 0.025473 0.171409 21.00000 -1.50000 AFIX 0 PART2 -21 C10' 1 0.922201 0.332853 0.241713 -21.00000 0.02691 AFIX 137 H10D 2 0.864605 0.320504 0.331565 -21.00000 -1.50000 H10E 2 0.893866 0.428758 0.202907 -21.00000 -1.50000 H10F 2 1.026091 0.310131 0.232926 -21.00000 -1.50000 AFIX 0 C11' 1 0.947170 0.090810 0.222795 -21.00000 0.03423 AFIX 137 H11D 2 0.931874 0.032428 0.176421 -21.00000 -1.50000 H11E 2 0.893667 0.069876 0.312980 -21.00000 -1.50000 H11F 2 1.051472 0.073132 0.210856 -21.00000 -1.50000 AFIX 0 C12' 1 0.973542 0.273758 0.031805 -21.00000 0.03346 AFIX 137 H12D 2 1.078462 0.256460 0.017048 -21.00000 -1.50000 H12E 2 0.936365 0.371239 0.002711 -21.00000 -1.50000 H12F 2 0.956267 0.217069 -0.014887 -21.00000 -1.50000 AFIX 0 PART0 C13 1 0.305937 0.284913 0.523512 11.00000 0.01304 0.02944 = 0.02396 -0.00564 -0.00374 -0.00624 C14 1 0.264781 0.356609 0.622438 11.00000 0.02653 0.03088 = 0.02863 -0.00749 -0.01020 -0.00283 AFIX 43 H14 2 0.237258 0.454308 0.607622 11.00000 -1.20000 AFIX 0 C15 1 0.263399 0.286781 0.743325 11.00000 0.03483 0.04089 = 0.02595 -0.01020 -0.01050 -0.00351 AFIX 43 H15 2 0.234874 0.337286 0.810100 11.00000 -1.20000 AFIX 0 C16 1 0.303238 0.144501 0.766846 11.00000 0.02519 0.04128 = 0.02312 0.00005 -0.00659 -0.00944 AFIX 43 H16 2 0.301856 0.097298 0.849411 11.00000 -1.20000 AFIX 0 C17 1 0.345152 0.071491 0.668961 11.00000 0.02545 0.02967 = 0.02940 -0.00046 -0.00435 -0.00929 AFIX 43 H17 2 0.373826 -0.026142 0.684020 11.00000 -1.20000 AFIX 0 C18 1 0.345247 0.141047 0.548817 11.00000 0.02418 0.02953 = 0.02489 -0.00625 -0.00278 -0.00895 AFIX 43 H18 2 0.372485 0.090053 0.482620 11.00000 -1.20000 AFIX 0 C19 1 0.262348 0.549240 0.369494 11.00000 0.01716 0.02936 = 0.02204 -0.00491 -0.00351 -0.00355 C20 1 0.363635 0.613051 0.373743 11.00000 0.02046 0.03236 = 0.02530 -0.00675 -0.00557 -0.00576 AFIX 43 H20 2 0.458064 0.560001 0.373693 11.00000 -1.20000 AFIX 0 C21 1 0.328300 0.752555 0.378027 11.00000 0.02886 0.03332 = 0.03103 -0.00956 -0.00394 -0.00964 AFIX 43 H21 2 0.398038 0.794355 0.381509 11.00000 -1.20000 AFIX 0 C22 1 0.190752 0.831349 0.377227 11.00000 0.03357 0.02907 = 0.05399 -0.01376 -0.00420 -0.00293 AFIX 43 H22 2 0.166655 0.927142 0.379478 11.00000 -1.20000 AFIX 0 C23 1 0.088786 0.769784 0.373133 11.00000 0.02443 0.03523 = 0.07346 -0.01393 -0.01273 0.00367 AFIX 43 H23 2 -0.005503 0.823261 0.373194 11.00000 -1.20000 AFIX 0 C24 1 0.124596 0.630099 0.368951 11.00000 0.01941 0.03304 = 0.04974 -0.00793 -0.01010 -0.00225 AFIX 43 H24 2 0.054404 0.588740 0.365668 11.00000 -1.20000 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 954346' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mk87 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 N P S' _chemical_formula_weight 395.52 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' S S 0.1246 0.1234 '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 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.4026(3) _cell_length_b 10.6074(3) _cell_length_c 19.8992(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2195.75(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 25536 _cell_measurement_theta_min 2.7430 _cell_measurement_theta_max 29.9830 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98352 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 130250 _diffrn_reflns_av_R_equivalents 0.0580 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 30.99 _reflns_number_total 6715 _reflns_number_gt 6146 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. The hydrogen at N was found and refined freely. Methyls were refined as rigid groups allowed to rotate but not tip. Other hydrogens were included using a riding model starting from calculated positions. The compound is achiral and crystallises by chance in a Soehnke space group. ; _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^)+(0.0304P)^2^+0.5806P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(4) _chemical_absolute_configuration . _refine_ls_number_reflns 6715 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0706 _refine_ls_wR_factor_gt 0.0669 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 N N 1.03151(11) 0.58905(10) 0.50378(5) 0.0143(2) Uani 1 1 d . . . H01 H 1.0882(16) 0.6033(16) 0.4749(9) 0.019(4) Uiso 1 1 d . . . P P 0.80624(3) 0.67160(3) 0.657789(14) 0.01135(6) Uani 1 1 d . . . S S 0.72104(3) 0.83388(3) 0.639205(15) 0.01531(6) Uani 1 1 d . . . C1 C 1.00762(11) 0.66467(13) 0.55827(6) 0.0135(2) Uani 1 1 d . . . C2 C 0.90265(12) 0.61069(11) 0.59119(6) 0.0123(2) Uani 1 1 d . . . C3 C 0.86592(12) 0.50010(11) 0.55354(6) 0.0132(2) Uani 1 1 d . . . H3 H 0.7974 0.4445 0.5643 0.016 Uiso 1 1 calc R . . C4 C 0.94687(12) 0.48924(11) 0.49965(6) 0.0133(2) Uani 1 1 d . . . C5 C 1.09158(12) 0.78086(12) 0.56684(6) 0.0150(2) Uani 1 1 d . . . C6 C 1.04888(15) 0.88084(14) 0.51540(8) 0.0238(3) Uani 1 1 d . . . H6A H 1.0553 0.8459 0.4699 0.036 Uiso 1 1 calc R . . H6B H 1.1045 0.9551 0.5191 0.036 Uiso 1 1 calc R . . H6C H 0.9597 0.9052 0.5244 0.036 Uiso 1 1 calc R . . C7 C 1.23312(12) 0.74491(13) 0.55420(7) 0.0204(3) Uani 1 1 d . . . H7A H 1.2579 0.6766 0.5847 0.031 Uiso 1 1 calc R . . H7B H 1.2881 0.8184 0.5623 0.031 Uiso 1 1 calc R . . H7C H 1.2434 0.7169 0.5076 0.031 Uiso 1 1 calc R . . C8 C 1.08375(13) 0.83908(13) 0.63697(6) 0.0197(2) Uani 1 1 d . . . H8A H 0.9941 0.8596 0.6474 0.030 Uiso 1 1 calc R . . H8B H 1.1357 0.9161 0.6384 0.030 Uiso 1 1 calc R . . H8C H 1.1165 0.7788 0.6702 0.030 Uiso 1 1 calc R . . C9 C 0.95720(13) 0.39317(12) 0.44370(6) 0.0152(2) Uani 1 1 d . . . C10 C 1.09208(15) 0.33503(17) 0.44421(8) 0.0309(3) Uani 1 1 d . . . H10A H 1.1561 0.4010 0.4360 0.046 Uiso 1 1 calc R . . H10B H 1.0981 0.2708 0.4089 0.046 Uiso 1 1 calc R . . H10C H 1.1083 0.2961 0.4881 0.046 Uiso 1 1 calc R . . C11 C 0.93238(14) 0.45603(13) 0.37533(6) 0.0202(3) Uani 1 1 d . . . H11A H 0.8444 0.4890 0.3741 0.030 Uiso 1 1 calc R . . H11B H 0.9436 0.3938 0.3394 0.030 Uiso 1 1 calc R . . H11C H 0.9933 0.5254 0.3689 0.030 Uiso 1 1 calc R . . C12 C 0.85636(17) 0.29053(14) 0.45380(8) 0.0288(3) Uani 1 1 d . . . H12A H 0.8708 0.2488 0.4971 0.043 Uiso 1 1 calc R . . H12B H 0.8631 0.2285 0.4175 0.043 Uiso 1 1 calc R . . H12C H 0.7704 0.3284 0.4533 0.043 Uiso 1 1 calc R . . C13 C 0.90260(12) 0.67833(12) 0.73388(6) 0.0148(2) Uani 1 1 d . . . C14 C 0.87049(13) 0.76342(13) 0.78459(6) 0.0191(3) Uani 1 1 d . . . H14 H 0.7984 0.8176 0.7794 0.023 Uiso 1 1 calc R . . C15 C 0.94445(15) 0.76890(15) 0.84308(7) 0.0258(3) Uani 1 1 d . . . H15 H 0.9227 0.8266 0.8778 0.031 Uiso 1 1 calc R . . C16 C 1.04953(15) 0.69007(14) 0.85034(7) 0.0278(3) Uani 1 1 d . . . H16 H 1.1002 0.6944 0.8900 0.033 Uiso 1 1 calc R . . C17 C 1.08126(15) 0.60506(14) 0.80035(8) 0.0262(3) Uani 1 1 d . . . H17 H 1.1534 0.5511 0.8058 0.031 Uiso 1 1 calc R . . C18 C 1.00782(14) 0.59854(13) 0.74221(7) 0.0194(3) Uani 1 1 d . . . H18 H 1.0293 0.5396 0.7081 0.023 Uiso 1 1 calc R . . C19 C 0.68868(12) 0.54979(11) 0.67818(6) 0.0140(2) Uani 1 1 d . . . C20 C 0.72904(13) 0.43366(12) 0.70356(6) 0.0178(2) Uani 1 1 d . . . H20 H 0.8182 0.4158 0.7073 0.021 Uiso 1 1 calc R . . C21 C 0.63933(13) 0.34419(14) 0.72336(7) 0.0203(3) Uani 1 1 d . . . H21 H 0.6672 0.2652 0.7406 0.024 Uiso 1 1 calc R . . C22 C 0.50847(14) 0.37021(14) 0.71796(7) 0.0221(3) Uani 1 1 d . . . H22 H 0.4470 0.3092 0.7317 0.027 Uiso 1 1 calc R . . C23 C 0.46823(13) 0.48514(14) 0.69253(7) 0.0223(3) Uani 1 1 d . . . H23 H 0.3790 0.5027 0.6887 0.027 Uiso 1 1 calc R . . C24 C 0.55796(13) 0.57496(13) 0.67257(6) 0.0177(3) Uani 1 1 d . . . H24 H 0.5298 0.6536 0.6551 0.021 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 N 0.0134(5) 0.0182(5) 0.0115(5) -0.0028(4) 0.0035(4) -0.0018(4) P 0.01060(13) 0.01437(13) 0.00908(12) -0.00081(11) 0.00057(10) -0.00024(12) S 0.01533(14) 0.01622(13) 0.01439(13) -0.00113(11) -0.00157(10) 0.00292(12) C1 0.0139(5) 0.0156(5) 0.0108(5) -0.0010(5) 0.0005(4) 0.0006(5) C2 0.0128(6) 0.0144(5) 0.0099(5) -0.0009(4) 0.0005(4) 0.0012(5) C3 0.0138(6) 0.0146(5) 0.0110(5) -0.0010(4) -0.0003(4) -0.0013(4) C4 0.0141(5) 0.0147(5) 0.0111(5) -0.0008(4) -0.0011(4) 0.0000(4) C5 0.0131(6) 0.0179(6) 0.0141(5) -0.0015(4) 0.0029(4) -0.0034(5) C6 0.0251(7) 0.0217(7) 0.0248(7) 0.0041(5) -0.0029(6) -0.0058(6) C7 0.0141(6) 0.0258(7) 0.0214(6) -0.0049(5) 0.0026(5) -0.0040(5) C8 0.0196(6) 0.0222(6) 0.0173(5) -0.0063(5) 0.0046(5) -0.0082(5) C9 0.0173(6) 0.0168(6) 0.0114(5) -0.0024(4) 0.0008(4) 0.0010(5) C10 0.0303(8) 0.0369(8) 0.0254(7) -0.0146(7) -0.0079(6) 0.0177(8) C11 0.0273(7) 0.0212(6) 0.0121(6) -0.0024(5) -0.0008(5) 0.0001(5) C12 0.0445(9) 0.0233(7) 0.0185(7) -0.0063(5) 0.0069(6) -0.0122(6) C13 0.0150(5) 0.0186(6) 0.0110(5) 0.0019(4) -0.0007(4) -0.0035(5) C14 0.0183(6) 0.0257(7) 0.0134(6) -0.0025(5) 0.0013(5) -0.0042(5) C15 0.0317(8) 0.0336(8) 0.0122(6) -0.0031(5) -0.0011(5) -0.0100(6) C16 0.0341(8) 0.0313(8) 0.0178(6) 0.0070(5) -0.0129(6) -0.0122(6) C17 0.0266(7) 0.0229(7) 0.0293(7) 0.0097(6) -0.0128(6) -0.0037(6) C18 0.0198(6) 0.0187(6) 0.0198(6) 0.0026(5) -0.0038(5) -0.0016(5) C19 0.0146(6) 0.0183(6) 0.0092(5) -0.0018(4) 0.0022(4) -0.0038(5) C20 0.0169(6) 0.0200(6) 0.0166(6) -0.0010(5) 0.0020(5) -0.0013(5) C21 0.0250(6) 0.0190(6) 0.0170(6) -0.0010(5) 0.0035(5) -0.0038(6) C22 0.0223(7) 0.0262(7) 0.0178(6) -0.0036(5) 0.0064(5) -0.0103(5) C23 0.0140(6) 0.0308(7) 0.0222(7) -0.0037(6) 0.0034(5) -0.0055(5) C24 0.0153(6) 0.0231(6) 0.0149(6) -0.0017(5) 0.0013(5) -0.0014(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 N C1 1.3715(15) . ? N C4 1.3794(16) . ? P C2 1.7831(12) . ? P C13 1.8174(12) . ? P C19 1.8247(13) . ? P S 1.9711(5) . ? C1 C2 1.3962(17) . ? C1 C5 1.5201(18) . ? C2 C3 1.4434(16) . ? C3 C4 1.3684(17) . ? C4 C9 1.5131(17) . ? C5 C8 1.5283(17) . ? C5 C6 1.5394(19) . ? C5 C7 1.5415(18) . ? C9 C12 1.5252(19) . ? C9 C10 1.5328(19) . ? C9 C11 1.5369(18) . ? C13 C18 1.3934(19) . ? C13 C14 1.3945(18) . ? C14 C15 1.3963(18) . ? C15 C16 1.384(2) . ? C16 C17 1.383(2) . ? C17 C18 1.388(2) . ? C19 C24 1.3903(19) . ? C19 C20 1.3959(18) . ? C20 C21 1.3880(19) . ? C21 C22 1.393(2) . ? C22 C23 1.385(2) . ? C23 C24 1.3917(19) . ? 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 N C4 112.35(10) . . ? C2 P C13 108.86(6) . . ? C2 P C19 106.60(6) . . ? C13 P C19 102.25(6) . . ? C2 P S 115.46(4) . . ? C13 P S 111.72(5) . . ? C19 P S 111.03(4) . . ? N C1 C2 105.83(11) . . ? N C1 C5 117.31(10) . . ? C2 C1 C5 136.82(11) . . ? C1 C2 C3 107.27(10) . . ? C1 C2 P 129.79(10) . . ? C3 C2 P 122.09(9) . . ? C4 C3 C2 108.19(11) . . ? C3 C4 N 106.36(11) . . ? C3 C4 C9 132.61(11) . . ? N C4 C9 121.02(11) . . ? C1 C5 C8 113.54(10) . . ? C1 C5 C6 108.56(11) . . ? C8 C5 C6 108.26(11) . . ? C1 C5 C7 109.26(10) . . ? C8 C5 C7 107.45(11) . . ? C6 C5 C7 109.73(11) . . ? C4 C9 C12 109.57(10) . . ? C4 C9 C10 109.34(11) . . ? C12 C9 C10 109.97(13) . . ? C4 C9 C11 110.32(10) . . ? C12 C9 C11 108.11(11) . . ? C10 C9 C11 109.52(11) . . ? C18 C13 C14 119.69(12) . . ? C18 C13 P 120.56(10) . . ? C14 C13 P 119.75(10) . . ? C13 C14 C15 119.87(13) . . ? C16 C15 C14 119.81(14) . . ? C17 C16 C15 120.50(13) . . ? C16 C17 C18 120.05(14) . . ? C17 C18 C13 120.07(14) . . ? C24 C19 C20 119.51(12) . . ? C24 C19 P 120.11(10) . . ? C20 C19 P 120.25(10) . . ? C21 C20 C19 120.26(13) . . ? C20 C21 C22 119.97(14) . . ? C23 C22 C21 119.87(13) . . ? C22 C23 C24 120.28(13) . . ? C19 C24 C23 120.10(13) . . ? 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 C4 N C1 C2 0.28(14) . . . . ? C4 N C1 C5 -177.78(11) . . . . ? N C1 C2 C3 -0.06(13) . . . . ? C5 C1 C2 C3 177.43(14) . . . . ? N C1 C2 P -169.50(10) . . . . ? C5 C1 C2 P 8.0(2) . . . . ? C13 P C2 C1 -68.75(13) . . . . ? C19 P C2 C1 -178.37(11) . . . . ? S P C2 C1 57.81(13) . . . . ? C13 P C2 C3 123.17(10) . . . . ? C19 P C2 C3 13.55(12) . . . . ? S P C2 C3 -110.27(10) . . . . ? C1 C2 C3 C4 -0.18(14) . . . . ? P C2 C3 C4 170.25(9) . . . . ? C2 C3 C4 N 0.34(14) . . . . ? C2 C3 C4 C9 178.97(12) . . . . ? C1 N C4 C3 -0.40(14) . . . . ? C1 N C4 C9 -179.22(11) . . . . ? N C1 C5 C8 -164.44(11) . . . . ? C2 C1 C5 C8 18.3(2) . . . . ? N C1 C5 C6 75.11(14) . . . . ? C2 C1 C5 C6 -102.16(17) . . . . ? N C1 C5 C7 -44.52(15) . . . . ? C2 C1 C5 C7 138.20(15) . . . . ? C3 C4 C9 C12 -1.4(2) . . . . ? N C4 C9 C12 177.07(12) . . . . ? C3 C4 C9 C10 -121.99(16) . . . . ? N C4 C9 C10 56.48(16) . . . . ? C3 C4 C9 C11 117.51(15) . . . . ? N C4 C9 C11 -64.03(15) . . . . ? C2 P C13 C18 -25.11(12) . . . . ? C19 P C13 C18 87.41(11) . . . . ? S P C13 C18 -153.79(9) . . . . ? C2 P C13 C14 155.34(10) . . . . ? C19 P C13 C14 -92.14(11) . . . . ? S P C13 C14 26.66(11) . . . . ? C18 C13 C14 C15 0.52(19) . . . . ? P C13 C14 C15 -179.92(10) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C14 C15 C16 C17 -0.6(2) . . . . ? C15 C16 C17 C18 0.2(2) . . . . ? C16 C17 C18 C13 0.5(2) . . . . ? C14 C13 C18 C17 -0.87(19) . . . . ? P C13 C18 C17 179.58(11) . . . . ? C2 P C19 C24 -120.18(10) . . . . ? C13 P C19 C24 125.62(11) . . . . ? S P C19 C24 6.34(11) . . . . ? C2 P C19 C20 63.93(11) . . . . ? C13 P C19 C20 -50.27(11) . . . . ? S P C19 C20 -169.55(9) . . . . ? C24 C19 C20 C21 -0.30(19) . . . . ? P C19 C20 C21 175.61(10) . . . . ? C19 C20 C21 C22 0.0(2) . . . . ? C20 C21 C22 C23 0.3(2) . . . . ? C21 C22 C23 C24 -0.2(2) . . . . ? C20 C19 C24 C23 0.38(19) . . . . ? P C19 C24 C23 -175.54(10) . . . . ? C22 C23 C24 C19 -0.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H01 S 0.838(18) 2.740(18) 3.5569(11) 165.5(15) 4_566 C7 H7C S 0.98 2.98 3.9402(14) 167.0 4_566 C11 H11C S 0.98 2.80 3.7507(15) 162.5 4_566 C17 H17 S 0.95 2.87 3.7350(15) 152.6 3_746 _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.359 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.049 _iucr_refine_instructions_details ; TITL MK87 in P2(1)2(1)2(1) CELL 0.71073 10.402553 10.607355 19.899189 90.0000 90.0000 90.0000 ZERR 4.00 0.000300 0.000300 0.000500 0.0000 0.0000 0.0000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N P S UNIT 96 120 4 4 4 MERG 2 FMAP 2 EQIV $1 0.5 +x, 1.5-y, 1-z HTAB N S_$1 ACTA 61 CONF TEMP -173 PLAN 10 L.S. 4 WGHT 0.030400 0.580600 FVAR 3.83386 N 3 1.031511 0.589047 0.503779 11.00000 0.01341 0.01817 = 0.01146 -0.00282 0.00350 -0.00184 H01 2 1.088186 0.603299 0.474854 11.00000 0.01945 P 4 0.806237 0.671602 0.657789 11.00000 0.01060 0.01437 = 0.00908 -0.00081 0.00057 -0.00024 S 5 0.721045 0.833880 0.639205 11.00000 0.01533 0.01622 = 0.01439 -0.00113 -0.00157 0.00292 C1 1 1.007625 0.664671 0.558272 11.00000 0.01393 0.01560 = 0.01082 -0.00101 0.00047 0.00064 C2 1 0.902649 0.610694 0.591189 11.00000 0.01276 0.01443 = 0.00985 -0.00090 0.00048 0.00123 C3 1 0.865915 0.500097 0.553545 11.00000 0.01383 0.01465 = 0.01099 -0.00101 -0.00027 -0.00135 AFIX 43 H3 2 0.797384 0.444459 0.564320 11.00000 -1.20000 AFIX 0 C4 1 0.946871 0.489245 0.499652 11.00000 0.01406 0.01465 = 0.01107 -0.00080 -0.00107 0.00004 C5 1 1.091584 0.780855 0.566837 11.00000 0.01307 0.01789 = 0.01414 -0.00147 0.00290 -0.00337 C6 1 1.048885 0.880844 0.515404 11.00000 0.02507 0.02165 = 0.02481 0.00415 -0.00293 -0.00582 AFIX 137 H6A 2 1.055333 0.845890 0.469942 11.00000 -1.50000 H6B 2 1.104483 0.955102 0.519120 11.00000 -1.50000 H6C 2 0.959656 0.905195 0.524409 11.00000 -1.50000 AFIX 0 C7 1 1.233116 0.744909 0.554197 11.00000 0.01405 0.02584 = 0.02143 -0.00489 0.00260 -0.00402 AFIX 137 H7A 2 1.257913 0.676563 0.584693 11.00000 -1.50000 H7B 2 1.288051 0.818414 0.562288 11.00000 -1.50000 H7C 2 1.243361 0.716900 0.507573 11.00000 -1.50000 AFIX 0 C8 1 1.083754 0.839079 0.636969 11.00000 0.01960 0.02219 = 0.01731 -0.00625 0.00459 -0.00817 AFIX 137 H8A 2 0.994080 0.859596 0.647370 11.00000 -1.50000 H8B 2 1.135662 0.916134 0.638352 11.00000 -1.50000 H8C 2 1.116500 0.778842 0.670155 11.00000 -1.50000 AFIX 0 C9 1 0.957195 0.393174 0.443704 11.00000 0.01727 0.01677 = 0.01143 -0.00236 0.00080 0.00102 C10 1 1.092080 0.335025 0.444213 11.00000 0.03026 0.03686 = 0.02544 -0.01459 -0.00786 0.01773 AFIX 137 H10A 2 1.156082 0.401027 0.435959 11.00000 -1.50000 H10B 2 1.098081 0.270800 0.408950 11.00000 -1.50000 H10C 2 1.108316 0.296070 0.488055 11.00000 -1.50000 AFIX 0 C11 1 0.932377 0.456025 0.375332 11.00000 0.02732 0.02124 = 0.01214 -0.00236 -0.00076 0.00009 AFIX 137 H11A 2 0.844385 0.488952 0.374116 11.00000 -1.50000 H11B 2 0.943594 0.393777 0.339415 11.00000 -1.50000 H11C 2 0.993325 0.525422 0.368868 11.00000 -1.50000 AFIX 0 C12 1 0.856361 0.290531 0.453804 11.00000 0.04451 0.02332 = 0.01853 -0.00628 0.00693 -0.01222 AFIX 137 H12A 2 0.870756 0.248781 0.497088 11.00000 -1.50000 H12B 2 0.863097 0.228454 0.417500 11.00000 -1.50000 H12C 2 0.770437 0.328403 0.453315 11.00000 -1.50000 AFIX 0 C13 1 0.902600 0.678325 0.733883 11.00000 0.01500 0.01856 = 0.01095 0.00194 -0.00072 -0.00348 C14 1 0.870490 0.763418 0.784594 11.00000 0.01832 0.02573 = 0.01339 -0.00249 0.00133 -0.00418 AFIX 43 H14 2 0.798434 0.817558 0.779361 11.00000 -1.20000 AFIX 0 C15 1 0.944452 0.768896 0.843079 11.00000 0.03171 0.03363 = 0.01219 -0.00305 -0.00110 -0.01000 AFIX 43 H15 2 0.922697 0.826577 0.877784 11.00000 -1.20000 AFIX 0 C16 1 1.049527 0.690065 0.850342 11.00000 0.03413 0.03132 = 0.01782 0.00696 -0.01293 -0.01223 AFIX 43 H16 2 1.100244 0.694388 0.889977 11.00000 -1.20000 AFIX 0 C17 1 1.081257 0.605063 0.800353 11.00000 0.02658 0.02287 = 0.02926 0.00974 -0.01281 -0.00372 AFIX 43 H17 2 1.153373 0.551074 0.805799 11.00000 -1.20000 AFIX 0 C18 1 1.007818 0.598543 0.742207 11.00000 0.01975 0.01873 = 0.01977 0.00261 -0.00380 -0.00163 AFIX 43 H18 2 1.029320 0.539623 0.708055 11.00000 -1.20000 AFIX 0 C19 1 0.688681 0.549791 0.678177 11.00000 0.01456 0.01827 = 0.00918 -0.00179 0.00219 -0.00376 C20 1 0.729035 0.433665 0.703561 11.00000 0.01686 0.02000 = 0.01661 -0.00098 0.00196 -0.00128 AFIX 43 H20 2 0.818238 0.415803 0.707302 11.00000 -1.20000 AFIX 0 C21 1 0.639332 0.344193 0.723357 11.00000 0.02503 0.01902 = 0.01697 -0.00105 0.00353 -0.00375 AFIX 43 H21 2 0.667161 0.265249 0.740581 11.00000 -1.20000 AFIX 0 C22 1 0.508472 0.370210 0.717956 11.00000 0.02235 0.02620 = 0.01782 -0.00364 0.00639 -0.01026 AFIX 43 H22 2 0.446968 0.309225 0.731689 11.00000 -1.20000 AFIX 0 C23 1 0.468231 0.485137 0.692530 11.00000 0.01396 0.03079 = 0.02216 -0.00370 0.00342 -0.00551 AFIX 43 H23 2 0.378990 0.502744 0.688695 11.00000 -1.20000 AFIX 0 C24 1 0.557956 0.574964 0.672570 11.00000 0.01530 0.02307 = 0.01487 -0.00171 0.00130 -0.00136 AFIX 43 H24 2 0.529836 0.653607 0.655085 11.00000 -1.20000 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 954347' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mk80 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H34 Mo N O5 P' _chemical_formula_weight 531.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mo Mo -1.6832 0.6857 '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 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.7545(2) _cell_length_b 11.7669(3) _cell_length_c 18.8429(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2606.24(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 29672 _cell_measurement_theta_min 2.6710 _cell_measurement_theta_max 28.8670 _exptl_crystal_description fragment _exptl_crystal_colour 'pale brown-yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.595 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96679 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 138829 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.10 _reflns_number_total 5757 _reflns_number_gt 5466 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. The compound is achiral but crystallises by chance in a Sohncke space group. The hydrogen at N1 was found and refined freely. Methyls were refined as rigid groups allowed to rotate but not tip. Other hydrogens were included using a riding model starting from calculated positions. ; _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^)+(0.0284P)^2^+1.0279P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.06(2) _refine_ls_number_reflns 5757 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0557 _refine_ls_wR_factor_gt 0.0543 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Mo Mo 0.937231(14) 0.567712(15) 0.629041(8) 0.01695(5) Uani 1 1 d . . . N N 0.44896(16) 0.49320(15) 0.62258(10) 0.0223(4) Uani 1 1 d . . . H01 H 0.385(2) 0.481(2) 0.6219(14) 0.028(7) Uiso 1 1 d . . . P P 0.74134(5) 0.65068(5) 0.67059(3) 0.01701(11) Uani 1 1 d . . . C1 C 0.49981(17) 0.5737(2) 0.66495(11) 0.0222(4) Uani 1 1 d . . . C2 C 0.61700(17) 0.5655(2) 0.65035(10) 0.0194(4) Uani 1 1 d . . . C3 C 0.62956(18) 0.47892(19) 0.59758(11) 0.0193(4) Uani 1 1 d . . . H3 H 0.6996 0.4555 0.5771 0.023 Uiso 1 1 calc R . . C4 C 0.52545(17) 0.4355(2) 0.58136(10) 0.0199(4) Uani 1 1 d . . . C5 C 0.4236(2) 0.6378(2) 0.71737(13) 0.0302(5) Uani 1 1 d . . . C6 C 0.4345(3) 0.5834(2) 0.79147(13) 0.0391(6) Uani 1 1 d . . . H6A H 0.4155 0.5025 0.7885 0.059 Uiso 1 1 calc R . . H6B H 0.3821 0.6211 0.8244 0.059 Uiso 1 1 calc R . . H6C H 0.5127 0.5921 0.8086 0.059 Uiso 1 1 calc R . . C7 C 0.2980(2) 0.6264(3) 0.69564(19) 0.0529(9) Uani 1 1 d . . . H7A H 0.2766 0.5459 0.6953 0.079 Uiso 1 1 calc R . . H7B H 0.2873 0.6586 0.6481 0.079 Uiso 1 1 calc R . . H7C H 0.2502 0.6675 0.7297 0.079 Uiso 1 1 calc R . . C8 C 0.4479(2) 0.7645(2) 0.72239(14) 0.0340(6) Uani 1 1 d . . . H8A H 0.3919 0.8004 0.7537 0.051 Uiso 1 1 calc R . . H8B H 0.4430 0.7986 0.6750 0.051 Uiso 1 1 calc R . . H8C H 0.5244 0.7763 0.7416 0.051 Uiso 1 1 calc R . . C9 C 0.48933(19) 0.34941(19) 0.52651(11) 0.0214(4) Uani 1 1 d . . . C10 C 0.4073(2) 0.2628(2) 0.55804(13) 0.0301(5) Uani 1 1 d . . . H10A H 0.3872 0.2065 0.5218 0.045 Uiso 1 1 calc R . . H10B H 0.3383 0.3017 0.5743 0.045 Uiso 1 1 calc R . . H10C H 0.4436 0.2245 0.5983 0.045 Uiso 1 1 calc R . . C11 C 0.4287(3) 0.4112(2) 0.46560(12) 0.0394(6) Uani 1 1 d . . . H11A H 0.4797 0.4686 0.4453 0.059 Uiso 1 1 calc R . . H11B H 0.3599 0.4483 0.4837 0.059 Uiso 1 1 calc R . . H11C H 0.4077 0.3562 0.4288 0.059 Uiso 1 1 calc R . . C12 C 0.5938(2) 0.2885(3) 0.49868(16) 0.0406(7) Uani 1 1 d . . . H12A H 0.6443 0.3433 0.4754 0.061 Uiso 1 1 calc R . . H12B H 0.5707 0.2303 0.4644 0.061 Uiso 1 1 calc R . . H12C H 0.6341 0.2523 0.5382 0.061 Uiso 1 1 calc R . . C13 C 0.70108(19) 0.78955(18) 0.63068(15) 0.0288(5) Uani 1 1 d . . . H13 H 0.6440 0.8246 0.6634 0.035 Uiso 1 1 calc R . . C14 C 0.6402(3) 0.7732(3) 0.55842(19) 0.0585(9) Uani 1 1 d . . . H14A H 0.6130 0.8469 0.5411 0.088 Uiso 1 1 calc R . . H14B H 0.5755 0.7216 0.5644 0.088 Uiso 1 1 calc R . . H14C H 0.6937 0.7408 0.5240 0.088 Uiso 1 1 calc R . . C15 C 0.7961(3) 0.8735(3) 0.6235(2) 0.0598(10) Uani 1 1 d . . . H15A H 0.8450 0.8516 0.5837 0.090 Uiso 1 1 calc R . . H15B H 0.8410 0.8744 0.6673 0.090 Uiso 1 1 calc R . . H15C H 0.7645 0.9493 0.6149 0.090 Uiso 1 1 calc R . . C16 C 0.73668(19) 0.6727(2) 0.76797(11) 0.0236(5) Uani 1 1 d . . . H16 H 0.6592 0.7025 0.7797 0.028 Uiso 1 1 calc R . . C17 C 0.8227(2) 0.7611(2) 0.79350(14) 0.0362(6) Uani 1 1 d . . . H17A H 0.8293 0.7572 0.8453 0.054 Uiso 1 1 calc R . . H17B H 0.7970 0.8372 0.7796 0.054 Uiso 1 1 calc R . . H17C H 0.8970 0.7457 0.7719 0.054 Uiso 1 1 calc R . . C18 C 0.7499(2) 0.5592(2) 0.80637(12) 0.0322(5) Uani 1 1 d . . . H18A H 0.8281 0.5318 0.8009 0.048 Uiso 1 1 calc R . . H18B H 0.6971 0.5037 0.7860 0.048 Uiso 1 1 calc R . . H18C H 0.7329 0.5694 0.8569 0.048 Uiso 1 1 calc R . . C21 C 1.08232(19) 0.50427(19) 0.59365(11) 0.0224(5) Uani 1 1 d . . . O1 O 1.16810(14) 0.47067(14) 0.57273(10) 0.0301(4) Uani 1 1 d . . . C22 C 1.01485(19) 0.7233(2) 0.61910(13) 0.0277(5) Uani 1 1 d . . . O2 O 1.06830(17) 0.80299(15) 0.61543(12) 0.0460(5) Uani 1 1 d . . . C23 C 1.00698(18) 0.5635(2) 0.72794(11) 0.0264(5) Uani 1 1 d . . . O3 O 1.05364(16) 0.55883(19) 0.78070(8) 0.0406(4) Uani 1 1 d . . . C24 C 0.87862(19) 0.4066(2) 0.64996(12) 0.0262(5) Uani 1 1 d . . . O4 O 0.85378(16) 0.31648(15) 0.66485(11) 0.0391(4) Uani 1 1 d . . . C25 C 0.88229(18) 0.5702(2) 0.52551(11) 0.0271(5) Uani 1 1 d . . . O5 O 0.85949(16) 0.5699(2) 0.46685(8) 0.0472(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mo 0.01338(7) 0.01958(8) 0.01788(8) -0.00032(7) -0.00009(7) -0.00054(7) N 0.0128(9) 0.0274(9) 0.0268(9) -0.0100(8) 0.0002(8) -0.0001(7) P 0.0152(2) 0.0175(2) 0.0183(3) -0.0024(2) 0.0001(2) -0.0010(2) C1 0.0161(10) 0.0265(11) 0.0241(10) -0.0100(10) -0.0005(8) -0.0004(10) C2 0.0161(9) 0.0202(10) 0.0219(9) -0.0042(9) -0.0012(7) -0.0030(10) C3 0.0143(10) 0.0229(11) 0.0208(10) -0.0031(8) 0.0023(8) 0.0007(8) C4 0.0190(9) 0.0203(10) 0.0204(9) -0.0049(10) 0.0036(7) 0.0001(9) C5 0.0173(11) 0.0348(13) 0.0384(13) -0.0189(11) 0.0043(10) -0.0017(10) C6 0.0398(13) 0.0361(14) 0.0413(13) -0.0129(11) 0.0195(12) -0.0079(14) C7 0.0171(12) 0.068(2) 0.074(2) -0.0449(18) 0.0007(13) 0.0044(13) C8 0.0296(13) 0.0295(13) 0.0430(13) -0.0108(10) 0.0055(12) 0.0076(11) C9 0.0218(10) 0.0236(11) 0.0187(10) -0.0048(9) 0.0011(8) -0.0020(9) C10 0.0322(14) 0.0278(13) 0.0304(12) -0.0057(10) 0.0035(9) -0.0076(10) C11 0.0577(17) 0.0379(15) 0.0226(11) -0.0002(10) -0.0114(12) -0.0074(15) C12 0.0283(14) 0.0431(16) 0.0505(16) -0.0285(14) 0.0091(11) -0.0029(11) C13 0.0288(11) 0.0202(10) 0.0375(12) 0.0034(11) 0.0073(11) 0.0035(9) C14 0.062(2) 0.055(2) 0.058(2) 0.0245(17) -0.0138(17) 0.0059(18) C15 0.0421(17) 0.0342(15) 0.103(3) 0.0274(19) 0.0095(19) -0.0015(12) C16 0.0181(10) 0.0327(12) 0.0201(10) -0.0067(9) 0.0027(8) -0.0032(9) C17 0.0335(14) 0.0434(16) 0.0317(13) -0.0140(12) -0.0012(11) -0.0106(12) C18 0.0312(12) 0.0433(14) 0.0222(10) 0.0073(11) 0.0025(9) -0.0033(13) C21 0.0242(12) 0.0194(10) 0.0236(10) -0.0005(8) -0.0017(9) -0.0035(9) O1 0.0206(8) 0.0280(9) 0.0418(10) -0.0029(7) 0.0057(7) 0.0041(7) C22 0.0204(10) 0.0284(12) 0.0342(13) 0.0007(10) 0.0001(10) 0.0015(9) O2 0.0332(9) 0.0293(9) 0.0753(14) 0.0010(9) 0.0043(11) -0.0107(9) C23 0.0187(10) 0.0342(12) 0.0263(11) 0.0019(11) 0.0003(8) 0.0025(11) O3 0.0314(9) 0.0644(12) 0.0261(8) 0.0034(9) -0.0075(7) 0.0038(12) C24 0.0202(11) 0.0293(14) 0.0291(11) -0.0021(9) 0.0030(8) 0.0049(9) O4 0.0382(10) 0.0246(9) 0.0545(12) 0.0064(9) 0.0067(9) -0.0033(8) C25 0.0198(10) 0.0351(12) 0.0263(11) -0.0015(11) 0.0022(8) -0.0047(11) O5 0.0447(11) 0.0750(14) 0.0218(8) -0.0005(11) -0.0056(8) -0.0105(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 Mo C21 1.977(2) . ? Mo C23 2.036(2) . ? Mo C22 2.054(2) . ? Mo C24 2.055(2) . ? Mo C25 2.055(2) . ? Mo P 2.6208(6) . ? N C4 1.369(3) . ? N C1 1.376(3) . ? P C2 1.813(2) . ? P C16 1.854(2) . ? P C13 1.860(2) . ? C1 C2 1.408(3) . ? C1 C5 1.532(3) . ? C2 C3 1.431(3) . ? C3 C4 1.361(3) . ? C4 C9 1.508(3) . ? C5 C8 1.521(3) . ? C5 C7 1.537(3) . ? C5 C6 1.541(4) . ? C9 C12 1.516(3) . ? C9 C10 1.524(3) . ? C9 C11 1.534(3) . ? C13 C15 1.497(4) . ? C13 C14 1.550(4) . ? C16 C18 1.527(3) . ? C16 C17 1.529(3) . ? C21 O1 1.153(3) . ? C22 O2 1.131(3) . ? C23 O3 1.137(3) . ? C24 O4 1.135(3) . ? C25 O5 1.137(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 C21 Mo C23 87.26(9) . . ? C21 Mo C22 85.56(9) . . ? C23 Mo C22 85.78(10) . . ? C21 Mo C24 90.32(9) . . ? C23 Mo C24 86.38(10) . . ? C22 Mo C24 171.30(9) . . ? C21 Mo C25 87.50(9) . . ? C23 Mo C25 174.54(9) . . ? C22 Mo C25 92.30(10) . . ? C24 Mo C25 95.17(10) . . ? C21 Mo P 177.59(6) . . ? C23 Mo P 95.13(6) . . ? C22 Mo P 94.91(6) . . ? C24 Mo P 89.53(6) . . ? C25 Mo P 90.12(7) . . ? C4 N C1 112.70(18) . . ? C2 P C16 105.18(10) . . ? C2 P C13 101.28(11) . . ? C16 P C13 105.65(12) . . ? C2 P Mo 116.08(7) . . ? C16 P Mo 111.95(8) . . ? C13 P Mo 115.47(8) . . ? N C1 C2 105.33(19) . . ? N C1 C5 117.32(18) . . ? C2 C1 C5 137.1(2) . . ? C1 C2 C3 106.59(18) . . ? C1 C2 P 135.21(19) . . ? C3 C2 P 117.17(15) . . ? C4 C3 C2 109.32(18) . . ? C3 C4 N 106.05(18) . . ? C3 C4 C9 131.25(18) . . ? N C4 C9 122.51(18) . . ? C8 C5 C1 114.4(2) . . ? C8 C5 C7 106.4(2) . . ? C1 C5 C7 110.29(19) . . ? C8 C5 C6 109.6(2) . . ? C1 C5 C6 109.3(2) . . ? C7 C5 C6 106.5(2) . . ? C4 C9 C12 109.07(18) . . ? C4 C9 C10 111.10(18) . . ? C12 C9 C10 109.3(2) . . ? C4 C9 C11 109.00(19) . . ? C12 C9 C11 110.0(2) . . ? C10 C9 C11 108.3(2) . . ? C15 C13 C14 110.3(3) . . ? C15 C13 P 115.23(18) . . ? C14 C13 P 111.31(19) . . ? C18 C16 C17 112.3(2) . . ? C18 C16 P 110.10(16) . . ? C17 C16 P 112.77(17) . . ? O1 C21 Mo 177.88(19) . . ? O2 C22 Mo 172.5(2) . . ? O3 C23 Mo 174.7(2) . . ? O4 C24 Mo 174.5(2) . . ? O5 C25 Mo 175.2(2) . . ? 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 C21 Mo P C2 51.5(16) . . . . ? C23 Mo P C2 -121.27(11) . . . . ? C22 Mo P C2 152.55(11) . . . . ? C24 Mo P C2 -34.94(10) . . . . ? C25 Mo P C2 60.23(11) . . . . ? C21 Mo P C16 172.2(16) . . . . ? C23 Mo P C16 -0.51(11) . . . . ? C22 Mo P C16 -86.69(11) . . . . ? C24 Mo P C16 85.82(10) . . . . ? C25 Mo P C16 -179.01(11) . . . . ? C21 Mo P C13 -66.8(16) . . . . ? C23 Mo P C13 120.42(12) . . . . ? C22 Mo P C13 34.24(12) . . . . ? C24 Mo P C13 -153.25(11) . . . . ? C25 Mo P C13 -58.08(12) . . . . ? C4 N C1 C2 -0.8(3) . . . . ? C4 N C1 C5 -175.7(2) . . . . ? N C1 C2 C3 0.9(3) . . . . ? C5 C1 C2 C3 174.2(3) . . . . ? N C1 C2 P 168.42(18) . . . . ? C5 C1 C2 P -18.3(5) . . . . ? C16 P C2 C1 52.1(3) . . . . ? C13 P C2 C1 -57.7(3) . . . . ? Mo P C2 C1 176.4(2) . . . . ? C16 P C2 C3 -141.36(18) . . . . ? C13 P C2 C3 108.82(19) . . . . ? Mo P C2 C3 -17.0(2) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? P C2 C3 C4 -170.84(17) . . . . ? C2 C3 C4 N 0.2(3) . . . . ? C2 C3 C4 C9 175.2(2) . . . . ? C1 N C4 C3 0.4(3) . . . . ? C1 N C4 C9 -175.2(2) . . . . ? N C1 C5 C8 -138.2(2) . . . . ? C2 C1 C5 C8 49.1(4) . . . . ? N C1 C5 C7 -18.4(3) . . . . ? C2 C1 C5 C7 169.0(3) . . . . ? N C1 C5 C6 98.5(2) . . . . ? C2 C1 C5 C6 -74.2(4) . . . . ? C3 C4 C9 C12 14.3(4) . . . . ? N C4 C9 C12 -171.3(2) . . . . ? C3 C4 C9 C10 134.9(3) . . . . ? N C4 C9 C10 -50.7(3) . . . . ? C3 C4 C9 C11 -105.8(3) . . . . ? N C4 C9 C11 68.6(3) . . . . ? C2 P C13 C15 -166.9(2) . . . . ? C16 P C13 C15 83.7(3) . . . . ? Mo P C13 C15 -40.6(3) . . . . ? C2 P C13 C14 -40.3(2) . . . . ? C16 P C13 C14 -149.8(2) . . . . ? Mo P C13 C14 85.9(2) . . . . ? C2 P C16 C18 64.39(18) . . . . ? C13 P C16 C18 171.03(16) . . . . ? Mo P C16 C18 -62.51(17) . . . . ? C2 P C16 C17 -169.37(18) . . . . ? C13 P C16 C17 -62.7(2) . . . . ? Mo P C16 C17 63.74(19) . . . . ? C23 Mo C21 O1 -90(5) . . . . ? C22 Mo C21 O1 -4(5) . . . . ? C24 Mo C21 O1 -177(100) . . . . ? C25 Mo C21 O1 88(5) . . . . ? P Mo C21 O1 97(5) . . . . ? C21 Mo C22 O2 -32.4(17) . . . . ? C23 Mo C22 O2 55.2(17) . . . . ? C24 Mo C22 O2 30(2) . . . . ? C25 Mo C22 O2 -119.7(17) . . . . ? P Mo C22 O2 150.0(17) . . . . ? C21 Mo C23 O3 7(3) . . . . ? C22 Mo C23 O3 -79(3) . . . . ? C24 Mo C23 O3 98(3) . . . . ? C25 Mo C23 O3 -9(4) . . . . ? P Mo C23 O3 -173(3) . . . . ? C21 Mo C24 O4 57(2) . . . . ? C23 Mo C24 O4 -31(2) . . . . ? C22 Mo C24 O4 -5(3) . . . . ? C25 Mo C24 O4 144(2) . . . . ? P Mo C24 O4 -126(2) . . . . ? C21 Mo C25 O5 -10(3) . . . . ? C23 Mo C25 O5 6(4) . . . . ? C22 Mo C25 O5 76(3) . . . . ? C24 Mo C25 O5 -100(3) . . . . ? P Mo C25 O5 171(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.657 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.053 _iucr_refine_instructions_details ; TITL MK80 in P2(1)2(1)2(1) CELL 0.71073 11.754528 11.766887 18.842860 90.0000 90.0000 90.0000 ZERR 4.00 0.000200 0.000300 0.000400 0.0000 0.0000 0.0000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O P MO UNIT 92 136 4 20 4 4 MERG 2 FMAP 2 TEMP -173 SHEL 999 0.78 ACTA CONF OMIT 2 1 0 OMIT 4 2 0 OMIT 4 0 0 PLAN 10 L.S. 4 WGHT 0.028400 1.027900 FVAR 2.38978 MO 6 0.937231 0.567712 0.629041 11.00000 0.01338 0.01958 = 0.01788 -0.00032 -0.00009 -0.00054 N 3 0.448964 0.493204 0.622583 11.00000 0.01283 0.02737 = 0.02683 -0.01000 0.00017 -0.00006 H01 2 0.385192 0.481268 0.621904 11.00000 0.02779 P 5 0.741337 0.650684 0.670593 11.00000 0.01524 0.01747 = 0.01831 -0.00237 0.00005 -0.00097 C1 1 0.499815 0.573736 0.664948 11.00000 0.01606 0.02650 = 0.02414 -0.01001 -0.00049 -0.00040 C2 1 0.616995 0.565509 0.650350 11.00000 0.01610 0.02018 = 0.02190 -0.00419 -0.00122 -0.00298 C3 1 0.629556 0.478921 0.597584 11.00000 0.01429 0.02285 = 0.02079 -0.00311 0.00226 0.00073 AFIX 43 H3 2 0.699571 0.455468 0.577097 11.00000 -1.20000 AFIX 0 C4 1 0.525447 0.435452 0.581361 11.00000 0.01898 0.02028 = 0.02040 -0.00486 0.00357 0.00008 C5 1 0.423587 0.637811 0.717370 11.00000 0.01734 0.03480 = 0.03839 -0.01888 0.00427 -0.00174 C6 1 0.434462 0.583422 0.791472 11.00000 0.03980 0.03608 = 0.04128 -0.01291 0.01950 -0.00786 AFIX 137 H6A 2 0.415490 0.502460 0.788519 11.00000 -1.50000 H6B 2 0.382117 0.621141 0.824394 11.00000 -1.50000 H6C 2 0.512693 0.592082 0.808620 11.00000 -1.50000 AFIX 0 C7 1 0.298049 0.626422 0.695645 11.00000 0.01705 0.06814 = 0.07365 -0.04489 0.00068 0.00442 AFIX 137 H7A 2 0.276578 0.545948 0.695277 11.00000 -1.50000 H7B 2 0.287302 0.658570 0.648137 11.00000 -1.50000 H7C 2 0.250234 0.667485 0.729669 11.00000 -1.50000 AFIX 0 C8 1 0.447874 0.764545 0.722395 11.00000 0.02956 0.02953 = 0.04300 -0.01079 0.00546 0.00758 AFIX 137 H8A 2 0.391854 0.800391 0.753742 11.00000 -1.50000 H8B 2 0.442982 0.798616 0.675035 11.00000 -1.50000 H8C 2 0.524431 0.776268 0.741645 11.00000 -1.50000 AFIX 0 C9 1 0.489332 0.349412 0.526505 11.00000 0.02180 0.02357 = 0.01873 -0.00480 0.00109 -0.00203 C10 1 0.407297 0.262789 0.558039 11.00000 0.03219 0.02785 = 0.03040 -0.00572 0.00347 -0.00762 AFIX 137 H10A 2 0.387185 0.206489 0.521825 11.00000 -1.50000 H10B 2 0.338309 0.301651 0.574286 11.00000 -1.50000 H10C 2 0.443635 0.224518 0.598287 11.00000 -1.50000 AFIX 0 C11 1 0.428667 0.411194 0.465596 11.00000 0.05768 0.03794 = 0.02258 -0.00020 -0.01138 -0.00739 AFIX 137 H11A 2 0.479655 0.468559 0.445348 11.00000 -1.50000 H11B 2 0.359918 0.448286 0.483737 11.00000 -1.50000 H11C 2 0.407683 0.356196 0.428798 11.00000 -1.50000 AFIX 0 C12 1 0.593827 0.288461 0.498677 11.00000 0.02834 0.04312 = 0.05047 -0.02854 0.00910 -0.00293 AFIX 137 H12A 2 0.644288 0.343324 0.475435 11.00000 -1.50000 H12B 2 0.570654 0.230311 0.464365 11.00000 -1.50000 H12C 2 0.634090 0.252345 0.538243 11.00000 -1.50000 AFIX 0 C13 1 0.701084 0.789553 0.630684 11.00000 0.02876 0.02022 = 0.03747 0.00336 0.00734 0.00352 AFIX 13 H13 2 0.644044 0.824611 0.663412 11.00000 -1.20000 AFIX 0 C14 1 0.640245 0.773191 0.558416 11.00000 0.06210 0.05515 = 0.05835 0.02446 -0.01381 0.00586 AFIX 137 H14A 2 0.613012 0.846861 0.541099 11.00000 -1.50000 H14B 2 0.575537 0.721567 0.564439 11.00000 -1.50000 H14C 2 0.693721 0.740801 0.524022 11.00000 -1.50000 AFIX 0 C15 1 0.796094 0.873482 0.623524 11.00000 0.04207 0.03416 = 0.10322 0.02743 0.00954 -0.00147 AFIX 137 H15A 2 0.844965 0.851633 0.583657 11.00000 -1.50000 H15B 2 0.840981 0.874443 0.667348 11.00000 -1.50000 H15C 2 0.764538 0.949317 0.614879 11.00000 -1.50000 AFIX 0 C16 1 0.736678 0.672724 0.767975 11.00000 0.01809 0.03267 = 0.02012 -0.00669 0.00272 -0.00317 AFIX 13 H16 2 0.659240 0.702494 0.779691 11.00000 -1.20000 AFIX 0 C17 1 0.822727 0.761144 0.793500 11.00000 0.03346 0.04337 = 0.03175 -0.01403 -0.00116 -0.01063 AFIX 137 H17A 2 0.829320 0.757195 0.845287 11.00000 -1.50000 H17B 2 0.797003 0.837186 0.779625 11.00000 -1.50000 H17C 2 0.897021 0.745736 0.771950 11.00000 -1.50000 AFIX 0 C18 1 0.749892 0.559235 0.806371 11.00000 0.03117 0.04334 = 0.02224 0.00726 0.00253 -0.00332 AFIX 137 H18A 2 0.828135 0.531840 0.800899 11.00000 -1.50000 H18B 2 0.697113 0.503659 0.785964 11.00000 -1.50000 H18C 2 0.732911 0.569357 0.856896 11.00000 -1.50000 AFIX 0 C21 1 1.082318 0.504271 0.593650 11.00000 0.02416 0.01942 = 0.02355 -0.00047 -0.00168 -0.00351 O1 4 1.168100 0.470674 0.572734 11.00000 0.02059 0.02801 = 0.04181 -0.00289 0.00570 0.00406 C22 1 1.014851 0.723251 0.619104 11.00000 0.02041 0.02840 = 0.03417 0.00073 0.00008 0.00150 O2 4 1.068296 0.802985 0.615426 11.00000 0.03321 0.02935 = 0.07531 0.00104 0.00431 -0.01072 C23 1 1.006981 0.563484 0.727936 11.00000 0.01872 0.03417 = 0.02627 0.00191 0.00030 0.00248 O3 4 1.053641 0.558833 0.780705 11.00000 0.03136 0.06438 = 0.02613 0.00343 -0.00746 0.00377 C24 1 0.878621 0.406613 0.649963 11.00000 0.02019 0.02925 = 0.02906 -0.00211 0.00300 0.00490 O4 4 0.853777 0.316485 0.664851 11.00000 0.03819 0.02462 = 0.05452 0.00645 0.00671 -0.00331 C25 1 0.882291 0.570247 0.525508 11.00000 0.01976 0.03513 = 0.02631 -0.00154 0.00218 -0.00475 O5 4 0.859488 0.569905 0.466853 11.00000 0.04472 0.07503 = 0.02184 -0.00051 -0.00564 -0.01047 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 954348' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mk84 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H30 Mo N O5 P' _chemical_formula_weight 599.45 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' Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 10.5614(4) _cell_length_b 10.9521(4) _cell_length_c 14.1162(6) _cell_angle_alpha 74.208(4) _cell_angle_beta 79.031(3) _cell_angle_gamma 64.248(4) _cell_volume 1410.23(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 22847 _cell_measurement_theta_min 2.3990 _cell_measurement_theta_max 30.4580 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.559 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99555 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 75396 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.92 _reflns_number_total 8422 _reflns_number_gt 7585 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. The hydrogen at N was refined freely. Methyls were refined as rigid groups allowed to rotate but not tip. Other hydrogens were included using a riding model starting from calculated positions. ; _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^)+(0.0192P)^2^+0.8455P] 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 8422 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0570 _refine_ls_wR_factor_gt 0.0544 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.003 _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 Mo Mo 0.663058(12) 0.529394(11) 0.268433(8) 0.01084(3) Uani 1 1 d . . . P P 0.70121(3) 0.71897(3) 0.31862(2) 0.00998(6) Uani 1 1 d . . . O1 O 0.59813(12) 0.32255(11) 0.18925(8) 0.0217(2) Uani 1 1 d . . . O2 O 0.68228(14) 0.68472(13) 0.04384(8) 0.0317(3) Uani 1 1 d . . . O3 O 0.99248(12) 0.33488(12) 0.25930(9) 0.0289(3) Uani 1 1 d . . . O4 O 0.64144(13) 0.35548(12) 0.48813(8) 0.0273(2) Uani 1 1 d . . . O5 O 0.33051(11) 0.70191(12) 0.28139(9) 0.0259(2) Uani 1 1 d . . . N N 1.03236(13) 0.81556(12) 0.20784(9) 0.0143(2) Uani 1 1 d . . . H01 H 1.087(2) 0.8492(19) 0.2030(13) 0.021(5) Uiso 1 1 d . . . C1 C 0.92593(14) 0.82350(13) 0.28195(10) 0.0129(2) Uani 1 1 d . . . C2 C 0.86049(14) 0.74418(13) 0.26600(9) 0.0119(2) Uani 1 1 d . . . C3 C 0.93407(14) 0.69153(14) 0.17951(10) 0.0139(2) Uani 1 1 d . . . H3 H 0.9131 0.6338 0.1511 0.017 Uiso 1 1 calc R . . C4 C 1.03884(14) 0.73730(14) 0.14444(10) 0.0142(3) Uani 1 1 d . . . C5 C 0.90414(14) 0.91008(14) 0.35675(10) 0.0144(3) Uani 1 1 d . . . C6 C 0.95107(16) 0.81700(15) 0.45783(11) 0.0199(3) Uani 1 1 d . . . H6A H 0.9358 0.8750 0.5044 0.030 Uiso 1 1 calc R . . H6B H 1.0514 0.7559 0.4510 0.030 Uiso 1 1 calc R . . H6C H 0.8959 0.7607 0.4826 0.030 Uiso 1 1 calc R . . C7 C 0.74944(15) 1.01176(14) 0.36706(11) 0.0182(3) Uani 1 1 d . . . H7A H 0.7217 1.0728 0.3026 0.027 Uiso 1 1 calc R . . H7B H 0.7379 1.0678 0.4142 0.027 Uiso 1 1 calc R . . H7C H 0.6898 0.9598 0.3909 0.027 Uiso 1 1 calc R . . C8 C 0.99223(17) 0.99723(17) 0.32212(12) 0.0237(3) Uani 1 1 d . . . H8A H 0.9683 1.0546 0.2561 0.035 Uiso 1 1 calc R . . H8B H 1.0927 0.9355 0.3198 0.035 Uiso 1 1 calc R . . H8C H 0.9719 1.0572 0.3683 0.035 Uiso 1 1 calc R . . C9 C 1.14373(15) 0.71632(15) 0.05455(10) 0.0168(3) Uani 1 1 d . . . C10 C 1.26985(17) 0.57717(17) 0.07708(12) 0.0263(3) Uani 1 1 d . . . H10A H 1.3165 0.5752 0.1315 0.040 Uiso 1 1 calc R . . H10B H 1.3367 0.5651 0.0183 0.040 Uiso 1 1 calc R . . H10C H 1.2373 0.5019 0.0959 0.040 Uiso 1 1 calc R . . C11 C 1.19801(19) 0.83184(18) 0.02161(13) 0.0300(4) Uani 1 1 d . . . H11A H 1.1180 0.9222 0.0085 0.045 Uiso 1 1 calc R . . H11B H 1.2615 0.8185 -0.0387 0.045 Uiso 1 1 calc R . . H11C H 1.2492 0.8286 0.0740 0.045 Uiso 1 1 calc R . . C12 C 1.06936(18) 0.7190(2) -0.02959(12) 0.0313(4) Uani 1 1 d . . . H12A H 1.0390 0.6422 -0.0107 0.047 Uiso 1 1 calc R . . H12B H 1.1346 0.7091 -0.0893 0.047 Uiso 1 1 calc R . . H12C H 0.9869 0.8073 -0.0426 0.047 Uiso 1 1 calc R . . C13 C 0.69894(14) 0.69084(13) 0.45246(9) 0.0113(2) Uani 1 1 d . . . C14 C 0.80259(14) 0.56647(14) 0.49764(10) 0.0145(3) Uani 1 1 d . . . H14 H 0.8663 0.5028 0.4586 0.017 Uiso 1 1 calc R . . C15 C 0.81361(16) 0.53494(15) 0.59850(10) 0.0176(3) Uani 1 1 d . . . H15 H 0.8855 0.4509 0.6282 0.021 Uiso 1 1 calc R . . C16 C 0.71909(16) 0.62670(15) 0.65611(10) 0.0189(3) Uani 1 1 d . . . H16 H 0.7267 0.6059 0.7252 0.023 Uiso 1 1 calc R . . C17 C 0.61371(15) 0.74860(15) 0.61269(10) 0.0170(3) Uani 1 1 d . . . H17 H 0.5480 0.8103 0.6523 0.020 Uiso 1 1 calc R . . C18 C 0.60373(14) 0.78093(14) 0.51140(10) 0.0134(2) Uani 1 1 d . . . H18 H 0.5315 0.8650 0.4821 0.016 Uiso 1 1 calc R . . C19 C 0.55975(14) 0.88741(13) 0.27443(10) 0.0122(2) Uani 1 1 d . . . C20 C 0.58732(15) 0.97411(15) 0.18774(10) 0.0176(3) Uani 1 1 d . . . H20 H 0.6810 0.9504 0.1577 0.021 Uiso 1 1 calc R . . C21 C 0.47907(16) 1.09456(16) 0.14509(11) 0.0212(3) Uani 1 1 d . . . H21 H 0.4988 1.1515 0.0854 0.025 Uiso 1 1 calc R . . C22 C 0.34229(16) 1.13213(15) 0.18907(11) 0.0198(3) Uani 1 1 d . . . H22 H 0.2685 1.2149 0.1600 0.024 Uiso 1 1 calc R . . C23 C 0.31400(15) 1.04800(14) 0.27588(11) 0.0165(3) Uani 1 1 d . . . H23 H 0.2209 1.0745 0.3071 0.020 Uiso 1 1 calc R . . C24 C 0.42102(14) 0.92501(14) 0.31763(10) 0.0138(2) Uani 1 1 d . . . H24 H 0.3998 0.8664 0.3757 0.017 Uiso 1 1 calc R . . C25 C 0.62329(15) 0.39502(14) 0.22038(10) 0.0153(3) Uani 1 1 d . . . C26 C 0.67555(16) 0.63129(15) 0.12471(11) 0.0182(3) Uani 1 1 d . . . C27 C 0.87549(16) 0.40668(14) 0.26194(10) 0.0169(3) Uani 1 1 d . . . C28 C 0.64865(15) 0.42098(15) 0.41114(10) 0.0167(3) Uani 1 1 d . . . C29 C 0.45006(15) 0.64299(14) 0.27840(10) 0.0163(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mo 0.01051(6) 0.01118(5) 0.01110(5) -0.00281(4) -0.00073(4) -0.00447(4) P 0.00857(15) 0.01065(14) 0.01017(14) -0.00248(11) -0.00044(11) -0.00339(12) O1 0.0267(6) 0.0224(5) 0.0220(5) -0.0087(4) 0.0022(4) -0.0147(5) O2 0.0422(8) 0.0371(7) 0.0166(5) 0.0041(5) -0.0084(5) -0.0201(6) O3 0.0153(5) 0.0228(6) 0.0430(7) -0.0083(5) -0.0012(5) -0.0023(5) O4 0.0356(7) 0.0299(6) 0.0179(5) 0.0011(5) -0.0012(5) -0.0186(5) O5 0.0139(5) 0.0271(6) 0.0385(7) -0.0135(5) -0.0048(5) -0.0050(5) N 0.0111(5) 0.0174(6) 0.0168(6) -0.0051(4) 0.0014(4) -0.0082(5) C1 0.0102(6) 0.0129(6) 0.0143(6) -0.0032(5) -0.0002(5) -0.0037(5) C2 0.0098(6) 0.0121(6) 0.0124(6) -0.0025(5) -0.0010(5) -0.0033(5) C3 0.0136(6) 0.0152(6) 0.0132(6) -0.0043(5) 0.0001(5) -0.0059(5) C4 0.0125(6) 0.0162(6) 0.0136(6) -0.0049(5) 0.0012(5) -0.0054(5) C5 0.0126(6) 0.0148(6) 0.0181(6) -0.0065(5) 0.0001(5) -0.0065(5) C6 0.0222(7) 0.0206(7) 0.0193(7) -0.0074(6) -0.0065(6) -0.0072(6) C7 0.0162(7) 0.0146(6) 0.0235(7) -0.0077(5) 0.0005(5) -0.0047(5) C8 0.0235(8) 0.0260(8) 0.0309(8) -0.0147(6) 0.0058(6) -0.0167(7) C9 0.0141(6) 0.0210(7) 0.0145(6) -0.0048(5) 0.0033(5) -0.0075(6) C10 0.0228(8) 0.0258(8) 0.0207(7) -0.0069(6) 0.0052(6) -0.0027(6) C11 0.0314(9) 0.0292(9) 0.0283(8) -0.0080(7) 0.0140(7) -0.0167(7) C12 0.0239(8) 0.0547(11) 0.0165(7) -0.0117(7) 0.0040(6) -0.0169(8) C13 0.0119(6) 0.0121(6) 0.0111(6) -0.0022(5) -0.0007(5) -0.0062(5) C14 0.0138(6) 0.0128(6) 0.0154(6) -0.0037(5) -0.0014(5) -0.0036(5) C15 0.0202(7) 0.0150(6) 0.0163(6) 0.0003(5) -0.0067(5) -0.0059(6) C16 0.0245(8) 0.0213(7) 0.0119(6) -0.0010(5) -0.0025(5) -0.0115(6) C17 0.0168(7) 0.0207(7) 0.0143(6) -0.0063(5) 0.0023(5) -0.0083(6) C18 0.0115(6) 0.0134(6) 0.0148(6) -0.0033(5) -0.0009(5) -0.0045(5) C19 0.0105(6) 0.0119(6) 0.0137(6) -0.0023(5) -0.0031(5) -0.0036(5) C20 0.0137(7) 0.0194(7) 0.0164(6) 0.0010(5) -0.0019(5) -0.0064(6) C21 0.0186(7) 0.0200(7) 0.0193(7) 0.0051(6) -0.0045(6) -0.0070(6) C22 0.0164(7) 0.0145(6) 0.0252(7) 0.0005(5) -0.0087(6) -0.0033(5) C23 0.0103(6) 0.0151(6) 0.0242(7) -0.0053(5) -0.0018(5) -0.0044(5) C24 0.0123(6) 0.0131(6) 0.0166(6) -0.0031(5) -0.0009(5) -0.0058(5) C25 0.0147(6) 0.0166(6) 0.0133(6) -0.0023(5) 0.0009(5) -0.0064(5) C26 0.0183(7) 0.0189(7) 0.0192(7) -0.0042(5) -0.0047(5) -0.0079(6) C27 0.0193(7) 0.0148(6) 0.0178(6) -0.0037(5) -0.0006(5) -0.0083(6) C28 0.0167(7) 0.0180(6) 0.0179(7) -0.0062(5) -0.0006(5) -0.0083(5) C29 0.0175(7) 0.0163(6) 0.0183(7) -0.0053(5) -0.0032(5) -0.0081(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 Mo C25 1.9978(14) . ? Mo C29 2.0423(15) . ? Mo C26 2.0427(15) . ? Mo C27 2.0535(15) . ? Mo C28 2.0565(15) . ? Mo P 2.5712(4) . ? P C2 1.8094(14) . ? P C13 1.8269(13) . ? P C19 1.8323(13) . ? O1 C25 1.1450(17) . ? O2 C26 1.1367(18) . ? O3 C27 1.1404(18) . ? O4 C28 1.1372(18) . ? O5 C29 1.1397(18) . ? N C1 1.3720(17) . ? N C4 1.3724(17) . ? C1 C2 1.4038(18) . ? C1 C5 1.5264(18) . ? C2 C3 1.4352(18) . ? C3 C4 1.3635(19) . ? C4 C9 1.5142(19) . ? C5 C7 1.5321(19) . ? C5 C6 1.536(2) . ? C5 C8 1.5363(19) . ? C9 C10 1.527(2) . ? C9 C12 1.531(2) . ? C9 C11 1.534(2) . ? C13 C18 1.3940(18) . ? C13 C14 1.3991(18) . ? C14 C15 1.3857(19) . ? C15 C16 1.390(2) . ? C16 C17 1.386(2) . ? C17 C18 1.3893(19) . ? C19 C20 1.3987(19) . ? C19 C24 1.4002(19) . ? C20 C21 1.389(2) . ? C21 C22 1.387(2) . ? C22 C23 1.387(2) . ? C23 C24 1.3920(19) . ? 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 C25 Mo C29 86.87(5) . . ? C25 Mo C26 88.00(6) . . ? C29 Mo C26 89.80(6) . . ? C25 Mo C27 91.24(6) . . ? C29 Mo C27 177.20(6) . . ? C26 Mo C27 92.20(6) . . ? C25 Mo C28 89.58(5) . . ? C29 Mo C28 90.04(6) . . ? C26 Mo C28 177.59(5) . . ? C27 Mo C28 87.87(6) . . ? C25 Mo P 175.03(4) . . ? C29 Mo P 90.09(4) . . ? C26 Mo P 88.05(4) . . ? C27 Mo P 91.94(4) . . ? C28 Mo P 94.35(4) . . ? C2 P C13 106.60(6) . . ? C2 P C19 103.60(6) . . ? C13 P C19 108.53(6) . . ? C2 P Mo 116.75(4) . . ? C13 P Mo 112.05(4) . . ? C19 P Mo 108.77(4) . . ? C1 N C4 112.70(12) . . ? N C1 C2 105.72(11) . . ? N C1 C5 118.44(12) . . ? C2 C1 C5 135.83(12) . . ? C1 C2 C3 106.43(11) . . ? C1 C2 P 134.14(10) . . ? C3 C2 P 118.79(10) . . ? C4 C3 C2 109.34(12) . . ? C3 C4 N 105.80(12) . . ? C3 C4 C9 131.05(12) . . ? N C4 C9 123.13(12) . . ? C1 C5 C7 110.63(11) . . ? C1 C5 C6 111.11(11) . . ? C7 C5 C6 110.18(12) . . ? C1 C5 C8 110.44(11) . . ? C7 C5 C8 107.00(11) . . ? C6 C5 C8 107.34(12) . . ? C4 C9 C10 110.44(12) . . ? C4 C9 C12 108.26(12) . . ? C10 C9 C12 109.61(13) . . ? C4 C9 C11 111.24(12) . . ? C10 C9 C11 108.43(13) . . ? C12 C9 C11 108.83(14) . . ? C18 C13 C14 118.67(12) . . ? C18 C13 P 125.77(10) . . ? C14 C13 P 115.56(10) . . ? C15 C14 C13 120.90(13) . . ? C14 C15 C16 119.75(13) . . ? C17 C16 C15 119.94(13) . . ? C16 C17 C18 120.28(13) . . ? C17 C18 C13 120.43(13) . . ? C20 C19 C24 118.64(12) . . ? C20 C19 P 118.80(10) . . ? C24 C19 P 122.10(10) . . ? C21 C20 C19 120.63(13) . . ? C22 C21 C20 120.39(14) . . ? C21 C22 C23 119.50(13) . . ? C22 C23 C24 120.53(13) . . ? C23 C24 C19 120.27(13) . . ? O1 C25 Mo 176.96(12) . . ? O2 C26 Mo 177.88(13) . . ? O3 C27 Mo 177.81(13) . . ? O4 C28 Mo 176.48(12) . . ? O5 C29 Mo 176.40(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C25 Mo P C2 -95.2(5) . . . . ? C29 Mo P C2 -147.44(6) . . . . ? C26 Mo P C2 -57.64(6) . . . . ? C27 Mo P C2 34.50(6) . . . . ? C28 Mo P C2 122.52(6) . . . . ? C25 Mo P C13 141.5(5) . . . . ? C29 Mo P C13 89.25(6) . . . . ? C26 Mo P C13 179.05(6) . . . . ? C27 Mo P C13 -88.81(6) . . . . ? C28 Mo P C13 -0.80(6) . . . . ? C25 Mo P C19 21.5(5) . . . . ? C29 Mo P C19 -30.73(6) . . . . ? C26 Mo P C19 59.07(6) . . . . ? C27 Mo P C19 151.21(6) . . . . ? C28 Mo P C19 -120.78(6) . . . . ? C4 N C1 C2 0.64(15) . . . . ? C4 N C1 C5 -178.66(12) . . . . ? N C1 C2 C3 -0.23(14) . . . . ? C5 C1 C2 C3 178.88(14) . . . . ? N C1 C2 P -170.57(11) . . . . ? C5 C1 C2 P 8.5(3) . . . . ? C13 P C2 C1 -46.02(15) . . . . ? C19 P C2 C1 68.39(15) . . . . ? Mo P C2 C1 -172.09(12) . . . . ? C13 P C2 C3 144.57(10) . . . . ? C19 P C2 C3 -101.02(11) . . . . ? Mo P C2 C3 18.49(12) . . . . ? C1 C2 C3 C4 -0.24(15) . . . . ? P C2 C3 C4 171.86(10) . . . . ? C2 C3 C4 N 0.61(15) . . . . ? C2 C3 C4 C9 -177.94(14) . . . . ? C1 N C4 C3 -0.79(16) . . . . ? C1 N C4 C9 177.90(12) . . . . ? N C1 C5 C7 129.11(13) . . . . ? C2 C1 C5 C7 -49.9(2) . . . . ? N C1 C5 C6 -108.17(14) . . . . ? C2 C1 C5 C6 72.8(2) . . . . ? N C1 C5 C8 10.84(17) . . . . ? C2 C1 C5 C8 -168.19(15) . . . . ? C3 C4 C9 C10 -83.07(19) . . . . ? N C4 C9 C10 98.60(16) . . . . ? C3 C4 C9 C12 36.9(2) . . . . ? N C4 C9 C12 -141.39(15) . . . . ? C3 C4 C9 C11 156.47(16) . . . . ? N C4 C9 C11 -21.86(19) . . . . ? C2 P C13 C18 112.29(12) . . . . ? C19 P C13 C18 1.27(13) . . . . ? Mo P C13 C18 -118.85(11) . . . . ? C2 P C13 C14 -68.21(11) . . . . ? C19 P C13 C14 -179.24(10) . . . . ? Mo P C13 C14 60.65(11) . . . . ? C18 C13 C14 C15 -2.0(2) . . . . ? P C13 C14 C15 178.49(11) . . . . ? C13 C14 C15 C16 1.1(2) . . . . ? C14 C15 C16 C17 0.5(2) . . . . ? C15 C16 C17 C18 -1.3(2) . . . . ? C16 C17 C18 C13 0.4(2) . . . . ? C14 C13 C18 C17 1.2(2) . . . . ? P C13 C18 C17 -179.30(11) . . . . ? C2 P C19 C20 24.60(12) . . . . ? C13 P C19 C20 137.62(11) . . . . ? Mo P C19 C20 -100.24(11) . . . . ? C2 P C19 C24 -163.22(11) . . . . ? C13 P C19 C24 -50.20(12) . . . . ? Mo P C19 C24 71.94(11) . . . . ? C24 C19 C20 C21 -0.4(2) . . . . ? P C19 C20 C21 172.05(11) . . . . ? C19 C20 C21 C22 1.3(2) . . . . ? C20 C21 C22 C23 -0.4(2) . . . . ? C21 C22 C23 C24 -1.5(2) . . . . ? C22 C23 C24 C19 2.4(2) . . . . ? C20 C19 C24 C23 -1.5(2) . . . . ? P C19 C24 C23 -173.66(10) . . . . ? C29 Mo C25 O1 64(2) . . . . ? C26 Mo C25 O1 -26(2) . . . . ? C27 Mo C25 O1 -118(2) . . . . ? C28 Mo C25 O1 154(2) . . . . ? P Mo C25 O1 11(3) . . . . ? C25 Mo C26 O2 -8(4) . . . . ? C29 Mo C26 O2 -95(4) . . . . ? C27 Mo C26 O2 83(4) . . . . ? C28 Mo C26 O2 -9(5) . . . . ? P Mo C26 O2 175(4) . . . . ? C25 Mo C27 O3 -37(3) . . . . ? C29 Mo C27 O3 11(4) . . . . ? C26 Mo C27 O3 -125(3) . . . . ? C28 Mo C27 O3 53(3) . . . . ? P Mo C27 O3 147(3) . . . . ? C25 Mo C28 O4 17(2) . . . . ? C29 Mo C28 O4 104(2) . . . . ? C26 Mo C28 O4 17(3) . . . . ? C27 Mo C28 O4 -75(2) . . . . ? P Mo C28 O4 -166(2) . . . . ? C25 Mo C29 O5 -10(2) . . . . ? C26 Mo C29 O5 78(2) . . . . ? C27 Mo C29 O5 -57(3) . . . . ? C28 Mo C29 O5 -99(2) . . . . ? P Mo C29 O5 166(2) . . . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.479 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.070 _iucr_refine_instructions_details ; TITL MK84 in P-1 New: P-1 CELL 0.71073 10.561368 10.952079 14.116168 74.2076 79.0306 64.2478 ZERR 2.00 0.000400 0.000400 0.000600 0.0040 0.0030 0.0040 LATT 1 SFAC C H Mo O P N UNIT 58 60 2 10 2 2 OMIT 1 -3 4 TEMP -173 L.S. 4 FMAP 2 PLAN 10 ACTA 60 CONF WGHT 0.019200 0.845500 FVAR 3.66143 MO 3 0.663058 0.529394 0.268433 11.00000 0.01051 0.01118 = 0.01110 -0.00281 -0.00073 -0.00447 P 5 0.701206 0.718973 0.318616 11.00000 0.00857 0.01065 = 0.01017 -0.00248 -0.00044 -0.00339 O1 4 0.598135 0.322552 0.189254 11.00000 0.02666 0.02243 = 0.02196 -0.00874 0.00224 -0.01474 O2 4 0.682282 0.684721 0.043843 11.00000 0.04217 0.03711 = 0.01656 0.00412 -0.00839 -0.02008 O3 4 0.992482 0.334883 0.259303 11.00000 0.01530 0.02283 = 0.04301 -0.00830 -0.00124 -0.00232 O4 4 0.641441 0.355483 0.488133 11.00000 0.03557 0.02989 = 0.01792 0.00108 -0.00124 -0.01855 O5 4 0.330512 0.701911 0.281386 11.00000 0.01391 0.02711 = 0.03853 -0.01351 -0.00481 -0.00500 N 6 1.032357 0.815562 0.207842 11.00000 0.01113 0.01735 = 0.01683 -0.00514 0.00138 -0.00821 H01 2 1.087082 0.849180 0.202986 11.00000 0.02117 C1 1 0.925930 0.823504 0.281948 11.00000 0.01019 0.01286 = 0.01429 -0.00325 -0.00019 -0.00369 C2 1 0.860487 0.744176 0.266005 11.00000 0.00981 0.01212 = 0.01236 -0.00247 -0.00105 -0.00333 C3 1 0.934067 0.691530 0.179509 11.00000 0.01362 0.01519 = 0.01323 -0.00428 0.00008 -0.00588 AFIX 43 H3 2 0.913062 0.633828 0.151130 11.00000 -1.20000 AFIX 0 C4 1 1.038839 0.737303 0.144443 11.00000 0.01255 0.01615 = 0.01363 -0.00487 0.00117 -0.00543 C5 1 0.904139 0.910076 0.356755 11.00000 0.01258 0.01484 = 0.01810 -0.00649 0.00015 -0.00653 C6 1 0.951069 0.816999 0.457827 11.00000 0.02216 0.02062 = 0.01933 -0.00735 -0.00645 -0.00717 AFIX 137 H6A 2 0.935840 0.875002 0.504421 11.00000 -1.50000 H6B 2 1.051441 0.755948 0.450993 11.00000 -1.50000 H6C 2 0.895870 0.760656 0.482559 11.00000 -1.50000 AFIX 0 C7 1 0.749443 1.011758 0.367059 11.00000 0.01616 0.01463 = 0.02346 -0.00770 0.00048 -0.00469 AFIX 137 H7A 2 0.721659 1.072793 0.302627 11.00000 -1.50000 H7B 2 0.737887 1.067751 0.414220 11.00000 -1.50000 H7C 2 0.689832 0.959771 0.390923 11.00000 -1.50000 AFIX 0 C8 1 0.992226 0.997229 0.322117 11.00000 0.02346 0.02605 = 0.03088 -0.01474 0.00576 -0.01674 AFIX 137 H8A 2 0.968268 1.054594 0.256087 11.00000 -1.50000 H8B 2 1.092744 0.935475 0.319842 11.00000 -1.50000 H8C 2 0.971858 1.057214 0.368326 11.00000 -1.50000 AFIX 0 C9 1 1.143729 0.716323 0.054545 11.00000 0.01408 0.02099 = 0.01449 -0.00483 0.00332 -0.00754 C10 1 1.269846 0.577165 0.077078 11.00000 0.02279 0.02576 = 0.02067 -0.00686 0.00524 -0.00267 AFIX 137 H10A 2 1.316508 0.575211 0.131539 11.00000 -1.50000 H10B 2 1.336652 0.565081 0.018262 11.00000 -1.50000 H10C 2 1.237321 0.501889 0.095897 11.00000 -1.50000 AFIX 0 C11 1 1.198011 0.831836 0.021609 11.00000 0.03136 0.02917 = 0.02831 -0.00804 0.01405 -0.01673 AFIX 137 H11A 2 1.118024 0.922176 0.008479 11.00000 -1.50000 H11B 2 1.261530 0.818505 -0.038657 11.00000 -1.50000 H11C 2 1.249152 0.828611 0.073969 11.00000 -1.50000 AFIX 0 C12 1 1.069363 0.718988 -0.029586 11.00000 0.02390 0.05466 = 0.01649 -0.01175 0.00396 -0.01687 AFIX 137 H12A 2 1.039013 0.642220 -0.010714 11.00000 -1.50000 H12B 2 1.134614 0.709144 -0.089277 11.00000 -1.50000 H12C 2 0.986866 0.807307 -0.042617 11.00000 -1.50000 AFIX 0 C13 1 0.698937 0.690838 0.452462 11.00000 0.01193 0.01213 = 0.01113 -0.00221 -0.00067 -0.00620 C14 1 0.802589 0.566470 0.497644 11.00000 0.01384 0.01284 = 0.01536 -0.00366 -0.00138 -0.00362 AFIX 43 H14 2 0.866281 0.502774 0.458647 11.00000 -1.20000 AFIX 0 C15 1 0.813605 0.534939 0.598500 11.00000 0.02022 0.01495 = 0.01630 0.00033 -0.00667 -0.00593 AFIX 43 H15 2 0.885485 0.450923 0.628155 11.00000 -1.20000 AFIX 0 C16 1 0.719093 0.626699 0.656111 11.00000 0.02455 0.02131 = 0.01191 -0.00099 -0.00249 -0.01149 AFIX 43 H16 2 0.726738 0.605853 0.725198 11.00000 -1.20000 AFIX 0 C17 1 0.613712 0.748604 0.612688 11.00000 0.01679 0.02071 = 0.01431 -0.00635 0.00234 -0.00835 AFIX 43 H17 2 0.548013 0.810341 0.652343 11.00000 -1.20000 AFIX 0 C18 1 0.603725 0.780930 0.511402 11.00000 0.01150 0.01339 = 0.01480 -0.00329 -0.00090 -0.00447 AFIX 43 H18 2 0.531537 0.864982 0.482118 11.00000 -1.20000 AFIX 0 C19 1 0.559755 0.887408 0.274435 11.00000 0.01047 0.01194 = 0.01374 -0.00232 -0.00311 -0.00356 C20 1 0.587322 0.974111 0.187737 11.00000 0.01373 0.01941 = 0.01638 0.00095 -0.00188 -0.00640 AFIX 43 H20 2 0.680985 0.950384 0.157738 11.00000 -1.20000 AFIX 0 C21 1 0.479069 1.094562 0.145088 11.00000 0.01859 0.02001 = 0.01928 0.00506 -0.00454 -0.00695 AFIX 43 H21 2 0.498846 1.151545 0.085434 11.00000 -1.20000 AFIX 0 C22 1 0.342286 1.132134 0.189070 11.00000 0.01635 0.01455 = 0.02520 0.00054 -0.00874 -0.00334 AFIX 43 H22 2 0.268497 1.214858 0.159984 11.00000 -1.20000 AFIX 0 C23 1 0.314004 1.048001 0.275876 11.00000 0.01029 0.01512 = 0.02420 -0.00532 -0.00183 -0.00440 AFIX 43 H23 2 0.220856 1.074544 0.307068 11.00000 -1.20000 AFIX 0 C24 1 0.421025 0.925010 0.317629 11.00000 0.01233 0.01314 = 0.01661 -0.00310 -0.00095 -0.00582 AFIX 43 H24 2 0.399850 0.866352 0.375662 11.00000 -1.20000 AFIX 0 C25 1 0.623288 0.395022 0.220382 11.00000 0.01475 0.01657 = 0.01326 -0.00231 0.00091 -0.00643 C26 1 0.675553 0.631288 0.124707 11.00000 0.01827 0.01885 = 0.01924 -0.00418 -0.00473 -0.00785 C27 1 0.875492 0.406676 0.261936 11.00000 0.01931 0.01480 = 0.01780 -0.00368 -0.00063 -0.00832 C28 1 0.648654 0.420978 0.411136 11.00000 0.01668 0.01801 = 0.01792 -0.00616 -0.00060 -0.00826 C29 1 0.450059 0.642986 0.278399 11.00000 0.01754 0.01632 = 0.01828 -0.00535 -0.00320 -0.00807 HKLF 4 ; _database_code_depnum_ccdc_archive 'CCDC 954349' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mk85 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H29 Mn N O3 P' _chemical_formula_weight 501.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 12.2638(5) _cell_length_b 11.1697(4) _cell_length_c 19.4812(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.593(4) _cell_angle_gamma 90.00 _cell_volume 2593.85(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 14515 _cell_measurement_theta_min 2.8190 _cell_measurement_theta_max 29.2330 _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.284 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.598 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98114 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 94219 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 30.97 _reflns_number_total 7875 _reflns_number_gt 6186 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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. One tert-butyl group is disordered and was refined on two positions (ca. 50:50 ratio). ; _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^)+(0.0338P)^2^+1.5218P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7875 _refine_ls_number_parameters 305 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0900 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.045 _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 Mn Mn 0.276373(19) 0.90755(2) 0.332670(12) 0.01585(6) Uani 1 1 d . . . P P 0.20107(3) 0.68199(3) 0.440082(19) 0.01588(8) Uani 1 1 d . . . N N 0.38033(10) 0.77950(11) 0.29642(7) 0.0177(2) Uani 1 1 d . . . O1 O 0.05936(10) 1.03106(11) 0.28650(6) 0.0291(3) Uani 1 1 d . . . O2 O 0.30391(13) 1.00699(12) 0.47564(7) 0.0378(3) Uani 1 1 d . . . O3 O 0.39761(12) 1.10978(12) 0.28764(8) 0.0399(3) Uani 1 1 d . . . C1 C 0.37428(12) 0.74939(13) 0.36397(8) 0.0165(3) Uani 1 1 d . A . C2 C 0.25847(12) 0.72660(13) 0.36544(7) 0.0156(3) Uani 1 1 d . . . C3 C 0.19655(12) 0.74220(13) 0.29454(7) 0.0159(3) Uani 1 1 d . . . H3 H 0.1178 0.7329 0.2777 0.019 Uiso 1 1 calc R . . C4 C 0.27342(12) 0.77415(13) 0.25337(8) 0.0164(3) Uani 1 1 d . . . C5 C 0.48361(13) 0.72643(15) 0.41843(8) 0.0222(3) Uani 1 1 d D . . C6 C 0.4962(4) 0.5876(4) 0.4257(3) 0.0343(11) Uiso 0.499(9) 1 d PDU A 1 H6A H 0.5693 0.5680 0.4567 0.052 Uiso 0.499(9) 1 calc PR A 1 H6B H 0.4908 0.5521 0.3790 0.052 Uiso 0.499(9) 1 calc PR A 1 H6C H 0.4363 0.5554 0.4460 0.052 Uiso 0.499(9) 1 calc PR A 1 C7 C 0.4830(3) 0.7759(5) 0.49431(19) 0.0228(9) Uiso 0.499(9) 1 d PDU A 1 H7A H 0.4177 0.7441 0.5091 0.034 Uiso 0.499(9) 1 calc PR A 1 H7B H 0.4792 0.8635 0.4929 0.034 Uiso 0.499(9) 1 calc PR A 1 H7C H 0.5518 0.7507 0.5280 0.034 Uiso 0.499(9) 1 calc PR A 1 C8 C 0.5825(3) 0.7777(4) 0.39713(19) 0.0208(9) Uiso 0.499(9) 1 d PDU A 1 H8A H 0.5741 0.8648 0.3925 0.031 Uiso 0.499(9) 1 calc PR A 1 H8B H 0.5879 0.7433 0.3518 0.031 Uiso 0.499(9) 1 calc PR A 1 H8C H 0.6508 0.7589 0.4331 0.031 Uiso 0.499(9) 1 calc PR A 1 C6' C 0.5191(4) 0.5997(3) 0.4016(3) 0.0312(11) Uiso 0.501(9) 1 d PDU A 2 H6'1 H 0.5919 0.5803 0.4329 0.047 Uiso 0.501(9) 1 calc PR A 2 H6'2 H 0.5252 0.5965 0.3524 0.047 Uiso 0.501(9) 1 calc PR A 2 H6'3 H 0.4629 0.5418 0.4088 0.047 Uiso 0.501(9) 1 calc PR A 2 C7' C 0.4781(3) 0.7357(5) 0.49265(18) 0.0215(9) Uiso 0.501(9) 1 d PDU A 2 H7'1 H 0.5523 0.7192 0.5232 0.032 Uiso 0.501(9) 1 calc PR A 2 H7'2 H 0.4239 0.6775 0.5023 0.032 Uiso 0.501(9) 1 calc PR A 2 H7'3 H 0.4545 0.8167 0.5020 0.032 Uiso 0.501(9) 1 calc PR A 2 C8' C 0.5737(4) 0.8178(5) 0.4018(2) 0.0306(10) Uiso 0.501(9) 1 d PDU A 2 H8'1 H 0.5494 0.9000 0.4076 0.046 Uiso 0.501(9) 1 calc PR A 2 H8'2 H 0.5805 0.8062 0.3531 0.046 Uiso 0.501(9) 1 calc PR A 2 H8'3 H 0.6465 0.8035 0.4344 0.046 Uiso 0.501(9) 1 calc PR A 2 C9 C 0.25487(13) 0.78052(14) 0.17395(8) 0.0192(3) Uani 1 1 d . . . C10 C 0.29602(15) 0.66044(16) 0.15076(9) 0.0283(4) Uani 1 1 d . . . H10A H 0.3763 0.6512 0.1721 0.042 Uiso 1 1 calc R . . H10B H 0.2834 0.6589 0.0992 0.042 Uiso 1 1 calc R . . H10C H 0.2545 0.5947 0.1662 0.042 Uiso 1 1 calc R . . C11 C 0.13052(14) 0.79540(18) 0.13939(9) 0.0289(4) Uani 1 1 d . . . H11A H 0.0885 0.7281 0.1526 0.043 Uiso 1 1 calc R . . H11B H 0.1198 0.7972 0.0879 0.043 Uiso 1 1 calc R . . H11C H 0.1033 0.8705 0.1554 0.043 Uiso 1 1 calc R . . C12 C 0.32276(16) 0.88240(17) 0.15194(9) 0.0305(4) Uani 1 1 d . . . H12A H 0.2918 0.9594 0.1622 0.046 Uiso 1 1 calc R . . H12B H 0.3188 0.8767 0.1012 0.046 Uiso 1 1 calc R . . H12C H 0.4012 0.8763 0.1783 0.046 Uiso 1 1 calc R . . C13 C 0.18447(12) 0.52051(13) 0.42442(8) 0.0172(3) Uani 1 1 d . . . C14 C 0.15242(13) 0.45320(15) 0.47658(8) 0.0207(3) Uani 1 1 d . . . H14 H 0.1387 0.4924 0.5170 0.025 Uiso 1 1 calc R . . C15 C 0.14020(14) 0.33007(15) 0.47048(9) 0.0241(3) Uani 1 1 d . . . H15 H 0.1176 0.2855 0.5063 0.029 Uiso 1 1 calc R . . C16 C 0.16083(14) 0.27242(15) 0.41231(9) 0.0262(3) Uani 1 1 d . . . H16 H 0.1525 0.1880 0.4080 0.031 Uiso 1 1 calc R . . C17 C 0.19349(18) 0.33714(16) 0.36034(10) 0.0348(4) Uani 1 1 d . . . H17 H 0.2082 0.2971 0.3204 0.042 Uiso 1 1 calc R . . C18 C 0.20501(17) 0.46093(16) 0.36614(9) 0.0299(4) Uani 1 1 d . . . H18 H 0.2271 0.5050 0.3300 0.036 Uiso 1 1 calc R . . C19 C 0.05700(12) 0.73736(13) 0.40887(8) 0.0170(3) Uani 1 1 d . . . C20 C -0.02978(13) 0.67296(14) 0.36522(8) 0.0198(3) Uani 1 1 d . . . H20 H -0.0167 0.5937 0.3514 0.024 Uiso 1 1 calc R . . C21 C -0.13525(14) 0.72423(16) 0.34197(9) 0.0245(3) Uani 1 1 d . . . H21 H -0.1939 0.6797 0.3124 0.029 Uiso 1 1 calc R . . C22 C -0.15539(14) 0.83973(16) 0.36161(9) 0.0263(4) Uani 1 1 d . . . H22 H -0.2271 0.8751 0.3446 0.032 Uiso 1 1 calc R . . C23 C -0.07049(14) 0.90370(15) 0.40631(9) 0.0250(3) Uani 1 1 d . . . H23 H -0.0843 0.9825 0.4205 0.030 Uiso 1 1 calc R . . C24 C 0.03439(13) 0.85251(14) 0.43013(8) 0.0211(3) Uani 1 1 d . . . H24 H 0.0918 0.8962 0.4613 0.025 Uiso 1 1 calc R . . C25 C 0.14466(13) 0.98366(14) 0.30444(8) 0.0202(3) Uani 1 1 d . . . C26 C 0.29577(14) 0.96905(14) 0.41981(9) 0.0246(3) Uani 1 1 d . . . C27 C 0.35032(14) 1.03124(15) 0.30492(9) 0.0260(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn 0.01540(11) 0.01417(11) 0.01723(11) 0.00035(8) 0.00235(8) -0.00075(8) P 0.01820(18) 0.01671(18) 0.01304(16) -0.00020(14) 0.00429(14) 0.00049(14) N 0.0164(6) 0.0191(6) 0.0180(6) -0.0003(5) 0.0046(5) 0.0006(5) O1 0.0263(6) 0.0324(7) 0.0285(6) 0.0072(5) 0.0063(5) 0.0096(5) O2 0.0557(9) 0.0279(7) 0.0246(6) -0.0082(5) -0.0012(6) 0.0040(6) O3 0.0370(8) 0.0291(7) 0.0547(9) 0.0068(6) 0.0130(7) -0.0115(6) C1 0.0154(7) 0.0158(7) 0.0178(7) -0.0009(5) 0.0029(5) 0.0006(5) C2 0.0179(7) 0.0135(6) 0.0154(6) 0.0004(5) 0.0038(5) 0.0005(5) C3 0.0157(7) 0.0157(7) 0.0162(7) -0.0010(5) 0.0035(5) -0.0019(5) C4 0.0162(7) 0.0154(7) 0.0176(7) 0.0003(5) 0.0043(5) -0.0012(5) C5 0.0150(7) 0.0271(8) 0.0226(8) -0.0001(6) 0.0005(6) 0.0038(6) C9 0.0196(7) 0.0231(7) 0.0152(7) 0.0015(6) 0.0045(6) -0.0021(6) C10 0.0331(9) 0.0294(9) 0.0225(8) -0.0047(7) 0.0068(7) 0.0008(7) C11 0.0244(8) 0.0444(11) 0.0167(7) 0.0040(7) 0.0021(6) 0.0028(7) C12 0.0392(10) 0.0335(10) 0.0205(8) 0.0017(7) 0.0106(7) -0.0127(8) C13 0.0187(7) 0.0159(7) 0.0173(7) 0.0004(5) 0.0045(5) 0.0020(5) C14 0.0219(7) 0.0224(7) 0.0177(7) 0.0009(6) 0.0047(6) -0.0005(6) C15 0.0240(8) 0.0226(8) 0.0249(8) 0.0072(6) 0.0041(6) -0.0024(6) C16 0.0269(8) 0.0160(7) 0.0348(9) 0.0021(7) 0.0052(7) 0.0033(6) C17 0.0552(12) 0.0203(8) 0.0348(10) -0.0052(7) 0.0224(9) 0.0041(8) C18 0.0487(11) 0.0207(8) 0.0261(8) 0.0013(7) 0.0206(8) 0.0023(8) C19 0.0185(7) 0.0184(7) 0.0159(7) 0.0014(5) 0.0078(5) 0.0012(6) C20 0.0217(7) 0.0202(7) 0.0181(7) -0.0009(6) 0.0058(6) -0.0005(6) C21 0.0208(8) 0.0302(9) 0.0218(8) 0.0016(7) 0.0038(6) -0.0020(7) C22 0.0194(8) 0.0297(9) 0.0314(9) 0.0095(7) 0.0091(7) 0.0051(7) C23 0.0274(8) 0.0190(7) 0.0326(9) 0.0024(7) 0.0153(7) 0.0040(6) C24 0.0230(8) 0.0189(7) 0.0237(7) -0.0023(6) 0.0100(6) -0.0016(6) C25 0.0243(8) 0.0196(7) 0.0172(7) 0.0010(6) 0.0061(6) -0.0012(6) C26 0.0280(8) 0.0165(7) 0.0259(8) -0.0001(6) -0.0007(7) 0.0008(6) C27 0.0232(8) 0.0213(8) 0.0326(9) 0.0007(7) 0.0048(7) -0.0011(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 Mn C25 1.7936(16) . ? Mn C26 1.7946(17) . ? Mn C27 1.8038(17) . ? Mn C3 2.1399(14) . ? Mn C4 2.1404(15) . ? Mn C1 2.1424(15) . ? Mn N 2.1431(13) . ? Mn C2 2.1463(14) . ? P C2 1.8274(15) . ? P C13 1.8326(15) . ? P C19 1.8356(15) . ? N C1 1.3771(19) . ? N C4 1.3817(19) . ? O1 C25 1.1511(19) . ? O2 C26 1.149(2) . ? O3 C27 1.145(2) . ? C1 C2 1.450(2) . ? C1 C5 1.523(2) . ? C2 C3 1.422(2) . ? C3 C4 1.419(2) . ? C4 C9 1.512(2) . ? C5 C7' 1.467(4) . ? C5 C8 1.486(4) . ? C5 C6' 1.538(4) . ? C5 C6 1.562(4) . ? C5 C7 1.580(4) . ? C5 C8' 1.592(4) . ? C9 C11 1.524(2) . ? C9 C12 1.530(2) . ? C9 C10 1.538(2) . ? C13 C18 1.389(2) . ? C13 C14 1.393(2) . ? C14 C15 1.386(2) . ? C15 C16 1.377(2) . ? C16 C17 1.378(2) . ? C17 C18 1.392(2) . ? C19 C20 1.396(2) . ? C19 C24 1.399(2) . ? C20 C21 1.390(2) . ? C21 C22 1.384(2) . ? C22 C23 1.388(3) . ? C23 C24 1.384(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 Mn C26 91.04(7) . . ? C25 Mn C27 91.44(7) . . ? C26 Mn C27 91.50(8) . . ? C25 Mn C3 89.83(6) . . ? C26 Mn C3 127.36(7) . . ? C27 Mn C3 141.10(7) . . ? C25 Mn C4 104.32(6) . . ? C26 Mn C4 157.69(7) . . ? C27 Mn C4 103.97(7) . . ? C3 Mn C4 38.73(5) . . ? C25 Mn C1 151.91(7) . . ? C26 Mn C1 96.06(6) . . ? C27 Mn C1 115.42(7) . . ? C3 Mn C1 64.36(6) . . ? C4 Mn C1 62.92(5) . . ? C25 Mn N 141.07(6) . . ? C26 Mn N 127.61(6) . . ? C27 Mn N 91.86(7) . . ? C3 Mn N 64.45(5) . . ? C4 Mn N 37.64(5) . . ? C1 Mn N 37.49(5) . . ? C25 Mn C2 112.94(6) . . ? C26 Mn C2 94.54(7) . . ? C27 Mn C2 154.71(7) . . ? C3 Mn C2 38.75(5) . . ? C4 Mn C2 64.76(5) . . ? C1 Mn C2 39.52(5) . . ? N Mn C2 65.16(5) . . ? C2 P C13 100.63(7) . . ? C2 P C19 99.51(7) . . ? C13 P C19 102.47(7) . . ? C1 N C4 108.24(12) . . ? C1 N Mn 71.23(8) . . ? C4 N Mn 71.08(8) . . ? N C1 C2 109.56(12) . . ? N C1 C5 118.06(13) . . ? C2 C1 C5 131.50(13) . . ? N C1 Mn 71.28(8) . . ? C2 C1 Mn 70.39(8) . . ? C5 C1 Mn 132.82(11) . . ? C3 C2 C1 105.15(12) . . ? C3 C2 P 126.07(11) . . ? C1 C2 P 128.75(11) . . ? C3 C2 Mn 70.38(8) . . ? C1 C2 Mn 70.10(8) . . ? P C2 Mn 125.38(7) . . ? C4 C3 C2 107.80(13) . . ? C4 C3 Mn 70.65(8) . . ? C2 C3 Mn 70.87(8) . . ? N C4 C3 109.23(12) . . ? N C4 C9 120.81(13) . . ? C3 C4 C9 129.05(13) . . ? N C4 Mn 71.29(8) . . ? C3 C4 Mn 70.61(8) . . ? C9 C4 Mn 132.76(11) . . ? C7' C5 C8 118.5(2) . . ? C7' C5 C1 115.95(18) . . ? C8 C5 C1 112.53(19) . . ? C7' C5 C6' 110.9(2) . . ? C8 C5 C6' 90.3(2) . . ? C1 C5 C6' 104.68(19) . . ? C7' C5 C6 90.4(2) . . ? C8 C5 C6 109.8(2) . . ? C1 C5 C6 106.40(19) . . ? C6' C5 C6 22.95(17) . . ? C7' C5 C7 16.56(18) . . ? C8 C5 C7 108.1(2) . . ? C1 C5 C7 113.31(18) . . ? C6' C5 C7 125.8(2) . . ? C6 C5 C7 106.5(2) . . ? C7' C5 C8' 110.5(2) . . ? C8 C5 C8' 17.30(19) . . ? C1 C5 C8' 106.8(2) . . ? C6' C5 C8' 107.6(3) . . ? C6 C5 C8' 126.6(3) . . ? C7 C5 C8' 97.0(2) . . ? C4 C9 C11 110.58(12) . . ? C4 C9 C12 111.16(13) . . ? C11 C9 C12 110.42(14) . . ? C4 C9 C10 106.19(13) . . ? C11 C9 C10 109.18(14) . . ? C12 C9 C10 109.19(13) . . ? C18 C13 C14 118.30(14) . . ? C18 C13 P 124.97(12) . . ? C14 C13 P 116.69(11) . . ? C15 C14 C13 121.10(15) . . ? C16 C15 C14 119.84(15) . . ? C15 C16 C17 120.03(16) . . ? C16 C17 C18 120.20(16) . . ? C13 C18 C17 120.53(16) . . ? C20 C19 C24 118.59(14) . . ? C20 C19 P 124.40(12) . . ? C24 C19 P 117.01(12) . . ? C21 C20 C19 120.29(15) . . ? C22 C21 C20 120.45(16) . . ? C21 C22 C23 119.79(15) . . ? C24 C23 C22 119.91(15) . . ? C23 C24 C19 120.92(15) . . ? O1 C25 Mn 179.03(15) . . ? O2 C26 Mn 177.26(16) . . ? O3 C27 Mn 179.66(19) . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.634 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.065 _iucr_refine_instructions_details ; TITL MK85 in P2(1)/c CELL 0.71073 12.263813 11.169660 19.481237 90.0000 103.5927 90.0000 ZERR 4.00 0.000500 0.000400 0.000700 0.0000 0.0040 0.0000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O P MN UNIT 108 116 4 12 4 4 MERG 2 FMAP 2 TEMP -173 PLAN 10 ACTA 60 L.S. 4 WGHT 0.033800 1.521800 FVAR 2.21257 0.49911 MN 6 0.276373 0.907550 0.332670 11.00000 0.01540 0.01417 = 0.01723 0.00035 0.00235 -0.00075 P 5 0.201075 0.681986 0.440082 11.00000 0.01820 0.01671 = 0.01304 -0.00020 0.00429 0.00049 N 3 0.380326 0.779497 0.296420 11.00000 0.01644 0.01908 = 0.01797 -0.00032 0.00462 0.00064 O1 4 0.059357 1.031065 0.286500 11.00000 0.02629 0.03243 = 0.02854 0.00721 0.00629 0.00957 O2 4 0.303911 1.006994 0.475637 11.00000 0.05569 0.02785 = 0.02462 -0.00824 -0.00120 0.00401 O3 4 0.397612 1.109781 0.287642 11.00000 0.03702 0.02914 = 0.05467 0.00678 0.01297 -0.01146 C1 1 0.374279 0.749394 0.363971 11.00000 0.01545 0.01584 = 0.01782 -0.00093 0.00290 0.00064 C2 1 0.258467 0.726601 0.365440 11.00000 0.01792 0.01348 = 0.01538 0.00041 0.00381 0.00051 C3 1 0.196549 0.742199 0.294543 11.00000 0.01569 0.01565 = 0.01622 -0.00104 0.00348 -0.00186 AFIX 43 H3 2 0.117782 0.732894 0.277727 11.00000 -1.20000 AFIX 0 C4 1 0.273415 0.774153 0.253373 11.00000 0.01621 0.01541 = 0.01765 0.00025 0.00427 -0.00116 SAME C5 C6' > C8' SADI C5 C6 C5 C7 C5 C8 SADI C6 C7 C7 C8 C8 C6 SIMU 0.02 0.04 0.9 C5 > C8' C5 1 0.483609 0.726426 0.418433 11.00000 0.01498 0.02711 = 0.02265 -0.00013 0.00047 0.00379 PART1 21 C6 1 0.496171 0.587574 0.425718 21.00000 0.03435 AFIX 137 H6A 2 0.569254 0.568048 0.456668 21.00000 -1.50000 H6B 2 0.490803 0.552115 0.379027 21.00000 -1.50000 H6C 2 0.436339 0.555426 0.446030 21.00000 -1.50000 AFIX 0 C7 1 0.482993 0.775907 0.494310 21.00000 0.02283 AFIX 137 H7A 2 0.417659 0.744133 0.509148 21.00000 -1.50000 H7B 2 0.479180 0.863537 0.492870 21.00000 -1.50000 H7C 2 0.551758 0.750748 0.527979 21.00000 -1.50000 AFIX 0 C8 1 0.582515 0.777716 0.397129 21.00000 0.02082 AFIX 137 H8A 2 0.574086 0.864786 0.392455 21.00000 -1.50000 H8B 2 0.587925 0.743315 0.351771 21.00000 -1.50000 H8C 2 0.650760 0.758870 0.433113 21.00000 -1.50000 AFIX 0 PART2 -21 C6' 1 0.519131 0.599747 0.401593 -21.00000 0.03121 AFIX 137 H6'1 2 0.591936 0.580305 0.432900 -21.00000 -1.50000 H6'2 2 0.525189 0.596484 0.352356 -21.00000 -1.50000 H6'3 2 0.462895 0.541754 0.408795 -21.00000 -1.50000 AFIX 0 C7' 1 0.478102 0.735747 0.492652 -21.00000 0.02149 AFIX 137 H7'1 2 0.552260 0.719224 0.523164 -21.00000 -1.50000 H7'2 2 0.423859 0.677505 0.502343 -21.00000 -1.50000 H7'3 2 0.454508 0.816741 0.502033 -21.00000 -1.50000 AFIX 0 C8' 1 0.573675 0.817837 0.401793 -21.00000 0.03059 AFIX 137 H8'1 2 0.549412 0.900049 0.407602 -21.00000 -1.50000 H8'2 2 0.580536 0.806208 0.353124 -21.00000 -1.50000 H8'3 2 0.646504 0.803508 0.434414 -21.00000 -1.50000 AFIX 0 PART0 C9 1 0.254868 0.780520 0.173951 11.00000 0.01956 0.02307 = 0.01525 0.00155 0.00453 -0.00208 C10 1 0.296019 0.660440 0.150757 11.00000 0.03313 0.02943 = 0.02252 -0.00475 0.00681 0.00079 AFIX 137 H10A 2 0.376301 0.651224 0.172096 11.00000 -1.50000 H10B 2 0.283442 0.658870 0.099192 11.00000 -1.50000 H10C 2 0.254537 0.594706 0.166204 11.00000 -1.50000 AFIX 0 C11 1 0.130521 0.795398 0.139386 11.00000 0.02436 0.04441 = 0.01667 0.00398 0.00208 0.00277 AFIX 137 H11A 2 0.088501 0.728064 0.152639 11.00000 -1.50000 H11B 2 0.119848 0.797228 0.087938 11.00000 -1.50000 H11C 2 0.103275 0.870466 0.155359 11.00000 -1.50000 AFIX 0 C12 1 0.322759 0.882405 0.151942 11.00000 0.03918 0.03352 = 0.02046 0.00172 0.01060 -0.01273 AFIX 137 H12A 2 0.291784 0.959438 0.162212 11.00000 -1.50000 H12B 2 0.318835 0.876707 0.101220 11.00000 -1.50000 H12C 2 0.401151 0.876342 0.178293 11.00000 -1.50000 AFIX 0 C13 1 0.184475 0.520513 0.424422 11.00000 0.01867 0.01595 = 0.01726 0.00041 0.00455 0.00199 C14 1 0.152416 0.453198 0.476583 11.00000 0.02188 0.02245 = 0.01771 0.00088 0.00466 -0.00048 AFIX 43 H14 2 0.138701 0.492366 0.517019 11.00000 -1.20000 AFIX 0 C15 1 0.140197 0.330068 0.470477 11.00000 0.02401 0.02259 = 0.02486 0.00723 0.00410 -0.00239 AFIX 43 H15 2 0.117641 0.285512 0.506318 11.00000 -1.20000 AFIX 0 C16 1 0.160832 0.272416 0.412313 11.00000 0.02692 0.01601 = 0.03479 0.00214 0.00520 0.00325 AFIX 43 H16 2 0.152548 0.187993 0.408029 11.00000 -1.20000 AFIX 0 C17 1 0.193487 0.337142 0.360336 11.00000 0.05521 0.02034 = 0.03477 -0.00516 0.02238 0.00409 AFIX 43 H17 2 0.208178 0.297150 0.320421 11.00000 -1.20000 AFIX 0 C18 1 0.205008 0.460932 0.366144 11.00000 0.04871 0.02071 = 0.02611 0.00134 0.02063 0.00230 AFIX 43 H18 2 0.227092 0.505033 0.329964 11.00000 -1.20000 AFIX 0 C19 1 0.056998 0.737364 0.408869 11.00000 0.01846 0.01842 = 0.01588 0.00139 0.00784 0.00119 C20 1 -0.029779 0.672963 0.365224 11.00000 0.02165 0.02017 = 0.01812 -0.00092 0.00577 -0.00049 AFIX 43 H20 2 -0.016684 0.593728 0.351352 11.00000 -1.20000 AFIX 0 C21 1 -0.135254 0.724232 0.341967 11.00000 0.02077 0.03018 = 0.02179 0.00158 0.00375 -0.00202 AFIX 43 H21 2 -0.193943 0.679712 0.312383 11.00000 -1.20000 AFIX 0 C22 1 -0.155395 0.839725 0.361611 11.00000 0.01942 0.02974 = 0.03138 0.00949 0.00914 0.00508 AFIX 43 H22 2 -0.227101 0.875099 0.344555 11.00000 -1.20000 AFIX 0 C23 1 -0.070488 0.903697 0.406311 11.00000 0.02739 0.01903 = 0.03256 0.00244 0.01526 0.00395 AFIX 43 H23 2 -0.084342 0.982497 0.420537 11.00000 -1.20000 AFIX 0 C24 1 0.034387 0.852513 0.430128 11.00000 0.02301 0.01890 = 0.02371 -0.00230 0.01003 -0.00164 AFIX 43 H24 2 0.091808 0.896193 0.461346 11.00000 -1.20000 AFIX 0 C25 1 0.144661 0.983663 0.304443 11.00000 0.02433 0.01958 = 0.01720 0.00104 0.00613 -0.00118 C26 1 0.295768 0.969050 0.419814 11.00000 0.02798 0.01653 = 0.02593 -0.00010 -0.00071 0.00079 C27 1 0.350321 1.031240 0.304924 11.00000 0.02320 0.02134 = 0.03258 0.00068 0.00485 -0.00110 HKLF 4 ; #============================================================================= # end of cif data for "MK85" (compound 5-Mn(CO)3) #============================================================================= #============================================================================= # end of combined cif data #============================================================================= _database_code_depnum_ccdc_archive 'CCDC 954350'