# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _publ_contact_author ; Sun, Yu (concerning X-ray structure analysis) Technische Universit\"at Kaiserslautern Fachbereich Chemie Erwin-Schr\"odinger-Str. Geb. 54 D-67663 Kaiserslautern, Germany ; _publ_contact_author_email sun@chemie.uni-kl.de loop_ _publ_author_name _publ_author_address A.Reis ; Technische Universit\"at Kaiserslautern Fachbereich Chemie Erwin-Schr\"odinger-Str. Geb. 54 D-67663 Kaiserslautern, Germany ; D.Dehe ; Technische Universit\"at Kaiserslautern Fachbereich Chemie Erwin-Schr\"odinger-Str. Geb. 54 D-67663 Kaiserslautern, Germany ; S.Farsadpour ; Technische Universit\"at Kaiserslautern Fachbereich Chemie Erwin-Schr\"odinger-Str. Geb. 54 D-67663 Kaiserslautern, Germany ; I.Munstein ; Technische Universit\"at Kaiserslautern Fachbereich Chemie Erwin-Schr\"odinger-Str. Geb. 54 D-67663 Kaiserslautern, Germany ; Yu.Sun ; Technische Universit\"at Kaiserslautern Fachbereich Chemie Erwin-Schr\"odinger-Str. Geb. 54 D-67663 Kaiserslautern, Germany ; W.R.Thiel ; Technische Universit\"at Kaiserslautern Fachbereich Chemie Erwin-Schr\"odinger-Str. Geb. 54 D-67663 Kaiserslautern, Germany ; _publ_contact_author_name 'Sun, Yu' data_0837o _database_code_depnum_ccdc_archive 'CCDC 827385' #TrackingRef '- 0837o.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H14 N P' _chemical_formula_weight 287.28 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 8.4168(5) _cell_length_b 9.9909(8) _cell_length_c 10.6003(9) _cell_angle_alpha 107.361(7) _cell_angle_beta 104.961(6) _cell_angle_gamma 107.851(6) _cell_volume 747.45(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3480 _cell_measurement_theta_min 5.0845 _cell_measurement_theta_max 62.515 _exptl_crystal_description 'transaprent prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 1.544 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68590 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini S Ultra' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 16.1399 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6228 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 62.62 _reflns_number_total 2349 _reflns_number_gt 1900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SIR92 (Giacovazzo et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2349 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0881 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 C1 C 0.7079(2) 0.11739(18) 0.85396(17) 0.0256(4) Uani 1 1 d . . . C2 C 0.7070(2) -0.01679(19) 0.76299(19) 0.0317(4) Uani 1 1 d . . . H2 H 0.5959 -0.0967 0.6914 0.038 Uiso 1 1 calc R . . C3 C 0.8668(3) -0.0348(2) 0.7760(2) 0.0362(4) Uani 1 1 d . . . H3 H 0.8637 -0.1270 0.7132 0.043 Uiso 1 1 calc R . . C4 C 1.0299(2) 0.0794(2) 0.8789(2) 0.0366(4) Uani 1 1 d . . . H4 H 1.1380 0.0651 0.8873 0.044 Uiso 1 1 calc R . . C5 C 1.0362(2) 0.2144(2) 0.96963(19) 0.0334(4) Uani 1 1 d . . . H5 H 1.1486 0.2946 1.0391 0.040 Uiso 1 1 calc R . . C6 C 0.8756(2) 0.23197(19) 0.95817(17) 0.0277(4) Uani 1 1 d . . . C7 C 0.8844(2) 0.3740(2) 1.05558(18) 0.0304(4) Uani 1 1 d . . . C8 C 0.3216(2) -0.02328(18) 0.70555(17) 0.0254(4) Uani 1 1 d . . . C9 C 0.2312(2) -0.03080(19) 0.57189(18) 0.0312(4) Uani 1 1 d . . . H9 H 0.2727 0.0556 0.5496 0.037 Uiso 1 1 calc R . . C10 C 0.0813(2) -0.1632(2) 0.47098(19) 0.0354(4) Uani 1 1 d . . . H10 H 0.0206 -0.1668 0.3802 0.043 Uiso 1 1 calc R . . C11 C 0.0196(2) -0.2899(2) 0.50152(19) 0.0355(4) Uani 1 1 d . . . H11 H -0.0835 -0.3802 0.4322 0.043 Uiso 1 1 calc R . . C12 C 0.1086(2) -0.28458(19) 0.63385(19) 0.0355(4) Uani 1 1 d . . . H12 H 0.0670 -0.3719 0.6549 0.043 Uiso 1 1 calc R . . C13 C 0.2582(2) -0.15230(19) 0.73561(18) 0.0315(4) Uani 1 1 d . . . H13 H 0.3180 -0.1492 0.8264 0.038 Uiso 1 1 calc R . . C14 C 0.5286(2) 0.29685(18) 0.77859(17) 0.0260(4) Uani 1 1 d . . . C15 C 0.6286(2) 0.3159(2) 0.69412(18) 0.0323(4) Uani 1 1 d . . . H15 H 0.6863 0.2493 0.6702 0.039 Uiso 1 1 calc R . . C16 C 0.6449(2) 0.4313(2) 0.6446(2) 0.0374(4) Uani 1 1 d . . . H16 H 0.7125 0.4431 0.5864 0.045 Uiso 1 1 calc R . . C17 C 0.5621(2) 0.5295(2) 0.68024(19) 0.0380(4) Uani 1 1 d . . . H17 H 0.5741 0.6093 0.6473 0.046 Uiso 1 1 calc R . . C18 C 0.4622(2) 0.5112(2) 0.76374(19) 0.0363(4) Uani 1 1 d . . . H18 H 0.4051 0.5782 0.7878 0.044 Uiso 1 1 calc R . . C19 C 0.4452(2) 0.39561(19) 0.81233(18) 0.0308(4) Uani 1 1 d . . . H19 H 0.3760 0.3835 0.8693 0.037 Uiso 1 1 calc R . . N1 N 0.8912(2) 0.48476(18) 1.13357(17) 0.0394(4) Uani 1 1 d . . . P1 P 0.50511(6) 0.15144(5) 0.85296(4) 0.02544(16) 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 C1 0.0249(9) 0.0276(9) 0.0275(9) 0.0144(7) 0.0108(7) 0.0113(7) C2 0.0330(10) 0.0288(9) 0.0328(9) 0.0113(8) 0.0138(8) 0.0125(8) C3 0.0431(12) 0.0356(10) 0.0441(11) 0.0202(9) 0.0248(10) 0.0238(9) C4 0.0331(11) 0.0497(11) 0.0462(11) 0.0297(10) 0.0223(9) 0.0256(9) C5 0.0258(10) 0.0403(10) 0.0357(10) 0.0203(8) 0.0110(8) 0.0116(8) C6 0.0281(10) 0.0313(9) 0.0267(9) 0.0155(7) 0.0116(7) 0.0120(8) C7 0.0212(9) 0.0333(10) 0.0280(9) 0.0119(8) 0.0051(7) 0.0047(8) C8 0.0222(9) 0.0262(8) 0.0267(9) 0.0081(7) 0.0098(7) 0.0108(7) C9 0.0320(10) 0.0288(9) 0.0305(9) 0.0117(8) 0.0105(8) 0.0114(8) C10 0.0340(10) 0.0351(10) 0.0290(9) 0.0092(8) 0.0054(8) 0.0137(8) C11 0.0290(10) 0.0263(9) 0.0363(10) 0.0039(8) 0.0061(8) 0.0071(8) C12 0.0366(11) 0.0247(9) 0.0414(11) 0.0128(8) 0.0145(9) 0.0093(8) C13 0.0315(10) 0.0297(9) 0.0299(9) 0.0117(8) 0.0092(8) 0.0115(8) C14 0.0208(9) 0.0215(8) 0.0259(9) 0.0053(7) 0.0032(7) 0.0054(7) C15 0.0294(10) 0.0330(10) 0.0351(10) 0.0135(8) 0.0129(8) 0.0136(8) C16 0.0316(11) 0.0406(10) 0.0403(11) 0.0217(9) 0.0130(9) 0.0110(9) C17 0.0345(11) 0.0282(9) 0.0398(11) 0.0158(8) 0.0021(9) 0.0071(8) C18 0.0323(10) 0.0288(10) 0.0390(10) 0.0087(8) 0.0041(8) 0.0149(8) C19 0.0250(9) 0.0285(9) 0.0293(9) 0.0057(7) 0.0063(7) 0.0085(7) N1 0.0334(9) 0.0358(9) 0.0357(9) 0.0077(8) 0.0099(7) 0.0074(7) P1 0.0227(2) 0.0254(2) 0.0251(2) 0.00821(18) 0.00863(18) 0.00870(18) _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 C1 C2 1.395(2) . ? C1 C6 1.405(2) . ? C1 P1 1.8379(16) . ? C2 C3 1.388(2) . ? C2 H2 0.9500 . ? C3 C4 1.378(3) . ? C3 H3 0.9500 . ? C4 C5 1.380(3) . ? C4 H4 0.9500 . ? C5 C6 1.395(2) . ? C5 H5 0.9500 . ? C6 C7 1.452(2) . ? C7 N1 1.141(2) . ? C8 C9 1.392(2) . ? C8 C13 1.400(2) . ? C8 P1 1.8295(17) . ? C9 C10 1.387(2) . ? C9 H9 0.9500 . ? C10 C11 1.379(3) . ? C10 H10 0.9500 . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.392(2) . ? C14 C15 1.393(2) . ? C14 P1 1.8328(17) . ? C15 C16 1.388(2) . ? C15 H15 0.9500 . ? C16 C17 1.386(3) . ? C16 H16 0.9500 . ? C17 C18 1.382(3) . ? C17 H17 0.9500 . ? C18 C19 1.382(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 C1 C6 117.43(15) . . ? C2 C1 P1 124.86(13) . . ? C6 C1 P1 117.65(12) . . ? C3 C2 C1 120.73(17) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C4 C3 C2 120.82(16) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.06(16) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.23(17) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C1 121.71(15) . . ? C5 C6 C7 118.54(16) . . ? C1 C6 C7 119.74(15) . . ? N1 C7 C6 179.02(19) . . ? C9 C8 C13 118.58(16) . . ? C9 C8 P1 124.24(13) . . ? C13 C8 P1 116.87(13) . . ? C10 C9 C8 120.61(16) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C11 C10 C9 120.44(17) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 119.69(17) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 120.22(17) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C8 120.46(16) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? C19 C14 C15 118.79(16) . . ? C19 C14 P1 117.60(13) . . ? C15 C14 P1 123.58(12) . . ? C16 C15 C14 120.54(16) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.88(17) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C18 C17 C16 119.97(17) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.13(16) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 120.69(16) . . ? C18 C19 H19 119.7 . . ? C14 C19 H19 119.7 . . ? C8 P1 C14 103.51(7) . . ? C8 P1 C1 103.18(7) . . ? C14 P1 C1 101.00(7) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 62.62 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.233 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.047 data_07248o _database_code_depnum_ccdc_archive 'CCDC 827386' #TrackingRef '- 07248o.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 O2 P' _chemical_formula_weight 306.28 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' O O 0.0492 0.0322 '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 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 7.8941(2) _cell_length_b 28.6950(7) _cell_length_c 7.0857(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.221(3) _cell_angle_gamma 90.00 _cell_volume 1592.33(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6492 _cell_measurement_theta_min 4.6205 _cell_measurement_theta_max 62.7397 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 1.559 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini S Ultra' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 16.1399 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13185 _diffrn_reflns_av_R_equivalents 0.0997 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 5.86 _diffrn_reflns_theta_max 62.68 _reflns_number_total 2504 _reflns_number_gt 2062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.' _computing_structure_solution 'SIR92 (Giacovazzo et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2504 _refine_ls_number_parameters 202 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.124 _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 C1 C 0.9535(2) 0.58057(6) 0.3833(3) 0.0292(5) Uani 1 1 d . . . C2 C 1.0763(3) 0.54896(6) 0.3335(3) 0.0312(5) Uani 1 1 d . . . H2 H 1.0746 0.5399 0.2043 0.037 Uiso 1 1 calc R . . C3 C 1.1991(3) 0.53088(6) 0.4689(3) 0.0309(5) Uani 1 1 d . . . H3 H 1.2830 0.5102 0.4322 0.037 Uiso 1 1 calc R . . C4 C 1.2006(2) 0.54292(6) 0.6599(3) 0.0294(5) Uani 1 1 d . . . C5 C 1.0765(3) 0.57334(7) 0.7112(3) 0.0342(5) Uani 1 1 d . . . H5 H 1.0751 0.5813 0.8411 0.041 Uiso 1 1 calc R . . C6 C 0.9555(2) 0.59197(7) 0.5741(3) 0.0317(5) Uani 1 1 d . . . H6 H 0.8723 0.6129 0.6110 0.038 Uiso 1 1 calc R . . C7 C 1.3321(3) 0.52401(7) 0.8058(3) 0.0330(5) Uani 1 1 d . . . C8 C 0.6676(2) 0.64123(7) 0.3283(3) 0.0311(5) Uani 1 1 d . . . C9 C 0.5416(2) 0.61925(7) 0.4186(3) 0.0351(5) Uani 1 1 d . . . H9 H 0.5239 0.5866 0.4040 0.042 Uiso 1 1 calc R . . C10 C 0.4422(3) 0.64486(8) 0.5292(3) 0.0378(5) Uani 1 1 d . . . H10 H 0.3595 0.6295 0.5935 0.045 Uiso 1 1 calc R . . C11 C 0.4629(2) 0.69268(8) 0.5465(3) 0.0358(5) Uani 1 1 d . . . H11 H 0.3947 0.7101 0.6223 0.043 Uiso 1 1 calc R . . C12 C 0.5828(3) 0.71479(7) 0.4531(3) 0.0359(5) Uani 1 1 d . . . H12 H 0.5951 0.7477 0.4622 0.043 Uiso 1 1 calc R . . C13 C 0.6860(2) 0.68945(7) 0.3460(3) 0.0319(5) Uani 1 1 d . . . H13 H 0.7698 0.7050 0.2842 0.038 Uiso 1 1 calc R . . C14 C 0.9297(2) 0.64761(7) 0.0860(3) 0.0280(5) Uani 1 1 d . . . C15 C 0.8567(3) 0.67089(7) -0.0767(3) 0.0345(5) Uani 1 1 d . . . H15 H 0.7418 0.6644 -0.1267 0.041 Uiso 1 1 calc R . . C16 C 0.9492(3) 0.70352(7) -0.1672(3) 0.0393(5) Uani 1 1 d . . . H16 H 0.8970 0.7194 -0.2771 0.047 Uiso 1 1 calc R . . C17 C 1.1171(3) 0.71280(7) -0.0970(3) 0.0393(5) Uani 1 1 d . . . H17 H 1.1805 0.7351 -0.1580 0.047 Uiso 1 1 calc R . . C18 C 1.1922(3) 0.68946(7) 0.0623(3) 0.0380(5) Uani 1 1 d . . . H18 H 1.3082 0.6952 0.1097 0.046 Uiso 1 1 calc R . . C19 C 1.0980(3) 0.65754(7) 0.1531(3) 0.0352(5) Uani 1 1 d . . . H19 H 1.1504 0.6421 0.2641 0.042 Uiso 1 1 calc R . . P1 P 0.79855(6) 0.604274(17) 0.19132(7) 0.0315(2) Uani 1 1 d . . . O1 O 1.45418(19) 0.50058(5) 0.7587(2) 0.0420(4) Uani 1 1 d . . . O2 O 1.3154(2) 0.53329(6) 0.9800(2) 0.0491(5) Uani 1 1 d D . . H2O H 1.403(3) 0.5229(9) 1.062(3) 0.059 Uiso 1 1 d 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 C1 0.0309(11) 0.0235(9) 0.0348(12) -0.0027(8) 0.0112(9) -0.0024(8) C2 0.0371(11) 0.0266(10) 0.0334(12) -0.0029(8) 0.0183(9) -0.0004(8) C3 0.0327(11) 0.0239(10) 0.0403(12) 0.0004(8) 0.0209(10) 0.0027(8) C4 0.0325(11) 0.0235(10) 0.0354(11) 0.0002(8) 0.0161(9) 0.0011(8) C5 0.0402(12) 0.0298(10) 0.0359(12) -0.0046(9) 0.0177(9) 0.0050(9) C6 0.0315(11) 0.0284(10) 0.0362(12) -0.0046(8) 0.0078(9) 0.0084(8) C7 0.0376(12) 0.0275(10) 0.0376(12) 0.0037(8) 0.0190(10) 0.0053(8) C8 0.0247(10) 0.0319(10) 0.0368(12) -0.0001(8) 0.0048(9) 0.0019(8) C9 0.0290(11) 0.0324(11) 0.0445(13) -0.0005(9) 0.0077(10) -0.0034(8) C10 0.0275(11) 0.0426(12) 0.0450(13) 0.0051(10) 0.0110(10) 0.0012(9) C11 0.0252(11) 0.0476(12) 0.0342(12) -0.0032(9) 0.0026(9) 0.0077(9) C12 0.0364(11) 0.0293(10) 0.0419(12) -0.0029(9) 0.0050(10) 0.0036(9) C13 0.0297(11) 0.0319(10) 0.0351(11) -0.0024(9) 0.0077(9) -0.0024(8) C14 0.0270(10) 0.0304(10) 0.0269(11) -0.0065(8) 0.0046(8) 0.0028(8) C15 0.0325(11) 0.0384(11) 0.0324(12) -0.0100(9) 0.0029(9) 0.0069(9) C16 0.0561(15) 0.0336(11) 0.0297(11) 0.0019(9) 0.0110(10) 0.0113(10) C17 0.0509(14) 0.0332(11) 0.0377(12) -0.0005(9) 0.0205(11) 0.0012(9) C18 0.0324(12) 0.0407(12) 0.0409(13) 0.0025(10) 0.0048(10) -0.0032(9) C19 0.0355(12) 0.0356(11) 0.0342(12) 0.0042(9) 0.0037(9) -0.0002(9) P1 0.0289(3) 0.0299(3) 0.0367(4) -0.0063(2) 0.0074(3) -0.00167(19) O1 0.0442(9) 0.0434(8) 0.0427(9) 0.0045(7) 0.0220(8) 0.0179(7) O2 0.0495(10) 0.0670(11) 0.0329(10) 0.0035(7) 0.0136(8) 0.0264(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.390(3) . ? C1 C2 1.405(3) . ? C1 P1 1.841(2) . ? C2 C3 1.377(3) . ? C2 H2 0.9500 . ? C3 C4 1.396(3) . ? C3 H3 0.9500 . ? C4 C5 1.394(3) . ? C4 C7 1.473(3) . ? C5 C6 1.381(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.254(2) . ? C7 O2 1.286(3) . ? C8 C13 1.395(3) . ? C8 C9 1.399(3) . ? C8 P1 1.840(2) . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.376(3) . ? C11 H11 0.9500 . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C19 1.383(3) . ? C14 C15 1.393(3) . ? C14 P1 1.836(2) . ? C15 C16 1.393(3) . ? C15 H15 0.9500 . ? C16 C17 1.381(3) . ? C16 H16 0.9500 . ? C17 C18 1.380(3) . ? C17 H17 0.9500 . ? C18 C19 1.388(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O2 H2O 0.894(17) . ? 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 C6 C1 C2 118.20(19) . . ? C6 C1 P1 123.86(15) . . ? C2 C1 P1 117.94(15) . . ? C3 C2 C1 121.09(18) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.13(17) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.13(19) . . ? C5 C4 C7 120.28(18) . . ? C3 C4 C7 120.59(17) . . ? C6 C5 C4 120.40(19) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 121.01(18) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? O1 C7 O2 122.8(2) . . ? O1 C7 C4 120.52(18) . . ? O2 C7 C4 116.71(17) . . ? C13 C8 C9 118.56(18) . . ? C13 C8 P1 124.04(15) . . ? C9 C8 P1 117.39(15) . . ? C10 C9 C8 120.30(19) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 120.38(19) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.67(19) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.55(19) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.48(18) . . ? C12 C13 H13 119.8 . . ? C8 C13 H13 119.8 . . ? C19 C14 C15 117.74(18) . . ? C19 C14 P1 124.49(15) . . ? C15 C14 P1 117.73(15) . . ? C16 C15 C14 121.1(2) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C17 C16 C15 119.9(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C18 C17 C16 119.66(19) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 120.0(2) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C14 C19 C18 121.6(2) . . ? C14 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C14 P1 C8 101.95(9) . . ? C14 P1 C1 101.20(8) . . ? C8 P1 C1 100.84(9) . . ? C7 O2 H2O 113.1(17) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 62.68 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.266 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.056