# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_l0272a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 O2 P' _chemical_formula_sum 'C18 H23 O2 P' _chemical_formula_weight 302.33 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.8020(7) _cell_length_b 10.1477(8) _cell_length_c 10.3699(8) _cell_angle_alpha 90.00 _cell_angle_beta 114.980(2) _cell_angle_gamma 90.00 _cell_volume 839.59(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5083 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 26.84 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.166 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6686 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details SADABS-2008/1 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa ApexII' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11820 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.62 _reflns_number_total 3775 _reflns_number_gt 3256 _reflns_threshold_expression I>2\s(I) _computing_data_collection Apex2 _computing_cell_refinement 'SAINT V7.68A' _computing_data_reduction 'SAINT V7.68A, SADABS-2008/1' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0431P)^2^+0.0730P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _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(8) _chemical_absolute_configuration ad _refine_ls_number_reflns 3775 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0737 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.51913(5) 0.33353(4) 0.17776(5) 0.02605(11) Uani 1 1 d . . . O1 O 0.48306(17) 0.19367(12) 0.12593(15) 0.0350(3) Uani 1 1 d . . . O2 O 0.47513(17) 0.57926(12) 0.08156(15) 0.0343(3) Uani 1 1 d . . . H2 H 0.479(3) 0.624(2) 0.014(3) 0.045(7) Uiso 1 1 d . . . C1 C 0.4236(2) 0.45025(16) 0.0284(2) 0.0303(4) Uani 1 1 d . . . H1 H 0.4695 0.4306 -0.0428 0.036 Uiso 1 1 calc R . . C2 C 0.2357(2) 0.43315(18) -0.0440(2) 0.0307(4) Uani 1 1 d . . . C3 C 0.1282(2) 0.52249(18) -0.0243(2) 0.0316(4) Uani 1 1 d . . . H3 H 0.1731 0.5965 0.0359 0.038 Uiso 1 1 calc R . . C4 C -0.0442(2) 0.5052(2) -0.0915(2) 0.0357(4) Uani 1 1 d . . . H4 H -0.1155 0.5690 -0.0786 0.043 Uiso 1 1 calc R . . C5 C -0.1145(2) 0.39633(19) -0.1772(2) 0.0387(5) Uani 1 1 d . . . C6 C -0.0060(3) 0.30635(19) -0.1960(2) 0.0454(5) Uani 1 1 d . . . H6 H -0.0510 0.2311 -0.2542 0.055 Uiso 1 1 calc R . . C7 C 0.1653(2) 0.3241(2) -0.13179(19) 0.0408(4) Uani 1 1 d . . . H7 H 0.2363 0.2617 -0.1473 0.049 Uiso 1 1 calc R . . C8 C -0.3024(3) 0.3756(2) -0.2468(2) 0.0500(6) Uani 1 1 d . . . H8A H -0.3412 0.3716 -0.3503 0.075 Uiso 1 1 calc R . . H8B H -0.3577 0.4489 -0.2223 0.075 Uiso 1 1 calc R . . H8C H -0.3298 0.2927 -0.2129 0.075 Uiso 1 1 calc R . . C9 C 0.4278(2) 0.36702(16) 0.30094(18) 0.0238(4) Uani 1 1 d . . . C10 C 0.4114(2) 0.49417(18) 0.3454(2) 0.0311(4) Uani 1 1 d . . . H10 H 0.4504 0.5679 0.3116 0.037 Uiso 1 1 calc R . . C11 C 0.3382(2) 0.5123(2) 0.4388(2) 0.0375(5) Uani 1 1 d . . . H11 H 0.3264 0.5988 0.4683 0.045 Uiso 1 1 calc R . . C12 C 0.2824(2) 0.4064(2) 0.4893(2) 0.0401(5) Uani 1 1 d . . . H12 H 0.2338 0.4197 0.5545 0.048 Uiso 1 1 calc R . . C13 C 0.2971(2) 0.2802(2) 0.4451(2) 0.0394(5) Uani 1 1 d . . . H13 H 0.2580 0.2070 0.4797 0.047 Uiso 1 1 calc R . . C14 C 0.3686(2) 0.26046(18) 0.3505(2) 0.0304(4) Uani 1 1 d . . . H14 H 0.3771 0.1738 0.3194 0.036 Uiso 1 1 calc R . . C15 C 0.7475(2) 0.36461(17) 0.2656(2) 0.0310(4) Uani 1 1 d . . . C16 C 0.8268(3) 0.2420(2) 0.3557(3) 0.0458(6) Uani 1 1 d . . . H16A H 0.7949 0.1636 0.2949 0.069 Uiso 1 1 calc R . . H16B H 0.7871 0.2332 0.4304 0.069 Uiso 1 1 calc R . . H16C H 0.9491 0.2510 0.3992 0.069 Uiso 1 1 calc R . . C17 C 0.8106(3) 0.3795(2) 0.1487(2) 0.0428(5) Uani 1 1 d . . . H17A H 0.9334 0.3801 0.1922 0.064 Uiso 1 1 calc R . . H17B H 0.7688 0.4625 0.0975 0.064 Uiso 1 1 calc R . . H17C H 0.7697 0.3056 0.0821 0.064 Uiso 1 1 calc R . . C18 C 0.7953(2) 0.4877(2) 0.3611(2) 0.0385(5) Uani 1 1 d . . . H18A H 0.7688 0.4731 0.4427 0.058 Uiso 1 1 calc R . . H18B H 0.7320 0.5638 0.3065 0.058 Uiso 1 1 calc R . . H18C H 0.9156 0.5047 0.3948 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0335(2) 0.01852(19) 0.0323(2) -0.0007(2) 0.01994(18) -0.00072(19) O1 0.0456(8) 0.0222(7) 0.0447(9) -0.0053(6) 0.0263(7) -0.0016(6) O2 0.0459(8) 0.0223(6) 0.0362(8) 0.0026(6) 0.0188(7) -0.0069(6) C1 0.0425(11) 0.0241(9) 0.0280(10) -0.0010(7) 0.0185(9) -0.0027(7) C2 0.0395(10) 0.0255(9) 0.0276(9) 0.0024(7) 0.0148(8) -0.0020(8) C3 0.0417(11) 0.0230(9) 0.0315(10) 0.0014(7) 0.0167(9) -0.0034(7) C4 0.0414(11) 0.0293(9) 0.0361(11) 0.0065(8) 0.0161(9) 0.0019(8) C5 0.0418(11) 0.0317(11) 0.0324(11) 0.0057(9) 0.0059(9) -0.0027(8) C6 0.0494(12) 0.0300(13) 0.0394(12) -0.0058(8) 0.0017(9) -0.0037(8) C7 0.0471(10) 0.0339(10) 0.0356(10) -0.0073(10) 0.0118(8) 0.0021(10) C8 0.0426(11) 0.0433(12) 0.0492(14) 0.0057(10) 0.0049(10) -0.0047(9) C9 0.0236(7) 0.0256(9) 0.0229(8) 0.0016(6) 0.0104(7) 0.0019(6) C10 0.0327(10) 0.0270(9) 0.0355(11) -0.0017(8) 0.0164(8) 0.0021(8) C11 0.0325(10) 0.0416(11) 0.0389(12) -0.0087(9) 0.0156(9) 0.0046(8) C12 0.0287(10) 0.0609(14) 0.0352(12) 0.0020(10) 0.0178(9) 0.0062(9) C13 0.0304(10) 0.0468(12) 0.0449(13) 0.0155(9) 0.0198(10) 0.0019(9) C14 0.0279(9) 0.0243(9) 0.0389(12) 0.0057(8) 0.0141(9) 0.0020(7) C15 0.0342(9) 0.0264(10) 0.0398(11) 0.0034(7) 0.0228(8) 0.0024(7) C16 0.0340(11) 0.0418(13) 0.0655(16) 0.0177(11) 0.0246(11) 0.0057(9) C17 0.0426(11) 0.0446(11) 0.0542(13) -0.0008(10) 0.0332(10) -0.0036(9) C18 0.0330(10) 0.0387(11) 0.0458(13) -0.0035(10) 0.0186(10) -0.0042(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.5034(13) . ? P1 C9 1.8058(16) . ? P1 C1 1.8463(19) . ? P1 C15 1.8501(19) . ? O2 C1 1.419(2) . ? O2 H2 0.85(2) . ? C1 C2 1.510(3) . ? C1 H1 1.0000 . ? C2 C3 1.387(3) . ? C2 C7 1.400(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C5 1.388(3) . ? C4 H4 0.9500 . ? C5 C6 1.393(3) . ? C5 C8 1.514(3) . ? C6 C7 1.379(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.390(2) . ? C9 C10 1.398(2) . ? C10 C11 1.384(3) . ? C10 H10 0.9500 . ? C11 C12 1.373(3) . ? C11 H11 0.9500 . ? C12 C13 1.384(3) . ? C12 H12 0.9500 . ? C13 C14 1.386(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.536(3) . ? C15 C18 1.538(3) . ? C15 C17 1.538(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C9 109.91(7) . . ? O1 P1 C1 110.68(8) . . ? C9 P1 C1 106.96(8) . . ? O1 P1 C15 111.00(8) . . ? C9 P1 C15 109.61(8) . . ? C1 P1 C15 108.58(8) . . ? C1 O2 H2 107.1(16) . . ? O2 C1 C2 113.74(15) . . ? O2 C1 P1 107.96(13) . . ? C2 C1 P1 111.01(12) . . ? O2 C1 H1 108.0 . . ? C2 C1 H1 108.0 . . ? P1 C1 H1 108.0 . . ? C3 C2 C7 118.05(17) . . ? C3 C2 C1 121.60(17) . . ? C7 C2 C1 120.35(16) . . ? C2 C3 C4 120.86(17) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C5 121.27(19) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 117.68(18) . . ? C4 C5 C8 121.17(19) . . ? C6 C5 C8 121.15(18) . . ? C7 C6 C5 121.41(18) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C6 C7 C2 120.71(19) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 119.30(16) . . ? C14 C9 P1 117.62(13) . . ? C10 C9 P1 123.07(13) . . ? C11 C10 C9 119.79(18) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 120.65(19) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.95(17) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 120.14(17) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C9 120.15(18) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? C16 C15 C18 109.60(16) . . ? C16 C15 C17 109.67(15) . . ? C18 C15 C17 109.60(15) . . ? C16 C15 P1 106.36(12) . . ? C18 C15 P1 113.60(12) . . ? C17 C15 P1 107.92(13) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 O1 P1 C1 O2 -174.54(11) . . . . ? C9 P1 C1 O2 65.75(14) . . . . ? C15 P1 C1 O2 -52.46(14) . . . . ? O1 P1 C1 C2 60.17(14) . . . . ? C9 P1 C1 C2 -59.55(14) . . . . ? C15 P1 C1 C2 -177.76(12) . . . . ? O2 C1 C2 C3 -17.0(2) . . . . ? P1 C1 C2 C3 104.97(17) . . . . ? O2 C1 C2 C7 164.07(17) . . . . ? P1 C1 C2 C7 -73.9(2) . . . . ? C7 C2 C3 C4 -0.9(3) . . . . ? C1 C2 C3 C4 -179.88(17) . . . . ? C2 C3 C4 C5 1.8(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C3 C4 C5 C8 178.15(17) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C8 C5 C6 C7 -179.4(2) . . . . ? C5 C6 C7 C2 0.7(3) . . . . ? C3 C2 C7 C6 -0.3(3) . . . . ? C1 C2 C7 C6 178.66(18) . . . . ? O1 P1 C9 C14 11.61(16) . . . . ? C1 P1 C9 C14 131.81(14) . . . . ? C15 P1 C9 C14 -110.65(14) . . . . ? O1 P1 C9 C10 -167.04(14) . . . . ? C1 P1 C9 C10 -46.83(17) . . . . ? C15 P1 C9 C10 70.70(16) . . . . ? C14 C9 C10 C11 0.6(3) . . . . ? P1 C9 C10 C11 179.22(14) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C10 C11 C12 C13 -0.9(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C9 0.8(3) . . . . ? C10 C9 C14 C13 -1.2(3) . . . . ? P1 C9 C14 C13 -179.95(15) . . . . ? O1 P1 C15 C16 -41.08(15) . . . . ? C9 P1 C15 C16 80.52(15) . . . . ? C1 P1 C15 C16 -162.96(13) . . . . ? O1 P1 C15 C18 -161.73(13) . . . . ? C9 P1 C15 C18 -40.12(15) . . . . ? C1 P1 C15 C18 76.39(15) . . . . ? O1 P1 C15 C17 76.53(14) . . . . ? C9 P1 C15 C17 -161.86(12) . . . . ? C1 P1 C15 C17 -45.35(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 O2 H2 O1 0.85(2) 1.77(3) 2.6042(19) 168(2) 2_655 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.321 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.036 #===END _database_code_depnum_ccdc_archive 'CCDC 953762' ####################################################################### # # 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_mo_molan083_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 O2 P' _chemical_formula_weight 288.31 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 21.4308(14) _cell_length_b 6.0890(4) _cell_length_c 13.0171(8) _cell_angle_alpha 90.00 _cell_angle_beta 116.360(2) _cell_angle_gamma 90.00 _cell_volume 1522.01(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7613 _cell_measurement_theta_min 6.363 _cell_measurement_theta_max 54.104 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9349 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15838 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3320 _reflns_number_gt 2992 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0352P)^2^+0.7414P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(8) _refine_ls_number_reflns 3320 _refine_ls_number_parameters 185 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0764 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.66365(2) 0.78981(7) 0.27051(4) 0.01543(11) Uani 1 1 d . . . O1 O 0.68328(6) 0.5520(2) 0.29481(11) 0.0193(3) Uani 1 1 d . . . O2 O 0.73670(7) 0.8915(2) 0.48374(11) 0.0191(3) Uani 1 1 d . . . H2 H 0.7654 0.9700 0.5367 0.029 Uiso 1 1 calc R . . C1 C 0.73037(9) 0.9689(3) 0.37601(15) 0.0165(4) Uani 1 1 d . . . H1 H 0.7137 1.1244 0.3639 0.020 Uiso 1 1 calc R . . C2 C 0.79830(9) 0.9520(3) 0.36629(15) 0.0167(4) Uani 1 1 d . . . C3 C 0.82137(10) 1.1275(3) 0.32314(16) 0.0210(4) Uani 1 1 d . . . H3 H 0.7941 1.2571 0.2979 0.025 Uiso 1 1 calc R . . C4 C 0.88431(10) 1.1122(3) 0.31718(17) 0.0244(4) Uani 1 1 d . . . H4 H 0.9001 1.2324 0.2885 0.029 Uiso 1 1 calc R . . C5 C 0.92419(10) 0.9235(4) 0.35271(18) 0.0258(5) Uani 1 1 d . . . H5 H 0.9671 0.9139 0.3481 0.031 Uiso 1 1 calc R . . C6 C 0.90125(10) 0.7483(3) 0.39512(17) 0.0253(5) Uani 1 1 d . . . H6 H 0.9284 0.6182 0.4195 0.030 Uiso 1 1 calc R . . C7 C 0.83856(9) 0.7634(4) 0.40188(16) 0.0213(4) Uani 1 1 d . . . H7 H 0.8231 0.6434 0.4312 0.026 Uiso 1 1 calc R . . C8 C 0.66052(9) 0.8756(3) 0.13508(16) 0.0177(4) Uani 1 1 d . . . C9 C 0.67822(9) 0.7215(3) 0.07459(16) 0.0216(4) Uani 1 1 d . . . H9 H 0.6901 0.5766 0.1039 0.026 Uiso 1 1 calc R . . C10 C 0.67882(9) 0.7761(4) -0.02884(15) 0.0244(4) Uani 1 1 d . . . H10 H 0.6914 0.6693 -0.0695 0.029 Uiso 1 1 calc R . . C11 C 0.66095(10) 0.9871(3) -0.07220(17) 0.0247(5) Uani 1 1 d . . . H11 H 0.6603 1.0241 -0.1436 0.030 Uiso 1 1 calc R . . C12 C 0.64402(11) 1.1441(3) -0.01159(17) 0.0263(5) Uani 1 1 d . . . H12 H 0.6320 1.2887 -0.0413 0.032 Uiso 1 1 calc R . . C13 C 0.64453(10) 1.0904(3) 0.09252(17) 0.0226(4) Uani 1 1 d . . . H13 H 0.6341 1.1992 0.1349 0.027 Uiso 1 1 calc R . . C14 C 0.57840(9) 0.8426(3) 0.26885(16) 0.0195(4) Uani 1 1 d . . . C15 C 0.52405(10) 0.7158(4) 0.16645(18) 0.0314(5) Uani 1 1 d . . . H15A H 0.5372 0.5605 0.1727 0.047 Uiso 1 1 calc R . . H15B H 0.5218 0.7764 0.0951 0.047 Uiso 1 1 calc R . . H15C H 0.4784 0.7296 0.1660 0.047 Uiso 1 1 calc R . . C16 C 0.55919(12) 1.0850(4) 0.2594(2) 0.0335(5) Uani 1 1 d . . . H16A H 0.5160 1.1029 0.2670 0.050 Uiso 1 1 calc R . . H16B H 0.5526 1.1412 0.1847 0.050 Uiso 1 1 calc R . . H16C H 0.5967 1.1670 0.3206 0.050 Uiso 1 1 calc R . . C17 C 0.58071(9) 0.7492(4) 0.38001(17) 0.0251(5) Uani 1 1 d . . . H17A H 0.6160 0.8279 0.4459 0.038 Uiso 1 1 calc R . . H17B H 0.5926 0.5928 0.3860 0.038 Uiso 1 1 calc R . . H17C H 0.5350 0.7673 0.3791 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0181(2) 0.0130(2) 0.0148(2) -0.0001(2) 0.00703(17) 0.0007(2) O1 0.0223(7) 0.0142(7) 0.0202(7) 0.0007(5) 0.0084(6) 0.0017(5) O2 0.0217(7) 0.0211(7) 0.0136(6) -0.0025(5) 0.0071(5) -0.0040(5) C1 0.0200(9) 0.0139(9) 0.0156(9) -0.0009(7) 0.0078(8) 0.0002(7) C2 0.0201(9) 0.0167(9) 0.0132(9) -0.0027(8) 0.0074(7) -0.0034(8) C3 0.0241(10) 0.0203(10) 0.0163(10) 0.0014(8) 0.0070(8) -0.0015(8) C4 0.0280(10) 0.0264(11) 0.0193(10) 0.0024(8) 0.0111(9) -0.0072(8) C5 0.0221(10) 0.0325(12) 0.0278(11) -0.0029(9) 0.0156(9) -0.0051(8) C6 0.0230(9) 0.0210(12) 0.0317(11) -0.0009(9) 0.0120(8) 0.0003(8) C7 0.0220(9) 0.0196(11) 0.0228(9) 0.0003(9) 0.0104(7) -0.0026(8) C8 0.0165(8) 0.0191(9) 0.0147(9) -0.0005(7) 0.0045(7) -0.0014(7) C9 0.0228(9) 0.0211(11) 0.0187(10) -0.0015(7) 0.0072(8) 0.0011(7) C10 0.0234(9) 0.0303(10) 0.0209(9) -0.0074(11) 0.0111(7) -0.0017(10) C11 0.0283(10) 0.0308(12) 0.0166(10) -0.0019(9) 0.0115(8) -0.0086(9) C12 0.0359(12) 0.0216(11) 0.0210(11) 0.0023(9) 0.0122(9) -0.0051(9) C13 0.0307(10) 0.0193(10) 0.0199(10) -0.0028(8) 0.0132(8) -0.0010(8) C14 0.0181(9) 0.0226(11) 0.0179(9) 0.0015(7) 0.0081(7) 0.0020(7) C15 0.0192(10) 0.0469(15) 0.0248(11) -0.0068(9) 0.0069(9) -0.0022(9) C16 0.0335(12) 0.0247(11) 0.0527(15) 0.0087(11) 0.0285(11) 0.0101(9) C17 0.0207(9) 0.0321(13) 0.0250(10) 0.0020(9) 0.0124(8) -0.0054(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.5016(13) . ? P1 C8 1.8111(19) . ? P1 C1 1.8372(18) . ? P1 C14 1.8456(18) . ? O2 C1 1.427(2) . ? C1 C2 1.520(2) . ? C2 C7 1.387(3) . ? C2 C3 1.396(3) . ? C3 C4 1.388(3) . ? C4 C5 1.383(3) . ? C5 C6 1.388(3) . ? C6 C7 1.388(3) . ? C8 C9 1.382(3) . ? C8 C13 1.402(3) . ? C9 C10 1.392(3) . ? C10 C11 1.387(3) . ? C11 C12 1.387(3) . ? C12 C13 1.389(3) . ? C14 C16 1.523(3) . ? C14 C15 1.533(3) . ? C14 C17 1.535(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C8 111.65(8) . . ? O1 P1 C1 111.25(8) . . ? C8 P1 C1 103.69(8) . . ? O1 P1 C14 110.71(8) . . ? C8 P1 C14 109.25(8) . . ? C1 P1 C14 110.07(8) . . ? O2 C1 C2 112.51(14) . . ? O2 C1 P1 103.97(12) . . ? C2 C1 P1 110.74(12) . . ? C7 C2 C3 119.29(17) . . ? C7 C2 C1 120.32(16) . . ? C3 C2 C1 120.38(17) . . ? C4 C3 C2 119.87(18) . . ? C5 C4 C3 120.55(18) . . ? C4 C5 C6 119.75(18) . . ? C5 C6 C7 119.87(19) . . ? C2 C7 C6 120.67(19) . . ? C9 C8 C13 119.27(18) . . ? C9 C8 P1 117.25(14) . . ? C13 C8 P1 123.40(15) . . ? C8 C9 C10 120.77(19) . . ? C11 C10 C9 119.68(19) . . ? C12 C11 C10 120.13(18) . . ? C11 C12 C13 120.13(19) . . ? C12 C13 C8 119.98(19) . . ? C16 C14 C15 110.13(17) . . ? C16 C14 C17 109.21(17) . . ? C15 C14 C17 109.10(16) . . ? C16 C14 P1 113.61(13) . . ? C15 C14 P1 106.77(13) . . ? C17 C14 P1 107.89(12) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.285 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 946519'