# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # 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_1_OAC_RDR_[3] _database_code_depnum_ccdc_archive 'CCDC 908447' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 Cl N2 O3' _chemical_formula_weight 312.79 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.4814(2) _cell_length_b 15.0113(6) _cell_length_c 18.9143(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.881(2) _cell_angle_gamma 90.00 _cell_volume 1556.14(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4419 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 23.29 _exptl_crystal_description Flake _exptl_crystal_colour brown _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6726 _exptl_absorpt_correction_T_max 0.7449 _exptl_absorpt_process_details 'Bruker AXScale' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11368 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 23.35 _reflns_number_total 2250 _reflns_number_gt 1885 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.8623P] 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 2250 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 Cl Cl -0.40285(9) -0.58194(3) 0.89424(3) 0.02744(16) Uani 1 1 d . . . C1 C -0.3225(3) -0.24408(12) 0.48574(10) 0.0220(4) Uani 1 1 d . . . H1A H -0.2314 -0.2136 0.5243 0.026 Uiso 1 1 calc R . . H1B H -0.2021 -0.2750 0.4560 0.026 Uiso 1 1 calc R . . C2 C -0.4891(4) -0.31251(12) 0.51767(10) 0.0223(5) Uani 1 1 d . . . C3 C -0.4429(3) -0.43712(12) 0.59681(10) 0.0212(4) Uani 1 1 d . . . C4 C -0.3038(3) -0.45392(12) 0.65668(10) 0.0232(5) Uani 1 1 d . . . H4A H -0.1561 -0.4222 0.6649 0.028 Uiso 1 1 calc R . . C5 C -0.3801(3) -0.51706(12) 0.70464(10) 0.0243(5) Uani 1 1 d . . . H5A H -0.2836 -0.5292 0.7457 0.029 Uiso 1 1 calc R . . C6 C -0.5974(3) -0.56284(11) 0.69319(10) 0.0200(4) Uani 1 1 d . . . C7 C -0.7326(4) -0.54687(12) 0.63157(10) 0.0240(5) Uani 1 1 d . . . H7A H -0.8786 -0.5794 0.6227 0.029 Uiso 1 1 calc R . . C8 C -0.6556(4) -0.48373(12) 0.58295(10) 0.0250(5) Uani 1 1 d . . . H8A H -0.7477 -0.4728 0.5409 0.030 Uiso 1 1 calc R . . C9 C -0.8390(4) -0.68795(13) 0.74201(11) 0.0249(5) Uani 1 1 d . . . C10 C -0.8936(4) -0.73363(14) 0.81075(11) 0.0370(6) Uani 1 1 d . . . H10A H -0.9153 -0.7976 0.8024 0.056 Uiso 1 1 calc R . . H10B H -1.0434 -0.7088 0.8304 0.056 Uiso 1 1 calc R . . H10C H -0.7577 -0.7243 0.8442 0.056 Uiso 1 1 calc R . . C11 C -0.5912(4) -0.21553(13) 0.38002(10) 0.0235(5) Uani 1 1 d . . . H11A H -0.7557 -0.2349 0.3945 0.028 Uiso 1 1 calc R . . H11B H -0.5030 -0.2675 0.3608 0.028 Uiso 1 1 calc R . . C12 C -0.6088(4) -0.14128(14) 0.32545(11) 0.0315(5) Uani 1 1 d . . . H12A H -0.7681 -0.1105 0.3284 0.038 Uiso 1 1 calc R . . H12B H -0.5919 -0.1656 0.2771 0.038 Uiso 1 1 calc R . . C13 C -0.3991(4) -0.07643(13) 0.34274(11) 0.0296(5) Uani 1 1 d . . . H13A H -0.2892 -0.0706 0.3019 0.036 Uiso 1 1 calc R . . H13B H -0.4637 -0.0168 0.3547 0.036 Uiso 1 1 calc R . . C14 C -0.2637(3) -0.11682(12) 0.40597(10) 0.0243(5) Uani 1 1 d . . . H14A H -0.1228 -0.1527 0.3904 0.029 Uiso 1 1 calc R . . H14B H -0.2043 -0.0697 0.4385 0.029 Uiso 1 1 calc R . . C15 C -0.6154(3) -0.11837(12) 0.48633(10) 0.0245(5) Uani 1 1 d . . . H15C H -0.5172 -0.0879 0.5227 0.037 Uiso 1 1 calc R . . H15B H -0.7375 -0.1560 0.5090 0.037 Uiso 1 1 calc R . . H15A H -0.6977 -0.0741 0.4563 0.037 Uiso 1 1 calc R . . N1 N -0.4520(3) -0.17545(9) 0.44175(8) 0.0190(4) Uani 1 1 d . . . N2 N -0.6719(3) -0.62182(10) 0.74691(9) 0.0239(4) Uani 1 1 d . . . H19 H -0.6011 -0.6147 0.7886 0.028(6) Uiso 1 1 calc R . . O1 O -0.3449(2) -0.37197(8) 0.55168(7) 0.0252(3) Uani 1 1 d . . . O2 O -0.7070(2) -0.31411(9) 0.51507(8) 0.0334(4) Uani 1 1 d . . . O3 O -0.9396(3) -0.70947(9) 0.68592(8) 0.0322(4) 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 Cl 0.0305(3) 0.0291(3) 0.0226(3) 0.0023(2) -0.0043(2) -0.0019(2) C1 0.0200(10) 0.0216(10) 0.0242(11) 0.0013(8) -0.0022(8) 0.0016(8) C2 0.0285(12) 0.0202(10) 0.0182(11) -0.0007(8) 0.0000(9) 0.0022(9) C3 0.0265(11) 0.0188(10) 0.0184(11) 0.0018(8) 0.0027(9) 0.0017(8) C4 0.0235(11) 0.0202(10) 0.0259(12) -0.0018(9) 0.0000(9) -0.0018(8) C5 0.0290(11) 0.0237(11) 0.0201(11) 0.0011(9) -0.0030(9) 0.0004(9) C6 0.0262(11) 0.0161(9) 0.0178(11) -0.0026(8) 0.0020(8) -0.0001(8) C7 0.0269(11) 0.0207(10) 0.0244(12) -0.0016(9) -0.0002(9) -0.0026(8) C8 0.0303(11) 0.0243(11) 0.0203(11) 0.0015(9) -0.0049(9) 0.0002(9) C9 0.0272(11) 0.0217(10) 0.0258(13) -0.0020(9) 0.0028(10) -0.0003(9) C10 0.0463(14) 0.0371(13) 0.0278(13) 0.0042(10) 0.0029(11) -0.0132(11) C11 0.0254(11) 0.0244(10) 0.0207(11) -0.0025(9) -0.0037(9) -0.0019(8) C12 0.0357(12) 0.0351(12) 0.0235(12) 0.0061(10) -0.0040(10) -0.0035(10) C13 0.0289(11) 0.0295(11) 0.0306(12) 0.0086(10) 0.0033(9) -0.0020(9) C14 0.0208(10) 0.0206(10) 0.0315(12) 0.0058(9) 0.0022(9) -0.0039(8) C15 0.0268(11) 0.0234(10) 0.0234(11) -0.0033(9) 0.0008(9) 0.0041(8) N1 0.0196(8) 0.0180(8) 0.0194(9) 0.0011(7) 0.0002(7) -0.0008(6) N2 0.0330(10) 0.0234(9) 0.0152(9) 0.0002(7) -0.0029(8) -0.0065(7) O1 0.0265(7) 0.0229(7) 0.0264(8) 0.0090(6) 0.0001(6) -0.0003(6) O2 0.0245(9) 0.0317(8) 0.0439(10) 0.0131(7) 0.0018(7) -0.0006(6) O3 0.0374(8) 0.0315(8) 0.0276(9) -0.0011(7) -0.0046(7) -0.0112(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 C1 N1 1.496(2) . ? C1 C2 1.507(3) . ? C2 O2 1.195(2) . ? C2 O1 1.349(2) . ? C3 C4 1.379(3) . ? C3 C8 1.381(3) . ? C3 O1 1.410(2) . ? C4 C5 1.381(3) . ? C5 C6 1.389(3) . ? C6 C7 1.392(3) . ? C6 N2 1.413(2) . ? C7 C8 1.391(3) . ? C9 O3 1.231(2) . ? C9 N2 1.353(2) . ? C9 C10 1.504(3) . ? C11 N1 1.510(2) . ? C11 C12 1.521(3) . ? C12 C13 1.538(3) . ? C13 C14 1.524(3) . ? C14 N1 1.523(2) . ? C15 N1 1.507(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 N1 C1 C2 114.02(15) . . ? O2 C2 O1 125.76(17) . . ? O2 C2 C1 127.49(18) . . ? O1 C2 C1 106.73(16) . . ? C4 C3 C8 121.17(17) . . ? C4 C3 O1 114.41(16) . . ? C8 C3 O1 124.39(17) . . ? C3 C4 C5 119.73(18) . . ? C4 C5 C6 120.30(18) . . ? C5 C6 C7 119.30(17) . . ? C5 C6 N2 117.03(17) . . ? C7 C6 N2 123.64(17) . . ? C8 C7 C6 120.51(18) . . ? C3 C8 C7 118.93(18) . . ? O3 C9 N2 123.06(18) . . ? O3 C9 C10 122.19(18) . . ? N2 C9 C10 114.75(18) . . ? N1 C11 C12 105.00(15) . . ? C11 C12 C13 106.26(16) . . ? C14 C13 C12 105.58(16) . . ? N1 C14 C13 104.68(15) . . ? C1 N1 C15 111.18(14) . . ? C1 N1 C11 112.66(14) . . ? C15 N1 C11 111.20(14) . . ? C1 N1 C14 109.03(14) . . ? C15 N1 C14 109.44(14) . . ? C11 N1 C14 102.98(14) . . ? C9 N2 C6 127.83(17) . . ? C2 O1 C3 121.45(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.172 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.040 data_2_OAC_RDR_[5] _database_code_depnum_ccdc_archive 'CCDC 908448' #TrackingRef '15068_web_deposit_cif_file_0_PatrickBarber_1351611074.OAC RDR Prodrug IL 10-30-12.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H37 Cl N O3 P' _chemical_formula_weight 429.95 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.5949(7) _cell_length_b 14.3513(10) _cell_length_c 17.5913(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.6940(10) _cell_angle_gamma 90.00 _cell_volume 2363.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3685 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 23.24 _exptl_crystal_description shard _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6772 _exptl_absorpt_correction_T_max 0.7449 _exptl_absorpt_process_details 'Bruker AXScale' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11639 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 23.26 _reflns_number_total 3395 _reflns_number_gt 2732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+2.5224P] 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 3395 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Cl1 Cl 0.53860(7) -0.13265(5) -0.25979(4) 0.0370(2) Uani 1 1 d . . . P1 P 0.21013(8) 0.36169(5) 0.16067(4) 0.0309(2) Uani 1 1 d . . . O1 O 0.35148(19) 0.22184(14) -0.00091(12) 0.0381(5) Uani 1 1 d . . . O2 O 0.1246(2) 0.25806(17) 0.00428(13) 0.0505(6) Uani 1 1 d . . . O3 O 0.0920(2) 0.07662(17) -0.35879(14) 0.0559(7) Uani 1 1 d . . . N1 N 0.2913(2) 0.02084(16) -0.27756(14) 0.0317(6) Uani 1 1 d . . . H0A H 0.3621 -0.0187 -0.2755 0.038 Uiso 1 1 calc R . . C1 C 0.3199(3) 0.2930(2) 0.11165(17) 0.0332(7) Uani 1 1 d . . . H1A H 0.4033 0.3312 0.1065 0.040 Uiso 1 1 calc R . . H1B H 0.3566 0.2391 0.1452 0.040 Uiso 1 1 calc R . . C2 C 0.2498(3) 0.25708(19) 0.03260(18) 0.0328(7) Uani 1 1 d . . . C3 C 0.3212(3) 0.1733(2) -0.07247(17) 0.0314(7) Uani 1 1 d . . . C4 C 0.4116(3) 0.0992(2) -0.07519(18) 0.0352(7) Uani 1 1 d . . . H4A H 0.4818 0.0823 -0.0303 0.042 Uiso 1 1 calc R . . C5 C 0.3991(3) 0.0499(2) -0.14360(17) 0.0330(7) Uani 1 1 d . . . H5A H 0.4607 -0.0014 -0.1457 0.040 Uiso 1 1 calc R . . C6 C 0.2967(3) 0.07473(19) -0.20973(17) 0.0292(7) Uani 1 1 d . . . C7 C 0.2090(3) 0.15082(19) -0.20578(17) 0.0328(7) Uani 1 1 d . . . H7A H 0.1406 0.1695 -0.2508 0.039 Uiso 1 1 calc R . . C8 C 0.2203(3) 0.1995(2) -0.13683(17) 0.0345(7) Uani 1 1 d . . . H8A H 0.1587 0.2507 -0.1341 0.041 Uiso 1 1 calc R . . C9 C 0.1922(3) 0.0220(2) -0.34502(18) 0.0351(7) Uani 1 1 d . . . C10 C 0.2110(4) -0.0506(2) -0.40338(18) 0.0455(8) Uani 1 1 d . . . H10A H 0.1344 -0.0446 -0.4502 0.068 Uiso 1 1 calc R . . H10B H 0.2073 -0.1127 -0.3808 0.068 Uiso 1 1 calc R . . H10C H 0.3037 -0.0418 -0.4172 0.068 Uiso 1 1 calc R . . C11 C 0.1550(3) 0.4685(2) 0.10986(18) 0.0355(7) Uani 1 1 d . . . H11A H 0.1081 0.4529 0.0554 0.043 Uiso 1 1 calc R . . H11B H 0.0820 0.4980 0.1340 0.043 Uiso 1 1 calc R . . C12 C 0.2715(3) 0.5404(2) 0.10794(18) 0.0376(7) Uani 1 1 d . . . H12A H 0.3157 0.5597 0.1619 0.045 Uiso 1 1 calc R . . H12B H 0.3467 0.5116 0.0851 0.045 Uiso 1 1 calc R . . C13 C 0.2125(4) 0.6256(2) 0.0605(2) 0.0491(9) Uani 1 1 d . . . H13A H 0.1646 0.6057 0.0073 0.059 Uiso 1 1 calc R . . H13B H 0.1397 0.6554 0.0846 0.059 Uiso 1 1 calc R . . C14 C 0.3269(4) 0.6967(3) 0.0549(2) 0.0669(11) Uani 1 1 d . . . H14A H 0.2832 0.7499 0.0237 0.100 Uiso 1 1 calc R . . H14B H 0.3984 0.6680 0.0302 0.100 Uiso 1 1 calc R . . H14C H 0.3730 0.7181 0.1073 0.100 Uiso 1 1 calc R . . C15 C 0.3244(3) 0.3793(3) 0.25468(17) 0.0448(8) Uani 1 1 d . . . H15A H 0.3627 0.3179 0.2751 0.054 Uiso 1 1 calc R . . H15B H 0.4065 0.4179 0.2481 0.054 Uiso 1 1 calc R . . C16 C 0.2582(4) 0.4243(3) 0.31423(19) 0.0496(9) Uani 1 1 d . . . H16A H 0.1823 0.3833 0.3256 0.060 Uiso 1 1 calc R . . H16B H 0.2134 0.4837 0.2933 0.060 Uiso 1 1 calc R . . C17 C 0.3688(4) 0.4433(3) 0.38980(18) 0.0542(10) Uani 1 1 d . . . H17A H 0.4079 0.3836 0.4135 0.065 Uiso 1 1 calc R . . H17B H 0.4486 0.4804 0.3783 0.065 Uiso 1 1 calc R . . C18 C 0.2994(4) 0.4955(3) 0.4455(2) 0.0600(10) Uani 1 1 d . . . H18A H 0.3700 0.5073 0.4940 0.090 Uiso 1 1 calc R . . H18B H 0.2206 0.4584 0.4568 0.090 Uiso 1 1 calc R . . H18C H 0.2623 0.5550 0.4221 0.090 Uiso 1 1 calc R . . C19 C 0.0487(3) 0.3026(2) 0.16866(18) 0.0359(7) Uani 1 1 d . . . H19A H 0.0048 0.3375 0.2060 0.043 Uiso 1 1 calc R . . H19B H -0.0188 0.3051 0.1173 0.043 Uiso 1 1 calc R . . C20 C 0.0650(3) 0.2017(2) 0.1946(2) 0.0437(8) Uani 1 1 d . . . H20A H 0.1455 0.1964 0.2405 0.052 Uiso 1 1 calc R . . H20B H 0.0879 0.1633 0.1523 0.052 Uiso 1 1 calc R . . C21 C -0.0703(3) 0.1644(3) 0.2156(2) 0.0507(9) Uani 1 1 d . . . H21A H -0.0547 0.0983 0.2312 0.061 Uiso 1 1 calc R . . H21B H -0.0871 0.1993 0.2613 0.061 Uiso 1 1 calc R . . C22 C -0.2026(4) 0.1709(3) 0.1511(2) 0.0678(11) Uani 1 1 d . . . H22A H -0.2847 0.1464 0.1695 0.102 Uiso 1 1 calc R . . H22B H -0.1890 0.1344 0.1062 0.102 Uiso 1 1 calc R . . H22C H -0.2202 0.2362 0.1356 0.102 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 Cl1 0.0343(4) 0.0312(4) 0.0438(5) -0.0017(3) 0.0053(3) 0.0041(3) P1 0.0330(4) 0.0340(4) 0.0258(4) -0.0024(3) 0.0064(3) -0.0043(3) O1 0.0311(11) 0.0430(13) 0.0410(13) -0.0102(10) 0.0093(9) 0.0034(9) O2 0.0319(12) 0.0764(17) 0.0417(13) -0.0147(12) 0.0049(10) 0.0034(11) O3 0.0495(14) 0.0545(15) 0.0552(15) -0.0104(12) -0.0068(11) 0.0217(12) N1 0.0295(12) 0.0288(13) 0.0373(15) 0.0016(11) 0.0081(11) 0.0064(10) C1 0.0319(15) 0.0309(16) 0.0371(17) 0.0031(13) 0.0085(13) -0.0002(13) C2 0.0336(17) 0.0260(16) 0.0400(18) 0.0021(13) 0.0106(14) 0.0004(12) C3 0.0310(15) 0.0305(16) 0.0343(17) -0.0024(13) 0.0104(13) -0.0008(13) C4 0.0303(15) 0.0366(17) 0.0373(18) 0.0024(14) 0.0044(13) 0.0033(13) C5 0.0277(15) 0.0311(16) 0.0413(18) 0.0018(14) 0.0101(13) 0.0055(12) C6 0.0275(14) 0.0259(16) 0.0362(17) 0.0015(13) 0.0116(13) -0.0024(12) C7 0.0291(15) 0.0303(16) 0.0375(18) 0.0027(14) 0.0040(13) 0.0016(13) C8 0.0310(15) 0.0288(16) 0.0445(19) 0.0005(14) 0.0102(14) 0.0042(12) C9 0.0335(16) 0.0339(17) 0.0374(18) 0.0029(14) 0.0070(14) 0.0016(14) C10 0.053(2) 0.045(2) 0.0377(18) -0.0013(16) 0.0071(15) 0.0093(16) C11 0.0373(16) 0.0307(16) 0.0389(18) -0.0036(14) 0.0089(14) 0.0016(13) C12 0.0422(17) 0.0311(17) 0.0383(18) -0.0038(14) 0.0061(14) -0.0046(14) C13 0.053(2) 0.0349(19) 0.058(2) 0.0051(16) 0.0109(17) 0.0040(15) C14 0.082(3) 0.043(2) 0.072(3) 0.013(2) 0.008(2) -0.011(2) C15 0.0416(18) 0.060(2) 0.0317(18) -0.0028(16) 0.0065(14) -0.0096(16) C16 0.0481(19) 0.053(2) 0.048(2) -0.0056(17) 0.0098(16) -0.0015(16) C17 0.048(2) 0.081(3) 0.0335(19) -0.0140(18) 0.0077(16) -0.0163(19) C18 0.050(2) 0.073(3) 0.054(2) -0.014(2) 0.0047(18) -0.0030(19) C19 0.0322(15) 0.0421(18) 0.0329(17) 0.0003(14) 0.0061(13) -0.0031(13) C20 0.0412(17) 0.0405(19) 0.052(2) 0.0080(16) 0.0151(15) -0.0018(14) C21 0.0461(19) 0.050(2) 0.059(2) 0.0148(17) 0.0174(17) -0.0045(16) C22 0.053(2) 0.064(3) 0.085(3) 0.012(2) 0.012(2) -0.017(2) _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 C15 1.790(3) . ? P1 C11 1.794(3) . ? P1 C1 1.795(3) . ? P1 C19 1.798(3) . ? O1 C2 1.344(3) . ? O1 C3 1.412(3) . ? O2 C2 1.195(3) . ? O3 C9 1.222(3) . ? N1 C9 1.348(4) . ? N1 C6 1.413(4) . ? C1 C2 1.497(4) . ? C3 C8 1.371(4) . ? C3 C4 1.380(4) . ? C4 C5 1.378(4) . ? C5 C6 1.394(4) . ? C6 C7 1.390(4) . ? C7 C8 1.383(4) . ? C9 C10 1.501(4) . ? C11 C12 1.527(4) . ? C12 C13 1.519(4) . ? C13 C14 1.518(5) . ? C15 C16 1.487(4) . ? C16 C17 1.532(4) . ? C17 C18 1.501(5) . ? C19 C20 1.517(4) . ? C20 C21 1.522(4) . ? C21 C22 1.509(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 P1 C11 113.18(16) . . ? C15 P1 C1 102.47(14) . . ? C11 P1 C1 111.68(14) . . ? C15 P1 C19 110.95(15) . . ? C11 P1 C19 106.06(14) . . ? C1 P1 C19 112.67(14) . . ? C2 O1 C3 123.3(2) . . ? C9 N1 C6 128.6(2) . . ? C2 C1 P1 116.4(2) . . ? O2 C2 O1 125.5(3) . . ? O2 C2 C1 126.0(3) . . ? O1 C2 C1 108.4(2) . . ? C8 C3 C4 121.2(3) . . ? C8 C3 O1 124.8(3) . . ? C4 C3 O1 113.8(2) . . ? C5 C4 C3 119.4(3) . . ? C4 C5 C6 120.5(3) . . ? C7 C6 C5 118.9(3) . . ? C7 C6 N1 124.2(3) . . ? C5 C6 N1 116.9(2) . . ? C8 C7 C6 120.6(3) . . ? C3 C8 C7 119.4(3) . . ? O3 C9 N1 123.7(3) . . ? O3 C9 C10 121.1(3) . . ? N1 C9 C10 115.2(3) . . ? C12 C11 P1 116.8(2) . . ? C13 C12 C11 111.7(2) . . ? C14 C13 C12 112.9(3) . . ? C16 C15 P1 116.2(2) . . ? C15 C16 C17 111.6(3) . . ? C18 C17 C16 109.5(3) . . ? C20 C19 P1 116.1(2) . . ? C19 C20 C21 111.8(3) . . ? C22 C21 C20 114.7(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.974 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.049