# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email d.v.griffiths@qmul.ac.uk _publ_contact_author_name 'Vaughan Griffiths' loop_ _publ_author_name 'P. Duncanson' 'Y. Cheong' 'M. Motevalli' 'D. V. Griffiths' data_pd-9-151 _database_code_depnum_ccdc_archive 'CCDC 865150' #TrackingRef '9329_web_deposit_cif_file_0_Yuen-KiCheong_1327944984.pd-9-151-Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 N1 O5 P1' _chemical_formula_sum 'C19 H18 N O5 P' _chemical_formula_weight 371.31 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' 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5690(2) _cell_length_b 8.7336(2) _cell_length_c 11.8798(3) _cell_angle_alpha 81.6460(10) _cell_angle_beta 85.9310(10) _cell_angle_gamma 88.264(2) _cell_volume 877.23(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11236 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9425 _exptl_absorpt_correction_T_max 0.9688 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius Roper CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 20152 _diffrn_reflns_av_R_equivalents 0.0416 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 27.63 _reflns_number_total 4033 _reflns_number_gt 3408 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0438P)^2^+0.4893P] 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 4033 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1037 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.22579(16) 0.90219(17) 0.72039(12) 0.0166(3) Uani 1 1 d . . . C2 C 0.21972(17) 1.05074(17) 0.63182(12) 0.0172(3) Uani 1 1 d . . . C3 C 0.05278(17) 1.09128(18) 0.62519(12) 0.0180(3) Uani 1 1 d . . . C4 C -0.03621(17) 0.97518(18) 0.69056(12) 0.0177(3) Uani 1 1 d . . . C5 C -0.19814(18) 0.98259(19) 0.69926(13) 0.0218(3) Uani 1 1 d . . . H5 H -0.2580 0.9029 0.7436 0.026 Uiso 1 1 calc R . . C6 C -0.26891(19) 1.1121(2) 0.64008(14) 0.0255(4) Uani 1 1 d . . . H6 H -0.3799 1.1204 0.6437 0.031 Uiso 1 1 calc R . . C7 C -0.18188(19) 1.2304(2) 0.57536(13) 0.0243(3) Uani 1 1 d . . . H7 H -0.2343 1.3182 0.5371 0.029 Uiso 1 1 calc R . . C8 C -0.01952(19) 1.22100(18) 0.56634(13) 0.0211(3) Uani 1 1 d . . . H8 H 0.0404 1.3003 0.5215 0.025 Uiso 1 1 calc R . . C9 C 0.04454(18) 0.69825(18) 0.73052(13) 0.0202(3) Uani 1 1 d . . . C10 C 0.20418(18) 0.63754(18) 0.70508(12) 0.0196(3) Uani 1 1 d . . . C11 C 0.30930(17) 0.75861(17) 0.68936(12) 0.0176(3) Uani 1 1 d . . . C12 C 0.46477(18) 0.73543(19) 0.65387(13) 0.0206(3) Uani 1 1 d . . . H12 H 0.5366 0.8179 0.6430 0.025 Uiso 1 1 calc R . . C13 C 0.5117(2) 0.5875(2) 0.63477(14) 0.0256(4) Uani 1 1 d . . . H13 H 0.6175 0.5686 0.6100 0.031 Uiso 1 1 calc R . . C14 C 0.4068(2) 0.46555(19) 0.65119(14) 0.0273(4) Uani 1 1 d . . . H14 H 0.4425 0.3651 0.6382 0.033 Uiso 1 1 calc R . . C15 C 0.2511(2) 0.48943(18) 0.68620(13) 0.0244(3) Uani 1 1 d . . . H15 H 0.1791 0.4072 0.6969 0.029 Uiso 1 1 calc R . . C16 C 0.1851(2) 1.1308(2) 0.99437(14) 0.0301(4) Uani 1 1 d . . . H16A H 0.2881 1.1079 1.0265 0.036 Uiso 1 1 calc R . . H16B H 0.1040 1.0759 1.0474 0.036 Uiso 1 1 calc R . . C17 C 0.1517(3) 1.3001(2) 0.97942(18) 0.0481(6) Uani 1 1 d . . . H17A H 0.2331 1.3534 0.9274 0.072 Uiso 1 1 calc R . . H17B H 0.1505 1.3371 1.0535 0.072 Uiso 1 1 calc R . . H17C H 0.0496 1.3214 0.9476 0.072 Uiso 1 1 calc R . . C18 C 0.3666(3) 0.6854(2) 0.98585(18) 0.0436(5) Uani 1 1 d . . . H18A H 0.4743 0.7181 0.9594 0.052 Uiso 1 1 calc R . . H18B H 0.3463 0.5888 0.9553 0.052 Uiso 1 1 calc R . . C19 C 0.3505(4) 0.6582(3) 1.1122(2) 0.0619(7) Uani 1 1 d . . . H19A H 0.3814 0.7510 1.1419 0.093 Uiso 1 1 calc R . . H19B H 0.4180 0.5705 1.1405 0.093 Uiso 1 1 calc R . . H19C H 0.2414 0.6351 1.1378 0.093 Uiso 1 1 calc R . . N1 N 0.06139(14) 0.85503(14) 0.74209(10) 0.0171(3) Uani 1 1 d . . . O1 O 0.33297(13) 1.11844(13) 0.58399(9) 0.0227(2) Uani 1 1 d . . . O2 O -0.08003(14) 0.63406(14) 0.73537(10) 0.0285(3) Uani 1 1 d . . . O3 O 0.46863(13) 0.98075(14) 0.84021(10) 0.0254(3) Uani 1 1 d . . . O4 O 0.18530(13) 1.07930(14) 0.88161(9) 0.0244(3) Uani 1 1 d . . . O5 O 0.25393(14) 0.80647(14) 0.94506(10) 0.0275(3) Uani 1 1 d . . . P1 P 0.30188(4) 0.94725(5) 0.85277(3) 0.01810(12) 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 0.0142(7) 0.0206(7) 0.0152(7) -0.0028(6) -0.0003(5) -0.0042(6) C2 0.0200(7) 0.0186(7) 0.0140(7) -0.0053(6) -0.0012(5) -0.0030(6) C3 0.0188(7) 0.0225(7) 0.0138(7) -0.0056(6) -0.0016(5) -0.0019(6) C4 0.0179(7) 0.0232(7) 0.0132(7) -0.0052(6) -0.0031(5) -0.0015(6) C5 0.0172(7) 0.0317(8) 0.0172(7) -0.0054(6) -0.0007(6) -0.0037(6) C6 0.0187(8) 0.0381(9) 0.0210(8) -0.0082(7) -0.0039(6) 0.0024(7) C7 0.0261(8) 0.0294(8) 0.0186(8) -0.0066(6) -0.0064(6) 0.0058(7) C8 0.0249(8) 0.0239(8) 0.0151(7) -0.0035(6) -0.0028(6) -0.0011(6) C9 0.0233(8) 0.0220(8) 0.0152(7) -0.0004(6) -0.0021(6) -0.0067(6) C10 0.0238(8) 0.0212(7) 0.0138(7) -0.0012(6) -0.0024(6) -0.0033(6) C11 0.0200(7) 0.0194(7) 0.0137(7) -0.0024(5) -0.0028(5) -0.0015(6) C12 0.0199(7) 0.0252(8) 0.0173(7) -0.0043(6) -0.0019(6) -0.0022(6) C13 0.0266(8) 0.0291(9) 0.0216(8) -0.0067(7) -0.0018(6) 0.0056(7) C14 0.0371(10) 0.0213(8) 0.0245(8) -0.0060(6) -0.0051(7) 0.0049(7) C15 0.0342(9) 0.0199(8) 0.0196(8) -0.0019(6) -0.0050(7) -0.0048(7) C16 0.0335(9) 0.0402(10) 0.0194(8) -0.0139(7) 0.0015(7) -0.0060(8) C17 0.0786(17) 0.0364(11) 0.0308(10) -0.0153(9) 0.0111(10) -0.0108(11) C18 0.0539(13) 0.0330(10) 0.0428(12) 0.0054(9) -0.0185(10) 0.0009(9) C19 0.095(2) 0.0546(14) 0.0346(12) 0.0094(11) -0.0260(12) -0.0027(14) N1 0.0133(6) 0.0216(6) 0.0163(6) -0.0020(5) -0.0011(5) -0.0044(5) O1 0.0206(6) 0.0246(6) 0.0220(6) -0.0009(4) 0.0013(4) -0.0066(4) O2 0.0245(6) 0.0304(6) 0.0310(6) -0.0036(5) -0.0007(5) -0.0127(5) O3 0.0166(5) 0.0376(7) 0.0239(6) -0.0091(5) -0.0020(4) -0.0056(5) O4 0.0243(6) 0.0323(6) 0.0192(6) -0.0123(5) -0.0033(4) 0.0039(5) O5 0.0279(6) 0.0334(7) 0.0196(6) 0.0040(5) -0.0047(5) -0.0062(5) P1 0.0161(2) 0.0238(2) 0.0150(2) -0.00420(15) -0.00162(14) -0.00272(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.4742(18) . ? C1 C11 1.504(2) . ? C1 C2 1.549(2) . ? C1 P1 1.8423(15) . ? C2 O1 1.2137(18) . ? C2 C3 1.468(2) . ? C3 C8 1.395(2) . ? C3 C4 1.395(2) . ? C4 C5 1.384(2) . ? C4 N1 1.4171(19) . ? C5 C6 1.389(2) . ? C5 H5 0.9500 . ? C6 C7 1.396(2) . ? C6 H6 0.9500 . ? C7 C8 1.389(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 O2 1.2146(19) . ? C9 N1 1.409(2) . ? C9 C10 1.479(2) . ? C10 C15 1.387(2) . ? C10 C11 1.393(2) . ? C11 C12 1.386(2) . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 C14 1.397(2) . ? C13 H13 0.9500 . ? C14 C15 1.388(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 O4 1.4736(19) . ? C16 C17 1.484(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O5 1.463(2) . ? C18 C19 1.483(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O3 P1 1.4601(11) . ? O4 P1 1.5626(12) . ? O5 P1 1.5676(12) . ? 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 C11 103.48(11) . . ? N1 C1 C2 104.49(11) . . ? C11 C1 C2 120.31(12) . . ? N1 C1 P1 109.91(9) . . ? C11 C1 P1 108.24(10) . . ? C2 C1 P1 109.90(10) . . ? O1 C2 C3 129.49(14) . . ? O1 C2 C1 125.20(14) . . ? C3 C2 C1 105.24(12) . . ? C8 C3 C4 120.64(14) . . ? C8 C3 C2 129.86(14) . . ? C4 C3 C2 109.49(13) . . ? C5 C4 C3 122.01(14) . . ? C5 C4 N1 127.11(14) . . ? C3 C4 N1 110.87(13) . . ? C4 C5 C6 116.85(15) . . ? C4 C5 H5 121.6 . . ? C6 C5 H5 121.6 . . ? C5 C6 C7 122.00(15) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C8 C7 C6 120.64(15) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C3 117.84(15) . . ? C7 C8 H8 121.1 . . ? C3 C8 H8 121.1 . . ? O2 C9 N1 124.55(15) . . ? O2 C9 C10 129.29(15) . . ? N1 C9 C10 106.05(13) . . ? C15 C10 C11 121.34(15) . . ? C15 C10 C9 128.85(15) . . ? C11 C10 C9 109.50(14) . . ? C12 C11 C10 121.11(14) . . ? C12 C11 C1 129.94(14) . . ? C10 C11 C1 108.92(13) . . ? C11 C12 C13 117.59(15) . . ? C11 C12 H12 121.2 . . ? C13 C12 H12 121.2 . . ? C12 C13 C14 121.43(16) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C15 C14 C13 120.78(15) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C10 C15 C14 117.74(15) . . ? C10 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? O4 C16 C17 107.91(15) . . ? O4 C16 H16A 110.1 . . ? C17 C16 H16A 110.1 . . ? O4 C16 H16B 110.1 . . ? C17 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O5 C18 C19 108.65(19) . . ? O5 C18 H18A 110.0 . . ? C19 C18 H18A 110.0 . . ? O5 C18 H18B 110.0 . . ? C19 C18 H18B 110.0 . . ? H18A C18 H18B 108.3 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C9 N1 C4 122.98(12) . . ? C9 N1 C1 111.47(12) . . ? C4 N1 C1 108.87(11) . . ? C16 O4 P1 119.04(11) . . ? C18 O5 P1 122.07(12) . . ? O3 P1 O4 117.83(7) . . ? O3 P1 O5 115.31(7) . . ? O4 P1 O5 103.55(7) . . ? O3 P1 C1 112.88(7) . . ? O4 P1 C1 100.80(6) . . ? O5 P1 C1 104.64(7) . . ? 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 N1 C1 C2 O1 -173.22(14) . . . . ? C11 C1 C2 O1 -57.8(2) . . . . ? P1 C1 C2 O1 68.91(17) . . . . ? N1 C1 C2 C3 9.53(14) . . . . ? C11 C1 C2 C3 124.99(14) . . . . ? P1 C1 C2 C3 -108.35(11) . . . . ? O1 C2 C3 C8 -3.1(3) . . . . ? C1 C2 C3 C8 174.01(15) . . . . ? O1 C2 C3 C4 176.99(15) . . . . ? C1 C2 C3 C4 -5.91(16) . . . . ? C8 C3 C4 C5 0.5(2) . . . . ? C2 C3 C4 C5 -179.58(13) . . . . ? C8 C3 C4 N1 179.80(13) . . . . ? C2 C3 C4 N1 -0.27(17) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? N1 C4 C5 C6 -179.51(14) . . . . ? C4 C5 C6 C7 -0.5(2) . . . . ? C5 C6 C7 C8 1.2(2) . . . . ? C6 C7 C8 C3 -0.9(2) . . . . ? C4 C3 C8 C7 0.2(2) . . . . ? C2 C3 C8 C7 -179.76(14) . . . . ? O2 C9 C10 C15 -3.6(3) . . . . ? N1 C9 C10 C15 -179.99(15) . . . . ? O2 C9 C10 C11 169.84(15) . . . . ? N1 C9 C10 C11 -6.51(16) . . . . ? C15 C10 C11 C12 0.2(2) . . . . ? C9 C10 C11 C12 -173.85(13) . . . . ? C15 C10 C11 C1 -177.97(14) . . . . ? C9 C10 C11 C1 7.98(16) . . . . ? N1 C1 C11 C12 175.84(15) . . . . ? C2 C1 C11 C12 59.9(2) . . . . ? P1 C1 C11 C12 -67.56(18) . . . . ? N1 C1 C11 C10 -6.20(15) . . . . ? C2 C1 C11 C10 -122.18(14) . . . . ? P1 C1 C11 C10 110.40(12) . . . . ? C10 C11 C12 C13 -0.1(2) . . . . ? C1 C11 C12 C13 177.66(15) . . . . ? C11 C12 C13 C14 -0.4(2) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C11 C10 C15 C14 0.1(2) . . . . ? C9 C10 C15 C14 172.91(15) . . . . ? C13 C14 C15 C10 -0.5(2) . . . . ? O2 C9 N1 C4 -42.1(2) . . . . ? C10 C9 N1 C4 134.46(14) . . . . ? O2 C9 N1 C1 -174.14(14) . . . . ? C10 C9 N1 C1 2.42(16) . . . . ? C5 C4 N1 C9 53.0(2) . . . . ? C3 C4 N1 C9 -126.30(15) . . . . ? C5 C4 N1 C1 -173.96(14) . . . . ? C3 C4 N1 C1 6.78(16) . . . . ? C11 C1 N1 C9 2.13(15) . . . . ? C2 C1 N1 C9 128.85(12) . . . . ? P1 C1 N1 C9 -113.29(11) . . . . ? C11 C1 N1 C4 -136.68(12) . . . . ? C2 C1 N1 C4 -9.97(14) . . . . ? P1 C1 N1 C4 107.90(11) . . . . ? C17 C16 O4 P1 144.84(14) . . . . ? C19 C18 O5 P1 131.97(17) . . . . ? C16 O4 P1 O3 -68.15(13) . . . . ? C16 O4 P1 O5 60.50(12) . . . . ? C16 O4 P1 C1 168.60(11) . . . . ? C18 O5 P1 O3 -20.98(16) . . . . ? C18 O5 P1 O4 -151.16(14) . . . . ? C18 O5 P1 C1 103.63(14) . . . . ? N1 C1 P1 O3 174.55(9) . . . . ? C11 C1 P1 O3 62.19(12) . . . . ? C2 C1 P1 O3 -70.99(12) . . . . ? N1 C1 P1 O4 -58.83(11) . . . . ? C11 C1 P1 O4 -171.19(10) . . . . ? C2 C1 P1 O4 55.62(11) . . . . ? N1 C1 P1 O5 48.41(11) . . . . ? C11 C1 P1 O5 -63.95(11) . . . . ? C2 C1 P1 O5 162.86(10) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.452 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.055 # Attachment '9330_web_deposit_cif_file_1_Yuen-KiCheong_1327944984.pd-10-02_Final.cif' data_pd-10-02 _database_code_depnum_ccdc_archive 'CCDC 865151' #TrackingRef '9330_web_deposit_cif_file_1_Yuen-KiCheong_1327944984.pd-10-02_Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 N1 O5' _chemical_formula_sum 'C23 H20 N O5 P' _chemical_formula_weight 421.37 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 22.2526(5) _cell_length_b 7.0132(2) _cell_length_c 25.1963(6) _cell_angle_alpha 90.00 _cell_angle_beta 106.297(2) _cell_angle_gamma 90.00 _cell_volume 3774.19(16) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 20198 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description Fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9468 _exptl_absorpt_correction_T_max 0.9927 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 19986 _diffrn_reflns_av_R_equivalents 0.0538 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4293 _reflns_number_gt 3406 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0122P)^2^+11.9589P] 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 4293 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 0.11533(10) 0.8332(3) 0.11189(9) 0.0184(4) Uani 1 1 d . . . C2 C 0.09173(10) 0.8064(3) 0.15859(9) 0.0187(4) Uani 1 1 d . . . C3 C 0.02898(10) 0.7474(3) 0.13712(9) 0.0185(4) Uani 1 1 d . . . C4 C -0.00871(11) 0.7088(3) 0.17151(10) 0.0239(5) Uani 1 1 d . . . H4 H -0.0506 0.6659 0.1570 0.029 Uiso 1 1 calc R . . C5 C 0.01750(11) 0.7355(4) 0.22777(10) 0.0261(5) Uani 1 1 d . . . H5 H -0.0072 0.7112 0.2523 0.031 Uiso 1 1 calc R . . C6 C 0.07938(11) 0.7974(4) 0.24950(10) 0.0262(5) Uani 1 1 d . . . H6 H 0.0956 0.8159 0.2883 0.031 Uiso 1 1 calc R . . C7 C 0.11730(11) 0.8321(3) 0.21550(9) 0.0229(5) Uani 1 1 d . . . H7 H 0.1595 0.8721 0.2304 0.027 Uiso 1 1 calc R . . C8 C 0.06941(10) 0.7999(3) 0.06404(9) 0.0179(4) Uani 1 1 d . . . C9 C 0.06654(10) 0.8173(3) 0.00598(9) 0.0168(4) Uani 1 1 d . . . C10 C 0.11578(10) 0.8837(3) -0.01237(9) 0.0199(5) Uani 1 1 d . . . H10 H 0.1541 0.9178 0.0138 0.024 Uiso 1 1 calc R . . C11 C 0.10975(11) 0.9013(3) -0.06912(10) 0.0227(5) Uani 1 1 d . . . H11 H 0.1439 0.9486 -0.0810 0.027 Uiso 1 1 calc R . . C12 C 0.05541(11) 0.8512(3) -0.10749(9) 0.0224(5) Uani 1 1 d . . . H12 H 0.0522 0.8631 -0.1457 0.027 Uiso 1 1 calc R . . C13 C 0.00385(10) 0.7817(3) -0.09098(9) 0.0194(5) Uani 1 1 d . . . C14 C 0.00924(10) 0.7666(3) -0.03347(9) 0.0178(4) Uani 1 1 d . . . C15 C -0.04324(10) 0.7004(3) -0.01690(9) 0.0180(4) Uani 1 1 d . . . C16 C -0.04121(10) 0.6874(3) 0.04219(9) 0.0188(4) Uani 1 1 d . . . C17 C -0.09743(10) 0.6477(3) -0.05599(10) 0.0219(5) Uani 1 1 d . . . H17 H -0.1318 0.6014 -0.0444 0.026 Uiso 1 1 calc R . . C18 C -0.10267(11) 0.6611(3) -0.11252(10) 0.0235(5) Uani 1 1 d . . . H18 H -0.1404 0.6242 -0.1390 0.028 Uiso 1 1 calc R . . C19 C -0.05332(11) 0.7275(3) -0.12963(10) 0.0232(5) Uani 1 1 d . . . H19 H -0.0574 0.7374 -0.1681 0.028 Uiso 1 1 calc R . . C20 C 0.28677(11) 1.0456(4) 0.20382(10) 0.0250(5) Uani 1 1 d . . . H20A H 0.2858 0.9626 0.2353 0.030 Uiso 1 1 calc R . . H20B H 0.2490 1.1275 0.1949 0.030 Uiso 1 1 calc R . . C21 C 0.34497(12) 1.1671(4) 0.21871(11) 0.0342(6) Uani 1 1 d . . . H21A H 0.3820 1.0848 0.2289 0.051 Uiso 1 1 calc R . . H21B H 0.3446 1.2495 0.2500 0.051 Uiso 1 1 calc R . . H21C H 0.3461 1.2460 0.1869 0.051 Uiso 1 1 calc R . . C22 C 0.29391(11) 0.5509(3) 0.08169(11) 0.0258(5) Uani 1 1 d . . . H22A H 0.3276 0.5595 0.1169 0.031 Uiso 1 1 calc R . . H22B H 0.3127 0.5739 0.0510 0.031 Uiso 1 1 calc R . . C23 C 0.26573(12) 0.3550(4) 0.07604(11) 0.0295(6) Uani 1 1 d . . . H23A H 0.2482 0.3306 0.1070 0.044 Uiso 1 1 calc R . . H23B H 0.2981 0.2602 0.0763 0.044 Uiso 1 1 calc R . . H23C H 0.2324 0.3463 0.0412 0.044 Uiso 1 1 calc R . . N1 N 0.01539(8) 0.7424(3) 0.07932(7) 0.0177(4) Uani 1 1 d . . . O1 O 0.17496(7) 0.9010(2) 0.11476(6) 0.0188(3) Uani 1 1 d . . . O2 O 0.23304(7) 0.6264(2) 0.17679(7) 0.0245(4) Uani 1 1 d . . . O3 O 0.28769(7) 0.9288(2) 0.15565(6) 0.0223(4) Uani 1 1 d . . . O4 O 0.24624(7) 0.6983(2) 0.08071(7) 0.0236(4) Uani 1 1 d . . . O5 O -0.08522(7) 0.6355(2) 0.05848(7) 0.0238(4) Uani 1 1 d . . . P1 P 0.23606(3) 0.77171(8) 0.13616(2) 0.01846(14) 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 0.0161(10) 0.0189(11) 0.0210(11) 0.0001(9) 0.0065(8) -0.0002(8) C2 0.0169(10) 0.0181(11) 0.0206(11) 0.0002(9) 0.0044(9) 0.0028(9) C3 0.0209(11) 0.0157(11) 0.0195(11) -0.0001(9) 0.0066(9) 0.0023(9) C4 0.0200(11) 0.0258(12) 0.0277(12) 0.0048(10) 0.0098(9) 0.0041(9) C5 0.0276(13) 0.0322(13) 0.0225(11) 0.0044(10) 0.0139(10) 0.0044(10) C6 0.0284(13) 0.0315(13) 0.0182(11) 0.0005(10) 0.0060(10) 0.0033(11) C7 0.0224(12) 0.0243(12) 0.0216(11) -0.0007(10) 0.0056(9) 0.0022(9) C8 0.0167(10) 0.0149(10) 0.0230(11) 0.0003(9) 0.0072(9) 0.0002(8) C9 0.0183(11) 0.0136(10) 0.0193(10) 0.0011(8) 0.0064(9) 0.0026(8) C10 0.0182(11) 0.0186(11) 0.0232(11) 0.0008(9) 0.0064(9) 0.0009(9) C11 0.0239(12) 0.0219(11) 0.0250(12) 0.0024(9) 0.0116(10) 0.0018(9) C12 0.0282(12) 0.0209(11) 0.0195(11) 0.0012(9) 0.0092(9) 0.0040(10) C13 0.0210(11) 0.0163(10) 0.0200(11) -0.0012(9) 0.0044(9) 0.0045(9) C14 0.0183(11) 0.0135(10) 0.0211(11) -0.0002(8) 0.0051(9) 0.0026(8) C15 0.0196(11) 0.0128(10) 0.0212(11) 0.0001(8) 0.0049(9) 0.0027(8) C16 0.0167(11) 0.0159(11) 0.0234(11) 0.0003(9) 0.0051(9) 0.0013(8) C17 0.0169(11) 0.0188(11) 0.0283(12) -0.0004(9) 0.0036(9) 0.0003(9) C18 0.0224(12) 0.0204(11) 0.0232(12) -0.0012(9) -0.0010(9) 0.0021(9) C19 0.0277(12) 0.0209(11) 0.0186(11) -0.0001(9) 0.0025(9) 0.0043(10) C20 0.0237(12) 0.0292(13) 0.0212(11) -0.0041(10) 0.0050(9) -0.0025(10) C21 0.0302(14) 0.0316(14) 0.0348(14) -0.0017(12) -0.0009(11) -0.0064(11) C22 0.0201(11) 0.0270(13) 0.0325(13) -0.0034(11) 0.0111(10) 0.0031(10) C23 0.0294(13) 0.0258(13) 0.0353(14) 0.0006(11) 0.0125(11) 0.0039(10) N1 0.0154(9) 0.0201(9) 0.0183(9) -0.0003(7) 0.0061(7) -0.0004(7) O1 0.0139(7) 0.0197(8) 0.0232(8) 0.0008(6) 0.0057(6) 0.0001(6) O2 0.0222(8) 0.0269(9) 0.0242(8) 0.0035(7) 0.0064(7) 0.0006(7) O3 0.0176(8) 0.0268(9) 0.0228(8) -0.0029(7) 0.0063(6) -0.0042(7) O4 0.0226(8) 0.0261(9) 0.0230(8) -0.0012(7) 0.0080(7) 0.0041(7) O5 0.0180(8) 0.0263(9) 0.0289(9) 0.0000(7) 0.0091(7) -0.0023(7) P1 0.0159(3) 0.0207(3) 0.0185(3) 0.0002(2) 0.0045(2) -0.0002(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C8 1.364(3) . ? C1 O1 1.392(3) . ? C1 C2 1.429(3) . ? C2 C7 1.398(3) . ? C2 C3 1.410(3) . ? C3 C4 1.391(3) . ? C3 N1 1.402(3) . ? C4 C5 1.386(3) . ? C4 H4 0.9500 . ? C5 C6 1.400(3) . ? C5 H5 0.9500 . ? C6 C7 1.382(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 N1 1.420(3) . ? C8 C9 1.451(3) . ? C9 C10 1.384(3) . ? C9 C14 1.425(3) . ? C10 C11 1.404(3) . ? C10 H10 0.9500 . ? C11 C12 1.365(3) . ? C11 H11 0.9500 . ? C12 C13 1.412(3) . ? C12 H12 0.9500 . ? C13 C19 1.420(3) . ? C13 C14 1.424(3) . ? C14 C15 1.424(3) . ? C15 C17 1.376(3) . ? C15 C16 1.480(3) . ? C16 O5 1.219(3) . ? C16 N1 1.396(3) . ? C17 C18 1.399(3) . ? C17 H17 0.9500 . ? C18 C19 1.369(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 O3 1.469(3) . ? C20 C21 1.507(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 O4 1.476(3) . ? C22 C23 1.500(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O1 P1 1.5969(16) . ? O2 P1 1.4594(17) . ? O3 P1 1.5681(16) . ? O4 P1 1.5641(16) . ? 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 C8 C1 O1 124.82(19) . . ? C8 C1 C2 110.36(19) . . ? O1 C1 C2 124.6(2) . . ? C7 C2 C3 120.4(2) . . ? C7 C2 C1 133.6(2) . . ? C3 C2 C1 106.00(19) . . ? C4 C3 N1 130.5(2) . . ? C4 C3 C2 121.5(2) . . ? N1 C3 C2 107.92(18) . . ? C5 C4 C3 117.2(2) . . ? C5 C4 H4 121.4 . . ? C3 C4 H4 121.4 . . ? C4 C5 C6 121.8(2) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 121.1(2) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C2 118.0(2) . . ? C6 C7 H7 121.0 . . ? C2 C7 H7 121.0 . . ? C1 C8 N1 106.87(18) . . ? C1 C8 C9 133.3(2) . . ? N1 C8 C9 119.75(19) . . ? C10 C9 C14 119.2(2) . . ? C10 C9 C8 123.4(2) . . ? C14 C9 C8 117.37(19) . . ? C9 C10 C11 120.8(2) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C12 C11 C10 120.8(2) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 120.8(2) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C19 122.4(2) . . ? C12 C13 C14 118.8(2) . . ? C19 C13 C14 118.8(2) . . ? C15 C14 C13 118.7(2) . . ? C15 C14 C9 121.6(2) . . ? C13 C14 C9 119.66(19) . . ? C17 C15 C14 120.3(2) . . ? C17 C15 C16 118.5(2) . . ? C14 C15 C16 121.3(2) . . ? O5 C16 N1 121.1(2) . . ? O5 C16 C15 123.8(2) . . ? N1 C16 C15 115.12(18) . . ? C15 C17 C18 121.1(2) . . ? C15 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C19 C18 C17 119.9(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C13 121.2(2) . . ? C18 C19 H19 119.4 . . ? C13 C19 H19 119.4 . . ? O3 C20 C21 108.10(19) . . ? O3 C20 H20A 110.1 . . ? C21 C20 H20A 110.1 . . ? O3 C20 H20B 110.1 . . ? C21 C20 H20B 110.1 . . ? H20A C20 H20B 108.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 C23 111.11(18) . . ? O4 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? O4 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C16 N1 C3 126.45(18) . . ? C16 N1 C8 124.75(18) . . ? C3 N1 C8 108.80(17) . . ? C1 O1 P1 122.14(14) . . ? C20 O3 P1 118.14(14) . . ? C22 O4 P1 119.94(15) . . ? O2 P1 O4 116.32(10) . . ? O2 P1 O3 116.43(10) . . ? O4 P1 O3 103.54(9) . . ? O2 P1 O1 115.54(9) . . ? O4 P1 O1 102.03(9) . . ? O3 P1 O1 100.73(9) . . ? 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 C8 C1 C2 C7 -175.7(2) . . . . ? O1 C1 C2 C7 -1.3(4) . . . . ? C8 C1 C2 C3 2.1(3) . . . . ? O1 C1 C2 C3 176.5(2) . . . . ? C7 C2 C3 C4 -1.6(3) . . . . ? C1 C2 C3 C4 -179.8(2) . . . . ? C7 C2 C3 N1 177.3(2) . . . . ? C1 C2 C3 N1 -0.9(2) . . . . ? N1 C3 C4 C5 -176.9(2) . . . . ? C2 C3 C4 C5 1.7(3) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C4 C5 C6 C7 -0.9(4) . . . . ? C5 C6 C7 C2 1.0(4) . . . . ? C3 C2 C7 C6 0.2(3) . . . . ? C1 C2 C7 C6 177.8(2) . . . . ? O1 C1 C8 N1 -176.82(19) . . . . ? C2 C1 C8 N1 -2.5(2) . . . . ? O1 C1 C8 C9 1.2(4) . . . . ? C2 C1 C8 C9 175.6(2) . . . . ? C1 C8 C9 C10 -2.0(4) . . . . ? N1 C8 C9 C10 175.8(2) . . . . ? C1 C8 C9 C14 179.4(2) . . . . ? N1 C8 C9 C14 -2.8(3) . . . . ? C14 C9 C10 C11 0.0(3) . . . . ? C8 C9 C10 C11 -178.6(2) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C11 C12 C13 C19 -179.8(2) . . . . ? C11 C12 C13 C14 0.6(3) . . . . ? C12 C13 C14 C15 178.7(2) . . . . ? C19 C13 C14 C15 -0.9(3) . . . . ? C12 C13 C14 C9 -1.4(3) . . . . ? C19 C13 C14 C9 179.0(2) . . . . ? C10 C9 C14 C15 -179.0(2) . . . . ? C8 C9 C14 C15 -0.3(3) . . . . ? C10 C9 C14 C13 1.1(3) . . . . ? C8 C9 C14 C13 179.79(19) . . . . ? C13 C14 C15 C17 1.6(3) . . . . ? C9 C14 C15 C17 -178.3(2) . . . . ? C13 C14 C15 C16 -178.04(19) . . . . ? C9 C14 C15 C16 2.1(3) . . . . ? C17 C15 C16 O5 -1.3(3) . . . . ? C14 C15 C16 O5 178.4(2) . . . . ? C17 C15 C16 N1 179.68(19) . . . . ? C14 C15 C16 N1 -0.6(3) . . . . ? C14 C15 C17 C18 -1.2(3) . . . . ? C16 C15 C17 C18 178.5(2) . . . . ? C15 C17 C18 C19 0.0(3) . . . . ? C17 C18 C19 C13 0.7(3) . . . . ? C12 C13 C19 C18 -179.8(2) . . . . ? C14 C13 C19 C18 -0.2(3) . . . . ? O5 C16 N1 C3 -0.6(3) . . . . ? C15 C16 N1 C3 178.49(19) . . . . ? O5 C16 N1 C8 178.3(2) . . . . ? C15 C16 N1 C8 -2.6(3) . . . . ? C4 C3 N1 C16 -2.8(4) . . . . ? C2 C3 N1 C16 178.5(2) . . . . ? C4 C3 N1 C8 178.2(2) . . . . ? C2 C3 N1 C8 -0.5(2) . . . . ? C1 C8 N1 C16 -177.2(2) . . . . ? C9 C8 N1 C16 4.4(3) . . . . ? C1 C8 N1 C3 1.8(2) . . . . ? C9 C8 N1 C3 -176.50(19) . . . . ? C8 C1 O1 P1 -111.4(2) . . . . ? C2 C1 O1 P1 75.1(3) . . . . ? C21 C20 O3 P1 172.87(16) . . . . ? C23 C22 O4 P1 93.2(2) . . . . ? C22 O4 P1 O2 -45.17(19) . . . . ? C22 O4 P1 O3 83.86(17) . . . . ? C22 O4 P1 O1 -171.83(16) . . . . ? C20 O3 P1 O2 -58.37(19) . . . . ? C20 O3 P1 O4 172.67(16) . . . . ? C20 O3 P1 O1 67.38(17) . . . . ? C1 O1 P1 O2 -29.88(19) . . . . ? C1 O1 P1 O4 97.29(17) . . . . ? C1 O1 P1 O3 -156.21(16) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.325 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.066 # Attachment '9331_web_deposit_cif_file_2_Yuen-KiCheong_1327944984.pd-9-131-Fiinal.cif' data_pd-9-131 _database_code_depnum_ccdc_archive 'CCDC 865152' #TrackingRef '9331_web_deposit_cif_file_2_Yuen-KiCheong_1327944984.pd-9-131-Fiinal.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 Cl2 N1 O5 P1' _chemical_formula_sum 'C15 H14 Cl2 N O5 P' _chemical_formula_weight 390.14 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' 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 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 12.4096(3) _cell_length_b 9.6934(2) _cell_length_c 27.4755(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.9430(10) _cell_angle_gamma 90.00 _cell_volume 3300.70(13) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 32472 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.516 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9038 _exptl_absorpt_correction_T_max 0.9697 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 29073 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.57 _reflns_number_total 7515 _reflns_number_gt 6115 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0000P)^2^+11.1938P] 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 7515 _refine_ls_number_parameters 437 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _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 Cl1B Cl 0.05320(7) 0.03812(9) 0.20407(3) 0.02227(18) Uani 1 1 d . . . P1B P -0.19748(7) 0.18690(9) 0.15721(3) 0.01643(18) Uani 1 1 d . . . P1A P -0.69261(7) 0.45171(9) 0.14229(3) 0.01670(18) Uani 1 1 d . . . Cl1A Cl -0.43220(7) 0.59292(9) 0.18375(3) 0.02369(19) Uani 1 1 d . . . Cl2A Cl -0.33446(8) 0.60853(10) 0.07131(4) 0.0307(2) Uani 1 1 d . . . Cl2B Cl 0.16344(7) 0.01049(10) 0.09487(3) 0.0277(2) Uani 1 1 d . . . O2B O -0.0229(2) 0.3708(3) 0.23069(8) 0.0220(5) Uani 1 1 d . . . O5B O -0.20527(19) 0.0630(2) 0.12030(8) 0.0192(5) Uani 1 1 d . . . O2A O -0.5209(2) 0.2683(3) 0.21616(9) 0.0242(5) Uani 1 1 d . . . O5A O -0.70305(19) 0.5686(2) 0.10266(9) 0.0211(5) Uani 1 1 d . . . O4A O -0.67760(19) 0.5308(3) 0.19152(9) 0.0225(5) Uani 1 1 d . . . O4B O -0.18812(19) 0.1171(2) 0.20839(8) 0.0186(5) Uani 1 1 d . . . O3A O -0.77491(19) 0.3438(3) 0.13840(9) 0.0220(5) Uani 1 1 d . . . C4B C -0.0571(3) 0.2499(3) 0.15293(11) 0.0157(6) Uani 1 1 d . . . O3B O -0.2781(2) 0.2956(3) 0.14869(9) 0.0256(6) Uani 1 1 d . . . O1A O -0.4484(2) 0.3486(3) 0.02049(9) 0.0258(6) Uani 1 1 d . . . N1A N -0.5528(2) 0.3218(3) 0.08781(10) 0.0161(6) Uani 1 1 d . . . O1B O 0.0548(2) 0.2647(3) 0.03743(8) 0.0242(5) Uani 1 1 d . . . C4A C -0.5539(3) 0.3833(3) 0.13685(11) 0.0163(7) Uani 1 1 d . . . C5B C -0.0378(3) 0.3761(3) 0.18702(12) 0.0191(7) Uani 1 1 d . . . C3B C 0.0253(3) 0.1368(3) 0.15415(12) 0.0171(7) Uani 1 1 d . . . C11A C -0.5548(3) 0.1758(3) 0.09256(12) 0.0178(7) Uani 1 1 d . . . C5A C -0.5356(3) 0.2601(3) 0.17254(12) 0.0183(7) Uani 1 1 d . . . C11B C -0.0505(3) 0.4532(4) 0.10593(12) 0.0179(7) Uani 1 1 d . . . C1B C 0.0276(3) 0.2353(3) 0.07768(12) 0.0172(7) Uani 1 1 d . . . C2B C 0.0674(3) 0.1245(3) 0.11082(12) 0.0179(7) Uani 1 1 d . . . C6B C -0.0461(3) 0.4966(3) 0.15436(12) 0.0171(7) Uani 1 1 d . . . C8A C -0.5536(3) -0.0997(4) 0.11714(14) 0.0254(8) Uani 1 1 d . . . H8A H -0.5543 -0.1952 0.1249 0.031 Uiso 1 1 calc R . . C10B C -0.0521(3) 0.5456(4) 0.06779(13) 0.0204(7) Uani 1 1 d . . . H10B H -0.0541 0.5154 0.0348 0.024 Uiso 1 1 calc R . . C2A C -0.4310(3) 0.5000(4) 0.09067(13) 0.0199(7) Uani 1 1 d . . . C7A C -0.5456(3) -0.0028(4) 0.15440(14) 0.0233(7) Uani 1 1 d . . . H7A H -0.5403 -0.0302 0.1876 0.028 Uiso 1 1 calc R . . C6A C -0.5456(3) 0.1363(4) 0.14123(12) 0.0184(7) Uani 1 1 d . . . C9B C -0.0506(3) 0.6847(4) 0.07975(13) 0.0228(7) Uani 1 1 d . . . H9B H -0.0516 0.7510 0.0542 0.027 Uiso 1 1 calc R . . C10A C -0.5624(3) 0.0801(4) 0.05528(13) 0.0218(7) Uani 1 1 d . . . H10A H -0.5687 0.1078 0.0221 0.026 Uiso 1 1 calc R . . N1B N -0.0513(2) 0.3055(3) 0.10321(9) 0.0156(6) Uani 1 1 d . . . C3A C -0.4691(3) 0.4929(3) 0.13517(12) 0.0168(7) Uani 1 1 d . . . C1A C -0.4749(3) 0.3858(4) 0.06013(12) 0.0191(7) Uani 1 1 d . . . C9A C -0.5605(3) -0.0588(4) 0.06843(14) 0.0239(8) Uani 1 1 d . . . H9A H -0.5639 -0.1271 0.0436 0.029 Uiso 1 1 calc R . . C7B C -0.0448(3) 0.6370(4) 0.16613(13) 0.0215(7) Uani 1 1 d . . . H7B H -0.0421 0.6672 0.1991 0.026 Uiso 1 1 calc R . . C12A C -0.7504(3) 0.5415(4) 0.05366(13) 0.0248(8) Uani 1 1 d . . . H12A H -0.8126 0.4781 0.0554 0.030 Uiso 1 1 calc R . . H12B H -0.6963 0.4982 0.0333 0.030 Uiso 1 1 calc R . . C12B C -0.2731(3) 0.0257(4) 0.22512(13) 0.0220(7) Uani 1 1 d . . . H12C H -0.3419 0.0447 0.2065 0.026 Uiso 1 1 calc R . . H12D H -0.2839 0.0425 0.2601 0.026 Uiso 1 1 calc R . . C8B C -0.0477(3) 0.7307(4) 0.12787(14) 0.0241(8) Uani 1 1 d . . . H8B H -0.0476 0.8269 0.1345 0.029 Uiso 1 1 calc R . . C13A C -0.7864(3) 0.6770(4) 0.03207(14) 0.0280(8) Uani 1 1 d . . . H13A H -0.8414 0.7177 0.0520 0.042 Uiso 1 1 calc R . . H13B H -0.8167 0.6623 -0.0012 0.042 Uiso 1 1 calc R . . H13C H -0.7245 0.7396 0.0313 0.042 Uiso 1 1 calc R . . C14B C -0.2661(3) 0.0750(5) 0.07345(13) 0.0311(9) Uani 1 1 d . . . H14A H -0.2716 0.1731 0.0636 0.037 Uiso 1 1 calc R . . H14B H -0.3400 0.0382 0.0762 0.037 Uiso 1 1 calc R . . C14A C -0.7688(3) 0.6020(4) 0.21297(14) 0.0265(8) Uani 1 1 d . . . H14C H -0.7793 0.5655 0.2460 0.032 Uiso 1 1 calc R . . H14D H -0.8358 0.5859 0.1926 0.032 Uiso 1 1 calc R . . C13B C -0.2403(3) -0.1215(4) 0.21770(14) 0.0304(9) Uani 1 1 d . . . H13D H -0.2329 -0.1386 0.1829 0.046 Uiso 1 1 calc R . . H13E H -0.2955 -0.1830 0.2299 0.046 Uiso 1 1 calc R . . H13F H -0.1712 -0.1390 0.2355 0.046 Uiso 1 1 calc R . . C15B C -0.2088(4) -0.0049(5) 0.03653(14) 0.0343(9) Uani 1 1 d . . . H15A H -0.1350 0.0303 0.0348 0.052 Uiso 1 1 calc R . . H15B H -0.2470 0.0049 0.0046 0.052 Uiso 1 1 calc R . . H15C H -0.2064 -0.1025 0.0458 0.052 Uiso 1 1 calc R . . C15A C -0.7449(3) 0.7530(4) 0.21562(16) 0.0353(10) Uani 1 1 d . . . H15D H -0.6754 0.7677 0.2334 0.053 Uiso 1 1 calc R . . H15E H -0.8020 0.8001 0.2326 0.053 Uiso 1 1 calc R . . H15F H -0.7418 0.7903 0.1826 0.053 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 Cl1B 0.0236(4) 0.0237(4) 0.0195(4) 0.0038(3) 0.0010(3) 0.0059(3) P1B 0.0157(4) 0.0162(4) 0.0175(4) 0.0024(3) 0.0018(3) 0.0002(3) P1A 0.0146(4) 0.0170(4) 0.0185(4) -0.0016(3) 0.0014(3) 0.0005(3) Cl1A 0.0234(4) 0.0240(4) 0.0233(4) -0.0051(3) -0.0023(3) -0.0034(3) Cl2A 0.0255(5) 0.0323(5) 0.0350(5) 0.0010(4) 0.0097(4) -0.0105(4) Cl2B 0.0273(5) 0.0257(5) 0.0311(5) -0.0026(4) 0.0104(4) 0.0085(4) O2B 0.0274(13) 0.0243(13) 0.0145(11) -0.0021(10) 0.0019(10) 0.0018(11) O5B 0.0203(12) 0.0172(12) 0.0195(12) 0.0009(9) -0.0028(9) -0.0014(9) O2A 0.0290(14) 0.0261(14) 0.0175(12) 0.0003(10) -0.0004(10) 0.0003(11) O5A 0.0209(12) 0.0176(12) 0.0242(13) 0.0004(10) -0.0041(10) 0.0000(10) O4A 0.0186(12) 0.0262(14) 0.0228(12) -0.0096(10) 0.0009(10) 0.0029(10) O4B 0.0195(12) 0.0208(12) 0.0159(11) 0.0019(9) 0.0033(9) -0.0027(10) O3A 0.0193(12) 0.0219(13) 0.0249(13) -0.0008(10) 0.0008(10) -0.0063(10) C4B 0.0172(16) 0.0154(16) 0.0150(15) 0.0017(12) 0.0049(12) 0.0006(13) O3B 0.0211(13) 0.0221(13) 0.0339(14) 0.0060(11) 0.0050(11) 0.0065(10) O1A 0.0279(14) 0.0274(14) 0.0230(13) -0.0013(11) 0.0100(11) -0.0009(11) N1A 0.0188(14) 0.0149(14) 0.0147(13) -0.0036(11) 0.0019(11) 0.0016(11) O1B 0.0299(14) 0.0261(14) 0.0171(12) -0.0003(10) 0.0068(10) -0.0008(11) C4A 0.0191(16) 0.0167(16) 0.0130(15) -0.0009(12) -0.0007(12) -0.0014(13) C5B 0.0215(17) 0.0167(17) 0.0192(17) -0.0003(13) 0.0037(13) 0.0010(13) C3B 0.0187(16) 0.0149(16) 0.0179(16) 0.0009(13) 0.0019(13) -0.0015(13) C11A 0.0121(15) 0.0164(16) 0.0248(17) -0.0001(13) 0.0007(13) 0.0001(12) C5A 0.0176(16) 0.0173(17) 0.0200(17) 0.0008(13) 0.0015(13) -0.0003(13) C11B 0.0166(16) 0.0185(17) 0.0188(16) 0.0001(13) 0.0021(13) -0.0014(13) C1B 0.0182(16) 0.0177(16) 0.0156(16) -0.0023(13) 0.0011(12) -0.0030(13) C2B 0.0156(16) 0.0150(16) 0.0231(17) -0.0031(13) 0.0020(13) -0.0008(13) C6B 0.0151(15) 0.0172(16) 0.0193(16) 0.0008(13) 0.0026(12) 0.0018(13) C8A 0.0224(18) 0.0143(17) 0.040(2) -0.0008(15) 0.0023(16) 0.0003(14) C10B 0.0195(17) 0.0201(17) 0.0218(17) 0.0044(14) 0.0042(13) -0.0010(14) C2A 0.0160(16) 0.0176(17) 0.0262(18) 0.0012(14) 0.0014(13) -0.0018(13) C7A 0.0175(17) 0.0227(18) 0.0294(19) 0.0041(15) -0.0005(14) -0.0002(14) C6A 0.0147(16) 0.0177(17) 0.0227(17) 0.0003(14) 0.0000(13) 0.0010(13) C9B 0.0180(17) 0.0223(18) 0.0284(19) 0.0057(15) 0.0034(14) 0.0009(14) C10A 0.0182(17) 0.0244(19) 0.0228(18) -0.0034(14) 0.0021(13) -0.0012(14) N1B 0.0176(14) 0.0164(14) 0.0129(13) 0.0013(11) 0.0018(10) 0.0005(11) C3A 0.0151(15) 0.0136(16) 0.0214(16) -0.0018(13) -0.0020(12) 0.0037(12) C1A 0.0169(16) 0.0187(17) 0.0219(17) 0.0030(14) 0.0025(13) 0.0038(13) C9A 0.0166(17) 0.0231(19) 0.033(2) -0.0129(15) 0.0059(14) -0.0009(14) C7B 0.0188(17) 0.0210(18) 0.0247(18) -0.0033(14) 0.0023(13) 0.0015(14) C12A 0.030(2) 0.0217(18) 0.0219(18) 0.0023(15) -0.0043(15) 0.0008(15) C12B 0.0198(17) 0.0239(19) 0.0226(17) 0.0010(14) 0.0054(14) -0.0047(14) C8B 0.0248(19) 0.0153(17) 0.032(2) 0.0002(15) 0.0042(15) 0.0004(14) C13A 0.0231(19) 0.027(2) 0.034(2) 0.0065(16) -0.0032(16) -0.0001(15) C14B 0.027(2) 0.044(2) 0.0212(19) -0.0002(17) -0.0088(15) 0.0050(18) C14A 0.0174(17) 0.032(2) 0.030(2) -0.0082(16) 0.0046(15) 0.0050(15) C13B 0.044(2) 0.0197(19) 0.029(2) 0.0017(16) 0.0097(17) -0.0040(17) C15B 0.041(2) 0.038(2) 0.0234(19) -0.0068(17) -0.0062(17) 0.0077(19) C15A 0.037(2) 0.024(2) 0.046(3) 0.0037(18) 0.0124(19) 0.0101(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl1B C3B 1.693(3) . ? P1B O3B 1.463(3) . ? P1B O4B 1.559(2) . ? P1B O5B 1.572(2) . ? P1B C4B 1.855(3) . ? P1A O3A 1.462(2) . ? P1A O4A 1.558(2) . ? P1A O5A 1.572(3) . ? P1A C4A 1.858(3) . ? Cl1A C3A 1.694(3) . ? Cl2A C2A 1.700(3) . ? Cl2B C2B 1.699(3) . ? O2B C5B 1.206(4) . ? O5B C14B 1.463(4) . ? O2A C5A 1.206(4) . ? O5A C12A 1.465(4) . ? O4A C14A 1.474(4) . ? O4B C12B 1.469(4) . ? C4B N1B 1.474(4) . ? C4B C3B 1.498(4) . ? C4B C5B 1.552(5) . ? O1A C1A 1.209(4) . ? N1A C1A 1.404(4) . ? N1A C11A 1.421(4) . ? N1A C4A 1.474(4) . ? O1B C1B 1.207(4) . ? C4A C3A 1.498(5) . ? C4A C5A 1.555(5) . ? C5B C6B 1.473(5) . ? C3B C2B 1.330(4) . ? C11A C10A 1.382(5) . ? C11A C6A 1.390(5) . ? C5A C6A 1.478(5) . ? C11B C10B 1.378(5) . ? C11B C6B 1.394(5) . ? C11B N1B 1.434(4) . ? C1B N1B 1.409(4) . ? C1B C2B 1.477(5) . ? C6B C7B 1.399(5) . ? C8A C7A 1.390(5) . ? C8A C9A 1.394(5) . ? C8A H8A 0.9500 . ? C10B C9B 1.388(5) . ? C10B H10B 0.9500 . ? C2A C3A 1.335(5) . ? C2A C1A 1.476(5) . ? C7A C6A 1.396(5) . ? C7A H7A 0.9500 . ? C9B C8B 1.394(5) . ? C9B H9B 0.9500 . ? C10A C9A 1.394(5) . ? C10A H10A 0.9500 . ? C9A H9A 0.9500 . ? C7B C8B 1.388(5) . ? C7B H7B 0.9500 . ? C12A C13A 1.500(5) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C12B C13B 1.500(5) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C8B H8B 0.9500 . ? C13A H13A 0.9800 . ? C13A H13B 0.9800 . ? C13A H13C 0.9800 . ? C14B C15B 1.486(5) . ? C14B H14A 0.9900 . ? C14B H14B 0.9900 . ? C14A C15A 1.495(5) . ? C14A H14C 0.9900 . ? C14A H14D 0.9900 . ? C13B H13D 0.9800 . ? C13B H13E 0.9800 . ? C13B H13F 0.9800 . ? C15B H15A 0.9800 . ? C15B H15B 0.9800 . ? C15B H15C 0.9800 . ? C15A H15D 0.9800 . ? C15A H15E 0.9800 . ? C15A H15F 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 O3B P1B O4B 118.37(14) . . ? O3B P1B O5B 115.35(14) . . ? O4B P1B O5B 104.45(13) . . ? O3B P1B C4B 112.92(15) . . ? O4B P1B C4B 99.97(14) . . ? O5B P1B C4B 103.73(14) . . ? O3A P1A O4A 117.88(15) . . ? O3A P1A O5A 115.65(14) . . ? O4A P1A O5A 104.39(14) . . ? O3A P1A C4A 112.66(15) . . ? O4A P1A C4A 100.11(14) . . ? O5A P1A C4A 104.20(14) . . ? C14B O5B P1B 121.2(2) . . ? C12A O5A P1A 121.5(2) . . ? C14A O4A P1A 121.2(2) . . ? C12B O4B P1B 121.5(2) . . ? N1B C4B C3B 102.8(2) . . ? N1B C4B C5B 104.9(3) . . ? C3B C4B C5B 118.6(3) . . ? N1B C4B P1B 105.7(2) . . ? C3B C4B P1B 113.6(2) . . ? C5B C4B P1B 109.7(2) . . ? C1A N1A C11A 120.4(3) . . ? C1A N1A C4A 110.8(3) . . ? C11A N1A C4A 108.5(3) . . ? N1A C4A C3A 102.7(3) . . ? N1A C4A C5A 104.9(3) . . ? C3A C4A C5A 119.0(3) . . ? N1A C4A P1A 105.7(2) . . ? C3A C4A P1A 113.8(2) . . ? C5A C4A P1A 109.2(2) . . ? O2B C5B C6B 130.0(3) . . ? O2B C5B C4B 125.3(3) . . ? C6B C5B C4B 104.7(3) . . ? C2B C3B C4B 110.2(3) . . ? C2B C3B Cl1B 126.9(3) . . ? C4B C3B Cl1B 122.8(2) . . ? C10A C11A C6A 121.8(3) . . ? C10A C11A N1A 127.0(3) . . ? C6A C11A N1A 111.2(3) . . ? O2A C5A C6A 129.5(3) . . ? O2A C5A C4A 125.9(3) . . ? C6A C5A C4A 104.6(3) . . ? C10B C11B C6B 121.9(3) . . ? C10B C11B N1B 127.6(3) . . ? C6B C11B N1B 110.6(3) . . ? O1B C1B N1B 125.2(3) . . ? O1B C1B C2B 129.6(3) . . ? N1B C1B C2B 105.3(3) . . ? C3B C2B C1B 110.6(3) . . ? C3B C2B Cl2B 127.1(3) . . ? C1B C2B Cl2B 122.1(2) . . ? C11B C6B C7B 120.9(3) . . ? C11B C6B C5B 109.9(3) . . ? C7B C6B C5B 129.1(3) . . ? C7A C8A C9A 120.9(3) . . ? C7A C8A H8A 119.6 . . ? C9A C8A H8A 119.6 . . ? C11B C10B C9B 116.9(3) . . ? C11B C10B H10B 121.6 . . ? C9B C10B H10B 121.6 . . ? C3A C2A C1A 110.1(3) . . ? C3A C2A Cl2A 127.4(3) . . ? C1A C2A Cl2A 122.1(3) . . ? C8A C7A C6A 117.6(3) . . ? C8A C7A H7A 121.2 . . ? C6A C7A H7A 121.2 . . ? C11A C6A C7A 121.0(3) . . ? C11A C6A C5A 109.7(3) . . ? C7A C6A C5A 129.4(3) . . ? C10B C9B C8B 122.3(3) . . ? C10B C9B H9B 118.8 . . ? C8B C9B H9B 118.8 . . ? C11A C10A C9A 117.2(3) . . ? C11A C10A H10A 121.4 . . ? C9A C10A H10A 121.4 . . ? C1B N1B C11B 120.4(3) . . ? C1B N1B C4B 110.7(3) . . ? C11B N1B C4B 108.5(3) . . ? C2A C3A C4A 110.3(3) . . ? C2A C3A Cl1A 126.7(3) . . ? C4A C3A Cl1A 123.0(2) . . ? O1A C1A N1A 125.6(3) . . ? O1A C1A C2A 128.8(3) . . ? N1A C1A C2A 105.5(3) . . ? C10A C9A C8A 121.6(3) . . ? C10A C9A H9A 119.2 . . ? C8A C9A H9A 119.2 . . ? C8B C7B C6B 117.5(3) . . ? C8B C7B H7B 121.2 . . ? C6B C7B H7B 121.2 . . ? O5A C12A C13A 107.7(3) . . ? O5A C12A H12A 110.2 . . ? C13A C12A H12A 110.2 . . ? O5A C12A H12B 110.2 . . ? C13A C12A H12B 110.2 . . ? H12A C12A H12B 108.5 . . ? O4B C12B C13B 109.1(3) . . ? O4B C12B H12C 109.9 . . ? C13B C12B H12C 109.9 . . ? O4B C12B H12D 109.9 . . ? C13B C12B H12D 109.9 . . ? H12C C12B H12D 108.3 . . ? C7B C8B C9B 120.5(3) . . ? C7B C8B H8B 119.7 . . ? C9B C8B H8B 119.7 . . ? C12A C13A H13A 109.5 . . ? C12A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C12A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? O5B C14B C15B 108.4(3) . . ? O5B C14B H14A 110.0 . . ? C15B C14B H14A 110.0 . . ? O5B C14B H14B 110.0 . . ? C15B C14B H14B 110.0 . . ? H14A C14B H14B 108.4 . . ? O4A C14A C15A 108.9(3) . . ? O4A C14A H14C 109.9 . . ? C15A C14A H14C 109.9 . . ? O4A C14A H14D 109.9 . . ? C15A C14A H14D 109.9 . . ? H14C C14A H14D 108.3 . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C14B C15B H15A 109.5 . . ? C14B C15B H15B 109.5 . . ? H15A C15B H15B 109.5 . . ? C14B C15B H15C 109.5 . . ? H15A C15B H15C 109.5 . . ? H15B C15B H15C 109.5 . . ? C14A C15A H15D 109.5 . . ? C14A C15A H15E 109.5 . . ? H15D C15A H15E 109.5 . . ? C14A C15A H15F 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 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 O3B P1B O5B C14B 17.3(3) . . . . ? O4B P1B O5B C14B 149.0(3) . . . . ? C4B P1B O5B C14B -106.7(3) . . . . ? O3A P1A O5A C12A -29.8(3) . . . . ? O4A P1A O5A C12A -161.0(2) . . . . ? C4A P1A O5A C12A 94.4(3) . . . . ? O3A P1A O4A C14A -55.8(3) . . . . ? O5A P1A O4A C14A 74.1(3) . . . . ? C4A P1A O4A C14A -178.3(3) . . . . ? O3B P1B O4B C12B 69.7(3) . . . . ? O5B P1B O4B C12B -60.2(3) . . . . ? C4B P1B O4B C12B -167.3(2) . . . . ? O3B P1B C4B N1B -59.4(2) . . . . ? O4B P1B C4B N1B 173.8(2) . . . . ? O5B P1B C4B N1B 66.1(2) . . . . ? O3B P1B C4B C3B -171.4(2) . . . . ? O4B P1B C4B C3B 61.8(2) . . . . ? O5B P1B C4B C3B -45.8(3) . . . . ? O3B P1B C4B C5B 53.2(3) . . . . ? O4B P1B C4B C5B -73.5(2) . . . . ? O5B P1B C4B C5B 178.8(2) . . . . ? C1A N1A C4A C3A 0.9(3) . . . . ? C11A N1A C4A C3A 135.1(3) . . . . ? C1A N1A C4A C5A -124.1(3) . . . . ? C11A N1A C4A C5A 10.1(3) . . . . ? C1A N1A C4A P1A 120.4(2) . . . . ? C11A N1A C4A P1A -105.3(2) . . . . ? O3A P1A C4A N1A 61.7(2) . . . . ? O4A P1A C4A N1A -172.2(2) . . . . ? O5A P1A C4A N1A -64.4(2) . . . . ? O3A P1A C4A C3A 173.6(2) . . . . ? O4A P1A C4A C3A -60.3(3) . . . . ? O5A P1A C4A C3A 47.5(3) . . . . ? O3A P1A C4A C5A -50.7(3) . . . . ? O4A P1A C4A C5A 75.4(2) . . . . ? O5A P1A C4A C5A -176.8(2) . . . . ? N1B C4B C5B O2B -170.1(3) . . . . ? C3B C4B C5B O2B -56.1(5) . . . . ? P1B C4B C5B O2B 76.7(4) . . . . ? N1B C4B C5B C6B 11.9(3) . . . . ? C3B C4B C5B C6B 125.9(3) . . . . ? P1B C4B C5B C6B -101.2(3) . . . . ? N1B C4B C3B C2B -3.1(4) . . . . ? C5B C4B C3B C2B -118.2(3) . . . . ? P1B C4B C3B C2B 110.6(3) . . . . ? N1B C4B C3B Cl1B 179.3(2) . . . . ? C5B C4B C3B Cl1B 64.1(4) . . . . ? P1B C4B C3B Cl1B -67.1(3) . . . . ? C1A N1A C11A C10A -55.9(5) . . . . ? C4A N1A C11A C10A 175.0(3) . . . . ? C1A N1A C11A C6A 122.7(3) . . . . ? C4A N1A C11A C6A -6.4(4) . . . . ? N1A C4A C5A O2A 172.5(3) . . . . ? C3A C4A C5A O2A 58.5(5) . . . . ? P1A C4A C5A O2A -74.6(4) . . . . ? N1A C4A C5A C6A -10.1(3) . . . . ? C3A C4A C5A C6A -124.1(3) . . . . ? P1A C4A C5A C6A 102.8(3) . . . . ? C4B C3B C2B C1B 6.0(4) . . . . ? Cl1B C3B C2B C1B -176.5(3) . . . . ? C4B C3B C2B Cl2B -180.0(2) . . . . ? Cl1B C3B C2B Cl2B -2.4(5) . . . . ? O1B C1B C2B C3B 172.8(3) . . . . ? N1B C1B C2B C3B -6.4(4) . . . . ? O1B C1B C2B Cl2B -1.7(5) . . . . ? N1B C1B C2B Cl2B 179.1(2) . . . . ? C10B C11B C6B C7B 1.0(5) . . . . ? N1B C11B C6B C7B -179.9(3) . . . . ? C10B C11B C6B C5B -176.1(3) . . . . ? N1B C11B C6B C5B 3.0(4) . . . . ? O2B C5B C6B C11B 172.8(4) . . . . ? C4B C5B C6B C11B -9.3(4) . . . . ? O2B C5B C6B C7B -4.0(6) . . . . ? C4B C5B C6B C7B 173.8(3) . . . . ? C6B C11B C10B C9B -0.9(5) . . . . ? N1B C11B C10B C9B -179.8(3) . . . . ? C9A C8A C7A C6A 0.5(5) . . . . ? C10A C11A C6A C7A -1.2(5) . . . . ? N1A C11A C6A C7A -179.9(3) . . . . ? C10A C11A C6A C5A 178.2(3) . . . . ? N1A C11A C6A C5A -0.5(4) . . . . ? C8A C7A C6A C11A 0.9(5) . . . . ? C8A C7A C6A C5A -178.4(3) . . . . ? O2A C5A C6A C11A -176.0(3) . . . . ? C4A C5A C6A C11A 6.7(4) . . . . ? O2A C5A C6A C7A 3.3(6) . . . . ? C4A C5A C6A C7A -174.0(3) . . . . ? C11B C10B C9B C8B 0.0(5) . . . . ? C6A C11A C10A C9A 0.0(5) . . . . ? N1A C11A C10A C9A 178.5(3) . . . . ? O1B C1B N1B C11B -47.0(5) . . . . ? C2B C1B N1B C11B 132.3(3) . . . . ? O1B C1B N1B C4B -174.9(3) . . . . ? C2B C1B N1B C4B 4.3(3) . . . . ? C10B C11B N1B C1B 55.3(5) . . . . ? C6B C11B N1B C1B -123.8(3) . . . . ? C10B C11B N1B C4B -175.8(3) . . . . ? C6B C11B N1B C4B 5.1(4) . . . . ? C3B C4B N1B C1B -1.1(3) . . . . ? C5B C4B N1B C1B 123.6(3) . . . . ? P1B C4B N1B C1B -120.4(2) . . . . ? C3B C4B N1B C11B -135.2(3) . . . . ? C5B C4B N1B C11B -10.5(3) . . . . ? P1B C4B N1B C11B 105.4(2) . . . . ? C1A C2A C3A C4A -7.3(4) . . . . ? Cl2A C2A C3A C4A 179.8(3) . . . . ? C1A C2A C3A Cl1A 173.9(2) . . . . ? Cl2A C2A C3A Cl1A 1.1(5) . . . . ? N1A C4A C3A C2A 4.0(4) . . . . ? C5A C4A C3A C2A 119.3(3) . . . . ? P1A C4A C3A C2A -109.7(3) . . . . ? N1A C4A C3A Cl1A -177.2(2) . . . . ? C5A C4A C3A Cl1A -61.9(4) . . . . ? P1A C4A C3A Cl1A 69.1(3) . . . . ? C11A N1A C1A O1A 44.3(5) . . . . ? C4A N1A C1A O1A 172.4(3) . . . . ? C11A N1A C1A C2A -133.0(3) . . . . ? C4A N1A C1A C2A -4.9(3) . . . . ? C3A C2A C1A O1A -169.5(4) . . . . ? Cl2A C2A C1A O1A 3.7(5) . . . . ? C3A C2A C1A N1A 7.6(4) . . . . ? Cl2A C2A C1A N1A -179.1(2) . . . . ? C11A C10A C9A C8A 1.4(5) . . . . ? C7A C8A C9A C10A -1.7(5) . . . . ? C11B C6B C7B C8B -0.3(5) . . . . ? C5B C6B C7B C8B 176.3(3) . . . . ? P1A O5A C12A C13A 159.0(2) . . . . ? P1B O4B C12B C13B 99.1(3) . . . . ? C6B C7B C8B C9B -0.6(5) . . . . ? C10B C9B C8B C7B 0.8(6) . . . . ? P1B O5B C14B C15B 144.3(3) . . . . ? P1A O4A C14A C15A -117.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.407 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.091 # Attachment '9332_web_deposit_cif_file_3_Yuen-KiCheong_1327944984.pd-9-135-Final.cif' data_pd-9-135 _database_code_depnum_ccdc_archive 'CCDC 865153' #TrackingRef '9332_web_deposit_cif_file_3_Yuen-KiCheong_1327944984.pd-9-135-Final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H5 Cl2 N1 O2' _chemical_formula_sum 'C11 H5 Cl2 N O2' _chemical_formula_weight 254.06 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 n b' _symmetry_space_group_name_Hall 'P -2bc 2a' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, y+1/2, -z+1/2' 'x+1/2, -y, -z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 3.7524(7) _cell_length_b 12.666(3) _cell_length_c 21.009(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 998.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 27438 _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.91 _exptl_crystal_description lath _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.629 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8337 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm' _diffrn_reflns_number 5015 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 27.66 _reflns_number_total 1941 _reflns_number_gt 1681 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0991P)^2^+5.7713P] 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 0.2(2) _refine_ls_number_reflns 1941 _refine_ls_number_parameters 149 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2260 _refine_ls_wR_factor_gt 0.2141 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 0.834(2) 0.7267(6) 0.6721(3) 0.0248(14) Uani 1 1 d . . . C2 C 0.737(2) 0.6748(6) 0.6120(4) 0.0289(17) Uani 1 1 d . . . C3 C 0.582(2) 0.5811(7) 0.6246(3) 0.034(2) Uani 1 1 d . . . C4 C 0.558(2) 0.5688(7) 0.6924(4) 0.0308(18) Uani 1 1 d . . . C5 C 0.452(2) 0.5027(6) 0.7397(3) 0.0233(14) Uani 1 1 d . . . C6 C 0.5373(19) 0.5538(6) 0.8001(3) 0.0252(16) Uani 1 1 d . . . C7 C 0.688(2) 0.6538(6) 0.7867(3) 0.0265(16) Uani 1 1 d . . . C8 C 0.802(2) 0.7215(6) 0.8326(3) 0.0267(15) Uani 1 1 d . . . H8 H 0.9068 0.7875 0.8222 0.032 Uiso 1 1 calc R . . C9 C 0.759(2) 0.6898(7) 0.8954(3) 0.0322(18) Uani 1 1 d . . . H9 H 0.8350 0.7354 0.9286 0.039 Uiso 1 1 calc R . . C10 C 0.606(2) 0.5927(7) 0.9109(4) 0.037(2) Uani 1 1 d . . . H10 H 0.5769 0.5739 0.9543 0.044 Uiso 1 1 calc R . . C11 C 0.497(2) 0.5230(7) 0.8634(3) 0.0313(18) Uani 1 1 d . . . H11 H 0.3973 0.4563 0.8740 0.038 Uiso 1 1 calc R . . Cl1 Cl 0.8427(6) 0.72691(16) 0.53967(8) 0.0355(5) Uani 1 1 d . . . Cl2 Cl 0.4399(6) 0.48712(15) 0.57220(8) 0.0340(5) Uani 1 1 d . . . N1 N 0.7051(17) 0.6619(5) 0.7184(3) 0.0258(14) Uani 1 1 d . . . O1 O 0.9846(15) 0.8125(4) 0.6778(2) 0.0339(14) Uani 1 1 d . . . O2 O 0.3067(16) 0.4088(4) 0.7301(2) 0.0318(13) Uani 1 1 d . . . H2O H 0.18(3) 0.373(7) 0.760(5) 0.05(3) Uiso 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 0.018(3) 0.031(4) 0.026(3) 0.000(3) 0.000(4) 0.002(3) C2 0.023(4) 0.038(4) 0.027(3) -0.004(3) 0.004(3) -0.007(3) C3 0.024(4) 0.062(6) 0.014(3) -0.004(3) -0.005(3) 0.016(4) C4 0.020(4) 0.049(5) 0.024(4) 0.003(3) 0.002(3) 0.001(4) C5 0.011(3) 0.030(4) 0.028(3) -0.004(3) 0.003(3) 0.003(3) C6 0.014(4) 0.037(4) 0.025(3) 0.000(3) 0.001(3) 0.000(3) C7 0.017(4) 0.042(4) 0.020(3) -0.005(3) 0.002(3) 0.012(3) C8 0.017(4) 0.034(4) 0.029(3) -0.001(3) -0.002(3) -0.002(3) C9 0.021(4) 0.054(5) 0.022(3) -0.003(3) -0.003(3) 0.001(4) C10 0.034(5) 0.049(5) 0.028(4) 0.004(4) 0.002(4) 0.015(4) C11 0.024(4) 0.045(5) 0.025(3) 0.010(3) -0.003(3) -0.004(4) Cl1 0.0331(10) 0.0497(11) 0.0236(7) 0.0049(8) 0.0024(8) -0.0047(9) Cl2 0.0308(10) 0.0454(11) 0.0258(8) -0.0081(7) -0.0006(8) -0.0027(9) N1 0.024(3) 0.037(3) 0.016(3) 0.001(2) 0.003(2) -0.001(3) O1 0.033(3) 0.040(3) 0.029(3) -0.004(2) -0.003(3) -0.008(3) O2 0.028(3) 0.042(3) 0.025(2) 0.000(2) -0.001(2) -0.011(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.231(9) . ? C1 N1 1.362(9) . ? C1 C2 1.468(10) . ? C2 C3 1.349(12) . ? C2 Cl1 1.704(8) . ? C3 C4 1.435(10) . ? C3 Cl2 1.707(8) . ? C4 C5 1.358(10) . ? C4 N1 1.412(10) . ? C5 O2 1.325(9) . ? C5 C6 1.460(10) . ? C6 C11 1.395(10) . ? C6 C7 1.415(11) . ? C7 C8 1.360(11) . ? C7 N1 1.440(8) . ? C8 C9 1.388(10) . ? C8 H8 0.9500 . ? C9 C10 1.394(13) . ? C9 H9 0.9500 . ? C10 C11 1.394(12) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? O2 H2O 0.92(11) . ? 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 C1 N1 128.7(6) . . ? O1 C1 C2 126.3(6) . . ? N1 C1 C2 104.9(6) . . ? C3 C2 C1 109.4(7) . . ? C3 C2 Cl1 128.1(6) . . ? C1 C2 Cl1 122.4(6) . . ? C2 C3 C4 108.5(7) . . ? C2 C3 Cl2 128.5(6) . . ? C4 C3 Cl2 123.0(7) . . ? C5 C4 N1 110.2(6) . . ? C5 C4 C3 144.2(8) . . ? N1 C4 C3 105.6(7) . . ? O2 C5 C4 124.2(7) . . ? O2 C5 C6 128.4(7) . . ? C4 C5 C6 107.4(7) . . ? C11 C6 C7 118.9(7) . . ? C11 C6 C5 133.0(7) . . ? C7 C6 C5 108.1(6) . . ? C8 C7 C6 123.3(7) . . ? C8 C7 N1 130.4(8) . . ? C6 C7 N1 106.2(6) . . ? C7 C8 C9 117.0(7) . . ? C7 C8 H8 121.5 . . ? C9 C8 H8 121.5 . . ? C8 C9 C10 121.6(8) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 120.8(7) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C6 118.2(8) . . ? C10 C11 H11 120.9 . . ? C6 C11 H11 120.9 . . ? C1 N1 C4 111.4(6) . . ? C1 N1 C7 140.5(7) . . ? C4 N1 C7 108.0(6) . . ? C5 O2 H2O 124(6) . . ? 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 C1 C2 C3 178.8(9) . . . . ? N1 C1 C2 C3 -3.9(9) . . . . ? O1 C1 C2 Cl1 2.7(13) . . . . ? N1 C1 C2 Cl1 179.9(6) . . . . ? C1 C2 C3 C4 1.9(10) . . . . ? Cl1 C2 C3 C4 177.8(6) . . . . ? C1 C2 C3 Cl2 -176.6(7) . . . . ? Cl1 C2 C3 Cl2 -0.8(13) . . . . ? C2 C3 C4 C5 -178.7(11) . . . . ? Cl2 C3 C4 C5 0.0(17) . . . . ? C2 C3 C4 N1 0.8(9) . . . . ? Cl2 C3 C4 N1 179.4(5) . . . . ? N1 C4 C5 O2 -179.5(7) . . . . ? C3 C4 C5 O2 -0.1(18) . . . . ? N1 C4 C5 C6 -0.8(9) . . . . ? C3 C4 C5 C6 178.7(11) . . . . ? O2 C5 C6 C11 0.1(14) . . . . ? C4 C5 C6 C11 -178.5(9) . . . . ? O2 C5 C6 C7 -179.7(7) . . . . ? C4 C5 C6 C7 1.7(8) . . . . ? C11 C6 C7 C8 1.2(11) . . . . ? C5 C6 C7 C8 -179.0(7) . . . . ? C11 C6 C7 N1 178.3(7) . . . . ? C5 C6 C7 N1 -1.9(8) . . . . ? C6 C7 C8 C9 -1.4(12) . . . . ? N1 C7 C8 C9 -177.7(7) . . . . ? C7 C8 C9 C10 0.3(12) . . . . ? C8 C9 C10 C11 1.1(13) . . . . ? C9 C10 C11 C6 -1.2(12) . . . . ? C7 C6 C11 C10 0.2(11) . . . . ? C5 C6 C11 C10 -179.6(8) . . . . ? O1 C1 N1 C4 -178.3(9) . . . . ? C2 C1 N1 C4 4.5(9) . . . . ? O1 C1 N1 C7 -3.5(17) . . . . ? C2 C1 N1 C7 179.4(9) . . . . ? C5 C4 N1 C1 176.2(7) . . . . ? C3 C4 N1 C1 -3.4(9) . . . . ? C5 C4 N1 C7 -0.4(9) . . . . ? C3 C4 N1 C7 180.0(6) . . . . ? C8 C7 N1 C1 3.2(16) . . . . ? C6 C7 N1 C1 -173.6(9) . . . . ? C8 C7 N1 C4 178.2(8) . . . . ? C6 C7 N1 C4 1.4(8) . . . . ? 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 H2O O1 0.92(11) 1.67(11) 2.588(8) 172(10) 2_446 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 27.66 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.587 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.142