data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 As Cl2 P' _chemical_formula_sum 'C18 H22 As Cl2 P' _chemical_formula_weight 415.15 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' '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' 'As' 'As' 0.0499 2.0058 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.556(4) _cell_length_b 11.052(3) _cell_length_c 14.829(5) _cell_angle_alpha 90.00 _cell_angle_beta 108.209(6) _cell_angle_gamma 90.00 _cell_volume 1799.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6641 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 28.8 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 2.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.807 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 14.7059 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10821 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.33 _reflns_number_total 3253 _reflns_number_gt 3000 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 (Rigaku, 2010)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 (Rigaku, 2010)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 (Rigaku, 2010)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0295P)^2^+0.2793P] 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 3253 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0587 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 As1 As 0.648765(16) 0.411733(16) 0.072004(12) 0.01274(8) Uani 1 1 d . . . Cl1 Cl 0.83288(4) 0.39949(4) 0.02928(3) 0.02016(12) Uani 1 1 d . . . Cl2 Cl 0.46207(4) 0.43643(4) 0.12616(3) 0.01683(12) Uani 1 1 d . . . P1 P 0.73984(4) 0.31247(4) 0.22162(3) 0.01265(12) Uani 1 1 d . . . C1 C 0.70421(16) 0.56336(16) 0.14213(13) 0.0131(4) Uani 1 1 d . . . C2 C 0.68859(16) 0.67621(16) 0.10031(13) 0.0146(4) Uani 1 1 d . . . H2A H 0.6525 0.6819 0.0334 0.018 Uiso 1 1 calc R . . C3 C 0.72468(16) 0.78469(16) 0.15393(13) 0.0163(4) Uani 1 1 d . . . H3A H 0.7142 0.8609 0.1228 0.020 Uiso 1 1 calc R . . C4 C 0.77463(16) 0.77807(15) 0.25069(13) 0.0137(4) Uani 1 1 d . . . C5 C 0.78808(15) 0.66316(15) 0.29365(13) 0.0130(4) Uani 1 1 d . . . C6 C 0.83482(16) 0.66775(16) 0.39352(13) 0.0142(4) Uani 1 1 d . . . C7 C 0.85116(16) 0.56090(17) 0.44393(14) 0.0178(4) Uani 1 1 d . . . H7A H 0.8813 0.5617 0.5113 0.021 Uiso 1 1 calc R . . C8 C 0.82237(17) 0.44949(17) 0.39384(14) 0.0166(4) Uani 1 1 d . . . H8A H 0.8352 0.3759 0.4287 0.020 Uiso 1 1 calc R . . C9 C 0.77615(16) 0.44535(16) 0.29576(13) 0.0137(4) Uani 1 1 d . . . C10 C 0.75617(15) 0.55442(16) 0.24259(13) 0.0123(4) Uani 1 1 d . . . C11 C 0.82050(17) 0.87185(16) 0.32852(13) 0.0176(4) Uani 1 1 d . . . H11A H 0.7558 0.9312 0.3270 0.021 Uiso 1 1 calc R . . H11B H 0.8917 0.9156 0.3211 0.021 Uiso 1 1 calc R . . C12 C 0.85682(16) 0.79884(17) 0.42293(13) 0.0179(4) Uani 1 1 d . . . H12A H 0.9436 0.8125 0.4592 0.022 Uiso 1 1 calc R . . H12B H 0.8061 0.8230 0.4627 0.022 Uiso 1 1 calc R . . C13 C 0.88329(16) 0.23608(16) 0.22637(13) 0.0150(4) Uani 1 1 d . . . H13A H 0.9325 0.2946 0.2021 0.018 Uiso 1 1 calc R . . C14 C 0.85950(18) 0.12525(17) 0.16067(14) 0.0209(4) Uani 1 1 d . . . H14A H 0.9373 0.0927 0.1580 0.031 Uiso 1 1 calc R . . H14B H 0.8093 0.1491 0.0968 0.031 Uiso 1 1 calc R . . H14C H 0.8167 0.0632 0.1853 0.031 Uiso 1 1 calc R . . C15 C 0.95895(17) 0.20291(17) 0.32831(13) 0.0192(4) Uani 1 1 d . . . H15A H 1.0320 0.1585 0.3274 0.029 Uiso 1 1 calc R . . H15B H 0.9101 0.1521 0.3568 0.029 Uiso 1 1 calc R . . H15C H 0.9830 0.2769 0.3659 0.029 Uiso 1 1 calc R . . C16 C 0.64450(16) 0.20139(16) 0.25934(13) 0.0169(4) Uani 1 1 d . . . H16A H 0.7014 0.1389 0.2978 0.020 Uiso 1 1 calc R . . C17 C 0.55797(18) 0.13480(18) 0.17346(14) 0.0233(5) Uani 1 1 d . . . H17A H 0.5201 0.0664 0.1957 0.035 Uiso 1 1 calc R . . H17B H 0.6042 0.1049 0.1327 0.035 Uiso 1 1 calc R . . H17C H 0.4945 0.1906 0.1373 0.035 Uiso 1 1 calc R . . C18 C 0.57646(18) 0.25473(17) 0.32385(14) 0.0208(4) Uani 1 1 d . . . H18A H 0.5285 0.1911 0.3415 0.031 Uiso 1 1 calc R . . H18B H 0.5220 0.3193 0.2900 0.031 Uiso 1 1 calc R . . H18C H 0.6354 0.2878 0.3813 0.031 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 As1 0.01484(12) 0.01189(12) 0.01128(12) -0.00060(7) 0.00376(9) -0.00008(7) Cl1 0.0217(3) 0.0231(3) 0.0195(3) 0.00482(19) 0.0119(2) 0.0049(2) Cl2 0.0156(2) 0.0178(2) 0.0172(3) -0.00022(18) 0.00541(19) -0.00016(19) P1 0.0157(2) 0.0104(2) 0.0123(3) -0.00001(19) 0.00502(19) -0.00060(19) C1 0.0105(9) 0.0152(10) 0.0144(10) -0.0015(7) 0.0051(7) -0.0014(7) C2 0.0150(9) 0.0168(10) 0.0128(10) 0.0013(8) 0.0052(7) -0.0006(8) C3 0.0178(10) 0.0120(10) 0.0196(11) 0.0040(7) 0.0066(8) -0.0010(8) C4 0.0119(9) 0.0119(9) 0.0189(11) -0.0024(7) 0.0069(8) -0.0017(7) C5 0.0102(9) 0.0146(10) 0.0153(10) -0.0015(7) 0.0057(7) -0.0016(7) C6 0.0122(9) 0.0157(10) 0.0153(10) -0.0039(8) 0.0053(7) -0.0019(8) C7 0.0206(10) 0.0203(10) 0.0126(10) -0.0006(8) 0.0054(8) -0.0006(8) C8 0.0203(10) 0.0145(10) 0.0154(10) 0.0026(8) 0.0064(8) 0.0012(8) C9 0.0147(9) 0.0124(9) 0.0144(10) -0.0016(7) 0.0050(8) -0.0019(8) C10 0.0096(9) 0.0134(9) 0.0153(10) 0.0002(7) 0.0060(7) 0.0004(7) C11 0.0188(9) 0.0138(10) 0.0211(11) -0.0032(8) 0.0075(8) -0.0005(8) C12 0.0200(10) 0.0164(10) 0.0179(11) -0.0032(8) 0.0065(8) -0.0031(8) C13 0.0157(9) 0.0143(9) 0.0160(10) 0.0015(7) 0.0066(8) 0.0017(8) C14 0.0248(11) 0.0192(10) 0.0188(11) -0.0023(8) 0.0072(9) 0.0033(9) C15 0.0175(10) 0.0205(11) 0.0187(11) 0.0008(8) 0.0040(8) 0.0019(8) C16 0.0197(10) 0.0126(10) 0.0193(11) 0.0029(8) 0.0077(8) -0.0001(8) C17 0.0242(11) 0.0184(10) 0.0275(12) -0.0028(9) 0.0085(9) -0.0061(9) C18 0.0233(10) 0.0213(11) 0.0212(11) 0.0046(8) 0.0116(9) -0.0017(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag As1 C1 1.9707(18) . ? As1 P1 2.4029(7) . ? As1 Cl1 2.4060(8) . ? As1 Cl2 2.5410(8) . ? P1 C9 1.8037(18) . ? P1 C13 1.8419(19) . ? P1 C16 1.8492(19) . ? C1 C2 1.379(2) . ? C1 C10 1.425(3) . ? C2 C3 1.427(2) . ? C2 H2A 0.9500 . ? C3 C4 1.371(3) . ? C3 H3A 0.9500 . ? C4 C5 1.407(2) . ? C4 C11 1.518(2) . ? C5 C10 1.407(2) . ? C5 C6 1.410(3) . ? C6 C7 1.379(3) . ? C6 C12 1.511(3) . ? C7 C8 1.423(3) . ? C7 H7A 0.9500 . ? C8 C9 1.385(3) . ? C8 H8A 0.9500 . ? C9 C10 1.419(2) . ? C11 C12 1.556(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.536(3) . ? C13 C15 1.536(3) . ? C13 H13A 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C18 1.533(3) . ? C16 C17 1.539(3) . ? C16 H16A 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 As1 P1 85.68(6) . . ? C1 As1 Cl1 91.05(5) . . ? P1 As1 Cl1 92.82(2) . . ? C1 As1 Cl2 84.84(5) . . ? P1 As1 Cl2 85.84(2) . . ? Cl1 As1 Cl2 175.758(17) . . ? C9 P1 C13 108.34(8) . . ? C9 P1 C16 113.78(9) . . ? C13 P1 C16 107.36(8) . . ? C9 P1 As1 98.19(6) . . ? C13 P1 As1 111.96(6) . . ? C16 P1 As1 116.87(6) . . ? C2 C1 C10 119.07(16) . . ? C2 C1 As1 123.80(14) . . ? C10 C1 As1 117.00(13) . . ? C1 C2 C3 122.33(17) . . ? C1 C2 H2A 118.8 . . ? C3 C2 H2A 118.8 . . ? C4 C3 C2 119.50(16) . . ? C4 C3 H3A 120.2 . . ? C2 C3 H3A 120.2 . . ? C3 C4 C5 118.21(16) . . ? C3 C4 C11 133.78(17) . . ? C5 C4 C11 108.00(15) . . ? C10 C5 C4 123.64(17) . . ? C10 C5 C6 123.09(16) . . ? C4 C5 C6 113.25(16) . . ? C7 C6 C5 118.77(16) . . ? C7 C6 C12 133.03(17) . . ? C5 C6 C12 108.20(15) . . ? C6 C7 C8 119.22(18) . . ? C6 C7 H7A 120.4 . . ? C8 C7 H7A 120.4 . . ? C9 C8 C7 121.84(17) . . ? C9 C8 H8A 119.1 . . ? C7 C8 H8A 119.1 . . ? C8 C9 C10 119.85(16) . . ? C8 C9 P1 127.38(14) . . ? C10 C9 P1 112.74(13) . . ? C5 C10 C9 117.19(16) . . ? C5 C10 C1 117.22(16) . . ? C9 C10 C1 125.58(16) . . ? C4 C11 C12 105.18(14) . . ? C4 C11 H11A 110.7 . . ? C12 C11 H11A 110.7 . . ? C4 C11 H11B 110.7 . . ? C12 C11 H11B 110.7 . . ? H11A C11 H11B 108.8 . . ? C6 C12 C11 105.30(14) . . ? C6 C12 H12A 110.7 . . ? C11 C12 H12A 110.7 . . ? C6 C12 H12B 110.7 . . ? C11 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C14 C13 C15 111.60(15) . . ? C14 C13 P1 111.15(12) . . ? C15 C13 P1 112.08(13) . . ? C14 C13 H13A 107.2 . . ? C15 C13 H13A 107.2 . . ? P1 C13 H13A 107.2 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C16 C17 111.90(16) . . ? C18 C16 P1 113.81(13) . . ? C17 C16 P1 111.20(13) . . ? C18 C16 H16A 106.5 . . ? C17 C16 H16A 106.5 . . ? P1 C16 H16A 106.5 . . ? 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 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 As1 P1 C9 7.47(8) . . . . ? Cl1 As1 P1 C9 98.31(6) . . . . ? Cl2 As1 P1 C9 -77.66(6) . . . . ? C1 As1 P1 C13 -106.16(8) . . . . ? Cl1 As1 P1 C13 -15.32(6) . . . . ? Cl2 As1 P1 C13 168.71(6) . . . . ? C1 As1 P1 C16 129.45(9) . . . . ? Cl1 As1 P1 C16 -139.71(7) . . . . ? Cl2 As1 P1 C16 44.32(7) . . . . ? P1 As1 C1 C2 177.54(15) . . . . ? Cl1 As1 C1 C2 84.79(15) . . . . ? Cl2 As1 C1 C2 -96.26(15) . . . . ? P1 As1 C1 C10 -6.60(13) . . . . ? Cl1 As1 C1 C10 -99.35(13) . . . . ? Cl2 As1 C1 C10 79.60(13) . . . . ? C10 C1 C2 C3 1.2(3) . . . . ? As1 C1 C2 C3 176.94(13) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C2 C3 C4 C11 -178.97(18) . . . . ? C3 C4 C5 C10 1.8(3) . . . . ? C11 C4 C5 C10 -179.13(16) . . . . ? C3 C4 C5 C6 -177.11(16) . . . . ? C11 C4 C5 C6 2.0(2) . . . . ? C10 C5 C6 C7 0.5(3) . . . . ? C4 C5 C6 C7 179.43(16) . . . . ? C10 C5 C6 C12 -179.29(15) . . . . ? C4 C5 C6 C12 -0.4(2) . . . . ? C5 C6 C7 C8 1.0(3) . . . . ? C12 C6 C7 C8 -179.22(18) . . . . ? C6 C7 C8 C9 -1.2(3) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C7 C8 C9 P1 177.79(14) . . . . ? C13 P1 C9 C8 -69.57(18) . . . . ? C16 P1 C9 C8 49.74(19) . . . . ? As1 P1 C9 C8 173.96(16) . . . . ? C13 P1 C9 C10 108.46(14) . . . . ? C16 P1 C9 C10 -132.23(13) . . . . ? As1 P1 C9 C10 -8.01(13) . . . . ? C4 C5 C10 C9 179.38(16) . . . . ? C6 C5 C10 C9 -1.8(3) . . . . ? C4 C5 C10 C1 -1.9(3) . . . . ? C6 C5 C10 C1 176.90(16) . . . . ? C8 C9 C10 C5 1.6(3) . . . . ? P1 C9 C10 C5 -176.61(13) . . . . ? C8 C9 C10 C1 -177.03(17) . . . . ? P1 C9 C10 C1 4.8(2) . . . . ? C2 C1 C10 C5 0.4(3) . . . . ? As1 C1 C10 C5 -175.69(12) . . . . ? C2 C1 C10 C9 178.99(16) . . . . ? As1 C1 C10 C9 2.9(2) . . . . ? C3 C4 C11 C12 176.24(19) . . . . ? C5 C4 C11 C12 -2.65(19) . . . . ? C7 C6 C12 C11 178.92(19) . . . . ? C5 C6 C12 C11 -1.30(19) . . . . ? C4 C11 C12 C6 2.36(18) . . . . ? C9 P1 C13 C14 -177.14(13) . . . . ? C16 P1 C13 C14 59.58(15) . . . . ? As1 P1 C13 C14 -69.96(14) . . . . ? C9 P1 C13 C15 57.21(15) . . . . ? C16 P1 C13 C15 -66.07(14) . . . . ? As1 P1 C13 C15 164.39(11) . . . . ? C9 P1 C16 C18 19.50(16) . . . . ? C13 P1 C16 C18 139.37(14) . . . . ? As1 P1 C16 C18 -93.93(13) . . . . ? C9 P1 C16 C17 146.98(13) . . . . ? C13 P1 C16 C17 -93.15(14) . . . . ? As1 P1 C16 C17 33.54(15) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.334 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.062