Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Matyas Czugler' _publ_contact_author_address ; X-ray Diffraction ChemResCent, HungAcadSci Pusztaszeri u. 59-67 Budapest 1025 HUNGARY ; _publ_contact_author_email MCZ@CHEMRES.HU _publ_section_title ; Intra- and Intermolecular Interactions and Water Pincer in the Crystal Structure of a 3-P Substituted 1,2,3,6-Tertrahydrophosphinine Oxide Hydrate ; loop_ _publ_author_name 'Matyas Czugler' 'Laszlo Fabian' 'Gyorgy Keglevich' 'Tamas Kortvelyesi' 'Melinda Sipos' data_sm01 _database_code_depnum_ccdc_archive 'CCDC 604746' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H23 Cl O2 P2, H2 O' _chemical_formula_sum 'C24 H25 Cl O3 P2' _chemical_formula_weight 458.83 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' 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 orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.277(2) _cell_length_b 16.356(2) _cell_length_c 23.341(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4686.9(13) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 55211 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 27.56 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.49 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.322 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8692 _exptl_absorpt_correction_T_max 0.9331 _exptl_absorpt_process_details ? _exptl_special_details ; T. Higashi, NUMABS, a numerical absorption correction program, September 1998 ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-Axis Rapid' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 69157 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5363 _reflns_number_gt 4339 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+1.3426P] 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 5363 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.92077(3) 0.14666(3) 0.463176(17) 0.03278(11) Uani 1 1 d . . . C2 C 0.84509(14) 0.22954(9) 0.49596(7) 0.0344(3) Uani 1 1 d . . . H2A H 0.8962 0.2645 0.5161 0.041 Uiso 1 1 calc R . . H2B H 0.8124 0.2619 0.4657 0.041 Uiso 1 1 calc R . . C3 C 0.75369(12) 0.20422(9) 0.53860(6) 0.0278(3) Uani 1 1 d . . . H3 H 0.6979 0.2470 0.5371 0.033 Uiso 1 1 calc R . . C4 C 0.69887(12) 0.12506(9) 0.52130(7) 0.0306(3) Uani 1 1 d . . . C5 C 0.74811(13) 0.05844(9) 0.50118(7) 0.0321(3) Uani 1 1 d . . . C6 C 0.87051(13) 0.05705(10) 0.49926(7) 0.0351(3) Uani 1 1 d . . . H6A H 0.8950 0.0084 0.4792 0.042 Uiso 1 1 calc R . . H6B H 0.8992 0.0552 0.5380 0.042 Uiso 1 1 calc R . . O7 O 1.04122(10) 0.15588(8) 0.46624(6) 0.0467(3) Uani 1 1 d . . . P8 P 0.81135(3) 0.20610(2) 0.611160(16) 0.02795(10) Uani 1 1 d . . . Cl9 Cl 0.55750(3) 0.12762(3) 0.52574(2) 0.04876(13) Uani 1 1 d . . . C10 C 0.69028(16) -0.01510(11) 0.47789(9) 0.0496(5) Uani 1 1 d . . . H10A H 0.6132 -0.0054 0.4780 0.074 Uiso 1 1 calc R . . H10B H 0.7064 -0.0618 0.5014 0.074 Uiso 1 1 calc R . . H10C H 0.7143 -0.0253 0.4394 0.074 Uiso 1 1 calc R . . C11 C 0.87623(15) 0.13677(10) 0.39011(7) 0.0386(4) Uani 1 1 d . . . C12 C 0.93971(19) 0.08711(13) 0.35491(9) 0.0573(5) Uani 1 1 d . . . H12 H 1.0012 0.0614 0.3696 0.069 Uiso 1 1 calc R . . C13 C 0.9111(3) 0.07624(16) 0.29818(10) 0.0760(8) Uani 1 1 d . . . H13 H 0.9537 0.0432 0.2747 0.091 Uiso 1 1 calc R . . C14 C 0.8209(3) 0.11356(17) 0.27642(9) 0.0750(7) Uani 1 1 d . . . H14 H 0.8022 0.1057 0.2382 0.090 Uiso 1 1 calc R . . C15 C 0.7579(2) 0.16228(16) 0.31026(9) 0.0673(6) Uani 1 1 d . . . H15 H 0.6967 0.1877 0.2950 0.081 Uiso 1 1 calc R . . C16 C 0.78478(17) 0.17413(13) 0.36742(8) 0.0521(5) Uani 1 1 d . . . H16 H 0.7414 0.2071 0.3905 0.063 Uiso 1 1 calc R . . O17 O 0.90657(9) 0.15077(7) 0.61827(5) 0.0374(3) Uani 1 1 d . . . C18 C 0.84697(13) 0.31247(10) 0.62101(6) 0.0320(3) Uani 1 1 d . . . C19 C 0.95414(15) 0.33282(12) 0.63259(8) 0.0456(4) Uani 1 1 d . . . H19 H 1.0069 0.2921 0.6350 0.055 Uiso 1 1 calc R . . C20 C 0.98272(18) 0.41434(13) 0.64066(9) 0.0560(5) Uani 1 1 d . . . H20 H 1.0549 0.4281 0.6480 0.067 Uiso 1 1 calc R . . C21 C 0.90527(19) 0.47443(12) 0.63786(8) 0.0530(5) Uani 1 1 d . . . H21 H 0.9249 0.5287 0.6438 0.064 Uiso 1 1 calc R . . C22 C 0.79885(19) 0.45498(11) 0.62635(8) 0.0507(5) Uani 1 1 d . . . H22 H 0.7465 0.4960 0.6245 0.061 Uiso 1 1 calc R . . C23 C 0.76927(16) 0.37423(10) 0.61746(7) 0.0413(4) Uani 1 1 d . . . H23 H 0.6973 0.3613 0.6091 0.050 Uiso 1 1 calc R . . C24 C 0.70755(13) 0.18497(9) 0.66371(7) 0.0334(3) Uani 1 1 d . . . C25 C 0.60176(15) 0.21472(12) 0.66057(8) 0.0463(4) Uani 1 1 d . . . H25 H 0.5788 0.2433 0.6283 0.056 Uiso 1 1 calc R . . C26 C 0.53051(18) 0.20155(14) 0.70569(10) 0.0597(6) Uani 1 1 d . . . H26 H 0.4596 0.2214 0.7036 0.072 Uiso 1 1 calc R . . C27 C 0.56357(19) 0.15949(14) 0.75348(10) 0.0627(6) Uani 1 1 d . . . H27 H 0.5153 0.1514 0.7837 0.075 Uiso 1 1 calc R . . C28 C 0.66789(19) 0.12918(14) 0.75683(9) 0.0590(6) Uani 1 1 d . . . H28 H 0.6900 0.1004 0.7892 0.071 Uiso 1 1 calc R . . C29 C 0.73990(16) 0.14154(11) 0.71198(8) 0.0444(4) Uani 1 1 d . . . H29 H 0.8102 0.1207 0.7142 0.053 Uiso 1 1 calc R . . O30 O 1.12959(15) 0.16073(15) 0.57888(9) 0.0821(6) Uani 1 1 d . . . H30A H 1.107(3) 0.159(2) 0.5480(14) 0.099 Uiso 1 1 d . . . H30B H 1.078(3) 0.151(2) 0.5980(15) 0.099 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 P1 0.0282(2) 0.0392(2) 0.0309(2) -0.00346(16) 0.00481(15) -0.00469(16) C2 0.0396(9) 0.0337(8) 0.0299(7) -0.0016(6) 0.0069(6) -0.0075(6) C3 0.0258(7) 0.0293(7) 0.0283(7) -0.0010(6) -0.0001(6) 0.0005(6) C4 0.0226(7) 0.0357(8) 0.0336(8) 0.0023(6) -0.0033(6) -0.0030(6) C5 0.0297(8) 0.0313(8) 0.0355(8) 0.0012(6) -0.0007(6) -0.0031(6) C6 0.0315(8) 0.0344(8) 0.0394(8) -0.0014(6) 0.0025(7) 0.0015(6) O7 0.0291(6) 0.0606(8) 0.0505(7) -0.0059(6) 0.0049(5) -0.0081(6) P8 0.02536(19) 0.0314(2) 0.02709(19) -0.00052(14) 0.00109(14) -0.00025(15) Cl9 0.0233(2) 0.0496(3) 0.0734(3) -0.0036(2) -0.00458(19) -0.00148(17) C10 0.0462(11) 0.0398(10) 0.0628(12) -0.0107(8) -0.0026(9) -0.0092(8) C11 0.0417(9) 0.0427(9) 0.0313(8) -0.0040(7) 0.0049(7) -0.0073(7) C12 0.0699(14) 0.0569(12) 0.0451(11) -0.0128(9) 0.0071(10) 0.0070(10) C13 0.112(2) 0.0736(16) 0.0427(12) -0.0215(11) 0.0132(13) 0.0058(15) C14 0.109(2) 0.0829(17) 0.0327(10) -0.0086(11) -0.0061(12) -0.0178(16) C15 0.0728(16) 0.0852(17) 0.0437(11) 0.0033(11) -0.0157(11) -0.0032(13) C16 0.0508(12) 0.0668(13) 0.0389(10) -0.0054(9) -0.0001(8) 0.0000(10) O17 0.0301(6) 0.0423(6) 0.0397(6) -0.0007(5) -0.0020(5) 0.0069(5) C18 0.0379(9) 0.0341(8) 0.0241(7) -0.0014(6) 0.0007(6) -0.0043(6) C19 0.0399(10) 0.0453(10) 0.0518(11) -0.0075(8) 0.0022(8) -0.0063(8) C20 0.0514(12) 0.0541(12) 0.0625(13) -0.0077(10) 0.0009(10) -0.0203(10) C21 0.0773(15) 0.0356(9) 0.0461(10) 0.0014(8) -0.0014(10) -0.0150(9) C22 0.0741(14) 0.0363(9) 0.0417(10) 0.0017(7) -0.0110(9) 0.0033(9) C23 0.0483(10) 0.0386(9) 0.0369(9) 0.0001(7) -0.0082(7) -0.0001(8) C24 0.0354(8) 0.0333(8) 0.0316(8) 0.0001(6) 0.0055(6) -0.0022(6) C25 0.0400(10) 0.0496(10) 0.0492(10) 0.0072(8) 0.0120(8) 0.0063(8) C26 0.0454(11) 0.0645(13) 0.0691(14) 0.0007(11) 0.0241(10) 0.0042(10) C27 0.0655(14) 0.0729(14) 0.0497(12) -0.0006(10) 0.0276(10) -0.0148(11) C28 0.0678(14) 0.0706(14) 0.0387(10) 0.0148(9) 0.0064(9) -0.0147(11) C29 0.0440(10) 0.0515(10) 0.0377(9) 0.0081(8) 0.0011(8) -0.0037(8) O30 0.0444(10) 0.1269(17) 0.0751(12) -0.0229(12) -0.0047(8) 0.0038(10) _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 O7 1.4882(13) . ? P1 C11 1.7984(17) . ? P1 C6 1.7995(16) . ? P1 C2 1.8127(16) . ? C2 C3 1.556(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.514(2) . ? C3 P8 1.8359(15) . ? C3 H3 0.9800 . ? C4 C5 1.332(2) . ? C4 Cl9 1.7392(16) . ? C5 C10 1.499(2) . ? C5 C6 1.504(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? P8 O17 1.4877(12) . ? P8 C24 1.8022(16) . ? P8 C18 1.8085(16) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.384(3) . ? C11 C12 1.394(3) . ? C12 C13 1.381(3) . ? C12 H12 0.9300 . ? C13 C14 1.362(4) . ? C13 H13 0.9300 . ? C14 C15 1.363(4) . ? C14 H14 0.9300 . ? C15 C16 1.388(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C18 C19 1.384(2) . ? C18 C23 1.392(2) . ? C19 C20 1.391(3) . ? C19 H19 0.9300 . ? C20 C21 1.369(3) . ? C20 H20 0.9300 . ? C21 C22 1.371(3) . ? C21 H21 0.9300 . ? C22 C23 1.385(3) . ? C22 H22 0.9300 . ? C23 H23 0.9300 . ? C24 C25 1.389(2) . ? C24 C29 1.390(2) . ? C25 C26 1.386(3) . ? C25 H25 0.9300 . ? C26 C27 1.372(3) . ? C26 H26 0.9300 . ? C27 C28 1.376(3) . ? C27 H27 0.9300 . ? C28 C29 1.385(3) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? O30 H30A 0.77(3) . ? O30 H30B 0.79(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O7 P1 C11 110.91(8) . . ? O7 P1 C6 113.62(8) . . ? C11 P1 C6 105.44(8) . . ? O7 P1 C2 114.42(8) . . ? C11 P1 C2 108.16(8) . . ? C6 P1 C2 103.63(7) . . ? C3 C2 P1 116.15(10) . . ? C3 C2 H2A 108.2 . . ? P1 C2 H2A 108.2 . . ? C3 C2 H2B 108.2 . . ? P1 C2 H2B 108.2 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 112.18(12) . . ? C4 C3 P8 115.58(10) . . ? C2 C3 P8 107.92(10) . . ? C4 C3 H3 106.9 . . ? C2 C3 H3 106.9 . . ? P8 C3 H3 106.9 . . ? C5 C4 C3 126.30(14) . . ? C5 C4 Cl9 119.58(12) . . ? C3 C4 Cl9 114.03(11) . . ? C4 C5 C10 124.72(15) . . ? C4 C5 C6 118.46(14) . . ? C10 C5 C6 116.78(14) . . ? C5 C6 P1 110.15(11) . . ? C5 C6 H6A 109.6 . . ? P1 C6 H6A 109.6 . . ? C5 C6 H6B 109.6 . . ? P1 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? O17 P8 C24 111.29(7) . . ? O17 P8 C18 112.39(7) . . ? C24 P8 C18 105.60(7) . . ? O17 P8 C3 113.31(7) . . ? C24 P8 C3 110.61(7) . . ? C18 P8 C3 103.10(7) . . ? C5 C10 H10A 109.5 . . ? C5 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C5 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.05(17) . . ? C16 C11 P1 124.74(14) . . ? C12 C11 P1 116.20(15) . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 120.5(2) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C16 120.3(2) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 119.9(2) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C19 C18 C23 119.25(16) . . ? C19 C18 P8 119.09(13) . . ? C23 C18 P8 121.66(13) . . ? C18 C19 C20 119.78(19) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C21 C20 C19 120.42(19) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 120.29(18) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C21 C22 C23 120.02(19) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C18 120.23(18) . . ? C22 C23 H23 119.9 . . ? C18 C23 H23 119.9 . . ? C25 C24 C29 119.28(16) . . ? C25 C24 P8 123.93(13) . . ? C29 C24 P8 116.60(13) . . ? C26 C25 C24 119.72(19) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C27 C26 C25 120.6(2) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C28 120.15(19) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C29 119.9(2) . . ? C27 C28 H28 120.0 . . ? C29 C28 H28 120.0 . . ? C28 C29 C24 120.33(19) . . ? C28 C29 H29 119.8 . . ? C24 C29 H29 119.8 . . ? H30A O30 H30B 104(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.351 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.044