# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1177 #======================================================================= data_global #======================================================================= _audit_creation_date 8-12-98 # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondance ; ; _publ_contact_author_address # Address of author for correspondance ; ; _publ_contact_author_phone 'xxxxxxxxxx' _publ_contact_author_fax 'xxxxxxxxxx' _publ_contact_author_email xxx@xx.xx.xx _publ_requested_journal 'Acta Crystallographica C' _publ_contact_letter ; Please consider this CIF submission for publication as a new structure paper in Acta Crystallographica Section C. The figures, chemical structure diagram (scheme), Transfert of Copyright Agreement form and structure factors will be sent on receipt of your acknowledgement letter ; _publ_requested_category FM #======================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Dupont Karl' #<--'Last name, first name' ; Research School of Chemistry National Laboratory Ouchnock Islandia ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. Enraf-Nonius, Cad4-Express Operations Manual, Delft, 1994. Fair, C.K. (1990). MolEN, An Interactive Intelligent System for Crystal Structure Analysis, User Manual, Enraf - Nonius, Delft, The Netherlands. North, A.C.T., Phillips, D.C., Mathews, F.S. (1968). Acta Cryst., A24, 351-359. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #======================================================================= # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the ? in the data_? line below # by a unique identifier. data_phosind #======================================================================= # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C14H20P2S' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14H20P2S' _chemical_formula_weight 282.33 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 P ? 0.090 0.095 International_Tables_Vol_IV_Table_2.3.1 S ? 0.110 0.124 International_Tables_Vol_IV_Table_2.3.1 #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 9.861(1) _cell_length_b 15.219(2) _cell_length_c 10.715(1) _cell_angle_alpha 90 _cell_angle_beta 110.95(1) _cell_angle_gamma 90 _cell_volume 1501.9(6) _cell_formula_units_z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 17.0 _cell_special_details ; ? ; _exptl_crystal_description plate _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.25 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.395 _exptl_absorpt_correction_type psi_scans_(North,_Phillips,_Mathews,_1968) _exptl_absorpt_correction_T_min 0.9189 _exptl_absorpt_correction_T_max 1.0000 #======================================================================= # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_radiation_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Enraf_Nonius_CAD4 _diffrn_measurement_method \q/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 9 0 -5 -3 0 1 1 -6 _diffrn_reflns_number 4725 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_sigmaI/netI 0.500 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 29.98 _reflns_number_total 4353 _reflns_number_gt 3572 _reflns_threshold_expression >2.0\s(I) _computing_data_collection 'CAD4_(Enraf-Nonius,_1994)' _computing_cell_refinement CAD4_(Enraf-Nonius,_1994) _computing_data_reduction 'process_MolEN_(Fair,_1990)' _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_MolEN_(Fair,_1990) _computing_molecular_graphics ? _computing_publication_material BTABLE_PTABLE_CIF_IN_MolEN_(Fair,_1990) #======================================================================= # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3572 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details ; ? ; _refine_ls_R_factor_all 0.048 _refine_ls_R_factor_gt 0.033 _refine_ls_wR_factor_all 0.056 _refine_ls_wR_factor_ref 0.053 _refine_ls_goodness_of_fit_all 1.173 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_shift/su_max 0.018 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 0.286 _refine_diff_density_min -0.371 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol S10 1.25599(4) 0.16665(3) 0.86455(4) 0.0321(2) Uij ? ? S P1 0.69992(4) 0.00197(2) 0.62312(3) 0.0290(1) Uij ? ? P P9 1.04656(3) 0.18524(2) 0.80913(3) 0.0242(1) Uij ? ? P C2 0.7245(1) 0.01455(9) 0.4719(1) 0.0291(6) Uij ? ? C C3 0.8249(1) 0.06622(9) 0.4429(1) 0.0275(5) Uij ? ? C C4 0.9273(1) 0.11820(8) 0.5425(1) 0.0251(5) Uij ? ? C C5 0.9270(1) 0.12009(8) 0.6723(1) 0.0220(4) Uij ? ? C C6 0.8338(1) 0.07222(8) 0.7210(1) 0.0227(4) Uij ? ? C C7 0.8617(1) 0.08668(9) 0.8653(1) 0.0257(5) Uij ? ? C C8 0.9678(1) 0.14511(9) 0.9257(1) 0.0273(5) Uij ? ? C C11 0.8258(2) 0.0680(1) 0.3028(1) 0.0382(6) Uij ? ? C C12 1.0365(1) 0.17146(9) 0.5058(1) 0.0338(5) Uij ? ? C C13 0.9900(2) 0.2982(1) 0.7692(2) 0.0348(6) Uij ? ? C C14 0.7753(1) 0.0373(1) 0.9332(1) 0.0341(5) Uij ? ? C C15 0.6316(1) 0.0819(1) 0.9185(2) 0.0468(7) Uij ? ? C C16 1.0247(2) 0.1725(1) 1.0702(1) 0.0390(7) Uij ? ? C C17 0.9595(3) 0.2577(1) 1.0961(2) 0.065(1) Uij ? ? C H01 0.666(2) -0.017(1) 0.400(1) 0.032(4) Uiso ? ? H H02A 0.750(2) 0.026(1) 0.250(2) 0.059(6) Uiso ? ? H H03B 0.934(2) 0.046(1) 0.310(2) 0.055(6) Uiso ? ? H H04C 0.805(2) 0.126(1) 0.261(2) 0.040(5) Uiso ? ? H H05C 1.087(2) 0.134(1) 0.466(2) 0.051(5) Uiso ? ? H H06B 0.985(2) 0.214(1) 0.436(2) 0.057(6) Uiso ? ? H H07A 1.108(2) 0.191(1) 0.579(2) 0.053(6) Uiso ? ? H H08A 0.878(2) 0.306(1) 0.746(2) 0.063(6) Uiso ? ? H H09C 1.039(2) 0.334(1) 0.835(2) 0.045(5) Uiso ? ? H H010 1.009(2) 0.316(1) 0.696(2) 0.049(5) Uiso ? ? H H011 0.755(2) -0.023(1) 0.894(2) 0.040(5) Uiso ? ? H H012 0.830(2) 0.031(1) 1.028(2) 0.042(5) Uiso ? ? H H013 0.563(2) 0.081(1) 0.822(2) 0.059(6) Uiso ? ? H H014 0.644(3) 0.145(2) 0.954(3) 0.12(1) Uiso ? ? H H015 0.586(2) 0.044(1) 0.970(2) 0.047(5) Uiso ? ? H H016 1.015(2) 0.125(1) 1.128(2) 0.053(5) Uiso ? ? H H017 1.151(2) 0.172(2) 1.116(2) 0.085(8) Uiso ? ? H H018 0.970(2) 0.305(2) 1.042(2) 0.092(9) Uiso ? ? H H019 1.001(2) 0.263(1) 1.190(2) 0.075(7) Uiso ? ? H H020 0.839(3) 0.247(2) 1.083(3) 0.16(1) Uiso ? ? H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol S10 0.0185(1) 0.0391(2) 0.0459(2) -0.0034(1) 0.0072(1) 0.0000(1) S P1 0.0244(1) 0.0311(2) 0.0322(1) -0.0074(1) 0.0102(1) -0.0020(1) P P9 0.0196(1) 0.0247(1) 0.0293(1) -0.0016(1) 0.0076(1) -0.0020(1) P C2 0.0296(6) 0.0308(6) 0.0270(5) -0.0007(5) 0.0053(4) -0.0058(5) C C3 0.0311(5) 0.0268(5) 0.0249(4) 0.0078(4) 0.0114(4) 0.0003(4) C C4 0.0228(4) 0.0241(5) 0.0287(5) 0.0046(4) 0.0127(3) 0.0028(4) C C5 0.0179(4) 0.0230(5) 0.0260(4) 0.0007(4) 0.0088(3) -0.0004(4) C C6 0.0185(4) 0.0246(5) 0.0256(4) 0.0012(4) 0.0097(3) 0.0001(4) C C7 0.0224(4) 0.0286(6) 0.0263(4) 0.0049(4) 0.0116(3) 0.0026(4) C C8 0.0239(5) 0.0329(6) 0.0258(5) 0.0045(5) 0.0081(4) -0.0024(5) C C11 0.0508(7) 0.0410(8) 0.0267(5) 0.0087(6) 0.0169(4) -0.0001(5) C C12 0.0286(5) 0.0347(6) 0.0388(5) 0.0042(5) 0.0204(4) 0.0084(5) C C13 0.0369(6) 0.0254(6) 0.0450(7) 0.0003(5) 0.0111(5) -0.0024(6) C C14 0.0315(5) 0.0385(7) 0.0327(5) 0.0040(5) 0.0179(4) 0.0072(5) C C15 0.0337(5) 0.0563(9) 0.0542(7) 0.0071(6) 0.0286(4) 0.0126(7) C C16 0.0395(7) 0.0567(9) 0.0264(6) 0.0023(7) 0.0081(5) -0.0089(6) C C17 0.112(1) 0.053(1) 0.0450(7) 0.006(1) 0.0353(7) -0.0174(7) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S10 P9 1.9548(5) . . ? P1 C2 1.732(2) . . ? P1 C6 1.731(1) . . ? P9 C5 1.813(1) . . ? P9 C8 1.797(2) . . ? P9 C13 1.811(1) . . ? C2 C3 1.384(2) . . ? C2 H01 0.91(1) . . ? C3 C4 1.419(2) . . ? C3 C11 1.505(2) . . ? C4 C5 1.391(2) . . ? C4 C12 1.509(2) . . ? C5 C6 1.411(2) . . ? C6 C7 1.487(2) . . ? C7 C8 1.350(2) . . ? C7 C14 1.504(2) . . ? C8 C16 1.505(2) . . ? C11 H02A 0.99(2) . . ? C11 H03B 1.10(2) . . ? C11 H04C 0.98(2) . . ? C12 H05C 0.95(2) . . ? C12 H06B 0.98(2) . . ? C12 H07A 0.90(2) . . ? C13 H08A 1.05(2) . . ? C13 H09C 0.88(2) . . ? C13 H010 0.91(2) . . ? C14 C15 1.528(2) . . ? C14 H011 0.99(2) . . ? C14 H012 0.97(1) . . ? C15 H013 1.01(2) . . ? C15 H014 1.02(3) . . ? C15 H015 1.01(2) . . ? C16 C17 1.516(3) . . ? C16 H016 0.98(2) . . ? C16 H017 1.16(2) . . ? C17 H018 0.95(3) . . ? C17 H019 0.94(2) . . ? C17 H020 1.16(3) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 P1 C6 99.62(7) . . . ? S10 P9 C5 118.51(5) . . . ? S10 P9 C8 114.32(4) . . . ? S10 P9 C13 114.33(5) . . . ? C5 P9 C8 93.37(6) . . . ? C5 P9 C13 105.77(6) . . . ? C8 P9 C13 108.29(8) . . . ? P1 C2 C3 128.5(1) . . . ? P1 C2 H01 118(1) . . . ? C3 C2 H01 113(1) . . . ? C2 C3 C4 121.4(1) . . . ? C2 C3 C11 119.6(1) . . . ? C4 C3 C11 118.9(1) . . . ? C3 C4 C5 120.5(1) . . . ? C3 C4 C12 119.1(1) . . . ? C5 C4 C12 120.4(1) . . . ? P9 C5 C4 125.9(1) . . . ? P9 C5 C6 107.69(9) . . . ? C4 C5 C6 126.4(1) . . . ? P1 C6 C5 123.45(9) . . . ? P1 C6 C7 122.6(1) . . . ? C5 C6 C7 114.0(1) . . . ? C6 C7 C8 114.8(1) . . . ? C6 C7 C14 120.2(1) . . . ? C8 C7 C14 125.0(1) . . . ? P9 C8 C7 110.2(1) . . . ? P9 C8 C16 121.7(1) . . . ? C7 C8 C16 128.0(1) . . . ? C3 C11 H02A 106(1) . . . ? C3 C11 H03B 106.0(9) . . . ? C3 C11 H04C 113(1) . . . ? H02A C11 H03B 111(1) . . . ? H02A C11 H04C 108(1) . . . ? H03B C11 H04C 110(1) . . . ? C4 C12 H05C 109(1) . . . ? C4 C12 H06B 109(1) . . . ? C4 C12 H07A 111(1) . . . ? H05C C12 H06B 105(1) . . . ? H05C C12 H07A 102(1) . . . ? H06B C12 H07A 118(1) . . . ? P9 C13 H08A 111(1) . . . ? P9 C13 H09C 111(1) . . . ? P9 C13 H010 110(1) . . . ? H08A C13 H09C 110(1) . . . ? H08A C13 H010 106(1) . . . ? H09C C13 H010 105(1) . . . ? C7 C14 C15 113.1(1) . . . ? C7 C14 H011 108(1) . . . ? C7 C14 H012 110(1) . . . ? C15 C14 H011 108(1) . . . ? C15 C14 H012 107(1) . . . ? H011 C14 H012 107(1) . . . ? C14 C15 H013 111(1) . . . ? C14 C15 H014 113(1) . . . ? C14 C15 H015 105(1) . . . ? H013 C15 H014 109(1) . . . ? H013 C15 H015 106(1) . . . ? H014 C15 H015 110(2) . . . ? C8 C16 C17 113.5(1) . . . ? C8 C16 H016 111(1) . . . ? C8 C16 H017 112(1) . . . ? C17 C16 H016 111(1) . . . ? C17 C16 H017 112(1) . . . ? H016 C16 H017 93(1) . . . ? C16 C17 H018 112(1) . . . ? C16 C17 H019 102(1) . . . ? C16 C17 H020 110(1) . . . ? H018 C17 H019 119(1) . . . ? H018 C17 H020 111(1) . . . ? H019 C17 H020 100(2) . . . ?