#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200150.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200150 loop_ _publ_author_name 'Horn, E.' 'Kurosawa, K.' 'Tiekink, E. R. T.' _publ_section_title ; Monoclinic form of 1-(dicyclohexylthiophosphinoyl)-N-phenylthioformamide ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o321 _journal_page_last o322 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C19 H28 N P S2' _chemical_formula_sum 'C19 H28 N P S2' _chemical_formula_weight 365.53 _chemical_name_common 1-(dicyclohexylthiophosphinoyl)-N-phenylthioformamide _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 105.426(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.0740(10) _cell_length_b 18.139(2) _cell_length_c 11.3858(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 12.2 _cell_measurement_theta_min 11.0 _cell_volume 2005.6(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1992)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution ; SIR92 (Altomare et al., 1994) ; _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Rigaku AFC-7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .7107 _diffrn_reflns_av_R_equivalents .025 _diffrn_reflns_av_sigmaI/netI .097 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 6358 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 30.1 _diffrn_reflns_theta_min 2.7 _diffrn_standards_decay_% .63 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .345 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 784 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .15 _refine_diff_density_max .21 _refine_diff_density_min -.16 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.688 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 208 _refine_ls_number_reflns 3143 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt .040 _refine_ls_shift/esd_mean .001 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.004|Fo|^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .028 _reflns_number_gt 3143 _reflns_number_total 6054 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6013.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2200150 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy S1 .39714(8) .20810(4) .11082(7) .0586(2) Uani d . . 1.00 S2 .28158(7) .06445(4) .40850(6) .0547(2) Uani d . . 1.00 P1 .39855(6) .09220(3) .30227(6) .0385(2) Uani d . . 1.00 N1 .2560(2) .21695(10) .2808(2) .0435(6) Uani d . . 1.00 C1 .3403(2) .18220(10) .2265(2) .0379(6) Uani d . . 1.00 C2 .1907(2) .28700(10) .2620(2) .0410(7) Uani d . . 1.00 C3 .2116(2) .33950(10) .1811(2) .0480(8) Uani d . . 1.00 C4 .1426(3) .40620(10) .1726(2) .0581(9) Uani d . . 1.00 C5 .0542(3) .42100(10) .2427(3) .0632(9) Uani d . . 1.00 C6 .0348(3) .3688(2) .3238(3) .0670(10) Uani d . . 1.00 C7 .1021(3) .30190(10) .3345(2) .0550(9) Uani d . . 1.00 C8 .5784(2) .10640(10) .3875(2) .0412(7) Uani d . . 1.00 C9 .5899(3) .17200(10) .4746(2) .0519(8) Uani d . . 1.00 C10 .7367(3) .18060(10) .5543(2) .0645(9) Uani d . . 1.00 C11 .8383(3) .18820(10) .4780(3) .0662(9) Uani d . . 1.00 C12 .8283(3) .1227(2) .3930(3) .0690(10) Uani d . . 1.00 C13 .6824(3) .11330(10) .3107(2) .0572(9) Uani d . . 1.00 C14 .3931(2) .02700(10) .1799(2) .0407(7) Uani d . . 1.00 C15 .2473(3) .01700(10) .0981(2) .0551(8) Uani d . . 1.00 C16 .2462(3) -.0380(2) -.0042(2) .0664(10) Uani d . . 1.00 C17 .3101(3) -.11150(10) .0461(3) .0658(10) Uani d . . 1.00 C18 .4526(3) -.10220(10) .1302(3) .0620(9) Uani d . . 1.00 C19 .4538(3) -.04760(10) .2319(2) .0525(8) Uani d . . 1.00 H1 .2361 .1900 .3435 .0521 Uiso calc . . 1.00 H2 .2725 .3301 .1319 .0576 Uiso calc . . 1.00 H3 .1568 .4425 .1170 .0697 Uiso calc . . 1.00 H4 .0070 .4668 .2353 .0758 Uiso calc . . 1.00 H5 -.0257 .3788 .3731 .0800 Uiso calc . . 1.00 H6 .0881 .2661 .3910 .0660 Uiso calc . . 1.00 H7 .6052 .0631 .4383 .0495 Uiso calc . . 1.00 H8 .5631 .2166 .4274 .0622 Uiso calc . . 1.00 H9 .5287 .1641 .5264 .0622 Uiso calc . . 1.00 H10 .7419 .2243 .6044 .0774 Uiso calc . . 1.00 H11 .7608 .1376 .6061 .0774 Uiso calc . . 1.00 H12 .8183 .2330 .4300 .0795 Uiso calc . . 1.00 H13 .9309 .1908 .5315 .0795 Uiso calc . . 1.00 H14 .8911 .1302 .3426 .0825 Uiso calc . . 1.00 H15 .8542 .0784 .4414 .0825 Uiso calc . . 1.00 H16 .6785 .0691 .2619 .0686 Uiso calc . . 1.00 H17 .6589 .1558 .2576 .0686 Uiso calc . . 1.00 H18 .4499 .0464 .1303 .0488 Uiso calc . . 1.00 H19 .1883 -.0012 .1466 .0661 Uiso calc . . 1.00 H20 .2129 .0642 .0626 .0661 Uiso calc . . 1.00 H21 .1517 -.0463 -.0508 .0797 Uiso calc . . 1.00 H22 .2981 -.0175 -.0570 .0797 Uiso calc . . 1.00 H23 .2517 -.1347 .0908 .0790 Uiso calc . . 1.00 H24 .3157 -.1428 -.0214 .0790 Uiso calc . . 1.00 H25 .4850 -.1496 .1660 .0745 Uiso calc . . 1.00 H26 .5137 -.0844 .0834 .0745 Uiso calc . . 1.00 H27 .5479 -.0403 .2801 .0630 Uiso calc . . 1.00 H28 .3994 -.0673 .2833 .0630 Uiso calc . . 1.00 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 S1 .0833(5) .0449(4) .0609(4) .0122(4) .0422(4) .0146(3) S2 .0665(5) .0497(4) .0583(4) .0028(4) .0345(4) .0140(3) P1 .0460(4) .0315(3) .0410(3) .0029(3) .0170(3) .0051(3) N1 .0490(10) .0410(10) .0470(10) .0076(10) .0221(10) .0105(9) C1 .0410(10) .0330(10) .0410(10) .0030(10) .0130(10) .0040(10) C2 .0360(10) .0380(10) .0480(10) .0050(10) .0080(10) -.0020(10) C3 .047(2) .0400(10) .060(2) .0070(10) .0200(10) .0030(10) C4 .060(2) .0380(10) .075(2) .0060(10) .015(2) .0050(10) C5 .058(2) .048(2) .080(2) .0150(10) .012(2) -.008(2) C6 .055(2) .072(2) .077(2) .020(2) .025(2) -.008(2) C7 .052(2) .057(2) .062(2) .0090(10) .0260(10) .0070(10) C8 .0450(10) .0320(10) .0470(10) .0060(10) .0120(10) .0040(10) C9 .059(2) .042(2) .053(2) .0050(10) .0120(10) -.0060(10) C10 .069(2) .051(2) .065(2) .001(2) .003(2) -.0070(10) C11 .054(2) .046(2) .090(2) -.0020(10) .003(2) .001(2) C12 .048(2) .063(2) .096(2) .0000(10) .022(2) -.009(2) C13 .050(2) .059(2) .067(2) .0000(10) .0230(10) -.0080(10) C14 .049(2) .0330(10) .0420(10) -.0010(10) .0170(10) .0010(10) C15 .058(2) .045(2) .059(2) .0000(10) .0100(10) -.0010(10) C16 .073(2) .056(2) .062(2) -.007(2) .006(2) -.0090(10) C17 .082(2) .044(2) .073(2) -.013(2) .025(2) -.0140(10) C18 .075(2) .0380(10) .075(2) .0010(10) .025(2) -.0080(10) C19 .060(2) .0370(10) .061(2) .0050(10) .0180(10) .0000(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 . . 1.639(2) no S2 P1 . . 1.9655(8) no P1 C1 . . 1.866(2) no P1 C8 . . 1.832(2) no P1 C14 . . 1.817(2) no N1 C1 . . 1.334(3) no N1 C2 . . 1.420(3) no C2 C3 . . 1.380(3) no C2 C7 . . 1.393(3) no C3 C4 . . 1.387(3) no C4 C5 . . 1.371(3) no C5 C6 . . 1.372(4) no C6 C7 . . 1.380(3) no C8 C9 . . 1.534(3) no C8 C13 . . 1.538(3) no C9 C10 . . 1.524(3) no C10 C11 . . 1.514(4) no C11 C12 . . 1.518(4) no C12 C13 . . 1.528(3) no C14 C15 . . 1.527(3) no C14 C19 . . 1.537(3) no C15 C16 . . 1.532(3) no C16 C17 . . 1.524(4) no C17 C18 . . 1.509(4) no C18 C19 . . 1.522(3) no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .003 .002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H .000 .000 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; P .102 .094 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; S .125 .123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N .006 .003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 5 1 1 5 0 1 5 1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag S2 P1 C1 110.00(7) no S2 P1 C8 112.35(8) no S2 P1 C14 113.86(8) no C1 P1 C8 105.51(10) no C1 P1 C14 105.85(10) no C8 P1 C14 108.70(10) no C1 N1 C2 132.8(2) no C1 N1 H1 113.6 no C2 N1 H1 113.6 no S1 C1 P1 119.20(10) no S1 C1 N1 129.6(2) no P1 C1 N1 111.1(2) no N1 C2 C3 124.8(2) no N1 C2 C7 115.4(2) no C3 C2 C7 119.8(2) no C2 C3 C4 119.1(2) no C2 C3 H2 120.4 no C4 C3 H2 120.4 no C3 C4 C5 121.4(2) no C3 C4 H3 119.3 no C5 C4 H3 119.3 no C4 C5 C6 119.2(2) no C4 C5 H4 120.4 no C6 C5 H4 120.4 no C5 C6 C7 120.8(2) no C5 C6 H5 119.6 no C7 C6 H5 119.6 no C2 C7 C6 119.7(2) no C2 C7 H6 120.2 no C6 C7 H6 120.2 no P1 C8 C9 110.2(2) no P1 C8 C13 116.0(2) no P1 C8 H7 106.3 no C9 C8 C13 111.0(2) no C9 C8 H7 106.3 no C13 C8 H7 106.3 no C8 C9 C10 111.0(2) no C8 C9 H8 109.1 no C8 C9 H9 109.1 no C10 C9 H8 109.1 no C10 C9 H9 109.1 no H8 C9 H9 109.5 no C9 C10 C11 111.4(2) no C9 C10 H10 109.0 no C9 C10 H11 109.0 no C11 C10 H10 109.0 no C11 C10 H11 109.0 no H10 C10 H11 109.5 no C10 C11 C12 110.7(2) no C10 C11 H12 109.2 no C10 C11 H13 109.2 no C12 C11 H12 109.2 no C12 C11 H13 109.2 no H12 C11 H13 109.5 no C11 C12 C13 111.6(2) no C11 C12 H14 108.9 no C11 C12 H15 108.9 no C13 C12 H14 108.9 no C13 C12 H15 108.9 no H14 C12 H15 109.5 no C8 C13 C12 110.5(2) no C8 C13 H16 109.2 no C8 C13 H17 109.2 no C12 C13 H16 109.2 no C12 C13 H17 109.2 no H16 C13 H17 109.5 no P1 C14 C15 111.9(2) no P1 C14 C19 110.5(2) no P1 C14 H18 108.0 no C15 C14 C19 110.5(2) no C15 C14 H18 108.0 no C19 C14 H18 108.0 no C14 C15 C16 110.6(2) no C14 C15 H19 109.2 no C14 C15 H20 109.2 no C16 C15 H19 109.2 no C16 C15 H20 109.2 no H19 C15 H20 109.5 no C15 C16 C17 111.6(2) no C15 C16 H21 109.0 no C15 C16 H22 109.0 no C17 C16 H21 108.9 no C17 C16 H22 108.9 no H21 C16 H22 109.5 no C16 C17 C18 112.1(2) no C16 C17 H23 108.8 no C16 C17 H24 108.8 no C18 C17 H23 108.8 no C18 C17 H24 108.8 no H23 C17 H24 109.5 no C17 C18 C19 111.7(2) no C17 C18 H25 108.9 no C17 C18 H26 108.9 no C19 C18 H25 108.9 no C19 C18 H26 108.9 no H25 C18 H26 109.5 no C14 C19 C18 111.0(2) no C14 C19 H27 109.1 no C14 C19 H28 109.1 no C18 C19 H27 109.1 no C18 C19 H28 109.1 no H27 C19 H28 109.5 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 C9 3.536(2) 4_554 no _cod_database_fobs_code 2200150 _journal_paper_doi 10.1107/S160053680100410X