#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008968.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_2008968 loop_ _publ_author_name S.Renganayaki E.Subramanian 'S.Shanmuga Sundara Raj' 'Hoong-Kun Fun' _publ_section_title ; Chloro(diisopropylamino)(phenyl)phosphine sulfide ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1525 _journal_page_last 1526 _journal_paper_doi 10.1107/S0108270199006435 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C12 H19 Cl N P S' _chemical_formula_weight 275.76 _chemical_name_systematic ; Phenyl(diisopropylamino)-chlorophosphine sulphide ; _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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.5540(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.6086(3) _cell_length_b 11.5661(4) _cell_length_c 14.7650(5) _cell_measurement_reflns_used 3243 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.35 _cell_measurement_theta_min 1.12 _cell_volume 1469.58(9) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'XP in SHELXTL' _computing_publication_material ; SHELXTL, PLATON (Spek, 1990) and PARST (Nardelli, 1995) ; _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type ; Siemens SMART CCD area detector diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0817 _diffrn_reflns_av_sigmaI/netI 0.1075 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 11387 _diffrn_reflns_theta_full 28.32 _diffrn_reflns_theta_max 28.32 _diffrn_reflns_theta_min 2.24 _exptl_absorpt_coefficient_mu 0.487 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_method none _exptl_crystal_description block _exptl_crystal_F_000 584 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.278 _refine_diff_density_min -0.385 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 221 _refine_ls_number_reflns 3622 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.1601 _refine_ls_R_factor_gt 0.0619 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0420P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1250 _reflns_number_gt 1757 _reflns_number_total 3622 _reflns_threshold_expression ' I>2\s(I) ' _cod_data_source_file sk1290.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2008968 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' 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol P1 0.27369(9) 0.27489(8) 0.13778(5) 0.0394(2) Uani d . 1 . . P S1 0.38367(10) 0.14548(9) 0.19021(6) 0.0587(3) Uani d . 1 . . S Cl1 0.38060(10) 0.42818(8) 0.17641(6) 0.0643(3) Uani d . 1 . . Cl N1 0.2525(3) 0.2795(2) 0.02787(15) 0.0420(6) Uani d . 1 . . N C1 0.0805(3) 0.2923(3) 0.17984(19) 0.0396(7) Uani d . 1 . . C C2 0.0332(4) 0.3814(4) 0.2345(2) 0.0516(9) Uani d . 1 . . C C3 -0.1171(5) 0.3845(5) 0.2658(3) 0.0663(12) Uani d . 1 . . C C4 -0.2191(5) 0.2987(5) 0.2432(3) 0.0707(13) Uani d . 1 . . C C5 -0.1735(4) 0.2095(5) 0.1899(3) 0.0682(12) Uani d . 1 . . C C6 -0.0249(4) 0.2053(4) 0.1586(3) 0.0543(9) Uani d . 1 . . C C7 0.3461(5) 0.2108(4) -0.0378(3) 0.0628(11) Uani d . 1 . . C C8 0.2978(9) 0.0860(5) -0.0408(5) 0.0924(18) Uani d . 1 . . C C9 0.5186(6) 0.2302(7) -0.0264(4) 0.0920(17) Uani d . 1 . . C C10 0.1579(4) 0.3760(3) -0.0118(2) 0.0463(8) Uani d . 1 . . C C11 0.0276(6) 0.3307(5) -0.0727(3) 0.0704(13) Uani d . 1 . . C C12 0.2570(7) 0.4658(4) -0.0581(3) 0.0717(13) Uani d . 1 . . C H11A -0.033(4) 0.272(3) -0.039(3) 0.085(14) Uiso d . 1 . . H H12A 0.299(4) 0.432(3) -0.108(2) 0.067(12) Uiso d . 1 . . H H8A 0.346(5) 0.049(5) -0.092(3) 0.15(2) Uiso d . 1 . . H H2 0.096(3) 0.436(2) 0.2480(17) 0.027(8) Uiso d . 1 . . H H11B -0.038(4) 0.393(4) -0.093(3) 0.088(14) Uiso d . 1 . . H H9B 0.548(7) 0.305(5) -0.035(4) 0.16(3) Uiso d . 1 . . H H4 -0.321(4) 0.304(3) 0.267(2) 0.080(12) Uiso d . 1 . . H H9A 0.560(5) 0.195(4) 0.028(3) 0.097(16) Uiso d . 1 . . H H12B 0.345(4) 0.491(3) -0.017(3) 0.093(16) Uiso d . 1 . . H H11C 0.072(5) 0.300(4) -0.122(3) 0.088(15) Uiso d . 1 . . H H8B 0.329(5) 0.049(4) 0.010(3) 0.12(2) Uiso d . 1 . . H H9C 0.571(5) 0.193(4) -0.074(3) 0.116(17) Uiso d . 1 . . H H12C 0.201(4) 0.531(4) -0.077(3) 0.098(16) Uiso d . 1 . . H H6 0.012(4) 0.144(3) 0.121(2) 0.074(12) Uiso d . 1 . . H H5 -0.242(4) 0.149(3) 0.176(2) 0.077(13) Uiso d . 1 . . H H3 -0.142(4) 0.447(4) 0.298(3) 0.101(17) Uiso d . 1 . . H H8C 0.195(5) 0.074(4) -0.055(3) 0.11(2) Uiso d . 1 . . H H10 0.111(3) 0.413(2) 0.0385(19) 0.041(8) Uiso d . 1 . . H H7 0.314(4) 0.240(3) -0.095(2) 0.069(11) Uiso d . 1 . . 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 P1 0.0367(5) 0.0446(5) 0.0370(4) -0.0031(4) -0.0006(3) 0.0035(4) S1 0.0455(5) 0.0664(7) 0.0641(6) 0.0079(4) -0.0027(4) 0.0234(5) Cl1 0.0640(6) 0.0660(7) 0.0628(6) -0.0240(5) 0.0014(5) -0.0105(5) N1 0.0508(15) 0.0414(16) 0.0337(13) 0.0106(13) 0.0015(11) 0.0024(12) C1 0.0420(18) 0.046(2) 0.0312(15) 0.0028(16) -0.0029(13) 0.0068(15) C2 0.052(3) 0.058(3) 0.045(2) 0.003(2) -0.0017(18) 0.0043(19) C3 0.065(3) 0.082(3) 0.053(2) 0.027(3) 0.007(2) 0.007(2) C4 0.041(2) 0.109(4) 0.062(3) 0.015(3) 0.006(2) 0.029(3) C5 0.044(2) 0.088(3) 0.073(3) -0.014(2) -0.004(2) 0.008(3) C6 0.041(2) 0.061(3) 0.061(2) -0.0037(18) 0.0040(18) -0.003(2) C7 0.082(3) 0.062(3) 0.044(2) 0.026(2) 0.009(2) -0.005(2) C8 0.127(6) 0.062(4) 0.087(4) 0.028(3) -0.011(4) -0.027(3) C9 0.074(4) 0.122(5) 0.082(4) 0.030(4) 0.030(3) 0.013(4) C10 0.060(2) 0.044(2) 0.0350(17) 0.0068(17) 0.0007(17) 0.0007(16) C11 0.082(3) 0.071(3) 0.057(3) 0.016(3) -0.023(3) -0.007(3) C12 0.101(4) 0.060(3) 0.054(3) 0.005(3) 0.011(3) 0.021(2) 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' 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 N1 P1 C1 105.10(10) y N1 P1 S1 117.90(10) y C1 P1 S1 113.40(10) y N1 P1 Cl1 106.50(10) y C1 P1 Cl1 102.50(10) y S1 P1 Cl1 110.20(10) y C10 N1 C7 116.0(2) ? C10 N1 P1 117.4(2) ? C7 N1 P1 125.3(2) ? C2 C1 C6 118.3(3) ? C2 C1 P1 125.2(3) ? C6 C1 P1 116.5(2) ? C1 C2 C3 120.6(4) ? C4 C3 C2 120.1(4) ? C3 C4 C5 120.0(4) ? C4 C5 C6 120.4(4) ? C5 C6 C1 120.6(4) ? C8 C7 N1 111.9(4) ? C8 C7 C9 114.7(5) ? N1 C7 C9 113.2(4) ? N1 C10 C11 111.3(3) ? N1 C10 C12 112.4(3) ? C11 C10 C12 112.7(4) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 N1 . 1.629(2) y P1 C1 . 1.802(3) y P1 S1 . 1.9230(10) y P1 Cl1 . 2.0710(10) y N1 C10 . 1.492(4) y N1 C7 . 1.505(4) y C1 C2 . 1.377(5) ? C1 C6 . 1.385(4) ? C2 C3 . 1.386(5) ? C3 C4 . 1.360(6) ? C4 C5 . 1.362(6) ? C5 C6 . 1.373(5) ? C7 C8 . 1.503(7) ? C7 C9 . 1.506(7) ? C10 C11 . 1.512(5) ? C10 C12 . 1.519(5) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C2 H2 Cl1 1_555 0.85(2) 2.70(3) 3.180(4) 117(2) yes C11 H11C Cg1 4_565 0.90(4) 2.926 3.577 130.27 yes C12 H12C Cg1 3_565 0.93(4) 3.026 3.897 155.95 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4421845 2 PubChem 139056811