#------------------------------------------------------------------------------ #$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/47/2014711.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_2014711 loop_ _publ_author_name 'Millar, David' 'Zakharov, Lev N.' 'Rheingold, Arnold L.' 'Linda H. Doerrer' _publ_section_title ; Aurophilic interactions in \m-p-phenylenediethynyl-bis[(trimethyl phosphite)gold(I)] dichloromethane hemisolvate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first m90 _journal_page_last m92 _journal_paper_doi 10.1107/S0108270104033402 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac '[Au2 (C10 H4) (C3 H9 O3 P)2], 0.5C H2 Cl2' _chemical_formula_moiety 'C16 H22 Au2 O6 P2, 0.5 C H2 Cl2' _chemical_formula_sum 'C16.5 H33 Au2 Cl O6 P2' _chemical_formula_weight 808.69 _chemical_name_systematic ; \m-(p-phenylenediethynyl)-bis[(trimethyl phosphite)gold(I)] dichloromethane hemisolvate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 105.2250(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 16.6892(9) _cell_length_b 13.8568(8) _cell_length_c 20.4250(12) _cell_measurement_reflns_used 5620 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 2.53 _cell_volume 4557.7(4) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_molecular_graphics 'SHELXTL (Bruker, 2000)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w scans' _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 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0169 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 18988 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.94 _diffrn_standards_decay_% no _diffrn_standards_number no _exptl_absorpt_coefficient_mu 13.147 _exptl_absorpt_correction_T_max 0.3014 _exptl_absorpt_correction_T_min 0.1600 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 2.357 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 3000 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.888 _refine_diff_density_min -0.896 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 5101 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0248 _refine_ls_R_factor_gt 0.0202 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+20.4573P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.0515 _reflns_number_gt 4364 _reflns_number_total 5101 _reflns_threshold_expression I>2\s(I) _cod_data_source_file jz1684.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_original_formula_sum 'C16.5 H33 Au2 Cl1 O6 P2' _cod_database_code 2014711 _cod_database_fobs_code 2014711 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 Au1 0.268333(8) 0.247168(8) 0.703911(6) 0.01723(5) Uani d . 1 . . Au Au2 0.078153(8) 0.753356(8) 0.203780(6) 0.01685(5) Uani d . 1 . . Au P1 0.31078(6) 0.15126(6) 0.79510(4) 0.02124(19) Uani d . 1 . . P P2 0.03857(5) 0.84523(6) 0.11004(4) 0.01784(17) Uani d . 1 . . P O1 0.3355(3) 0.1958(2) 0.86847(14) 0.0630(12) Uani d . 1 . . O O2 0.39111(16) 0.09516(19) 0.79001(13) 0.0293(6) Uani d . 1 . . O O3 0.24760(15) 0.07199(17) 0.80695(11) 0.0214(5) Uani d . 1 . . O O4 0.11540(14) 0.89541(17) 0.09349(12) 0.0219(5) Uani d . 1 . . O O5 -0.02113(15) 0.93378(17) 0.11065(12) 0.0225(5) Uani d . 1 . . O O6 -0.01239(15) 0.79279(19) 0.04238(12) 0.0241(5) Uani d . 1 . . O C1 0.2400(2) 0.3292(2) 0.62044(16) 0.0177(6) Uani d . 1 . . C C2 0.2224(2) 0.3780(2) 0.56982(16) 0.0170(6) Uani d . 1 . . C C3 0.1986(2) 0.4371(2) 0.50999(16) 0.0170(6) Uani d . 1 . . C C4 0.1802(2) 0.3972(2) 0.44500(16) 0.0186(7) Uani d . 1 . . C H4 0.1832 0.3307 0.4398 0.022 Uiso calc R 1 . . H C5 0.1574(2) 0.4559(2) 0.38798(16) 0.0177(6) Uani d . 1 . . C H5 0.1451 0.4281 0.3451 0.021 Uiso calc R 1 . . H C6 0.1526(2) 0.5562(2) 0.39406(16) 0.0173(6) Uani d . 1 . . C C7 0.1713(2) 0.5960(2) 0.45958(17) 0.0223(7) Uani d . 1 . . C H7 0.1687 0.6625 0.4649 0.027 Uiso calc R 1 . . H C8 0.1937(2) 0.5373(2) 0.51626(16) 0.0204(7) Uani d . 1 . . C H8 0.2056 0.5649 0.5592 0.024 Uiso calc R 1 . . H C9 0.1301(2) 0.6173(2) 0.33532(16) 0.0191(7) Uani d . 1 . . C C10 0.1116(2) 0.6704(2) 0.28663(16) 0.0186(7) Uani d . 1 . . C C11 0.3268(4) 0.2883(4) 0.8858(2) 0.068(2) Uani d . 1 . . C H11A 0.3806 0.3174 0.9018 0.102 Uiso calc R 1 . . H H11B 0.2984 0.2903 0.9210 0.102 Uiso calc R 1 . . H H11C 0.2952 0.3230 0.8469 0.102 Uiso calc R 1 . . H C12 0.4307(2) 0.0228(3) 0.84000(19) 0.0328(9) Uani d . 1 . . C H12A 0.4661 0.0542 0.8788 0.039 Uiso calc R 1 . . H H12B 0.4631 -0.0201 0.8203 0.039 Uiso calc R 1 . . H H12C 0.3888 -0.0134 0.8537 0.039 Uiso calc R 1 . . H C13 0.2145(2) 0.0059(2) 0.75163(18) 0.0253(8) Uani d . 1 . . C H13A 0.1956 0.0415 0.7101 0.030 Uiso calc R 1 . . H H13B 0.1688 -0.0292 0.7605 0.030 Uiso calc R 1 . . H H13C 0.2571 -0.0386 0.7476 0.030 Uiso calc R 1 . . H C14 0.1076(2) 0.9598(3) 0.0364(2) 0.0327(9) Uani d . 1 . . C H14A 0.0812 0.9265 -0.0048 0.039 Uiso calc R 1 . . H H14B 0.1618 0.9810 0.0346 0.039 Uiso calc R 1 . . H H14C 0.0747 1.0147 0.0415 0.039 Uiso calc R 1 . . H C15 -0.0983(2) 0.9190(3) 0.1292(2) 0.0355(9) Uani d . 1 . . C H15A -0.1336 0.8767 0.0969 0.043 Uiso calc R 1 . . H H15B -0.1257 0.9799 0.1294 0.043 Uiso calc R 1 . . H H15C -0.0868 0.8907 0.1736 0.043 Uiso calc R 1 . . H C16 0.0178(3) 0.7021(3) 0.0237(2) 0.0389(10) Uani d . 1 . . C H16A 0.0684 0.7128 0.0107 0.047 Uiso calc R 1 . . H H16B -0.0230 0.6745 -0.0137 0.047 Uiso calc R 1 . . H H16C 0.0283 0.6588 0.0616 0.047 Uiso calc R 1 . . H C17 -0.0116(7) 0.2125(7) 0.2280(4) 0.046(2) Uiso d PD 0.50 A -1 C H17A -0.0637 0.2468 0.2220 0.056 Uiso calc PR 0.50 A -1 H H17B 0.0330 0.2589 0.2429 0.056 Uiso calc PR 0.50 A -1 H Cl1 -0.0036(2) 0.1253(3) 0.2923(2) 0.0921(12) Uani d PD 0.50 A -1 Cl Cl2 -0.0069(3) 0.1656(4) 0.1506(3) 0.1178(17) Uani d PD 0.50 A -1 Cl 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 Au1 0.02684(8) 0.01502(7) 0.00959(7) -0.00155(5) 0.00433(5) 0.00245(4) Au2 0.01786(7) 0.01849(8) 0.01276(7) 0.00057(5) 0.00149(5) 0.00550(4) P1 0.0350(5) 0.0170(4) 0.0099(4) -0.0039(4) 0.0026(3) 0.0026(3) P2 0.0176(4) 0.0215(4) 0.0134(4) 0.0011(3) 0.0023(3) 0.0053(3) O1 0.144(4) 0.0214(15) 0.0117(14) -0.0185(19) -0.0008(17) 0.0012(11) O2 0.0222(13) 0.0403(15) 0.0226(13) -0.0019(11) 0.0010(10) 0.0130(11) O3 0.0284(13) 0.0203(12) 0.0175(12) 0.0009(10) 0.0095(10) 0.0027(9) O4 0.0192(12) 0.0275(13) 0.0191(12) 0.0020(10) 0.0052(10) 0.0103(10) O5 0.0224(12) 0.0246(12) 0.0234(13) 0.0064(10) 0.0113(10) 0.0103(10) O6 0.0215(13) 0.0288(14) 0.0182(13) 0.0044(10) -0.0014(10) 0.0007(10) C1 0.0239(17) 0.0159(15) 0.0119(15) -0.0006(13) 0.0025(13) -0.0004(12) C2 0.0182(16) 0.0206(16) 0.0129(15) -0.0020(13) 0.0055(12) -0.0028(12) C3 0.0169(15) 0.0217(16) 0.0134(15) -0.0005(13) 0.0057(12) 0.0036(12) C4 0.0253(17) 0.0168(15) 0.0141(15) -0.0003(13) 0.0059(13) -0.0006(12) C5 0.0183(16) 0.0233(16) 0.0116(15) -0.0006(13) 0.0041(12) -0.0005(12) C6 0.0163(15) 0.0238(16) 0.0125(15) 0.0024(13) 0.0050(12) 0.0044(12) C7 0.034(2) 0.0180(16) 0.0173(17) 0.0037(14) 0.0105(14) 0.0025(13) C8 0.0285(18) 0.0234(17) 0.0106(15) 0.0009(14) 0.0074(13) -0.0008(13) C9 0.0195(16) 0.0233(17) 0.0154(16) 0.0019(13) 0.0063(13) 0.0015(13) C10 0.0172(15) 0.0221(17) 0.0155(16) 0.0019(13) 0.0023(12) 0.0036(13) C11 0.095(4) 0.057(3) 0.030(2) 0.052(3) -0.021(3) -0.021(2) C12 0.032(2) 0.036(2) 0.025(2) 0.0030(17) -0.0025(16) 0.0115(16) C13 0.0268(19) 0.0225(17) 0.0243(19) -0.0049(14) 0.0025(15) 0.0021(14) C14 0.028(2) 0.041(2) 0.031(2) 0.0031(17) 0.0111(16) 0.0210(18) C15 0.026(2) 0.037(2) 0.049(3) 0.0067(17) 0.0207(19) 0.0128(19) C16 0.034(2) 0.038(2) 0.036(2) 0.0067(19) -0.0066(18) -0.0138(19) Cl1 0.0421(16) 0.082(2) 0.142(4) 0.0004(16) 0.006(2) 0.037(2) Cl2 0.115(3) 0.120(4) 0.136(4) -0.071(3) 0.063(3) -0.038(3) 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' 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' Au Au -2.0133 8.8022 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 Au1 P1 . . 174.78(10) yes C1 Au1 Au2 . 6_566 89.32(10) yes P1 Au1 Au2 . 6_566 95.56(3) yes C10 Au2 P2 . . 179.03(10) yes C10 Au2 Au1 . 6_565 86.65(9) yes P2 Au2 Au1 . 6_565 94.13(2) yes Au1 Au2 Au2 6_565 2_555 149.550(10) yes O1 P1 O2 . . 104.0(2) no O1 P1 O3 . . 98.36(17) no O2 P1 O3 . . 106.25(14) no O1 P1 Au1 . . 120.33(12) yes O2 P1 Au1 . . 109.00(10) yes O3 P1 Au1 . . 117.34(10) yes O4 P2 O5 . . 102.10(13) no O4 P2 O6 . . 107.15(14) no O5 P2 O6 . . 99.58(13) no O4 P2 Au2 . . 111.09(9) yes O5 P2 Au2 . . 118.48(9) yes O6 P2 Au2 . . 116.76(10) yes C11 O1 P1 . . 127.2(3) no C12 O2 P1 . . 121.9(2) no C13 O3 P1 . . 116.9(2) no C14 O4 P2 . . 122.7(2) no C15 O5 P2 . . 119.8(2) no C16 O6 P2 . . 118.8(2) no C2 C1 Au1 . . 179.4(3) yes C1 C2 C3 . . 177.9(4) yes C4 C3 C8 . . 118.5(3) no C4 C3 C2 . . 121.6(3) no C8 C3 C2 . . 119.9(3) no C5 C4 C3 . . 120.5(3) no C5 C4 H4 . . 119.7 no C3 C4 H4 . . 119.7 no C4 C5 C6 . . 121.1(3) no C4 C5 H5 . . 119.4 no C6 C5 H5 . . 119.4 no C5 C6 C7 . . 118.1(3) no C5 C6 C9 . . 121.3(3) no C7 C6 C9 . . 120.6(3) no C8 C7 C6 . . 120.7(3) no C8 C7 H7 . . 119.7 no C6 C7 H7 . . 119.7 no C7 C8 C3 . . 121.1(3) no C7 C8 H8 . . 119.4 no C3 C8 H8 . . 119.4 no C10 C9 C6 . . 178.7(4) yes C9 C10 Au2 . . 177.5(3) yes O1 C11 H11A . . 109.5 no O1 C11 H11B . . 109.5 no H11A C11 H11B . . 109.5 no O1 C11 H11C . . 109.5 no H11A C11 H11C . . 109.5 no H11B C11 H11C . . 109.5 no O2 C12 H12A . . 109.5 no O2 C12 H12B . . 109.5 no H12A C12 H12B . . 109.5 no O2 C12 H12C . . 109.5 no H12A C12 H12C . . 109.5 no H12B C12 H12C . . 109.5 no O3 C13 H13A . . 109.5 no O3 C13 H13B . . 109.5 no H13A C13 H13B . . 109.5 no O3 C13 H13C . . 109.5 no H13A C13 H13C . . 109.5 no H13B C13 H13C . . 109.5 no O4 C14 H14A . . 109.5 no O4 C14 H14B . . 109.5 no H14A C14 H14B . . 109.5 no O4 C14 H14C . . 109.5 no H14A C14 H14C . . 109.5 no H14B C14 H14C . . 109.5 no O5 C15 H15A . . 109.5 no O5 C15 H15B . . 109.5 no H15A C15 H15B . . 109.5 no O5 C15 H15C . . 109.5 no H15A C15 H15C . . 109.5 no H15B C15 H15C . . 109.5 no O6 C16 H16A . . 109.5 no O6 C16 H16B . . 109.5 no H16A C16 H16B . . 109.5 no O6 C16 H16C . . 109.5 no H16A C16 H16C . . 109.5 no H16B C16 H16C . . 109.5 no Cl2 C17 Cl1 . . 114.2(6) no Cl2 C17 H17A . . 108.7 no Cl1 C17 H17A . . 108.7 no Cl2 C17 H17B . . 108.7 no Cl1 C17 H17B . . 108.7 no H17A C17 H17B . . 107.6 no 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 Au1 C1 . 2.000(3) yes Au1 P1 . 2.2459(8) yes Au1 Au2 6_566 3.1733(2) no Au2 Au2 2 3.5995(3) yes Au2 C10 . 2.000(3) yes Au2 P2 . 2.2492(8) yes Au2 Au1 6_565 3.1733(2) yes P1 O1 . 1.572(3) yes P1 O2 . 1.577(3) yes P1 O3 . 1.585(2) yes P2 O4 . 1.571(2) yes P2 O5 . 1.583(2) yes P2 O6 . 1.595(2) yes O1 C11 . 1.347(6) no O2 C12 . 1.460(4) no O3 C13 . 1.447(4) no O4 C14 . 1.447(4) no O5 C15 . 1.449(4) no O6 C16 . 1.442(5) no C1 C2 . 1.205(4) yes C2 C3 . 1.438(4) yes C3 C4 . 1.396(4) no C3 C8 . 1.398(5) no C4 C5 . 1.390(4) no C4 H4 . 0.9300 no C5 C6 . 1.400(5) no C5 H5 . 0.9300 no C6 C7 . 1.405(5) no C6 C9 . 1.435(4) yes C7 C8 . 1.384(5) no C7 H7 . 0.9300 no C8 H8 . 0.9300 no C9 C10 . 1.210(5) yes C11 H11A . 0.9600 no C11 H11B . 0.9600 no C11 H11C . 0.9600 no C12 H12A . 0.9600 no C12 H12B . 0.9600 no C12 H12C . 0.9600 no C13 H13A . 0.9600 no C13 H13B . 0.9600 no C13 H13C . 0.9600 no C14 H14A . 0.9600 no C14 H14B . 0.9600 no C14 H14C . 0.9600 no C15 H15A . 0.9600 no C15 H15B . 0.9600 no C15 H15C . 0.9600 no C16 H16A . 0.9600 no C16 H16B . 0.9600 no C16 H16C . 0.9600 no C17 Cl2 . 1.730(9) no C17 Cl1 . 1.763(8) no C17 H17A . 0.9700 no C17 H17B . 0.9700 no