#------------------------------------------------------------------------------ #$Date: 2011-01-02 20:00:31 +0000 (Sun, 02 Jan 2011) $ #$Revision: 5310 $ #$URL: svn://www.crystallography.net/cod/cif/2/2205040.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_2205040 loop_ _publ_author_name 'Huang, Xiao-Bo' 'Liu, Miao-Chang' 'Wu, Hua-Yue' 'Ding, Jin-Chang' 'Hu, Mao-Lin' _publ_section_title ; (Z)-Ethyl 3-phenyl-2-[(triphenylphosphoranylidene)amino]prop-2-enoate ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o280 _journal_page_last o281 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C29 H26 N O2 P' _chemical_formula_moiety 'C29 H26 N O2 P' _chemical_formula_sum 'C29 H26 N O2 P' _chemical_formula_weight 451.48 _chemical_name_systematic ; (Z)-Ethyl 3-phenyl-2-[(triphenylphosphoranylidene)amino]prop-2-enoate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 106.000(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.1918(9) _cell_length_b 17.7185(16) _cell_length_c 14.1563(13) _cell_measurement_reflns_used 3745 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 24.78 _cell_measurement_theta_min 2.38 _cell_volume 2457.4(4) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 2002)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX area-detector' _diffrn_measurement_method '\f and \w' _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 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 12947 _diffrn_reflns_theta_full 25.27 _diffrn_reflns_theta_max 25.27 _diffrn_reflns_theta_min 1.89 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_T_max 0.9717 _exptl_absorpt_correction_T_min 0.9435 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.234 _refine_diff_density_min -0.338 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 299 _refine_ls_number_reflns 4440 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.116 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0540 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.6164P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1248 _refine_ls_wR_factor_ref 0.1306 _reflns_number_gt 3764 _reflns_number_total 4440 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6440.cif _[local]_cod_cif_authors_sg_H-M 'P 21/n' _[local]_cod_cif_authors_sg_Hall -P2yn _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 ; _cod_database_code 2205040 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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_type_symbol P1 0.79316(5) 0.18677(3) 0.85497(4) 0.03841(17) Uani d . 1 P O1 0.90051(16) 0.18463(10) 0.69043(11) 0.0603(4) Uani d . 1 O O2 0.77025(16) 0.16356(10) 0.53807(11) 0.0606(4) Uani d . 1 O N1 0.69189(17) 0.14060(10) 0.77117(12) 0.0448(4) Uani d . 1 N C1 0.6462(2) 0.11897(13) 0.96965(16) 0.0517(5) Uani d . 1 C H1 0.6244 0.0827 0.9203 0.062 Uiso calc R 1 H C2 0.6031(3) 0.11021(16) 1.05292(19) 0.0672(7) Uani d . 1 C H2 0.5529 0.0678 1.0599 0.081 Uiso calc R 1 H C3 0.6338(3) 0.16358(19) 1.12559(19) 0.0762(8) Uani d . 1 C H3 0.6049 0.1572 1.1819 0.091 Uiso calc R 1 H C4 0.7067(3) 0.22606(18) 1.11538(19) 0.0778(8) Uani d . 1 C H4 0.7264 0.2626 1.1645 0.093 Uiso calc R 1 H C5 0.7513(3) 0.23538(14) 1.03276(16) 0.0599(6) Uani d . 1 C H5 0.8015 0.2780 1.0265 0.072 Uiso calc R 1 H C6 0.7221(2) 0.18175(11) 0.95898(14) 0.0422(5) Uani d . 1 C C7 0.6850(3) 0.32639(13) 0.80195(19) 0.0613(6) Uani d . 1 C H7 0.6032 0.3027 0.8008 0.074 Uiso calc R 1 H C8 0.6855(3) 0.40155(15) 0.7756(2) 0.0717(7) Uani d . 1 C H8 0.6038 0.4283 0.7573 0.086 Uiso calc R 1 H C9 0.8056(3) 0.43708(13) 0.77638(17) 0.0606(6) Uani d . 1 C H9 0.8052 0.4875 0.7581 0.073 Uiso calc R 1 H C10 0.9255(3) 0.39802(13) 0.80403(17) 0.0563(6) Uani d . 1 C H10 1.0070 0.4221 0.8050 0.068 Uiso calc R 1 H C11 0.9266(2) 0.32274(12) 0.83067(16) 0.0486(5) Uani d . 1 C H11 1.0088 0.2966 0.8491 0.058 Uiso calc R 1 H C12 0.8068(2) 0.28633(11) 0.83007(14) 0.0419(5) Uani d . 1 C C13 1.0550(2) 0.17980(13) 0.98709(17) 0.0576(6) Uani d . 1 C H13 1.0368 0.2267 1.0102 0.069 Uiso calc R 1 H C14 1.1755(3) 0.14302(15) 1.0318(2) 0.0691(7) Uani d . 1 C H14 1.2390 0.1658 1.0841 0.083 Uiso calc R 1 H C15 1.2020(3) 0.07342(16) 0.9999(2) 0.0682(7) Uani d . 1 C H15 1.2829 0.0487 1.0309 0.082 Uiso calc R 1 H C16 1.1096(3) 0.03988(14) 0.9221(2) 0.0647(7) Uani d . 1 C H16 1.1276 -0.0076 0.9007 0.078 Uiso calc R 1 H C17 0.9896(2) 0.07664(12) 0.87560(17) 0.0531(6) Uani d . 1 C H17 0.9276 0.0540 0.8224 0.064 Uiso calc R 1 H C18 0.9612(2) 0.14700(11) 0.90777(14) 0.0412(5) Uani d . 1 C C19 0.8305(4) 0.1973(3) 0.3934(2) 0.1110(13) Uani d . 1 C H19A 0.7936 0.1501 0.3648 0.167 Uiso calc R 1 H H19B 0.9036 0.2124 0.3669 0.167 Uiso calc R 1 H H19C 0.7602 0.2351 0.3787 0.167 Uiso calc R 1 H C20 0.8831(3) 0.18858(19) 0.50134(19) 0.0744(8) Uani d . 1 C H20A 0.9563 0.1517 0.5172 0.089 Uiso calc R 1 H H20B 0.9185 0.2363 0.5313 0.089 Uiso calc R 1 H C21 0.7940(2) 0.16401(12) 0.63596(15) 0.0449(5) Uani d . 1 C C22 0.6761(2) 0.13873(11) 0.67161(14) 0.0405(5) Uani d . 1 C C23 0.5623(2) 0.11266(11) 0.60597(14) 0.0446(5) Uani d . 1 C H23 0.5656 0.1113 0.5410 0.054 Uiso calc R 1 H C24 0.4350(2) 0.08636(12) 0.62304(15) 0.0463(5) Uani d . 1 C C25 0.3390(2) 0.05129(15) 0.54653(18) 0.0627(6) Uani d . 1 C H25 0.3585 0.0447 0.4866 0.075 Uiso calc R 1 H C26 0.2162(3) 0.02604(18) 0.5567(2) 0.0851(9) Uani d . 1 C H26 0.1541 0.0026 0.5043 0.102 Uiso calc R 1 H C27 0.1854(3) 0.0355(2) 0.6443(3) 0.0943(10) Uani d . 1 C H27 0.1025 0.0184 0.6516 0.113 Uiso calc R 1 H C28 0.2773(3) 0.0704(2) 0.7209(2) 0.0865(9) Uani d . 1 C H28 0.2560 0.0774 0.7801 0.104 Uiso calc R 1 H C29 0.4011(3) 0.09512(15) 0.71123(18) 0.0635(7) Uani d . 1 C H29 0.4629 0.1180 0.7643 0.076 Uiso calc R 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 0.0417(3) 0.0378(3) 0.0348(3) -0.0017(2) 0.0090(2) -0.0001(2) O1 0.0524(10) 0.0792(12) 0.0478(9) -0.0134(8) 0.0114(8) -0.0015(8) O2 0.0565(10) 0.0871(12) 0.0405(8) -0.0151(8) 0.0173(7) -0.0005(8) N1 0.0494(10) 0.0475(10) 0.0367(9) -0.0072(8) 0.0104(8) 0.0007(7) C1 0.0561(14) 0.0522(13) 0.0478(12) -0.0017(11) 0.0158(11) 0.0038(10) C2 0.0665(17) 0.0772(18) 0.0632(16) -0.0040(14) 0.0265(13) 0.0159(14) C3 0.084(2) 0.104(2) 0.0498(15) 0.0072(17) 0.0338(14) 0.0087(15) C4 0.102(2) 0.087(2) 0.0506(14) -0.0046(17) 0.0310(15) -0.0152(14) C5 0.0758(17) 0.0591(14) 0.0472(13) -0.0073(12) 0.0206(12) -0.0081(11) C6 0.0440(12) 0.0440(11) 0.0380(10) 0.0045(9) 0.0104(9) 0.0033(9) C7 0.0536(14) 0.0549(14) 0.0745(17) 0.0050(11) 0.0162(12) 0.0157(12) C8 0.0715(18) 0.0561(15) 0.0821(19) 0.0178(13) 0.0119(14) 0.0185(13) C9 0.0881(19) 0.0390(12) 0.0521(13) 0.0009(13) 0.0149(13) 0.0040(10) C10 0.0693(16) 0.0465(13) 0.0540(13) -0.0125(12) 0.0184(12) -0.0057(10) C11 0.0509(13) 0.0425(12) 0.0524(13) -0.0026(10) 0.0144(10) -0.0027(9) C12 0.0482(12) 0.0403(11) 0.0356(10) 0.0020(9) 0.0090(9) 0.0011(8) C13 0.0590(15) 0.0496(13) 0.0557(14) 0.0031(11) 0.0012(11) -0.0026(10) C14 0.0589(16) 0.0678(17) 0.0658(16) -0.0007(13) -0.0080(13) 0.0079(13) C15 0.0517(15) 0.0686(17) 0.0801(18) 0.0119(12) 0.0109(13) 0.0203(14) C16 0.0651(16) 0.0528(14) 0.0777(17) 0.0153(12) 0.0220(14) 0.0029(13) C17 0.0544(14) 0.0481(13) 0.0556(13) 0.0022(10) 0.0130(11) -0.0035(10) C18 0.0426(11) 0.0408(11) 0.0397(11) -0.0016(9) 0.0106(9) 0.0035(9) C19 0.086(2) 0.192(4) 0.0652(19) -0.016(2) 0.0376(17) 0.021(2) C20 0.0582(16) 0.111(2) 0.0610(16) -0.0113(15) 0.0279(13) 0.0073(15) C21 0.0514(13) 0.0429(11) 0.0393(11) -0.0004(10) 0.0108(10) -0.0002(9) C22 0.0490(12) 0.0370(10) 0.0342(10) 0.0024(9) 0.0090(9) 0.0035(8) C23 0.0524(13) 0.0468(12) 0.0330(10) 0.0008(10) 0.0087(9) 0.0030(9) C24 0.0461(12) 0.0466(12) 0.0428(11) 0.0011(9) 0.0063(10) 0.0082(9) C25 0.0586(15) 0.0708(16) 0.0524(14) -0.0085(13) 0.0047(12) 0.0010(12) C26 0.0634(18) 0.099(2) 0.082(2) -0.0275(16) 0.0023(15) -0.0027(17) C27 0.0557(18) 0.125(3) 0.102(2) -0.0244(18) 0.0219(17) 0.014(2) C28 0.0641(18) 0.129(3) 0.0718(18) -0.0113(18) 0.0280(15) 0.0093(18) C29 0.0525(15) 0.0862(18) 0.0508(14) -0.0043(13) 0.0129(11) 0.0016(13) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 P1 C12 115.46(9) N1 P1 C18 117.30(10) C12 P1 C18 110.14(9) N1 P1 C6 105.15(9) C12 P1 C6 105.97(9) C18 P1 C6 100.92(9) C21 O2 C20 115.62(18) C22 N1 P1 130.85(15) C2 C1 C6 120.2(2) C2 C1 H1 119.9 C6 C1 H1 119.9 C3 C2 C1 120.4(2) C3 C2 H2 119.8 C1 C2 H2 119.8 C4 C3 C2 120.0(2) C4 C3 H3 120.0 C2 C3 H3 120.0 C3 C4 C5 120.3(2) C3 C4 H4 119.8 C5 C4 H4 119.8 C4 C5 C6 120.4(2) C4 C5 H5 119.8 C6 C5 H5 119.8 C5 C6 C1 118.7(2) C5 C6 P1 121.92(17) C1 C6 P1 119.18(16) C8 C7 C12 120.0(2) C8 C7 H7 120.0 C12 C7 H7 120.0 C9 C8 C7 120.6(2) C9 C8 H8 119.7 C7 C8 H8 119.7 C10 C9 C8 119.7(2) C10 C9 H9 120.2 C8 C9 H9 120.2 C9 C10 C11 120.4(2) C9 C10 H10 119.8 C11 C10 H10 119.8 C12 C11 C10 120.6(2) C12 C11 H11 119.7 C10 C11 H11 119.7 C11 C12 C7 118.8(2) C11 C12 P1 124.75(16) C7 C12 P1 116.26(16) C14 C13 C18 120.1(2) C14 C13 H13 119.9 C18 C13 H13 119.9 C15 C14 C13 120.4(2) C15 C14 H14 119.8 C13 C14 H14 119.8 C14 C15 C16 120.2(2) C14 C15 H15 119.9 C16 C15 H15 119.9 C15 C16 C17 120.0(2) C15 C16 H16 120.0 C17 C16 H16 120.0 C16 C17 C18 120.4(2) C16 C17 H17 119.8 C18 C17 H17 119.8 C17 C18 C13 118.9(2) C17 C18 P1 118.30(16) C13 C18 P1 122.27(16) C20 C19 H19A 109.5 C20 C19 H19B 109.5 H19A C19 H19B 109.5 C20 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 O2 C20 C19 107.6(2) O2 C20 H20A 110.2 C19 C20 H20A 110.2 O2 C20 H20B 110.2 C19 C20 H20B 110.2 H20A C20 H20B 108.5 O1 C21 O2 122.6(2) O1 C21 C22 122.84(18) O2 C21 C22 114.50(18) C23 C22 N1 123.32(19) C23 C22 C21 119.17(18) N1 C22 C21 117.47(18) C22 C23 C24 128.92(19) C22 C23 H23 115.5 C24 C23 H23 115.5 C25 C24 C29 116.9(2) C25 C24 C23 118.7(2) C29 C24 C23 124.3(2) C26 C25 C24 122.0(3) C26 C25 H25 119.0 C24 C25 H25 119.0 C27 C26 C25 119.8(3) C27 C26 H26 120.1 C25 C26 H26 120.1 C28 C27 C26 119.7(3) C28 C27 H27 120.2 C26 C27 H27 120.2 C27 C28 C29 120.6(3) C27 C28 H28 119.7 C29 C28 H28 119.7 C28 C29 C24 120.9(2) C28 C29 H29 119.5 C24 C29 H29 119.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 N1 1.5706(17) P1 C12 1.812(2) P1 C18 1.812(2) P1 C6 1.813(2) O1 C21 1.202(2) O2 C21 1.339(2) O2 C20 1.456(3) N1 C22 1.374(2) C1 C2 1.375(3) C1 C6 1.387(3) C1 H1 0.9300 C2 C3 1.369(4) C2 H2 0.9300 C3 C4 1.363(4) C3 H3 0.9300 C4 C5 1.377(4) C4 H4 0.9300 C5 C6 1.382(3) C5 H5 0.9300 C7 C8 1.383(3) C7 C12 1.390(3) C7 H7 0.9300 C8 C9 1.374(4) C8 H8 0.9300 C9 C10 1.364(3) C9 H9 0.9300 C10 C11 1.385(3) C10 H10 0.9300 C11 C12 1.379(3) C11 H11 0.9300 C13 C14 1.380(3) C13 C18 1.386(3) C13 H13 0.9300 C14 C15 1.366(4) C14 H14 0.9300 C15 C16 1.371(4) C15 H15 0.9300 C16 C17 1.381(3) C16 H16 0.9300 C17 C18 1.385(3) C17 H17 0.9300 C19 C20 1.481(4) C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 C20 H20A 0.9700 C20 H20B 0.9700 C21 C22 1.495(3) C22 C23 1.352(3) C23 C24 1.460(3) C23 H23 0.9300 C24 C25 1.390(3) C24 C29 1.393(3) C25 C26 1.374(4) C25 H25 0.9300 C26 C27 1.370(4) C26 H26 0.9300 C27 C28 1.370(4) C27 H27 0.9300 C28 C29 1.378(4) C28 H28 0.9300 C29 H29 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C1 H1 N1 0.93 2.61 2.997(3) 106 C23 H23 O2 0.93 2.29 2.711(3) 107 C29 H29 N1 0.93 2.34 2.961(3) 124