#------------------------------------------------------------------------------ #$Date: 2008-02-04 17:24:24 +0000 (Mon, 04 Feb 2008) $ #$Revision: 87 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203396.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2203396 loop_ _publ_author_name 'Girija, C. R.' 'Noor Shahina Begum' _publ_section_title ; 1-Dimethylamino-3-dimethyliminio-2-(p-methoxyphenyl)prop-1-ene perchlorate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o535 _journal_page_last o536 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H21 N2 O + , Cl O4 -' _chemical_formula_moiety 'C14 H21 N2 O + , Cl O4 -' _chemical_formula_sum 'C14 H21 Cl N2 O5' _chemical_formula_weight 332.79 _chemical_name_common 'vinamidinium salt derivative' _chemical_name_systematic ; 1-Dimethylamino-3-dimethyliminio-2-(p-methoxyphenyl)prop-1-ene perchlorate ; _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.0 _cell_angle_beta 92.228(5) _cell_angle_gamma 90.0 _cell_formula_units_Z 2 _cell_length_a 7.295(2) _cell_length_b 13.117(3) _cell_length_c 8.793(2) _cell_measurement_reflns_used 8589 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.39 _cell_measurement_theta_min 2.32 _cell_volume 840.7(4) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.918 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoKa _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 8565 _diffrn_reflns_theta_full 25.0 _diffrn_reflns_theta_max 27.33 _diffrn_reflns_theta_min 2.32 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.168 _refine_diff_density_min -0.126 _refine_ls_abs_structure_details 'Flack (1983); 1577 Friedel pairs' _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 3404 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0431 _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^)+(0.0634P)^2^+0.0303P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1073 _refine_ls_wR_factor_ref 0.1126 _reflns_number_gt 2910 _reflns_number_total 3404 _reflns_threshold_expression I>2\s(I) _[local]_cod_original_file ci6331.cif loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cl1 0.27289(8) 0.90408(4) 0.94298(7) 0.06917(19) Uani d . 1 Cl O1 0.1574(5) 0.8754(3) 1.0572(3) 0.1317(11) Uani d . 1 O O2 0.2413(5) 1.0055(2) 0.9029(4) 0.1359(11) Uani d . 1 O O3 0.4567(4) 0.8873(4) 0.9781(5) 0.1554(14) Uani d . 1 O O4 0.2229(4) 0.8448(3) 0.8110(3) 0.1131(8) Uani d . 1 O O5 0.8308(3) 0.66330(17) 0.7480(2) 0.0834(6) Uani d . 1 O N1 0.2710(3) 0.57731(18) 0.1773(2) 0.0681(6) Uani d . 1 N N2 0.1303(3) 0.34506(18) 0.5870(3) 0.0709(6) Uani d . 1 N C1 0.2042(4) 0.5057(2) 0.2623(3) 0.0640(6) Uani d . 1 C H1 0.1113 0.4677 0.2142 0.077 Uiso calc R 1 H C2 0.2465(3) 0.47522(19) 0.4129(3) 0.0588(6) Uani d . 1 C C3 0.1350(3) 0.3965(2) 0.4585(3) 0.0638(6) Uani d . 1 C H3 0.0474 0.3762 0.3851 0.077 Uiso calc R 1 H C4 0.3981(3) 0.52261(19) 0.5080(3) 0.0562(5) Uani d . 1 C C5 0.3632(3) 0.59848(19) 0.6110(3) 0.0576(5) Uani d . 1 C H5 0.2424 0.6176 0.6255 0.069 Uiso calc R 1 H C6 0.5030(3) 0.6473(2) 0.6938(3) 0.0602(6) Uani d . 1 C H6 0.4756 0.6988 0.7621 0.072 Uiso calc R 1 H C7 0.6829(3) 0.6193(2) 0.6747(3) 0.0627(6) Uani d . 1 C C8 0.7201(4) 0.5426(3) 0.5734(3) 0.0766(8) Uani d . 1 C H8 0.8408 0.5228 0.5600 0.092 Uiso calc R 1 H C9 0.5793(4) 0.4948(2) 0.4913(3) 0.0690(7) Uani d . 1 C H9 0.6067 0.4429 0.4237 0.083 Uiso calc R 1 H C10 0.2121(6) 0.5828(3) 0.0161(4) 0.0990(11) Uani d . 1 C H10A 0.1108 0.5373 -0.0031 0.149 Uiso calc R 1 H H10B 0.3121 0.5635 -0.0457 0.149 Uiso calc R 1 H H10C 0.1749 0.6513 -0.0085 0.149 Uiso calc R 1 H C11 0.4171(4) 0.6488(2) 0.2220(4) 0.0789(8) Uani d . 1 C H11A 0.3976 0.6736 0.3229 0.118 Uiso calc R 1 H H11B 0.4161 0.7050 0.1522 0.118 Uiso calc R 1 H H11C 0.5335 0.6147 0.2205 0.118 Uiso calc R 1 H C12 -0.0107(6) 0.2679(3) 0.6047(4) 0.1107(13) Uani d . 1 C H12A -0.0787 0.2591 0.5100 0.166 Uiso calc R 1 H H12B -0.0923 0.2891 0.6817 0.166 Uiso calc R 1 H H12C 0.0460 0.2044 0.6343 0.166 Uiso calc R 1 H C13 0.2541(5) 0.3596(3) 0.7200(4) 0.0931(10) Uani d . 1 C H13A 0.3569 0.4003 0.6922 0.140 Uiso calc R 1 H H13B 0.2968 0.2944 0.7564 0.140 Uiso calc R 1 H H13C 0.1899 0.3935 0.7987 0.140 Uiso calc R 1 H C14 0.7938(5) 0.7280(3) 0.8734(4) 0.0837(8) Uani d . 1 C H14A 0.9072 0.7534 0.9175 0.125 Uiso calc R 1 H H14B 0.7305 0.6899 0.9485 0.125 Uiso calc R 1 H H14C 0.7187 0.7841 0.8388 0.125 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 Cl1 0.0655(3) 0.0669(3) 0.0754(4) -0.0042(3) 0.0073(2) 0.0043(3) O1 0.160(3) 0.143(3) 0.0958(17) -0.037(2) 0.0484(16) -0.0009(16) O2 0.154(3) 0.0753(16) 0.182(3) 0.0012(16) 0.050(2) 0.0129(18) O3 0.0841(17) 0.201(4) 0.179(3) 0.011(2) -0.0228(17) -0.007(3) O4 0.126(2) 0.1233(19) 0.0905(16) -0.0041(16) 0.0084(14) -0.0155(15) O5 0.0644(11) 0.0971(14) 0.0883(14) -0.0110(10) -0.0044(10) -0.0101(11) N1 0.0759(14) 0.0759(15) 0.0529(11) 0.0057(11) 0.0075(10) 0.0020(10) N2 0.0843(15) 0.0675(13) 0.0618(12) -0.0084(11) 0.0142(10) -0.0067(11) C1 0.0698(14) 0.0709(16) 0.0514(12) -0.0004(12) 0.0036(10) -0.0103(11) C2 0.0622(13) 0.0638(14) 0.0505(12) 0.0000(11) 0.0041(10) -0.0070(10) C3 0.0681(13) 0.0711(15) 0.0527(12) -0.0085(14) 0.0082(9) -0.0120(13) C4 0.0586(12) 0.0617(13) 0.0486(11) 0.0008(10) 0.0060(9) -0.0025(10) C5 0.0531(12) 0.0643(13) 0.0557(12) 0.0055(10) 0.0068(10) -0.0013(11) C6 0.0658(14) 0.0643(14) 0.0508(12) 0.0008(11) 0.0054(11) -0.0075(10) C7 0.0585(13) 0.0704(15) 0.0594(14) -0.0030(11) 0.0037(11) -0.0008(12) C8 0.0512(13) 0.094(2) 0.0847(19) 0.0124(13) 0.0072(12) -0.0105(15) C9 0.0649(14) 0.0735(17) 0.0690(15) 0.0082(12) 0.0078(12) -0.0190(13) C10 0.132(3) 0.105(3) 0.0593(17) -0.002(2) 0.0005(18) 0.0153(17) C11 0.085(2) 0.0778(18) 0.0746(17) -0.0006(15) 0.0140(15) 0.0120(14) C12 0.146(3) 0.101(2) 0.088(2) -0.055(2) 0.032(2) -0.006(2) C13 0.112(3) 0.091(2) 0.0745(19) -0.0077(18) -0.0143(17) 0.0182(17) C14 0.092(2) 0.0770(18) 0.081(2) -0.0223(15) -0.0091(15) -0.0112(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 O3 1.382(3) ? Cl1 O1 1.388(3) ? Cl1 O2 1.393(3) ? Cl1 O4 1.433(3) ? O5 C7 1.363(3) ? O5 C14 1.426(4) ? N1 C1 1.307(3) y N1 C11 1.462(4) y N1 C10 1.467(4) y N2 C3 1.317(3) y N2 C12 1.456(4) y N2 C13 1.462(4) y C1 C2 1.406(4) y C1 H1 0.93 ? C2 C3 1.383(4) y C2 C4 1.496(3) y C3 H3 0.93 ? C4 C5 1.376(3) ? C4 C9 1.384(3) ? C5 C6 1.387(3) ? C5 H5 0.93 ? C6 C7 1.380(4) ? C6 H6 0.93 ? C7 C8 1.377(4) ? C8 C9 1.383(4) ? C8 H8 0.93 ? C9 H9 0.93 ? C10 H10A 0.96 ? C10 H10B 0.96 ? C10 H10C 0.96 ? C11 H11A 0.96 ? C11 H11B 0.96 ? C11 H11C 0.96 ? C12 H12A 0.96 ? C12 H12B 0.96 ? C12 H12C 0.96 ? C13 H13A 0.96 ? C13 H13B 0.96 ? C13 H13C 0.96 ? C14 H14A 0.96 ? C14 H14B 0.96 ? C14 H14C 0.96 ? 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 O3 Cl1 O1 114.0(2) ? O3 Cl1 O2 111.0(3) ? O1 Cl1 O2 110.0(2) ? O3 Cl1 O4 108.0(2) ? O1 Cl1 O4 107.25(19) ? O2 Cl1 O4 106.2(2) ? C7 O5 C14 116.6(2) ? C1 N1 C11 126.2(2) y C1 N1 C10 119.2(3) y C11 N1 C10 114.3(3) y C3 N2 C12 119.4(2) y C3 N2 C13 125.7(2) y C12 N2 C13 114.9(3) y N1 C1 C2 132.1(2) ? N1 C1 H1 113.9 ? C2 C1 H1 113.9 ? C3 C2 C1 112.1(2) y C3 C2 C4 125.3(2) y C1 C2 C4 122.6(2) y N2 C3 C2 131.8(2) ? N2 C3 H3 114.1 ? C2 C3 H3 114.1 ? C5 C4 C9 117.5(2) ? C5 C4 C2 121.1(2) ? C9 C4 C2 121.3(2) ? C4 C5 C6 121.9(2) ? C4 C5 H5 119.0 ? C6 C5 H5 119.0 ? C7 C6 C5 119.8(2) ? C7 C6 H6 120.1 ? C5 C6 H6 120.1 ? O5 C7 C8 116.3(2) ? O5 C7 C6 124.6(2) ? C8 C7 C6 119.1(2) ? C7 C8 C9 120.5(2) ? C7 C8 H8 119.7 ? C9 C8 H8 119.7 ? C8 C9 C4 121.2(2) ? C8 C9 H9 119.4 ? C4 C9 H9 119.4 ? N1 C10 H10A 109.5 ? N1 C10 H10B 109.5 ? H10A C10 H10B 109.5 ? N1 C10 H10C 109.5 ? H10A C10 H10C 109.5 ? H10B C10 H10C 109.5 ? N1 C11 H11A 109.5 ? N1 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? N1 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? N2 C12 H12A 109.5 ? N2 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? N2 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 109.5 ? N2 C13 H13A 109.5 ? N2 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? N2 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? O5 C14 H14A 109.5 ? O5 C14 H14B 109.5 ? H14A C14 H14B 109.5 ? O5 C14 H14C 109.5 ? H14A C14 H14C 109.5 ? H14B C14 H14C 109.5 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C11 N1 C1 C2 -0.1(5) ? C10 N1 C1 C2 172.8(3) ? N1 C1 C2 C3 178.1(3) ? N1 C1 C2 C4 -3.2(5) ? C12 N2 C3 C2 177.2(3) ? C13 N2 C3 C2 -1.3(5) ? C1 C2 C3 N2 178.7(3) ? C4 C2 C3 N2 -0.1(5) ? C3 C2 C4 C5 -83.8(3) y C1 C2 C4 C5 97.7(3) y C3 C2 C4 C9 98.9(3) y C1 C2 C4 C9 -79.7(3) y C9 C4 C5 C6 1.2(4) ? C2 C4 C5 C6 -176.3(2) ? C4 C5 C6 C7 -0.6(4) ? C14 O5 C7 C8 -168.1(3) ? C14 O5 C7 C6 12.9(4) ? C5 C6 C7 O5 178.8(2) ? C5 C6 C7 C8 -0.2(4) ? O5 C7 C8 C9 -178.7(3) ? C6 C7 C8 C9 0.4(4) ? C7 C8 C9 C4 0.3(5) ? C5 C4 C9 C8 -1.0(4) ? C2 C4 C9 C8 176.4(3) ? 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 C11 H11C O2 2_646 0.96 2.46 3.341(5) 152 yes