#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/33/2203398.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_2203398 loop_ _publ_author_name 'Girija, C. R.' 'Noor Shahina Begum' 'Sridhar, M. A.' 'Lokanath, N. K.' 'Prasad, J. S.' _publ_section_title ; 1-Dimethylamino-3-dimethyliminio-1-(p-methylphenyl)prop-1-ene perchlorate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o589 _journal_page_last o591 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H21 N2 1+, Cl O4 1-' _chemical_formula_moiety 'C14 H21 N2 1+, Cl O4 1-' _chemical_formula_sum 'C14 H21 Cl N2 O4' _chemical_formula_weight 316.78 _chemical_name_systematic ; 1-Dimethylamino-3-dimethyliminio-1-(p-methylphenyl)prop-1-ene perchlorate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 115.501(18) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.601(3) _cell_length_b 12.409(2) _cell_length_c 12.664(4) _cell_measurement_reflns_used 23 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 4.4 _cell_measurement_theta_min 3.5 _cell_volume 1645.5(8) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992) ; _computing_data_reduction ; TEXSAN (Molecular Structure Corporation, 1995) ; _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution TEXSAN _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku AFC-7S' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoKa _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0995 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 3045 _diffrn_reflns_theta_full 25 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.42 _diffrn_standards_decay_% -10.40 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.422 _refine_diff_density_min -0.344 _refine_ls_extinction_coef 0.024(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 196 _refine_ls_number_reflns 2890 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.083 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0751 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1546P)^2^+0.6164P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2207 _refine_ls_wR_factor_ref 0.2718 _reflns_number_gt 1649 _reflns_number_total 2890 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6343.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/a' _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. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1645.4(8) _cod_database_code 2203398 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,-z -x,-y,-z 1/2+x,1/2-y,z 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 Cl 0.0656(7) 0.0799(9) 0.0978(10) -0.0038(5) 0.0289(6) -0.0203(6) O1 0.135(3) 0.121(3) 0.078(3) 0.008(3) 0.020(2) -0.015(2) O2 0.106(3) 0.121(3) 0.136(4) 0.034(3) 0.027(3) -0.004(3) O3 0.127(4) 0.257(7) 0.202(6) -0.056(4) 0.102(4) -0.034(5) O4 0.146(4) 0.095(3) 0.225(6) -0.011(3) 0.048(4) -0.073(4) N1 0.061(2) 0.0560(19) 0.086(2) -0.0113(15) 0.0271(18) 0.0038(17) N2 0.067(2) 0.0590(19) 0.101(3) -0.0014(18) 0.036(2) 0.0135(19) C1 0.054(2) 0.0411(18) 0.083(3) 0.0051(16) 0.024(2) 0.0024(18) C2 0.053(2) 0.048(2) 0.084(3) 0.0023(16) 0.023(2) 0.0006(19) C3 0.057(2) 0.053(2) 0.091(3) 0.0040(19) 0.026(2) 0.009(2) C4 0.053(2) 0.049(2) 0.084(3) -0.0035(16) 0.026(2) -0.0010(19) C5 0.057(2) 0.066(3) 0.089(3) 0.0056(19) 0.025(2) -0.005(2) C6 0.055(2) 0.085(3) 0.092(3) -0.002(2) 0.019(2) 0.004(3) C7 0.074(3) 0.070(3) 0.079(3) -0.018(2) 0.028(2) -0.005(2) C8 0.081(3) 0.067(3) 0.097(4) 0.002(2) 0.028(3) -0.016(2) C9 0.066(3) 0.061(2) 0.098(3) 0.009(2) 0.019(2) -0.006(2) C10 0.083(3) 0.084(3) 0.075(3) -0.019(3) 0.025(3) -0.004(2) C11 0.099(4) 0.097(4) 0.100(4) -0.049(3) 0.034(3) 0.002(3) C12 0.082(3) 0.064(3) 0.132(5) -0.020(2) 0.048(3) -0.009(3) C13 0.103(4) 0.118(5) 0.134(5) -0.016(3) 0.061(4) 0.034(4) C14 0.099(4) 0.113(4) 0.093(4) -0.033(3) 0.021(3) -0.022(3) 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_occupancy _atom_site_type_symbol Cl 0.12016(11) 0.05315(10) 0.30803(11) 0.0833(5) Uani 1.000 Cl O1 0.0698(4) 0.0370(4) 0.1861(3) 0.1204(17) Uani 1.000 O O2 0.2334(4) -0.0085(4) 0.3626(4) 0.1298(19) Uani 1.000 O O3 0.0295(5) 0.0235(6) 0.3464(6) 0.184(3) Uani 1.000 O O4 0.1529(5) 0.1619(4) 0.3401(6) 0.167(3) Uani 1.000 O N1 0.5578(3) 0.2068(3) 0.5990(3) 0.0693(11) Uani 1.000 N N2 0.3312(3) -0.0200(3) 0.7511(4) 0.0757(14) Uani 1.000 N C1 0.5356(3) 0.1663(3) 0.6848(4) 0.0613(13) Uani 1.000 C C2 0.4400(4) 0.0893(3) 0.6651(4) 0.0640(14) Uani 1.000 C C3 0.4172(4) 0.0519(3) 0.7572(4) 0.0691(14) Uani 1.000 C C4 0.6177(4) 0.2060(3) 0.8052(4) 0.0632(14) Uani 1.000 C C5 0.7372(4) 0.1592(4) 0.8715(4) 0.0729(16) Uani 1.000 C C6 0.8126(4) 0.1988(4) 0.9822(4) 0.0818(16) Uani 1.000 C C7 0.7739(4) 0.2824(4) 1.0295(4) 0.0761(17) Uani 1.000 C C8 0.6550(5) 0.3270(4) 0.9645(4) 0.0853(19) Uani 1.000 C C9 0.5787(4) 0.2888(3) 0.8544(4) 0.0807(16) Uani 1.000 C C10 0.4834(5) 0.1744(4) 0.4761(4) 0.0838(17) Uani 1.000 C C11 0.6599(5) 0.2837(5) 0.6178(5) 0.102(2) Uani 1.000 C C12 0.2501(5) -0.0764(4) 0.6451(5) 0.092(2) Uani 1.000 C C13 0.3169(6) -0.0492(5) 0.8578(6) 0.115(3) Uani 1.000 C C14 0.8576(6) 0.3232(5) 1.1513(5) 0.109(2) Uani 1.000 C H2 0.39174 0.06334 0.58992 0.0766 Uiso 1.000 H H3 0.46771 0.08041 0.83071 0.0828 Uiso 1.000 H H5 0.76557 0.10198 0.84140 0.0877 Uiso 1.000 H H6 0.89200 0.16754 1.02573 0.0982 Uiso 1.000 H H8 0.62642 0.38338 0.99537 0.1023 Uiso 1.000 H H9 0.49880 0.31961 0.81225 0.0967 Uiso 1.000 H H10A 0.50858 0.21749 0.42657 0.1255 Uiso 1.000 H H10B 0.49920 0.09978 0.46713 0.1255 Uiso 1.000 H H10C 0.39410 0.18481 0.45449 0.1255 Uiso 1.000 H H11A 0.72366 0.25024 0.59954 0.1520 Uiso 1.000 H H11B 0.62539 0.34525 0.56820 0.1520 Uiso 1.000 H H11C 0.69774 0.30628 0.69817 0.1520 Uiso 1.000 H H12A 0.17102 -0.09501 0.64771 0.1378 Uiso 1.000 H H12B 0.23321 -0.03092 0.57877 0.1378 Uiso 1.000 H H12C 0.29223 -0.14092 0.63844 0.1378 Uiso 1.000 H H13A 0.22938 -0.04020 0.84413 0.1719 Uiso 1.000 H H13B 0.34166 -0.12302 0.87744 0.1719 Uiso 1.000 H H13C 0.37029 -0.00351 0.92114 0.1719 Uiso 1.000 H H14A 0.93011 0.27657 1.18780 0.1631 Uiso 1.000 H H14B 0.88624 0.39486 1.14655 0.1631 Uiso 1.000 H H14C 0.80953 0.32415 1.19693 0.1631 Uiso 1.000 H 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O1 Cl O2 108.5(3) no O1 Cl O3 109.1(4) no O1 Cl O4 112.6(4) no O2 Cl O3 111.7(4) no O2 Cl O4 107.3(3) no O3 Cl O4 107.7(4) no C1 N1 C10 122.2(4) yes C1 N1 C11 123.2(4) yes C10 N1 C11 114.6(4) yes C3 N2 C12 123.8(4) yes C3 N2 C13 119.6(5) yes C12 N2 C13 116.5(4) yes N1 C1 C2 122.2(4) yes N1 C1 C4 116.8(4) yes C2 C1 C4 121.0(4) no C1 C2 C3 120.2(4) no N2 C3 C2 126.4(4) yes C1 C4 C5 120.5(4) no C1 C4 C9 121.3(4) no C5 C4 C9 118.2(4) no C4 C5 C6 119.4(4) no C5 C6 C7 122.0(5) no C6 C7 C8 118.4(4) no C6 C7 C14 120.9(5) no C8 C7 C14 120.8(5) no C7 C8 C9 120.5(5) no C4 C9 C8 121.6(5) no C1 C2 H2 119.97 no C3 C2 H2 119.86 no N2 C3 H3 116.85 no C2 C3 H3 116.72 no C4 C5 H5 120.28 no C6 C5 H5 120.33 no C5 C6 H6 119.00 no C7 C6 H6 119.01 no C7 C8 H8 119.76 no C9 C8 H8 119.71 no C4 C9 H9 119.23 no C8 C9 H9 119.21 no N1 C10 H10A 109.47 no N1 C10 H10B 109.46 no N1 C10 H10C 109.51 no H10A C10 H10B 109.42 no H10A C10 H10C 109.47 no H10B C10 H10C 109.50 no N1 C11 H11A 109.50 no N1 C11 H11B 109.46 no N1 C11 H11C 109.41 no H11A C11 H11B 109.53 no H11A C11 H11C 109.49 no H11B C11 H11C 109.44 no N2 C12 H12A 109.51 no N2 C12 H12B 109.52 no N2 C12 H12C 109.44 no H12A C12 H12B 109.48 no H12A C12 H12C 109.41 no H12B C12 H12C 109.47 no N2 C13 H13A 109.47 no N2 C13 H13B 109.42 no N2 C13 H13C 109.50 no H13A C13 H13B 109.44 no H13A C13 H13C 109.50 no H13B C13 H13C 109.49 no C7 C14 H14A 109.51 no C7 C14 H14B 109.49 no C7 C14 H14C 109.48 no H14A C14 H14B 109.47 no H14A C14 H14C 109.46 no H14B C14 H14C 109.42 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl O1 1.410(4) no Cl O2 1.417(5) no Cl O3 1.385(7) no Cl O4 1.413(5) no N1 C1 1.319(6) yes N1 C10 1.474(6) yes N1 C11 1.459(7) yes N2 C3 1.316(6) yes N2 C12 1.446(7) yes N2 C13 1.476(8) yes C1 C2 1.402(6) yes C1 C4 1.491(6) yes C2 C3 1.383(7) yes C4 C5 1.401(7) no C4 C9 1.375(6) no C5 C6 1.384(7) no C6 C7 1.367(7) no C7 C8 1.382(7) no C7 C14 1.513(7) no C8 C9 1.375(7) no C2 H2 0.9299 no C3 H3 0.9303 no C5 H5 0.9305 no C6 H6 0.9304 no C8 H8 0.9294 no C9 H9 0.9296 no C10 H10A 0.9604 no C10 H10B 0.9601 no C10 H10C 0.9595 no C11 H11A 0.9593 no C11 H11B 0.9600 no C11 H11C 0.9604 no C12 H12A 0.9603 no C12 H12B 0.9596 no C12 H12C 0.9605 no C13 H13A 0.9602 no C13 H13B 0.9602 no C13 H13C 0.9595 no C14 H14A 0.9598 no C14 H14B 0.9602 no C14 H14C 0.9605 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 O3 C12 3.356(9) 3_556 no O4 C12 3.416(7) 2_556 no O1 H9 2.8152 2_546 no O1 H5 2.7048 3_656 no O1 H6 2.7196 1_454 no O2 H12B 2.7526 . no O2 H5 2.8366 3_656 no O2 H2 2.8112 . no O3 H12A 2.5207 3_556 no O4 H10C 2.5532 . no O4 H14A 2.8518 1_454 no O4 H12C 2.5134 2_556 no O4 H10A 2.7966 4_455 no C2 C11 3.424(8) 4_455 no C3 C9 3.418(6) . no C3 C11 3.413(8) 4_455 no C5 C11 3.322(8) . no C6 C13 3.526(9) 3_657 no C7 C13 3.580(8) 3_657 no C9 C3 3.418(6) . no C9 C11 3.507(8) . no C11 C2 3.424(8) 4_555 no C11 C9 3.507(8) . no C11 C3 3.413(8) 4_555 no C11 C5 3.322(8) . no C12 O3 3.356(9) 3_556 no C12 O4 3.416(7) 2_546 no C13 C6 3.526(9) 3_657 no C13 C7 3.580(8) 3_657 no C2 H10B 2.8734 . no C2 H12B 2.6301 . no C2 H11A 3.0263 4_455 no C2 H10C 2.7530 . no C3 H14B 2.8442 2_647 no C3 H11C 2.9153 4_455 no C4 H3 2.4586 . no C4 H11C 2.3090 . no C5 H11C 2.7375 . no C5 H3 3.0994 . no C7 H13B 2.9083 3_657 no C9 H3 2.8464 . no C9 H11C 2.8673 . no C10 H2 2.5352 . no C12 H2 2.6803 . no H2 O2 2.8112 . no H2 C10 2.5352 . no H2 C12 2.6803 . no H2 H10B 2.4178 . no H2 H10C 2.2923 . no H2 H12B 2.1323 . no H3 C4 2.4586 . no H3 C5 3.0994 . no H3 C9 2.8464 . no H3 H13C 2.1881 . no H5 O1 2.7048 3_656 no H5 O2 2.8366 3_656 no H6 O1 2.7196 1_656 no H6 H14A 2.3361 . no H9 O1 2.8152 2_556 no H10A H11A 2.5462 . no H10A H11B 2.3396 . no H10A O4 2.7966 4_555 no H10B C2 2.8734 . no H10B H2 2.4178 . no H10C O4 2.5532 . no H10C C2 2.7530 . no H10C H2 2.2923 . no H11A H10A 2.5462 . no H11A C2 3.0263 4_555 no H11B H10A 2.3396 . no H11B H12B 2.5974 4_555 no H11C C4 2.3090 . no H11C C5 2.7375 . no H11C C9 2.8673 . no H11C C3 2.9153 4_555 no H12A H13A 2.3787 . no H12A O3 2.5207 3_556 no H12B O2 2.7526 . no H12B C2 2.6301 . no H12B H2 2.1323 . no H12B H11B 2.5974 4_455 no H12C O4 2.5134 2_546 no H13A H12A 2.3787 . no H13B C7 2.9083 3_657 no H13C H3 2.1881 . no H14A O4 2.8518 1_656 no H14A H6 2.3361 . no H14B C3 2.8442 2_657 no 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 O2 . 0.93 2.81 3.740(6) 177 yes C10 H10C O4 . 0.96 2.55 3.465(9) 159 yes C12 H12B O2 . 0.96 2.75 3.599(9) 147 yes C12 H12B O3 . 0.96 2.95 3.750(8) 141 yes C5 H5 O1 3_656 0.93 2.71 3.589(7) 159 yes C5 H5 O2 3_656 0.93 2.84 3.643(8) 146 yes C6 H6 O1 1_656 0.93 2.72 3.601(6) 158 yes C14 H14A O4 1_656 0.96 2.85 3.796(8) 168 yes C8 H8 O1 4_556 0.93 2.93 3.754(8) 148 yes C9 H9 O1 2_556 0.93 2.82 3.458(6) 127 yes C10 H10A O4 4_555 0.96 2.80 3.725(10) 163 yes C13 H13A O3 3_556 0.96 2.94 3.740(8) 142 yes C12 H12A O3 3_556 0.96 2.52 3.356(9) 145 yes C12 H12C O4 2_546 0.96 2.51 3.416(7) 156 yes 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 C10 N1 C1 C2 0.3(6) no C11 N1 C1 C2 -177.5(4) no C10 N1 C1 C4 -180.0(4) no C11 N1 C1 C4 2.3(6) no C12 N2 C3 C2 3.6(7) no C13 N2 C3 C2 -178.4(5) no N1 C1 C4 C9 95.5(5) y C2 C1 C4 C5 95.1(6) y N1 C1 C4 C5 -84.7(5) y C2 C1 C4 C9 -84.7(5) y N1 C1 C2 C3 -177.7(4) no C4 C1 C2 C3 2.5(6) no C1 C2 C3 N2 -179.8(4) no C1 C4 C5 C6 178.8(4) no C5 C4 C9 C8 1.4(7) no C1 C4 C9 C8 -178.8(4) no C9 C4 C5 C6 -1.4(7) no C4 C5 C6 C7 0.2(8) no C5 C6 C7 C8 0.9(8) no C5 C6 C7 C14 179.3(5) no C14 C7 C8 C9 -179.2(5) no C6 C7 C8 C9 -0.9(8) no C7 C8 C9 C4 -0.3(8) no _cod_database_fobs_code 2203398