#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/33/2203399.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_2203399 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-methoxyphenyl)prop-1-ene perchlorate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o592 _journal_page_last o594 _journal_paper_doi 10.1107/S1600536804005586 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H21 N2 O 1+, Cl O4 1-' _chemical_formula_moiety 'C14 H21 N2 O 1+, Cl O4 1-' _chemical_formula_sum 'C14 H21 Cl N2 O5' _chemical_formula_weight 332.78 _chemical_name_systematic ; 1-Dimethylamino-3-dimethyliminio-1-(p-methoxyphenyl)prop-1-ene perchlorate ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 93.10(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.239(3) _cell_length_b 12.399(2) _cell_length_c 16.152(3) _cell_measurement_reflns_used 15 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 8.02 _cell_measurement_theta_min 6.9 _cell_volume 1647.6(7) _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 'DIRDIF96 (Beurskens et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.907 _diffrn_measured_fraction_theta_max 0.907 _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 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 4573 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.07 _diffrn_standards_decay_% -2.9 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 704 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.503 _refine_diff_density_min -0.414 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 204 _refine_ls_number_reflns 2632 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0497 _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^)+(0.0694P)^2^+1.1572P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1391 _refine_ls_wR_factor_ref 0.1481 _reflns_number_gt 2165 _reflns_number_total 2632 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ci6344.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. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1647.5(7) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2203399 _cod_database_fobs_code 2203399 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z 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 Cl 0.72695(10) 0.31905(6) 0.39881(4) 0.0600(3) Uani d . 1 Cl O1 0.5710(4) 0.2722(4) 0.4108(2) 0.1301(13) Uani d . 1 O O2 0.8148(3) 0.3136(2) 0.47693(16) 0.0924(9) Uani d . 1 O O3 0.7067(7) 0.4225(3) 0.3712(3) 0.180(2) Uani d . 1 O O4 0.8005(4) 0.2541(3) 0.34001(16) 0.1127(11) Uani d . 1 O O5 0.1412(3) 0.51292(16) -0.12847(11) 0.0585(5) Uani d . 1 O N1 0.3821(3) 0.20799(18) 0.16951(13) 0.0504(6) Uani d . 1 N N2 0.1457(3) 0.49010(19) 0.32478(13) 0.0544(6) Uani d . 1 N C1 0.3109(3) 0.3041(2) 0.17392(16) 0.0439(6) Uani d . 1 C C2 0.2743(4) 0.3489(2) 0.25039(16) 0.0510(7) Uani d . 1 C H2 0.3137 0.3156 0.2990 0.061 Uiso calc R 1 H C3 0.1820(3) 0.4407(2) 0.25574(16) 0.0495(7) Uani d . 1 C H3 0.1413 0.4708 0.2061 0.059 Uiso calc R 1 H C4 0.2676(3) 0.3615(2) 0.09501(15) 0.0416(6) Uani d . 1 C C5 0.3253(3) 0.4644(2) 0.08034(16) 0.0471(6) Uani d . 1 C H5 0.3919 0.4982 0.1208 0.057 Uiso calc R 1 H C6 0.2859(3) 0.5181(2) 0.00675(16) 0.0478(6) Uani d . 1 C H6 0.3262 0.5870 -0.0021 0.057 Uiso calc R 1 H C7 0.1863(3) 0.4684(2) -0.05329(15) 0.0443(6) Uani d . 1 C C8 0.1236(3) 0.3666(2) -0.03908(16) 0.0488(6) Uani d . 1 C H8 0.0541 0.3340 -0.0789 0.059 Uiso calc R 1 H C9 0.1645(3) 0.3139(2) 0.03425(16) 0.0478(6) Uani d . 1 C H9 0.1226 0.2455 0.0433 0.057 Uiso calc R 1 H C10 0.4131(5) 0.1397(2) 0.2427(2) 0.0683(9) Uani d . 1 C H10A 0.3215 0.1429 0.2770 0.102 Uiso calc R 1 H H10B 0.5084 0.1649 0.2736 0.102 Uiso calc R 1 H H10C 0.4296 0.0666 0.2255 0.102 Uiso calc R 1 H C11 0.4583(4) 0.1683(3) 0.0951(2) 0.0655(8) Uani d . 1 C H11A 0.4498 0.2223 0.0526 0.098 Uiso calc R 1 H H11B 0.4041 0.1038 0.0758 0.098 Uiso calc R 1 H H11C 0.5709 0.1527 0.1085 0.098 Uiso calc R 1 H C12 0.1999(5) 0.4485(3) 0.40635(17) 0.0697(9) Uani d . 1 C H12A 0.3135 0.4313 0.4067 0.105 Uiso calc R 1 H H12B 0.1393 0.3847 0.4182 0.105 Uiso calc R 1 H H12C 0.1823 0.5022 0.4478 0.105 Uiso calc R 1 H C13 0.0405(5) 0.5848(3) 0.3225(2) 0.0746(10) Uani d . 1 C H13A 0.0196 0.6073 0.2661 0.112 Uiso calc R 1 H H13B 0.0930 0.6422 0.3536 0.112 Uiso calc R 1 H H13C -0.0604 0.5672 0.3464 0.112 Uiso calc R 1 H C14 0.2051(4) 0.6161(3) -0.1474(2) 0.0688(9) Uani d . 1 C H14A 0.1582 0.6402 -0.1999 0.103 Uiso calc R 1 H H14B 0.3210 0.6112 -0.1502 0.103 Uiso calc R 1 H H14C 0.1794 0.6666 -0.1050 0.103 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 Cl 0.0657(5) 0.0604(5) 0.0537(4) 0.0127(4) 0.0013(3) 0.0058(3) O1 0.087(2) 0.214(4) 0.089(2) -0.026(2) 0.0046(16) -0.010(2) O2 0.0962(19) 0.108(2) 0.0695(15) 0.0219(16) -0.0216(14) -0.0145(14) O3 0.288(6) 0.080(2) 0.171(4) 0.053(3) -0.005(4) 0.044(2) O4 0.132(3) 0.144(3) 0.0633(15) 0.055(2) 0.0152(16) -0.0091(17) O5 0.0718(14) 0.0573(11) 0.0456(10) -0.0043(10) -0.0039(9) 0.0096(9) N1 0.0591(15) 0.0466(12) 0.0452(12) 0.0034(11) -0.0012(10) -0.0018(9) N2 0.0671(16) 0.0539(13) 0.0424(12) 0.0046(12) 0.0033(11) -0.0047(10) C1 0.0432(15) 0.0442(14) 0.0440(14) -0.0030(11) -0.0018(11) -0.0019(10) C2 0.0637(18) 0.0514(15) 0.0371(13) 0.0050(14) -0.0039(12) 0.0010(11) C3 0.0554(17) 0.0526(15) 0.0401(14) 0.0012(13) -0.0002(12) -0.0024(11) C4 0.0428(14) 0.0439(13) 0.0386(12) 0.0003(11) 0.0060(11) -0.0025(10) C5 0.0494(16) 0.0470(14) 0.0447(14) -0.0040(12) -0.0009(12) -0.0055(11) C6 0.0528(16) 0.0417(13) 0.0491(14) -0.0050(12) 0.0050(12) 0.0000(11) C7 0.0466(15) 0.0472(14) 0.0393(13) 0.0052(12) 0.0053(11) 0.0014(11) C8 0.0545(17) 0.0500(15) 0.0414(13) -0.0072(13) -0.0028(12) -0.0035(11) C9 0.0564(17) 0.0427(14) 0.0443(14) -0.0083(12) 0.0043(12) -0.0022(11) C10 0.092(2) 0.0489(16) 0.0614(18) 0.0087(17) -0.0156(17) 0.0060(14) C11 0.071(2) 0.0595(18) 0.0668(19) 0.0134(16) 0.0138(16) -0.0082(15) C12 0.101(3) 0.067(2) 0.0418(15) 0.0055(18) 0.0053(16) -0.0034(13) C13 0.088(3) 0.066(2) 0.069(2) 0.0192(18) 0.0057(18) -0.0123(16) C14 0.083(2) 0.0607(19) 0.0623(18) -0.0022(17) 0.0047(17) 0.0194(15) 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 O3 Cl O4 111.5(3) ? O3 Cl O2 112.4(3) ? O4 Cl O2 110.77(17) ? O3 Cl O1 109.3(3) ? O4 Cl O1 106.3(2) ? O2 Cl O1 106.16(19) ? C7 O5 C14 117.9(2) ? C1 N1 C10 122.1(2) y C1 N1 C11 123.5(2) y C10 N1 C11 113.7(2) y C3 N2 C13 120.9(3) y C3 N2 C12 121.7(2) y C13 N2 C12 117.3(2) y N1 C1 C2 121.2(2) ? N1 C1 C4 118.0(2) ? C2 C1 C4 120.8(2) ? C3 C2 C1 122.0(2) ? C3 C2 H2 119.0 ? C1 C2 H2 119.0 ? N2 C3 C2 126.1(3) ? N2 C3 H3 117.0 ? C2 C3 H3 117.0 ? C5 C4 C9 118.1(2) ? C5 C4 C1 121.3(2) ? C9 C4 C1 120.6(2) ? C6 C5 C4 121.5(2) ? C6 C5 H5 119.2 ? C4 C5 H5 119.2 ? C7 C6 C5 119.4(2) ? C7 C6 H6 120.3 ? C5 C6 H6 120.3 ? O5 C7 C6 124.5(2) ? O5 C7 C8 115.3(2) ? C6 C7 C8 120.1(2) ? C9 C8 C7 119.8(2) ? C9 C8 H8 120.1 ? C7 C8 H8 120.1 ? C8 C9 C4 121.0(2) ? C8 C9 H9 119.5 ? C4 C9 H9 119.5 ? 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_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl O3 1.365(3) ? Cl O4 1.407(3) ? Cl O2 1.422(3) ? Cl O1 1.432(3) ? O5 C7 1.367(3) ? O5 C14 1.423(4) ? N1 C1 1.332(3) y N1 C10 1.466(4) y N1 C11 1.470(4) y N2 C3 1.321(3) y N2 C13 1.459(4) y N2 C12 1.462(4) y C1 C2 1.402(4) y C1 C4 1.486(3) y C2 C3 1.374(4) y C2 H2 0.93 ? C3 H3 0.93 ? C4 C5 1.386(4) ? C4 C9 1.394(4) ? C5 C6 1.386(4) ? C5 H5 0.93 ? C6 C7 1.381(4) ? C6 H6 0.93 ? C7 C8 1.388(4) ? C8 C9 1.379(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_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 C3 H3 O5 3_565 0.93 2.59 3.325(4) 136 yes C10 H10C O3 2_645 0.96 2.59 3.379(5) 140 yes C11 H11A O1 4_554 0.96 2.55 3.251(5) 130 yes C11 H11B O3 2_645 0.96 2.59 3.393(6) 141 yes C12 H12C O2 3_666 0.96 2.59 3.506(4) 160 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 5.6(4) ? C11 N1 C1 C2 -164.8(3) ? C10 N1 C1 C4 -173.1(3) ? C11 N1 C1 C4 16.5(4) ? N1 C1 C2 C3 -171.2(3) ? C4 C1 C2 C3 7.4(4) ? C13 N2 C3 C2 -177.4(3) ? C12 N2 C3 C2 -1.5(5) ? C1 C2 C3 N2 -177.9(3) ? N1 C1 C4 C5 -123.3(3) y C2 C1 C4 C5 58.0(4) y N1 C1 C4 C9 58.1(3) y C2 C1 C4 C9 -120.5(3) y C9 C4 C5 C6 -1.7(4) ? C1 C4 C5 C6 179.7(2) ? C4 C5 C6 C7 0.4(4) ? C14 O5 C7 C6 2.1(4) ? C14 O5 C7 C8 -178.4(3) ? C5 C6 C7 O5 -179.1(2) ? C5 C6 C7 C8 1.4(4) ? O5 C7 C8 C9 178.7(2) ? C6 C7 C8 C9 -1.8(4) ? C7 C8 C9 C4 0.4(4) ? C5 C4 C9 C8 1.3(4) ? C1 C4 C9 C8 179.9(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9199269 2 PubChem 11024087