#------------------------------------------------------------------------------ #$Date: 2018-09-27 05:13:35 +0100 (Thu, 27 Sep 2018) $ #$Revision: 211196 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202336.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_2202336 loop_ _publ_author_name 'Marciniak, Bernard' 'Pavlyuk, Volodymyr' 'Rozycka-Sokolowska, Ewa' _publ_section_title ; 6-(3-Iodopropyl)benzo[f][1,7]naphthyridin-6-ium iodide ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1178 _journal_page_last o1180 _journal_paper_doi 10.1107/S1600536803015800 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C15 H14 I N2 1+, I 1-' _chemical_formula_moiety 'C15 H14 I N2 1+, I 1-' _chemical_formula_sum 'C15 H14 I2 N2' _chemical_formula_weight 475.8 _chemical_melting_point .173E-171 _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 120.71(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.8960(10) _cell_length_b 12.547(2) _cell_length_c 13.454(2) _cell_measurement_reflns_used 27 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 22 _cell_measurement_theta_min 3 _cell_volume 1581.4(5) _computing_cell_refinement 'DARCH Package' _computing_data_collection 'DARCH Package (Burevestnik, 1991)' _computing_data_reduction 'DARCH package' _computing_molecular_graphics 'ORTEP-3 (Farrugia,1997) and PLATON (Spek,2000)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type DARCH-1 _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'BSW x-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3784 _diffrn_reflns_theta_full 27.45 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 2.17 _diffrn_standards_decay_% negligible _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.966 _exptl_absorpt_correction_T_max .702 _exptl_absorpt_correction_T_min .491 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(DIFABS; Walker & Stuart, 1983)' _exptl_crystal_colour 'clear pale yellow' _exptl_crystal_density_diffrn 2.000 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description tablet _exptl_crystal_F_000 896 _exptl_crystal_size_max .29 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .09 _refine_diff_density_max 1.355 _refine_diff_density_min -1.335 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.192 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 3622 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.192 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0427 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.038P)^2^+1.109P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0945 _refine_ls_wR_factor_ref 0.0954 _reflns_number_gt 3075 _reflns_number_total 3622 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6305.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 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 'P 21/c' _cod_database_code 2202336 _cod_database_fobs_code 2202336 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 I1 0.34454(4) 0.44544(3) 0.27367(3) 0.05835(12) Uani d . 1 . . I I2 0.61764(4) 0.09761(4) 0.45654(3) 0.06918(15) Uani d . 1 . . I N1 0.2450(5) 0.3524(3) 0.5084(4) 0.0534(10) Uani d . 1 . . N N2 0.1508(5) 0.6291(4) 0.4363(3) 0.0592(12) Uani d . 1 . . N C1 0.2646(7) 0.4620(4) 0.5067(5) 0.0548(13) Uani d . 1 . . C H1 0.3532 0.4952 0.5477 0.096(9) Uiso calc R 1 . . H C2 0.1389(6) 0.5158(4) 0.4378(4) 0.0491(12) Uani d . 1 . . C C3 0.0242(7) 0.6907(4) 0.3579(5) 0.0655(15) Uani d . 1 . . C H3 0.0346 0.7634 0.3512 0.096(9) Uiso calc R 1 . . H C4 -0.1033(7) 0.6490(5) 0.2964(5) 0.0627(14) Uani d . 1 . . C H4 -0.1834 0.6885 0.2457 0.096(9) Uiso calc R 1 . . H C5 -0.1075(7) 0.5437(4) 0.3133(5) 0.0549(12) Uani d . 1 . . C H5 -0.1982 0.5135 0.2779 0.096(9) Uiso calc R 1 . . H C6 0.0069(6) 0.4728(4) 0.3775(5) 0.0514(13) Uani d . 1 . . C C7 0.0013(7) 0.3605(4) 0.3890(5) 0.0538(13) Uani d . 1 . . C C8 -0.1307(7) 0.3133(4) 0.3265(5) 0.0523(12) Uani d . 1 . . C H8 -0.2112 0.3562 0.2872 0.096(9) Uiso calc R 1 . . H C9 -0.1460(7) 0.2090(4) 0.3209(5) 0.0564(13) Uani d . 1 . . C H9 -0.2334 0.1789 0.2680 0.096(9) Uiso calc R 1 . . H C10 -0.0314(7) 0.1435(4) 0.3944(5) 0.0594(14) Uani d . 1 . . C H10 -0.0477 0.0707 0.3945 0.096(9) Uiso calc R 1 . . H C11 0.1132(5) 0.1837(4) 0.4711(3) 0.0523(13) Uani d . 1 . . C H11 0.1907 0.1433 0.5243 0.096(9) Uiso calc R 1 . . H C12 0.1155(7) 0.2958(5) 0.4509(5) 0.0566(13) Uani d . 1 . . C C13 0.3911(6) 0.2913(4) 0.5803(5) 0.087(2) Uani d . 1 . . C H13A 0.4663 0.3428 0.6236 0.18(2) Uiso calc R 1 . . H H13B 0.3855 0.2450 0.6357 0.18(2) Uiso calc R 1 . . H C14 0.4316(7) 0.2239(6) 0.5060(6) 0.0767(19) Uani d . 1 . . C H14A 0.3574 0.1714 0.4637 0.18(2) Uiso calc R 1 . . H H14B 0.4361 0.2698 0.4499 0.18(2) Uiso calc R 1 . . H C15 0.5701(6) 0.1683(6) 0.5746(5) 0.0759(19) Uani d . 1 . . C H15A 0.5636 0.1143 0.6233 0.18(2) Uiso calc R 1 . . H H15B 0.6443 0.2186 0.6236 0.18(2) 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 I1 0.0659(2) 0.0649(2) 0.0599(2) 0.00025(16) 0.04346(19) -0.00008(17) I2 0.0508(2) 0.0782(3) 0.0472(2) 0.02681(18) 0.00232(16) 0.00022(18) N1 0.079(3) 0.048(2) 0.049(2) 0.002(2) 0.044(2) 0.0045(19) N2 0.093(4) 0.047(2) 0.057(3) -0.002(2) 0.052(3) 0.004(2) C1 0.082(4) 0.051(3) 0.055(3) 0.001(3) 0.053(3) 0.001(2) C2 0.081(4) 0.044(2) 0.059(3) 0.010(2) 0.063(3) 0.002(2) C3 0.082(4) 0.038(3) 0.062(3) 0.002(3) 0.027(3) -0.002(2) C4 0.084(4) 0.050(3) 0.054(3) -0.006(3) 0.036(3) -0.005(3) C5 0.074(3) 0.051(3) 0.052(3) -0.003(2) 0.041(3) 0.003(2) C6 0.081(4) 0.047(3) 0.063(3) 0.009(2) 0.063(3) 0.002(2) C7 0.088(4) 0.049(3) 0.059(3) 0.006(3) 0.062(3) 0.004(2) C8 0.082(4) 0.046(3) 0.060(3) 0.008(2) 0.059(3) 0.005(2) C9 0.085(4) 0.055(3) 0.059(3) -0.011(3) 0.058(3) -0.008(2) C10 0.084(4) 0.048(3) 0.050(3) -0.004(3) 0.036(3) -0.005(2) C11 0.093(4) 0.041(2) 0.064(3) 0.011(2) 0.070(3) 0.006(2) C12 0.079(4) 0.057(3) 0.064(3) 0.003(3) 0.058(3) 0.000(3) C13 0.073(4) 0.106(5) 0.057(4) 0.039(4) 0.016(3) 0.012(4) C14 0.056(3) 0.085(5) 0.052(3) 0.023(3) 0.001(3) 0.002(3) C15 0.052(3) 0.105(5) 0.041(3) 0.023(3) 0.002(2) 0.000(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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 0.0000 '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 C1 N1 C12 127.4(5) C1 N1 C13 112.0(4) C12 N1 C13 120.5(3) C2 N2 C3 118.6(4) C2 C1 N1 112.7(5) C2 C1 H1 123.6 N1 C1 H1 123.6 C6 C2 C1 126.7(5) C6 C2 N2 117.7(4) C1 C2 N2 115.5(5) C4 C3 N2 123.5(5) C4 C3 H3 118.3 N2 C3 H3 118.3 C3 C4 C5 113.7(6) C3 C4 H4 123.1 C5 C4 H4 123.1 C4 C5 C6 128.8(6) C4 C5 H5 115.6 C6 C5 H5 115.6 C2 C6 C5 116.9(5) C2 C6 C7 114.9(5) C5 C6 C7 128.2(6) C12 C7 C8 117.6(5) C12 C7 C6 125.6(5) C8 C7 C6 116.7(5) C9 C8 C7 121.7(6) C9 C8 H8 119.2 C7 C8 H8 119.2 C8 C9 C10 120.2(6) C8 C9 H9 119.9 C10 C9 H9 119.9 C9 C10 C11 123.2(5) C9 C10 H10 118.4 C11 C10 H10 118.4 C12 C11 C10 108.7(4) C12 C11 H11 125.6 C10 C11 H11 125.6 C7 C12 N1 112.6(3) C7 C12 C11 127.1(5) N1 C12 C11 120.0(4) C14 C13 N1 113.8(3) C14 C13 H13A 108.8 N1 C13 H13A 108.8 C14 C13 H13B 108.8 N1 C13 H13B 108.8 H13A C13 H13B 107.7 C15 C14 C13 113.1(5) C15 C14 H14A 108.9 C13 C14 H14A 108.9 C15 C14 H14B 108.9 C13 C14 H14B 108.9 H14A C14 H14B 107.8 C14 C15 I2 107.1(4) C14 C15 H15A 110.3 I2 C15 H15A 110.3 C14 C15 H15B 110.3 I2 C15 H15B 110.3 H15A C15 H15B 108.6 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 I2 C15 . 2.102(7) ? N1 C1 . 1.394(6) ? N1 C12 . 1.407(7) ? N1 C13 . 1.577(5) ? N2 C2 . 1.429(6) ? N2 C3 . 1.458(6) ? C1 C2 . 1.376(8) ? C1 H1 . 0.9300 ? C2 C6 . 1.352(8) ? C3 C4 . 1.310(9) ? C3 H3 . 0.9300 ? C4 C5 . 1.346(8) ? C4 H4 . 0.9300 ? C5 C6 . 1.411(8) ? C5 H5 . 0.9300 ? C6 C7 . 1.422(7) ? C7 C12 . 1.357(7) ? C7 C8 . 1.375(8) ? C8 C9 . 1.316(7) ? C8 H8 . 0.9300 ? C9 C10 . 1.397(8) ? C9 H9 . 0.9300 ? C10 C11 . 1.463(6) ? C10 H10 . 0.9300 ? C11 C12 . 1.435(5) ? C11 H11 . 0.9300 ? C13 C14 . 1.537(7) ? C13 H13A . 0.9700 ? C13 H13B . 0.9700 ? C14 C15 . 1.481(8) ? C14 H14A . 0.9700 ? C14 H14B . 0.9700 ? C15 H15A . 0.9700 ? C15 H15B . 0.9700 ? 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 C1 H1 I1 3_666 0.93 3.02 3.919(7) 164 C11 H11 I1 4_566 0.93 3.09 3.882(4) 144 C13 H13B I1 4_566 0.97 3.19 4.147(5) 167 C14 H14B I1 . 0.97 3.01 3.920(7) 157 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 C12 N1 C1 C2 -1.2(7) C13 N1 C1 C2 175.9(3) N1 C1 C2 C6 1.1(6) N1 C1 C2 N2 177.4(4) C3 N2 C2 C6 -8.4(6) C3 N2 C2 C1 174.9(5) C2 N2 C3 C4 6.7(9) N2 C3 C4 C5 0.9(9) C3 C4 C5 C6 -7.3(9) C1 C2 C6 C5 179.3(4) N2 C2 C6 C5 3.1(6) C1 C2 C6 C7 0.5(6) N2 C2 C6 C7 -175.8(4) C4 C5 C6 C2 5.4(8) C4 C5 C6 C7 -175.9(5) C2 C6 C7 C12 -2.3(7) C5 C6 C7 C12 179.0(5) C2 C6 C7 C8 -178.3(4) C5 C6 C7 C8 3.0(7) C12 C7 C8 C9 -3.8(7) C6 C7 C8 C9 172.5(4) C7 C8 C9 C10 11.1(7) C8 C9 C10 C11 -6.8(8) C9 C10 C11 C12 -3.9(7) C8 C7 C12 N1 178.2(4) C6 C7 C12 N1 2.2(7) C8 C7 C12 C11 -8.7(7) C6 C7 C12 C11 175.2(4) C1 N1 C12 C7 -0.3(7) C13 N1 C12 C7 -177.1(3) C1 N1 C12 C11 -174.0(4) C13 N1 C12 C11 9.2(6) C10 C11 C12 C7 11.8(7) C10 C11 C12 N1 -175.5(4) C1 N1 C13 C14 -109.5(4) C12 N1 C13 C14 67.7(5) N1 C13 C14 C15 179.1(5) C13 C14 C15 I2 -172.9(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21131596