#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014692.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_2014692 loop_ _publ_author_name 'Basok, Stepan S.' 'Croitoru Lilia' 'Fonari, Marina S.' 'Ganin, Eduard V.' 'Gelmboldt, Vladimir O.' 'Lipkowski, Janusz' 'Simonov, Yurii A.' _publ_section_title ; A new phase of 7,16-dibenzyl-1,4,10,13-tetraoxa-7,16-diazacyclooctadecane, and 7,16-dibenzyl-1,4,10,13-tetraoxa-7,16-diazoniacyclooctadecane bis(tetrafluoroborate) monohydrate, both determined at 123K ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o188 _journal_page_last o192 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C26 H40 N2 O4 2+, 2B F4 -, H2 O' _chemical_formula_moiety 'C26 H40 N2 O4, 2B F4, H2 O' _chemical_formula_sum 'C26 H40 B2 F8 N2 O4.2' _chemical_formula_weight 621.48 _chemical_melting_point 169.0(10) _chemical_name_common ; N,N'-dibenzyl-1,4,10,13-tetraoxa-7,16-diazoniacyclooctadecane bis tetrafluoroborate monohydrate ; _chemical_name_systematic ; N,N'-dibenzyl-1,4,10,13-tetraoxa-7,16-diazoniacyclooctadecane bis tetrafluoroborate monohydrate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 69.342(4) _cell_angle_beta 72.226(4) _cell_angle_gamma 81.480(4) _cell_formula_units_Z 1 _cell_length_a 7.9290(6) _cell_length_b 9.3870(6) _cell_length_c 11.6070(7) _cell_measurement_reflns_used 3035 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1 _cell_volume 768.98(9) _computing_cell_refinement 'COLLECT and DENZO' _computing_data_collection 'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction 'COLLECT and DENZO' _computing_molecular_graphics 'ORTEP for Windows (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type ' Nonius KappaCCD area-detector diffractometer' _diffrn_measurement_method '\f and \w scans' _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 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4974 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.50 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 326 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.177 _refine_diff_density_min -0.252 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 198 _refine_ls_number_reflns 2660 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0406 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.1724P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0972 _refine_ls_wR_factor_ref 0.1023 _reflns_number_gt 2159 _reflns_number_total 2660 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gd1362.cif _[local]_cod_data_source_block II _[local]_cod_chemical_formula_sum_orig 'C26 H40 B2 F8 N2 O4.20' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '168--170' was changed to '169.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '168--170' was changed to '169.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2014692 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.63995(18) 0.00507(14) -0.26512(13) 0.0255(3) Uani d . 1 . . N H1N 0.599(2) -0.008(2) -0.1798(19) 0.038 Uiso d . 1 . . H C2 0.3942(2) 0.13891(18) 0.28211(16) 0.0309(4) Uani d . 1 . . C H2A 0.3304 0.1384 0.3701 0.037 Uiso calc R 1 . . H H2B 0.5226 0.1431 0.2705 0.037 Uiso calc R 1 . . H C3 0.3336(2) 0.27758(18) 0.18699(15) 0.0296(4) Uani d . 1 . . C H3A 0.2026 0.2854 0.2075 0.036 Uiso calc R 1 . . H H3B 0.3753 0.3713 0.1882 0.036 Uiso calc R 1 . . H O4 0.40852(15) 0.25841(12) 0.06524(10) 0.0308(3) Uani d . 1 . . O C5 0.3292(2) 0.36037(18) -0.03014(15) 0.0311(4) Uani d . 1 . . C H5A 0.3513 0.4670 -0.0438 0.037 Uiso calc R 1 . . H H5B 0.1994 0.3487 -0.0019 0.037 Uiso calc R 1 . . H C6 0.4078(2) 0.32474(18) -0.15215(16) 0.0326(4) Uani d . 1 . . C H6A 0.3621 0.4001 -0.2215 0.039 Uiso calc R 1 . . H H6B 0.5384 0.3296 -0.1774 0.039 Uiso calc R 1 . . H O7 0.36008(15) 0.17417(12) -0.13226(10) 0.0317(3) Uani d . 1 . . O C8 0.3523(2) 0.1520(2) -0.24600(16) 0.0348(4) Uani d . 1 . . C H8A 0.2846 0.2389 -0.2924 0.042 Uiso calc R 1 . . H H8B 0.2891 0.0581 -0.2227 0.042 Uiso calc R 1 . . H C9 0.5357(2) 0.13856(18) -0.33235(15) 0.0307(4) Uani d . 1 . . C H9A 0.5264 0.1253 -0.4111 0.037 Uiso calc R 1 . . H H9B 0.5981 0.2333 -0.3575 0.037 Uiso calc R 1 . . H C10 0.8355(2) 0.03204(17) -0.30300(15) 0.0270(4) Uani d . 1 . . C H10A 0.9002 -0.0650 -0.2690 0.032 Uiso calc R 1 . . H H10B 0.8808 0.0672 -0.3975 0.032 Uiso calc R 1 . . H C11 0.8701(2) 0.14913(17) -0.25252(14) 0.0247(4) Uani d . 1 . . C C12 0.9169(2) 0.29523(18) -0.33387(15) 0.0312(4) Uani d . 1 . . C H12A 0.9283 0.3218 -0.4227 0.037 Uiso calc R 1 . . H C13 0.9470(2) 0.40214(18) -0.28615(17) 0.0347(4) Uani d . 1 . . C H13A 0.9785 0.5019 -0.3421 0.042 Uiso calc R 1 . . H C14 0.9311(2) 0.36360(19) -0.15688(17) 0.0338(4) Uani d . 1 . . C H14A 0.9528 0.4367 -0.1242 0.041 Uiso calc R 1 . . H C15 0.8839(2) 0.2191(2) -0.07526(16) 0.0338(4) Uani d . 1 . . C H15A 0.8720 0.1931 0.0136 0.041 Uiso calc R 1 . . H C16 0.8539(2) 0.11163(18) -0.12296(15) 0.0291(4) Uani d . 1 . . C H16A 0.8221 0.0120 -0.0667 0.035 Uiso calc R 1 . . H B1 0.7890(3) 0.2304(2) 0.33341(18) 0.0291(4) Uani d . 1 . . B F1 0.86572(15) 0.26613(14) 0.20294(9) 0.0513(3) Uani d . 1 . . F F2 0.63511(14) 0.31951(11) 0.35620(10) 0.0448(3) Uani d . 1 . . F F3 0.74774(14) 0.07671(10) 0.38617(10) 0.0418(3) Uani d . 1 . . F F4 0.90924(14) 0.25270(11) 0.39029(9) 0.0382(3) Uani d . 1 . . F O1W 0.372(2) 0.4751(17) 0.5008(14) 0.064(7) Uiso d P 0.102(6) A -1 O 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 N1 0.0273(8) 0.0249(7) 0.0253(7) -0.0001(6) -0.0062(6) -0.0107(6) C2 0.0332(10) 0.0306(9) 0.0347(9) -0.0047(7) -0.0096(7) -0.0161(7) C3 0.0328(10) 0.0272(8) 0.0313(9) -0.0038(7) -0.0054(7) -0.0142(7) O4 0.0301(7) 0.0311(6) 0.0287(6) 0.0047(5) -0.0054(5) -0.0114(5) C5 0.0330(10) 0.0248(8) 0.0313(9) 0.0017(7) -0.0057(7) -0.0082(7) C6 0.0358(10) 0.0240(8) 0.0316(9) -0.0006(7) -0.0040(7) -0.0063(7) O7 0.0359(7) 0.0277(6) 0.0300(6) -0.0026(5) -0.0037(5) -0.0116(5) C8 0.0328(11) 0.0394(10) 0.0359(9) 0.0048(8) -0.0111(8) -0.0177(8) C9 0.0336(10) 0.0304(9) 0.0277(9) 0.0049(7) -0.0101(7) -0.0103(7) C10 0.0244(9) 0.0257(8) 0.0302(8) -0.0008(7) -0.0028(7) -0.0123(7) C11 0.0206(9) 0.0246(8) 0.0288(8) 0.0008(6) -0.0034(6) -0.0122(7) C12 0.0343(10) 0.0285(9) 0.0288(9) -0.0021(7) -0.0046(7) -0.0102(7) C13 0.0377(11) 0.0226(8) 0.0434(10) -0.0019(7) -0.0098(8) -0.0109(7) C14 0.0304(10) 0.0331(9) 0.0473(11) 0.0046(7) -0.0130(8) -0.0247(8) C15 0.0328(10) 0.0420(10) 0.0307(9) 0.0034(8) -0.0102(7) -0.0173(8) C16 0.0270(10) 0.0270(8) 0.0310(9) -0.0013(7) -0.0057(7) -0.0084(7) B1 0.0309(11) 0.0293(10) 0.0298(10) -0.0024(8) -0.0052(8) -0.0154(8) F1 0.0532(8) 0.0721(8) 0.0283(6) 0.0016(6) -0.0084(5) -0.0203(5) F2 0.0420(7) 0.0322(6) 0.0514(6) 0.0076(5) -0.0057(5) -0.0130(5) F3 0.0384(7) 0.0283(5) 0.0654(7) -0.0016(4) -0.0191(5) -0.0190(5) F4 0.0471(7) 0.0388(6) 0.0351(5) -0.0129(5) -0.0120(5) -0.0147(4) 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 N1 C9 . 1.503(2) no N1 C2 2_655 1.506(2) no N1 C10 . 1.511(2) no N1 H1N . 0.911(19) no C2 C3 . 1.506(2) no C2 N1 2_655 1.506(2) no C2 H2A . 0.9900 no C2 H2B . 0.9900 no C3 O4 . 1.4204(18) no C3 H3A . 0.9900 no C3 H3B . 0.9900 no O4 C5 . 1.427(2) no C5 C6 . 1.497(2) no C5 H5A . 0.9900 no C5 H5B . 0.9900 no C6 O7 . 1.4384(19) no C6 H6A . 0.9900 no C6 H6B . 0.9900 no O7 C8 . 1.428(2) no C8 C9 . 1.510(2) no C8 H8A . 0.9900 no C8 H8B . 0.9900 no C9 H9A . 0.9900 no C9 H9B . 0.9900 no C10 C11 . 1.506(2) no C10 H10A . 0.9900 no C10 H10B . 0.9900 no C11 C16 . 1.387(2) no C11 C12 . 1.390(2) no C12 C13 . 1.384(2) no C12 H12A . 0.9500 no C13 C14 . 1.383(3) no C13 H13A . 0.9500 no C14 C15 . 1.380(2) no C14 H14A . 0.9500 no C15 C16 . 1.388(2) no C15 H15A . 0.9500 no C16 H16A . 0.9500 no B1 F2 . 1.384(2) no B1 F1 . 1.384(2) no B1 F4 . 1.389(2) no B1 F3 . 1.399(2) no 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C9 N1 C2 . 2_655 110.74(13) no C9 N1 C10 . . 112.99(12) no C2 N1 C10 2_655 . 112.23(12) no C9 N1 H1N . . 107.2(12) no C2 N1 H1N 2_655 . 106.6(11) no C10 N1 H1N . . 106.7(12) no C3 C2 N1 . 2_655 110.96(13) no C3 C2 H2A . . 109.4 no N1 C2 H2A 2_655 . 109.4 no C3 C2 H2B . . 109.4 no N1 C2 H2B 2_655 . 109.4 no H2A C2 H2B . . 108.0 no O4 C3 C2 . . 106.18(12) no O4 C3 H3A . . 110.5 no C2 C3 H3A . . 110.5 no O4 C3 H3B . . 110.5 no C2 C3 H3B . . 110.5 ? H3A C3 H3B . . 108.7 ? C3 O4 C5 . . 112.73(12) no O4 C5 C6 . . 108.82(13) no O4 C5 H5A . . 109.9 no C6 C5 H5A . . 109.9 no O4 C5 H5B . . 109.9 no C6 C5 H5B . . 109.9 no H5A C5 H5B . . 108.3 no O7 C6 C5 . . 108.55(13) no O7 C6 H6A . . 110.0 no C5 C6 H6A . . 110.0 no O7 C6 H6B . . 110.0 no C5 C6 H6B . . 110.0 no H6A C6 H6B . . 108.4 no C8 O7 C6 . . 113.76(12) no O7 C8 C9 . . 111.22(15) no O7 C8 H8A . . 109.4 no C9 C8 H8A . . 109.4 no O7 C8 H8B . . 109.4 no C9 C8 H8B . . 109.4 no H8A C8 H8B . . 108.0 no N1 C9 C8 . . 110.48(13) no N1 C9 H9A . . 109.6 no C8 C9 H9A . . 109.6 no N1 C9 H9B . . 109.6 no C8 C9 H9B . . 109.6 no H9A C9 H9B . . 108.1 no C11 C10 N1 . . 111.42(12) no C11 C10 H10A . . 109.3 no N1 C10 H10A . . 109.3 no C11 C10 H10B . . 109.3 no N1 C10 H10B . . 109.3 no H10A C10 H10B . . 108.0 no C16 C11 C12 . . 119.29(15) no C16 C11 C10 . . 119.76(14) no C12 C11 C10 . . 120.95(14) no C13 C12 C11 . . 120.39(15) no C13 C12 H12A . . 119.8 no C11 C12 H12A . . 119.8 no C14 C13 C12 . . 119.93(15) no C14 C13 H13A . . 120.0 no C12 C13 H13A . . 120.0 no C15 C14 C13 . . 120.12(16) no C15 C14 H14A . . 119.9 no C13 C14 H14A . . 119.9 no C14 C15 C16 . . 120.04(15) no C14 C15 H15A . . 120.0 no C16 C15 H15A . . 120.0 no C11 C16 C15 . . 120.23(15) no C11 C16 H16A . . 119.9 no C15 C16 H16A . . 119.9 no F2 B1 F1 . . 109.83(15) no F2 B1 F4 . . 110.94(14) no F1 B1 F4 . . 109.28(15) no F2 B1 F3 . . 109.12(14) no F1 B1 F3 . . 109.59(14) no F4 B1 F3 . . 108.05(15) 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 N1 H1N O4 2_655 0.91(2) 2.25(2) 2.709(2) 110.2(14) yes N1 H1N O7 . 0.91(2) 2.43(2) 2.901(2) 112.6(14) yes C2 H2B F3 . 0.99 2.43 3.278(2) 143 yes C10 H10B F4 1_554 0.99 2.43 3.345(2) 154 yes C12 H12A F4 1_554 0.95 2.53 3.383(2) 150 yes C13 H13A F4 2_765 0.95 2.41 3.279(2) 152 yes C15 H15A F1 . 0.95 2.51 3.368(2) 151 yes C16 H16A O7 2_655 0.95 2.52 3.395(2) 154 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_site_symmetry_1 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 C2 C3 O4 2_655 . . -50.1(2) yes C2 C3 O4 C5 . . . 165.40(10) yes C3 O4 C5 C6 . . . -176.20(10) yes O4 C5 C6 O7 . . . 64.6(2) yes C5 C6 O7 C8 . . . 152.60(10) yes C6 O7 C8 C9 . . . 74.0(2) yes O7 C8 C9 N1 . . . 60.3(2) yes C8 C9 N1 C2 . . 2_655 86.8(2) yes C9 N1 C2 C3 . 2_655 2_655 -164.00(10) yes