#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2014602.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_2014602 loop_ _publ_author_name 'L\"u, Zheng-Liang' 'Liu, Zhi-Liang' 'Zhang, De-Qing' _publ_section_title ; Tris(2,2'-bioxazoline-\k^2^N,N')copper(II) diperchlorate and tris(2,2'-bioxazoline-\k^2^N,N')nickel(II) diperchlorate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first m147 _journal_page_last m150 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac '[Ni (C6 H8 N2 O2)3] (Cl O4)2' _chemical_formula_moiety 'C18 H24 Ni N6 O6 2+ , 2Cl O4 -' _chemical_formula_sum 'C18 H24 Cl2 N6 Ni O14' _chemical_formula_weight 678.04 _chemical_name_common ; tris(2,2'-bisoxazoline-k^2^N,N')nickel(II) diperchlorate ; _chemical_name_systematic ; tris[2,2'-bi(4,5-dihydrooxazole)-k^2^N,N']nickel(II) diperchlorate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 101.14(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.3911(19) _cell_length_b 17.683(4) _cell_length_c 16.743(3) _cell_measurement_reflns_used 345 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 1.69 _cell_volume 2728.0(10) _computing_cell_refinement RAPID-AUTO _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_data_reduction 'CrystalStructure (Rigaku/MSC, 2002)' _computing_molecular_graphics SHELXL97 _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.949 _diffrn_measured_fraction_theta_max 0.949 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method oscillation _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rolating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.1075 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 21381 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 1.69 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.985 _exptl_absorpt_correction_T_max 0.896 _exptl_absorpt_correction_T_min 0.804 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(ABSCOR; Higashi, 1995)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1392 _exptl_crystal_size_max 0.211 _exptl_crystal_size_mid 0.165 _exptl_crystal_size_min 0.112 _refine_diff_density_max 0.623 _refine_diff_density_min -0.342 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 370 _refine_ls_number_reflns 5940 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.933 _refine_ls_R_factor_all 0.1164 _refine_ls_R_factor_gt 0.0511 _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^)+(0.0298P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.1039 _reflns_number_gt 2979 _reflns_number_total 5940 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file av1208.cif _[local]_cod_data_source_block II _[local]_cod_cif_authors_sg_H-M P21/n _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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 2728.0(9) _cod_database_code 2014602 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_type_symbol Ni 0.39912(5) 0.12931(3) 0.24517(3) 0.04193(14) Uani d . 1 Ni N1 0.3211(3) 0.13468(17) 0.35590(17) 0.0497(8) Uani d . 1 N N2 0.1888(3) 0.17470(17) 0.20645(19) 0.0487(8) Uani d . 1 N N3 0.4455(3) 0.14860(18) 0.12980(17) 0.0494(8) Uani d . 1 N N4 0.5180(3) 0.23227(17) 0.26417(19) 0.0478(8) Uani d . 1 N N5 0.3385(3) 0.01582(17) 0.21778(18) 0.0506(8) Uani d . 1 N N6 0.5924(3) 0.07173(18) 0.29429(18) 0.0487(8) Uani d . 1 N O1 0.1250(4) 0.16979(19) 0.4076(2) 0.0876(10) Uani d . 1 O O2 -0.0121(3) 0.21525(16) 0.24855(19) 0.0672(8) Uani d . 1 O O3 0.5574(3) 0.22775(18) 0.05702(18) 0.0772(9) Uani d . 1 O O4 0.6680(3) 0.30441(16) 0.20577(18) 0.0734(9) Uani d . 1 O O5 0.4294(4) -0.10238(16) 0.2196(2) 0.0797(9) Uani d . 1 O O6 0.6930(3) -0.04385(16) 0.31415(18) 0.0738(9) Uani d . 1 O O7 0.2469(6) -0.1671(3) 0.4718(3) 0.1495(17) Uani d . 1 O O8 0.1607(7) -0.0499(3) 0.4468(4) 0.203(3) Uani d . 1 O O9 0.1506(5) -0.1349(3) 0.3428(2) 0.175(2) Uani d . 1 O O10 0.3661(5) -0.0845(3) 0.4022(3) 0.1426(17) Uani d . 1 O O11 0.2292(5) -0.0735(2) -0.0370(2) 0.1295(15) Uani d . 1 O O12 0.1200(4) -0.0515(2) -0.17209(19) 0.1083(12) Uani d . 1 O O13 0.1204(4) 0.0414(2) -0.0752(2) 0.1062(12) Uani d . 1 O O14 0.3384(3) 0.0115(2) -0.1142(2) 0.0938(10) Uani d . 1 O C1 0.1921(5) 0.1620(2) 0.3455(2) 0.0549(10) Uani d . 1 C C2 0.3653(5) 0.1185(3) 0.4434(2) 0.0772(14) Uani d . 1 C H2A 0.4469 0.1498 0.4681 0.093 Uiso calc R 1 H H2B 0.3912 0.0657 0.4528 0.093 Uiso calc R 1 H C3 0.2289(7) 0.1383(3) 0.4769(3) 0.112(2) Uani d . 1 C H3A 0.1893 0.0935 0.4979 0.135 Uiso calc R 1 H H3B 0.2514 0.1753 0.5203 0.135 Uiso calc R 1 H C4 0.1212(4) 0.1844(2) 0.2635(3) 0.0493(10) Uani d . 1 C C5 0.0900(4) 0.1989(2) 0.1305(2) 0.0658(12) Uani d . 1 C H5A 0.0596 0.1561 0.0951 0.079 Uiso calc R 1 H H5B 0.1363 0.2360 0.1013 0.079 Uiso calc R 1 H C6 -0.0388(5) 0.2335(3) 0.1614(3) 0.0747(13) Uani d . 1 C H6A -0.0424 0.2878 0.1531 0.090 Uiso calc R 1 H H6B -0.1295 0.2116 0.1336 0.090 Uiso calc R 1 H C7 0.5219(4) 0.2066(2) 0.1266(2) 0.0534(10) Uani d . 1 C C8 0.4076(4) 0.1185(3) 0.0471(2) 0.0699(13) Uani d . 1 C H8A 0.3032 0.1166 0.0286 0.084 Uiso calc R 1 H H8B 0.4473 0.0682 0.0438 0.084 Uiso calc R 1 H C9 0.4771(6) 0.1751(3) -0.0026(3) 0.0891(16) Uani d . 1 C H9A 0.5421 0.1496 -0.0324 0.107 Uiso calc R 1 H H9B 0.4034 0.2016 -0.0411 0.107 Uiso calc R 1 H C10 0.5699(4) 0.2499(2) 0.2028(3) 0.0529(10) Uani d . 1 C C11 0.5915(5) 0.2824(2) 0.3301(3) 0.0671(12) Uani d . 1 C H11A 0.6516 0.2534 0.3730 0.081 Uiso calc R 1 H H11B 0.5214 0.3112 0.3532 0.081 Uiso calc R 1 H C12 0.6844(6) 0.3346(3) 0.2881(3) 0.0979(17) Uani d . 1 C H12A 0.6497 0.3864 0.2871 0.117 Uiso calc R 1 H H12B 0.7852 0.3333 0.3156 0.117 Uiso calc R 1 H C13 0.4440(5) -0.0292(2) 0.2395(2) 0.0544(10) Uani d . 1 C C14 0.2159(5) -0.0295(3) 0.1720(3) 0.0773(14) Uani d . 1 C H14A 0.1885 -0.0122 0.1162 0.093 Uiso calc R 1 H H14B 0.1320 -0.0270 0.1978 0.093 Uiso calc R 1 H C15 0.2775(6) -0.1091(3) 0.1758(3) 0.0865(15) Uani d . 1 C H15A 0.2232 -0.1425 0.2048 0.104 Uiso calc R 1 H H15B 0.2737 -0.1290 0.1214 0.104 Uiso calc R 1 H C16 0.5804(4) 0.0008(2) 0.2837(2) 0.0537(10) Uani d . 1 C C17 0.7428(4) 0.0871(2) 0.3380(2) 0.0645(12) Uani d . 1 C H17A 0.7430 0.1117 0.3899 0.077 Uiso calc R 1 H H17B 0.7944 0.1187 0.3057 0.077 Uiso calc R 1 H C18 0.8099(5) 0.0087(3) 0.3501(3) 0.0833(15) Uani d . 1 C H18A 0.8916 0.0045 0.3227 0.100 Uiso calc R 1 H H18B 0.8431 -0.0019 0.4075 0.100 Uiso calc R 1 H Cl2 0.20326(13) -0.01923(7) -0.09911(7) 0.0716(3) Uani d . 1 Cl Cl1 0.22549(15) -0.10577(8) 0.41391(8) 0.0829(4) Uani d . 1 Cl 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 Ni 0.0385(2) 0.0434(3) 0.0434(3) 0.0009(2) 0.00666(19) 0.0025(2) N1 0.057(2) 0.0462(18) 0.0453(18) 0.0039(16) 0.0089(15) 0.0022(16) N2 0.0425(17) 0.050(2) 0.0522(19) 0.0022(15) 0.0060(16) 0.0095(16) N3 0.0448(18) 0.064(2) 0.0380(18) -0.0047(16) 0.0048(14) 0.0005(16) N4 0.0448(18) 0.0459(19) 0.0511(19) -0.0049(15) 0.0052(16) 0.0027(16) N5 0.0438(18) 0.051(2) 0.058(2) -0.0068(16) 0.0129(16) -0.0007(17) N6 0.0490(19) 0.051(2) 0.0480(18) 0.0066(15) 0.0130(15) 0.0020(16) O1 0.095(2) 0.106(3) 0.071(2) 0.031(2) 0.0390(19) 0.0025(19) O2 0.0499(17) 0.0685(19) 0.086(2) 0.0191(14) 0.0193(15) 0.0055(17) O3 0.080(2) 0.098(2) 0.0570(18) -0.0074(18) 0.0221(17) 0.0180(19) O4 0.072(2) 0.063(2) 0.090(2) -0.0213(16) 0.0253(18) -0.0048(18) O5 0.090(2) 0.0484(18) 0.106(2) -0.0021(16) 0.0325(19) -0.0121(17) O6 0.068(2) 0.0633(19) 0.089(2) 0.0291(16) 0.0107(18) 0.0122(17) O7 0.217(5) 0.133(4) 0.114(3) 0.006(4) 0.070(3) 0.005(3) O8 0.233(6) 0.160(5) 0.213(6) 0.077(4) 0.034(5) -0.067(4) O9 0.178(5) 0.244(5) 0.092(3) -0.096(4) -0.002(3) -0.047(3) O10 0.107(3) 0.161(4) 0.147(4) -0.021(3) -0.008(3) 0.041(3) O11 0.134(3) 0.145(4) 0.103(3) 0.003(3) 0.007(2) 0.058(3) O12 0.131(3) 0.114(3) 0.074(2) -0.026(2) 0.005(2) -0.030(2) O13 0.076(2) 0.118(3) 0.125(3) 0.003(2) 0.020(2) -0.041(2) O14 0.071(2) 0.119(3) 0.095(2) -0.004(2) 0.0246(19) -0.004(2) C1 0.065(3) 0.048(2) 0.056(3) -0.003(2) 0.022(2) -0.005(2) C2 0.100(4) 0.074(3) 0.053(3) 0.011(3) 0.003(3) 0.000(2) C3 0.156(6) 0.133(5) 0.054(3) 0.050(4) 0.036(3) 0.003(3) C4 0.046(2) 0.042(2) 0.063(3) -0.0005(17) 0.016(2) 0.001(2) C5 0.051(2) 0.075(3) 0.068(3) 0.001(2) 0.002(2) 0.018(2) C6 0.056(3) 0.068(3) 0.096(4) 0.014(2) 0.004(3) 0.015(3) C7 0.046(2) 0.065(3) 0.049(2) 0.000(2) 0.0102(19) 0.007(2) C8 0.062(3) 0.097(4) 0.048(2) -0.002(3) 0.005(2) -0.010(3) C9 0.093(4) 0.121(4) 0.052(3) 0.006(3) 0.011(3) 0.006(3) C10 0.040(2) 0.050(3) 0.068(3) -0.0032(18) 0.008(2) 0.006(2) C11 0.065(3) 0.059(3) 0.075(3) -0.005(2) 0.008(2) -0.011(2) C12 0.117(4) 0.084(4) 0.097(4) -0.046(3) 0.033(3) -0.027(3) C13 0.067(3) 0.041(2) 0.060(3) -0.002(2) 0.025(2) -0.004(2) C14 0.073(3) 0.077(4) 0.079(3) -0.027(3) 0.008(3) -0.011(3) C15 0.100(4) 0.063(3) 0.103(4) -0.019(3) 0.038(3) -0.020(3) C16 0.063(3) 0.052(3) 0.052(2) 0.016(2) 0.023(2) 0.010(2) C17 0.041(2) 0.087(3) 0.060(3) 0.005(2) -0.004(2) 0.005(2) C18 0.063(3) 0.104(4) 0.077(3) 0.031(3) -0.003(3) 0.013(3) Cl2 0.0709(8) 0.0790(8) 0.0622(7) -0.0005(6) 0.0066(6) -0.0051(7) Cl1 0.0852(9) 0.0838(9) 0.0748(8) -0.0043(7) 0.0034(7) -0.0258(7) 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' N N 0.0061 0.0033 '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' Ni Ni 0.3393 1.1124 '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' 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 N1 Ni N2 77.95(12) yes N1 Ni N3 165.71(12) yes N1 Ni N4 95.22(12) yes N1 Ni N5 96.21(12) yes N1 Ni N6 95.60(12) yes N2 Ni N3 90.22(12) yes N2 Ni N4 98.81(11) yes N2 Ni N5 95.60(12) yes N2 Ni N6 170.86(12) yes N3 Ni N4 78.53(12) yes N3 Ni N5 92.86(12) yes N3 Ni N6 97.01(12) yes N4 Ni N5 163.19(12) yes N4 Ni N6 88.14(12) yes N5 Ni N6 78.53(12) yes C1 N1 C2 106.6(3) ? C1 N1 Ni 111.9(3) ? C2 N1 Ni 141.4(3) ? C4 N2 C5 106.7(3) ? C4 N2 Ni 113.5(2) ? C5 N2 Ni 139.8(3) ? C7 N3 C8 107.0(3) ? C7 N3 Ni 113.3(3) ? C8 N3 Ni 139.5(3) ? C10 N4 C11 105.2(3) ? C10 N4 Ni 111.4(3) ? C11 N4 Ni 141.3(3) ? C13 N5 C14 107.0(3) ? C13 N5 Ni 111.8(3) ? C14 N5 Ni 140.6(3) ? C16 N6 C17 107.5(3) ? C16 N6 Ni 112.2(3) ? C17 N6 Ni 140.4(3) ? C1 O1 C3 103.6(3) ? C4 O2 C6 104.4(3) ? C7 O3 C9 103.6(3) ? C10 O4 C12 104.3(3) ? C13 O5 C15 104.1(3) ? C16 O6 C18 104.8(3) ? N1 C1 O1 120.8(4) ? N1 C1 C4 118.5(4) ? O1 C1 C4 120.7(4) ? N1 C2 C3 103.0(4) ? N1 C2 H2A 111.2 ? C3 C2 H2A 111.2 ? N1 C2 H2B 111.2 ? C3 C2 H2B 111.2 ? H2A C2 H2B 109.1 ? O1 C3 C2 105.7(4) ? O1 C3 H3A 110.6 ? C2 C3 H3A 110.6 ? O1 C3 H3B 110.6 ? C2 C3 H3B 110.6 ? H3A C3 H3B 108.7 ? N2 C4 O2 120.3(4) ? N2 C4 C1 118.1(4) ? O2 C4 C1 121.6(4) ? N2 C5 C6 103.3(3) ? N2 C5 H5A 111.1 ? C6 C5 H5A 111.1 ? N2 C5 H5B 111.1 ? C6 C5 H5B 111.1 ? H5A C5 H5B 109.1 ? O2 C6 C5 104.7(3) ? O2 C6 H6A 110.8 ? C5 C6 H6A 110.8 ? O2 C6 H6B 110.8 ? C5 C6 H6B 110.8 ? H6A C6 H6B 108.9 ? N3 C7 O3 120.7(4) ? N3 C7 C10 117.7(4) ? O3 C7 C10 121.7(4) ? N3 C8 C9 103.0(4) ? N3 C8 H8A 111.2 ? C9 C8 H8A 111.2 ? N3 C8 H8B 111.2 ? C9 C8 H8B 111.2 ? H8A C8 H8B 109.1 ? O3 C9 C8 105.3(3) ? O3 C9 H9A 110.7 ? C8 C9 H9A 110.7 ? O3 C9 H9B 110.7 ? C8 C9 H9B 110.7 ? H9A C9 H9B 108.8 ? N4 C10 O4 121.6(4) ? N4 C10 C7 118.3(3) ? O4 C10 C7 120.0(4) ? N4 C11 C12 104.1(3) ? N4 C11 H11A 110.9 ? C12 C11 H11A 110.9 ? N4 C11 H11B 110.9 ? C12 C11 H11B 110.9 ? H11A C11 H11B 109.0 ? O4 C12 C11 104.3(3) ? O4 C12 H12A 110.9 ? C11 C12 H12A 110.9 ? O4 C12 H12B 110.9 ? C11 C12 H12B 110.9 ? H12A C12 H12B 108.9 ? N5 C13 O5 120.0(4) ? N5 C13 C16 118.8(4) ? O5 C13 C16 121.2(4) ? N5 C14 C15 103.1(4) ? N5 C14 H14A 111.1 ? C15 C14 H14A 111.1 ? N5 C14 H14B 111.1 ? C15 C14 H14B 111.1 ? H14A C14 H14B 109.1 ? O5 C15 C14 105.6(3) ? O5 C15 H15A 110.6 ? C14 C15 H15A 110.6 ? O5 C15 H15B 110.6 ? C14 C15 H15B 110.6 ? H15A C15 H15B 108.7 ? N6 C16 O6 119.2(4) ? N6 C16 C13 118.5(4) ? O6 C16 C13 122.3(4) ? N6 C17 C18 103.2(3) ? N6 C17 H17A 111.1 ? C18 C17 H17A 111.1 ? N6 C17 H17B 111.1 ? C18 C17 H17B 111.1 ? H17A C17 H17B 109.1 ? O6 C18 C17 105.3(3) ? O6 C18 H18A 110.7 ? C17 C18 H18A 110.7 ? O6 C18 H18B 110.7 ? C17 C18 H18B 110.7 ? H18A C18 H18B 108.8 ? O11 Cl2 O13 109.4(3) ? O11 Cl2 O12 110.4(2) ? O13 Cl2 O12 107.5(2) ? O11 Cl2 O14 110.7(2) ? O13 Cl2 O14 108.1(2) ? O12 Cl2 O14 110.7(2) ? O8 Cl1 O9 116.2(4) ? O8 Cl1 O10 111.8(4) ? O9 Cl1 O10 108.4(3) ? O8 Cl1 O7 107.1(3) ? O9 Cl1 O7 106.5(3) ? O10 Cl1 O7 106.2(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Ni N1 2.123(3) yes Ni N2 2.114(3) yes Ni N3 2.089(3) yes Ni N4 2.127(3) yes Ni N5 2.112(3) yes Ni N6 2.105(3) yes N1 C1 1.284(5) ? N1 C2 1.471(5) ? N2 C4 1.256(4) ? N2 C5 1.484(4) ? N3 C7 1.259(5) ? N3 C8 1.462(4) ? N4 C10 1.258(5) ? N4 C11 1.479(5) ? N5 C13 1.267(5) ? N5 C14 1.488(5) ? N6 C16 1.269(4) ? N6 C17 1.485(4) ? O1 C1 1.323(5) ? O1 C3 1.474(5) ? O2 C4 1.343(4) ? O2 C6 1.468(5) ? O3 C7 1.326(4) ? O3 C9 1.463(5) ? O4 C10 1.328(4) ? O4 C12 1.458(5) ? O5 C13 1.337(4) ? O5 C15 1.477(5) ? O6 C16 1.339(4) ? O6 C18 1.475(5) ? O7 Cl1 1.443(4) ? O8 Cl1 1.333(5) ? O9 Cl1 1.361(4) ? O10 Cl1 1.422(4) ? O11 Cl2 1.402(4) ? O12 Cl2 1.435(3) ? O13 Cl2 1.426(4) ? O14 Cl2 1.447(3) ? C1 C4 1.461(5) ? C2 C3 1.535(6) ? C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 H3A 0.9700 ? C3 H3B 0.9700 ? C5 C6 1.532(5) ? C5 H5A 0.9700 ? C5 H5B 0.9700 ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 C10 1.482(5) ? C8 C9 1.527(6) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? C11 C12 1.532(6) ? C11 H11A 0.9700 ? C11 H11B 0.9700 ? C12 H12A 0.9700 ? C12 H12B 0.9700 ? C13 C16 1.450(6) ? C14 C15 1.518(6) ? C14 H14A 0.9700 ? C14 H14B 0.9700 ? C15 H15A 0.9700 ? C15 H15B 0.9700 ? C17 C18 1.521(5) ? C17 H17A 0.9700 ? C17 H17B 0.9700 ? C18 H18A 0.9700 ? C18 H18B 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 C5 H5B O7 2 0.97 2.48 3.451(6) 179 C17 H17A O7 3_656 0.97 2.50 3.468(6) 176 C15 H15A O9 . 0.97 2.54 3.277(7) 133 C8 H8A O13 . 0.97 2.57 3.345(5) 137 C8 H8B O14 3_655 0.97 2.55 3.347(6) 139