#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206829.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_2206829 loop_ _publ_author_name 'Chen, Guang' 'Zhao, Bin' 'Sun, Min' 'Qi, Wei' _publ_section_title ; [N,N'-Bis(2-hydroxynaphthylmethylene)-1,2-ethanediaminato]zinc(II) ; _journal_coeditor_code YA6260 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first m1869 _journal_page_last m1870 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac '[Zn (C24 H18 N2 O2)]' _chemical_formula_moiety 'C24 H18 N2 O2 Zn' _chemical_formula_sum 'C24 H18 N2 O2 Zn' _chemical_formula_weight 431.77 _chemical_name_systematic ; ? ; _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 99.920(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.6810(10) _cell_length_b 8.1840(10) _cell_length_c 12.9570(10) _cell_measurement_reflns_used 2849 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.9 _cell_measurement_theta_min 2.7 _cell_volume 1846.9(3) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _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 0.061 _diffrn_reflns_av_sigmaI/netI 0.066 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 9152 _diffrn_reflns_theta_full 27.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.3 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.354 _exptl_absorpt_correction_T_max 0.755 _exptl_absorpt_correction_T_min 0.663 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 888 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.64 _refine_diff_density_min -0.40 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 4153 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.01 _refine_ls_R_factor_all 0.072 _refine_ls_R_factor_gt 0.051 _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^)+(0.0753P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.127 _refine_ls_wR_factor_ref 0.137 _reflns_number_gt 3029 _reflns_number_total 4153 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ya6260.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_database_code 2206829 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_type_symbol Zn1 0.022954(19) 0.33477(4) 0.07297(3) 0.03501(15) Uani d . 1 Zn O1 0.09689(11) 0.4212(3) 0.17690(15) 0.0333(5) Uani d . 1 O O2 -0.04847(11) 0.4332(3) 0.14147(14) 0.0324(5) Uani d . 1 O N1 0.09373(14) 0.2323(3) 0.00696(18) 0.0318(5) Uani d . 1 N N2 -0.05060(14) 0.2595(3) -0.03401(18) 0.0300(5) Uani d . 1 N C1 0.21010(18) 0.3180(4) 0.1207(2) 0.0334(7) Uani d . 1 C C2 0.17118(17) 0.4107(4) 0.1863(2) 0.0328(7) Uani d . 1 C C3 0.21539(18) 0.5026(4) 0.2698(2) 0.0398(7) Uani d . 1 C H3 0.1902 0.5695 0.3110 0.048 Uiso calc R 1 H C4 0.29259(19) 0.4941(4) 0.2898(3) 0.0449(8) Uani d . 1 C H4 0.3194 0.5548 0.3449 0.054 Uiso calc R 1 H C5 0.33438(19) 0.3949(5) 0.2290(3) 0.0445(8) Uani d . 1 C C6 0.4156(2) 0.3808(6) 0.2523(3) 0.0608(11) Uani d . 1 C H6 0.4424 0.4371 0.3095 0.073 Uiso calc R 1 H C7 0.4547(2) 0.2885(6) 0.1941(4) 0.0714(13) Uani d . 1 C H7 0.5079 0.2803 0.2112 0.086 Uiso calc R 1 H C8 0.4150(2) 0.2051(5) 0.1079(4) 0.0633(11) Uani d . 1 C H8 0.4421 0.1414 0.0672 0.076 Uiso calc R 1 H C9 0.3373(2) 0.2154(5) 0.0822(3) 0.0509(9) Uani d . 1 C H9 0.3123 0.1596 0.0236 0.061 Uiso calc R 1 H C10 0.29369(18) 0.3085(4) 0.1422(3) 0.0388(7) Uani d . 1 C C11 0.16768(18) 0.2337(4) 0.0334(2) 0.0347(7) Uani d . 1 C H11 0.1956 0.1743 -0.0083 0.042 Uiso calc R 1 H C12 0.05967(19) 0.1355(4) -0.0862(3) 0.0393(7) Uani d . 1 C H12A 0.0558 0.0215 -0.0673 0.047 Uiso calc R 1 H H12B 0.0916 0.1430 -0.1398 0.047 Uiso calc R 1 H C13 -0.01894(18) 0.2038(4) -0.1267(2) 0.0378(7) Uani d . 1 C H13A -0.0155 0.2945 -0.1738 0.045 Uiso calc R 1 H H13B -0.0516 0.1203 -0.1643 0.045 Uiso calc R 1 H C14 -0.12390(18) 0.2639(4) -0.0405(2) 0.0342(7) Uani d . 1 C H14 -0.1533 0.2178 -0.0998 0.041 Uiso calc R 1 H C15 -0.16416(18) 0.3333(3) 0.0351(2) 0.0313(6) Uani d . 1 C C16 -0.12240(17) 0.4222(4) 0.1194(2) 0.0321(6) Uani d . 1 C C17 -0.16514(18) 0.5123(4) 0.1856(2) 0.0384(7) Uani d . 1 C H17 -0.1386 0.5729 0.2410 0.046 Uiso calc R 1 H C18 -0.24248(19) 0.5110(4) 0.1694(3) 0.0466(8) Uani d . 1 C H18 -0.2679 0.5728 0.2131 0.056 Uiso calc R 1 H C19 -0.28649(19) 0.4178(4) 0.0873(3) 0.0452(8) Uani d . 1 C C20 -0.3675(2) 0.4170(5) 0.0708(3) 0.0600(11) Uani d . 1 C H20 -0.3928 0.4788 0.1145 0.072 Uiso calc R 1 H C21 -0.4088(2) 0.3293(6) -0.0065(4) 0.0721(14) Uani d . 1 C H21 -0.4622 0.3300 -0.0161 0.087 Uiso calc R 1 H C22 -0.3710(2) 0.2374(6) -0.0722(3) 0.0614(11) Uani d . 1 C H22 -0.3997 0.1767 -0.1259 0.074 Uiso calc R 1 H C23 -0.2926(2) 0.2340(5) -0.0598(3) 0.0496(9) Uani d . 1 C H23 -0.2688 0.1700 -0.1041 0.060 Uiso calc R 1 H C24 -0.24742(18) 0.3271(4) 0.0200(3) 0.0372(7) Uani d . 1 C 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 Zn1 0.0384(2) 0.0396(2) 0.0272(2) 0.00038(16) 0.00605(15) -0.00013(15) O1 0.0340(11) 0.0419(12) 0.0236(10) 0.0007(9) 0.0038(8) -0.0029(9) O2 0.0336(11) 0.0404(12) 0.0228(10) 0.0012(9) 0.0041(8) -0.0037(9) N1 0.0410(14) 0.0326(13) 0.0226(12) 0.0007(11) 0.0080(10) 0.0000(11) N2 0.0374(14) 0.0304(13) 0.0220(12) -0.0007(11) 0.0049(10) -0.0001(10) C1 0.0357(16) 0.0351(16) 0.0301(16) 0.0000(13) 0.0069(12) 0.0066(13) C2 0.0368(16) 0.0343(16) 0.0269(15) -0.0020(13) 0.0039(12) 0.0060(13) C3 0.0465(19) 0.0407(18) 0.0320(17) -0.0055(15) 0.0060(14) -0.0034(14) C4 0.0433(19) 0.050(2) 0.0388(18) -0.0114(16) 0.0004(14) -0.0026(16) C5 0.0394(18) 0.046(2) 0.046(2) -0.0061(15) 0.0024(15) 0.0083(17) C6 0.038(2) 0.073(3) 0.068(3) -0.0071(19) -0.0014(18) -0.002(2) C7 0.0315(19) 0.082(3) 0.099(4) 0.003(2) 0.007(2) 0.001(3) C8 0.042(2) 0.073(3) 0.077(3) 0.0123(19) 0.016(2) -0.001(2) C9 0.043(2) 0.058(2) 0.053(2) 0.0048(17) 0.0122(17) 0.0010(19) C10 0.0364(17) 0.0382(18) 0.0420(19) 0.0023(13) 0.0080(14) 0.0104(15) C11 0.0400(17) 0.0374(17) 0.0286(16) 0.0048(14) 0.0116(13) 0.0027(13) C12 0.0454(18) 0.0406(18) 0.0322(17) 0.0027(14) 0.0078(14) -0.0078(14) C13 0.0485(19) 0.0433(19) 0.0213(15) -0.0043(14) 0.0057(13) -0.0070(13) C14 0.0418(18) 0.0327(16) 0.0261(15) -0.0041(13) 0.0003(13) 0.0039(13) C15 0.0364(16) 0.0292(15) 0.0279(15) 0.0001(12) 0.0043(12) 0.0053(12) C16 0.0381(17) 0.0308(16) 0.0279(15) 0.0058(13) 0.0074(12) 0.0103(13) C17 0.0434(18) 0.0383(18) 0.0342(17) 0.0073(14) 0.0084(13) -0.0004(14) C18 0.0475(19) 0.045(2) 0.049(2) 0.0100(16) 0.0143(16) 0.0000(17) C19 0.0374(18) 0.046(2) 0.053(2) 0.0054(15) 0.0111(15) 0.0129(17) C20 0.043(2) 0.065(3) 0.074(3) 0.0098(19) 0.017(2) 0.011(2) C21 0.0306(19) 0.081(3) 0.100(4) -0.002(2) 0.000(2) 0.019(3) C22 0.047(2) 0.070(3) 0.064(3) -0.012(2) -0.0025(19) 0.003(2) C23 0.0424(19) 0.055(2) 0.049(2) -0.0059(17) 0.0012(16) 0.0055(18) C24 0.0379(17) 0.0372(17) 0.0350(17) -0.0015(13) 0.0027(13) 0.0100(14) 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' Zn Zn 0.2839 1.4301 '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 Zn1 N2 86.91(11) y N1 Zn1 O1 93.49(10) y N2 Zn1 O1 176.90(10) y N1 Zn1 O2 178.54(10) y N2 Zn1 O2 93.16(10) y O1 Zn1 O2 86.52(9) y C2 O1 Zn1 128.25(19) ? C16 O2 Zn1 127.71(19) ? C11 N1 C12 118.1(3) ? C11 N1 Zn1 127.7(2) ? C12 N1 Zn1 114.2(2) ? C14 N2 C13 118.3(3) ? C14 N2 Zn1 128.0(2) ? C13 N2 Zn1 113.44(19) ? C2 C1 C11 119.8(3) ? C2 C1 C10 120.0(3) ? C11 C1 C10 120.2(3) ? O1 C2 C1 124.8(3) ? O1 C2 C3 116.5(3) ? C1 C2 C3 118.7(3) ? C4 C3 C2 121.4(3) ? C4 C3 H3 119.3 ? C2 C3 H3 119.3 ? C3 C4 C5 121.9(3) ? C3 C4 H4 119.0 ? C5 C4 H4 119.0 ? C10 C5 C6 119.0(4) ? C10 C5 C4 118.9(3) ? C6 C5 C4 122.1(3) ? C7 C6 C5 121.8(4) ? C7 C6 H6 119.1 ? C5 C6 H6 119.1 ? C6 C7 C8 119.3(4) ? C6 C7 H7 120.3 ? C8 C7 H7 120.3 ? C9 C8 C7 121.0(4) ? C9 C8 H8 119.5 ? C7 C8 H8 119.5 ? C8 C9 C10 121.6(4) ? C8 C9 H9 119.2 ? C10 C9 H9 119.2 ? C9 C10 C5 117.2(3) ? C9 C10 C1 123.8(3) ? C5 C10 C1 119.0(3) ? N1 C11 C1 125.8(3) ? N1 C11 H11 117.1 ? C1 C11 H11 117.1 ? N1 C12 C13 107.8(2) ? N1 C12 H12A 110.1 ? C13 C12 H12A 110.1 ? N1 C12 H12B 110.1 ? C13 C12 H12B 110.1 ? H12A C12 H12B 108.5 ? N2 C13 C12 106.7(2) ? N2 C13 H13A 110.4 ? C12 C13 H13A 110.4 ? N2 C13 H13B 110.4 ? C12 C13 H13B 110.4 ? H13A C13 H13B 108.6 ? N2 C14 C15 125.7(3) ? N2 C14 H14 117.1 ? C15 C14 H14 117.1 ? C16 C15 C14 118.8(3) ? C16 C15 C24 120.4(3) ? C14 C15 C24 120.6(3) ? O2 C16 C15 125.6(3) ? O2 C16 C17 116.5(3) ? C15 C16 C17 117.8(3) ? C18 C17 C16 121.7(3) ? C18 C17 H17 119.1 ? C16 C17 H17 119.1 ? C17 C18 C19 121.9(3) ? C17 C18 H18 119.0 ? C19 C18 H18 119.0 ? C20 C19 C24 119.7(4) ? C20 C19 C18 121.6(3) ? C24 C19 C18 118.7(3) ? C21 C20 C19 121.5(4) ? C21 C20 H20 119.2 ? C19 C20 H20 119.2 ? C20 C21 C22 119.2(4) ? C20 C21 H21 120.4 ? C22 C21 H21 120.4 ? C23 C22 C21 121.6(4) ? C23 C22 H22 119.2 ? C21 C22 H22 119.2 ? C22 C23 C24 120.5(4) ? C22 C23 H23 119.7 ? C24 C23 H23 119.7 ? C19 C24 C23 117.3(3) ? C19 C24 C15 119.4(3) ? C23 C24 C15 123.3(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Zn1 N1 1.836(2) y Zn1 N2 1.836(2) y Zn1 O1 1.848(2) y Zn1 O2 1.849(2) y O1 C2 1.301(3) ? O2 C16 1.292(3) ? N1 C11 1.293(4) ? N1 C12 1.482(4) ? N2 C14 1.285(4) ? N2 C13 1.481(4) ? C1 C2 1.404(4) ? C1 C11 1.424(4) ? C1 C10 1.458(4) ? C2 C3 1.434(4) ? C3 C4 1.347(4) ? C3 H3 0.9300 ? C4 C5 1.424(5) ? C4 H4 0.9300 ? C5 C10 1.415(5) ? C5 C6 1.420(5) ? C6 C7 1.341(6) ? C6 H6 0.9300 ? C7 C8 1.392(6) ? C7 H7 0.9300 ? C8 C9 1.360(5) ? C8 H8 0.9300 ? C9 C10 1.409(5) ? C9 H9 0.9300 ? C11 H11 0.9300 ? C12 C13 1.506(4) ? C12 H12A 0.9700 ? C12 H12B 0.9700 ? C13 H13A 0.9700 ? C13 H13B 0.9700 ? C14 C15 1.425(4) ? C14 H14 0.9300 ? C15 C16 1.410(4) ? C15 C24 1.452(4) ? C16 C17 1.440(4) ? C17 C18 1.347(4) ? C17 H17 0.9300 ? C18 C19 1.427(5) ? C18 H18 0.9300 ? C19 C20 1.412(5) ? C19 C24 1.412(5) ? C20 C21 1.342(6) ? C20 H20 0.9300 ? C21 C22 1.391(6) ? C21 H21 0.9300 ? C22 C23 1.368(5) ? C22 H22 0.9300 ? C23 C24 1.415(5) ? C23 H23 0.9300 ? 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 N1 Zn1 O1 C2 3.3(3) ? O2 Zn1 O1 C2 -178.1(3) ? N2 Zn1 O2 C16 7.9(2) ? O1 Zn1 O2 C16 -175.2(2) ? N2 Zn1 N1 C11 176.3(3) ? O1 Zn1 N1 C11 -0.6(3) ? N2 Zn1 N1 C12 -4.8(2) ? O1 Zn1 N1 C12 178.2(2) ? N1 Zn1 N2 C14 170.6(3) ? O2 Zn1 N2 C14 -7.9(3) ? N1 Zn1 N2 C13 -16.2(2) ? O2 Zn1 N2 C13 165.3(2) ? Zn1 O1 C2 C1 -5.1(4) ? Zn1 O1 C2 C3 174.4(2) ? C11 C1 C2 O1 3.3(5) ? C10 C1 C2 O1 -176.7(3) ? C11 C1 C2 C3 -176.2(3) ? C10 C1 C2 C3 3.8(4) ? O1 C2 C3 C4 176.7(3) ? C1 C2 C3 C4 -3.8(5) ? C2 C3 C4 C5 0.5(5) ? C3 C4 C5 C10 2.8(5) ? C3 C4 C5 C6 -177.5(4) ? C10 C5 C6 C7 0.3(6) ? C4 C5 C6 C7 -179.3(4) ? C5 C6 C7 C8 0.6(7) ? C6 C7 C8 C9 -0.3(7) ? C7 C8 C9 C10 -0.9(7) ? C8 C9 C10 C5 1.7(5) ? C8 C9 C10 C1 -177.3(4) ? C6 C5 C10 C9 -1.4(5) ? C4 C5 C10 C9 178.2(3) ? C6 C5 C10 C1 177.6(3) ? C4 C5 C10 C1 -2.7(5) ? C2 C1 C10 C9 178.4(3) ? C11 C1 C10 C9 -1.6(5) ? C2 C1 C10 C5 -0.6(4) ? C11 C1 C10 C5 179.4(3) ? C12 N1 C11 C1 -179.3(3) ? Zn1 N1 C11 C1 -0.5(5) ? C2 C1 C11 N1 -0.4(5) ? C10 C1 C11 N1 179.6(3) ? C11 N1 C12 C13 -157.4(3) ? Zn1 N1 C12 C13 23.7(3) ? C14 N2 C13 C12 -153.9(3) ? Zn1 N2 C13 C12 32.2(3) ? N1 C12 C13 N2 -34.0(3) y C13 N2 C14 C15 -171.5(3) ? Zn1 N2 C14 C15 1.5(5) ? N2 C14 C15 C16 7.8(5) ? N2 C14 C15 C24 -178.5(3) ? Zn1 O2 C16 C15 -1.5(4) ? Zn1 O2 C16 C17 -179.86(19) ? C14 C15 C16 O2 -7.8(4) ? C24 C15 C16 O2 178.5(3) ? C14 C15 C16 C17 170.6(3) ? C24 C15 C16 C17 -3.1(4) ? O2 C16 C17 C18 179.4(3) ? C15 C16 C17 C18 0.9(4) ? C16 C17 C18 C19 1.4(5) ? C17 C18 C19 C20 180.0(3) ? C17 C18 C19 C24 -1.3(5) ? C24 C19 C20 C21 1.3(6) ? C18 C19 C20 C21 180.0(4) ? C19 C20 C21 C22 -0.2(7) ? C20 C21 C22 C23 0.1(7) ? C21 C22 C23 C24 -1.1(6) ? C20 C19 C24 C23 -2.2(5) ? C18 C19 C24 C23 179.1(3) ? C20 C19 C24 C15 177.8(3) ? C18 C19 C24 C15 -1.0(5) ? C22 C23 C24 C19 2.1(5) ? C22 C23 C24 C15 -177.8(3) ? C16 C15 C24 C19 3.2(4) ? C14 C15 C24 C19 -170.4(3) ? C16 C15 C24 C23 -176.9(3) ? C14 C15 C24 C23 9.5(5) ?