data_2010338 _journal_name_full 'Acta Crystallographica' _journal_year 1994 _journal_volume C50 _journal_page_first 2072 _journal_page_last 2074 _publ_section_title ; 8-Chloro-3,6-dioxaoctyl (E,E)-2-Chloro-3-(3,5-dichloro-2-hydroxyphenylazo)-2-butenoate ; loop_ _publ_author_name 'Ramm, Matthias' 'Baumann, Hendrik' 'Kirschke, Klaus' _chemical_formula_moiety 'C16 H18 Cl4 N2 O5' _chemical_formula_sum 'C16 H18 Cl4 N2 O5' _chemical_formula_weight 460.14 _chemical_melting_point '71 -72_C' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'X,Y,Z' '1/2+X,1/2-Y,1/2+Z' '-X,-Y,-Z' '1/2-X,1/2+Y,1/2-Z' _cell_length_a 7.1189(4) _cell_length_b 25.685(3) _cell_length_c 11.1476(9) _cell_angle_alpha 90 _cell_angle_beta 98.641(6) _cell_angle_gamma 90 _cell_volume 2015.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_density_diffrn 1.517 _diffrn_ambient_temperature 293 _refine_ls_R_factor_obs 0.045 _refine_ls_wR_factor_obs 0.071 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type Cl1 0.27730(19) 0.02987(4) 0.06612(7) 0.0816(4) Uani Cl2 0.27354(19) 0.20683(4) 0.32066(9) 0.0862(4) Uani Cl3 0.22017(14) -0.12438(4) 0.77274(7) 0.0671(3) Uani Cl4 -0.94626(16) -0.17921(4) 0.02035(10) 0.0793(3) Uani O1 0.2722(4) -0.02052(9) 0.29773(19) 0.0613(8) Uani O2 0.2695(5) -0.11181(11) 0.4347(2) 0.0828(12) Uani O3 0.1964(3) -0.17503(9) 0.5537(2) 0.0575(8) Uani O4 -0.1038(3) -0.19167(10) 0.3518(2) 0.0644(8) Uani O5 -0.5642(4) -0.16776(10) 0.1887(2) 0.0688(9) Uani N1 0.2556(4) 0.03340(11) 0.5294(2) 0.0503(8) Uani N2 0.2508(4) -0.01559(10) 0.5260(2) 0.0476(8) Uani C1 0.2648(5) 0.05756(13) 0.4170(3) 0.0468(9) Uani C2 0.2705(5) 0.03084(12) 0.3071(3) 0.0468(9) Uani C3 0.2774(5) 0.06122(13) 0.2034(3) 0.0532(10) Uani C4 0.2799(5) 0.11463(13) 0.2072(3) 0.0547(10) Uani C5 0.2742(5) 0.13962(13) 0.3167(3) 0.0562(10) Uani C6 0.2645(5) 0.11164(13) 0.4210(3) 0.0538(10) Uani C7 0.2414(5) -0.03989(14) 0.6390(3) 0.0500(10) Uani C8 0.2355(6) -0.00657(15) 0.7479(3) 0.0664(11) Uani C9 0.2349(5) -0.09207(14) 0.6383(3) 0.0496(10) Uani C10 0.2361(5) -0.12654(14) 0.5301(3) 0.0510(10) Uani C11 0.1946(5) -0.21376(14) 0.4582(3) 0.0601(11) Uani C12 -0.0026(5) -0.23223(13) 0.4179(3) 0.0574(10) Uani C13 -0.2902(6) -0.20558(15) 0.2979(4) 0.0691(12) Uani C14 -0.3685(6) -0.15970(17) 0.2271(4) 0.0720(14) Uani C15 -0.6513(6) -0.12308(15) 0.1284(4) 0.0702(14) Uani C16 -0.8574(6) -0.12765(16) 0.1198(4) 0.0747(14) Uani H1 0.256(7) -0.037(2) 0.399(4) 0.29(4) Uiso H4 0.279(5) 0.1339(12) 0.130(3) 0.120(19) Uiso H6 0.256(5) 0.1292(13) 0.490(3) 0.15(2) Uiso H81 0.182(6) -0.0257(16) 0.804(4) 0.22(3) Uiso H82 0.127(5) 0.0158(14) 0.725(3) 0.16(2) Uiso H83 0.351(5) 0.0133(14) 0.763(3) 0.16(2) Uiso H111 0.240(5) -0.2033(13) 0.390(3) 0.13(2) Uiso H112 0.273(5) -0.2381(14) 0.487(3) 0.15(2) Uiso H121 -0.058(5) -0.2408(12) 0.487(3) 0.119(19) Uiso H122 -0.010(4) -0.2609(12) 0.363(3) 0.103(18) Uiso H131 -0.341(6) -0.2150(16) 0.374(4) 0.21(3) Uiso H132 -0.296(5) -0.2344(13) 0.259(3) 0.14(2) Uiso H141 -0.342(8) -0.156(2) 0.150(5) 0.30(4) Uiso H142 -0.359(6) -0.1309(16) 0.285(4) 0.20(3) Uiso H151 -0.604(5) -0.1211(14) 0.057(3) 0.16(2) Uiso H152 -0.601(5) -0.0910(13) 0.187(3) 0.15(2) Uiso H161 -0.934(6) -0.1010(16) 0.080(4) 0.20(3) Uiso H162 -0.904(5) -0.1400(15) 0.195(3) 0.17(2) Uiso 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 Cl1 0.1224(9) 0.0820(6) 0.0387(3) -0.0090(4) 0.0063(5) 0.0121(6) Cl2 0.1258(9) 0.0572(4) 0.0842(5) -0.0050(4) 0.0437(5) -0.0051(6) Cl3 0.0653(6) 0.0942(6) 0.0416(3) 0.0081(4) 0.0075(4) -0.0165(5) Cl4 0.0715(7) 0.0761(5) 0.0836(6) 0.0083(5) -0.0097(5) -0.0088(5) O1 0.0827(18) 0.0574(12) 0.0429(10) -0.0086(9) 0.0065(11) 0.0081(12) O2 0.133(3) 0.0711(15) 0.0492(11) -0.0046(11) 0.0296(14) -0.0156(16) O3 0.0555(15) 0.0639(13) 0.0520(11) 0.0028(10) 0.0050(11) -0.0017(12) O4 0.0517(15) 0.0694(13) 0.0683(14) -0.0015(12) -0.0036(12) -0.0012(13) O5 0.0569(16) 0.0715(14) 0.0734(15) -0.0019(12) -0.0050(13) 0.0006(13) N1 0.0413(15) 0.0658(15) 0.0438(12) -0.0067(12) 0.0065(11) -0.0026(13) N2 0.0364(15) 0.0641(14) 0.0418(11) -0.0030(11) 0.0044(11) -0.0004(13) C1 0.0355(17) 0.0642(17) 0.0406(13) -0.0070(13) 0.0057(12) 0.0000(15) C2 0.0381(18) 0.0587(16) 0.0419(13) -0.0062(13) 0.0005(13) 0.0066(15) C3 0.051(2) 0.0653(17) 0.0404(13) -0.0057(14) -0.0028(14) 0.0089(17) C4 0.053(2) 0.0651(18) 0.0452(14) 0.0005(14) 0.0052(15) 0.0071(17) C5 0.055(2) 0.0565(16) 0.0587(16) -0.0061(15) 0.0139(15) 0.0035(17) C6 0.051(2) 0.0629(18) 0.0485(15) -0.0114(14) 0.0109(15) -0.0015(17) C7 0.0368(18) 0.078(2) 0.0352(12) -0.0048(13) 0.0054(12) -0.0101(16) C8 0.071(2) 0.085(2) 0.0460(14) -0.0160(16) 0.0179(15) -0.017(2) C9 0.0347(18) 0.075(2) 0.0381(13) 0.0023(13) 0.0023(13) -0.0069(16) C10 0.0359(18) 0.0697(19) 0.0460(14) 0.0027(15) 0.0019(13) -0.0014(16) C11 0.056(2) 0.0621(19) 0.0629(18) 0.0000(16) 0.0112(17) 0.0115(18) C12 0.054(2) 0.0575(17) 0.0603(17) -0.0063(16) 0.0077(16) 0.0058(17) C13 0.057(2) 0.075(2) 0.071(2) -0.0098(19) -0.004(2) -0.006(2) C14 0.052(2) 0.092(3) 0.068(2) -0.001(2) -0.0038(19) -0.004(2) C15 0.067(3) 0.063(2) 0.077(2) -0.0052(18) -0.001(2) -0.001(2) C16 0.072(3) 0.079(2) 0.070(2) -0.0025(19) 0.001(2) 0.018(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C3 . . 1.729(3) yes Cl2 C5 . . 1.727(3) yes Cl3 C9 . . 1.730(4) yes Cl4 C16 . . 1.781(4) yes O1 C2 . . 1.324(4) yes O2 C10 . . 1.186(4) yes O3 C10 . . 1.312(4) yes O3 C11 . . 1.456(4) yes O4 C12 . . 1.410(4) yes O4 C13 . . 1.418(5) yes O5 C14 . . 1.410(5) yes O5 C15 . . 1.424(5) yes N1 N2 . . 1.259(4) yes N1 C1 . . 1.409(4) yes N2 C7 . . 1.416(4) yes C1 C2 . . 1.410(5) yes C1 C6 . . 1.390(5) yes C2 C3 . . 1.402(5) yes C3 C4 . . 1.373(5) yes C4 C5 . . 1.385(5) yes C5 C6 . . 1.377(5) yes C7 C8 . . 1.491(5) yes C7 C9 . . 1.341(5) yes C9 C10 . . 1.497(5) yes C11 C12 . . 1.486(5) yes C13 C14 . . 1.480(6) yes C15 C16 . . 1.461(6) yes O1 H1 . . 1.23(5) no C4 H4 . . 0.99(3) no C6 H6 . . 0.90(3) no C8 H81 . . 0.92(4) no C8 H82 . . 0.97(4) no C8 H83 . . 0.96(4) no C11 H111 . . 0.91(3) no C11 H112 . . 0.87(4) no C12 H121 . . 0.94(3) no C12 H122 . . 0.95(3) no C13 H131 . . 1.00(4) no C13 H132 . . 0.86(3) no C14 H141 . . 0.91(6) no C14 H142 . . 0.98(4) no C15 H151 . . 0.91(3) no C15 H152 . . 1.08(3) no C16 H161 . . 0.94(4) no C16 H162 . . 1.00(3) no