#------------------------------------------------------------------------------ #$Date: 2015-04-02 14:22:18 +0300 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/50/2005007.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_2005007 loop_ _publ_author_name 'De Ridder, D. J. A.' 'Goubitz, K.' 'Reiss, C. A.' 'Schenk, H.' 'Hiemstra, H.' _publ_section_title ; One Bicyclic \b-Lactam and Two Bicyclic \g-Lactam Compounds ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1473 _journal_page_last 1479 _journal_paper_doi 10.1107/S0108270195014788 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C11 H16 Cl N O3' _chemical_formula_sum 'C11 H16 Cl N O3' _chemical_formula_weight 245.71 _chemical_melting_point .102E-101 _chemical_name_systematic ;(5R^*^,7S^*^,9S^*^)-7-chloro-7-methyl-3-oxo-octahydro-indolizidine-5- carboxylic acid methyl ester ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_type_scat_source 'IntTabIV 2.2B_and_2.3.1' _audit_creation_method from_xtal_archive_file_using_CIFIO _cell_angle_alpha 90 _cell_angle_beta 99.99(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.732(2) _cell_length_b 13.903(3) _cell_length_c 9.116(2) _cell_measurement_reflns_used 23 _cell_measurement_temperature 293 _cell_measurement_theta_max 19 _cell_measurement_theta_min 15 _cell_volume 1214.7(5) _computing_cell_refinement 'LATCON (local program) ' _computing_data_collection 'CAD-4 software (Enraf-Nonius 1989)' _computing_data_reduction 'Xtal ADDREF (Davenport & Hall, 1990)' _computing_molecular_graphics 'xtal ORTEP (Davenport, Hall & Dreissig, 1990)' _computing_publication_material ;xtal BONDLA (Dreissig, Doherty, Stewart & Hall, 1990), CIFIO (Hall, 1990) ; _computing_structure_refinement 'Xtal CRYLSQ (Olthof-Hazekamp, 1990)' _computing_structure_solution 'Xtal SIMPEL (Schenk & Hall, 1990)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source xray_tube _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2257 _diffrn_reflns_reduction_process perpendicular_monochr_Lp _diffrn_reflns_theta_max 24.92 _diffrn_reflns_theta_min 2.27 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.30 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_meas ? _exptl_crystal_description 'plate shaped crystal' _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.13 _refine_diff_density_max .206 _refine_diff_density_min -.252 _refine_ls_extinction_coef 1.1E-5(2) _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_all .783 _refine_ls_goodness_of_fit_obs .783 _refine_ls_hydrogen_treatment ;H atoms: restrained at 1.00 \%A from their carrier atom with U~eq~=0.10 \%A^2^ ; _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 146 _refine_ls_number_reflns 1172 _refine_ls_number_restraints 16 _refine_ls_R_factor_all .048 _refine_ls_R_factor_obs .048 _refine_ls_shift/esd_max .009 _refine_ls_shift/esd_mean .001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w^-1^ = [1.5 + 0.02\s(F)^2^ + 0.0001/\s(F)]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .047 _refine_ls_wR_factor_obs .047 _reflns_number_observed 1172 _reflns_number_total 2221 _reflns_observed_criterion refl_observed_if_Inet_>_2.5__sigma(Inet) _[local]_cod_data_source_file jz1068.cif _[local]_cod_data_source_block 2 _[local]_cod_cif_authors_sg_H-M 'P 21/a' _cod_depositor_comments ; 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w^-1^ = [1.5 + 0.02\s(F)^2^ + 0.0001/\s(F)]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w^-1^ = [1.5 + 0.02\s(F)^2^ + 0.0001/\s(F)]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2005007 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,1/2+y,-z -x,-y,-z 1/2+x,1/2-y,+z 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 .037(2) .050(2) .044(2) -.008(2) .007(2) -.003(2) C2 .033(2) .050(3) .048(3) -.005(2) .008(2) -.005(2) C3 .047(3) .052(3) .055(3) .008(2) .016(2) .006(2) C4 .065(3) .050(3) .054(3) -.001(3) .028(3) .001(2) C5 .056(3) .052(3) .064(3) -.011(2) .024(3) -.011(3) C6 .040(3) .052(3) .058(3) -.007(2) .015(2) -.008(2) C7 .054(3) .069(3) .061(3) -.005(3) .003(2) -.017(3) C8 .056(3) .085(4) .051(3) .004(3) .007(3) -.007(3) C9 .041(3) .058(3) .051(3) .008(2) .010(2) -.004(3) C10 .037(2) .051(3) .044(3) -.008(2) .005(2) .002(2) C11 .095(5) .092(5) .053(3) .013(4) .006(3) -.016(3) C12 .116(5) .047(3) .074(4) .003(3) .035(4) .006(3) O1 .061(2) .069(2) .061(2) -.011(2) .016(2) .010(2) O2 .044(2) .065(2) .064(2) .013(2) -.003(2) -.004(2) O3 .055(2) .066(2) .050(2) .009(2) -.002(2) -.010(2) Cl .0800(10) .0760(9) .0759(9) -.0128(8) .0464(8) -.0137(8) 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 _atom_site_calc_flag _atom_site_calc_attached_atom N1 .3242(3) .6502(3) -.0053(4) .044(2) Uani ? ? C2 .4149(4) .6742(3) .1334(5) .043(2) Uani ? ? C3 .4587(4) .5828(3) .2221(4) .050(3) Uani ? ? C4 .3390(5) .5119(3) .2312(5) .054(3) Uani ? ? C5 .2532(5) .4934(3) .0770(5) .056(3) Uani ? ? C6 .2058(4) .5840(3) -.0078(5) .050(3) Uani ? ? C7 .1563(4) .5693(4) -.1758(5) .062(3) Uani ? ? C8 .2017(5) .6617(4) -.2459(5) .065(3) Uani ? ? C9 .3201(5) .7006(4) -.1328(5) .050(3) Uani ? ? C10 .3499(5) .7513(3) .2181(5) .044(2) Uani ? ? C11 .3744(5) .8342(4) .4486(5) .081(4) Uani ? ? C12 .3968(5) .4190(3) .3105(5) .077(4) Uani ? ? O1 .4011(3) .7648(3) -.1514(3) .063(2) Uani ? ? O2 .2483(3) .7978(2) .1685(3) .059(2) Uani ? ? O3 .4255(3) .7649(2) .3531(3) .058(2) Uani ? ? Cl .2226(2) .5671(1) .3462(2) .0736(9) Uani ? ? H2 .50181 .70263 .10636 .10000 Uiso calc H2 H31 .53025 .54894 .17433 .10000 Uiso calc H3 H32 .50125 .60190 .32590 .10000 Uiso calc H3 H51 .31117 .45522 .01751 .10000 Uiso calc H5 H52 .16864 .45513 .08926 .10000 Uiso calc H5 H6 .13057 .61615 .03698 .10000 Uiso calc H6 H71 .20200 .51161 -.21195 .10000 Uiso calc H7 H72 .05245 .56120 -.19905 .10000 Uiso calc H7 H81 .23358 .64755 -.34219 .10000 Uiso calc H8 H82 .12287 .70921 -.26424 .10000 Uiso calc H8 H111 .36754 .89762 .39540 .10000 Uiso calc H11 H112 .27914 .81316 .46184 .10000 Uiso calc H11 H113 .43085 .84453 .54964 .10000 Uiso calc H11 H121 .46463 .38870 .25352 .10000 Uiso calc H12 H122 .44556 .43494 .41343 .10000 Uiso calc H12 H123 .31918 .37295 .31635 .10000 Uiso calc H12 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C .002 .002 H 0 0 N .004 .003 O .008 .006 Cl .132 .159 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 1 0 -1 3 1 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 C2 N1 C6 120.9(3) yes C2 N1 C9 123.6(4) yes C6 N1 C9 113.9(3) yes H2 C2 N1 106.8(4) no H2 C2 C10 106.8(4) no H2 C2 C3 106.8(3) no N1 C2 C3 110.0(3) yes N1 C2 C10 111.2(3) yes C3 C2 C10 114.8(4) yes H32 C3 H31 109.3(4) no H32 C3 C2 108.2(4) no H32 C3 C4 108.2(4) no H31 C3 C2 108.2(4) no H31 C3 C4 108.2(4) no C2 C3 C4 114.7(3) yes C3 C4 C5 110.9(4) yes C3 C4 C12 110.2(4) yes C3 C4 Cl 108.0(3) yes C5 C4 C12 112.9(4) yes C5 C4 Cl 107.6(3) yes C12 C4 Cl 107.1(3) yes H51 C5 H52 109.3(4) no H51 C5 C6 108.5(4) no H51 C5 C4 108.5(4) no H52 C5 C6 108.5(4) no H52 C5 C4 108.4(4) no C4 C5 C6 113.6(4) yes H6 C6 N1 109.9(4) no H6 C6 C5 110.1(4) no H6 C6 C7 109.9(4) no N1 C6 C5 110.2(3) yes N1 C6 C7 102.0(4) yes C5 C6 C7 114.5(4) yes H71 C7 H72 109.3(4) no H71 C7 C8 110.9(4) no H71 C7 C6 110.8(4) no H72 C7 C8 111.0(4) no H72 C7 C6 110.9(4) no C6 C7 C8 103.9(4) yes H81 C8 H82 109.1(4) no H81 C8 C9 110.8(4) no H81 C8 C7 110.9(5) no H82 C8 C9 110.4(5) no H82 C8 C7 110.6(4) no C7 C8 C9 104.9(4) yes N1 C9 C8 107.9(4) yes N1 C9 O1 125.1(4) yes C8 C9 O1 127.0(4) yes C2 C10 O2 125.1(4) yes C2 C10 O3 110.9(4) yes O2 C10 O3 123.9(4) yes H113 C11 H112 107.7(5) no H113 C11 H111 107.4(5) no H113 C11 O3 117.4(4) no H112 C11 H111 109.3(5) no H112 C11 O3 107.5(4) no H111 C11 O3 107.2(4) no H123 C12 H122 109.4(5) no H123 C12 H121 109.3(5) no H123 C12 C4 110.2(4) no H122 C12 H121 109.4(5) no H122 C12 C4 109.3(4) no H121 C12 C4 109.2(4) no C10 O3 C11 117.3(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.450(5) yes N1 C6 1.472(6) yes N1 C9 1.352(6) yes C2 H2 1.003(4) no C2 C3 1.526(6) yes C2 C10 1.521(6) yes C3 H32 1.001(4) no C3 H31 1.001(4) no C3 C4 1.539(7) yes C4 C5 1.527(6) yes C4 C12 1.537(7) yes C4 Cl 1.840(5) yes C5 H51 1.000(5) no C5 H52 1.002(5) no C5 C6 1.508(6) yes C6 H6 1.003(5) no C6 C7 1.537(7) yes C7 H71 1.000(5) no C7 H72 1.002(4) no C7 C8 1.534(7) yes C8 H81 1.000(5) no C8 H82 1.005(5) no C8 C9 1.507(6) yes C9 O1 1.222(6) yes C10 O2 1.202(5) yes C10 O3 1.333(5) yes C11 H113 .998(4) no C11 H112 .999(5) no C11 H111 1.003(5) no C11 O3 1.444(6) yes C12 H123 .999(5) no C12 H122 1.000(5) no C12 H121 1.001(5) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag N1 H2 1.987(3) . no O3 H111 1.987(3) . no O3 H112 1.988(3) . no N1 H6 2.043(4) . no C10 H2 2.050(5) . no C3 H2 2.054(4) . no C6 H51 2.056(5) . no C6 H52 2.058(5) . no C2 H32 2.070(4) . no C2 H31 2.071(4) . no C4 H52 2.074(5) . no C4 H51 2.074(5) . no C5 H6 2.078(5) . no C4 H31 2.082(5) . no C4 H32 2.082(5) . no C9 H82 2.082(4) . no C9 H81 2.083(4) . no C4 H121 2.093(5) . no C4 H122 2.093(5) . no O3 H113 2.100(3) . no C7 H6 2.101(5) . no C4 H123 2.103(5) . no C7 H81 2.109(5) . no C8 H71 2.109(6) . no C7 H82 2.110(5) . no C6 H71 2.110(5) . no C8 H72 2.112(5) . no C6 H72 2.113(4) . no O2 O3 2.237(4) . no N1 O1 2.284(5) . no C8 N1 2.313(5) . no C7 N1 2.338(6) . no C2 O3 2.353(5) . no C6 C9 2.367(7) . no O2 H2 2.367(3) 4_465 no C10 C11 2.372(7) . no O3 H32 2.409(3) . no C7 C9 2.411(7) . no C6 C8 2.419(7) . no C2 O2 2.421(5) . no C3 N1 2.439(5) . no C5 N1 2.444(6) . no C8 O1 2.445(6) . no C10 N1 2.452(6) . no C2 C9 2.469(6) . no C3 C12 2.523(7) . no C3 C5 2.526(6) . no O1 H2 2.536(3) . no C4 C6 2.540(6) . no C2 C6 2.542(6) . no C5 C12 2.554(6) . no C9 H2 2.558(4) . no C5 C7 2.561(7) . no C3 C10 2.568(6) . no O1 H82 2.573(4) 4_565 no C2 C4 2.581(7) . no C10 H112 2.585(5) . no C10 H111 2.585(5) . no O2 H111 2.592(3) . no C5 H71 2.607(5) . no O3 H2 2.634(3) . no C10 H32 2.636(4) . no C7 H51 2.640(5) . no O2 H112 2.647(3) . no C12 H31 2.655(5) . no C11 O2 2.682(5) . no C12 H51 2.704(5) . no O1 H81 2.712(3) . no C3 H122 2.713(4) . no C3 H121 2.714(5) . no Cl C12 2.722(5) . no N1 H51 2.723(4) . no Cl C5 2.723(5) . no C12 H32 2.733(5) . no C5 H123 2.737(5) . no Cl C3 2.739(5) . no N1 H31 2.747(3) . no O1 H121 2.748(4) 3_665 no O2 H51 2.768(3) 2 no N1 O2 2.770(5) . no C12 H52 2.774(5) . no C3 H51 2.785(4) . no Cl H52 2.7860(10) . no Cl H32 2.792(2) . no C5 H121 2.792(4) . no C5 H31 2.798(4) . no N1 H71 2.810(3) . no O1 H52 2.814(4) 2 no C9 H121 2.819(5) 3_665 no Cl H122 2.828(2) . no O1 H123 2.828(3) 2 no O1 H82 2.832(3) . no C3 O3 2.841(6) . no C4 H6 2.847(5) . no C8 H6 2.855(5) . no C9 H6 2.857(5) . no C2 O1 2.868(5) . no C2 H6 2.870(4) . no C4 N1 2.874(6) . no C7 H52 2.875(5) . no Cl H123 2.887(2) . no Cl H6 2.8880(10) . no O1 H72 2.904(4) 4_565 no C9 H71 2.908(5) . no N1 H82 2.912(3) . no C6 H82 2.914(5) . no O2 H2 2.940(3) . no O2 H6 2.941(3) . no C3 C6 2.943(5) . no C12 H82 2.949(5) 2_545 no C8 H113 2.954(4) 4_464 no C2 C5 2.963(6) . no O1 H113 3.002(3) 1_554 no C8 H123 3.006(6) 2 no O2 H31 3.015(3) 4_465 no O2 H71 3.027(3) 2 no Cl H81 3.037(2) 1_556 no N1 H81 3.044(3) . no C5 H72 3.055(4) . no O1 H6 3.057(3) 4_565 no C10 H6 3.097(4) . no C9 H123 3.097(5) 2 no C7 H111 3.098(5) 2_545 no C11 H123 3.136(5) 2_556 no Cl C10 3.155(5) . no N1 H72 3.166(3) . no Cl C6 3.211(5) . no C9 H72 3.219(5) . no C2 O2 3.229(5) 4_565 no C6 H81 3.230(5) . no C9 C10 3.239(6) . no C9 O2 3.244(6) . no C10 H113 3.257(4) . no C7 H113 3.257(4) 4_464 no C6 C10 3.258(6) . no C12 H112 3.261(5) 2_546 no C11 H71 3.276(5) 2 no N1 H32 3.276(3) . no Cl C2 3.277(5) . no N1 H52 3.293(4) . no C11 H82 3.297(5) 4_566 no C3 H122 3.301(4) 3_666 no Cl H72 3.3020(10) 3_565 no C12 H32 3.303(5) 3_666 no O2 H32 3.314(3) 4_465 no C2 H51 3.322(4) . no C6 H2 3.326(4) . no C4 C10 3.333(7) . no C8 H121 3.334(5) 3_665 no C6 H31 3.339(4) . no C8 O1 3.350(6) 4_465 no N1 H121 3.354(4) 3_665 no C5 H32 3.370(4) . no C6 O2 3.370(6) . no C3 H6 3.375(4) . no C10 H31 3.376(5) . no C3 H52 3.376(4) . no Cl O3 3.379(4) . no C3 O2 3.379(5) 4_565 no C4 H2 3.386(5) . no C12 H122 3.386(5) 3_666 no C3 H123 3.391(5) . no C5 H122 3.403(4) . no C7 H52 3.406(5) 3_565 no O2 H52 3.409(3) 2 no C5 H31 3.422(5) 3_665 no C10 H2 3.424(4) 4_465 no C7 O1 3.425(6) 4_465 no C3 H51 3.430(4) 3_665 no C5 H72 3.436(5) 3_565 no C7 H31 3.464(5) 3_665 no C10 O1 3.495(6) . no C5 O2 3.521(6) 2_545 no O2 O1 3.526(5) . no C6 O1 3.537(6) . no C8 H121 3.542(5) 2 no Cl H111 3.548(2) 2_546 no C9 H52 3.560(5) 2 no C3 H71 3.570(4) 3_665 no Cl H122 3.5740(10) 3_666 no C8 H112 3.577(5) 1_554 no N1 H31 3.578(4) 3_665 no C5 C9 3.580(7) . no O3 H112 3.581(3) 4_565 no O1 H112 3.583(3) 1_554 no O3 H122 3.591(3) 3_666 no Cl H112 3.593(2) . no C9 H82 3.594(5) 4_565 no Cl H111 3.595(2) 4_465 no C7 O1 3.596(6) . no C3 O2 3.607(6) . no Cl H51 3.611(2) . no N1 O3 3.615(5) . no C4 H122 3.617(5) 3_666 no Cl H121 3.620(2) . no Cl O2 3.620(4) . no Cl H31 3.620(2) . no C11 H81 3.627(5) 1_556 no C5 O1 3.628(6) 2_545 no C6 H52 3.631(4) 3_565 no Cl H113 3.634(2) 2_546 no O3 H31 3.645(3) . no C10 H71 3.653(5) 2 no C3 C9 3.668(6) . no C12 O1 3.674(6) 3_665 no C11 H72 3.675(5) 4_566 no O2 H113 3.675(3) . no C2 H51 3.676(4) 3_665 no C12 H81 3.677(5) 3_665 no C9 H51 3.683(5) . no C6 O1 3.685(5) 4_465 no C11 H81 3.689(5) 4_566 no O1 H51 3.693(4) 2 no C12 O1 3.694(6) 2_545 no O3 H82 3.697(3) 4_566 no C6 H31 3.698(5) 3_665 no Cl N1 3.698(4) . no C11 H32 3.699(5) . no C2 C11 3.708(7) . no C2 C8 3.715(6) . no C11 H32 3.717(5) 4_465 no C8 C12 3.724(7) 2 no C5 C8 3.726(7) . no Cl O3 3.726(4) 4_465 no C10 H51 3.734(4) 2 no C2 C7 3.734(6) . no C11 O1 3.737(6) 1_556 no C4 O3 3.741(6) . no C5 H2 3.764(5) . no C3 H112 3.772(4) 4_565 no C8 H51 3.775(5) . no C12 H113 3.778(5) 2_546 no O2 H32 3.782(3) . no C2 H6 3.784(4) 4_565 no O3 H71 3.796(3) 2 no C9 H31 3.805(5) . no C9 H31 3.807(5) 3_665 no C9 C12 3.812(7) 3_665 no C6 H2 3.813(5) 4_465 no C6 H32 3.814(4) . no C11 H122 3.821(5) 2_556 no C9 H113 3.825(5) 1_554 no C9 H121 3.830(5) 2 no O1 H123 3.842(4) 3_665 no C8 C11 3.851(6) 4_464 no Cl H113 3.852(2) 4_465 no C2 H52 3.853(4) . no N1 H51 3.859(4) 3_665 no C5 C10 3.870(7) . no C7 O2 3.885(6) 2_545 no C9 C12 3.888(7) 2 no C10 H6 3.892(5) 4_565 no C11 C12 3.897(8) 2_556 no C8 H31 3.901(5) 3_665 no C4 H72 3.904(5) 3_565 no C6 C12 3.907(6) . no C4 C7 3.908(7) . no O2 O3 3.911(5) 4_465 no O3 H81 3.912(3) 4_566 no C2 C12 3.914(7) . no Cl C11 3.916(6) 4_465 no O1 H121 3.918(3) 2 no C7 H121 3.920(5) 3_665 no C8 H111 3.934(5) 2_545 no Cl C11 3.936(6) 2_546 no Cl H112 3.942(2) 2_546 no C6 H72 3.948(5) 3_565 no O3 H81 3.958(3) 1_556 no O1 H6 3.965(4) . no C9 H51 3.966(5) 2 no C10 H52 3.967(5) 2 no C9 H112 3.969(5) 1_554 no C2 H112 3.977(4) . no Cl C8 3.982(5) 1_556 no C8 H2 3.989(4) . no C2 H111 3.993(4) . no C11 H2 3.995(5) . no C5 H6 4.000(4) 3_565 no C2 H121 4.002(4) 3_665 no C12 H81 4.008(5) 2_545 no O1 H71 4.010(4) . no C11 H72 4.025(5) 2 no C3 H111 4.028(4) 4_565 no C4 H71 4.028(5) . no C12 H111 4.036(5) 2_546 no C10 O2 4.039(6) 4_565 no Cl C11 4.045(5) . no C9 O1 4.080(6) 4_465 no C7 C11 4.086(7) 2_545 no C4 O2 4.090(6) . no C12 O3 4.134(6) 3_666 no Cl H71 4.140(2) 1_556 no C4 O1 4.147(6) 2_545 no O2 O1 4.155(4) 4_465 no C5 C9 4.178(7) 2_545 no C8 O2 4.179(6) . no Cl C7 4.198(5) 3_565 no C3 O1 4.201(5) . no C8 C12 4.203(7) 3_665 no C4 C9 4.209(7) . no C3 C11 4.211(7) . no Cl H2 4.216(2) . no C7 C11 4.219(6) 4_464 no N1 O2 4.220(4) 4_565 no C8 C11 4.237(7) 1_554 no Cl H2 4.245(2) 4_465 no Cl H71 4.245(2) 3_565 no C3 C12 4.249(6) 3_666 no C3 C7 4.260(6) . no N1 O1 4.269(5) 4_465 no C8 O3 4.269(5) 4_464 no C6 O2 4.291(6) 2_545 no C12 N1 4.291(6) . no C2 C10 4.296(6) 4_565 no C5 O2 4.315(6) . no C12 C12 4.316(7) 3_666 no C5 C10 4.317(6) 2_545 no C12 N1 4.320(7) 3_665 no C5 C7 4.323(7) 3_565 no C9 C11 4.358(7) 1_554 no C3 C11 4.366(6) 4_565 no C3 C5 4.367(7) 3_665 no C3 C7 4.387(6) 3_665 no C6 O3 4.391(5) . no C8 C10 4.405(6) . no Cl C10 4.408(5) 4_465 no Cl C12 4.419(5) 3_666 no C7 C10 4.437(7) 2_545 no Cl C7 4.515(5) 1_556 no 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 C6 N1 C2 C3 47.7(5) yes N1 C2 C3 C4 -45.8(5) yes C2 C3 C4 C5 49.2(5) yes C3 C4 C5 C6 -51.0(5) yes C4 C5 C6 N1 49.4(5) yes C5 C6 N1 C2 -50.0(5) yes C9 N1 C6 C7 22.1(5) yes N1 C6 C7 C8 -26.6(4) yes C6 C7 C8 C9 23.3(5) yes C7 C8 C9 N1 -10.6(5) yes C8 C9 N1 C6 -7.5(5) yes C10 C2 C3 C4 80.5(5) ? C10 C2 C3 H31 -158.7(3) ? C10 C2 C3 H32 -40.3(5) ? N1 C2 C3 H31 75.0(4) ? N1 C2 C3 H32 -166.6(4) ? H2 C2 C3 C4 -161.3(4) ? H2 C2 C3 H31 -40.4(5) ? H2 C2 C3 H32 77.9(5) ? C3 C2 C10 O2 -136.8(5) ? C3 C2 C10 O3 46.9(5) ? N1 C2 C10 O2 -11.1(6) ? N1 C2 C10 O3 172.6(4) ? H2 C2 C10 O2 105.0(5) ? H2 C2 C10 O3 -71.3(5) ? C3 C2 N1 C9 -147.7(4) ? C10 C2 N1 C6 -80.6(5) ? C10 C2 N1 C9 84.0(5) ? H2 C2 N1 C6 163.2(4) ? H2 C2 N1 C9 -32.2(6) ? C2 C3 C4 Cl -68.4(4) ? C2 C3 C4 C12 174.9(4) ? H31 C3 C4 Cl 170.7(3) ? H31 C3 C4 C5 -71.6(5) ? H31 C3 C4 C12 54.1(5) ? H32 C3 C4 Cl 52.4(4) ? H32 C3 C4 C5 170.1(4) ? H32 C3 C4 C12 -64.2(5) ? Cl C4 C5 C6 66.9(5) ? Cl C4 C5 H51 -172.3(3) ? Cl C4 C5 H52 -53.7(5) ? C3 C4 C5 H51 69.8(5) ? C3 C4 C5 H52 -171.6(4) ? C12 C4 C5 C6 -175.1(4) ? C12 C4 C5 H51 -54.4(6) ? C12 C4 C5 H52 64.2(6) ? Cl C4 C12 H121 -177.1(3) ? Cl C4 C12 H122 -57.4(5) ? Cl C4 C12 H123 62.9(5) ? C3 C4 C12 H121 -59.9(5) ? C3 C4 C12 H122 59.8(6) ? C3 C4 C12 H123 -180.0(4) ? C5 C4 C12 H121 64.7(6) ? C5 C4 C12 H122 -175.7(4) ? C5 C4 C12 H123 -55.4(6) ? C4 C5 C6 C7 163.6(4) ? C4 C5 C6 H6 -72.0(5) ? H51 C5 C6 C7 42.9(5) ? H51 C5 C6 N1 -71.4(5) ? H51 C5 C6 H6 167.2(4) ? H52 C5 C6 C7 -75.8(5) ? H52 C5 C6 N1 170.0(4) ? H52 C5 C6 H6 48.6(5) ? C5 C6 C7 C8 -145.6(4) ? C5 C6 C7 H71 -26.5(6) ? C5 C6 C7 H72 95.0(5) ? N1 C6 C7 H71 92.5(5) ? N1 C6 C7 H72 -145.9(4) ? H6 C6 C7 C8 89.9(5) ? H6 C6 C7 H71 -151.0(4) ? H6 C6 C7 H72 -29.5(6) ? C5 C6 N1 C9 144.1(4) ? C7 C6 N1 C2 -172.0(4) ? H6 C6 N1 C2 71.5(5) ? H6 C6 N1 C9 -94.4(5) ? C6 C7 C8 H81 142.9(4) ? C6 C7 C8 H82 -95.8(4) ? H71 C7 C8 C9 -95.8(5) ? H71 C7 C8 H81 23.9(5) ? H71 C7 C8 H82 145.1(4) ? H72 C7 C8 C9 142.5(4) ? H72 C7 C8 H81 -97.8(5) ? H72 C7 C8 H82 23.5(6) ? C7 C8 C9 O1 167.9(5) ? H81 C8 C9 N1 -130.4(5) ? H81 C8 C9 O1 48.2(7) ? H82 C8 C9 N1 108.6(5) ? H82 C8 C9 O1 -72.9(7) ? C8 C9 N1 C2 -173.0(4) ? O1 C9 N1 C2 8.4(7) ? O1 C9 N1 C6 173.9(5) ? C2 C10 O3 C11 -178.2(4) ? O2 C10 O3 C11 5.4(7) ? H111 C11 O3 C10 -59.0(5) ? H112 C11 O3 C10 58.5(5) ? H113 C11 O3 C10 -179.9(4) ?