#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/50/2005006.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_2005006 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_volume 52 _journal_year 1996 _chemical_formula_moiety 'C10 H14 Cl N O3' _chemical_formula_sum 'C10 H14 Cl N O3' _chemical_formula_weight 231.68 _chemical_name_systematic ; (2R^*^,4S^*^,6S^*^)-4-chloro-4-methyl-8-oxo-1-azabicyclo[4.2.0]octane -2-carboxylic acid methyl ester ; _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_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 111.00(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.456(2) _cell_length_b 12.237(2) _cell_length_c 9.531(1) _cell_measurement_reflns_used 23 _cell_measurement_temperature 293 _cell_measurement_theta_max 20.7 _cell_measurement_theta_min 17.9 _cell_volume 1138.5(3) _computing_cell_refinement 'LATCON (local program) ' _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ;xtal SORTRF (Hall, Spadaccini & Stewart, 1990), 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_av_sigmaI/netI 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2134 _diffrn_reflns_reduction_process perpendicular_monochr_Lp _diffrn_reflns_theta_max 24.89 _diffrn_reflns_theta_min 2.09 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 83 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.32 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description 'plate shaped crystal' _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.10 _refine_diff_density_max .347 _refine_diff_density_min -.302 _refine_ls_extinction_coef 4.4E-5(3) _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_all .87 _refine_ls_goodness_of_fit_obs .87 _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 137 _refine_ls_number_reflns 1397 _refine_ls_number_restraints 14 _refine_ls_R_factor_all .049 _refine_ls_R_factor_obs .049 _refine_ls_shift/esd_max .002 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w^-1^ = [1.5 + 0.02\s(F)^2^ + 0.0001/\s(F)]' _refine_ls_wR_factor_all .049 _refine_ls_wR_factor_obs .049 _reflns_number_observed 1398 _reflns_number_total 2100 _reflns_observed_criterion refl_observed_if_I_>_2.5_sigma(I) _[local]_cod_data_source_file jz1068.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'None' changed to 'none' 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 2005006 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,1/2-z -x,-y,-z +x,1/2-y,1/2+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_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom N1 .5560(3) .6577(2) .2094(3) .043(2) Uani ? ? C2 .6935(4) .6695(3) .2117(4) .042(2) Uani ? ? C3 .7666(3) .5575(3) .2473(4) .044(2) Uani ? ? C4 .7364(4) .4912(3) .3675(4) .044(2) Uani ? ? C5 .5836(4) .4790(3) .3335(4) .046(2) Uani ? ? C6 .5135(4) .5894(3) .3129(4) .045(2) Uani ? ? C7 .3657(4) .5990(3) .1981(5) .054(2) Uani ? ? C8 .4301(4) .6616(3) .0998(5) .049(2) Uani ? ? C9 .7690(4) .7615(3) .3178(4) .043(2) Uani ? ? C10 .9825(5) .8495(3) .4278(5) .074(3) Uani ? ? C11 .8085(4) .3811(3) .3909(5) .062(2) Uani ? ? O1 .3897(3) .6994(3) -.0251(3) .067(2) Uani ? ? O2 .7165(3) .8257(2) .3750(3) .059(2) Uani ? ? O3 .9010(3) .7633(2) .3322(3) .054(1) Uani ? ? Cl .8095(1) .56524(9) .5476(1) .0605(6) Uani ? ? H2 .68716 .69067 .10802 .10000 Uiso calc C2 H31 .73735 .51344 .15265 .10000 Uiso calc C3 H32 .86770 .57048 .28244 .10000 Uiso calc C3 H51 .54231 .43539 .23921 .10000 Uiso calc C5 H52 .56927 .43981 .41880 .10000 Uiso calc C5 H6 .52624 .62674 .41034 .10000 Uiso calc C6 H71 .32127 .52812 .15516 .10000 Uiso calc C7 H72 .30186 .64287 .23270 .10000 Uiso calc C7 H101 1.04896 .79486 .49188 .10000 Uiso calc C10 H102 1.01316 .87402 .34484 .10000 Uiso calc C10 H103 .93853 .90322 .47562 .10000 Uiso calc C10 H111 .77586 .33953 .29410 .10000 Uiso calc C11 H112 .90956 .39317 .42320 .10000 Uiso calc C11 H113 .78865 .33766 .46959 .10000 Uiso calc C11 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 .048(2) .039(2) .042(2) -.0020(10) .0170(10) .0060(10) C2 .053(2) .039(2) .035(2) -.004(2) .018(2) .002(2) C3 .053(2) .039(2) .043(2) -.004(2) .022(2) -.005(2) C4 .052(2) .036(2) .042(2) -.003(2) .015(2) -.002(2) C5 .053(2) .038(2) .051(2) -.002(2) .023(2) .007(2) C6 .050(2) .043(2) .047(2) -.004(2) .025(2) .003(2) C7 .049(2) .047(2) .070(3) .000(2) .024(2) .002(2) C8 .051(2) .039(2) .053(2) .004(2) .015(2) -.003(2) C9 .057(2) .035(2) .040(2) -.002(2) .019(2) .009(2) C10 .075(3) .049(3) .076(3) -.015(2) .002(3) -.005(2) C11 .062(3) .041(2) .077(3) .005(2) .018(2) .008(2) O1 .069(2) .070(2) .053(2) .006(2) .0100(10) .013(2) O2 .080(2) .041(2) .062(2) .0010(10) .034(2) -.0040(10) O3 .052(2) .044(2) .063(2) -.0100(10) .0160(10) -.0030(10) Cl .0739(7) .0598(6) .0413(5) -.0054(6) .0128(5) -.0026(5) 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 -3 1 1 -1 2 3 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 125.8(3) yes C2 N1 C8 134.3(3) yes C6 N1 C8 95.3(3) yes H2 C2 N1 107.4(3) no H2 C2 C9 107.4(3) no H2 C2 C3 107.4(3) no N1 C2 C3 109.1(3) yes N1 C2 C9 111.2(3) yes C3 C2 C9 114.2(3) yes H31 C3 H32 109.5(4) no H31 C3 C4 108.2(3) no H31 C3 C2 108.2(3) no H32 C3 C4 108.2(3) no H32 C3 C2 108.2(3) no C2 C3 C4 114.6(3) yes C3 C4 C5 112.2(3) yes C3 C4 C11 110.8(4) yes C3 C4 Cl 108.0(2) yes C5 C4 C11 111.9(3) yes C5 C4 Cl 107.4(3) yes C11 C4 Cl 106.3(2) yes H52 C5 H51 109.5(3) no H52 C5 C6 109.0(4) no H52 C5 C4 109.0(3) no H51 C5 C6 109.0(3) no H51 C5 C4 109.0(4) no C4 C5 C6 111.3(3) yes H6 C6 N1 112.9(3) no H6 C6 C5 112.9(3) no H6 C6 C7 112.9(4) no N1 C6 C5 110.1(3) yes N1 C6 C7 87.0(3) yes C5 C6 C7 118.3(3) yes H71 C7 H72 109.5(4) no H71 C7 C8 115.0(4) no H71 C7 C6 115.0(3) no H72 C7 C8 115.0(3) no H72 C7 C6 115.1(4) no C6 C7 C8 85.7(3) yes N1 C8 C7 91.7(3) yes N1 C8 O1 132.4(4) yes C7 C8 O1 135.9(4) yes C2 C9 O2 124.9(4) yes C2 C9 O3 110.5(3) yes O2 C9 O3 124.6(3) yes H102 C10 H101 109.5(5) no H102 C10 H103 119.6(4) no H102 C10 O3 90.3(3) no H101 C10 H103 119.5(4) no H101 C10 O3 91.2(3) no H103 C10 O3 120.0(4) no H111 C11 H112 109.5(5) no H111 C11 H113 109.1(4) no H111 C11 C4 109.1(3) no H112 C11 H113 109.1(3) no H112 C11 C4 109.1(3) no H113 C11 C4 110.8(4) no C9 O3 C10 115.4(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.437(5) yes N1 C6 1.478(5) yes N1 C8 1.357(4) yes C2 H2 1.000(4) no C2 C3 1.548(5) yes C2 C9 1.529(5) yes C3 H31 1.000(3) no C3 H32 1.000(3) no C3 C4 1.526(6) yes C4 C5 1.519(6) yes C4 C11 1.521(5) yes C4 Cl 1.847(4) yes C5 H52 1.000(4) no C5 H51 1.000(3) no C5 C6 1.516(5) yes C6 H6 1.000(4) no C6 C7 1.545(5) yes C7 H71 1.000(4) no C7 H72 1.000(5) no C7 C8 1.538(7) yes C8 O1 1.204(5) yes C9 O2 1.196(5) yes C9 O3 1.337(5) yes C10 H102 1.000(5) no C10 H101 1.000(4) no C10 H103 1.001(5) no C10 O3 1.453(5) yes C11 H111 1.000(4) no C11 H112 1.000(4) no C11 H113 1.000(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 O3 H102 1.767(3) . no O3 H101 1.780(2) . no N1 H2 1.981(4) . no C9 H2 2.062(3) . no C4 H31 2.069(4) . no C4 H32 2.069(4) . no C6 H51 2.071(4) . no C6 H52 2.071(4) . no C4 H52 2.074(4) . no C4 H51 2.074(3) . no C4 H112 2.076(4) . no C4 H111 2.076(4) . no C3 H2 2.078(3) . no N1 C7 2.081(5) . no N1 H6 2.083(3) . no C2 H31 2.088(4) . no C2 H32 2.088(4) . no C4 H113 2.096(4) . no C6 C8 2.097(5) . no C5 H6 2.117(4) . no O3 H103 2.137(3) . no C7 H6 2.143(4) . no C8 H71 2.161(4) . no C8 H72 2.161(5) . no C6 H71 2.167(3) . no C6 H72 2.167(4) . no O2 O3 2.243(5) . no N1 O1 2.344(4) . no C2 O3 2.357(4) . no O2 H2 2.357(3) 4_565 no C9 C10 2.359(6) . no O2 H103 2.369(3) . no O3 H32 2.408(3) . no C2 O2 2.421(5) . no N1 C3 2.432(5) . no N1 C9 2.448(5) . no N1 C5 2.454(5) . no C4 C6 2.505(5) . no C3 C11 2.508(5) . no O2 H71 2.508(3) 2_655 no C5 C11 2.519(6) . no C3 C5 2.528(6) . no C7 O1 2.545(6) . no C9 H103 2.550(3) . no O1 H111 2.572(3) 3_665 no C2 C8 2.575(5) . no C3 C9 2.583(5) . no C2 C4 2.587(5) . no C2 C6 2.596(6) . no C9 H32 2.625(4) . no C5 C7 2.628(5) . no C11 H101 2.629(4) 3_766 no O3 H2 2.633(2) . no C7 H51 2.656(4) . no C10 O2 2.659(6) . no C11 H31 2.668(4) . no C8 H2 2.685(4) . no C5 H113 2.698(3) . no C11 H32 2.698(4) . no C3 H111 2.700(4) . no C3 H112 2.700(3) . no C11 Cl 2.702(4) . no C11 H52 2.706(5) . no O1 H113 2.707(3) 2_655 no C11 H51 2.719(4) . no C5 Cl 2.721(3) . no C5 H71 2.726(3) . no C3 Cl 2.735(4) . no N1 H51 2.744(3) . no H101 H111 2.7464(3) 3_766 no N1 H72 2.751(3) . no O1 H6 2.752(3) 4_564 no C3 H51 2.759(4) . no C5 H111 2.763(4) . no N1 O2 2.764(4) . no C5 H31 2.779(5) . no N1 H31 2.781(3) . no C8 H6 2.796(4) . no Cl H112 2.7970(10) . no Cl H32 2.8040(10) . no N1 H71 2.810(3) . no N1 C4 2.818(4) . no Cl H52 2.8210(10) . no C9 H101 2.829(4) . no C9 H102 2.829(4) . no C3 O3 2.857(4) . no O2 H51 2.863(3) 2_655 no Cl H113 2.8700(10) . no Cl H6 2.8760(10) . no O1 H72 2.894(3) 4_564 no Cl H112 2.8950(10) 3_766 no C4 H6 2.896(4) . no O1 H51 2.903(3) 3_665 no O1 H2 2.910(3) . no C3 C6 2.956(6) . no O1 H71 2.956(3) . no O2 H2 2.956(3) . no Cl H102 2.9650(10) 4_565 no O1 H31 2.978(3) 3_665 no O1 H72 2.996(4) . no C6 H52 3.000(4) 3_666 no C2 C5 3.011(6) . no C8 H113 3.037(4) 2_655 no C2 H6 3.048(4) . no C7 H52 3.089(4) . no O1 H52 3.091(3) 2_655 no C8 H51 3.112(4) . no C6 Cl 3.116(3) . no O3 H112 3.117(2) 3_766 no C5 C8 3.157(5) . no C9 Cl 3.175(4) . no C10 H103 3.184(4) 3_776 no C2 O1 3.191(4) . no C11 H72 3.200(4) 2_645 no C10 H113 3.202(4) 3_766 no C8 H31 3.229(4) 3_665 no C9 H2 3.229(4) 4_565 no O2 H6 3.237(3) . no O2 H31 3.242(3) 4_565 no C2 Cl 3.250(3) . no N1 H32 3.258(3) . no O2 H101 3.270(3) . no O2 H102 3.270(3) . no Cl O3 3.289(3) 4_565 no C6 O1 3.298(4) . no N1 H52 3.304(3) . no C2 O2 3.304(5) 4_564 no C7 H111 3.307(4) 2_655 no C5 H6 3.311(4) 3_666 no C10 H112 3.311(4) 3_766 no C2 H51 3.328(4) . no C6 H2 3.345(4) . no O3 H113 3.351(2) 3_766 no C6 H31 3.352(4) . no C5 H32 3.369(4) . no C5 H112 3.371(4) . no C4 C9 3.376(5) . no Cl H2 3.3790(10) 4_565 no C3 H52 3.379(4) . no C3 H113 3.380(4) . no C9 H31 3.380(4) . no C4 H2 3.380(4) . no C6 C9 3.390(6) . no C11 H102 3.396(5) 2_745 no C9 H6 3.398(4) . no C5 H72 3.405(4) . no C8 H52 3.409(4) 2_655 no C7 H31 3.413(4) 3_665 no C9 H71 3.432(4) 2_655 no C5 H52 3.438(4) 3_666 no C7 H113 3.440(4) 2_655 no C7 H101 3.443(4) 4_464 no C8 H111 3.458(4) 2_655 no C7 O2 3.462(5) 2_645 no C9 Cl 3.476(4) 4_564 no C6 O1 3.489(5) 4_565 no C2 C7 3.492(6) . no C11 O1 3.498(5) 3_665 no C7 H52 3.499(4) 3_666 no C3 H6 3.500(4) . no C8 H6 3.505(4) 4_564 no C6 O2 3.510(5) . no Cl O3 3.523(3) . no C3 C8 3.527(5) . no C3 H102 3.544(4) 2_745 no N1 Cl 3.545(3) . no C8 H51 3.550(5) 3_665 no C7 O1 3.554(5) 4_565 no C10 H72 3.557(4) 4_665 no Cl O2 3.559(3) . no C8 H31 3.564(4) . no O2 H52 3.567(3) 2_655 no C11 O1 3.574(6) 2_645 no C10 Cl 3.577(4) 4_564 no C5 O2 3.584(4) 2_645 no Cl H32 3.5860(10) 3_766 no C8 H111 3.597(4) 3_665 no Cl H111 3.6030(10) . no C3 O2 3.604(5) . no C10 C11 3.608(5) 3_766 no N1 O3 3.609(4) . no Cl H51 3.6170(10) . no C8 C9 3.619(5) . no Cl H31 3.6200(10) . no O3 H31 3.621(3) . no O1 H101 3.625(3) 4_464 no N1 H51 3.634(3) 2_655 no C8 H51 3.653(4) 2_655 no C3 H103 3.675(4) 4_564 no O1 H111 3.677(4) 2_655 no C11 O3 3.683(4) 3_766 no C3 O2 3.685(5) 4_564 no C8 C11 3.688(6) 2_655 no C10 H71 3.700(4) 2_655 no C2 C10 3.709(5) . no C10 H32 3.718(4) . no C2 H6 3.731(3) 4_564 no C11 H32 3.735(3) 3_766 no C10 H111 3.737(4) 3_766 no Cl H72 3.7380(10) 3_666 no Cl H71 3.7380(10) 3_666 no N1 H52 3.739(3) 2_655 no C10 H71 3.740(4) 4_665 no O2 H32 3.746(3) . no C3 H112 3.751(3) 3_766 no C5 O1 3.751(5) 3_665 no C3 H71 3.759(4) 3_665 no C9 H51 3.762(4) 2_655 no C5 H2 3.765(4) . no C8 O2 3.775(4) . no C8 H101 3.779(4) 4_464 no O1 H102 3.788(3) 4_464 no C4 H112 3.794(4) 3_766 no N1 H6 3.813(3) 4_564 no C3 O1 3.815(5) 3_665 no C4 O3 3.818(5) . no C6 H32 3.824(4) . no Cl O2 3.826(4) 4_565 no Cl H103 3.8300(10) 4_565 no C10 H111 3.834(5) 2_755 no C4 O1 3.839(5) 3_665 no C5 O1 3.841(5) 2_645 no C6 H2 3.846(3) 4_565 no O2 H32 3.846(3) 4_565 no C10 H31 3.847(5) 2_755 no C7 H103 3.851(4) 2_645 no C7 C11 3.852(5) 2_655 no O1 H51 3.858(3) 2_655 no C4 C7 3.858(5) . no C6 H6 3.861(4) 3_666 no C6 C11 3.863(6) . no O1 O2 3.874(5) 4_564 no C9 H112 3.876(3) 3_766 no C11 Cl 3.880(5) 3_766 no C10 C10 3.903(6) 3_776 no C4 C8 3.906(5) . no C2 H52 3.915(4) . no C2 C11 3.918(5) . no C7 H2 3.919(5) . no Cl H101 3.9240(10) . no C10 H112 3.931(5) 2_755 no C5 C6 3.942(6) 3_666 no C8 H52 3.944(4) . no C5 C8 3.946(5) 2_645 no N1 O1 3.955(5) 4_565 no C7 C10 3.961(5) 4_464 no C11 H112 3.965(4) 3_766 no C2 Cl 3.976(4) 4_564 no O1 H6 3.976(3) . no O3 H112 3.979(3) 2_755 no C10 H2 3.982(4) . no C5 C9 3.993(5) . no O1 H113 3.996(3) 3_665 no C2 H102 4.000(4) . no O2 H72 4.001(3) 2_655 no N1 H2 4.003(3) 4_565 no C10 H32 4.004(5) 2_755 no C10 H102 4.009(4) 3_776 no C7 H102 4.017(3) 4_464 no C2 H101 4.023(3) . no C11 H102 4.025(4) 3_766 no C6 O2 4.039(4) 2_645 no C7 Cl 4.057(5) 3_666 no C3 C7 4.080(6) . no Cl H52 4.0860(10) 3_666 no C4 O2 4.101(5) . no N1 O2 4.105(5) 4_564 no C8 O1 4.115(6) 4_565 no C10 O1 4.162(6) 4_665 no N1 C5 4.163(5) 2_655 no C5 C5 4.167(6) 3_666 no C3 C8 4.181(5) 3_665 no C2 C9 4.190(6) 4_564 no C9 O2 4.194(5) 4_564 no C9 O1 4.207(4) . no Cl H2 4.2070(10) . no Cl H111 4.2130(10) 3_766 no O2 O3 4.228(4) 4_565 no C3 O1 4.238(4) . no C3 C10 4.248(5) . no C5 O1 4.255(4) . no N1 C11 4.260(5) . no C10 Cl 4.261(5) . no C4 O1 4.262(5) 2_645 no C8 O2 4.265(6) 4_564 no C6 C6 4.279(6) 3_666 no C10 C11 4.348(7) 2_755 no C7 C9 4.349(5) 2_645 no C5 C9 4.352(5) 2_645 no C8 C10 4.371(6) 4_464 no C6 C8 4.386(6) 4_565 no C3 C10 4.391(6) 2_745 no C3 C7 4.404(5) 3_665 no C5 C7 4.408(6) 3_666 no C3 Cl 4.417(4) 3_766 no C7 C9 4.426(6) . no C5 C8 4.429(6) 3_665 no C6 Cl 4.469(5) 3_666 no C4 Cl 4.575(4) 3_766 no Cl Cl 4.673(2) 3_766 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 39.0(4) yes N1 C2 C3 C4 -40.5(3) yes C2 C3 C4 C5 52.2(4) yes C3 C4 C5 C6 -55.6(4) yes C4 C5 C6 N1 48.3(4) yes C5 C6 N1 C2 -44.0(4) yes C8 N1 C6 C7 -4.4(3) yes N1 C6 C7 C8 3.9(3) yes C6 C7 C8 N1 -4.2(3) yes C7 C8 N1 C6 4.4(3) yes C6 N1 C2 C9 -87.8(4) no C6 N1 C2 H2 155.0(3) no C8 N1 C2 C3 -110.7(4) no C8 N1 C2 C9 122.5(4) no C8 N1 C2 H2 5.3(6) no C2 N1 C6 C7 -163.2(3) no C2 N1 C6 H6 83.2(5) no C8 N1 C6 C5 114.7(3) no C8 N1 C6 H6 -118.1(4) no C2 N1 C8 C7 160.2(4) no C2 N1 C8 O1 -19.1(8) no C6 N1 C8 O1 -174.8(5) no N1 C2 C3 H31 80.3(4) no N1 C2 C3 H32 -161.2(3) no C9 C2 C3 C4 84.5(4) no C9 C2 C3 H31 -154.7(4) no C9 C2 C3 H32 -36.2(5) no H2 C2 C3 C4 -156.5(3) no H2 C2 C3 H31 -35.8(4) no H2 C2 C3 H32 82.7(4) no N1 C2 C9 O2 -10.0(5) no N1 C2 C9 O3 172.8(3) no C3 C2 C9 O2 -133.9(4) no C3 C2 C9 O3 48.9(4) no H2 C2 C9 O2 107.1(5) no H2 C2 C9 O3 -70.0(4) no C2 C3 C4 C11 178.0(3) no C2 C3 C4 Cl -66.0(3) no H31 C3 C4 C5 -68.5(4) no H31 C3 C4 C11 57.3(4) no H31 C3 C4 Cl 173.3(2) no H32 C3 C4 C5 173.0(3) no H32 C3 C4 C11 -61.2(4) no H32 C3 C4 Cl 54.8(4) no C3 C4 C5 H51 64.6(4) no C3 C4 C5 H52 -175.9(3) no C11 C4 C5 C6 179.1(3) no C11 C4 C5 H51 -60.6(4) no C11 C4 C5 H52 58.8(4) no Cl C4 C5 C6 62.9(3) no Cl C4 C5 H51 -176.9(2) no Cl C4 C5 H52 -57.4(4) no C3 C4 C11 H111 -59.8(4) no C3 C4 C11 H112 59.8(4) no C3 C4 C11 H113 -180.0(3) no C5 C4 C11 H111 66.2(5) no C5 C4 C11 H112 -174.2(3) no C5 C4 C11 H113 -54.0(4) no Cl C4 C11 H111 -176.9(3) no Cl C4 C11 H112 -57.3(4) no Cl C4 C11 H113 62.9(4) no C4 C5 C6 C7 145.9(4) no C4 C5 C6 H6 -79.0(5) no H51 C5 C6 N1 -72.0(4) no H51 C5 C6 C7 25.7(6) no H51 C5 C6 H6 160.8(4) no H52 C5 C6 N1 168.5(3) no H52 C5 C6 C7 -93.8(4) no H52 C5 C6 H6 41.3(5) no N1 C6 C7 H71 119.6(4) no N1 C6 C7 H72 -111.8(4) no C5 C6 C7 C8 -107.3(4) no C5 C6 C7 H71 8.4(6) no C5 C6 C7 H72 137.0(4) no H6 C6 C7 C8 117.6(4) no H6 C6 C7 H71 -126.7(4) no H6 C6 C7 H72 1.9(5) no C6 C7 C8 O1 175.0(5) no H71 C7 C8 N1 -119.9(3) no H71 C7 C8 O1 59.3(7) no H72 C7 C8 N1 111.4(3) no H72 C7 C8 O1 -69.3(6) no C2 C9 O3 C10 178.5(3) no O2 C9 O3 C10 1.3(5) no H101 C10 O3 C9 124.3(4) no H102 C10 O3 C9 -126.2(3) no H103 C10 O3 C9 -1.3(5) no _journal_paper_doi 10.1107/S0108270195014788