#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2005008.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_2005008 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 'C13 H19 N O3' _chemical_formula_sum 'C13 H19 N O3' _chemical_formula_weight 237.28 _chemical_melting_point .61E-60 _chemical_name_systematic ;(5R^*^,6S^*^,10R^*^)-3oxo-6-vinyl-oactahydro-pyrrolo[1,2-a]azepine-5- carboxylic acid methyl ester ; _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_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 118.305(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.5793(5) _cell_length_b 13.5240(8) _cell_length_c 10.4365(6) _cell_measurement_reflns_used 23 _cell_measurement_temperature 293 _cell_measurement_theta_max 47.0 _cell_measurement_theta_min 36.5 _cell_volume 1314.66(14) _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, Dreissig & Hall, 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 CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2634 _diffrn_reflns_reduction_process perpendicular_monochr_Lp _diffrn_reflns_theta_max 69.81 _diffrn_reflns_theta_min 4.9 _diffrn_standards_decay_% 5.4 _diffrn_standards_interval_time 83 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.65 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description 'block shaped crystal' _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max .217 _refine_diff_density_min -.171 _refine_ls_extinction_coef 6.7E-6(3) _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_all .643 _refine_ls_goodness_of_fit_obs .643 _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 155 _refine_ls_number_reflns 1933 _refine_ls_number_restraints 19 _refine_ls_R_factor_all .047 _refine_ls_R_factor_obs .047 _refine_ls_shift/esd_max .001 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w^-1^ = [0.75 + 0.01\s(F)^2^ + 0.0001/\s(F)]' _refine_ls_wR_factor_all .042 _refine_ls_wR_factor_obs .042 _reflns_number_observed 1937 _reflns_number_total 2596 _reflns_observed_criterion refl_observed_if_Inet_>_2.5__sigma(Inet) _[local]_cod_data_source_file jz1068.cif _[local]_cod_data_source_block 3 _[local]_cod_cif_authors_sg_H-M 'P 21/n' _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_original_cell_volume 1314.70(10) _cod_database_code 2005008 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 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 .0550(10) .0540(10) .0394(9) .0117(9) .0183(9) .0032(9) C2 .0460(10) .0500(10) .0380(10) .0020(10) .0191(9) .0022(9) C3 .0510(10) .0510(10) .0420(10) -.0050(10) .0210(10) -.0020(10) C4 .058(2) .083(2) .0560(10) -.0160(10) .0120(10) -.0110(10) C5 .072(2) .104(2) .0480(10) -.001(2) .0010(10) -.006(2) C6 .073(2) .102(2) .0470(10) .019(2) .0060(10) .014(2) C7 .071(2) .062(2) .0450(10) .0150(10) .0230(10) .0120(10) C8 .103(2) .064(2) .081(2) .025(2) .039(2) .024(2) C9 .084(2) .060(2) .078(2) .0220(10) .023(2) .0000(10) C10 .059(2) .061(2) .0550(10) .0120(10) .0190(10) -.0050(10) C11 .0530(10) .0440(10) .0370(10) .0010(10) .0200(10) -.0015(9) C12 .069(2) .087(2) .0530(10) .019(2) .0050(10) .0160(10) C13 .080(2) .0480(10) .0500(10) -.0130(10) .0280(10) -.0010(10) C14 .111(2) .055(2) .073(2) .018(2) .038(2) .0110(10) O1 .117(2) .0850(10) .0490(10) .0230(10) .0320(10) -.0080(10) O2 .0498(9) .0720(10) .0590(10) -.0088(9) .0200(8) .0097(9) O3 .0580(10) .0660(10) .0402(8) .0036(8) .0158(7) .0127(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 N1 .2351(2) .60310(10) .5360(2) .0510(9) Uani C2 .2827(2) .5047(2) .5960(2) .0450(10) Uani C3 .2529(2) .4262(2) .4781(2) .0490(10) Uani C4 .0906(3) .4202(2) .3685(3) .0710(10) Uani C5 .0435(3) .4894(3) .2388(3) .086(2) Uani C6 .0502(3) .5988(2) .2740(3) .083(2) Uani C7 .1971(3) .6366(2) .3877(2) .0610(10) Uani C8 .2004(3) .7505(2) .4060(3) .085(2) Uani C9 .1778(3) .7687(2) .5364(3) .080(2) Uani C10 .2312(3) .6752(2) .6236(3) .0620(10) Uani C11 .4418(2) .5068(2) .7031(2) .0450(10) Uani C12 .6215(3) .4396(2) .9217(3) .079(2) Uani C13 .3077(3) .3267(2) .5479(2) .0610(10) Uani C14 .4044(4) .2770(2) .5327(3) .082(2) Uani O1 .2652(2) .66290(10) .7520(2) .0870(10) Uani O2 .5299(2) .54990(10) .6832(2) .0625(9) Uani O3 .4716(2) .45210(10) .8197(2) .0578(8) Uani H2 .22864 .48466 .65096 .10000 Uiso H3 .30609 .44587 .42318 .10000 Uiso H41 .06557 .34944 .33227 .10000 Uiso H42 .03352 .43716 .42050 .10000 Uiso H51 .11020 .47759 .19460 .10000 Uiso H52 -.05651 .47147 .16221 .10000 Uiso H61 .01614 .63849 .18153 .10000 Uiso H62 -.02056 .61128 .31277 .10000 Uiso H7 .27362 .61411 .36032 .10000 Uiso H81 .29643 .77958 .42209 .10000 Uiso H82 .12328 .78351 .31488 .10000 Uiso H91 .23340 .82884 .59538 .10000 Uiso H92 .07305 .78083 .50695 .10000 Uiso H121 .67160 .40826 .86988 .10000 Uiso H122 .66614 .50692 .95733 .10000 Uiso H123 .64689 .39845 1.01074 .10000 Uiso H13 .26738 .29682 .61034 .10000 Uiso H141 .44281 .21037 .57929 .10000 Uiso H142 .44751 .30532 .47116 .10000 Uiso loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C .017 .009 H 0 0 N .029 .018 O .047 .032 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 5 2 3 1 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 C7 126.8(2) yes C2 N1 C10 119.0(2) yes C7 N1 C10 114.1(2) yes H2 C2 N1 108.2(2) no H2 C2 C11 108.2(2) no H2 C2 C3 108.0(2) no N1 C2 C3 112.9(2) yes N1 C2 C11 109.7(2) yes C3 C2 C11 109.7(2) yes H3 C3 C13 108.5(2) no H3 C3 C2 108.3(2) no H3 C3 C4 108.4(2) no C2 C3 C4 111.2(2) yes C2 C3 C13 110.1(2) yes C4 C3 C13 110.3(2) yes H42 C4 H41 107.3(3) no H42 C4 C5 108.1(2) no H42 C4 C3 109.0(2) no H41 C4 C5 109.3(2) no H41 C4 C3 109.0(2) no C3 C4 C5 113.9(2) yes H52 C5 H51 107.1(3) no H52 C5 C6 109.8(3) no H52 C5 C4 109.6(3) no H51 C5 C6 107.4(3) no H51 C5 C4 107.4(3) no C4 C5 C6 115.3(2) yes H61 C6 H62 107.1(3) no H61 C6 C5 109.4(3) no H61 C6 C7 109.6(3) no H62 C6 C5 107.3(3) no H62 C6 C7 107.7(2) no C5 C6 C7 115.3(2) yes H7 C7 N1 110.1(2) no H7 C7 C6 109.4(2) no H7 C7 C8 110.8(3) no N1 C7 C6 112.5(2) yes N1 C7 C8 101.4(2) yes C6 C7 C8 112.5(2) yes H82 C8 H81 106.2(3) no H82 C8 C9 111.8(3) no H82 C8 C7 111.1(2) no H81 C8 C9 111.0(2) no H81 C8 C7 111.3(3) no C7 C8 C9 105.6(3) yes H92 C9 H91 106.7(3) no H92 C9 C10 111.3(3) no H92 C9 C8 111.8(2) no H91 C9 C10 111.2(2) no H91 C9 C8 112.4(3) no C8 C9 C10 103.6(2) yes N1 C10 C9 108.7(2) yes N1 C10 O1 123.8(2) yes C9 C10 O1 127.5(3) yes C2 C11 O2 124.4(2) yes C2 C11 O3 111.3(2) yes O2 C11 O3 124.3(2) yes H123 C12 H122 106.6(2) no H123 C12 H121 106.5(3) no H123 C12 O3 117.8(3) no H122 C12 H121 107.6(3) no H122 C12 O3 108.9(2) no H121 C12 O3 109.0(2) no H13 C13 C14 117.9(2) no H13 C13 C3 118.8(3) no C3 C13 C14 123.3(3) yes H141 C14 H142 116.0(4) no H141 C14 C13 124.3(4) no H142 C14 C13 119.7(3) no C11 O3 C12 116.3(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.455(3) yes N1 C7 1.474(3) yes N1 C10 1.351(3) yes C2 H2 1.021(3) no C2 C3 1.540(3) yes C2 C11 1.516(3) yes C3 H3 1.011(3) no C3 C4 1.550(3) yes C3 C13 1.509(3) yes C4 H42 1.011(3) no C4 H41 1.016(3) no C4 C5 1.522(4) yes C5 H52 1.007(2) no C5 H51 1.023(4) no C5 C6 1.518(5) yes C6 H61 1.010(3) no C6 H62 1.020(4) no C6 C7 1.528(3) yes C7 H7 1.024(3) no C7 C8 1.551(4) yes C8 H82 1.016(3) no C8 H81 1.026(4) no C8 C9 1.510(5) yes C9 H92 1.013(3) no C9 H91 1.022(3) no C9 C10 1.502(4) yes C10 O1 1.223(3) yes C11 O2 1.198(3) yes C11 O3 1.329(3) yes C12 H123 1.004(3) no C12 H122 1.012(3) no C12 H121 1.012(3) no C12 O3 1.441(3) yes C13 H13 1.017(3) no C13 C14 1.295(5) yes C14 H141 1.013(3) no C14 H142 1.022(4) 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 C14 H13 1.986(4) . no C13 H142 2.008(3) . no O3 H122 2.0120(10) . no O3 H121 2.013(2) . no N1 H2 2.021(2) . no C13 H141 2.045(3) . no N1 H7 2.064(2) . no C5 H62 2.065(4) . no C13 H3 2.066(3) . no C6 H51 2.068(3) . no C5 H42 2.072(3) . no C4 H51 2.073(3) . no C11 H2 2.075(3) . no C7 H62 2.079(3) . no C5 H61 2.083(3) . no C6 H52 2.086(3) . no C4 H52 2.088(2) . no C2 H3 2.090(3) . no C5 H41 2.091(3) . no C3 H2 2.094(3) . no C7 H61 2.095(2) . no C10 H92 2.095(2) . no C10 H91 2.100(3) . no C4 H3 2.100(3) . no C6 H7 2.103(3) . no O3 H123 2.1060(10) . no C9 H81 2.107(4) . no C8 H92 2.107(4) . no C3 H42 2.109(2) . no C9 H82 2.110(3) . no C3 H41 2.112(2) . no C8 H91 2.121(3) . no C7 H82 2.138(2) . no C8 H7 2.140(3) . no C7 H81 2.148(3) . no C3 H13 2.188(2) . no O2 O3 2.235(3) . no N1 O1 2.271(3) . no N1 C9 2.320(3) . no N1 C8 2.341(4) . no O1 H123 2.345(2) 3_667 no C2 O3 2.351(2) . no C11 C12 2.353(3) . no C8 C10 2.367(5) . no O3 H2 2.3680(10) . no C7 C10 2.372(4) . no C2 O2 2.405(3) . no C2 C10 2.418(3) . no N1 C11 2.429(3) . no O1 H13 2.436(2) 2_556 no C7 C9 2.438(4) . no C9 O1 2.448(4) . no O2 H3 2.464(2) 3_666 no C3 C14 2.470(4) . no N1 C3 2.496(3) . no N1 C6 2.497(3) . no C2 C13 2.499(3) . no C3 C11 2.499(3) . no C13 H41 2.501(2) . no C4 C13 2.510(3) . no C14 H3 2.545(3) . no C2 C4 2.549(3) . no C6 C8 2.561(4) . no C2 H42 2.561(2) . no C4 C6 2.567(4) . no C5 C7 2.573(4) . no C3 C5 2.575(3) . no O2 H82 2.579(2) 4_565 no O1 H2 2.586(2) . no O2 H122 2.587(2) . no C5 H3 2.588(3) . no C11 H122 2.589(2) . no C6 H82 2.590(3) . no C11 H121 2.590(2) . no C10 H2 2.595(3) . no N1 H62 2.6040(10) . no O2 H142 2.617(2) 3_666 no C2 C7 2.619(3) . no O2 H121 2.636(2) . no C3 H142 2.657(3) . no C12 O2 2.660(3) . no C8 H61 2.693(3) . no C13 H2 2.697(3) . no C3 H51 2.698(2) . no C11 H3 2.701(2) . no O1 H91 2.702(2) . no N1 H3 2.704(2) . no C6 H42 2.721(3) . no C5 H7 2.730(3) . no C4 H2 2.739(2) . no C2 O1 2.748(3) . no C7 H3 2.777(3) . no C4 H62 2.784(3) . no C7 H51 2.788(2) . no C8 H62 2.793(3) . no C2 H13 2.824(2) . no C2 H7 2.832(2) . no N1 O2 2.839(2) . no C4 H13 2.859(2) . no N1 H81 2.875(2) . no C10 H81 2.876(3) . no C3 H7 2.876(2) . no O1 H92 2.879(2) . no N1 H92 2.883(2) . no C11 C13 2.896(3) . no N1 H42 2.932(2) . no C7 H92 2.937(3) . no C13 H42 2.959(3) . no C3 C7 2.967(3) . no O2 H3 2.9760(10) . no N1 C4 2.997(3) . no C10 C11 3.014(3) . no C11 O1 3.018(4) . no C10 H42 3.024(3) 3_566 no C13 O3 3.043(3) . no O3 H13 3.0610(10) . no C14 H81 3.067(4) 3_666 no C5 H141 3.086(3) 4_454 no C10 H7 3.099(3) . no C4 C7 3.108(4) . no O1 H42 3.109(2) 3_566 no O3 H92 3.110(2) 2_546 no N1 H91 3.117(2) . no C9 H62 3.120(3) . no C6 H91 3.121(3) 4_464 no N1 H42 3.130(2) 3_566 no C9 H122 3.132(3) 4_464 no C12 H52 3.159(2) 1_656 no C3 O2 3.165(2) . no C6 H3 3.168(3) . no O2 H2 3.168(2) . no O1 H92 3.169(2) 4_565 no O3 H91 3.176(2) 2_546 no N1 H82 3.177(2) . no O1 H41 3.183(2) 3_566 no N1 C5 3.183(3) . no C10 H62 3.190(2) . no C4 H141 3.193(3) 4_454 no C3 C6 3.202(4) . no C10 H82 3.216(3) . no O2 H7 3.216(2) 3_666 no C3 O3 3.219(2) . no C10 H13 3.221(3) 2_556 no C9 H7 3.246(3) . no C14 H41 3.248(3) 4 no C11 H123 3.250(2) . no C11 H13 3.273(2) . no C4 H7 3.285(3) . no O2 H7 3.2850(10) . no C7 H91 3.289(3) . no C12 H92 3.295(3) 2_546 no O1 H52 3.295(3) 3_566 no O3 H123 3.301(2) 3_667 no C7 H42 3.309(3) . no C11 H82 3.311(2) 4_565 no C14 H61 3.316(4) 2_545 no C7 H2 3.319(3) . no O3 H122 3.326(2) 3_667 no C14 H41 3.328(3) . no C12 O1 3.329(3) 3_667 no C6 C9 3.331(4) . no C2 C6 3.335(3) . no N1 H61 3.340(2) . no C14 H121 3.356(3) 4_454 no C2 H41 3.356(2) . no C2 H42 3.361(3) 3_566 no C6 H81 3.366(3) . no C8 H122 3.371(3) 4_464 no C10 O2 3.374(3) . no C13 O1 3.376(4) 2_546 no C2 C5 3.376(3) . no C14 H7 3.378(3) 3_666 no C6 C10 3.380(4) . no C6 H92 3.387(3) . no C9 H61 3.397(3) 4_565 no C10 H41 3.398(3) 3_566 no C8 H142 3.400(3) 3_666 no O2 H51 3.414(2) 3_666 no C3 H141 3.415(2) . no C7 H142 3.416(3) 3_666 no C6 H41 3.417(3) . no C4 H61 3.419(3) . no C13 H123 3.420(3) 4_454 no C3 H52 3.424(2) . no C7 H52 3.425(2) . no C3 O2 3.448(4) 3_666 no O1 O3 3.455(3) . no C8 O2 3.459(3) 4_464 no C11 H7 3.468(2) . no O1 H141 3.468(3) 2_556 no C9 H13 3.471(3) 2_556 no C2 H62 3.481(2) . no N1 O3 3.489(2) . no C14 H82 3.499(4) 2_545 no C11 C14 3.509(4) . no C4 C14 3.510(4) . no C2 C14 3.519(4) . no C9 H62 3.523(2) 4_565 no C4 H2 3.529(3) 3_566 no C12 H91 3.530(3) 4_565 no C7 O1 3.536(3) . no C14 H123 3.538(3) 4_454 no C14 O2 3.538(4) 3_666 no C4 O1 3.539(4) 3_566 no C7 C11 3.540(3) . no C10 H123 3.542(3) 3_667 no C8 O1 3.545(4) . no C8 H61 3.546(3) 4_565 no C11 H3 3.549(3) 3_666 no O1 O2 3.549(3) . no C8 H142 3.556(3) 2 no C14 H52 3.572(3) 4 no C6 H2 3.575(4) 3_566 no O2 H81 3.5800(10) 4_565 no N1 H51 3.586(2) . no C5 H2 3.588(4) 3_566 no C3 H62 3.589(2) . no O1 H122 3.594(2) 3_667 no C12 O3 3.595(4) 3_667 no O1 H82 3.598(3) 4_565 no C7 O2 3.603(3) . no C4 H42 3.611(3) 3_566 no N1 H142 3.613(2) 3_666 no C7 H121 3.614(3) 3_666 no C14 O3 3.614(3) . no C12 H141 3.615(3) 4 no C13 H121 3.617(2) 4_454 no C11 H142 3.627(3) 3_666 no C9 O3 3.627(4) 2_556 no O3 H3 3.6500(10) . no O2 H123 3.661(2) . no C11 H142 3.664(2) . no C13 O2 3.672(3) . no C5 H122 3.674(2) 1_454 no O1 H62 3.674(2) 4_565 no C12 H7 3.677(3) 3_666 no C9 H123 3.677(3) 2_556 no C4 C10 3.678(4) 3_566 no C2 H62 3.683(3) 3_566 no C12 H13 3.688(3) 4 no C2 C12 3.691(3) . no C10 H82 3.695(2) 4_565 no C2 C9 3.702(3) . no C9 H61 3.706(3) . no C2 H51 3.710(2) . no C6 H42 3.724(3) 3_566 no C9 H42 3.729(3) 3_566 no C4 H142 3.739(3) . no C8 H141 3.741(4) 3_666 no C3 C10 3.746(4) . no C6 H81 3.748(2) 4_464 no C12 H51 3.748(3) 3_666 no O3 O3 3.750(2) 3_667 no C11 H7 3.751(3) 3_666 no C10 H61 3.751(3) 4_565 no C14 H121 3.754(3) . no C11 H123 3.755(3) 3_667 no C2 C8 3.756(4) . no C4 H62 3.759(3) 3_566 no C2 H142 3.763(3) . no C4 H92 3.770(3) 3_566 no C10 H62 3.770(2) 4_565 no C13 H41 3.775(2) 4 no C5 H2 3.788(3) . no C6 H2 3.792(3) . no C5 H91 3.793(3) 4_464 no C6 H142 3.795(3) 2 no C9 H41 3.795(4) 3_566 no O1 H121 3.800(2) 3_667 no C14 O1 3.805(5) 2_546 no N1 C13 3.806(3) . no C12 H2 3.807(2) . no C5 C13 3.809(3) . no O2 O2 3.814(3) 3_666 no O2 H142 3.843(2) . no C13 H51 3.849(2) . no C10 O3 3.851(3) . no C12 H122 3.876(4) 3_667 no C10 H42 3.877(2) . no C14 H2 3.879(4) . no C13 H121 3.881(2) . no C4 C11 3.882(3) . no C6 H121 3.888(4) 3_666 no C5 O1 3.901(4) 3_566 no C12 H123 3.906(3) 3_667 no C12 H82 3.910(3) 4_565 no C5 H123 3.913(3) 1_454 no O2 H92 3.925(2) 4_565 no O3 H82 3.930(2) 4_565 no C13 O2 3.934(4) 3_666 no C8 C14 3.935(5) 3_666 no C5 C8 3.940(4) . no C5 H121 3.941(4) 3_666 no O1 H81 3.941(2) . no C7 H42 3.948(3) 3_566 no C13 H91 3.948(3) 2_546 no C12 C14 3.949(4) 4 no C6 C9 3.952(4) 4_464 no C2 H121 3.956(2) . no C10 H92 3.964(2) 4_565 no C12 H91 3.967(3) 2_546 no C12 H92 3.973(3) 4_565 no C10 H142 3.974(3) 3_666 no C9 H2 3.983(3) . no C14 O2 3.985(3) . no N1 H41 3.986(2) . no C12 C12 3.992(5) 3_667 no C14 H51 3.995(3) 4 no C12 H41 3.997(3) 4 no O3 H92 4.004(2) 4_565 no C11 H92 4.007(2) 4_565 no C12 C13 4.016(4) 4 no C6 H141 4.017(3) 2 no C7 H142 4.017(2) 2 no C3 H62 4.018(3) 3_566 no C11 H42 4.020(2) . no C2 H122 4.021(2) . no C10 H3 4.025(3) . no N1 C4 4.027(4) 3_566 no C2 H123 4.027(2) 3_667 no C13 H62 4.030(3) 3_566 no C6 H122 4.030(2) 1_454 no C10 H52 4.033(3) 3_566 no C12 C13 4.036(3) . no C9 O1 4.053(3) 4_464 no C7 C14 4.063(5) 3_666 no C9 O2 4.073(3) 4_464 no C9 C12 4.084(4) 4_464 no C4 C14 4.090(4) 4_454 no C5 C14 4.096(4) 4_454 no C9 C12 4.108(5) 2_556 no C8 C11 4.153(3) 4_464 no C7 O2 4.156(4) 3_666 no C5 C12 4.162(3) 1_454 no C4 C10 4.177(4) . no C10 C13 4.179(4) 2_556 no C8 C14 4.183(5) 2 no C6 C14 4.211(5) 2 no C12 C14 4.213(4) . no C5 O2 4.223(4) 3_666 no C11 O2 4.251(3) 3_666 no C3 O1 4.252(3) . no C8 O1 4.258(4) 4_464 no C2 C4 4.261(4) 3_566 no C6 C10 4.262(4) 4_464 no C4 C9 4.271(5) 3_566 no C8 O2 4.280(3) . no O1 O3 4.283(2) 3_667 no C8 C12 4.291(4) 4_464 no C2 O2 4.294(3) 3_666 no C4 O2 4.316(4) 3_666 no C9 C11 4.331(3) . no C11 C12 4.335(4) 3_667 no C5 C10 4.339(4) . no C9 C13 4.340(5) 2_556 no C6 O1 4.344(4) 4_464 no C6 C8 4.372(4) 4_464 no C9 C11 4.395(3) 4_464 no C5 C10 4.406(5) 3_566 no C8 C11 4.414(3) . no C7 C14 4.420(4) 2 no C3 C12 4.422(3) . 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 C7 N1 C2 C3 -15.6(3) yes N1 C2 C3 C4 -58.6(3) yes C2 C3 C4 C5 89.7(3) yes C3 C4 C5 C6 -67.9(4) yes C4 C5 C6 C7 56.5(4) yes C5 C6 C7 N1 -72.5(4) yes C6 C7 N1 C2 75.6(3) yes C10 N1 C7 C8 12.1(3) yes N1 C7 C8 C9 -23.0(3) yes C7 C8 C9 C10 25.7(3) yes C8 C9 C10 N1 -18.8(3) yes C9 C10 N1 C7 4.0(3) yes C7 N1 C2 C11 107.0(2) no C7 N1 C2 H2 -135.1(2) no C10 N1 C2 C3 168.4(2) no C10 N1 C2 C11 -68.9(3) no C10 N1 C2 H2 49.0(3) no C2 N1 C7 C8 -164.0(2) no C2 N1 C7 H7 -46.7(3) no C10 N1 C7 C6 -108.3(3) no C10 N1 C7 H7 129.4(2) no C2 N1 C10 C9 -179.6(2) no C2 N1 C10 O1 -.3(4) no C7 N1 C10 O1 -176.7(3) no N1 C2 C3 C13 178.8(2) no N1 C2 C3 H3 60.3(2) no C11 C2 C3 C4 178.7(2) no C11 C2 C3 C13 56.1(3) no C11 C2 C3 H3 -62.4(2) no H2 C2 C3 C4 60.9(2) no H2 C2 C3 C13 -61.6(3) no H2 C2 C3 H3 179.9(2) no N1 C2 C11 O2 -42.8(3) no N1 C2 C11 O3 139.3(2) no C3 C2 C11 O2 81.7(3) no C3 C2 C11 O3 -96.2(2) no H2 C2 C11 O2 -160.7(2) no H2 C2 C11 O3 21.4(3) no C2 C3 C4 H41 -147.9(2) no C2 C3 C4 H42 -31.1(3) no C13 C3 C4 C5 -147.8(3) no C13 C3 C4 H41 -25.5(4) no C13 C3 C4 H42 91.4(3) no H3 C3 C4 C5 -29.1(3) no H3 C3 C4 H41 93.2(3) no H3 C3 C4 H42 -149.9(2) no C2 C3 C13 C14 -120.0(3) no C2 C3 C13 H13 59.8(3) no C4 C3 C13 C14 116.9(3) no C4 C3 C13 H13 -63.3(3) no H3 C3 C13 C14 -1.7(3) no H3 C3 C13 H13 178.2(2) no C3 C4 C5 H51 51.7(3) no C3 C4 C5 H52 167.7(3) no H41 C4 C5 C6 169.9(3) no H41 C4 C5 H51 -70.5(3) no H41 C4 C5 H52 45.5(4) no H42 C4 C5 C6 53.4(3) no H42 C4 C5 H51 173.0(2) no H42 C4 C5 H52 -70.9(3) no C4 C5 C6 H61 -179.4(3) no C4 C5 C6 H62 -63.5(3) no H51 C5 C6 C7 -63.1(3) no H51 C5 C6 H61 60.9(3) no H51 C5 C6 H62 176.9(2) no H52 C5 C6 C7 -179.2(3) no H52 C5 C6 H61 -55.1(4) no H52 C5 C6 H62 60.8(3) no C5 C6 C7 C8 173.7(3) no C5 C6 C7 H7 50.2(4) no H61 C6 C7 N1 163.5(3) no H61 C6 C7 C8 49.8(4) no H61 C6 C7 H7 -73.7(3) no H62 C6 C7 N1 47.3(3) no H62 C6 C7 C8 -66.4(4) no H62 C6 C7 H7 170.0(2) no N1 C7 C8 H81 97.4(3) no N1 C7 C8 H82 -144.4(3) no C6 C7 C8 C9 97.4(3) no C6 C7 C8 H81 -142.1(3) no C6 C7 C8 H82 -24.0(5) no H7 C7 C8 C9 -139.9(2) no H7 C7 C8 H81 -19.4(3) no H7 C7 C8 H82 98.7(3) no C7 C8 C9 H91 145.8(2) no C7 C8 C9 H92 -94.3(3) no H81 C8 C9 C10 -95.1(3) no H81 C8 C9 H91 25.0(3) no H81 C8 C9 H92 145.0(2) no H82 C8 C9 C10 146.6(2) no H82 C8 C9 H91 -93.3(3) no H82 C8 C9 H92 26.6(4) no C8 C9 C10 O1 161.9(3) no H91 C9 C10 N1 -139.7(3) no H91 C9 C10 O1 41.0(5) no H92 C9 C10 N1 101.5(3) no H92 C9 C10 O1 -77.9(4) no C2 C11 O3 C12 173.4(2) no O2 C11 O3 C12 -4.5(3) no H121 C12 O3 C11 -58.5(3) no H122 C12 O3 C11 58.6(3) no H123 C12 O3 C11 -180.0(2) no C3 C13 C14 H141 179.6(2) no C3 C13 C14 H142 .3(4) no H13 C13 C14 H141 -.3(4) no H13 C13 C14 H142 -179.6(2) no