#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200302.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_2200302 loop_ _publ_author_name 'Nagel, Norbert' 'Schweitzer, Harald' 'Urbach, Hansj\"org' 'Heyse, Winfried' 'M\"uller, Barbara' 'Berchtold, Harald' _publ_section_title ; Ramipril ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o463 _journal_page_last o465 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C23 H32 N2 O5' _chemical_formula_moiety 'C23 H32 N2 O5' _chemical_formula_sum 'C23 H32 N2 O5' _chemical_formula_weight 416.51 _chemical_melting_point 382.15 _chemical_name_common Ramipril _chemical_name_systematic ; 1-[2-(1-ethoxycarbonyl-3-phenylpropylamino)propionyl]octahydrocyclopenta[b]- pyrrole-2-carboxylic acid ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.4845(11) _cell_length_b 13.937(2) _cell_length_c 22.012(3) _cell_measurement_reflns_used 2316 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18.20 _cell_measurement_theta_min 2.36 _cell_volume 2296.1(6) _computing_cell_refinement 'SAINT+ (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT+ _computing_molecular_graphics 'SHELXTL-PC XP (Bruker, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .988 _diffrn_measured_fraction_theta_max .988 _diffrn_measurement_device_type 'Bruker AXS four-circle' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .1662 _diffrn_reflns_av_sigmaI/netI .1287 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 15851 _diffrn_reflns_theta_full 23.31 _diffrn_reflns_theta_max 23.31 _diffrn_reflns_theta_min 2.36 _diffrn_standards_decay_% negligible' _exptl_absorpt_coefficient_mu .085 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 896 _exptl_crystal_size_max .7 _exptl_crystal_size_mid .05 _exptl_crystal_size_min .03 _refine_diff_density_max .131 _refine_diff_density_min -.141 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -2.0(19) _refine_ls_extinction_coef none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .918 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 279 _refine_ls_number_reflns 3291 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .918 _refine_ls_R_factor_all .1558 _refine_ls_R_factor_gt .0643 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0263P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .0854 _reflns_number_gt 1640 _reflns_number_total 3291 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6021.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Y' changed to 'y' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (34 times). '_geom_bond_publ_flag' value 'N' changed to 'n' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (30 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '109\%C' was changed to '382.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '109\%C' was changed to '382.15' - it was converted from degrees Celsius(C) to Kelvins(K). '_geom_bond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (34 times). '_geom_bond_publ_flag' value 'N' changed to 'n' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (30 times). '_geom_angle_publ_flag' value 'N' changed to 'n' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (76 times). '_geom_angle_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (43 times). '_geom_torsion_publ_flag' value 'N' changed to 'n' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (58 times). '_geom_hbond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 2296.0(6) _cod_database_code 2200302 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' '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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O01 .8534(4) .2836(3) .11780(14) .0676(10) Uani d . 1 . . O H1 .939(7) .336(4) .101(2) .109(19) Uiso d . 1 . . H O02 .9727(5) .1845(2) .04956(14) .0710(10) Uani d . 1 . . O O03 .7016(4) -.0561(2) -.00152(12) .0675(10) Uani d . 1 . . O O04 .8473(4) .2369(2) -.17916(14) .0729(10) Uani d . 1 . . O O05 .6397(4) .1236(2) -.19571(14) .0803(11) Uani d . 1 . . O N01 .7448(5) .0376(2) .08079(16) .0547(10) Uani d . 1 . . N N02 .5954(6) .1032(3) -.07252(18) .0526(12) Uani d . 1 . . N H2 .589(5) .049(2) -.0805(16) .039(15) Uiso d . 1 . . H C01 .7351(6) .1286(3) .11407(18) .0584(12) Uani d . 1 . . C H01 .6144 .1553 .1105 .070 Uiso calc R 1 . . H C02 .7694(8) .0984(4) .1801(2) .0944(17) Uani d . 1 . . C H021 .8316 .1487 .2021 .113 Uiso calc R 1 . . H H022 .6579 .0846 .2008 .113 Uiso calc R 1 . . H C03 .8840(9) .0091(4) .1756(2) .0900(17) Uani d . 1 . . C H03 .8515 -.0358 .2080 .108 Uiso calc R 1 . . H C04 .8450(7) -.0370(3) .1131(2) .0692(15) Uani d . 1 . . C H04 .7715 -.0947 .1180 .083 Uiso calc R 1 . . H C05 1.0878(10) .0224(5) .1744(3) .119(2) Uani d . 1 . . C H051 1.1194 .0833 .1560 .143 Uiso calc R 1 . . H H052 1.1366 .0201 .2152 .143 Uiso calc R 1 . . H C06 1.1574(8) -.0604(5) .1366(3) .115(2) Uani d . 1 . . C H062 1.2775 -.0480 .1220 .138 Uiso calc R 1 . . H H061 1.1565 -.1199 .1594 .138 Uiso calc R 1 . . H C07 1.0250(7) -.0628(3) .0852(2) .0769(15) Uani d . 1 . . C H071 1.0207 -.1262 .0671 .092 Uiso calc R 1 . . H H072 1.0575 -.0168 .0541 .092 Uiso calc R 1 . . H C08 .8697(7) .2008(3) .0902(2) .0520(12) Uani d . 1 . . C C09 .6838(5) .0214(3) .0242(2) .0515(13) Uani d . 1 . . C C10 .5754(5) .1012(3) -.00601(18) .0483(12) Uani d . 1 . . C H10 .6131 .1632 .0106 .058 Uiso calc R 1 . . H C11 .3784(5) .0845(3) .00971(18) .0705(14) Uani d . 1 . . C H111 .3414 .0232 -.0056 .106 Uiso calc R 1 . . H H112 .3069 .1341 -.0084 .106 Uiso calc R 1 . . H H113 .3635 .0859 .0530 .106 Uiso calc R 1 . . H C12 .7651(6) .1439(3) -.09581(17) .0468(11) Uani d . 1 . . C H12 .7865 .2047 -.0747 .056 Uiso calc R 1 . . H C13 .7382(8) .1659(4) -.1625(2) .0581(14) Uani d . 1 . . C C14 .8554(8) .2576(4) -.2443(2) .0966(19) Uani d . 1 . . C H141 .8798 .3253 -.2503 .116 Uiso calc R 1 . . H H142 .7409 .2432 -.2628 .116 Uiso calc R 1 . . H C15 .9973(9) .1995(4) -.2738(2) .125(2) Uani d . 1 . . C H151 1.1101 .2128 -.2548 .188 Uiso calc R 1 . . H H152 1.0037 .2157 -.3162 .188 Uiso calc R 1 . . H H153 .9697 .1326 -.2695 .188 Uiso calc R 1 . . H C16 .9326(5) .0823(3) -.08925(17) .0499(12) Uani d . 1 . . C H161 1.0351 .1199 -.1018 .060 Uiso calc R 1 . . H H162 .9483 .0666 -.0466 .060 Uiso calc R 1 . . H C17 .9309(6) -.0108(3) -.12562(19) .0674(13) Uani d . 1 . . C H171 .8300 -.0495 -.1129 .081 Uiso calc R 1 . . H H172 .9154 .0041 -.1683 .081 Uiso calc R 1 . . H C18 1.1002(7) -.0677(3) -.1175(2) .0586(13) Uani d . 1 . . C C19 1.2530(9) -.0455(3) -.14919(19) .0693(14) Uani d . 1 . . C H19 1.2520 .0061 -.1760 .083 Uiso calc R 1 . . H C20 1.4077(8) -.0979(5) -.1421(3) .0842(17) Uani d . 1 . . C H20 1.5082 -.0830 -.1651 .101 Uiso calc R 1 . . H C21 1.4137(11) -.1717(5) -.1014(3) .100(2) Uani d . 1 . . C H21 1.5191 -.2057 -.0952 .119 Uiso calc R 1 . . H C22 1.2611(11) -.1951(4) -.0696(3) .0953(19) Uani d . 1 . . C H22 1.2632 -.2462 -.0425 .114 Uiso calc R 1 . . H C23 1.1063(8) -.1441(4) -.0777(2) .0825(16) Uani d . 1 . . C H23 1.0043 -.1611 -.0560 .099 Uiso calc R 1 . . H 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 O01 .080(3) .060(2) .062(2) -.0136(19) .0148(19) -.009(2) O02 .086(3) .058(2) .069(2) -.0111(18) .025(2) -.0078(19) O03 .088(3) .0458(18) .069(2) -.0039(17) -.0168(17) -.0041(18) O04 .089(3) .079(2) .051(2) .003(2) .005(2) .0188(18) O05 .095(3) .099(3) .046(2) -.003(2) -.0097(19) -.013(2) N01 .079(3) .046(2) .039(2) -.005(2) -.006(2) .006(2) N02 .063(3) .041(3) .054(3) .002(3) -.006(2) -.010(2) C01 .085(4) .054(3) .037(3) -.011(3) .012(3) .000(3) C02 .151(5) .081(4) .051(3) -.013(4) .012(4) .002(3) C03 .138(6) .090(5) .042(3) -.023(4) -.022(4) .020(3) C04 .082(4) .061(4) .064(4) -.011(3) -.012(3) .018(3) C05 .153(7) .118(5) .088(5) -.020(5) -.069(5) .009(4) C06 .120(5) .110(5) .114(5) -.006(4) -.049(5) .038(4) C07 .084(4) .068(3) .079(4) -.004(3) -.022(4) .024(3) C08 .059(4) .054(3) .043(3) -.003(3) -.007(3) .000(3) C09 .056(3) .045(3) .053(3) -.007(3) -.001(3) .013(3) C10 .059(3) .053(3) .033(3) -.007(3) .001(2) -.006(2) C11 .055(3) .083(3) .073(3) -.005(3) .006(3) .001(3) C12 .053(3) .045(3) .043(3) -.001(3) -.005(3) -.010(2) C13 .071(4) .062(4) .042(4) .020(3) .005(3) -.003(3) C14 .115(5) .113(5) .062(4) .018(4) .010(4) .031(3) C15 .140(6) .166(6) .069(4) .015(5) .021(4) .003(4) C16 .053(3) .052(3) .045(3) .007(3) -.006(2) -.001(2) C17 .069(3) .069(3) .064(3) .014(3) -.010(3) -.015(3) C18 .063(4) .050(3) .062(4) .011(3) -.007(3) -.024(3) C19 .079(4) .060(3) .069(3) .014(4) -.003(4) -.021(3) C20 .072(5) .077(4) .104(5) .003(4) .002(4) -.041(4) C21 .106(6) .065(5) .128(6) .027(4) -.038(5) -.035(4) C22 .110(6) .062(4) .113(5) .021(5) -.015(5) .004(3) C23 .091(5) .069(4) .088(4) .011(4) -.002(4) -.014(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O01 C08 . 1.311(5) y O01 H1 . 1.04(6) y O02 C08 . 1.202(5) y O03 C09 . 1.226(5) y O04 C13 . 1.334(5) y O04 C14 . 1.463(4) y O05 C13 . 1.194(5) y N01 C09 . 1.347(4) y N01 C01 . 1.466(4) y N01 C04 . 1.467(5) y N02 C10 . 1.472(5) y N02 C12 . 1.482(5) y N02 H2 . .77(3) y C01 C08 . 1.518(5) y C01 C02 . 1.534(5) y C01 H01 . .9800 n C02 C03 . 1.515(6) y C02 H021 . .9700 n C02 H022 . .9700 n C03 C05 . 1.537(6) y C03 C04 . 1.546(6) y C03 H03 . .9800 n C04 C07 . 1.523(6) y C04 H04 . .9800 n C05 C06 . 1.513(6) y C05 H051 . .9700 n C05 H052 . .9700 n C06 C07 . 1.505(6) y C06 H062 . .9700 n C06 H061 . .9700 n C07 H071 . .9700 n C07 H072 . .9700 n C09 C10 . 1.529(5) y C10 C11 . 1.532(5) y C10 H10 . .9800 n C11 H111 . .9600 n C11 H112 . .9600 n C11 H113 . .9600 n C12 C13 . 1.513(5) y C12 C16 . 1.527(5) y C12 H12 . .9800 n C14 C15 . 1.485(6) y C14 H141 . .9700 n C14 H142 . .9700 n C15 H151 . .9600 n C15 H152 . .9600 n C15 H153 . .9600 n C16 C17 . 1.524(4) y C16 H161 . .9700 n C16 H162 . .9700 n C17 C18 . 1.506(5) y C17 H171 . .9700 n C17 H172 . .9700 n C18 C19 . 1.374(6) y C18 C23 . 1.381(6) y C19 C20 . 1.378(6) y C19 H19 . .9300 n C20 C21 . 1.365(7) y C20 H20 . .9300 n C21 C22 . 1.378(7) y C21 H21 . .9300 n C22 C23 . 1.371(7) y C22 H22 . .9300 n C23 H23 . .9300 n loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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 C08 O01 H1 114(2) n C13 O04 C14 116.1(4) y C09 N01 C01 126.3(4) y C09 N01 C04 120.2(4) y C01 N01 C04 113.4(4) y C10 N02 C12 116.0(3) y C10 N02 H2 102(3) n C12 N02 H2 110(3) n N01 C01 C08 111.5(4) y N01 C01 C02 103.2(3) y C08 C01 C02 113.5(4) y N01 C01 H01 109.5 n C08 C01 H01 109.5 n C02 C01 H01 109.5 n C03 C02 C01 104.9(4) y C03 C02 H021 110.8 n C01 C02 H021 110.8 n C03 C02 H022 110.8 n C01 C02 H022 110.8 n H021 C02 H022 108.8 n C02 C03 C05 117.6(5) y C02 C03 C04 107.1(4) y C05 C03 C04 102.8(5) y C02 C03 H03 109.6 n C05 C03 H03 109.6 n C04 C03 H03 109.6 n N01 C04 C07 115.1(4) y N01 C04 C03 103.5(4) y C07 C04 C03 106.9(4) y N01 C04 H04 110.4 n C07 C04 H04 110.4 n C03 C04 H04 110.4 n C06 C05 C03 105.0(5) y C06 C05 H051 110.7 n C03 C05 H051 110.7 n C06 C05 H052 110.7 n C03 C05 H052 110.7 n H051 C05 H052 108.8 n C07 C06 C05 101.7(5) y C07 C06 H062 111.4 n C05 C06 H062 111.4 n C07 C06 H061 111.4 n C05 C06 H061 111.4 n H062 C06 H061 109.3 n C06 C07 C04 105.9(4) y C06 C07 H071 110.6 n C04 C07 H071 110.6 n C06 C07 H072 110.6 n C04 C07 H072 110.6 n H071 C07 H072 108.7 n O02 C08 O01 124.8(4) y O02 C08 C01 124.0(5) y O01 C08 C01 111.2(4) y O03 C09 N01 122.6(4) y O03 C09 C10 119.9(4) y N01 C09 C10 117.3(4) y N02 C10 C09 113.1(4) y N02 C10 C11 109.0(3) y C09 C10 C11 107.6(3) y N02 C10 H10 109.1 n C09 C10 H10 109.1 n C11 C10 H10 109.1 n C10 C11 H111 109.5 n C10 C11 H112 109.5 n H111 C11 H112 109.5 n C10 C11 H113 109.5 n H111 C11 H113 109.5 n H112 C11 H113 109.5 n N02 C12 C13 107.4(4) y N02 C12 C16 117.1(3) y C13 C12 C16 108.3(3) y N02 C12 H12 107.9 n C13 C12 H12 107.9 n C16 C12 H12 107.9 n O05 C13 O04 125.2(5) y O05 C13 C12 125.2(5) y O04 C13 C12 109.6(5) y O04 C14 C15 110.5(4) y O04 C14 H141 109.5 n C15 C14 H141 109.5 n O04 C14 H142 109.5 n C15 C14 H142 109.5 n H141 C14 H142 108.1 n C14 C15 H151 109.5 n C14 C15 H152 109.5 n H151 C15 H152 109.5 n C14 C15 H153 109.5 n H151 C15 H153 109.5 n H152 C15 H153 109.5 n C17 C16 C12 115.0(3) n C17 C16 H161 108.5 n C12 C16 H161 108.5 n C17 C16 H162 108.5 n C12 C16 H162 108.5 n H161 C16 H162 107.5 n C18 C17 C16 112.3(3) y C18 C17 H171 109.1 n C16 C17 H171 109.1 n C18 C17 H172 109.1 n C16 C17 H172 109.1 n H171 C17 H172 107.9 n C19 C18 C23 117.9(5) y C19 C18 C17 121.5(5) y C23 C18 C17 120.6(6) y C18 C19 C20 121.5(5) y C18 C19 H19 119.2 n C20 C19 H19 119.2 n C21 C20 C19 120.1(6) y C21 C20 H20 120.0 n C19 C20 H20 120.0 n C20 C21 C22 119.0(7) y C20 C21 H21 120.5 n C22 C21 H21 120.5 n C23 C22 C21 120.8(6) y C23 C22 H22 119.6 n C21 C22 H22 119.6 n C22 C23 C18 120.6(6) y C22 C23 H23 119.7 n C18 C23 H23 119.7 n loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O01 H1 N02 4_555 1.04(6) 1.58(6) 2.601(5) 168(4) y N02 H2 O03 . .78(3) 2.43(3) 2.829(5) 114(3) y C03 H03 O05 2_655 .98 2.45 3.388(6) 161 y 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 C09 N01 C01 C08 -74.4(5) n C04 N01 C01 C08 100.3(4) n C09 N01 C01 C02 163.4(4) n C04 N01 C01 C02 -21.9(5) n N01 C01 C02 C03 28.0(5) n C08 C01 C02 C03 -92.8(5) n C01 C02 C03 C05 89.8(5) n C01 C02 C03 C04 -25.2(5) n C09 N01 C04 C07 65.4(5) n C01 N01 C04 C07 -109.7(4) n C09 N01 C04 C03 -178.5(4) n C01 N01 C04 C03 6.4(5) n C02 C03 C04 N01 12.1(5) n C05 C03 C04 N01 -112.5(5) n C02 C03 C04 C07 134.0(4) n C05 C03 C04 C07 9.4(5) n C02 C03 C05 C06 -149.4(4) n C04 C03 C05 C06 -32.1(5) n C03 C05 C06 C07 42.6(5) n C05 C06 C07 C04 -36.1(5) n N01 C04 C07 C06 130.8(4) n C03 C04 C07 C06 16.6(5) n N01 C01 C08 O02 -.9(6) n C02 C01 C08 O02 115.1(5) n N01 C01 C08 O01 176.4(4) n C02 C01 C08 O01 -67.6(5) n C01 N01 C09 O03 177.7(4) n C04 N01 C09 O03 3.3(6) n C01 N01 C09 C10 -7.4(6) n C04 N01 C09 C10 178.2(3) n C12 N02 C10 C09 -76.2(4) n C12 N02 C10 C11 164.2(3) n O03 C09 C10 N02 -35.6(5) n N01 C09 C10 N02 149.4(4) n O03 C09 C10 C11 84.7(5) n N01 C09 C10 C11 -90.3(4) n C10 N02 C12 C13 -163.9(4) n C10 N02 C12 C16 74.0(5) n C14 O04 C13 O05 -5.5(6) n C14 O04 C13 C12 171.8(4) n N02 C12 C13 O05 -29.5(6) n C16 C12 C13 O05 97.8(5) n N02 C12 C13 O04 153.3(3) n C16 C12 C13 O04 -79.4(4) n C13 O04 C14 C15 -89.9(5) n N02 C12 C16 C17 64.8(4) n C13 C12 C16 C17 -56.8(5) n C12 C16 C17 C18 179.5(4) n C16 C17 C18 C19 -80.5(5) n C16 C17 C18 C23 99.3(5) n C23 C18 C19 C20 .6(6) n C17 C18 C19 C20 -179.6(4) n C18 C19 C20 C21 -2.3(7) n C19 C20 C21 C22 2.7(8) n C20 C21 C22 C23 -1.4(9) n C21 C22 C23 C18 -.3(8) n C19 C18 C23 C22 .7(7) n C17 C18 C23 C22 -179.1(4) n _cod_database_fobs_code 2200302