#------------------------------------------------------------------------------ #$Date: 2011-01-03 14:48:23 +0200 (Mon, 03 Jan 2011) $ #$Revision: 5312 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7101714.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7101714 loop_ _publ_author_name 'Bower, John F' 'Riis-Johannessen, Thomas' 'Szeto, Peter' 'Whitehead, Andrew J' 'Gallagher, Timothy' _publ_section_title ; Stereospecific construction of substituted piperidines. Synthesis of (-)-paroxetine and (+)-laccarin. ; _journal_issue 7 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 728 _journal_page_last 730 _journal_year 2007 _chemical_absolute_configuration unk _chemical_formula_moiety 'C17 H20 N2 O2' _chemical_formula_sum 'C17 H20 N2 O2' _chemical_formula_weight 284.35 _chemical_name_common ; (7S,7aR)-3-Acetyl-4-benzyl-7-methyl-1,4,5,6,7,7a- hexahydropyrrolo(3,2-b)pyridin-2-one ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 103.461(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.6357(16) _cell_length_b 14.869(3) _cell_length_c 10.9996(17) _cell_measurement_reflns_used 1900 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 69.0 _cell_measurement_theta_min 4.21 _cell_volume 1532.6(5) _computing_cell_refinement 'SMART v5.625 (Bruker-AXS, 1997-2001)' _computing_data_collection 'SMART v5.625 (Bruker-AXS, 1997-2001)' _computing_data_reduction ; SAINT v7.06A (Bruker-AXS, 1997-2003) & SHELXTL v6.14 (Bruker-AXS, 2003) ; _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.602 _diffrn_detector_type 'Bruker-AXS SMART 6000' _diffrn_measured_fraction_theta_full 0.869 _diffrn_measured_fraction_theta_max 0.869 _diffrn_measurement_details 'frames, 0.3\% width' _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker-AXS D8' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'glass fibre' _diffrn_radiation_collimation 'Osmic CMF12-38Cu6 (blue) mirror optics' _diffrn_radiation_monochromator 'Osmic CMF12-38Cu6 (blue) mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0880 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 8214 _diffrn_reflns_theta_full 68.96 _diffrn_reflns_theta_max 68.96 _diffrn_reflns_theta_min 4.13 _diffrn_source rotating-anode _diffrn_source_current 120 _diffrn_source_power 4.8 _diffrn_source_size '3 x 0.3mm' _diffrn_source_target Cu _diffrn_source_type 'MAC Science M18XCE' _diffrn_source_voltage 40 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu 0.651 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_correction_T_min 0.53 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2.10 (Sheldrick, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method none _exptl_crystal_description prism _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.348 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 384 _refine_ls_number_reflns 3909 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0647 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1210P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1679 _refine_ls_wR_factor_ref 0.1783 _reflns_number_gt 3459 _reflns_number_total 3909 _reflns_threshold_expression >2\s(I) _[local]_cod_data_source_file b617260a.txt _[local]_cod_data_source_block 18a _[local]_cod_cif_authors_sg_H-M 'P 21' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' 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_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 7101714 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.9374(5) -0.0181(3) 0.7882(4) 0.0284(11) Uani 1 1 d . H1A H 0.9620 -0.0820 0.8073 0.034 Uiso 1 1 calc R H1B H 1.0156 0.0096 0.7566 0.034 Uiso 1 1 calc R C2 C 0.7974(5) -0.0127(3) 0.6859(4) 0.0313(11) Uani 1 1 d . H2A H 0.7253 -0.0524 0.7092 0.038 Uiso 1 1 calc R H2B H 0.8152 -0.0351 0.6061 0.038 Uiso 1 1 calc R C3 C 0.7366(5) 0.0843(3) 0.6661(4) 0.0262(10) Uani 1 1 d . H3 H 0.6421 0.0855 0.6891 0.031 Uiso 1 1 calc R C4 C 0.8403(5) 0.1480(3) 0.7558(4) 0.0236(10) Uani 1 1 d . H4 H 0.9303 0.1556 0.7264 0.028 Uiso 1 1 calc R C7 C 0.8750(4) 0.1144(3) 0.8912(4) 0.0220(9) Uani 1 1 d . C6 C 0.8405(4) 0.1806(3) 0.9713(4) 0.0214(10) Uani 1 1 d . C5 C 0.7774(4) 0.2562(3) 0.8891(4) 0.0196(9) Uani 1 1 d . C8 C 0.7147(5) 0.1154(3) 0.5286(4) 0.0325(11) Uani 1 1 d . H8A H 0.6821 0.1780 0.5211 0.049 Uiso 1 1 calc R H8B H 0.6430 0.0772 0.4748 0.049 Uiso 1 1 calc R H8C H 0.8052 0.1106 0.5028 0.049 Uiso 1 1 calc R C9 C 0.8662(5) 0.1843(3) 1.1108(4) 0.0252(10) Uani 1 1 d . C10 C 0.7795(5) 0.2503(4) 1.1685(4) 0.0376(12) Uani 1 1 d . H10A H 0.7904 0.2360 1.2571 0.056 Uiso 1 1 calc R H10B H 0.6787 0.2459 1.1252 0.056 Uiso 1 1 calc R H10C H 0.8136 0.3116 1.1602 0.056 Uiso 1 1 calc R C11 C 0.9545(5) -0.0238(3) 1.0232(4) 0.0249(10) Uani 1 1 d . H11A H 0.9733 0.0181 1.0951 0.030 Uiso 1 1 calc R H11B H 1.0423 -0.0596 1.0277 0.030 Uiso 1 1 calc R C12 C 0.8348(4) -0.0872(3) 1.0356(3) 0.0207(10) Uani 1 1 d . C13 C 0.8688(5) -0.1696(3) 1.0961(4) 0.0255(10) Uani 1 1 d . H13 H 0.9660 -0.1876 1.1197 0.031 Uiso 1 1 calc R C14 C 0.7643(5) -0.2268(3) 1.1230(4) 0.0270(11) Uani 1 1 d . H14 H 0.7901 -0.2824 1.1647 0.032 Uiso 1 1 calc R C15 C 0.6213(5) -0.2003(3) 1.0872(4) 0.0268(10) Uani 1 1 d . H15 H 0.5492 -0.2380 1.1056 0.032 Uiso 1 1 calc R C16 C 0.5838(5) -0.1198(3) 1.0254(4) 0.0266(11) Uani 1 1 d . H16 H 0.4861 -0.1029 1.0006 0.032 Uiso 1 1 calc R C17 C 0.6889(5) -0.0629(3) 0.9992(4) 0.0264(10) Uani 1 1 d . H17 H 0.6622 -0.0077 0.9567 0.032 Uiso 1 1 calc R N1 N 0.9248(4) 0.0293(2) 0.9063(3) 0.0235(8) Uani 1 1 d . N2 N 0.7770(4) 0.2355(2) 0.7678(3) 0.0243(9) Uani 1 1 d . H2 H 0.7423 0.2711 0.7041 0.029 Uiso 1 1 calc R O1 O 0.7350(3) 0.3306(2) 0.9210(3) 0.0264(7) Uani 1 1 d . O2 O 0.9571(3) 0.1375(2) 1.1823(3) 0.0384(9) Uani 1 1 d . C18 C 0.2989(5) 0.2334(3) 0.3035(4) 0.0250(10) Uani 1 1 d . H18A H 0.3108 0.2982 0.3241 0.030 Uiso 1 1 calc R H18B H 0.2025 0.2245 0.2489 0.030 Uiso 1 1 calc R C19 C 0.4124(5) 0.2037(3) 0.2340(4) 0.0292(11) Uani 1 1 d . H19A H 0.5084 0.2176 0.2860 0.035 Uiso 1 1 calc R H19B H 0.3996 0.2381 0.1551 0.035 Uiso 1 1 calc R C20 C 0.4023(5) 0.1014(3) 0.2041(4) 0.0237(10) Uani 1 1 d . H20 H 0.4984 0.0740 0.2377 0.028 Uiso 1 1 calc R C21 C 0.2952(5) 0.0578(3) 0.2716(4) 0.0222(10) Uani 1 1 d . H21 H 0.1959 0.0697 0.2222 0.027 Uiso 1 1 calc R C24 C 0.3094(4) 0.0910(3) 0.4075(3) 0.0177(9) Uani 1 1 d . C23 C 0.3252(4) 0.0169(3) 0.4894(3) 0.0188(9) Uani 1 1 d . C22 C 0.3301(4) -0.0640(3) 0.4127(4) 0.0192(9) Uani 1 1 d . C25 C 0.3564(6) 0.0809(3) 0.0624(4) 0.0423(14) Uani 1 1 d . H25A H 0.3496 0.0156 0.0496 0.063 Uiso 1 1 calc R H25B H 0.4272 0.1055 0.0203 0.063 Uiso 1 1 calc R H25C H 0.2633 0.1084 0.0274 0.063 Uiso 1 1 calc R C26 C 0.3109(4) 0.0152(3) 0.6216(4) 0.0244(10) Uani 1 1 d . C27 C 0.3658(5) -0.0665(3) 0.7011(4) 0.0360(12) Uani 1 1 d . H27A H 0.3491 -0.0585 0.7850 0.054 Uiso 1 1 calc R H27B H 0.4683 -0.0734 0.7071 0.054 Uiso 1 1 calc R H27C H 0.3154 -0.1203 0.6626 0.054 Uiso 1 1 calc R C28 C 0.3558(5) 0.2292(3) 0.5418(4) 0.0224(9) Uani 1 1 d . H28A H 0.4478 0.2599 0.5454 0.027 Uiso 1 1 calc R H28B H 0.3706 0.1855 0.6115 0.027 Uiso 1 1 calc R C29 C 0.2463(4) 0.2980(3) 0.5590(3) 0.0200(9) Uani 1 1 d . C30 C 0.0987(5) 0.2830(3) 0.5135(4) 0.0281(11) Uani 1 1 d . H30 H 0.0661 0.2301 0.4671 0.034 Uiso 1 1 calc R C31 C 0.0004(5) 0.3464(4) 0.5370(4) 0.0363(12) Uani 1 1 d . H31 H -0.0989 0.3359 0.5067 0.044 Uiso 1 1 calc R C32 C 0.0465(5) 0.4243(3) 0.6041(4) 0.0316(11) Uani 1 1 d . H32 H -0.0206 0.4672 0.6193 0.038 Uiso 1 1 calc R C33 C 0.1927(5) 0.4389(3) 0.6490(4) 0.0248(10) Uani 1 1 d . H33 H 0.2247 0.4916 0.6960 0.030 Uiso 1 1 calc R C34 C 0.2921(5) 0.3775(3) 0.6259(3) 0.0213(10) Uani 1 1 d . H34 H 0.3912 0.3891 0.6553 0.026 Uiso 1 1 calc R N3 N 0.3127(4) 0.1799(2) 0.4214(3) 0.0218(8) Uani 1 1 d . N4 N 0.3145(4) -0.0382(2) 0.2902(3) 0.0249(9) Uani 1 1 d . H4A H 0.3162 -0.0762 0.2292 0.030 Uiso 1 1 calc R O3 O 0.3435(3) -0.14404(19) 0.4467(3) 0.0237(7) Uani 1 1 d . O4 O 0.2537(4) 0.0764(2) 0.6681(3) 0.0380(9) Uani 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.038(3) 0.019(2) 0.033(2) -0.006(2) 0.0175(19) 0.008(2) C2 0.043(3) 0.020(3) 0.032(2) -0.0017(19) 0.0117(19) -0.005(2) C3 0.027(3) 0.019(2) 0.034(2) -0.006(2) 0.0114(17) -0.003(2) C4 0.025(2) 0.019(2) 0.028(2) 0.0004(18) 0.0100(16) 0.002(2) C7 0.017(2) 0.019(2) 0.033(2) -0.0009(19) 0.0113(16) -0.0032(19) C6 0.018(2) 0.015(2) 0.034(2) -0.0064(19) 0.0102(17) -0.0080(18) C5 0.016(2) 0.014(2) 0.030(2) -0.0031(18) 0.0084(16) -0.0055(18) C8 0.043(3) 0.022(3) 0.029(2) -0.004(2) 0.0018(19) 0.005(2) C9 0.025(3) 0.024(2) 0.027(2) -0.0034(19) 0.0059(17) 0.003(2) C10 0.044(3) 0.037(3) 0.033(2) 0.002(2) 0.011(2) 0.010(3) C11 0.023(3) 0.018(2) 0.032(2) 0.0020(19) 0.0043(16) 0.0044(19) C12 0.020(2) 0.024(2) 0.0180(19) -0.0038(17) 0.0034(15) 0.0034(19) C13 0.026(2) 0.023(2) 0.026(2) -0.0057(19) 0.0049(17) 0.003(2) C14 0.038(3) 0.023(3) 0.021(2) -0.0069(18) 0.0087(18) 0.003(2) C15 0.028(3) 0.032(3) 0.021(2) -0.004(2) 0.0078(17) -0.003(2) C16 0.025(2) 0.033(3) 0.021(2) -0.0038(19) 0.0049(16) 0.000(2) C17 0.029(3) 0.028(3) 0.021(2) -0.0006(19) 0.0034(16) 0.005(2) N1 0.023(2) 0.017(2) 0.0319(18) -0.0020(16) 0.0094(14) 0.0038(16) N2 0.031(2) 0.0134(19) 0.0285(18) 0.0004(16) 0.0073(14) 0.0030(16) O1 0.0299(18) 0.0189(17) 0.0347(16) -0.0008(13) 0.0163(13) 0.0012(14) O2 0.039(2) 0.040(2) 0.0320(16) -0.0045(15) -0.0007(14) 0.0133(17) C18 0.035(3) 0.011(2) 0.030(2) 0.0028(19) 0.0114(17) 0.001(2) C19 0.043(3) 0.018(2) 0.029(2) 0.0046(19) 0.0151(19) -0.008(2) C20 0.028(2) 0.018(2) 0.030(2) 0.0098(19) 0.0152(17) 0.004(2) C21 0.024(3) 0.015(2) 0.027(2) 0.0030(18) 0.0070(16) 0.0023(19) C24 0.009(2) 0.018(2) 0.0272(19) 0.0018(18) 0.0062(14) -0.0020(18) C23 0.016(2) 0.013(2) 0.027(2) 0.0030(18) 0.0050(15) -0.0020(19) C22 0.010(2) 0.017(2) 0.031(2) -0.0005(19) 0.0069(15) 0.0016(18) C25 0.078(4) 0.019(3) 0.039(3) 0.004(2) 0.031(3) 0.010(3) C26 0.028(3) 0.020(2) 0.026(2) 0.000(2) 0.0097(17) -0.009(2) C27 0.043(3) 0.033(3) 0.029(2) 0.012(2) 0.005(2) -0.008(3) C28 0.021(2) 0.014(2) 0.032(2) -0.0027(18) 0.0072(16) 0.0001(18) C29 0.025(2) 0.019(2) 0.0181(18) 0.0054(18) 0.0095(15) 0.0024(19) C30 0.025(3) 0.031(3) 0.031(2) -0.006(2) 0.0097(17) -0.001(2) C31 0.021(2) 0.053(4) 0.035(2) -0.001(2) 0.0056(18) 0.004(2) C32 0.033(3) 0.035(3) 0.030(2) 0.003(2) 0.0122(18) 0.011(2) C33 0.038(3) 0.021(2) 0.0193(19) 0.0021(18) 0.0149(17) 0.005(2) C34 0.024(2) 0.025(3) 0.0164(18) 0.0036(18) 0.0079(15) -0.0018(19) N3 0.030(2) 0.014(2) 0.0229(16) 0.0011(15) 0.0085(14) 0.0015(16) N4 0.030(2) 0.018(2) 0.0286(18) 0.0016(16) 0.0107(14) 0.0010(17) O3 0.0236(16) 0.0108(15) 0.0393(16) 0.0028(13) 0.0124(12) 0.0012(13) O4 0.059(2) 0.028(2) 0.0346(17) -0.0014(15) 0.0247(15) -0.0018(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 N1 C1 C2 111.8(4) N1 C1 H1A 109.3 C2 C1 H1A 109.3 N1 C1 H1B 109.3 C2 C1 H1B 109.3 H1A C1 H1B 107.9 C1 C2 C3 112.8(4) C1 C2 H2A 109.0 C3 C2 H2A 109.0 C1 C2 H2B 109.0 C3 C2 H2B 109.0 H2A C2 H2B 107.8 C8 C3 C2 112.0(4) C8 C3 C4 111.1(4) C2 C3 C4 108.2(3) C8 C3 H3 108.5 C2 C3 H3 108.5 C4 C3 H3 108.5 N2 C4 C7 101.8(3) N2 C4 C3 112.4(3) C7 C4 C3 112.4(4) N2 C4 H4 110.0 C7 C4 H4 110.0 C3 C4 H4 110.0 N1 C7 C6 134.9(4) N1 C7 C4 114.6(4) C6 C7 C4 110.4(4) C7 C6 C5 105.7(3) C7 C6 C9 131.2(4) C5 C6 C9 122.9(4) O1 C5 N2 122.9(4) O1 C5 C6 127.7(4) N2 C5 C6 109.4(4) C3 C8 H8A 109.5 C3 C8 H8B 109.5 H8A C8 H8B 109.5 C3 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 O2 C9 C6 123.4(4) O2 C9 C10 118.2(4) C6 C9 C10 118.4(4) C9 C10 H10A 109.5 C9 C10 H10B 109.5 H10A C10 H10B 109.5 C9 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 N1 C11 C12 114.3(3) N1 C11 H11A 108.7 C12 C11 H11A 108.7 N1 C11 H11B 108.7 C12 C11 H11B 108.7 H11A C11 H11B 107.6 C13 C12 C17 117.8(4) C13 C12 C11 119.2(4) C17 C12 C11 122.7(4) C12 C13 C14 122.2(4) C12 C13 H13 118.9 C14 C13 H13 118.9 C15 C14 C13 118.6(4) C15 C14 H14 120.7 C13 C14 H14 120.7 C16 C15 C14 120.7(4) C16 C15 H15 119.7 C14 C15 H15 119.7 C15 C16 C17 120.4(4) C15 C16 H16 119.8 C17 C16 H16 119.8 C16 C17 C12 120.4(4) C16 C17 H17 119.8 C12 C17 H17 119.8 C7 N1 C11 126.8(4) C7 N1 C1 115.5(3) C11 N1 C1 117.4(3) C5 N2 C4 112.6(3) C5 N2 H2 123.7 C4 N2 H2 123.7 N3 C18 C19 110.3(3) N3 C18 H18A 109.6 C19 C18 H18A 109.6 N3 C18 H18B 109.6 C19 C18 H18B 109.6 H18A C18 H18B 108.1 C18 C19 C20 111.7(4) C18 C19 H19A 109.3 C20 C19 H19A 109.3 C18 C19 H19B 109.3 C20 C19 H19B 109.3 H19A C19 H19B 107.9 C21 C20 C25 109.5(4) C21 C20 C19 108.9(3) C25 C20 C19 113.3(4) C21 C20 H20 108.3 C25 C20 H20 108.3 C19 C20 H20 108.3 N4 C21 C20 113.7(4) N4 C21 C24 101.4(3) C20 C21 C24 114.3(3) N4 C21 H21 109.0 C20 C21 H21 109.0 C24 C21 H21 109.0 N3 C24 C23 135.0(4) N3 C24 C21 115.0(3) C23 C24 C21 109.9(3) C24 C23 C22 106.6(3) C24 C23 C26 128.0(4) C22 C23 C26 124.4(4) O3 C22 N4 122.8(4) O3 C22 C23 128.5(4) N4 C22 C23 108.7(4) C20 C25 H25A 109.5 C20 C25 H25B 109.5 H25A C25 H25B 109.5 C20 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 O4 C26 C23 122.8(4) O4 C26 C27 118.7(4) C23 C26 C27 118.4(4) C26 C27 H27A 109.5 C26 C27 H27B 109.5 H27A C27 H27B 109.5 C26 C27 H27C 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 N3 C28 C29 112.8(3) N3 C28 H28A 109.0 C29 C28 H28A 109.0 N3 C28 H28B 109.0 C29 C28 H28B 109.0 H28A C28 H28B 107.8 C34 C29 C30 119.1(4) C34 C29 C28 119.4(4) C30 C29 C28 121.5(4) C31 C30 C29 119.8(4) C31 C30 H30 120.1 C29 C30 H30 120.1 C32 C31 C30 120.8(4) C32 C31 H31 119.6 C30 C31 H31 119.6 C31 C32 C33 119.2(4) C31 C32 H32 120.4 C33 C32 H32 120.4 C34 C33 C32 121.0(4) C34 C33 H33 119.5 C32 C33 H33 119.5 C33 C34 C29 120.2(4) C33 C34 H34 119.9 C29 C34 H34 119.9 C24 N3 C28 126.0(4) C24 N3 C18 115.6(3) C28 N3 C18 117.3(3) C22 N4 C21 113.2(4) C22 N4 H4A 123.4 C21 N4 H4A 123.4 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.507(5) C1 C2 1.545(6) C1 H1A 0.9900 C1 H1B 0.9900 C2 C3 1.553(7) C2 H2A 0.9900 C2 H2B 0.9900 C3 C8 1.548(6) C3 C4 1.553(6) C3 H3 1.0000 C4 N2 1.455(5) C4 C7 1.532(6) C4 H4 1.0000 C7 N1 1.349(6) C7 C6 1.411(6) C6 C5 1.482(6) C6 C9 1.498(6) C5 O1 1.257(5) C5 N2 1.369(5) C8 H8A 0.9800 C8 H8B 0.9800 C8 H8C 0.9800 C9 O2 1.244(5) C9 C10 1.519(6) C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 C11 N1 1.480(5) C11 C12 1.520(6) C11 H11A 0.9900 C11 H11B 0.9900 C12 C13 1.397(6) C12 C17 1.416(6) C13 C14 1.401(6) C13 H13 0.9500 C14 C15 1.399(7) C14 H14 0.9500 C15 C16 1.383(7) C15 H15 0.9500 C16 C17 1.400(6) C16 H16 0.9500 C17 H17 0.9500 N2 H2 0.8800 C18 N3 1.502(5) C18 C19 1.538(6) C18 H18A 0.9900 C18 H18B 0.9900 C19 C20 1.554(6) C19 H19A 0.9900 C19 H19B 0.9900 C20 C21 1.547(6) C20 C25 1.549(6) C20 H20 1.0000 C21 N4 1.448(5) C21 C24 1.550(6) C21 H21 1.0000 C24 N3 1.329(5) C24 C23 1.409(6) C23 C22 1.477(6) C23 C26 1.493(5) C22 O3 1.244(5) C22 N4 1.376(5) C25 H25A 0.9800 C25 H25B 0.9800 C25 H25C 0.9800 C26 O4 1.235(5) C26 C27 1.518(6) C27 H27A 0.9800 C27 H27B 0.9800 C27 H27C 0.9800 C28 N3 1.485(5) C28 C29 1.513(6) C28 H28A 0.9900 C28 H28B 0.9900 C29 C34 1.407(6) C29 C30 1.412(6) C30 C31 1.402(7) C30 H30 0.9500 C31 C32 1.390(7) C31 H31 0.9500 C32 C33 1.397(6) C32 H32 0.9500 C33 C34 1.389(6) C33 H33 0.9500 C34 H34 0.9500 N4 H4A 0.8800 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O3 0.88 2.10 2.975(4) 179.0 2_656 N4 H4A O1 0.88 2.12 2.985(5) 165.8 2_646 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 N1 C1 C2 C3 49.1(5) C1 C2 C3 C8 124.1(4) C1 C2 C3 C4 1.3(5) C8 C3 C4 N2 71.1(5) C2 C3 C4 N2 -165.6(3) C8 C3 C4 C7 -174.7(4) C2 C3 C4 C7 -51.4(5) N2 C4 C7 N1 174.4(3) C3 C4 C7 N1 53.9(5) N2 C4 C7 C6 -3.0(4) C3 C4 C7 C6 -123.5(4) N1 C7 C6 C5 -174.4(4) C4 C7 C6 C5 2.4(5) N1 C7 C6 C9 9.8(8) C4 C7 C6 C9 -173.5(4) C7 C6 C5 O1 -177.8(4) C9 C6 C5 O1 -1.5(7) C7 C6 C5 N2 -0.7(4) C9 C6 C5 N2 175.5(4) C7 C6 C9 O2 19.5(7) C5 C6 C9 O2 -155.8(4) C7 C6 C9 C10 -162.1(5) C5 C6 C9 C10 22.6(6) N1 C11 C12 C13 145.8(4) N1 C11 C12 C17 -40.4(6) C17 C12 C13 C14 -1.2(6) C11 C12 C13 C14 172.8(4) C12 C13 C14 C15 0.4(6) C13 C14 C15 C16 0.6(6) C14 C15 C16 C17 -0.9(6) C15 C16 C17 C12 0.0(6) C13 C12 C17 C16 1.0(6) C11 C12 C17 C16 -172.8(4) C6 C7 N1 C11 2.6(8) C4 C7 N1 C11 -174.0(4) C6 C7 N1 C1 176.5(5) C4 C7 N1 C1 -0.1(5) C12 C11 N1 C7 97.1(5) C12 C11 N1 C1 -76.6(5) C2 C1 N1 C7 -51.4(5) C2 C1 N1 C11 123.0(4) O1 C5 N2 C4 175.9(4) C6 C5 N2 C4 -1.3(5) C7 C4 N2 C5 2.6(4) C3 C4 N2 C5 123.1(4) N3 C18 C19 C20 56.9(5) C18 C19 C20 C21 -8.6(5) C18 C19 C20 C25 113.5(4) C25 C20 C21 N4 77.3(5) C19 C20 C21 N4 -158.3(4) C25 C20 C21 C24 -166.9(4) C19 C20 C21 C24 -42.5(4) N4 C21 C24 N3 172.5(4) C20 C21 C24 N3 49.7(5) N4 C21 C24 C23 -3.7(4) C20 C21 C24 C23 -126.5(4) N3 C24 C23 C22 -172.0(4) C21 C24 C23 C22 3.1(4) N3 C24 C23 C26 19.4(8) C21 C24 C23 C26 -165.5(4) C24 C23 C22 O3 179.8(4) C26 C23 C22 O3 -11.1(6) C24 C23 C22 N4 -1.2(4) C26 C23 C22 N4 167.9(4) C24 C23 C26 O4 15.5(7) C22 C23 C26 O4 -151.2(4) C24 C23 C26 C27 -166.0(4) C22 C23 C26 C27 27.3(6) N3 C28 C29 C34 -147.7(3) N3 C28 C29 C30 34.7(5) C34 C29 C30 C31 -0.9(6) C28 C29 C30 C31 176.7(4) C29 C30 C31 C32 0.4(7) C30 C31 C32 C33 -0.4(7) C31 C32 C33 C34 1.0(6) C32 C33 C34 C29 -1.6(6) C30 C29 C34 C33 1.5(6) C28 C29 C34 C33 -176.2(4) C23 C24 N3 C28 8.7(7) C21 C24 N3 C28 -166.2(4) C23 C24 N3 C18 176.2(4) C21 C24 N3 C18 1.3(5) C29 C28 N3 C24 -128.1(4) C29 C28 N3 C18 64.6(5) C19 C18 N3 C24 -54.4(5) C19 C18 N3 C28 114.2(4) O3 C22 N4 C21 177.8(4) C23 C22 N4 C21 -1.3(5) C20 C21 N4 C22 126.1(4) C24 C21 N4 C22 3.0(4)