#------------------------------------------------------------------------------ #$Date: 2014-09-06 00:49:45 +0300 (Sat, 06 Sep 2014) $ #$Revision: 122813 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/75/1517511.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_1517511 loop_ _publ_author_name 'Bailey, Stephen J.' 'Wales, Steven M.' 'Willis, Anthony C.' 'Keller, Paul A.' _publ_section_title ; Ring-opening and -expansion of 2,2'-biaziridine: access to diverse enantiopure linear and bicyclic vicinal diamines. ; _journal_issue 16 _journal_name_full 'Organic letters' _journal_page_first 4344 _journal_page_last 4347 _journal_paper_doi 10.1021/ol502164b _journal_volume 16 _journal_year 2014 _chemical_absolute_configuration ad _chemical_compound_source ' from U of Wollongong' _chemical_formula_moiety 'C20 H24 N2 O4 S2' _chemical_formula_sum 'C20 H24 N2 O4 S2' _chemical_formula_weight 420.55 _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' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _audit_creation_date 13-12-20 _audit_creation_method CRYSTALS_ver_14.40 _audit_update_record ; 2013-12-20 - Report on C20 H24 N2 O4 S2 by Anthony C. Willis for Paul Keller 2013-12-20 - passes checkcif tests with minor warnings ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.3346(1) _cell_length_b 10.9278(2) _cell_length_c 18.3511(4) _cell_measurement_reflns_used 20881 _cell_measurement_temperature 200 _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3 _cell_volume 2072.47(6) _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 200 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 27673 _diffrn_reflns_theta_full 27.486 _diffrn_reflns_theta_max 27.486 _diffrn_reflns_theta_min 2.713 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.285 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 888 _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.18 _refine_diff_density_min -0.36 _refine_ls_abs_structure_details 'Flack (1983), 2064 Friedel-pairs' _refine_ls_abs_structure_Flack 0.02(6) _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9978 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 4758 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0339 _refine_ls_shift/su_max 0.0006516 _refine_ls_shift/su_mean 0.0000757 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.60P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0867 _refine_ls_wR_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.0867 _reflns_limit_h_max 13 _reflns_limit_h_min -13 _reflns_limit_k_max 14 _reflns_limit_k_min 0 _reflns_limit_l_max 23 _reflns_limit_l_min 0 _reflns_number_gt 4326 _reflns_number_total 4760 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 3.22 _oxford_diffrn_Wilson_scale 2.16 _oxford_refine_ls_r_factor_ref 0.0389 _oxford_refine_ls_scale 0.6845(13) _oxford_reflns_number_all 4758 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _oxford_structure_analysis_title 'kel1309 At 12:40 on 18/12 - scalepack' _[local]_cod_data_source_file ol502164b_si_005.cif _[local]_cod_data_source_block kel1309 _[local]_cod_cif_authors_sg_H-M 'P 21 21 21 ' _[local]_cod_cif_authors_sg_Hall 'P 2ac 2ab ' _cod_database_code 1517511 _iucr_refine_instruction_details_constraints ; BLOCK SCALE X'S, U'S CONT ENANTIO RIDE N ( 1,X'S) H ( 1,X'S) RIDE C ( 1,X'S) H ( 11,X'S) H ( 12,X'S) RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) H ( 42,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) H ( 133,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) H ( 203,X'S) END ; _iucr_refine_instruction_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn S1 S 0.25577(4) 0.37405(4) 0.55661(2) 0.0370 1.0000 Uani . S2 S 0.61850(4) 0.80405(4) 0.61107(3) 0.0410 1.0000 Uani . O1 O 0.32852(14) 0.29378(14) 0.60274(8) 0.0455 1.0000 Uani . O2 O 0.12803(13) 0.40982(14) 0.57670(8) 0.0495 1.0000 Uani . O3 O 0.56270(15) 0.89234(13) 0.65904(10) 0.0544 1.0000 Uani . O4 O 0.64742(15) 0.83747(13) 0.53720(9) 0.0505 1.0000 Uani . N1 N 0.33888(14) 0.49985(14) 0.54953(10) 0.0380 1.0000 Uani . N2 N 0.51117(14) 0.69169(14) 0.60443(9) 0.0390 1.0000 Uani . C1 C 0.5145(2) 0.5327(2) 0.45845(11) 0.0440 1.0000 Uani . C2 C 0.47928(17) 0.49246(17) 0.53605(10) 0.0350 1.0000 Uani . C3 C 0.55326(18) 0.56318(16) 0.59200(10) 0.0351 1.0000 Uani . C4 C 0.5006(2) 0.5988(2) 0.66379(11) 0.0459 1.0000 Uani . C5 C 0.6523(2) 0.5009(2) 0.43874(12) 0.0509 1.0000 Uani . C6 C 0.7418(3) 0.5795(3) 0.42350(13) 0.0706 1.0000 Uani . C7 C 0.24654(18) 0.30561(16) 0.46964(10) 0.0342 1.0000 Uani . C8 C 0.34108(18) 0.22322(17) 0.44783(12) 0.0403 1.0000 Uani . C9 C 0.3338(2) 0.17103(18) 0.37974(12) 0.0443 1.0000 Uani . C10 C 0.2326(2) 0.19796(19) 0.33236(11) 0.0423 1.0000 Uani . C11 C 0.13909(19) 0.2810(2) 0.35555(11) 0.0439 1.0000 Uani . C12 C 0.14566(17) 0.33602(18) 0.42323(11) 0.0391 1.0000 Uani . C13 C 0.2274(3) 0.1410(2) 0.25757(13) 0.0617 1.0000 Uani . C14 C 0.76003(19) 0.74464(16) 0.65131(11) 0.0386 1.0000 Uani . C15 C 0.7734(2) 0.74615(19) 0.72663(12) 0.0453 1.0000 Uani . C16 C 0.8813(2) 0.6914(2) 0.75759(12) 0.0504 1.0000 Uani . C17 C 0.9749(2) 0.63463(19) 0.71451(12) 0.0454 1.0000 Uani . C18 C 0.96137(19) 0.63870(18) 0.63941(12) 0.0434 1.0000 Uani . C19 C 0.85418(17) 0.69288(17) 0.60756(11) 0.0395 1.0000 Uani . C20 C 1.0851(3) 0.5649(3) 0.74865(16) 0.0655 1.0000 Uani . H1 H 0.3030 0.5522 0.5246 0.0459 1.0000 Uiso R H11 H 0.5049 0.6218 0.4558 0.0520 1.0000 Uiso R H12 H 0.4544 0.4944 0.4243 0.0539 1.0000 Uiso R H21 H 0.5040 0.4063 0.5444 0.0408 1.0000 Uiso R H31 H 0.6483 0.5459 0.5916 0.0413 1.0000 Uiso R H41 H 0.5575 0.6006 0.7055 0.0534 1.0000 Uiso R H42 H 0.4152 0.5726 0.6764 0.0549 1.0000 Uiso R H51 H 0.6739 0.4184 0.4370 0.0625 1.0000 Uiso R H61 H 0.7248 0.6645 0.4265 0.0851 1.0000 Uiso R H62 H 0.8251 0.5523 0.4108 0.0849 1.0000 Uiso R H81 H 0.4092 0.2039 0.4800 0.0490 1.0000 Uiso R H91 H 0.4006 0.1157 0.3654 0.0542 1.0000 Uiso R H111 H 0.0681 0.3015 0.3241 0.0529 1.0000 Uiso R H121 H 0.0844 0.3937 0.4387 0.0478 1.0000 Uiso R H131 H 0.1423 0.1385 0.2386 0.0909 1.0000 Uiso R H132 H 0.2793 0.1884 0.2249 0.0938 1.0000 Uiso R H133 H 0.2622 0.0585 0.2565 0.0926 1.0000 Uiso R H151 H 0.7094 0.7803 0.7548 0.0556 1.0000 Uiso R H161 H 0.8922 0.6912 0.8087 0.0593 1.0000 Uiso R H181 H 1.0209 0.6020 0.6092 0.0520 1.0000 Uiso R H191 H 0.8450 0.6950 0.5567 0.0473 1.0000 Uiso R H201 H 1.1568 0.5626 0.7169 0.0981 1.0000 Uiso R H202 H 1.1159 0.6019 0.7919 0.0979 1.0000 Uiso R H203 H 1.0591 0.4837 0.7588 0.0989 1.0000 Uiso R 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 S1 0.0324(2) 0.0387(2) 0.0400(2) -0.00138(19) 0.00463(19) -0.00417(18) S2 0.0359(2) 0.0332(2) 0.0540(3) -0.0025(2) 0.0026(2) -0.00149(18) O1 0.0482(7) 0.0481(8) 0.0401(7) 0.0086(7) -0.0005(6) -0.0047(6) O2 0.0334(7) 0.0582(9) 0.0568(8) -0.0118(7) 0.0124(6) -0.0042(6) O3 0.0498(8) 0.0355(7) 0.0779(11) -0.0145(8) 0.0055(8) 0.0031(6) O4 0.0501(8) 0.0456(8) 0.0557(9) 0.0119(7) 0.0002(7) -0.0041(7) N1 0.0304(7) 0.0337(8) 0.0499(9) -0.0012(7) -0.0012(7) -0.0012(6) N2 0.0338(7) 0.0344(8) 0.0489(9) -0.0018(8) 0.0044(7) -0.0018(6) C1 0.0423(10) 0.0484(11) 0.0413(11) 0.0026(9) -0.0015(8) 0.0020(9) C2 0.0320(8) 0.0316(9) 0.0413(10) 0.0006(7) 0.0011(7) -0.0012(7) C3 0.0334(8) 0.0308(8) 0.0412(10) 0.0036(7) 0.0004(7) -0.0018(7) C4 0.0449(11) 0.0494(12) 0.0435(11) -0.0018(9) 0.0059(9) -0.0128(9) C5 0.0518(12) 0.0580(13) 0.0428(11) 0.0041(10) 0.0066(10) 0.0096(10) C6 0.0553(14) 0.108(2) 0.0486(12) 0.0063(13) 0.0124(11) -0.0080(15) C7 0.0310(8) 0.0308(8) 0.0409(9) 0.0019(7) 0.0022(7) -0.0020(8) C8 0.0335(8) 0.0398(10) 0.0476(11) -0.0003(9) -0.0045(8) 0.0050(7) C9 0.0434(10) 0.0397(10) 0.0498(12) -0.0060(8) -0.0013(9) 0.0069(8) C10 0.0455(10) 0.0382(9) 0.0431(10) -0.0002(8) -0.0029(8) -0.0047(8) C11 0.0377(10) 0.0500(11) 0.0441(11) 0.0064(9) -0.0053(8) -0.0004(8) C12 0.0295(8) 0.0397(10) 0.0481(11) 0.0057(8) 0.0011(7) 0.0037(7) C13 0.0747(16) 0.0606(14) 0.0499(13) -0.0107(11) -0.0079(12) -0.0012(13) C14 0.0355(9) 0.0344(9) 0.0458(10) -0.0047(7) 0.0023(8) -0.0059(8) C15 0.0439(11) 0.0456(11) 0.0463(11) -0.0106(9) 0.0048(9) -0.0047(9) C16 0.0532(12) 0.0542(12) 0.0437(11) -0.0087(10) -0.0054(9) -0.0063(11) C17 0.0414(10) 0.0386(10) 0.0562(12) -0.0068(9) -0.0068(9) -0.0037(9) C18 0.0391(9) 0.0360(10) 0.0553(12) -0.0083(9) 0.0045(8) -0.0008(8) C19 0.0365(9) 0.0373(9) 0.0447(10) -0.0038(9) 0.0018(8) -0.0037(7) C20 0.0628(15) 0.0588(14) 0.0750(17) -0.0084(13) -0.0247(13) 0.0082(12) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 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 O1 S1 O2 120.08(9) yes O1 S1 N1 106.72(9) yes O2 S1 N1 106.15(9) yes O1 S1 C7 107.65(9) yes O2 S1 C7 107.46(9) yes N1 S1 C7 108.34(8) yes O3 S2 O4 119.63(10) yes O3 S2 N2 105.98(9) yes O4 S2 N2 104.96(9) yes O3 S2 C14 109.01(10) yes O4 S2 C14 108.46(10) yes N2 S2 C14 108.24(8) yes S1 N1 C2 119.14(13) yes S1 N1 H1 113.3 no C2 N1 H1 112.9 no S2 N2 C3 120.95(12) yes S2 N2 C4 119.90(13) yes C3 N2 C4 59.45(12) yes C2 C1 C5 112.34(17) yes C2 C1 H11 107.9 no C5 C1 H11 108.2 no C2 C1 H12 108.8 no C5 C1 H12 110.3 no H11 C1 H12 109.2 no C1 C2 N1 111.95(16) yes C1 C2 C3 111.58(16) yes N1 C2 C3 111.08(15) yes C1 C2 H21 110.9 no N1 C2 H21 106.3 no C3 C2 H21 104.7 no C2 C3 N2 116.33(15) yes C2 C3 C4 124.06(17) yes N2 C3 C4 60.44(13) yes C2 C3 H31 113.6 no N2 C3 H31 117.8 no C4 C3 H31 114.7 no N2 C4 C3 60.11(12) yes N2 C4 H41 121.3 no C3 C4 H41 119.1 no N2 C4 H42 116.6 no C3 C4 H42 118.4 no H41 C4 H42 112.2 no C1 C5 C6 125.0(2) yes C1 C5 H51 117.3 no C6 C5 H51 117.7 no C5 C6 H61 120.4 no C5 C6 H62 119.9 no H61 C6 H62 119.6 no S1 C7 C8 119.85(14) yes S1 C7 C12 119.64(15) yes C8 C7 C12 120.50(18) yes C7 C8 C9 119.51(18) yes C7 C8 H81 119.4 no C9 C8 H81 121.1 no C8 C9 C10 121.39(18) yes C8 C9 H91 118.3 no C10 C9 H91 120.4 no C9 C10 C11 117.94(18) yes C9 C10 C13 120.5(2) yes C11 C10 C13 121.50(19) yes C10 C11 C12 121.64(18) yes C10 C11 H111 119.9 no C12 C11 H111 118.4 no C7 C12 C11 119.00(18) yes C7 C12 H121 118.9 no C11 C12 H121 122.1 no C10 C13 H131 112.4 no C10 C13 H132 109.1 no H131 C13 H132 107.9 no C10 C13 H133 112.9 no H131 C13 H133 108.0 no H132 C13 H133 106.3 no S2 C14 C15 119.69(15) yes S2 C14 C19 119.43(16) yes C15 C14 C19 120.83(19) yes C14 C15 C16 118.9(2) yes C14 C15 H151 119.5 no C16 C15 H151 121.6 no C15 C16 C17 121.1(2) yes C15 C16 H161 120.3 no C17 C16 H161 118.6 no C16 C17 C18 118.7(2) yes C16 C17 C20 120.9(2) yes C18 C17 C20 120.4(2) yes C17 C18 C19 120.91(19) yes C17 C18 H181 121.2 no C19 C18 H181 117.8 no C18 C19 C14 119.51(19) yes C18 C19 H191 120.7 no C14 C19 H191 119.8 no C17 C20 H201 110.6 no C17 C20 H202 112.8 no H201 C20 H202 105.3 no C17 C20 H203 110.0 no H201 C20 H203 108.6 no H202 C20 H203 109.4 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 1.4322(15) yes S1 O2 1.4254(14) yes S1 N1 1.6261(16) yes S1 C7 1.7650(18) yes S2 O3 1.4278(15) yes S2 O4 1.4355(16) yes S2 N2 1.6591(16) yes S2 C14 1.762(2) yes N1 C2 1.474(2) yes N1 H1 0.821 no N2 C3 1.488(2) yes N2 C4 1.493(3) yes C1 C2 1.534(3) yes C1 C5 1.510(3) yes C1 H11 0.980 no C1 H12 0.977 no C2 C3 1.495(3) yes C2 H21 0.987 no C3 C4 1.478(3) yes C3 H31 1.000 no C4 H41 0.965 no C4 H42 0.956 no C5 C6 1.293(4) yes C5 H51 0.929 no C6 H61 0.948 no C6 H62 0.940 no C7 C8 1.388(3) yes C7 C12 1.387(3) yes C8 C9 1.376(3) yes C8 H81 0.943 no C9 C10 1.392(3) yes C9 H91 0.954 no C10 C11 1.392(3) yes C10 C13 1.508(3) yes C11 C12 1.382(3) yes C11 H111 0.960 no C12 H121 0.938 no C13 H131 0.946 no C13 H132 0.957 no C13 H133 0.971 no C14 C15 1.389(3) yes C14 C19 1.382(3) yes C15 C16 1.386(3) yes C15 H151 0.919 no C16 C17 1.395(3) yes C16 H161 0.945 no C17 C18 1.386(3) yes C17 C20 1.507(3) yes C18 C19 1.385(3) yes C18 H181 0.920 no C19 H191 0.939 no C20 H201 0.943 no C20 H202 0.946 no C20 H203 0.946 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 O1 C15 3.344(3) 3_646 no O1 C11 3.399(2) 2_556 no O1 C16 3.539(3) 3_646 no O2 C18 3.248(2) 1_455 no O2 C9 3.266(2) 2_456 no O2 C8 3.333(2) 2_456 no O2 O4 3.469(2) 2_466 no O3 C12 3.439(2) 2_566 no O3 C13 3.520(3) 4_565 no O4 N1 3.100(2) 2_566 no C6 C13 3.405(3) 3_655 no C10 C20 3.553(4) 4_664 no 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_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N1 H1 O4 2_466 162 0.82 2.31 3.100(3) yes 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 S1 N1 C2 C1 108.7(2) no S1 N1 C2 C3 -125.8(2) no S1 C7 C8 C9 -179.5(2) no S1 C7 C12 C11 -179.5(2) no S2 N2 C3 C2 -135.3(1) no S2 N2 C3 C4 108.7(2) no S2 N2 C4 C3 -110.5(1) no S2 C14 C15 C16 175.6(2) no S2 C14 C19 C18 -175.6(1) no O1 S1 N1 C2 45.0(2) no O1 S1 C7 C8 -25.3(2) no O1 S1 C7 C12 155.6(2) no O2 S1 N1 C2 174.2(1) no O2 S1 C7 C8 -155.9(2) no O2 S1 C7 C12 25.0(2) no O3 S2 N2 C3 -149.3(1) no O3 S2 N2 C4 -79.1(2) no O3 S2 C14 C15 25.3(2) no O3 S2 C14 C19 -157.1(1) no O4 S2 N2 C3 83.2(2) no O4 S2 N2 C4 153.4(1) no O4 S2 C14 C15 157.1(2) no O4 S2 C14 C19 -25.4(2) no N1 S1 C7 C8 89.8(2) no N1 S1 C7 C12 -89.3(2) no N1 C2 C1 C5 -168.0(2) no N1 C2 C3 N2 -51.1(2) no N1 C2 C3 C4 19.6(2) no N2 S2 C14 C15 -89.5(2) no N2 S2 C14 C19 88.0(2) no N2 C3 C2 C1 74.5(2) no N2 C4 C3 C2 -103.4(2) no C1 C2 C3 C4 145.3(2) no C2 N1 S1 C7 -70.6(2) no C2 C1 C5 C6 -116.9(2) no C2 C3 N2 C4 116.0(2) no C3 N2 S2 C14 -32.5(2) no C3 C2 C1 C5 66.8(2) no C4 N2 S2 C14 37.7(2) no C7 C8 C9 C10 -0.8(3) no C7 C12 C11 C10 -1.4(3) no C8 C7 C12 C11 1.4(3) no C8 C9 C10 C11 0.8(3) no C8 C9 C10 C13 179.2(2) no C9 C8 C7 C12 -0.4(3) no C9 C10 C11 C12 0.3(3) no C12 C11 C10 C13 -178.1(2) no C14 C15 C16 C17 -0.5(3) no C14 C19 C18 C17 0.6(3) no C15 C14 C19 C18 1.9(3) no C15 C16 C17 C18 3.0(3) no C15 C16 C17 C20 -174.1(2) no C16 C15 C14 C19 -1.9(3) no C16 C17 C18 C19 -3.0(3) no C19 C18 C17 C20 174.0(2) no loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag 2 5 0 x 1 0 2 x 3 3 0 x