#------------------------------------------------------------------------------ #$Date: 2021-09-06 15:22:24 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268910 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158163.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_7158163 loop_ _publ_author_name 'Shi, Di' 'Cao, Jinlian' 'Weng, Peimin' 'Yan, Xiaosheng' 'Li, Zhao' 'Jiang, Yun-Bao' _publ_section_title ; Chalcogen bonding mediates the formation of supramolecular helices of azapeptides in crystals. ; _journal_issue 29 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 6397 _journal_page_last 6401 _journal_paper_doi 10.1039/d1ob01053k _journal_volume 19 _journal_year 2021 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C15 H16 N4 O2 S2' _chemical_formula_sum 'C15 H16 N4 O2 S2' _chemical_formula_weight 348.44 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2021-05-13 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2021-05-17 deposited with the CCDC. 2021-07-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.545(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.1096(3) _cell_length_b 8.1557(2) _cell_length_c 10.7216(4) _cell_measurement_reflns_used 2449 _cell_measurement_temperature 99.97(11) _cell_measurement_theta_max 70.4320 _cell_measurement_theta_min 4.3980 _cell_volume 827.78(5) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 99.97(11) _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.944 _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_unetI/netI 0.0510 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.944 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4847 _diffrn_reflns_point_group_measured_fraction_full 0.839 _diffrn_reflns_point_group_measured_fraction_max 0.799 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.386 _diffrn_reflns_theta_min 4.404 _exptl_absorpt_coefficient_mu 3.044 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.75574 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.398 _exptl_crystal_description block _exptl_crystal_F_000 364 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.286 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.057 _refine_ls_abs_structure_details ; Flack x determined using 884 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.001(16) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 217 _refine_ls_number_reflns 2570 _refine_ls_number_restraints 54 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0379 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.0991P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0952 _refine_ls_wR_factor_ref 0.0965 _reflns_Friedel_coverage 0.574 _reflns_Friedel_fraction_full 0.673 _reflns_Friedel_fraction_max 0.630 _reflns_number_gt 2511 _reflns_number_total 2570 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01053k2.cif _cod_data_source_block exp_1885 _cod_depositor_comments 'Adding full bibliography for 7158162--7158163.cif.' _cod_database_code 7158163 _shelx_shelxl_version_number 2014/8 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Shared sites {S002, C002} {C005, S005} 3. Restrained distances C00I-H00I 0.93 with sigma of 0.02 C005-H005 0.93 with sigma of 0.02 4. Uiso/Uaniso restraints and constraints Uanis(C005) = Uanis(S005) Uanis(S002) = Uanis(C002) 5. Rigid body (RIGU) restrains S002, C005, C00E, C00I, C00J, C00B, N007, C00C with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 6. Others Fixed Sof: S002(0.8) C005(0.8) H00J(0.8) H00A(0.2) C002(0.2) S005(0.2) 7.a Ternary CH refined with riding coordinates: C00C(H00C) 7.b Aromatic/amide H refined with riding coordinates: N006(H006), N007(H007), N008(H008), N009(H009), C00F(H00F), C00H(H00H), C00J(H00J), C00J(H00A), C00L(H00L), C00M(H00M), C00N(H00N) 7.c Idealised Me refined as rotating group: C00K(H00B,H00D,H00E) ; _shelx_res_file ; exp_1885.res created by SHELXL-2014/8 TITL exp_1885_a.res in P2(1) REM Old TITL exp_1885_a.res in P2(1) REM SHELXT solution in P2(1) REM R1 0.082, Rweak 0.035, Alpha 0.003, Orientation as input REM Flack x = 0.055 ( 0.014 ) from Parsons' quotients REM Formula found by SHELXT: C13 N6 O2 S2 CELL 1.54184 10.1096 8.1557 10.7216 90 110.545 90 ZERR 2 0.0003 0.0002 0.0004 0 0.004 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 30 32 8 4 4 DFIX 0.93 C00I H00I DFIX 0.93 C005 H005 RIGU 0.001 0.001 S002 C005 C00E C00I C00J C00B N007 C00C EADP C005 S005 EADP S002 C002 EXYZ S002 C002 EXYZ C005 S005 L.S. 10 PLAN 3 CONF BOND $H list 4 MORE -1 fmap 2 acta REM REM REM WGHT 0.057500 0.099100 FVAR 1.01187 S001 5 0.951659 0.604024 0.822478 11.00000 0.03545 0.03004 = 0.02115 -0.00254 0.01344 -0.00406 PART 1 S002 5 0.276005 0.352524 0.072312 10.80000 0.02496 0.04297 = 0.03234 -0.00063 0.01124 -0.00156 PART 0 O003 4 0.876140 0.697351 0.389181 11.00000 0.02396 0.02531 = 0.02792 -0.00295 0.00823 0.00329 O004 4 0.740664 0.302918 0.316292 11.00000 0.01712 0.02788 = 0.02291 0.00295 0.00707 0.00098 PART 1 C005 1 0.317530 0.475492 -0.036496 10.80000 0.03195 0.04439 = 0.03354 0.00426 0.01280 0.00233 PART 0 N006 3 1.024263 0.492829 0.496181 11.00000 0.01789 0.02445 = 0.01917 -0.00164 0.00906 0.00136 AFIX 43 H006 2 1.071520 0.407923 0.488981 11.00000 -1.20000 AFIX 0 N007 3 0.781636 0.477992 0.172318 11.00000 0.01739 0.02594 = 0.02044 0.00232 0.00520 -0.00057 AFIX 43 H007 2 0.749695 0.527747 0.096894 11.00000 -1.20000 AFIX 0 N008 3 1.034425 0.549673 0.621011 11.00000 0.02072 0.02979 = 0.01838 -0.00354 0.00623 -0.00505 AFIX 43 H008 2 1.109078 0.602269 0.667818 11.00000 -1.20000 AFIX 0 N009 3 0.817251 0.439182 0.596664 11.00000 0.01926 0.02912 = 0.02093 -0.00283 0.01003 -0.00203 AFIX 43 H009 2 0.823673 0.389304 0.528346 11.00000 -1.20000 AFIX 0 C00A 1 0.939876 0.571129 0.385657 11.00000 0.01506 0.02201 = 0.02386 -0.00187 0.00831 -0.00326 C00B 1 0.694201 0.388067 0.215440 11.00000 0.02129 0.02001 = 0.02106 -0.00349 0.00938 0.00003 C00C 1 0.930493 0.490166 0.254450 11.00000 0.01756 0.02195 = 0.01943 0.00173 0.00616 0.00027 AFIX 13 H00C 2 0.971395 0.379929 0.272308 11.00000 -1.20000 AFIX 0 C00D 1 0.686373 0.423814 0.620685 11.00000 0.02153 0.02412 = 0.02908 -0.00265 0.01360 -0.00315 C00E 1 0.540989 0.397640 0.136815 11.00000 0.02108 0.02125 = 0.02060 -0.00343 0.00851 0.00038 C00F 1 0.565262 0.481228 0.522234 11.00000 0.02665 0.03556 = 0.02994 -0.00214 0.01056 -0.00249 AFIX 43 H00F 2 0.570506 0.530589 0.445914 11.00000 -1.20000 AFIX 0 C00G 1 0.929902 0.525019 0.672270 11.00000 0.02149 0.02229 = 0.02242 0.00262 0.00764 0.00352 C00H 1 0.680332 0.350294 0.733820 11.00000 0.03020 0.02809 = 0.03556 0.00367 0.01790 0.00443 AFIX 43 H00H 2 0.762078 0.312064 0.799195 11.00000 -1.20000 AFIX 0 C00I 1 0.478033 0.488906 0.017967 11.00000 0.02491 0.03213 = 0.02673 0.00292 0.00902 0.00007 C00J 1 0.442211 0.316772 0.176543 11.00000 0.02265 0.02922 = 0.02634 -0.00216 0.01104 -0.00199 PART 1 AFIX 43 H00J 2 0.464806 0.250583 0.251776 10.80000 -1.20000 AFIX 43 PART 0 PART 2 H00A 2 0.464806 0.250583 0.251776 10.20000 -1.20000 AFIX 0 PART 0 C00K 1 1.010241 0.590825 0.184454 11.00000 0.02264 0.03211 = 0.02665 0.00103 0.01135 -0.00274 AFIX 137 H00B 2 0.999062 0.541744 0.099972 11.00000 -1.50000 H00D 2 1.108677 0.593840 0.238430 11.00000 -1.50000 H00E 2 0.973336 0.700446 0.170766 11.00000 -1.50000 AFIX 0 C00L 1 0.549118 0.333941 0.748970 11.00000 0.04376 0.02819 = 0.04514 -0.00124 0.03187 -0.00271 AFIX 43 H00L 2 0.543835 0.284729 0.825330 11.00000 -1.20000 AFIX 0 C00M 1 0.436219 0.463841 0.539440 11.00000 0.02102 0.05036 = 0.04514 -0.00815 0.00993 -0.00290 AFIX 43 H00M 2 0.354482 0.502475 0.474288 11.00000 -1.20000 AFIX 0 C00N 1 0.427811 0.389642 0.652488 11.00000 0.02617 0.04128 = 0.05263 -0.01322 0.02234 -0.01025 AFIX 43 H00N 2 0.340895 0.377566 0.663100 11.00000 -1.20000 AFIX 0 PART 2 C002 1 0.276005 0.352524 0.072312 10.20000 0.02496 0.04297 = 0.03234 -0.00063 0.01124 -0.00156 S005 5 0.317530 0.475492 -0.036496 10.20000 0.03195 0.04439 = 0.03354 0.00426 0.01280 0.00233 PART 0 H00I 2 0.524790 0.548359 -0.029826 11.00000 0.01545 H005 2 0.272350 0.524997 -0.114560 11.00000 0.05325 HKLF 4 REM exp_1885_a.res in P2(1) REM R1 = 0.0379 for 2511 Fo > 4sig(Fo) and 0.0388 for all 2570 data REM 217 parameters refined using 54 restraints END WGHT 0.0575 0.0991 REM Highest difference peak 0.286, deepest hole -0.308, 1-sigma level 0.057 Q1 1 1.0400 0.3519 0.5006 11.00000 0.05 0.29 Q2 1 0.9185 0.5979 0.7294 11.00000 0.05 0.27 Q3 1 0.2701 0.4060 -0.0242 11.00000 0.05 0.24 ; _shelx_res_checksum 9496 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S001 S 0.95166(9) 0.60402(11) 0.82248(8) 0.0279(2) Uani 1 1 d . . . . . S002 S 0.27600(11) 0.35252(15) 0.07231(10) 0.0331(3) Uani 0.8 1 d . U P A 1 O003 O 0.8761(2) 0.6974(3) 0.3892(2) 0.0260(5) Uani 1 1 d . . . . . O004 O 0.7407(2) 0.3029(3) 0.3163(2) 0.0226(5) Uani 1 1 d . . . . . C005 C 0.3175(3) 0.4755(4) -0.0365(2) 0.0363(6) Uani 0.8 1 d D U P A 1 N006 N 1.0243(3) 0.4928(4) 0.4962(3) 0.0198(6) Uani 1 1 d . . . . . H006 H 1.0715 0.4079 0.4890 0.024 Uiso 1 1 calc R . . . . N007 N 0.7816(3) 0.4780(4) 0.1723(3) 0.0216(6) Uani 1 1 d . U . . . H007 H 0.7497 0.5277 0.0969 0.026 Uiso 1 1 calc R . . . . N008 N 1.0344(3) 0.5497(4) 0.6210(3) 0.0231(6) Uani 1 1 d . . . . . H008 H 1.1091 0.6023 0.6678 0.028 Uiso 1 1 calc R . . . . N009 N 0.8173(3) 0.4392(4) 0.5967(3) 0.0223(6) Uani 1 1 d . . . . . H009 H 0.8237 0.3893 0.5283 0.027 Uiso 1 1 calc R . . . . C00A C 0.9399(3) 0.5711(4) 0.3857(3) 0.0199(7) Uani 1 1 d . . . . . C00B C 0.6942(3) 0.3881(4) 0.2154(3) 0.0203(6) Uani 1 1 d . U . . . C00C C 0.9305(3) 0.4902(4) 0.2545(3) 0.0197(6) Uani 1 1 d . U . . . H00C H 0.9714 0.3799 0.2723 0.024 Uiso 1 1 calc R . . . . C00D C 0.6864(3) 0.4238(4) 0.6207(3) 0.0237(7) Uani 1 1 d . . . . . C00E C 0.5410(3) 0.3976(4) 0.1368(3) 0.0207(6) Uani 1 1 d . U . . . C00F C 0.5653(4) 0.4812(5) 0.5222(4) 0.0305(8) Uani 1 1 d . . . . . H00F H 0.5705 0.5306 0.4459 0.037 Uiso 1 1 calc R . . . . C00G C 0.9299(3) 0.5250(4) 0.6723(3) 0.0221(7) Uani 1 1 d . . . . . C00H C 0.6803(4) 0.3503(5) 0.7338(4) 0.0296(8) Uani 1 1 d . . . . . H00H H 0.7621 0.3121 0.7992 0.036 Uiso 1 1 calc R . . . . C00I C 0.4780(4) 0.4889(5) 0.0180(4) 0.0279(7) Uani 1 1 d D U . . . C00J C 0.4422(4) 0.3168(5) 0.1765(3) 0.0254(7) Uani 1 1 d . U . . . H00J H 0.4648 0.2506 0.2518 0.030 Uiso 0.8 1 calc R . P A 1 H00A H 0.4648 0.2506 0.2518 0.030 Uiso 0.2 1 calc R . P A 2 C00K C 1.0102(3) 0.5908(5) 0.1845(3) 0.0264(7) Uani 1 1 d . . . . . H00B H 0.9991 0.5417 0.1000 0.040 Uiso 1 1 calc GR . . . . H00D H 1.1087 0.5938 0.2384 0.040 Uiso 1 1 calc GR . . . . H00E H 0.9733 0.7004 0.1708 0.040 Uiso 1 1 calc GR . . . . C00L C 0.5491(4) 0.3339(5) 0.7490(4) 0.0347(9) Uani 1 1 d . . . . . H00L H 0.5438 0.2847 0.8253 0.042 Uiso 1 1 calc R . . . . C00M C 0.4362(4) 0.4638(6) 0.5394(4) 0.0393(9) Uani 1 1 d . . . . . H00M H 0.3545 0.5025 0.4743 0.047 Uiso 1 1 calc R . . . . C00N C 0.4278(4) 0.3896(5) 0.6525(4) 0.0378(9) Uani 1 1 d . . . . . H00N H 0.3409 0.3776 0.6631 0.045 Uiso 1 1 calc R . . . . C002 C 0.27600(11) 0.35252(15) 0.07231(10) 0.0331(3) Uani 0.2 1 d . . P A 2 S005 S 0.3175(3) 0.4755(4) -0.0365(2) 0.0363(6) Uani 0.2 1 d . . P A 2 H00I H 0.525(3) 0.548(4) -0.030(3) 0.015(9) Uiso 1 1 d D . . . . H005 H 0.272(5) 0.525(6) -0.115(3) 0.053(15) Uiso 1 1 d 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 S001 0.0355(5) 0.0300(4) 0.0211(4) -0.0025(4) 0.0134(3) -0.0041(4) S002 0.0250(5) 0.0430(6) 0.0323(5) -0.0006(5) 0.0112(4) -0.0016(5) O003 0.0240(12) 0.0253(13) 0.0279(12) -0.0030(10) 0.0082(10) 0.0033(10) O004 0.0171(11) 0.0279(14) 0.0229(11) 0.0030(10) 0.0071(9) 0.0010(9) C005 0.0319(11) 0.0444(13) 0.0335(11) 0.0043(11) 0.0128(9) 0.0023(10) N006 0.0179(13) 0.0245(15) 0.0192(13) -0.0016(11) 0.0091(11) 0.0014(11) N007 0.0174(11) 0.0259(13) 0.0204(12) 0.0023(11) 0.0052(9) -0.0006(9) N008 0.0207(13) 0.0298(16) 0.0184(13) -0.0035(12) 0.0062(10) -0.0051(11) N009 0.0193(13) 0.0291(15) 0.0209(13) -0.0028(12) 0.0100(11) -0.0020(12) C00A 0.0151(13) 0.0220(18) 0.0239(16) -0.0019(13) 0.0083(12) -0.0033(13) C00B 0.0213(12) 0.0200(15) 0.0211(13) -0.0035(12) 0.0094(10) 0.0000(10) C00C 0.0176(12) 0.0220(16) 0.0194(14) 0.0017(13) 0.0062(10) 0.0003(11) C00D 0.0215(16) 0.0241(17) 0.0291(17) -0.0027(14) 0.0136(13) -0.0032(14) C00E 0.0211(11) 0.0213(15) 0.0206(12) -0.0034(11) 0.0085(9) 0.0004(9) C00F 0.0266(18) 0.036(2) 0.0299(18) -0.0021(17) 0.0106(14) -0.0025(16) C00G 0.0215(15) 0.0223(17) 0.0224(17) 0.0026(14) 0.0076(13) 0.0035(13) C00H 0.0302(18) 0.0281(18) 0.0356(18) 0.0037(17) 0.0179(15) 0.0044(16) C00I 0.0249(14) 0.0321(17) 0.0267(14) 0.0029(13) 0.0090(11) 0.0001(11) C00J 0.0226(13) 0.0292(17) 0.0263(14) -0.0022(13) 0.0110(11) -0.0020(11) C00K 0.0226(16) 0.0321(19) 0.0266(16) 0.0010(16) 0.0114(13) -0.0027(15) C00L 0.044(2) 0.0282(18) 0.045(2) -0.0012(18) 0.0319(18) -0.0027(17) C00M 0.0210(17) 0.050(2) 0.045(2) -0.008(2) 0.0099(16) -0.0029(18) C00N 0.0262(18) 0.041(2) 0.053(2) -0.013(2) 0.0223(17) -0.0103(17) C002 0.0250(5) 0.0430(6) 0.0323(5) -0.0006(5) 0.0112(4) -0.0016(5) S005 0.0319(11) 0.0444(13) 0.0335(11) 0.0043(11) 0.0128(9) 0.0023(10) 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' S S 0.3331 0.5567 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C00J S002 C005 97.37(15) . . ? S002 C005 H005 138(3) . . ? C00I C005 S002 105.4(2) . . ? C00I C005 H005 117(4) . . ? N008 N006 H006 120.1 . . ? C00A N006 H006 120.1 . . ? C00A N006 N008 119.9(3) . . ? C00B N007 H007 120.3 . . ? C00B N007 C00C 119.5(3) . . ? C00C N007 H007 120.3 . . ? N006 N008 H008 118.9 . . ? C00G N008 N006 122.3(3) . . ? C00G N008 H008 118.9 . . ? C00D N009 H009 117.4 . . ? C00G N009 H009 117.4 . . ? C00G N009 C00D 125.2(3) . . ? O003 C00A N006 123.2(3) . . ? O003 C00A C00C 122.0(3) . . ? N006 C00A C00C 114.8(3) . . ? O004 C00B N007 120.9(3) . . ? O004 C00B C00E 122.0(3) . . ? N007 C00B C00E 117.1(3) . . ? N007 C00C C00A 107.7(3) . . ? N007 C00C H00C 109.3 . . ? N007 C00C C00K 110.7(3) . . ? C00A C00C H00C 109.3 . . ? C00K C00C C00A 110.4(3) . . ? C00K C00C H00C 109.3 . . ? C00F C00D N009 117.1(3) . . ? C00H C00D N009 121.6(3) . . ? C00H C00D C00F 121.2(3) . . ? C00I C00E C00B 126.0(3) . . ? C00J C00E C00B 121.5(3) . . ? C00J C00E C00I 112.5(3) . . ? C00D C00F H00F 120.5 . . ? C00M C00F C00D 119.0(4) . . ? C00M C00F H00F 120.5 . . ? N008 C00G S001 118.1(2) . . ? N009 C00G S001 125.4(3) . . ? N009 C00G N008 116.5(3) . . ? C00D C00H H00H 120.6 . . ? C00D C00H C00L 118.8(3) . . ? C00L C00H H00H 120.6 . . ? C005 C00I H00I 120(2) . . ? C00E C00I C005 112.8(3) . . ? C00E C00I S005 112.8(3) . . ? C00E C00I H00I 127(2) . . ? S005 C00I H00I 120(2) . . ? S002 C00J H00J 124.0 . . ? C00E C00J S002 111.9(3) . . ? C00E C00J H00J 124.0 . . ? C00E C00J H00A 124.0 . . ? C00E C00J C002 111.9(3) . . ? C002 C00J H00A 124.0 . . ? C00C C00K H00B 109.5 . . ? C00C C00K H00D 109.5 . . ? C00C C00K H00E 109.5 . . ? H00B C00K H00D 109.5 . . ? H00B C00K H00E 109.5 . . ? H00D C00K H00E 109.5 . . ? C00H C00L H00L 119.6 . . ? C00N C00L C00H 120.9(4) . . ? C00N C00L H00L 119.6 . . ? C00F C00M H00M 119.6 . . ? C00N C00M C00F 120.7(4) . . ? C00N C00M H00M 119.6 . . ? C00L C00N C00M 119.4(3) . . ? C00L C00N H00N 120.3 . . ? C00M C00N H00N 120.3 . . ? C00J C002 S005 97.37(15) . . ? C00I S005 C002 105.4(2) . . ? C00I S005 H005 117(4) . . ? C002 S005 H005 138(3) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S001 C00G 1.676(3) . ? S002 C005 1.699(3) . ? S002 C00J 1.685(4) . ? O003 C00A 1.222(4) . ? O004 C00B 1.231(4) . ? C005 C00I 1.523(4) . ? C005 H005 0.90(2) . ? N006 H006 0.8600 . ? N006 N008 1.386(4) . ? N006 C00A 1.353(4) . ? N007 H007 0.8600 . ? N007 C00B 1.349(4) . ? N007 C00C 1.456(4) . ? N008 H008 0.8600 . ? N008 C00G 1.366(4) . ? N009 H009 0.8600 . ? N009 C00D 1.439(4) . ? N009 C00G 1.340(4) . ? C00A C00C 1.527(4) . ? C00B C00E 1.483(4) . ? C00C H00C 0.9800 . ? C00C C00K 1.520(5) . ? C00D C00F 1.388(5) . ? C00D C00H 1.374(5) . ? C00E C00I 1.419(5) . ? C00E C00J 1.383(5) . ? C00F H00F 0.9300 . ? C00F C00M 1.387(5) . ? C00H H00H 0.9300 . ? C00H C00L 1.398(5) . ? C00I S005 1.523(4) . ? C00I H00I 0.94(2) . ? C00J H00J 0.9300 . ? C00J H00A 0.9300 . ? C00J C002 1.685(4) . ? C00K H00B 0.9600 . ? C00K H00D 0.9600 . ? C00K H00E 0.9600 . ? C00L H00L 0.9300 . ? C00L C00N 1.375(6) . ? C00M H00M 0.9300 . ? C00M C00N 1.384(6) . ? C00N H00N 0.9300 . ? C002 S005 1.699(3) . ? S005 H005 0.90(2) . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S002 C005 C00I C00E 0.5(4) . . . . ? O003 C00A C00C N007 -49.1(4) . . . . ? O003 C00A C00C C00K 71.8(4) . . . . ? O004 C00B C00E C00I -178.4(3) . . . . ? O004 C00B C00E C00J 2.9(5) . . . . ? C005 S002 C00J C00E 0.8(3) . . . . ? N006 N008 C00G S001 -178.3(2) . . . . ? N006 N008 C00G N009 1.5(5) . . . . ? N006 C00A C00C N007 131.3(3) . . . . ? N006 C00A C00C C00K -107.8(3) . . . . ? N007 C00B C00E C00I 2.0(5) . . . . ? N007 C00B C00E C00J -176.7(3) . . . . ? N008 N006 C00A O003 4.1(5) . . . . ? N008 N006 C00A C00C -176.2(3) . . . . ? N009 C00D C00F C00M 177.9(3) . . . . ? N009 C00D C00H C00L -177.7(4) . . . . ? C00A N006 N008 C00G 75.5(4) . . . . ? C00B N007 C00C C00A -61.6(4) . . . . ? C00B N007 C00C C00K 177.6(3) . . . . ? C00B C00E C00I C005 -178.8(3) . . . . ? C00B C00E C00I S005 -178.8(3) . . . . ? C00B C00E C00J S002 178.3(3) . . . . ? C00B C00E C00J C002 178.3(3) . . . . ? C00C N007 C00B O004 -7.5(5) . . . . ? C00C N007 C00B C00E 172.1(3) . . . . ? C00D N009 C00G S001 11.1(5) . . . . ? C00D N009 C00G N008 -168.6(3) . . . . ? C00D C00F C00M C00N -0.4(6) . . . . ? C00D C00H C00L C00N 0.2(6) . . . . ? C00E C00I S005 C002 0.5(4) . . . . ? C00E C00J C002 S005 0.8(3) . . . . ? C00F C00D C00H C00L -0.1(6) . . . . ? C00F C00M C00N C00L 0.5(7) . . . . ? C00G N009 C00D C00F 119.4(4) . . . . ? C00G N009 C00D C00H -62.9(5) . . . . ? C00H C00D C00F C00M 0.2(6) . . . . ? C00H C00L C00N C00M -0.5(6) . . . . ? C00I C00E C00J S002 -0.6(4) . . . . ? C00I C00E C00J C002 -0.6(4) . . . . ? C00J S002 C005 C00I -0.7(3) . . . . ? C00J C00E C00I C005 0.0(4) . . . . ? C00J C00E C00I S005 0.0(4) . . . . ? C00J C002 S005 C00I -0.7(3) . . . . ?