#------------------------------------------------------------------------------ #$Date: 2021-09-06 15:22:24 +0300 (Mon, 06 Sep 2021) $ #$Revision: 268910 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158162.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_7158162 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, C2 H3 N' _chemical_formula_sum 'C17 H19 N5 O2 S2' _chemical_formula_weight 389.49 _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 geom _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 94.034(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.0334(2) _cell_length_b 8.7125(2) _cell_length_c 12.1508(3) _cell_measurement_reflns_used 3433 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 30.1320 _cell_measurement_theta_min 4.1760 _cell_volume 953.94(4) _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 100.01(10) _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.860 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_unetI/netI 0.0475 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.860 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5890 _diffrn_reflns_point_group_measured_fraction_full 0.887 _diffrn_reflns_point_group_measured_fraction_max 0.707 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.716 _diffrn_reflns_theta_min 3.588 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.85893 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_description block _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.593 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.062 _refine_ls_abs_structure_details ; Flack x determined using 1298 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 237 _refine_ls_number_reflns 4193 _refine_ls_number_restraints 63 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0401 _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^)+(0.0571P)^2^+0.1849P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1030 _refine_ls_wR_factor_ref 0.1091 _reflns_Friedel_coverage 0.550 _reflns_Friedel_fraction_full 0.762 _reflns_Friedel_fraction_max 0.533 _reflns_number_gt 3862 _reflns_number_total 4193 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01053k2.cif _cod_data_source_block exp_12393 _cod_depositor_comments 'Adding full bibliography for 7158162--7158163.cif.' _cod_database_code 7158162 _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 N(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained planarity C00K, C00B, C00N, C00A, S002 with sigma of 0.1 3. Uiso/Uaniso restraints and constraints Uanis(S002) \\sim Ueq, Uanis(C00A) \\sim Ueq, Uanis(C00N) \\sim Ueq, Uanis(C00K) \\sim Ueq, Uanis(C00B) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04 4. Rigid body (RIGU) restrains C00A, C00N, S002, C00K, C00B with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 5.a Ternary CH refined with riding coordinates: C00H(H00H) 5.b Aromatic/amide H refined with riding coordinates: N005(H005), N006(H006), N007(H007), N008(H008), C00A(H00A), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P) 5.c Idealised Me refined as rotating group: C00O(H00E,H00F,H00G), C00Q(H00B,H00C,H00D) ; _shelx_res_file ; exp_12393.res created by SHELXL-2014/8 TITL exp_12393_a.res in P2(1) REM Old TITL exp_12393_a.res in P2(1) REM SHELXT solution in P2(1) REM R1 0.075, Rweak 0.029, Alpha 0.001, Orientation as input REM Flack x = 0.000 ( 0.035 ) from Parsons' quotients REM Formula found by SHELXT: C18 N4 O2 S2 CELL 0.71073 9.0334 8.7125 12.1508 90 94.034 90 ZERR 2 0.0002 0.0002 0.0003 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O S UNIT 34 38 10 4 4 FLAT C00K C00B C00N C00A S002 RIGU 0.001 0.001 C00A C00N S002 C00K C00B ISOR 0.02 0.04 S002 C00A C00N C00K C00B L.S. 10 PLAN 2 CONF BOND $H list 4 MORE -1 fmap 2 acta REM REM REM WGHT 0.057100 0.184900 FVAR 0.95018 S001 5 0.337302 0.478459 0.762063 11.00000 0.02478 0.02652 = 0.01694 -0.00414 0.00558 -0.00602 S002 5 -0.126573 0.232130 0.657394 11.00000 0.02270 0.03588 = 0.02952 -0.00411 0.00177 -0.00206 O003 4 0.313938 0.193644 0.333119 11.00000 0.01890 0.02118 = 0.01774 0.00250 0.00250 0.00073 O004 4 0.438412 0.566393 0.408563 11.00000 0.02348 0.01657 = 0.02526 -0.00202 0.00253 0.00186 N005 3 0.279998 0.311340 0.575892 11.00000 0.01815 0.01718 = 0.01764 -0.00297 0.00305 -0.00263 AFIX 43 H005 2 0.314996 0.278896 0.516122 11.00000 -1.20000 AFIX 0 N006 3 0.509350 0.423243 0.604177 11.00000 0.01774 0.02121 = 0.01770 -0.00486 0.00205 -0.00247 AFIX 43 H006 2 0.573766 0.474246 0.644828 11.00000 -1.20000 AFIX 0 N007 3 0.547739 0.368681 0.503703 11.00000 0.01808 0.01855 = 0.01758 -0.00182 0.00199 0.00305 AFIX 43 H007 2 0.597743 0.284999 0.500487 11.00000 -1.20000 AFIX 0 N008 3 0.433290 0.353641 0.224948 11.00000 0.02094 0.02001 = 0.01580 0.00246 0.00058 -0.00267 AFIX 43 H008 2 0.431804 0.405095 0.164480 11.00000 -1.20000 AFIX 0 N009 3 0.417367 0.604932 0.054744 11.00000 0.02830 0.02587 = 0.03244 0.00374 0.00377 0.00023 C00A 1 -0.085929 0.115272 0.547042 11.00000 0.01748 0.02567 = 0.01370 -0.00332 0.00104 0.00516 AFIX 43 H00A 2 -0.148166 0.043266 0.511197 11.00000 -1.20000 AFIX 0 C00B 1 0.132676 0.265623 0.592730 11.00000 0.01874 0.01899 = 0.01735 0.00342 -0.00078 0.00154 C00C 1 0.375136 0.726983 0.066379 11.00000 0.02083 0.02339 = 0.02298 0.00537 0.00097 -0.00384 C00D 1 0.320736 0.260158 0.243329 11.00000 0.01804 0.01394 = 0.01748 0.00049 0.00288 0.00216 C00E 1 0.506862 0.446629 0.409757 11.00000 0.01392 0.01737 = 0.01981 -0.00272 0.00322 -0.00330 C00F 1 0.372293 0.398817 0.641114 11.00000 0.01870 0.01551 = 0.01886 0.00367 0.00002 0.00036 C00G 1 0.206301 0.235187 0.149859 11.00000 0.01879 0.01565 = 0.01886 0.00158 0.00154 0.00403 C00H 1 0.557989 0.369349 0.305828 11.00000 0.01880 0.02045 = 0.01876 -0.00113 0.00413 0.00201 AFIX 13 H00H 2 0.596603 0.267038 0.325262 11.00000 -1.20000 AFIX 0 C00I 1 0.001001 0.151276 -0.021043 11.00000 0.01929 0.02745 = 0.02247 0.00181 -0.00312 -0.00162 AFIX 43 H00I 2 -0.066570 0.120786 -0.078141 11.00000 -1.20000 AFIX 0 C00J 1 0.135928 0.213731 -0.044626 11.00000 0.02140 0.02498 = 0.01673 0.00151 0.00123 0.00154 AFIX 43 H00J 2 0.158307 0.227644 -0.117503 11.00000 -1.20000 AFIX 0 C00K 1 0.041039 0.319401 0.668561 11.00000 0.02062 0.02345 = 0.02222 -0.00008 0.00109 0.00169 AFIX 43 H00K 2 0.067578 0.395041 0.720239 11.00000 -1.20000 AFIX 0 C00L 1 0.237639 0.255491 0.040861 11.00000 0.01712 0.01866 = 0.02013 0.00305 0.00374 -0.00082 AFIX 43 H00L 2 0.328181 0.297730 0.024806 11.00000 -1.20000 AFIX 0 C00M 1 0.069453 0.175875 0.173190 11.00000 0.02017 0.02557 = 0.02052 0.00400 0.00235 -0.00263 AFIX 43 H00M 2 0.046401 0.163960 0.246098 11.00000 -1.20000 AFIX 0 C00N 1 0.065226 0.153214 0.522328 11.00000 0.02037 0.03009 = 0.02421 -0.00548 0.00280 -0.00308 AFIX 43 H00N 2 0.112876 0.107514 0.465359 11.00000 -1.20000 AFIX 0 C00O 1 0.321842 0.883245 0.081125 11.00000 0.02728 0.02467 = 0.04017 0.00187 0.00028 0.00200 AFIX 137 H00E 2 0.384964 0.954025 0.046019 11.00000 -1.50000 H00F 2 0.323247 0.906266 0.158455 11.00000 -1.50000 H00G 2 0.222254 0.892243 0.048602 11.00000 -1.50000 AFIX 0 C00P 1 -0.033605 0.134085 0.087623 11.00000 0.01862 0.03257 = 0.02930 0.00494 0.00073 -0.00576 AFIX 43 H00P 2 -0.125430 0.094734 0.103430 11.00000 -1.20000 AFIX 0 C00Q 1 0.680201 0.463026 0.258577 11.00000 0.01998 0.03535 = 0.02458 -0.00356 0.00505 -0.00500 AFIX 137 H00B 2 0.711207 0.413670 0.193408 11.00000 -1.50000 H00C 2 0.763036 0.470727 0.312285 11.00000 -1.50000 H00D 2 0.643658 0.563933 0.240151 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_12393_a.res in P2(1) REM R1 = 0.0401 for 3862 Fo > 4sig(Fo) and 0.0452 for all 4193 data REM 237 parameters refined using 63 restraints END WGHT 0.0571 0.1849 REM Highest difference peak 0.593, deepest hole -0.465, 1-sigma level 0.062 Q1 1 -0.1221 0.0768 0.5491 11.00000 0.05 0.59 Q2 1 -0.0403 0.1473 0.5415 11.00000 0.05 0.47 ; _shelx_res_checksum 96391 _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 0.33730(9) 0.47846(9) 0.76206(6) 0.02255(19) Uani 1 1 d . . . . . S002 S -0.12657(9) 0.23213(11) 0.65739(7) 0.0294(2) Uani 1 1 d . U . . . O003 O 0.3139(2) 0.1936(2) 0.33312(18) 0.0192(5) Uani 1 1 d . . . . . O004 O 0.4384(2) 0.5664(3) 0.40856(19) 0.0217(5) Uani 1 1 d . . . . . N005 N 0.2800(3) 0.3113(3) 0.5759(2) 0.0176(5) Uani 1 1 d . . . . . H005 H 0.3150 0.2789 0.5161 0.021 Uiso 1 1 calc R . . . . N006 N 0.5093(3) 0.4232(3) 0.6042(2) 0.0188(5) Uani 1 1 d . . . . . H006 H 0.5738 0.4742 0.6448 0.023 Uiso 1 1 calc R . . . . N007 N 0.5477(3) 0.3687(3) 0.5037(2) 0.0180(5) Uani 1 1 d . . . . . H007 H 0.5977 0.2850 0.5005 0.022 Uiso 1 1 calc R . . . . N008 N 0.4333(3) 0.3536(3) 0.2249(2) 0.0190(5) Uani 1 1 d . . . . . H008 H 0.4318 0.4051 0.1645 0.023 Uiso 1 1 calc R . . . . N009 N 0.4174(3) 0.6049(4) 0.0547(3) 0.0288(6) Uani 1 1 d . . . . . C00A C -0.0859(3) 0.1153(4) 0.5470(2) 0.0190(6) Uani 1 1 d . U . . . H00A H -0.1482 0.0433 0.5112 0.023 Uiso 1 1 calc R . . . . C00B C 0.1327(3) 0.2656(4) 0.5927(3) 0.0185(6) Uani 1 1 d . U . . . C00C C 0.3751(3) 0.7270(4) 0.0664(3) 0.0224(6) Uani 1 1 d . . . . . C00D C 0.3207(3) 0.2602(3) 0.2433(2) 0.0164(6) Uani 1 1 d . . . . . C00E C 0.5069(3) 0.4466(3) 0.4098(3) 0.0169(6) Uani 1 1 d . . . . . C00F C 0.3723(3) 0.3988(4) 0.6411(3) 0.0178(6) Uani 1 1 d . . . . . C00G C 0.2063(3) 0.2352(4) 0.1499(2) 0.0178(6) Uani 1 1 d . . . . . C00H C 0.5580(3) 0.3693(4) 0.3058(3) 0.0192(6) Uani 1 1 d . . . . . H00H H 0.5966 0.2670 0.3253 0.023 Uiso 1 1 calc R . . . . C00I C 0.0010(4) 0.1513(4) -0.0210(3) 0.0233(7) Uani 1 1 d . . . . . H00I H -0.0666 0.1208 -0.0781 0.028 Uiso 1 1 calc R . . . . C00J C 0.1359(3) 0.2137(4) -0.0446(3) 0.0210(6) Uani 1 1 d . . . . . H00J H 0.1583 0.2276 -0.1175 0.025 Uiso 1 1 calc R . . . . C00K C 0.0410(4) 0.3194(4) 0.6686(3) 0.0221(6) Uani 1 1 d . U . . . H00K H 0.0676 0.3950 0.7202 0.027 Uiso 1 1 calc R . . . . C00L C 0.2376(3) 0.2555(4) 0.0409(2) 0.0185(6) Uani 1 1 d . . . . . H00L H 0.3282 0.2977 0.0248 0.022 Uiso 1 1 calc R . . . . C00M C 0.0695(3) 0.1759(4) 0.1732(3) 0.0220(7) Uani 1 1 d . . . . . H00M H 0.0464 0.1640 0.2461 0.026 Uiso 1 1 calc R . . . . C00N C 0.0652(4) 0.1532(4) 0.5223(3) 0.0248(7) Uani 1 1 d . U . . . H00N H 0.1129 0.1075 0.4654 0.030 Uiso 1 1 calc R . . . . C00O C 0.3218(4) 0.8832(4) 0.0811(3) 0.0308(8) Uani 1 1 d . . . . . H00E H 0.3850 0.9540 0.0460 0.046 Uiso 1 1 calc GR . . . . H00F H 0.3232 0.9063 0.1585 0.046 Uiso 1 1 calc GR . . . . H00G H 0.2223 0.8922 0.0486 0.046 Uiso 1 1 calc GR . . . . C00P C -0.0336(4) 0.1341(4) 0.0876(3) 0.0269(7) Uani 1 1 d . . . . . H00P H -0.1254 0.0947 0.1034 0.032 Uiso 1 1 calc R . . . . C00Q C 0.6802(4) 0.4630(5) 0.2586(3) 0.0265(7) Uani 1 1 d . . . . . H00B H 0.7112 0.4137 0.1934 0.040 Uiso 1 1 calc GR . . . . H00C H 0.7630 0.4707 0.3123 0.040 Uiso 1 1 calc GR . . . . H00D H 0.6437 0.5639 0.2402 0.040 Uiso 1 1 calc GR . . . . 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 0.0248(4) 0.0265(4) 0.0169(3) -0.0041(3) 0.0056(3) -0.0060(3) S002 0.0227(4) 0.0359(5) 0.0295(4) -0.0041(4) 0.0018(3) -0.0021(4) O003 0.0189(10) 0.0212(12) 0.0177(11) 0.0025(9) 0.0025(8) 0.0007(9) O004 0.0235(11) 0.0166(11) 0.0253(12) -0.0020(10) 0.0025(9) 0.0019(9) N005 0.0182(12) 0.0172(12) 0.0176(12) -0.0030(10) 0.0030(9) -0.0026(10) N006 0.0177(12) 0.0212(13) 0.0177(12) -0.0049(10) 0.0020(9) -0.0025(11) N007 0.0181(11) 0.0186(13) 0.0176(12) -0.0018(11) 0.0020(10) 0.0030(10) N008 0.0209(12) 0.0200(13) 0.0158(12) 0.0025(10) 0.0006(10) -0.0027(11) N009 0.0283(14) 0.0259(16) 0.0324(16) 0.0037(13) 0.0038(12) 0.0002(13) C00A 0.0175(11) 0.0257(14) 0.0137(12) -0.0033(11) 0.0010(9) 0.0052(10) C00B 0.0187(11) 0.0190(13) 0.0173(12) 0.0034(10) -0.0008(9) 0.0015(10) C00C 0.0208(14) 0.0234(16) 0.0230(16) 0.0054(15) 0.0010(11) -0.0038(14) C00D 0.0180(13) 0.0139(14) 0.0175(14) 0.0005(11) 0.0029(10) 0.0022(12) C00E 0.0139(12) 0.0174(15) 0.0198(14) -0.0027(12) 0.0032(10) -0.0033(11) C00F 0.0187(14) 0.0155(14) 0.0189(14) 0.0037(12) 0.0000(11) 0.0004(12) C00G 0.0188(13) 0.0157(14) 0.0189(14) 0.0016(13) 0.0015(10) 0.0040(12) C00H 0.0188(14) 0.0204(15) 0.0188(15) -0.0011(12) 0.0041(11) 0.0020(12) C00I 0.0193(14) 0.0274(18) 0.0225(17) 0.0018(14) -0.0031(12) -0.0016(13) C00J 0.0214(14) 0.0250(16) 0.0167(14) 0.0015(13) 0.0012(11) 0.0015(13) C00K 0.0206(12) 0.0235(14) 0.0222(14) -0.0001(11) 0.0011(10) 0.0017(11) C00L 0.0171(13) 0.0187(15) 0.0201(15) 0.0030(13) 0.0037(11) -0.0008(12) C00M 0.0202(14) 0.0256(17) 0.0205(16) 0.0040(13) 0.0023(12) -0.0026(13) C00N 0.0204(12) 0.0301(15) 0.0242(14) -0.0055(12) 0.0028(10) -0.0031(11) C00O 0.0273(17) 0.0247(19) 0.040(2) 0.0019(16) 0.0003(15) 0.0020(15) C00P 0.0186(15) 0.033(2) 0.0293(18) 0.0049(15) 0.0007(12) -0.0058(14) C00Q 0.0200(15) 0.035(2) 0.0246(16) -0.0036(16) 0.0050(12) -0.0050(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 C00K S002 C00A 95.08(16) . . ? C00B N005 H005 115.7 . . ? C00F N005 H005 115.7 . . ? C00F N005 C00B 128.5(3) . . ? N007 N006 H006 119.0 . . ? C00F N006 H006 119.0 . . ? C00F N006 N007 122.0(3) . . ? N006 N007 H007 119.9 . . ? C00E N007 N006 120.2(2) . . ? C00E N007 H007 119.9 . . ? C00D N008 H008 119.7 . . ? C00D N008 C00H 120.6(3) . . ? C00H N008 H008 119.7 . . ? S002 C00A H00A 127.0 . . ? C00N C00A S002 106.1(2) . . ? C00N C00A H00A 127.0 . . ? C00K C00B N005 128.4(3) . . ? C00K C00B C00N 113.0(3) . . ? C00N C00B N005 118.5(3) . . ? N009 C00C C00O 179.7(4) . . ? O003 C00D N008 121.2(3) . . ? O003 C00D C00G 121.7(3) . . ? N008 C00D C00G 117.1(3) . . ? O004 C00E N007 123.3(3) . . ? O004 C00E C00H 123.5(3) . . ? N007 C00E C00H 113.2(3) . . ? N005 C00F S001 127.1(2) . . ? N005 C00F N006 115.7(3) . . ? N006 C00F S001 117.1(2) . . ? C00L C00G C00D 122.0(3) . . ? C00L C00G C00M 119.2(3) . . ? C00M C00G C00D 118.5(3) . . ? N008 C00H C00E 109.6(2) . . ? N008 C00H H00H 108.9 . . ? N008 C00H C00Q 110.2(3) . . ? C00E C00H H00H 108.9 . . ? C00Q C00H C00E 110.2(3) . . ? C00Q C00H H00H 108.9 . . ? C00J C00I H00I 120.0 . . ? C00J C00I C00P 120.1(3) . . ? C00P C00I H00I 120.0 . . ? C00I C00J H00J 120.2 . . ? C00I C00J C00L 119.7(3) . . ? C00L C00J H00J 120.2 . . ? S002 C00K H00K 124.0 . . ? C00B C00K S002 111.9(3) . . ? C00B C00K H00K 124.0 . . ? C00G C00L C00J 120.9(3) . . ? C00G C00L H00L 119.5 . . ? C00J C00L H00L 119.5 . . ? C00G C00M H00M 119.9 . . ? C00G C00M C00P 120.2(3) . . ? C00P C00M H00M 119.9 . . ? C00A C00N H00N 123.1 . . ? C00B C00N C00A 113.8(3) . . ? C00B C00N H00N 123.1 . . ? C00C C00O H00E 109.5 . . ? C00C C00O H00F 109.5 . . ? C00C C00O H00G 109.5 . . ? H00E C00O H00F 109.5 . . ? H00E C00O H00G 109.5 . . ? H00F C00O H00G 109.5 . . ? C00I C00P C00M 119.9(3) . . ? C00I C00P H00P 120.0 . . ? C00M C00P H00P 120.0 . . ? C00H C00Q H00B 109.5 . . ? C00H C00Q H00C 109.5 . . ? C00H C00Q H00D 109.5 . . ? H00B C00Q H00C 109.5 . . ? H00B C00Q H00D 109.5 . . ? H00C C00Q H00D 109.5 . . ? 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 C00F 1.675(3) . ? S002 C00A 1.743(3) . ? S002 C00K 1.691(3) . ? O003 C00D 1.241(4) . ? O004 C00E 1.212(4) . ? N005 H005 0.8600 . ? N005 C00B 1.418(4) . ? N005 C00F 1.346(4) . ? N006 H006 0.8600 . ? N006 N007 1.377(4) . ? N006 C00F 1.363(4) . ? N007 H007 0.8600 . ? N007 C00E 1.357(4) . ? N008 H008 0.8600 . ? N008 C00D 1.334(4) . ? N008 C00H 1.448(4) . ? N009 C00C 1.142(5) . ? C00A H00A 0.9300 . ? C00A C00N 1.457(4) . ? C00B C00K 1.364(4) . ? C00B C00N 1.410(5) . ? C00C C00O 1.459(5) . ? C00D C00G 1.497(4) . ? C00E C00H 1.531(4) . ? C00G C00L 1.385(4) . ? C00G C00M 1.387(4) . ? C00H H00H 0.9800 . ? C00H C00Q 1.518(4) . ? C00I H00I 0.9300 . ? C00I C00J 1.383(4) . ? C00I C00P 1.386(5) . ? C00J H00J 0.9300 . ? C00J C00L 1.386(4) . ? C00K H00K 0.9300 . ? C00L H00L 0.9300 . ? C00M H00M 0.9300 . ? C00M C00P 1.394(5) . ? C00N H00N 0.9300 . ? C00O H00E 0.9600 . ? C00O H00F 0.9600 . ? C00O H00G 0.9600 . ? C00P H00P 0.9300 . ? C00Q H00B 0.9600 . ? C00Q H00C 0.9600 . ? C00Q H00D 0.9600 . ? 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 C00A C00N C00B 1.2(3) . . . . ? O003 C00D C00G C00L -153.9(3) . . . . ? O003 C00D C00G C00M 19.8(5) . . . . ? O004 C00E C00H N008 -52.0(4) . . . . ? O004 C00E C00H C00Q 69.5(4) . . . . ? N005 C00B C00K S002 179.4(3) . . . . ? N005 C00B C00N C00A -179.9(3) . . . . ? N006 N007 C00E O004 1.2(4) . . . . ? N006 N007 C00E C00H -179.7(2) . . . . ? N007 N006 C00F S001 -177.2(2) . . . . ? N007 N006 C00F N005 3.4(4) . . . . ? N007 C00E C00H N008 128.9(3) . . . . ? N007 C00E C00H C00Q -109.6(3) . . . . ? N008 C00D C00G C00L 24.1(5) . . . . ? N008 C00D C00G C00M -162.2(3) . . . . ? C00A S002 C00K C00B -0.4(3) . . . . ? C00B N005 C00F S001 0.1(5) . . . . ? C00B N005 C00F N006 179.5(3) . . . . ? C00D N008 C00H C00E -66.9(4) . . . . ? C00D N008 C00H C00Q 171.7(3) . . . . ? C00D C00G C00L C00J 172.0(3) . . . . ? C00D C00G C00M C00P -172.4(3) . . . . ? C00F N005 C00B C00K 12.1(5) . . . . ? C00F N005 C00B C00N -169.8(3) . . . . ? C00F N006 N007 C00E 81.3(4) . . . . ? C00G C00M C00P C00I 0.3(5) . . . . ? C00H N008 C00D O003 5.7(5) . . . . ? C00H N008 C00D C00G -172.3(3) . . . . ? C00I C00J C00L C00G 0.2(5) . . . . ? C00J C00I C00P C00M -1.8(5) . . . . ? C00K S002 C00A C00N -0.4(2) . . . . ? C00K C00B C00N C00A -1.6(4) . . . . ? C00L C00G C00M C00P 1.5(5) . . . . ? C00M C00G C00L C00J -1.7(5) . . . . ? C00N C00B C00K S002 1.2(4) . . . . ? C00P C00I C00J C00L 1.6(5) . . . . ?