#------------------------------------------------------------------------------ #$Date: 2025-02-22 04:53:29 +0200 (Sat, 22 Feb 2025) $ #$Revision: 297834 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312763.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_2312763 loop_ _publ_author_name 'Vlahakis, Niko' 'Qu, Songrong' 'Richards, Logan S.' 'Moraes, Lygia Silva de' 'Cascio, Duilio' 'Nelson, Hosea M.' 'Rodriguez, Jose A.' _publ_section_title ; Fast event-based electron counting for small-molecule structure determination by MicroED. ; _journal_coeditor_code YP3239 _journal_issue 3 _journal_name_full 'Acta crystallographica. Section C, Structural chemistry' _journal_paper_doi 10.1107/S2053229624012300 _journal_volume 81 _journal_year 2025 _chemical_absolute_configuration rm _chemical_formula_iupac 'C10 H16 N2 O3 S1' _chemical_formula_moiety 'C10 H16 N2 O3 S1' _chemical_formula_sum 'C10 H16 N2 O3 S' _chemical_formula_weight 244.31 _chemical_name_common biotin _chemical_name_systematic ; 5-[(3aS,4S,6aR)-2-Oxohexahydro-1H-\ thieno[3,4-d]imidazol-4-yl]pentanoic acid ; _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/3 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.170(2) _cell_length_b 10.1100(19) _cell_length_c 20.710(3) _cell_measurement_reflns_used 4422 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 0.900 _cell_measurement_theta_min 0.099 _cell_volume 1082.5(5) _computing_structure_refinement ; SHELXL2019 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT2018 (Sheldrick, 2015a) ; _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.856 _diffrn_measured_fraction_theta_max 0.847 _diffrn_measurement_device_type TEM _diffrn_measurement_method 'continuous rotation 3D ED' _diffrn_radiation_type electron _diffrn_radiation_wavelength 0.0251 _diffrn_reflns_av_R_equivalents 0.1409 _diffrn_reflns_av_unetI/netI 0.1667 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 4422 _diffrn_reflns_theta_full 0.863 _diffrn_reflns_theta_max 0.900 _diffrn_reflns_theta_min 0.099 _diffrn_source FEG _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.000 _exptl_absorpt_correction_type none _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.499 _exptl_crystal_description needle _exptl_crystal_F_000 196 _exptl_crystal_size_max 0.010 _exptl_crystal_size_mid 0.0005 _exptl_crystal_size_min 0.00015 _refine_diff_density_max 0.232 _refine_diff_density_min -0.205 _refine_ls_abs_structure_details ; All f" are zero, so absolute structure could not be determined ; _refine_ls_extinction_coef 1047E1(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method ; SHELXL2019 (Sheldrick, 2015b) ; _refine_ls_goodness_of_fit_ref 1.325 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 148 _refine_ls_number_reflns 1926 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.325 _refine_ls_R_factor_all 0.1856 _refine_ls_R_factor_gt 0.1586 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3832 _refine_ls_wR_factor_ref 0.4094 _reflns_number_gt 1397 _reflns_number_total 1926 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file yp3239.cif _cod_data_source_block a _cod_original_formula_sum 'C10 H16 N2 O3 S1' _cod_database_code 2312763 _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. ; _shelx_hkl_file ; 0 1 2 3210.95 577.92 0 1 3 508.12 91.93 0 -1 -3 596.88 107.81 0 1 4 128.55 27.53 0 -1 -4 67.99 16.99 0 1 5 2260.32 408.02 0 -1 -5 1917.35 346.39 0 2 3 5471.00 984.36 0 -2 -3 6366.59 1145.04 0 2 4 4201.37 756.25 0 -2 -4 4778.24 860.03 0 2 5 159.86 29.24 0 -2 -5 233.59 42.46 0 2 6 430.15 78.18 0 -2 -6 361.92 65.98 0 2 7 5086.43 915.61 0 -2 -7 4725.55 850.29 0 2 8 1528.30 277.10 0 -2 -8 1287.01 233.12 0 2 9 33.51 26.79 0 -2 -9 32.27 23.63 0 2 10 948.01 176.35 0 -2 -10 1064.17 196.13 0 2 11 -9.59 33.53 0 -2 -11 5.60 24.43 0 3 4 2332.49 420.40 0 -3 -4 2498.96 450.70 0 3 5 102.33 21.07 0 -3 -5 114.51 22.94 0 3 6 3903.72 703.04 0 -3 -6 3563.92 641.93 0 3 7 539.99 97.57 0 -3 -7 751.25 135.79 0 3 8 366.92 66.85 0 -3 -8 217.08 40.22 0 3 9 203.35 38.12 0 -3 -9 292.65 54.26 0 3 10 460.43 85.05 0 -3 -10 512.07 93.93 0 3 11 323.47 62.11 0 -3 -11 473.61 88.43 0 3 12 46.91 29.58 0 -3 -12 -1.81 16.81 0 3 13 111.71 43.41 0 -3 -13 96.93 33.82 0 3 14 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12.60 16.69 -6 2 -1 15.83 23.55 6 -2 2 101.97 28.18 -6 2 2 90.19 30.42 6 2 -2 128.47 34.40 -6 -2 -2 68.09 25.70 6 2 2 77.13 22.58 -6 -2 2 69.36 28.58 6 -2 -2 130.42 31.06 -6 2 -2 77.49 28.47 6 -2 3 15.19 15.65 6 2 -3 17.08 19.43 -6 -2 -3 20.51 21.99 -6 -2 3 21.79 26.53 6 -2 -3 15.49 17.42 -6 2 -3 36.93 24.64 6 -2 4 18.03 16.59 6 2 -4 9.60 20.39 6 2 4 13.50 19.53 -6 -2 4 22.81 27.08 6 -2 -4 11.12 18.05 -6 2 -4 -3.27 19.54 6 -2 5 39.14 18.25 6 2 -5 13.63 23.37 -6 -2 -5 46.18 23.36 6 2 5 43.54 22.09 -6 -2 5 46.54 27.08 6 -2 -5 21.10 17.52 -6 2 -5 20.16 21.75 6 -2 6 42.41 18.04 6 2 -6 46.97 24.05 -6 -2 -6 29.00 18.79 6 2 6 55.53 22.50 -6 -2 6 46.68 29.66 6 -2 -6 47.36 19.03 -6 2 -6 65.59 26.04 6 -2 7 12.30 13.28 6 2 -7 16.85 21.59 -6 -2 -7 -0.22 19.04 6 2 7 8.28 18.86 -6 2 -7 11.61 18.54 6 3 0 39.06 20.84 -6 -3 0 13.05 23.95 6 -3 0 91.06 26.95 6 -3 1 35.01 17.40 6 3 -1 39.80 22.75 -6 -3 -1 52.29 28.34 6 3 1 51.10 22.88 -6 -3 1 36.82 31.69 6 -3 -1 25.48 17.60 6 -3 2 28.76 17.00 6 3 -2 7.84 18.30 -6 -3 -2 1.14 21.06 6 3 2 17.00 17.53 -6 -3 2 6.03 25.25 6 -3 -2 24.97 18.05 6 -3 3 16.78 16.53 6 3 -3 29.63 23.72 -6 -3 -3 13.03 27.03 6 3 3 26.55 19.42 -6 -3 3 32.27 27.71 6 -3 -3 16.82 18.74 -6 3 -3 25.50 23.26 6 -3 4 29.90 16.54 6 3 -4 41.25 23.15 -6 -3 -4 17.77 19.29 6 3 4 15.32 18.35 -6 -3 4 41.49 27.76 6 -3 -4 7.00 16.65 -6 3 -4 30.40 21.38 6 -3 5 37.33 17.79 6 3 -5 1.32 23.34 -6 -3 -5 16.67 20.50 -6 -3 5 -2.62 27.90 6 -3 -5 13.84 20.65 -6 3 -5 30.40 23.02 6 3 -6 2.06 24.50 6 3 6 11.22 17.72 -6 3 -6 8.70 21.51 6 4 0 -4.62 21.75 -6 -4 0 0.74 26.45 6 -4 0 25.77 17.51 6 -4 1 62.48 20.78 6 4 -1 33.58 23.83 -6 -4 -1 21.56 25.99 6 4 1 49.81 24.18 -6 -4 1 42.80 29.58 6 -4 2 15.80 16.94 6 4 -2 7.17 20.18 -6 -4 -2 11.60 21.58 6 4 2 17.92 19.88 -6 -4 2 1.82 26.30 6 4 -3 -6.63 24.17 -6 -4 -3 11.59 24.54 6 4 3 3.20 22.08 -6 -4 3 5.49 30.58 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 95204 _shelx_res_file ; TITL biotin_spot11_0p3dps_0p3fps_mov05_a.res in P2(1)2(1)2(1) a.res created by SHELXL-2019/3 at 16:34:19 on 11-Jul-2024 REM Old TITL GGYMLG in space group P 1 21 1 . REM SHELXT solution in P2(1)2(1)2(1): R1 0.298, Rweak 0.282, Alpha 0.038 REM 0.000 for 0 systematic absences, Orientation as input REM Flack x = 0.121 ( 0.138 ) from 461 Parsons' quotients REM Formula found by SHELXT: C12 N O2 S CELL 0.02510 5.1700 10.1100 20.7100 90.000 90.000 90.000 ZERR 1.000 0.0020 0.0019 0.0033 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C 0.600 40.938 0.136 0.374 0.547 3.278 1.225 13.013 0 0 0 0 0.76 12.011 SFAC N 0.482 31.526 0.135 0.324 0.519 2.607 1.075 10.017 0 0 0 0 0.71 14.007 SFAC O 0.392 25.675 0.144 0.306 0.511 2.272 0.937 8.270 0 0 0 0 0.66 15.999 SFAC S 1.390 40.169 0.348 0.365 0.915 2.890 2.506 13.043 0 0 0 0 1.05 32.065 SFAC H 0.129 37.737 0.036 0.553 0.127 3.772 0.236 13.518 0 0 0 0 0.31 1.008 UNIT 40 8 12 4 64 L.S. 1000 BOND LIST 4 FMAP 2 PLAN 20 DFIX 1 O7 H11 ACTA TEMP -173 WGHT 0.200000 EXTI10468.270508 FVAR 5.74610 S1 4 0.447151 0.629131 0.548162 11.00000 0.04103 0.06294 = 0.06455 0.00511 0.00656 0.00103 C2 1 0.272907 0.682789 0.664210 11.00000 0.04637 0.04258 = 0.06369 0.01483 0.00367 0.01432 AFIX 13 H3 5 0.156699 0.744934 0.688076 11.00000 -1.20000 AFIX 0 O1 3 0.581853 0.424239 0.746089 11.00000 0.06581 0.04263 = 0.05607 -0.00307 -0.02006 0.00045 C4 1 0.394937 0.750979 0.608197 11.00000 0.05078 0.02946 = 0.08348 0.00104 -0.02565 -0.00932 AFIX 23 H5A 5 0.561126 0.791672 0.621210 11.00000 -1.20000 H5B 5 0.279576 0.821350 0.591594 11.00000 -1.20000 AFIX 0 C5 1 0.142985 0.555961 0.568406 11.00000 0.04177 0.03005 = 0.03150 0.01580 -0.00145 0.01225 AFIX 13 H6 5 0.006644 0.616251 0.550889 11.00000 -1.20000 AFIX 0 C3 1 0.122586 0.563237 0.641236 11.00000 0.02710 0.04628 = 0.06731 0.01275 0.00750 -0.00326 AFIX 13 H4 5 -0.061673 0.566286 0.655848 11.00000 -1.20000 AFIX 0 O7 3 0.524065 0.517278 0.310914 11.00000 0.05533 0.04890 = 0.06641 0.01129 0.01771 0.00462 AFIX 88 H11 5 0.703990 0.527528 0.291153 11.00000 -1.50000 AFIX 0 N2 2 0.259503 0.461450 0.671520 11.00000 0.04852 0.02752 = 0.04619 0.00655 -0.01542 0.00170 AFIX 43 H2 5 0.222096 0.377591 0.665004 11.00000 -1.20000 AFIX 0 C6 1 0.084540 0.423110 0.543198 11.00000 0.05246 0.03205 = 0.04221 -0.01875 -0.00723 -0.00581 AFIX 23 H7A 5 -0.077660 0.392651 0.563801 11.00000 -1.20000 H7B 5 0.223863 0.362837 0.557680 11.00000 -1.20000 AFIX 0 C9 1 0.252261 0.374367 0.365956 11.00000 0.04463 0.03968 = 0.06825 -0.00014 -0.00073 0.00548 AFIX 23 H10A 5 0.103149 0.423018 0.347641 11.00000 -1.20000 H10B 5 0.209890 0.278886 0.365124 11.00000 -1.20000 AFIX 0 C1 1 0.442050 0.497255 0.709197 11.00000 0.03910 0.03084 = 0.03118 0.00425 -0.01463 0.00332 C10 1 0.485288 0.398373 0.324455 11.00000 0.04749 0.04305 = 0.05374 -0.02403 0.01886 -0.00898 N1 2 0.463433 0.626933 0.707444 11.00000 0.04964 0.04350 = 0.04539 -0.01514 -0.03089 -0.00561 AFIX 43 H1 5 0.577570 0.673122 0.729473 11.00000 -1.20000 AFIX 0 C8 1 0.289703 0.415245 0.432021 11.00000 0.05428 0.02199 = 0.05581 0.00403 -0.00859 -0.00114 AFIX 23 H9A 5 0.352328 0.507775 0.432597 11.00000 -1.20000 H9B 5 0.424798 0.359130 0.451955 11.00000 -1.20000 AFIX 0 O00F 3 0.622083 0.307723 0.302014 11.00000 0.05115 0.03884 = 0.11954 0.00876 0.01892 0.00268 C7 1 0.054424 0.406205 0.470369 11.00000 0.05195 0.03635 = 0.06816 0.01339 -0.00568 0.00708 AFIX 23 H8A 5 -0.025508 0.318811 0.462195 11.00000 -1.20000 H8B 5 -0.067987 0.474312 0.454688 11.00000 -1.20000 REM ##### REM ##### AFIX 0 HKLF 4 REM biotin_spot11_0p3dps_0p3fps_mov05_a.res in P2(1)2(1)2(1) REM wR2 = 0.4094, GooF = S = 1.325, Restrained GooF = 1.325 for all data REM R1 = 0.1586 for 1397 Fo > 4sig(Fo) and 0.1856 for all 1926 data REM 148 parameters refined using 1 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.232, deepest hole -0.205, 1-sigma level 0.065 Q1 1 0.4656 0.5657 0.5007 11.00000 0.05 0.23 Q2 1 0.4701 0.5617 0.6621 11.00000 0.05 0.23 Q3 1 0.0196 0.4316 0.5919 11.00000 0.05 0.21 Q4 1 0.4699 0.6954 0.5793 11.00000 0.05 0.21 Q5 1 0.5253 0.5800 0.3590 11.00000 0.05 0.20 Q6 1 0.5470 0.4639 0.7712 11.00000 0.05 0.19 Q7 1 0.5034 0.4493 0.3530 11.00000 0.05 0.19 Q8 1 0.0911 0.5838 0.5974 11.00000 0.05 0.18 Q9 1 0.3729 0.6776 0.6619 11.00000 0.05 0.18 Q10 1 0.1023 0.3558 0.4177 11.00000 0.05 0.18 Q11 1 0.0692 0.4773 0.4271 11.00000 0.05 0.17 Q12 1 0.0223 0.5613 0.4268 11.00000 0.05 0.16 Q13 1 0.4315 0.8126 0.5767 11.00000 0.05 0.15 Q14 1 0.2023 0.5646 0.6263 11.00000 0.05 0.14 Q15 1 0.4579 0.6619 0.5239 11.00000 0.05 0.14 Q16 1 -0.1587 0.3163 0.5520 11.00000 0.05 0.13 Q17 1 0.3611 0.2542 0.3112 11.00000 0.05 0.12 Q18 1 0.3175 0.3615 0.4790 11.00000 0.05 0.12 Q19 1 0.5897 0.3813 0.7130 11.00000 0.05 0.12 Q20 1 0.2893 0.2796 0.3190 11.00000 0.05 0.11 ; _shelx_res_checksum 5829 loop_ _space_group_symop_operation_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_type_symbol _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_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.4472(12) 0.6291(8) 0.5482(4) 0.056(2) Uani d 1 . . C C2 0.273(3) 0.6828(15) 0.6642(7) 0.051(4) Uani d 1 . . H H3 0.156699 0.744934 0.688076 0.061 Uiso calc 1 . . O O1 0.582(2) 0.4242(13) 0.7461(6) 0.055(3) Uani d 1 . . C C4 0.395(3) 0.7510(15) 0.6082(8) 0.055(4) Uani d 1 . . H H5A 0.561126 0.791672 0.621210 0.065 Uiso calc 1 . . H H5B 0.279576 0.821350 0.591594 0.065 Uiso calc 1 . . C C5 0.143(2) 0.5560(11) 0.5684(6) 0.034(3) Uani d 1 . . H H6 0.006644 0.616251 0.550889 0.041 Uiso calc 1 . . C C3 0.123(2) 0.5632(15) 0.6412(7) 0.047(3) Uani d 1 . . H H4 -0.061673 0.566286 0.655848 0.056 Uiso calc 1 . . O O7 0.524(2) 0.5173(13) 0.3109(7) 0.057(3) Uani d 1 . . H H11 0.704(10) 0.528(2) 0.291(5) 0.085 Uiso calc 1 . . N N2 0.260(2) 0.4614(12) 0.6715(6) 0.041(3) Uani d 1 . . H H2 0.222096 0.377591 0.665004 0.049 Uiso calc 1 . . C C6 0.085(2) 0.4231(13) 0.5432(6) 0.042(3) Uani d 1 . . H H7A -0.077660 0.392651 0.563801 0.051 Uiso calc 1 . . H H7B 0.223863 0.362837 0.557680 0.051 Uiso calc 1 . . C C9 0.252(3) 0.3744(14) 0.3660(8) 0.051(3) Uani d 1 . . H H10A 0.103149 0.423018 0.347641 0.061 Uiso calc 1 . . H H10B 0.209890 0.278886 0.365124 0.061 Uiso calc 1 . . C C1 0.442(2) 0.4973(11) 0.7092(6) 0.034(3) Uani d 1 . . C C10 0.485(2) 0.3984(14) 0.3245(7) 0.048(4) Uani d 1 . . N N1 0.463(2) 0.6269(11) 0.7074(6) 0.046(3) Uani d 1 . . H H1 0.577570 0.673122 0.729473 0.055 Uiso calc 1 . . C C8 0.290(2) 0.4152(13) 0.4320(7) 0.044(3) Uani d 1 . . H H9A 0.352328 0.507775 0.432597 0.053 Uiso calc 1 . . H H9B 0.424798 0.359130 0.451955 0.053 Uiso calc 1 . . O O00F 0.622(2) 0.3077(14) 0.3020(9) 0.070(4) Uani d 1 . . C C7 0.054(3) 0.4062(15) 0.4704(7) 0.052(3) Uani d 1 . . H H8A -0.025508 0.318811 0.462195 0.063 Uiso calc 1 . . H H8B -0.067987 0.474312 0.454688 0.063 Uiso calc 1 . . 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 S1 0.041(3) 0.063(5) 0.065(5) 0.001(3) 0.007(3) 0.005(3) C2 0.046(7) 0.043(9) 0.064(11) 0.014(6) 0.004(6) 0.015(6) O1 0.066(6) 0.043(8) 0.056(8) 0.000(5) -0.020(6) -0.003(5) C4 0.051(8) 0.029(9) 0.083(12) -0.009(5) -0.026(7) 0.001(6) C5 0.042(5) 0.030(7) 0.031(7) 0.012(4) -0.001(4) 0.016(4) C3 0.027(5) 0.046(9) 0.067(10) -0.003(5) 0.007(5) 0.013(6) O7 0.055(6) 0.049(8) 0.066(9) 0.005(5) 0.018(6) 0.011(5) N2 0.049(5) 0.028(7) 0.046(7) 0.002(4) -0.015(5) 0.007(4) C6 0.052(6) 0.032(7) 0.042(8) -0.006(5) -0.007(6) -0.019(5) C9 0.045(6) 0.040(9) 0.068(11) 0.005(6) -0.001(6) 0.000(6) C1 0.039(5) 0.031(8) 0.031(7) 0.003(5) -0.015(5) 0.004(4) C10 0.047(6) 0.043(9) 0.054(9) -0.009(6) 0.019(6) -0.024(6) N1 0.050(5) 0.043(8) 0.045(8) -0.006(5) -0.031(5) -0.015(4) C8 0.054(7) 0.022(7) 0.056(9) -0.001(5) -0.009(6) 0.004(5) O00F 0.051(6) 0.039(8) 0.120(14) 0.003(5) 0.019(7) 0.009(7) C7 0.052(6) 0.036(9) 0.068(10) 0.007(6) -0.006(6) 0.013(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0000 0.0000 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 S1 C5 . . 89.4(7) ? N1 C2 C4 . . 112.0(12) ? N1 C2 C3 . . 103.4(11) ? C4 C2 C3 . . 110.0(13) ? C2 C4 S1 . . 106.8(11) ? C6 C5 C3 . . 112.5(10) ? C6 C5 S1 . . 118.3(9) ? C3 C5 S1 . . 106.0(9) ? N2 C3 C5 . . 112.1(12) ? N2 C3 C2 . . 100.8(10) ? C5 C3 C2 . . 108.4(10) ? C1 N2 C3 . . 116.1(12) ? C5 C6 C7 . . 118.3(12) ? C8 C9 C10 . . 112.9(11) ? O1 C1 N2 . . 128.0(13) ? O1 C1 N1 . . 122.8(11) ? N2 C1 N1 . . 109.1(11) ? O00F C10 O7 . . 122.1(13) ? O00F C10 C9 . . 123.4(13) ? O7 C10 C9 . . 114.4(11) ? C1 N1 C2 . . 110.4(11) ? C9 C8 C7 . . 112.8(11) ? C8 C7 C6 . . 116.6(12) ? 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 S1 C4 . 1.771(19) ? S1 C5 . 1.788(13) ? C2 N1 . 1.446(17) ? C2 C4 . 1.49(2) ? C2 C3 . 1.51(2) ? O1 C1 . 1.285(17) ? C5 C6 . 1.472(17) ? C5 C3 . 1.514(19) ? C3 N2 . 1.398(17) ? O7 C10 . 1.251(19) ? N2 C1 . 1.277(16) ? C6 C7 . 1.53(2) ? C9 C8 . 1.44(2) ? C9 C10 . 1.500(18) ? C1 N1 . 1.316(17) ? C10 O00F . 1.247(19) ? C8 C7 . 1.46(2) ?