#------------------------------------------------------------------------------ #$Date: 2020-05-28 04:45:35 +0300 (Thu, 28 May 2020) $ #$Revision: 252419 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240583.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_7240583 loop_ _publ_author_name 'Fellowes, Thomas' 'van Koeverden, Martin P.' 'White, Jonathan' _publ_section_title ; Thermal conversion of a pyridine solvate to a de-solvate facilitated by rearrangement of chalcogen bonds. The solvate and non-solvate structures of N-(2-nitro-4-(3-oxobenzo[d][1,2]selenazol-2(3H)-yl)phenyl)picolinamide ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00662A _journal_year 2020 _chemical_formula_sum 'C24 H17 N5 O4 Se' _chemical_formula_weight 518.39 _space_group_crystal_system monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yc' _space_group_name_H-M_alt 'P 1 c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2020-05-02 deposited with the CCDC. 2020-05-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.154(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 4.9726(2) _cell_length_b 14.6836(5) _cell_length_c 14.4255(5) _cell_measurement_reflns_used 3423 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 75.4450 _cell_measurement_theta_min 3.0190 _cell_volume 1042.64(7) _computing_cell_refinement 'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_unetI/netI 0.0714 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 6794 _diffrn_reflns_point_group_measured_fraction_full 0.750 _diffrn_reflns_point_group_measured_fraction_max 0.710 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.785 _diffrn_reflns_theta_min 3.010 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.829 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88658 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.651 _exptl_crystal_description needle _exptl_crystal_F_000 524 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.033 _exptl_crystal_size_min 0.026 _refine_diff_density_max 0.635 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.091 _refine_ls_abs_structure_details ; Flack x determined using 848 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 307 _refine_ls_number_reflns 3132 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.098 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0422 _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^)+(0.0561P)^2^+0.3921P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1088 _refine_ls_wR_factor_ref 0.1106 _reflns_Friedel_coverage 0.451 _reflns_Friedel_fraction_full 0.501 _reflns_Friedel_fraction_max 0.443 _reflns_number_gt 2977 _reflns_number_total 3132 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00662a2.cif _cod_data_source_block 1PYR _cod_original_sg_symbol_H-M 'P c' _cod_database_code 7240583 _shelx_shelxl_version_number 2016/6 _chemical_oxdiff_usercomment 'Tom Fellowes Se intermediate with pyridine' _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. ; _oxdiff_exptl_absorpt_empirical_full_min 0.759 _oxdiff_exptl_absorpt_empirical_full_max 1.299 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL shelxt_a.res in Pc shelx.res created by SHELXL-2016/6 at 12:23:10 on 24-Apr-2020 CELL 1.54184 4.9726 14.6836 14.4255 90.000 98.154 90.000 ZERR 2.00 0.0002 0.0005 0.0005 0.000 0.004 0.000 LATT -1 SYMM X, - Y, 1/2 + Z SFAC C H N O SE UNIT 48 34 10 8 2 MERG 2 bind N5 Se1 HTAB C6 N5 HTAB C9 O1 HTAB C12 O4 HTAB C13 Se1 EQIV $1 x-2, -y+2, z-1/2 HTAB C18 O1_$1 EQIV $2 x, -y+1, z-1/2 HTAB C21 O1_$2 HTAB N3 N4 HTAB N3 O3 FMAP 2 PLAN 20 ACTA HTAB 2.00000 BOND $H CONF L.S. 10 TEMP -143.00 WGHT 0.056100 0.392100 FVAR 2.91498 C1 1 1.232952 0.511047 0.672937 11.00000 0.02132 0.02195 = 0.03080 0.00262 0.00744 -0.00128 C2 1 1.309333 0.597268 0.708795 11.00000 0.02356 0.01576 = 0.02703 0.00376 0.00297 0.00263 C3 1 1.530530 0.606849 0.777747 11.00000 0.02755 0.02061 = 0.02820 -0.00231 0.00018 0.00141 AFIX 43 H3 2 1.585177 0.665562 0.800853 11.00000 -1.20000 AFIX 0 C4 1 1.672637 0.529832 0.813084 11.00000 0.02776 0.02580 = 0.02611 0.00154 -0.00670 0.00577 AFIX 43 H4 2 1.826941 0.535827 0.859711 11.00000 -1.20000 AFIX 0 C5 1 1.588408 0.444264 0.780049 11.00000 0.03179 0.02180 = 0.02642 0.00511 0.00354 0.00617 AFIX 43 H5 2 1.683687 0.391914 0.805695 11.00000 -1.20000 AFIX 0 C6 1 1.367278 0.433498 0.710132 11.00000 0.02836 0.01477 = 0.03206 0.00374 0.00306 0.00260 AFIX 43 H6 2 1.309680 0.374611 0.688401 11.00000 -1.20000 AFIX 0 C7 1 1.133763 0.674019 0.670759 11.00000 0.02724 0.01644 = 0.02295 0.00401 -0.00037 0.00105 C8 1 0.731528 0.701924 0.552942 11.00000 0.02121 0.01542 = 0.01949 0.00137 0.00189 0.00249 C9 1 0.748866 0.795881 0.553054 11.00000 0.02026 0.01739 = 0.02403 -0.00013 0.00244 0.00228 AFIX 43 H9 2 0.898111 0.825070 0.589689 11.00000 -1.20000 AFIX 0 C10 1 0.551019 0.847921 0.500336 11.00000 0.02356 0.01249 = 0.02555 0.00168 0.00072 0.00117 C11 1 0.324854 0.808970 0.443231 11.00000 0.01764 0.01876 = 0.02407 0.00132 0.00222 0.00272 C12 1 0.314230 0.713490 0.443465 11.00000 0.02110 0.01262 = 0.03001 -0.00237 -0.00049 -0.00332 AFIX 43 H12 2 0.167971 0.683691 0.405880 11.00000 -1.20000 AFIX 0 C13 1 0.510189 0.661460 0.496744 11.00000 0.02577 0.01467 = 0.02737 0.00284 0.00004 -0.00353 AFIX 43 H13 2 0.494649 0.596976 0.495271 11.00000 -1.20000 AFIX 0 C14 1 -0.077992 0.831966 0.323398 11.00000 0.02489 0.01939 = 0.02727 0.00014 0.00441 -0.00150 C15 1 -0.263968 0.907056 0.283481 11.00000 0.02458 0.01648 = 0.02454 0.00118 0.00560 0.00117 C16 1 -0.497019 0.884098 0.222132 11.00000 0.02515 0.02567 = 0.02770 0.00119 0.00071 0.00013 AFIX 43 H16 2 -0.537524 0.822443 0.205752 11.00000 -1.20000 AFIX 0 C17 1 -0.667405 0.954004 0.185873 11.00000 0.02197 0.03597 = 0.02718 0.00583 0.00041 0.00457 AFIX 43 H17 2 -0.829039 0.941124 0.144456 11.00000 -1.20000 AFIX 0 C18 1 -0.599064 1.042313 0.210729 11.00000 0.03604 0.02985 = 0.03034 0.00679 0.00506 0.01209 AFIX 43 H18 2 -0.712318 1.091243 0.186143 11.00000 -1.20000 AFIX 0 C19 1 -0.362804 1.059368 0.272148 11.00000 0.03690 0.02312 = 0.03192 0.00204 0.00167 0.00804 AFIX 43 H19 2 -0.318420 1.120705 0.288790 11.00000 -1.20000 AFIX 0 C20 1 1.151699 0.333800 0.469443 11.00000 0.03012 0.02235 = 0.03907 0.00184 0.00542 -0.00062 AFIX 43 H20 2 1.258002 0.379910 0.446034 11.00000 -1.20000 AFIX 0 C21 1 1.152767 0.246933 0.431302 11.00000 0.03627 0.02564 = 0.03417 -0.00268 0.00656 0.00283 AFIX 43 H21 2 1.257190 0.234340 0.382528 11.00000 -1.20000 AFIX 0 C22 1 1.000703 0.179192 0.464975 11.00000 0.03384 0.02020 = 0.03206 -0.00449 -0.00449 0.00131 AFIX 43 H22 2 1.000860 0.118973 0.440906 11.00000 -1.20000 AFIX 0 C23 1 0.847619 0.201376 0.534903 11.00000 0.03557 0.01775 = 0.04471 0.00084 0.00560 -0.00240 AFIX 43 H23 2 0.738970 0.156688 0.559480 11.00000 -1.20000 AFIX 0 C24 1 0.856064 0.290366 0.568443 11.00000 0.03811 0.02003 = 0.03869 0.00214 0.00941 0.00285 AFIX 43 H24 2 0.748712 0.305730 0.615640 11.00000 -1.20000 AFIX 0 N1 3 0.929996 0.645389 0.604098 11.00000 0.02092 0.01698 = 0.02619 -0.00044 -0.00141 -0.00131 N2 3 0.593237 0.946210 0.505062 11.00000 0.02464 0.01468 = 0.02548 -0.00060 -0.00076 0.00148 N3 3 0.125377 0.861203 0.390498 11.00000 0.02251 0.01142 = 0.02877 -0.00288 0.00032 -0.00040 AFIX 43 H3A 2 0.130909 0.920130 0.401723 11.00000 -1.20000 AFIX 0 N4 3 -0.193718 0.992871 0.309194 11.00000 0.03030 0.01978 = 0.02981 0.00151 -0.00062 0.00488 N5 3 1.008602 0.354872 0.537040 11.00000 0.03249 0.01868 = 0.03144 0.00014 0.00205 0.00354 O1 4 1.173013 0.753575 0.698214 11.00000 0.03368 0.01768 = 0.03576 -0.00418 -0.00552 0.00283 O2 4 0.815202 0.974488 0.542888 11.00000 0.02651 0.01834 = 0.03554 0.00008 -0.00972 -0.00219 O3 4 0.409545 0.998586 0.471944 11.00000 0.02680 0.01658 = 0.03492 -0.00081 -0.00429 0.00519 O4 4 -0.112347 0.753323 0.296037 11.00000 0.03595 0.01754 = 0.03740 -0.00125 -0.01029 0.00137 SE1 5 0.938548 0.516591 0.573034 11.00000 0.02385 0.01385 = 0.02819 0.00086 0.00031 0.00041 HKLF 4 REM shelxt_a.res in Pc REM R1 = 0.0422 for 2977 Fo > 4sig(Fo) and 0.0447 for all 3132 data REM 307 parameters refined using 2 restraints END WGHT 0.0561 0.3921 REM Instructions for potential hydrogen bonds HTAB C6 N5 HTAB C9 O1 HTAB C12 O4 HTAB C13 Se1 HTAB C18 O1_$1 HTAB C21 O1_$2 HTAB N3 N4 HTAB N3 O3 REM Highest difference peak 0.635, deepest hole -0.727, 1-sigma level 0.091 Q1 1 0.9392 0.4321 0.5715 11.00000 0.05 0.64 Q2 1 0.9310 0.6020 0.5752 11.00000 0.05 0.54 Q3 1 1.0452 0.5160 0.5192 11.00000 0.05 0.52 Q4 1 0.8177 0.4994 0.5086 11.00000 0.05 0.48 Q5 1 1.0639 0.5002 0.6405 11.00000 0.05 0.41 Q6 1 0.0975 0.9803 0.4193 11.00000 0.05 0.41 Q7 1 0.8372 0.5104 0.6457 11.00000 0.05 0.38 Q8 1 0.9284 0.5481 0.4843 11.00000 0.05 0.37 Q9 1 0.9327 0.5548 0.6627 11.00000 0.05 0.34 Q10 1 0.9108 0.5686 0.6425 11.00000 0.05 0.34 Q11 1 1.3275 0.4833 0.7356 11.00000 0.05 0.31 Q12 1 0.3491 0.7468 0.4364 11.00000 0.05 0.29 Q13 1 1.5898 0.5645 0.7819 11.00000 0.05 0.29 Q14 1 0.9350 0.4810 0.6605 11.00000 0.05 0.29 Q15 1 0.9575 0.4650 0.4936 11.00000 0.05 0.29 Q16 1 0.0257 0.7499 0.3395 11.00000 0.05 0.29 Q17 1 1.1569 0.2757 0.3082 11.00000 0.05 0.28 Q18 1 1.0738 0.4327 0.4361 11.00000 0.05 0.28 Q19 1 0.6210 0.6792 0.5347 11.00000 0.05 0.28 Q20 1 1.6327 0.5991 0.8397 11.00000 0.05 0.28 ; _shelx_res_checksum 51376 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -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_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 C1 C 1.2330(12) 0.5110(4) 0.6729(5) 0.0243(12) Uani 1 1 d . . . . . C2 C 1.3093(12) 0.5973(4) 0.7088(4) 0.0222(11) Uani 1 1 d . . . . . C3 C 1.5305(13) 0.6068(4) 0.7777(4) 0.0258(12) Uani 1 1 d . . . . . H3 H 1.585177 0.665562 0.800853 0.031 Uiso 1 1 calc R U . . . C4 C 1.6726(13) 0.5298(4) 0.8131(4) 0.0276(12) Uani 1 1 d . . . . . H4 H 1.826941 0.535827 0.859711 0.033 Uiso 1 1 calc R U . . . C5 C 1.5884(13) 0.4443(4) 0.7800(4) 0.0267(12) Uani 1 1 d . . . . . H5 H 1.683687 0.391914 0.805695 0.032 Uiso 1 1 calc R U . . . C6 C 1.3673(12) 0.4335(4) 0.7101(4) 0.0252(12) Uani 1 1 d . . . . . H6 H 1.309680 0.374611 0.688401 0.030 Uiso 1 1 calc R U . . . C7 C 1.1338(12) 0.6740(4) 0.6708(4) 0.0226(11) Uani 1 1 d . . . . . C8 C 0.7315(11) 0.7019(4) 0.5529(4) 0.0188(10) Uani 1 1 d . . . . . C9 C 0.7489(12) 0.7959(4) 0.5531(4) 0.0206(11) Uani 1 1 d . . . . . H9 H 0.898111 0.825070 0.589689 0.025 Uiso 1 1 calc R U . . . C10 C 0.5510(11) 0.8479(4) 0.5003(4) 0.0208(11) Uani 1 1 d . . . . . C11 C 0.3249(11) 0.8090(4) 0.4432(4) 0.0202(11) Uani 1 1 d . . . . . C12 C 0.3142(12) 0.7135(4) 0.4435(4) 0.0216(11) Uani 1 1 d . . . . . H12 H 0.167971 0.683691 0.405880 0.026 Uiso 1 1 calc R U . . . C13 C 0.5102(12) 0.6615(4) 0.4967(4) 0.0230(11) Uani 1 1 d . . . . . H13 H 0.494649 0.596976 0.495271 0.028 Uiso 1 1 calc R U . . . C14 C -0.0780(13) 0.8320(4) 0.3234(4) 0.0238(12) Uani 1 1 d . . . . . C15 C -0.2640(12) 0.9071(4) 0.2835(4) 0.0217(11) Uani 1 1 d . . . . . C16 C -0.4970(13) 0.8841(4) 0.2221(5) 0.0265(12) Uani 1 1 d . . . . . H16 H -0.537524 0.822443 0.205752 0.032 Uiso 1 1 calc R U . . . C17 C -0.6674(13) 0.9540(5) 0.1859(4) 0.0287(13) Uani 1 1 d . . . . . H17 H -0.829039 0.941124 0.144456 0.034 Uiso 1 1 calc R U . . . C18 C -0.5991(15) 1.0423(5) 0.2107(5) 0.0320(14) Uani 1 1 d . . . . . H18 H -0.712318 1.091243 0.186143 0.038 Uiso 1 1 calc R U . . . C19 C -0.3628(14) 1.0594(5) 0.2721(5) 0.0310(13) Uani 1 1 d . . . . . H19 H -0.318420 1.120705 0.288790 0.037 Uiso 1 1 calc R U . . . C20 C 1.1517(13) 0.3338(4) 0.4694(5) 0.0305(13) Uani 1 1 d . . . . . H20 H 1.258002 0.379910 0.446034 0.037 Uiso 1 1 calc R U . . . C21 C 1.1528(14) 0.2469(4) 0.4313(5) 0.0319(13) Uani 1 1 d . . . . . H21 H 1.257190 0.234340 0.382528 0.038 Uiso 1 1 calc R U . . . C22 C 1.0007(13) 0.1792(4) 0.4650(5) 0.0296(13) Uani 1 1 d . . . . . H22 H 1.000860 0.118973 0.440906 0.035 Uiso 1 1 calc R U . . . C23 C 0.8476(15) 0.2014(4) 0.5349(5) 0.0327(14) Uani 1 1 d . . . . . H23 H 0.738970 0.156688 0.559480 0.039 Uiso 1 1 calc R U . . . C24 C 0.8561(14) 0.2904(4) 0.5684(5) 0.0319(14) Uani 1 1 d . . . . . H24 H 0.748712 0.305730 0.615640 0.038 Uiso 1 1 calc R U . . . N1 N 0.9300(10) 0.6454(3) 0.6041(3) 0.0218(10) Uani 1 1 d . . . . . N2 N 0.5932(10) 0.9462(3) 0.5051(4) 0.0220(9) Uani 1 1 d . . . . . N3 N 0.1254(10) 0.8612(3) 0.3905(4) 0.0212(10) Uani 1 1 d . . . . . H3A H 0.130909 0.920130 0.401723 0.025 Uiso 1 1 calc R U . . . N4 N -0.1937(11) 0.9929(4) 0.3092(4) 0.0271(11) Uani 1 1 d . . . . . N5 N 1.0086(12) 0.3549(4) 0.5370(4) 0.0278(11) Uani 1 1 d . . . . . O1 O 1.1730(9) 0.7536(3) 0.6982(3) 0.0301(9) Uani 1 1 d . . . . . O2 O 0.8152(9) 0.9745(3) 0.5429(3) 0.0282(10) Uani 1 1 d . . . . . O3 O 0.4095(10) 0.9986(3) 0.4719(4) 0.0269(9) Uani 1 1 d . . . . . O4 O -0.1123(10) 0.7533(3) 0.2960(4) 0.0318(10) Uani 1 1 d . . . . . Se1 Se 0.93855(7) 0.51659(3) 0.57303(5) 0.02229(18) 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 0.021(3) 0.022(3) 0.031(3) 0.003(2) 0.007(2) -0.001(2) C2 0.024(3) 0.016(2) 0.027(3) 0.004(2) 0.003(2) 0.003(2) C3 0.028(3) 0.021(3) 0.028(3) -0.002(2) 0.000(2) 0.001(2) C4 0.028(3) 0.026(3) 0.026(3) 0.002(2) -0.007(2) 0.006(2) C5 0.032(3) 0.022(3) 0.026(3) 0.005(2) 0.004(2) 0.006(2) C6 0.028(3) 0.015(3) 0.032(3) 0.004(2) 0.003(2) 0.003(2) C7 0.027(3) 0.016(3) 0.023(3) 0.004(2) 0.000(2) 0.001(2) C8 0.021(2) 0.015(3) 0.019(3) 0.0014(19) 0.002(2) 0.002(2) C9 0.020(2) 0.017(3) 0.024(3) 0.000(2) 0.002(2) 0.002(2) C10 0.024(3) 0.012(3) 0.026(3) 0.002(2) 0.001(2) 0.001(2) C11 0.018(2) 0.019(3) 0.024(3) 0.001(2) 0.002(2) 0.003(2) C12 0.021(2) 0.013(3) 0.030(3) -0.002(2) 0.000(2) -0.003(2) C13 0.026(3) 0.015(3) 0.027(3) 0.003(2) 0.000(2) -0.004(2) C14 0.025(3) 0.019(3) 0.027(3) 0.000(2) 0.004(2) -0.001(2) C15 0.025(3) 0.016(3) 0.025(3) 0.001(2) 0.006(2) 0.001(2) C16 0.025(3) 0.026(3) 0.028(3) 0.001(2) 0.001(2) 0.000(2) C17 0.022(3) 0.036(4) 0.027(3) 0.006(3) 0.000(2) 0.005(3) C18 0.036(3) 0.030(3) 0.030(3) 0.007(3) 0.005(3) 0.012(3) C19 0.037(3) 0.023(3) 0.032(3) 0.002(2) 0.002(3) 0.008(3) C20 0.030(3) 0.022(3) 0.039(3) 0.002(2) 0.005(3) -0.001(2) C21 0.036(3) 0.026(3) 0.034(3) -0.003(2) 0.007(3) 0.003(3) C22 0.034(3) 0.020(3) 0.032(3) -0.004(2) -0.004(3) 0.001(2) C23 0.036(3) 0.018(3) 0.045(4) 0.001(3) 0.006(3) -0.002(2) C24 0.038(3) 0.020(3) 0.039(4) 0.002(3) 0.009(3) 0.003(2) N1 0.021(2) 0.017(2) 0.026(2) -0.0004(17) -0.001(2) -0.0013(18) N2 0.025(2) 0.015(2) 0.025(2) -0.0006(18) -0.0008(19) 0.0015(18) N3 0.023(2) 0.011(2) 0.029(2) -0.0029(18) 0.0003(19) -0.0004(18) N4 0.030(3) 0.020(2) 0.030(3) 0.002(2) -0.001(2) 0.005(2) N5 0.032(3) 0.019(2) 0.031(3) 0.000(2) 0.002(2) 0.004(2) O1 0.034(2) 0.018(2) 0.036(2) -0.0042(17) -0.0055(18) 0.0028(17) O2 0.027(2) 0.018(2) 0.036(2) 0.0001(17) -0.0097(19) -0.0022(16) O3 0.027(2) 0.0166(19) 0.035(2) -0.0008(18) -0.0043(19) 0.0052(18) O4 0.036(2) 0.018(2) 0.037(2) -0.0012(17) -0.0103(19) 0.0014(18) Se1 0.0238(3) 0.0139(3) 0.0282(3) 0.0009(3) 0.00031(18) 0.0004(3) 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' Se Se -0.7943 1.1372 '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 C6 C1 C2 120.6(6) . . ? C6 C1 Se1 127.1(5) . . ? C2 C1 Se1 112.3(5) . . ? C3 C2 C1 120.3(6) . . ? C3 C2 C7 123.8(5) . . ? C1 C2 C7 115.9(5) . . ? C2 C3 C4 119.5(6) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 119.8(6) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.4(6) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 118.3(6) . . ? C1 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? O1 C7 N1 125.8(5) . . ? O1 C7 C2 122.7(5) . . ? N1 C7 C2 111.5(5) . . ? C9 C8 C13 117.8(5) . . ? C9 C8 N1 123.1(5) . . ? C13 C8 N1 119.0(5) . . ? C8 C9 C10 120.7(5) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C11 122.7(5) . . ? C9 C10 N2 115.7(5) . . ? C11 C10 N2 121.6(5) . . ? N3 C11 C12 121.9(5) . . ? N3 C11 C10 122.7(5) . . ? C12 C11 C10 115.4(5) . . ? C13 C12 C11 122.0(5) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C8 121.4(5) . . ? C12 C13 H13 119.3 . . ? C8 C13 H13 119.3 . . ? O4 C14 N3 125.5(6) . . ? O4 C14 C15 121.3(6) . . ? N3 C14 C15 113.3(5) . . ? N4 C15 C16 124.1(6) . . ? N4 C15 C14 117.4(5) . . ? C16 C15 C14 118.5(5) . . ? C17 C16 C15 117.9(6) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C18 C17 C16 119.0(6) . . ? C18 C17 H17 120.5 . . ? C16 C17 H17 120.5 . . ? C17 C18 C19 119.4(6) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? N4 C19 C18 123.0(6) . . ? N4 C19 H19 118.5 . . ? C18 C19 H19 118.5 . . ? N5 C20 C21 122.6(6) . . ? N5 C20 H20 118.7 . . ? C21 C20 H20 118.7 . . ? C22 C21 C20 119.3(6) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 118.2(6) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? C22 C23 C24 118.8(6) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? N5 C24 C23 122.7(6) . . ? N5 C24 H24 118.7 . . ? C23 C24 H24 118.7 . . ? C7 N1 C8 125.6(5) . . ? C7 N1 Se1 115.1(4) . . ? C8 N1 Se1 119.1(4) . . ? O2 N2 O3 121.8(5) . . ? O2 N2 C10 117.9(5) . . ? O3 N2 C10 120.2(5) . . ? C14 N3 C11 127.8(5) . . ? C14 N3 H3A 116.1 . . ? C11 N3 H3A 116.1 . . ? C15 N4 C19 116.5(6) . . ? C20 N5 C24 118.4(6) . . ? C20 N5 Se1 119.2(4) . . ? C24 N5 Se1 120.6(4) . . ? C1 Se1 N1 84.7(2) . . ? C1 Se1 N5 90.1(2) . . ? N1 Se1 N5 173.2(2) . . ? 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 C1 C6 1.389(9) . ? C1 C2 1.400(9) . ? C1 Se1 1.905(7) . ? C2 C3 1.382(9) . ? C2 C7 1.482(8) . ? C3 C4 1.391(9) . ? C3 H3 0.9500 . ? C4 C5 1.387(9) . ? C4 H4 0.9500 . ? C5 C6 1.392(9) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.240(7) . ? C7 N1 1.361(8) . ? C8 C9 1.382(8) . ? C8 C13 1.403(8) . ? C8 N1 1.415(7) . ? C9 C10 1.385(8) . ? C9 H9 0.9500 . ? C10 C11 1.417(8) . ? C10 N2 1.459(7) . ? C11 N3 1.392(7) . ? C11 C12 1.403(8) . ? C12 C13 1.383(8) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O4 1.224(8) . ? C14 N3 1.366(8) . ? C14 C15 1.500(8) . ? C15 N4 1.346(8) . ? C15 C16 1.396(9) . ? C16 C17 1.385(9) . ? C16 H16 0.9500 . ? C17 C18 1.375(11) . ? C17 H17 0.9500 . ? C18 C19 1.390(10) . ? C18 H18 0.9500 . ? C19 N4 1.348(9) . ? C19 H19 0.9500 . ? C20 N5 1.323(9) . ? C20 C21 1.389(9) . ? C20 H20 0.9500 . ? C21 C22 1.379(10) . ? C21 H21 0.9500 . ? C22 C23 1.386(10) . ? C22 H22 0.9500 . ? C23 C24 1.392(9) . ? C23 H23 0.9500 . ? C24 N5 1.332(9) . ? C24 H24 0.9500 . ? N1 Se1 1.945(5) . ? N2 O2 1.232(7) . ? N2 O3 1.237(7) . ? N3 H3A 0.8800 . ? N5 Se1 2.466(5) . ? 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 C6 H6 N5 0.95 2.48 3.080(8) 120.8 . C9 H9 O1 0.95 2.19 2.822(7) 122.7 . C12 H12 O4 0.95 2.21 2.843(7) 123.4 . C13 H13 Se1 0.95 2.61 3.100(6) 112.3 . C18 H18 O1 0.95 2.36 3.200(8) 147.0 2_374 C21 H21 O1 0.95 2.64 3.378(8) 135.1 2_564 N3 H3A N4 0.88 2.22 2.665(7) 111.2 . N3 H3A O3 0.88 1.97 2.641(7) 132.2 . 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 C6 C1 C2 C3 4.1(9) . . . . ? Se1 C1 C2 C3 -176.0(5) . . . . ? C6 C1 C2 C7 -173.7(5) . . . . ? Se1 C1 C2 C7 6.2(7) . . . . ? C1 C2 C3 C4 -1.7(10) . . . . ? C7 C2 C3 C4 175.9(6) . . . . ? C2 C3 C4 C5 -1.1(10) . . . . ? C3 C4 C5 C6 1.6(10) . . . . ? C2 C1 C6 C5 -3.5(9) . . . . ? Se1 C1 C6 C5 176.5(5) . . . . ? C4 C5 C6 C1 0.7(9) . . . . ? C3 C2 C7 O1 0.1(10) . . . . ? C1 C2 C7 O1 177.9(6) . . . . ? C3 C2 C7 N1 -179.6(6) . . . . ? C1 C2 C7 N1 -1.9(8) . . . . ? C13 C8 C9 C10 1.0(9) . . . . ? N1 C8 C9 C10 178.8(5) . . . . ? C8 C9 C10 C11 -0.8(9) . . . . ? C8 C9 C10 N2 -179.2(5) . . . . ? C9 C10 C11 N3 179.8(5) . . . . ? N2 C10 C11 N3 -2.0(8) . . . . ? C9 C10 C11 C12 0.0(8) . . . . ? N2 C10 C11 C12 178.2(5) . . . . ? N3 C11 C12 C13 -179.1(6) . . . . ? C10 C11 C12 C13 0.7(8) . . . . ? C11 C12 C13 C8 -0.5(9) . . . . ? C9 C8 C13 C12 -0.4(9) . . . . ? N1 C8 C13 C12 -178.3(5) . . . . ? O4 C14 C15 N4 -172.3(6) . . . . ? N3 C14 C15 N4 7.4(8) . . . . ? O4 C14 C15 C16 7.5(9) . . . . ? N3 C14 C15 C16 -172.8(5) . . . . ? N4 C15 C16 C17 -0.4(9) . . . . ? C14 C15 C16 C17 179.9(6) . . . . ? C15 C16 C17 C18 0.7(9) . . . . ? C16 C17 C18 C19 -0.6(10) . . . . ? C17 C18 C19 N4 0.1(11) . . . . ? N5 C20 C21 C22 -0.4(11) . . . . ? C20 C21 C22 C23 1.2(10) . . . . ? C21 C22 C23 C24 -0.6(10) . . . . ? C22 C23 C24 N5 -1.0(11) . . . . ? O1 C7 N1 C8 1.7(10) . . . . ? C2 C7 N1 C8 -178.6(5) . . . . ? O1 C7 N1 Se1 176.9(5) . . . . ? C2 C7 N1 Se1 -3.4(6) . . . . ? C9 C8 N1 C7 11.7(9) . . . . ? C13 C8 N1 C7 -170.5(6) . . . . ? C9 C8 N1 Se1 -163.4(4) . . . . ? C13 C8 N1 Se1 14.4(7) . . . . ? C9 C10 N2 O2 10.6(8) . . . . ? C11 C10 N2 O2 -167.8(6) . . . . ? C9 C10 N2 O3 -169.3(5) . . . . ? C11 C10 N2 O3 12.3(8) . . . . ? O4 C14 N3 C11 -2.7(10) . . . . ? C15 C14 N3 C11 177.6(5) . . . . ? C12 C11 N3 C14 -10.5(9) . . . . ? C10 C11 N3 C14 169.8(6) . . . . ? C16 C15 N4 C19 -0.1(9) . . . . ? C14 C15 N4 C19 179.7(6) . . . . ? C18 C19 N4 C15 0.2(10) . . . . ? C21 C20 N5 C24 -1.2(10) . . . . ? C21 C20 N5 Se1 -165.9(5) . . . . ? C23 C24 N5 C20 1.9(10) . . . . ? C23 C24 N5 Se1 166.4(5) . . . . ?