#------------------------------------------------------------------------------ #$Date: 2020-05-28 04:45:35 +0300 (Thu, 28 May 2020) $ #$Revision: 252419 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240584.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_7240584 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 'C19 H12 N4 O4 Se' _chemical_formula_weight 439.29 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens mixed _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.652(3) _cell_length_b 7.5250(15) _cell_length_c 34.367(7) _cell_measurement_reflns_used 3751 _cell_measurement_temperature 100.0(2) _cell_measurement_theta_max 32.3 _cell_measurement_theta_min 2.3 _cell_volume 3272.0(12) _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_collection 'AS QEGUI' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _diffrn_ambient_temperature 100.0(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.888 _diffrn_measurement_device_type 'Dectris Eiger 16M' _diffrn_measurement_method 'Omega Scan' _diffrn_radiation_monochromator 'Silicon Double Crystal' _diffrn_radiation_source 'MX2 Beamline Australian Synchrotron' _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.82656 _diffrn_reflns_av_R_equivalents 0.0803 _diffrn_reflns_av_unetI/netI 0.0545 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.888 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_number 35758 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.888 _diffrn_reflns_theta_full 29.731 _diffrn_reflns_theta_max 32.284 _diffrn_reflns_theta_min 2.325 _exptl_absorpt_coefficient_mu 3.383 _exptl_absorpt_correction_T_max 0.86 _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'XDS (Kabsch, 1993)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.784 _exptl_crystal_description needle _exptl_crystal_F_000 1760 _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.005 _exptl_crystal_size_min 0.005 _refine_diff_density_max 0.972 _refine_diff_density_min -1.364 _refine_diff_density_rms 0.113 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 257 _refine_ls_number_reflns 3282 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0601 _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^)+(0.1223P)^2^+1.2109P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1641 _refine_ls_wR_factor_ref 0.1802 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2513 _reflns_number_total 3282 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00662a2.cif _cod_data_source_block 1DMF _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 3272.0(11) _cod_database_code 7240584 _shelx_shelxl_version_number 2016/6 _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_res_file ; TITL shelxt_a.res in Pbca shelx.res created by SHELXL-2016/6 at 11:37:57 on 07-Oct-2019 CELL 0.82656 12.6520 7.5250 34.3670 90.000 90.000 90.000 ZERR 8.00 0.0025 0.0015 0.0069 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 H N O SE DISP $C 0.00511 0.00239 15.74444 DISP $H -0.00002 0.00000 0.66615 DISP $N 0.00955 0.00480 28.17579 DISP $O 0.01604 0.00875 47.81841 DISP $Se -0.69429 2.86778 13226.25234 UNIT 152 96 32 32 8 MERG 2 HTAB C9 O1 HTAB C12 O4 HTAB C13 Se1 EQIV $1 x-1/2, y, -z+3/2 HTAB C6 O1_$1 HTAB N3 O3 HTAB N3 N4 HTAB C9 O1 HTAB C12 O4 HTAB C13 Se1 HTAB C6 O1_$1 HTAB N3 O3 HTAB N3 N4 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 10 WGHT 0.122300 1.210900 FVAR 0.20385 SE1 5 0.068172 0.562213 0.733705 11.00000 0.03444 0.05845 = 0.04074 -0.00216 0.00045 -0.00048 O1 4 0.382265 0.593616 0.730815 11.00000 0.03071 0.05856 = 0.04076 -0.00575 -0.00294 -0.00257 O4 4 0.081043 0.168316 0.547882 11.00000 0.04005 0.08650 = 0.05172 -0.01238 -0.00060 -0.00561 O3 4 0.456429 0.254304 0.578776 11.00000 0.04350 0.08116 = 0.04947 -0.01108 0.00638 0.00092 N3 3 0.252958 0.243717 0.563008 11.00000 0.03734 0.05819 = 0.03789 -0.00030 0.00229 -0.00089 N1 3 0.208556 0.540657 0.713836 11.00000 0.03362 0.05623 = 0.03838 -0.00147 -0.00107 -0.00012 N4 3 0.324784 0.090004 0.499739 11.00000 0.04764 0.05529 = 0.04307 -0.00039 0.00148 0.00039 N2 3 0.439647 0.318031 0.610975 11.00000 0.03765 0.07041 = 0.04313 -0.00494 0.00207 0.00157 O2 4 0.510877 0.348069 0.633546 11.00000 0.03791 0.16248 = 0.06124 -0.03346 -0.00456 0.00706 C11 1 0.243086 0.319667 0.599763 11.00000 0.03908 0.04795 = 0.03706 0.00223 0.00280 -0.00276 C8 1 0.223348 0.469930 0.675654 11.00000 0.03848 0.04769 = 0.03710 0.00081 0.00279 -0.00080 C10 1 0.331377 0.356213 0.623448 11.00000 0.03585 0.05091 = 0.04232 0.00171 0.00336 0.00036 C9 1 0.322061 0.426569 0.660944 11.00000 0.03677 0.05381 = 0.04467 0.00219 -0.00136 -0.00246 AFIX 43 H9 2 0.382157 0.444301 0.676035 11.00000 -1.20000 AFIX 0 C12 1 0.144371 0.368183 0.615178 11.00000 0.03638 0.05690 = 0.04471 0.00140 -0.00183 -0.00290 AFIX 43 H12 2 0.083790 0.349738 0.600394 11.00000 -1.20000 AFIX 0 C13 1 0.135108 0.442644 0.651774 11.00000 0.03544 0.05347 = 0.04511 -0.00018 0.00243 0.00177 AFIX 43 H13 2 0.068598 0.475476 0.660777 11.00000 -1.20000 AFIX 0 C2 1 0.242739 0.665433 0.775253 11.00000 0.04153 0.05038 = 0.03724 0.00142 -0.00312 -0.00108 C1 1 0.133870 0.656064 0.778908 11.00000 0.03930 0.04979 = 0.03913 0.00030 -0.00362 -0.00095 C15 1 0.218298 0.096208 0.502425 11.00000 0.04726 0.05485 = 0.03622 0.00233 0.00156 -0.00043 C6 1 0.082977 0.710073 0.812738 11.00000 0.03763 0.05430 = 0.05066 0.00164 -0.00104 0.00172 AFIX 43 H6 2 0.009874 0.702614 0.815049 11.00000 -1.20000 AFIX 0 C7 1 0.288200 0.598614 0.738236 11.00000 0.04215 0.04762 = 0.03992 0.00105 0.00135 -0.00231 C4 1 0.253676 0.788845 0.839431 11.00000 0.04303 0.06139 = 0.03609 -0.00408 -0.00266 -0.00165 AFIX 43 H4 2 0.293037 0.836351 0.859780 11.00000 -1.20000 AFIX 0 C3 1 0.304166 0.731934 0.805843 11.00000 0.03902 0.05664 = 0.04274 0.00408 0.00042 0.00121 AFIX 43 H3 2 0.377354 0.737837 0.803688 11.00000 -1.20000 AFIX 0 C5 1 0.144110 0.775125 0.842815 11.00000 0.04077 0.05797 = 0.04419 -0.00226 0.00155 0.00112 AFIX 43 H5 2 0.111564 0.810530 0.865807 11.00000 -1.20000 AFIX 0 C19 1 0.365035 0.021882 0.466936 11.00000 0.04770 0.06535 = 0.04680 -0.00096 0.00616 0.00004 AFIX 43 H19 2 0.438161 0.016645 0.464439 11.00000 -1.20000 AFIX 0 C14 1 0.175393 0.171986 0.539685 11.00000 0.04563 0.05634 = 0.04101 0.00293 -0.00089 -0.00245 C18 1 0.303587 -0.041440 0.436409 11.00000 0.06591 0.05704 = 0.04228 0.00147 0.00489 0.00223 AFIX 43 H18 2 0.334683 -0.089398 0.414251 11.00000 -1.20000 AFIX 0 C16 1 0.150375 0.037154 0.473776 11.00000 0.04882 0.06056 = 0.04356 0.00045 -0.00347 -0.00050 AFIX 43 H16 2 0.077462 0.042768 0.476977 11.00000 -1.20000 AFIX 0 C17 1 0.195046 -0.031085 0.439931 11.00000 0.06243 0.05935 = 0.03887 -0.00075 -0.00709 -0.00428 AFIX 43 H17 2 0.151879 -0.069648 0.419721 11.00000 -1.20000 AFIX 0 H3A 2 0.312970 0.226961 0.552474 11.00000 0.07069 HKLF 4 1.0 0.00 1.00 0.00 1.00 0.00 0.00 0.00 0.00 -1.00 REM shelxt_a.res in Pbca REM R1 = 0.0601 for 2513 Fo > 4sig(Fo) and 0.0758 for all 3282 data REM 257 parameters refined using 0 restraints END WGHT 0.1223 1.2109 REM Highest difference peak 0.972, deepest hole -1.364, 1-sigma level 0.113 Q1 1 0.0648 0.6620 0.7185 11.00000 0.05 0.97 Q2 1 0.4199 0.5669 0.7335 11.00000 0.05 0.94 Q3 1 0.0678 0.4596 0.7492 11.00000 0.05 0.83 Q4 1 0.0680 0.6631 0.7499 11.00000 0.05 0.82 Q5 1 0.0653 0.4639 0.7192 11.00000 0.05 0.74 Q6 1 0.4274 0.8146 0.7336 11.00000 0.05 0.43 Q7 1 0.4200 0.1827 0.5474 11.00000 0.05 0.42 Q8 1 0.0660 0.5779 0.7998 11.00000 0.05 0.42 Q9 1 0.2928 0.5662 0.7683 11.00000 0.05 0.39 Q10 1 0.1548 0.3211 0.6193 11.00000 0.05 0.38 Q11 1 0.2047 0.0633 0.4934 11.00000 0.05 0.38 Q12 1 0.1725 0.0550 0.4600 11.00000 0.05 0.37 Q13 1 0.2550 0.0844 0.4999 11.00000 0.05 0.32 Q14 1 0.3514 0.3134 0.6223 11.00000 0.05 0.32 Q15 1 0.2117 0.5821 0.7112 11.00000 0.05 0.32 Q16 1 0.1799 0.7926 0.8411 11.00000 0.05 0.32 Q17 1 0.2696 0.5505 0.7271 11.00000 0.05 0.31 Q18 1 0.2858 0.4644 0.6687 11.00000 0.05 0.31 Q19 1 0.2045 0.4394 0.6680 11.00000 0.05 0.30 Q20 1 0.4580 0.2654 0.7018 11.00000 0.05 0.29 ; _shelx_res_checksum 14022 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' '-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_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 Se1 Se 0.06817(3) 0.56221(6) 0.73370(2) 0.0445(2) Uani 1 1 d . . . . . O1 O 0.3823(2) 0.5936(4) 0.73082(8) 0.0433(7) Uani 1 1 d . . . . . O4 O 0.0810(2) 0.1683(5) 0.54788(10) 0.0594(9) Uani 1 1 d . . . . . O3 O 0.4564(2) 0.2543(5) 0.57878(9) 0.0580(9) Uani 1 1 d . . . . . N3 N 0.2530(3) 0.2437(5) 0.56301(10) 0.0445(8) Uani 1 1 d . . . . . N1 N 0.2086(3) 0.5407(5) 0.71384(10) 0.0427(8) Uani 1 1 d . . . . . N4 N 0.3248(3) 0.0900(5) 0.49974(11) 0.0487(9) Uani 1 1 d . . . . . N2 N 0.4396(3) 0.3180(6) 0.61097(11) 0.0504(9) Uani 1 1 d . . . . . O2 O 0.5109(3) 0.3481(7) 0.63355(11) 0.0872(14) Uani 1 1 d . . . . . C11 C 0.2431(3) 0.3197(5) 0.59976(12) 0.0414(9) Uani 1 1 d . . . . . C8 C 0.2233(3) 0.4699(6) 0.67565(11) 0.0411(9) Uani 1 1 d . . . . . C10 C 0.3314(3) 0.3562(6) 0.62345(12) 0.0430(9) Uani 1 1 d . . . . . C9 C 0.3221(3) 0.4266(6) 0.66094(13) 0.0451(10) Uani 1 1 d . . . . . H9 H 0.382157 0.444301 0.676035 0.054 Uiso 1 1 calc R U . . . C12 C 0.1444(3) 0.3682(6) 0.61518(12) 0.0460(9) Uani 1 1 d . . . . . H12 H 0.083790 0.349738 0.600394 0.055 Uiso 1 1 calc R U . . . C13 C 0.1351(3) 0.4426(6) 0.65177(13) 0.0447(10) Uani 1 1 d . . . . . H13 H 0.068598 0.475476 0.660777 0.054 Uiso 1 1 calc R U . . . C2 C 0.2427(3) 0.6654(6) 0.77525(12) 0.0430(9) Uani 1 1 d . . . . . C1 C 0.1339(3) 0.6561(6) 0.77891(11) 0.0427(9) Uani 1 1 d . . . . . C15 C 0.2183(3) 0.0962(6) 0.50242(12) 0.0461(10) Uani 1 1 d . . . . . C6 C 0.0830(3) 0.7101(6) 0.81274(14) 0.0475(10) Uani 1 1 d . . . . . H6 H 0.009874 0.702614 0.815049 0.057 Uiso 1 1 calc R U . . . C7 C 0.2882(4) 0.5986(6) 0.73824(12) 0.0432(9) Uani 1 1 d . . . . . C4 C 0.2537(3) 0.7888(6) 0.83943(12) 0.0468(10) Uani 1 1 d . . . . . H4 H 0.293037 0.836351 0.859780 0.056 Uiso 1 1 calc R U . . . C3 C 0.3042(3) 0.7319(6) 0.80584(12) 0.0461(10) Uani 1 1 d . . . . . H3 H 0.377354 0.737837 0.803688 0.055 Uiso 1 1 calc R U . . . C5 C 0.1441(3) 0.7751(6) 0.84281(12) 0.0476(10) Uani 1 1 d . . . . . H5 H 0.111564 0.810530 0.865807 0.057 Uiso 1 1 calc R U . . . C19 C 0.3650(4) 0.0219(7) 0.46694(13) 0.0533(11) Uani 1 1 d . . . . . H19 H 0.438161 0.016645 0.464439 0.064 Uiso 1 1 calc R U . . . C14 C 0.1754(3) 0.1720(6) 0.53968(12) 0.0477(10) Uani 1 1 d . . . . . C18 C 0.3036(4) -0.0414(6) 0.43641(14) 0.0551(12) Uani 1 1 d . . . . . H18 H 0.334683 -0.089398 0.414251 0.066 Uiso 1 1 calc R U . . . C16 C 0.1504(4) 0.0372(6) 0.47378(13) 0.0510(10) Uani 1 1 d . . . . . H16 H 0.077462 0.042768 0.476977 0.061 Uiso 1 1 calc R U . . . C17 C 0.1950(4) -0.0311(6) 0.43993(13) 0.0536(11) Uani 1 1 d . . . . . H17 H 0.151879 -0.069648 0.419721 0.064 Uiso 1 1 calc R U . . . H3A H 0.313(5) 0.227(7) 0.5525(16) 0.071(17) Uiso 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 Se1 0.0344(3) 0.0585(4) 0.0407(3) -0.00216(17) 0.00045(16) -0.00048(17) O1 0.0307(15) 0.0586(18) 0.0408(15) -0.0057(12) -0.0029(11) -0.0026(12) O4 0.0401(16) 0.087(3) 0.0517(19) -0.0124(17) -0.0006(14) -0.0056(15) O3 0.0435(15) 0.081(2) 0.0495(18) -0.0111(16) 0.0064(14) 0.0009(15) N3 0.0373(17) 0.058(2) 0.0379(17) -0.0003(16) 0.0023(15) -0.0009(15) N1 0.0336(16) 0.056(2) 0.0384(17) -0.0015(15) -0.0011(14) -0.0001(14) N4 0.048(2) 0.055(2) 0.0431(19) -0.0004(16) 0.0015(17) 0.0004(16) N2 0.0377(18) 0.070(3) 0.043(2) -0.0049(18) 0.0021(15) 0.0016(16) O2 0.0379(17) 0.162(4) 0.061(2) -0.033(3) -0.0046(17) 0.007(2) C11 0.0391(19) 0.048(2) 0.0371(19) 0.0022(16) 0.0028(16) -0.0028(17) C8 0.038(2) 0.048(2) 0.0371(19) 0.0008(16) 0.0028(17) -0.0008(16) C10 0.0358(19) 0.051(2) 0.042(2) 0.0017(18) 0.0034(17) 0.0004(17) C9 0.037(2) 0.054(3) 0.045(2) 0.0022(18) -0.0014(18) -0.0025(16) C12 0.036(2) 0.057(3) 0.045(2) 0.0014(19) -0.0018(17) -0.0029(18) C13 0.035(2) 0.053(3) 0.045(2) -0.0002(17) 0.0024(18) 0.0018(16) C2 0.042(2) 0.050(3) 0.0372(19) 0.0014(17) -0.0031(16) -0.0011(18) C1 0.039(2) 0.050(2) 0.0391(19) 0.0003(17) -0.0036(17) -0.0009(17) C15 0.047(2) 0.055(2) 0.036(2) 0.0023(18) 0.0016(18) -0.0004(19) C6 0.0376(19) 0.054(3) 0.051(2) 0.002(2) -0.0010(18) 0.0017(18) C7 0.042(2) 0.048(2) 0.040(2) 0.0010(17) 0.0014(18) -0.0023(18) C4 0.043(2) 0.061(3) 0.036(2) -0.0041(19) -0.0027(17) -0.0016(19) C3 0.0390(19) 0.057(3) 0.043(2) 0.0041(18) 0.0004(18) 0.0012(18) C5 0.041(2) 0.058(3) 0.044(2) -0.0023(19) 0.0016(18) 0.0011(18) C19 0.048(2) 0.065(3) 0.047(2) -0.001(2) 0.006(2) 0.000(2) C14 0.046(2) 0.056(3) 0.041(2) 0.0029(18) -0.0009(18) -0.0025(18) C18 0.066(3) 0.057(3) 0.042(2) 0.0015(19) 0.005(2) 0.002(2) C16 0.049(2) 0.061(3) 0.044(2) 0.0005(19) -0.003(2) -0.0005(19) C17 0.062(3) 0.059(3) 0.039(2) -0.0008(19) -0.007(2) -0.004(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0051 0.0024 '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 0.0096 0.0048 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0160 0.0088 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.6943 2.8678 '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 C1 Se1 N1 85.24(16) . . ? C14 N3 C11 128.7(4) . . ? C14 N3 H3A 109(4) . . ? C11 N3 H3A 122(4) . . ? C7 N1 C8 125.4(3) . . ? C7 N1 Se1 115.8(3) . . ? C8 N1 Se1 118.8(3) . . ? C19 N4 C15 116.7(4) . . ? O2 N2 O3 121.5(3) . . ? O2 N2 C10 118.2(4) . . ? O3 N2 C10 120.2(3) . . ? N3 C11 C12 121.9(4) . . ? N3 C11 C10 122.2(3) . . ? C12 C11 C10 115.9(4) . . ? C9 C8 C13 118.0(4) . . ? C9 C8 N1 122.7(4) . . ? C13 C8 N1 119.2(4) . . ? C9 C10 C11 122.6(4) . . ? C9 C10 N2 115.0(4) . . ? C11 C10 N2 122.3(4) . . ? C8 C9 C10 120.1(4) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C13 C12 C11 121.6(4) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C8 121.7(4) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? C1 C2 C3 120.1(4) . . ? C1 C2 C7 116.5(4) . . ? C3 C2 C7 123.4(4) . . ? C2 C1 C6 121.5(4) . . ? C2 C1 Se1 112.3(3) . . ? C6 C1 Se1 126.2(3) . . ? N4 C15 C16 124.1(4) . . ? N4 C15 C14 115.6(4) . . ? C16 C15 C14 120.3(4) . . ? C5 C6 C1 118.1(4) . . ? C5 C6 H6 121.0 . . ? C1 C6 H6 121.0 . . ? O1 C7 N1 125.2(4) . . ? O1 C7 C2 124.7(4) . . ? N1 C7 C2 110.2(4) . . ? C3 C4 C5 120.3(4) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C3 C2 118.7(4) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C6 C5 C4 121.4(4) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? N4 C19 C18 123.6(4) . . ? N4 C19 H19 118.2 . . ? C18 C19 H19 118.2 . . ? O4 C14 N3 124.6(4) . . ? O4 C14 C15 122.6(4) . . ? N3 C14 C15 112.8(4) . . ? C17 C18 C19 118.1(4) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? C15 C16 C17 117.5(4) . . ? C15 C16 H16 121.2 . . ? C17 C16 H16 121.2 . . ? C18 C17 C16 119.9(4) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? 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 Se1 C1 1.898(4) . ? Se1 N1 1.910(3) . ? O1 C7 1.218(5) . ? O4 C14 1.227(5) . ? O3 N2 1.225(5) . ? N3 C14 1.377(6) . ? N3 C11 1.392(5) . ? N3 H3A 0.85(6) . ? N1 C7 1.382(6) . ? N1 C8 1.428(5) . ? N4 C19 1.339(6) . ? N4 C15 1.351(6) . ? N2 O2 1.210(5) . ? N2 C10 1.464(5) . ? C11 C12 1.405(6) . ? C11 C10 1.409(6) . ? C8 C9 1.386(6) . ? C8 C13 1.401(6) . ? C10 C9 1.398(6) . ? C9 H9 0.9300 . ? C12 C13 1.382(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C2 C1 1.385(6) . ? C2 C3 1.400(6) . ? C2 C7 1.484(6) . ? C1 C6 1.390(6) . ? C15 C16 1.380(6) . ? C15 C14 1.503(6) . ? C6 C5 1.381(6) . ? C6 H6 0.9300 . ? C4 C3 1.387(6) . ? C4 C5 1.395(6) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? C5 H5 0.9300 . ? C19 C18 1.390(7) . ? C19 H19 0.9300 . ? C18 C17 1.381(7) . ? C18 H18 0.9300 . ? C16 C17 1.391(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 C9 H9 O1 0.93 2.19 2.815(5) 123.6 . C12 H12 O4 0.93 2.26 2.873(5) 122.6 . C13 H13 Se1 0.93 2.59 3.075(4) 113.0 . C6 H6 O1 0.93 2.40 3.075(5) 129.3 6_557 N3 H3A O3 0.85(6) 2.04(6) 2.632(5) 126(5) . N3 H3A N4 0.85(6) 2.09(6) 2.625(5) 120(5) . C9 H9 O1 0.93 2.19 2.815(5) 123.6 . C12 H12 O4 0.93 2.26 2.873(5) 122.6 . C13 H13 Se1 0.93 2.59 3.075(4) 113.0 . C6 H6 O1 0.93 2.40 3.075(5) 129.3 6_557 N3 H3A O3 0.85(6) 2.04(6) 2.632(5) 126(5) . N3 H3A N4 0.85(6) 2.09(6) 2.625(5) 120(5) . 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 C14 N3 C11 C12 -14.1(7) . . . . ? C14 N3 C11 C10 167.3(4) . . . . ? C7 N1 C8 C9 10.1(6) . . . . ? Se1 N1 C8 C9 -170.8(3) . . . . ? C7 N1 C8 C13 -169.9(4) . . . . ? Se1 N1 C8 C13 9.2(5) . . . . ? N3 C11 C10 C9 -177.7(4) . . . . ? C12 C11 C10 C9 3.7(6) . . . . ? N3 C11 C10 N2 0.4(7) . . . . ? C12 C11 C10 N2 -178.2(4) . . . . ? O2 N2 C10 C9 0.6(7) . . . . ? O3 N2 C10 C9 179.2(4) . . . . ? O2 N2 C10 C11 -177.6(5) . . . . ? O3 N2 C10 C11 1.0(7) . . . . ? C13 C8 C9 C10 -0.6(6) . . . . ? N1 C8 C9 C10 179.4(4) . . . . ? C11 C10 C9 C8 -2.6(6) . . . . ? N2 C10 C9 C8 179.2(4) . . . . ? N3 C11 C12 C13 179.6(4) . . . . ? C10 C11 C12 C13 -1.7(6) . . . . ? C11 C12 C13 C8 -1.4(7) . . . . ? C9 C8 C13 C12 2.6(6) . . . . ? N1 C8 C13 C12 -177.4(4) . . . . ? C3 C2 C1 C6 -0.6(7) . . . . ? C7 C2 C1 C6 178.1(4) . . . . ? C3 C2 C1 Se1 179.8(3) . . . . ? C7 C2 C1 Se1 -1.4(5) . . . . ? N1 Se1 C1 C2 1.1(3) . . . . ? N1 Se1 C1 C6 -178.4(4) . . . . ? C19 N4 C15 C16 0.1(7) . . . . ? C19 N4 C15 C14 179.5(4) . . . . ? C2 C1 C6 C5 0.5(7) . . . . ? Se1 C1 C6 C5 179.9(3) . . . . ? C8 N1 C7 O1 -1.7(7) . . . . ? Se1 N1 C7 O1 179.1(4) . . . . ? C8 N1 C7 C2 179.2(4) . . . . ? Se1 N1 C7 C2 0.1(5) . . . . ? C1 C2 C7 O1 -178.2(4) . . . . ? C3 C2 C7 O1 0.5(7) . . . . ? C1 C2 C7 N1 0.9(6) . . . . ? C3 C2 C7 N1 179.6(4) . . . . ? C5 C4 C3 C2 1.7(7) . . . . ? C1 C2 C3 C4 -0.5(7) . . . . ? C7 C2 C3 C4 -179.1(4) . . . . ? C1 C6 C5 C4 0.8(7) . . . . ? C3 C4 C5 C6 -1.9(7) . . . . ? C15 N4 C19 C18 -0.2(7) . . . . ? C11 N3 C14 O4 2.0(8) . . . . ? C11 N3 C14 C15 -177.8(4) . . . . ? N4 C15 C14 O4 -172.0(4) . . . . ? C16 C15 C14 O4 7.5(7) . . . . ? N4 C15 C14 N3 7.8(6) . . . . ? C16 C15 C14 N3 -172.7(4) . . . . ? N4 C19 C18 C17 1.0(7) . . . . ? N4 C15 C16 C17 -0.7(7) . . . . ? C14 C15 C16 C17 179.8(4) . . . . ? C19 C18 C17 C16 -1.6(7) . . . . ? C15 C16 C17 C18 1.5(7) . . . . ?