#------------------------------------------------------------------------------ #$Date: 2026-05-05 10:30:03 +0100 (Tue, 05 May 2026) $ #$Revision: 305843 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064357.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_7064357 loop_ _publ_author_name 'Yue, Yikun' 'Zhang, Yixin' 'Li, Weijie' 'Lu, Zhande' 'Jin, Yiyang' 'Hu, Botao' 'Yang, Lu' _publ_section_title ; Catalyst-free direct C--H selenoxylation of (hetero)arenes ; _journal_issue 15 _journal_name_full 'New Journal of Chemistry' _journal_page_first 6243 _journal_page_last 6247 _journal_paper_doi 10.1039/D6NJ00684A _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C15 H12 I N O Se' _chemical_formula_sum 'C15 H12 I N O Se' _chemical_formula_weight 428.12 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2024-01-09 _audit_creation_method ; Olex2 1.5-beta (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2024-03-12 deposited with the CCDC. 2026-03-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.984(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.21500(17) _cell_length_b 18.6047(3) _cell_length_c 10.31540(18) _cell_measurement_reflns_used 6868 _cell_measurement_temperature 295.53(10) _cell_measurement_theta_max 72.6000 _cell_measurement_theta_min 5.1610 _cell_volume 1472.02(5) _computing_cell_refinement 'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))' _computing_data_reduction 'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS (Sheldrick, 2008)' _diffrn_ambient_environment air _diffrn_ambient_temperature 295.53(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -59.00 -33.00 0.50 0.32 -- -103.75 61.00 150.00 52 2 \w -61.00 -34.00 0.50 0.32 -- -103.75 61.00 120.00 54 3 \w -106.00 -77.00 0.50 0.32 -- -103.75 77.00 -30.00 58 4 \w -64.00 -26.00 0.50 0.32 -- -103.75 77.00 -30.00 76 5 \w -71.00 -29.00 0.50 0.32 -- -103.75 61.00 -90.00 84 6 \w -51.00 -23.00 0.50 0.32 -- -103.75 45.00-180.00 56 7 \w -51.00 -26.00 0.50 0.32 -- -103.75 45.00 -30.00 50 8 \w -48.00 -23.00 0.50 0.32 -- -103.75 45.00 60.00 50 9 \w -50.00 -24.00 0.50 0.32 -- -103.75 45.00 120.00 52 10 \w -51.00 -26.00 0.50 0.32 -- -103.75 45.00 150.00 50 11 \w -18.00 45.00 0.50 0.08 -- -37.45 19.00 30.00 126 12 \w -26.00 45.00 0.50 0.08 -- -37.45 19.00 90.00 142 13 \w -18.00 45.00 0.50 0.08 -- -37.45 19.00 30.00 126 14 \w -26.00 45.00 0.50 0.08 -- -37.45 19.00 -30.00 142 15 \w -26.00 45.00 0.50 0.08 -- -37.45 19.00-120.00 142 16 \w -86.00 2.00 0.50 0.08 -- -37.45 110.00 -44.00 176 17 \w -85.00 -24.00 0.50 0.32 -- -103.75 110.00 -44.00 122 18 \w -146.00 -79.00 0.50 0.32 -- -103.75-110.00-139.00 134 19 \w -177.00-133.00 0.50 0.32 -- -103.75 -61.00 60.00 88 20 \w -128.00 -75.00 0.50 0.32 -- -103.75 -61.00 60.00 106 21 \w -90.00 -65.00 0.50 0.32 -- -103.75 -77.00 150.00 50 22 \w -155.00-104.00 0.50 0.32 -- -103.75 -77.00 150.00 102 23 \w 41.00 66.00 0.50 0.32 -- 110.61 -61.00-120.00 50 24 \w 69.00 101.00 0.50 0.32 -- 110.61 -77.00-120.00 64 25 \w 37.00 62.00 0.50 0.32 -- 110.61 -77.00-120.00 50 26 \w 30.00 111.00 0.50 0.32 -- 110.61-110.00-139.00 162 27 \w 30.00 111.00 0.50 0.32 -- 110.61-110.00-139.00 162 28 \w 20.00 90.00 0.50 0.08 -- 37.45-110.00-139.00 140 29 \w 100.00 178.00 0.50 0.32 -- 110.61 110.00 -44.00 156 30 \w 113.00 150.00 0.50 0.32 -- 110.61 178.00 120.00 74 31 \w 84.00 110.00 0.50 0.32 -- 110.61 178.00 120.00 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1505481000 _diffrn_orient_matrix_UB_12 0.0028875000 _diffrn_orient_matrix_UB_13 0.0557833000 _diffrn_orient_matrix_UB_21 0.0330352000 _diffrn_orient_matrix_UB_22 0.0809031000 _diffrn_orient_matrix_UB_23 0.0296999000 _diffrn_orient_matrix_UB_31 -0.1288443000 _diffrn_orient_matrix_UB_32 0.0174421000 _diffrn_orient_matrix_UB_33 -0.1469036000 _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 0.0847 _diffrn_reflns_av_unetI/netI 0.0658 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 9157 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 66.598 _diffrn_reflns_theta_max 66.598 _diffrn_reflns_theta_min 4.754 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 19.846 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.06552 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.932 _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 1.102 _refine_diff_density_min -1.073 _refine_diff_density_rms 0.372 _refine_ls_extinction_coef 0.0070(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2600 _refine_ls_number_restraints 143 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0798 _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^)+(0.1644P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1987 _refine_ls_wR_factor_ref 0.2014 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2467 _reflns_number_total 2600 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6nj00684a2.cif _cod_data_source_block 3163 _cod_depositor_comments 'Adding full bibliography for 7064357.cif.' _cod_database_code 7064357 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H N O Se' _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_estimated_absorpt_t_max 0.242 _shelx_estimated_absorpt_t_min 0.168 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Rigid body (RIGU) restrains C7, I1, C3, C2, C4, C1, H2, H4, C5, C6, C8, H5, N1, Se1, C15, O1, C9, H7, H15A, H15B, H15C, C10, C14, H10, C11, C13, H14, H11, C12, H13, H12 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.007 3.a Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14) 3.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C) ; _shelx_res_file ; TITL 3163_auto_a.res in P2(1)/n 3163.res created by SHELXL-2018/3 at 15:34:30 on 09-Jan-2024 REM Old TITL 3163_auto in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.321, Rweak 0.022, Alpha 0.049, Orientation as input REM Formula found by SHELXT: C11 C5 Se1 CELL 1.54184 8.215002 18.604743 10.3154 90 110.9842 90 ZERR 4 0.00017 0.000338 0.00018 0 0.0022 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H I N O Se UNIT 60 48 4 4 4 4 RIGU 0.001 0.007 C7 I1 C3 C2 C4 C1 H2 H4 C5 C6 C8 H5 N1 Se1 C15 O1 C9 H7 = H15A H15B H15C C10 C14 H10 C11 C13 H14 H11 C12 H13 H12 L.S. 20 PLAN 8 SIZE 0.1 0.12 0.14 TEMP 0 CONF BOND $H fmap 2 MORE -1 ACTA SHEL 999 0.84 REM REM REM WGHT 0.164400 EXTI 0.006995 FVAR 0.42754 I1 3 0.242885 0.166838 0.866689 11.00000 0.09522 0.02040 = 0.04116 0.01454 0.03215 -0.00355 SE1 6 0.359604 0.469535 0.595159 11.00000 0.04029 0.00589 = 0.02678 -0.00058 0.02266 -0.00482 O1 5 0.567218 0.463488 0.702154 11.00000 0.03345 0.04663 = 0.05450 -0.01071 0.01560 -0.01152 N1 4 0.245427 0.305126 0.321364 11.00000 0.05049 0.02544 = 0.02236 -0.00447 0.02061 -0.00287 C1 1 0.279188 0.310055 0.549303 11.00000 0.03517 0.01003 = 0.02026 -0.00218 0.01435 0.00260 C2 1 0.278994 0.281799 0.674736 11.00000 0.04420 0.00804 = 0.02109 -0.00217 0.01587 -0.00023 AFIX 43 H2 2 0.300156 0.310975 0.752266 11.00000 -1.20000 AFIX 0 C3 1 0.246834 0.210128 0.680093 11.00000 0.05069 0.00889 = 0.03059 -0.00060 0.01903 -0.00141 C4 1 0.215581 0.162770 0.566694 11.00000 0.06186 0.00995 = 0.03990 -0.00806 0.02490 -0.00636 AFIX 43 H4 2 0.197114 0.114014 0.575817 11.00000 -1.20000 AFIX 0 C5 1 0.213095 0.191076 0.440130 11.00000 0.05682 0.01437 = 0.03369 -0.01106 0.02049 -0.00470 AFIX 43 H5 2 0.191900 0.161658 0.362919 11.00000 -1.20000 AFIX 0 C6 1 0.242869 0.263659 0.432932 11.00000 0.03955 0.01460 = 0.02290 -0.00614 0.01717 0.00086 C7 1 0.280890 0.373617 0.363146 11.00000 0.05235 0.02379 = 0.02254 -0.00020 0.02603 -0.00279 AFIX 43 H7 2 0.290585 0.411093 0.306686 11.00000 -1.20000 AFIX 0 C8 1 0.301032 0.380864 0.501472 11.00000 0.04288 0.01384 = 0.02144 0.00267 0.02155 0.00486 C9 1 0.236360 0.454615 0.720630 11.00000 0.03428 0.00454 = 0.02000 -0.00300 0.01901 -0.00112 C10 1 0.058347 0.446272 0.669620 11.00000 0.03333 0.02462 = 0.03866 0.00675 0.01865 0.00055 AFIX 43 H10 2 -0.004033 0.447315 0.574543 11.00000 -1.20000 AFIX 0 C11 1 -0.028338 0.436029 0.765056 11.00000 0.05311 0.04026 = 0.06203 0.00413 0.04141 -0.00248 AFIX 43 H11 2 -0.148842 0.430717 0.733482 11.00000 -1.20000 AFIX 0 C12 1 0.068817 0.434057 0.905578 11.00000 0.07828 0.03407 = 0.05855 0.00000 0.04522 -0.00946 AFIX 43 H12 2 0.012896 0.425919 0.968267 11.00000 -1.20000 AFIX 0 C13 1 0.245997 0.443860 0.954395 11.00000 0.08276 0.05469 = 0.03227 -0.01079 0.03611 -0.02329 AFIX 43 H13 2 0.308509 0.443867 1.049473 11.00000 -1.20000 AFIX 0 C14 1 0.332642 0.453839 0.861291 11.00000 0.04837 0.02382 = 0.02151 -0.00204 0.01467 -0.01304 AFIX 43 H14 2 0.452975 0.459852 0.893441 11.00000 -1.20000 AFIX 0 C15 1 0.223864 0.275883 0.184711 11.00000 0.07749 0.04720 = 0.02826 -0.01532 0.02734 -0.01163 AFIX 137 H15A 2 0.301610 0.235968 0.195200 11.00000 -1.50000 H15B 2 0.250080 0.312440 0.129469 11.00000 -1.50000 H15C 2 0.105735 0.260029 0.139693 11.00000 -1.50000 AFIX 0 HKLF 4 REM 3163_auto_a.res in P2(1)/n REM wR2 = 0.2014, GooF = S = 1.077, Restrained GooF = 1.060 for all data REM R1 = 0.0798 for 2467 Fo > 4sig(Fo) and 0.0811 for all 2600 data REM 174 parameters refined using 143 restraints END WGHT 0.1676 0.0000 REM Highest difference peak 1.102, deepest hole -1.073, 1-sigma level 0.372 Q1 1 0.2841 0.4689 0.6367 11.00000 0.05 1.10 Q2 1 0.3208 0.1628 0.8271 11.00000 0.05 1.08 Q3 1 0.1626 0.1628 0.9044 11.00000 0.05 0.97 Q4 1 0.4431 0.4713 0.5593 11.00000 0.05 0.95 Q5 1 0.2368 0.0914 0.8598 11.00000 0.05 0.61 ; _shelx_res_checksum 39881 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 8.469 _oxdiff_exptl_absorpt_empirical_full_min 0.403 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, 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 I1 I 0.24288(8) 0.16684(3) 0.86669(5) 0.0501(4) Uani 1 1 d . . . . . Se1 Se 0.35960(7) 0.46953(3) 0.59516(5) 0.0214(4) Uani 1 1 d . . . . . O1 O 0.5672(6) 0.4635(3) 0.7022(6) 0.0449(13) Uani 1 1 d . . . . . N1 N 0.2454(7) 0.3051(3) 0.3214(5) 0.0307(10) Uani 1 1 d . . . . . C1 C 0.2792(7) 0.3101(3) 0.5493(6) 0.0206(10) Uani 1 1 d . . . . . C2 C 0.2790(7) 0.2818(3) 0.6747(6) 0.0233(10) Uani 1 1 d . . . . . H2 H 0.300156 0.310975 0.752266 0.028 Uiso 1 1 calc R U . . . C3 C 0.2468(8) 0.2101(3) 0.6801(6) 0.0288(12) Uani 1 1 d . . . . . C4 C 0.2156(9) 0.1628(4) 0.5667(8) 0.0354(14) Uani 1 1 d . . . . . H4 H 0.197114 0.114014 0.575817 0.042 Uiso 1 1 calc R U . . . C5 C 0.2131(9) 0.1911(4) 0.4401(7) 0.0338(13) Uani 1 1 d . . . . . H5 H 0.191900 0.161658 0.362919 0.041 Uiso 1 1 calc R U . . . C6 C 0.2429(7) 0.2637(3) 0.4329(6) 0.0240(10) Uani 1 1 d . . . . . C7 C 0.2809(8) 0.3736(4) 0.3631(6) 0.0294(12) Uani 1 1 d . . . . . H7 H 0.290585 0.411093 0.306686 0.035 Uiso 1 1 calc R U . . . C8 C 0.3010(7) 0.3809(3) 0.5015(5) 0.0233(11) Uani 1 1 d . . . . . C9 C 0.2364(7) 0.4546(3) 0.7206(5) 0.0171(9) Uani 1 1 d . . . . . C10 C 0.0583(7) 0.4463(4) 0.6696(7) 0.0306(12) Uani 1 1 d . . . . . H10 H -0.004033 0.447315 0.574543 0.037 Uiso 1 1 calc R U . . . C11 C -0.0283(10) 0.4360(5) 0.7651(9) 0.0461(16) Uani 1 1 d . . . . . H11 H -0.148842 0.430717 0.733482 0.055 Uiso 1 1 calc R U . . . C12 C 0.0688(12) 0.4341(5) 0.9056(9) 0.0513(17) Uani 1 1 d . . . . . H12 H 0.012896 0.425919 0.968267 0.062 Uiso 1 1 calc R U . . . C13 C 0.2460(13) 0.4439(5) 0.9544(8) 0.0523(19) Uani 1 1 d . . . . . H13 H 0.308509 0.443867 1.049473 0.063 Uiso 1 1 calc R U . . . C14 C 0.3326(9) 0.4538(4) 0.8613(6) 0.0306(13) Uani 1 1 d . . . . . H14 H 0.452975 0.459852 0.893441 0.037 Uiso 1 1 calc R U . . . C15 C 0.2239(11) 0.2759(5) 0.1847(7) 0.0487(19) Uani 1 1 d . . . . . H15A H 0.301610 0.235968 0.195200 0.073 Uiso 1 1 calc R U . . . H15B H 0.250080 0.312440 0.129469 0.073 Uiso 1 1 calc R U . . . H15C H 0.105735 0.260029 0.139693 0.073 Uiso 1 1 calc R U . . . 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 I1 0.0952(6) 0.0204(4) 0.0412(5) 0.01454(17) 0.0321(3) -0.0035(2) Se1 0.0403(5) 0.0059(5) 0.0268(5) -0.00058(19) 0.0227(3) -0.00482(19) O1 0.033(2) 0.047(4) 0.055(3) -0.011(2) 0.016(2) -0.0115(19) N1 0.050(3) 0.025(2) 0.022(2) -0.0045(16) 0.0206(18) -0.0029(19) C1 0.035(2) 0.010(2) 0.0203(19) -0.0022(15) 0.0143(17) 0.0026(17) C2 0.044(3) 0.008(2) 0.021(2) -0.0022(17) 0.0159(18) -0.0002(18) C3 0.051(3) 0.009(2) 0.031(2) -0.0006(18) 0.019(2) -0.0014(19) C4 0.062(4) 0.010(3) 0.040(3) -0.0081(19) 0.025(2) -0.006(2) C5 0.057(3) 0.014(2) 0.034(3) -0.0111(19) 0.020(2) -0.005(2) C6 0.040(2) 0.015(2) 0.0229(19) -0.0061(16) 0.0172(17) 0.0009(17) C7 0.052(3) 0.024(3) 0.023(2) -0.0002(17) 0.026(2) -0.003(2) C8 0.043(3) 0.014(2) 0.021(2) 0.0027(17) 0.0215(18) 0.0049(19) C9 0.0343(19) 0.005(2) 0.0200(19) -0.0030(16) 0.0190(15) -0.0011(16) C10 0.033(2) 0.025(3) 0.039(3) 0.007(2) 0.0187(18) 0.0005(19) C11 0.053(3) 0.040(5) 0.062(3) 0.004(3) 0.041(2) -0.002(3) C12 0.078(3) 0.034(4) 0.059(3) 0.000(3) 0.045(2) -0.009(3) C13 0.083(3) 0.055(6) 0.032(3) -0.011(3) 0.036(3) -0.023(3) C14 0.048(3) 0.024(3) 0.0215(19) -0.0020(19) 0.0147(17) -0.013(2) C15 0.077(4) 0.047(5) 0.028(3) -0.015(3) 0.027(3) -0.012(4) 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' I I -0.3257 6.8362 '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 O1 Se1 C8 107.0(3) . . ? O1 Se1 C9 101.8(3) . . ? C8 Se1 C9 96.8(2) . . ? C6 N1 C15 124.0(6) . . ? C7 N1 C6 109.0(5) . . ? C7 N1 C15 126.9(6) . . ? C2 C1 C6 119.0(6) . . ? C2 C1 C8 134.7(5) . . ? C6 C1 C8 106.3(5) . . ? C1 C2 H2 121.0 . . ? C3 C2 C1 118.0(6) . . ? C3 C2 H2 121.0 . . ? C2 C3 I1 118.6(5) . . ? C2 C3 C4 123.8(6) . . ? C4 C3 I1 117.5(5) . . ? C3 C4 H4 120.8 . . ? C5 C4 C3 118.3(6) . . ? C5 C4 H4 120.8 . . ? C4 C5 H5 120.8 . . ? C6 C5 C4 118.3(6) . . ? C6 C5 H5 120.8 . . ? N1 C6 C1 107.5(6) . . ? C5 C6 N1 130.0(6) . . ? C5 C6 C1 122.5(6) . . ? N1 C7 H7 124.6 . . ? N1 C7 C8 110.8(6) . . ? C8 C7 H7 124.6 . . ? C1 C8 Se1 131.7(4) . . ? C7 C8 Se1 121.9(5) . . ? C7 C8 C1 106.3(5) . . ? C10 C9 Se1 120.1(4) . . ? C10 C9 C14 122.1(5) . . ? C14 C9 Se1 117.8(4) . . ? C9 C10 H10 120.7 . . ? C9 C10 C11 118.6(6) . . ? C11 C10 H10 120.7 . . ? C10 C11 H11 120.5 . . ? C12 C11 C10 119.1(7) . . ? C12 C11 H11 120.5 . . ? C11 C12 H12 119.3 . . ? C13 C12 C11 121.3(7) . . ? C13 C12 H12 119.3 . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 120.0(7) . . ? C14 C13 H13 120.0 . . ? C9 C14 C13 118.8(6) . . ? C9 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 I1 C3 2.097(6) . ? Se1 O1 1.671(5) . ? Se1 C8 1.885(6) . ? Se1 C9 1.928(5) . ? N1 C6 1.392(8) . ? N1 C7 1.343(9) . ? N1 C15 1.461(8) . ? C1 C2 1.397(8) . ? C1 C6 1.421(8) . ? C1 C8 1.440(8) . ? C2 H2 0.9300 . ? C2 C3 1.364(9) . ? C3 C4 1.413(9) . ? C4 H4 0.9300 . ? C4 C5 1.401(10) . ? C5 H5 0.9300 . ? C5 C6 1.379(10) . ? C7 H7 0.9300 . ? C7 C8 1.383(8) . ? C9 C10 1.374(8) . ? C9 C14 1.382(8) . ? C10 H10 0.9300 . ? C10 C11 1.419(10) . ? C11 H11 0.9300 . ? C11 C12 1.382(13) . ? C12 H12 0.9300 . ? C12 C13 1.371(13) . ? C13 H13 0.9300 . ? C13 C14 1.398(10) . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 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 I1 C3 C4 C5 178.3(5) . . . . ? Se1 C9 C10 C11 -179.4(6) . . . . ? Se1 C9 C14 C13 179.3(6) . . . . ? O1 Se1 C8 C1 68.7(6) . . . . ? O1 Se1 C8 C7 -107.0(5) . . . . ? N1 C7 C8 Se1 177.8(4) . . . . ? N1 C7 C8 C1 1.2(7) . . . . ? C1 C2 C3 I1 -179.3(4) . . . . ? C1 C2 C3 C4 0.7(10) . . . . ? C2 C1 C6 N1 178.1(5) . . . . ? C2 C1 C6 C5 -2.2(9) . . . . ? C2 C1 C8 Se1 6.0(10) . . . . ? C2 C1 C8 C7 -177.9(6) . . . . ? C2 C3 C4 C5 -1.6(11) . . . . ? C3 C4 C5 C6 0.6(10) . . . . ? C4 C5 C6 N1 -179.1(6) . . . . ? C4 C5 C6 C1 1.3(10) . . . . ? C6 N1 C7 C8 -0.7(7) . . . . ? C6 C1 C2 C3 1.2(8) . . . . ? C6 C1 C8 Se1 -177.3(4) . . . . ? C6 C1 C8 C7 -1.2(6) . . . . ? C7 N1 C6 C1 0.0(7) . . . . ? C7 N1 C6 C5 -179.7(7) . . . . ? C8 C1 C2 C3 177.6(6) . . . . ? C8 C1 C6 N1 0.7(6) . . . . ? C8 C1 C6 C5 -179.6(6) . . . . ? C9 Se1 C8 C1 -35.9(6) . . . . ? C9 Se1 C8 C7 148.4(5) . . . . ? C9 C10 C11 C12 -0.6(12) . . . . ? C10 C9 C14 C13 0.3(11) . . . . ? C10 C11 C12 C13 1.9(14) . . . . ? C11 C12 C13 C14 -2.1(15) . . . . ? C12 C13 C14 C9 0.9(13) . . . . ? C14 C9 C10 C11 -0.5(10) . . . . ? C15 N1 C6 C1 176.3(6) . . . . ? C15 N1 C6 C5 -3.4(11) . . . . ? C15 N1 C7 C8 -176.9(6) . . . . ?