#------------------------------------------------------------------------------ #$Date: 2019-08-14 06:33:32 +0300 (Wed, 14 Aug 2019) $ #$Revision: 217522 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/33/7233377.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_7233377 loop_ _publ_author_name 'Jakubczyk, Micha\/l' 'Mkrtchyan, Satenik' 'Madura, Izabela D.' 'Marek, Paulina H.' 'Iaroshenko, Viktor O.' _publ_section_title ; Copper-catalyzed direct C--H arylselenation of 4-nitro-pyrazoles and other heterocycles with selenium powder and aryl iodides. Access to unsymmetrical heteroaryl selenides ; _journal_issue 44 _journal_name_full 'RSC Advances' _journal_page_first 25368 _journal_paper_doi 10.1039/C9RA05004C _journal_volume 9 _journal_year 2019 _chemical_formula_moiety 'C17 H17 N3 Se' _chemical_formula_sum 'C17 H17 N3 Se' _chemical_formula_weight 342.29 _chemical_name_systematic ; 3-methyl-1-phenyl-4-(p-tolylselanyl)-1H-pyrazol-5-amine ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2019-06-13 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-06-13 deposited with the CCDC. 2019-08-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.138(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5515(5) _cell_length_b 5.93199(19) _cell_length_c 21.5896(11) _cell_measurement_reflns_used 3989 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.1780 _cell_measurement_theta_min 4.4670 _cell_volume 1577.18(12) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _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 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3347 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.986 _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 19.00 51.00 1.00 45.00 -- 11.71 -99.00 -90.00 32 2 \w -28.00 93.00 1.00 45.00 -- 11.71 19.00 -30.00 121 3 \w -77.00 -51.00 1.00 45.00 -- 11.71 179.00 -60.00 26 4 \w 17.00 48.00 1.00 45.00 -- 11.71 -99.00 30.00 31 5 \w -77.00 83.00 1.00 45.00 -- 11.71 0.00-120.00 160 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0169716000 _diffrn_orient_matrix_UB_12 0.0041635000 _diffrn_orient_matrix_UB_13 -0.0332855000 _diffrn_orient_matrix_UB_21 0.0218682000 _diffrn_orient_matrix_UB_22 -0.1091277000 _diffrn_orient_matrix_UB_23 -0.0024847000 _diffrn_orient_matrix_UB_31 -0.0505145000 _diffrn_orient_matrix_UB_32 -0.0486533000 _diffrn_orient_matrix_UB_33 0.0027160000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_unetI/netI 0.0357 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 14178 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_min 3.308 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.378 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.74530 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.442 _exptl_crystal_description block _exptl_crystal_F_000 696 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.371 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 3579 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0365 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+0.6249P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.0819 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2659 _reflns_number_total 3579 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra05004c2.cif _cod_data_source_block 5b _cod_original_cell_volume 1577.19(11) _cod_database_code 7233377 _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 0.648 _shelx_estimated_absorpt_t_min 0.287 _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. Restrained distances N3-H3B = N3-H3A 0.82 with sigma of 0.05 3.a Aromatic/amide H refined with riding coordinates: C16(H16), C20(H20), C13(H13), C17(H17), C19(H19), C9(H9), C12(H12), C11(H11), C10(H10) 3.b Idealised Me refined as rotating group: C21(H21A,H21B,H21C), C7(H7A,H7B,H7C) ; _shelx_res_file ; TITL mja_7_ki_f2028_a.res in P2(1)/c mja_7_ki_f2028.res created by SHELXL-2018/3 at 18:31:38 on 13-Jun-2019 REM Old TITL mja_7_KI_F2028 in P21/c #14 REM SHELXT solution in P2(1)/c REM R1 0.141, Rweak 0.131, Alpha 0.030, Orientation as input REM Formula found by SHELXT: C21 N3 Br CELL 0.71073 12.551505 5.931992 21.589627 90 101.1377 90 ZERR 4 0.000453 0.000191 0.001055 0 0.004 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N Se UNIT 68 68 12 4 DFIX 0.82 0.05 N3 H3b N3 H3a L.S. 16 PLAN 5 SIZE 0.2 0.4 0.7 TEMP 20(2) BOND $H LIST 4 MORE -1 CONF fmap 2 acta 52 OMIT -2 55 OMIT -3 2 7 REM REM REM WGHT 0.032000 0.624900 FVAR 0.43954 SE1 4 0.272735 -0.100844 0.544937 11.00000 0.06168 0.03844 = 0.05675 0.00844 0.02271 0.00149 N2 3 0.316175 0.313737 0.404830 11.00000 0.03955 0.04780 = 0.03759 0.00283 0.00650 -0.00753 N3 3 0.453265 0.256310 0.497629 11.00000 0.05270 0.05001 = 0.04320 0.00804 -0.00127 -0.01479 N1 3 0.209906 0.253262 0.379273 11.00000 0.03897 0.06549 = 0.04277 0.00139 0.00736 -0.00726 C15 1 0.219098 0.106222 0.600387 11.00000 0.03645 0.04056 = 0.04285 0.00430 0.00995 -0.00800 C3 1 0.351988 0.214775 0.461316 11.00000 0.04241 0.03497 = 0.03787 -0.00142 0.00836 -0.00476 C4 1 0.268744 0.081916 0.473344 11.00000 0.04617 0.04045 = 0.03922 -0.00107 0.01287 -0.00152 C6 1 0.370742 0.471811 0.372496 11.00000 0.04507 0.04020 = 0.03131 -0.00112 0.00463 -0.00563 C16 1 0.170782 0.309124 0.579371 11.00000 0.05951 0.04034 = 0.04104 0.00932 0.01534 -0.00140 AFIX 43 H16 2 0.165981 0.353098 0.537576 11.00000 -1.20000 AFIX 0 C20 1 0.227995 0.046605 0.663157 11.00000 0.04488 0.04746 = 0.04530 0.01392 0.00665 -0.00212 AFIX 43 H20 2 0.262270 -0.087258 0.677984 11.00000 -1.20000 AFIX 0 C5 1 0.183392 0.112159 0.421422 11.00000 0.03870 0.05842 = 0.04658 -0.00391 0.01403 -0.00640 C13 1 0.475071 0.429070 0.364261 11.00000 0.04829 0.04423 = 0.04403 0.00191 0.00777 -0.00241 AFIX 43 H13 2 0.508676 0.293562 0.378128 11.00000 -1.20000 AFIX 0 C18 1 0.135099 0.386897 0.683275 11.00000 0.05163 0.04763 = 0.04832 -0.00254 0.01757 -0.01264 C17 1 0.129979 0.445009 0.620760 11.00000 0.06456 0.04046 = 0.05341 0.00772 0.01744 0.00015 AFIX 43 H17 2 0.097736 0.581061 0.606191 11.00000 -1.20000 AFIX 0 C19 1 0.186072 0.185562 0.703728 11.00000 0.05368 0.05683 = 0.03772 0.00827 0.01043 -0.01118 AFIX 43 H19 2 0.192131 0.143262 0.745743 11.00000 -1.20000 AFIX 0 C9 1 0.319852 0.669689 0.350378 11.00000 0.05200 0.04675 = 0.05197 0.00048 0.01015 0.00259 AFIX 43 H9 2 0.249261 0.698519 0.355543 11.00000 -1.20000 AFIX 0 C12 1 0.529424 0.587051 0.335510 11.00000 0.05187 0.06384 = 0.04899 -0.00149 0.01443 -0.01219 AFIX 43 H12 2 0.600379 0.559338 0.330852 11.00000 -1.20000 AFIX 0 C11 1 0.479585 0.785170 0.313678 11.00000 0.07214 0.05652 = 0.05398 0.00804 0.01195 -0.02133 AFIX 43 H11 2 0.516617 0.891925 0.294407 11.00000 -1.20000 AFIX 0 C10 1 0.374496 0.825011 0.320459 11.00000 0.08210 0.04280 = 0.06491 0.01160 0.00513 -0.00210 AFIX 43 H10 2 0.339946 0.957627 0.304770 11.00000 -1.20000 AFIX 0 C21 1 0.085475 0.533266 0.726988 11.00000 0.08540 0.06529 = 0.06153 -0.00720 0.03236 -0.00585 AFIX 137 H21A 2 0.113933 0.683420 0.726782 11.00000 -1.50000 H21B 2 0.102722 0.473067 0.769011 11.00000 -1.50000 H21C 2 0.008076 0.536786 0.713090 11.00000 -1.50000 AFIX 0 C7 1 0.073627 0.004189 0.411112 11.00000 0.04820 0.09813 = 0.07243 0.00175 0.01159 -0.02202 AFIX 137 H7A 2 0.036858 0.048480 0.444255 11.00000 -1.50000 H7B 2 0.081560 -0.156785 0.411307 11.00000 -1.50000 H7C 2 0.032047 0.051609 0.371159 11.00000 -1.50000 AFIX 0 H3A 2 0.458654 0.207733 0.533109 11.00000 0.06624 H3B 2 0.495530 0.326546 0.484272 11.00000 0.13705 HKLF 4 REM mja_7_ki_f2028_a.res in P2(1)/c REM wR2 = 0.0819, GooF = S = 1.020, Restrained GooF = 1.020 for all data REM R1 = 0.0365 for 2659 Fo > 4sig(Fo) and 0.0596 for all 3579 data REM 200 parameters refined using 2 restraints END WGHT 0.0320 0.6249 REM Highest difference peak 0.371, deepest hole -0.261, 1-sigma level 0.052 Q1 1 0.3612 -0.0929 0.5470 11.00000 0.05 0.37 Q2 1 0.1899 -0.1053 0.5429 11.00000 0.05 0.32 Q3 1 0.0605 -0.1059 0.4474 11.00000 0.05 0.27 Q4 1 0.1347 0.0872 0.4188 11.00000 0.05 0.27 Q5 1 0.2294 0.0860 0.6320 11.00000 0.05 0.20 ; _shelx_res_checksum 92965 _olex2_date_sample_data_collection 2018-03-09 _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 1.207 _oxdiff_exptl_absorpt_empirical_full_min 0.866 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Se1 Se 0.27274(2) -0.10084(4) 0.54494(2) 0.05078(11) Uani 1 1 d . N2 N 0.31617(15) 0.3137(3) 0.40483(10) 0.0418(5) Uani 1 1 d . N3 N 0.45326(19) 0.2563(4) 0.49763(13) 0.0500(6) Uani 1 1 d D N1 N 0.20991(15) 0.2533(4) 0.37927(10) 0.0491(5) Uani 1 1 d . C15 C 0.21910(18) 0.1062(4) 0.60039(12) 0.0396(5) Uani 1 1 d . C3 C 0.35199(18) 0.2148(4) 0.46132(11) 0.0383(5) Uani 1 1 d . C4 C 0.2687(2) 0.0819(4) 0.47334(12) 0.0413(6) Uani 1 1 d . C6 C 0.37074(18) 0.4718(4) 0.37250(11) 0.0392(5) Uani 1 1 d . C16 C 0.1708(2) 0.3091(4) 0.57937(12) 0.0462(6) Uani 1 1 d . H16 H 0.165981 0.353098 0.537576 0.055 Uiso 1 1 calc R C20 C 0.22800(19) 0.0466(4) 0.66316(13) 0.0462(6) Uani 1 1 d . H20 H 0.262270 -0.087258 0.677984 0.055 Uiso 1 1 calc R C5 C 0.18339(19) 0.1122(4) 0.42142(13) 0.0471(6) Uani 1 1 d . C13 C 0.4751(2) 0.4291(4) 0.36426(12) 0.0457(6) Uani 1 1 d . H13 H 0.508676 0.293562 0.378128 0.055 Uiso 1 1 calc R C18 C 0.1351(2) 0.3869(4) 0.68327(13) 0.0481(6) Uani 1 1 d . C17 C 0.1300(2) 0.4450(4) 0.62076(14) 0.0520(7) Uani 1 1 d . H17 H 0.097736 0.581061 0.606191 0.062 Uiso 1 1 calc R C19 C 0.1861(2) 0.1856(5) 0.70373(13) 0.0492(6) Uani 1 1 d . H19 H 0.192131 0.143262 0.745743 0.059 Uiso 1 1 calc R C9 C 0.3199(2) 0.6697(4) 0.35038(13) 0.0502(6) Uani 1 1 d . H9 H 0.249261 0.698519 0.355543 0.060 Uiso 1 1 calc R C12 C 0.5294(2) 0.5871(5) 0.33551(13) 0.0543(7) Uani 1 1 d . H12 H 0.600379 0.559338 0.330852 0.065 Uiso 1 1 calc R C11 C 0.4796(2) 0.7852(5) 0.31368(14) 0.0609(8) Uani 1 1 d . H11 H 0.516617 0.891925 0.294407 0.073 Uiso 1 1 calc R C10 C 0.3745(3) 0.8250(5) 0.32046(15) 0.0645(8) Uani 1 1 d . H10 H 0.339946 0.957627 0.304770 0.077 Uiso 1 1 calc R C21 C 0.0855(3) 0.5333(5) 0.72699(15) 0.0683(8) Uani 1 1 d . H21A H 0.113933 0.683420 0.726782 0.102 Uiso 1 1 calc GR H21B H 0.102722 0.473067 0.769011 0.102 Uiso 1 1 calc GR H21C H 0.008076 0.536786 0.713090 0.102 Uiso 1 1 calc GR C7 C 0.0736(2) 0.0042(6) 0.41111(16) 0.0729(9) Uani 1 1 d . H7A H 0.036858 0.048480 0.444255 0.109 Uiso 1 1 calc GR H7B H 0.081560 -0.156785 0.411307 0.109 Uiso 1 1 calc GR H7C H 0.032047 0.051609 0.371159 0.109 Uiso 1 1 calc GR H3A H 0.459(2) 0.208(5) 0.5331(13) 0.066(10) Uiso 1 1 d D H3B H 0.496(3) 0.327(7) 0.484(2) 0.137(19) Uiso 1 1 d 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 0.06168(18) 0.03844(15) 0.0567(2) 0.00844(13) 0.02271(13) 0.00149(12) N2 0.0396(10) 0.0478(11) 0.0376(12) 0.0028(10) 0.0065(9) -0.0075(9) N3 0.0527(13) 0.0500(14) 0.0432(16) 0.0080(12) -0.0013(11) -0.0148(11) N1 0.0390(10) 0.0655(14) 0.0428(13) 0.0014(11) 0.0074(9) -0.0073(10) C15 0.0364(11) 0.0406(12) 0.0429(15) 0.0043(11) 0.0100(10) -0.0080(10) C3 0.0424(12) 0.0350(12) 0.0379(14) -0.0014(11) 0.0084(11) -0.0048(10) C4 0.0462(12) 0.0404(13) 0.0392(15) -0.0011(11) 0.0129(11) -0.0015(11) C6 0.0451(13) 0.0402(12) 0.0313(14) -0.0011(10) 0.0046(10) -0.0056(11) C16 0.0595(15) 0.0403(13) 0.0410(16) 0.0093(12) 0.0153(12) -0.0014(12) C20 0.0449(13) 0.0475(14) 0.0453(16) 0.0139(12) 0.0066(11) -0.0021(11) C5 0.0387(12) 0.0584(16) 0.0466(16) -0.0039(13) 0.0140(12) -0.0064(12) C13 0.0483(14) 0.0442(14) 0.0440(16) 0.0019(12) 0.0078(11) -0.0024(11) C18 0.0516(14) 0.0476(14) 0.0483(17) -0.0025(13) 0.0176(12) -0.0126(13) C17 0.0646(16) 0.0405(14) 0.0534(18) 0.0077(12) 0.0174(14) 0.0002(12) C19 0.0537(14) 0.0568(15) 0.0377(16) 0.0083(13) 0.0104(12) -0.0112(13) C9 0.0520(14) 0.0468(14) 0.0520(18) 0.0005(13) 0.0102(13) 0.0026(12) C12 0.0519(15) 0.0638(18) 0.0490(17) -0.0015(14) 0.0144(13) -0.0122(14) C11 0.0721(19) 0.0565(17) 0.0540(19) 0.0080(15) 0.0120(15) -0.0213(16) C10 0.082(2) 0.0428(15) 0.065(2) 0.0116(14) 0.0051(16) -0.0021(15) C21 0.085(2) 0.0653(19) 0.062(2) -0.0072(16) 0.0324(17) -0.0059(17) C7 0.0482(15) 0.098(2) 0.072(2) 0.002(2) 0.0116(15) -0.0220(17) 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' Se Se -0.0929 2.2259 '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 C4 Se1 C15 100.73(10) N1 N2 C6 119.5(2) C3 N2 N1 111.92(18) C3 N2 C6 128.51(19) C3 N3 H3A 112(2) C3 N3 H3B 120(4) H3A N3 H3B 127(4) C5 N1 N2 103.9(2) C16 C15 Se1 122.32(19) C20 C15 Se1 118.30(18) C20 C15 C16 119.4(2) N2 C3 N3 123.0(2) N2 C3 C4 106.7(2) C4 C3 N3 130.2(2) C3 C4 Se1 125.87(19) C3 C4 C5 105.5(2) C5 C4 Se1 128.66(19) C13 C6 N2 120.1(2) C9 C6 N2 119.8(2) C9 C6 C13 120.0(2) C15 C16 H16 120.3 C17 C16 C15 119.5(2) C17 C16 H16 120.3 C15 C20 H20 120.0 C19 C20 C15 120.0(2) C19 C20 H20 120.0 N1 C5 C4 112.0(2) N1 C5 C7 120.9(3) C4 C5 C7 127.0(3) C6 C13 H13 120.0 C12 C13 C6 119.9(2) C12 C13 H13 120.0 C17 C18 C19 117.2(2) C17 C18 C21 121.5(3) C19 C18 C21 121.3(3) C16 C17 C18 122.4(2) C16 C17 H17 118.8 C18 C17 H17 118.8 C20 C19 C18 121.5(2) C20 C19 H19 119.3 C18 C19 H19 119.3 C6 C9 H9 120.3 C6 C9 C10 119.5(2) C10 C9 H9 120.3 C13 C12 H12 119.8 C11 C12 C13 120.4(2) C11 C12 H12 119.8 C12 C11 H11 120.2 C12 C11 C10 119.6(3) C10 C11 H11 120.2 C9 C10 H10 119.7 C11 C10 C9 120.5(3) C11 C10 H10 119.7 C18 C21 H21A 109.5 C18 C21 H21B 109.5 C18 C21 H21C 109.5 H21A C21 H21B 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C5 C7 H7A 109.5 C5 C7 H7B 109.5 C5 C7 H7C 109.5 H7A C7 H7B 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Se1 C15 1.925(2) Se1 C4 1.881(2) N2 N1 1.389(3) N2 C3 1.350(3) N2 C6 1.421(3) N3 C3 1.381(3) N3 H3A 0.81(3) N3 H3B 0.77(4) N1 C5 1.325(3) C15 C16 1.384(3) C15 C20 1.384(3) C3 C4 1.373(3) C4 C5 1.404(4) C6 C13 1.379(3) C6 C9 1.377(3) C16 H16 0.9300 C16 C17 1.374(4) C20 H20 0.9300 C20 C19 1.379(4) C5 C7 1.496(3) C13 H13 0.9300 C13 C12 1.376(4) C18 C17 1.382(4) C18 C19 1.386(4) C18 C21 1.503(4) C17 H17 0.9300 C19 H19 0.9300 C9 H9 0.9300 C9 C10 1.381(4) C12 H12 0.9300 C12 C11 1.371(4) C11 H11 0.9300 C11 C10 1.375(4) C10 H10 0.9300 C21 H21A 0.9600 C21 H21B 0.9600 C21 H21C 0.9600 C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 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 Se1 C15 C16 C17 177.21(19) Se1 C15 C20 C19 -177.03(18) Se1 C4 C5 N1 -179.52(18) Se1 C4 C5 C7 0.3(4) N2 N1 C5 C4 0.5(3) N2 N1 C5 C7 -179.2(2) N2 C3 C4 Se1 178.90(17) N2 C3 C4 C5 -0.7(3) N2 C6 C13 C12 -177.0(2) N2 C6 C9 C10 178.3(2) N3 C3 C4 Se1 -3.3(4) N3 C3 C4 C5 177.1(3) N1 N2 C3 N3 -176.9(2) N1 N2 C3 C4 1.1(3) N1 N2 C6 C13 -133.4(2) N1 N2 C6 C9 47.7(3) C15 Se1 C4 C3 90.9(2) C15 Se1 C4 C5 -89.6(2) C15 C16 C17 C18 -0.1(4) C15 C20 C19 C18 -0.4(4) C3 N2 N1 C5 -1.0(3) C3 N2 C6 C13 50.0(4) C3 N2 C6 C9 -128.8(3) C3 C4 C5 N1 0.1(3) C3 C4 C5 C7 179.9(3) C6 N2 N1 C5 -178.1(2) C6 N2 C3 N3 -0.1(4) C6 N2 C3 C4 177.9(2) C6 C13 C12 C11 -1.4(4) C6 C9 C10 C11 -1.2(4) C16 C15 C20 C19 1.9(3) C20 C15 C16 C17 -1.7(4) C13 C6 C9 C10 -0.5(4) C13 C12 C11 C10 -0.2(4) C17 C18 C19 C20 -1.3(4) C19 C18 C17 C16 1.5(4) C9 C6 C13 C12 1.8(4) C12 C11 C10 C9 1.6(5) C21 C18 C17 C16 -177.2(3) C21 C18 C19 C20 177.5(2)