#------------------------------------------------------------------------------ #$Date: 2021-12-01 03:41:23 +0200 (Wed, 01 Dec 2021) $ #$Revision: 270954 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158423.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_7158423 loop_ _publ_author_name 'Jagdev, Kesar' 'Tanini, Damiano' 'Lownes, Jack W.' 'Figliola, Carlotta' 'Male, Louise' 'Capperucci, Antonella' 'Grainger, Richard S.' _publ_section_title ; Glutathione peroxidase mimics based on conformationally-restricted, peri-like, 4,5-disubstituted fluorene dichalcogenides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB02153B _journal_year 2021 _chemical_formula_moiety 'C15 H12 Se2' _chemical_formula_sum 'C15 H12 Se2' _chemical_formula_weight 350.17 _space_group_crystal_system tetragonal _space_group_IT_number 82 _space_group_name_Hall 'I -4' _space_group_name_H-M_alt 'I -4' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-05-10 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-07-25 deposited with the CCDC. 2021-11-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 17.1924(2) _cell_length_b 17.1924(2) _cell_length_c 8.8177(2) _cell_measurement_reflns_used 10977 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 74.2920 _cell_measurement_theta_min 5.1020 _cell_volume 2606.32(7) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _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_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.1768 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.990 _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 -65.00 30.00 1.00 1.00 -- -42.56 38.00 60.00 95 2 \w 20.00 115.00 1.00 1.00 -- 42.56 38.00-150.00 95 3 \w 23.00 98.00 1.00 1.00 -- 42.56-125.00-180.00 75 4 \w 79.00 177.00 1.00 1.94 -- 106.63 61.00-180.00 98 5 \w 35.00 118.00 1.00 1.94 -- 106.63-125.00-180.00 83 6 \w 75.00 178.00 1.00 1.94 -- 106.63 77.00 150.00 103 7 \w 44.00 143.00 1.00 1.94 -- 106.63-163.00 55.00 99 8 \w 20.00 178.00 1.00 1.94 -- 106.63 0.00 30.00 158 9 \w 79.00 177.00 1.00 1.94 -- 106.63 59.00 166.23 98 10 \w -116.00 -11.00 1.00 1.00 -- -42.56 -77.00 -60.00 105 11 \w -69.00 28.00 1.00 1.00 -- -42.56 57.00 -90.00 97 12 \w 16.00 113.00 1.00 1.00 -- 42.56 57.00 90.00 97 13 \w 76.00 172.00 1.00 1.94 -- 106.63 72.00-142.00 96 14 \w 36.00 134.00 1.00 1.94 -- 106.63 -61.00 150.00 98 15 \w 83.00 178.00 1.00 1.94 -- 106.63 30.00 90.00 95 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0318070000 _diffrn_orient_matrix_UB_12 -0.0642087000 _diffrn_orient_matrix_UB_13 -0.1048809000 _diffrn_orient_matrix_UB_21 0.0827033000 _diffrn_orient_matrix_UB_22 0.0328620000 _diffrn_orient_matrix_UB_23 0.0190145000 _diffrn_orient_matrix_UB_31 0.0126584000 _diffrn_orient_matrix_UB_32 -0.0533288000 _diffrn_orient_matrix_UB_33 0.1384349000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_unetI/netI 0.0134 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 12547 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.575 _diffrn_reflns_theta_min 3.636 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 6.862 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_correction_T_min 0.786 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.785 _exptl_crystal_description block _exptl_crystal_F_000 1360 _exptl_crystal_size_max 0.126 _exptl_crystal_size_mid 0.123 _exptl_crystal_size_min 0.081 _refine_diff_density_max 0.210 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.046 _refine_ls_abs_structure_details ; Flack x determined using 1192 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.040(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 2627 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.065 _refine_ls_R_factor_all 0.0147 _refine_ls_R_factor_gt 0.0146 _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^)+(0.0198P)^2^+1.7030P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0369 _reflns_Friedel_coverage 0.854 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.971 _reflns_number_gt 2608 _reflns_number_total 2627 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob02153b2.cif _cod_data_source_block dimethyl-9H-fluoreno-diselenine _cod_original_cell_volume 2606.32(8) _cod_database_code 7158423 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H12 Se2' _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. ; _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8) 2.b Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) ; _shelx_res_file ; TITL kj-4-244_2ndsample#2_newint_gaussian_a.res in I-4 kj-4-244.res created by SHELXL-2018/3 at 18:31:37 on 10-May-2019 REM Old TITL KJ-4-244_2ndSample#2_NewInt_Gaussian in I-4 REM SHELXT solution in I-4 REM R1 0.053, Rweak 0.031, Alpha 0.004, Orientation as input REM Flack x = -0.043 ( 0.008 ) from Parsons' quotients REM Formula found by SHELXT: C15 Se2 CELL 1.54184 17.1924 17.1924 8.8177 90 90 90 ZERR 8 0.0002 0.0002 0.0002 0 0 0 LATT -2 SYMM -X,-Y,+Z SYMM +Y,-X,-Z SYMM -Y,+X,-Z SFAC C H Se UNIT 120 96 16 L.S. 10 PLAN 5 BOND $H CONF list 4 fmap 2 acta REM REM REM WGHT 0.019800 1.703000 FVAR 0.29693 C1 1 0.269473 0.472334 0.910477 11.00000 0.02873 0.02446 = 0.01737 -0.00343 -0.00269 0.00920 AFIX 43 H1 2 0.302622 0.483107 0.991132 11.00000 -1.20000 AFIX 0 C2 1 0.211284 0.415915 0.924298 11.00000 0.03261 0.02337 = 0.01902 0.00430 0.00513 0.00896 AFIX 43 H2 2 0.206988 0.387820 1.014037 11.00000 -1.20000 AFIX 0 C3 1 0.160118 0.401194 0.807098 11.00000 0.02243 0.01630 = 0.02607 0.00248 0.00612 0.00238 AFIX 43 H3 2 0.120646 0.364802 0.819988 11.00000 -1.20000 AFIX 0 C4 1 0.167245 0.440558 0.669461 11.00000 0.01646 0.01572 = 0.02032 -0.00120 0.00373 0.00195 C5 1 0.218919 0.545847 0.377461 11.00000 0.01911 0.02051 = 0.02128 0.00079 0.00394 0.00170 C6 1 0.245916 0.602462 0.277711 11.00000 0.03294 0.03032 = 0.02202 0.00557 0.00633 0.00344 AFIX 43 H6 2 0.226831 0.604709 0.179121 11.00000 -1.20000 AFIX 0 C7 1 0.301567 0.655671 0.326109 11.00000 0.03676 0.02641 = 0.03631 0.00890 0.01475 -0.00574 AFIX 43 H7 2 0.318839 0.693871 0.259459 11.00000 -1.20000 AFIX 0 C8 1 0.331847 0.652871 0.472029 11.00000 0.02725 0.02444 = 0.03786 0.00153 0.00834 -0.00947 AFIX 43 H8 2 0.369910 0.688016 0.502369 11.00000 -1.20000 AFIX 0 C9 1 0.329489 0.579773 0.733356 11.00000 0.01692 0.02554 = 0.02889 -0.00228 -0.00172 -0.00295 C10 1 0.276744 0.511762 0.774602 11.00000 0.01566 0.01934 = 0.02244 -0.00377 -0.00005 0.00362 C11 1 0.227497 0.494175 0.652456 11.00000 0.01483 0.01503 = 0.01855 -0.00116 0.00094 0.00419 C12 1 0.246813 0.544598 0.524660 11.00000 0.01360 0.01509 = 0.02178 0.00057 0.00368 0.00151 C13 1 0.304484 0.596936 0.571650 11.00000 0.01694 0.02200 = 0.02693 -0.00110 0.00338 -0.00092 C14 1 0.415889 0.555742 0.738789 11.00000 0.01803 0.04759 = 0.04605 -0.00256 -0.00464 -0.00027 AFIX 137 H14A 2 0.430430 0.544648 0.841655 11.00000 -1.50000 H14B 2 0.447442 0.597418 0.700510 11.00000 -1.50000 H14C 2 0.423564 0.510205 0.677584 11.00000 -1.50000 AFIX 0 C15 1 0.314974 0.649273 0.839019 11.00000 0.03024 0.02774 = 0.03490 -0.00707 -0.00552 -0.00707 AFIX 137 H15A 2 0.260653 0.662198 0.838143 11.00000 -1.50000 H15B 2 0.344691 0.693140 0.804662 11.00000 -1.50000 H15C 2 0.330502 0.635929 0.940308 11.00000 -1.50000 AFIX 0 SE1 3 0.085126 0.433347 0.523659 11.00000 0.01610 0.02674 = 0.03003 0.00168 -0.00285 -0.00423 SE2 3 0.154786 0.462560 0.302686 11.00000 0.03161 0.02538 = 0.01904 -0.00012 -0.00527 -0.00230 HKLF 4 REM kj-4-244_2ndsample#2_newint_gaussian_a.res in I-4 REM wR2 = 0.0369, GooF = S = 1.065, Restrained GooF = 1.065 for all data REM R1 = 0.0146 for 2608 Fo > 4sig(Fo) and 0.0147 for all 2627 data REM 156 parameters refined using 0 restraints END WGHT 0.0198 1.7051 REM Highest difference peak 0.210, deepest hole -0.347, 1-sigma level 0.046 Q1 1 0.1174 0.4920 0.3187 11.00000 0.05 0.21 Q2 1 0.3090 0.5448 0.7469 11.00000 0.05 0.18 Q3 1 0.3270 0.6090 0.7906 11.00000 0.05 0.18 Q4 1 0.3287 0.5887 0.6514 11.00000 0.05 0.17 Q5 1 0.2540 0.4992 0.7205 11.00000 0.05 0.17 ; _shelx_res_checksum 32490 _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 1.256 _oxdiff_exptl_absorpt_empirical_full_min 0.825 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+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 C1 C 0.26947(17) 0.47233(16) 0.9105(3) 0.0235(6) Uani 1 1 d . . . . . H1 H 0.302622 0.483107 0.991132 0.028 Uiso 1 1 calc R . . . . C2 C 0.21128(17) 0.41591(16) 0.9243(3) 0.0250(6) Uani 1 1 d . . . . . H2 H 0.206988 0.387820 1.014037 0.030 Uiso 1 1 calc R . . . . C3 C 0.16012(15) 0.40119(14) 0.8071(3) 0.0216(5) Uani 1 1 d . . . . . H3 H 0.120646 0.364802 0.819988 0.026 Uiso 1 1 calc R . . . . C4 C 0.16725(15) 0.44056(15) 0.6695(3) 0.0175(5) Uani 1 1 d . . . . . C5 C 0.21892(16) 0.54585(16) 0.3775(3) 0.0203(5) Uani 1 1 d . . . . . C6 C 0.24592(18) 0.60246(17) 0.2777(3) 0.0284(6) Uani 1 1 d . . . . . H6 H 0.226831 0.604709 0.179121 0.034 Uiso 1 1 calc R . . . . C7 C 0.30157(19) 0.65567(18) 0.3261(4) 0.0332(7) Uani 1 1 d . . . . . H7 H 0.318839 0.693871 0.259459 0.040 Uiso 1 1 calc R . . . . C8 C 0.33185(17) 0.65287(16) 0.4720(4) 0.0298(6) Uani 1 1 d . . . . . H8 H 0.369910 0.688016 0.502369 0.036 Uiso 1 1 calc R . . . . C9 C 0.32949(15) 0.57977(16) 0.7334(3) 0.0238(6) Uani 1 1 d . . . . . C10 C 0.27674(15) 0.51176(15) 0.7746(3) 0.0191(5) Uani 1 1 d . . . . . C11 C 0.22750(14) 0.49418(14) 0.6525(3) 0.0161(5) Uani 1 1 d . . . . . C12 C 0.24681(13) 0.54460(14) 0.5247(3) 0.0168(5) Uani 1 1 d . . . . . C13 C 0.30448(15) 0.59694(15) 0.5717(3) 0.0220(5) Uani 1 1 d . . . . . C14 C 0.41589(17) 0.5557(2) 0.7388(4) 0.0372(8) Uani 1 1 d . . . . . H14A H 0.430430 0.544648 0.841655 0.056 Uiso 1 1 calc GR . . . . H14B H 0.447442 0.597418 0.700510 0.056 Uiso 1 1 calc GR . . . . H14C H 0.423564 0.510205 0.677584 0.056 Uiso 1 1 calc GR . . . . C15 C 0.31497(18) 0.64927(18) 0.8390(4) 0.0310(7) Uani 1 1 d . . . . . H15A H 0.260653 0.662198 0.838143 0.046 Uiso 1 1 calc GR . . . . H15B H 0.344691 0.693140 0.804662 0.046 Uiso 1 1 calc GR . . . . H15C H 0.330502 0.635929 0.940308 0.046 Uiso 1 1 calc GR . . . . Se1 Se 0.08513(2) 0.43335(2) 0.52366(3) 0.02429(8) Uani 1 1 d . . . . . Se2 Se 0.15479(2) 0.46256(2) 0.30269(3) 0.02534(8) 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 0.0287(14) 0.0245(13) 0.0174(12) -0.0034(10) -0.0027(11) 0.0092(11) C2 0.0326(15) 0.0234(14) 0.0190(13) 0.0043(11) 0.0051(11) 0.0090(11) C3 0.0224(12) 0.0163(11) 0.0261(13) 0.0025(11) 0.0061(11) 0.0024(9) C4 0.0165(12) 0.0157(11) 0.0203(13) -0.0012(9) 0.0037(9) 0.0019(9) C5 0.0191(12) 0.0205(13) 0.0213(13) 0.0008(10) 0.0039(10) 0.0017(10) C6 0.0329(15) 0.0303(14) 0.0220(15) 0.0056(12) 0.0063(12) 0.0034(12) C7 0.0368(16) 0.0264(15) 0.0363(18) 0.0089(13) 0.0148(14) -0.0057(12) C8 0.0272(13) 0.0244(13) 0.0379(17) 0.0015(13) 0.0083(13) -0.0095(11) C9 0.0169(12) 0.0255(13) 0.0289(15) -0.0023(11) -0.0017(10) -0.0030(10) C10 0.0157(11) 0.0193(12) 0.0224(14) -0.0038(10) -0.0001(10) 0.0036(9) C11 0.0148(11) 0.0150(11) 0.0185(13) -0.0012(9) 0.0009(9) 0.0042(9) C12 0.0136(10) 0.0151(10) 0.0218(12) 0.0006(10) 0.0037(10) 0.0015(8) C13 0.0169(12) 0.0220(13) 0.0269(14) -0.0011(11) 0.0034(10) -0.0009(9) C14 0.0180(14) 0.0476(19) 0.046(2) -0.0026(15) -0.0046(13) -0.0003(12) C15 0.0302(15) 0.0277(15) 0.0349(17) -0.0071(13) -0.0055(13) -0.0071(12) Se1 0.01610(13) 0.02674(15) 0.03003(15) 0.00168(12) -0.00285(11) -0.00423(11) Se2 0.03161(16) 0.02538(15) 0.01904(13) -0.00012(11) -0.00527(12) -0.00230(12) 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' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -3 -2 5 0.0655 2 -2 -6 0.0659 1 -11 0 0.0515 0 9 3 0.0488 0 -9 3 0.0650 4 5 5 0.0554 6 1 5 0.0576 -3 -1 -5 0.0544 9 6 2 0.0358 -8 -7 2 0.0515 10 -4 0 0.0475 -2 7 -5 0.0570 -7 6 3 0.0554 7 -9 0 0.0506 -1 -1 -6 0.0577 5 10 0 0.0539 6 8 3 0.0423 -5 -10 0 0.0415 -7 0 -4 0.0530 7 9 -1 0.0495 9 -6 -1 0.0496 5 -4 5 0.0635 8 7 -2 0.0578 -11 -1 1 0.0488 -8 -8 0 0.0356 -11 2 1 0.0523 -9 5 2 0.0538 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 C2 C1 H1 120.6 . . ? C10 C1 H1 120.6 . . ? C10 C1 C2 118.7(3) . . ? C1 C2 H2 119.4 . . ? C3 C2 C1 121.2(3) . . ? C3 C2 H2 119.4 . . ? C2 C3 H3 119.8 . . ? C2 C3 C4 120.4(2) . . ? C4 C3 H3 119.8 . . ? C3 C4 Se1 119.2(2) . . ? C11 C4 C3 118.6(2) . . ? C11 C4 Se1 121.24(19) . . ? C6 C5 Se2 119.7(2) . . ? C12 C5 C6 119.2(3) . . ? C12 C5 Se2 120.6(2) . . ? C5 C6 H6 120.1 . . ? C7 C6 C5 119.7(3) . . ? C7 C6 H6 120.1 . . ? C6 C7 H7 119.4 . . ? C8 C7 C6 121.3(3) . . ? C8 C7 H7 119.4 . . ? C7 C8 H8 120.5 . . ? C13 C8 C7 119.0(3) . . ? C13 C8 H8 120.5 . . ? C10 C9 C14 111.1(2) . . ? C10 C9 C15 110.8(2) . . ? C13 C9 C10 101.8(2) . . ? C13 C9 C14 110.7(3) . . ? C13 C9 C15 111.9(2) . . ? C15 C9 C14 110.2(2) . . ? C1 C10 C9 129.6(2) . . ? C1 C10 C11 120.3(2) . . ? C11 C10 C9 110.0(2) . . ? C4 C11 C10 120.5(2) . . ? C4 C11 C12 130.1(2) . . ? C10 C11 C12 109.1(2) . . ? C5 C12 C11 130.9(2) . . ? C5 C12 C13 120.8(2) . . ? C13 C12 C11 108.3(2) . . ? C8 C13 C9 129.4(3) . . ? C8 C13 C12 119.9(3) . . ? C12 C13 C9 110.7(2) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 Se1 Se2 99.66(8) . . ? C5 Se2 Se1 99.65(8) . . ? 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 H1 0.9300 . ? C1 C2 1.399(4) . ? C1 C10 1.382(4) . ? C2 H2 0.9300 . ? C2 C3 1.381(4) . ? C3 H3 0.9300 . ? C3 C4 1.395(4) . ? C4 C11 1.395(4) . ? C4 Se1 1.913(3) . ? C5 C6 1.392(4) . ? C5 C12 1.384(4) . ? C5 Se2 1.924(3) . ? C6 H6 0.9300 . ? C6 C7 1.391(5) . ? C7 H7 0.9300 . ? C7 C8 1.389(5) . ? C8 H8 0.9300 . ? C8 C13 1.385(4) . ? C9 C10 1.524(4) . ? C9 C13 1.518(4) . ? C9 C14 1.543(4) . ? C9 C15 1.536(4) . ? C10 C11 1.403(4) . ? C11 C12 1.460(4) . ? C12 C13 1.402(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? Se1 Se2 2.3416(4) . ? 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 C1 C2 C3 C4 2.4(4) . . . . ? C1 C10 C11 C4 4.4(4) . . . . ? C1 C10 C11 C12 179.3(2) . . . . ? C2 C1 C10 C9 174.2(3) . . . . ? C2 C1 C10 C11 -1.2(4) . . . . ? C2 C3 C4 C11 0.7(4) . . . . ? C2 C3 C4 Se1 -168.6(2) . . . . ? C3 C4 C11 C10 -4.1(4) . . . . ? C3 C4 C11 C12 -177.8(2) . . . . ? C4 C11 C12 C5 -10.9(4) . . . . ? C4 C11 C12 C13 170.3(3) . . . . ? C5 C6 C7 C8 1.0(5) . . . . ? C5 C12 C13 C8 2.7(4) . . . . ? C5 C12 C13 C9 -175.6(2) . . . . ? C6 C5 C12 C11 178.1(3) . . . . ? C6 C5 C12 C13 -3.2(4) . . . . ? C6 C7 C8 C13 -1.5(5) . . . . ? C7 C8 C13 C9 177.6(3) . . . . ? C7 C8 C13 C12 -0.3(4) . . . . ? C9 C10 C11 C4 -171.9(2) . . . . ? C9 C10 C11 C12 3.1(3) . . . . ? C10 C1 C2 C3 -2.1(4) . . . . ? C10 C9 C13 C8 -179.6(3) . . . . ? C10 C9 C13 C12 -1.5(3) . . . . ? C10 C11 C12 C5 174.8(2) . . . . ? C10 C11 C12 C13 -4.0(3) . . . . ? C11 C12 C13 C8 -178.3(2) . . . . ? C11 C12 C13 C9 3.3(3) . . . . ? C12 C5 C6 C7 1.4(4) . . . . ? C13 C9 C10 C1 -176.8(3) . . . . ? C13 C9 C10 C11 -1.0(3) . . . . ? C14 C9 C10 C1 65.3(4) . . . . ? C14 C9 C10 C11 -118.9(3) . . . . ? C14 C9 C13 C8 -61.4(4) . . . . ? C14 C9 C13 C12 116.7(3) . . . . ? C15 C9 C10 C1 -57.6(4) . . . . ? C15 C9 C10 C11 118.1(3) . . . . ? C15 C9 C13 C8 62.0(4) . . . . ? C15 C9 C13 C12 -119.9(3) . . . . ? Se1 C4 C11 C10 165.06(19) . . . . ? Se1 C4 C11 C12 -8.7(4) . . . . ? Se2 C5 C6 C7 -170.2(2) . . . . ? Se2 C5 C12 C11 -10.4(4) . . . . ? Se2 C5 C12 C13 168.3(2) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -2.6188 -1.6331 5.4983 -0.5551 -0.1657 0.8151 1.8557 -2.0419 -5.5469 0.7719 -0.0191 -0.6355 1.1515 -11.0822 -0.2079 0.7700 -0.2729 0.5768 -0.3127 8.9553 3.4119 -0.9428 0.3333 -0.0092 0.3130 -9.3910 3.0724 0.2907 -0.2243 0.9301 3.5048 4.7680 4.8572 -0.7041 0.5389 0.4625 5.5676 1.0027 4.9380 -0.4052 0.5873 0.7006 -3.2054 -0.5032 -5.4781 0.5049 -0.3858 -0.7721 8.7533 6.2494 1.5413 -0.2845 0.9586 -0.0091 -7.6034 -6.9773 2.1726 -0.0217 -0.8168 0.5766 10.4439 -3.9411 0.1930 0.5650 0.7379 0.3691 -1.6569 6.6640 -4.5050 -0.0081 -0.0037 -1.0000 -6.7246 6.4386 3.1588 -0.9586 -0.2845 0.0088 6.5348 -9.0364 -0.1786 0.8068 0.2401 0.5399 -1.0347 -0.6368 -5.6905 0.6048 -0.2147 -0.7669 4.7469 10.0917 0.0201 -0.4991 0.7246 -0.4753 6.2707 7.8352 2.5092 -0.5668 0.8238 0.0089 -4.9929 -9.9537 -0.3194 0.5138 -0.7461 0.4234 -7.2808 0.3851 -4.3392 0.1988 -0.6720 -0.7134 7.1000 8.5150 -0.6370 -0.2541 0.8549 -0.4524 9.0285 -6.4843 -0.5366 0.7598 0.5234 0.3858 4.7751 -3.8041 4.7906 -0.1063 0.3610 0.9265 8.0154 6.7878 -1.9278 0.0213 0.8493 -0.5274 -11.0691 -1.1283 0.5118 -0.3333 -0.9428 -0.0091 -7.9620 -7.8081 -0.2327 0.2725 -0.9195 0.2834 -10.7118 2.2879 1.1211 -0.6052 -0.7894 -0.1024 -9.2069 4.7181 2.1559 -0.8219 -0.5654 -0.0697