#------------------------------------------------------------------------------ #$Date: 2020-07-06 06:43:56 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253976 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157532.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_7157532 loop_ _publ_author_name 'Sahoo, Sushree Ranjan' 'Sarkar, Debayan' 'Henkel, Felix' 'Reuter, Hans' _publ_section_title ; Copper(i) catalyzed synthesis of selanyl methylene 4-chromanol and aurone derivatives. ; _journal_issue 24 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4619 _journal_page_last 4627 _journal_paper_doi 10.1039/d0ob00632g _journal_volume 18 _journal_year 2020 _chemical_formula_sum 'C23 H18 O3 Se' _chemical_formula_weight 421.33 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-11-05 deposited with the CCDC. 2020-06-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.773(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 12.2311(4) _cell_length_b 5.5378(2) _cell_length_c 13.6984(4) _cell_measurement_reflns_used 966 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.17 _cell_measurement_theta_min 2.35 _cell_volume 923.13(5) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_unetI/netI 0.0195 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 87218 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.999 _diffrn_reflns_theta_min 2.989 _exptl_absorpt_coefficient_mu 2.055 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_correction_T_min 0.581 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker SADABS' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.516 _exptl_crystal_description prism _exptl_crystal_F_000 428 _exptl_crystal_size_max 0.486 _exptl_crystal_size_mid 0.132 _exptl_crystal_size_min 0.064 _refine_diff_density_max 0.242 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.043 _refine_ls_abs_structure_details ; Flack x determined using 1824 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.008(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 4465 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0238 _refine_ls_R_factor_gt 0.0211 _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^)+(0.0252P)^2^+0.2542P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.0498 _reflns_Friedel_coverage 0.815 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 4229 _reflns_number_total 4465 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00632g2.cif _cod_data_source_block SRS_2349_0m_b _cod_depositor_comments 'Adding full bibliography for 7157532.cif.' _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7157532 _shelx_shelxl_version_number 2014/7 _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_min 0.435 _shelx_estimated_absorpt_t_max 0.880 _shelx_res_file ; SRS_2349_0m_b.res created by SHELXL-2014/7 TITL SRS_2349_0m_b.res in P2(1) CELL 0.71073 12.2311 5.5378 13.6984 90.000 95.773 90.000 ZERR 2.000 0.0004 0.0002 0.0004 0.000 0.002 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H O Se UNIT 46 36 6 2 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! OMIT 1 0 0 OMIT 0 0 1 OMIT 1 0 1 OMIT -3 56 L.S. 10 ACTA BOND $H FMAP 2 PLAN 5 CONF SIZE 0.064 0.132 0.486 TEMP -123 WGHT 0.025200 0.254200 FVAR 0.82873 0.03700 0.03692 0.02615 0.04550 SE1 4 0.311950 1.038157 0.806419 11.00000 0.02050 0.02915 = 0.02328 -0.00719 0.00347 -0.00339 C1 1 0.252856 0.797722 0.716397 11.00000 0.01756 0.02143 = 0.01536 0.00109 0.00070 0.00152 C2 1 0.173546 0.656122 0.745700 11.00000 0.01804 0.02200 = 0.01487 -0.00090 0.00058 0.00063 C3 1 0.124793 0.658175 0.840362 11.00000 0.01743 0.02614 = 0.01544 0.00074 0.00268 0.00259 O1 3 0.148000 0.800746 0.907636 11.00000 0.02506 0.03358 = 0.01896 -0.00651 0.00537 -0.00278 C4 1 0.046041 0.459774 0.832409 11.00000 0.01909 0.02555 = 0.01481 0.00200 0.00198 0.00121 C5 1 -0.025383 0.366827 0.896191 11.00000 0.02263 0.03330 = 0.01715 0.00108 0.00624 -0.00044 AFIX 43 H5 2 -0.028125 0.431960 0.960057 11.00000 41.00000 AFIX 0 C6 1 -0.091914 0.176634 0.862979 11.00000 0.02334 0.03293 = 0.02495 0.00495 0.00937 -0.00264 AFIX 43 H6 2 -0.141671 0.110454 0.904770 11.00000 41.00000 AFIX 0 C7 1 -0.087821 0.078452 0.768763 11.00000 0.02122 0.02911 = 0.02472 0.00220 0.00342 -0.00378 AFIX 43 H7 2 -0.134414 -0.053159 0.748283 11.00000 41.00000 AFIX 0 C8 1 -0.016618 0.170987 0.705050 11.00000 0.02042 0.02463 = 0.01900 -0.00030 0.00148 -0.00037 O3 3 -0.004128 0.091536 0.612686 11.00000 0.03034 0.03344 = 0.02087 -0.00733 0.00683 -0.01012 C9 1 0.049397 0.363857 0.739334 11.00000 0.01718 0.02507 = 0.01657 0.00287 0.00371 0.00053 O2 3 0.122754 0.477984 0.684342 11.00000 0.02017 0.02486 = 0.01516 -0.00123 0.00564 -0.00533 C10 1 -0.073655 -0.100671 0.575229 11.00000 0.03242 0.02821 = 0.02782 -0.00713 0.00048 -0.00576 AFIX 137 H10A 2 -0.060149 -0.243497 0.616943 11.00000 51.00000 H10B 2 -0.057942 -0.139125 0.508218 11.00000 51.00000 H10C 2 -0.150679 -0.051543 0.574773 11.00000 51.00000 AFIX 0 C11 1 0.456361 1.095206 0.757661 11.00000 0.02111 0.02467 = 0.02492 0.00579 0.00218 -0.00487 AFIX 23 H11A 2 0.452601 1.048880 0.687601 11.00000 31.00000 H11B 2 0.474168 1.269438 0.762671 11.00000 31.00000 AFIX 0 C12 1 0.545230 0.954142 0.814488 11.00000 0.02006 0.02328 = 0.02399 0.00622 0.00235 -0.00496 C13 1 0.581388 1.020777 0.910808 11.00000 0.02706 0.02924 = 0.02577 0.00151 0.00035 -0.00583 AFIX 43 H13 2 0.550638 1.158645 0.938980 11.00000 31.00000 AFIX 0 C14 1 0.661590 0.887823 0.965577 11.00000 0.02811 0.04336 = 0.02572 0.00826 -0.00331 -0.00590 AFIX 43 H14 2 0.685358 0.934639 1.031001 11.00000 31.00000 AFIX 0 C15 1 0.707243 0.686694 0.925176 11.00000 0.02705 0.04092 = 0.04020 0.01851 -0.00064 0.00155 AFIX 43 H15 2 0.761397 0.594068 0.963101 11.00000 31.00000 AFIX 0 C16 1 0.673479 0.621224 0.829055 11.00000 0.03481 0.03093 = 0.04015 0.00667 0.00695 0.00787 AFIX 43 H16 2 0.705478 0.485188 0.800670 11.00000 31.00000 AFIX 0 C17 1 0.593056 0.754329 0.774453 11.00000 0.02865 0.03030 = 0.02803 0.00187 0.00105 -0.00158 AFIX 43 H17 2 0.570312 0.708296 0.708731 11.00000 31.00000 AFIX 0 C21 1 0.288470 0.782397 0.615839 11.00000 0.01480 0.02135 = 0.01687 0.00023 0.00231 -0.00249 C22 1 0.258327 0.962912 0.548104 11.00000 0.02962 0.02662 = 0.02449 0.00473 0.00963 0.00909 AFIX 43 H22 2 0.217322 1.098080 0.566708 11.00000 21.00000 AFIX 0 C23 1 0.288164 0.945883 0.452984 11.00000 0.03864 0.03117 = 0.02457 0.01144 0.01034 0.01000 AFIX 43 H23 2 0.266542 1.068876 0.406676 11.00000 21.00000 AFIX 0 C24 1 0.348848 0.752116 0.425256 11.00000 0.02342 0.03459 = 0.01949 -0.00020 0.00841 0.00131 AFIX 43 H24 2 0.368548 0.740861 0.360073 11.00000 21.00000 AFIX 0 C25 1 0.380673 0.574899 0.492945 11.00000 0.02920 0.02597 = 0.02504 -0.00323 0.00541 0.00928 AFIX 43 H25 2 0.424065 0.443103 0.474824 11.00000 21.00000 AFIX 0 C26 1 0.349399 0.588518 0.587802 11.00000 0.02919 0.02402 = 0.02015 0.00313 0.00178 0.00529 AFIX 43 H26 2 0.370066 0.463742 0.633568 11.00000 21.00000 AFIX 0 HKLF 4 REM SRS_2349_0m_b.res in P2(1) REM R1 = 0.0211 for 4229 Fo > 4sig(Fo) and 0.0238 for all 4465 data REM 249 parameters refined using 1 restraints END WGHT 0.0252 0.2543 REM Highest difference peak 0.242, deepest hole -0.210, 1-sigma level 0.043 Q1 1 0.2805 1.0174 0.8585 11.00000 0.05 0.24 Q2 1 0.3978 1.0429 0.7841 11.00000 0.05 0.24 Q3 1 0.3178 0.6950 0.6016 11.00000 0.05 0.23 Q4 1 0.0300 0.4120 0.7885 11.00000 0.05 0.23 Q5 1 0.0821 0.5452 0.8405 11.00000 0.05 0.23 ; _shelx_res_checksum 10447 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 0.31195(2) 1.03816(5) 0.80642(2) 0.02422(7) Uani 1 1 d . . . . . C1 C 0.25286(19) 0.7977(4) 0.71640(17) 0.0182(5) Uani 1 1 d . . . . . C2 C 0.1735(2) 0.6561(4) 0.74570(17) 0.0184(5) Uani 1 1 d . . . . . C3 C 0.1248(2) 0.6582(5) 0.84036(17) 0.0196(5) Uani 1 1 d . . . . . O1 O 0.14800(15) 0.8007(4) 0.90764(12) 0.0257(4) Uani 1 1 d . . . . . C4 C 0.0460(2) 0.4598(4) 0.83241(17) 0.0198(5) Uani 1 1 d . . . . . C5 C -0.0254(2) 0.3668(5) 0.89619(18) 0.0241(5) Uani 1 1 d . . . . . H5 H -0.0281 0.4320 0.9601 0.026(5) Uiso 1 1 calc R U . . . C6 C -0.0919(2) 0.1766(5) 0.86298(19) 0.0266(6) Uani 1 1 d . . . . . H6 H -0.1417 0.1105 0.9048 0.026(5) Uiso 1 1 calc R U . . . C7 C -0.0878(2) 0.0785(5) 0.76876(18) 0.0249(6) Uani 1 1 d . . . . . H7 H -0.1344 -0.0532 0.7483 0.026(5) Uiso 1 1 calc R U . . . C8 C -0.0166(2) 0.1710(5) 0.70505(18) 0.0214(5) Uani 1 1 d . . . . . O3 O -0.00413(15) 0.0915(3) 0.61269(12) 0.0279(5) Uani 1 1 d . . . . . C9 C 0.04940(19) 0.3639(5) 0.73933(17) 0.0195(5) Uani 1 1 d . . . . . O2 O 0.12275(13) 0.4780(3) 0.68434(11) 0.0198(4) Uani 1 1 d . . . . . C10 C -0.0737(2) -0.1007(5) 0.5752(2) 0.0297(6) Uani 1 1 d . . . . . H10A H -0.0601 -0.2435 0.6169 0.046(6) Uiso 1 1 calc R U . . . H10B H -0.0579 -0.1391 0.5082 0.046(6) Uiso 1 1 calc R U . . . H10C H -0.1507 -0.0515 0.5748 0.046(6) Uiso 1 1 calc R U . . . C11 C 0.4564(2) 1.0952(4) 0.75766(18) 0.0236(6) Uani 1 1 d . . . . . H11A H 0.4526 1.0489 0.6876 0.037(3) Uiso 1 1 calc R U . . . H11B H 0.4742 1.2694 0.7627 0.037(3) Uiso 1 1 calc R U . . . C12 C 0.5452(2) 0.9541(4) 0.81449(18) 0.0224(5) Uani 1 1 d . . . . . C13 C 0.58139(19) 1.0208(7) 0.91081(17) 0.0275(5) Uani 1 1 d . . . . . H13 H 0.5506 1.1586 0.9390 0.037(3) Uiso 1 1 calc R U . . . C14 C 0.6616(2) 0.8878(6) 0.9656(2) 0.0328(6) Uani 1 1 d . . . . . H14 H 0.6854 0.9346 1.0310 0.037(3) Uiso 1 1 calc R U . . . C15 C 0.7072(2) 0.6867(6) 0.9252(2) 0.0363(7) Uani 1 1 d . . . . . H15 H 0.7614 0.5941 0.9631 0.037(3) Uiso 1 1 calc R U . . . C16 C 0.6735(3) 0.6212(5) 0.8291(2) 0.0351(7) Uani 1 1 d . . . . . H16 H 0.7055 0.4852 0.8007 0.037(3) Uiso 1 1 calc R U . . . C17 C 0.5931(2) 0.7543(5) 0.7745(2) 0.0291(6) Uani 1 1 d . . . . . H17 H 0.5703 0.7083 0.7087 0.037(3) Uiso 1 1 calc R U . . . C21 C 0.28847(19) 0.7824(5) 0.61584(17) 0.0176(5) Uani 1 1 d . . . . . C22 C 0.2583(2) 0.9629(5) 0.54810(19) 0.0264(6) Uani 1 1 d . . . . . H22 H 0.2173 1.0981 0.5667 0.037(4) Uiso 1 1 calc R U . . . C23 C 0.2882(2) 0.9459(5) 0.4530(2) 0.0310(6) Uani 1 1 d . . . . . H23 H 0.2665 1.0689 0.4067 0.037(4) Uiso 1 1 calc R U . . . C24 C 0.3488(2) 0.7521(5) 0.42526(19) 0.0254(6) Uani 1 1 d . . . . . H24 H 0.3685 0.7409 0.3601 0.037(4) Uiso 1 1 calc R U . . . C25 C 0.3807(2) 0.5749(5) 0.49294(18) 0.0266(6) Uani 1 1 d . . . . . H25 H 0.4241 0.4431 0.4748 0.037(4) Uiso 1 1 calc R U . . . C26 C 0.3494(2) 0.5885(4) 0.58780(18) 0.0245(6) Uani 1 1 d . . . . . H26 H 0.3701 0.4637 0.6336 0.037(4) 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 Se1 0.02050(11) 0.02915(12) 0.02328(11) -0.00719(13) 0.00347(7) -0.00339(13) C1 0.0176(11) 0.0214(12) 0.0154(11) 0.0011(9) 0.0007(9) 0.0015(9) C2 0.0180(11) 0.0220(12) 0.0149(11) -0.0009(9) 0.0006(9) 0.0006(9) C3 0.0174(12) 0.0261(13) 0.0154(11) 0.0007(10) 0.0027(9) 0.0026(10) O1 0.0251(9) 0.0336(10) 0.0190(9) -0.0065(8) 0.0054(7) -0.0028(8) C4 0.0191(11) 0.0256(12) 0.0148(11) 0.0020(9) 0.0020(9) 0.0012(9) C5 0.0226(12) 0.0333(14) 0.0171(12) 0.0011(10) 0.0062(9) -0.0004(11) C6 0.0233(13) 0.0329(14) 0.0249(13) 0.0050(11) 0.0094(10) -0.0026(11) C7 0.0212(11) 0.0291(18) 0.0247(11) 0.0022(11) 0.0034(9) -0.0038(11) C8 0.0204(12) 0.0246(13) 0.0190(12) -0.0003(10) 0.0015(9) -0.0004(10) O3 0.0303(9) 0.0334(14) 0.0209(8) -0.0073(7) 0.0068(7) -0.0101(8) C9 0.0172(11) 0.0251(12) 0.0166(11) 0.0029(9) 0.0037(9) 0.0005(10) O2 0.0202(8) 0.0249(11) 0.0152(7) -0.0012(6) 0.0056(6) -0.0053(6) C10 0.0324(15) 0.0282(14) 0.0278(14) -0.0071(11) 0.0005(11) -0.0058(12) C11 0.0211(11) 0.0247(16) 0.0249(12) 0.0058(9) 0.0022(9) -0.0049(9) C12 0.0201(12) 0.0233(12) 0.0240(12) 0.0062(9) 0.0023(9) -0.0050(9) C13 0.0271(11) 0.0292(14) 0.0258(11) 0.0015(14) 0.0003(9) -0.0058(15) C14 0.0281(14) 0.0434(17) 0.0257(14) 0.0083(13) -0.0033(11) -0.0059(13) C15 0.0270(15) 0.0409(17) 0.0402(17) 0.0185(14) -0.0006(12) 0.0016(13) C16 0.0348(16) 0.0309(15) 0.0401(17) 0.0067(12) 0.0069(13) 0.0079(12) C17 0.0286(14) 0.0303(14) 0.0280(14) 0.0019(11) 0.0010(11) -0.0016(12) C21 0.0148(11) 0.0213(11) 0.0169(11) 0.0002(9) 0.0023(9) -0.0025(9) C22 0.0296(13) 0.0266(13) 0.0245(12) 0.0047(9) 0.0096(10) 0.0091(10) C23 0.0386(15) 0.0312(14) 0.0246(13) 0.0114(11) 0.0103(12) 0.0100(12) C24 0.0234(13) 0.0346(15) 0.0195(12) -0.0002(10) 0.0084(10) 0.0013(11) C25 0.0292(12) 0.0260(17) 0.0250(11) -0.0032(11) 0.0054(9) 0.0093(11) C26 0.0292(12) 0.0240(16) 0.0201(11) 0.0031(9) 0.0018(9) 0.0053(10) 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' O O 0.0106 0.0060 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Se1 C11 100.76(10) . . ? C2 C1 C21 122.1(2) . . ? C2 C1 Se1 116.98(18) . . ? C21 C1 Se1 120.74(18) . . ? C1 C2 O2 121.6(2) . . ? C1 C2 C3 128.7(2) . . ? O2 C2 C3 109.7(2) . . ? O1 C3 C4 130.0(2) . . ? O1 C3 C2 125.5(2) . . ? C4 C3 C2 104.5(2) . . ? C9 C4 C5 120.9(2) . . ? C9 C4 C3 106.1(2) . . ? C5 C4 C3 133.0(2) . . ? C6 C5 C4 117.4(2) . . ? C6 C5 H5 121.3 . . ? C4 C5 H5 121.3 . . ? C5 C6 C7 121.6(2) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 121.0(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? O3 C8 C7 126.8(2) . . ? O3 C8 C9 116.5(2) . . ? C7 C8 C9 116.7(2) . . ? C8 O3 C10 117.2(2) . . ? O2 C9 C4 114.0(2) . . ? O2 C9 C8 123.6(2) . . ? C4 C9 C8 122.3(2) . . ? C9 O2 C2 105.56(17) . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 Se1 111.65(16) . . ? C12 C11 H11A 109.3 . . ? Se1 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? Se1 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C17 C12 C13 118.5(3) . . ? C17 C12 C11 121.6(2) . . ? C13 C12 C11 119.9(2) . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 120.0(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 121.0(3) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C26 C21 C22 119.2(2) . . ? C26 C21 C1 121.1(2) . . ? C22 C21 C1 119.7(2) . . ? C21 C22 C23 120.0(2) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 120.6(2) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 119.5(2) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 120.2(2) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C21 C26 C25 120.5(2) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? 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 Se1 C1 1.907(2) . ? Se1 C11 1.976(2) . ? C1 C2 1.340(3) . ? C1 C21 1.488(3) . ? C2 O2 1.400(3) . ? C2 C3 1.481(3) . ? C3 O1 1.225(3) . ? C3 C4 1.458(3) . ? C4 C9 1.386(3) . ? C4 C5 1.395(3) . ? C5 C6 1.380(4) . ? C5 H5 0.9500 . ? C6 C7 1.406(4) . ? C6 H6 0.9500 . ? C7 C8 1.391(4) . ? C7 H7 0.9500 . ? C8 O3 1.363(3) . ? C8 C9 1.392(3) . ? O3 C10 1.425(3) . ? C9 O2 1.381(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.492(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.390(4) . ? C12 C13 1.398(3) . ? C13 C14 1.385(4) . ? C13 H13 0.9500 . ? C14 C15 1.386(5) . ? C14 H14 0.9500 . ? C15 C16 1.388(4) . ? C15 H15 0.9500 . ? C16 C17 1.386(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C21 C26 1.383(3) . ? C21 C22 1.388(3) . ? C22 C23 1.391(4) . ? C22 H22 0.9500 . ? C23 C24 1.380(4) . ? C23 H23 0.9500 . ? C24 C25 1.379(4) . ? C24 H24 0.9500 . ? C25 C26 1.393(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C21 C1 C2 O2 2.8(4) . . . . ? Se1 C1 C2 O2 178.41(16) . . . . ? C21 C1 C2 C3 -176.3(2) . . . . ? Se1 C1 C2 C3 -0.6(4) . . . . ? C1 C2 C3 O1 2.7(4) . . . . ? O2 C2 C3 O1 -176.4(2) . . . . ? C1 C2 C3 C4 -177.8(2) . . . . ? O2 C2 C3 C4 3.1(3) . . . . ? O1 C3 C4 C9 177.5(3) . . . . ? C2 C3 C4 C9 -1.9(3) . . . . ? O1 C3 C4 C5 -1.0(5) . . . . ? C2 C3 C4 C5 179.6(3) . . . . ? C9 C4 C5 C6 0.1(4) . . . . ? C3 C4 C5 C6 178.4(3) . . . . ? C4 C5 C6 C7 0.4(4) . . . . ? C5 C6 C7 C8 -0.4(4) . . . . ? C6 C7 C8 O3 179.5(2) . . . . ? C6 C7 C8 C9 -0.1(4) . . . . ? C7 C8 O3 C10 2.5(4) . . . . ? C9 C8 O3 C10 -178.0(2) . . . . ? C5 C4 C9 O2 178.9(2) . . . . ? C3 C4 C9 O2 0.2(3) . . . . ? C5 C4 C9 C8 -0.6(4) . . . . ? C3 C4 C9 C8 -179.3(2) . . . . ? O3 C8 C9 O2 1.6(4) . . . . ? C7 C8 C9 O2 -178.8(2) . . . . ? O3 C8 C9 C4 -179.0(2) . . . . ? C7 C8 C9 C4 0.5(4) . . . . ? C4 C9 O2 C2 1.8(3) . . . . ? C8 C9 O2 C2 -178.8(2) . . . . ? C1 C2 O2 C9 177.9(2) . . . . ? C3 C2 O2 C9 -3.0(2) . . . . ? Se1 C11 C12 C17 107.6(2) . . . . ? Se1 C11 C12 C13 -71.8(3) . . . . ? C17 C12 C13 C14 -1.2(4) . . . . ? C11 C12 C13 C14 178.2(2) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C13 C14 C15 C16 1.0(5) . . . . ? C14 C15 C16 C17 -1.1(5) . . . . ? C15 C16 C17 C12 0.1(5) . . . . ? C13 C12 C17 C16 1.1(4) . . . . ? C11 C12 C17 C16 -178.3(3) . . . . ? C2 C1 C21 C26 -72.3(3) . . . . ? Se1 C1 C21 C26 112.2(2) . . . . ? C2 C1 C21 C22 106.3(3) . . . . ? Se1 C1 C21 C22 -69.2(3) . . . . ? C26 C21 C22 C23 0.8(4) . . . . ? C1 C21 C22 C23 -177.9(3) . . . . ? C21 C22 C23 C24 -0.8(5) . . . . ? C22 C23 C24 C25 -0.4(5) . . . . ? C23 C24 C25 C26 1.6(4) . . . . ? C22 C21 C26 C25 0.3(4) . . . . ? C1 C21 C26 C25 179.0(2) . . . . ? C24 C25 C26 C21 -1.6(4) . . . . ?