#------------------------------------------------------------------------------ #$Date: 2017-03-16 08:11:19 +0200 (Thu, 16 Mar 2017) $ #$Revision: 194293 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/78/7227861.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_7227861 loop_ _publ_author_name 'Deng, Shulin' 'Zeng, Delong' 'Luo, Yi' 'Zhao, Jianfu' 'Li, Xiaoling' 'Zhao, Zhennan' 'Chen, Tianfeng' _publ_section_title ; Enhancement of cell uptake and antitumor activity of selenadiazole derivatives through interaction and delivery by serum albumin ; _journal_issue 27 _journal_name_full 'RSC Adv.' _journal_page_first 16721 _journal_paper_doi 10.1039/C6RA28801D _journal_volume 7 _journal_year 2017 _chemical_formula_moiety 'C10 H7 N2 O2 Se, C10 H10 N2 O2 Se' _chemical_formula_sum 'C20 H20 N4 O4 Se2' _chemical_formula_weight 538.32 _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' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2016-11-02 _audit_creation_method ; Olex2 1.2 (compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874) ; _audit_update_record ; 2016-11-11 deposited with the CCDC. 2017-03-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 112.119(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 21.9362(9) _cell_length_b 4.53698(16) _cell_length_c 23.8161(11) _cell_measurement_reflns_used 2127 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 62.6698 _cell_measurement_theta_min 3.4646 _cell_volume 2195.83(17) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0288 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -83.00 -53.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -32.9934 178.0000 60.0000 30 #__ type_ start__ end____ width___ exp.time_ 2 omega 14.00 102.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 32.9934 57.0000 0.0000 88 #__ type_ start__ end____ width___ exp.time_ 3 omega 49.00 110.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 32.9934 -178.0000 -30.0000 61 #__ type_ start__ end____ width___ exp.time_ 4 omega 35.00 91.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 32.9934 178.0000 -180.0000 56 #__ type_ start__ end____ width___ exp.time_ 5 omega 29.00 56.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 -30.0000 120.0000 27 #__ type_ start__ end____ width___ exp.time_ 6 omega 34.00 112.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 -61.0000 60.0000 78 #__ type_ start__ end____ width___ exp.time_ 7 omega 67.00 157.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 45.0000 150.0000 90 #__ type_ start__ end____ width___ exp.time_ 8 omega 37.00 102.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 15.0000 0.0000 65 #__ type_ start__ end____ width___ exp.time_ 9 omega 24.00 63.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 -30.0000 -120.0000 39 #__ type_ start__ end____ width___ exp.time_ 10 omega 139.00 164.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 15.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 11 omega 21.00 66.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 -45.0000 0.0000 45 #__ type_ start__ end____ width___ exp.time_ 12 omega 68.00 110.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 45.0000 -90.0000 42 #__ type_ start__ end____ width___ exp.time_ 13 omega 28.00 60.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 -30.0000 30.0000 32 #__ type_ start__ end____ width___ exp.time_ 14 omega 19.00 64.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - 90.5000 -94.0000 30.0000 45 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0472722000 _diffrn_orient_matrix_UB_12 0.0784249000 _diffrn_orient_matrix_UB_13 -0.0647133000 _diffrn_orient_matrix_UB_21 -0.0440097000 _diffrn_orient_matrix_UB_22 -0.2638679000 _diffrn_orient_matrix_UB_23 0.0005657000 _diffrn_orient_matrix_UB_31 -0.0396239000 _diffrn_orient_matrix_UB_32 0.1990687000 _diffrn_orient_matrix_UB_33 0.0262453000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_unetI/netI 0.0504 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 6476 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 62.762 _diffrn_reflns_theta_max 62.762 _diffrn_reflns_theta_min 3.468 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 4.503 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.48607 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.628 _exptl_crystal_description acicular _exptl_crystal_F_000 1072 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.899 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.113 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 268 _refine_ls_number_reflns 3471 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.124 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0551 _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^)+(0.0895P)^2^+0.3005P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1435 _refine_ls_wR_factor_ref 0.1594 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2859 _reflns_number_total 3471 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL CHENTIANFENG_LY_ZHENGBINGCHUN in P2(1)/n chentianfeng_ly_zhengbingchun.res created by SHELXL-2016/4 at 16:46:08 on 02-Nov-2016 CELL 1.54184 21.936236 4.536981 23.816147 90 112.1188 90 ZERR 4 0.000945 0.000163 0.001094 0 0.0053 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Se UNIT 80 80 16 16 8 EQIV $1 1+X,2+Y,+Z SADI 0.005 C13 C12 C8_$1 C9_$1 SADI 0.005 Se1 N4 N1 Se2 SADI 0.005 N4 Se1 Se2 N1 L.S. 40 PLAN 1 BOND MORE -1 BOND $H CONF fmap 2 acta REM REM REM WGHT 0.089500 0.300500 FVAR 2.87859 C1 1 0.053800 -0.862386 0.163581 11.00000 0.05524 0.05579 = 0.04087 0.00542 0.02027 0.00690 C2 1 0.001017 -1.019089 0.119224 11.00000 0.05170 0.05238 = 0.04632 0.00382 0.02097 0.00168 C3 1 -0.040747 -1.200545 0.137582 11.00000 0.06122 0.06351 = 0.05830 0.00650 0.02660 0.00146 C4 1 -0.029497 -1.218042 0.197665 11.00000 0.06243 0.06395 = 0.06624 0.01366 0.03463 0.00669 C5 1 0.023996 -1.059291 0.242320 11.00000 0.06838 0.08158 = 0.05282 0.00375 0.02727 0.00283 C6 1 0.064711 -0.890162 0.226617 11.00000 0.07004 0.08382 = 0.04003 0.00016 0.01673 -0.00161 C7 1 -0.072005 -1.393555 0.221135 11.00000 0.06888 0.08088 = 0.07202 0.01445 0.03566 0.00072 C8 1 -0.168223 -1.675138 0.195801 11.00000 0.08816 0.11199 = 0.11323 0.03205 0.04631 -0.01207 AFIX 23 H8A 2 -0.148175 -1.842986 0.221295 11.00000 -1.20000 H8B 2 -0.184348 -1.540964 0.218778 11.00000 -1.20000 AFIX 0 C9 1 -0.220773 -1.769957 0.143198 11.00000 0.11030 0.19379 = 0.11928 0.04137 0.02071 -0.06182 AFIX 23 H9A 2 -0.205156 -1.923708 0.123647 11.00000 -1.20000 H9B 2 -0.235512 -1.606190 0.115122 11.00000 -1.20000 AFIX 0 C10 1 -0.279101 -1.887765 0.157062 11.00000 0.09711 0.21574 = 0.19148 0.04258 0.05328 -0.05836 AFIX 137 H10A 2 -0.264525 -2.046110 0.185785 11.00000 -1.50000 H10B 2 -0.312493 -1.958628 0.120367 11.00000 -1.50000 H10C 2 -0.296813 -1.732334 0.173715 11.00000 -1.50000 AFIX 0 C11 1 0.555849 0.759536 0.087854 11.00000 0.08164 0.10779 = 0.10872 -0.01991 0.05252 -0.02245 AFIX 137 H11A 2 0.540465 0.910639 0.057541 11.00000 -1.50000 H11B 2 0.585694 0.632116 0.078531 11.00000 -1.50000 H11C 2 0.578143 0.848560 0.126816 11.00000 -1.50000 AFIX 0 C12 1 0.497767 0.581436 0.088920 11.00000 0.08302 0.08294 = 0.10257 -0.00009 0.04536 -0.00942 AFIX 23 H12A 2 0.482794 0.452803 0.053808 11.00000 -1.20000 H12B 2 0.512484 0.457559 0.124752 11.00000 -1.20000 AFIX 0 C13 1 0.443693 0.753934 0.088949 11.00000 0.08305 0.07219 = 0.12405 0.00391 0.05962 -0.01400 AFIX 23 H13A 2 0.425270 0.861943 0.051122 11.00000 -1.20000 H13B 2 0.458820 0.895817 0.121794 11.00000 -1.20000 AFIX 0 C14 1 0.346168 0.459645 0.046792 11.00000 0.07184 0.06467 = 0.07904 0.00599 0.04102 0.00200 C15 1 0.299456 0.259501 0.061679 11.00000 0.05706 0.05722 = 0.06079 0.00187 0.02950 0.00443 C16 1 0.245319 0.141302 0.013069 11.00000 0.07459 0.08131 = 0.04932 0.00627 0.02692 -0.00887 AFIX 43 H16 2 0.239900 0.191656 -0.026379 11.00000 -1.20000 AFIX 0 C17 1 0.201282 -0.041817 0.021897 11.00000 0.07501 0.08334 = 0.04424 0.00490 0.02272 -0.01093 AFIX 43 H17 2 0.165444 -0.112192 -0.010779 11.00000 -1.20000 AFIX 0 C18 1 0.210931 -0.126227 0.083078 11.00000 0.05464 0.05704 = 0.03763 -0.00040 0.01564 0.00601 C19 1 0.265469 -0.013094 0.131342 11.00000 0.05023 0.04497 = 0.04404 -0.00028 0.02005 0.00508 C20 1 0.310390 0.186339 0.119767 11.00000 0.04769 0.06394 = 0.05448 -0.00159 0.01945 -0.00021 AFIX 43 H20 2 0.346212 0.263405 0.151556 11.00000 -1.20000 AFIX 0 N2 3 -0.004756 -0.987500 0.062021 11.00000 0.06523 0.06841 = 0.04571 -0.00088 0.02132 -0.01166 N3 3 0.271580 -0.093250 0.186757 11.00000 0.06508 0.06169 = 0.04675 -0.00457 0.02089 -0.01092 N4 3 0.169883 -0.314648 0.097892 11.00000 0.04948 0.06326 = 0.04606 -0.00152 0.01292 -0.00849 O1 4 -0.065517 -1.408794 0.272720 11.00000 0.12916 0.14208 = 0.08012 0.01763 0.06078 -0.02624 O2 4 -0.119994 -1.527012 0.177295 11.00000 0.08043 0.10276 = 0.08915 0.02205 0.04239 -0.01612 O3 4 0.392902 0.567176 0.096240 11.00000 0.06982 0.07346 = 0.09697 0.00640 0.03851 -0.01622 O4 4 0.340801 0.511221 -0.004083 11.00000 0.10099 0.11988 = 0.08641 0.02303 0.04960 -0.01440 SE1 5 0.058488 -0.738157 0.061952 11.00000 0.05652 0.06868 = 0.04485 0.00555 0.01820 -0.00569 SE2 5 0.204140 -0.330895 0.178294 11.00000 0.05840 0.06103 = 0.04196 0.00389 0.01823 -0.00226 N1 3 0.088239 -0.703339 0.141522 11.00000 0.05678 HKLF 4 REM CHENTIANFENG_LY_ZHENGBINGCHUN in P2(1)/n REM R1 = 0.0551 for 2859 Fo > 4sig(Fo) and 0.0667 for all 3471 data REM 268 parameters refined using 2 restraints END WGHT 0.0892 0.3133 REM Highest difference peak 0.899, deepest hole -0.515, 1-sigma level 0.113 Q1 1 0.1070 -0.6894 0.1048 11.00000 0.05 0.73 REM The information below was added by Olex2. REM REM R1 = 0.0551 for 2859 Fo > 4sig(Fo) and 0.0667 for all 7205 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.90, deepest hole -0.52 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0667 REM R1_gt = 0.0551 REM wR_ref = 0.1594 REM GOOF = 1.094 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 7205 REM Reflections_gt = 2859 REM Parameters = n/a REM Hole = -0.52 REM Peak = 0.90 REM Flack = n/a ; _cod_data_source_file c6ra28801d2.cif _cod_data_source_block PBS _cod_original_cell_volume 2195.84(18) _cod_database_code 7227861 _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. ; _exptl_absorpt_special_details acicular _reflns_odcompleteness_completeness 99.84 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 61.08 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances C13-C12 \\sim C8_$1-C9_$1 with sigma of 0.005 Se1-N4 \\sim N1-Se2 with sigma of 0.005 N4-Se1 \\sim Se2-N1 with sigma of 0.005 3.a Secondary CH2 refined with riding coordinates: C8(H8a,H8b), C9(H9a,H9b), C12(H12a,H12b), C13(H13a,H13b) 3.b Aromatic/amide H refined with riding coordinates: C16(H16), C17(H17), C20(H20) 3.c Idealised Me refined as rotating group: C10(H10a,H10b,H10c), C11(H11a,H11b,H11c) ; _shelx_shelxl_version_number 2016/4 _olex2_submission_special_instructions 'No special instructions were received' 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 C1 C 0.0538(3) -0.8624(13) 0.1636(2) 0.0500(12) Uani 1 1 d . C2 C 0.0010(3) -1.0191(12) 0.1192(2) 0.0494(12) Uani 1 1 d . C3 C -0.0407(3) -1.2005(14) 0.1376(3) 0.0598(15) Uani 1 1 d . C4 C -0.0295(3) -1.2180(14) 0.1977(3) 0.0612(15) Uani 1 1 d . C5 C 0.0240(3) -1.0593(17) 0.2423(3) 0.0663(16) Uani 1 1 d . C6 C 0.0647(3) -0.8902(17) 0.2266(3) 0.0658(16) Uani 1 1 d . C7 C -0.0720(3) -1.3936(17) 0.2211(3) 0.0713(17) Uani 1 1 d . C8 C -0.1682(4) -1.675(2) 0.1958(4) 0.102(3) Uani 1 1 d . H8A H -0.148175 -1.842986 0.221295 0.122 Uiso 1 1 calc R H8B H -0.184348 -1.540964 0.218778 0.122 Uiso 1 1 calc R C9 C -0.2208(5) -1.770(3) 0.1432(5) 0.148(5) Uani 1 1 d . H9A H -0.205156 -1.923708 0.123647 0.177 Uiso 1 1 calc R H9B H -0.235512 -1.606190 0.115122 0.177 Uiso 1 1 calc R C10 C -0.2791(5) -1.888(4) 0.1571(6) 0.168(6) Uani 1 1 d . H10A H -0.264525 -2.046110 0.185785 0.253 Uiso 1 1 calc GR H10B H -0.312493 -1.958628 0.120367 0.253 Uiso 1 1 calc GR H10C H -0.296813 -1.732334 0.173715 0.253 Uiso 1 1 calc GR C11 C 0.5558(4) 0.760(2) 0.0879(5) 0.095(3) Uani 1 1 d . H11A H 0.540465 0.910639 0.057541 0.142 Uiso 1 1 calc GR H11B H 0.585694 0.632116 0.078531 0.142 Uiso 1 1 calc GR H11C H 0.578143 0.848560 0.126816 0.142 Uiso 1 1 calc GR C12 C 0.4978(4) 0.5814(18) 0.0889(4) 0.086(2) Uani 1 1 d . H12A H 0.482794 0.452803 0.053808 0.104 Uiso 1 1 calc R H12B H 0.512484 0.457559 0.124752 0.104 Uiso 1 1 calc R C13 C 0.4437(4) 0.7539(17) 0.0889(4) 0.087(2) Uani 1 1 d . H13A H 0.425270 0.861943 0.051122 0.104 Uiso 1 1 calc R H13B H 0.458820 0.895817 0.121794 0.104 Uiso 1 1 calc R C14 C 0.3462(3) 0.4596(15) 0.0468(3) 0.0682(16) Uani 1 1 d . C15 C 0.2995(3) 0.2595(13) 0.0617(3) 0.0562(14) Uani 1 1 d . C16 C 0.2453(3) 0.1413(16) 0.0131(3) 0.0674(17) Uani 1 1 d . H16 H 0.239900 0.191656 -0.026379 0.081 Uiso 1 1 calc R C17 C 0.2013(3) -0.0418(16) 0.0219(3) 0.0675(16) Uani 1 1 d . H17 H 0.165444 -0.112192 -0.010779 0.081 Uiso 1 1 calc R C18 C 0.2109(3) -0.1262(13) 0.0831(2) 0.0503(12) Uani 1 1 d . C19 C 0.2655(2) -0.0131(11) 0.1313(2) 0.0457(11) Uani 1 1 d . C20 C 0.3104(3) 0.1863(14) 0.1198(3) 0.0553(14) Uani 1 1 d . H20 H 0.346212 0.263405 0.151556 0.066 Uiso 1 1 calc R N2 N -0.0048(2) -0.9875(12) 0.0620(2) 0.0597(12) Uani 1 1 d . N3 N 0.2716(2) -0.0932(11) 0.1868(2) 0.0579(12) Uani 1 1 d . N4 N 0.1699(2) -0.3146(10) 0.0979(2) 0.0544(11) Uani 1 1 d . O1 O -0.0655(3) -1.4088(17) 0.2727(3) 0.111(2) Uani 1 1 d . O2 O -0.1200(2) -1.5270(13) 0.1773(2) 0.0877(15) Uani 1 1 d . O3 O 0.3929(2) 0.5672(11) 0.0962(2) 0.0780(13) Uani 1 1 d . O4 O 0.3408(3) 0.5112(15) -0.0041(3) 0.0982(17) Uani 1 1 d . Se1 Se 0.05849(3) -0.73816(15) 0.06195(3) 0.0569(2) Uani 1 1 d . Se2 Se 0.20414(3) -0.33089(14) 0.17829(2) 0.0540(2) Uani 1 1 d . N1 N 0.0882(2) -0.7033(10) 0.1415(2) 0.0568(12) 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 C1 0.055(3) 0.056(3) 0.041(3) 0.005(2) 0.020(2) 0.007(3) C2 0.052(3) 0.052(3) 0.046(3) 0.004(2) 0.021(2) 0.002(2) C3 0.061(3) 0.064(4) 0.058(3) 0.007(3) 0.027(3) 0.001(3) C4 0.062(3) 0.064(4) 0.066(4) 0.014(3) 0.035(3) 0.007(3) C5 0.068(4) 0.082(4) 0.053(3) 0.004(3) 0.027(3) 0.003(3) C6 0.070(4) 0.084(4) 0.040(3) 0.000(3) 0.017(3) -0.002(3) C7 0.069(4) 0.081(5) 0.072(4) 0.014(4) 0.036(3) 0.001(4) C8 0.088(5) 0.112(7) 0.113(7) 0.032(6) 0.046(5) -0.012(5) C9 0.110(8) 0.194(13) 0.119(9) 0.041(8) 0.021(7) -0.062(8) C10 0.097(7) 0.216(16) 0.191(13) 0.043(12) 0.053(8) -0.058(9) C11 0.082(5) 0.108(6) 0.109(6) -0.020(5) 0.053(5) -0.022(5) C12 0.083(5) 0.083(5) 0.103(6) 0.000(4) 0.045(4) -0.009(4) C13 0.083(5) 0.072(5) 0.124(7) 0.004(4) 0.060(5) -0.014(4) C14 0.072(4) 0.065(4) 0.079(4) 0.006(3) 0.041(4) 0.002(3) C15 0.057(3) 0.057(3) 0.061(3) 0.002(3) 0.029(3) 0.004(3) C16 0.075(4) 0.081(4) 0.049(3) 0.006(3) 0.027(3) -0.009(3) C17 0.075(4) 0.083(4) 0.044(3) 0.005(3) 0.023(3) -0.011(4) C18 0.055(3) 0.057(3) 0.038(3) 0.000(2) 0.016(2) 0.006(3) C19 0.050(3) 0.045(3) 0.044(3) 0.000(2) 0.020(2) 0.005(2) C20 0.048(3) 0.064(4) 0.054(3) -0.002(3) 0.019(3) 0.000(3) N2 0.065(3) 0.068(3) 0.046(2) -0.001(2) 0.021(2) -0.012(2) N3 0.065(3) 0.062(3) 0.047(2) -0.005(2) 0.021(2) -0.011(2) N4 0.049(2) 0.063(3) 0.046(2) -0.002(2) 0.013(2) -0.008(2) O1 0.129(5) 0.142(6) 0.080(4) 0.018(4) 0.061(4) -0.026(4) O2 0.080(3) 0.103(4) 0.089(3) 0.022(3) 0.042(3) -0.016(3) O3 0.070(3) 0.073(3) 0.097(3) 0.006(3) 0.039(3) -0.016(2) O4 0.101(4) 0.120(5) 0.086(3) 0.023(3) 0.050(3) -0.014(3) Se1 0.0565(4) 0.0687(4) 0.0449(4) 0.0056(3) 0.0182(3) -0.0057(3) Se2 0.0584(4) 0.0610(4) 0.0420(3) 0.0039(2) 0.0182(3) -0.0023(3) 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' 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 C2 C1 C6 120.0(5) N1 C1 C2 114.4(5) N1 C1 C6 125.6(6) C3 C2 C1 119.9(5) N2 C2 C1 116.3(5) N2 C2 C3 123.8(5) C4 C3 C2 118.4(6) C3 C4 C5 121.4(6) C3 C4 C7 122.4(6) C5 C4 C7 116.2(6) C6 C5 C4 121.6(5) C5 C6 C1 118.6(6) O1 C7 C4 125.0(7) O1 C7 O2 122.9(7) O2 C7 C4 112.0(6) H8A C8 H8B 108.4 C9 C8 H8A 110.0 C9 C8 H8B 110.0 C9 C8 O2 108.4(8) O2 C8 H8A 110.0 O2 C8 H8B 110.0 C8 C9 H9A 109.1 C8 C9 H9B 109.1 C8 C9 C10 112.6(10) H9A C9 H9B 107.8 C10 C9 H9A 109.1 C10 C9 H9B 109.1 C9 C10 H10A 109.5 C9 C10 H10B 109.5 C9 C10 H10C 109.5 H10A C10 H10B 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 H11A C11 H11B 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C12 C11 H11A 109.5 C12 C11 H11B 109.5 C12 C11 H11C 109.5 C11 C12 H12A 108.7 C11 C12 H12B 108.7 H12A C12 H12B 107.6 C13 C12 C11 114.4(7) C13 C12 H12A 108.7 C13 C12 H12B 108.7 C12 C13 H13A 109.5 C12 C13 H13B 109.5 C12 C13 O3 110.8(6) H13A C13 H13B 108.1 O3 C13 H13A 109.5 O3 C13 H13B 109.5 O3 C14 C15 112.2(6) O4 C14 C15 122.7(7) O4 C14 O3 125.1(6) C16 C15 C14 118.1(6) C20 C15 C14 120.9(6) C20 C15 C16 121.0(6) C15 C16 H16 118.8 C17 C16 C15 122.4(6) C17 C16 H16 118.8 C16 C17 H17 120.7 C16 C17 C18 118.6(6) C18 C17 H17 120.7 C19 C18 C17 119.0(5) N4 C18 C17 124.1(5) N4 C18 C19 116.9(5) C18 C19 C20 120.4(5) N3 C19 C18 116.7(5) N3 C19 C20 122.9(5) C15 C20 C19 118.7(5) C15 C20 H20 120.7 C19 C20 H20 120.7 C2 N2 Se1 107.1(4) C19 N3 Se2 106.6(4) C18 N4 Se2 104.4(3) C7 O2 C8 115.3(6) C14 O3 C13 118.4(6) N1 Se1 N2 91.7(2) N4 Se2 N3 95.3(2) C1 N1 Se1 110.5(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.429(8) C1 C6 1.434(8) C1 N1 1.291(7) C2 C3 1.418(8) C2 N2 1.328(7) C3 C4 1.360(9) C4 C5 1.445(10) C4 C7 1.486(9) C5 C6 1.333(10) C7 O1 1.184(8) C7 O2 1.318(9) C8 H8A 0.9700 C8 H8B 0.9700 C8 C9 1.413(10) C8 O2 1.455(9) C9 H9A 0.9700 C9 H9B 0.9700 C9 C10 1.533(14) C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600 C11 C12 1.517(11) C12 H12A 0.9700 C12 H12B 0.9700 C12 C13 1.421(9) C13 H13A 0.9700 C13 H13B 0.9700 C13 O3 1.461(8) C14 C15 1.508(9) C14 O3 1.329(8) C14 O4 1.196(8) C15 C16 1.415(9) C15 C20 1.353(8) C16 H16 0.9300 C16 C17 1.349(9) C17 H17 0.9300 C17 C18 1.443(8) C18 C19 1.407(7) C18 N4 1.380(7) C19 C20 1.439(8) C19 N3 1.326(7) C20 H20 0.9300 N2 Se1 1.791(5) N3 Se2 1.780(5) N4 Se2 1.776(5) Se1 N1 1.764(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 C1 C2 C3 C4 0.6(9) C1 C2 N2 Se1 -1.4(6) C2 C1 C6 C5 -1.3(9) C2 C1 N1 Se1 -0.9(6) C2 C3 C4 C5 -0.7(9) C2 C3 C4 C7 177.7(6) C2 N2 Se1 N1 0.8(4) C3 C2 N2 Se1 179.9(5) C3 C4 C5 C6 -0.3(11) C3 C4 C7 O1 -177.6(8) C3 C4 C7 O2 0.5(10) C4 C5 C6 C1 1.3(10) C4 C7 O2 C8 -173.1(7) C5 C4 C7 O1 0.9(11) C5 C4 C7 O2 179.0(6) C6 C1 C2 C3 0.4(8) C6 C1 C2 N2 -178.3(6) C6 C1 N1 Se1 179.1(5) C7 C4 C5 C6 -178.8(7) C9 C8 O2 C7 171.8(9) C11 C12 C13 O3 -174.2(7) C12 C13 O3 C14 -89.6(9) C14 C15 C16 C17 179.4(7) C14 C15 C20 C19 -178.0(5) C15 C14 O3 C13 177.1(5) C15 C16 C17 C18 -1.8(11) C16 C15 C20 C19 -0.5(9) C16 C17 C18 C19 0.5(9) C16 C17 C18 N4 -179.2(6) C17 C18 C19 C20 0.7(8) C17 C18 C19 N3 178.9(5) C17 C18 N4 Se2 -178.7(5) C18 C19 C20 C15 -0.7(8) C18 C19 N3 Se2 0.3(6) C18 N4 Se2 N3 -1.2(4) C19 C18 N4 Se2 1.6(6) C19 N3 Se2 N4 0.5(4) C20 C15 C16 C17 1.8(10) C20 C19 N3 Se2 178.5(4) N2 C2 C3 C4 179.2(6) N2 Se1 N1 C1 0.1(4) N3 C19 C20 C15 -178.8(6) N4 C18 C19 C20 -179.6(5) N4 C18 C19 N3 -1.4(7) O1 C7 O2 C8 5.1(12) O2 C8 C9 C10 -171.4(11) O3 C14 C15 C16 176.9(6) O3 C14 C15 C20 -5.5(9) O4 C14 C15 C16 -3.3(10) O4 C14 C15 C20 174.3(7) O4 C14 O3 C13 -2.6(11) N1 C1 C2 C3 -179.7(5) N1 C1 C2 N2 1.6(8) N1 C1 C6 C5 178.7(6)