# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Q1 #TrackingRef '2-((1R)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-7-methylbenzo[d][1,2]selenazol-3(2H)-one.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H29 N3 O2 Se' _chemical_formula_sum 'C28 H29 N3 O2 Se' _chemical_formula_weight 518.50 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.2900(5) _cell_length_b 16.2681(10) _cell_length_c 16.8894(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2552.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 9759 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 23.02 _exptl_crystal_description irregular _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 1.500 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6453 _exptl_absorpt_correction_T_max 0.7535 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16444 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 24.09 _reflns_number_total 3449 _reflns_number_gt 3054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+0.0765P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration unk _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.010(8) _refine_ls_number_reflns 3449 _refine_ls_number_parameters 316 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0616 _refine_ls_wR_factor_gt 0.0590 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL Q1 in P2(1)2(1)2(1) CELL 0.71073 9.2900 16.2681 16.8894 90.000 90.000 90.000 ZERR 4.00 0.0005 0.0010 0.0010 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O SE UNIT 112 116 12 8 4 TEMP 21 SIZE 0.32 0.25 0.20 ACTA 50 L.S. 12 EADP C18A C18B EADP C19A C19B SADI C17 C18A C17 C18B SADI C18A C19A C18B C19B FMAP 2 PLAN 10 BOND $H CONF WGHT 0.032500 0.076500 FVAR 0.14491 0.71651 SE1 5 0.086903 1.103210 0.406845 11.00000 0.04441 0.04872 = 0.05066 0.00626 0.00240 -0.00286 O1 4 -0.125100 0.740338 0.519626 11.00000 0.07305 0.07900 = 0.09261 0.01303 0.01034 -0.01843 O2 4 0.164502 0.949646 0.581006 11.00000 0.07149 0.06148 = 0.05532 0.00612 -0.00068 0.02157 N1 3 0.029392 0.839867 0.221519 11.00000 0.06219 0.09372 = 0.06500 -0.01732 -0.00654 -0.01197 N2 3 0.457389 1.041408 0.464721 11.00000 0.04609 0.06921 = 0.07905 -0.02910 0.00128 -0.00736 N3 3 0.157028 1.011525 0.459528 11.00000 0.03796 0.04493 = 0.04458 -0.00012 0.00183 0.00493 C1 1 0.253854 0.954340 0.418823 11.00000 0.03649 0.04387 = 0.05427 -0.00275 -0.00171 0.00347 AFIX 13 H1 2 0.276510 0.910364 0.456471 11.00000 -1.20000 AFIX 0 C2 1 0.176270 0.914645 0.349664 11.00000 0.03919 0.04956 = 0.05048 -0.00526 0.00083 0.00372 C3 1 0.199355 0.936270 0.272910 11.00000 0.04914 0.06782 = 0.05810 -0.00437 -0.00183 -0.01009 AFIX 43 H3 2 0.266898 0.976698 0.261273 11.00000 -1.20000 AFIX 0 C4 1 0.123349 0.898812 0.211119 11.00000 0.07075 0.09893 = 0.05096 -0.00624 -0.00207 -0.01149 AFIX 43 H4 2 0.140609 0.916846 0.159737 11.00000 -1.20000 AFIX 0 C5 1 0.002293 0.817583 0.296736 11.00000 0.04703 0.06204 = 0.06220 -0.00938 -0.00394 -0.00154 C6 1 0.070368 0.853203 0.363620 11.00000 0.03703 0.04607 = 0.05910 -0.00816 -0.00418 0.00335 C7 1 0.028310 0.826480 0.440149 11.00000 0.04503 0.04513 = 0.06265 -0.00417 0.00023 -0.00162 AFIX 43 H7 2 0.071279 0.849198 0.484810 11.00000 -1.20000 AFIX 0 C8 1 -0.075072 0.767505 0.448367 11.00000 0.04808 0.05748 = 0.08189 0.00919 0.00646 -0.00170 C9 1 -0.135847 0.729476 0.382607 11.00000 0.05735 0.06358 = 0.10519 -0.00027 -0.00526 -0.01644 AFIX 43 H9 2 -0.201589 0.686986 0.389638 11.00000 -1.20000 AFIX 0 C10 1 -0.100450 0.753564 0.308951 11.00000 0.05736 0.07417 = 0.08891 -0.01828 -0.01169 -0.01651 AFIX 43 H10 2 -0.143318 0.728271 0.265563 11.00000 -1.20000 AFIX 0 C11 1 0.396585 0.995409 0.396701 11.00000 0.03945 0.05684 = 0.05136 -0.00541 -0.00253 -0.00072 AFIX 13 H11 2 0.376430 1.035286 0.354646 11.00000 -1.20000 AFIX 0 C12 1 0.506510 0.933851 0.364188 11.00000 0.04157 0.06468 = 0.06921 -0.01481 0.00790 -0.00022 AFIX 23 H12A 2 0.479686 0.878373 0.379197 11.00000 -1.20000 H12B 2 0.509478 0.936907 0.306854 11.00000 -1.20000 AFIX 0 C13 1 0.654212 0.955377 0.398750 11.00000 0.03938 0.09273 = 0.09331 -0.02020 0.00727 0.00453 AFIX 13 H13 2 0.728616 0.921755 0.373390 11.00000 -1.20000 AFIX 0 C14 1 0.649500 0.936813 0.487002 11.00000 0.05725 0.12434 = 0.09214 -0.01037 -0.01370 0.01502 AFIX 23 H14A 2 0.738620 0.953819 0.512046 11.00000 -1.20000 H14B 2 0.636833 0.878315 0.495666 11.00000 -1.20000 AFIX 0 C15 1 0.521779 0.984772 0.522024 11.00000 0.05242 0.11382 = 0.07195 -0.02172 -0.01002 -0.00517 AFIX 23 H15A 2 0.449079 0.946166 0.539816 11.00000 -1.20000 H15B 2 0.554426 1.015676 0.567740 11.00000 -1.20000 AFIX 0 C16 1 0.571300 1.094534 0.432402 11.00000 0.06092 0.09049 = 0.10577 -0.02635 0.00210 -0.02890 AFIX 23 H16A 2 0.617256 1.123804 0.475584 11.00000 -1.20000 H16B 2 0.528086 1.134976 0.397532 11.00000 -1.20000 AFIX 0 C17 1 0.686997 1.045975 0.385963 11.00000 0.04481 0.11942 = 0.09640 -0.03178 0.00616 -0.01993 AFIX 13 H17 2 0.781542 1.058143 0.408876 11.00000 -1.20000 AFIX 0 PART -1 C18A 1 0.686087 1.074874 0.299155 21.00000 0.06049 0.10465 = 0.12063 -0.00887 0.01844 0.00395 AFIX 43 H18A 2 0.601751 1.100727 0.283031 21.00000 -1.20000 AFIX 0 C19A 1 0.784668 1.068809 0.244888 21.00000 0.11753 0.29803 = 0.09349 0.04719 -0.00034 -0.03486 AFIX 93 H19A 2 0.872084 1.043696 0.256504 21.00000 -1.20000 H19B 2 0.767807 1.089582 0.194433 21.00000 -1.20000 AFIX 0 PART -2 C18B 1 0.740502 1.051695 0.299862 -21.00000 0.06049 0.10465 = 0.12063 -0.00887 0.01844 0.00395 AFIX 43 H18B 2 0.805575 1.019052 0.272252 -21.00000 -1.20000 AFIX 0 C19B 1 0.665832 1.117321 0.276696 -21.00000 0.11753 0.29803 = 0.09349 0.04719 -0.00034 -0.03486 AFIX 93 H19C 2 0.604205 1.143541 0.311983 -21.00000 -1.20000 H19D 2 0.675321 1.136922 0.225234 -21.00000 -1.20000 AFIX 0 PART 0 C20 1 -0.085190 0.784006 0.588445 11.00000 0.09832 0.07995 = 0.09044 0.02044 0.02535 -0.00170 AFIX 137 H20A 2 0.016490 0.778312 0.596970 11.00000 -1.50000 H20B 2 -0.136326 0.762314 0.633201 11.00000 -1.50000 H20C 2 -0.108597 0.841088 0.581960 11.00000 -1.50000 AFIX 0 C21 1 0.122533 1.005625 0.537425 11.00000 0.04056 0.04669 = 0.04760 -0.00222 -0.00393 0.00073 C22 1 0.024517 1.072050 0.560375 11.00000 0.04866 0.05006 = 0.04090 -0.00480 -0.00067 0.00225 C23 1 -0.005737 1.129128 0.502441 11.00000 0.04059 0.04482 = 0.05278 -0.00040 -0.00637 -0.00429 C24 1 -0.099415 1.195643 0.515279 11.00000 0.05368 0.04810 = 0.06173 -0.00134 -0.00163 0.00791 C25 1 -0.160092 1.199071 0.589794 11.00000 0.09069 0.07560 = 0.07140 -0.01259 0.00692 0.03574 AFIX 43 H25 2 -0.222219 1.242254 0.601379 11.00000 -1.20000 AFIX 0 C26 1 -0.133214 1.141918 0.647533 11.00000 0.12041 0.10211 = 0.05099 0.00730 0.02760 0.05122 AFIX 43 H26 2 -0.178010 1.146477 0.696580 11.00000 -1.20000 AFIX 0 C27 1 -0.040658 1.078135 0.633271 11.00000 0.09146 0.07167 = 0.05162 0.00514 0.00566 0.02520 AFIX 43 H27 2 -0.022056 1.039361 0.672418 11.00000 -1.20000 AFIX 0 C28 1 -0.131154 1.255658 0.451150 11.00000 0.07577 0.05531 = 0.08169 0.00338 -0.01013 0.00824 AFIX 137 H28A 2 -0.159925 1.307089 0.474090 11.00000 -1.50000 H28B 2 -0.207496 1.234859 0.418498 11.00000 -1.50000 H28C 2 -0.046522 1.263753 0.419481 11.00000 -1.50000 HKLF 4 REM Q1 in P2(1)2(1)2(1) REM R1 = 0.0275 for 3054 Fo > 4sig(Fo) and 0.0361 for all 3449 data REM 316 parameters refined using 2 restraints END WGHT 0.0325 0.0764 REM Highest difference peak 0.240, deepest hole -0.148, 1-sigma level 0.042 Q1 1 0.0828 1.1150 0.4672 11.00000 0.05 0.24 Q2 1 0.0810 1.1006 0.3391 11.00000 0.05 0.24 Q3 1 0.5768 1.0861 0.2429 11.00000 0.05 0.21 Q4 1 0.1978 1.1053 0.4028 11.00000 0.05 0.20 Q5 1 0.3642 1.0994 0.2288 11.00000 0.05 0.19 Q6 1 -0.1148 1.2257 0.4008 11.00000 0.05 0.17 Q7 1 -0.0487 1.1013 0.3788 11.00000 0.05 0.17 Q8 1 0.0621 0.8366 0.4002 11.00000 0.05 0.17 Q9 1 0.5591 1.0620 0.5593 11.00000 0.05 0.16 Q10 1 0.0606 1.0958 0.5765 11.00000 0.05 0.16 ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.08690(3) 1.103210(18) 0.406845(18) 0.04793(12) Uani 1 1 d . . . O1 O -0.1251(3) 0.74034(17) 0.51963(17) 0.0816(8) Uani 1 1 d . . . O2 O 0.1645(3) 0.94965(14) 0.58101(13) 0.0628(6) Uani 1 1 d . . . N1 N 0.0294(3) 0.8399(2) 0.22152(19) 0.0736(9) Uani 1 1 d . . . N2 N 0.4574(3) 1.04141(18) 0.46472(18) 0.0648(8) Uani 1 1 d . . . N3 N 0.1570(3) 1.01152(14) 0.45953(14) 0.0425(6) Uani 1 1 d . . . C1 C 0.2539(3) 0.95434(17) 0.41882(19) 0.0449(8) Uani 1 1 d . . . H1 H 0.2765 0.9104 0.4565 0.054 Uiso 1 1 calc R . . C2 C 0.1763(3) 0.91464(18) 0.34966(18) 0.0464(8) Uani 1 1 d . . . C3 C 0.1994(4) 0.9363(2) 0.2729(2) 0.0584(9) Uani 1 1 d . . . H3 H 0.2669 0.9767 0.2613 0.070 Uiso 1 1 calc R . . C4 C 0.1233(4) 0.8988(3) 0.2111(2) 0.0735(10) Uani 1 1 d . . . H4 H 0.1406 0.9168 0.1597 0.088 Uiso 1 1 calc R . . C5 C 0.0023(4) 0.8176(2) 0.2967(2) 0.0571(9) Uani 1 1 d . . . C6 C 0.0704(3) 0.85320(18) 0.36362(19) 0.0474(8) Uani 1 1 d . . . C7 C 0.0283(3) 0.82648(19) 0.4401(2) 0.0509(8) Uani 1 1 d . . . H7 H 0.0713 0.8492 0.4848 0.061 Uiso 1 1 calc R . . C8 C -0.0751(4) 0.7675(2) 0.4484(2) 0.0625(9) Uani 1 1 d . . . C9 C -0.1358(4) 0.7295(2) 0.3826(3) 0.0754(11) Uani 1 1 d . . . H9 H -0.2016 0.6870 0.3896 0.090 Uiso 1 1 calc R . . C10 C -0.1005(4) 0.7536(2) 0.3090(3) 0.0735(11) Uani 1 1 d . . . H10 H -0.1433 0.7283 0.2656 0.088 Uiso 1 1 calc R . . C11 C 0.3966(3) 0.99541(18) 0.39670(17) 0.0492(8) Uani 1 1 d . . . H11 H 0.3764 1.0353 0.3546 0.059 Uiso 1 1 calc R . . C12 C 0.5065(3) 0.9339(2) 0.3642(2) 0.0585(9) Uani 1 1 d . . . H12A H 0.4797 0.8784 0.3792 0.070 Uiso 1 1 calc R . . H12B H 0.5095 0.9369 0.3069 0.070 Uiso 1 1 calc R . . C13 C 0.6542(4) 0.9554(2) 0.3987(3) 0.0751(11) Uani 1 1 d . A . H13 H 0.7286 0.9218 0.3734 0.090 Uiso 1 1 calc R . . C14 C 0.6495(5) 0.9368(3) 0.4870(3) 0.0912(13) Uani 1 1 d . . . H14A H 0.7386 0.9538 0.5120 0.109 Uiso 1 1 calc R . . H14B H 0.6368 0.8783 0.4957 0.109 Uiso 1 1 calc R . . C15 C 0.5218(4) 0.9848(3) 0.5220(2) 0.0794(12) Uani 1 1 d . . . H15A H 0.4491 0.9462 0.5398 0.095 Uiso 1 1 calc R . . H15B H 0.5544 1.0157 0.5677 0.095 Uiso 1 1 calc R . . C16 C 0.5713(4) 1.0945(3) 0.4324(2) 0.0857(12) Uani 1 1 d . A . H16A H 0.6173 1.1238 0.4756 0.103 Uiso 1 1 calc R . . H16B H 0.5281 1.1350 0.3975 0.103 Uiso 1 1 calc R . . C17 C 0.6870(4) 1.0460(3) 0.3860(3) 0.0869(13) Uani 1 1 d D . . H17 H 0.7815 1.0581 0.4089 0.104 Uiso 1 1 calc R A . C18A C 0.6861(9) 1.0749(6) 0.2992(5) 0.095(3) Uani 0.717(11) 1 d PD A -1 H18A H 0.6018 1.1007 0.2830 0.114 Uiso 0.717(11) 1 calc PR A -1 C19A C 0.7847(10) 1.0688(7) 0.2449(5) 0.170(5) Uani 0.717(11) 1 d PD A -1 H19A H 0.8721 1.0437 0.2565 0.204 Uiso 0.717(11) 1 calc PR A -1 H19B H 0.7678 1.0896 0.1944 0.204 Uiso 0.717(11) 1 calc PR A -1 C18B C 0.741(3) 1.0517(19) 0.2999(11) 0.095(3) Uani 0.283(11) 1 d PD A -2 H18B H 0.8056 1.0191 0.2723 0.114 Uiso 0.283(11) 1 calc PR A -2 C19B C 0.666(3) 1.1173(19) 0.2767(17) 0.170(5) Uani 0.283(11) 1 d PD A -2 H19C H 0.6042 1.1435 0.3120 0.204 Uiso 0.283(11) 1 calc PR A -2 H19D H 0.6753 1.1369 0.2252 0.204 Uiso 0.283(11) 1 calc PR A -2 C20 C -0.0852(5) 0.7840(2) 0.5884(2) 0.0896(12) Uani 1 1 d . . . H20A H 0.0165 0.7783 0.5970 0.134 Uiso 1 1 calc R . . H20B H -0.1363 0.7623 0.6332 0.134 Uiso 1 1 calc R . . H20C H -0.1086 0.8411 0.5820 0.134 Uiso 1 1 calc R . . C21 C 0.1225(3) 1.0056(2) 0.53742(18) 0.0449(8) Uani 1 1 d . . . C22 C 0.0245(3) 1.07205(19) 0.56038(17) 0.0465(8) Uani 1 1 d . . . C23 C -0.0057(3) 1.12913(18) 0.50244(18) 0.0461(8) Uani 1 1 d . . . C24 C -0.0994(4) 1.19564(18) 0.51528(19) 0.0545(8) Uani 1 1 d . . . C25 C -0.1601(4) 1.1991(2) 0.5898(2) 0.0792(11) Uani 1 1 d . . . H25 H -0.2222 1.2423 0.6014 0.095 Uiso 1 1 calc R . . C26 C -0.1332(5) 1.1419(3) 0.6475(2) 0.0912(15) Uani 1 1 d . . . H26 H -0.1780 1.1465 0.6966 0.109 Uiso 1 1 calc R . . C27 C -0.0407(4) 1.0781(2) 0.6333(2) 0.0716(12) Uani 1 1 d . . . H27 H -0.0221 1.0394 0.6724 0.086 Uiso 1 1 calc R . . C28 C -0.1312(4) 1.2557(2) 0.4511(2) 0.0709(11) Uani 1 1 d . . . H28A H -0.1599 1.3071 0.4741 0.106 Uiso 1 1 calc R . . H28B H -0.2075 1.2349 0.4185 0.106 Uiso 1 1 calc R . . H28C H -0.0465 1.2638 0.4195 0.106 Uiso 1 1 calc R . . 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 0.04441(17) 0.04872(18) 0.05066(18) 0.00626(15) 0.00240(17) -0.00286(15) O1 0.073(2) 0.0790(18) 0.093(2) 0.0130(17) 0.0103(16) -0.0184(14) O2 0.0715(15) 0.0615(14) 0.0553(14) 0.0061(13) -0.0007(13) 0.0216(12) N1 0.062(2) 0.094(2) 0.065(2) -0.0173(18) -0.0065(18) -0.0120(18) N2 0.0461(19) 0.0692(19) 0.079(2) -0.0291(17) 0.0013(16) -0.0074(14) N3 0.0380(13) 0.0449(15) 0.0446(15) -0.0001(12) 0.0018(13) 0.0049(12) C1 0.0365(17) 0.0439(17) 0.054(2) -0.0028(16) -0.0017(17) 0.0035(13) C2 0.0392(17) 0.050(2) 0.0505(19) -0.0053(15) 0.0008(16) 0.0037(15) C3 0.049(2) 0.068(2) 0.058(2) -0.0044(19) -0.0018(19) -0.0101(17) C4 0.071(3) 0.099(3) 0.0510(19) -0.006(2) -0.002(2) -0.011(3) C5 0.047(2) 0.062(2) 0.062(2) -0.0094(18) -0.0039(19) -0.0015(18) C6 0.0370(18) 0.0461(17) 0.0591(19) -0.0082(16) -0.0042(19) 0.0033(16) C7 0.0450(19) 0.0451(19) 0.063(2) -0.0042(15) 0.0002(17) -0.0016(16) C8 0.048(2) 0.057(2) 0.082(2) 0.009(2) 0.006(2) -0.002(2) C9 0.057(2) 0.064(2) 0.105(3) 0.000(2) -0.005(2) -0.0164(18) C10 0.057(2) 0.074(2) 0.089(3) -0.018(2) -0.012(2) -0.017(2) C11 0.0395(17) 0.0568(18) 0.0514(17) -0.0054(16) -0.0025(19) -0.0007(15) C12 0.0416(19) 0.065(2) 0.069(2) -0.0148(17) 0.0079(18) -0.0002(17) C13 0.0394(19) 0.093(3) 0.093(3) -0.020(3) 0.007(2) 0.0045(19) C14 0.057(3) 0.124(4) 0.092(3) -0.010(3) -0.014(2) 0.015(2) C15 0.052(2) 0.114(3) 0.072(3) -0.022(2) -0.010(2) -0.005(2) C16 0.061(2) 0.090(3) 0.106(3) -0.026(2) 0.002(2) -0.029(3) C17 0.045(2) 0.119(4) 0.096(3) -0.032(3) 0.006(2) -0.020(2) C18A 0.060(7) 0.105(9) 0.121(6) -0.009(4) 0.018(6) 0.004(5) C19A 0.118(8) 0.298(14) 0.093(6) 0.047(7) 0.000(6) -0.035(8) C18B 0.060(7) 0.105(9) 0.121(6) -0.009(4) 0.018(6) 0.004(5) C19B 0.118(8) 0.298(14) 0.093(6) 0.047(7) 0.000(6) -0.035(8) C20 0.098(3) 0.080(3) 0.090(3) 0.020(3) 0.025(4) -0.002(2) C21 0.041(2) 0.0467(19) 0.0476(18) -0.0022(16) -0.0039(16) 0.0007(15) C22 0.0487(19) 0.0501(19) 0.0409(17) -0.0048(15) -0.0007(16) 0.0022(15) C23 0.0406(18) 0.045(2) 0.0528(18) -0.0004(15) -0.0064(17) -0.0043(15) C24 0.054(2) 0.0481(19) 0.062(2) -0.0013(16) -0.002(2) 0.0079(18) C25 0.091(3) 0.076(3) 0.071(2) -0.013(2) 0.007(3) 0.036(2) C26 0.120(4) 0.102(3) 0.051(2) 0.007(2) 0.028(2) 0.051(3) C27 0.091(3) 0.072(3) 0.052(2) 0.0051(18) 0.006(2) 0.025(2) C28 0.076(3) 0.055(2) 0.082(2) 0.003(2) -0.010(2) 0.0082(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N3 1.855(2) . ? Se1 C23 1.878(3) . ? O1 C8 1.364(4) . ? O1 C20 1.412(5) . ? O2 C21 1.234(4) . ? N1 C4 1.309(5) . ? N1 C5 1.345(4) . ? N2 C15 1.464(5) . ? N2 C16 1.471(5) . ? N2 C11 1.483(4) . ? N3 C21 1.357(4) . ? N3 C1 1.465(4) . ? C1 C2 1.517(4) . ? C1 C11 1.531(4) . ? C1 H1 0.9800 . ? C2 C3 1.360(4) . ? C2 C6 1.422(4) . ? C3 C4 1.400(5) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.418(4) . ? C5 C10 1.428(5) . ? C6 C7 1.419(4) . ? C7 C8 1.365(5) . ? C7 H7 0.9300 . ? C8 C9 1.391(5) . ? C9 C10 1.345(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.532(4) . ? C11 H11 0.9800 . ? C12 C13 1.532(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C17 1.520(6) . ? C13 C14 1.521(6) . ? C13 H13 0.9800 . ? C14 C15 1.538(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.547(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18B 1.540(17) . ? C17 C18A 1.540(9) . ? C17 H17 0.9800 . ? C18A C19A 1.299(11) . ? C18A H18A 0.9300 . ? C19A H19A 0.9300 . ? C19A H19B 0.9300 . ? C18B C19B 1.332(19) . ? C18B H18B 0.9300 . ? C19B H19C 0.9300 . ? C19B H19D 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.465(4) . ? C22 C27 1.376(5) . ? C22 C23 1.378(4) . ? C23 C24 1.405(4) . ? C24 C25 1.380(5) . ? C24 C28 1.488(4) . ? C25 C26 1.370(5) . ? C25 H25 0.9300 . ? C26 C27 1.369(5) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? 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 N3 Se1 C23 85.93(12) . . ? C8 O1 C20 118.3(3) . . ? C4 N1 C5 116.7(3) . . ? C15 N2 C16 108.7(3) . . ? C15 N2 C11 110.5(3) . . ? C16 N2 C11 106.4(3) . . ? C21 N3 C1 123.7(2) . . ? C21 N3 Se1 116.0(2) . . ? C1 N3 Se1 120.07(18) . . ? N3 C1 C2 109.9(2) . . ? N3 C1 C11 111.7(2) . . ? C2 C1 C11 114.2(3) . . ? N3 C1 H1 106.9 . . ? C2 C1 H1 106.9 . . ? C11 C1 H1 106.9 . . ? C3 C2 C6 116.7(3) . . ? C3 C2 C1 123.3(3) . . ? C6 C2 C1 120.0(3) . . ? C2 C3 C4 121.2(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? N1 C4 C3 123.7(3) . . ? N1 C4 H4 118.1 . . ? C3 C4 H4 118.1 . . ? N1 C5 C6 124.0(3) . . ? N1 C5 C10 117.3(3) . . ? C6 C5 C10 118.8(3) . . ? C5 C6 C7 118.5(3) . . ? C5 C6 C2 117.6(3) . . ? C7 C6 C2 123.8(3) . . ? C8 C7 C6 120.1(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? O1 C8 C7 123.9(3) . . ? O1 C8 C9 115.0(3) . . ? C7 C8 C9 121.1(3) . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C5 120.6(3) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? N2 C11 C1 111.2(2) . . ? N2 C11 C12 110.7(2) . . ? C1 C11 C12 112.3(2) . . ? N2 C11 H11 107.5 . . ? C1 C11 H11 107.5 . . ? C12 C11 H11 107.5 . . ? C13 C12 C11 108.1(3) . . ? C13 C12 H12A 110.1 . . ? C11 C12 H12A 110.1 . . ? C13 C12 H12B 110.1 . . ? C11 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? C17 C13 C14 109.7(4) . . ? C17 C13 C12 110.3(3) . . ? C14 C13 C12 107.6(3) . . ? C17 C13 H13 109.7 . . ? C14 C13 H13 109.7 . . ? C12 C13 H13 109.7 . . ? C13 C14 C15 107.4(3) . . ? C13 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? C13 C14 H14B 110.2 . . ? C15 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? N2 C15 C14 112.3(3) . . ? N2 C15 H15A 109.1 . . ? C14 C15 H15A 109.1 . . ? N2 C15 H15B 109.1 . . ? C14 C15 H15B 109.1 . . ? H15A C15 H15B 107.9 . . ? N2 C16 C17 112.8(3) . . ? N2 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? N2 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C13 C17 C18B 104.9(12) . . ? C13 C17 C18A 115.5(5) . . ? C13 C17 C16 106.5(3) . . ? C18B C17 C16 132.2(9) . . ? C18A C17 C16 108.8(4) . . ? C13 C17 H17 108.6 . . ? C18B C17 H17 94.1 . . ? C18A C17 H17 108.6 . . ? C16 C17 H17 108.6 . . ? C19A C18A C17 130.1(8) . . ? C19A C18A H18A 114.9 . . ? C17 C18A H18A 114.9 . . ? C18A C19A H19A 120.0 . . ? C18A C19A H19B 120.0 . . ? H19A C19A H19B 120.0 . . ? C19B C18B C17 99.1(18) . . ? C19B C18B H18B 130.5 . . ? C17 C18B H18B 130.5 . . ? C18B C19B H19C 120.0 . . ? C18B C19B H19D 120.0 . . ? H19C C19B H19D 120.0 . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C21 N3 123.8(3) . . ? O2 C21 C22 125.6(3) . . ? N3 C21 C22 110.5(3) . . ? C27 C22 C23 119.8(3) . . ? C27 C22 C21 124.3(3) . . ? C23 C22 C21 115.8(3) . . ? C22 C23 C24 122.4(3) . . ? C22 C23 Se1 111.5(2) . . ? C24 C23 Se1 126.1(2) . . ? C25 C24 C23 115.1(3) . . ? C25 C24 C28 123.8(3) . . ? C23 C24 C28 121.0(3) . . ? C26 C25 C24 123.2(3) . . ? C26 C25 H25 118.4 . . ? C24 C25 H25 118.4 . . ? C27 C26 C25 120.2(3) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C22 119.2(3) . . ? C26 C27 H27 120.4 . . ? C22 C27 H27 120.4 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C23 Se1 N3 C21 -3.5(2) . . . . ? C23 Se1 N3 C1 -178.5(2) . . . . ? C21 N3 C1 C2 122.1(3) . . . . ? Se1 N3 C1 C2 -63.4(3) . . . . ? C21 N3 C1 C11 -110.2(3) . . . . ? Se1 N3 C1 C11 64.3(3) . . . . ? N3 C1 C2 C3 104.2(3) . . . . ? C11 C1 C2 C3 -22.1(4) . . . . ? N3 C1 C2 C6 -73.9(3) . . . . ? C11 C1 C2 C6 159.8(3) . . . . ? C6 C2 C3 C4 -0.8(5) . . . . ? C1 C2 C3 C4 -178.9(3) . . . . ? C5 N1 C4 C3 2.8(6) . . . . ? C2 C3 C4 N1 -2.0(6) . . . . ? C4 N1 C5 C6 -0.9(5) . . . . ? C4 N1 C5 C10 179.8(3) . . . . ? N1 C5 C6 C7 177.6(3) . . . . ? C10 C5 C6 C7 -3.0(5) . . . . ? N1 C5 C6 C2 -1.7(5) . . . . ? C10 C5 C6 C2 177.6(3) . . . . ? C3 C2 C6 C5 2.4(4) . . . . ? C1 C2 C6 C5 -179.4(3) . . . . ? C3 C2 C6 C7 -176.9(3) . . . . ? C1 C2 C6 C7 1.4(4) . . . . ? C5 C6 C7 C8 0.3(5) . . . . ? C2 C6 C7 C8 179.5(3) . . . . ? C20 O1 C8 C7 10.4(5) . . . . ? C20 O1 C8 C9 -170.7(3) . . . . ? C6 C7 C8 O1 -177.7(3) . . . . ? C6 C7 C8 C9 3.3(5) . . . . ? O1 C8 C9 C10 176.8(4) . . . . ? C7 C8 C9 C10 -4.1(6) . . . . ? C8 C9 C10 C5 1.2(6) . . . . ? N1 C5 C10 C9 -178.3(4) . . . . ? C6 C5 C10 C9 2.3(6) . . . . ? C15 N2 C11 C1 76.2(3) . . . . ? C16 N2 C11 C1 -165.9(3) . . . . ? C15 N2 C11 C12 -49.4(3) . . . . ? C16 N2 C11 C12 68.5(4) . . . . ? N3 C1 C11 N2 47.7(3) . . . . ? C2 C1 C11 N2 173.1(2) . . . . ? N3 C1 C11 C12 172.4(2) . . . . ? C2 C1 C11 C12 -62.3(3) . . . . ? N2 C11 C12 C13 -14.2(4) . . . . ? C1 C11 C12 C13 -139.1(3) . . . . ? C11 C12 C13 C17 -51.3(4) . . . . ? C11 C12 C13 C14 68.3(4) . . . . ? C17 C13 C14 C15 64.8(4) . . . . ? C12 C13 C14 C15 -55.3(4) . . . . ? C16 N2 C15 C14 -53.5(4) . . . . ? C11 N2 C15 C14 63.0(4) . . . . ? C13 C14 C15 N2 -8.0(5) . . . . ? C15 N2 C16 C17 63.1(4) . . . . ? C11 N2 C16 C17 -55.9(4) . . . . ? C14 C13 C17 C18B 160.9(10) . . . . ? C12 C13 C17 C18B -80.7(10) . . . . ? C14 C13 C17 C18A -176.5(4) . . . . ? C12 C13 C17 C18A -58.1(5) . . . . ? C14 C13 C17 C16 -55.5(4) . . . . ? C12 C13 C17 C16 62.8(4) . . . . ? N2 C16 C17 C13 -7.5(5) . . . . ? N2 C16 C17 C18B 121.6(18) . . . . ? N2 C16 C17 C18A 117.5(5) . . . . ? C13 C17 C18A C19A -80.9(12) . . . . ? C18B C17 C18A C19A -13(3) . . . . ? C16 C17 C18A C19A 159.5(10) . . . . ? C13 C17 C18B C19B 135(2) . . . . ? C18A C17 C18B C19B 15(3) . . . . ? C16 C17 C18B C19B 5(3) . . . . ? C1 N3 C21 O2 -3.1(4) . . . . ? Se1 N3 C21 O2 -177.8(2) . . . . ? C1 N3 C21 C22 179.6(3) . . . . ? Se1 N3 C21 C22 4.9(3) . . . . ? O2 C21 C22 C27 -3.8(5) . . . . ? N3 C21 C22 C27 173.4(3) . . . . ? O2 C21 C22 C23 178.7(3) . . . . ? N3 C21 C22 C23 -4.0(4) . . . . ? C27 C22 C23 C24 1.5(5) . . . . ? C21 C22 C23 C24 179.1(3) . . . . ? C27 C22 C23 Se1 -176.2(3) . . . . ? C21 C22 C23 Se1 1.4(3) . . . . ? N3 Se1 C23 C22 1.1(2) . . . . ? N3 Se1 C23 C24 -176.6(3) . . . . ? C22 C23 C24 C25 -0.7(5) . . . . ? Se1 C23 C24 C25 176.7(3) . . . . ? C22 C23 C24 C28 -179.3(3) . . . . ? Se1 C23 C24 C28 -1.9(5) . . . . ? C23 C24 C25 C26 -0.6(6) . . . . ? C28 C24 C25 C26 177.9(4) . . . . ? C24 C25 C26 C27 1.0(7) . . . . ? C25 C26 C27 C22 -0.2(7) . . . . ? C23 C22 C27 C26 -1.1(6) . . . . ? C21 C22 C27 C26 -178.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.893 _diffrn_reflns_theta_full 24.09 _diffrn_measured_fraction_theta_full 0.893 _refine_diff_density_max 0.240 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.042 _database_code_depnum_ccdc_archive 'CCDC 930741' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Q2 #TrackingRef '2-((1R)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)benzo[d][1,2]selenazol-3(2H)-one .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; C27 H27 N3 O2 Se, C2 H6 O, H2 O ; _chemical_formula_sum 'C29 H35 N3 O4 Se' _chemical_formula_weight 568.56 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5877(15) _cell_length_b 15.441(2) _cell_length_c 10.1760(17) _cell_angle_alpha 90.00 _cell_angle_beta 112.072(9) _cell_angle_gamma 90.00 _cell_volume 1396.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4598 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 23.77 _exptl_crystal_description irregular _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 1.383 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7237 _exptl_absorpt_correction_T_max 0.7889 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11855 _diffrn_reflns_av_R_equivalents 0.0970 _diffrn_reflns_av_sigmaI/netI 0.1415 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 24.98 _reflns_number_total 4768 _reflns_number_gt 3046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR 92' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0005P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration unk _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.028(9) _refine_ls_number_reflns 4768 _refine_ls_number_parameters 363 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.1002 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0716 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.924 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL Q2 in P 21 CELL 0.71073 9.5877 15.4414 10.1760 90.000 112.072 90.000 ZERR 2 0.0015 0.0023 0.0017 0.000 0.009 0.000 LATT -1 SYMM -X, 0.50000+Y,-Z SFAC C H N O SE UNIT 58 70 6 8 2 MERG 2 L.S. 12 SIZE 0.25 0.20 0.18 ACTA HTAB BOND $H CONF SADI C17 C18A C17 C18B EADP C18A C18B SADI C18A C19A C18B C19B EADP C19A C19B SADI C17 C19A C17 C19B DFIX 1.43 O1EA C28A DFIX 1.43 O1EA C28B DFIX 1.52 C28A C29A DFIX 1.52 C28B C29B EADP C28A C28B EADP C29A C29B EXYZ O1EA O1EB EADP O1EA O1EB SADI O1EA H1E O1EB H1E DFIX 0.84 O1W H1W DFIX 0.84 O1W H2W OMIT -1 50 OMIT 0 0 1 OMIT -1 0 1 OMIT -6 11 4 OMIT 1 -3 0 TEMP 21 FMAP 2 PLAN 10 WGHT 0.000500 FVAR 0.21515 0.73148 0.87112 SE1 5 1.031582 -0.037556 0.850895 11.00000 0.05041 0.04576 = 0.04616 0.00062 0.01738 -0.00067 O1 4 0.553679 0.021165 1.196584 11.00000 0.06039 0.09741 = 0.05874 0.00091 0.03067 -0.01143 O2 4 0.629662 0.056498 0.788138 11.00000 0.04058 0.09719 = 0.05567 -0.01331 0.01663 -0.00065 N1 3 1.166592 0.061280 1.400628 11.00000 0.06827 0.06708 = 0.03616 -0.00309 0.01787 -0.01072 N2 3 0.924578 0.178041 0.732531 11.00000 0.07122 0.04916 = 0.03853 0.00750 0.02454 -0.00017 N3 3 0.882176 0.030026 0.875259 11.00000 0.04146 0.03879 = 0.03768 -0.00464 0.01627 -0.01006 C1 1 0.924838 0.113324 0.953562 11.00000 0.04154 0.04980 = 0.02617 -0.00108 0.00985 0.00333 AFIX 13 H1 2 0.831365 0.143066 0.944487 11.00000 -1.20000 AFIX 0 C2 1 1.010434 0.095321 1.110723 11.00000 0.04471 0.04530 = 0.03421 -0.00003 0.02081 0.00229 C3 1 1.162046 0.099665 1.171534 11.00000 0.05025 0.07379 = 0.03663 -0.00386 0.01691 -0.00616 AFIX 43 H3 2 1.217440 0.114546 1.116963 11.00000 -1.20000 AFIX 0 C4 1 1.237587 0.081639 1.318450 11.00000 0.03854 0.07831 = 0.04310 0.00516 -0.00243 -0.00296 AFIX 43 H4 2 1.342114 0.084541 1.357315 11.00000 -1.20000 AFIX 0 C5 1 1.013423 0.055925 1.342799 11.00000 0.05519 0.04278 = 0.03143 0.00438 0.01309 -0.00544 C6 1 0.929756 0.068650 1.197193 11.00000 0.05950 0.03421 = 0.03223 -0.00391 0.02120 -0.00233 C7 1 0.773637 0.057492 1.146117 11.00000 0.05324 0.05056 = 0.03501 -0.00354 0.02026 -0.00013 AFIX 43 H7 2 0.716984 0.064967 1.050053 11.00000 -1.20000 AFIX 0 C8 1 0.703802 0.035724 1.236139 11.00000 0.04788 0.05388 = 0.05065 0.00111 0.02243 -0.00588 C9 1 0.787612 0.025002 1.380996 11.00000 0.07823 0.06585 = 0.03893 0.00396 0.02862 -0.00445 AFIX 43 H9 2 0.738954 0.011353 1.441988 11.00000 -1.20000 AFIX 0 C10 1 0.940023 0.034416 1.433351 11.00000 0.07531 0.05925 = 0.02913 0.00126 0.01581 -0.01195 AFIX 43 H10 2 0.995155 0.026482 1.529619 11.00000 -1.20000 AFIX 0 C11 1 1.007945 0.171220 0.886845 11.00000 0.06565 0.03702 = 0.03501 -0.00141 0.02217 -0.00864 AFIX 13 H11 2 1.105339 0.144162 0.902426 11.00000 -1.20000 AFIX 0 C12 1 1.038809 0.262292 0.955235 11.00000 0.11881 0.05971 = 0.05543 -0.00788 0.04914 -0.01672 AFIX 23 H12A 2 0.969846 0.274302 1.002432 11.00000 -1.20000 H12B 2 1.140896 0.265578 1.024789 11.00000 -1.20000 AFIX 0 C13 1 1.016478 0.327687 0.836718 11.00000 0.13648 0.03201 = 0.07595 0.00292 0.05114 -0.01508 AFIX 13 H13 2 1.051081 0.384935 0.877523 11.00000 -1.20000 AFIX 0 C14 1 0.848714 0.330409 0.750018 11.00000 0.13780 0.06380 = 0.08734 0.01822 0.05769 0.02880 AFIX 23 H14A 2 0.828067 0.367929 0.668412 11.00000 -1.20000 H14B 2 0.795243 0.352639 0.807040 11.00000 -1.20000 AFIX 0 C15 1 0.796825 0.236372 0.700971 11.00000 0.09599 0.07796 = 0.06266 0.02010 0.02991 0.01717 AFIX 23 H15A 2 0.732172 0.215951 0.748362 11.00000 -1.20000 H15B 2 0.738808 0.236135 0.599683 11.00000 -1.20000 AFIX 0 C16 1 1.028659 0.214866 0.671993 11.00000 0.09553 0.05633 = 0.04725 0.00916 0.03560 -0.01316 AFIX 23 H16A 2 0.974449 0.225020 0.571507 11.00000 -1.20000 H16B 2 1.107579 0.173116 0.681919 11.00000 -1.20000 AFIX 0 C17 1 1.101142 0.300572 0.743270 11.00000 0.11376 0.06336 = 0.05253 0.01095 0.03706 -0.02396 AFIX 13 H17 2 1.083367 0.344377 0.669040 11.00000 -1.20000 AFIX 0 PART -1 C18A 1 1.265550 0.293554 0.822715 31.00000 0.12440 0.05825 = 0.07776 -0.00796 0.03273 -0.04147 AFIX 43 H18A 2 1.304769 0.341183 0.880833 31.00000 -1.20000 AFIX 0 C19A 1 1.362827 0.239339 0.829951 31.00000 0.14565 0.10314 = 0.07917 0.00932 0.02947 -0.01486 AFIX 93 H19A 2 1.336442 0.188918 0.776251 31.00000 -1.20000 H19B 2 1.462482 0.248925 0.889101 31.00000 -1.20000 AFIX 0 PART -2 C18B 1 1.258633 0.329971 0.816270 -31.00000 0.12440 0.05825 = 0.07776 -0.00796 0.03273 -0.04147 AFIX 43 H18B 2 1.265922 0.375511 0.878319 -31.00000 -1.20000 AFIX 0 C19B 1 1.382710 0.309172 0.815402 -31.00000 0.14565 0.10314 = 0.07917 0.00932 0.02947 -0.01486 AFIX 93 H19C 2 1.389930 0.264285 0.757350 -31.00000 -1.20000 H19D 2 1.468891 0.338401 0.872801 -31.00000 -1.20000 AFIX 0 PART 0 C20 1 0.466119 0.019223 1.050699 11.00000 0.05384 0.10984 = 0.07652 -0.00482 0.02514 -0.00384 AFIX 137 H20A 2 0.460767 0.076359 1.011908 11.00000 -1.50000 H20B 2 0.366517 -0.000566 1.036296 11.00000 -1.50000 H20C 2 0.511229 -0.019452 1.004183 11.00000 -1.50000 AFIX 0 C21 1 0.739749 0.013836 0.789512 11.00000 0.04575 0.06619 = 0.03382 0.00347 0.02029 -0.01329 C22 1 0.733286 -0.062992 0.701393 11.00000 0.04558 0.06175 = 0.03625 -0.00738 0.01710 -0.02411 C23 1 0.871865 -0.098238 0.720361 11.00000 0.05843 0.04963 = 0.03529 0.01316 0.02125 -0.00801 C24 1 0.880872 -0.172358 0.641991 11.00000 0.08861 0.05214 = 0.05769 -0.00499 0.03724 -0.00710 AFIX 43 H24 2 0.973119 -0.197527 0.654492 11.00000 -1.20000 AFIX 0 C25 1 0.750143 -0.205481 0.547875 11.00000 0.11469 0.07040 = 0.06964 -0.02215 0.04907 -0.03296 AFIX 43 H25 2 0.753903 -0.254557 0.496329 11.00000 -1.20000 AFIX 0 C26 1 0.612719 -0.168933 0.526331 11.00000 0.08828 0.11083 = 0.06890 -0.04351 0.03592 -0.04895 AFIX 43 H26 2 0.525860 -0.192517 0.459247 11.00000 -1.20000 AFIX 0 C27 1 0.602789 -0.097720 0.603310 11.00000 0.06996 0.10532 = 0.05825 -0.02505 0.03334 -0.02949 AFIX 43 H27 2 0.509717 -0.073267 0.589635 11.00000 -1.20000 AFIX 0 PART -1 O1EA 4 1.219512 -0.129265 0.769296 21.00000 0.09834 0.10256 = 0.14143 -0.00662 0.06643 0.00137 C28A 1 1.318023 -0.194596 0.834606 21.00000 0.11141 0.14881 = 0.08658 0.01376 0.00707 0.06964 AFIX 23 H28A 2 1.265563 -0.235516 0.872003 21.00000 -1.20000 H28B 2 1.398925 -0.169788 0.915013 21.00000 -1.20000 AFIX 0 C29A 1 1.383876 -0.241744 0.753250 21.00000 0.17666 0.09925 = 0.13311 -0.00434 0.08076 0.01667 AFIX 137 H29A 2 1.305989 -0.266775 0.672453 21.00000 -1.50000 H29B 2 1.446330 -0.286931 0.810359 21.00000 -1.50000 H29C 2 1.443936 -0.203477 0.721806 21.00000 -1.50000 AFIX 0 PART -2 O1EB 4 1.219512 -0.129265 0.769296 -21.00000 0.09834 0.10256 = 0.14143 -0.00662 0.06643 0.00137 C28B 1 1.275632 -0.203289 0.714659 -21.00000 0.11141 0.14881 = 0.08658 0.01376 0.00707 0.06964 AFIX 23 H28C 2 1.263500 -0.193145 0.616891 -21.00000 -1.20000 H28D 2 1.220050 -0.255120 0.718336 -21.00000 -1.20000 AFIX 0 C29B 1 1.437996 -0.214187 0.804869 -21.00000 0.17666 0.09925 = 0.13311 -0.00434 0.08076 0.01667 AFIX 137 H29D 2 1.487439 -0.244837 0.752565 -21.00000 -1.50000 H29E 2 1.447448 -0.246451 0.888434 -21.00000 -1.50000 H29F 2 1.483706 -0.158295 0.831725 -21.00000 -1.50000 AFIX 0 PART 0 H1E 2 1.286758 -0.103851 0.769012 11.00000 0.05101 MOLE 3 O1W 4 0.673774 0.517147 1.307552 11.00000 0.05635 0.13599 = 0.05621 -0.01529 0.01484 0.00605 H1W 2 0.577992 0.526868 1.284957 11.00000 0.07660 H2W 2 0.714830 0.525498 1.395627 11.00000 0.08716 HKLF 4 REM Q2 in P 21 REM R1 = 0.0441 for 3046 Fo > 4sig(Fo) and 0.1002 for all 4768 data REM 363 parameters refined using 11 restraints END WGHT 0.0000 0.0000 REM Highest difference peak 0.576, deepest hole -0.276, 1-sigma level 0.062 Q1 1 0.9122 -0.0345 0.8101 11.00000 0.05 0.58 Q2 1 1.1446 -0.0399 0.8865 11.00000 0.05 0.50 Q3 1 1.0830 0.0708 1.1268 11.00000 0.05 0.31 Q4 1 0.9113 -0.0366 1.4602 11.00000 0.05 0.26 Q5 1 0.9147 0.3557 0.8738 11.00000 0.05 0.25 Q6 1 0.8136 -0.0352 0.7113 11.00000 0.05 0.25 Q7 1 0.5551 -0.0320 1.2793 11.00000 0.05 0.24 Q8 1 0.7318 0.0869 1.4175 11.00000 0.05 0.23 Q9 1 0.8734 0.0845 1.1846 11.00000 0.05 0.23 Q10 1 0.7605 0.0592 1.3385 11.00000 0.05 0.22 ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 1.03158(5) -0.03756(4) 0.85090(5) 0.04767(14) Uani 1 1 d . . . O1 O 0.5537(4) 0.0212(2) 1.1966(4) 0.0698(11) Uani 1 1 d . . . O2 O 0.6297(4) 0.0565(2) 0.7881(4) 0.0649(10) Uani 1 1 d . . . N1 N 1.1666(5) 0.0613(3) 1.4006(4) 0.0577(11) Uani 1 1 d . . . N2 N 0.9246(5) 0.1780(2) 0.7325(4) 0.0518(11) Uani 1 1 d . . . N3 N 0.8822(4) 0.0300(2) 0.8753(4) 0.0389(9) Uani 1 1 d . . . C1 C 0.9248(5) 0.1133(3) 0.9536(5) 0.0400(11) Uani 1 1 d . . . H1 H 0.8314 0.1431 0.9445 0.048 Uiso 1 1 calc R . . C2 C 1.0104(6) 0.0953(3) 1.1107(6) 0.0397(13) Uani 1 1 d . . . C3 C 1.1620(6) 0.0997(3) 1.1715(6) 0.0534(15) Uani 1 1 d . . . H3 H 1.2174 0.1145 1.1170 0.064 Uiso 1 1 calc R . . C4 C 1.2376(6) 0.0816(3) 1.3185(6) 0.0585(16) Uani 1 1 d . . . H4 H 1.3421 0.0845 1.3573 0.070 Uiso 1 1 calc R . . C5 C 1.0134(6) 0.0559(3) 1.3428(5) 0.0441(12) Uani 1 1 d . . . C6 C 0.9298(6) 0.0687(3) 1.1972(5) 0.0408(12) Uani 1 1 d . . . C7 C 0.7736(5) 0.0575(3) 1.1461(5) 0.0452(12) Uani 1 1 d . . . H7 H 0.7170 0.0650 1.0501 0.054 Uiso 1 1 calc R . . C8 C 0.7038(6) 0.0357(3) 1.2361(6) 0.0497(13) Uani 1 1 d . . . C9 C 0.7876(7) 0.0250(3) 1.3810(6) 0.0591(15) Uani 1 1 d . . . H9 H 0.7390 0.0114 1.4420 0.071 Uiso 1 1 calc R . . C10 C 0.9400(7) 0.0344(3) 1.4334(5) 0.0557(14) Uani 1 1 d . . . H10 H 0.9952 0.0265 1.5296 0.067 Uiso 1 1 calc R . . C11 C 1.0079(5) 0.1712(3) 0.8868(5) 0.0449(13) Uani 1 1 d . . . H11 H 1.1053 0.1442 0.9024 0.054 Uiso 1 1 calc R . . C12 C 1.0388(8) 0.2623(3) 0.9552(6) 0.0732(18) Uani 1 1 d . . . H12A H 0.9698 0.2743 1.0024 0.088 Uiso 1 1 calc R . . H12B H 1.1409 0.2656 1.0248 0.088 Uiso 1 1 calc R . . C13 C 1.0165(10) 0.3277(4) 0.8367(7) 0.078(3) Uani 1 1 d . A . H13 H 1.0511 0.3849 0.8775 0.094 Uiso 1 1 calc R . . C14 C 0.8487(10) 0.3304(4) 0.7500(8) 0.092(3) Uani 1 1 d . . . H14A H 0.8281 0.3679 0.6684 0.110 Uiso 1 1 calc R . . H14B H 0.7952 0.3526 0.8070 0.110 Uiso 1 1 calc R . . C15 C 0.7968(7) 0.2364(4) 0.7010(6) 0.0788(18) Uani 1 1 d . . . H15A H 0.7322 0.2160 0.7484 0.095 Uiso 1 1 calc R . . H15B H 0.7388 0.2361 0.5997 0.095 Uiso 1 1 calc R . . C16 C 1.0287(6) 0.2149(3) 0.6720(5) 0.0638(16) Uani 1 1 d . A . H16A H 0.9744 0.2250 0.5715 0.077 Uiso 1 1 calc R . . H16B H 1.1076 0.1731 0.6819 0.077 Uiso 1 1 calc R . . C17 C 1.1011(8) 0.3006(4) 0.7433(6) 0.0749(19) Uani 1 1 d D . . H17 H 1.0834 0.3444 0.6690 0.090 Uiso 1 1 calc R A . C18A C 1.2656(11) 0.2936(7) 0.8227(10) 0.088(3) Uani 0.871(14) 1 d PD A -1 H18A H 1.3048 0.3412 0.8808 0.106 Uiso 0.871(14) 1 calc PR A -1 C19A C 1.3628(12) 0.2393(8) 0.8300(10) 0.113(4) Uani 0.871(14) 1 d PD A -1 H19A H 1.3364 0.1889 0.7763 0.136 Uiso 0.871(14) 1 calc PR A -1 H19B H 1.4625 0.2489 0.8891 0.136 Uiso 0.871(14) 1 calc PR A -1 C18B C 1.259(3) 0.330(4) 0.816(7) 0.088(3) Uani 0.129(14) 1 d PD A -2 H18B H 1.2659 0.3755 0.8783 0.106 Uiso 0.129(14) 1 calc PR A -2 C19B C 1.383(3) 0.309(5) 0.815(6) 0.113(4) Uani 0.129(14) 1 d PD A -2 H19C H 1.3899 0.2643 0.7574 0.136 Uiso 0.129(14) 1 calc PR A -2 H19D H 1.4689 0.3384 0.8728 0.136 Uiso 0.129(14) 1 calc PR A -2 C20 C 0.4661(6) 0.0192(4) 1.0507(6) 0.0799(18) Uani 1 1 d . . . H20A H 0.4608 0.0764 1.0119 0.120 Uiso 1 1 calc R . . H20B H 0.3665 -0.0006 1.0363 0.120 Uiso 1 1 calc R . . H20C H 0.5112 -0.0195 1.0042 0.120 Uiso 1 1 calc R . . C21 C 0.7397(6) 0.0138(3) 0.7895(5) 0.0470(13) Uani 1 1 d . . . C22 C 0.7333(6) -0.0630(3) 0.7014(5) 0.0474(15) Uani 1 1 d . . . C23 C 0.8719(6) -0.0982(3) 0.7204(5) 0.0467(13) Uani 1 1 d . . . C24 C 0.8809(7) -0.1724(3) 0.6420(6) 0.0633(16) Uani 1 1 d . . . H24 H 0.9731 -0.1975 0.6545 0.076 Uiso 1 1 calc R . . C25 C 0.7501(9) -0.2055(4) 0.5479(7) 0.081(2) Uani 1 1 d . . . H25 H 0.7539 -0.2546 0.4963 0.097 Uiso 1 1 calc R . . C26 C 0.6127(8) -0.1689(4) 0.5263(7) 0.087(2) Uani 1 1 d . . . H26 H 0.5259 -0.1925 0.4592 0.105 Uiso 1 1 calc R . . C27 C 0.6028(7) -0.0977(4) 0.6033(6) 0.0751(18) Uani 1 1 d . . . H27 H 0.5097 -0.0733 0.5896 0.090 Uiso 1 1 calc R . . O1EA O 1.2195(6) -0.1293(4) 0.7693(7) 0.1079(18) Uani 0.731(12) 1 d PD B -1 C28A C 1.3180(13) -0.1946(8) 0.8346(13) 0.124(4) Uani 0.731(12) 1 d PD B -1 H28A H 1.2656 -0.2355 0.8720 0.149 Uiso 0.731(12) 1 calc PR B -1 H28B H 1.3989 -0.1698 0.9150 0.149 Uiso 0.731(12) 1 calc PR B -1 C29A C 1.3839(19) -0.2417(11) 0.7532(19) 0.130(6) Uani 0.731(12) 1 d PD B -1 H29A H 1.3060 -0.2668 0.6725 0.195 Uiso 0.731(12) 1 calc PR B -1 H29B H 1.4463 -0.2869 0.8104 0.195 Uiso 0.731(12) 1 calc PR B -1 H29C H 1.4439 -0.2035 0.7218 0.195 Uiso 0.731(12) 1 calc PR B -1 O1EB O 1.2195(6) -0.1293(4) 0.7693(7) 0.1079(18) Uani 0.269(12) 1 d PD B -2 C28B C 1.276(3) -0.2033(19) 0.715(3) 0.124(4) Uani 0.269(12) 1 d PD B -2 H28C H 1.2635 -0.1931 0.6169 0.149 Uiso 0.269(12) 1 calc PR B -2 H28D H 1.2200 -0.2551 0.7183 0.149 Uiso 0.269(12) 1 calc PR B -2 C29B C 1.438(4) -0.214(4) 0.805(6) 0.130(6) Uani 0.269(12) 1 d PD B -2 H29D H 1.4874 -0.2448 0.7526 0.195 Uiso 0.269(12) 1 calc PR B -2 H29E H 1.4474 -0.2465 0.8884 0.195 Uiso 0.269(12) 1 calc PR B -2 H29F H 1.4837 -0.1583 0.8317 0.195 Uiso 0.269(12) 1 calc PR B -2 H1E H 1.287(6) -0.104(4) 0.769(6) 0.051(19) Uiso 1 1 d D . . O1W O 0.6738(6) 0.5171(3) 1.3076(5) 0.0847(13) Uani 1 1 d D . . H1W H 0.578(3) 0.527(3) 1.285(6) 0.077(19) Uiso 1 1 d D . . H2W H 0.715(6) 0.525(4) 1.396(2) 0.09(2) 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 0.0504(3) 0.0458(2) 0.0462(3) 0.0006(4) 0.0174(2) -0.0007(4) O1 0.060(3) 0.097(3) 0.059(3) 0.001(2) 0.031(2) -0.011(2) O2 0.041(2) 0.097(3) 0.056(3) -0.013(2) 0.017(2) -0.001(2) N1 0.068(3) 0.067(3) 0.036(3) -0.003(2) 0.018(3) -0.011(2) N2 0.071(3) 0.049(2) 0.039(3) 0.008(2) 0.025(3) 0.000(2) N3 0.041(2) 0.039(2) 0.038(2) -0.0046(19) 0.016(2) -0.0101(18) C1 0.042(3) 0.050(3) 0.026(3) -0.001(2) 0.010(3) 0.003(2) C2 0.045(3) 0.045(3) 0.034(3) 0.000(2) 0.021(3) 0.002(2) C3 0.050(4) 0.074(4) 0.037(3) -0.004(3) 0.017(3) -0.006(3) C4 0.039(3) 0.078(4) 0.043(4) 0.005(3) -0.002(3) -0.003(3) C5 0.055(4) 0.043(3) 0.031(3) 0.004(3) 0.013(3) -0.005(2) C6 0.060(4) 0.034(3) 0.032(3) -0.004(2) 0.021(3) -0.002(3) C7 0.053(3) 0.051(3) 0.035(3) -0.004(2) 0.020(3) 0.000(2) C8 0.048(3) 0.054(3) 0.051(4) 0.001(3) 0.022(3) -0.006(3) C9 0.078(4) 0.066(3) 0.039(4) 0.004(3) 0.029(4) -0.004(3) C10 0.075(4) 0.059(3) 0.029(3) 0.001(3) 0.016(3) -0.012(3) C11 0.066(4) 0.037(3) 0.035(3) -0.001(2) 0.022(3) -0.009(2) C12 0.119(6) 0.060(4) 0.055(4) -0.008(3) 0.049(4) -0.017(4) C13 0.136(8) 0.032(3) 0.076(6) 0.003(3) 0.051(6) -0.015(4) C14 0.138(8) 0.064(4) 0.087(6) 0.018(4) 0.058(6) 0.029(5) C15 0.096(5) 0.078(4) 0.063(4) 0.020(3) 0.030(4) 0.017(4) C16 0.096(5) 0.056(3) 0.047(3) 0.009(3) 0.036(4) -0.013(3) C17 0.114(6) 0.063(4) 0.053(4) 0.011(3) 0.037(5) -0.024(4) C18A 0.124(8) 0.058(7) 0.078(6) -0.008(6) 0.033(6) -0.041(6) C19A 0.146(9) 0.103(8) 0.079(6) 0.009(6) 0.029(7) -0.015(7) C18B 0.124(8) 0.058(7) 0.078(6) -0.008(6) 0.033(6) -0.041(6) C19B 0.146(9) 0.103(8) 0.079(6) 0.009(6) 0.029(7) -0.015(7) C20 0.054(4) 0.110(5) 0.077(5) -0.005(4) 0.025(4) -0.004(3) C21 0.046(4) 0.066(3) 0.034(3) 0.003(3) 0.020(3) -0.013(3) C22 0.046(3) 0.062(4) 0.036(3) -0.007(3) 0.017(3) -0.024(2) C23 0.058(3) 0.050(3) 0.035(3) 0.013(3) 0.021(3) -0.008(3) C24 0.089(5) 0.052(3) 0.058(4) -0.005(3) 0.037(4) -0.007(3) C25 0.115(6) 0.070(4) 0.070(5) -0.022(4) 0.049(5) -0.033(4) C26 0.088(5) 0.111(5) 0.069(5) -0.044(4) 0.036(5) -0.049(4) C27 0.070(4) 0.105(5) 0.058(4) -0.025(4) 0.033(4) -0.029(4) O1EA 0.098(4) 0.103(4) 0.141(5) -0.007(3) 0.066(4) 0.001(4) C28A 0.111(10) 0.149(10) 0.087(9) 0.014(9) 0.007(9) 0.070(8) C29A 0.177(16) 0.099(13) 0.133(16) -0.004(9) 0.081(12) 0.017(11) O1EB 0.098(4) 0.103(4) 0.141(5) -0.007(3) 0.066(4) 0.001(4) C28B 0.111(10) 0.149(10) 0.087(9) 0.014(9) 0.007(9) 0.070(8) C29B 0.177(16) 0.099(13) 0.133(16) -0.004(9) 0.081(12) 0.017(11) O1W 0.056(3) 0.136(4) 0.056(3) -0.015(3) 0.015(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C23 1.860(5) . ? Se1 N3 1.863(3) . ? O1 C8 1.360(6) . ? O1 C20 1.405(6) . ? O2 C21 1.240(6) . ? N1 C4 1.300(6) . ? N1 C5 1.364(6) . ? N2 C15 1.456(6) . ? N2 C16 1.470(5) . ? N2 C11 1.474(5) . ? N3 C21 1.339(6) . ? N3 C1 1.487(5) . ? C1 C11 1.517(6) . ? C1 C2 1.524(7) . ? C1 H1 0.9800 . ? C2 C3 1.351(7) . ? C2 C6 1.433(6) . ? C3 C4 1.422(7) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C10 1.394(6) . ? C5 C6 1.409(6) . ? C6 C7 1.398(6) . ? C7 C8 1.364(6) . ? C7 H7 0.9300 . ? C8 C9 1.398(7) . ? C9 C10 1.362(7) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.547(7) . ? C11 H11 0.9800 . ? C12 C13 1.525(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.517(9) . ? C13 C17 1.523(7) . ? C13 H13 0.9800 . ? C14 C15 1.555(9) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.543(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18A 1.481(10) . ? C17 C18B 1.48(2) . ? C17 H17 0.9800 . ? C18A C19A 1.235(10) . ? C18A H18A 0.9300 . ? C19A H19A 0.9300 . ? C19A H19B 0.9300 . ? C18B C19B 1.24(2) . ? C18B H18B 0.9300 . ? C19B H19C 0.9300 . ? C19B H19D 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.474(6) . ? C22 C23 1.381(6) . ? C22 C27 1.382(7) . ? C23 C24 1.416(7) . ? C24 C25 1.359(8) . ? C24 H24 0.9300 . ? C25 C26 1.373(8) . ? C25 H25 0.9300 . ? C26 C27 1.374(8) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? O1EA C28A 1.371(10) . ? O1EA H1E 0.76(5) . ? C28A C29A 1.417(13) . ? C28A H28A 0.9700 . ? C28A H28B 0.9700 . ? C29A H29A 0.9600 . ? C29A H29B 0.9600 . ? C29A H29C 0.9600 . ? C28B C29B 1.49(2) . ? C28B H28C 0.9700 . ? C28B H28D 0.9700 . ? C29B H29D 0.9600 . ? C29B H29E 0.9600 . ? C29B H29F 0.9600 . ? O1W H1W 0.87(2) . ? O1W H2W 0.84(2) . ? 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 C23 Se1 N3 84.80(19) . . ? C8 O1 C20 117.5(4) . . ? C4 N1 C5 118.4(4) . . ? C15 N2 C16 108.4(4) . . ? C15 N2 C11 110.7(4) . . ? C16 N2 C11 107.0(4) . . ? C21 N3 C1 121.2(4) . . ? C21 N3 Se1 117.1(3) . . ? C1 N3 Se1 119.0(3) . . ? N3 C1 C11 110.8(3) . . ? N3 C1 C2 109.6(4) . . ? C11 C1 C2 114.3(4) . . ? N3 C1 H1 107.3 . . ? C11 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C3 C2 C6 118.0(5) . . ? C3 C2 C1 122.3(4) . . ? C6 C2 C1 119.7(5) . . ? C2 C3 C4 120.5(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? N1 C4 C3 122.7(5) . . ? N1 C4 H4 118.6 . . ? C3 C4 H4 118.6 . . ? N1 C5 C10 117.3(5) . . ? N1 C5 C6 122.7(4) . . ? C10 C5 C6 120.0(5) . . ? C7 C6 C5 118.7(4) . . ? C7 C6 C2 123.8(5) . . ? C5 C6 C2 117.4(5) . . ? C8 C7 C6 120.5(5) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? O1 C8 C7 125.0(5) . . ? O1 C8 C9 114.7(5) . . ? C7 C8 C9 120.3(5) . . ? C10 C9 C8 120.4(5) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C5 120.1(5) . . ? C9 C10 H10 120.0 . . ? C5 C10 H10 120.0 . . ? N2 C11 C1 110.7(4) . . ? N2 C11 C12 110.5(4) . . ? C1 C11 C12 112.2(4) . . ? N2 C11 H11 107.8 . . ? C1 C11 H11 107.8 . . ? C12 C11 H11 107.8 . . ? C13 C12 C11 107.4(4) . . ? C13 C12 H12A 110.2 . . ? C11 C12 H12A 110.2 . . ? C13 C12 H12B 110.2 . . ? C11 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C14 C13 C17 110.0(6) . . ? C14 C13 C12 106.3(6) . . ? C17 C13 C12 111.2(5) . . ? C14 C13 H13 109.7 . . ? C17 C13 H13 109.7 . . ? C12 C13 H13 109.7 . . ? C13 C14 C15 107.6(6) . . ? C13 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? C13 C14 H14B 110.2 . . ? C15 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? N2 C15 C14 111.5(6) . . ? N2 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? N2 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? N2 C16 C17 113.0(4) . . ? N2 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? N2 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18A C17 C13 112.8(6) . . ? C18B C17 C13 107(2) . . ? C18A C17 C16 113.1(6) . . ? C18B C17 C16 134(2) . . ? C13 C17 C16 106.1(5) . . ? C18A C17 H17 108.2 . . ? C18B C17 H17 91.4 . . ? C13 C17 H17 108.2 . . ? C16 C17 H17 108.2 . . ? C19A C18A C17 135.0(9) . . ? C19A C18A H18A 112.5 . . ? C17 C18A H18A 112.5 . . ? C18A C19A H19A 120.0 . . ? C18A C19A H19B 120.0 . . ? H19A C19A H19B 120.0 . . ? C19B C18B C17 136(4) . . ? C19B C18B H18B 112.0 . . ? C17 C18B H18B 112.0 . . ? C18B C19B H19C 120.0 . . ? C18B C19B H19D 120.0 . . ? H19C C19B H19D 120.0 . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C21 N3 124.3(5) . . ? O2 C21 C22 125.4(5) . . ? N3 C21 C22 110.2(5) . . ? C23 C22 C27 120.7(5) . . ? C23 C22 C21 114.4(5) . . ? C27 C22 C21 124.8(5) . . ? C22 C23 C24 119.9(5) . . ? C22 C23 Se1 113.1(4) . . ? C24 C23 Se1 127.0(4) . . ? C25 C24 C23 117.8(5) . . ? C25 C24 H24 121.1 . . ? C23 C24 H24 121.1 . . ? C24 C25 C26 122.2(6) . . ? C24 C25 H25 118.9 . . ? C26 C25 H25 118.9 . . ? C25 C26 C27 120.4(6) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C26 C27 C22 119.0(6) . . ? C26 C27 H27 120.5 . . ? C22 C27 H27 120.5 . . ? C28A O1EA H1E 87(5) . . ? O1EA C28A C29A 118.2(12) . . ? O1EA C28A H28A 107.8 . . ? C29A C28A H28A 107.8 . . ? O1EA C28A H28B 107.8 . . ? C29A C28A H28B 107.8 . . ? H28A C28A H28B 107.1 . . ? C29A C28A H1E 106(2) . . ? H28A C28A H1E 136.1 . . ? H28B C28A H1E 88.3 . . ? C29B C28B H28C 110.2 . . ? C29B C28B H28D 110.2 . . ? H28C C28B H28D 108.5 . . ? C28B C29B H29D 109.5 . . ? C28B C29B H29E 109.5 . . ? H29D C29B H29E 109.5 . . ? C28B C29B H29F 109.5 . . ? H29D C29B H29F 109.5 . . ? H29E C29B H29F 109.5 . . ? H1W O1W H2W 106(6) . . ? 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 C23 Se1 N3 C21 -5.4(3) . . . . ? C23 Se1 N3 C1 -167.3(3) . . . . ? C21 N3 C1 C11 -105.4(5) . . . . ? Se1 N3 C1 C11 55.7(4) . . . . ? C21 N3 C1 C2 127.6(4) . . . . ? Se1 N3 C1 C2 -71.4(4) . . . . ? N3 C1 C2 C3 100.2(5) . . . . ? C11 C1 C2 C3 -24.8(7) . . . . ? N3 C1 C2 C6 -76.7(5) . . . . ? C11 C1 C2 C6 158.3(4) . . . . ? C6 C2 C3 C4 -2.6(7) . . . . ? C1 C2 C3 C4 -179.5(5) . . . . ? C5 N1 C4 C3 0.9(8) . . . . ? C2 C3 C4 N1 -0.7(8) . . . . ? C4 N1 C5 C10 -179.7(4) . . . . ? C4 N1 C5 C6 2.2(7) . . . . ? N1 C5 C6 C7 176.7(4) . . . . ? C10 C5 C6 C7 -1.3(7) . . . . ? N1 C5 C6 C2 -5.3(7) . . . . ? C10 C5 C6 C2 176.6(4) . . . . ? C3 C2 C6 C7 -176.9(5) . . . . ? C1 C2 C6 C7 0.1(7) . . . . ? C3 C2 C6 C5 5.3(7) . . . . ? C1 C2 C6 C5 -177.7(4) . . . . ? C5 C6 C7 C8 0.8(7) . . . . ? C2 C6 C7 C8 -177.0(4) . . . . ? C20 O1 C8 C7 7.2(7) . . . . ? C20 O1 C8 C9 -171.5(5) . . . . ? C6 C7 C8 O1 -178.1(5) . . . . ? C6 C7 C8 C9 0.5(7) . . . . ? O1 C8 C9 C10 177.5(5) . . . . ? C7 C8 C9 C10 -1.3(8) . . . . ? C8 C9 C10 C5 0.8(7) . . . . ? N1 C5 C10 C9 -177.6(5) . . . . ? C6 C5 C10 C9 0.5(7) . . . . ? C15 N2 C11 C1 76.7(5) . . . . ? C16 N2 C11 C1 -165.4(4) . . . . ? C15 N2 C11 C12 -48.2(5) . . . . ? C16 N2 C11 C12 69.7(5) . . . . ? N3 C1 C11 N2 49.8(5) . . . . ? C2 C1 C11 N2 174.2(4) . . . . ? N3 C1 C11 C12 173.7(4) . . . . ? C2 C1 C11 C12 -61.9(6) . . . . ? N2 C11 C12 C13 -17.3(7) . . . . ? C1 C11 C12 C13 -141.3(5) . . . . ? C11 C12 C13 C14 70.7(6) . . . . ? C11 C12 C13 C17 -49.1(7) . . . . ? C17 C13 C14 C15 65.0(6) . . . . ? C12 C13 C14 C15 -55.6(7) . . . . ? C16 N2 C15 C14 -53.3(6) . . . . ? C11 N2 C15 C14 63.8(5) . . . . ? C13 C14 C15 N2 -8.9(7) . . . . ? C15 N2 C16 C17 65.8(6) . . . . ? C11 N2 C16 C17 -53.6(5) . . . . ? C14 C13 C17 C18A -177.9(6) . . . . ? C12 C13 C17 C18A -60.4(8) . . . . ? C14 C13 C17 C18B 160(3) . . . . ? C12 C13 C17 C18B -83(3) . . . . ? C14 C13 C17 C16 -53.5(6) . . . . ? C12 C13 C17 C16 64.0(7) . . . . ? N2 C16 C17 C18A 113.7(6) . . . . ? N2 C16 C17 C18B 123(4) . . . . ? N2 C16 C17 C13 -10.5(7) . . . . ? C18B C17 C18A C19A -149(8) . . . . ? C13 C17 C18A C19A 132.9(10) . . . . ? C16 C17 C18A C19A 12.4(13) . . . . ? C18A C17 C18B C19B 47(6) . . . . ? C13 C17 C18B C19B 157(9) . . . . ? C16 C17 C18B C19B 23(13) . . . . ? C1 N3 C21 O2 -14.4(7) . . . . ? Se1 N3 C21 O2 -175.9(4) . . . . ? C1 N3 C21 C22 167.3(4) . . . . ? Se1 N3 C21 C22 5.9(4) . . . . ? O2 C21 C22 C23 178.8(5) . . . . ? N3 C21 C22 C23 -3.0(5) . . . . ? O2 C21 C22 C27 0.7(8) . . . . ? N3 C21 C22 C27 179.0(5) . . . . ? C27 C22 C23 C24 -2.0(7) . . . . ? C21 C22 C23 C24 179.9(4) . . . . ? C27 C22 C23 Se1 177.1(4) . . . . ? C21 C22 C23 Se1 -1.1(5) . . . . ? N3 Se1 C23 C22 3.4(3) . . . . ? N3 Se1 C23 C24 -177.7(4) . . . . ? C22 C23 C24 C25 1.0(7) . . . . ? Se1 C23 C24 C25 -177.8(4) . . . . ? C23 C24 C25 C26 0.8(8) . . . . ? C24 C25 C26 C27 -1.7(10) . . . . ? C25 C26 C27 C22 0.7(9) . . . . ? C23 C22 C27 C26 1.1(8) . . . . ? C21 C22 C27 C26 179.0(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.576 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 930742' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N O Se' _chemical_formula_sum 'C15 H13 N O Se' _chemical_formula_weight 302.22 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4368(2) _cell_length_b 10.9926(2) _cell_length_c 11.5312(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.8070(10) _cell_angle_gamma 90.00 _cell_volume 1290.03(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6269 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 30.44 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.897 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6236 _exptl_absorpt_correction_T_max 0.8687 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14580 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 30.65 _reflns_number_total 3981 _reflns_number_gt 3157 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0433P)^2^+0.1516P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3981 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL JS09 in P2(1)/c CELL 0.71073 10.4368 10.9926 11.5312 90.000 102.807 90.000 ZERR 4.00 0.0002 0.0002 0.0002 0.000 0.001 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N O SE UNIT 60 52 4 4 4 TEMP 25 SIZE 0.18 0.15 0.05 ACTA HTAB L.S. 12 FMAP 2 PLAN 5 BOND $H WGHT 0.043300 0.151600 FVAR 0.18467 SE1 5 0.460934 0.469783 0.767852 11.00000 0.03354 0.03600 = 0.04033 0.00268 0.00654 -0.00015 O1 4 0.698505 0.734039 0.721900 11.00000 0.03157 0.04618 = 0.07052 0.00349 0.00490 -0.00716 N1 3 0.603102 0.575895 0.799421 11.00000 0.02813 0.03853 = 0.04301 0.00077 0.00138 0.00023 C7 1 0.609020 0.659323 0.713893 11.00000 0.02779 0.03545 = 0.04666 -0.00216 0.00771 0.00386 C2 1 0.495081 0.648507 0.613471 11.00000 0.03039 0.03419 = 0.03842 -0.00042 0.00865 0.00401 C1 1 0.406629 0.556413 0.623550 11.00000 0.02969 0.03351 = 0.03460 -0.00184 0.00520 0.00375 C6 1 0.294808 0.534086 0.533956 11.00000 0.03565 0.04156 = 0.03984 -0.00646 0.00347 0.00156 C15 1 0.201182 0.432499 0.543840 11.00000 0.04455 0.05470 = 0.06511 -0.00283 -0.00325 -0.01220 AFIX 137 H15A 2 0.155019 0.408358 0.465721 11.00000 -1.50000 H15B 2 0.139293 0.459907 0.588562 11.00000 -1.50000 H15C 2 0.249501 0.364422 0.583544 11.00000 -1.50000 AFIX 0 C5 1 0.276383 0.608509 0.434890 11.00000 0.04662 0.05456 = 0.03604 -0.00543 -0.00096 0.00593 AFIX 43 H5 2 0.202842 0.596480 0.373656 11.00000 -1.20000 AFIX 0 C4 1 0.364502 0.701102 0.423732 11.00000 0.05756 0.05324 = 0.03477 0.00525 0.00946 0.00872 AFIX 43 H4 2 0.348752 0.749573 0.355948 11.00000 -1.20000 AFIX 0 C3 1 0.474288 0.720908 0.512378 11.00000 0.04372 0.04216 = 0.04415 0.00463 0.01458 0.00122 AFIX 43 H3 2 0.533731 0.781824 0.504811 11.00000 -1.20000 AFIX 0 C8 1 0.711067 0.558882 0.904538 11.00000 0.03531 0.04806 = 0.03780 -0.00650 0.00139 0.00728 AFIX 23 H8A 2 0.677441 0.517961 0.966155 11.00000 -1.20000 H8B 2 0.743702 0.637935 0.934905 11.00000 -1.20000 AFIX 0 C9 1 0.823358 0.485446 0.877432 11.00000 0.02980 0.04461 = 0.03097 -0.00230 0.00048 0.00435 C14 1 0.930338 0.542988 0.849060 11.00000 0.03446 0.05432 = 0.04316 0.00305 0.00185 -0.00072 AFIX 43 H14 2 0.933035 0.627449 0.845602 11.00000 -1.20000 AFIX 0 C13 1 1.033081 0.474965 0.825885 11.00000 0.03190 0.09130 = 0.04838 0.00253 0.00742 0.00285 AFIX 43 H13 2 1.104765 0.514133 0.806986 11.00000 -1.20000 AFIX 0 C12 1 1.030634 0.350314 0.830416 11.00000 0.04460 0.08734 = 0.05238 -0.00762 0.00574 0.02792 AFIX 43 H12 2 1.100040 0.305129 0.814394 11.00000 -1.20000 AFIX 0 C11 1 0.925297 0.293018 0.858687 11.00000 0.06062 0.05071 = 0.06109 -0.00432 0.00160 0.02089 AFIX 43 H11 2 0.923403 0.208522 0.861991 11.00000 -1.20000 AFIX 0 C10 1 0.821926 0.359303 0.882328 11.00000 0.04255 0.04558 = 0.04666 0.00370 0.00732 0.00465 AFIX 43 H10 2 0.750920 0.319344 0.901641 11.00000 -1.20000 HKLF 4 REM JS09 in P2(1)/c REM R1 = 0.0271 for 3157 Fo > 4sig(Fo) and 0.0395 for all 3981 data REM 164 parameters refined using 0 restraints END WGHT 0.0433 0.1516 REM Highest difference peak 0.280, deepest hole -0.520, 1-sigma level 0.077 Q1 1 0.4750 0.6819 0.5704 11.00000 0.05 0.28 Q2 1 0.2267 0.3324 0.4922 11.00000 0.05 0.27 Q3 1 0.2048 0.3920 0.6392 11.00000 0.05 0.26 Q4 1 0.4484 0.6204 0.6274 11.00000 0.05 0.26 Q5 1 0.0980 0.4595 0.4969 11.00000 0.05 0.24 ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.460934(15) 0.469783(14) 0.767852(14) 0.03688(7) Uani 1 1 d . . . O1 O 0.69851(11) 0.73404(12) 0.72190(12) 0.0504(3) Uani 1 1 d . . . N1 N 0.60310(12) 0.57590(13) 0.79942(12) 0.0376(3) Uani 1 1 d . . . C7 C 0.60902(14) 0.65932(14) 0.71389(15) 0.0367(3) Uani 1 1 d . . . C2 C 0.49508(14) 0.64851(14) 0.61347(14) 0.0342(3) Uani 1 1 d . . . C1 C 0.40663(15) 0.55641(14) 0.62355(14) 0.0329(3) Uani 1 1 d . . . C6 C 0.29481(17) 0.53409(15) 0.53396(16) 0.0398(4) Uani 1 1 d . . . C15 C 0.2012(2) 0.4325(2) 0.5438(2) 0.0572(5) Uani 1 1 d . . . H15A H 0.1550 0.4084 0.4657 0.086 Uiso 1 1 calc R . . H15B H 0.1393 0.4599 0.5886 0.086 Uiso 1 1 calc R . . H15C H 0.2495 0.3644 0.5835 0.086 Uiso 1 1 calc R . . C5 C 0.27638(18) 0.60851(18) 0.43489(15) 0.0473(4) Uani 1 1 d . . . H5 H 0.2028 0.5965 0.3737 0.057 Uiso 1 1 calc R . . C4 C 0.36450(18) 0.70110(18) 0.42373(15) 0.0486(4) Uani 1 1 d . . . H4 H 0.3488 0.7496 0.3559 0.058 Uiso 1 1 calc R . . C3 C 0.47429(16) 0.72091(16) 0.51238(15) 0.0426(4) Uani 1 1 d . . . H3 H 0.5337 0.7818 0.5048 0.051 Uiso 1 1 calc R . . C8 C 0.71107(17) 0.55888(17) 0.90454(15) 0.0414(4) Uani 1 1 d . . . H8A H 0.6774 0.5180 0.9662 0.050 Uiso 1 1 calc R . . H8B H 0.7437 0.6379 0.9349 0.050 Uiso 1 1 calc R . . C9 C 0.82336(15) 0.48545(16) 0.87743(14) 0.0361(3) Uani 1 1 d . . . C14 C 0.93034(17) 0.54299(18) 0.84906(16) 0.0450(4) Uani 1 1 d . . . H14 H 0.9330 0.6274 0.8456 0.054 Uiso 1 1 calc R . . C13 C 1.03308(19) 0.4750(2) 0.82589(19) 0.0574(5) Uani 1 1 d . . . H13 H 1.1048 0.5141 0.8070 0.069 Uiso 1 1 calc R . . C12 C 1.0306(2) 0.3503(2) 0.83042(19) 0.0622(6) Uani 1 1 d . . . H12 H 1.1000 0.3051 0.8144 0.075 Uiso 1 1 calc R . . C11 C 0.9253(2) 0.2930(2) 0.85869(19) 0.0593(5) Uani 1 1 d . . . H11 H 0.9234 0.2085 0.8620 0.071 Uiso 1 1 calc R . . C10 C 0.82193(17) 0.35930(17) 0.88233(16) 0.0453(4) Uani 1 1 d . . . H10 H 0.7509 0.3193 0.9016 0.054 Uiso 1 1 calc R . . 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 0.03354(9) 0.03600(10) 0.04033(10) 0.00268(6) 0.00654(7) -0.00015(6) O1 0.0316(6) 0.0462(7) 0.0705(9) 0.0035(6) 0.0049(6) -0.0072(5) N1 0.0281(6) 0.0385(7) 0.0430(7) 0.0008(6) 0.0014(5) 0.0002(5) C7 0.0278(7) 0.0355(8) 0.0467(9) -0.0022(7) 0.0077(6) 0.0039(6) C2 0.0304(7) 0.0342(7) 0.0384(8) -0.0004(6) 0.0087(6) 0.0040(6) C1 0.0297(7) 0.0335(7) 0.0346(7) -0.0018(6) 0.0052(6) 0.0038(6) C6 0.0356(8) 0.0416(9) 0.0398(8) -0.0065(7) 0.0035(7) 0.0016(6) C15 0.0445(10) 0.0547(11) 0.0651(13) -0.0028(10) -0.0032(9) -0.0122(9) C5 0.0466(9) 0.0546(11) 0.0360(8) -0.0054(8) -0.0010(7) 0.0059(8) C4 0.0576(11) 0.0532(10) 0.0348(8) 0.0052(7) 0.0095(8) 0.0087(9) C3 0.0437(8) 0.0422(8) 0.0442(9) 0.0046(7) 0.0146(7) 0.0012(7) C8 0.0353(8) 0.0481(9) 0.0378(8) -0.0065(7) 0.0014(7) 0.0073(7) C9 0.0298(7) 0.0446(8) 0.0310(7) -0.0023(6) 0.0005(6) 0.0044(6) C14 0.0345(8) 0.0543(11) 0.0432(9) 0.0031(8) 0.0019(7) -0.0007(7) C13 0.0319(9) 0.0913(17) 0.0484(11) 0.0025(10) 0.0074(8) 0.0029(9) C12 0.0446(10) 0.0873(17) 0.0524(11) -0.0076(11) 0.0057(9) 0.0279(11) C11 0.0606(12) 0.0507(11) 0.0611(12) -0.0043(9) 0.0016(10) 0.0209(10) C10 0.0426(9) 0.0456(9) 0.0467(9) 0.0037(8) 0.0073(7) 0.0046(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 1.8588(14) . ? Se1 C1 1.8918(16) . ? O1 C7 1.2317(19) . ? N1 C7 1.358(2) . ? N1 C8 1.473(2) . ? C7 C2 1.469(2) . ? C2 C3 1.388(2) . ? C2 C1 1.392(2) . ? C1 C6 1.398(2) . ? C6 C5 1.383(3) . ? C6 C15 1.505(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C5 C4 1.397(3) . ? C5 H5 0.9300 . ? C4 C3 1.373(2) . ? C4 H4 0.9300 . ? C3 H3 0.9300 . ? C8 C9 1.512(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C14 1.384(2) . ? C9 C10 1.388(2) . ? C14 C13 1.381(3) . ? C14 H14 0.9300 . ? C13 C12 1.372(3) . ? C13 H13 0.9300 . ? C12 C11 1.368(3) . ? C12 H12 0.9300 . ? C11 C10 1.378(3) . ? C11 H11 0.9300 . ? C10 H10 0.9300 . ? 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 N1 Se1 C1 85.81(6) . . ? C7 N1 C8 122.26(14) . . ? C7 N1 Se1 116.38(11) . . ? C8 N1 Se1 120.89(12) . . ? O1 C7 N1 123.48(15) . . ? O1 C7 C2 125.51(15) . . ? N1 C7 C2 111.01(13) . . ? C3 C2 C1 120.26(15) . . ? C3 C2 C7 124.33(15) . . ? C1 C2 C7 115.40(14) . . ? C2 C1 C6 121.75(15) . . ? C2 C1 Se1 111.38(11) . . ? C6 C1 Se1 126.86(13) . . ? C5 C6 C1 116.54(16) . . ? C5 C6 C15 121.85(16) . . ? C1 C6 C15 121.60(16) . . ? C6 C15 H15A 109.5 . . ? C6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C5 C4 122.22(16) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C3 C4 C5 120.31(17) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C3 C2 118.91(16) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? N1 C8 C9 112.61(14) . . ? N1 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N1 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.8 . . ? C14 C9 C10 118.86(16) . . ? C14 C9 C8 120.52(16) . . ? C10 C9 C8 120.61(16) . . ? C13 C14 C9 119.99(18) . . ? C13 C14 H14 120.0 . . ? C9 C14 H14 120.0 . . ? C12 C13 C14 120.8(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C11 C12 C13 119.46(18) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C10 C9 120.27(18) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.65 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.280 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.077 _database_code_depnum_ccdc_archive 'CCDC 953729'