#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:41:06 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270498 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158322.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_7158322 loop_ _publ_author_name 'Shen, Jinhui' 'Yu, Aimin' 'Meng, Xiangtai' _publ_section_title ; Stereoselective [4 + 3] annulation of azadienes and ethyl 4-bromo-3-oxobutanoate: construction of benzindeno-fused azepine derivatives. ; _journal_issue 41 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 9026 _journal_page_last 9030 _journal_paper_doi 10.1039/d1ob01749g _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C29 H27 N O5 S' _chemical_formula_sum 'C29 H27 N O5 S' _chemical_formula_weight 501.57 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-11-05 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-09-07 deposited with the CCDC. 2021-09-29 downloaded from the CCDC. ; _cell_angle_alpha 97.036(14) _cell_angle_beta 110.448(14) _cell_angle_gamma 105.848(14) _cell_formula_units_Z 2 _cell_length_a 10.9106(16) _cell_length_b 11.628(2) _cell_length_c 11.7739(19) _cell_measurement_reflns_used 1483 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 32.8570 _cell_measurement_theta_min 3.1980 _cell_volume 1306.5(4) _computing_cell_refinement 'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 296.15 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 2.00 41.00 1.00 55.00 -- 30.00 54.00-120.00 39 2 \w 83.00 108.00 1.00 55.00 -- 30.00 54.00 120.00 25 3 \w -74.00 12.00 1.00 55.00 -- 30.00 54.00 120.00 86 4 \w -74.00 108.00 1.00 55.00 -- 30.00 54.00 -30.00 182 ; _diffrn_measurement_device 'two-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Mini (ROW)' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0186961000 _diffrn_orient_matrix_UB_12 0.0105189000 _diffrn_orient_matrix_UB_13 -0.0608669000 _diffrn_orient_matrix_UB_21 -0.0646737000 _diffrn_orient_matrix_UB_22 0.0017050000 _diffrn_orient_matrix_UB_23 -0.0004998000 _diffrn_orient_matrix_UB_31 0.0301582000 _diffrn_orient_matrix_UB_32 0.0644718000 _diffrn_orient_matrix_UB_33 0.0261786000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_unetI/netI 0.0947 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 6911 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 2.724 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.79249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.275 _exptl_crystal_description block _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.612 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 345 _refine_ls_number_reflns 4571 _refine_ls_number_restraints 436 _refine_ls_restrained_S_all 1.133 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0691 _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^)+(0.1011P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1701 _refine_ls_wR_factor_ref 0.2161 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2596 _reflns_number_total 4571 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01749g2.cif _cod_data_source_block 8 _cod_depositor_comments 'Adding full bibliography for 7158322--7158326.cif.' _cod_database_code 7158322 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.994 _shelx_estimated_absorpt_t_min 0.987 _reflns_odcompleteness_completeness 99.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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 H1A-C1 0.96 with sigma of 0.002 C1-H1B 0.96 with sigma of 0.002 H00A-H00C = H1B-H1A 1.566 with sigma of 0.002 3. Uiso/Uaniso restraints and constraints C007 \\sim C008 \\sim C009 \\sim C00A \\sim C00B \\sim C00C \\sim C00D \\sim C00E \\sim C00G \\sim C00H \\sim C00I \\sim C00J \\sim C00K \\sim C00L \\sim C00M \\sim C00N \\sim C00O \\sim C00P \\sim C00Q \\sim C00R \\sim C00S \\sim C00T \\sim C00U \\sim C00V \\sim C00W \\sim C00X \\sim C00Y \\sim C1 \\sim C0AA \\sim C2: within 2.7A with sigma of 0.004 and sigma for terminal atoms of 0.008 4. Others Fixed Sof: C0AA(0.5) H0AA(0.5) H0AB(0.5) H0AC(0.5) C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) 5.a Ternary CH refined with riding coordinates: C007(H007), C00B(H00B) 5.b Secondary CH2 refined with riding coordinates: C00H(H00A,H00C), C00M(H00D,H00F) 5.c Aromatic/amide H refined with riding coordinates: C00E(H00E), C00G(H00G), C00K(H00K), C00L(H00L), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X) 5.d Idealised Me refined as rotating group: C00Y(H00H,H00I,H00J), C0AA(H0AA,H0AB,H0AC), C2(H2A,H2B,H2C) ; _shelx_res_file ; TITL 8_a.res in P-1 8.res created by SHELXL-2018/3 at 08:54:35 on 05-Nov-2019 REM Old TITL 8 in P-1 #2 REM SHELXT solution in P-1 REM R1 0.329, Rweak 0.048, Alpha 0.058, Orientation as input REM Formula found by SHELXT: C29 N O4 S CELL 0.71073 10.9106 11.6282 11.7739 97.036 110.448 105.848 ZERR 2 0.0016 0.0021 0.0019 0.014 0.014 0.014 LATT 1 SFAC C H N O S UNIT 58 54 2 10 2 DFIX 0.96 0.002 H1a C1 DFIX 0.96 0.002 C1 H1b DFIX 1.566 0.002 H00a H00c H1b H1a SIMU 0.004 0.008 2.7 $C L.S. 20 0 0 PLAN 20 SIZE 0.08 0.06 0.04 TEMP 23 FREE C2 H1b BOND $H list 4 fmap 2 53 acta OMIT -3 50 OMIT 1 0 1 OMIT 1 1 0 OMIT -1 -1 1 OMIT -7 -5 3 OMIT 0 1 1 OMIT 3 -6 11 OMIT -8 -4 4 OMIT -2 -4 3 OMIT -2 1 2 REM REM REM WGHT 0.101100 FVAR 0.78800 S001 5 0.721034 0.521032 0.458895 11.00000 0.04126 0.04655 = 0.04388 0.00273 0.01899 0.01826 O002 4 0.845048 0.589903 0.447671 11.00000 0.03894 0.05458 = 0.05550 0.00769 0.02150 0.01220 O003 4 0.639412 0.584554 0.493938 11.00000 0.05211 0.05613 = 0.06185 0.00125 0.02809 0.02756 N004 3 0.622381 0.424996 0.322472 11.00000 0.04171 0.04483 = 0.04110 0.00269 0.01992 0.01058 O005 4 0.544866 -0.043064 0.204326 11.00000 0.08925 0.04023 = 0.09337 0.00514 0.03195 0.01523 O006 4 0.368242 0.122960 0.225263 11.00000 0.05026 0.05658 = 0.13202 -0.00215 0.03292 0.00625 C007 1 0.647884 0.199338 0.164714 11.00000 0.05027 0.04860 = 0.04960 0.00752 0.02084 0.02435 AFIX 13 H007 2 0.569093 0.143948 0.089805 11.00000 -1.20000 AFIX 0 C008 1 0.666699 0.328586 0.149388 11.00000 0.05143 0.04825 = 0.04505 0.01112 0.02272 0.02530 C009 1 0.761567 0.430726 0.565519 11.00000 0.04541 0.06998 = 0.04934 0.01475 0.02845 0.02844 C00A 1 0.659447 0.426591 0.217709 11.00000 0.05110 0.04847 = 0.04542 0.01057 0.02304 0.02666 C00B 1 0.613050 0.177319 0.277897 11.00000 0.04780 0.04597 = 0.05107 0.01010 0.02035 0.02092 AFIX 13 H00B 2 0.689515 0.233333 0.353948 11.00000 -1.20000 AFIX 0 C00C 1 0.776545 0.168478 0.169271 11.00000 0.05132 0.05114 = 0.05125 0.00363 0.01985 0.02623 C00D 1 0.681048 0.533796 0.162676 11.00000 0.05762 0.04974 = 0.04840 0.01449 0.02096 0.02702 C00E 1 0.879296 0.396648 0.586137 11.00000 0.04946 0.07450 = 0.05495 0.01915 0.02663 0.02517 AFIX 43 H00E 2 0.935321 0.421901 0.543470 11.00000 -1.20000 AFIX 0 O00F 4 0.646565 0.044874 0.408196 11.00000 0.14560 0.06257 = 0.08133 0.03465 0.03054 0.03605 C00G 1 0.912392 0.325365 0.670014 11.00000 0.05304 0.07735 = 0.06103 0.02141 0.02337 0.02981 AFIX 43 H00G 2 0.991566 0.303848 0.683917 11.00000 -1.20000 AFIX 0 C00H 1 0.490380 0.335224 0.303974 11.00000 0.04382 0.04906 = 0.05137 0.00661 0.02217 0.02067 AFIX 23 H00A 2 0.415959 0.350565 0.240197 11.00000 -1.20000 H00C 2 0.476418 0.346853 0.380964 11.00000 -1.20000 AFIX 0 C00I 1 0.480622 0.202724 0.265604 11.00000 0.04698 0.04885 = 0.05501 0.00829 0.02165 0.01792 C00J 1 0.706770 0.499234 0.057774 11.00000 0.06175 0.05318 = 0.04859 0.01526 0.02137 0.02418 C00K 1 0.768348 0.077637 0.076858 11.00000 0.05578 0.05519 = 0.05350 0.00019 0.02212 0.02277 AFIX 43 H00K 2 0.682655 0.032709 0.012223 11.00000 -1.20000 AFIX 0 C00L 1 0.885929 0.052598 0.079171 11.00000 0.05856 0.05921 = 0.05985 -0.00196 0.02661 0.02503 AFIX 43 H00L 2 0.878756 -0.007878 0.015335 11.00000 -1.20000 AFIX 0 C00M 1 0.696593 0.366670 0.040432 11.00000 0.06016 0.05407 = 0.04778 0.01020 0.02359 0.02323 AFIX 23 H00D 2 0.783116 0.357567 0.042677 11.00000 -1.20000 H00F 2 0.621948 0.317476 -0.038518 11.00000 -1.20000 AFIX 0 C00N 1 0.595137 0.045550 0.288791 11.00000 0.05444 0.05307 = 0.06470 0.01408 0.02281 0.01946 C00O 1 0.830630 0.285581 0.733370 11.00000 0.05711 0.07942 = 0.05673 0.02386 0.02296 0.02434 C00P 1 0.680391 0.392975 0.630002 11.00000 0.05082 0.08022 = 0.05308 0.01785 0.02707 0.02637 AFIX 43 H00P 2 0.602753 0.416460 0.618226 11.00000 -1.20000 AFIX 0 C00Q 1 0.676702 0.649595 0.196324 11.00000 0.06688 0.05211 = 0.05606 0.01393 0.01928 0.02614 AFIX 43 H00Q 2 0.657523 0.671549 0.265264 11.00000 -1.20000 AFIX 0 C00R 1 0.734573 0.584180 -0.010186 11.00000 0.07357 0.05853 = 0.05180 0.01907 0.02034 0.01943 AFIX 43 H00R 2 0.755420 0.563037 -0.078294 11.00000 -1.20000 AFIX 0 C00S 1 1.011259 0.115253 0.173418 11.00000 0.05638 0.06756 = 0.06447 -0.00248 0.02185 0.03053 AFIX 43 H00S 2 1.089730 0.097099 0.175259 11.00000 -1.20000 AFIX 0 C00T 1 0.701514 0.733181 0.125353 11.00000 0.07678 0.05362 = 0.06065 0.01706 0.01607 0.02399 AFIX 43 H00T 2 0.698256 0.811762 0.146069 11.00000 -1.20000 AFIX 0 C00U 1 0.731176 0.699117 0.023455 11.00000 0.07920 0.05816 = 0.05808 0.02184 0.01574 0.01725 AFIX 43 H00U 2 0.749107 0.756021 -0.022810 11.00000 -1.20000 AFIX 0 C00V 1 0.713696 0.320875 0.711503 11.00000 0.05646 0.08589 = 0.05625 0.02181 0.02778 0.02145 AFIX 43 H00V 2 0.656920 0.294802 0.753305 11.00000 -1.20000 AFIX 0 C00W 1 0.903863 0.232134 0.263625 11.00000 0.05735 0.06692 = 0.06393 -0.00968 0.01524 0.02780 AFIX 43 H00W 2 0.911944 0.293797 0.326850 11.00000 -1.20000 AFIX 0 C00X 1 1.021662 0.205475 0.265943 11.00000 0.05860 0.07526 = 0.07005 -0.00916 0.01291 0.02689 AFIX 43 H00X 2 1.107658 0.249245 0.330692 11.00000 -1.20000 AFIX 0 C00Y 1 0.864328 0.204342 0.822376 11.00000 0.08171 0.09846 = 0.07471 0.03723 0.02326 0.02735 AFIX 137 H00H 2 0.912323 0.155567 0.796342 11.00000 -1.50000 H00I 2 0.779692 0.151044 0.822091 11.00000 -1.50000 H00J 2 0.922354 0.254864 0.905173 11.00000 -1.50000 AFIX 0 C1 1 0.649576 -0.076105 0.434185 11.00000 0.14933 0.07523 = 0.09467 0.02842 0.00801 0.01354 PART 1 C0AA 1 0.806123 -0.061154 0.470256 10.50000 0.15663 0.08630 = 0.10812 0.03409 0.00554 0.02516 AFIX 137 H0AA 2 0.829419 -0.050071 0.399953 10.50000 -1.50000 H0AB 2 0.822104 -0.133588 0.493971 10.50000 -1.50000 H0AC 2 0.863042 0.009385 0.539009 10.50000 -1.50000 AFIX 0 PART 0 PART 2 C2 1 0.723738 -0.074046 0.528846 10.50000 0.16325 0.09211 = 0.10828 0.03613 0.00111 0.01969 AFIX 137 H2A 2 0.805889 -0.084635 0.523348 10.50000 -1.50000 H2B 2 0.680460 -0.139415 0.559523 10.50000 -1.50000 H2C 2 0.748538 0.003679 0.584940 10.50000 -1.50000 AFIX 0 PART 0 H1A 2 0.563733 -0.122112 0.364121 11.00000 0.06850 H1B 2 0.631632 -0.064149 0.508250 11.00000 0.15618 HKLF 4 REM 8_a.res in P-1 REM wR2 = 0.2161, GooF = S = 1.023, Restrained GooF = 1.133 for all data REM R1 = 0.0691 for 2596 Fo > 4sig(Fo) and 0.1293 for all 4571 data REM 345 parameters refined using 436 restraints END WGHT 0.1011 0.0000 REM Highest difference peak 0.612, deepest hole -0.520, 1-sigma level 0.060 Q1 1 0.9352 -0.0576 0.3669 11.00000 0.05 0.61 Q2 1 1.0467 0.2606 0.2350 11.00000 0.05 0.29 Q3 1 0.9471 0.0555 0.1365 11.00000 0.05 0.29 Q4 1 0.9970 0.1376 0.2835 11.00000 0.05 0.28 Q5 1 0.8874 0.1822 0.2969 11.00000 0.05 0.26 Q6 1 0.9253 0.2850 0.2158 11.00000 0.05 0.24 Q7 1 0.6270 0.5014 0.3384 11.00000 0.05 0.23 Q8 1 0.7227 0.2585 0.6941 11.00000 0.05 0.22 Q9 1 0.5264 -0.1174 0.4048 11.00000 0.05 0.21 Q10 1 0.8201 0.0471 0.0425 11.00000 0.05 0.21 Q11 1 0.6401 -0.1431 0.3537 11.00000 0.05 0.21 Q12 1 0.6747 0.5521 0.4828 11.00000 0.05 0.19 Q13 1 0.8556 0.3969 0.1369 11.00000 0.05 0.19 Q14 1 0.4927 -0.0927 0.4362 11.00000 0.05 0.19 Q15 1 0.9031 0.3986 0.4766 11.00000 0.05 0.18 Q16 1 0.7054 0.5226 0.2828 11.00000 0.05 0.18 Q17 1 0.7990 0.3175 0.7397 11.00000 0.05 0.18 Q18 1 0.9356 0.3505 0.2566 11.00000 0.05 0.17 Q19 1 0.7325 0.4470 0.0440 11.00000 0.05 0.17 Q20 1 0.8144 -0.0073 0.5856 11.00000 0.05 0.17 ; _shelx_res_checksum 34426 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.259 _oxdiff_exptl_absorpt_empirical_full_min 0.842 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S001 S 0.72103(10) 0.52103(10) 0.45890(9) 0.0434(3) Uani 1 1 d . . . . . O002 O 0.8450(3) 0.5899(3) 0.4477(3) 0.0503(7) Uani 1 1 d . . . . . O003 O 0.6394(3) 0.5846(3) 0.4939(3) 0.0544(8) Uani 1 1 d . . . . . N004 N 0.6224(3) 0.4250(3) 0.3225(3) 0.0432(8) Uani 1 1 d . . . . . O005 O 0.5449(4) -0.0431(3) 0.2043(3) 0.0782(11) Uani 1 1 d . . . . . O006 O 0.3682(3) 0.1230(3) 0.2253(4) 0.0857(12) Uani 1 1 d . . . . . C007 C 0.6479(4) 0.1993(4) 0.1647(4) 0.0480(8) Uani 1 1 d . U . . . H007 H 0.569093 0.143948 0.089805 0.058 Uiso 1 1 calc R . . . . C008 C 0.6667(4) 0.3286(4) 0.1494(4) 0.0454(8) Uani 1 1 d . U . . . C009 C 0.7616(4) 0.4307(4) 0.5655(4) 0.0502(9) Uani 1 1 d . U . . . C00A C 0.6594(4) 0.4266(4) 0.2177(4) 0.0452(8) Uani 1 1 d . U . . . C00B C 0.6130(4) 0.1773(4) 0.2779(4) 0.0472(8) Uani 1 1 d . U . . . H00B H 0.689515 0.233333 0.353948 0.057 Uiso 1 1 calc R . . . . C00C C 0.7765(4) 0.1685(4) 0.1693(4) 0.0503(8) Uani 1 1 d . U . . . C00D C 0.6810(4) 0.5338(4) 0.1627(4) 0.0498(8) Uani 1 1 d . U . . . C00E C 0.8793(4) 0.3966(4) 0.5861(4) 0.0567(9) Uani 1 1 d . U . . . H00E H 0.935321 0.421901 0.543470 0.068 Uiso 1 1 calc R . . . . O00F O 0.6466(5) 0.0449(3) 0.4082(4) 0.0990(14) Uani 1 1 d . . . . . C00G C 0.9124(5) 0.3254(5) 0.6700(4) 0.0615(10) Uani 1 1 d . U . . . H00G H 0.991566 0.303848 0.683917 0.074 Uiso 1 1 calc R . . . . C00H C 0.4904(4) 0.3352(4) 0.3040(4) 0.0466(9) Uani 1 1 d . U . . . H00A H 0.415959 0.350565 0.240197 0.056 Uiso 1 1 calc DR . . . . H00C H 0.476418 0.346853 0.380964 0.056 Uiso 1 1 calc DR . . . . C00I C 0.4806(5) 0.2027(4) 0.2656(4) 0.0500(9) Uani 1 1 d . U . . . C00J C 0.7068(5) 0.4992(4) 0.0578(4) 0.0534(8) Uani 1 1 d . U . . . C00K C 0.7683(5) 0.0776(4) 0.0769(4) 0.0551(9) Uani 1 1 d . U . . . H00K H 0.682655 0.032709 0.012223 0.066 Uiso 1 1 calc R . . . . C00L C 0.8859(5) 0.0526(4) 0.0792(4) 0.0588(10) Uani 1 1 d . U . . . H00L H 0.878756 -0.007878 0.015335 0.071 Uiso 1 1 calc R . . . . C00M C 0.6966(5) 0.3667(4) 0.0404(4) 0.0528(8) Uani 1 1 d . U . . . H00D H 0.783116 0.357567 0.042677 0.063 Uiso 1 1 calc R . . . . H00F H 0.621948 0.317476 -0.038518 0.063 Uiso 1 1 calc R . . . . C00N C 0.5951(5) 0.0456(5) 0.2888(5) 0.0575(10) Uani 1 1 d . U . . . C00O C 0.8306(5) 0.2856(5) 0.7334(4) 0.0634(10) Uani 1 1 d . U . . . C00P C 0.6804(5) 0.3930(5) 0.6300(4) 0.0585(10) Uani 1 1 d . U . . . H00P H 0.602753 0.416460 0.618226 0.070 Uiso 1 1 calc R . . . . C00Q C 0.6767(5) 0.6496(4) 0.1963(4) 0.0585(9) Uani 1 1 d . U . . . H00Q H 0.657523 0.671549 0.265264 0.070 Uiso 1 1 calc R . . . . C00R C 0.7346(5) 0.5842(4) -0.0102(4) 0.0628(10) Uani 1 1 d . U . . . H00R H 0.755420 0.563037 -0.078294 0.075 Uiso 1 1 calc R . . . . C00S C 1.0113(5) 0.1153(5) 0.1734(4) 0.0632(10) Uani 1 1 d . U . . . H00S H 1.089730 0.097099 0.175259 0.076 Uiso 1 1 calc R . . . . C00T C 0.7015(5) 0.7332(5) 0.1254(4) 0.0663(11) Uani 1 1 d . U . . . H00T H 0.698256 0.811762 0.146069 0.080 Uiso 1 1 calc R . . . . C00U C 0.7312(5) 0.6991(5) 0.0235(5) 0.0692(11) Uani 1 1 d . U . . . H00U H 0.749107 0.756021 -0.022810 0.083 Uiso 1 1 calc R . . . . C00V C 0.7137(5) 0.3209(5) 0.7115(4) 0.0649(10) Uani 1 1 d . U . . . H00V H 0.656920 0.294802 0.753305 0.078 Uiso 1 1 calc R . . . . C00W C 0.9039(5) 0.2321(5) 0.2636(4) 0.0663(10) Uani 1 1 d . U . . . H00W H 0.911944 0.293797 0.326850 0.080 Uiso 1 1 calc R . . . . C00X C 1.0217(5) 0.2055(5) 0.2659(5) 0.0734(11) Uani 1 1 d . U . . . H00X H 1.107658 0.249245 0.330692 0.088 Uiso 1 1 calc R . . . . C00Y C 0.8643(6) 0.2043(6) 0.8224(5) 0.0865(15) Uani 1 1 d . U . . . H00H H 0.912323 0.155567 0.796342 0.130 Uiso 1 1 calc GR . . . . H00I H 0.779692 0.151044 0.822091 0.130 Uiso 1 1 calc GR . . . . H00J H 0.922354 0.254864 0.905173 0.130 Uiso 1 1 calc GR . . . . C1 C 0.6496(9) -0.0761(7) 0.4342(8) 0.123(2) Uani 1 1 d D U . . . C0AA C 0.8061(19) -0.0612(15) 0.4703(16) 0.133(4) Uani 0.5 1 d . U P A 1 H0AA H 0.829419 -0.050071 0.399953 0.200 Uiso 0.5 1 calc GR . P A 1 H0AB H 0.822104 -0.133588 0.493971 0.200 Uiso 0.5 1 calc GR . P A 1 H0AC H 0.863042 0.009385 0.539009 0.200 Uiso 0.5 1 calc GR . P A 1 C2 C 0.724(2) -0.0740(15) 0.5288(16) 0.141(4) Uani 0.5 1 d . U P A 2 H2A H 0.805889 -0.084635 0.523348 0.211 Uiso 0.5 1 calc GR . P A 2 H2B H 0.680460 -0.139415 0.559523 0.211 Uiso 0.5 1 calc GR . P A 2 H2C H 0.748538 0.003679 0.584940 0.211 Uiso 0.5 1 calc GR . P A 2 H1A H 0.564(2) -0.122(3) 0.364(2) 0.068(14) Uiso 1 1 d D . . . . H1B H 0.632(4) -0.064(7) 0.508(2) 0.16(4) 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 S001 0.0413(6) 0.0465(6) 0.0439(6) 0.0027(5) 0.0190(5) 0.0183(5) O002 0.0389(16) 0.0546(18) 0.0555(18) 0.0077(14) 0.0215(14) 0.0122(15) O003 0.0521(18) 0.0561(18) 0.0618(19) 0.0013(15) 0.0281(15) 0.0276(16) N004 0.0417(19) 0.045(2) 0.0411(19) 0.0027(15) 0.0199(16) 0.0106(17) O005 0.089(3) 0.0402(18) 0.093(3) 0.0051(18) 0.032(2) 0.0152(19) O006 0.050(2) 0.057(2) 0.132(3) -0.002(2) 0.033(2) 0.0062(19) C007 0.0503(13) 0.0486(13) 0.0496(13) 0.0075(11) 0.0208(11) 0.0244(12) C008 0.0514(14) 0.0482(14) 0.0451(14) 0.0111(12) 0.0227(12) 0.0253(13) C009 0.0454(16) 0.070(2) 0.0493(17) 0.0148(15) 0.0285(14) 0.0284(15) C00A 0.0511(14) 0.0485(14) 0.0454(14) 0.0106(12) 0.0230(12) 0.0267(13) C00B 0.0478(15) 0.0460(15) 0.0511(15) 0.0101(13) 0.0203(13) 0.0209(13) C00C 0.0513(14) 0.0511(15) 0.0513(15) 0.0036(12) 0.0199(12) 0.0262(13) C00D 0.0576(15) 0.0497(14) 0.0484(14) 0.0145(12) 0.0210(13) 0.0270(13) C00E 0.0495(17) 0.074(2) 0.0550(18) 0.0192(16) 0.0266(15) 0.0252(16) O00F 0.146(4) 0.063(2) 0.081(3) 0.035(2) 0.031(3) 0.036(3) C00G 0.0530(17) 0.077(2) 0.0610(18) 0.0214(16) 0.0234(15) 0.0298(16) C00H 0.0438(17) 0.0491(18) 0.0514(18) 0.0066(15) 0.0222(15) 0.0207(15) C00I 0.0470(17) 0.0488(17) 0.0550(17) 0.0083(15) 0.0217(14) 0.0179(15) C00J 0.0617(15) 0.0532(15) 0.0486(14) 0.0153(13) 0.0214(13) 0.0242(13) C00K 0.0558(16) 0.0552(17) 0.0535(16) 0.0002(14) 0.0221(14) 0.0228(15) C00L 0.0586(17) 0.0592(18) 0.0598(18) -0.0020(15) 0.0266(15) 0.0250(16) C00M 0.0602(15) 0.0541(15) 0.0478(15) 0.0102(13) 0.0236(13) 0.0232(14) C00N 0.0544(18) 0.0531(18) 0.0647(19) 0.0141(16) 0.0228(16) 0.0195(16) C00O 0.0571(18) 0.079(2) 0.0567(18) 0.0239(16) 0.0230(15) 0.0243(17) C00P 0.0508(17) 0.080(2) 0.0531(18) 0.0179(16) 0.0271(15) 0.0264(16) C00Q 0.0669(17) 0.0521(16) 0.0561(17) 0.0139(14) 0.0193(15) 0.0261(15) C00R 0.0736(18) 0.0585(17) 0.0518(16) 0.0191(14) 0.0203(15) 0.0194(16) C00S 0.0564(17) 0.0676(19) 0.0645(19) -0.0025(16) 0.0219(15) 0.0305(16) C00T 0.0768(19) 0.0536(18) 0.0607(18) 0.0171(16) 0.0161(17) 0.0240(17) C00U 0.079(2) 0.0582(18) 0.0581(18) 0.0218(16) 0.0157(17) 0.0172(17) C00V 0.0565(18) 0.086(2) 0.0562(18) 0.0218(16) 0.0278(15) 0.0215(17) C00W 0.0574(16) 0.0669(18) 0.0639(18) -0.0097(15) 0.0152(15) 0.0278(15) C00X 0.0586(18) 0.075(2) 0.0701(19) -0.0092(17) 0.0129(16) 0.0269(17) C00Y 0.082(3) 0.098(3) 0.075(3) 0.037(2) 0.023(2) 0.027(3) C1 0.149(4) 0.075(3) 0.095(3) 0.028(3) 0.008(3) 0.014(3) C0AA 0.157(7) 0.086(5) 0.108(6) 0.034(5) 0.006(6) 0.025(6) C2 0.163(7) 0.092(6) 0.108(7) 0.036(6) 0.001(6) 0.020(6) 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O002 S001 O003 119.55(18) . . ? O002 S001 N004 105.88(17) . . ? O002 S001 C009 109.36(18) . . ? O003 S001 N004 108.04(17) . . ? O003 S001 C009 106.93(19) . . ? N004 S001 C009 106.4(2) . . ? C00A N004 S001 122.4(3) . . ? C00A N004 C00H 117.5(3) . . ? C00H N004 S001 120.1(3) . . ? C008 C007 H007 107.4 . . ? C008 C007 C00B 113.0(3) . . ? C008 C007 C00C 109.1(4) . . ? C00B C007 H007 107.4 . . ? C00C C007 H007 107.4 . . ? C00C C007 C00B 112.4(3) . . ? C007 C008 C00M 120.7(3) . . ? C00A C008 C007 131.2(4) . . ? C00A C008 C00M 108.1(4) . . ? C00E C009 S001 119.3(3) . . ? C00P C009 S001 121.5(3) . . ? C00P C009 C00E 119.2(4) . . ? N004 C00A C00D 123.5(3) . . ? C008 C00A N004 125.1(4) . . ? C008 C00A C00D 111.1(4) . . ? C007 C00B H00B 108.9 . . ? C00I C00B C007 110.4(3) . . ? C00I C00B H00B 108.9 . . ? C00I C00B C00N 109.2(4) . . ? C00N C00B C007 110.7(3) . . ? C00N C00B H00B 108.9 . . ? C00K C00C C007 121.0(4) . . ? C00W C00C C007 120.8(4) . . ? C00W C00C C00K 118.2(4) . . ? C00J C00D C00A 107.5(4) . . ? C00Q C00D C00A 131.5(4) . . ? C00Q C00D C00J 121.0(4) . . ? C009 C00E H00E 120.1 . . ? C00G C00E C009 119.9(4) . . ? C00G C00E H00E 120.1 . . ? C00N O00F C1 115.5(5) . . ? C00E C00G H00G 119.3 . . ? C00O C00G C00E 121.3(4) . . ? C00O C00G H00G 119.3 . . ? N004 C00H H00A 108.8 . . ? N004 C00H H00C 108.8 . . ? N004 C00H C00I 113.8(3) . . ? H00A C00H H00C 107.7 . . ? C00I C00H H00A 108.8 . . ? C00I C00H H00C 108.8 . . ? O006 C00I C00B 123.1(4) . . ? O006 C00I C00H 118.8(4) . . ? C00B C00I C00H 118.1(4) . . ? C00D C00J C00M 108.8(4) . . ? C00R C00J C00D 119.6(4) . . ? C00R C00J C00M 131.5(4) . . ? C00C C00K H00K 119.6 . . ? C00C C00K C00L 120.9(4) . . ? C00L C00K H00K 119.6 . . ? C00K C00L H00L 119.7 . . ? C00S C00L C00K 120.6(4) . . ? C00S C00L H00L 119.7 . . ? C008 C00M H00D 110.9 . . ? C008 C00M H00F 110.9 . . ? C00J C00M C008 104.4(3) . . ? C00J C00M H00D 110.9 . . ? C00J C00M H00F 110.9 . . ? H00D C00M H00F 108.9 . . ? O005 C00N C00B 126.0(5) . . ? O005 C00N O00F 125.0(5) . . ? O00F C00N C00B 109.0(4) . . ? C00G C00O C00V 117.8(4) . . ? C00G C00O C00Y 121.4(4) . . ? C00V C00O C00Y 120.8(5) . . ? C009 C00P H00P 119.9 . . ? C00V C00P C009 120.1(4) . . ? C00V C00P H00P 119.9 . . ? C00D C00Q H00Q 120.6 . . ? C00D C00Q C00T 118.7(5) . . ? C00T C00Q H00Q 120.6 . . ? C00J C00R H00R 120.3 . . ? C00U C00R C00J 119.4(5) . . ? C00U C00R H00R 120.3 . . ? C00L C00S H00S 120.3 . . ? C00L C00S C00X 119.5(4) . . ? C00X C00S H00S 120.3 . . ? C00Q C00T H00T 120.1 . . ? C00U C00T C00Q 119.8(5) . . ? C00U C00T H00T 120.1 . . ? C00R C00U C00T 121.4(5) . . ? C00R C00U H00U 119.3 . . ? C00T C00U H00U 119.3 . . ? C00O C00V H00V 119.2 . . ? C00P C00V C00O 121.6(5) . . ? C00P C00V H00V 119.2 . . ? C00C C00W H00W 119.7 . . ? C00C C00W C00X 120.6(4) . . ? C00X C00W H00W 119.7 . . ? C00S C00X C00W 120.3(5) . . ? C00S C00X H00X 119.9 . . ? C00W C00X H00X 119.9 . . ? C00O C00Y H00H 109.5 . . ? C00O C00Y H00I 109.5 . . ? C00O C00Y H00J 109.5 . . ? H00H C00Y H00I 109.5 . . ? H00H C00Y H00J 109.5 . . ? H00I C00Y H00J 109.5 . . ? O00F C1 C0AA 101.8(8) . . ? O00F C1 H1A 94(3) . . ? O00F C1 H1B 96(6) . . ? C0AA C1 H1A 136(3) . . ? C0AA C1 H1B 110(3) . . ? C2 C1 O00F 116.4(11) . . ? C2 C1 H1A 146(3) . . ? C2 C1 H1B 56(3) . . ? H1A C1 H1B 109.2(3) . . ? C1 C0AA H0AA 109.5 . . ? C1 C0AA H0AB 109.5 . . ? C1 C0AA H0AC 109.5 . . ? H0AA C0AA H0AB 109.5 . . ? H0AA C0AA H0AC 109.5 . . ? H0AB C0AA H0AC 109.5 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? C1 C2 H1B 53.8(12) . . ? H2A C2 H2B 109.5 . . ? H2A C2 H2C 109.5 . . ? H2A C2 H1B 163.2 . . ? H2B C2 H2C 109.5 . . ? H2B C2 H1B 80.0 . . ? H2C C2 H1B 78.9 . . ? 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 S001 O002 1.431(3) . ? S001 O003 1.432(3) . ? S001 N004 1.638(3) . ? S001 C009 1.750(5) . ? N004 C00A 1.427(5) . ? N004 C00H 1.454(5) . ? O005 C00N 1.188(5) . ? O006 C00I 1.206(5) . ? C007 H007 0.9800 . ? C007 C008 1.502(6) . ? C007 C00B 1.540(6) . ? C007 C00C 1.526(5) . ? C008 C00A 1.350(5) . ? C008 C00M 1.517(6) . ? C009 C00E 1.396(5) . ? C009 C00P 1.376(6) . ? C00A C00D 1.474(6) . ? C00B H00B 0.9800 . ? C00B C00I 1.514(5) . ? C00B C00N 1.518(6) . ? C00C C00K 1.381(5) . ? C00C C00W 1.368(6) . ? C00D C00J 1.396(6) . ? C00D C00Q 1.375(6) . ? C00E H00E 0.9300 . ? C00E C00G 1.381(6) . ? O00F C00N 1.321(6) . ? O00F C1 1.482(8) . ? C00G H00G 0.9300 . ? C00G C00O 1.375(7) . ? C00H H00A 0.9700 . ? C00H H00C 0.9700 . ? C00H C00I 1.515(6) . ? C00J C00M 1.498(6) . ? C00J C00R 1.381(6) . ? C00K H00K 0.9300 . ? C00K C00L 1.383(6) . ? C00L H00L 0.9300 . ? C00L C00S 1.353(6) . ? C00M H00D 0.9700 . ? C00M H00F 0.9700 . ? C00O C00V 1.395(6) . ? C00O C00Y 1.513(7) . ? C00P H00P 0.9300 . ? C00P C00V 1.370(6) . ? C00Q H00Q 0.9300 . ? C00Q C00T 1.389(6) . ? C00R H00R 0.9300 . ? C00R C00U 1.361(6) . ? C00S H00S 0.9300 . ? C00S C00X 1.367(6) . ? C00T H00T 0.9300 . ? C00T C00U 1.388(7) . ? C00U H00U 0.9300 . ? C00V H00V 0.9300 . ? C00W H00W 0.9300 . ? C00W C00X 1.394(6) . ? C00X H00X 0.9300 . ? C00Y H00H 0.9600 . ? C00Y H00I 0.9600 . ? C00Y H00J 0.9600 . ? C1 C0AA 1.562(19) . ? C1 C2 1.118(16) . ? C1 H1A 0.960(2) . ? C1 H1B 0.961(2) . ? C0AA H0AA 0.9600 . ? C0AA H0AB 0.9600 . ? C0AA H0AC 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C2 H1B 0.99(5) . ?