#------------------------------------------------------------------------------ #$Date: 2019-04-30 01:07:39 +0300 (Tue, 30 Apr 2019) $ #$Revision: 214831 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/33/7123347.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_7123347 loop_ _publ_author_name 'Ge, Jiemin' 'Wu, Xueli' 'Bao, Xiaoguang' _publ_section_title ; Rhodium(II)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: A combined experimental and computational study ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC02294E _journal_year 2019 _chemical_formula_moiety 'C37 H36 N4 O3 S' _chemical_formula_sum 'C37 H36 N4 O3 S' _chemical_formula_weight 616.76 _chemical_name_systematic 5-(4-methoxyphenyl)-1,7,9-triphenyl-3-tosyloctahydro-1H-purine _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2019-03-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-03-15 deposited with the CCDC. 2019-04-29 downloaded from the CCDC. ; _cell_angle_alpha 74.55(2) _cell_angle_beta 87.703(15) _cell_angle_gamma 79.93(2) _cell_formula_units_Z 2 _cell_length_a 9.503(6) _cell_length_b 10.244(7) _cell_length_c 17.165(11) _cell_measurement_reflns_used 8527 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.13 _cell_measurement_theta_min 2.45 _cell_volume 1585.8(18) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 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 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_unetI/netI 0.0638 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 26413 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.612 _diffrn_reflns_theta_min 2.508 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_correction_T_min 0.6650 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1703 before and 0.0678 after correction. The Ratio of minimum to maximum transmission is 0.8920. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.292 _exptl_crystal_description block _exptl_crystal_F_000 652 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Ethyl acetate' _refine_diff_density_max 0.377 _refine_diff_density_min -0.392 _refine_diff_density_rms 0.077 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 408 _refine_ls_number_reflns 7341 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0583 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.4221P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1447 _refine_ls_wR_factor_ref 0.1646 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4840 _reflns_number_total 7341 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc02294e2.cif _cod_data_source_block cc_a _cod_database_code 7123347 _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. ; _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. Rigid bond restraints C00U, C00D with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 3.a Ternary CH refined with riding coordinates: C00G(H00G) 3.b Secondary CH2 refined with riding coordinates: C00J(H00A,H00B), C00L(H00C,H00D), C00R(H00H,H00J) 3.c Aromatic/amide H refined with riding coordinates: C00E(H00E), C00F(H00F), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C017(H017), C019(H019) 3.d Idealised Me refined as rotating group: C016(H01A,H01B,H01C), C018(H01D,H01E,H01F) ; _shelx_res_file ; TITL CC_a.res in P-1 cc_a.res created by SHELXL-2018/3 at 22:38:20 on 14-Mar-2019 REM Old TITL CC in P-1 REM SHELXT solution in P-1 REM R1 0.175, Rweak 0.019, Alpha 0.054, Orientation as input REM Formula found by SHELXT: C37 N5 O2 S CELL 0.71073 9.5035 10.2437 17.1647 74.554 87.703 79.931 ZERR 2 0.0062 0.0071 0.0108 0.021 0.015 0.021 LATT 1 SFAC C H N O S UNIT 74 72 8 6 2 DELU 0.001 0.001 C00U C00D L.S. 10 PLAN 20 TEMP 23 BOND $H LIST 6 fmap 2 acta OMIT 0 1 1 OMIT 1 0 0 OMIT -1 0 2 OMIT 1 2 2 REM REM REM WGHT 0.080500 0.422100 FVAR 0.82523 S001 5 0.637733 0.648682 0.858082 11.00000 0.03982 0.03610 = 0.03900 -0.01241 -0.00610 0.00060 O002 4 0.694101 0.771301 0.823251 11.00000 0.05540 0.03493 = 0.06930 -0.00972 -0.01377 -0.00655 O003 4 0.523418 0.651725 0.914384 11.00000 0.05059 0.06370 = 0.04186 -0.02401 0.00184 0.00315 N004 3 0.581515 0.593052 0.785839 11.00000 0.03341 0.04053 = 0.03288 -0.01119 -0.00286 0.00095 N006 3 0.311840 0.644656 0.646374 11.00000 0.04419 0.03167 = 0.03972 -0.00769 -0.01198 0.00133 N007 3 0.603964 0.688093 0.644502 11.00000 0.03819 0.04657 = 0.03627 -0.00655 0.00139 0.00729 N008 3 0.401497 0.474290 0.753863 11.00000 0.05749 0.02872 = 0.04690 -0.00645 -0.01769 -0.00213 C009 1 0.244351 0.809995 0.729440 11.00000 0.03606 0.03135 = 0.03796 -0.00317 0.00138 0.00215 C00A 1 0.682267 0.713925 0.573005 11.00000 0.04178 0.04036 = 0.04001 -0.01353 0.00358 -0.00736 C00B 1 0.282707 0.708177 0.564293 11.00000 0.03361 0.04325 = 0.04111 -0.00741 -0.00626 -0.00097 C00C 1 0.364659 0.715852 0.700385 11.00000 0.03366 0.02903 = 0.03519 -0.00762 -0.00353 0.00081 C00D 1 0.019853 0.979816 0.779156 11.00000 0.04670 0.04868 = 0.04230 -0.00594 0.00470 0.01092 C00E 1 0.270289 0.906089 0.766314 11.00000 0.04392 0.04990 = 0.05394 -0.02124 0.00173 -0.00036 AFIX 43 H00E 2 0.364136 0.913819 0.774903 11.00000 -1.20000 AFIX 0 C00F 1 0.917994 0.528239 0.874729 11.00000 0.04335 0.04669 = 0.05058 -0.00698 -0.00710 -0.00560 AFIX 43 H00F 2 0.935401 0.601919 0.832510 11.00000 -1.20000 AFIX 0 C00G 1 0.427675 0.594500 0.773805 11.00000 0.03443 0.02853 = 0.03749 -0.00699 -0.00300 -0.00002 AFIX 13 H00G 2 0.375217 0.603801 0.822905 11.00000 -1.20000 AFIX 0 C00H 1 0.457002 0.341967 0.800156 11.00000 0.03928 0.03065 = 0.05204 -0.00369 -0.00830 -0.00514 C00I 1 0.102241 0.798427 0.720274 11.00000 0.03811 0.04246 = 0.06055 -0.01155 0.00164 -0.00291 AFIX 43 H00I 2 0.082110 0.731941 0.696594 11.00000 -1.20000 AFIX 0 C00J 1 0.673459 0.594021 0.716254 11.00000 0.03764 0.04655 = 0.03785 -0.01206 -0.00315 0.00636 AFIX 23 H00A 2 0.762506 0.621702 0.725554 11.00000 -1.20000 H00B 2 0.695459 0.502198 0.708575 11.00000 -1.20000 AFIX 0 C00K 1 0.782073 0.521309 0.903515 11.00000 0.04092 0.03875 = 0.03782 -0.01033 -0.00939 -0.00237 C00L 1 0.486969 0.789406 0.661212 11.00000 0.03770 0.03170 = 0.03904 -0.00621 -0.00008 0.00137 AFIX 23 H00C 2 0.453987 0.857047 0.611334 11.00000 -1.20000 H00D 2 0.519580 0.836627 0.697291 11.00000 -1.20000 AFIX 0 C00M 1 0.302161 0.632040 0.507361 11.00000 0.04723 0.05163 = 0.04752 -0.01648 -0.00694 -0.00054 AFIX 43 H00M 2 0.334793 0.537805 0.523813 11.00000 -1.20000 AFIX 0 C00N 1 0.477470 0.316497 0.882823 11.00000 0.05303 0.03834 = 0.04815 -0.00552 -0.00072 -0.00284 AFIX 43 H00N 2 0.454686 0.387817 0.907629 11.00000 -1.20000 AFIX 0 C00O 1 0.202928 0.909380 0.456353 11.00000 0.06067 0.05485 = 0.05098 0.00123 -0.01128 0.00538 AFIX 43 H00O 2 0.168220 1.003171 0.439181 11.00000 -1.20000 AFIX 0 C00P 1 -0.007702 0.882010 0.745119 11.00000 0.04154 0.05206 = 0.06777 -0.01429 0.00492 -0.00198 AFIX 43 H00P 2 -0.101568 0.871894 0.738705 11.00000 -1.20000 AFIX 0 C00Q 1 0.229696 0.848710 0.537092 11.00000 0.04942 0.04526 = 0.04370 -0.00700 -0.00955 0.00305 AFIX 43 H00Q 2 0.212386 0.901627 0.573973 11.00000 -1.20000 AFIX 0 C00R 1 0.372575 0.500177 0.668813 11.00000 0.05124 0.03368 = 0.04810 -0.01044 -0.01480 -0.00005 AFIX 23 H00H 2 0.305274 0.444800 0.659404 11.00000 -1.20000 H00J 2 0.459608 0.481874 0.639177 11.00000 -1.20000 AFIX 0 C00S 1 0.619737 0.794423 0.500351 11.00000 0.05009 0.05986 = 0.04178 -0.00548 0.00385 -0.00761 AFIX 43 H00S 2 0.523472 0.833034 0.499399 11.00000 -1.20000 AFIX 0 C00T 1 0.755882 0.414645 0.968229 11.00000 0.05090 0.05397 = 0.03889 -0.00547 -0.00566 -0.00730 AFIX 43 H00T 2 0.663903 0.410989 0.988328 11.00000 -1.20000 AFIX 0 C00U 1 0.157904 0.993268 0.791436 11.00000 0.06302 0.05111 = 0.05743 -0.02586 -0.00244 -0.00280 AFIX 43 H00U 2 0.176417 1.059206 0.816036 11.00000 -1.20000 AFIX 0 C00V 1 1.028983 0.424516 0.909126 11.00000 0.04154 0.05634 = 0.06202 -0.01621 -0.01206 -0.00052 AFIX 43 H00V 2 1.120943 0.428147 0.888991 11.00000 -1.20000 AFIX 0 C00W 1 1.005529 0.315719 0.972830 11.00000 0.05576 0.04809 = 0.05219 -0.01470 -0.02181 0.00401 C00X 1 0.545615 0.103658 0.810753 11.00000 0.06325 0.03345 = 0.08239 -0.01149 -0.00537 -0.00336 AFIX 43 H00X 2 0.568729 0.031700 0.786476 11.00000 -1.20000 AFIX 0 C00Y 1 0.491525 0.233899 0.764270 11.00000 0.05814 0.03747 = 0.05908 -0.01234 -0.00769 -0.00460 AFIX 43 H00Y 2 0.478195 0.249315 0.708966 11.00000 -1.20000 AFIX 0 C00Z 1 0.825873 0.655776 0.571340 11.00000 0.04536 0.07094 = 0.05254 -0.01649 0.00769 -0.00240 AFIX 43 H00Z 2 0.870969 0.599367 0.618500 11.00000 -1.20000 AFIX 0 C010 1 0.226752 0.833271 0.400303 11.00000 0.07060 0.08076 = 0.04031 -0.00696 -0.01187 0.00084 AFIX 43 H010 2 0.211271 0.875281 0.345504 11.00000 -1.20000 AFIX 0 C011 1 0.869199 0.313641 1.002396 11.00000 0.07294 0.04950 = 0.04645 -0.00074 -0.01767 -0.00580 AFIX 43 H011 2 0.852722 0.242518 1.046493 11.00000 -1.20000 AFIX 0 C012 1 0.273428 0.695302 0.426950 11.00000 0.06350 0.07801 = 0.04443 -0.02265 -0.00722 -0.00189 AFIX 43 H012 2 0.286168 0.642626 0.389868 11.00000 -1.20000 AFIX 0 C013 1 0.565524 0.079495 0.892248 11.00000 0.06417 0.03458 = 0.07946 0.00962 -0.00559 -0.00237 AFIX 43 H013 2 0.601946 -0.008451 0.923245 11.00000 -1.20000 AFIX 0 C014 1 0.531248 0.186334 0.928060 11.00000 0.06807 0.04657 = 0.05484 0.00520 -0.00343 -0.00667 AFIX 43 H014 2 0.544686 0.170079 0.983417 11.00000 -1.20000 AFIX 0 C015 1 0.696177 0.818534 0.429912 11.00000 0.07145 0.06466 = 0.04501 -0.00645 0.00644 -0.01581 AFIX 43 H015 2 0.651463 0.873164 0.382207 11.00000 -1.20000 AFIX 0 C016 1 -0.082146 1.176619 0.823372 11.00000 0.10680 0.10318 = 0.14435 -0.09253 0.01950 0.00057 AFIX 137 H01A 2 -0.042287 1.239370 0.779841 11.00000 -1.50000 H01B 2 -0.018720 1.149015 0.869185 11.00000 -1.50000 H01C 2 -0.173092 1.220949 0.837932 11.00000 -1.50000 AFIX 0 C017 1 0.838676 0.762273 0.429518 11.00000 0.07429 0.09367 = 0.05845 -0.02115 0.02982 -0.02388 AFIX 43 H017 2 0.891136 0.779036 0.382044 11.00000 -1.20000 AFIX 0 O17 4 -0.099864 1.062482 0.799187 11.00000 0.05765 0.07183 = 0.07973 -0.03392 0.00672 0.00891 C018 1 1.126743 0.201811 1.008387 11.00000 0.07837 0.06344 = 0.08440 -0.01314 -0.03953 0.01675 AFIX 137 H01D 2 1.125977 0.125915 0.985603 11.00000 -1.50000 H01E 2 1.115664 0.172281 1.065923 11.00000 -1.50000 H01F 2 1.215858 0.234628 0.996301 11.00000 -1.50000 AFIX 0 C019 1 0.901599 0.681256 0.500287 11.00000 0.05003 0.10143 = 0.06665 -0.01912 0.02154 -0.00283 AFIX 43 H019 2 0.997711 0.642453 0.500477 11.00000 -1.20000 AFIX 0 HKLF 4 REM CC_a.res in P-1 REM wR2 = 0.1646, GooF = S = 1.035, Restrained GooF = 1.035 for all data REM R1 = 0.0583 for 4840 Fo > 4sig(Fo) and 0.0994 for all 7341 data REM 408 parameters refined using 1 restraints END WGHT 0.0818 0.4003 REM Highest difference peak 0.377, deepest hole -0.392, 1-sigma level 0.077 Q1 1 0.2349 1.0025 0.8204 11.00000 0.05 0.38 Q2 1 0.0058 1.0986 0.8403 11.00000 0.05 0.34 Q3 1 0.3429 0.8987 0.7918 11.00000 0.05 0.30 Q4 1 0.1290 0.4030 0.7484 11.00000 0.05 0.27 Q5 1 0.3310 1.0808 0.3848 11.00000 0.05 0.26 Q6 1 0.5349 0.8563 0.7137 11.00000 0.05 0.24 Q7 1 0.1458 0.4610 0.6832 11.00000 0.05 0.24 Q8 1 0.2389 0.4616 0.6794 11.00000 0.05 0.23 Q9 1 0.0733 1.0046 0.8177 11.00000 0.05 0.23 Q10 1 0.9789 0.3579 0.8406 11.00000 0.05 0.23 Q11 1 0.5876 0.9587 0.6683 11.00000 0.05 0.22 Q12 1 0.8841 0.4750 0.7885 11.00000 0.05 0.22 Q13 1 0.5380 0.8867 0.6529 11.00000 0.05 0.22 Q14 1 0.3481 1.0237 0.4265 11.00000 0.05 0.21 Q15 1 -0.0255 1.2819 0.8605 11.00000 0.05 0.21 Q16 1 0.0118 1.4503 0.7564 11.00000 0.05 0.21 Q17 1 0.6406 0.8509 0.6775 11.00000 0.05 0.21 Q18 1 0.1738 1.3199 0.7698 11.00000 0.05 0.21 Q19 1 0.5944 0.8548 0.6533 11.00000 0.05 0.21 Q20 1 0.1881 0.3636 0.7034 11.00000 0.05 0.21 ; _shelx_res_checksum 3017 _olex2_submission_special_instructions 'No special instructions were received' 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 S001 S 0.63773(6) 0.64868(5) 0.85808(3) 0.03852(17) Uani 1 1 d . . O002 O 0.69410(17) 0.77130(15) 0.82325(10) 0.0537(4) Uani 1 1 d . . O003 O 0.52342(17) 0.65172(17) 0.91438(9) 0.0517(4) Uani 1 1 d . . N004 N 0.58151(17) 0.59305(17) 0.78584(10) 0.0361(4) Uani 1 1 d . . N006 N 0.31184(19) 0.64466(16) 0.64637(10) 0.0395(4) Uani 1 1 d . . N007 N 0.60396(18) 0.68809(18) 0.64450(10) 0.0430(4) Uani 1 1 d . . N008 N 0.4015(2) 0.47429(17) 0.75386(11) 0.0452(5) Uani 1 1 d . . C009 C 0.2444(2) 0.8100(2) 0.72944(12) 0.0373(5) Uani 1 1 d . . C00A C 0.6823(2) 0.7139(2) 0.57300(13) 0.0402(5) Uani 1 1 d . . C00B C 0.2827(2) 0.7082(2) 0.56429(13) 0.0406(5) Uani 1 1 d . . C00C C 0.3647(2) 0.71585(19) 0.70038(12) 0.0334(4) Uani 1 1 d . . C00D C 0.0199(3) 0.9798(2) 0.77916(14) 0.0496(6) Uani 1 1 d . U C00E C 0.2703(3) 0.9061(2) 0.76631(14) 0.0488(6) Uani 1 1 d . . H00E H 0.364136 0.913819 0.774903 0.059 Uiso 1 1 calc R . C00F C 0.9180(2) 0.5282(2) 0.87473(14) 0.0481(6) Uani 1 1 d . . H00F H 0.935401 0.601919 0.832510 0.058 Uiso 1 1 calc R . C00G C 0.4277(2) 0.59450(19) 0.77380(12) 0.0344(5) Uani 1 1 d . . H00G H 0.375217 0.603801 0.822905 0.041 Uiso 1 1 calc R . C00H C 0.4570(2) 0.3420(2) 0.80016(13) 0.0419(5) Uani 1 1 d . . C00I C 0.1022(2) 0.7984(2) 0.72027(15) 0.0480(6) Uani 1 1 d . . H00I H 0.082110 0.731941 0.696594 0.058 Uiso 1 1 calc R . C00J C 0.6735(2) 0.5940(2) 0.71625(12) 0.0421(5) Uani 1 1 d . . H00A H 0.762506 0.621702 0.725554 0.051 Uiso 1 1 calc R . H00B H 0.695459 0.502198 0.708575 0.051 Uiso 1 1 calc R . C00K C 0.7821(2) 0.5213(2) 0.90351(12) 0.0394(5) Uani 1 1 d . . C00L C 0.4870(2) 0.7894(2) 0.66121(13) 0.0376(5) Uani 1 1 d . . H00C H 0.453987 0.857047 0.611334 0.045 Uiso 1 1 calc R . H00D H 0.519580 0.836627 0.697291 0.045 Uiso 1 1 calc R . C00M C 0.3022(2) 0.6320(3) 0.50736(14) 0.0489(6) Uani 1 1 d . . H00M H 0.334793 0.537805 0.523813 0.059 Uiso 1 1 calc R . C00N C 0.4775(3) 0.3165(2) 0.88282(14) 0.0482(6) Uani 1 1 d . . H00N H 0.454686 0.387817 0.907629 0.058 Uiso 1 1 calc R . C00O C 0.2029(3) 0.9094(3) 0.45635(15) 0.0600(7) Uani 1 1 d . . H00O H 0.168220 1.003171 0.439181 0.072 Uiso 1 1 calc R . C00P C -0.0077(3) 0.8820(3) 0.74512(16) 0.0550(6) Uani 1 1 d . . H00P H -0.101568 0.871894 0.738705 0.066 Uiso 1 1 calc R . C00Q C 0.2297(2) 0.8487(2) 0.53709(14) 0.0482(6) Uani 1 1 d . . H00Q H 0.212386 0.901627 0.573973 0.058 Uiso 1 1 calc R . C00R C 0.3726(3) 0.5002(2) 0.66881(13) 0.0449(5) Uani 1 1 d . . H00H H 0.305274 0.444800 0.659404 0.054 Uiso 1 1 calc R . H00J H 0.459608 0.481874 0.639177 0.054 Uiso 1 1 calc R . C00S C 0.6197(3) 0.7944(3) 0.50035(14) 0.0524(6) Uani 1 1 d . . H00S H 0.523472 0.833034 0.499399 0.063 Uiso 1 1 calc R . C00T C 0.7559(3) 0.4146(2) 0.96823(13) 0.0493(6) Uani 1 1 d . . H00T H 0.663903 0.410989 0.988328 0.059 Uiso 1 1 calc R . C00U C 0.1579(3) 0.9933(3) 0.79144(15) 0.0557(6) Uani 1 1 d . U H00U H 0.176417 1.059206 0.816036 0.067 Uiso 1 1 calc R . C00V C 1.0290(3) 0.4245(3) 0.90913(16) 0.0538(6) Uani 1 1 d . . H00V H 1.120943 0.428147 0.888991 0.065 Uiso 1 1 calc R . C00W C 1.0055(3) 0.3157(2) 0.97283(15) 0.0527(6) Uani 1 1 d . . C00X C 0.5456(3) 0.1037(2) 0.81075(18) 0.0609(7) Uani 1 1 d . . H00X H 0.568729 0.031700 0.786476 0.073 Uiso 1 1 calc R . C00Y C 0.4915(3) 0.2339(2) 0.76427(16) 0.0519(6) Uani 1 1 d . . H00Y H 0.478195 0.249315 0.708966 0.062 Uiso 1 1 calc R . C00Z C 0.8259(3) 0.6558(3) 0.57134(16) 0.0574(6) Uani 1 1 d . . H00Z H 0.870969 0.599367 0.618500 0.069 Uiso 1 1 calc R . C010 C 0.2268(3) 0.8333(3) 0.40030(16) 0.0670(8) Uani 1 1 d . . H010 H 0.211271 0.875281 0.345504 0.080 Uiso 1 1 calc R . C011 C 0.8692(3) 0.3136(3) 1.00240(15) 0.0587(7) Uani 1 1 d . . H011 H 0.852722 0.242518 1.046493 0.070 Uiso 1 1 calc R . C012 C 0.2734(3) 0.6953(3) 0.42695(15) 0.0618(7) Uani 1 1 d . . H012 H 0.286168 0.642626 0.389868 0.074 Uiso 1 1 calc R . C013 C 0.5655(3) 0.0795(3) 0.89225(18) 0.0648(8) Uani 1 1 d . . H013 H 0.601946 -0.008451 0.923245 0.078 Uiso 1 1 calc R . C014 C 0.5312(3) 0.1863(3) 0.92806(16) 0.0604(7) Uani 1 1 d . . H014 H 0.544686 0.170079 0.983417 0.072 Uiso 1 1 calc R . C015 C 0.6962(3) 0.8185(3) 0.42991(16) 0.0616(7) Uani 1 1 d . . H015 H 0.651463 0.873164 0.382207 0.074 Uiso 1 1 calc R . C016 C -0.0821(4) 1.1766(4) 0.8234(3) 0.1093(14) Uani 1 1 d . . H01A H -0.042287 1.239370 0.779841 0.164 Uiso 1 1 calc GR . H01B H -0.018720 1.149015 0.869185 0.164 Uiso 1 1 calc GR . H01C H -0.173092 1.220949 0.837932 0.164 Uiso 1 1 calc GR . C017 C 0.8387(3) 0.7623(3) 0.42952(18) 0.0749(8) Uani 1 1 d . . H017 H 0.891136 0.779036 0.382044 0.090 Uiso 1 1 calc R . O17 O -0.09986(19) 1.0625(2) 0.79919(12) 0.0697(5) Uani 1 1 d . . C018 C 1.1267(3) 0.2018(3) 1.00839(19) 0.0791(9) Uani 1 1 d . . H01D H 1.125977 0.125915 0.985603 0.119 Uiso 1 1 calc GR . H01E H 1.115664 0.172281 1.065923 0.119 Uiso 1 1 calc GR . H01F H 1.215858 0.234628 0.996301 0.119 Uiso 1 1 calc GR . C019 C 0.9016(3) 0.6813(3) 0.50029(18) 0.0751(9) Uani 1 1 d . . H019 H 0.997711 0.642453 0.500477 0.090 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 S001 0.0398(3) 0.0361(3) 0.0390(3) -0.0124(2) -0.0061(2) 0.0006(2) O002 0.0554(10) 0.0349(8) 0.0693(11) -0.0097(8) -0.0138(8) -0.0065(7) O003 0.0506(9) 0.0637(10) 0.0419(9) -0.0240(8) 0.0018(7) 0.0032(8) N004 0.0334(9) 0.0405(9) 0.0329(9) -0.0112(7) -0.0029(7) 0.0009(7) N006 0.0442(10) 0.0317(9) 0.0397(10) -0.0077(7) -0.0120(8) 0.0013(8) N007 0.0382(10) 0.0466(10) 0.0363(10) -0.0065(8) 0.0014(8) 0.0073(8) N008 0.0575(12) 0.0287(9) 0.0469(11) -0.0064(8) -0.0177(9) -0.0021(8) C009 0.0361(11) 0.0313(10) 0.0380(11) -0.0032(8) 0.0014(9) 0.0022(9) C00A 0.0418(12) 0.0404(11) 0.0400(12) -0.0135(9) 0.0036(10) -0.0074(10) C00B 0.0336(11) 0.0433(12) 0.0411(12) -0.0074(9) -0.0063(9) -0.0010(9) C00C 0.0337(10) 0.0290(10) 0.0352(10) -0.0076(8) -0.0035(8) 0.0008(8) C00D 0.0467(11) 0.0487(13) 0.0423(12) -0.0059(10) 0.0047(10) 0.0109(10) C00E 0.0439(13) 0.0499(13) 0.0539(14) -0.0212(11) 0.0017(11) -0.0004(11) C00F 0.0434(13) 0.0467(13) 0.0506(13) -0.0070(11) -0.0071(11) -0.0056(10) C00G 0.0344(11) 0.0285(10) 0.0375(11) -0.0070(8) -0.0030(9) 0.0000(8) C00H 0.0393(12) 0.0307(10) 0.0520(13) -0.0037(9) -0.0083(10) -0.0051(9) C00I 0.0381(12) 0.0425(12) 0.0606(15) -0.0116(11) 0.0016(11) -0.0029(10) C00J 0.0376(11) 0.0465(12) 0.0378(11) -0.0121(9) -0.0031(9) 0.0064(10) C00K 0.0409(12) 0.0387(11) 0.0378(11) -0.0103(9) -0.0094(9) -0.0024(9) C00L 0.0377(11) 0.0317(10) 0.0390(11) -0.0062(9) -0.0001(9) 0.0014(9) C00M 0.0472(13) 0.0516(13) 0.0475(13) -0.0165(11) -0.0069(11) -0.0005(11) C00N 0.0530(14) 0.0383(12) 0.0481(13) -0.0055(10) -0.0007(11) -0.0028(10) C00O 0.0607(16) 0.0549(15) 0.0510(15) 0.0012(12) -0.0113(12) 0.0054(12) C00P 0.0415(13) 0.0521(14) 0.0678(16) -0.0143(12) 0.0049(12) -0.0020(11) C00Q 0.0494(13) 0.0453(13) 0.0437(13) -0.0070(10) -0.0096(11) 0.0030(11) C00R 0.0512(13) 0.0337(11) 0.0481(13) -0.0104(10) -0.0148(11) 0.0000(10) C00S 0.0501(14) 0.0599(15) 0.0418(13) -0.0055(11) 0.0039(11) -0.0076(12) C00T 0.0509(14) 0.0540(14) 0.0389(12) -0.0055(10) -0.0057(10) -0.0073(11) C00U 0.0630(12) 0.0511(14) 0.0574(15) -0.0259(12) -0.0024(12) -0.0028(12) C00V 0.0415(13) 0.0563(15) 0.0620(15) -0.0162(13) -0.0121(11) -0.0005(11) C00W 0.0558(15) 0.0481(13) 0.0522(14) -0.0147(11) -0.0218(12) 0.0040(12) C00X 0.0633(17) 0.0334(12) 0.082(2) -0.0115(12) -0.0054(14) -0.0034(11) C00Y 0.0581(15) 0.0375(12) 0.0591(15) -0.0123(11) -0.0077(12) -0.0046(11) C00Z 0.0454(14) 0.0709(17) 0.0525(14) -0.0165(13) 0.0077(11) -0.0024(12) C010 0.0706(18) 0.081(2) 0.0403(14) -0.0070(13) -0.0119(13) 0.0008(15) C011 0.0729(19) 0.0495(14) 0.0465(14) -0.0007(11) -0.0177(13) -0.0058(13) C012 0.0635(16) 0.0780(19) 0.0444(14) -0.0227(13) -0.0072(12) -0.0019(14) C013 0.0642(17) 0.0346(13) 0.079(2) 0.0096(12) -0.0056(15) -0.0024(12) C014 0.0681(17) 0.0466(14) 0.0548(15) 0.0052(12) -0.0034(13) -0.0067(12) C015 0.0714(18) 0.0647(16) 0.0450(14) -0.0065(12) 0.0064(13) -0.0158(14) C016 0.107(3) 0.103(3) 0.144(3) -0.093(3) 0.019(2) 0.001(2) C017 0.074(2) 0.094(2) 0.0584(18) -0.0211(16) 0.0298(16) -0.0239(18) O17 0.0577(11) 0.0718(12) 0.0797(13) -0.0339(10) 0.0067(9) 0.0089(9) C018 0.078(2) 0.0634(17) 0.084(2) -0.0131(15) -0.0395(17) 0.0168(15) C019 0.0500(16) 0.101(2) 0.0667(19) -0.0191(17) 0.0215(14) -0.0028(16) 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 O002 S001 O003 119.17(11) O002 S001 N004 109.23(10) O002 S001 C00K 107.09(11) O003 S001 N004 106.25(10) O003 S001 C00K 109.31(11) N004 S001 C00K 104.91(10) C00G N004 S001 121.73(13) C00J N004 S001 117.06(15) C00J N004 C00G 116.94(16) C00B N006 C00C 122.21(17) C00B N006 C00R 117.75(17) C00R N006 C00C 110.65(15) C00A N007 C00J 118.48(18) C00A N007 C00L 121.92(18) C00J N007 C00L 113.91(17) C00G N008 C00R 111.76(17) C00H N008 C00G 122.07(17) C00H N008 C00R 120.76(17) C00E C009 C00C 122.0(2) C00E C009 C00I 117.7(2) C00I C009 C00C 120.4(2) C00S C00A N007 121.7(2) C00S C00A C00Z 117.2(2) C00Z C00A N007 121.0(2) C00M C00B N006 120.84(19) C00M C00B C00Q 117.8(2) C00Q C00B N006 121.38(19) N006 C00C C009 111.85(17) N006 C00C C00G 102.89(15) N006 C00C C00L 111.03(17) C009 C00C C00G 109.43(17) C009 C00C C00L 113.04(17) C00L C00C C00G 108.04(16) C00P C00D C00U 120.8(2) C00P C00D O17 115.0(2) C00U C00D O17 124.2(2) C009 C00E H00E 119.5 C009 C00E C00U 121.0(2) C00U C00E H00E 119.5 C00K C00F H00F 120.3 C00K C00F C00V 119.3(2) C00V C00F H00F 120.3 N004 C00G C00C 111.21(16) N004 C00G H00G 109.4 N008 C00G N004 112.80(16) N008 C00G C00C 104.37(16) N008 C00G H00G 109.4 C00C C00G H00G 109.4 C00N C00H N008 120.4(2) C00N C00H C00Y 119.0(2) C00Y C00H N008 120.6(2) C009 C00I H00I 119.2 C00P C00I C009 121.6(2) C00P C00I H00I 119.2 N004 C00J H00A 109.6 N004 C00J H00B 109.6 N007 C00J N004 110.31(17) N007 C00J H00A 109.6 N007 C00J H00B 109.6 H00A C00J H00B 108.1 C00F C00K S001 120.19(18) C00F C00K C00T 120.8(2) C00T C00K S001 119.05(18) N007 C00L C00C 108.92(17) N007 C00L H00C 109.9 N007 C00L H00D 109.9 C00C C00L H00C 109.9 C00C C00L H00D 109.9 H00C C00L H00D 108.3 C00B C00M H00M 119.8 C012 C00M C00B 120.4(2) C012 C00M H00M 119.8 C00H C00N H00N 119.9 C014 C00N C00H 120.2(2) C014 C00N H00N 119.9 C00Q C00O H00O 119.5 C00Q C00O C010 121.0(2) C010 C00O H00O 119.5 C00D C00P C00I 119.9(2) C00D C00P H00P 120.1 C00I C00P H00P 120.1 C00B C00Q H00Q 119.7 C00O C00Q C00B 120.6(2) C00O C00Q H00Q 119.7 N006 C00R H00H 111.3 N006 C00R H00J 111.3 N008 C00R N006 102.50(16) N008 C00R H00H 111.3 N008 C00R H00J 111.3 H00H C00R H00J 109.2 C00A C00S H00S 119.1 C015 C00S C00A 121.8(2) C015 C00S H00S 119.1 C00K C00T H00T 120.7 C011 C00T C00K 118.7(2) C011 C00T H00T 120.7 C00D C00U C00E 118.9(2) C00D C00U H00U 120.6 C00E C00U H00U 120.6 C00F C00V H00V 119.4 C00W C00V C00F 121.1(2) C00W C00V H00V 119.4 C00V C00W C018 120.5(3) C011 C00W C00V 118.4(2) C011 C00W C018 121.1(3) C00Y C00X H00X 119.7 C013 C00X H00X 119.7 C013 C00X C00Y 120.6(2) C00H C00Y H00Y 120.0 C00X C00Y C00H 120.0(2) C00X C00Y H00Y 120.0 C00A C00Z H00Z 119.8 C019 C00Z C00A 120.5(3) C019 C00Z H00Z 119.8 C00O C010 H010 120.7 C012 C010 C00O 118.6(2) C012 C010 H010 120.7 C00T C011 H011 119.2 C00W C011 C00T 121.7(2) C00W C011 H011 119.2 C00M C012 H012 119.2 C010 C012 C00M 121.6(2) C010 C012 H012 119.2 C00X C013 H013 120.2 C00X C013 C014 119.6(2) C014 C013 H013 120.2 C00N C014 C013 120.6(2) C00N C014 H014 119.7 C013 C014 H014 119.7 C00S C015 H015 119.8 C00S C015 C017 120.3(3) C017 C015 H015 119.8 H01A C016 H01B 109.5 H01A C016 H01C 109.5 H01B C016 H01C 109.5 O17 C016 H01A 109.5 O17 C016 H01B 109.5 O17 C016 H01C 109.5 C015 C017 H017 120.6 C019 C017 C015 118.7(3) C019 C017 H017 120.6 C016 O17 C00D 118.7(2) C00W C018 H01D 109.5 C00W C018 H01E 109.5 C00W C018 H01F 109.5 H01D C018 H01E 109.5 H01D C018 H01F 109.5 H01E C018 H01F 109.5 C00Z C019 H019 119.2 C017 C019 C00Z 121.5(3) C017 C019 H019 119.2 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S001 O002 1.4254(19) S001 O003 1.4266(18) S001 N004 1.6382(18) S001 C00K 1.764(2) N004 C00G 1.482(3) N004 C00J 1.450(3) N006 C00B 1.402(3) N006 C00C 1.473(3) N006 C00R 1.445(3) N007 C00A 1.397(3) N007 C00J 1.446(3) N007 C00L 1.458(3) N008 C00G 1.426(3) N008 C00H 1.399(3) N008 C00R 1.441(3) C009 C00C 1.520(3) C009 C00E 1.364(3) C009 C00I 1.395(3) C00A C00S 1.389(3) C00A C00Z 1.393(3) C00B C00M 1.392(3) C00B C00Q 1.397(3) C00C C00G 1.568(3) C00C C00L 1.531(3) C00D C00P 1.353(4) C00D C00U 1.373(4) C00D O17 1.384(3) C00E H00E 0.9300 C00E C00U 1.400(3) C00F H00F 0.9300 C00F C00K 1.371(3) C00F C00V 1.383(3) C00G H00G 0.9800 C00H C00N 1.388(3) C00H C00Y 1.390(3) C00I H00I 0.9300 C00I C00P 1.361(3) C00J H00A 0.9700 C00J H00B 0.9700 C00K C00T 1.384(3) C00L H00C 0.9700 C00L H00D 0.9700 C00M H00M 0.9300 C00M C012 1.375(3) C00N H00N 0.9300 C00N C014 1.373(3) C00O H00O 0.9300 C00O C00Q 1.373(3) C00O C010 1.380(4) C00P H00P 0.9300 C00Q H00Q 0.9300 C00R H00H 0.9700 C00R H00J 0.9700 C00S H00S 0.9300 C00S C015 1.373(4) C00T H00T 0.9300 C00T C011 1.383(3) C00U H00U 0.9300 C00V H00V 0.9300 C00V C00W 1.380(4) C00W C011 1.374(4) C00W C018 1.506(3) C00X H00X 0.9300 C00X C00Y 1.381(3) C00X C013 1.369(4) C00Y H00Y 0.9300 C00Z H00Z 0.9300 C00Z C019 1.378(4) C010 H010 0.9300 C010 C012 1.362(4) C011 H011 0.9300 C012 H012 0.9300 C013 H013 0.9300 C013 C014 1.378(4) C014 H014 0.9300 C015 H015 0.9300 C015 C017 1.376(4) C016 H01A 0.9600 C016 H01B 0.9600 C016 H01C 0.9600 C016 O17 1.379(4) C017 H017 0.9300 C017 C019 1.367(4) C018 H01D 0.9600 C018 H01E 0.9600 C018 H01F 0.9600 C019 H019 0.9300