#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:41:00 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257408 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/72/1557289.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_1557289 loop_ _publ_author_name 'Zhang, Xiang' 'Li, Xiang' 'Li, Jun-Long' 'Wang, Qi-Wei' 'Zou, Wen-Lin' 'Liu, Yan-Qing' 'Jia, Zhi-Qiang' 'Peng, Fu' 'Han, Bo' _publ_section_title ; Regiodivergent construction of medium-sized heterocycles from vinylethylene carbonates and allylidenemalononitriles ; _journal_issue 11 _journal_name_full 'Chemical Science' _journal_page_first 2888 _journal_page_last 2894 _journal_paper_doi 10.1039/C9SC06377C _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C25 H21 N2 O3' _chemical_formula_sum 'C25 H22 N2 O3' _chemical_formula_weight 398.44 _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 geom _atom_sites_solution_primary direct _audit_creation_date 2019-07-22 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _audit_update_record ; 2019-07-29 deposited with the CCDC. 2020-02-10 downloaded from the CCDC. ; _cell_angle_alpha 87.285(6) _cell_angle_beta 85.531(8) _cell_angle_gamma 74.852(9) _cell_formula_units_Z 2 _cell_length_a 7.8691(9) _cell_length_b 9.8641(8) _cell_length_c 13.1840(9) _cell_measurement_reflns_used 3691 _cell_measurement_temperature 225(100) _cell_measurement_theta_max 71.6710 _cell_measurement_theta_min 4.6310 _cell_volume 984.41(16) _computing_cell_refinement 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _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_environment N~2~ _diffrn_ambient_temperature 225(100) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 15.9595 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.974 _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 -63.00 31.00 1.00 1.00 -- -36.42 77.00 60.00 94 2 \w -104.00 -20.00 1.00 1.00 -- -36.42 -57.00 -60.00 84 3 \w -108.00 -7.00 1.00 1.00 -- -36.42 -19.00 120.00 101 4 \w -53.00 31.00 1.00 1.00 -- -36.42 57.00 -60.00 84 5 \w 1.00 75.00 1.00 1.00 -- 36.42 -99.00 150.00 74 6 \w -31.00 53.00 1.00 1.00 -- 36.42 -57.00-180.00 84 7 \w 23.00 90.00 1.00 1.00 -- 36.42-125.00 30.00 67 8 \w 30.00 96.00 1.00 1.00 -- 36.42-136.00 141.00 66 9 \w 36.00 113.00 1.00 3.06 -- 106.21-111.00 30.00 77 10 \w 38.00 124.00 1.00 3.06 -- 106.21 -45.00 60.00 86 11 \w 37.00 109.00 1.00 3.06 -- 106.21 -94.00 90.00 72 12 \w 100.00 176.00 1.00 3.06 -- 106.21 111.00 -30.00 76 13 \w 89.00 175.00 1.00 3.06 -- 106.21 45.00 -30.00 86 14 \w 89.00 175.00 1.00 3.06 -- 106.21 45.00 150.00 86 15 \w 36.00 113.00 1.00 3.06 -- 106.21-111.00 -90.00 77 16 \w 36.00 113.00 1.00 3.06 -- 106.21-111.00-180.00 77 17 \w 89.00 175.00 1.00 3.06 -- 106.21 45.00 60.00 86 18 \w 39.00 124.00 1.00 3.06 -- 106.21 -61.00 -30.00 85 19 \w 38.00 124.00 1.00 3.06 -- 106.21 -45.00-180.00 86 20 \w 89.00 175.00 1.00 3.06 -- 106.21 45.00 90.00 86 21 \w 39.00 124.00 1.00 3.06 -- 106.21 -61.00-120.00 85 22 \w 89.00 175.00 1.00 3.06 -- 106.21 45.00 30.00 86 23 \w -104.00 -20.00 1.00 1.00 -- -36.42 -57.00 120.00 84 24 \w -104.00 -10.00 1.00 1.00 -- -36.42 -77.00 60.00 94 25 \w 10.00 104.00 1.00 1.00 -- 36.42 77.00 150.00 94 26 \w 10.00 104.00 1.00 1.00 -- 36.42 77.00 60.00 94 27 \w 10.00 104.00 1.00 1.00 -- 36.42 77.00 -30.00 94 28 \w 10.00 104.00 1.00 1.00 -- 36.42 77.00-120.00 94 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Gemini, Dual, Cu at home/near, EosS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0045949000 _diffrn_orient_matrix_UB_12 0.0222620000 _diffrn_orient_matrix_UB_13 -0.1165287000 _diffrn_orient_matrix_UB_21 -0.0950854000 _diffrn_orient_matrix_UB_22 0.1564867000 _diffrn_orient_matrix_UB_23 0.0129862000 _diffrn_orient_matrix_UB_31 0.1796242000 _diffrn_orient_matrix_UB_32 0.0348775000 _diffrn_orient_matrix_UB_33 0.0008357000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_unetI/netI 0.0560 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 10529 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.358 _diffrn_reflns_theta_min 3.364 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.62449 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) 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 1.344 _exptl_crystal_description needle _exptl_crystal_F_000 420 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.715 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.098 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 3791 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0793 _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^)+(0.1564P)^2^+0.2886P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2132 _refine_ls_wR_factor_ref 0.2314 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3208 _reflns_number_total 3791 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc06377c2.cif _cod_data_source_block ljl-zx-0719-150k _cod_depositor_comments ;Adding full bibliography for 1557287--1557289.cif. Adding full bibliography for 1557287--1557289.cif. ; _cod_original_cell_volume 984.42(16) _cod_database_code 1557289 _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. ; _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, {H00I,H00C,H00E} of C00I, {H00A,H00B,H00H} of C00H, All C(H,H) groups At 1.5 times of: {H00U,H00V,H00W} of C00U 2. Others Sof(H00H)=Sof(H00C)=Sof(H00E)=Sof(O2A)=1-FVAR(1) Sof(H00A)=Sof(H00B)=Sof(H00I)=Sof(O2)=FVAR(1) 3.a Ternary CH refined with riding coordinates: C00D(H00D) 3.b Secondary CH2 refined with riding coordinates: C00H(H00A,H00B), C00I(H00C,H00E), C00J(H00F,H00J), C00P(H00L,H00P) 3.c Aromatic/amide H refined with riding coordinates: C008(H008), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T) 3.d Idealised Me refined as rotating group: C00U(H00U,H00V,H00W) ; _shelx_res_file ; ljl-zx-0719-150k.res created by SHELXL-2014/7 TITL ljl-zx-0719-150k_a.res in P-1 REM Old TITL ljl-zx-0719-150k in P-1 #2 REM SHELXT solution in P-1 REM R1 0.168, Rweak 0.008, Alpha 0.036, Orientation as input REM Formula found by SHELXT: C25 N3 O2 CELL 1.54184 7.869091 9.86408 13.184037 87.2845 85.5314 74.8522 ZERR 2 0.000899 0.000762 0.000859 0.0058 0.0078 0.0088 LATT 1 SFAC C H N O UNIT 50 44 4 6 L.S. 10 PLAN 20 BOND $H LIST 6 fmap 2 ACTA REM REM REM WGHT 0.156400 0.288600 FVAR 1.00794 0.74253 O002 4 0.618820 -0.017741 0.092498 11.00000 0.04525 0.02094 = 0.03194 -0.00397 0.00461 -0.00749 N003 3 0.922639 0.071526 0.228328 11.00000 0.02929 0.03266 = 0.03574 -0.00268 0.00117 -0.00591 C005 1 0.784012 0.113256 0.265775 11.00000 0.02715 0.02143 = 0.02504 0.00056 -0.00294 -0.00657 C006 1 0.524913 0.418796 0.236653 11.00000 0.02849 0.01979 = 0.02138 -0.00055 -0.00358 -0.00508 C007 1 0.474459 0.281827 0.256460 11.00000 0.02339 0.02030 = 0.02135 -0.00193 -0.00121 -0.00348 C008 1 0.678968 0.420296 0.177097 11.00000 0.02960 0.02191 = 0.02274 -0.00199 -0.00196 -0.00732 AFIX 43 H008 2 0.752745 0.336240 0.153640 11.00000 -1.20000 AFIX 0 C00A 1 0.436093 0.194978 0.165795 11.00000 0.02577 0.02207 = 0.02074 -0.00223 -0.00084 -0.00675 C00B 1 0.580713 0.107710 0.095124 11.00000 0.02733 0.02459 = 0.01940 -0.00171 -0.00241 -0.00613 C00C 1 0.604667 0.160529 0.316831 11.00000 0.02399 0.02190 = 0.02274 -0.00082 -0.00094 -0.00491 C00D 1 0.350572 0.119331 0.253223 11.00000 0.02578 0.02434 = 0.02381 -0.00125 0.00093 -0.00872 AFIX 13 H00D 2 0.262250 0.070723 0.237705 11.00000 -1.20000 AFIX 0 C00E 1 0.234598 0.270799 0.417055 11.00000 0.02215 0.03054 = 0.02321 -0.00080 -0.00052 -0.00321 C00F 1 0.634440 0.197455 0.420487 11.00000 0.02358 0.03165 = 0.02809 -0.00139 -0.00096 -0.00315 C00G 1 0.419258 0.546301 0.272632 11.00000 0.03004 0.02748 = 0.02496 -0.00128 -0.00137 -0.00488 AFIX 43 H00G 2 0.316899 0.547592 0.313340 11.00000 -1.20000 AFIX 0 C00H 1 0.130501 0.358049 0.248607 11.00000 0.02464 0.03412 = 0.02507 -0.00460 0.00096 -0.00458 PART 1 AFIX 23 H00A 2 0.021816 0.349430 0.285168 21.00000 -1.20000 H00B 2 0.133813 0.455509 0.250465 21.00000 -1.20000 AFIX 43 PART 0 PART 2 H00H 2 0.015580 0.383067 0.277793 -21.00000 -1.20000 AFIX 0 PART 0 C00I 1 0.299896 0.288413 0.097026 11.00000 0.02596 0.03196 = 0.02165 -0.00216 -0.00062 -0.00269 PART 1 AFIX 43 H00I 2 0.327674 0.319132 0.031564 21.00000 -1.20000 AFIX 23 PART 0 PART 2 H00C 2 0.361684 0.327913 0.041485 -21.00000 -1.20000 H00E 2 0.234415 0.230788 0.067879 -21.00000 -1.20000 AFIX 0 PART 0 C00J 1 0.504573 0.041558 0.315995 11.00000 0.02900 0.02090 = 0.02566 0.00077 0.00071 -0.00856 AFIX 23 H00F 2 0.576354 -0.041807 0.282688 11.00000 -1.20000 H00J 2 0.464505 0.016446 0.384024 11.00000 -1.20000 AFIX 0 C00K 1 0.258101 0.373139 0.479967 11.00000 0.02868 0.03198 = 0.02760 -0.00285 0.00046 -0.00526 AFIX 43 H00K 2 0.317203 0.438812 0.453982 11.00000 -1.20000 AFIX 0 C00L 1 0.288171 0.265714 0.303475 11.00000 0.02482 0.02561 = 0.02273 -0.00004 0.00000 -0.00782 C00M 1 0.616072 0.671413 0.187401 11.00000 0.05084 0.02186 = 0.02724 0.00296 -0.00821 -0.01307 AFIX 43 H00M 2 0.644854 0.755596 0.170156 11.00000 -1.20000 AFIX 0 C00N 1 0.143573 0.175149 0.457677 11.00000 0.03086 0.03845 = 0.03281 0.00117 -0.00165 -0.01265 AFIX 43 H00N 2 0.125192 0.107195 0.416334 11.00000 -1.20000 AFIX 0 C00O 1 0.464676 0.670437 0.248600 11.00000 0.04495 0.02220 = 0.02997 -0.00459 -0.00457 -0.00392 AFIX 43 H00O 2 0.393112 0.754360 0.273663 11.00000 -1.20000 AFIX 0 C00P 1 0.787689 0.125266 -0.043524 11.00000 0.03142 0.03165 = 0.02925 -0.00571 0.00741 -0.00402 AFIX 23 H00L 2 0.734574 0.106229 -0.103460 11.00000 -1.20000 H00P 2 0.859100 0.037219 -0.016812 11.00000 -1.20000 AFIX 0 C00Q 1 0.723672 0.545625 0.152353 11.00000 0.03502 0.03231 = 0.02462 0.00185 -0.00114 -0.01314 AFIX 43 H00Q 2 0.826298 0.544977 0.112084 11.00000 -1.20000 AFIX 0 C00R 1 0.193962 0.377655 0.580991 11.00000 0.03422 0.04002 = 0.02775 -0.00687 0.00185 -0.00241 AFIX 43 H00R 2 0.210939 0.446074 0.622409 11.00000 -1.20000 AFIX 0 C00S 1 0.105310 0.281738 0.620603 11.00000 0.03487 0.05241 = 0.02264 0.00243 0.00491 -0.00343 AFIX 43 H00S 2 0.062692 0.285460 0.688494 11.00000 -1.20000 AFIX 0 C00T 1 0.079687 0.179586 0.559091 11.00000 0.03182 0.04848 = 0.03383 0.00863 0.00092 -0.01250 AFIX 43 H00T 2 0.020118 0.114443 0.585534 11.00000 -1.20000 AFIX 0 C00U 1 0.899247 0.225861 -0.070023 11.00000 0.03668 0.03991 = 0.03909 -0.00444 0.01091 -0.01063 AFIX 137 H00U 2 0.989974 0.186314 -0.121209 11.00000 -1.50000 H00V 2 0.952357 0.242723 -0.010334 11.00000 -1.50000 H00W 2 0.826776 0.312899 -0.095480 11.00000 -1.50000 AFIX 0 O1 4 0.651213 0.191496 0.033126 11.00000 0.03075 0.02273 = 0.02471 -0.00242 0.00441 -0.00551 PART 1 O2 4 0.128919 0.321690 0.144872 21.00000 0.01871 0.04088 = 0.02006 -0.00715 -0.00275 -0.00369 PART 0 N3 3 0.666227 0.220280 0.499719 11.00000 0.03352 0.06802 = 0.03043 -0.01169 -0.00510 -0.00576 PART 2 O2A 4 0.178978 0.399935 0.150500 -21.00000 0.05675 0.02636 = 0.05542 0.00344 -0.00673 -0.00274 HKLF 4 REM ljl-zx-0719-150k_a.res in P-1 REM R1 = 0.0793 for 3208 Fo > 4sig(Fo) and 0.0877 for all 3791 data REM 282 parameters refined using 0 restraints END WGHT 0.1567 0.2840 REM Highest difference peak 0.715, deepest hole -0.466, 1-sigma level 0.098 Q1 1 0.3107 0.2171 0.0397 11.00000 0.05 0.72 Q2 1 0.3351 0.3765 0.0838 11.00000 0.05 0.48 Q3 1 0.4722 0.2464 0.2042 11.00000 0.05 0.44 Q4 1 0.6989 0.1408 0.2837 11.00000 0.05 0.42 Q5 1 0.3065 0.1635 0.2956 11.00000 0.05 0.42 Q6 1 0.0504 0.4059 0.1757 11.00000 0.05 0.42 Q7 1 0.8665 0.1385 0.2599 11.00000 0.05 0.40 Q8 1 0.7450 0.4681 0.1936 11.00000 0.05 0.38 Q9 1 0.5590 0.2415 0.2783 11.00000 0.05 0.38 Q10 1 0.6780 0.2640 0.4383 11.00000 0.05 0.37 Q11 1 1.0599 0.0960 0.2444 11.00000 0.05 0.37 Q12 1 0.2162 0.1019 0.2532 11.00000 0.05 0.36 Q13 1 0.4899 0.3426 0.2411 11.00000 0.05 0.36 Q14 1 0.0886 0.4555 0.2729 11.00000 0.05 0.35 Q15 1 1.0363 0.1138 0.2657 11.00000 0.05 0.35 Q16 1 0.5659 0.4241 0.1783 11.00000 0.05 0.34 Q17 1 0.7430 0.0370 -0.0691 11.00000 0.05 0.33 Q18 1 1.0489 0.1823 0.0205 11.00000 0.05 0.32 Q19 1 0.2928 0.2945 0.4542 11.00000 0.05 0.32 Q20 1 0.2542 0.2709 0.3583 11.00000 0.05 0.31 ; _shelx_res_checksum 18871 _shelx_shelxl_version_number 2014/7 _olex2_date_sample_data_collection 2019-07-19 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.873 _oxdiff_exptl_absorpt_empirical_full_min 0.697 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_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O002 O 0.6188(3) -0.01774(18) 0.09250(13) 0.0332(4) Uani 1 1 d . . . . N003 N 0.9226(3) 0.0715(2) 0.22833(17) 0.0331(5) Uani 1 1 d . . . . C005 C 0.7840(3) 0.1133(2) 0.26577(17) 0.0245(5) Uani 1 1 d . . . . C006 C 0.5249(3) 0.4188(2) 0.23665(16) 0.0233(5) Uani 1 1 d . . . . C007 C 0.4745(3) 0.2818(2) 0.25646(16) 0.0221(5) Uani 1 1 d . . . . C008 C 0.6790(3) 0.4203(2) 0.17710(16) 0.0246(5) Uani 1 1 d . . . . H008 H 0.7527 0.3362 0.1536 0.029 Uiso 1 1 calc R . . . C00A C 0.4361(3) 0.1950(2) 0.16579(16) 0.0227(5) Uani 1 1 d . . . . C00B C 0.5807(3) 0.1077(2) 0.09512(16) 0.0238(5) Uani 1 1 d . . . . C00C C 0.6047(3) 0.1605(2) 0.31683(17) 0.0231(5) Uani 1 1 d . . . . C00D C 0.3506(3) 0.1193(2) 0.25322(17) 0.0243(5) Uani 1 1 d . . . . H00D H 0.2623 0.0707 0.2377 0.029 Uiso 1 1 calc R . . . C00E C 0.2346(3) 0.2708(3) 0.41705(17) 0.0260(5) Uani 1 1 d . . . . C00F C 0.6344(3) 0.1975(3) 0.42049(18) 0.0285(5) Uani 1 1 d . . . . C00G C 0.4193(3) 0.5463(3) 0.27263(17) 0.0280(5) Uani 1 1 d . . . . H00G H 0.3169 0.5476 0.3133 0.034 Uiso 1 1 calc R . . . C00H C 0.1305(3) 0.3580(3) 0.24861(18) 0.0285(5) Uani 1 1 d . . . . H00A H 0.0218 0.3494 0.2852 0.034 Uiso 0.743(10) 1 calc R P A 1 H00B H 0.1338 0.4555 0.2505 0.034 Uiso 0.743(10) 1 calc R P A 1 H00H H 0.0156 0.3831 0.2778 0.034 Uiso 0.257(10) 1 calc R P A 2 C00I C 0.2999(3) 0.2884(3) 0.09703(17) 0.0274(5) Uani 1 1 d . . . . H00I H 0.3277 0.3191 0.0316 0.033 Uiso 0.743(10) 1 calc R P A 1 H00C H 0.3617 0.3279 0.0415 0.033 Uiso 0.257(10) 1 calc R P A 2 H00E H 0.2344 0.2308 0.0679 0.033 Uiso 0.257(10) 1 calc R P A 2 C00J C 0.5046(3) 0.0416(2) 0.31599(17) 0.0250(5) Uani 1 1 d . . . . H00F H 0.5764 -0.0418 0.2827 0.030 Uiso 1 1 calc R . . . H00J H 0.4645 0.0164 0.3840 0.030 Uiso 1 1 calc R . . . C00K C 0.2581(3) 0.3731(3) 0.47997(18) 0.0300(5) Uani 1 1 d . . . . H00K H 0.3172 0.4388 0.4540 0.036 Uiso 1 1 calc R . . . C00L C 0.2882(3) 0.2657(2) 0.30347(17) 0.0243(5) Uani 1 1 d . . . . C00M C 0.6161(4) 0.6714(3) 0.18740(19) 0.0324(6) Uani 1 1 d . . . . H00M H 0.6449 0.7556 0.1702 0.039 Uiso 1 1 calc R . . . C00N C 0.1436(3) 0.1751(3) 0.4577(2) 0.0334(6) Uani 1 1 d . . . . H00N H 0.1252 0.1072 0.4163 0.040 Uiso 1 1 calc R . . . C00O C 0.4647(4) 0.6704(3) 0.24860(19) 0.0330(6) Uani 1 1 d . . . . H00O H 0.3931 0.7544 0.2737 0.040 Uiso 1 1 calc R . . . C00P C 0.7877(3) 0.1253(3) -0.04352(19) 0.0319(6) Uani 1 1 d . . . . H00L H 0.7346 0.1062 -0.1035 0.038 Uiso 1 1 calc R . . . H00P H 0.8591 0.0372 -0.0168 0.038 Uiso 1 1 calc R . . . C00Q C 0.7237(3) 0.5456(3) 0.15235(18) 0.0300(5) Uani 1 1 d . . . . H00Q H 0.8263 0.5450 0.1121 0.036 Uiso 1 1 calc R . . . C00R C 0.1940(3) 0.3777(3) 0.58099(19) 0.0354(6) Uani 1 1 d . . . . H00R H 0.2109 0.4461 0.6224 0.042 Uiso 1 1 calc R . . . C00S C 0.1053(4) 0.2817(3) 0.62060(19) 0.0386(6) Uani 1 1 d . . . . H00S H 0.0627 0.2855 0.6885 0.046 Uiso 1 1 calc R . . . C00T C 0.0797(4) 0.1796(3) 0.5591(2) 0.0381(6) Uani 1 1 d . . . . H00T H 0.0201 0.1144 0.5855 0.046 Uiso 1 1 calc R . . . C00U C 0.8992(4) 0.2259(3) -0.0700(2) 0.0390(6) Uani 1 1 d . . . . H00U H 0.9900 0.1863 -0.1212 0.059 Uiso 1 1 calc GR . . . H00V H 0.9524 0.2427 -0.0103 0.059 Uiso 1 1 calc GR . . . H00W H 0.8268 0.3129 -0.0955 0.059 Uiso 1 1 calc GR . . . O1 O 0.6512(2) 0.19150(16) 0.03313(12) 0.0266(4) Uani 1 1 d . . . . O2 O 0.1289(3) 0.3217(3) 0.14487(16) 0.0270(10) Uani 0.743(10) 1 d . P A 1 N3 N 0.6662(3) 0.2203(3) 0.49972(18) 0.0449(6) Uani 1 1 d . . . . O2A O 0.1790(13) 0.3999(10) 0.1505(7) 0.048(3) Uani 0.257(10) 1 d . P A 2 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 O002 0.0452(10) 0.0209(8) 0.0319(9) -0.0040(7) 0.0046(8) -0.0075(7) N003 0.0293(11) 0.0327(11) 0.0357(11) -0.0027(9) 0.0012(9) -0.0059(8) C005 0.0271(12) 0.0214(11) 0.0250(11) 0.0006(9) -0.0029(9) -0.0066(9) C006 0.0285(11) 0.0198(11) 0.0214(10) -0.0005(8) -0.0036(8) -0.0051(8) C007 0.0234(10) 0.0203(10) 0.0213(10) -0.0019(8) -0.0012(8) -0.0035(8) C008 0.0296(11) 0.0219(11) 0.0227(10) -0.0020(8) -0.0020(9) -0.0073(8) C00A 0.0258(11) 0.0221(11) 0.0207(10) -0.0022(8) -0.0008(8) -0.0067(8) C00B 0.0273(11) 0.0246(11) 0.0194(10) -0.0017(8) -0.0024(8) -0.0061(8) C00C 0.0240(11) 0.0219(11) 0.0227(10) -0.0008(8) -0.0009(8) -0.0049(8) C00D 0.0258(11) 0.0243(11) 0.0238(10) -0.0013(9) 0.0009(8) -0.0087(8) C00E 0.0221(10) 0.0305(12) 0.0232(11) -0.0008(9) -0.0005(8) -0.0032(8) C00F 0.0236(11) 0.0317(12) 0.0281(12) -0.0014(9) -0.0010(9) -0.0031(9) C00G 0.0300(11) 0.0275(12) 0.0250(11) -0.0013(9) -0.0014(9) -0.0049(9) C00H 0.0246(11) 0.0341(13) 0.0251(11) -0.0046(9) 0.0010(9) -0.0046(9) C00I 0.0260(11) 0.0320(12) 0.0217(10) -0.0022(9) -0.0006(9) -0.0027(9) C00J 0.0290(11) 0.0209(11) 0.0257(11) 0.0008(9) 0.0007(9) -0.0086(8) C00K 0.0287(12) 0.0320(13) 0.0276(12) -0.0029(10) 0.0005(9) -0.0053(9) C00L 0.0248(11) 0.0256(11) 0.0227(11) 0.0000(9) 0.0000(8) -0.0078(9) C00M 0.0508(15) 0.0219(11) 0.0272(11) 0.0030(9) -0.0082(10) -0.0131(10) C00N 0.0309(12) 0.0384(14) 0.0328(13) 0.0012(10) -0.0017(10) -0.0127(10) C00O 0.0449(14) 0.0222(12) 0.0300(12) -0.0046(9) -0.0046(10) -0.0039(10) C00P 0.0314(12) 0.0317(12) 0.0293(12) -0.0057(10) 0.0074(10) -0.0040(10) C00Q 0.0350(13) 0.0323(13) 0.0246(11) 0.0018(9) -0.0011(9) -0.0131(10) C00R 0.0342(13) 0.0400(14) 0.0277(12) -0.0069(10) 0.0018(10) -0.0024(11) C00S 0.0349(13) 0.0524(17) 0.0226(11) 0.0024(11) 0.0049(10) -0.0034(11) C00T 0.0318(13) 0.0485(16) 0.0338(13) 0.0086(12) 0.0009(10) -0.0125(11) C00U 0.0367(14) 0.0399(15) 0.0391(14) -0.0044(12) 0.0109(11) -0.0106(11) O1 0.0307(9) 0.0227(8) 0.0247(8) -0.0024(6) 0.0044(6) -0.0055(6) O2 0.0187(11) 0.041(2) 0.0201(11) -0.0071(9) -0.0028(8) -0.0037(10) N3 0.0335(12) 0.0680(17) 0.0304(12) -0.0117(11) -0.0051(9) -0.0058(11) O2A 0.057(6) 0.026(5) 0.055(5) 0.003(4) -0.007(4) -0.003(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N003 C005 C00C 177.2(2) C008 C006 C007 119.5(2) C008 C006 C00G 118.1(2) C00G C006 C007 122.4(2) C006 C007 C00A 121.47(18) C006 C007 C00C 117.64(18) C006 C007 C00L 125.70(19) C00C C007 C00A 100.25(16) C00C C007 C00L 101.10(17) C00L C007 C00A 83.56(16) C006 C008 H008 119.5 C00Q C008 C006 120.9(2) C00Q C008 H008 119.5 C00B C00A C007 123.15(18) C00B C00A C00D 118.77(18) C00B C00A C00I 106.37(17) C00D C00A C007 83.14(15) C00I C00A C007 111.25(17) C00I C00A C00D 112.95(18) O002 C00B C00A 124.7(2) O002 C00B O1 125.2(2) O1 C00B C00A 109.92(18) C005 C00C C007 114.01(18) C005 C00C C00J 110.43(18) C00F C00C C005 104.68(18) C00F C00C C007 114.56(18) C00F C00C C00J 113.57(19) C00J C00C C007 99.85(17) C00A C00D H00D 119.1 C00A C00D C00L 86.09(16) C00J C00D C00A 104.73(17) C00J C00D H00D 119.1 C00J C00D C00L 102.93(17) C00L C00D H00D 119.1 C00K C00E C00L 123.6(2) C00N C00E C00K 118.5(2) C00N C00E C00L 117.7(2) N3 C00F C00C 176.1(3) C006 C00G H00G 119.6 C00O C00G C006 120.8(2) C00O C00G H00G 119.6 H00A C00H H00B 107.7 C00L C00H H00A 108.9 C00L C00H H00B 108.9 C00L C00H H00H 123.7 O2 C00H H00A 108.9 O2 C00H H00B 108.9 O2 C00H C00L 113.41(19) O2A C00H H00H 123.7 O2A C00H C00L 112.7(4) C00A C00I H00I 124.0 C00A C00I H00C 109.0 C00A C00I H00E 109.0 H00C C00I H00E 107.8 O2 C00I C00A 112.0(2) O2 C00I H00I 124.0 O2A C00I C00A 112.7(4) O2A C00I H00C 109.0 O2A C00I H00E 109.0 C00C C00J H00F 112.0 C00C C00J H00J 112.0 C00D C00J C00C 98.91(17) C00D C00J H00F 112.0 C00D C00J H00J 112.0 H00F C00J H00J 109.7 C00E C00K H00K 119.8 C00R C00K C00E 120.4(2) C00R C00K H00K 119.8 C00D C00L C007 82.91(16) C00E C00L C007 123.45(18) C00E C00L C00D 118.42(19) C00E C00L C00H 107.06(18) C00H C00L C007 113.63(18) C00H C00L C00D 109.49(18) C00O C00M H00M 120.4 C00Q C00M H00M 120.4 C00Q C00M C00O 119.2(2) C00E C00N H00N 119.5 C00T C00N C00E 121.0(3) C00T C00N H00N 119.5 C00G C00O C00M 120.7(2) C00G C00O H00O 119.7 C00M C00O H00O 119.7 H00L C00P H00P 108.6 C00U C00P H00L 110.3 C00U C00P H00P 110.3 O1 C00P H00L 110.3 O1 C00P H00P 110.3 O1 C00P C00U 107.0(2) C008 C00Q H00Q 119.9 C00M C00Q C008 120.2(2) C00M C00Q H00Q 119.9 C00K C00R H00R 119.7 C00S C00R C00K 120.6(3) C00S C00R H00R 119.7 C00R C00S H00S 120.1 C00R C00S C00T 119.9(2) C00T C00S H00S 120.1 C00N C00T H00T 120.2 C00S C00T C00N 119.6(3) C00S C00T H00T 120.2 C00P C00U H00U 109.5 C00P C00U H00V 109.5 C00P C00U H00W 109.5 H00U C00U H00V 109.5 H00U C00U H00W 109.5 H00V C00U H00W 109.5 C00B O1 C00P 117.44(18) C00I O2 C00H 111.2(2) C00H O2A C00I 112.2(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O002 C00B 1.196(3) N003 C005 1.142(3) C005 C00C 1.483(3) C006 C007 1.511(3) C006 C008 1.395(3) C006 C00G 1.395(3) C007 C00A 1.594(3) C007 C00C 1.585(3) C007 C00L 1.590(3) C008 H008 0.9300 C008 C00Q 1.389(3) C00A C00B 1.518(3) C00A C00D 1.549(3) C00A C00I 1.541(3) C00B O1 1.328(3) C00C C00F 1.482(3) C00C C00J 1.576(3) C00D H00D 0.9800 C00D C00J 1.534(3) C00D C00L 1.560(3) C00E C00K 1.394(3) C00E C00L 1.523(3) C00E C00N 1.391(4) C00F N3 1.139(3) C00G H00G 0.9300 C00G C00O 1.379(4) C00H H00A 0.9700 C00H H00B 0.9700 C00H H00H 0.9300 C00H C00L 1.542(3) C00H O2 1.432(3) C00H O2A 1.394(9) C00I H00I 0.9300 C00I H00C 0.9700 C00I H00E 0.9700 C00I O2 1.404(3) C00I O2A 1.426(9) C00J H00F 0.9700 C00J H00J 0.9700 C00K H00K 0.9300 C00K C00R 1.386(3) C00M H00M 0.9300 C00M C00O 1.388(4) C00M C00Q 1.384(4) C00N H00N 0.9300 C00N C00T 1.390(4) C00O H00O 0.9300 C00P H00L 0.9700 C00P H00P 0.9700 C00P C00U 1.501(4) C00P O1 1.459(3) C00Q H00Q 0.9300 C00R H00R 0.9300 C00R C00S 1.377(4) C00S H00S 0.9300 C00S C00T 1.387(4) C00T H00T 0.9300 C00U H00U 0.9600 C00U H00V 0.9600 C00U H00W 0.9600