#------------------------------------------------------------------------------ #$Date: 2019-11-10 07:43:51 +0200 (Sun, 10 Nov 2019) $ #$Revision: 225897 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/57/4515772.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_4515772 loop_ _publ_author_name 'Zhang, Bo-Sheng' 'Li, Yuke' 'An, Yang' 'Zhang, Zhe' 'Liu, Ce' 'Wang, Xin-Gang' 'Liang, Yong-Min' _publ_section_title ; Carboxylate Ligand-Exchanged Amination/C(sp3)--H Arylation Reaction via Pd/Norbornene Cooperative Catalysis ; _journal_issue 12 _journal_name_full 'ACS Catalysis' _journal_page_first 11827 _journal_paper_doi 10.1021/acscatal.8b04163 _journal_volume 8 _journal_year 2018 _chemical_absolute_configuration unk _chemical_formula_moiety 'C16 H22 N2 O3' _chemical_formula_sum 'C16 H22 N2 O3' _chemical_formula_weight 290.36 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2018-09-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.5957(9) _cell_length_b 18.8441(17) _cell_length_c 7.6415(5) _cell_measurement_reflns_used 1240 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.5770 _cell_measurement_theta_min 3.8450 _cell_volume 1525.8(2) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -51.00 69.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 22.9430 0.0000 -180.0000 120 #__ type_ start__ end____ width___ exp.time_ 2 omega 57.00 91.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 22.9430 -178.0000 -120.0000 34 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0533197000 _diffrn_orient_matrix_UB_12 0.0199904000 _diffrn_orient_matrix_UB_13 0.0264600000 _diffrn_orient_matrix_UB_21 0.0403598000 _diffrn_orient_matrix_UB_22 -0.0275913000 _diffrn_orient_matrix_UB_23 -0.0291692000 _diffrn_orient_matrix_UB_31 0.0028304000 _diffrn_orient_matrix_UB_32 0.0159095000 _diffrn_orient_matrix_UB_33 -0.0841697000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_unetI/netI 0.0541 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 3745 _diffrn_reflns_theta_full 26.01 _diffrn_reflns_theta_max 26.01 _diffrn_reflns_theta_min 3.46 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.45556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) 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 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.251 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.0(15) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 2616 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0469 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.1322P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0947 _refine_ls_wR_factor_ref 0.1048 _reflns_number_gt 2157 _reflns_number_total 2616 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL zhangbsh_0906 in Pna21 #33 REM reset to Pna21 #33 CELL 0.71073 10.59573 18.844053 7.641534 90 90 90 ZERR 4 0.000915 0.001675 0.000527 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,0.5+Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SFAC C H N O UNIT 64 88 8 12 L.S. 10 PLAN 20 BOND $H HTAB CONF fmap 2 acta SHEL 999 0.81 REM REM REM WGHT 0.040000 0.132200 FVAR 5.57076 N1 3 -0.215292 -0.334592 -0.334648 11.00000 0.02173 0.03411 = 0.02336 0.00323 -0.00096 0.00388 C6 1 -0.119417 -0.295995 -0.052001 11.00000 0.02879 0.03228 = 0.02992 -0.00176 0.00470 0.00632 AFIX 43 H6 2 -0.192224 -0.271475 -0.020951 11.00000 -1.20000 AFIX 0 O1 4 0.331824 -0.395946 0.014055 11.00000 0.02964 0.04938 = 0.03335 -0.00679 -0.01275 0.00855 O2 4 0.375650 -0.477911 -0.191137 11.00000 0.03270 0.05862 = 0.03613 -0.00534 -0.00075 0.01971 O3 4 -0.428167 -0.300632 -0.546196 11.00000 0.02666 0.05393 = 0.03636 0.00356 -0.00385 0.01149 C15 1 0.307548 -0.432491 -0.133706 11.00000 0.02562 0.03850 = 0.02717 0.00442 0.00038 0.00355 N2 3 0.198093 -0.410068 -0.212526 11.00000 0.02760 0.04143 = 0.02461 -0.00493 -0.00490 0.00995 C12 1 0.152933 -0.444852 -0.379221 11.00000 0.02652 0.03432 = 0.02377 -0.00572 -0.00103 0.00261 C5 1 -0.112609 -0.330418 -0.213259 11.00000 0.02516 0.02968 = 0.02313 0.00241 0.00007 0.00392 C7 1 -0.017905 -0.298280 0.061929 11.00000 0.03525 0.03269 = 0.01849 -0.00686 0.00272 0.00187 AFIX 43 H7 2 -0.023598 -0.274184 0.167847 11.00000 -1.20000 AFIX 0 C9 1 0.099638 -0.367743 -0.139200 11.00000 0.02402 0.02837 = 0.02253 0.00117 0.00183 0.00242 C4 1 -0.341453 -0.324727 -0.259308 11.00000 0.02474 0.06402 = 0.03202 0.00765 0.00349 0.00173 AFIX 23 H4A 2 -0.352033 -0.275836 -0.222406 11.00000 -1.20000 H4B 2 -0.351509 -0.355034 -0.157655 11.00000 -1.20000 AFIX 0 C10 1 0.000312 -0.364336 -0.257294 11.00000 0.02791 0.03348 = 0.02096 -0.00174 -0.00180 0.00437 C8 1 0.092194 -0.335265 0.023810 11.00000 0.03366 0.02809 = 0.02279 0.00178 -0.00390 -0.00147 AFIX 43 H8 2 0.158065 -0.338162 0.103923 11.00000 -1.20000 AFIX 0 C16 1 0.444297 -0.417908 0.107029 11.00000 0.02458 0.07798 = 0.03123 0.00335 -0.00744 0.00665 AFIX 137 H16A 2 0.513933 -0.420357 0.026886 11.00000 -1.50000 H16B 2 0.430608 -0.463771 0.158327 11.00000 -1.50000 H16C 2 0.462925 -0.384159 0.197522 11.00000 -1.50000 AFIX 0 C11 1 0.034360 -0.401291 -0.424336 11.00000 0.03511 0.05833 = 0.02950 -0.01234 -0.00849 0.01533 AFIX 23 H11A 2 0.052278 -0.367193 -0.516125 11.00000 -1.20000 H11B 2 -0.033679 -0.432045 -0.462561 11.00000 -1.20000 AFIX 0 C2 1 -0.203948 -0.289999 -0.489712 11.00000 0.02409 0.07462 = 0.03534 0.01799 0.00188 0.00528 AFIX 23 H2A 2 -0.121394 -0.296427 -0.542236 11.00000 -1.20000 H2B 2 -0.212805 -0.240484 -0.457261 11.00000 -1.20000 AFIX 0 C13 1 0.250292 -0.438130 -0.525189 11.00000 0.03720 0.06065 = 0.02902 -0.00100 0.00065 -0.00514 AFIX 137 H13A 2 0.277188 -0.389624 -0.534351 11.00000 -1.50000 H13B 2 0.213314 -0.452861 -0.633973 11.00000 -1.50000 H13C 2 0.321679 -0.467671 -0.499155 11.00000 -1.50000 AFIX 0 C3 1 -0.440079 -0.343327 -0.396118 11.00000 0.03016 0.05072 = 0.05642 0.01067 -0.00571 -0.00472 AFIX 23 H3A 2 -0.430982 -0.392800 -0.428829 11.00000 -1.20000 H3B 2 -0.523610 -0.337057 -0.346529 11.00000 -1.20000 AFIX 0 C14 1 0.118950 -0.521228 -0.344248 11.00000 0.06831 0.04572 = 0.04337 0.00366 -0.01429 -0.01596 AFIX 137 H14A 2 0.192616 -0.546493 -0.305939 11.00000 -1.50000 H14B 2 0.087242 -0.542488 -0.449610 11.00000 -1.50000 H14C 2 0.055352 -0.523342 -0.254923 11.00000 -1.50000 AFIX 0 C1 1 -0.305654 -0.310023 -0.619907 11.00000 0.03279 0.10513 = 0.02908 0.00316 -0.00027 0.02423 AFIX 23 H1A 2 -0.297569 -0.280772 -0.723756 11.00000 -1.20000 H1B 2 -0.294890 -0.359185 -0.654444 11.00000 -1.20000 HKLF 4 REM zhangbsh_0906 in Pna21 #33 REM R1 = 0.0469 for 2157 Fo > 4sig(Fo) and 0.0607 for all 2616 data REM 193 parameters refined using 1 restraints END WGHT 0.0395 0.1114 REM Highest difference peak 0.251, deepest hole -0.220, 1-sigma level 0.045 Q1 1 -0.0028 -0.4389 -0.3567 11.00000 0.05 0.25 Q2 1 0.2066 -0.4049 -0.4839 11.00000 0.05 0.19 Q3 1 0.3018 -0.3471 -0.0293 11.00000 0.05 0.17 Q4 1 -0.0825 -0.2191 -0.1287 11.00000 0.05 0.17 Q5 1 0.4131 -0.4875 -0.6055 11.00000 0.05 0.16 Q6 1 0.1918 -0.5370 -0.4027 11.00000 0.05 0.15 Q7 1 -0.0376 -0.2612 -0.3538 11.00000 0.05 0.14 Q8 1 -0.3585 -0.3985 -0.1957 11.00000 0.05 0.14 Q9 1 0.2195 -0.3367 0.1688 11.00000 0.05 0.14 Q10 1 0.2840 -0.5687 -0.3828 11.00000 0.05 0.13 Q11 1 -0.0244 -0.4891 -0.3987 11.00000 0.05 0.13 Q12 1 -0.3332 -0.4074 -0.2099 11.00000 0.05 0.13 Q13 1 0.1677 -0.5712 -0.5547 11.00000 0.05 0.13 Q14 1 -0.3600 -0.4397 -0.3971 11.00000 0.05 0.13 Q15 1 0.1483 -0.5699 -0.2485 11.00000 0.05 0.13 Q16 1 0.3804 -0.3453 -0.1443 11.00000 0.05 0.13 Q17 1 0.2201 -0.4891 -0.6990 11.00000 0.05 0.13 Q18 1 0.3056 -0.3241 0.1180 11.00000 0.05 0.13 Q19 1 0.0409 -0.3976 0.1853 11.00000 0.05 0.12 Q20 1 -0.1689 -0.3993 -0.6428 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0469 for 2157 Fo > 4sig(Fo) and 0.0607 for all 4414 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.25, deepest hole -0.22 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0607 REM R1_gt = 0.0469 REM wR_ref = 0.1048 REM GOOF = 1.064 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 4414 REM Reflections_gt = 2157 REM Parameters = n/a REM Hole = -0.22 REM Peak = 0.25 REM Flack = -1.0(15) ; _cod_data_source_file cs8b04163_si_003.cif _cod_data_source_block zhangbsh_0906 _cod_database_code 4515772 _reflns_odcompleteness_completeness 99.45 _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.a Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C11(H11A,H11B), C2(H2A,H2B), C3(H3A,H3B), C1(H1A,H1B) 2.b Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C8(H8) 2.c Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C) ; _olex2_date_sample_data_collection 2018-09-06 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x+1/2, y+1/2, z+1/2' 4 'x+1/2, -y+1/2, 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_calc_flag _atom_site_refinement_flags_posn N1 N -0.21529(18) -0.33459(12) -0.3346(3) 0.0264(5) Uani 1 d . C6 C -0.1194(2) -0.29599(16) -0.0520(3) 0.0303(7) Uani 1 d . H6 H -0.1922 -0.2715 -0.0210 0.036 Uiso 1 calc R O1 O 0.33182(16) -0.39595(12) 0.0141(2) 0.0375(5) Uani 1 d . O2 O 0.37565(17) -0.47791(13) -0.1911(2) 0.0425(6) Uani 1 d . O3 O -0.42817(16) -0.30063(12) -0.5462(2) 0.0390(5) Uani 1 d . C15 C 0.3075(2) -0.43249(16) -0.1337(4) 0.0304(7) Uani 1 d . N2 N 0.19809(18) -0.41007(13) -0.2125(3) 0.0312(6) Uani 1 d . C12 C 0.1529(2) -0.44485(15) -0.3792(3) 0.0282(6) Uani 1 d . C5 C -0.1126(2) -0.33042(15) -0.2133(3) 0.0260(6) Uani 1 d . C7 C -0.0179(2) -0.29828(16) 0.0619(3) 0.0288(6) Uani 1 d . H7 H -0.0236 -0.2742 0.1678 0.035 Uiso 1 calc R C9 C 0.0996(2) -0.36774(15) -0.1392(3) 0.0250(6) Uani 1 d . C4 C -0.3415(2) -0.32473(19) -0.2593(4) 0.0403(8) Uani 1 d . H4A H -0.3520 -0.2758 -0.2224 0.048 Uiso 1 calc R H4B H -0.3515 -0.3550 -0.1577 0.048 Uiso 1 calc R C10 C 0.0003(2) -0.36434(16) -0.2573(3) 0.0275(6) Uani 1 d . C8 C 0.0922(2) -0.33526(15) 0.0238(3) 0.0282(6) Uani 1 d . H8 H 0.1581 -0.3382 0.1039 0.034 Uiso 1 calc R C16 C 0.4443(2) -0.4179(2) 0.1070(4) 0.0446(9) Uani 1 d . H16A H 0.5139 -0.4204 0.0269 0.067 Uiso 1 calc GR H16B H 0.4306 -0.4638 0.1583 0.067 Uiso 1 calc GR H16C H 0.4629 -0.3842 0.1975 0.067 Uiso 1 calc GR C11 C 0.0344(3) -0.40129(19) -0.4243(4) 0.0410(8) Uani 1 d . H11A H 0.0523 -0.3672 -0.5161 0.049 Uiso 1 calc R H11B H -0.0337 -0.4320 -0.4626 0.049 Uiso 1 calc R C2 C -0.2039(2) -0.2900(2) -0.4897(4) 0.0447(9) Uani 1 d . H2A H -0.1214 -0.2964 -0.5422 0.054 Uiso 1 calc R H2B H -0.2128 -0.2405 -0.4573 0.054 Uiso 1 calc R C13 C 0.2503(3) -0.4381(2) -0.5252(4) 0.0423(8) Uani 1 d . H13A H 0.2772 -0.3896 -0.5344 0.063 Uiso 1 calc GR H13B H 0.2133 -0.4529 -0.6340 0.063 Uiso 1 calc GR H13C H 0.3217 -0.4677 -0.4992 0.063 Uiso 1 calc GR C3 C -0.4401(3) -0.34333(19) -0.3961(4) 0.0458(8) Uani 1 d . H3A H -0.4310 -0.3928 -0.4288 0.055 Uiso 1 calc R H3B H -0.5236 -0.3371 -0.3465 0.055 Uiso 1 calc R C14 C 0.1190(3) -0.52123(18) -0.3442(4) 0.0525(9) Uani 1 d . H14A H 0.1926 -0.5465 -0.3059 0.079 Uiso 1 calc GR H14B H 0.0872 -0.5425 -0.4496 0.079 Uiso 1 calc GR H14C H 0.0554 -0.5233 -0.2549 0.079 Uiso 1 calc GR C1 C -0.3057(3) -0.3100(2) -0.6199(4) 0.0557(11) Uani 1 d . H1A H -0.2976 -0.2808 -0.7238 0.067 Uiso 1 calc R H1B H -0.2949 -0.3592 -0.6544 0.067 Uiso 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 N1 0.0217(10) 0.0341(14) 0.0234(11) 0.0032(11) -0.0010(8) 0.0039(10) C6 0.0288(13) 0.0323(18) 0.0299(15) -0.0018(14) 0.0047(12) 0.0063(13) O1 0.0296(9) 0.0494(14) 0.0333(11) -0.0068(11) -0.0127(8) 0.0086(10) O2 0.0327(9) 0.0586(16) 0.0361(11) -0.0053(11) -0.0007(8) 0.0197(10) O3 0.0267(9) 0.0539(15) 0.0364(11) 0.0036(11) -0.0038(8) 0.0115(10) C15 0.0256(13) 0.0385(19) 0.0272(14) 0.0044(15) 0.0004(11) 0.0035(13) N2 0.0276(10) 0.0414(15) 0.0246(12) -0.0049(12) -0.0049(9) 0.0099(11) C12 0.0265(12) 0.0343(17) 0.0238(13) -0.0057(14) -0.0010(11) 0.0026(12) C5 0.0252(11) 0.0297(16) 0.0231(13) 0.0024(13) 0.0001(10) 0.0039(12) C7 0.0353(13) 0.0327(17) 0.0185(13) -0.0069(12) 0.0027(10) 0.0019(13) C9 0.0240(11) 0.0284(16) 0.0225(12) 0.0012(13) 0.0018(10) 0.0024(12) C4 0.0247(12) 0.064(2) 0.0320(14) 0.0077(17) 0.0035(10) 0.0017(14) C10 0.0279(13) 0.0335(17) 0.0210(12) -0.0017(13) -0.0018(10) 0.0044(12) C8 0.0337(13) 0.0281(16) 0.0228(14) 0.0018(13) -0.0039(11) -0.0015(13) C16 0.0246(13) 0.078(3) 0.0312(15) 0.0033(17) -0.0074(12) 0.0067(16) C11 0.0351(14) 0.058(2) 0.0295(15) -0.0123(16) -0.0085(11) 0.0153(16) C2 0.0241(13) 0.075(3) 0.0353(17) 0.0180(17) 0.0019(11) 0.0053(15) C13 0.0372(14) 0.061(2) 0.0290(16) -0.0010(17) 0.0007(12) -0.0051(15) C3 0.0302(14) 0.051(2) 0.056(2) 0.0107(18) -0.0057(13) -0.0047(15) C14 0.068(2) 0.046(2) 0.0434(18) 0.0037(19) -0.0143(17) -0.0160(19) C1 0.0328(15) 0.105(3) 0.0291(16) 0.003(2) -0.0003(12) 0.0242(18) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C5 N1 C4 115.5(2) C5 N1 C2 115.6(2) C2 N1 C4 108.7(2) C5 C6 H6 120.0 C7 C6 H6 120.0 C7 C6 C5 120.1(2) C15 O1 C16 115.0(2) C3 O3 C1 109.4(2) O1 C15 N2 111.8(2) O2 C15 O1 123.7(2) O2 C15 N2 124.4(3) C15 N2 C12 120.3(2) C15 N2 C9 128.1(2) C9 N2 C12 110.00(18) N2 C12 C11 102.5(2) N2 C12 C13 111.5(2) C13 C12 C11 110.1(2) C14 C12 N2 109.9(2) C14 C12 C11 110.7(2) C14 C12 C13 111.8(3) C6 C5 N1 124.0(2) C6 C5 C10 118.0(2) C10 C5 N1 118.0(2) C6 C7 H7 118.8 C6 C7 C8 122.4(2) C8 C7 H7 118.8 C10 C9 N2 108.9(2) C8 C9 N2 129.7(2) C8 C9 C10 121.3(2) N1 C4 H4A 109.9 N1 C4 H4B 109.9 N1 C4 C3 109.1(2) H4A C4 H4B 108.3 C3 C4 H4A 109.9 C3 C4 H4B 109.9 C5 C10 C11 128.6(2) C9 C10 C5 120.9(2) C9 C10 C11 110.5(2) C7 C8 H8 121.4 C9 C8 C7 117.1(2) C9 C8 H8 121.4 O1 C16 H16A 109.5 O1 C16 H16B 109.5 O1 C16 H16C 109.5 H16A C16 H16B 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C12 C11 H11A 110.8 C12 C11 H11B 110.8 C10 C11 C12 104.7(2) C10 C11 H11A 110.8 C10 C11 H11B 110.8 H11A C11 H11B 108.9 N1 C2 H2A 109.8 N1 C2 H2B 109.8 N1 C2 C1 109.4(3) H2A C2 H2B 108.2 C1 C2 H2A 109.8 C1 C2 H2B 109.8 C12 C13 H13A 109.5 C12 C13 H13B 109.5 C12 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 O3 C3 C4 111.6(2) O3 C3 H3A 109.3 O3 C3 H3B 109.3 C4 C3 H3A 109.3 C4 C3 H3B 109.3 H3A C3 H3B 108.0 C12 C14 H14A 109.5 C12 C14 H14B 109.5 C12 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 O3 C1 C2 110.9(2) O3 C1 H1A 109.5 O3 C1 H1B 109.5 C2 C1 H1A 109.5 C2 C1 H1B 109.5 H1A C1 H1B 108.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C5 1.432(3) N1 C4 1.467(3) N1 C2 1.458(4) C6 H6 0.9300 C6 C5 1.394(4) C6 C7 1.384(4) O1 C15 1.347(3) O1 C16 1.448(3) O2 C15 1.202(3) O3 C3 1.407(4) O3 C1 1.426(3) C15 N2 1.373(3) N2 C12 1.510(3) N2 C9 1.428(3) C12 C11 1.540(4) C12 C13 1.525(4) C12 C14 1.507(4) C5 C10 1.398(3) C7 H7 0.9300 C7 C8 1.390(4) C9 C10 1.388(3) C9 C8 1.390(3) C4 H4A 0.9700 C4 H4B 0.9700 C4 C3 1.519(4) C10 C11 1.498(4) C8 H8 0.9300 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C11 H11A 0.9700 C11 H11B 0.9700 C2 H2A 0.9700 C2 H2B 0.9700 C2 C1 1.514(4) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C3 H3A 0.9700 C3 H3B 0.9700 C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C1 H1A 0.9700 C1 H1B 0.9700 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 N1 C5 C10 C9 -174.2(3) N1 C5 C10 C11 5.1(5) N1 C4 C3 O3 -59.2(4) N1 C2 C1 O3 59.8(4) C6 C5 C10 C9 4.3(4) C6 C5 C10 C11 -176.4(3) C6 C7 C8 C9 3.0(4) O1 C15 N2 C12 -179.3(2) O1 C15 N2 C9 -15.6(4) O2 C15 N2 C12 2.5(4) O2 C15 N2 C9 166.2(3) C15 N2 C12 C11 -177.1(2) C15 N2 C12 C13 -59.4(3) C15 N2 C12 C14 65.1(3) C15 N2 C9 C10 -173.3(3) C15 N2 C9 C8 4.3(5) N2 C12 C11 C10 -17.9(3) N2 C9 C10 C5 175.3(3) N2 C9 C10 C11 -4.2(3) N2 C9 C8 C7 -178.4(3) C12 N2 C9 C10 -8.2(3) C12 N2 C9 C8 169.3(3) C5 N1 C4 C3 -170.1(3) C5 N1 C2 C1 169.5(2) C5 C6 C7 C8 -1.3(4) C5 C10 C11 C12 -165.0(3) C7 C6 C5 N1 176.0(3) C7 C6 C5 C10 -2.4(4) C9 N2 C12 C11 16.5(3) C9 N2 C12 C13 134.2(3) C9 N2 C12 C14 -101.3(3) C9 C10 C11 C12 14.4(3) C4 N1 C5 C6 -22.0(4) C4 N1 C5 C10 156.4(3) C4 N1 C2 C1 -58.6(3) C10 C9 C8 C7 -1.1(4) C8 C9 C10 C5 -2.6(4) C8 C9 C10 C11 178.0(3) C16 O1 C15 O2 -3.3(4) C16 O1 C15 N2 178.5(2) C2 N1 C5 C6 106.5(3) C2 N1 C5 C10 -75.0(3) C2 N1 C4 C3 58.0(3) C13 C12 C11 C10 -136.6(3) C3 O3 C1 C2 -59.4(4) C14 C12 C11 C10 99.3(3) C1 O3 C3 C4 59.3(3) loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_meas _refln_F_squared_sigma _refln_scale_group_code 0 0 -9 19.2038 115.339 2 0 0 -8 3074.92 434.276 2 0 0 -7 182.939 142.049 2 0 0 -6 9297.75 611.613 2 0 0 -5 139.626 94.4934 2 0 0 -5 17.6847 30.8423 1 0 0 -4 36726.7 960.813 2 0 0 -4 36038.7 782.757 1 0 0 -3 -4.72291 48.8147 2 0 0 -3 0.66528 44.5978 1 0 0 -2 58682.2 798.474 1 0 0 -2 60060.5 839.586 2 0 0 2 60077 808.606 1 0 0 3 31.0739 37.7285 1 0 -1 -9 -65.3605 133.763 2 0 -1 -8 52.7801 140.429 2 0 1 -8 59.6146 117.994 2 0 -1 -7 5136.84 501.038 2 0 1 -7 5179.23 509.858 2 0 1 -6 49.7005 121.404 2 0 -1 -6 -26.4694 98.9612 2 0 1 -5 8526.58 528.61 2 0 -1 -5 9509.51 552.34 2 0 1 -5 8251.17 295.87 1 0 1 -4 47.1194 69.9486 2 0 1 -4 -10.3169 26.1768 1 0 -1 -4 -15.5299 58.7708 2 0 1 -3 82131.7 859.9 1 0 -1 -3 82136.8 1271.27 1 0 1 -3 82855.2 1246.3 2 0 -1 -3 81716.6 1212.72 2 0 -1 -2 20.0057 39.3568 1 0 -1 -2 46.5417 33.3804 2 0 1 2 13.385 34.816 1 0 1 3 79274.8 1283.73 1 0 1 4 18.6671 42.6203 1 0 -2 -9 153.196 151.708 2 0 -2 -8 806.161 224.669 2 0 -2 -7 124.364 129.768 2 0 2 -7 -60.5508 121.702 2 0 2 -6 8734.45 602.268 2 0 -2 -6 9161.5 600.316 2 0 2 -5 2.00357 9.95833 1 0 -2 -5 76.1497 88.962 2 0 2 -5 -56.442 118.255 2 0 2 -4 49129.3 1143.36 2 0 -2 -4 49474.7 1096.23 2 0 2 -4 46387.1 438.769 1 0 2 -3 58.0842 58.3786 2 0 -2 -3 -27.7759 38.0324 2 0 -2 -2 70133.2 1215.74 1 0 2 1 78.65 62.8082 1 0 2 2 68375.6 1205.53 1 0 2 3 211.497 90.1617 1 0 2 4 45152.6 1165.25 1 0 2 5 -114.83 78.3194 1 0 -3 -9 3440.3 490.394 2 0 -3 -8 83.497 125.464 2 0 -3 -7 7272.68 596.344 2 0 -3 -6 -21.6105 97.7326 2 0 -3 -5 16578.7 722.753 2 0 -3 -4 94.2645 82.3096 2 0 3 -1 154698 1154.74 1 0 3 1 151442 1755.53 1 0 -3 1 157442 1137.98 1 0 3 2 25.9796 54.344 1 0 3 3 22398.2 836.588 1 0 3 4 -61.1568 70.5433 1 0 3 5 15143.3 768.189 1 0 -4 -9 62.9009 152.607 2 0 -4 -8 4714.15 531.29 2 0 -4 -7 -3.49911 115.053 2 0 -4 -6 7084.83 533.992 2 0 -4 -5 -97.7985 96.5068 2 0 4 -2 10447.1 271.69 1 0 4 -1 -7.60476 41.9491 1 0 4 0 156434 1748.04 1 0 -4 1 8.41646 40.5714 1 0 4 1 44.8141 96.9045 1 0 -4 2 9600.84 194.195 1 0 4 2 9784.07 550.641 1 0 4 3 30.815 85.2224 1 0 4 4 12238 708.233 1 0 4 5 -73.4577 77.5432 1 0 4 6 6593.22 566.8 1 0 -5 -9 1246.98 318.144 2 0 -5 -8 -52.4561 148.979 2 0 -5 -7 1787.23 312.587 2 0 -5 -6 -8.55583 85.0991 2 0 -5 -5 812.485 165.863 2 0 5 -2 17.8712 25.5632 1 0 5 -1 65681 1097.44 1 0 5 0 107.795 70.8471 1 0 5 1 70066.8 1459.06 1 0 -5 1 70132.7 1105.63 1 0 -5 2 40.6094 17.6097 1 0 5 2 -34.9061 63.8753 1 0 5 3 88768.6 1915.39 1 0 5 4 30.4325 70.4055 1 0 5 5 797.025 211.136 1 0 5 6 -16.9071 101.155 1 0 -6 -9 31.6386 120.768 2 0 -6 -8 2962.66 432.796 2 0 -6 -7 -6.28088 98.6778 2 0 -6 -6 1215.32 244.852 2 0 6 -2 61617.1 1014.2 1 0 6 -1 17.4293 43.8238 1 0 6 0 45485.2 1143.56 1 0 6 1 7.83785 62.5947 1 0 -6 1 -8.48643 33.6535 1 0 -6 2 62654.3 923.839 1 0 6 2 62569.1 1597.56 1 0 -6 3 127.126 25.2175 1 0 6 3 81.4727 100.363 1 0 6 4 8844.96 679.239 1 0 6 5 35.6389 72.9341 1 0 6 6 639.574 196.475 1 0 -7 -9 2957.88 482.088 2 0 -7 -8 -21.1677 124.894 2 0 -7 -7 8506.61 670.842 2 0 -7 -6 -23.534 106.66 2 0 7 -2 42.9748 62.5235 1 0 7 -1 21300.7 767.043 1 0 7 0 194.656 105.624 1 0 7 1 23257.7 962.511 1 0 7 2 -21.2041 125.889 1 0 -7 2 -8.27491 25.7438 1 0 7 3 22522.5 1074.01 1 0 -7 3 22800.9 396.688 1 0 7 4 -1.7356 80.5145 1 0 7 5 4174.25 506.958 1 0 7 6 -42.307 110.901 1 0 7 7 6811.33 691.81 1 0 -8 -9 -38.6725 159.16 2 0 -8 -8 360.748 183.443 2 0 -8 -7 29.8669 122.188 2 0 -8 -6 6081.44 535.096 2 0 8 -3 48.6429 45.2192 1 0 8 -2 24573 803.463 1 0 8 -1 10.4846 55.822 1 0 8 0 136921 2294.47 1 0 8 1 -80.3095 102.179 1 0 8 2 26426.2 1157.9 1 0 -8 3 61.2065 31.1703 1 0 8 3 24.6959 109.199 1 0 8 4 4316.45 515.937 1 0 8 5 -40.4994 110.886 1 0 8 6 5222.44 609.007 1 0 8 7 -121.201 130.218 1 0 -9 -8 85.4637 164.352 2 0 -9 -7 4488.28 522.939 2 0 9 -3 14774.4 587.554 1 0 9 -2 34.7494 60.0045 1 0 9 -1 8455.14 562.218 1 0 9 0 121.625 133.435 1 0 9 1 9292.51 680.88 1 0 9 2 26.305 101.318 1 0 -9 3 13017.5 428.841 1 0 9 3 13606.2 924.782 1 0 -9 4 -4.51939 11.1487 1 0 9 4 -5.92288 103.245 1 0 9 5 1684.85 352.596 1 0 9 6 9.66291 161.346 1 0 9 7 4383.67 594.907 1 0 -10 -8 6424.23 671.57 2 0 -10 -7 47.171 105.022 2 0 10 -3 72.1045 64.1806 1 0 10 -2 43995.8 1243.67 1 0 10 -1 -2.06803 80.4544 1 0 10 0 17397.4 913.264 1 0 10 1 61.4363 100.688 1 0 10 2 46351.7 1685.3 1 0 10 3 -268.196 164.118 1 0 10 4 13231.1 982.698 1 0 10 5 61.9353 129.474 1 0 10 6 1080.47 314.779 1 0 10 7 15.5784 135.778 1 0 -11 -8 52.3596 132.237 2 0 -11 -7 1320.54 299.135 2 0 11 -3 11467.1 617.65 1 0 11 -2 45.9891 65.7916 1 0 11 -1 27361.4 1125.66 1 0 11 0 506.721 202.434 1 0 11 1 27645.9 1278 1 0 11 2 225.734 182.376 1 0 11 3 11498.1 911.536 1 0 11 4 168.55 229.14 1 0 11 5 3585.21 557.178 1 0 11 6 14.1896 160.339 1 0 11 7 1189.19 355.305 1 0 -12 -8 4876.02 633.995 2 0 12 -3 10.0551 57.9698 1 0 12 -2 28843.2 1129.77 1 0 12 -1 43.0298 108.812 1 0 12 0 1579.56 328.737 1 0 12 1 -12.2336 103.791 1 0 12 2 27207.5 1384.68 1 0 12 3 3.8453 144.87 1 0 12 4 5926.7 713.609 1 0 12 5 -9.89179 125.652 1 0 12 6 537.924 257.07 1 0 12 7 55.4039 165.927 1 0 -13 -8 299.162 207.093 2 0 13 -3 10001.8 649.442 1 0 13 -2 -56.5199 113.238 1 0 13 -1 8763.29 705.712 1 0 13 0 1293.86 308.228 1 0 13 1 9170.63 796.489 1 0 13 2 -9.81779 116.029 1 0 13 3 10246 934.87 1 0 13 4 -89.6351 164.034 1 0 13 5 18339.4 1321.54 1 0 13 6 -33.0219 197.651 1 0 13 7 1404.05 385.254 1 0 -14 -8 4863.54 662.992 2 0 14 -3 77.5871 119.711 1 0 14 -2 5637.12 550.511 1 0 14 -1 -29.7654 124.392 1 0 14 0 1004.02 310.712 1 0 14 1 -180.327 161.104 1 0 14 2 4831.75 630.685 1 0 14 3 34.4141 166.153 1 0 14 4 2477.41 494.298 1 0 14 5 52.689 158.651 1 0 14 6 452.099 205.606 1 0 14 7 73.3997 152.722 1 0 15 -3 5465.07 532.305 1 0 15 -2 -221.626 139.83 1 0 15 -1 3263.19 475.684 1 0 15 0 808.637 269.804 1 0 15 1 2177.44 425.256 1 0 15 2 23.0636 131.47 1 0 15 3 5755.9 740.137 1 0 15 4 -16.9844 158.708 1 0 15 5 530.063 318.035 1 0 15 6 -87.0549 179.634 1 0 15 7 757.274 314.753 1 0 16 -3 48.2766 90.8296 1 0 16 -2 6779.71 662.51 1 0 16 -1 -131.325 149.316 1 0 16 0 3729.39 545.745 1 0 16 1 40.1754 136.977 1 0 16 2 7490.63 833.691 1 0 16 3 10.6423 137.09 1 0 16 4 3354.16 610.196 1 0 16 5 -19.1623 142.945 1 0 16 6 380.596 202.07 1 0 16 7 91.5406 156.839 1 0 17 -2 60.271 119.35 1 0 17 -1 771.236 261.919 1 0 17 0 489.672 237.933 1 0 17 1 677.98 271.744 1 0 17 2 -69.4066 164.509 1 0 17 3 15142.3 1256.83 1 0 17 4 44.3367 172.145 1 0 17 5 3345.2 635.848 1 0 17 6 385.905 272.864 1 0 17 7 364.573 261.023 1 0 18 -2 4540.52 580.309 1 0 18 -1 -134.567 147.858 1 0 18 0 175.303 152.133 1 0 18 1 -199.181 183.865 1 0 18 2 5820.55 761.303 1 0 18 3 49.6735 133.02 1 0 18 4 79.4196 149.59 1 0 18 5 -111.653 217.991 1 0 18 6 1329.17 451.209 1 0 19 -2 78.3583 153.691 1 0 19 -1 1644.5 391.631 1 0 19 0 688.803 299.945 1 0 19 1 1646.59 407.175 1 0 19 2 59.2517 185.496 1 0 19 3 498.741 279.143 1 0 19 4 -127.869 184.046 1 0 19 5 400.216 214.844 1 0 20 -2 9933.3 909.265 1 0 20 -1 -251.882 203.835 1 0 20 0 297.183 206.148 1 0 20 1 -263.131 215.338 1 0 20 2 8633.31 1008.05 1 0 20 3 -182.4 211.937 1 0 20 4 381.593 253.612 1 0 20 5 102.767 188.985 1 0 21 -2 -331.714 197.153 1 0 21 -1 1225.22 355.373 1 0 21 0 297.607 239.659 1 0 21 1 295.851 247.171 1 0 21 2 -343.482 252.686 1 0 21 3 1990.58 525.939 1 0 21 4 -318.139 247.514 1 0 22 -1 -146.769 164.005 1 0 22 0 3913.57 668.91 1 0 22 1 -11.8812 146.922 1 0 22 2 5211.15 806.14 1 0 22 3 17.4752 234.816 1 0 23 -1 1303.87 392.201 1 0 23 0 794.167 339.42 1 0 23 1 1188.77 408.483 1 0 23 2 -10.6496 206.574 1 0 24 -1 -12.7628 142.88 1 0 24 0 585.299 307.475 1 0 24 1 121.97 211.294 1 0 25 0 617.489 314.314 1 -1 0 -9 21.085 127.609 2 1 0 -8 -84.4036 132.543 2 -1 0 -8 -365.258 178.858 2 -1 0 -7 -0.54727 116.142 2 1 0 -7 72.9747 125.997 2 1 0 -6 76.1936 126.305 2 -1 0 -6 -131.671 122.549 2 -1 0 -5 -39.1506 91.1504 2 1 0 -5 -41.2271 76.3216 2 1 0 -4 62.7877 58.2026 2 -1 0 -4 5.53261 54.899 1 -1 0 -4 120.832 74.0695 2 1 0 -4 8.13791 22.0071 1 1 0 -3 31.0722 26.8706 1 1 0 -3 42.772 44.3493 2 -1 0 -3 1.0845 32.7321 1 -1 0 -3 -13.1227 39.2993 2 -1 0 -2 8.48695 28.3041 2 1 0 -2 -3.42932 12.6085 1 1 0 -2 -1.70836 22.3808 2 -1 0 2 47.3832 34.772 1 -1 0 3 48.7449 38.675 1 -1 0 4 25.5536 35.8547 1 -1 0 5 60.5078 60.7022 1 -1 0 6 -105.757 67.0567 1 -1 1 -9 544.3 217.923 2 -1 -1 -9 442.877 194.586 2 1 -1 -9 589.474 229.971 2 -1 -1 -8 498.006 179.719 2 1 -1 -8 771.393 218.249 2 -1 1 -8 436.956 174.906 2 -1 -1 -7 2014.46 326.631 2 1 -1 -7 2641.1 367.139 2 -1 1 -7 2158.3 318.87 2 1 1 -7 2117.33 334.414 2 1 1 -6 1459.88 248.07 2 -1 1 -6 1278.34 245.236 2 -1 -1 -6 1358.35 230.369 2 1 -1 -6 1225.41 229.475 2 -1 1 -5 24447.1 720.794 1 -1 -1 -5 24550 875.05 2 1 -1 -5 24306.6 883.985 2 1 1 -5 24205.5 901.218 2 -1 1 -5 24923 896.079 2 1 1 -5 22938 453.582 1 -1 1 -4 355.726 107.363 2 1 -1 -4 365.299 104.429 2 1 1 -4 369.869 104.218 2 -1 -1 -4 321.446 100.446 2 1 1 -4 388.45 55.6779 1 -1 1 -4 346.714 82.3105 1 -1 -1 -3 20566.4 607.928 2 1 1 -3 21198.7 358.187 1 1 -1 -3 20518.5 613.776 2 -1 1 -3 20706 619.974 2 1 -1 -3 21494.6 524.11 1 1 1 -3 21385.5 650.493 2 -1 1 -3 20607 572.505 1 -1 -1 -3 21085.5 727.169 1 1 -1 -2 17102.3 409.49 1 1 1 -2 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