#------------------------------------------------------------------------------ #$Date: 2024-07-04 07:50:12 +0300 (Thu, 04 Jul 2024) $ #$Revision: 292730 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572057.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_1572057 loop_ _publ_author_name 'Zhou, Yu-Qiang' 'He, Kui-Cheng' 'Zheng, Wei-Hao' 'Lv, Jing-Fang' 'He, Shi-Mei' 'Yu, Ning' 'Yang, Yun-Bo' 'Liu, Lv-Yan' 'Jiang, Kun' 'Wei, Ye' _publ_section_title ; 1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls. ; _journal_issue 20 _journal_name_full 'Chemical science' _journal_page_first 7502 _journal_page_last 7514 _journal_paper_doi 10.1039/d4sc01858c _journal_volume 15 _journal_year 2024 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C30 H29 N O2' _chemical_formula_sum 'C30 H29 N O2' _chemical_formula_weight 435.54 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2023-05-11 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-11-09 deposited with the CCDC. 2024-04-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.15719(19) _cell_length_b 11.2106(2) _cell_length_c 27.1349(6) _cell_measurement_reflns_used 7509 _cell_measurement_temperature 291.19(10) _cell_measurement_theta_max 71.4420 _cell_measurement_theta_min 3.9350 _cell_volume 2481.41(9) _computing_cell_refinement 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _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_environment air _diffrn_ambient_temperature 291.19(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.0243 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.983 _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 -103.00 -19.00 1.00 1.00 -- -35.97 -57.00-120.00 84 2 \w -105.00 -17.00 1.00 1.00 -- -35.97 -38.00 -60.00 88 3 \w 28.00 90.00 1.00 1.00 -- 35.97-126.00 0.00 62 4 \w -35.00 65.00 1.00 1.00 -- 35.97 -19.00 -90.00 100 5 \w 103.00 176.00 1.00 1.39 -- 107.97 77.00-120.00 73 6 \w 103.00 176.00 1.00 1.39 -- 107.97 77.00-180.00 73 7 \w 39.00 106.00 1.00 1.39 -- 107.97 -95.00-120.00 67 8 \w 40.00 125.00 1.00 1.39 -- 107.97 -45.00-120.00 85 9 \w 38.00 109.00 1.00 1.39 -- 107.97-112.00 60.00 71 10 \w 87.00 178.00 1.00 1.39 -- 107.97 30.00 60.00 91 11 \w -103.00 -19.00 1.00 1.00 -- -35.97 -57.00 60.00 84 12 \w -103.00 -19.00 1.00 1.00 -- -35.97 -57.00 150.00 84 13 \w -53.00 31.00 1.00 1.00 -- -35.97 57.00-120.00 84 14 \w 6.00 75.00 1.00 1.00 -- 35.97 -99.00 150.00 69 15 \w 70.00 95.00 1.00 1.39 -- 107.97 15.00 150.00 25 16 \w 91.00 176.00 1.00 1.39 -- 107.97 45.00 -30.00 85 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, 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 0.0004618000 _diffrn_orient_matrix_UB_12 -0.1283914000 _diffrn_orient_matrix_UB_13 0.0201785000 _diffrn_orient_matrix_UB_21 -0.0349503000 _diffrn_orient_matrix_UB_22 -0.0481145000 _diffrn_orient_matrix_UB_23 -0.0521236000 _diffrn_orient_matrix_UB_31 0.1857045000 _diffrn_orient_matrix_UB_32 -0.0087647000 _diffrn_orient_matrix_UB_33 -0.0098516000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_unetI/netI 0.0297 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 13056 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.955 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.727 _diffrn_reflns_theta_min 4.267 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.02596 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.166 _exptl_crystal_description block _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.31 _refine_diff_density_max 0.188 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.029 _refine_ls_abs_structure_details ; Flack x determined using 1574 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.13(18) _refine_ls_extinction_coef 0.0036(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 304 _refine_ls_number_reflns 4632 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0502 _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^)+(0.0803P)^2^+0.1720P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1411 _refine_ls_wR_factor_ref 0.1460 _reflns_Friedel_coverage 0.696 _reflns_Friedel_fraction_full 0.961 _reflns_Friedel_fraction_max 0.917 _reflns_number_gt 4280 _reflns_number_total 4632 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL ZYQ-3-crystal in P212121 #19 REM reset to P212121 #19 CELL 1.54184 8.15719 11.21059 27.13488 90 90 90 ZERR 4 0.00019 0.00023 0.00057 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 120 116 4 8 L.S. 40 PLAN 20 SIZE 0.38 0.32 0.31 TEMP 291.19(10) BOND fmap 2 53 acta REM REM REM WGHT 0.080300 0.172000 EXTI 0.003557 FVAR 7.45525 O1 4 -0.442439 -0.249762 -0.225773 11.00000 0.06108 0.08102 = 0.06996 -0.00215 -0.00747 -0.00423 O2 4 -0.242701 -0.258640 -0.281014 11.00000 0.13179 0.14149 = 0.10405 -0.05970 0.04377 -0.05085 N1 3 -0.571506 -0.382263 -0.080395 11.00000 0.04590 0.07264 = 0.08170 0.01414 0.01117 0.00031 C1 1 -0.400126 -0.557874 -0.082780 11.00000 0.04707 0.05479 = 0.05606 0.00763 -0.00327 -0.01060 C2 1 -0.529239 -0.629285 -0.067158 11.00000 0.05449 0.07115 = 0.08667 0.01228 -0.00178 -0.01878 AFIX 43 H2 2 -0.634353 -0.597451 -0.065374 11.00000 -1.20000 AFIX 0 C3 1 -0.503415 -0.747139 -0.054226 11.00000 0.08604 0.06897 = 0.10605 0.02525 -0.00395 -0.03428 AFIX 43 H3 2 -0.590882 -0.794541 -0.044238 11.00000 -1.20000 AFIX 0 C4 1 -0.348463 -0.793570 -0.056213 11.00000 0.09759 0.05352 = 0.10711 0.02689 0.00457 -0.01182 AFIX 43 H4 2 -0.330577 -0.872559 -0.047225 11.00000 -1.20000 AFIX 0 C5 1 -0.219070 -0.724213 -0.071409 11.00000 0.07236 0.05637 = 0.08182 0.01742 -0.00201 0.00270 AFIX 43 H5 2 -0.114569 -0.757228 -0.072727 11.00000 -1.20000 AFIX 0 C6 1 -0.241545 -0.604729 -0.084956 11.00000 0.05069 0.05198 = 0.05588 0.00905 -0.00463 -0.00696 C7 1 -0.097667 -0.525491 -0.099125 11.00000 0.04324 0.05613 = 0.06741 0.01207 -0.00236 -0.00137 C8 1 0.043015 -0.596373 -0.122659 11.00000 0.05679 0.07458 = 0.10800 0.02638 0.01081 0.01532 AFIX 137 H8A 2 0.001275 -0.643153 -0.149505 11.00000 -1.50000 H8B 2 0.091006 -0.648161 -0.098458 11.00000 -1.50000 H8C 2 0.124749 -0.542134 -0.134735 11.00000 -1.50000 AFIX 0 C9 1 -0.034735 -0.462777 -0.052673 11.00000 0.06627 0.08123 = 0.08647 0.01482 -0.02291 -0.01687 AFIX 137 H9A 2 0.051381 -0.408384 -0.061418 11.00000 -1.50000 H9B 2 0.006758 -0.521117 -0.029976 11.00000 -1.50000 H9C 2 -0.122906 -0.419527 -0.037513 11.00000 -1.50000 AFIX 0 C10 1 -0.156705 -0.432140 -0.136530 11.00000 0.04531 0.05295 = 0.06296 0.01147 0.00613 0.00027 AFIX 23 H10A 2 -0.069849 -0.374491 -0.141902 11.00000 -1.20000 H10B 2 -0.178418 -0.471420 -0.167705 11.00000 -1.20000 AFIX 0 C11 1 -0.308236 -0.367509 -0.120352 11.00000 0.04134 0.05032 = 0.05090 0.00709 -0.00146 -0.00294 C12 1 -0.430145 -0.430815 -0.095185 11.00000 0.04102 0.05462 = 0.05775 0.00761 -0.00238 -0.00422 C13 1 -0.594588 -0.267007 -0.090154 11.00000 0.05129 0.07599 = 0.09442 0.01232 0.01655 0.01117 AFIX 43 H13 2 -0.692736 -0.232176 -0.080303 11.00000 -1.20000 AFIX 0 C14 1 -0.481970 -0.196934 -0.113869 11.00000 0.06062 0.05677 = 0.08536 0.00679 0.01045 0.00927 AFIX 43 H14 2 -0.503447 -0.116477 -0.119165 11.00000 -1.20000 AFIX 0 C15 1 -0.336058 -0.246461 -0.129909 11.00000 0.04596 0.05036 = 0.05841 0.00473 0.00028 -0.00154 C16 1 -0.209674 -0.171001 -0.154307 11.00000 0.04754 0.04230 = 0.06714 0.01108 -0.00167 0.00012 C17 1 -0.101226 -0.104674 -0.123549 11.00000 0.05194 0.04710 = 0.07195 0.00743 -0.00203 0.00038 C18 1 -0.108613 -0.111921 -0.071515 11.00000 0.08600 0.06518 = 0.07006 0.00727 -0.00962 -0.01447 AFIX 43 H18 2 -0.185669 -0.161610 -0.056796 11.00000 -1.20000 AFIX 0 C19 1 -0.005253 -0.047649 -0.042767 11.00000 0.11699 0.07744 = 0.07792 0.00186 -0.01906 -0.01706 AFIX 43 H19 2 -0.011653 -0.054227 -0.008656 11.00000 -1.20000 AFIX 0 C20 1 0.110051 0.027897 -0.063801 11.00000 0.09653 0.08727 = 0.10867 -0.00623 -0.03121 -0.02273 AFIX 43 H20 2 0.179662 0.071838 -0.043622 11.00000 -1.20000 AFIX 0 C21 1 0.122170 0.038227 -0.113156 11.00000 0.06869 0.06645 = 0.11789 0.00327 -0.00913 -0.01741 AFIX 43 H21 2 0.199393 0.089750 -0.126670 11.00000 -1.20000 AFIX 0 C22 1 0.018737 -0.028429 -0.144582 11.00000 0.05288 0.05160 = 0.08882 0.00959 -0.00137 -0.00305 C23 1 0.030398 -0.023091 -0.196780 11.00000 0.05413 0.06488 = 0.09311 0.01623 0.00791 -0.01143 AFIX 43 H23 2 0.106371 0.027649 -0.211395 11.00000 -1.20000 AFIX 0 C24 1 -0.067190 -0.090579 -0.225173 11.00000 0.06169 0.06343 = 0.07065 0.01263 0.01053 -0.00493 AFIX 43 H24 2 -0.053535 -0.088365 -0.259187 11.00000 -1.20000 AFIX 0 C25 1 -0.189819 -0.164777 -0.205108 11.00000 0.05086 0.04560 = 0.06838 0.00917 0.00462 0.00220 C26 1 -0.294008 -0.230022 -0.241345 11.00000 0.06879 0.04916 = 0.06739 0.00120 0.00537 0.00109 C27 1 -0.569268 -0.315242 -0.254594 11.00000 0.06822 0.06429 = 0.09259 -0.01329 -0.01866 -0.00021 C28 1 -0.614089 -0.241634 -0.297712 11.00000 0.22269 0.15922 = 0.17197 0.05471 -0.13366 -0.07462 AFIX 137 H28A 2 -0.656969 -0.166489 -0.286682 11.00000 -1.50000 H28B 2 -0.695769 -0.282412 -0.316815 11.00000 -1.50000 H28C 2 -0.518649 -0.228181 -0.317652 11.00000 -1.50000 AFIX 0 C29 1 -0.709382 -0.320450 -0.219756 11.00000 0.07491 0.24626 = 0.15577 -0.06548 -0.00255 -0.04979 AFIX 137 H29A 2 -0.692190 -0.383997 -0.196611 11.00000 -1.50000 H29B 2 -0.808831 -0.334616 -0.237746 11.00000 -1.50000 H29C 2 -0.717742 -0.246105 -0.202380 11.00000 -1.50000 AFIX 0 C30 1 -0.508453 -0.434121 -0.268639 11.00000 0.09889 0.06578 = 0.38070 -0.06123 -0.00115 -0.01309 AFIX 137 H30A 2 -0.412061 -0.425705 -0.288636 11.00000 -1.50000 H30B 2 -0.591565 -0.475490 -0.286951 11.00000 -1.50000 H30C 2 -0.482079 -0.478688 -0.239488 11.00000 -1.50000 AFIX 0 HKLF 4 REM ZYQ-3-crystal in P212121 #19 REM R1 = 0.0502 for 4280 Fo > 4sig(Fo) and 0.0533 for all 4632 data REM 304 parameters refined using 0 restraints END WGHT 0.0803 0.1720 REM Highest difference peak 0.188, deepest hole -0.164, 1-sigma level 0.029 Q1 1 -0.6021 -0.4217 -0.2168 11.00000 0.05 0.19 Q2 1 -0.4041 -0.3198 -0.2319 11.00000 0.05 0.16 Q3 1 -0.6701 -0.2580 -0.2513 11.00000 0.05 0.13 Q4 1 -0.3076 -0.1830 -0.2804 11.00000 0.05 0.13 Q5 1 -0.6503 -0.2276 -0.2988 11.00000 0.05 0.12 Q6 1 -0.4525 -0.3591 -0.3180 11.00000 0.05 0.12 Q7 1 -0.2651 -0.3284 -0.2583 11.00000 0.05 0.12 Q8 1 -0.4464 -0.6047 -0.0613 11.00000 0.05 0.12 Q9 1 -0.0989 -0.0415 -0.1412 11.00000 0.05 0.12 Q10 1 -0.2387 -0.1221 -0.1813 11.00000 0.05 0.11 Q11 1 -0.1707 -0.5669 -0.0953 11.00000 0.05 0.11 Q12 1 -0.3406 -0.5716 -0.0878 11.00000 0.05 0.10 Q13 1 -0.7269 -0.3069 -0.1981 11.00000 0.05 0.10 Q14 1 -0.6359 -0.3403 -0.3242 11.00000 0.05 0.10 Q15 1 -0.1665 -0.2212 -0.1822 11.00000 0.05 0.10 Q16 1 -0.6510 -0.4302 -0.0607 11.00000 0.05 0.10 Q17 1 -0.6571 -0.5630 -0.0625 11.00000 0.05 0.09 Q18 1 -0.0849 -0.0058 -0.1957 11.00000 0.05 0.09 Q19 1 -0.2150 -0.1041 -0.1372 11.00000 0.05 0.09 Q20 1 -0.5456 -0.4035 -0.1660 11.00000 0.05 0.09 REM The information below was added by Olex2. REM REM R1 = 0.0502 for 4280 Fo > 4sig(Fo) and 0.0533 for all 13114 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.19, deepest hole -0.16 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0533 REM R1_gt = 0.0502 REM wR_ref = 0.1460 REM GOOF = 1.057 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 13114 REM Reflections_gt = 4280 REM Parameters = n/a REM Hole = -0.16 REM Peak = 0.19 REM Flack = -0.13(18) ; _cod_data_source_file d4sc01858c2.cif _cod_data_source_block zyq-3-crystal _cod_original_cell_volume 2481.40(9) _cod_database_code 1572057 _shelxl_version_number 2014-1 _chemical_oxdiff_usercomment 'C1 H1 N1 O1' _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 0.845 _shelx_estimated_absorpt_t_min 0.814 _reflns_odcompleteness_completeness 99.88 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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: C10(H10A,H10B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C) ; _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 27.136 _oxdiff_exptl_absorpt_empirical_full_min 0.372 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 O1 O -0.4424(3) -0.2498(2) -0.22577(8) 0.0707(6) Uani 1 1 d . . . . . O2 O -0.2427(5) -0.2586(3) -0.28101(11) 0.1258(14) Uani 1 1 d . . . . . N1 N -0.5715(3) -0.3823(2) -0.08040(10) 0.0667(7) Uani 1 1 d . . . . . C1 C -0.4001(3) -0.5579(2) -0.08278(9) 0.0526(6) Uani 1 1 d . . . . . C2 C -0.5292(4) -0.6293(3) -0.06716(13) 0.0708(8) Uani 1 1 d . . . . . H2 H -0.6344 -0.5975 -0.0654 0.085 Uiso 1 1 calc R . . . . C3 C -0.5034(5) -0.7471(3) -0.05423(16) 0.0870(11) Uani 1 1 d . . . . . H3 H -0.5909 -0.7945 -0.0442 0.104 Uiso 1 1 calc R . . . . C4 C -0.3485(5) -0.7936(3) -0.05621(15) 0.0861(11) Uani 1 1 d . . . . . H4 H -0.3306 -0.8726 -0.0472 0.103 Uiso 1 1 calc R . . . . C5 C -0.2191(5) -0.7242(3) -0.07141(12) 0.0702(8) Uani 1 1 d . . . . . H5 H -0.1146 -0.7572 -0.0727 0.084 Uiso 1 1 calc R . . . . C6 C -0.2415(3) -0.6047(2) -0.08496(9) 0.0529(6) Uani 1 1 d . . . . . C7 C -0.0977(3) -0.5255(3) -0.09912(10) 0.0556(6) Uani 1 1 d . . . . . C8 C 0.0430(4) -0.5964(3) -0.12266(15) 0.0798(10) Uani 1 1 d . . . . . H8A H 0.0013 -0.6432 -0.1495 0.120 Uiso 1 1 calc GR . . . . H8B H 0.0910 -0.6482 -0.0985 0.120 Uiso 1 1 calc GR . . . . H8C H 0.1247 -0.5421 -0.1347 0.120 Uiso 1 1 calc GR . . . . C9 C -0.0347(4) -0.4628(3) -0.05267(13) 0.0780(10) Uani 1 1 d . . . . . H9A H 0.0514 -0.4084 -0.0614 0.117 Uiso 1 1 calc GR . . . . H9B H 0.0068 -0.5211 -0.0300 0.117 Uiso 1 1 calc GR . . . . H9C H -0.1229 -0.4195 -0.0375 0.117 Uiso 1 1 calc GR . . . . C10 C -0.1567(3) -0.4321(2) -0.13653(10) 0.0537(6) Uani 1 1 d . . . . . H10A H -0.0698 -0.3745 -0.1419 0.064 Uiso 1 1 calc R . . . . H10B H -0.1784 -0.4714 -0.1677 0.064 Uiso 1 1 calc R . . . . C11 C -0.3082(3) -0.3675(2) -0.12035(9) 0.0475(5) Uani 1 1 d . . . . . C12 C -0.4301(3) -0.4308(2) -0.09518(9) 0.0511(6) Uani 1 1 d . . . . . C13 C -0.5946(4) -0.2670(3) -0.09015(13) 0.0739(9) Uani 1 1 d . . . . . H13 H -0.6927 -0.2322 -0.0803 0.089 Uiso 1 1 calc R . . . . C14 C -0.4820(4) -0.1969(3) -0.11387(13) 0.0676(8) Uani 1 1 d . . . . . H14 H -0.5034 -0.1165 -0.1192 0.081 Uiso 1 1 calc R . . . . C15 C -0.3361(3) -0.2465(2) -0.12991(9) 0.0516(6) Uani 1 1 d . . . . . C16 C -0.2097(3) -0.1710(2) -0.15431(10) 0.0523(6) Uani 1 1 d . . . . . C17 C -0.1012(4) -0.1047(2) -0.12355(11) 0.0570(6) Uani 1 1 d . . . . . C18 C -0.1086(5) -0.1119(3) -0.07151(12) 0.0737(9) Uani 1 1 d . . . . . H18 H -0.1857 -0.1616 -0.0568 0.088 Uiso 1 1 calc R . . . . C19 C -0.0053(5) -0.0476(3) -0.04277(15) 0.0908(12) Uani 1 1 d . . . . . H19 H -0.0117 -0.0542 -0.0087 0.109 Uiso 1 1 calc R . . . . C20 C 0.1101(6) 0.0279(4) -0.06380(18) 0.0975(12) Uani 1 1 d . . . . . H20 H 0.1797 0.0718 -0.0436 0.117 Uiso 1 1 calc R . . . . C21 C 0.1222(4) 0.0382(3) -0.11316(17) 0.0843(10) Uani 1 1 d . . . . . H21 H 0.1994 0.0897 -0.1267 0.101 Uiso 1 1 calc R . . . . C22 C 0.0187(4) -0.0284(3) -0.14458(13) 0.0644(7) Uani 1 1 d . . . . . C23 C 0.0304(4) -0.0231(3) -0.19678(13) 0.0707(8) Uani 1 1 d . . . . . H23 H 0.1064 0.0276 -0.2114 0.085 Uiso 1 1 calc R . . . . C24 C -0.0672(4) -0.0906(3) -0.22517(11) 0.0653(8) Uani 1 1 d . . . . . H24 H -0.0535 -0.0884 -0.2592 0.078 Uiso 1 1 calc R . . . . C25 C -0.1898(4) -0.1648(2) -0.20511(10) 0.0549(6) Uani 1 1 d . . . . . C26 C -0.2940(4) -0.2300(2) -0.24134(11) 0.0618(7) Uani 1 1 d . . . . . C27 C -0.5693(5) -0.3152(3) -0.25459(13) 0.0750(9) Uani 1 1 d . . . . . C28 C -0.6141(11) -0.2416(6) -0.2977(3) 0.185(4) Uani 1 1 d . . . . . H28A H -0.6570 -0.1665 -0.2867 0.277 Uiso 1 1 calc GR . . . . H28B H -0.6958 -0.2824 -0.3168 0.277 Uiso 1 1 calc GR . . . . H28C H -0.5186 -0.2282 -0.3177 0.277 Uiso 1 1 calc GR . . . . C29 C -0.7094(6) -0.3205(7) -0.2198(2) 0.159(3) Uani 1 1 d . . . . . H29A H -0.6922 -0.3840 -0.1966 0.238 Uiso 1 1 calc GR . . . . H29B H -0.8088 -0.3346 -0.2377 0.238 Uiso 1 1 calc GR . . . . H29C H -0.7177 -0.2461 -0.2024 0.238 Uiso 1 1 calc GR . . . . C30 C -0.5085(7) -0.4341(4) -0.2686(4) 0.182(4) Uani 1 1 d . . . . . H30A H -0.4121 -0.4257 -0.2886 0.273 Uiso 1 1 calc GR . . . . H30B H -0.5916 -0.4755 -0.2870 0.273 Uiso 1 1 calc GR . . . . H30C H -0.4821 -0.4787 -0.2395 0.273 Uiso 1 1 calc GR . . . . 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 O1 0.0611(13) 0.0810(14) 0.0700(11) -0.0022(10) -0.0075(10) -0.0042(12) O2 0.132(3) 0.141(3) 0.1041(19) -0.060(2) 0.044(2) -0.051(2) N1 0.0459(12) 0.0726(15) 0.0817(15) 0.0141(13) 0.0112(12) 0.0003(12) C1 0.0471(13) 0.0548(14) 0.0561(12) 0.0076(11) -0.0033(11) -0.0106(12) C2 0.0545(16) 0.0711(18) 0.087(2) 0.0123(16) -0.0018(16) -0.0188(15) C3 0.086(3) 0.069(2) 0.106(3) 0.0252(18) -0.004(2) -0.034(2) C4 0.098(3) 0.0535(17) 0.107(3) 0.0269(18) 0.005(2) -0.0118(18) C5 0.072(2) 0.0564(15) 0.0818(18) 0.0174(14) -0.0020(17) 0.0027(15) C6 0.0507(14) 0.0520(13) 0.0559(12) 0.0090(11) -0.0046(12) -0.0070(12) C7 0.0432(13) 0.0561(14) 0.0674(15) 0.0121(12) -0.0024(12) -0.0014(12) C8 0.0568(17) 0.075(2) 0.108(2) 0.0264(18) 0.0108(19) 0.0153(16) C9 0.0663(19) 0.081(2) 0.086(2) 0.0148(18) -0.0229(17) -0.0169(18) C10 0.0453(13) 0.0530(13) 0.0630(14) 0.0115(12) 0.0061(12) 0.0003(11) C11 0.0413(12) 0.0503(12) 0.0509(11) 0.0071(10) -0.0015(10) -0.0029(11) C12 0.0410(12) 0.0546(13) 0.0577(12) 0.0076(11) -0.0024(11) -0.0042(11) C13 0.0513(16) 0.0760(19) 0.094(2) 0.0123(17) 0.0165(17) 0.0112(16) C14 0.0606(17) 0.0568(15) 0.0854(18) 0.0068(14) 0.0105(16) 0.0093(13) C15 0.0460(14) 0.0504(13) 0.0584(12) 0.0047(11) 0.0003(11) -0.0015(11) C16 0.0475(13) 0.0423(11) 0.0671(14) 0.0111(10) -0.0017(12) 0.0001(11) C17 0.0519(15) 0.0471(13) 0.0720(15) 0.0074(12) -0.0020(13) 0.0004(12) C18 0.086(2) 0.0652(18) 0.0701(17) 0.0073(15) -0.0096(17) -0.0145(18) C19 0.117(3) 0.077(2) 0.0779(19) 0.0019(17) -0.019(2) -0.017(2) C20 0.097(3) 0.087(2) 0.109(3) -0.006(2) -0.031(3) -0.023(2) C21 0.069(2) 0.0665(19) 0.118(3) 0.003(2) -0.009(2) -0.0174(17) C22 0.0529(16) 0.0516(14) 0.0888(19) 0.0096(14) -0.0014(14) -0.0030(13) C23 0.0541(16) 0.0649(16) 0.093(2) 0.0162(16) 0.0079(16) -0.0114(15) C24 0.0617(17) 0.0634(16) 0.0706(16) 0.0126(13) 0.0105(15) -0.0049(15) C25 0.0509(15) 0.0456(12) 0.0684(15) 0.0092(11) 0.0046(13) 0.0022(11) C26 0.0688(18) 0.0492(13) 0.0674(15) 0.0012(12) 0.0054(15) 0.0011(14) C27 0.068(2) 0.0643(17) 0.093(2) -0.0133(16) -0.0187(18) -0.0002(17) C28 0.223(8) 0.159(5) 0.172(5) 0.055(5) -0.134(6) -0.075(6) C29 0.075(3) 0.246(8) 0.156(5) -0.065(5) -0.003(3) -0.050(4) C30 0.099(4) 0.066(2) 0.381(13) -0.061(4) -0.001(5) -0.013(3) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C26 O1 C27 124.0(3) . . ? C13 N1 C12 117.2(3) . . ? C2 C1 C6 119.9(3) . . ? C2 C1 C12 119.8(3) . . ? C6 C1 C12 120.3(2) . . ? C3 C2 C1 120.8(3) . . ? C4 C3 C2 119.6(3) . . ? C3 C4 C5 120.4(3) . . ? C4 C5 C6 121.3(3) . . ? C1 C6 C5 118.0(3) . . ? C1 C6 C7 120.4(2) . . ? C5 C6 C7 121.6(3) . . ? C6 C7 C8 112.3(2) . . ? C6 C7 C9 108.6(2) . . ? C6 C7 C10 108.8(2) . . ? C8 C7 C10 108.2(2) . . ? C9 C7 C8 109.2(3) . . ? C9 C7 C10 109.6(3) . . ? C11 C10 C7 113.2(2) . . ? C12 C11 C10 118.9(2) . . ? C12 C11 C15 117.8(2) . . ? C15 C11 C10 123.2(2) . . ? N1 C12 C1 117.7(2) . . ? N1 C12 C11 123.6(2) . . ? C11 C12 C1 118.7(2) . . ? N1 C13 C14 123.7(3) . . ? C13 C14 C15 119.7(3) . . ? C11 C15 C16 121.4(2) . . ? C14 C15 C11 118.0(2) . . ? C14 C15 C16 120.5(2) . . ? C17 C16 C15 117.8(2) . . ? C25 C16 C15 123.4(2) . . ? C25 C16 C17 118.8(2) . . ? C18 C17 C16 121.8(3) . . ? C18 C17 C22 117.7(3) . . ? C22 C17 C16 120.4(3) . . ? C19 C18 C17 121.1(3) . . ? C18 C19 C20 120.6(4) . . ? C21 C20 C19 120.7(4) . . ? C20 C21 C22 120.7(4) . . ? C17 C22 C23 118.2(3) . . ? C21 C22 C17 119.2(3) . . ? C21 C22 C23 122.6(3) . . ? C24 C23 C22 120.6(3) . . ? C23 C24 C25 122.1(3) . . ? C16 C25 C24 119.7(3) . . ? C16 C25 C26 124.3(3) . . ? C24 C25 C26 116.0(3) . . ? O1 C26 C25 113.5(3) . . ? O2 C26 O1 124.8(3) . . ? O2 C26 C25 121.6(3) . . ? C28 C27 O1 108.2(3) . . ? C28 C27 C29 109.6(6) . . ? C29 C27 O1 102.7(3) . . ? C30 C27 O1 110.4(4) . . ? C30 C27 C28 112.6(6) . . ? C30 C27 C29 112.9(5) . . ? 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 O1 C26 1.301(4) . ? O1 C27 1.490(4) . ? O2 C26 1.199(4) . ? N1 C12 1.337(4) . ? N1 C13 1.332(4) . ? C1 C2 1.389(4) . ? C1 C6 1.397(4) . ? C1 C12 1.484(4) . ? C2 C3 1.383(5) . ? C3 C4 1.368(6) . ? C4 C5 1.374(5) . ? C5 C6 1.401(4) . ? C6 C7 1.521(4) . ? C7 C8 1.535(4) . ? C7 C9 1.532(4) . ? C7 C10 1.535(4) . ? C10 C11 1.499(3) . ? C11 C12 1.400(3) . ? C11 C15 1.400(3) . ? C13 C14 1.369(4) . ? C14 C15 1.384(4) . ? C15 C16 1.489(4) . ? C16 C17 1.425(4) . ? C16 C25 1.390(4) . ? C17 C18 1.416(4) . ? C17 C22 1.419(4) . ? C18 C19 1.356(5) . ? C19 C20 1.388(5) . ? C20 C21 1.348(6) . ? C21 C22 1.413(5) . ? C22 C23 1.421(5) . ? C23 C24 1.342(5) . ? C24 C25 1.410(4) . ? C25 C26 1.491(4) . ? C27 C28 1.478(7) . ? C27 C29 1.484(7) . ? C27 C30 1.472(6) . ?