#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:10:40 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257958 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240442.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_7240442 loop_ _publ_author_name 'Zhang, Hua' 'Zhan, Xiao-Yu' 'Dong, Yu' 'Yang, Jian' 'He, Shuai' 'Shi, Zhi-Chuan' 'Zhang, Xiao-Mei' 'Wang, Ji-Yu' _publ_section_title ; Dehydration in water: frustrated Lewis pairs directly catalyzed allylization of electron-rich arenes and allyl alcohols ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 16942 _journal_page_last 16948 _journal_paper_doi 10.1039/D0RA02912B _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C27 H21 N3' _chemical_formula_sum 'C27 H21 N3' _chemical_formula_weight 387.47 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_block_doi 10.5517/ccdc.csd.cc244tgl _audit_creation_date 2019-10-31 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-12-09 deposited with the CCDC. 2020-04-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.603(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.7508(9) _cell_length_b 5.6719(4) _cell_length_c 26.3268(15) _cell_measurement_reflns_used 2880 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.6350 _cell_measurement_theta_min 3.5420 _cell_volume 2035.3(2) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _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 293.15 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0874 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -11.00 51.40 0.8000 1.0000 omega____ theta____ kappa____ phi______ frames - -14.9669 77.0000 -150.0000 78 #__ type_ start__ end____ width___ exp.time_ 2 omega -60.00 -34.40 0.8000 1.0000 omega____ theta____ kappa____ phi______ frames - -14.9669 129.0000 -154.0000 32 #__ type_ start__ end____ width___ exp.time_ 3 omega -67.00 -42.20 0.8000 1.0000 omega____ theta____ kappa____ phi______ frames - -14.9669 141.0000 17.0000 31 #__ type_ start__ end____ width___ exp.time_ 4 omega -83.00 3.40 0.8000 1.0000 omega____ theta____ kappa____ phi______ frames - -14.9669 -38.0000 -90.0000 108 #__ type_ start__ end____ width___ exp.time_ 5 omega -23.00 21.00 0.8000 1.0000 omega____ theta____ kappa____ phi______ frames - 16.9981 -99.0000 -150.0000 55 #__ type_ start__ end____ width___ exp.time_ 6 omega 19.00 43.80 0.8000 1.0000 omega____ theta____ kappa____ phi______ frames - 16.9981 -141.0000 -39.0000 31 #__ type_ start__ end____ width___ exp.time_ 7 omega 46.00 70.80 0.8000 1.0000 omega____ theta____ kappa____ phi______ frames - 16.9981 -129.0000 132.0000 31 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0034153000 _diffrn_orient_matrix_UB_12 0.0009368000 _diffrn_orient_matrix_UB_13 -0.0266450000 _diffrn_orient_matrix_UB_21 0.0510529000 _diffrn_orient_matrix_UB_22 -0.0224601000 _diffrn_orient_matrix_UB_23 0.0052213000 _diffrn_orient_matrix_UB_31 -0.0092968000 _diffrn_orient_matrix_UB_32 -0.1231171000 _diffrn_orient_matrix_UB_33 -0.0011758000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_unetI/netI 0.0404 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 11967 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.371 _diffrn_reflns_theta_min 3.123 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.99032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.140 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 271 _refine_ls_number_reflns 4148 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0514 _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^)+(0.0412P)^2^+0.4790P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1046 _refine_ls_wR_factor_ref 0.1173 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2956 _reflns_number_total 4148 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02912b2.cif _cod_data_source_block 191030_s2_zh _cod_depositor_comments 'Adding full bibliography for 7240441--7240442.cif.' _cod_original_cell_volume 2035.2(2) _cod_database_code 7240442 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula c12h12n2o2 _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 0.981 _shelx_estimated_absorpt_t_min 0.974 _reflns_odcompleteness_completeness 99.74 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Ternary CH refined with riding coordinates: C13(H13) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27) ; _shelx_res_file ; 191030_s2_zh.res created by SHELXL-2014/7 TITL 191030_s2_zh in P21/n #14 REM reset to P21/n #14 CELL 0.71073 13.75078 5.67188 26.32677 90 97.6034 90 ZERR 4 0.00087 0.00037 0.00145 0 0.0053 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N UNIT 108 84 12 L.S. 4 PLAN 20 SIZE 0.25 0.3 0.35 TEMP 20 htab conf bond $h fmap 2 acta SHEL 999 0.8 REM REM REM WGHT 0.041200 0.479000 FVAR 6.44910 N1 3 0.470630 0.386036 0.372005 11.00000 0.03405 0.04553 = 0.03995 0.00368 0.00112 -0.00143 N2 3 0.337730 0.129046 0.357442 11.00000 0.03804 0.05561 = 0.05526 -0.00104 0.00682 -0.00517 N3 3 0.457011 0.095719 0.431703 11.00000 0.05536 0.05459 = 0.04561 0.00829 0.00965 -0.00265 C1 1 0.448083 0.530636 0.328691 11.00000 0.03204 0.04787 = 0.03511 0.00071 0.00465 0.00608 C2 1 0.374465 0.518340 0.287222 11.00000 0.03667 0.06159 = 0.04395 -0.00410 0.00030 0.00039 AFIX 43 H2 2 0.328574 0.397007 0.284348 11.00000 -1.20000 AFIX 0 C3 1 0.371772 0.691764 0.250558 11.00000 0.04400 0.07435 = 0.03875 0.00314 -0.00428 0.01119 AFIX 43 H3 2 0.323200 0.686384 0.222418 11.00000 -1.20000 AFIX 0 C4 1 0.439462 0.874668 0.254329 11.00000 0.05257 0.06242 = 0.03884 0.01058 0.00608 0.01222 AFIX 43 H4 2 0.434668 0.991124 0.229255 11.00000 -1.20000 AFIX 0 C5 1 0.513677 0.885007 0.294924 11.00000 0.04176 0.05089 = 0.03900 0.00492 0.00818 0.00415 AFIX 43 H5 2 0.559418 1.006626 0.297334 11.00000 -1.20000 AFIX 0 C6 1 0.518924 0.709788 0.332312 11.00000 0.03008 0.04621 = 0.03354 0.00029 0.00680 0.00660 C7 1 0.586787 0.670496 0.378081 11.00000 0.03140 0.04389 = 0.03336 -0.00021 0.00422 0.00482 C8 1 0.555494 0.476672 0.400537 11.00000 0.03556 0.04832 = 0.03427 0.00092 -0.00081 0.00344 AFIX 43 H8 2 0.586148 0.411669 0.430937 11.00000 -1.20000 AFIX 0 C9 1 0.418541 0.193599 0.387700 11.00000 0.03847 0.04540 = 0.04096 -0.00124 0.01061 0.00377 C10 1 0.293785 -0.062107 0.373163 11.00000 0.04739 0.06001 = 0.06930 -0.00560 0.01531 -0.01087 AFIX 43 H10 2 0.237487 -0.116798 0.353162 11.00000 -1.20000 AFIX 0 C11 1 0.326982 -0.181943 0.417054 11.00000 0.05942 0.05444 = 0.07317 0.00294 0.02598 -0.00887 AFIX 43 H11 2 0.295318 -0.315856 0.426981 11.00000 -1.20000 AFIX 0 C12 1 0.409230 -0.094247 0.445548 11.00000 0.06606 0.05791 = 0.05476 0.01065 0.01852 0.00051 AFIX 43 H12 2 0.433114 -0.170086 0.475974 11.00000 -1.20000 AFIX 0 C13 1 0.674644 0.821230 0.396620 11.00000 0.03786 0.04101 = 0.03777 -0.00516 0.00123 0.00317 AFIX 13 H13 2 0.649565 0.980708 0.400938 11.00000 -1.20000 AFIX 0 C14 1 0.747304 0.840972 0.357820 11.00000 0.03342 0.03942 = 0.03383 0.00262 -0.00326 0.00078 C15 1 0.807294 1.039026 0.358627 11.00000 0.05566 0.04346 = 0.05238 -0.00039 -0.00064 -0.00639 AFIX 43 H15 2 0.802001 1.157789 0.382462 11.00000 -1.20000 AFIX 0 C16 1 0.874600 1.060682 0.324341 11.00000 0.04977 0.05609 = 0.06809 0.01649 0.00184 -0.01599 AFIX 43 H16 2 0.914375 1.193673 0.325382 11.00000 -1.20000 AFIX 0 C17 1 0.883320 0.888367 0.288862 11.00000 0.04010 0.07103 = 0.05099 0.01692 0.00715 0.00128 AFIX 43 H17 2 0.928597 0.903684 0.265771 11.00000 -1.20000 AFIX 0 C18 1 0.824484 0.692866 0.287776 11.00000 0.04606 0.06185 = 0.04872 -0.00224 0.00995 0.00318 AFIX 43 H18 2 0.829975 0.574891 0.263788 11.00000 -1.20000 AFIX 0 C19 1 0.757167 0.669520 0.321963 11.00000 0.03797 0.04567 = 0.04665 -0.00342 0.00564 -0.00453 AFIX 43 H19 2 0.717861 0.535666 0.320717 11.00000 -1.20000 AFIX 0 C20 1 0.722401 0.743380 0.448843 11.00000 0.04070 0.06327 = 0.03583 -0.00794 0.00257 -0.00095 AFIX 43 H20 2 0.692723 0.791902 0.476834 11.00000 -1.20000 AFIX 0 C21 1 0.800991 0.615089 0.458486 11.00000 0.04708 0.04918 = 0.04047 -0.00295 0.00579 0.00071 AFIX 43 H21 2 0.830547 0.567669 0.430374 11.00000 -1.20000 AFIX 0 C22 1 0.848406 0.536514 0.509263 11.00000 0.03629 0.04856 = 0.04149 0.00223 -0.00036 -0.00566 C23 1 0.842967 0.665535 0.553071 11.00000 0.05665 0.05588 = 0.04813 -0.00359 -0.00440 0.00266 AFIX 43 H23 2 0.807212 0.805167 0.551114 11.00000 -1.20000 AFIX 0 C24 1 0.889809 0.590561 0.599812 11.00000 0.07970 0.08445 = 0.04512 -0.00768 -0.00990 0.00372 AFIX 43 H24 2 0.885197 0.679880 0.629021 11.00000 -1.20000 AFIX 0 C25 1 0.942865 0.386620 0.603639 11.00000 0.05974 0.08785 = 0.05301 0.01872 -0.01504 -0.00083 AFIX 43 H25 2 0.974697 0.337438 0.635233 11.00000 -1.20000 AFIX 0 C26 1 0.948833 0.255488 0.560751 11.00000 0.05643 0.06129 = 0.07430 0.01569 -0.00502 0.00939 AFIX 43 H26 2 0.984299 0.115413 0.563088 11.00000 -1.20000 AFIX 0 C27 1 0.902352 0.330378 0.513954 11.00000 0.05861 0.06009 = 0.05506 -0.00195 -0.00031 0.00586 AFIX 43 H27 2 0.907405 0.240242 0.484911 11.00000 -1.20000 AFIX 0 HKLF 4 REM 191030_s2_zh in P21/n #14 REM R1 = 0.0514 for 2956 Fo > 4sig(Fo) and 0.0781 for all 4148 data REM 271 parameters refined using 0 restraints END WGHT 0.0411 0.4803 REM Instructions for potential hydrogen bonds HTAB C2 N2 REM Highest difference peak 0.140, deepest hole -0.177, 1-sigma level 0.036 Q1 1 0.5624 0.3562 0.4372 11.00000 0.05 0.14 Q2 1 0.7245 0.8209 0.3257 11.00000 0.05 0.14 Q3 1 0.7745 0.7212 0.4845 11.00000 0.05 0.14 Q4 1 0.8939 0.9370 0.6107 11.00000 0.05 0.13 Q5 1 0.7221 0.8330 0.3796 11.00000 0.05 0.13 Q6 1 0.7393 0.5895 0.4451 11.00000 0.05 0.13 Q7 1 0.7886 0.7773 0.4550 11.00000 0.05 0.13 Q8 1 0.7769 0.7148 0.3543 11.00000 0.05 0.12 Q9 1 0.5997 0.5264 0.3760 11.00000 0.05 0.12 Q10 1 0.5548 0.6483 0.4007 11.00000 0.05 0.11 Q11 1 0.6980 0.9184 0.4744 11.00000 0.05 0.11 Q12 1 0.7452 1.1848 0.4027 11.00000 0.05 0.11 Q13 1 0.8487 0.3889 0.5157 11.00000 0.05 0.11 Q14 1 0.8972 0.4989 0.5034 11.00000 0.05 0.11 Q15 1 1.0127 0.2668 0.5165 11.00000 0.05 0.11 Q16 1 0.3801 0.1404 0.2982 11.00000 0.05 0.11 Q17 1 0.4797 0.2232 0.3604 11.00000 0.05 0.11 Q18 1 0.9553 0.3365 0.4808 11.00000 0.05 0.11 Q19 1 0.6094 0.9212 0.2857 11.00000 0.05 0.11 Q20 1 0.5457 1.2202 0.2790 11.00000 0.05 0.11 ; _shelx_res_checksum 56723 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 N1 N 0.47063(10) 0.3860(3) 0.37200(5) 0.0402(4) Uani 1 1 d . . . . . N2 N 0.33773(11) 0.1290(3) 0.35744(6) 0.0496(4) Uani 1 1 d . . . . . N3 N 0.45701(12) 0.0957(3) 0.43170(6) 0.0516(4) Uani 1 1 d . . . . . C1 C 0.44808(12) 0.5306(3) 0.32869(6) 0.0383(4) Uani 1 1 d . . . . . C2 C 0.37447(13) 0.5183(4) 0.28722(7) 0.0479(5) Uani 1 1 d . . . . . H2 H 0.3286 0.3970 0.2843 0.057 Uiso 1 1 calc R . . . . C3 C 0.37177(14) 0.6918(4) 0.25056(7) 0.0532(5) Uani 1 1 d . . . . . H3 H 0.3232 0.6864 0.2224 0.064 Uiso 1 1 calc R . . . . C4 C 0.43946(15) 0.8747(4) 0.25433(7) 0.0513(5) Uani 1 1 d . . . . . H4 H 0.4347 0.9911 0.2293 0.062 Uiso 1 1 calc R . . . . C5 C 0.51368(13) 0.8850(3) 0.29492(6) 0.0436(4) Uani 1 1 d . . . . . H5 H 0.5594 1.0066 0.2973 0.052 Uiso 1 1 calc R . . . . C6 C 0.51892(12) 0.7098(3) 0.33231(6) 0.0364(4) Uani 1 1 d . . . . . C7 C 0.58679(12) 0.6705(3) 0.37808(6) 0.0362(4) Uani 1 1 d . . . . . C8 C 0.55549(12) 0.4767(3) 0.40054(6) 0.0399(4) Uani 1 1 d . . . . . H8 H 0.5861 0.4117 0.4309 0.048 Uiso 1 1 calc R . . . . C9 C 0.41854(13) 0.1936(3) 0.38770(6) 0.0411(4) Uani 1 1 d . . . . . C10 C 0.29378(15) -0.0621(4) 0.37316(8) 0.0582(6) Uani 1 1 d . . . . . H10 H 0.2375 -0.1168 0.3532 0.070 Uiso 1 1 calc R . . . . C11 C 0.32698(16) -0.1819(4) 0.41705(8) 0.0608(6) Uani 1 1 d . . . . . H11 H 0.2953 -0.3159 0.4270 0.073 Uiso 1 1 calc R . . . . C12 C 0.40923(17) -0.0942(4) 0.44555(8) 0.0586(6) Uani 1 1 d . . . . . H12 H 0.4331 -0.1701 0.4760 0.070 Uiso 1 1 calc R . . . . C13 C 0.67464(13) 0.8212(3) 0.39662(6) 0.0392(4) Uani 1 1 d . . . . . H13 H 0.6496 0.9807 0.4009 0.047 Uiso 1 1 calc R . . . . C14 C 0.74730(12) 0.8410(3) 0.35782(6) 0.0362(4) Uani 1 1 d . . . . . C15 C 0.80729(15) 1.0390(3) 0.35863(7) 0.0512(5) Uani 1 1 d . . . . . H15 H 0.8020 1.1578 0.3825 0.061 Uiso 1 1 calc R . . . . C16 C 0.87460(15) 1.0607(4) 0.32434(8) 0.0585(6) Uani 1 1 d . . . . . H16 H 0.9144 1.1937 0.3254 0.070 Uiso 1 1 calc R . . . . C17 C 0.88332(14) 0.8884(4) 0.28886(7) 0.0539(5) Uani 1 1 d . . . . . H17 H 0.9286 0.9037 0.2658 0.065 Uiso 1 1 calc R . . . . C18 C 0.82448(14) 0.6929(4) 0.28778(7) 0.0519(5) Uani 1 1 d . . . . . H18 H 0.8300 0.5749 0.2638 0.062 Uiso 1 1 calc R . . . . C19 C 0.75717(13) 0.6695(3) 0.32196(6) 0.0434(4) Uani 1 1 d . . . . . H19 H 0.7179 0.5357 0.3207 0.052 Uiso 1 1 calc R . . . . C20 C 0.72240(14) 0.7434(3) 0.44884(6) 0.0468(5) Uani 1 1 d . . . . . H20 H 0.6927 0.7919 0.4768 0.056 Uiso 1 1 calc R . . . . C21 C 0.80099(14) 0.6151(3) 0.45849(7) 0.0456(5) Uani 1 1 d . . . . . H21 H 0.8305 0.5677 0.4304 0.055 Uiso 1 1 calc R . . . . C22 C 0.84841(13) 0.5365(3) 0.50926(6) 0.0426(4) Uani 1 1 d . . . . . C23 C 0.84297(15) 0.6655(4) 0.55307(7) 0.0546(5) Uani 1 1 d . . . . . H23 H 0.8072 0.8052 0.5511 0.065 Uiso 1 1 calc R . . . . C24 C 0.88981(18) 0.5906(4) 0.59981(8) 0.0714(7) Uani 1 1 d . . . . . H24 H 0.8852 0.6799 0.6290 0.086 Uiso 1 1 calc R . . . . C25 C 0.94287(17) 0.3866(5) 0.60364(8) 0.0689(7) Uani 1 1 d . . . . . H25 H 0.9747 0.3374 0.6352 0.083 Uiso 1 1 calc R . . . . C26 C 0.94883(16) 0.2555(4) 0.56075(9) 0.0652(6) Uani 1 1 d . . . . . H26 H 0.9843 0.1154 0.5631 0.078 Uiso 1 1 calc R . . . . C27 C 0.90235(15) 0.3304(4) 0.51395(8) 0.0586(6) Uani 1 1 d . . . . . H27 H 0.9074 0.2402 0.4849 0.070 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 N1 0.0341(8) 0.0455(9) 0.0400(8) 0.0037(7) 0.0011(6) -0.0014(7) N2 0.0380(9) 0.0556(11) 0.0553(9) -0.0010(8) 0.0068(7) -0.0052(8) N3 0.0554(10) 0.0546(10) 0.0456(9) 0.0083(8) 0.0097(8) -0.0026(8) C1 0.0320(9) 0.0479(11) 0.0351(9) 0.0007(8) 0.0047(7) 0.0061(8) C2 0.0367(10) 0.0616(13) 0.0439(10) -0.0041(9) 0.0003(8) 0.0004(9) C3 0.0440(12) 0.0743(15) 0.0387(10) 0.0031(10) -0.0043(8) 0.0112(11) C4 0.0526(12) 0.0624(13) 0.0388(10) 0.0106(9) 0.0061(9) 0.0122(10) C5 0.0418(11) 0.0509(11) 0.0390(10) 0.0049(8) 0.0082(8) 0.0041(9) C6 0.0301(9) 0.0462(11) 0.0335(9) 0.0003(7) 0.0068(7) 0.0066(8) C7 0.0314(9) 0.0439(10) 0.0334(9) -0.0002(8) 0.0042(7) 0.0048(8) C8 0.0356(10) 0.0483(11) 0.0343(9) 0.0009(8) -0.0008(7) 0.0034(8) C9 0.0385(10) 0.0454(11) 0.0410(10) -0.0012(8) 0.0106(8) 0.0038(8) C10 0.0474(13) 0.0600(14) 0.0693(14) -0.0056(11) 0.0153(10) -0.0109(10) C11 0.0594(14) 0.0544(13) 0.0732(15) 0.0029(11) 0.0260(12) -0.0089(11) C12 0.0661(15) 0.0579(14) 0.0548(12) 0.0107(10) 0.0185(11) 0.0005(12) C13 0.0379(10) 0.0410(10) 0.0378(9) -0.0052(8) 0.0012(7) 0.0032(8) C14 0.0334(9) 0.0394(10) 0.0338(9) 0.0026(7) -0.0033(7) 0.0008(8) C15 0.0557(13) 0.0435(12) 0.0524(11) -0.0004(9) -0.0006(9) -0.0064(10) C16 0.0498(13) 0.0561(14) 0.0681(14) 0.0165(11) 0.0018(10) -0.0160(10) C17 0.0401(11) 0.0710(15) 0.0510(11) 0.0169(11) 0.0072(9) 0.0013(11) C18 0.0461(12) 0.0618(14) 0.0487(11) -0.0022(9) 0.0099(9) 0.0032(10) C19 0.0380(10) 0.0457(11) 0.0466(10) -0.0034(8) 0.0056(8) -0.0045(8) C20 0.0407(11) 0.0633(13) 0.0358(9) -0.0079(9) 0.0026(8) -0.0009(10) C21 0.0471(12) 0.0492(12) 0.0405(10) -0.0029(8) 0.0058(8) 0.0007(9) C22 0.0363(10) 0.0486(11) 0.0415(10) 0.0022(8) -0.0004(8) -0.0057(9) C23 0.0566(13) 0.0559(13) 0.0481(11) -0.0036(9) -0.0044(9) 0.0027(10) C24 0.0797(17) 0.0845(18) 0.0451(12) -0.0077(11) -0.0099(11) 0.0037(14) C25 0.0597(15) 0.0879(18) 0.0530(13) 0.0187(12) -0.0150(11) -0.0008(13) C26 0.0564(14) 0.0613(15) 0.0743(15) 0.0157(12) -0.0050(11) 0.0094(11) C27 0.0586(14) 0.0601(14) 0.0551(12) -0.0019(10) -0.0003(10) 0.0059(11) 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' 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 C8 N1 C1 107.45(14) . . ? C9 N1 C1 128.97(14) . . ? C9 N1 C8 123.49(14) . . ? C9 N2 C10 114.51(17) . . ? C9 N3 C12 114.88(17) . . ? C2 C1 N1 131.91(17) . . ? C2 C1 C6 121.16(16) . . ? C6 C1 N1 106.92(14) . . ? C1 C2 H2 121.1 . . ? C3 C2 C1 117.71(18) . . ? C3 C2 H2 121.1 . . ? C2 C3 H3 119.0 . . ? C2 C3 C4 121.92(17) . . ? C4 C3 H3 119.0 . . ? C3 C4 H4 119.7 . . ? C5 C4 C3 120.53(17) . . ? C5 C4 H4 119.7 . . ? C4 C5 H5 120.6 . . ? C4 C5 C6 118.76(18) . . ? C6 C5 H5 120.6 . . ? C1 C6 C7 108.19(14) . . ? C5 C6 C1 119.87(15) . . ? C5 C6 C7 131.94(17) . . ? C6 C7 C13 125.86(15) . . ? C8 C7 C6 106.53(15) . . ? C8 C7 C13 127.61(15) . . ? N1 C8 H8 124.5 . . ? C7 C8 N1 110.90(15) . . ? C7 C8 H8 124.5 . . ? N2 C9 N1 117.27(16) . . ? N3 C9 N1 115.04(16) . . ? N3 C9 N2 127.69(18) . . ? N2 C10 H10 118.2 . . ? N2 C10 C11 123.6(2) . . ? C11 C10 H10 118.2 . . ? C10 C11 H11 121.8 . . ? C12 C11 C10 116.3(2) . . ? C12 C11 H11 121.8 . . ? N3 C12 C11 123.0(2) . . ? N3 C12 H12 118.5 . . ? C11 C12 H12 118.5 . . ? C7 C13 H13 106.4 . . ? C7 C13 C14 113.13(13) . . ? C7 C13 C20 111.25(15) . . ? C14 C13 H13 106.4 . . ? C20 C13 H13 106.4 . . ? C20 C13 C14 112.78(14) . . ? C15 C14 C13 119.25(16) . . ? C19 C14 C13 122.76(16) . . ? C19 C14 C15 117.99(17) . . ? C14 C15 H15 119.7 . . ? C16 C15 C14 120.58(18) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.63(19) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 120.4 . . ? C16 C17 C18 119.17(18) . . ? C18 C17 H17 120.4 . . ? C17 C18 H18 119.7 . . ? C17 C18 C19 120.59(19) . . ? C19 C18 H18 119.7 . . ? C14 C19 C18 121.04(18) . . ? C14 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C13 C20 H20 116.8 . . ? C21 C20 C13 126.31(17) . . ? C21 C20 H20 116.8 . . ? C20 C21 H21 116.5 . . ? C20 C21 C22 127.01(17) . . ? C22 C21 H21 116.5 . . ? C23 C22 C21 122.12(17) . . ? C23 C22 C27 117.59(17) . . ? C27 C22 C21 120.26(17) . . ? C22 C23 H23 119.6 . . ? C22 C23 C24 120.9(2) . . ? C24 C23 H23 119.6 . . ? C23 C24 H24 119.7 . . ? C25 C24 C23 120.6(2) . . ? C25 C24 H24 119.7 . . ? C24 C25 H25 120.3 . . ? C26 C25 C24 119.44(19) . . ? C26 C25 H25 120.3 . . ? C25 C26 H26 120.0 . . ? C25 C26 C27 120.0(2) . . ? C27 C26 H26 120.0 . . ? C22 C27 H27 119.3 . . ? C26 C27 C22 121.40(19) . . ? C26 C27 H27 119.3 . . ? 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 N1 C1 1.406(2) . ? N1 C8 1.399(2) . ? N1 C9 1.398(2) . ? N2 C9 1.330(2) . ? N2 C10 1.333(2) . ? N3 C9 1.330(2) . ? N3 C12 1.337(2) . ? C1 C2 1.389(2) . ? C1 C6 1.402(2) . ? C2 H2 0.9300 . ? C2 C3 1.375(3) . ? C3 H3 0.9300 . ? C3 C4 1.389(3) . ? C4 H4 0.9300 . ? C4 C5 1.378(2) . ? C5 H5 0.9300 . ? C5 C6 1.394(2) . ? C6 C7 1.440(2) . ? C7 C8 1.346(2) . ? C7 C13 1.508(2) . ? C8 H8 0.9300 . ? C10 H10 0.9300 . ? C10 C11 1.366(3) . ? C11 H11 0.9300 . ? C11 C12 1.366(3) . ? C12 H12 0.9300 . ? C13 H13 0.9800 . ? C13 C14 1.525(2) . ? C13 C20 1.509(2) . ? C14 C15 1.392(2) . ? C14 C19 1.374(2) . ? C15 H15 0.9300 . ? C15 C16 1.381(3) . ? C16 H16 0.9300 . ? C16 C17 1.368(3) . ? C17 H17 0.9300 . ? C17 C18 1.371(3) . ? C18 H18 0.9300 . ? C18 C19 1.380(2) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C20 C21 1.300(2) . ? C21 H21 0.9300 . ? C21 C22 1.477(2) . ? C22 C23 1.376(2) . ? C22 C27 1.381(3) . ? C23 H23 0.9300 . ? C23 C24 1.378(3) . ? C24 H24 0.9300 . ? C24 C25 1.364(3) . ? C25 H25 0.9300 . ? C25 C26 1.364(3) . ? C26 H26 0.9300 . ? C26 C27 1.378(3) . ? C27 H27 0.9300 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 179.48(17) . . . . ? N1 C1 C6 C5 -178.32(14) . . . . ? N1 C1 C6 C7 1.16(18) . . . . ? N2 C10 C11 C12 0.7(3) . . . . ? C1 N1 C8 C7 0.71(19) . . . . ? C1 N1 C9 N2 2.4(3) . . . . ? C1 N1 C9 N3 -177.87(16) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C1 C6 C7 C8 -0.74(18) . . . . ? C1 C6 C7 C13 179.79(15) . . . . ? C2 C1 C6 C5 2.7(2) . . . . ? C2 C1 C6 C7 -177.83(15) . . . . ? C2 C3 C4 C5 1.5(3) . . . . ? C3 C4 C5 C6 -0.6(3) . . . . ? C4 C5 C6 C1 -1.4(2) . . . . ? C4 C5 C6 C7 179.23(17) . . . . ? C5 C6 C7 C8 178.66(18) . . . . ? C5 C6 C7 C13 -0.8(3) . . . . ? C6 C1 C2 C3 -1.8(3) . . . . ? C6 C7 C8 N1 0.02(19) . . . . ? C6 C7 C13 C14 -58.2(2) . . . . ? C6 C7 C13 C20 173.62(15) . . . . ? C7 C13 C14 C15 153.56(16) . . . . ? C7 C13 C14 C19 -27.1(2) . . . . ? C7 C13 C20 C21 100.8(2) . . . . ? C8 N1 C1 C2 177.70(18) . . . . ? C8 N1 C1 C6 -1.15(18) . . . . ? C8 N1 C9 N2 178.46(15) . . . . ? C8 N1 C9 N3 -1.8(2) . . . . ? C8 C7 C13 C14 122.43(18) . . . . ? C8 C7 C13 C20 -5.7(2) . . . . ? C9 N1 C1 C2 -5.8(3) . . . . ? C9 N1 C1 C6 175.39(16) . . . . ? C9 N1 C8 C7 -176.06(15) . . . . ? C9 N2 C10 C11 1.0(3) . . . . ? C9 N3 C12 C11 -0.2(3) . . . . ? C10 N2 C9 N1 176.99(16) . . . . ? C10 N2 C9 N3 -2.7(3) . . . . ? C10 C11 C12 N3 -1.1(3) . . . . ? C12 N3 C9 N1 -177.38(16) . . . . ? C12 N3 C9 N2 2.3(3) . . . . ? C13 C7 C8 N1 179.47(15) . . . . ? C13 C14 C15 C16 179.27(16) . . . . ? C13 C14 C19 C18 -179.38(16) . . . . ? C13 C20 C21 C22 -179.71(17) . . . . ? C14 C13 C20 C21 -27.5(3) . . . . ? C14 C15 C16 C17 0.2(3) . . . . ? C15 C14 C19 C18 0.0(3) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C17 C18 C19 C14 0.1(3) . . . . ? C19 C14 C15 C16 -0.1(3) . . . . ? C20 C13 C14 C15 -79.1(2) . . . . ? C20 C13 C14 C19 100.30(19) . . . . ? C20 C21 C22 C23 -29.2(3) . . . . ? C20 C21 C22 C27 152.3(2) . . . . ? C21 C22 C23 C24 -178.5(2) . . . . ? C21 C22 C27 C26 178.77(19) . . . . ? C22 C23 C24 C25 0.1(4) . . . . ? C23 C22 C27 C26 0.3(3) . . . . ? C23 C24 C25 C26 -0.4(4) . . . . ? C24 C25 C26 C27 0.7(4) . . . . ? C25 C26 C27 C22 -0.6(3) . . . . ? C27 C22 C23 C24 0.0(3) . . . . ?