#------------------------------------------------------------------------------ #$Date: 2021-05-29 07:23:51 +0300 (Sat, 29 May 2021) $ #$Revision: 265607 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/29/7242946.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_7242946 loop_ _publ_author_name 'Laurent, Mazarine' 'Bostyn, St\'ephane' 'Marchivie, Mathieu' 'Robin, Yves' 'Routier, Sylvain' 'Buron, Fr\'ed\'eric' _publ_section_title ; Aminations and arylations by direct C--O activation for the design of 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidines ; _journal_issue 32 _journal_name_full 'RSC Advances' _journal_page_first 19363 _journal_page_last 19377 _journal_paper_doi 10.1039/D1RA03092B _journal_volume 11 _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C22 H18 F3 N3' _chemical_formula_sum 'C22 H18 F3 N3' _chemical_formula_weight 381.39 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-03-31 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-04-01 deposited with the CCDC. 2021-05-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.051(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.3849(12) _cell_length_b 5.8934(4) _cell_length_c 22.187(2) _cell_measurement_reflns_used 7784 _cell_measurement_temperature 299.59 _cell_measurement_theta_max 26.31 _cell_measurement_theta_min 2.77 _cell_volume 1889.7(3) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 299.59 _diffrn_detector_area_resol_mean 8 _diffrn_measured_fraction_theta_full 0.927 _diffrn_measured_fraction_theta_max 0.927 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_unetI/netI 0.0430 _diffrn_reflns_Laue_measured_fraction_full 0.927 _diffrn_reflns_Laue_measured_fraction_max 0.927 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 16348 _diffrn_reflns_point_group_measured_fraction_full 0.926 _diffrn_reflns_point_group_measured_fraction_max 0.926 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.242 _diffrn_reflns_theta_min 1.409 _diffrn_source 'sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.5986 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1312 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.8031. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.341 _exptl_crystal_description needle _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.241 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.050 _refine_ls_abs_structure_details ; Flack x determined using 1628 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 525 _refine_ls_number_reflns 6319 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0543 _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^)+(0.0820P)^2^+0.3594P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1351 _refine_ls_wR_factor_ref 0.1503 _reflns_Friedel_coverage 0.807 _reflns_Friedel_fraction_full 0.926 _reflns_Friedel_fraction_max 0.926 _reflns_number_gt 4557 _reflns_number_total 6319 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra03092b2.cif _cod_data_source_block mzl_e_501_0m _cod_original_cell_volume 1889.8(3) _cod_database_code 7242946 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.990 _shelx_estimated_absorpt_t_min 0.961 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Others Sof(F3AA)=1-FVAR(1) Sof(F3BA)=FVAR(1) Sof(F3BB)=1-FVAR(2) Sof(F3AB)=FVAR(2) 3.a Ternary CH refined with riding coordinates: C3A(H3A), C3B(H3B) 3.b Secondary CH2 refined with riding coordinates: C1A(H1AA,H1AB), C2A(H2AA,H2AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C1B(H1BA, H1BB), C2B(H2BA,H2BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB) 3.c Aromatic/amide H refined with riding coordinates: C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A), C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B), C22B(H22B) ; _shelx_res_file ; TITL mzl_e_501_0m_a.res in P2(1) mzl_e_501_0m.res created by SHELXL-2018/3 at 18:10:59 on 31-Mar-2021 REM Old TITL MZL_E_501_0m in P2(1) REM SHELXT solution in P2(1) REM R1 0.186, Rweak 0.077, Alpha 0.009, Orientation as input REM Flack x = -0.435 ( 0.416 ) from Parsons' quotients REM Formula found by SHELXT: C47 N7 F3AB CELL 0.71073 15.3849 5.8934 22.1872 90 110.051 90 ZERR 4 0.0012 0.0004 0.002 0 0.004 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H F N UNIT 88 72 12 12 EQIV $1 2-X,1.5+Y,1-Z EQIV $2 -X,1.5+Y,-Z EQIV $3 +X,-1+Y,+Z EQIV $4 -X,-0.5+Y,-Z EQIV $5 1+X,1+Y,+Z EQIV $6 +X,1+Y,+Z EQIV $7 1+X,2+Y,+Z L.S. 4 0 0 PLAN 4 SIZE 0.1 0.1 0.4 TEMP 26.44 HTAB C3A F2A_$1 HTAB C3B F1B_$2 HTAB C19B F1A_$3 HTAB C21B F3BA HTAB C12B N2B_$4 HTAB C19A N3B_$5 HTAB C2A N2A_$6 HTAB C4B N2B_$6 HTAB C15A F3BB_$7 BOND $H list 4 fmap 2 53 acta MORE -1 CONF SHEL 99 0.8333 OMIT 3 0 8 OMIT 5 0 5 OMIT 0 0 10 OMIT 4 0 7 OMIT 8 1 8 OMIT 2 0 9 OMIT 4 1 8 REM REM REM WGHT 0.082000 0.359400 FVAR 0.62129 0.52497 0.47337 C1A 1 1.354323 1.824301 0.502854 11.00000 0.08529 0.03755 = 0.06608 -0.00319 0.02944 -0.00289 AFIX 23 H1AA 2 1.321027 1.901271 0.462954 11.00000 -1.20000 H1AB 2 1.407858 1.915858 0.525772 11.00000 -1.20000 AFIX 0 C2A 1 1.291461 1.805282 0.543287 11.00000 0.09084 0.04244 = 0.07614 -0.00640 0.03739 0.00741 AFIX 23 H2AA 2 1.318876 1.885330 0.583574 11.00000 -1.20000 H2AB 2 1.231678 1.872849 0.520543 11.00000 -1.20000 AFIX 0 C3A 1 1.279606 1.553970 0.556069 11.00000 0.06053 0.05129 = 0.04564 -0.00571 0.02726 -0.00430 AFIX 13 H3A 2 1.237360 1.531257 0.580045 11.00000 -1.20000 AFIX 0 C4A 1 1.376162 1.458938 0.591753 11.00000 0.07191 0.05418 = 0.03902 -0.00356 0.00677 -0.00611 AFIX 23 H4AA 2 1.403356 1.537396 0.632325 11.00000 -1.20000 H4AB 2 1.371862 1.298939 0.600595 11.00000 -1.20000 AFIX 0 C5A 1 1.436783 1.490773 0.550656 11.00000 0.05667 0.05289 = 0.04993 -0.00838 0.00942 -0.00361 AFIX 23 H5AA 2 1.489984 1.582840 0.573905 11.00000 -1.20000 H5AB 2 1.459250 1.343990 0.542692 11.00000 -1.20000 AFIX 0 C6A 1 1.305606 1.465793 0.458104 11.00000 0.03879 0.03518 = 0.03802 -0.00077 0.01420 -0.00078 C7A 1 1.247198 1.435264 0.492871 11.00000 0.04764 0.04078 = 0.03879 -0.00053 0.01669 0.00220 C8A 1 1.157189 1.196968 0.417345 11.00000 0.03622 0.05618 = 0.03881 0.00156 0.01222 -0.00291 C9A 1 1.283319 1.356706 0.399032 11.00000 0.03481 0.03908 = 0.03574 0.00372 0.00920 -0.00138 C10A 1 1.080725 1.028371 0.396368 11.00000 0.04003 0.06679 = 0.03822 -0.00314 0.01295 -0.00980 C11A 1 1.022691 0.994832 0.430772 11.00000 0.04520 0.08828 = 0.05515 -0.00389 0.01806 -0.00877 AFIX 43 H11A 2 1.030223 1.080700 0.467386 11.00000 -1.20000 AFIX 0 C12A 1 0.953590 0.835192 0.411414 11.00000 0.04247 0.09394 = 0.06006 0.01038 0.02155 -0.01410 AFIX 43 H12A 2 0.915325 0.813210 0.435507 11.00000 -1.20000 AFIX 0 C13A 1 0.940076 0.708951 0.357827 11.00000 0.04795 0.08024 = 0.06513 0.00486 0.01796 -0.02292 C14A 1 0.998342 0.739647 0.323695 11.00000 0.10309 0.12588 = 0.08236 -0.04693 0.05158 -0.06387 AFIX 43 H14A 2 0.990623 0.652472 0.287284 11.00000 -1.20000 AFIX 0 C15A 1 1.068282 0.898292 0.342712 11.00000 0.07751 0.12231 = 0.06965 -0.02825 0.04281 -0.05510 AFIX 43 H15A 2 1.107310 0.917384 0.319052 11.00000 -1.20000 AFIX 0 C16A 1 0.864393 0.537162 0.333446 11.00000 0.04731 0.10033 = 0.14083 0.03321 0.02616 -0.02910 C17A 1 1.338464 1.364968 0.355690 11.00000 0.03775 0.04301 = 0.02946 0.00329 0.00871 0.00053 C18A 1 1.335725 1.181852 0.315573 11.00000 0.05258 0.05087 = 0.04919 -0.00297 0.01901 -0.00655 AFIX 43 H18A 2 1.298591 1.057408 0.315647 11.00000 -1.20000 AFIX 0 C19A 1 1.387305 1.182826 0.275822 11.00000 0.06412 0.05919 = 0.05346 -0.00805 0.02729 -0.00164 AFIX 43 H19A 2 1.385142 1.059167 0.249306 11.00000 -1.20000 AFIX 0 C20A 1 1.441915 1.365766 0.275208 11.00000 0.05959 0.08609 = 0.04431 0.00209 0.02858 0.00013 AFIX 43 H20A 2 1.477868 1.364702 0.248993 11.00000 -1.20000 AFIX 0 C21A 1 1.443642 1.549549 0.313000 11.00000 0.06468 0.07322 = 0.04985 -0.00348 0.02374 -0.02295 AFIX 43 H21A 2 1.479287 1.675326 0.311391 11.00000 -1.20000 AFIX 0 C22A 1 1.392920 1.550054 0.353542 11.00000 0.06117 0.05078 = 0.04681 -0.00622 0.02262 -0.01099 AFIX 43 H22A 2 1.395241 1.675189 0.379586 11.00000 -1.20000 AFIX 0 PART 1 F1A 3 0.785785 0.619076 0.337037 11.00000 0.06435 0.15313 = 0.29880 0.00358 0.01986 -0.03710 F2A 3 0.866955 0.391992 0.380273 11.00000 0.13436 0.13782 = 0.26193 0.05594 0.03209 -0.05730 PART 2 F3AA 3 0.883673 0.356046 0.305990 -21.00000 0.08348 0.07127 = 0.13826 -0.03618 0.04216 -0.04743 PART 1 F3BA 3 0.819946 0.547795 0.271443 21.00000 0.09915 0.20004 = 0.06931 -0.03362 0.00535 -0.09778 PART 0 N1A 4 1.385825 1.601535 0.488260 11.00000 0.04875 0.04082 = 0.04523 -0.00591 0.01434 -0.00958 N2A 4 1.172273 1.301887 0.473855 11.00000 0.04653 0.05483 = 0.04197 0.00203 0.02035 -0.00025 N3A 4 1.208790 1.219970 0.380040 11.00000 0.03949 0.05444 = 0.03705 -0.00095 0.01163 -0.00891 C1B 1 0.387151 0.198924 -0.051128 11.00000 0.08262 0.05514 = 0.05193 0.00771 0.03837 0.00555 AFIX 23 H1BA 2 0.413333 0.047374 -0.045006 11.00000 -1.20000 H1BB 2 0.418968 0.287119 -0.074110 11.00000 -1.20000 AFIX 0 C2B 1 0.284054 0.184678 -0.091651 11.00000 0.08748 0.06247 = 0.03901 0.00275 0.02529 -0.00441 AFIX 23 H2BA 2 0.272023 0.268572 -0.131299 11.00000 -1.20000 H2BB 2 0.266460 0.027722 -0.102304 11.00000 -1.20000 AFIX 0 C3B 1 0.227631 0.285325 -0.053043 11.00000 0.05864 0.05098 = 0.05188 0.00837 0.01473 0.00745 AFIX 13 H3B 2 0.160859 0.273266 -0.075911 11.00000 -1.20000 AFIX 0 C4B 1 0.259091 0.533466 -0.038041 11.00000 0.08066 0.04227 = 0.08367 0.00663 0.02855 0.01001 AFIX 23 H4BA 2 0.247313 0.617519 -0.077639 11.00000 -1.20000 H4BB 2 0.224912 0.604823 -0.013665 11.00000 -1.20000 AFIX 0 C5B 1 0.362683 0.535289 0.000819 11.00000 0.08122 0.03914 = 0.07385 0.00500 0.02818 -0.00415 AFIX 23 H5BA 2 0.394704 0.623545 -0.022011 11.00000 -1.20000 H5BB 2 0.372392 0.608820 0.041726 11.00000 -1.20000 AFIX 0 C6B 1 0.350489 0.175781 0.043266 11.00000 0.04802 0.03336 = 0.03928 -0.00162 0.01797 0.00117 C7B 1 0.257263 0.161296 0.009721 11.00000 0.04910 0.04161 = 0.03953 -0.00019 0.01678 0.00648 C8B 1 0.238568 -0.074936 0.084611 11.00000 0.04022 0.05481 = 0.03574 -0.00541 0.01190 -0.00588 C9B 1 0.386275 0.062474 0.101548 11.00000 0.04010 0.03677 = 0.03806 -0.00646 0.01559 -0.00249 C10B 1 0.179082 -0.231147 0.106150 11.00000 0.03809 0.06500 = 0.03849 0.00052 0.00946 -0.00523 C11B 1 0.088864 -0.264827 0.069619 11.00000 0.04175 0.09066 = 0.04415 0.01083 0.00658 -0.00592 AFIX 43 H11B 2 0.063390 -0.183550 0.031695 11.00000 -1.20000 AFIX 0 C12B 1 0.034365 -0.417830 0.087895 11.00000 0.03982 0.09005 = 0.06104 -0.00284 0.01223 -0.01267 AFIX 43 H12B 2 -0.027043 -0.438677 0.062058 11.00000 -1.20000 AFIX 0 C13B 1 0.069504 -0.537343 0.142948 11.00000 0.04499 0.07896 = 0.05943 0.00971 0.01103 -0.01534 C14B 1 0.159648 -0.500661 0.181096 11.00000 0.05700 0.14227 = 0.08824 0.06416 -0.00723 -0.03049 AFIX 43 H14B 2 0.184261 -0.578164 0.219752 11.00000 -1.20000 AFIX 0 C15B 1 0.214287 -0.348521 0.162303 11.00000 0.04502 0.14183 = 0.07939 0.04959 -0.00403 -0.03248 AFIX 43 H15B 2 0.275551 -0.326315 0.188253 11.00000 -1.20000 AFIX 0 C16B 1 0.012900 -0.703004 0.163175 11.00000 0.06188 0.11355 = 0.09080 -0.00089 0.02472 -0.03828 C17B 1 0.483323 0.061159 0.144420 11.00000 0.04022 0.04730 = 0.03603 -0.00457 0.01880 -0.00398 C18B 1 0.516501 -0.121138 0.185624 11.00000 0.04438 0.05307 = 0.04874 -0.00005 0.01980 -0.00339 AFIX 43 H18B 2 0.477246 -0.241757 0.185046 11.00000 -1.20000 AFIX 0 C19B 1 0.605993 -0.126177 0.227053 11.00000 0.04649 0.06766 = 0.05743 0.00979 0.00816 0.00429 AFIX 43 H19B 2 0.626947 -0.250131 0.254094 11.00000 -1.20000 AFIX 0 C20B 1 0.665124 0.050819 0.228959 11.00000 0.04618 0.09290 = 0.05873 -0.00569 0.01407 -0.00933 AFIX 43 H20B 2 0.725855 0.046914 0.257215 11.00000 -1.20000 AFIX 0 C21B 1 0.634018 0.232928 0.188977 11.00000 0.05379 0.07543 = 0.06182 -0.00841 0.02222 -0.02445 AFIX 43 H21B 2 0.673790 0.352954 0.190104 11.00000 -1.20000 AFIX 0 C22B 1 0.543635 0.239029 0.146908 11.00000 0.05771 0.05042 = 0.04963 -0.00553 0.02312 -0.01219 AFIX 43 H22B 2 0.523095 0.363564 0.120032 11.00000 -1.20000 AFIX 0 PART 1 F1B 3 -0.034446 -0.836306 0.116193 11.00000 0.18925 0.16516 = 0.17787 -0.03346 0.07426 -0.11428 F2B 3 -0.060041 -0.607573 0.171013 11.00000 0.17669 0.15974 = 0.28977 0.00934 0.17411 -0.03763 F3AB 3 0.032975 -0.726293 0.225163 31.00000 0.11337 0.15914 = 0.08384 0.03960 0.02751 -0.06372 PART 2 F3BB 3 0.057112 -0.886667 0.191484 -31.00000 0.09930 0.09840 = 0.15138 0.05963 0.05251 -0.01738 PART 0 N1B 4 0.402906 0.304329 0.012421 11.00000 0.06056 0.03932 = 0.05107 0.00193 0.02583 -0.00302 N2B 4 0.198805 0.037648 0.029133 11.00000 0.04294 0.05486 = 0.04407 0.00029 0.01092 0.00017 N3B 4 0.327614 -0.065498 0.121044 11.00000 0.03947 0.05362 = 0.03712 -0.00119 0.01232 -0.00607 HKLF 4 REM mzl_e_501_0m_a.res in P2(1) REM wR2 = 0.1503, GooF = S = 1.043, Restrained GooF = 1.042 for all data REM R1 = 0.0543 for 4557 Fo > 4sig(Fo) and 0.0820 for all 6319 data REM 525 parameters refined using 1 restraints END WGHT 0.0820 0.3594 REM Highest difference peak 0.241, deepest hole -0.279, 1-sigma level 0.050 Q1 1 0.8649 0.4656 0.2817 11.00000 0.05 0.24 Q2 1 0.8976 0.2785 0.2955 11.00000 0.05 0.22 Q3 1 0.8862 0.3558 0.3351 11.00000 0.05 0.20 Q4 1 0.1007 -0.9456 0.2106 11.00000 0.05 0.19 ; _shelx_res_checksum 25973 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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_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 C1A C 1.3543(4) 1.8243(8) 0.5029(3) 0.0621(14) Uani 1 1 d . . . . . H1AA H 1.321027 1.901271 0.462954 0.074 Uiso 1 1 calc R U . . . H1AB H 1.407858 1.915858 0.525772 0.074 Uiso 1 1 calc R U . . . C2A C 1.2915(4) 1.8053(9) 0.5433(3) 0.0675(15) Uani 1 1 d . . . . . H2AA H 1.318876 1.885330 0.583574 0.081 Uiso 1 1 calc R U . . . H2AB H 1.231678 1.872849 0.520543 0.081 Uiso 1 1 calc R U . . . C3A C 1.2796(3) 1.5540(8) 0.5561(2) 0.0501(12) Uani 1 1 d . . . . . H3A H 1.237360 1.531257 0.580045 0.060 Uiso 1 1 calc R U . . . C4A C 1.3762(4) 1.4589(9) 0.5918(2) 0.0582(14) Uani 1 1 d . . . . . H4AA H 1.403356 1.537396 0.632325 0.070 Uiso 1 1 calc R U . . . H4AB H 1.371862 1.298939 0.600595 0.070 Uiso 1 1 calc R U . . . C5A C 1.4368(4) 1.4908(8) 0.5507(2) 0.0555(13) Uani 1 1 d . . . . . H5AA H 1.489984 1.582840 0.573905 0.067 Uiso 1 1 calc R U . . . H5AB H 1.459250 1.343990 0.542692 0.067 Uiso 1 1 calc R U . . . C6A C 1.3056(3) 1.4658(7) 0.4581(2) 0.0371(10) Uani 1 1 d . . . . . C7A C 1.2472(3) 1.4353(7) 0.4929(2) 0.0419(11) Uani 1 1 d . . . . . C8A C 1.1572(3) 1.1970(8) 0.4173(2) 0.0439(11) Uani 1 1 d . . . . . C9A C 1.2833(3) 1.3567(7) 0.3990(2) 0.0373(10) Uani 1 1 d . . . . . C10A C 1.0807(3) 1.0284(9) 0.3964(2) 0.0485(12) Uani 1 1 d . . . . . C11A C 1.0227(4) 0.9948(11) 0.4308(3) 0.0627(15) Uani 1 1 d . . . . . H11A H 1.030223 1.080700 0.467386 0.075 Uiso 1 1 calc R U . . . C12A C 0.9536(4) 0.8352(11) 0.4114(3) 0.0645(15) Uani 1 1 d . . . . . H12A H 0.915325 0.813210 0.435507 0.077 Uiso 1 1 calc R U . . . C13A C 0.9401(4) 0.7090(11) 0.3578(3) 0.0648(15) Uani 1 1 d . . . . . C14A C 0.9983(5) 0.7396(14) 0.3237(3) 0.099(3) Uani 1 1 d . . . . . H14A H 0.990623 0.652472 0.287284 0.118 Uiso 1 1 calc R U . . . C15A C 1.0683(4) 0.8983(13) 0.3427(3) 0.085(2) Uani 1 1 d . . . . . H15A H 1.107310 0.917384 0.319052 0.102 Uiso 1 1 calc R U . . . C16A C 0.8644(5) 0.5372(16) 0.3334(5) 0.098(3) Uani 1 1 d . . . . . C17A C 1.3385(3) 1.3650(7) 0.35569(19) 0.0375(10) Uani 1 1 d . . . . . C18A C 1.3357(3) 1.1819(9) 0.3156(2) 0.0505(12) Uani 1 1 d . . . . . H18A H 1.298591 1.057408 0.315647 0.061 Uiso 1 1 calc R U . . . C19A C 1.3873(4) 1.1828(9) 0.2758(3) 0.0571(13) Uani 1 1 d . . . . . H19A H 1.385142 1.059167 0.249306 0.068 Uiso 1 1 calc R U . . . C20A C 1.4419(4) 1.3658(10) 0.2752(2) 0.0605(14) Uani 1 1 d . . . . . H20A H 1.477868 1.364702 0.248993 0.073 Uiso 1 1 calc R U . . . C21A C 1.4436(4) 1.5495(10) 0.3130(2) 0.0615(14) Uani 1 1 d . . . . . H21A H 1.479287 1.675326 0.311391 0.074 Uiso 1 1 calc R U . . . C22A C 1.3929(3) 1.5501(9) 0.3535(2) 0.0519(12) Uani 1 1 d . . . . . H22A H 1.395241 1.675189 0.379586 0.062 Uiso 1 1 calc R U . . . F1A F 0.7858(3) 0.6191(11) 0.3370(4) 0.183(3) Uani 1 1 d . . . A 1 F2A F 0.8670(4) 0.3920(11) 0.3803(4) 0.187(3) Uani 1 1 d . . . B 1 F3AA F 0.8837(7) 0.3560(17) 0.3060(6) 0.097(5) Uani 0.475(16) 1 d . . P A 2 F3BA F 0.8199(8) 0.548(3) 0.2714(4) 0.129(7) Uani 0.525(16) 1 d . . P A 1 N1A N 1.3858(3) 1.6015(6) 0.48826(19) 0.0454(10) Uani 1 1 d . . . . . N2A N 1.1723(3) 1.3019(7) 0.47386(18) 0.0464(9) Uani 1 1 d . . . . . N3A N 1.2088(3) 1.2200(6) 0.38004(18) 0.0440(9) Uani 1 1 d . . . . . C1B C 0.3872(4) 0.1989(9) -0.0511(2) 0.0593(14) Uani 1 1 d . . . . . H1BA H 0.413333 0.047374 -0.045006 0.071 Uiso 1 1 calc R U . . . H1BB H 0.418968 0.287119 -0.074110 0.071 Uiso 1 1 calc R U . . . C2B C 0.2841(4) 0.1847(10) -0.0917(2) 0.0621(14) Uani 1 1 d . . . . . H2BA H 0.272023 0.268572 -0.131299 0.074 Uiso 1 1 calc R U . . . H2BB H 0.266460 0.027722 -0.102304 0.074 Uiso 1 1 calc R U . . . C3B C 0.2276(4) 0.2853(9) -0.0530(2) 0.0549(13) Uani 1 1 d . . . . . H3B H 0.160859 0.273266 -0.075911 0.066 Uiso 1 1 calc R U . . . C4B C 0.2591(4) 0.5335(9) -0.0380(3) 0.0688(16) Uani 1 1 d . . . . . H4BA H 0.247313 0.617519 -0.077639 0.083 Uiso 1 1 calc R U . . . H4BB H 0.224912 0.604823 -0.013665 0.083 Uiso 1 1 calc R U . . . C5B C 0.3627(4) 0.5353(9) 0.0008(3) 0.0643(15) Uani 1 1 d . . . . . H5BA H 0.394704 0.623545 -0.022011 0.077 Uiso 1 1 calc R U . . . H5BB H 0.372392 0.608820 0.041726 0.077 Uiso 1 1 calc R U . . . C6B C 0.3505(3) 0.1758(7) 0.0433(2) 0.0394(10) Uani 1 1 d . . . . . C7B C 0.2573(3) 0.1613(7) 0.0097(2) 0.0430(11) Uani 1 1 d . . . . . C8B C 0.2386(3) -0.0749(8) 0.0846(2) 0.0439(11) Uani 1 1 d . . . . . C9B C 0.3863(3) 0.0625(7) 0.1015(2) 0.0377(10) Uani 1 1 d . . . . . C10B C 0.1791(3) -0.2311(9) 0.1061(2) 0.0481(12) Uani 1 1 d . . . . . C11B C 0.0889(3) -0.2648(10) 0.0696(2) 0.0610(15) Uani 1 1 d . . . . . H11B H 0.063390 -0.183550 0.031695 0.073 Uiso 1 1 calc R U . . . C12B C 0.0344(4) -0.4178(11) 0.0879(3) 0.0649(15) Uani 1 1 d . . . . . H12B H -0.027043 -0.438677 0.062058 0.078 Uiso 1 1 calc R U . . . C13B C 0.0695(4) -0.5373(10) 0.1429(3) 0.0629(15) Uani 1 1 d . . . . . C14B C 0.1596(4) -0.5007(14) 0.1811(4) 0.104(3) Uani 1 1 d . . . . . H14B H 0.184261 -0.578164 0.219752 0.125 Uiso 1 1 calc R U . . . C15B C 0.2143(4) -0.3485(14) 0.1623(3) 0.095(2) Uani 1 1 d . . . . . H15B H 0.275551 -0.326315 0.188253 0.114 Uiso 1 1 calc R U . . . C16B C 0.0129(5) -0.7030(15) 0.1632(4) 0.089(2) Uani 1 1 d . . . . . C17B C 0.4833(3) 0.0612(8) 0.1444(2) 0.0397(10) Uani 1 1 d . . . . . C18B C 0.5165(3) -0.1211(9) 0.1856(2) 0.0477(12) Uani 1 1 d . . . . . H18B H 0.477246 -0.241757 0.185046 0.057 Uiso 1 1 calc R U . . . C19B C 0.6060(3) -0.1262(10) 0.2271(3) 0.0597(14) Uani 1 1 d . . . . . H19B H 0.626947 -0.250131 0.254094 0.072 Uiso 1 1 calc R U . . . C20B C 0.6651(4) 0.0508(12) 0.2290(3) 0.0669(15) Uani 1 1 d . . . . . H20B H 0.725855 0.046914 0.257215 0.080 Uiso 1 1 calc R U . . . C21B C 0.6340(4) 0.2329(10) 0.1890(3) 0.0631(15) Uani 1 1 d . . . . . H21B H 0.673790 0.352954 0.190104 0.076 Uiso 1 1 calc R U . . . C22B C 0.5436(4) 0.2390(8) 0.1469(2) 0.0514(13) Uani 1 1 d . . . . . H22B H 0.523095 0.363564 0.120032 0.062 Uiso 1 1 calc R U . . . F1B F -0.0344(5) -0.8363(11) 0.1162(3) 0.174(3) Uani 1 1 d . . . C 1 F2B F -0.0600(5) -0.6076(12) 0.1710(4) 0.184(3) Uani 1 1 d . . . C 1 F3AB F 0.0330(10) -0.726(4) 0.2252(6) 0.120(9) Uani 0.47(2) 1 d . . P C 1 F3BB F 0.0571(6) -0.887(2) 0.1915(9) 0.114(7) Uani 0.53(2) 1 d . . P C 2 N1B N 0.4029(3) 0.3043(6) 0.01242(19) 0.0486(10) Uani 1 1 d . . . . . N2B N 0.1988(3) 0.0376(7) 0.02913(19) 0.0483(10) Uani 1 1 d . . . . . N3B N 0.3276(3) -0.0655(6) 0.12104(17) 0.0436(9) Uani 1 1 d . . . . . 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 C1A 0.085(4) 0.038(3) 0.066(4) -0.003(2) 0.029(3) -0.003(3) C2A 0.091(4) 0.042(3) 0.076(4) -0.006(3) 0.037(4) 0.007(3) C3A 0.061(3) 0.051(3) 0.046(3) -0.006(2) 0.027(3) -0.004(2) C4A 0.072(4) 0.054(3) 0.039(3) -0.004(2) 0.007(3) -0.006(3) C5A 0.057(3) 0.053(3) 0.050(3) -0.008(2) 0.009(3) -0.004(2) C6A 0.039(3) 0.035(2) 0.038(2) -0.0008(18) 0.014(2) -0.0008(18) C7A 0.048(3) 0.041(2) 0.039(3) -0.001(2) 0.017(2) 0.002(2) C8A 0.036(3) 0.056(3) 0.039(3) 0.002(2) 0.012(2) -0.003(2) C9A 0.035(2) 0.039(2) 0.036(2) 0.0037(19) 0.009(2) -0.0014(19) C10A 0.040(3) 0.067(3) 0.038(3) -0.003(2) 0.013(2) -0.010(2) C11A 0.045(3) 0.088(4) 0.055(3) -0.004(3) 0.018(3) -0.009(3) C12A 0.042(3) 0.094(4) 0.060(4) 0.010(3) 0.022(3) -0.014(3) C13A 0.048(3) 0.080(4) 0.065(4) 0.005(3) 0.018(3) -0.023(3) C14A 0.103(5) 0.126(6) 0.082(5) -0.047(4) 0.052(4) -0.064(5) C15A 0.078(4) 0.122(6) 0.070(4) -0.028(4) 0.043(4) -0.055(4) C16A 0.047(4) 0.100(6) 0.141(8) 0.033(6) 0.026(5) -0.029(4) C17A 0.038(2) 0.043(2) 0.029(2) 0.0033(19) 0.0087(19) 0.0005(19) C18A 0.053(3) 0.051(3) 0.049(3) -0.003(2) 0.019(3) -0.007(2) C19A 0.064(3) 0.059(3) 0.053(3) -0.008(3) 0.027(3) -0.002(3) C20A 0.060(3) 0.086(4) 0.044(3) 0.002(3) 0.029(3) 0.000(3) C21A 0.065(4) 0.073(3) 0.050(3) -0.003(3) 0.024(3) -0.023(3) C22A 0.061(3) 0.051(3) 0.047(3) -0.006(2) 0.023(3) -0.011(2) F1A 0.064(3) 0.153(5) 0.299(9) 0.004(6) 0.020(4) -0.037(3) F2A 0.134(5) 0.138(5) 0.262(8) 0.056(6) 0.032(5) -0.057(4) F3AA 0.083(7) 0.071(7) 0.138(10) -0.036(6) 0.042(7) -0.047(5) F3BA 0.099(8) 0.200(14) 0.069(6) -0.034(7) 0.005(5) -0.098(9) N1A 0.049(2) 0.041(2) 0.045(2) -0.0059(17) 0.014(2) -0.0096(17) N2A 0.047(2) 0.055(2) 0.042(2) 0.0020(19) 0.0204(19) -0.0002(19) N3A 0.039(2) 0.054(2) 0.037(2) -0.0010(17) 0.0116(18) -0.0089(17) C1B 0.083(4) 0.055(3) 0.052(3) 0.008(3) 0.038(3) 0.006(3) C2B 0.087(4) 0.062(3) 0.039(3) 0.003(3) 0.025(3) -0.004(3) C3B 0.059(3) 0.051(3) 0.052(3) 0.008(2) 0.015(3) 0.007(2) C4B 0.081(4) 0.042(3) 0.084(4) 0.007(3) 0.029(4) 0.010(3) C5B 0.081(4) 0.039(3) 0.074(4) 0.005(3) 0.028(3) -0.004(3) C6B 0.048(3) 0.033(2) 0.039(3) -0.002(2) 0.018(2) 0.001(2) C7B 0.049(3) 0.042(2) 0.040(3) 0.000(2) 0.017(2) 0.006(2) C8B 0.040(3) 0.055(3) 0.036(2) -0.005(2) 0.012(2) -0.006(2) C9B 0.040(3) 0.037(2) 0.038(3) -0.006(2) 0.016(2) -0.002(2) C10B 0.038(3) 0.065(3) 0.038(3) 0.001(2) 0.009(2) -0.005(2) C11B 0.042(3) 0.091(4) 0.044(3) 0.011(3) 0.007(3) -0.006(3) C12B 0.040(3) 0.090(4) 0.061(4) -0.003(3) 0.012(3) -0.013(3) C13B 0.045(3) 0.079(4) 0.059(3) 0.010(3) 0.011(3) -0.015(3) C14B 0.057(4) 0.142(7) 0.088(5) 0.064(5) -0.007(4) -0.030(4) C15B 0.045(3) 0.142(6) 0.079(5) 0.050(4) -0.004(3) -0.032(4) C16B 0.062(4) 0.114(6) 0.091(6) -0.001(5) 0.025(4) -0.038(5) C17B 0.040(3) 0.047(3) 0.036(2) -0.005(2) 0.019(2) -0.004(2) C18B 0.044(3) 0.053(3) 0.049(3) 0.000(2) 0.020(2) -0.003(2) C19B 0.046(3) 0.068(3) 0.057(3) 0.010(3) 0.008(3) 0.004(3) C20B 0.046(3) 0.093(4) 0.059(4) -0.006(3) 0.014(3) -0.009(3) C21B 0.054(4) 0.075(4) 0.062(3) -0.008(3) 0.022(3) -0.024(3) C22B 0.058(3) 0.050(3) 0.050(3) -0.006(2) 0.023(3) -0.012(2) F1B 0.189(6) 0.165(5) 0.178(6) -0.033(5) 0.074(5) -0.114(5) F2B 0.177(6) 0.160(5) 0.290(9) 0.009(6) 0.174(7) -0.038(5) F3AB 0.113(10) 0.159(16) 0.084(8) 0.040(8) 0.028(6) -0.064(10) F3BB 0.099(6) 0.098(9) 0.151(13) 0.060(9) 0.053(7) -0.017(5) N1B 0.061(3) 0.039(2) 0.051(2) 0.0019(18) 0.026(2) -0.0030(18) N2B 0.043(2) 0.055(2) 0.044(2) 0.000(2) 0.0109(19) 0.0002(19) N3B 0.039(2) 0.054(2) 0.037(2) -0.0012(18) 0.0123(18) -0.0061(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' F F 0.0171 0.0103 '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 H1AA C1A H1AB 107.8 . . ? C2A C1A H1AA 109.1 . . ? C2A C1A H1AB 109.1 . . ? N1A C1A H1AA 109.1 . . ? N1A C1A H1AB 109.1 . . ? N1A C1A C2A 112.6(4) . . ? C1A C2A H2AA 110.0 . . ? C1A C2A H2AB 110.0 . . ? H2AA C2A H2AB 108.4 . . ? C3A C2A C1A 108.6(4) . . ? C3A C2A H2AA 110.0 . . ? C3A C2A H2AB 110.0 . . ? C2A C3A H3A 112.1 . . ? C4A C3A C2A 107.1(5) . . ? C4A C3A H3A 112.1 . . ? C7A C3A C2A 107.6(4) . . ? C7A C3A H3A 112.1 . . ? C7A C3A C4A 105.5(4) . . ? C3A C4A H4AA 109.8 . . ? C3A C4A H4AB 109.8 . . ? H4AA C4A H4AB 108.3 . . ? C5A C4A C3A 109.3(4) . . ? C5A C4A H4AA 109.8 . . ? C5A C4A H4AB 109.8 . . ? C4A C5A H5AA 109.2 . . ? C4A C5A H5AB 109.2 . . ? H5AA C5A H5AB 107.9 . . ? N1A C5A C4A 112.1(4) . . ? N1A C5A H5AA 109.2 . . ? N1A C5A H5AB 109.2 . . ? C7A C6A C9A 117.9(4) . . ? C7A C6A N1A 115.7(4) . . ? C9A C6A N1A 126.4(4) . . ? C6A C7A C3A 113.1(4) . . ? N2A C7A C3A 123.1(4) . . ? N2A C7A C6A 123.7(4) . . ? N2A C8A C10A 117.6(4) . . ? N3A C8A C10A 116.6(4) . . ? N3A C8A N2A 125.6(4) . . ? C6A C9A C17A 125.7(4) . . ? N3A C9A C6A 118.7(4) . . ? N3A C9A C17A 115.6(4) . . ? C11A C10A C8A 121.2(4) . . ? C15A C10A C8A 120.3(4) . . ? C15A C10A C11A 118.5(5) . . ? C10A C11A H11A 119.8 . . ? C10A C11A C12A 120.4(5) . . ? C12A C11A H11A 119.8 . . ? C11A C12A H12A 119.4 . . ? C13A C12A C11A 121.3(5) . . ? C13A C12A H12A 119.4 . . ? C12A C13A C14A 118.7(5) . . ? C12A C13A C16A 123.6(6) . . ? C14A C13A C16A 117.7(6) . . ? C13A C14A H14A 119.6 . . ? C13A C14A C15A 120.7(6) . . ? C15A C14A H14A 119.6 . . ? C10A C15A C14A 120.4(5) . . ? C10A C15A H15A 119.8 . . ? C14A C15A H15A 119.8 . . ? F1A C16A C13A 110.1(8) . . ? F1A C16A F2A 88.3(6) . . ? F2A C16A C13A 109.9(7) . . ? F3AA C16A C13A 116.5(6) . . ? F3BA C16A C13A 114.1(7) . . ? F3BA C16A F1A 83.5(8) . . ? F3BA C16A F2A 135.4(8) . . ? C18A C17A C9A 119.4(4) . . ? C22A C17A C9A 122.3(4) . . ? C22A C17A C18A 118.3(4) . . ? C17A C18A H18A 119.7 . . ? C19A C18A C17A 120.7(5) . . ? C19A C18A H18A 119.7 . . ? C18A C19A H19A 120.0 . . ? C20A C19A C18A 120.1(5) . . ? C20A C19A H19A 120.0 . . ? C19A C20A H20A 120.0 . . ? C21A C20A C19A 120.1(4) . . ? C21A C20A H20A 120.0 . . ? C20A C21A H21A 119.8 . . ? C20A C21A C22A 120.4(5) . . ? C22A C21A H21A 119.8 . . ? C17A C22A H22A 119.8 . . ? C21A C22A C17A 120.3(5) . . ? C21A C22A H22A 119.8 . . ? C16A F1A F3BA 47.8(6) . . ? C16A F3BA F1A 48.7(5) . . ? C1A N1A C5A 107.1(4) . . ? C6A N1A C1A 107.8(4) . . ? C6A N1A C5A 106.6(3) . . ? C7A N2A C8A 114.7(4) . . ? C8A N3A C9A 119.4(4) . . ? H1BA C1B H1BB 107.9 . . ? C2B C1B H1BA 109.1 . . ? C2B C1B H1BB 109.1 . . ? N1B C1B H1BA 109.1 . . ? N1B C1B H1BB 109.1 . . ? N1B C1B C2B 112.3(4) . . ? C1B C2B H2BA 109.9 . . ? C1B C2B H2BB 109.9 . . ? H2BA C2B H2BB 108.3 . . ? C3B C2B C1B 108.7(4) . . ? C3B C2B H2BA 109.9 . . ? C3B C2B H2BB 109.9 . . ? C2B C3B H3B 112.1 . . ? C2B C3B C4B 107.0(5) . . ? C4B C3B H3B 112.1 . . ? C7B C3B C2B 106.3(4) . . ? C7B C3B H3B 112.1 . . ? C7B C3B C4B 106.8(5) . . ? C3B C4B H4BA 110.0 . . ? C3B C4B H4BB 110.0 . . ? H4BA C4B H4BB 108.4 . . ? C5B C4B C3B 108.5(5) . . ? C5B C4B H4BA 110.0 . . ? C5B C4B H4BB 110.0 . . ? C4B C5B H5BA 109.1 . . ? C4B C5B H5BB 109.1 . . ? H5BA C5B H5BB 107.8 . . ? N1B C5B C4B 112.6(4) . . ? N1B C5B H5BA 109.1 . . ? N1B C5B H5BB 109.1 . . ? C7B C6B C9B 118.8(4) . . ? C7B C6B N1B 115.2(4) . . ? C9B C6B N1B 126.0(4) . . ? C6B C7B C3B 113.7(4) . . ? N2B C7B C3B 122.7(4) . . ? N2B C7B C6B 123.5(4) . . ? N2B C8B C10B 117.5(4) . . ? N3B C8B C10B 116.7(4) . . ? N3B C8B N2B 125.8(4) . . ? C6B C9B C17B 126.5(4) . . ? N3B C9B C6B 118.0(4) . . ? N3B C9B C17B 115.5(4) . . ? C11B C10B C8B 120.9(4) . . ? C11B C10B C15B 118.3(5) . . ? C15B C10B C8B 120.8(5) . . ? C10B C11B H11B 119.4 . . ? C10B C11B C12B 121.2(5) . . ? C12B C11B H11B 119.4 . . ? C11B C12B H12B 119.7 . . ? C13B C12B C11B 120.6(5) . . ? C13B C12B H12B 119.7 . . ? C12B C13B C14B 118.8(5) . . ? C12B C13B C16B 121.6(6) . . ? C14B C13B C16B 119.6(6) . . ? C13B C14B H14B 119.8 . . ? C13B C14B C15B 120.3(6) . . ? C15B C14B H14B 119.8 . . ? C10B C15B C14B 120.7(6) . . ? C10B C15B H15B 119.7 . . ? C14B C15B H15B 119.7 . . ? F1B C16B C13B 112.3(6) . . ? F1B C16B F2B 95.4(7) . . ? F1B C16B F3AB 129.8(9) . . ? F2B C16B C13B 112.0(7) . . ? F3AB C16B C13B 115.9(7) . . ? F3AB C16B F2B 79.1(12) . . ? F3BB C16B C13B 115.2(7) . . ? C18B C17B C9B 119.5(4) . . ? C22B C17B C9B 122.6(4) . . ? C22B C17B C18B 117.9(4) . . ? C17B C18B H18B 119.4 . . ? C19B C18B C17B 121.1(5) . . ? C19B C18B H18B 119.4 . . ? C18B C19B H19B 119.8 . . ? C18B C19B C20B 120.4(5) . . ? C20B C19B H19B 119.8 . . ? C19B C20B H20B 120.2 . . ? C21B C20B C19B 119.6(5) . . ? C21B C20B H20B 120.2 . . ? C20B C21B H21B 119.9 . . ? C20B C21B C22B 120.3(5) . . ? C22B C21B H21B 119.9 . . ? C17B C22B H22B 119.7 . . ? C21B C22B C17B 120.7(5) . . ? C21B C22B H22B 119.7 . . ? C16B F2B F3AB 50.2(8) . . ? C16B F3AB F2B 50.7(6) . . ? C5B N1B C1B 107.3(4) . . ? C6B N1B C1B 107.2(4) . . ? C6B N1B C5B 107.3(4) . . ? C7B N2B C8B 114.7(4) . . ? C8B N3B C9B 119.2(4) . . ? 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 C1A H1AA 0.9700 . ? C1A H1AB 0.9700 . ? C1A C2A 1.532(8) . ? C1A N1A 1.473(6) . ? C2A H2AA 0.9700 . ? C2A H2AB 0.9700 . ? C2A C3A 1.531(8) . ? C3A H3A 0.9800 . ? C3A C4A 1.530(7) . ? C3A C7A 1.492(6) . ? C4A H4AA 0.9700 . ? C4A H4AB 0.9700 . ? C4A C5A 1.523(7) . ? C5A H5AA 0.9700 . ? C5A H5AB 0.9700 . ? C5A N1A 1.488(6) . ? C6A C7A 1.382(6) . ? C6A C9A 1.393(6) . ? C6A N1A 1.430(5) . ? C7A N2A 1.338(6) . ? C8A C10A 1.487(6) . ? C8A N2A 1.345(6) . ? C8A N3A 1.336(6) . ? C9A C17A 1.485(6) . ? C9A N3A 1.345(5) . ? C10A C11A 1.373(6) . ? C10A C15A 1.373(8) . ? C11A H11A 0.9300 . ? C11A C12A 1.374(8) . ? C12A H12A 0.9300 . ? C12A C13A 1.357(8) . ? C13A C14A 1.369(8) . ? C13A C16A 1.497(9) . ? C14A H14A 0.9300 . ? C14A C15A 1.378(8) . ? C15A H15A 0.9300 . ? C16A F1A 1.330(10) . ? C16A F2A 1.336(10) . ? C16A F3AA 1.312(12) . ? C16A F3BA 1.311(12) . ? C17A C18A 1.390(7) . ? C17A C22A 1.386(6) . ? C18A H18A 0.9300 . ? C18A C19A 1.374(7) . ? C19A H19A 0.9300 . ? C19A C20A 1.370(7) . ? C20A H20A 0.9300 . ? C20A C21A 1.364(8) . ? C21A H21A 0.9300 . ? C21A C22A 1.378(7) . ? C22A H22A 0.9300 . ? F1A F3BA 1.759(11) . ? C1B H1BA 0.9700 . ? C1B H1BB 0.9700 . ? C1B C2B 1.534(8) . ? C1B N1B 1.483(6) . ? C2B H2BA 0.9700 . ? C2B H2BB 0.9700 . ? C2B C3B 1.533(7) . ? C3B H3B 0.9800 . ? C3B C4B 1.541(8) . ? C3B C7B 1.499(7) . ? C4B H4BA 0.9700 . ? C4B H4BB 0.9700 . ? C4B C5B 1.530(8) . ? C5B H5BA 0.9700 . ? C5B H5BB 0.9700 . ? C5B N1B 1.481(7) . ? C6B C7B 1.373(6) . ? C6B C9B 1.390(6) . ? C6B N1B 1.439(6) . ? C7B N2B 1.338(6) . ? C8B C10B 1.488(6) . ? C8B N2B 1.347(6) . ? C8B N3B 1.332(6) . ? C9B C17B 1.470(6) . ? C9B N3B 1.356(5) . ? C10B C11B 1.361(7) . ? C10B C15B 1.364(8) . ? C11B H11B 0.9300 . ? C11B C12B 1.383(7) . ? C12B H12B 0.9300 . ? C12B C13B 1.352(8) . ? C13B C14B 1.372(8) . ? C13B C16B 1.477(9) . ? C14B H14B 0.9300 . ? C14B C15B 1.387(8) . ? C15B H15B 0.9300 . ? C16B F1B 1.309(9) . ? C16B F2B 1.319(10) . ? C16B F3AB 1.309(13) . ? C16B F3BB 1.317(12) . ? C17B C18B 1.389(7) . ? C17B C22B 1.388(6) . ? C18B H18B 0.9300 . ? C18B C19B 1.369(7) . ? C19B H19B 0.9300 . ? C19B C20B 1.375(8) . ? C20B H20B 0.9300 . ? C20B C21B 1.370(9) . ? C21B H21B 0.9300 . ? C21B C22B 1.384(7) . ? C22B H22B 0.9300 . ? F2B F3AB 1.674(17) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C2A H2AB N2A 0.97 2.77 3.516(7) 134.6 1_565 yes C3A H3A F2A 0.98 2.97 3.637(8) 126.1 2_766 yes C15A H15A F3BB 0.93 2.91 3.535(15) 126.2 1_675 yes C19A H19A N3B 0.93 2.77 3.552(6) 141.8 1_665 yes C3B H3B F1B 0.98 2.95 3.594(7) 124.5 2_565 yes C4B H4BB N2B 0.97 2.80 3.586(7) 138.8 1_565 yes C12B H12B N2B 0.93 2.73 3.646(7) 170.3 2_545 yes C19B H19B F1A 0.93 2.62 3.351(8) 135.9 1_545 yes C21B H21B F3BA 0.93 2.62 3.374(9) 138.9 . yes 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 C1A C2A C3A C4A 59.5(6) . . . . ? C1A C2A C3A C7A -53.5(6) . . . . ? C2A C1A N1A C5A -59.1(6) . . . . ? C2A C1A N1A C6A 55.2(6) . . . . ? C2A C3A C4A C5A -59.1(5) . . . . ? C2A C3A C7A C6A 56.1(6) . . . . ? C2A C3A C7A N2A -127.8(5) . . . . ? C3A C4A C5A N1A -0.5(6) . . . . ? C3A C7A N2A C8A -175.7(4) . . . . ? C4A C3A C7A C6A -58.0(5) . . . . ? C4A C3A C7A N2A 118.1(5) . . . . ? C4A C5A N1A C1A 59.6(5) . . . . ? C4A C5A N1A C6A -55.5(5) . . . . ? C6A C7A N2A C8A 0.0(6) . . . . ? C6A C9A C17A C18A 150.8(4) . . . . ? C6A C9A C17A C22A -29.3(6) . . . . ? C6A C9A N3A C8A 1.6(6) . . . . ? C7A C3A C4A C5A 55.3(5) . . . . ? C7A C6A C9A C17A -178.6(4) . . . . ? C7A C6A C9A N3A -2.8(6) . . . . ? C7A C6A N1A C1A -57.2(5) . . . . ? C7A C6A N1A C5A 57.5(5) . . . . ? C8A C10A C11A C12A -178.7(5) . . . . ? C8A C10A C15A C14A 179.1(6) . . . . ? C9A C6A C7A C3A 178.2(4) . . . . ? C9A C6A C7A N2A 2.1(7) . . . . ? C9A C6A N1A C1A 125.3(5) . . . . ? C9A C6A N1A C5A -119.9(5) . . . . ? C9A C17A C18A C19A -178.8(5) . . . . ? C9A C17A C22A C21A 179.4(5) . . . . ? C10A C8A N2A C7A 174.0(4) . . . . ? C10A C8A N3A C9A -174.9(4) . . . . ? C10A C11A C12A C13A -0.8(9) . . . . ? C11A C10A C15A C14A 0.7(10) . . . . ? C11A C12A C13A C14A 1.5(10) . . . . ? C11A C12A C13A C16A -178.3(6) . . . . ? C12A C13A C14A C15A -1.1(12) . . . . ? C12A C13A C16A F1A 42.9(10) . . . . ? C12A C13A C16A F2A -52.8(11) . . . . ? C12A C13A C16A F3AA -145.6(9) . . . . ? C12A C13A C16A F3BA 134.8(10) . . . . ? C13A C14A C15A C10A 0.0(12) . . . . ? C13A C16A F1A F3BA 113.3(8) . . . . ? C13A C16A F3BA F1A -109.2(10) . . . . ? C14A C13A C16A F1A -136.9(9) . . . . ? C14A C13A C16A F2A 127.4(8) . . . . ? C14A C13A C16A F3AA 34.7(12) . . . . ? C14A C13A C16A F3BA -45.0(13) . . . . ? C15A C10A C11A C12A -0.3(9) . . . . ? C16A C13A C14A C15A 178.7(7) . . . . ? C17A C9A N3A C8A 177.8(4) . . . . ? C17A C18A C19A C20A -0.3(8) . . . . ? C18A C17A C22A C21A -0.7(7) . . . . ? C18A C19A C20A C21A -1.5(9) . . . . ? C19A C20A C21A C22A 2.1(9) . . . . ? C20A C21A C22A C17A -0.9(8) . . . . ? C22A C17A C18A C19A 1.3(7) . . . . ? F2A C16A F1A F3BA -136.1(9) . . . . ? F2A C16A F3BA F1A 81.0(12) . . . . ? N1A C1A C2A C3A -0.5(7) . . . . ? N1A C6A C7A C3A 0.5(6) . . . . ? N1A C6A C7A N2A -175.6(4) . . . . ? N1A C6A C9A C17A -1.2(7) . . . . ? N1A C6A C9A N3A 174.6(4) . . . . ? N2A C8A C10A C11A 5.3(7) . . . . ? N2A C8A C10A C15A -173.0(6) . . . . ? N2A C8A N3A C9A 0.6(7) . . . . ? N3A C8A C10A C11A -178.8(5) . . . . ? N3A C8A C10A C15A 2.8(8) . . . . ? N3A C8A N2A C7A -1.4(7) . . . . ? N3A C9A C17A C18A -25.0(6) . . . . ? N3A C9A C17A C22A 154.8(4) . . . . ? C1B C2B C3B C4B 59.7(6) . . . . ? C1B C2B C3B C7B -54.2(5) . . . . ? C2B C1B N1B C5B -59.3(5) . . . . ? C2B C1B N1B C6B 55.7(5) . . . . ? C2B C3B C4B C5B -59.9(6) . . . . ? C2B C3B C7B C6B 57.5(5) . . . . ? C2B C3B C7B N2B -118.8(5) . . . . ? C3B C4B C5B N1B 0.4(7) . . . . ? C3B C7B N2B C8B 175.5(4) . . . . ? C4B C3B C7B C6B -56.4(5) . . . . ? C4B C3B C7B N2B 127.2(5) . . . . ? C4B C5B N1B C1B 59.1(6) . . . . ? C4B C5B N1B C6B -55.8(6) . . . . ? C6B C7B N2B C8B -0.5(6) . . . . ? C6B C9B C17B C18B -154.1(4) . . . . ? C6B C9B C17B C22B 27.7(7) . . . . ? C6B C9B N3B C8B -1.1(6) . . . . ? C7B C3B C4B C5B 53.6(6) . . . . ? C7B C6B C9B C17B -179.0(4) . . . . ? C7B C6B C9B N3B 2.9(6) . . . . ? C7B C6B N1B C1B -57.2(5) . . . . ? C7B C6B N1B C5B 57.8(5) . . . . ? C8B C10B C11B C12B 176.9(5) . . . . ? C8B C10B C15B C14B -177.5(7) . . . . ? C9B C6B C7B C3B -178.5(4) . . . . ? C9B C6B C7B N2B -2.1(6) . . . . ? C9B C6B N1B C1B 120.5(5) . . . . ? C9B C6B N1B C5B -124.4(5) . . . . ? C9B C17B C18B C19B -178.8(4) . . . . ? C9B C17B C22B C21B 178.6(4) . . . . ? C10B C8B N2B C7B -174.9(4) . . . . ? C10B C8B N3B C9B 175.7(4) . . . . ? C10B C11B C12B C13B 0.3(9) . . . . ? C11B C10B C15B C14B 0.9(11) . . . . ? C11B C12B C13B C14B 1.4(10) . . . . ? C11B C12B C13B C16B -179.5(7) . . . . ? C12B C13B C14B C15B -2.0(12) . . . . ? C12B C13B C16B F1B 46.0(11) . . . . ? C12B C13B C16B F2B -60.0(10) . . . . ? C12B C13B C16B F3AB -148.3(15) . . . . ? C12B C13B C16B F3BB 143.2(12) . . . . ? C13B C14B C15B C10B 0.8(13) . . . . ? C13B C16B F2B F3AB -113.7(10) . . . . ? C13B C16B F3AB F2B 109.3(10) . . . . ? C14B C13B C16B F1B -134.8(8) . . . . ? C14B C13B C16B F2B 119.1(9) . . . . ? C14B C13B C16B F3AB 30.8(17) . . . . ? C14B C13B C16B F3BB -37.7(14) . . . . ? C15B C10B C11B C12B -1.5(9) . . . . ? C16B C13B C14B C15B 178.9(8) . . . . ? C17B C9B N3B C8B -179.5(4) . . . . ? C17B C18B C19B C20B 0.3(8) . . . . ? C18B C17B C22B C21B 0.4(7) . . . . ? C18B C19B C20B C21B -0.1(8) . . . . ? C19B C20B C21B C22B 0.0(9) . . . . ? C20B C21B C22B C17B -0.2(8) . . . . ? C22B C17B C18B C19B -0.5(7) . . . . ? F1B C16B F2B F3AB 129.5(9) . . . . ? F1B C16B F3AB F2B -88.0(14) . . . . ? N1B C1B C2B C3B -0.2(6) . . . . ? N1B C6B C7B C3B -0.5(5) . . . . ? N1B C6B C7B N2B 175.8(4) . . . . ? N1B C6B C9B C17B 3.3(7) . . . . ? N1B C6B C9B N3B -174.8(4) . . . . ? N2B C8B C10B C11B 2.5(7) . . . . ? N2B C8B C10B C15B -179.1(6) . . . . ? N2B C8B N3B C9B -1.7(7) . . . . ? N3B C8B C10B C11B -175.1(5) . . . . ? N3B C8B C10B C15B 3.3(8) . . . . ? N3B C8B N2B C7B 2.5(7) . . . . ? N3B C9B C17B C18B 24.1(6) . . . . ? N3B C9B C17B C22B -154.1(4) . . . . ?