#------------------------------------------------------------------------------ #$Date: 2019-11-11 20:29:55 +0200 (Mon, 11 Nov 2019) $ #$Revision: 227275 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035863.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_4035863 loop_ _publ_author_name 'Bookser, Brett C.' 'Weinhouse, Michael I.' 'Burns, Aaron C.' 'Valiere, Andrew N.' 'Valdez, Lino J.' 'Stanczak, Pawel' 'Na, Jim' 'Rheingold, Arnold L.' 'Moore, Curtis E.' 'Dyck, Brian' _publ_section_title ; Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds. ; _journal_issue 12 _journal_name_full 'The Journal of organic chemistry' _journal_page_first 6334 _journal_page_last 6353 _journal_paper_doi 10.1021/acs.joc.8b00540 _journal_volume 83 _journal_year 2018 _chemical_formula_moiety 'C6 H5 Cl N4' _chemical_formula_sum 'C6 H5 Cl N4' _chemical_formula_weight 168.59 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2016-09-07 _audit_creation_method ; Olex2 1.2-beta (compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221) ; _cell_angle_alpha 90 _cell_angle_beta 108.474(19) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.008(8) _cell_length_b 13.971(15) _cell_length_c 7.564(9) _cell_measurement_reflns_used 1575 _cell_measurement_temperature 100 _cell_measurement_theta_max 25.283 _cell_measurement_theta_min 2.848 _cell_volume 702.4(14) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_collection 'APEX2 v2013.6-2 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'ShelXT (Sheldrick, 2008)' _diffrn_ambient_temperature 100 _diffrn_detector 'Bruker APEX-II CCD' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD Area Detector' _diffrn_measured_fraction_theta_full 0.927 _diffrn_measured_fraction_theta_max 0.765 _diffrn_measurement_device 'Kappa Four-Circle Diffractometer' _diffrn_measurement_device_type 'Bruker APEX II Ultra' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'Double Bounce Multilayer Mirrors' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_unetI/netI 0.0450 _diffrn_reflns_Laue_measured_fraction_full 0.927 _diffrn_reflns_Laue_measured_fraction_max 0.765 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 3813 _diffrn_reflns_point_group_measured_fraction_full 0.927 _diffrn_reflns_point_group_measured_fraction_max 0.765 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.535 _diffrn_reflns_theta_min 2.916 _diffrn_source 'Micro Focus Rotating Anode' _diffrn_source_type 'Bruker TXS' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.472 _exptl_absorpt_correction_T_max 0.2590 _exptl_absorpt_correction_T_min 0.2223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1295 before and 0.0488 after correction. The Ratio of minimum to maximum transmission is 0.8583. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.594 _exptl_crystal_description plate _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.237 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 1239 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.159 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0465 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.5939P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0982 _refine_ls_wR_factor_ref 0.1035 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1039 _reflns_number_total 1239 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jo8b00540_si_009.cif _cod_data_source_block dart174 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_database_code 4035863 _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 0.963 _shelx_estimated_absorpt_t_min 0.879 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Sof(C4')=Sof(C2')=Sof(C5')=Sof(H4)=Sof(N4')=Sof(C1')=Sof(H4AA)=Sof(H4AB)= Sof(H4AC)=Sof(N2')=Sof(C6')=Sof(H2AA)=Sof(N1')=1-FVAR(1) Sof(N2)=Sof(C6)=Sof(H6)=Sof(C2)=Sof(N1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)= Sof(N3)=Sof(C4)=Sof(C5)=Sof(H5)=FVAR(1) 3.a Aromatic/amide H refined with riding coordinates: C6(H6), C5(H5), C5'(H4), C6'(H2AA) 3.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C1'(H4AA,H4AB,H4AC) ; _shelx_res_file ; dart174.res created by SHELXL-2014/7 TITL dart174_a.res in P2(1)/c CELL 0.71073 7.008 13.9713 7.5637 90 108.474 90 ZERR 4 0.008 0.0154 0.0086 0 0.019 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N UNIT 24 20 4 16 L.S. 4 PLAN -10 0 0 SIZE 0.08 0.27 0.28 TEMP -173.15 list 4 BOND $H CONF fmap 2 acta MORE -1 REM REM REM WGHT 0.025900 0.593900 FVAR 0.73323 0.70013 CL1 3 0.462790 0.394511 0.625328 11.00000 0.03748 0.02480 = 0.06408 0.00945 0.02525 0.01454 N3' 4 0.706217 0.090161 0.664468 11.00000 0.03411 0.02147 = 0.05393 0.00080 0.01309 0.00518 PART 1 N2 4 1.051743 0.253783 0.723026 21.00000 0.01639 0.04014 = 0.04635 -0.00324 0.01478 -0.00282 C6 1 0.515890 0.110523 0.628916 21.00000 0.02078 0.01653 = 0.05409 -0.00574 0.01060 -0.00054 AFIX 43 H6 2 0.422355 0.059162 0.605762 21.00000 -1.20000 AFIX 0 C2 1 0.805016 0.166686 0.680206 21.00000 0.01361 0.02809 = 0.02540 0.00035 0.00261 0.00189 PART 0 C3' 1 0.737608 0.259264 0.672979 11.00000 0.02677 0.02832 = 0.02235 0.00305 0.00875 0.00483 PART 1 N1 4 0.907238 0.314580 0.702521 21.00000 0.01427 0.02344 = 0.04278 0.00212 0.00905 -0.00513 C1 1 0.940090 0.418327 0.716851 21.00000 0.03809 0.02801 = 0.06221 -0.00868 0.02234 -0.01853 AFIX 137 H1A 2 0.905764 0.442883 0.824331 21.00000 -1.50000 H1B 2 0.854786 0.449269 0.602917 21.00000 -1.50000 H1C 2 1.081676 0.432169 0.732881 21.00000 -1.50000 AFIX 0 N3 4 0.995198 0.164890 0.709216 21.00000 0.01281 0.04012 = 0.04917 -0.00112 0.00763 0.00484 C4 1 0.559805 0.282262 0.644965 21.00000 0.01770 0.01707 = 0.03020 0.00336 0.00725 0.00296 C5 1 0.442202 0.204246 0.623099 21.00000 0.01525 0.02163 = 0.03639 -0.00022 0.00730 0.00109 AFIX 43 H5 2 0.302433 0.213012 0.602723 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C4' 1 0.665572 0.348739 0.654851 -21.00000 0.01142 0.01711 = 0.03056 -0.00108 0.00626 0.00350 C2' 1 0.895595 0.222248 0.703509 -21.00000 0.02454 0.03005 = 0.03230 -0.00049 0.01103 0.00222 C5' 1 0.812468 0.412276 0.682569 -21.00000 0.03005 0.02100 = 0.03869 0.00655 0.01084 -0.00618 AFIX 43 H4 2 0.789601 0.479387 0.678036 -21.00000 -1.20000 AFIX 0 N4' 4 0.613297 0.166833 0.651966 -21.00000 0.01977 0.01651 = 0.04525 0.00224 0.00267 0.00605 C1' 1 0.420074 0.147533 0.609718 -21.00000 0.02785 0.00696 = 0.04388 -0.00397 0.01275 0.00121 AFIX 137 H4AA 2 0.348394 0.173152 0.485813 -21.00000 -1.50000 H4AB 2 0.367141 0.177031 0.702134 -21.00000 -1.50000 H4AC 2 0.400894 0.078053 0.609765 -21.00000 -1.50000 AFIX 0 N2' 4 0.906399 0.126817 0.709332 -21.00000 0.01170 0.03352 = 0.04854 -0.00234 -0.00011 0.00740 C6' 1 0.990092 0.375188 0.716407 -21.00000 0.03769 0.02179 = 0.04407 -0.00108 0.01848 0.00232 AFIX 43 H2AA 2 1.097190 0.419786 0.736388 -21.00000 -1.20000 AFIX 0 N1' 4 1.042668 0.284648 0.726923 -21.00000 0.01368 0.01964 = 0.03678 0.00383 -0.00528 -0.00094 HKLF 4 REM dart174_a.res in P2(1)/c REM R1 = 0.0465 for 1039 Fo > 4sig(Fo) and 0.0587 for all 1239 data REM 175 parameters refined using 0 restraints END WGHT 0.0254 0.5980 REM Highest difference peak 0.237, deepest hole -0.305, 1-sigma level 0.056 Q1 1 0.4185 0.3452 0.5757 11.00000 0.05 0.24 Q2 1 0.3816 0.3844 0.4930 11.00000 0.05 0.23 Q3 1 0.5583 0.4422 0.5120 11.00000 0.05 0.19 Q4 1 0.4676 0.3980 0.4663 11.00000 0.05 0.19 Q5 1 0.6463 0.0874 0.5271 11.00000 0.05 0.18 Q6 1 0.5578 0.3926 0.7723 11.00000 0.05 0.18 Q7 1 0.8881 0.4360 0.5390 11.00000 0.05 0.18 Q8 1 1.0233 0.4195 0.8776 11.00000 0.05 0.17 Q9 1 0.8775 0.3627 0.5465 11.00000 0.05 0.17 Q10 1 0.7383 0.1541 0.5575 11.00000 0.05 0.16 ; _shelx_res_checksum 71952 _shelx_hkl_file ; 0 0 -1 -0.20 0.50 0 0 -1 0.50 0.40 0 0 1 0.30 0.40 0 0 1 0.20 0.30 0 0 2 5668.93 236.38 0 0 2 5829.22 236.38 0 0 -2 6096.29 238.08 0 0 -2 5901.31 238.98 0 0 -3 0.50 1.00 0 0 -3 0.50 0.80 0 0 -4 779.22 32.50 0 0 -4 767.22 32.00 0 0 -5 -0.50 1.10 0 0 -5 3.30 1.60 0 0 -6 125.99 7.50 0 0 -7 5.50 2.60 0 0 -7 1.50 3.50 0 0 -8 10.50 4.80 0 -1 0 0.10 0.20 0 -1 0 0.40 0.20 0 1 -1 66.59 3.20 0 1 -1 64.89 3.30 0 -1 1 67.79 3.20 0 -1 1 64.59 3.40 0 1 -2 9753.42 392.16 0 1 -2 9888.41 392.36 0 -1 -2 9667.33 388.26 0 -1 2 9999.00 391.16 0 -1 -2 9199.38 388.36 0 -1 2 9569.34 391.86 0 1 -3 12.20 2.00 0 1 -3 12.00 1.60 0 -1 3 10.40 1.80 0 -1 -3 12.00 1.20 0 -1 -3 11.50 1.60 0 -1 3 14.40 1.70 0 1 -4 1210.58 49.80 0 1 -4 1258.37 49.40 0 -1 -4 1194.88 49.30 0 -1 4 1186.68 48.80 0 -1 4 1150.18 49.00 0 -1 -4 1201.58 48.90 0 1 -5 30.00 3.50 0 1 -5 23.00 2.80 0 -1 -5 25.50 2.40 0 -1 -5 31.90 2.90 0 1 -6 1.00 2.20 0 -1 -6 -1.90 1.80 0 1 -7 1.40 2.60 0 1 -7 -1.40 3.10 0 -1 -7 5.60 2.40 0 -1 -7 4.10 3.30 0 2 0 2656.13 102.99 0 -2 0 2387.76 103.49 0 -2 0 2505.35 102.69 0 2 -1 114.89 5.50 0 2 -1 117.29 5.30 0 -2 1 104.69 5.40 0 -2 1 116.39 5.30 0 2 -2 808.42 34.20 0 2 -2 850.01 34.00 0 -2 2 795.82 34.00 0 -2 2 848.82 34.40 0 2 -3 47.50 3.10 0 2 -3 42.30 3.40 0 -2 -3 45.40 2.10 0 -2 3 44.70 3.10 0 -2 -3 42.00 2.30 0 -2 3 47.60 3.50 0 2 -4 16.00 2.30 0 2 -4 17.30 2.60 0 -2 -4 20.20 2.20 0 -2 4 14.40 2.40 0 -2 -4 21.60 1.70 0 -2 4 14.70 2.10 0 2 -5 3.10 2.00 0 2 -5 1.80 1.60 0 -2 5 2.10 1.40 0 -2 -5 3.20 1.20 0 -2 5 2.90 1.40 0 -2 -5 2.20 1.50 0 2 -6 20.40 4.70 0 2 -6 25.50 4.00 0 -2 -6 10.30 2.30 0 2 -7 25.10 4.40 0 2 -7 31.90 5.80 0 3 0 0.80 0.90 0 -3 0 1.10 0.80 0 -3 0 0.80 0.90 0 3 -1 5.10 1.40 0 3 -1 4.10 1.20 0 3 -1 7.40 1.50 0 -3 1 3.80 1.30 0 -3 1 4.10 1.20 0 3 -2 944.81 39.40 0 3 -2 969.70 39.20 0 -3 2 950.00 39.50 0 -3 2 933.21 39.20 0 3 -3 5.40 1.40 0 3 -3 4.00 1.70 0 -3 3 3.10 1.50 0 -3 3 2.60 1.60 0 3 -4 6.70 1.80 0 3 -4 7.10 2.10 0 -3 -4 4.50 0.70 0 -3 4 9.70 2.10 0 -3 4 9.90 2.30 0 -3 -4 5.20 1.10 0 3 -5 8.60 2.10 0 3 -5 11.40 2.80 0 3 -5 7.70 3.10 0 -3 -5 9.90 1.70 0 -3 -5 7.10 1.20 0 -3 5 11.40 2.30 0 -3 5 7.30 2.20 0 3 -6 117.59 7.70 0 3 -6 119.29 8.60 0 -3 6 106.89 6.10 0 -3 -6 112.69 6.30 0 -3 6 108.39 6.30 0 3 -7 8.90 3.50 0 3 -7 2.20 3.50 0 4 0 2293.17 92.89 0 -4 0 2249.38 92.79 0 -4 0 2365.46 92.89 0 4 -1 302.77 12.80 0 4 -1 295.27 13.00 0 -4 1 276.77 12.80 0 -4 1 289.27 13.00 0 4 -2 6.90 1.80 0 4 -2 11.20 2.30 0 4 -2 10.10 1.80 0 -4 2 7.60 1.70 0 -4 2 8.50 2.00 0 4 -3 38.60 4.30 0 4 -3 32.00 3.50 0 4 -3 30.30 2.90 0 -4 3 28.60 3.50 0 -4 3 27.20 3.10 0 4 -4 375.06 17.00 0 4 -4 326.37 15.70 0 4 -4 337.57 16.20 0 -4 4 336.47 16.40 0 -4 4 348.07 15.90 0 4 -5 6.50 2.40 0 4 -5 4.30 2.20 0 4 -5 7.20 3.20 0 -4 -5 6.70 1.40 0 -4 5 6.00 2.20 0 -4 5 7.60 2.40 0 4 -6 -1.50 2.60 0 4 -6 5.40 2.90 0 -4 -6 2.70 1.50 0 -4 6 0.90 2.00 0 -4 6 0.90 2.00 0 4 -7 9.00 4.20 0 4 -7 6.40 3.40 0 5 0 1.40 1.00 0 -5 0 0.40 0.90 0 -5 0 1.80 1.10 0 5 -1 260.47 11.70 0 5 -1 259.77 11.90 0 -5 1 280.97 12.10 0 -5 -1 250.27 11.10 0 -5 -1 248.48 11.10 0 -5 1 248.68 11.70 0 5 -2 28.90 3.50 0 5 -2 23.60 3.00 0 5 -2 24.90 2.80 0 -5 2 22.90 3.10 0 -5 2 25.30 2.90 0 5 -3 42.80 3.80 0 5 -3 41.60 3.90 0 5 -3 42.70 3.50 0 -5 3 41.90 3.80 0 -5 3 40.10 3.70 0 5 -4 13.30 2.80 0 5 -4 8.10 2.10 0 5 -4 11.80 3.10 0 -5 4 9.10 2.30 0 -5 4 10.10 2.70 0 5 -5 85.69 6.40 0 5 -5 100.49 7.30 0 -5 -5 86.19 4.40 0 -5 5 74.69 6.30 0 -5 5 88.29 6.30 0 5 -6 4.20 3.40 0 5 -6 -1.90 2.40 0 -5 6 0.30 2.30 0 -5 -6 4.00 1.40 0 -5 6 2.70 3.00 0 5 -7 3.30 3.10 0 5 -7 10.10 4.40 0 6 0 1568.04 63.89 0 -6 0 1580.34 63.79 0 -6 0 1585.44 63.99 0 -6 0 1523.45 63.69 0 6 -1 8.70 2.10 0 -6 -1 5.30 1.30 0 -6 1 7.40 1.80 0 -6 1 7.20 2.00 0 -6 -1 7.50 1.30 0 6 -2 92.89 6.10 0 6 -2 98.79 5.70 0 -6 -2 98.69 4.70 0 -6 2 90.59 5.70 0 -6 2 100.99 6.20 0 6 -3 214.58 11.30 0 6 -3 224.78 11.10 0 6 -3 211.18 10.70 0 -6 3 221.08 10.90 0 -6 3 200.38 11.30 0 6 -4 125.29 8.40 0 6 -4 144.59 8.30 0 -6 4 128.09 8.00 0 -6 -4 136.69 5.70 0 -6 4 130.69 8.40 0 6 -5 8.40 3.70 0 6 -5 8.00 3.20 0 -6 5 9.00 2.90 0 -6 -5 8.70 1.20 0 -6 5 12.00 3.20 0 6 -6 10.30 3.30 0 6 -6 13.80 4.40 0 -6 6 6.50 4.00 0 -6 6 12.00 3.20 0 6 -7 25.00 5.70 0 7 0 4.80 1.60 0 -7 0 4.10 1.40 0 -7 0 2.70 1.40 0 -7 0 1.90 1.20 0 7 -1 21.80 3.10 0 -7 -1 14.60 2.00 0 -7 1 17.80 2.60 0 -7 -1 17.50 2.10 0 -7 1 17.50 2.80 0 7 -2 910.61 38.20 0 7 -2 909.11 37.80 0 -7 -2 901.41 36.70 0 -7 2 848.82 38.20 0 -7 -2 872.71 36.60 0 -7 2 906.31 37.90 0 7 -3 80.29 5.90 0 7 -3 87.99 5.50 0 -7 3 81.89 6.10 0 -7 -3 77.19 4.00 0 -7 3 77.99 5.80 0 7 -4 17.10 3.40 0 7 -4 24.10 4.50 0 -7 4 15.10 3.50 0 -7 -4 16.30 1.40 0 -7 4 14.90 3.30 0 7 -5 40.60 5.20 0 7 -5 37.60 5.80 0 -7 -5 31.20 2.20 0 -7 5 35.70 5.30 0 -7 5 37.60 5.10 0 7 -6 84.59 7.90 0 -7 6 91.69 7.50 0 7 -7 13.00 5.20 0 8 0 155.38 8.10 0 -8 0 150.08 7.70 0 -8 0 159.98 8.00 0 -8 0 145.99 8.00 0 8 -1 581.54 26.40 0 -8 1 621.04 26.50 0 -8 -1 617.44 25.60 0 -8 1 599.14 26.70 0 -8 -1 613.04 25.80 0 8 -2 5.30 2.20 0 -8 -2 5.40 1.50 0 -8 -2 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50.59 5.70 -4 9 1 50.49 5.30 -4 -9 1 49.80 6.70 -4 9 0 70.59 6.00 4 9 0 68.79 5.20 -4 -9 0 81.29 8.60 -4 9 -1 12.50 3.60 4 9 1 12.20 2.30 -4 -9 -1 11.60 4.00 -4 9 -2 51.89 6.50 4 -9 2 53.29 6.20 -4 -9 -2 41.40 6.50 -4 9 -3 -1.60 2.60 4 -9 3 2.70 2.90 -4 -9 -3 3.20 3.70 -4 9 -4 7.40 4.20 -4 -9 -4 6.90 4.10 4 -9 4 2.10 3.50 -4 -10 6 16.90 5.80 -4 -10 5 35.10 6.60 -4 -10 4 58.29 8.00 -4 -10 3 21.50 5.10 -4 -10 2 93.29 8.30 -4 10 1 90.79 6.50 -4 -10 1 103.09 8.40 4 10 0 86.69 4.60 4 10 0 84.39 5.80 -4 10 0 82.39 6.70 -4 -10 0 73.49 7.40 -4 10 -1 39.50 5.80 4 10 1 36.80 3.50 -4 -10 -1 32.60 5.80 -4 10 -2 112.49 8.70 4 -10 2 113.19 8.50 -4 -10 -2 114.39 9.40 -4 10 -3 55.29 7.10 4 -10 3 38.70 5.90 -4 -10 -3 60.69 7.90 -4 10 -4 60.59 7.90 4 -10 4 61.69 7.10 -4 -11 6 64.49 9.20 -4 -11 5 27.60 6.10 -4 -11 4 9.30 4.50 -4 -11 3 4.10 3.70 -4 -11 2 34.50 6.10 -4 11 1 41.20 4.90 4 11 -1 36.70 3.60 -4 -11 1 37.50 6.60 -4 11 0 98.89 7.20 4 11 0 98.69 5.20 4 11 0 91.59 6.30 -4 -11 0 102.59 10.30 -4 11 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11.00 4.70 -5 -7 -4 8.50 5.10 5 -7 4 2.40 3.40 -5 -8 6 8.30 4.30 -5 -8 5 12.80 5.00 -5 -8 4 32.20 6.20 -5 8 3 5.70 2.10 -5 -8 3 4.30 3.70 -5 8 2 19.40 3.70 -5 -8 2 19.00 5.00 -5 8 1 17.40 3.80 -5 -8 1 14.10 4.50 -5 8 0 10.90 3.60 5 8 0 11.40 3.00 -5 -8 0 9.90 4.50 -5 8 -1 113.19 8.70 5 8 1 111.79 7.10 -5 -8 -1 127.39 9.90 -5 8 -2 1.90 3.10 -5 -8 -2 3.00 4.00 -5 8 -3 11.10 4.20 5 -8 3 17.70 4.60 -5 -8 -3 8.50 4.80 -5 8 -4 -2.90 3.20 5 -8 4 6.00 4.00 -5 -8 -4 2.70 4.60 -5 -9 6 0.80 4.30 -5 -9 5 10.70 4.80 -5 -9 4 74.29 9.10 -5 9 3 2.70 1.80 -5 -9 3 2.00 3.70 -5 9 2 76.69 5.90 -5 -9 2 84.29 9.30 -5 9 1 119.39 8.00 -5 -9 1 117.29 9.70 -5 9 0 6.10 3.10 -5 -9 0 7.10 3.70 -5 9 -1 6.10 3.40 5 9 1 -0.20 2.70 -5 -9 -1 10.00 4.80 -5 9 -2 15.80 4.50 -5 -9 -2 17.00 5.30 -5 9 -3 102.29 9.00 5 -9 3 94.19 8.30 -5 -9 -3 105.59 11.30 -5 -10 6 64.79 9.30 -5 -10 5 12.40 4.90 -5 -10 4 50.19 7.80 -5 -10 3 12.00 4.50 -5 10 2 143.29 8.50 -5 -10 2 139.69 11.00 -5 10 1 61.19 6.40 -5 -10 1 57.19 7.90 -5 10 0 115.79 8.30 -5 -10 0 104.19 9.50 -5 10 -1 115.79 9.30 -5 -10 -1 144.39 10.90 -5 10 -2 24.90 5.20 -5 -10 -2 16.20 5.30 5 -10 2 23.60 4.80 -5 10 -3 8.60 4.20 -5 -10 -3 19.90 6.00 5 -10 3 12.30 4.60 -5 -11 5 80.69 10.60 -5 -11 4 107.09 11.70 -5 -11 3 117.19 10.30 -5 11 2 37.70 4.60 -5 -11 2 46.40 7.50 -5 11 1 -1.40 2.30 -5 -11 1 -0.20 3.40 -5 11 0 73.59 7.80 -5 -11 0 59.79 8.60 -5 11 -1 36.00 5.90 -5 -11 -1 37.50 7.00 -5 11 -2 10.30 4.00 5 -11 2 10.20 4.20 -5 -11 -2 11.20 5.10 -5 -12 4 2.70 4.30 -5 -12 3 62.89 9.10 -5 -12 2 8.50 4.70 -5 -12 1 104.59 10.10 -5 12 0 4.50 3.10 -5 -12 0 3.00 4.20 -5 12 -1 26.70 5.20 -5 -12 -1 25.50 6.50 5 -12 1 26.60 5.10 -5 12 -2 2.40 3.40 -5 -13 3 24.20 6.40 -5 -13 2 41.20 7.60 -5 -13 1 58.39 8.70 -5 13 0 10.60 3.50 -5 -13 0 11.70 5.00 -5 13 -1 16.00 4.30 -5 -13 -1 12.70 5.60 5 -13 1 19.40 4.80 -6 0 6 142.69 8.80 -6 0 5 -2.00 2.70 -6 0 4 44.10 6.20 -6 0 3 2.60 2.70 -6 0 2 49.80 6.70 -6 0 1 -3.30 1.90 -6 0 0 25.20 5.70 -6 0 -1 3.50 3.60 -6 0 -2 76.99 9.60 -6 0 -3 8.40 4.80 -6 0 -4 3.40 4.90 6 0 4 -4.10 3.80 -6 1 6 6.50 2.30 -6 -1 6 4.20 2.90 -6 1 5 21.00 4.10 -6 -1 5 21.80 4.50 -6 1 4 66.29 6.40 -6 -1 4 60.09 7.30 -6 1 3 43.40 5.90 -6 -1 3 39.70 6.10 -6 1 2 3.80 3.10 -6 -1 2 3.10 3.10 -6 1 1 78.89 7.50 -6 -1 1 90.99 7.90 -6 1 0 5.90 3.70 -6 -1 0 -0.90 2.90 -6 1 -1 77.59 9.00 6 1 1 51.99 5.10 -6 -1 -1 52.39 7.70 -6 1 -2 64.19 9.10 -6 -1 -2 66.09 8.90 -6 1 -3 17.40 5.50 -6 -1 -3 17.10 5.90 -6 1 -4 31.60 6.90 -6 -1 -4 48.60 8.70 -6 -2 6 0.50 2.60 -6 2 5 82.49 6.20 -6 -2 5 72.09 8.20 -6 2 4 0.90 2.50 -6 -2 4 -0.90 2.90 -6 2 3 26.80 4.90 -6 -2 3 23.80 5.20 -6 2 2 47.00 6.40 -6 -2 2 64.79 7.90 -6 2 1 29.20 5.20 -6 -2 1 34.20 6.00 -6 2 0 69.59 8.20 -6 -2 0 76.69 9.20 -6 2 -1 88.09 8.30 6 2 1 87.29 6.40 -6 -2 -1 94.99 9.10 6 2 2 1.90 2.20 -6 2 -2 5.10 3.70 -6 -2 -2 1.50 3.40 -6 2 -3 46.70 7.70 -6 -2 -3 37.50 7.70 -6 2 -4 29.40 6.90 -6 -2 -4 31.30 7.30 6 -2 4 27.40 4.70 -6 -3 6 10.20 3.80 -6 3 5 23.00 3.40 -6 -3 5 17.00 4.50 -6 3 4 148.29 8.90 -6 -3 4 117.49 9.80 -6 3 3 2.70 2.60 -6 -3 3 0.30 2.90 -6 3 2 11.60 3.50 -6 -3 2 15.90 4.50 -6 3 1 3.80 2.80 -6 -3 1 2.40 3.50 -6 3 0 204.08 13.00 -6 -3 0 203.38 13.60 6 3 1 23.10 3.70 -6 3 -1 13.50 4.40 -6 -3 -1 24.20 5.70 -6 3 -2 139.19 11.00 -6 -3 -2 154.58 12.00 -6 3 -3 32.20 6.50 -6 -3 -3 26.50 6.60 -6 3 -4 10.60 5.20 -6 -3 -4 4.50 4.90 6 -3 4 6.80 3.50 -6 -4 7 27.10 5.60 -6 -4 6 84.69 8.20 -6 4 5 3.50 1.80 -6 -4 5 2.40 3.20 -6 4 4 4.00 2.60 -6 -4 4 1.60 3.20 -6 4 3 361.06 18.60 -6 -4 3 388.06 20.40 -6 4 2 416.16 20.10 -6 -4 2 367.86 21.00 -6 4 1 261.27 14.80 -6 -4 1 258.97 15.80 -6 4 0 83.39 7.80 -6 -4 0 116.69 9.50 -6 4 -1 27.70 5.50 6 4 1 30.10 4.10 -6 -4 -1 28.30 6.10 -6 4 -2 26.50 6.10 6 4 2 17.30 4.70 -6 -4 -2 17.20 5.70 -6 4 -3 64.29 9.00 -6 -4 -3 89.79 10.70 -6 -5 7 8.70 4.40 -6 -5 6 23.40 5.50 -6 5 5 314.67 14.20 -6 -5 5 322.57 18.20 -6 -5 4 83.09 9.30 -6 5 3 209.68 11.90 -6 -5 3 208.38 13.70 -6 5 2 6.60 3.50 -6 -5 2 7.80 4.10 -6 5 1 378.16 19.60 -6 -5 1 379.16 20.80 -6 5 0 111.49 8.90 -6 -5 0 101.29 9.40 6 5 1 385.06 19.70 -6 5 -1 366.56 20.20 -6 -5 -1 365.16 20.90 -6 5 -2 52.99 7.70 -6 -5 -2 51.39 8.40 -6 5 -3 2.20 4.00 -6 -5 -3 -0.60 3.80 -6 -6 7 57.69 7.70 -6 -6 6 16.10 5.20 -6 -6 5 54.19 7.70 -6 6 4 116.39 7.00 -6 -6 4 93.39 9.10 -6 6 3 274.77 14.60 -6 -6 3 297.27 17.20 -6 6 2 26.10 4.90 -6 -6 2 23.20 5.90 -6 6 1 239.98 14.10 -6 -6 1 250.67 15.80 -6 6 0 2.50 3.40 -6 -6 0 3.30 3.80 -6 6 -1 24.10 5.20 -6 -6 -1 21.40 5.70 -6 6 -2 9.90 4.30 -6 -6 -2 3.10 4.70 -6 6 -3 26.30 6.10 -6 -6 -3 6.60 5.10 -6 -7 6 40.00 7.30 -6 -7 5 6.70 4.50 -6 7 4 29.90 3.60 -6 -7 4 27.10 6.20 -6 7 3 21.50 3.80 -6 -7 3 16.80 5.40 -6 7 2 35.20 5.40 -6 -7 2 31.10 6.20 -6 7 1 -2.20 2.70 -6 -7 1 3.70 3.70 -6 7 0 0.60 2.80 -6 -7 0 0.90 3.90 -6 7 -1 -0.50 3.00 -6 -7 -1 -4.90 3.60 -6 7 -2 5.60 3.80 -6 -7 -2 12.10 5.10 -6 7 -3 -0.90 3.50 -6 -7 -3 8.20 5.40 6 -7 3 1.10 3.10 -6 -8 6 13.40 5.50 -6 -8 5 4.40 4.10 -6 8 4 5.20 1.90 -6 -8 4 4.90 4.30 -6 8 3 155.38 9.00 -6 -8 3 144.69 11.60 -6 8 2 1.60 2.90 -6 -8 2 6.40 4.80 -6 8 1 75.89 6.90 -6 -8 1 84.99 10.50 -6 8 0 3.60 3.40 -6 -8 0 1.90 3.80 -6 8 -1 31.20 6.10 -6 -8 -1 14.00 5.20 -6 8 -2 1.60 3.30 -6 -8 -2 3.10 4.40 -6 -9 5 136.29 11.80 -6 -9 4 4.20 4.30 -6 9 3 50.39 4.70 -6 -9 3 51.69 8.00 -6 9 2 2.50 2.60 -6 -9 2 2.90 4.10 -6 9 1 125.49 9.10 -6 -9 1 131.39 11.00 -6 9 0 19.60 4.50 -6 -9 0 36.10 7.00 -6 9 -1 54.79 7.20 -6 -9 -1 37.70 7.80 -6 9 -2 21.40 5.20 -6 -9 -2 18.10 6.50 -6 -10 5 2.60 4.60 -6 -10 4 20.70 5.70 -6 -10 3 68.89 9.20 -6 10 2 53.79 6.00 -6 -10 2 57.49 8.50 -6 10 1 18.70 4.40 -6 -10 1 16.30 5.50 -6 10 0 8.00 3.80 -6 -10 0 -3.10 3.90 -6 10 -1 -0.20 3.00 -6 -10 -1 6.50 4.80 -6 -11 4 29.00 6.60 -6 -11 3 6.30 4.70 -6 11 2 0.80 2.50 -6 -11 2 -1.40 3.30 -6 11 1 25.20 4.50 -6 -11 1 26.10 6.40 -6 11 0 40.20 6.20 -6 -11 0 35.50 7.80 -6 11 -1 45.90 6.60 -6 -11 -1 48.90 8.80 -6 -12 3 55.99 8.90 -6 12 2 -2.30 2.20 -6 -12 2 -1.70 4.00 -6 12 1 56.09 6.60 -6 -12 1 73.59 10.40 -6 12 0 22.60 4.90 -6 -12 0 45.80 8.00 -7 0 6 10.00 3.70 -7 0 5 -1.70 2.90 -7 0 4 99.29 8.40 -7 0 3 2.90 3.50 -7 0 2 188.68 13.10 -7 0 1 -0.50 3.30 -7 0 0 11.20 4.40 -7 0 -1 2.10 3.80 -7 0 -2 22.30 6.50 -7 0 -3 -2.30 3.80 -7 1 6 14.70 4.40 -7 -1 6 12.40 4.00 -7 1 5 88.69 7.50 -7 -1 5 84.49 8.00 -7 1 4 20.70 4.80 -7 -1 4 23.90 5.30 -7 1 3 97.09 8.40 -7 -1 3 87.39 8.50 -7 1 2 85.99 8.20 -7 -1 2 81.19 9.40 -7 1 1 40.70 7.10 -7 -1 1 35.00 6.70 -7 1 0 100.29 9.60 -7 -1 0 95.39 9.30 -7 1 -1 28.30 6.40 -7 -1 -1 31.60 7.30 -7 1 -2 0.50 4.00 -7 -1 -2 6.60 5.10 -7 1 -3 6.30 5.30 -7 -1 -3 1.20 4.30 -7 -2 6 43.20 6.30 -7 2 5 27.70 4.80 -7 -2 5 23.00 5.40 -7 2 4 105.49 8.30 -7 -2 4 92.89 9.00 -7 2 3 152.78 10.70 -7 -2 3 151.08 11.70 -7 2 2 18.20 5.00 -7 -2 2 13.30 4.60 -7 2 1 136.99 10.30 -7 -2 1 115.69 10.70 -7 2 0 5.70 3.70 -7 -2 0 5.50 3.90 -7 2 -1 7.00 4.20 -7 -2 -1 10.60 5.20 -7 2 -2 2.70 4.40 -7 -2 -2 11.80 5.50 -7 -3 6 17.00 4.70 -7 3 5 6.60 3.00 -7 -3 5 8.30 4.20 -7 3 4 122.69 8.90 -7 -3 4 116.29 10.20 -7 3 3 -0.20 2.50 -7 -3 3 2.50 3.50 -7 3 2 81.29 9.00 -7 -3 2 76.09 9.70 -7 3 1 36.00 6.50 -7 -3 1 28.70 6.80 -7 3 0 -2.00 2.80 -7 -3 0 -2.00 3.10 -7 3 -1 10.30 4.40 -7 -3 -1 13.40 5.50 -7 3 -2 8.80 4.70 -7 -3 -2 8.90 5.10 -7 -4 6 169.28 12.30 -7 -4 5 123.99 10.30 -7 4 4 78.39 6.80 -7 -4 4 66.29 8.80 -7 4 3 7.10 3.50 -7 -4 3 10.10 4.40 -7 4 2 3.70 3.10 -7 -4 2 -0.70 3.80 -7 4 1 32.40 5.70 -7 -4 1 28.30 6.60 -7 4 0 -1.60 3.40 -7 -4 0 0.50 3.80 -7 4 -1 11.30 4.70 -7 -4 -1 7.00 4.30 -7 4 -2 2.60 4.20 -7 -4 -2 -3.30 3.80 -7 -5 6 12.10 4.90 -7 -5 5 148.79 11.60 -7 5 4 9.90 3.40 -7 -5 4 9.40 4.40 -7 5 3 193.98 12.00 -7 -5 3 191.48 13.60 -7 5 2 15.30 4.30 -7 -5 2 21.80 5.40 -7 5 1 41.30 6.80 -7 -5 1 30.70 6.70 -7 5 0 8.50 4.20 -7 -5 0 15.80 5.50 -7 5 -1 2.00 3.80 -7 -5 -1 0.00 3.50 -7 5 -2 7.10 4.60 -7 -5 -2 12.20 5.60 -7 -6 6 6.40 4.60 -7 -6 5 95.39 10.80 -7 6 4 34.50 4.80 -7 -6 4 24.80 6.30 -7 6 3 27.40 4.60 -7 -6 3 37.20 7.20 -7 6 2 74.29 7.30 -7 -6 2 80.19 9.80 -7 6 1 1.20 2.90 -7 -6 1 3.00 4.10 -7 6 0 0.60 3.20 -7 -6 0 8.90 4.90 -7 6 -1 60.69 8.40 -7 -6 -1 79.19 10.90 -7 6 -2 5.90 4.50 -7 -6 -2 16.10 6.00 -7 -7 5 2.60 4.40 -7 7 4 35.00 4.50 -7 -7 4 32.40 6.60 -7 7 3 6.50 3.10 -7 -7 3 4.70 4.20 -7 7 2 8.50 3.60 -7 -7 2 10.40 5.50 -7 7 1 9.40 4.30 -7 -7 1 8.00 4.90 -7 7 0 71.69 8.90 -7 -7 0 60.69 9.00 -7 7 -1 6.30 4.10 -7 -7 -1 6.20 4.70 -7 -8 5 43.60 7.90 -7 -8 4 12.50 5.20 -7 8 3 30.70 4.70 -7 -8 3 29.70 6.80 -7 8 2 13.00 3.80 -7 -8 2 19.70 5.80 -7 8 1 26.50 5.10 -7 -8 1 46.00 8.00 -7 8 0 6.50 3.70 -7 -8 0 4.10 4.80 -7 8 -1 8.70 4.50 -7 -8 -1 16.00 6.80 -7 -9 4 22.40 7.00 -7 9 3 10.90 3.30 -7 -9 3 17.10 6.30 -7 9 2 13.50 3.90 -7 -9 2 6.30 4.90 -7 9 1 43.50 6.80 -7 -9 1 30.60 7.30 -7 9 0 -2.40 2.90 -7 -9 0 -4.10 4.70 -7 10 3 1.10 2.60 -7 -10 3 6.00 5.40 -7 10 2 48.70 6.20 -7 -10 2 40.40 8.10 -7 10 1 35.40 5.60 -7 -10 1 43.00 8.10 -8 0 5 -3.00 3.00 -8 0 4 3.40 3.80 -8 0 3 -2.90 3.00 -8 0 2 5.50 4.10 -8 0 1 -1.80 3.40 -8 0 0 65.09 9.30 -8 0 -1 0.40 4.00 -8 -1 6 14.20 4.50 -8 1 5 26.10 5.40 -8 -1 5 15.80 4.70 -8 1 4 41.80 6.50 -8 -1 4 39.20 6.90 -8 1 3 4.90 4.00 -8 -1 3 3.90 3.60 -8 1 2 1.10 3.90 -8 -1 2 -1.00 3.50 -8 1 1 28.20 6.30 -8 -1 1 28.80 6.60 -8 1 0 -0.60 3.50 -8 -1 0 8.80 4.60 -8 1 -1 2.80 4.30 -8 -1 -1 3.10 4.70 -8 -2 6 9.00 4.50 -8 2 5 37.00 5.90 -8 -2 5 35.00 6.50 -8 2 4 2.80 3.50 -8 -2 4 0.90 3.30 -8 2 3 19.70 5.00 -8 -2 3 23.00 6.00 -8 2 2 18.60 5.50 -8 -2 2 12.00 4.80 -8 2 1 3.60 3.50 -8 -2 1 -0.60 3.50 -8 2 0 3.20 3.90 -8 -2 0 9.00 4.90 -8 2 -1 43.60 7.80 -8 -2 -1 40.90 8.30 -8 3 5 5.90 3.50 -8 -3 5 4.70 4.10 -8 3 4 4.40 3.90 -8 -3 4 6.00 4.00 -8 3 3 1.20 3.40 -8 -3 3 0.80 3.60 -8 3 2 17.00 4.80 -8 -3 2 18.50 5.60 -8 3 1 9.60 4.40 -8 -3 1 1.70 3.80 -8 3 0 50.09 7.90 -8 -3 0 48.10 8.70 -8 3 -1 5.50 4.00 -8 -3 -1 3.90 4.90 -8 4 5 0.30 2.80 -8 -4 5 0.40 3.90 -8 4 4 25.10 5.00 -8 -4 4 21.00 5.70 -8 4 3 39.00 6.00 -8 -4 3 30.90 6.80 -8 4 2 44.60 7.40 -8 -4 2 45.10 8.00 -8 4 1 21.40 5.70 -8 -4 1 14.80 5.90 -8 4 0 -4.70 2.80 -8 -4 0 2.80 4.60 -8 -5 5 48.10 8.40 -8 5 4 0.30 2.70 -8 -5 4 1.80 3.90 -8 5 3 4.60 3.60 -8 -5 3 5.60 4.40 -8 5 2 -1.90 2.90 -8 -5 2 0.20 3.50 -8 5 1 90.59 9.00 -8 -5 1 116.29 13.10 -8 5 0 -0.40 3.50 -8 -5 0 6.00 4.80 -8 6 4 2.20 3.00 -8 -6 4 4.40 4.70 -8 6 3 120.79 9.50 -8 -6 3 120.29 13.30 -8 6 2 13.70 4.70 -8 -6 2 19.00 6.00 -8 6 1 14.10 4.60 -8 -6 1 13.40 5.90 -8 6 0 6.80 4.40 -8 -6 0 15.00 6.10 -8 7 4 36.10 5.40 -8 -7 4 43.90 8.10 -8 7 3 7.90 3.50 -8 -7 3 -1.40 4.00 -8 7 2 5.80 3.50 -8 -7 2 10.80 5.10 -8 7 1 11.90 4.70 -8 -7 1 10.10 5.40 -8 8 2 14.40 4.60 -9 0 3 -2.40 3.10 -9 0 2 29.60 6.80 -9 1 3 2.00 3.70 -9 -1 3 -0.60 3.50 -9 1 2 64.69 9.10 -9 -1 2 71.29 9.90 -9 2 3 80.89 9.50 -9 -2 3 63.79 9.30 -9 2 2 9.40 4.70 -9 -2 2 4.00 4.30 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 36358 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.46279(11) 0.39451(5) 0.62533(11) 0.0400(3) Uani 1 1 d . . . . N3' N 0.7062(4) 0.09016(15) 0.6645(4) 0.0367(6) Uani 1 1 d . . . . N2 N 1.052(2) 0.2538(6) 0.723(2) 0.033(3) Uani 0.700(5) 1 d . P A 1 C6 C 0.5159(7) 0.1105(3) 0.6289(6) 0.0308(11) Uani 0.700(5) 1 d . P A 1 H6 H 0.4224 0.0592 0.6058 0.037 Uiso 0.700(5) 1 calc R P A 1 C2 C 0.8050(7) 0.1667(4) 0.6802(6) 0.0232(10) Uani 0.700(5) 1 d . P A 1 C3' C 0.7376(4) 0.25926(19) 0.6730(4) 0.0256(6) Uani 1 1 d . . . . N1 N 0.9072(5) 0.3146(3) 0.7025(5) 0.0268(10) Uani 0.700(5) 1 d . P A 1 C1 C 0.9401(11) 0.4183(4) 0.7169(10) 0.0413(16) Uani 0.700(5) 1 d . P A 1 H1A H 0.9058 0.4429 0.8243 0.062 Uiso 0.700(5) 1 calc GR P A 1 H1B H 0.8548 0.4493 0.6029 0.062 Uiso 0.700(5) 1 calc GR P A 1 H1C H 1.0817 0.4322 0.7329 0.062 Uiso 0.700(5) 1 calc GR P A 1 N3 N 0.9952(7) 0.1649(4) 0.7092(6) 0.0345(11) Uani 0.700(5) 1 d . P A 1 C4 C 0.5598(5) 0.2823(2) 0.6450(5) 0.0217(10) Uani 0.700(5) 1 d . P A 1 C5 C 0.4422(6) 0.2042(4) 0.6231(6) 0.0246(10) Uani 0.700(5) 1 d . P A 1 H5 H 0.3024 0.2130 0.6027 0.030 Uiso 0.700(5) 1 calc R P A 1 C4' C 0.6656(11) 0.3487(6) 0.6549(12) 0.020(2) Uani 0.300(5) 1 d . P A 2 C2' C 0.8956(17) 0.2222(8) 0.7035(14) 0.028(3) Uani 0.300(5) 1 d . P A 2 C5' C 0.8125(18) 0.4123(7) 0.6826(14) 0.030(3) Uani 0.300(5) 1 d . P A 2 H4 H 0.7896 0.4794 0.6780 0.036 Uiso 0.300(5) 1 calc R P A 2 N4' N 0.6133(11) 0.1668(5) 0.6520(11) 0.029(2) Uani 0.300(5) 1 d . P A 2 C1' C 0.4201(16) 0.1475(9) 0.6097(15) 0.026(2) Uani 0.300(5) 1 d . P A 2 H4AA H 0.3484 0.1732 0.4858 0.039 Uiso 0.300(5) 1 calc GR P A 2 H4AB H 0.3671 0.1770 0.7021 0.039 Uiso 0.300(5) 1 calc GR P A 2 H4AC H 0.4009 0.0781 0.6098 0.039 Uiso 0.300(5) 1 calc GR P A 2 N2' N 0.9064(18) 0.1268(8) 0.7093(14) 0.034(2) Uani 0.300(5) 1 d . P A 2 C6' C 0.990(2) 0.3752(10) 0.716(2) 0.033(3) Uani 0.300(5) 1 d . P A 2 H2AA H 1.0972 0.4198 0.7364 0.040 Uiso 0.300(5) 1 calc R P A 2 N1' N 1.043(5) 0.2846(16) 0.727(5) 0.026(5) Uani 0.300(5) 1 d . P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0375(4) 0.0248(4) 0.0641(6) 0.0094(4) 0.0253(4) 0.0145(3) N3' 0.0341(14) 0.0215(13) 0.0539(17) 0.0008(11) 0.0131(12) 0.0052(11) N2 0.016(3) 0.040(7) 0.046(3) -0.003(5) 0.015(2) -0.003(5) C6 0.021(2) 0.017(2) 0.054(3) -0.006(2) 0.011(2) -0.001(2) C2 0.014(2) 0.028(3) 0.025(3) 0.0004(19) 0.0026(17) 0.002(2) C3' 0.0268(15) 0.0283(14) 0.0224(16) 0.0030(12) 0.0087(11) 0.0048(12) N1 0.014(2) 0.023(2) 0.043(2) 0.0021(16) 0.0091(16) -0.0051(17) C1 0.038(4) 0.028(4) 0.062(4) -0.009(3) 0.022(3) -0.019(3) N3 0.013(2) 0.040(3) 0.049(3) -0.001(2) 0.0076(18) 0.005(2) C4 0.0177(19) 0.0171(19) 0.030(2) 0.0034(16) 0.0072(15) 0.0030(15) C5 0.015(2) 0.022(2) 0.036(3) 0.000(2) 0.0073(17) 0.0011(18) C4' 0.011(4) 0.017(4) 0.031(6) -0.001(4) 0.006(3) 0.004(3) C2' 0.025(6) 0.030(7) 0.032(6) 0.000(5) 0.011(4) 0.002(6) C5' 0.030(6) 0.021(5) 0.039(6) 0.007(4) 0.011(5) -0.006(5) N4' 0.020(4) 0.017(4) 0.045(6) 0.002(3) 0.003(4) 0.006(3) C1' 0.028(6) 0.007(5) 0.044(7) -0.004(5) 0.013(5) 0.001(5) N2' 0.012(5) 0.034(6) 0.049(6) -0.002(5) 0.000(4) 0.007(5) C6' 0.038(8) 0.022(8) 0.044(8) -0.001(6) 0.018(5) 0.002(6) N1' 0.014(7) 0.020(11) 0.037(7) 0.004(8) -0.005(5) -0.001(8) 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' Cl Cl 0.1484 0.1585 '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 C2 N3' C6 109.3(3) N4' N3' N2' 99.2(6) N1 N2 N3 114.3(10) N3' C6 H6 118.3 N3' C6 C5 123.5(4) C5 C6 H6 118.3 N3' C2 C3' 128.7(4) N3' C2 N3 120.7(6) N3 C2 C3' 110.6(5) C2 C3' N1 104.7(3) C4 C3' C2 124.5(3) C4 C3' N1 130.8(3) C4' C3' N4' 126.2(5) C2' C3' C4' 137.0(7) C2' C3' N4' 96.8(6) N2 N1 C3' 104.7(6) N2 N1 C1 122.8(6) C3' N1 C1 132.4(4) N1 C1 H1A 109.5 N1 C1 H1B 109.5 N1 C1 H1C 109.5 H1A C1 H1B 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 C2 N3 N2 105.6(7) C3' C4 Cl1 127.5(3) C3' C4 C5 110.8(3) C5 C4 Cl1 121.7(3) C6 C5 H5 118.4 C4 C5 C6 123.2(4) C4 C5 H5 118.4 C3' C4' Cl1 135.9(6) C5' C4' Cl1 112.8(7) C5' C4' C3' 111.1(7) C3' C2' N2' 119.0(13) C3' C2' N1' 112.5(13) N1' C2' N2' 128.5(16) C4' C5' H4 122.8 C6' C5' C4' 114.4(10) C6' C5' H4 122.8 N3' N4' C3' 116.8(6) N3' N4' C1' 108.4(9) C1' N4' C3' 134.6(8) N4' C1' H4AA 109.5 N4' C1' H4AB 109.5 N4' C1' H4AC 109.5 H4AA C1' H4AB 109.5 H4AA C1' H4AC 109.5 H4AB C1' H4AC 109.5 C2' N2' N3' 108.0(11) C5' C6' H2AA 115.4 C5' C6' N1' 129(2) N1' C6' H2AA 115.5 C6' N1' C2' 116(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C4 1.697(4) Cl1 C4' 1.509(8) N3' C6 1.306(5) N3' C2 1.259(6) N3' N4' 1.242(7) N3' N2' 1.430(13) N2 N1 1.293(12) N2 N3 1.298(12) C6 H6 0.9500 C6 C5 1.403(6) C2 C3' 1.372(6) C2 N3 1.281(7) C3' N1 1.376(4) C3' C4 1.238(4) C3' C4' 1.339(8) C3' C2' 1.177(11) C3' N4' 1.538(9) N1 C1 1.466(6) C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800 C4 C5 1.345(6) C5 H5 0.9500 C4' C5' 1.325(14) C2' N2' 1.335(16) C2' N1' 1.32(3) C5' H4 0.9500 C5' C6' 1.297(18) N4' C1' 1.317(13) C1' H4AA 0.9800 C1' H4AB 0.9800 C1' H4AC 0.9800 C6' H2AA 0.9500 C6' N1' 1.31(2) 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 Cl1 C4 C5 C6 176.6(4) Cl1 C4' C5' C6' 177.2(9) N3' C6 C5 C4 3.2(7) N3' C2 C3' N1 178.6(4) N3' C2 C3' C4 -1.5(6) N3' C2 N3 N2 -178.5(8) C6 N3' C2 C3' 3.2(6) C6 N3' C2 N3 -177.7(4) C2 N3' C6 C5 -3.9(6) C2 C3' N1 N2 0.1(8) C2 C3' N1 C1 -178.0(5) C2 C3' C4 Cl1 -177.3(3) C2 C3' C4 C5 0.1(5) C3' C2 N3 N2 0.8(8) C3' C4 C5 C6 -1.0(6) C3' C4' C5' C6' 1.4(14) C3' C2' N2' N3' 3.0(12) C3' C2' N1' C6' 1(3) N1 N2 N3 C2 -0.7(13) N1 C3' C4 Cl1 2.5(6) N1 C3' C4 C5 -180.0(4) N3 N2 N1 C3' 0.3(13) N3 N2 N1 C1 178.7(7) N3 C2 C3' N1 -0.6(4) N3 C2 C3' C4 179.3(4) C4 C3' N1 N2 -179.8(8) C4 C3' N1 C1 2.1(7) C4' C3' C2' N2' -179.4(8) C4' C3' C2' N1' 0(2) C4' C3' N4' N3' 176.4(6) C4' C3' N4' C1' 2.0(14) C4' C5' C6' N1' 0(3) C2' C3' C4' Cl1 -176.1(8) C2' C3' C4' C5' -1.7(13) C2' C3' N4' N3' -2.6(8) C2' C3' N4' C1' -177.0(11) C5' C6' N1' C2' -1(4) N4' N3' N2' C2' -4.1(9) N4' C3' C4' Cl1 5.3(12) N4' C3' C4' C5' 179.7(7) N4' C3' C2' N2' -0.5(10) N4' C3' C2' N1' 179.1(17) N2' N3' N4' C3' 4.1(8) N2' N3' N4' C1' 179.9(8) N2' C2' N1' C6' -179.1(17) N1' C2' N2' N3' -177(2)