#------------------------------------------------------------------------------ #$Date: 2019-11-11 20:29:11 +0200 (Mon, 11 Nov 2019) $ #$Revision: 227272 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035860.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_4035860 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 _atom_sites_solution_secondary difmap _audit_creation_date 2016-08-22 _audit_creation_method ; Olex2 1.2-beta (compiled 2016.08.19 svn.r3327 for OlexSys, GUI svn.r5215) ; _cell_angle_alpha 90 _cell_angle_beta 97.162(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 3.9913(2) _cell_length_b 6.7117(3) _cell_length_c 13.3807(7) _cell_measurement_reflns_used 997 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 67.868 _cell_measurement_theta_min 6.670 _cell_volume 355.65(3) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _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, 2015)' _diffrn_ambient_temperature 100.0 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.939 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_unetI/netI 0.0271 _diffrn_reflns_Laue_measured_fraction_full 0.939 _diffrn_reflns_Laue_measured_fraction_max 0.937 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2096 _diffrn_reflns_point_group_measured_fraction_full 0.939 _diffrn_reflns_point_group_measured_fraction_max 0.937 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.210 _diffrn_reflns_theta_min 6.669 _diffrn_source 'rotating anode' _diffrn_source_target Mo _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 4.203 _exptl_absorpt_correction_T_max 0.3200 _exptl_absorpt_correction_T_min 0.1847 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1021 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.5772. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.574 _exptl_crystal_description plate _exptl_crystal_F_000 172 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.47 _refine_diff_density_max 0.689 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.097 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 608 _refine_ls_number_restraints 87 _refine_ls_restrained_S_all 1.199 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0787 _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^)+(0.1567P)^2^+0.1472P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2115 _refine_ls_wR_factor_ref 0.2229 _reflns_Friedel_coverage 0.000 _reflns_number_gt 521 _reflns_number_total 608 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jo8b00540_si_006.cif _cod_data_source_block Dart170 _cod_database_code 4035860 _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. ; _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. Rigid body (RIGU) restrains All non-hydrogen atoms with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 3. Others Fixed Sof: Cl1(0.5) C1(0.5) H1(0.5) N4(0.5) N3(0.5) C5(0.5) C3(0.5) C2(0.5) H2(0.5) N2(0.5) N1(0.5) C4(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) 4.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2) 4.b Idealised Me refined as rotating group: C6(H6A,H6B,H6C) ; _shelx_res_file ; p21c_a.res created by SHELXL-2014/7 TITL p21c_a.res in P2(1)/c REM Old TITL p21c in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.351, Rweak 0.029, Alpha 0.086, Orientation as input REM Formula found by SHELXT: C7 N6 Cl2 CELL 1.54178 3.9913 6.7117 13.3807 90 97.162 90 ZERR 2 0.0002 0.0003 0.0007 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N UNIT 12 10 2 8 RIGU L.S. 10 PLAN 20 TEMP -173.15 BOND $H LIST 6 fmap 2 MORE -1 CONF ACTA OMIT 0 0 6 REM REM REM WGHT 0.156700 0.147200 FVAR 1.34503 PART -1 CL1 3 0.136116 0.193691 0.441646 10.50000 0.04178 0.04518 = 0.08616 -0.01773 0.01277 -0.00395 C1 1 0.398454 0.679145 0.325830 10.50000 0.04417 0.07210 = 0.04318 0.01105 0.00762 0.02045 AFIX 43 H1 2 0.359047 0.734342 0.260036 10.50000 -1.20000 AFIX 0 N4 4 0.865144 0.728761 0.594225 10.50000 0.04875 0.06254 = 0.09318 -0.02376 0.00890 -0.00827 N3 4 0.849916 0.610730 0.649641 10.50000 0.02952 0.07937 = 0.04232 -0.02383 0.00490 0.00080 C5 1 0.320344 0.420192 0.428432 10.50000 0.02986 0.04795 = 0.05335 -0.01569 0.00778 0.00353 C3 1 0.672294 0.691626 0.494396 10.50000 0.03367 0.03769 = 0.06718 -0.00992 0.02152 0.00515 C2 1 0.613333 0.789708 0.402223 10.50000 0.04338 0.04685 = 0.08041 0.01114 0.02663 0.00719 AFIX 43 H2 2 0.704921 0.916940 0.390362 10.50000 -1.20000 AFIX 0 N2 4 0.645300 0.460301 0.607212 10.50000 0.03761 0.06255 = 0.03736 -0.00146 0.00476 0.00407 N1 4 0.253672 0.505995 0.342047 10.50000 0.04326 0.08407 = 0.04239 -0.00868 -0.00019 0.01281 C4 1 0.530242 0.512246 0.507550 10.50000 0.02711 0.03234 = 0.03385 -0.00143 0.00880 0.00327 C6 1 0.573001 0.272390 0.659103 10.50000 0.06119 0.05839 = 0.04385 0.01311 0.01761 0.00414 AFIX 137 H6A 2 0.690941 0.273602 0.727873 10.50000 -1.50000 H6B 2 0.651032 0.158728 0.622252 10.50000 -1.50000 H6C 2 0.329326 0.260852 0.661423 10.50000 -1.50000 AFIX 0 HKLF 4 REM p21c_a.res in P2(1)/c REM R1 = 0.0787 for 521 Fo > 4sig(Fo) and 0.0850 for all 608 data REM 101 parameters refined using 87 restraints END WGHT 0.1543 0.1567 REM Highest difference peak 0.689, deepest hole -0.218, 1-sigma level 0.097 Q1 1 0.2238 0.1835 0.5096 11.00000 0.05 0.69 Q2 1 0.8849 0.7155 0.6435 11.00000 0.05 0.40 Q3 1 0.5855 0.6844 0.4519 11.00000 0.05 0.29 Q4 1 0.7187 0.5772 0.6452 11.00000 0.05 0.26 Q5 1 0.3051 0.5594 0.3341 11.00000 0.05 0.26 Q6 1 0.5133 0.7678 0.3752 11.00000 0.05 0.25 Q7 1 -0.0530 0.2428 0.4263 11.00000 0.05 0.10 Q8 1 -0.0440 0.1302 0.4410 11.00000 0.05 0.09 Q9 1 0.8360 0.2569 0.6757 11.00000 0.05 0.09 Q10 1 0.0967 0.3250 0.7380 11.00000 0.05 0.09 Q11 1 0.8819 0.7040 0.7272 11.00000 0.05 0.08 Q12 1 0.6142 1.1045 0.3875 11.00000 0.05 0.08 Q13 1 0.7857 0.9014 0.3933 11.00000 0.05 0.07 Q14 1 0.9775 0.5873 0.7720 11.00000 0.05 0.07 Q15 1 0.7350 0.1450 0.6728 11.00000 0.05 0.07 Q16 1 0.5071 0.9225 0.4859 11.00000 0.05 0.06 Q17 1 0.9180 1.0405 0.3022 11.00000 0.05 0.05 Q18 1 0.3932 0.7376 0.5439 11.00000 0.05 0.04 Q19 1 0.4236 0.9554 0.2717 11.00000 0.05 0.04 Q20 1 0.2229 0.9606 0.2245 11.00000 0.05 0.04 ; _shelx_res_checksum 26386 _shelx_hkl_file ; 1 0 0 647.685 18.4277 2 -1 0 0 677.893 18.4333 2 -3 0 0 69.6079 2.99361 3 -4 0 0 251.828 8.07543 5 -4 0 0 253.278 8.05406 3 0 -1 0 0.07284 0.16433 2 0 1 0 0.08120 0.16744 2 1 -1 0 2975.31 84.0939 2 -1 1 0 3108.71 84.0373 2 -3 -1 0 38.8376 2.04393 3 -3 1 0 33.5686 2.05667 5 -3 1 0 40.5955 2.29168 3 3 1 0 34.5380 2.44226 5 -4 -1 0 0.26422 0.68728 5 -4 -1 0 0.28401 0.69810 3 -4 1 0 0.07272 0.85117 3 0 -2 0 1553.25 43.2627 2 -1 -2 0 240.226 6.92317 2 -1 -2 0 237.812 6.91455 2 -1 2 0 250.298 7.42781 2 2 -2 0 11.4246 1.17835 2 -3 -2 0 65.8430 3.10401 3 -3 2 0 69.7175 3.25092 6 3 2 0 67.6924 3.50890 5 -3 2 0 68.7596 3.05119 3 3 2 0 67.7549 3.53305 1 -4 -2 0 149.733 5.37668 5 -4 -2 0 151.567 5.15524 3 -4 2 0 150.852 5.16225 3 0 -3 0 -0.0900 0.30882 2 1 -3 0 106.348 3.92088 2 -3 3 0 15.7939 1.75042 3 3 3 0 13.5155 1.87273 1 3 3 0 15.7138 1.97989 5 -3 3 0 17.5412 1.77310 6 -4 -3 0 1.60595 0.61727 3 -4 3 0 0.38468 0.86638 6 -4 3 0 1.71084 0.68174 3 4 3 0 0.02491 1.55701 1 0 -4 0 422.726 12.6049 2 2 4 0 11.0307 1.49553 1 -2 4 0 12.1370 1.31977 3 -2 4 0 12.6364 1.45454 6 -2 4 0 15.8016 1.80751 4 2 4 0 18.8139 1.99355 5 3 4 0 9.13358 1.61550 5 -3 4 0 9.99793 1.23474 3 3 4 0 9.36013 1.40252 1 -3 4 0 8.15132 1.19329 6 -3 4 0 9.37867 1.43081 4 -4 -4 0 0.27089 0.51671 5 -4 4 0 -0.5996 0.77422 6 -4 4 0 0.41378 0.47501 3 4 4 0 1.14898 1.11305 1 0 5 0 2.92578 1.16941 4 0 5 0 1.01948 1.06508 6 1 5 0 5.70976 1.41251 1 1 5 0 6.72443 1.40102 5 -1 5 0 5.24411 1.07428 6 -1 5 0 6.34169 1.30146 4 -1 5 0 4.61000 1.23345 3 -2 5 0 -0.1794 0.85852 4 2 5 0 0.52507 1.21590 1 2 5 0 0.03402 1.15146 5 -2 5 0 -0.5158 0.70900 6 -2 5 0 -0.6741 1.07567 3 3 5 0 0.08722 0.83804 1 -3 5 0 0.30262 0.68806 6 3 5 0 -0.3823 0.99283 5 -3 5 0 -0.0944 0.67092 3 0 6 0 33.3641 3.59439 4 1 6 0 -0.2180 1.31400 1 -1 6 0 -1.0050 1.07727 4 -1 6 0 1.02854 1.02880 6 -2 6 0 -0.7714 1.07506 4 2 6 0 -0.3467 1.09260 1 -2 6 0 -0.3107 0.72500 3 -2 6 0 0.84065 0.80158 6 2 6 0 0.26509 0.73649 5 -3 6 0 10.8740 1.38178 6 3 6 0 4.68197 0.80289 5 3 6 0 6.46464 0.83978 1 -1 7 0 7.39894 1.12542 6 -2 7 0 11.6781 1.11154 6 2 7 0 10.9815 1.12237 1 -4 0 1 0.12822 0.92960 5 -4 0 1 -0.4678 0.57768 3 -3 0 1 0.11976 0.82575 3 1 0 -1 0.12210 0.15683 2 1 0 -1 0.07078 0.11957 2 0 0 -1 -0.0020 0.10162 2 0 0 1 -0.0716 0.06346 2 1 0 1 0.25733 0.19767 2 -1 0 -1 0.33233 0.20458 2 -3 0 -1 1.09305 0.90071 3 -4 0 -1 0.72958 0.67292 5 -4 0 -1 -0.2836 0.67033 3 -4 -1 1 2.82806 1.00400 3 -4 -1 1 1.19924 0.97560 5 -4 1 1 1.62010 0.94887 5 -4 1 1 0.50151 0.91100 3 -3 -1 1 37.7804 2.16968 3 -3 1 1 36.8647 2.14972 5 3 1 -1 40.1339 2.54770 5 -3 1 1 38.2716 2.19791 3 2 -1 -1 30.9128 1.45484 2 1 -1 -1 4244.21 112.047 2 1 -1 -1 3881.98 112.148 2 0 -1 1 2247.43 64.0161 2 0 -1 -1 2343.90 64.5665 2 0 1 1 2362.72 63.9979 2 0 1 -1 2327.92 63.9973 2 1 -1 1 25.5465 1.23740 2 -1 -1 -1 26.6631 0.98529 2 -1 1 -1 28.5073 1.29315 2 1 1 1 26.1162 0.96515 2 -2 1 -1 91.9851 3.30343 2 -3 -1 -1 20.1715 1.86446 3 3 1 1 24.0212 2.12022 5 -3 1 -1 19.7005 1.85083 3 -3 1 -1 16.4058 2.01653 6 -4 -1 -1 10.2427 1.21022 3 -4 -1 -1 5.21667 1.07675 5 -4 1 -1 7.53798 1.20768 3 -4 -2 1 26.1908 1.71643 5 -4 -2 1 25.2704 1.75045 3 -4 2 1 24.2883 1.67470 3 -3 -2 1 43.5967 2.45458 3 -3 2 1 44.7310 2.26085 5 3 2 -1 45.9840 2.85080 5 3 2 -1 43.9896 2.94739 1 -3 2 1 44.2371 2.38101 3 -3 2 1 45.6855 2.60501 6 2 -2 -1 121.192 4.28586 2 1 -2 -1 9.60456 0.84564 2 -1 -2 1 7.59946 0.41124 2 -1 -2 1 8.46803 0.41504 2 0 -2 -1 6.42614 0.66460 2 0 -2 -1 6.34934 0.52877 2 0 -2 1 5.35163 0.61076 2 0 2 -1 5.52450 0.57207 2 -1 -2 -1 170.151 4.97852 2 -1 -2 -1 160.783 4.97136 2 -1 2 -1 167.436 5.32659 2 -2 2 -1 27.3405 1.66867 2 -3 -2 -1 13.3858 1.51779 3 3 2 1 14.2846 1.63024 5 -3 2 -1 11.3291 1.67608 6 3 2 1 13.3982 1.75776 1 -3 2 -1 10.2419 1.30931 3 -4 -2 -1 5.67896 1.21083 3 -4 2 -1 5.85031 0.89574 3 -4 -3 1 19.3387 1.45905 5 -4 3 1 18.5197 1.38667 3 4 3 -1 17.1325 1.82059 1 3 3 -1 34.2832 2.72278 1 3 3 -1 35.0763 2.58470 5 -3 3 1 34.4208 2.23196 3 -3 3 1 36.1060 2.47068 6 1 -3 -1 3.87121 0.73551 2 0 -3 -1 900.090 25.3449 2 0 3 -1 893.915 25.4608 2 -1 3 -1 82.7406 3.28286 2 2 3 1 23.9601 2.71099 5 -3 3 -1 168.523 5.89821 3 -3 3 -1 169.098 6.26575 6 3 3 1 171.789 6.46077 1 3 3 1 176.176 6.68581 5 -4 -3 -1 0.72901 0.86357 3 -4 3 -1 2.21473 0.69669 3 -4 3 -1 1.79113 0.91691 6 -4 -4 1 34.0806 1.60328 5 -4 4 1 32.1770 1.56908 3 -4 4 1 34.7078 1.91492 6 4 4 -1 36.4695 2.22104 1 -3 4 1 6.25543 1.19554 4 -3 4 1 5.59563 1.02192 6 3 4 -1 6.24789 1.41287 5 3 4 -1 5.30001 1.20413 1 -3 4 1 5.72144 1.17429 3 2 4 -1 123.244 4.76145 1 -2 4 1 119.033 4.67981 6 2 4 -1 116.765 4.71750 5 -2 4 1 122.631 4.46042 3 -2 4 1 116.505 4.62029 4 0 -4 1 94.5815 3.65592 2 0 -4 -1 98.0970 3.84324 2 2 4 1 108.833 4.40988 3 -2 4 -1 108.171 4.41120 6 2 4 1 106.786 4.48489 1 -2 4 -1 106.161 4.52475 4 -2 4 -1 104.187 4.10810 3 2 4 1 106.260 4.43907 5 -3 4 -1 80.5017 3.85646 4 3 4 1 92.9502 4.26801 5 3 4 1 89.8680 4.19004 1 -3 4 -1 88.8438 3.64849 3 -3 4 -1 88.2987 3.74987 6 -4 4 -1 3.18997 0.62657 6 -4 4 -1 3.98084 0.58650 3 4 4 1 3.17912 1.06299 1 -3 5 1 19.4274 1.60593 6 -3 5 1 20.5474 1.77391 3 3 5 -1 18.3232 1.72809 1 3 5 -1 19.7037 1.57151 5 2 5 -1 109.198 4.53656 5 -2 5 1 108.251 4.34248 3 -2 5 1 110.608 4.63363 4 -2 5 1 109.876 4.25295 6 2 5 -1 115.976 4.74402 1 -1 5 1 116.205 4.64574 3 -1 5 1 130.721 5.01306 4 1 5 -1 122.202 4.85486 1 -1 5 1 121.605 4.65524 6 0 5 1 38.6076 2.22511 6 0 5 -1 38.7067 2.43831 4 0 5 1 37.1936 2.43855 4 0 5 1 34.1669 2.32399 3 1 5 1 134.826 5.04442 1 -1 5 -1 136.001 4.87920 6 -1 5 -1 128.830 4.95424 4 1 5 1 127.540 4.86141 3 1 5 1 133.295 5.02845 5 2 5 1 13.9754 1.56580 1 2 5 1 13.5700 1.84090 5 -2 5 -1 9.46106 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-3 -2 -10 4.37054 0.83800 6 -3 2 -10 3.23747 1.14656 6 -3 -3 10 34.2905 1.96122 1 -3 3 10 31.2537 1.72109 5 -2 -3 10 15.0474 1.56727 1 -2 3 10 14.8984 1.78503 4 -2 3 10 13.9413 1.36861 5 -1 3 10 0.21204 0.86331 5 -1 3 10 -0.3723 1.02738 4 -1 3 10 -0.6259 1.39102 6 -1 3 10 1.01637 0.91637 1 0 3 10 0.14936 1.00910 3 0 3 10 0.82354 0.96890 1 0 3 10 -2.6269 1.24334 6 0 3 10 -0.3746 0.96835 5 0 3 -10 -0.6871 1.41029 4 -1 -3 -10 61.6130 4.14063 4 1 3 10 64.9162 3.56443 6 1 3 10 67.6648 3.11105 3 1 3 10 63.6953 3.34618 1 1 3 10 61.4868 3.08073 5 -1 3 -10 63.5382 3.64371 4 -2 -3 -10 9.39429 1.34543 6 -2 3 -10 6.20401 1.63543 4 2 3 10 5.77318 1.33412 1 -2 3 -10 8.59770 1.25587 6 2 3 10 9.62926 1.09278 3 -3 -4 10 0.87099 0.53902 1 -3 4 10 0.03848 0.36688 5 -2 -4 10 19.9952 1.66123 1 -2 4 10 19.3012 1.53557 5 -2 4 10 16.7661 1.65915 1 -2 4 10 17.1754 2.08872 4 -2 4 10 19.0432 1.62265 3 -1 4 10 4.47839 1.15685 1 -1 4 10 4.51398 1.92834 4 -1 4 10 4.52407 1.52522 6 -1 4 10 2.14231 1.02067 3 -1 4 10 4.66680 1.14727 5 0 4 10 16.7918 2.05956 6 0 4 10 14.6489 1.68989 5 0 4 10 16.9146 1.85862 3 0 4 -10 13.4461 2.03628 4 0 4 10 12.0922 1.39059 1 -1 4 -10 5.78753 1.36337 4 1 4 10 4.18295 1.35471 6 1 4 10 5.51915 1.13409 5 1 4 10 5.17084 1.08501 1 1 4 10 3.30501 1.09390 3 -2 -4 -10 3.07383 0.95506 6 2 4 10 3.82209 1.15072 1 -2 4 -10 4.29390 0.98842 4 2 4 10 3.78791 0.77981 3 -2 5 10 4.55748 0.82718 5 -2 5 10 6.51762 1.07319 6 -2 5 10 9.59382 1.28142 4 -1 5 10 1.28118 1.05696 6 -1 5 10 0.87384 0.80920 5 -1 5 10 2.02124 0.64677 3 -1 5 10 2.73226 1.88934 4 -1 5 10 2.51975 0.84652 1 0 5 10 24.3453 2.22696 6 0 5 10 20.1194 1.71315 1 0 5 10 22.2896 1.75588 3 0 5 -10 21.7202 1.81987 4 0 5 10 18.9727 1.49554 5 1 5 10 2.01883 1.24681 6 -1 5 -10 3.99226 1.10988 4 1 5 10 4.61483 0.96660 1 1 5 10 2.38217 0.71181 5 1 5 10 4.17305 0.98919 3 -1 6 10 29.1804 1.42646 3 -1 6 10 32.3397 1.52729 5 -1 6 10 31.6893 1.77652 6 0 -6 -10 -0.7934 0.88606 4 0 6 10 0.31242 0.78405 6 0 6 10 -0.2218 0.56841 3 0 6 10 0.49994 0.55545 5 0 6 10 -0.7110 0.84786 1 -3 0 11 -0.3329 0.48779 1 -3 0 11 -0.2142 0.56603 5 -2 0 11 -0.2569 0.49799 1 1 0 -11 -0.9109 1.65155 4 -1 0 11 0.61158 0.78493 1 0 0 -11 0.64907 1.57563 4 0 0 11 1.20803 0.89634 1 -1 0 -11 -1.9715 1.28582 6 -1 0 -11 0.77396 1.32332 4 -2 0 -11 -0.3078 0.72023 6 -2 0 -11 -0.4031 0.95735 4 -3 0 -11 -0.1348 0.69616 6 -3 -1 11 11.6575 1.11143 1 -3 1 11 11.3386 1.17404 5 -3 1 11 12.5954 1.38396 1 -2 -1 11 9.15680 1.16836 1 -2 1 11 8.74443 1.35358 5 -2 1 11 9.48675 1.11661 1 1 -1 -11 2.13888 1.82265 4 -1 -1 11 1.70134 0.86090 1 -1 1 11 3.55373 0.98171 1 1 1 -11 3.02660 1.39849 4 0 -1 -11 39.1050 3.01724 4 0 1 -11 39.7855 3.52228 4 0 1 11 41.3653 2.40446 1 -1 -1 -11 45.7550 3.04817 6 -1 -1 -11 46.6573 3.55425 4 -1 1 -11 42.1927 3.36418 4 -1 1 -11 45.1557 3.02147 6 -2 -1 -11 0.81776 1.08757 6 -2 1 -11 0.88710 1.13590 6 -2 1 -11 -0.3204 1.00438 4 -3 -1 -11 8.01216 1.01388 6 -3 1 -11 8.82026 0.95749 6 -3 -2 11 10.9361 1.23230 1 -3 2 11 13.6853 1.39820 5 -3 2 11 14.4301 1.33407 1 -2 -2 11 26.3083 1.95814 1 -2 2 11 22.3562 1.74916 1 -2 2 11 24.0264 1.83341 5 -1 -2 11 0.73476 0.80569 1 -1 2 11 0.54786 0.85886 1 -1 2 11 0.73502 0.93539 5 0 -2 -11 0.16026 1.03747 4 0 2 -11 -0.2954 1.54228 4 0 2 11 -0.1519 0.88000 6 0 2 11 -1.2722 0.59793 1 -1 -2 -11 3.57694 1.66767 4 -1 2 -11 1.38635 1.52766 4 1 2 11 0.64228 1.08517 1 -2 -2 -11 -0.1903 0.75775 6 -2 2 -11 -0.4182 1.04741 6 -2 2 -11 -0.0891 1.00063 4 -3 -3 11 6.10396 0.87292 1 -3 3 11 4.90034 0.75854 5 -2 -3 11 75.4118 2.96974 1 -2 3 11 74.0780 3.05481 1 -2 3 11 73.4407 3.19149 5 -1 3 11 -0.6537 1.26895 6 -1 3 11 1.50131 0.71229 1 -1 3 11 -0.2431 0.95918 5 0 -3 -11 2.22890 1.66229 4 0 3 11 2.03589 1.34065 6 0 3 11 2.63188 0.83597 5 0 3 -11 2.05471 1.14198 4 0 3 11 2.27482 1.10161 1 -1 -3 -11 13.9913 2.06030 4 1 3 11 15.6655 1.38815 3 1 3 11 13.5099 1.52580 1 -1 3 -11 17.3081 1.86704 4 -2 -3 -11 14.5974 1.62890 6 2 3 11 16.3490 1.29093 3 -2 3 -11 14.1113 1.68036 6 -2 3 -11 13.0577 1.70597 4 -2 4 11 9.07475 1.10533 4 -2 4 11 9.89939 1.01708 5 -2 4 11 7.93444 1.10487 1 -1 4 11 5.48237 1.42047 6 -1 4 11 9.54692 1.19330 1 -1 4 11 7.30960 1.15529 4 -1 4 11 6.45502 1.01091 3 0 -4 -11 89.2543 4.46800 4 0 4 11 91.6168 3.45510 3 0 4 11 94.7062 4.13888 6 0 4 11 91.2517 3.74229 5 0 4 11 87.3618 3.68594 1 0 4 -11 93.5479 4.30824 4 1 4 11 0.98336 0.90749 5 1 4 11 1.95394 1.06182 6 1 4 11 0.69806 1.08265 1 -1 4 -11 2.82783 1.04796 4 1 4 11 0.73147 0.97673 3 -2 -4 -11 11.9953 1.25715 6 2 4 11 11.8567 1.23266 1 -2 4 -11 10.1819 1.25216 4 -2 5 11 14.5763 0.99005 5 -2 5 11 15.1213 1.08049 3 -1 5 11 14.4657 1.10325 3 -1 5 11 15.2640 1.14736 5 -1 5 11 15.7757 1.52579 1 -1 5 11 13.3922 1.56113 6 0 -5 -11 41.6766 2.98048 4 0 5 11 40.5079 2.00869 5 0 5 11 39.6489 1.92223 3 0 5 11 40.5553 2.08862 1 0 5 11 40.8650 2.51177 6 1 5 11 5.34269 0.71536 3 -1 5 -11 7.55150 1.28020 4 1 5 11 7.11615 1.04105 1 -3 0 12 3.61542 0.64810 1 -2 0 12 57.7954 2.59615 1 1 0 -12 2.34330 1.75708 4 -1 0 12 1.40319 0.93130 1 0 0 -12 142.932 6.18094 4 0 0 12 133.729 4.98087 1 -1 0 -12 126.790 5.15148 4 -1 0 -12 126.662 5.03428 6 -2 0 -12 42.3879 2.40320 6 -2 0 -12 39.1122 2.30184 4 -3 -1 12 0.56927 0.48484 1 -3 1 12 0.69424 0.50906 1 -3 1 12 0.95767 0.52123 5 -2 -1 12 8.88405 1.14266 1 -2 1 12 5.62533 0.98104 1 -1 -1 12 5.62585 0.86875 1 1 -1 -12 5.44844 1.94793 4 -1 1 12 3.88306 1.06410 1 1 1 -12 7.28681 1.80124 4 0 -1 -12 88.4551 4.79729 4 0 1 -12 88.5621 4.59874 4 0 1 12 89.0887 3.69981 1 -1 -1 -12 9.18256 1.40402 6 -1 -1 -12 10.2093 1.68749 4 -1 1 -12 8.88910 1.63374 4 -1 1 -12 6.13297 1.40113 6 -2 -1 -12 1.74318 0.77129 6 -2 1 -12 0.83742 0.83405 4 -2 1 -12 0.98281 0.73292 6 -3 -2 12 51.9022 2.04442 1 -3 2 12 50.2252 2.02008 1 -3 2 12 51.6832 2.05678 5 -2 -2 12 0.17926 0.55932 1 2 -2 -12 -0.3896 1.68431 4 -2 2 12 0.13035 0.80858 1 -2 2 12 1.05135 0.72550 5 -1 -2 12 11.5796 1.38140 1 1 -2 -12 8.71286 2.06300 4 -1 2 12 9.05013 1.20268 1 0 -2 -12 1.46120 1.48955 4 0 2 12 0.84185 0.96639 1 0 2 12 0.62501 1.39171 6 0 2 -12 0.69392 1.14791 4 -1 -2 -12 17.0513 1.75070 6 -1 -2 -12 15.2340 2.02457 4 1 2 12 15.0754 1.51163 1 -1 2 -12 16.4714 1.86667 4 -2 -2 -12 0.15163 0.73634 6 -2 2 -12 0.78100 0.84863 4 -2 2 -12 0.44640 0.61333 6 -3 -3 12 0.13867 0.40322 1 -3 3 12 0.28056 0.37524 5 2 -3 -12 -1.0684 1.67425 4 -2 -3 12 1.50450 0.60715 1 -2 3 12 2.36952 0.68992 1 -2 3 12 0.04049 0.75199 5 1 -3 -12 6.58865 1.78264 4 -1 3 12 10.8191 1.37600 5 -1 3 12 7.05144 1.13412 1 0 -3 -12 4.12236 1.59282 4 0 3 12 4.77696 0.94156 1 0 3 -12 4.07305 1.57172 4 0 3 12 5.35031 1.33055 6 -1 -3 -12 2.01575 1.46907 4 -1 -3 -12 1.24022 0.78855 6 1 3 12 0.32169 1.02297 1 -1 3 -12 0.26693 1.23558 4 -2 -3 -12 8.32826 1.04187 6 -2 3 -12 7.74498 1.30484 4 2 -4 -12 0.22924 1.05703 4 -2 4 12 0.66243 0.49142 5 -2 4 12 0.69206 0.79435 1 1 -4 -12 1.27816 1.47599 4 -1 4 12 1.13588 1.02882 6 -1 4 12 2.13515 0.64584 5 -1 4 12 1.56832 0.90465 1 0 -4 -12 28.7526 2.79430 4 0 4 -12 22.3307 1.78536 4 0 4 12 25.3060 1.79588 6 0 4 12 23.8069 1.64390 1 0 4 12 23.3500 1.67983 5 -1 -4 -12 0.48461 0.71473 6 1 4 12 0.49583 0.77020 1 1 4 12 2.17325 1.09182 3 -1 4 -12 1.51019 0.99575 4 1 -5 -12 8.70285 1.24216 4 -1 5 12 6.21261 0.79299 6 -1 5 12 6.92751 0.76690 5 -1 5 12 9.36789 0.89120 1 0 -5 -12 -0.1514 1.29217 4 0 5 12 0.65670 0.54005 3 0 5 12 0.30760 0.58159 1 0 5 12 0.13262 0.42337 5 0 5 12 0.15153 0.74337 6 -3 0 13 0.03511 0.43039 1 -2 0 13 0.44477 0.61950 1 1 0 -13 1.63267 1.20756 4 -1 0 13 0.17005 0.95648 1 0 0 -13 0.57019 0.97216 4 -1 0 -13 -0.4513 1.09958 6 -1 0 -13 -1.0116 1.17218 4 -2 0 -13 0.16769 1.00613 4 -2 0 -13 -0.5559 0.86683 6 -3 -1 13 19.4962 1.15308 1 -3 1 13 19.3174 1.16779 1 -2 -1 13 0.39818 0.81381 1 -2 1 13 -0.1762 0.86063 1 1 -1 -13 16.3012 2.27027 4 1 1 -13 21.2721 2.45154 4 -1 1 13 18.3773 1.72680 1 0 -1 -13 30.3705 2.86991 4 0 1 13 32.2613 2.13915 1 0 1 -13 30.9444 2.82793 4 -1 -1 -13 9.25554 1.23821 6 -1 -1 -13 3.88475 1.38558 4 -1 1 -13 7.60065 1.44044 4 -2 -1 -13 7.43380 0.90878 6 -2 1 -13 4.33502 0.90614 6 -2 1 -13 5.98756 1.13170 4 -3 -2 13 5.51415 0.60296 1 -3 2 13 5.71557 0.59083 1 2 -2 -13 -1.5072 1.53482 4 -2 -2 13 0.89102 0.60120 1 -2 2 13 0.23878 0.50315 5 -2 2 13 0.01326 0.52270 1 1 -2 -13 53.0261 3.60535 4 -1 2 13 51.2838 2.48584 1 0 -2 -13 1.62290 1.13102 6 0 -2 -13 0.32489 0.90434 4 0 2 -13 3.14898 1.22728 4 0 2 13 1.16365 0.82322 1 -1 -2 -13 0.53731 0.99605 4 -1 -2 -13 -0.7758 0.76853 6 1 2 13 -0.2027 0.67827 1 -1 2 -13 0.68830 0.86106 4 -2 -2 -13 1.08707 0.66615 6 -2 2 -13 0.76478 0.64929 4 2 -3 -13 6.68536 1.55352 4 -2 3 13 6.61831 0.81079 5 -2 3 13 5.54474 0.87489 1 1 -3 -13 1.21385 1.00493 4 -1 3 13 1.35009 0.62410 1 -1 3 13 0.64070 0.60818 5 0 -3 -13 1.07905 1.35711 4 0 3 -13 0.95591 1.25517 4 0 3 13 0.91072 0.61663 1 -1 -3 -13 2.66293 0.88933 6 -1 -3 -13 4.40477 1.05363 4 -1 3 -13 3.96595 0.97466 4 1 3 13 3.36225 0.80867 1 2 -4 -13 0.93007 1.07958 4 -2 4 13 0.77041 0.35509 5 1 -4 -13 0.02213 0.84713 4 -1 4 13 0.38575 0.58997 5 -1 4 13 1.32380 0.54875 1 0 -4 -13 9.16123 1.33983 4 0 4 -13 6.49358 1.32689 4 0 4 13 8.87520 0.93387 1 -1 -4 -13 18.5368 1.41278 6 -1 4 -13 18.7181 1.27422 4 1 4 13 18.0449 1.14930 1 -2 0 14 4.33103 0.86923 1 -1 0 14 1.67899 0.87361 1 1 0 -14 1.53539 1.18533 4 0 0 -14 11.4107 1.60261 4 -1 0 -14 20.8323 1.86283 4 -2 -1 14 0.29539 0.77869 1 -2 1 14 0.45726 0.73539 1 1 -1 -14 46.9753 2.89610 4 -1 -1 14 44.8002 2.27405 1 1 1 -14 46.5235 2.96855 4 -1 1 14 45.7450 2.27713 1 0 -1 -14 23.6993 2.13253 4 0 1 -14 25.4370 2.16333 4 0 1 14 24.3681 1.89603 1 -1 -1 -14 11.9164 1.58339 4 -1 -1 -14 11.5843 1.21473 6 -1 1 -14 11.3041 1.35529 4 -2 -2 14 -0.1030 0.50212 1 -2 2 14 0.54406 0.49118 1 1 -2 -14 40.7529 2.67685 4 -1 2 14 40.7830 2.02499 1 0 -2 -14 0.30569 0.88803 4 0 2 -14 1.05301 0.90747 4 0 2 14 0.57958 0.66758 1 -1 -2 -14 0.51792 0.62040 6 -1 -2 -14 -0.3479 1.08133 4 -1 2 -14 0.18595 0.65590 4 2 -3 -14 6.04109 1.54483 4 -2 3 14 4.94182 0.73031 1 1 -3 -14 1.21637 0.88288 4 -1 3 14 1.13171 0.78966 1 0 -3 -14 10.0963 1.20090 6 0 -3 -14 11.4035 1.42291 4 0 3 14 12.4173 1.22737 1 0 3 -14 11.9989 1.28875 4 -1 -3 -14 5.19412 0.77235 6 -1 -3 -14 1.55640 1.16043 4 -1 3 -14 6.75963 0.84399 4 1 3 14 5.23814 1.10391 1 -2 0 15 -0.6387 0.45497 1 1 0 -15 0.30657 1.21677 4 -1 0 15 0.06543 0.81261 1 0 0 -15 -0.0435 0.74883 4 -1 0 -15 -0.3088 0.87752 4 -2 -1 15 0.34004 0.43822 1 -2 1 15 1.13134 0.50454 1 1 -1 -15 10.6561 1.35570 4 -1 1 15 12.5323 1.10909 1 0 -1 -15 1.15819 0.70339 4 0 1 -15 2.74813 0.97808 4 -1 -1 -15 1.78011 0.74572 4 -1 1 -15 1.27423 0.63386 4 1 -2 -15 7.23561 1.12562 4 -1 2 15 8.66516 0.91610 1 0 -2 -15 17.9663 1.53778 4 0 2 15 19.1293 1.42381 1 0 2 -15 19.7274 1.68036 4 0 0 0 0.00 0.00 0 _exptl_absorpt_process_details 'SADABS 2014/5' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 0.3200 _exptl_absorpt_correction_T_min 0.1847 _exptl_special_details ) The following wavelength and cell were deduced by SADABS from the direction cosines etc. They are given here for emergency use only: CELL 1.54185 3.992 6.714 13.387 90.007 97.184 89.976 ) ; _shelx_hkl_checksum 96531 _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_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.1361(5) 0.1937(3) 0.44165(19) 0.0573(8) Uani 0.5 1 d . U P A -1 C1 C 0.398(5) 0.679(2) 0.3258(14) 0.053(3) Uani 0.5 1 d . U P A -1 H1 H 0.3590 0.7343 0.2600 0.064 Uiso 0.5 1 calc R . P A -1 N4 N 0.865(2) 0.7288(15) 0.5942(9) 0.068(2) Uani 0.5 1 d . U P A -1 N3 N 0.8499(13) 0.6107(14) 0.6496(5) 0.0504(14) Uani 0.5 1 d . U P A -1 C5 C 0.3203(14) 0.4202(10) 0.4284(5) 0.0435(14) Uani 0.5 1 d . U P A -1 C3 C 0.6723(15) 0.6916(8) 0.4944(5) 0.0449(14) Uani 0.5 1 d . U P A -1 C2 C 0.6133(18) 0.7897(10) 0.4022(7) 0.0553(17) Uani 0.5 1 d . U P A -1 H2 H 0.7049 0.9169 0.3904 0.066 Uiso 0.5 1 calc R . P A -1 N2 N 0.6453(14) 0.4603(10) 0.6072(5) 0.0458(13) Uani 0.5 1 d . U P A -1 N1 N 0.2537(19) 0.5060(14) 0.3420(5) 0.0570(16) Uani 0.5 1 d . U P A -1 C4 C 0.530(5) 0.512(3) 0.5075(13) 0.0307(17) Uani 0.5 1 d . U P A -1 C6 C 0.573(5) 0.272(2) 0.6591(13) 0.054(3) Uani 0.5 1 d . U P A -1 H6A H 0.6909 0.2736 0.7279 0.080 Uiso 0.5 1 calc GR . P A -1 H6B H 0.6510 0.1587 0.6223 0.080 Uiso 0.5 1 calc GR . P A -1 H6C H 0.3293 0.2609 0.6614 0.080 Uiso 0.5 1 calc GR . P A -1 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 0.0418(11) 0.0452(13) 0.0862(16) -0.0177(9) 0.0128(9) -0.0039(7) C1 0.044(5) 0.072(6) 0.043(5) 0.011(4) 0.008(3) 0.020(4) N4 0.049(4) 0.063(5) 0.093(5) -0.024(3) 0.009(3) -0.008(3) N3 0.030(3) 0.079(4) 0.042(3) -0.024(3) 0.005(2) 0.001(3) C5 0.030(3) 0.048(3) 0.053(3) -0.016(3) 0.008(2) 0.004(2) C3 0.034(3) 0.038(3) 0.067(3) -0.010(2) 0.022(2) 0.0051(19) C2 0.043(4) 0.047(3) 0.080(4) 0.011(3) 0.027(3) 0.007(2) N2 0.038(3) 0.063(3) 0.037(3) -0.001(2) 0.005(2) 0.004(2) N1 0.043(4) 0.084(5) 0.042(3) -0.009(3) 0.000(2) 0.013(3) C4 0.027(5) 0.032(4) 0.034(4) -0.001(3) 0.009(3) 0.003(3) C6 0.061(6) 0.058(6) 0.044(6) 0.013(5) 0.018(5) 0.004(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 H1 117.9 N1 C1 H1 117.9 N1 C1 C2 124.2(14) N3 N4 C3 115.1(7) N4 N3 N2 109.4(6) N1 C5 Cl1 116.6(6) N1 C5 C4 121.0(11) C4 C5 Cl1 122.4(9) C2 C3 N4 137.1(7) C4 C3 N4 102.3(9) C4 C3 C2 120.6(9) C1 C2 H2 123.2 C3 C2 C1 113.7(9) C3 C2 H2 123.2 N3 N2 C4 108.5(9) N3 N2 C6 124.8(9) C4 N2 C6 126.7(10) C5 N1 C1 119.5(11) C3 C4 C5 120.9(14) C3 C4 N2 104.6(9) N2 C4 C5 134.5(14) N2 C6 H6A 109.5 N2 C6 H6B 109.5 N2 C6 H6C 109.5 H6A C6 H6B 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C5 1.707(8) C1 H1 0.9500 C1 C2 1.453(17) C1 N1 1.328(19) N4 N3 1.092(12) N4 C3 1.477(13) N3 N2 1.376(10) C5 N1 1.289(11) C5 C4 1.408(12) C3 C2 1.392(11) C3 C4 1.352(18) C2 H2 0.9500 N2 C4 1.399(18) N2 C6 1.485(16) C6 H6A 0.9800 C6 H6B 0.9800 C6 H6C 0.9800 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 C5 N1 C1 -177.7(10) Cl1 C5 C4 C3 179.9(12) Cl1 C5 C4 N2 1(3) N4 N3 N2 C4 0.2(13) N4 N3 N2 C6 178.2(11) N4 C3 C2 C1 179.0(10) N4 C3 C4 C5 180.0(16) N4 C3 C4 N2 -0.5(15) N3 N4 C3 C2 -179.5(7) N3 N4 C3 C4 0.7(13) N3 N2 C4 C5 180(2) N3 N2 C4 C3 0.2(17) C3 N4 N3 N2 -0.6(9) C2 C1 N1 C5 -5(2) C2 C3 C4 C5 0(2) C2 C3 C4 N2 179.7(8) N1 C1 C2 C3 3.6(19) N1 C5 C4 C3 -1(2) N1 C5 C4 N2 179.4(18) C4 C5 N1 C1 3.4(17) C4 C3 C2 C1 -1.2(16) C6 N2 C4 C5 2(3) C6 N2 C4 C3 -177.7(12)