#------------------------------------------------------------------------------ #$Date: 2019-11-11 20:30:40 +0200 (Mon, 11 Nov 2019) $ #$Revision: 227278 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035866.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_4035866 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 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2016-08-25 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _cell_angle_alpha 90 _cell_angle_beta 114.09(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.095(13) _cell_length_b 13.644(14) _cell_length_c 7.107(8) _cell_measurement_reflns_used 1986 _cell_measurement_temperature 100 _cell_measurement_theta_max 68.25 _cell_measurement_theta_min 6.49 _cell_volume 716.6(16) _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 'XM (Sheldrick, 2008)' _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 5.6 _diffrn_detector_type 'Bruker SMART CCD 6000 area detector' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_unetI/netI 0.0462 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 2848 _diffrn_reflns_point_group_measured_fraction_full 0.842 _diffrn_reflns_point_group_measured_fraction_max 0.835 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.276 _diffrn_reflns_theta_min 6.489 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 4.173 _exptl_absorpt_correction_T_max 0.3201 _exptl_absorpt_correction_T_min 0.2162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0863 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.6754. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colorless _exptl_crystal_colour_primary colorless _exptl_crystal_density_diffrn 1.563 _exptl_crystal_description plate _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.328 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.057 _refine_ls_abs_structure_details ; Flack x determined using 396 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.095(17) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 1106 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0314 _refine_ls_shift/su_max 0.059 _refine_ls_shift/su_mean 0.014 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0410P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.0743 _reflns_Friedel_coverage 0.668 _reflns_Friedel_fraction_full 0.684 _reflns_Friedel_fraction_max 0.673 _reflns_number_gt 1053 _reflns_number_total 1106 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jo8b00540_si_005.cif _cod_data_source_block dart169 _cod_original_cell_volume 716.5(16) _cod_database_code 4035866 _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.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2) 2.b Idealised Me refined as rotating group: C6(H6A,H6B,H6C) ; _shelx_res_file ; dart169.res created by SHELXL-2014/7 TITL dart169_a.res in Cc CELL 1.54184 8.095 13.6435 7.1066 90 114.088 90 ZERR 4 0.0132 0.0143 0.0075 0 0.044 0 LATT -7 SYMM +X,-Y,0.5+Z SFAC C H Cl N UNIT 24 20 4 16 L.S. 4 PLAN -3 0 0 TEMP -173.15 BOND $H MORE -1 CONF wpdb fmap 2 acta REM REM REM WGHT 0.041000 FVAR 0.14374 CL1 3 0.788124 0.559980 0.737334 11.00000 0.01755 0.03238 = 0.03045 -0.00378 0.00452 -0.00394 N2 4 0.515913 0.385981 0.511732 11.00000 0.01671 0.02689 = 0.02251 0.00106 0.00658 -0.00256 N4 4 0.224763 0.396305 0.271729 11.00000 0.01818 0.03233 = 0.02175 0.00097 0.00585 -0.00003 N1 4 0.494150 0.654834 0.501552 11.00000 0.02485 0.02659 = 0.03035 -0.00230 0.01300 -0.00125 N3 4 0.365398 0.341025 0.386977 11.00000 0.01693 0.02909 = 0.02347 0.00001 0.00627 -0.00400 C4 1 0.468363 0.481840 0.474759 11.00000 0.01865 0.02622 = 0.01808 0.00075 0.00903 -0.00081 C1 1 0.318032 0.660492 0.353891 11.00000 0.03033 0.02794 = 0.02873 0.00518 0.01487 0.00798 AFIX 43 H1 2 0.268185 0.723951 0.312277 11.00000 -1.20000 AFIX 0 C5 1 0.563951 0.568912 0.556008 11.00000 0.01864 0.03113 = 0.02402 0.00049 0.01042 0.00017 C3 1 0.289168 0.488958 0.326779 11.00000 0.01965 0.02864 = 0.02036 -0.00049 0.01054 -0.00098 C6 1 0.355779 0.235043 0.373366 11.00000 0.02571 0.02989 = 0.03365 -0.00075 0.00811 -0.00452 AFIX 137 H6A 2 0.351581 0.214246 0.239493 11.00000 -1.50000 H6B 2 0.246496 0.212437 0.387507 11.00000 -1.50000 H6C 2 0.462758 0.206777 0.483894 11.00000 -1.50000 AFIX 0 C2 1 0.211080 0.582216 0.263985 11.00000 0.02139 0.03456 = 0.02274 0.00366 0.00803 0.00677 AFIX 43 H2 2 0.090371 0.589915 0.164333 11.00000 -1.20000 AFIX 0 HKLF 4 REM dart169_a.res in Cc REM R1 = 0.0314 for 1053 Fo > 4sig(Fo) and 0.0335 for all 1106 data REM 101 parameters refined using 2 restraints END WGHT 0.0410 0.0000 REM Highest difference peak 0.328, deepest hole -0.172, 1-sigma level 0.057 Q1 1 0.7967 0.4957 0.7407 11.00000 0.05 0.33 Q2 1 0.5043 0.4346 0.4952 11.00000 0.05 0.27 Q3 1 0.0218 0.0097 0.5194 11.00000 0.05 0.26 ; _shelx_res_checksum 89010 _shelx_hkl_file ; -2 0 0 129.99 6.01 6 0 0 6.04 0.51 -6 0 0 5.23 0.44 -6 0 0 5.11 0.45 -6 0 0 4.34 0.45 -6 0 0 4.61 0.46 -8 0 0 0.53 0.20 -8 0 0 1.19 0.23 -8 0 0 0.73 0.22 1 -1 0 88.30 4.27 -1 -1 0 95.09 4.24 -3 -1 0 66.58 3.40 3 -1 0 79.63 3.47 5 -1 0 7.68 0.54 -7 -1 0 19.17 1.07 -7 -1 0 18.74 1.05 -7 -1 0 19.51 1.04 -7 1 0 20.65 1.14 -7 1 0 19.89 1.07 -7 1 0 19.52 1.05 -7 1 0 18.89 1.05 -7 1 0 19.52 1.08 0 -2 0 77.59 3.78 0 2 0 85.91 3.83 -2 -2 0 26.63 1.17 2 -2 0 23.16 1.23 4 -2 0 40.71 2.10 -4 -2 0 43.57 1.99 6 -2 0 18.36 1.18 -6 -2 0 19.02 1.01 -6 -2 0 17.95 1.02 -6 -2 0 19.36 1.04 -6 2 0 19.62 1.07 -6 2 0 20.43 1.05 -6 2 0 18.68 1.02 -6 2 0 19.22 1.02 -8 -2 0 7.14 0.49 -8 2 0 7.35 0.50 -8 2 0 7.99 0.53 -8 2 0 8.18 0.52 -8 2 0 8.10 0.51 -1 -3 0 45.93 2.09 1 -3 0 45.71 2.17 1 3 0 44.59 2.11 -1 3 0 42.75 2.16 3 -3 0 5.08 0.39 -3 -3 0 5.09 0.29 5 -3 0 7.50 0.57 -5 3 0 6.18 0.45 -5 3 0 5.97 0.45 -5 3 0 5.84 0.48 -5 3 0 5.73 0.45 -7 -3 0 1.78 0.41 -7 3 0 1.68 0.25 -7 3 0 1.53 0.24 -7 3 0 2.01 0.32 -7 3 0 1.80 0.28 0 -4 0 22.44 1.07 0 4 0 23.11 1.16 2 -4 0 13.31 0.78 -2 -4 0 13.74 0.66 4 -4 0 4.75 0.45 -4 -4 0 4.65 0.29 6 -4 0 9.28 0.78 -6 4 0 9.32 0.62 -6 4 0 9.53 0.62 -6 4 0 9.25 0.65 -6 4 0 9.60 0.61 -8 4 0 1.52 0.22 -8 4 0 1.46 0.21 -8 4 0 1.06 0.21 -8 4 0 1.83 0.25 -1 -5 0 0.69 0.09 1 -5 0 0.48 0.15 1 -5 0 0.69 0.08 -1 5 0 0.49 0.16 1 5 0 0.76 0.18 -3 -5 0 21.91 1.07 3 -5 0 22.31 1.25 5 -5 0 12.43 0.90 -5 -5 0 11.23 0.63 -5 5 0 12.15 0.71 -5 5 0 11.66 0.70 -5 5 0 12.23 0.70 -5 5 0 11.37 0.71 -7 5 0 9.82 0.62 -7 5 0 10.56 0.64 -7 5 0 10.47 0.66 -7 5 0 9.53 0.62 0 -6 0 6.46 0.35 0 6 0 7.04 0.50 2 -6 0 33.63 1.90 -2 -6 0 40.33 1.73 2 6 0 35.18 1.82 4 -6 0 4.34 0.52 -4 -6 0 4.75 0.31 -4 6 0 4.95 0.39 -4 6 0 5.06 0.43 -6 6 0 6.83 0.50 -6 6 0 7.09 0.55 -6 6 0 7.07 0.54 -6 6 0 7.17 0.51 -8 6 0 1.63 0.20 -8 6 0 1.64 0.19 -8 6 0 1.83 0.19 -1 -7 0 96.39 4.45 -1 7 0 91.02 4.61 1 7 0 98.65 4.59 -3 -7 0 16.66 0.90 3 -7 0 18.57 1.15 3 7 0 18.71 1.00 5 -7 0 31.66 1.89 -5 -7 0 31.40 1.68 -5 7 0 30.46 1.62 -5 7 0 32.98 1.64 -5 7 0 32.23 1.61 -5 7 0 34.56 1.64 -7 7 0 2.65 0.29 -7 7 0 2.82 0.33 -7 7 0 2.32 0.28 -7 7 0 2.10 0.30 0 -8 0 3.66 0.23 0 8 0 3.80 0.40 -2 -8 0 15.71 0.75 2 8 0 13.80 0.88 -4 -8 0 6.28 0.58 -4 -8 0 6.52 0.42 4 8 0 7.94 0.54 -4 8 0 6.66 0.53 -4 8 0 7.46 0.51 -6 8 0 7.20 0.48 -6 8 0 6.81 0.51 -6 8 0 6.95 0.48 -6 8 0 6.65 0.49 -1 -9 0 13.90 0.68 1 9 0 12.39 0.87 -3 -9 0 18.78 1.01 -3 -9 0 16.74 0.92 -3 -9 0 17.70 0.89 -3 9 0 18.22 0.96 3 9 0 15.94 1.04 -5 -9 0 23.14 1.31 -5 9 0 23.46 1.26 -5 9 0 24.88 1.26 7 -9 0 6.89 0.42 -7 9 0 6.62 0.39 -7 9 0 6.78 0.42 0 -10 0 8.77 0.59 0 10 0 9.16 0.71 0 10 0 8.24 0.56 2 -10 0 10.57 0.61 -2 -10 0 9.71 0.56 -2 -10 0 10.09 0.69 -2 -10 0 9.03 0.61 -2 10 0 9.77 0.63 2 10 0 11.62 0.78 -4 -10 0 11.36 0.74 4 10 0 10.30 0.74 6 -10 0 4.95 0.35 -6 10 0 3.47 0.37 -1 -11 0 14.60 0.86 1 -11 0 14.06 0.82 1 11 0 15.42 0.81 -1 11 0 14.06 0.80 1 11 0 14.50 1.00 1 11 0 13.95 0.75 3 -11 0 5.13 0.39 -3 -11 0 4.43 0.41 -3 -11 0 5.16 0.52 3 11 0 4.68 0.52 -3 11 0 5.76 0.45 5 -11 0 0.62 0.17 -5 -11 0 1.17 0.28 -5 11 0 0.89 0.20 0 -12 0 5.91 0.50 0 12 0 5.85 0.44 -2 -12 0 1.26 0.27 -2 12 0 1.19 0.23 2 12 0 1.06 0.22 2 12 0 1.08 0.43 4 -12 0 0.07 0.16 -4 -12 0 0.04 0.23 -4 12 0 0.25 0.19 6 -12 0 0.42 0.13 -6 12 0 0.42 0.13 -1 -13 0 0.65 0.24 1 -13 0 0.64 0.23 -1 13 0 0.48 0.20 1 13 0 0.61 0.19 3 -13 0 0.12 0.18 -3 -13 0 -0.01 0.21 -3 13 0 0.12 0.18 5 -13 0 0.09 0.13 -5 -13 0 0.51 0.20 -5 13 0 0.26 0.14 0 -14 0 3.52 0.41 0 14 0 3.39 0.37 -2 -14 0 1.26 0.25 -2 14 0 1.15 0.21 2 14 0 1.03 0.19 -4 -14 0 1.75 0.25 -4 14 0 2.13 0.26 -1 -15 0 6.05 0.47 1 15 0 5.39 0.41 -1 15 0 6.27 0.42 -3 -15 0 1.59 0.23 -3 15 0 1.39 0.19 0 -16 0 0.64 0.18 0 16 0 0.20 0.14 -2 -16 0 1.34 0.20 -2 16 0 1.18 0.16 -8 0 1 0.24 0.22 -8 0 1 0.04 0.16 -8 0 1 -0.28 0.23 -8 0 1 0.12 0.17 -6 0 1 -0.24 0.21 -6 0 1 0.01 0.16 6 0 -1 -0.03 0.15 -6 0 1 -0.07 0.20 2 0 -1 -0.04 0.03 2 0 -1 -0.01 0.06 0 0 1 0.01 0.05 0 0 -1 -0.01 0.03 2 0 1 0.04 0.07 -2 0 -1 0.05 0.04 4 0 1 0.01 0.11 -6 0 -1 0.19 0.18 -6 0 -1 0.03 0.20 -6 0 -1 -0.19 0.21 -6 0 -1 0.12 0.18 6 0 1 -0.02 0.17 -8 0 -1 0.04 0.14 -8 0 -1 -0.20 0.15 -8 0 -1 0.15 0.13 -9 -1 1 3.82 0.32 -9 -1 1 4.21 0.31 -9 1 1 3.81 0.32 -9 1 1 3.95 0.32 -9 1 1 4.42 0.32 -7 -1 1 9.61 0.66 7 -1 -1 9.11 0.74 -7 -1 1 10.57 0.67 -7 -1 1 10.55 0.66 -7 -1 1 10.31 0.69 -7 1 1 10.49 0.67 -7 1 1 10.28 0.66 -7 1 1 10.29 0.65 5 -1 -1 10.22 0.65 3 -1 -1 1.78 0.10 3 1 -1 1.96 0.12 1 -1 -1 1.47 0.09 1 1 -1 1.54 0.14 1 1 -1 1.45 0.09 1 -1 1 18.40 1.02 -1 -1 -1 21.16 0.96 -1 1 -1 21.62 0.96 -3 -1 -1 19.57 0.92 3 -1 1 18.56 1.02 -5 -1 -1 11.40 0.72 -5 -1 -1 11.60 0.71 5 -1 1 13.23 0.82 -5 -1 -1 12.55 0.70 -5 -1 -1 11.49 0.72 -5 1 -1 12.86 0.73 -5 1 -1 11.12 0.71 -5 1 -1 11.17 0.71 -5 1 -1 12.23 0.72 5 1 1 13.26 0.75 -7 -1 -1 4.62 0.39 -7 -1 -1 4.17 0.40 -7 -1 -1 5.19 0.40 -7 -1 -1 4.54 0.43 -7 1 -1 4.58 0.39 -7 1 -1 4.50 0.43 -7 1 -1 4.43 0.42 -7 1 -1 3.28 0.40 -8 -2 1 0.61 0.23 -8 -2 1 0.95 0.23 -8 -2 1 0.49 0.20 -8 2 1 0.86 0.24 -8 2 1 0.54 0.19 -8 2 1 0.72 0.20 -8 2 1 0.97 0.26 6 -2 -1 4.03 0.45 -6 -2 1 3.33 0.37 -6 -2 1 4.20 0.41 -6 -2 1 3.77 0.39 -6 2 1 3.99 0.39 -6 2 1 3.92 0.39 -6 2 1 4.36 0.40 4 -2 -1 13.40 0.77 4 2 -1 12.76 0.64 2 -2 -1 38.72 1.83 2 -2 -1 35.62 1.72 0 -2 -1 41.02 1.97 0 -2 1 41.75 2.05 0 2 -1 40.73 2.03 0 2 -1 44.66 1.97 0 2 1 43.40 2.02 -2 -2 -1 13.34 0.64 2 -2 1 14.17 0.76 -2 2 -1 12.22 0.62 -4 -2 -1 8.79 0.46 4 -2 1 8.68 0.62 -6 -2 -1 6.77 0.51 -6 -2 -1 6.48 0.52 -6 -2 -1 6.84 0.50 6 -2 1 5.80 0.62 -6 -2 -1 6.98 0.51 -6 2 -1 7.63 0.53 -6 2 -1 7.60 0.52 -6 2 -1 7.11 0.51 -6 2 -1 7.35 0.50 -6 2 -1 7.46 0.57 -8 -2 -1 5.60 0.36 -8 -2 -1 5.34 0.40 -8 2 -1 6.77 0.40 -8 2 -1 6.22 0.37 -8 2 -1 6.03 0.41 -9 3 1 5.61 0.38 -9 3 1 5.99 0.39 -9 3 1 6.15 0.38 -9 3 1 6.32 0.38 -7 -3 1 5.56 0.48 -7 -3 1 5.32 0.48 -7 3 1 5.65 0.45 -7 3 1 5.96 0.48 -7 3 1 5.09 0.49 5 -3 -1 28.57 1.52 5 3 -1 26.88 1.33 -3 -3 1 33.24 1.60 3 -3 -1 34.54 1.73 1 -3 -1 68.41 3.39 1 -3 -1 69.27 3.30 1 3 -1 73.41 3.37 -1 3 1 73.74 3.41 -1 -3 -1 52.57 2.43 1 -3 1 50.83 2.54 -1 3 -1 50.94 2.42 1 3 1 54.29 2.48 -3 -3 -1 16.87 0.89 3 -3 1 19.82 1.06 -5 -3 -1 8.37 0.55 -5 -3 -1 8.89 0.55 5 -3 1 8.90 0.71 -5 -3 -1 8.05 0.58 -5 3 -1 8.78 0.56 -5 3 -1 9.03 0.57 -5 3 -1 8.65 0.61 -5 3 -1 8.75 0.57 -7 -3 -1 4.09 0.37 -7 -3 -1 4.12 0.39 -7 -3 -1 4.17 0.38 -7 3 -1 4.36 0.42 -7 3 -1 4.29 0.39 -7 3 -1 3.89 0.42 -7 3 -1 4.87 0.41 -7 3 -1 4.40 0.38 -8 4 1 6.97 0.49 -8 4 1 6.25 0.45 -8 4 1 6.14 0.45 6 -4 -1 44.70 2.41 -6 -4 1 42.54 2.25 -6 4 1 43.44 2.20 -6 4 1 45.85 2.21 -6 4 1 46.65 2.24 -6 4 1 45.67 2.29 4 -4 -1 15.67 0.94 -2 -4 1 92.23 4.47 2 -4 -1 97.55 4.60 2 4 -1 98.90 4.53 0 -4 -1 84.53 3.96 0 -4 1 76.94 4.07 0 4 -1 90.20 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5 9.04 0.61 -9 5 5 11.42 0.57 7 -5 -5 3.46 0.37 -7 -5 5 3.02 0.41 -7 -5 5 3.14 0.41 -7 -5 5 3.11 0.41 -7 5 5 2.69 0.41 -7 5 5 3.57 0.37 -5 -5 5 11.53 0.74 -5 -5 5 11.86 0.72 5 -5 -5 12.53 0.73 -5 -5 5 11.95 0.80 5 5 -5 10.86 0.95 -5 5 5 11.73 0.74 5 5 -5 9.61 0.64 3 -5 -5 13.10 0.74 3 -5 -5 15.16 0.85 -3 -5 5 14.80 0.84 -3 -5 5 15.08 0.84 -3 5 5 14.37 0.87 3 5 -5 14.34 0.76 1 -5 -5 8.92 0.59 1 -5 -5 8.34 0.48 -1 -5 5 9.26 0.58 -1 -5 5 7.99 0.56 -1 5 5 8.23 0.59 1 5 -5 7.79 0.48 1 -5 5 27.09 1.41 -1 -5 -5 30.19 1.43 -1 -5 -5 30.59 1.44 -1 5 -5 28.59 1.42 1 5 5 27.50 1.46 1 5 5 25.26 1.68 3 -5 5 8.99 0.53 -3 -5 -5 8.87 0.56 -3 -5 -5 8.54 0.55 -3 5 -5 9.20 0.55 -3 5 -5 9.12 0.54 3 5 5 8.84 0.57 -8 -6 5 3.18 0.34 8 -6 -5 3.37 0.33 -8 -6 5 3.34 0.44 -8 6 5 3.14 0.34 -6 -6 5 4.54 0.56 -6 -6 5 3.63 0.41 6 -6 -5 2.84 0.41 -6 -6 5 3.41 0.44 -6 6 5 3.57 0.39 -4 -6 5 10.43 0.75 -4 -6 5 11.47 0.68 -4 -6 5 10.74 0.70 4 -6 -5 11.97 0.72 -4 6 5 10.87 0.70 4 6 -5 10.14 0.60 4 6 -5 9.31 0.91 -2 -6 5 4.22 0.43 2 -6 -5 4.33 0.30 2 -6 -5 4.56 0.45 -2 -6 5 4.23 0.45 -2 6 5 4.52 0.49 2 6 -5 4.16 0.31 0 -6 -5 6.05 0.49 0 -6 5 6.04 0.48 0 -6 5 7.06 0.48 0 -6 -5 5.91 0.51 0 6 5 6.49 0.51 -2 -6 -5 -0.01 0.18 2 -6 5 0.06 0.18 -2 -6 -5 0.30 0.19 2 6 5 0.11 0.23 4 -6 5 1.47 0.19 -4 -6 -5 1.50 0.21 -4 -6 -5 1.59 0.22 -4 6 -5 1.74 0.21 -7 -7 5 0.69 0.23 -7 -7 5 0.71 0.31 7 -7 -5 1.37 0.23 -7 7 5 0.91 0.25 5 -7 -5 1.24 0.26 -5 -7 5 1.65 0.28 -5 -7 5 1.81 0.34 -5 -7 5 1.22 0.28 -5 7 5 1.55 0.30 3 -7 -5 0.95 0.24 -3 -7 5 1.05 0.26 -3 -7 5 0.76 0.24 -3 7 5 0.49 0.28 -1 -7 5 4.50 0.43 1 -7 -5 3.76 0.46 -1 -7 5 4.86 0.43 1 -7 -5 3.66 0.40 -1 7 5 4.82 0.48 1 -7 5 0.96 0.23 -1 -7 -5 1.87 0.25 -1 -7 -5 1.27 0.23 1 -7 5 0.95 0.21 3 -7 5 4.87 0.35 -3 -7 -5 5.14 0.37 -3 -7 -5 4.81 0.37 8 -8 -5 1.53 0.26 -8 -8 5 1.46 0.20 -8 -8 5 2.44 0.32 -8 8 5 1.74 0.22 -6 -8 5 0.62 0.29 6 -8 -5 0.37 0.20 -6 -8 5 0.00 0.21 -6 8 5 0.04 0.23 -4 -8 5 0.35 0.23 -4 -8 5 0.41 0.32 4 -8 -5 0.42 0.22 -4 -8 5 0.31 0.25 -4 8 5 0.38 0.24 2 -8 -5 0.95 0.23 -2 -8 5 0.51 0.23 -2 -8 5 0.57 0.25 0 -8 5 2.89 0.32 0 -8 -5 2.58 0.27 0 -8 5 2.48 0.30 2 -8 5 0.66 0.17 -2 -8 -5 0.73 0.19 2 -8 5 0.80 0.19 -2 -8 -5 0.58 0.18 -7 -9 5 -0.03 0.17 -7 -9 5 -0.26 0.23 7 -9 -5 0.10 0.15 -7 9 5 0.01 0.17 -5 -9 5 0.71 0.24 -5 -9 5 1.23 0.31 5 -9 -5 1.03 0.23 -5 9 5 1.15 0.24 -3 -9 5 0.71 0.28 -3 -9 5 0.56 0.22 3 -9 -5 0.47 0.22 -1 -9 5 -0.07 0.20 1 -9 -5 -0.07 0.19 -1 -9 5 0.02 0.18 1 -9 -5 0.32 0.18 1 -9 5 1.00 0.22 1 -9 5 0.83 0.19 -1 -9 -5 1.52 0.20 -3 -9 -5 0.75 0.14 -6 -10 5 0.80 0.20 6 -10 -5 0.68 0.18 -6 -10 5 0.41 0.25 4 -10 -5 13.99 0.80 -4 -10 5 13.34 0.80 -2 -10 5 0.42 0.20 2 -10 -5 0.24 0.19 -2 10 5 -0.04 0.18 0 -10 5 6.54 0.46 0 -10 5 6.62 0.46 0 -10 -5 7.51 0.46 2 -10 5 2.10 0.21 2 -10 5 2.00 0.23 -2 -10 -5 2.64 0.23 -5 -11 5 3.49 0.41 -5 -11 5 3.84 0.33 5 -11 -5 3.22 0.35 3 -11 -5 2.66 0.34 -3 -11 5 2.22 0.31 1 -11 -5 11.71 0.70 -1 -11 5 13.47 0.71 1 -11 5 0.33 0.14 -1 -11 -5 0.07 0.13 4 -12 -5 20.01 1.01 -4 -12 5 19.40 1.00 -2 -12 5 1.45 0.21 2 -12 -5 1.97 0.28 -2 12 5 1.86 0.25 0 -12 5 8.09 0.48 0 12 5 8.84 0.49 3 -13 -5 0.86 0.17 -3 -13 5 0.64 0.15 -1 -13 5 2.90 0.24 1 -13 -5 2.54 0.28 -1 13 5 2.89 0.23 -8 0 6 6.29 0.43 -8 0 6 5.78 0.45 -8 0 6 6.18 0.56 -8 0 6 5.75 0.47 -6 0 6 12.36 0.74 -6 0 6 11.45 0.71 -6 0 6 12.42 0.76 -6 0 6 11.81 0.85 -4 0 6 19.71 1.07 -4 0 6 18.47 1.11 -4 0 6 18.67 1.17 4 0 -6 21.01 1.00 -2 0 6 6.94 0.55 2 0 -6 5.21 0.39 -2 0 6 6.34 0.48 0 0 6 5.94 0.46 -2 0 -6 22.68 1.25 -2 0 -6 23.47 1.16 -9 -1 6 9.05 0.50 -9 -1 6 9.27 0.51 9 -1 -6 7.95 0.49 -9 1 6 9.46 0.50 -9 1 6 8.85 0.49 -9 1 6 7.72 0.49 -7 -1 6 4.99 0.46 -7 -1 6 5.23 0.44 -7 -1 6 4.93 0.56 -7 -1 6 4.79 0.45 -7 1 6 4.52 0.42 -7 1 6 4.15 0.46 -7 1 6 5.16 0.58 -7 1 6 4.90 0.45 -5 -1 6 64.73 3.16 -5 -1 6 65.78 3.21 -5 -1 6 66.85 3.18 -5 -1 6 66.06 3.16 -5 1 6 67.12 3.23 -5 1 6 63.46 3.19 -5 1 6 64.40 3.15 -3 -1 6 7.73 0.61 3 -1 -6 7.60 0.47 -3 -1 6 7.95 0.55 3 1 -6 7.38 0.46 -3 1 6 7.70 0.54 -3 1 6 8.03 0.63 -1 -1 6 24.31 1.24 -1 -1 6 24.09 1.29 -1 1 6 21.70 1.23 -1 1 6 26.06 1.31 1 -1 6 3.14 0.34 -1 -1 -6 3.68 0.37 -3 -1 -6 0.85 0.16 -3 -1 -6 0.85 0.15 -3 1 -6 0.87 0.17 3 1 6 1.57 0.23 -3 1 -6 0.75 0.14 8 -2 -6 5.43 0.39 -8 -2 6 4.36 0.41 -8 -2 6 4.16 0.49 -8 -2 6 4.59 0.41 -8 2 6 4.60 0.36 -8 2 6 4.84 0.38 -8 2 6 4.65 0.42 -6 -2 6 1.98 0.36 -6 -2 6 2.17 0.30 -6 -2 6 2.15 0.32 -6 -2 6 1.62 0.31 -6 2 6 1.76 0.32 -6 2 6 2.15 0.30 4 -2 -6 3.14 0.27 -4 -2 6 2.10 0.33 -4 -2 6 2.59 0.38 4 2 -6 2.87 0.28 -4 2 6 3.74 0.38 -4 2 6 4.10 0.47 2 -2 -6 7.48 0.47 -2 -2 6 8.53 0.56 -2 -2 6 8.32 0.61 2 2 -6 6.93 0.46 -2 2 6 8.41 0.62 0 -2 6 3.52 0.38 0 -2 6 3.26 0.42 0 -2 -6 2.89 0.41 0 2 6 3.63 0.43 -2 -2 -6 0.35 0.17 -2 -2 -6 0.50 0.17 2 -2 6 0.56 0.19 2 2 6 0.38 0.23 -7 -3 6 0.94 0.23 -7 -3 6 0.99 0.26 7 -3 -6 0.66 0.19 -7 -3 6 0.74 0.29 -7 3 6 0.88 0.24 -7 3 6 0.81 0.26 -5 -3 6 -0.07 0.21 -5 -3 6 0.04 0.24 5 -3 -6 -0.02 0.18 -5 -3 6 -0.28 0.29 -5 3 6 0.34 0.27 -5 3 6 -0.02 0.21 -3 -3 6 1.91 0.35 3 -3 -6 1.84 0.23 -3 -3 6 1.54 0.29 3 3 -6 2.49 0.32 -3 3 6 2.79 0.38 -1 -3 6 1.29 0.30 1 -3 -6 1.53 0.27 -1 -3 6 1.28 0.29 -1 3 6 1.66 0.31 -1 -3 -6 12.03 0.66 1 -3 6 9.88 0.64 1 3 6 10.34 0.68 3 -3 6 3.14 0.27 3 -3 6 3.66 0.30 -3 -3 -6 3.58 0.28 -3 -3 -6 3.16 0.27 3 3 6 3.65 0.30 8 -4 -6 1.41 0.21 -8 -4 6 1.41 0.23 -8 -4 6 1.59 0.24 -8 -4 6 1.73 0.29 -8 4 6 1.27 0.25 -8 4 6 1.11 0.21 -6 -4 6 0.55 0.22 -6 -4 6 0.49 0.26 -6 -4 6 0.53 0.31 6 -4 -6 0.64 0.20 -6 4 6 0.79 0.27 -6 4 6 0.51 0.23 -4 -4 6 0.82 0.26 4 -4 -6 0.87 0.22 -4 -4 6 1.02 0.24 -4 4 6 0.61 0.29 -2 -4 6 2.23 0.31 -2 4 6 2.72 0.38 0 -4 6 0.36 0.23 0 -4 -6 0.57 0.21 0 -4 6 0.67 0.26 0 4 6 0.64 0.25 -2 -4 -6 4.24 0.36 2 -4 6 4.66 0.36 -2 -4 -6 4.96 0.38 2 4 6 4.48 0.39 7 -5 -6 1.05 0.22 -7 -5 6 1.39 0.25 -7 -5 6 1.27 0.25 -7 -5 6 1.55 0.32 -7 5 6 1.55 0.26 -5 -5 6 2.77 0.40 -5 -5 6 2.04 0.30 5 -5 -6 2.42 0.39 -5 -5 6 2.40 0.33 -5 5 6 2.57 0.36 -3 -5 6 3.46 0.41 -3 -5 6 3.47 0.38 3 -5 -6 2.52 0.41 -3 5 6 3.34 0.48 -1 -5 6 2.29 0.32 -1 5 6 2.24 0.35 1 -5 6 4.21 0.37 -1 -5 -6 4.01 0.37 -1 -5 -6 3.94 0.39 1 -5 6 3.30 0.38 1 5 6 4.25 0.38 8 -6 -6 3.04 0.29 -8 -6 6 2.82 0.37 -8 -6 6 2.90 0.30 -8 -6 6 2.73 0.34 -8 6 6 2.95 0.29 6 -6 -6 6.03 0.50 -6 -6 6 6.24 0.48 -6 -6 6 6.99 0.60 -6 -6 6 6.23 0.51 -6 6 6 6.59 0.49 -4 -6 6 7.00 0.50 -4 -6 6 5.55 0.50 4 -6 -6 5.27 0.50 -4 6 6 6.51 0.53 -2 -6 6 3.91 0.40 -2 -6 6 4.51 0.44 -2 6 6 4.63 0.48 0 -6 6 13.34 0.75 0 6 6 12.79 0.77 2 -6 6 3.68 0.29 -2 -6 -6 3.45 0.30 -2 -6 -6 3.71 0.30 -7 -7 6 4.14 0.36 7 -7 -6 3.11 0.35 -7 -7 6 4.06 0.45 -7 -7 6 3.39 0.33 -7 7 6 4.60 0.36 -5 -7 6 -0.30 0.20 -5 -7 6 1.14 0.44 -5 -7 6 0.01 0.21 5 -7 -6 0.12 0.20 -5 7 6 0.22 0.22 -3 -7 6 7.92 0.57 -3 -7 6 8.22 0.56 3 -7 -6 9.79 0.60 -3 7 6 7.85 0.60 -1 -7 6 2.23 0.28 -1 -7 6 1.53 0.23 -1 7 6 1.66 0.29 1 -7 6 6.14 0.43 -1 -7 -6 7.43 0.42 6 -8 -6 7.70 0.51 -6 -8 6 7.79 0.57 -6 -8 6 7.62 0.52 -6 8 6 7.83 0.50 -4 -8 6 9.34 0.61 -4 -8 6 9.91 0.62 4 -8 -6 9.26 0.63 -4 8 6 10.19 0.62 2 -8 -6 3.35 0.36 -2 -8 6 3.30 0.37 -2 -8 6 3.34 0.35 -2 8 6 3.46 0.39 0 -8 6 13.14 0.68 0 -8 6 12.45 0.67 0 -8 -6 11.42 0.65 5 -9 -6 4.16 0.38 -5 -9 6 4.27 0.38 -5 9 6 4.05 0.35 -3 -9 6 4.06 0.38 3 -9 -6 4.27 0.41 -3 -9 6 4.47 0.38 -1 -9 6 6.81 0.44 -1 -9 6 6.48 0.43 -1 -9 -6 0.82 0.13 1 -9 6 1.10 0.16 -6 -10 6 2.08 0.25 6 -10 -6 1.92 0.24 -4 -10 6 3.20 0.33 4 -10 -6 3.60 0.33 -2 -10 6 3.30 0.33 2 -10 -6 3.93 0.34 -2 -10 6 4.01 0.32 0 -10 6 4.60 0.30 0 -10 6 4.43 0.30 -3 -11 6 0.39 0.16 3 -11 -6 -0.01 0.14 -1 -11 6 0.57 0.13 -8 0 7 -0.02 0.19 -8 0 7 -0.16 0.15 8 0 -7 0.09 0.14 -6 0 7 0.08 0.19 -6 0 7 -0.04 0.22 -4 0 7 0.08 0.26 -4 0 7 0.10 0.21 -2 0 7 0.20 0.20 -2 0 7 0.09 0.28 0 0 7 0.22 0.22 7 -1 -7 1.32 0.21 -7 -1 7 1.84 0.32 -7 -1 7 1.18 0.23 -7 -1 7 1.08 0.23 -7 1 7 1.23 0.23 -7 1 7 1.07 0.23 -5 -1 7 3.08 0.37 -5 -1 7 2.87 0.40 5 -1 -7 2.37 0.36 -5 1 7 2.04 0.33 -5 1 7 2.64 0.34 -3 -1 7 0.47 0.28 -3 -1 7 0.60 0.23 -3 1 7 0.72 0.30 -3 1 7 0.54 0.22 -1 -1 7 0.13 0.20 -1 -1 7 -0.15 0.24 -1 1 7 -0.04 0.25 1 -1 7 0.97 0.21 1 -1 7 0.46 0.27 1 1 7 1.17 0.21 -8 -2 7 0.87 0.17 8 -2 -7 0.66 0.16 -8 -2 7 0.82 0.19 -8 2 7 0.68 0.20 -8 2 7 0.58 0.16 -6 -2 7 1.32 0.34 6 -2 -7 1.17 0.21 -6 -2 7 1.20 0.25 -6 2 7 1.73 0.29 -6 2 7 1.35 0.24 -4 -2 7 1.78 0.31 -4 -2 7 2.04 0.29 -4 2 7 1.99 0.33 -4 2 7 2.08 0.26 -2 -2 7 3.15 0.43 -2 -2 7 4.13 0.38 -2 2 7 3.50 0.45 0 -2 7 3.02 0.34 0 -2 7 2.79 0.31 0 2 7 2.70 0.34 -7 -3 7 3.17 0.32 7 -3 -7 2.82 0.32 -7 -3 7 3.04 0.44 -7 -3 7 2.86 0.33 -7 3 7 3.32 0.34 -7 3 7 2.96 0.30 5 -3 -7 4.41 0.43 -5 -3 7 4.45 0.43 -5 3 7 4.93 0.46 -3 -3 7 2.11 0.31 -3 -3 7 1.81 0.27 -3 3 7 2.00 0.33 -1 -3 7 10.36 0.62 -1 -3 7 10.19 0.65 -1 3 7 10.83 0.69 1 -3 7 1.61 0.24 1 -3 7 1.97 0.24 1 3 7 2.65 0.29 -6 -4 7 2.73 0.36 -6 -4 7 2.88 0.35 6 -4 -7 3.14 0.36 -6 -4 7 3.04 0.35 -6 4 7 2.77 0.36 4 -4 -7 7.14 0.52 -4 -4 7 6.35 0.50 -4 4 7 7.10 0.56 -2 -4 7 1.70 0.27 -2 4 7 2.39 0.33 0 -4 7 5.06 0.40 0 -4 7 5.74 0.39 0 4 7 5.77 0.43 -7 -5 7 5.43 0.37 -7 -5 7 5.45 0.37 7 -5 -7 5.04 0.38 -7 -5 7 4.62 0.43 -7 5 7 5.65 0.39 5 -5 -7 3.87 0.40 -5 -5 7 4.09 0.38 -5 -5 7 4.16 0.39 -5 5 7 4.54 0.44 -3 -5 7 2.33 0.29 -3 5 7 2.69 0.37 -1 -5 7 11.22 0.65 -1 5 7 11.67 0.69 1 -5 7 2.32 0.23 1 5 7 2.58 0.24 -6 -6 7 4.16 0.34 -6 -6 7 3.87 0.36 6 -6 -7 3.80 0.35 -6 6 7 4.64 0.35 4 -6 -7 2.12 0.33 -4 -6 7 2.94 0.33 -4 -6 7 2.68 0.32 -4 6 7 2.72 0.34 -2 -6 7 3.35 0.33 -2 6 7 3.15 0.36 0 -6 7 0.68 0.17 0 6 7 0.67 0.19 -5 -7 7 0.83 0.19 -5 -7 7 0.82 0.20 5 -7 -7 0.87 0.19 -5 7 7 0.72 0.21 -3 -7 7 0.40 0.19 -3 -7 7 0.59 0.19 -3 7 7 0.54 0.20 -1 -7 7 1.43 0.20 -1 7 7 1.54 0.22 -6 8 7 -0.06 0.14 -4 -8 7 0.33 0.16 4 -8 -7 0.38 0.16 -4 -8 7 0.31 0.17 -4 8 7 0.47 0.17 -2 -8 7 0.90 0.28 -2 -8 7 1.01 0.18 -3 -9 7 -0.35 0.13 -3 -9 7 -0.09 0.15 -6 0 8 20.93 1.03 -6 0 8 20.28 1.03 -4 0 8 0.43 0.17 -4 0 8 0.82 0.23 -2 0 8 4.05 0.37 -5 -1 8 1.67 0.24 -5 -1 8 1.48 0.22 -5 1 8 1.51 0.26 -5 1 8 1.51 0.21 -3 -1 8 11.17 0.62 -3 -1 8 11.17 0.65 -3 1 8 11.39 0.66 -1 -1 8 1.51 0.22 -1 1 8 1.76 0.25 -6 -2 8 2.19 0.25 -6 2 8 2.08 0.26 -4 -2 8 0.92 0.22 -4 -2 8 0.67 0.19 -4 2 8 0.55 0.22 -2 -2 8 0.06 0.16 -2 -2 8 0.21 0.17 -2 2 8 -0.21 0.18 -5 -3 8 0.95 0.20 -5 3 8 1.08 0.22 -3 -3 8 0.91 0.20 -3 3 8 0.85 0.22 -1 -3 8 3.88 0.27 -1 3 8 4.03 0.30 -6 -4 8 0.29 0.15 -6 4 8 0.73 0.16 -4 -4 8 1.21 0.20 -4 4 8 0.99 0.21 -2 -4 8 0.07 0.15 -2 4 8 -0.02 0.16 -5 -5 8 1.13 0.18 -5 5 8 1.37 0.19 -3 -5 8 2.00 0.23 -3 5 8 2.11 0.24 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 84755 _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, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn Cl1 Cl 0.78812(10) 0.55998(6) 0.73733(12) 0.0285(3) Uani 1 1 d . N2 N 0.5159(4) 0.3860(2) 0.5117(4) 0.0225(6) Uani 1 1 d . N4 N 0.2248(4) 0.3963(2) 0.2717(4) 0.0248(6) Uani 1 1 d . N1 N 0.4941(4) 0.6548(2) 0.5016(5) 0.0267(7) Uani 1 1 d . N3 N 0.3654(4) 0.3410(2) 0.3870(5) 0.0238(6) Uani 1 1 d . C4 C 0.4684(4) 0.4818(3) 0.4748(5) 0.0205(7) Uani 1 1 d . C1 C 0.3180(5) 0.6605(3) 0.3539(6) 0.0281(8) Uani 1 1 d . H1 H 0.2682 0.7240 0.3123 0.034 Uiso 1 1 calc R C5 C 0.5640(5) 0.5689(3) 0.5560(5) 0.0240(8) Uani 1 1 d . C3 C 0.2892(5) 0.4890(3) 0.3268(5) 0.0221(7) Uani 1 1 d . C6 C 0.3558(5) 0.2350(3) 0.3734(7) 0.0311(8) Uani 1 1 d . H6A H 0.3516 0.2142 0.2395 0.047 Uiso 1 1 calc GR H6B H 0.2465 0.2124 0.3875 0.047 Uiso 1 1 calc GR H6C H 0.4628 0.2068 0.4839 0.047 Uiso 1 1 calc GR C2 C 0.2111(5) 0.5822(3) 0.2640(5) 0.0265(8) Uani 1 1 d . H2 H 0.0904 0.5899 0.1643 0.032 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0175(4) 0.0324(4) 0.0304(4) -0.0038(4) 0.0045(3) -0.0039(4) N2 0.0167(14) 0.0269(16) 0.0225(14) 0.0011(12) 0.0066(11) -0.0026(11) N4 0.0182(13) 0.0323(17) 0.0217(14) 0.0010(12) 0.0059(11) 0.0000(12) N1 0.0249(14) 0.0266(17) 0.0304(15) -0.0023(13) 0.0130(12) -0.0012(13) N3 0.0169(13) 0.0291(16) 0.0235(13) 0.0000(12) 0.0063(10) -0.0040(13) C4 0.0186(18) 0.0262(18) 0.0181(16) 0.0008(14) 0.0090(13) -0.0008(14) C1 0.0303(19) 0.0279(19) 0.0287(19) 0.0052(15) 0.0149(15) 0.0080(15) C5 0.0186(16) 0.031(2) 0.0240(18) 0.0005(15) 0.0104(14) 0.0002(16) C3 0.0197(16) 0.0286(18) 0.0204(16) -0.0005(14) 0.0105(13) -0.0010(14) C6 0.0257(18) 0.030(2) 0.034(2) -0.0008(16) 0.0081(15) -0.0045(16) C2 0.0214(17) 0.035(2) 0.0227(17) 0.0037(14) 0.0080(13) 0.0068(15) 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 N3 N2 C4 101.8(3) N3 N4 C3 102.6(3) C5 N1 C1 117.9(3) N2 N3 N4 118.0(3) N2 N3 C6 121.0(3) N4 N3 C6 121.0(3) N2 C4 C5 132.0(3) N2 C4 C3 109.6(3) C3 C4 C5 118.4(3) N1 C1 H1 117.5 C2 C1 N1 125.0(3) C2 C1 H1 117.5 N1 C5 Cl1 118.7(3) N1 C5 C4 123.0(3) C4 C5 Cl1 118.4(3) N4 C3 C4 107.9(3) N4 C3 C2 132.6(3) C4 C3 C2 119.5(3) N3 C6 H6A 109.5 N3 C6 H6B 109.5 N3 C6 H6C 109.5 H6A C6 H6B 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 C1 C2 C3 116.3(3) C1 C2 H2 121.8 C3 C2 H2 121.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C5 1.749(4) N2 N3 1.329(4) N2 C4 1.358(5) N4 N3 1.332(4) N4 C3 1.362(5) N1 C1 1.385(5) N1 C5 1.290(5) N3 C6 1.449(5) C4 C5 1.407(5) C4 C3 1.405(5) C1 H1 0.9500 C1 C2 1.359(5) C3 C2 1.410(5) C6 H6A 0.9800 C6 H6B 0.9800 C6 H6C 0.9800 C2 H2 0.9500 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 N2 C4 C5 Cl1 1.0(5) N2 C4 C5 N1 -179.6(4) N2 C4 C3 N4 0.1(3) N2 C4 C3 C2 -179.8(3) N4 C3 C2 C1 -180.0(3) N1 C1 C2 C3 -0.7(5) N3 N2 C4 C5 179.7(3) N3 N2 C4 C3 -0.2(3) N3 N4 C3 C4 0.0(3) N3 N4 C3 C2 180.0(4) C4 N2 N3 N4 0.3(4) C4 N2 N3 C6 179.0(4) C4 C3 C2 C1 0.0(5) C1 N1 C5 Cl1 178.4(3) C1 N1 C5 C4 -1.1(5) C5 N1 C1 C2 1.3(5) C5 C4 C3 N4 -179.8(3) C5 C4 C3 C2 0.2(4) C3 N4 N3 N2 -0.2(4) C3 N4 N3 C6 -178.9(3) C3 C4 C5 Cl1 -179.1(3) C3 C4 C5 N1 0.4(5)