#------------------------------------------------------------------------------ #$Date: 2024-10-22 01:10:36 +0300 (Tue, 22 Oct 2024) $ #$Revision: 295572 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572914.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_1572914 loop_ _publ_author_name 'Limberg, Niklas' 'Rautiainen, J. Mikko' 'Lundell, Jan' 'Riedel, Sebastian' 'Puttreddy, Rakesh R.' 'Rissanen, Kari' _publ_section_title ; Dichlorine-Pyridine N-oxide Halogen-Bonded Complexes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC06270A _journal_year 2024 _chemical_formula_moiety 'Cl3, C11 H10 N O, C11 H9 N O' _chemical_formula_sum 'C22 H19 Cl3 N2 O2' _chemical_formula_weight 449.74 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2024-09-11 _audit_creation_method ; Olex2 1.5-alpha (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-09-13 deposited with the CCDC. 2024-10-21 downloaded from the CCDC. ; _cell_angle_alpha 71.538(19) _cell_angle_beta 81.375(19) _cell_angle_gamma 89.527(14) _cell_formula_units_Z 2 _cell_length_a 6.027(3) _cell_length_b 11.706(6) _cell_length_c 15.295(9) _cell_measurement_reflns_used 506 _cell_measurement_temperature 100.00 _cell_measurement_theta_max 22.591 _cell_measurement_theta_min 3.498 _cell_volume 1011.1(9) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'olex2.refine 1.5-alpha (Bourhis et al., 2015)' _computing_structure_solution 'olex2.solve 1.5-alpha (Bourhis et al., 2015)' _diffrn_ambient_temperature 100.00 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.974 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.2284 _diffrn_reflns_av_unetI/netI 0.3770 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.974 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3636 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.974 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.393 _diffrn_reflns_theta_min 2.656 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.475 _exptl_absorpt_correction_T_max 0.745210 _exptl_absorpt_correction_T_min 0.522247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. For component 1: wR2(int) was 0.1189 before and 0.0843 after correction. The Ratio of minimum to maximum transmission is 0.70. Final HKLF 4 output contains 17493 reflections, Rint = 0.2284 (2031 with I > 3sig(I), Rint = 0.1017) ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.477 _exptl_crystal_description needle _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.387 _exptl_crystal_size_mid 0.045 _exptl_crystal_size_min 0.025 _refine_diff_density_max 0.761 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.166 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 3636 _refine_ls_number_restraints 156 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.3614 _refine_ls_R_factor_gt 0.1321 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2983 _refine_ls_wR_factor_ref 0.4380 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1278 _reflns_number_total 3636 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc06270a3.cif _cod_data_source_block OGH_D49_27 _cod_original_cell_volume 1011.1(10) _cod_database_code 1572914 _shelx_shelxl_version_number 2019/1 _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 0.988 _shelx_estimated_absorpt_t_min 0.837 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.77152 0.22848 2. Uiso/Uaniso restraints and constraints Uanis(C12) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq, : with sigma of 0.005 and sigma for terminal atoms of 0.01 3.a Aromatic/amide H refined with riding coordinates: C19(H19), C18(H18), C7(H7), C22(H22), C4(H4), C11(H11), C21(H21), C9(H9), C8(H8), C1(H1A), C15(H15), C12(H12), C13(H13), C14(H14), C20(H20), C10(H10), C3(H3), C2(H2) 3.b Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL full1_P-1_a.res in P-1 hklf5.res created by SHELXL-2019/1 at 19:11:02 on 30-Aug-2024 REM Old TITL full1_P-1 in P-1 REM SHELXT solution in P-1: R1 0.265, Rweak 0.019, Alpha 0.074 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C22 Cl3 N2 O2 CELL 0.71073 6.0266 11.706 15.2954 71.538 81.375 89.527 ZERR 2 0.0031 0.0062 0.0094 0.019 0.019 0.014 LATT 1 SFAC C H Cl N O UNIT 44 38 6 4 4 ISOR 0.005 0.01 H2 C12 H1a H3 C10 C2 H15 H4 C21 H13 C17 C7 H21 C1 H11 C13 = C9 C4 H9 C8 H10 C22 H18 C6 O1 C11 H8 C16 C15 H22 H12 H7 C5 C3 N2 O2 H1 C20 = N1 C14 C19 H14 H19 C18 H20 L.S. 10 PLAN 10 SIZE 0.025 0.045 0.387 TEMP -173.15 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 acta MERG 0 REM REM REM WGHT 0.200000 BASF 0.22848 FVAR 0.58785 CL2 3 0.846713 0.076958 0.731488 11.00000 0.03943 0.02890 = 0.04467 -0.01107 -0.00259 -0.00224 CL3 3 0.903329 0.139582 0.568499 11.00000 0.04560 0.03217 = 0.04780 -0.00946 -0.00224 -0.00359 CL1 3 0.789227 0.015996 0.889970 11.00000 0.04882 0.02897 = 0.04854 -0.01122 -0.00494 0.00194 O1 5 1.004656 0.326334 0.310330 11.00000 0.02972 0.03775 = 0.04770 -0.01048 -0.00757 0.00420 AFIX 147 H1 2 0.987926 0.390577 0.267942 11.00000 -1.50000 AFIX 0 O2 5 1.052492 0.522448 0.188511 11.00000 0.02797 0.04192 = 0.03629 -0.00540 -0.00607 0.00229 N2 4 0.885476 0.590711 0.154447 11.00000 0.03081 0.03716 = 0.03716 -0.00560 -0.00691 0.00477 N1 4 0.804591 0.263390 0.342537 11.00000 0.03218 0.03178 = 0.03254 -0.00577 -0.00776 -0.00098 C19 1 0.877789 0.250432 0.090324 11.00000 0.03540 0.03492 = 0.03250 -0.00897 -0.00546 0.00683 AFIX 43 H19 2 1.003033 0.213678 0.066210 11.00000 -1.20000 AFIX 0 C18 1 0.905383 0.366515 0.091334 11.00000 0.03445 0.02874 = 0.03470 -0.00882 -0.00459 0.00202 AFIX 43 H18 2 1.047851 0.408178 0.071038 11.00000 -1.20000 AFIX 0 C7 1 0.448780 0.512079 0.344021 11.00000 0.02966 0.03203 = 0.03372 -0.01404 0.00332 0.00330 AFIX 43 H7 2 0.329163 0.478321 0.324900 11.00000 -1.20000 AFIX 0 C16 1 0.716675 0.552153 0.119489 11.00000 0.02903 0.02714 = 0.03272 -0.00918 -0.00613 0.00181 C17 1 0.715143 0.421823 0.123511 11.00000 0.02725 0.02727 = 0.03017 -0.00959 -0.00321 -0.00246 C22 1 0.504003 0.359204 0.151958 11.00000 0.02813 0.03370 = 0.02919 -0.01094 -0.00164 0.00326 AFIX 43 H22 2 0.373924 0.396877 0.171155 11.00000 -1.20000 AFIX 0 C4 1 0.423957 0.241447 0.408049 11.00000 0.03536 0.03453 = 0.03860 -0.01201 -0.00622 0.00046 AFIX 43 H4 2 0.290613 0.274072 0.430281 11.00000 -1.20000 AFIX 0 C11 1 0.796280 0.489362 0.405827 11.00000 0.03262 0.02932 = 0.02785 -0.00606 -0.00815 0.00218 AFIX 43 H11 2 0.916712 0.441515 0.428022 11.00000 -1.20000 AFIX 0 C21 1 0.491287 0.241287 0.151171 11.00000 0.03465 0.03138 = 0.03952 -0.00965 -0.00072 -0.00012 AFIX 43 H21 2 0.350420 0.197944 0.170859 11.00000 -1.20000 AFIX 0 C9 1 0.607662 0.676540 0.374717 11.00000 0.04505 0.03657 = 0.04276 -0.01551 -0.00370 -0.00012 AFIX 43 H9 2 0.601126 0.756952 0.376382 11.00000 -1.20000 AFIX 0 C6 1 0.623174 0.441539 0.372495 11.00000 0.03746 0.03298 = 0.03936 -0.01501 -0.00382 0.00400 C8 1 0.440894 0.630734 0.342160 11.00000 0.03801 0.03039 = 0.03399 -0.01025 -0.00594 0.00709 AFIX 43 H8 2 0.322487 0.679445 0.318827 11.00000 -1.20000 AFIX 0 C1 1 0.805235 0.145620 0.343357 11.00000 0.04161 0.04210 = 0.04387 -0.01327 -0.00180 0.00570 AFIX 43 H1A 2 0.939915 0.112745 0.322613 11.00000 -1.20000 AFIX 0 C15 1 0.559784 0.629306 0.084312 11.00000 0.03832 0.03389 = 0.03392 -0.01421 -0.00237 0.00738 AFIX 43 H15 2 0.442958 0.602803 0.059044 11.00000 -1.20000 AFIX 0 C5 1 0.619538 0.314920 0.375055 11.00000 0.03215 0.03164 = 0.03236 -0.00937 -0.00155 0.00413 C12 1 0.906702 0.708226 0.154384 11.00000 0.03629 0.03338 = 0.03813 -0.01371 0.00233 -0.00695 AFIX 43 H12 2 1.029392 0.734296 0.176745 11.00000 -1.20000 AFIX 0 C13 1 0.741339 0.787624 0.120262 11.00000 0.03406 0.03504 = 0.03951 -0.01216 -0.00973 -0.00032 AFIX 43 H13 2 0.747404 0.868252 0.121285 11.00000 -1.20000 AFIX 0 C14 1 0.570111 0.748282 0.085262 11.00000 0.04292 0.04094 = 0.04173 -0.01356 -0.00888 0.00379 AFIX 43 H14 2 0.458423 0.802118 0.061639 11.00000 -1.20000 AFIX 0 C20 1 0.676849 0.185329 0.122695 11.00000 0.04881 0.04335 = 0.04603 -0.01464 -0.00463 0.00418 AFIX 43 H20 2 0.666326 0.103334 0.125350 11.00000 -1.20000 AFIX 0 C10 1 0.784535 0.608130 0.405063 11.00000 0.03602 0.03417 = 0.03751 -0.01558 -0.00431 -0.00393 AFIX 43 H10 2 0.900278 0.642655 0.425788 11.00000 -1.20000 AFIX 0 C3 1 0.417518 0.123120 0.409502 11.00000 0.04418 0.04009 = 0.04229 -0.01521 -0.00926 0.00066 AFIX 43 H3 2 0.283283 0.074346 0.434201 11.00000 -1.20000 AFIX 0 C2 1 0.610619 0.076332 0.374244 11.00000 0.04449 0.03742 = 0.03748 -0.01084 -0.00999 -0.00077 AFIX 43 H2 2 0.607122 -0.003644 0.371656 11.00000 -1.20000 AFIX 0 HKLF 5 REM full1_P-1_a.res in P-1 REM wR2 = 0.4380, GooF = S = 1.086, Restrained GooF = 1.069 for all data REM R1 = 0.1321 for 1278 Fo > 4sig(Fo) and 0.3614 for all 3636 data REM 264 parameters refined using 156 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.761, deepest hole -0.788, 1-sigma level 0.166 Q1 1 0.9592 0.2024 0.3976 11.00000 0.05 0.72 Q2 1 0.5394 0.9429 0.1825 11.00000 0.05 0.63 Q3 1 0.5673 -0.0166 0.8881 11.00000 0.05 0.62 Q4 1 1.0343 0.5565 0.0753 11.00000 0.05 0.59 Q5 1 1.0583 0.3316 0.0117 11.00000 0.05 0.55 Q6 1 0.9037 0.9860 0.1074 11.00000 0.05 0.54 Q7 1 0.9387 0.0237 0.5663 11.00000 0.05 0.54 Q8 1 0.9537 0.2722 0.4573 11.00000 0.05 0.54 Q9 1 1.0702 0.2054 0.3219 11.00000 0.05 0.54 Q10 1 0.1505 0.2375 0.4123 11.00000 0.05 0.54 ; _shelx_res_checksum 3848 _shelx_hkl_file ; 1 0 0 12.9733 3.39912 1 2 0 0 10.0187 4.24512 1 3 0 2 473.207 35.1316 -2 3 0 0 473.207 35.1316 1 4 0 3 27.7007 9.49536 -2 4 0 0 27.7007 9.49536 1 5 0 4 -6.2509 23.2870 -2 5 0 0 -6.2509 23.2870 1 6 0 0 9.49423 6.15473 1 7 0 5 -8.1016 31.2090 -2 7 0 0 -8.1016 31.2090 1 7 1 5 -32.697 44.0400 -2 -7 1 0 -32.697 44.0400 1 6 1 4 -30.441 33.7818 -2 -6 1 0 -30.441 33.7818 1 5 1 4 134.385 16.5908 -2 -5 1 0 134.385 16.5908 1 4 1 3 122.318 18.4684 -2 -4 1 0 122.318 18.4684 1 3 1 2 463.177 28.0950 -2 -3 1 0 463.177 28.0950 1 -2 1 0 1776.42 29.4798 1 -1 1 0 11.2376 3.26660 1 1 1 0 825.904 17.3858 1 2 1 0 7.00644 5.81695 1 3 -1 2 207.290 31.2745 -2 3 1 0 207.290 31.2745 1 4 -1 3 17.1370 18.4630 -2 4 1 0 17.1370 18.4630 1 5 -1 4 17.1403 24.1816 -2 5 1 0 17.1403 24.1816 1 6 1 0 11.6044 10.2722 1 7 -1 5 10.0428 44.9450 -2 7 1 0 10.0428 44.9450 1 7 2 5 7.37891 39.3378 -2 -7 2 0 7.37891 39.3378 1 -6 2 0 30.0590 18.2833 1 -5 2 0 125.958 30.2213 1 4 2 3 12.4479 4.14422 -2 -4 2 0 12.4479 4.14422 1 3 2 2 114.272 11.1282 -2 -3 2 0 114.272 11.1282 1 -2 2 0 2125.85 19.0330 1 1 2 1 170.272 22.9867 -2 -1 2 0 170.272 22.9867 1 0 2 0 -5.0197 10.0457 -2 0 2 0 -5.0197 10.0457 1 1 2 0 1417.18 22.7113 1 2 2 0 64.0146 8.22542 1 3 -2 2 -12.183 16.3967 -2 3 2 0 -12.183 16.3967 1 4 -2 3 23.1373 16.1587 -2 4 2 0 23.1373 16.1587 1 5 -2 4 72.5428 34.2103 -2 5 2 0 72.5428 34.2103 1 6 2 0 -11.310 10.3613 1 7 -2 5 13.8340 70.0773 -2 7 2 0 13.8340 70.0773 1 7 3 5 -37.733 43.5873 -2 -7 3 0 -37.733 43.5873 1 -6 3 0 23.4446 7.57198 1 5 3 4 24.6149 41.7874 -2 -5 3 0 24.6149 41.7874 1 4 3 3 53.2271 18.4240 -2 -4 3 0 53.2271 18.4240 1 -3 3 0 313.363 25.5154 1 -2 3 0 -0.0534 1.95970 1 1 3 1 719.382 42.3842 -2 -1 3 0 719.382 42.3842 1 0 3 0 45.3881 13.9951 -2 0 3 0 45.3881 13.9951 1 1 3 0 160.278 11.1196 1 2 3 0 19.0219 6.95627 1 3 -3 2 62.0616 16.6014 -2 3 3 0 62.0616 16.6014 1 4 -3 3 -1.4537 15.3726 -2 4 3 0 -1.4537 15.3726 1 5 -3 4 -5.6205 53.9734 -2 5 3 0 -5.6205 53.9734 1 6 3 0 -10.366 11.1907 1 -6 4 0 22.5819 29.7889 1 5 4 4 171.221 30.8582 -2 -5 4 0 171.221 30.8582 1 4 4 3 427.484 34.6608 -2 -4 4 0 427.484 34.6608 1 3 4 2 19.9237 7.01777 -2 -3 4 0 19.9237 7.01777 1 -2 4 0 363.082 12.1611 1 1 4 1 360.689 35.7872 -2 -1 4 0 360.689 35.7872 1 0 4 0 15.1321 16.0001 -2 0 4 0 15.1321 16.0001 1 1 4 0 0.92643 10.9040 1 2 4 0 18.5826 8.11402 1 3 -4 2 76.6378 26.9385 -2 3 4 0 76.6378 26.9385 1 4 -4 3 24.7922 25.2501 -2 4 4 0 24.7922 25.2501 1 5 -4 4 20.7904 41.9278 -2 5 4 0 20.7904 41.9278 1 6 4 0 21.7524 18.0250 1 6 5 5 47.4792 58.0401 -2 -6 5 0 47.4792 58.0401 1 5 5 4 35.2894 26.1323 -2 -5 5 0 35.2894 26.1323 1 4 5 3 197.859 35.5569 -2 -4 5 0 197.859 35.5569 1 3 5 2 25.7636 12.8971 -2 -3 5 0 25.7636 12.8971 1 2 5 2 383.132 44.3957 -2 -2 5 0 383.132 44.3957 1 1 5 1 275.517 26.0392 -2 -1 5 0 275.517 26.0392 1 0 5 0 17.4739 17.9487 -2 0 5 0 17.4739 17.9487 1 1 5 0 13.5603 6.87076 1 2 5 0 111.419 16.8041 1 3 -5 2 115.114 36.6998 -2 3 5 0 115.114 36.6998 1 4 -5 3 8.77917 31.0964 -2 4 5 0 8.77917 31.0964 1 5 -5 4 -13.797 35.9086 -2 5 5 0 -13.797 35.9086 1 6 5 0 -1.7897 20.3927 1 6 6 5 -68.903 44.1612 -2 -6 6 0 -68.903 44.1612 1 5 6 4 45.8329 24.9902 -2 -5 6 0 45.8329 24.9902 1 4 6 3 170.595 25.1185 -2 -4 6 0 170.595 25.1185 1 3 6 2 175.421 17.9084 -2 -3 6 0 175.421 17.9084 1 -2 6 0 55.9803 7.97641 1 1 6 1 51.9324 17.6464 -2 -1 6 0 51.9324 17.6464 1 0 6 0 -10.263 13.5144 -2 0 6 0 -10.263 13.5144 1 1 -6 1 5.36422 46.7154 -2 1 6 0 5.36422 46.7154 1 2 6 0 2.07659 8.39266 1 3 -6 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-70.695 54.6645 -2 1 10 16 -70.695 54.6645 1 2 10 16 45.9979 14.6128 1 1 -1 17 16.6146 9.49423 1 0 0 17 -73.518 40.2037 -2 0 0 17 -73.518 40.2037 1 1 0 17 6.38462 9.74881 1 2 0 17 174.387 20.3784 1 -1 1 17 -15.316 11.3072 1 0 1 17 48.7334 39.6836 -2 0 1 17 48.7334 39.6836 1 -1 1 16 -88.914 65.9701 -2 1 1 17 -88.914 65.9701 1 2 1 17 9.68237 10.3949 1 3 1 17 4.88569 12.1617 1 1 2 18 -102.10 69.5643 -2 -1 2 17 -102.10 69.5643 1 0 2 17 21.0038 30.4999 -2 0 2 17 21.0038 30.4999 1 -1 2 16 -14.251 46.1012 -2 1 2 17 -14.251 46.1012 1 2 2 17 -12.706 11.1951 1 -3 2 15 -88.953 78.9173 -2 3 2 17 -88.953 78.9173 1 1 3 18 -69.328 52.7033 -2 -1 3 17 -69.328 52.7033 1 0 3 17 -7.9892 28.9380 -2 0 3 17 -7.9892 28.9380 1 -1 3 16 -65.189 74.7219 -2 1 3 17 -65.189 74.7219 1 2 3 17 -14.267 10.9044 1 3 3 17 28.9682 14.1886 1 1 4 18 -24.985 58.8513 -2 -1 4 17 -24.985 58.8513 1 0 4 17 -25.285 28.6588 -2 0 4 17 -25.285 28.6588 1 -1 4 16 -23.736 53.2130 -2 1 4 17 -23.736 53.2130 1 2 4 17 2.71112 6.73705 1 -3 4 15 -89.655 72.7475 -2 3 4 17 -89.655 72.7475 1 1 5 18 -44.322 58.4061 -2 -1 5 17 -44.322 58.4061 1 0 5 17 46.3741 61.6786 -2 0 5 17 46.3741 61.6786 1 -1 5 16 142.547 48.1664 -2 1 5 17 142.547 48.1664 1 2 5 17 -17.178 11.5658 1 -3 5 15 -102.99 119.358 -2 3 5 17 -102.99 119.358 1 1 6 18 86.2692 60.3399 -2 -1 6 17 86.2692 60.3399 1 0 6 17 -25.455 35.2398 -2 0 6 17 -25.455 35.2398 1 1 6 17 4.35164 8.03514 1 2 6 17 10.9821 14.5314 1 -3 6 15 4.51839 55.3723 -2 3 6 17 4.51839 55.3723 1 -1 7 17 -23.726 28.0190 1 0 7 17 -51.717 36.4827 -2 0 7 17 -51.717 36.4827 1 -1 7 16 -78.361 65.3275 -2 1 7 17 -78.361 65.3275 1 -2 7 16 -6.2770 80.6870 -2 2 7 17 -6.2770 80.6870 1 3 7 17 44.8989 9.18238 1 0 8 17 -79.367 32.4465 -2 0 8 17 -79.367 32.4465 1 -1 8 16 -17.570 62.7511 -2 1 8 17 -17.570 62.7511 1 2 8 17 -16.878 7.45951 1 0 9 17 -149.63 102.144 -2 0 9 17 -149.63 102.144 1 -1 9 16 42.4992 55.0091 -2 1 9 17 42.4992 55.0091 1 -1 2 17 -26.728 95.0191 -2 1 2 18 -26.728 95.0191 1 2 2 18 -7.9087 12.3866 1 0 3 18 15.4256 44.0489 -2 0 3 18 15.4256 44.0489 1 -1 3 17 28.3100 55.6227 -2 1 3 18 28.3100 55.6227 1 2 3 18 -7.9173 10.3547 1 0 4 18 16.1667 35.2010 -2 0 4 18 16.1667 35.2010 1 -1 4 17 -69.278 46.3284 -2 1 4 18 -69.278 46.3284 1 2 4 18 8.02022 11.4326 1 0 5 18 3.40668 42.5415 -2 0 5 18 3.40668 42.5415 1 -1 5 17 -45.802 50.6526 -2 1 5 18 -45.802 50.6526 1 2 5 18 -38.591 13.9115 1 0 6 18 39.1846 50.8400 -2 0 6 18 39.1846 50.8400 1 -1 6 17 -83.170 45.8414 -2 1 6 18 -83.170 45.8414 1 2 6 18 -12.913 10.1690 1 1 7 18 -21.207 10.8678 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 78285 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.8467(6) 0.0770(3) 0.7315(3) 0.0382(10) Uani 1 1 d . . . . . Cl3 Cl 0.9033(7) 0.1396(4) 0.5685(3) 0.0432(12) Uani 1 1 d . . . . . Cl1 Cl 0.7892(7) 0.0160(3) 0.8900(3) 0.0427(11) Uani 1 1 d . . . . . O1 O 1.0047(16) 0.3263(10) 0.3103(7) 0.039(3) Uani 1 1 d . U . . . H1 H 0.987926 0.390577 0.267942 0.058 Uiso 1 1 calc R U . . . O2 O 1.0525(16) 0.5224(9) 0.1885(7) 0.037(3) Uani 1 1 d . U . . . N2 N 0.885(2) 0.5907(12) 0.1544(9) 0.036(3) Uani 1 1 d . U . . . N1 N 0.805(2) 0.2634(11) 0.3425(8) 0.033(3) Uani 1 1 d . U . . . C19 C 0.878(3) 0.2504(14) 0.0903(10) 0.035(4) Uani 1 1 d . U . . . H19 H 1.003033 0.213678 0.066210 0.042 Uiso 1 1 calc R U . . . C18 C 0.905(2) 0.3665(14) 0.0913(10) 0.033(4) Uani 1 1 d . U . . . H18 H 1.047851 0.408178 0.071038 0.040 Uiso 1 1 calc R U . . . C7 C 0.449(2) 0.5121(14) 0.3440(10) 0.032(4) Uani 1 1 d . U . . . H7 H 0.329163 0.478321 0.324900 0.038 Uiso 1 1 calc R U . . . C16 C 0.717(2) 0.5522(13) 0.1195(10) 0.030(3) Uani 1 1 d . U . . . C17 C 0.715(2) 0.4218(13) 0.1235(10) 0.028(3) Uani 1 1 d . U . . . C22 C 0.504(2) 0.3592(14) 0.1520(10) 0.030(4) Uani 1 1 d . U . . . H22 H 0.373924 0.396877 0.171155 0.037 Uiso 1 1 calc R U . . . C4 C 0.424(2) 0.2414(14) 0.4080(11) 0.036(4) Uani 1 1 d . U . . . H4 H 0.290613 0.274072 0.430281 0.043 Uiso 1 1 calc R U . . . C11 C 0.796(2) 0.4894(14) 0.4058(10) 0.030(4) Uani 1 1 d . U . . . H11 H 0.916712 0.441515 0.428022 0.036 Uiso 1 1 calc R U . . . C21 C 0.491(3) 0.2413(14) 0.1512(11) 0.036(4) Uani 1 1 d . U . . . H21 H 0.350420 0.197944 0.170859 0.043 Uiso 1 1 calc R U . . . C9 C 0.608(3) 0.6765(15) 0.3747(11) 0.041(4) Uani 1 1 d . U . . . H9 H 0.601126 0.756952 0.376382 0.049 Uiso 1 1 calc R U . . . C6 C 0.623(3) 0.4415(14) 0.3725(10) 0.036(4) Uani 1 1 d . U . . . C8 C 0.441(2) 0.6307(14) 0.3422(10) 0.034(4) Uani 1 1 d . U . . . H8 H 0.322487 0.679445 0.318827 0.041 Uiso 1 1 calc R U . . . C1 C 0.805(3) 0.1456(16) 0.3434(11) 0.043(4) Uani 1 1 d . U . . . H1A H 0.939915 0.112745 0.322613 0.052 Uiso 1 1 calc R U . . . C15 C 0.560(3) 0.6293(14) 0.0843(10) 0.035(4) Uani 1 1 d . U . . . H15 H 0.442958 0.602803 0.059044 0.042 Uiso 1 1 calc R U . . . C5 C 0.620(3) 0.3149(14) 0.3751(10) 0.033(4) Uani 1 1 d . U . . . C12 C 0.907(3) 0.7082(15) 0.1544(11) 0.036(4) Uani 1 1 d . U . . . H12 H 1.029392 0.734296 0.176745 0.043 Uiso 1 1 calc R U . . . C13 C 0.741(2) 0.7876(15) 0.1203(10) 0.036(4) Uani 1 1 d . U . . . H13 H 0.747404 0.868252 0.121285 0.043 Uiso 1 1 calc R U . . . C14 C 0.570(3) 0.7483(15) 0.0853(11) 0.042(4) Uani 1 1 d . U . . . H14 H 0.458423 0.802118 0.061639 0.050 Uiso 1 1 calc R U . . . C20 C 0.677(3) 0.1853(16) 0.1227(11) 0.046(4) Uani 1 1 d . U . . . H20 H 0.666326 0.103334 0.125350 0.056 Uiso 1 1 calc R U . . . C10 C 0.785(2) 0.6081(15) 0.4051(10) 0.035(4) Uani 1 1 d . U . . . H10 H 0.900278 0.642655 0.425788 0.042 Uiso 1 1 calc R U . . . C3 C 0.418(3) 0.1231(15) 0.4095(11) 0.041(4) Uani 1 1 d . U . . . H3 H 0.283283 0.074346 0.434201 0.050 Uiso 1 1 calc R U . . . C2 C 0.611(3) 0.0763(15) 0.3742(10) 0.040(4) Uani 1 1 d . U . . . H2 H 0.607122 -0.003644 0.371656 0.048 Uiso 1 1 calc R U . . . 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 Cl2 0.039(2) 0.029(2) 0.045(2) -0.0111(18) -0.0026(19) -0.002(2) Cl3 0.046(2) 0.032(3) 0.048(3) -0.009(2) -0.002(2) -0.004(2) Cl1 0.049(3) 0.029(2) 0.049(3) -0.011(2) -0.005(2) 0.002(2) O1 0.030(5) 0.038(6) 0.048(6) -0.010(5) -0.008(5) 0.004(5) O2 0.028(5) 0.042(6) 0.036(5) -0.005(5) -0.006(4) 0.002(5) N2 0.031(5) 0.037(5) 0.037(5) -0.006(4) -0.007(4) 0.005(4) N1 0.032(5) 0.032(5) 0.033(5) -0.006(4) -0.008(4) -0.001(4) C19 0.035(5) 0.035(6) 0.032(5) -0.009(4) -0.005(4) 0.007(4) C18 0.034(5) 0.029(6) 0.035(5) -0.009(4) -0.005(4) 0.002(4) C7 0.030(5) 0.032(6) 0.034(5) -0.014(4) 0.003(4) 0.003(4) C16 0.029(5) 0.027(5) 0.033(5) -0.009(4) -0.006(4) 0.002(4) C17 0.027(5) 0.027(5) 0.030(5) -0.010(4) -0.003(4) -0.002(4) C22 0.028(5) 0.034(6) 0.029(5) -0.011(4) -0.002(4) 0.003(4) C4 0.035(5) 0.035(6) 0.039(5) -0.012(4) -0.006(4) 0.000(4) C11 0.033(5) 0.029(5) 0.028(5) -0.006(4) -0.008(4) 0.002(4) C21 0.035(5) 0.031(6) 0.040(6) -0.010(4) -0.001(4) 0.000(4) C9 0.045(6) 0.037(6) 0.043(6) -0.016(4) -0.004(4) 0.000(4) C6 0.037(5) 0.033(6) 0.039(5) -0.015(4) -0.004(4) 0.004(4) C8 0.038(5) 0.030(6) 0.034(5) -0.010(4) -0.006(4) 0.007(4) C1 0.042(6) 0.042(6) 0.044(6) -0.013(4) -0.002(4) 0.006(4) C15 0.038(5) 0.034(6) 0.034(5) -0.014(4) -0.002(4) 0.007(4) C5 0.032(5) 0.032(5) 0.032(5) -0.009(4) -0.002(4) 0.004(4) C12 0.036(5) 0.033(6) 0.038(6) -0.014(4) 0.002(4) -0.007(4) C13 0.034(5) 0.035(6) 0.040(5) -0.012(4) -0.010(4) 0.000(4) C14 0.043(6) 0.041(6) 0.042(6) -0.014(4) -0.009(4) 0.004(4) C20 0.049(6) 0.043(6) 0.046(6) -0.015(4) -0.005(4) 0.004(5) C10 0.036(5) 0.034(6) 0.038(5) -0.016(4) -0.004(4) -0.004(4) C3 0.044(6) 0.040(6) 0.042(6) -0.015(4) -0.009(4) 0.001(4) C2 0.044(5) 0.037(6) 0.037(5) -0.011(4) -0.010(4) -0.001(4) 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Cl2 Cl3 179.6(2) . . ? N1 O1 H1 109.5 . . ? O2 N2 C16 124.7(13) . . ? O2 N2 C12 112.9(13) . . ? C16 N2 C12 122.3(13) . . ? O1 N1 C1 115.7(12) . . ? O1 N1 C5 120.8(13) . . ? C5 N1 C1 123.4(14) . . ? C18 C19 H19 118.6 . . ? C20 C19 H19 118.6 . . ? C20 C19 C18 122.8(15) . . ? C19 C18 H18 121.1 . . ? C19 C18 C17 117.9(15) . . ? C17 C18 H18 121.1 . . ? C6 C7 H7 118.9 . . ? C6 C7 C8 122.2(15) . . ? C8 C7 H7 118.9 . . ? N2 C16 C17 116.6(12) . . ? C15 C16 N2 120.0(14) . . ? C15 C16 C17 123.3(14) . . ? C18 C17 C16 123.3(14) . . ? C22 C17 C18 120.2(13) . . ? C22 C17 C16 116.1(13) . . ? C17 C22 H22 120.8 . . ? C21 C22 C17 118.3(14) . . ? C21 C22 H22 120.8 . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C3 C4 C5 122.3(15) . . ? C6 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? C10 C11 C6 118.0(14) . . ? C22 C21 H21 119.1 . . ? C20 C21 C22 121.9(16) . . ? C20 C21 H21 119.1 . . ? C8 C9 H9 119.4 . . ? C8 C9 C10 121.1(16) . . ? C10 C9 H9 119.4 . . ? C7 C6 C11 119.2(15) . . ? C7 C6 C5 119.7(15) . . ? C11 C6 C5 121.0(14) . . ? C7 C8 H8 120.8 . . ? C9 C8 C7 118.5(14) . . ? C9 C8 H8 120.8 . . ? N1 C1 H1A 120.3 . . ? C2 C1 N1 119.4(15) . . ? C2 C1 H1A 120.3 . . ? C16 C15 H15 120.1 . . ? C16 C15 C14 119.8(15) . . ? C14 C15 H15 120.1 . . ? N1 C5 C4 116.0(14) . . ? N1 C5 C6 122.2(15) . . ? C4 C5 C6 121.7(14) . . ? N2 C12 H12 121.1 . . ? N2 C12 C13 117.8(14) . . ? C13 C12 H12 121.1 . . ? C12 C13 H13 120.2 . . ? C14 C13 C12 119.7(15) . . ? C14 C13 H13 120.2 . . ? C15 C14 H14 119.9 . . ? C13 C14 C15 120.3(15) . . ? C13 C14 H14 119.9 . . ? C19 C20 C21 118.7(16) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C11 C10 H10 119.5 . . ? C9 C10 C11 120.9(15) . . ? C9 C10 H10 119.5 . . ? C4 C3 H3 120.5 . . ? C4 C3 C2 118.9(16) . . ? C2 C3 H3 120.5 . . ? C1 C2 C3 119.8(16) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl2 Cl3 2.337(6) . ? Cl2 Cl1 2.272(6) . ? O1 H1 0.8400 . ? O1 N1 1.359(14) . ? O2 N2 1.343(14) . ? N2 C16 1.359(17) . ? N2 C12 1.382(19) . ? N1 C1 1.375(19) . ? N1 C5 1.367(18) . ? C19 H19 0.9500 . ? C19 C18 1.38(2) . ? C19 C20 1.37(2) . ? C18 H18 0.9500 . ? C18 C17 1.413(19) . ? C7 H7 0.9500 . ? C7 C6 1.368(19) . ? C7 C8 1.38(2) . ? C16 C17 1.507(19) . ? C16 C15 1.353(19) . ? C17 C22 1.412(18) . ? C22 H22 0.9500 . ? C22 C21 1.39(2) . ? C4 H4 0.9500 . ? C4 C5 1.395(19) . ? C4 C3 1.38(2) . ? C11 H11 0.9500 . ? C11 C6 1.418(19) . ? C11 C10 1.39(2) . ? C21 H21 0.9500 . ? C21 C20 1.38(2) . ? C9 H9 0.9500 . ? C9 C8 1.369(19) . ? C9 C10 1.38(2) . ? C6 C5 1.47(2) . ? C8 H8 0.9500 . ? C1 H1A 0.9500 . ? C1 C2 1.37(2) . ? C15 H15 0.9500 . ? C15 C14 1.40(2) . ? C12 H12 0.9500 . ? C12 C13 1.40(2) . ? C13 H13 0.9500 . ? C13 C14 1.376(19) . ? C14 H14 0.9500 . ? C20 H20 0.9500 . ? C10 H10 0.9500 . ? C3 H3 0.9500 . ? C3 C2 1.39(2) . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 C1 C2 -179.7(13) . . . . ? O1 N1 C5 C4 -178.9(12) . . . . ? O1 N1 C5 C6 3(2) . . . . ? O2 N2 C16 C17 3(2) . . . . ? O2 N2 C16 C15 -178.1(12) . . . . ? O2 N2 C12 C13 -180.0(13) . . . . ? N2 C16 C17 C18 -50.2(19) . . . . ? N2 C16 C17 C22 136.8(14) . . . . ? N2 C16 C15 C14 -1(2) . . . . ? N2 C12 C13 C14 -2(2) . . . . ? N1 C1 C2 C3 -4(2) . . . . ? C19 C18 C17 C16 -173.8(12) . . . . ? C19 C18 C17 C22 -1(2) . . . . ? C18 C19 C20 C21 5(2) . . . . ? C18 C17 C22 C21 3(2) . . . . ? C7 C6 C5 N1 136.0(16) . . . . ? C7 C6 C5 C4 -42(2) . . . . ? C16 N2 C12 C13 3(2) . . . . ? C16 C17 C22 C21 176.0(12) . . . . ? C16 C15 C14 C13 1(2) . . . . ? C17 C16 C15 C14 178.4(14) . . . . ? C17 C22 C21 C20 -1(2) . . . . ? C22 C21 C20 C19 -3(2) . . . . ? C4 C3 C2 C1 3(2) . . . . ? C11 C6 C5 N1 -49(2) . . . . ? C11 C6 C5 C4 133.4(16) . . . . ? C6 C7 C8 C9 -4(2) . . . . ? C6 C11 C10 C9 1(2) . . . . ? C8 C7 C6 C11 3(2) . . . . ? C8 C7 C6 C5 178.6(14) . . . . ? C8 C9 C10 C11 -2(2) . . . . ? C1 N1 C5 C4 -2(2) . . . . ? C1 N1 C5 C6 -179.4(13) . . . . ? C15 C16 C17 C18 130.5(17) . . . . ? C15 C16 C17 C22 -43(2) . . . . ? C5 N1 C1 C2 3(2) . . . . ? C5 C4 C3 C2 -2(2) . . . . ? C12 N2 C16 C17 179.6(13) . . . . ? C12 N2 C16 C15 -1(2) . . . . ? C12 C13 C14 C15 0(2) . . . . ? C20 C19 C18 C17 -3(2) . . . . ? C10 C11 C6 C7 -2(2) . . . . ? C10 C11 C6 C5 -177.3(14) . . . . ? C10 C9 C8 C7 3(2) . . . . ? C3 C4 C5 N1 1(2) . . . . ? C3 C4 C5 C6 179.0(13) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.77152 2 0.22848