#------------------------------------------------------------------------------ #$Date: 2024-10-22 01:10:36 +0300 (Tue, 22 Oct 2024) $ #$Revision: 295572 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572912.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_1572912 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, 2(C7 H9 N O), C14 H19 N2 O2' _chemical_formula_sum 'C28 H37 Cl3 N4 O4' _chemical_formula_weight 599.96 _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 mixed _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 85.903(9) _cell_angle_beta 88.725(7) _cell_angle_gamma 66.463(8) _cell_formula_units_Z 1 _cell_length_a 7.3618(17) _cell_length_b 8.291(2) _cell_length_c 13.265(3) _cell_measurement_reflns_used 2400 _cell_measurement_temperature 100.00 _cell_measurement_theta_max 26.298 _cell_measurement_theta_min 2.686 _cell_volume 740.4(3) _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 'XL (Sheldrick, 2008)' _computing_structure_solution 'olex2.solve 1.5-alpha (Bourhis et al., 2015)' _diffrn_ambient_temperature 100.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.992 _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 0.1199 _diffrn_reflns_av_unetI/netI 0.0735 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3040 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.457 _diffrn_reflns_theta_min 2.686 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.349 _exptl_absorpt_correction_T_max 0.745372 _exptl_absorpt_correction_T_min 0.621617 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. For component 1: wR2(int) was 0.0959 before and 0.0784 after correction. The Ratio of minimum to maximum transmission is 0.83. Final HKLF 4 output contains 28271 reflections, Rint = 0.1199 (7415 with I > 3sig(I), Rint = 0.0687) ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.346 _exptl_crystal_description plate _exptl_crystal_F_000 316 _exptl_crystal_size_max 0.261 _exptl_crystal_size_mid 0.093 _exptl_crystal_size_min 0.053 _refine_diff_density_max 0.400 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.079 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 184 _refine_ls_number_reflns 3040 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.1128 _refine_ls_R_factor_gt 0.0600 _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^)+(0.0550P)^2^+0.9600P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1249 _refine_ls_wR_factor_ref 0.1578 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1994 _reflns_number_total 3040 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc06270a3.cif _cod_data_source_block OGH_D49_35 _cod_database_code 1572912 _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 0.982 _shelx_estimated_absorpt_t_min 0.914 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.9043 0.0957 2.a Aromatic/amide H refined with riding coordinates: C2(H2A), C5(H5), C9(H9), C4(H4), C12(H12), C11(H11) 2.b Idealised Me refined as rotating group: C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C) ; _shelx_res_file ; TITL full1_P-1_a.res in P-1 ogh_d49_35.res created by SHELXL-2019/1 at 11:26:02 on 11-Sep-2024 REM Old TITL full1_P-1 in P-1 REM SHELXT solution in P-1: R1 0.157, Rweak 0.019, Alpha 0.044 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C28 Cl3 N4 O4 CELL 0.71073 7.3618 8.291 13.2649 85.903 88.725 66.463 ZERR 1 0.0017 0.0022 0.0033 0.009 0.007 0.008 LATT 1 SFAC C H Cl N O UNIT 28 37 3 4 4 L.S. 10 PLAN 2 SIZE 0.053 0.093 0.261 TEMP -173.15 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 acta MERG 0 REM REM REM WGHT 0.055000 0.960000 BASF 0.09570 FVAR 1.17637 CL2 3 0.500000 1.000000 1.000000 10.50000 0.03372 0.03117 = 0.03253 -0.00474 -0.00671 -0.01107 CL1 3 0.776424 0.746797 1.032508 11.00000 0.03957 0.03655 = 0.04153 -0.00711 -0.01159 -0.00451 O1 5 0.671412 0.399931 0.628519 11.00000 0.03650 0.02036 = 0.02977 -0.00300 -0.00325 -0.01043 O2 5 -0.106650 0.955823 0.556016 11.00000 0.02870 0.04539 = 0.02160 0.00827 -0.00913 -0.01527 N1 4 0.621031 0.565969 0.647922 11.00000 0.02443 0.02409 = 0.02021 0.00109 -0.00192 -0.00998 N2 4 -0.014171 0.894323 0.647220 11.00000 0.02445 0.02834 = 0.02082 0.00419 -0.00477 -0.01130 C2 1 0.624304 0.781108 0.755182 11.00000 0.02187 0.02594 = 0.02356 -0.00065 -0.00315 -0.00775 AFIX 43 H2A 2 0.665438 0.808374 0.816779 11.00000 -1.20000 AFIX 0 C5 1 0.510469 0.697396 0.579247 11.00000 0.02312 0.03131 = 0.02455 0.00604 -0.00562 -0.01197 AFIX 43 H5 2 0.471804 0.668193 0.517579 11.00000 -1.20000 AFIX 0 C8 1 0.081789 0.717937 0.667013 11.00000 0.02295 0.02540 = 0.02617 -0.00234 0.00360 -0.01038 C10 1 0.163975 0.775015 0.832513 11.00000 0.02489 0.03238 = 0.02431 0.00306 -0.00311 -0.01486 C3 1 0.511189 0.918758 0.687182 11.00000 0.02177 0.02417 = 0.02964 0.00198 0.00061 -0.00871 C1 1 0.678681 0.606940 0.736375 11.00000 0.02394 0.02762 = 0.02086 0.00040 -0.00191 -0.01023 C9 1 0.169584 0.659804 0.760665 11.00000 0.02544 0.02551 = 0.02634 0.00091 -0.00054 -0.01229 AFIX 43 H9 2 0.236242 0.536576 0.776561 11.00000 -1.20000 AFIX 0 C4 1 0.454974 0.869711 0.598043 11.00000 0.02198 0.03422 = 0.02856 0.00816 -0.00383 -0.01172 AFIX 43 H4 2 0.376233 0.958846 0.549548 11.00000 -1.20000 AFIX 0 C12 1 -0.026038 1.012566 0.714207 11.00000 0.02697 0.02102 = 0.02880 -0.00093 -0.00052 -0.00806 AFIX 43 H12 2 -0.095159 1.135142 0.697078 11.00000 -1.20000 AFIX 0 C11 1 0.062563 0.954827 0.807662 11.00000 0.03165 0.03000 = 0.02357 -0.00466 0.00035 -0.01279 AFIX 43 H11 2 0.054566 1.037678 0.855288 11.00000 -1.20000 AFIX 0 C14 1 0.264047 0.708917 0.933557 11.00000 0.03919 0.04023 = 0.02408 0.00396 -0.00753 -0.01907 AFIX 137 H14A 2 0.393907 0.715831 0.932192 11.00000 -1.50000 H14B 2 0.281265 0.586156 0.948455 11.00000 -1.50000 H14C 2 0.182261 0.781641 0.985952 11.00000 -1.50000 AFIX 0 C13 1 0.080541 0.601684 0.587265 11.00000 0.04162 0.03639 = 0.02873 -0.00778 0.00279 -0.02061 AFIX 137 H13A 2 0.147008 0.626287 0.526937 11.00000 -1.50000 H13B 2 -0.056617 0.623876 0.570213 11.00000 -1.50000 H13C 2 0.150407 0.478102 0.611970 11.00000 -1.50000 AFIX 0 C6 1 0.799654 0.455920 0.806827 11.00000 0.03626 0.02685 = 0.02488 0.00090 -0.00841 -0.00866 AFIX 137 H6A 2 0.727085 0.380961 0.823398 11.00000 -1.50000 H6B 2 0.826254 0.500457 0.868872 11.00000 -1.50000 H6C 2 0.925306 0.386865 0.774617 11.00000 -1.50000 AFIX 0 C7 1 0.450329 1.107860 0.707903 11.00000 0.03909 0.03152 = 0.03790 0.00155 0.00133 -0.01459 AFIX 137 H7A 2 0.473719 1.116301 0.779401 11.00000 -1.50000 H7B 2 0.309200 1.172805 0.692037 11.00000 -1.50000 H7C 2 0.528124 1.158587 0.665872 11.00000 -1.50000 AFIX 0 H2 2 0.000000 1.000000 0.500000 10.50000 0.07814 HKLF 5 REM full1_P-1_a.res in P-1 REM wR2 = 0.1578, GooF = S = 1.059, Restrained GooF = 1.059 for all data REM R1 = 0.0600 for 1994 Fo > 4sig(Fo) and 0.1128 for all 3040 data REM 184 parameters refined using 0 restraints END WGHT 0.0548 0.9681 REM Highest difference peak 0.400, deepest hole -0.442, 1-sigma level 0.079 Q1 1 0.9442 0.5069 0.9346 11.00000 0.05 0.40 Q2 1 0.6466 0.7028 1.0612 11.00000 0.05 0.39 ; _shelx_res_checksum 88515 _shelx_hkl_file ; 1 0 0 16.0045 7.74503 -2 1 0 0 16.0045 7.74503 1 2 0 0 569.240 37.2215 -2 2 0 0 569.240 37.2215 1 3 0 0 416.679 11.5733 1 4 0 0 344.946 14.8358 1 -5 0 1 86.6258 27.1609 -2 5 0 0 86.6258 27.1609 1 -6 0 1 147.197 25.5370 -2 6 0 0 147.197 25.5370 1 -7 0 1 348.381 18.6111 -2 7 0 0 348.381 18.6111 1 -8 0 1 13.0084 15.8640 -2 8 0 0 13.0084 15.8640 1 -8 1 1 174.081 48.9896 -2 -8 1 0 174.081 48.9896 1 -7 1 1 32.1117 17.4442 -2 -7 1 0 32.1117 17.4442 1 -6 1 1 160.609 17.1228 -2 -6 1 0 160.609 17.1228 1 -5 1 0 1.68201 5.67586 1 -4 1 0 179.652 24.7648 -2 -4 1 0 179.652 24.7648 1 -3 1 0 962.139 31.1092 -2 -3 1 0 962.139 31.1092 1 -2 1 0 2074.72 38.9913 -2 -2 1 0 2074.72 38.9913 1 -1 1 0 41.3499 8.86646 -2 -1 1 0 41.3499 8.86646 1 0 1 0 524.410 10.2552 1 1 1 0 11.6504 1.83886 1 -3 -1 1 65.7876 23.6688 -2 3 1 0 65.7876 23.6688 1 -4 -1 1 1124.70 44.7628 -2 4 1 0 1124.70 44.7628 1 -5 -1 1 288.351 26.3155 -2 5 1 0 288.351 26.3155 1 -6 -1 1 83.4011 9.96100 -2 6 1 0 83.4011 9.96100 1 -7 -1 1 72.4426 14.1095 -2 7 1 0 72.4426 14.1095 1 8 1 0 213.794 17.7450 1 -7 2 1 32.8807 37.6777 -2 -7 2 0 32.8807 37.6777 1 -6 2 0 80.9983 20.0351 -2 -6 2 0 80.9983 20.0351 1 -5 2 0 186.312 21.7236 -2 -5 2 0 186.312 21.7236 1 -4 2 0 17.4071 12.3458 -2 -4 2 0 17.4071 12.3458 1 -3 2 0 174.861 9.66115 -2 -3 2 0 174.861 9.66115 1 -2 2 0 3774.30 90.4636 -2 -2 2 0 3774.30 90.4636 1 -1 2 0 800.086 20.0595 1 0 2 0 18.3711 4.59785 1 1 2 0 691.689 13.4073 1 -2 -2 1 2240.73 41.2048 -2 2 2 0 2240.73 41.2048 1 -3 -2 1 99.8895 6.72757 -2 3 2 0 99.8895 6.72757 1 -4 -2 1 176.110 29.9461 -2 4 2 0 176.110 29.9461 1 -5 -2 1 319.074 27.2848 -2 5 2 0 319.074 27.2848 1 6 2 0 105.403 16.2661 1 7 2 0 -12.869 10.4305 1 8 2 0 5.16214 2.90571 1 -7 3 0 -28.900 27.3266 -2 -7 3 0 -28.900 27.3266 1 -6 3 0 40.0390 34.9413 -2 -6 3 0 40.0390 34.9413 1 -5 3 0 461.692 26.8921 -2 -5 3 0 461.692 26.8921 1 -4 3 0 225.445 13.4278 -2 -4 3 0 225.445 13.4278 1 -3 3 0 162.997 19.3791 -2 -3 3 0 162.997 19.3791 1 -2 3 0 138.113 10.0804 1 1 -3 1 104.912 36.8171 -2 -1 3 0 104.912 36.8171 1 0 -3 1 1240.36 65.7036 -2 0 3 0 1240.36 65.7036 1 -1 -3 1 1238.02 43.9310 -2 1 3 0 1238.02 43.9310 1 -2 -3 1 379.581 31.1674 -2 2 3 0 379.581 31.1674 1 -3 -3 1 848.814 38.9466 -2 3 3 0 848.814 38.9466 1 4 3 0 21.9116 4.86968 1 5 3 0 227.330 10.0058 1 6 3 0 329.876 10.7590 1 -7 -3 2 134.045 33.9729 -2 7 3 0 134.045 33.9729 1 -8 -3 2 -11.260 23.4112 -2 8 3 0 -11.260 23.4112 1 -9 -3 2 -30.934 30.0230 -2 9 3 0 -30.934 30.0230 1 -6 4 0 106.152 25.1051 -2 -6 4 0 106.152 25.1051 1 -5 4 0 122.021 27.9021 -2 -5 4 0 122.021 27.9021 1 4 -4 1 176.969 47.8470 -2 -4 4 0 176.969 47.8470 1 3 -4 1 360.496 30.9546 -2 -3 4 0 360.496 30.9546 1 2 -4 1 26.2231 15.1786 -2 -2 4 0 26.2231 15.1786 1 1 -4 1 128.193 15.7452 -2 -1 4 0 128.193 15.7452 1 0 -4 1 617.813 24.8291 -2 0 4 0 617.813 24.8291 1 -1 -4 1 284.097 35.5577 -2 1 4 0 284.097 35.5577 1 2 4 0 1088.00 23.9615 1 3 4 0 394.850 12.7631 1 4 4 0 471.159 16.9919 1 -5 -4 2 47.6389 19.9080 -2 5 4 0 47.6389 19.9080 1 6 4 0 19.5902 15.1531 1 -7 -4 2 443.913 48.4722 -2 7 4 0 443.913 48.4722 1 -8 -4 2 285.197 22.0820 -2 8 4 0 285.197 22.0820 1 9 4 0 26.5501 6.71460 1 5 -5 1 -20.427 29.3618 -2 -5 5 0 -20.427 29.3618 1 4 -5 1 292.106 23.8873 -2 -4 5 0 292.106 23.8873 1 3 -5 1 96.6509 17.8930 -2 -3 5 0 96.6509 17.8930 1 2 -5 1 143.619 20.0810 -2 -2 5 0 143.619 20.0810 1 1 -5 1 183.921 19.0034 -2 -1 5 0 183.921 19.0034 1 0 5 0 86.2543 8.71654 1 1 5 0 386.725 15.1254 1 2 5 0 49.3423 6.89379 1 -3 -5 2 435.648 18.6099 -2 3 5 0 435.648 18.6099 1 -4 -5 2 52.5754 13.7104 -2 4 5 0 52.5754 13.7104 1 -5 -5 2 51.4915 21.4384 -2 5 5 0 51.4915 21.4384 1 6 5 0 53.0165 7.90059 1 7 5 0 12.7561 6.78689 1 8 5 0 29.7715 6.46997 1 9 5 0 29.7297 6.62813 1 4 -6 1 4.38566 16.7698 -2 -4 6 0 4.38566 16.7698 1 3 -6 1 32.8577 18.8840 -2 -3 6 0 32.8577 18.8840 1 2 -6 1 204.050 22.9562 -2 -2 6 0 204.050 22.9562 1 1 -6 1 9.27697 41.6687 -2 -1 6 0 9.27697 41.6687 1 0 6 0 420.124 16.8615 1 -1 -6 2 37.1296 20.8742 -2 1 6 0 37.1296 20.8742 1 -2 -6 2 279.463 25.1569 -2 2 6 0 279.463 25.1569 1 -3 -6 2 108.549 25.4430 -2 3 6 0 108.549 25.4430 1 4 6 0 7.62174 5.08979 1 5 6 0 45.4340 4.48724 1 6 6 0 163.958 13.0134 1 7 6 0 208.344 14.2169 1 8 6 0 46.8468 9.30450 1 9 6 0 13.7037 10.3319 1 3 -7 1 1.73131 30.1169 -2 -3 7 0 1.73131 30.1169 1 -2 7 0 5.47003 7.83407 1 1 -7 2 264.442 38.3256 -2 -1 7 0 264.442 38.3256 1 0 -7 2 195.587 33.6102 -2 0 7 0 195.587 33.6102 1 -1 -7 2 34.4115 30.6780 -2 1 7 0 34.4115 30.6780 1 2 7 0 113.431 12.2355 1 3 7 0 88.1728 11.5306 1 4 7 0 7.23385 6.69379 1 5 7 0 12.1499 6.40607 1 6 7 0 70.0695 9.38935 1 7 7 0 0.86015 7.10342 1 8 7 0 44.7967 12.9219 1 2 -8 2 16.4841 38.2751 -2 -2 8 0 16.4841 38.2751 1 1 -8 2 11.6028 29.7917 -2 -1 8 0 11.6028 29.7917 1 0 -8 2 97.2410 31.7157 -2 0 8 0 97.2410 31.7157 1 -1 -8 2 71.3658 48.7075 -2 1 8 0 71.3658 48.7075 1 2 8 0 32.4304 9.94021 1 3 8 0 47.3045 9.72704 1 4 8 0 642.224 22.9370 1 5 8 0 140.875 11.2684 1 6 8 0 17.3153 9.62335 1 -7 -8 3 -23.231 35.3772 -2 7 8 0 -23.231 35.3772 1 8 8 0 14.9433 9.96324 1 0 -9 2 -77.592 49.8444 -2 0 9 0 -77.592 49.8444 1 1 9 0 109.501 13.6962 1 2 9 0 28.0685 8.77941 1 3 9 0 18.2042 12.3080 1 4 9 0 9.64250 8.62451 1 -5 -9 3 77.2083 46.3148 -2 5 9 0 77.2083 46.3148 1 6 9 0 85.3444 9.42459 1 7 9 0 112.877 14.9309 1 2 10 0 220.406 22.2102 1 -3 -10 3 48.9514 50.1734 -2 3 10 0 48.9514 50.1734 1 4 10 0 -15.907 8.98501 1 5 10 0 83.4016 13.4673 1 -5 -10 1 0.17116 10.2877 1 -4 -10 1 -19.306 9.38613 1 -3 -10 1 -22.125 10.4640 1 -2 -10 1 -33.682 14.5904 1 -7 -9 1 94.6230 17.0378 1 -6 -9 1 81.9000 9.86592 1 -5 -9 1 87.5403 12.0176 1 -4 -9 1 27.2493 10.0500 1 -3 -9 1 9.33662 9.63602 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11 9.04458 10.9014 1 -5 -6 11 -3.3676 9.96221 1 -4 -6 11 115.172 13.9232 1 -3 -6 11 6.53672 7.58057 1 -2 -6 11 -13.516 6.96578 1 -1 -6 11 -12.569 8.45684 1 0 -6 11 27.8904 10.0314 1 1 -6 11 44.6327 14.4503 1 -6 -5 11 78.7476 17.4066 1 -5 -5 11 11.7561 8.94858 1 -4 -5 11 -15.373 7.34422 1 -3 -5 11 33.4920 7.45863 1 -2 -5 11 130.088 9.79158 1 -1 -5 11 39.9733 8.30093 1 0 -5 11 -6.0734 6.86382 1 1 -5 11 153.721 14.2137 1 2 -5 11 -2.7173 8.58524 1 -6 -4 11 -8.4908 15.0229 1 -5 -4 11 33.4810 9.24059 1 -4 -4 11 -5.9321 9.93649 1 -3 -4 11 13.4947 7.68460 1 -2 -4 11 24.6663 6.96470 1 -1 -4 11 126.849 11.8097 1 0 -4 11 1.04186 8.32781 1 1 -4 11 6.59285 8.51365 1 2 -4 11 187.378 16.7260 1 3 -4 11 182.205 19.5414 1 -6 -3 11 3.81927 9.99585 1 -5 -3 11 13.2856 7.73355 1 -4 -3 11 104.140 12.7674 1 -3 -3 11 59.3225 10.7065 1 -2 -3 11 13.7247 6.73145 1 -1 -3 11 99.5082 9.63891 1 0 -3 11 87.3110 10.6217 1 1 -3 11 -2.4935 6.36023 1 2 -3 11 26.2772 8.05445 1 3 -3 11 45.8329 9.56542 1 4 -3 11 -20.204 12.4354 1 -6 -2 11 66.0952 13.0270 1 -5 -2 11 23.6764 7.69470 1 -4 -2 11 14.7656 9.79662 1 -3 -2 11 65.7252 6.62866 1 -2 -2 11 16.4603 6.65273 1 -1 -2 11 5.32033 6.97997 1 0 -2 11 1080.33 27.6207 1 1 -2 11 101.276 10.1875 1 2 -2 11 -0.5212 7.50741 1 3 -2 11 1.29556 7.20851 1 4 -2 11 77.1699 10.0601 1 5 -2 11 -4.9622 7.61698 1 -6 -1 11 5.61095 10.7572 1 -5 -1 11 55.9252 9.42465 1 -4 -1 11 2.18188 6.83324 1 -3 -1 11 175.058 13.6276 1 -2 -1 11 163.519 11.0424 1 -1 -1 11 63.6756 8.24553 1 0 -1 11 528.248 17.9204 1 1 -1 11 87.8023 8.79811 1 2 -1 11 743.804 23.8306 1 3 -1 11 68.4305 9.87499 1 4 -1 11 34.6381 8.87753 1 5 -1 11 48.7064 8.42368 1 -6 0 11 8.95274 13.4510 1 -5 0 11 4.72581 8.20009 1 -4 0 11 4.95068 6.98448 1 -3 0 11 31.5416 4.00563 1 -2 0 11 124.189 11.5344 1 -1 0 11 17.8761 6.39699 1 0 0 11 55.5766 7.51012 1 1 0 11 46.7544 7.79498 1 2 0 11 6.12222 5.61902 1 3 0 11 188.778 13.2989 1 4 0 11 77.2098 9.74941 1 6 1 10 -39.466 42.2758 -2 5 0 11 -39.466 42.2758 1 7 1 10 27.4878 44.6394 -2 6 0 11 27.4878 44.6394 1 -5 1 11 -9.7315 6.19072 1 -4 1 11 88.2917 10.2777 1 -3 1 11 1.20033 5.44374 1 -2 1 11 4.81237 6.02597 1 -1 1 11 12.2489 6.99303 1 0 1 11 1436.82 31.7246 1 1 1 11 642.148 19.1465 1 2 1 11 90.1751 8.68091 1 3 1 11 280.825 13.8522 1 4 1 11 -0.0594 6.52094 1 5 1 11 0.93828 5.85344 1 6 1 11 0.34754 8.48400 1 -5 2 11 8.82234 3.85265 1 -4 2 11 -2.1293 5.28810 1 -3 2 11 146.526 11.9081 1 -2 2 11 13.4164 6.21450 1 -1 2 11 6.33510 7.38213 1 0 2 11 327.444 18.6213 1 1 2 11 0.60617 7.87744 1 2 2 11 206.077 12.2743 1 3 2 11 49.5120 7.30505 1 4 2 11 370.998 15.5263 1 5 2 11 4.01127 4.13836 1 6 2 11 32.7436 12.8695 1 -4 3 11 10.8246 7.74379 1 -3 3 11 72.4634 9.04600 1 -2 3 11 103.692 9.52474 1 -1 3 11 16.3506 8.05289 1 0 3 11 10.3987 7.44261 1 1 3 11 360.489 20.7041 1 2 3 11 283.449 16.0835 1 3 3 11 42.2856 6.88213 1 4 3 11 -2.8578 6.76655 1 5 3 11 209.057 13.1386 1 6 3 11 -2.5242 11.4462 1 7 3 11 2.04571 11.7577 1 -4 4 11 17.8424 11.1251 1 -3 4 11 68.9515 10.3514 1 -2 4 11 208.673 14.6296 1 -1 4 11 10.2195 7.61322 1 0 4 11 3.63478 7.80499 1 1 4 11 27.1047 10.1684 1 2 4 11 234.298 17.4046 1 3 4 11 426.866 17.6633 1 4 4 11 37.3817 9.17780 1 6 5 9 96.5606 43.8818 -2 5 4 11 96.5606 43.8818 1 7 5 9 2.73010 40.8744 -2 6 4 11 2.73010 40.8744 1 7 4 11 -12.065 15.6513 1 -3 5 11 1.00891 10.2848 1 -2 5 11 23.4306 8.19910 1 -1 5 11 260.563 15.6842 1 0 5 11 666.039 25.0383 1 1 5 11 -16.462 7.97901 1 2 5 11 16.6264 8.68922 1 3 5 11 287.126 16.0545 1 4 5 11 17.6089 15.0529 1 6 6 9 -13.333 34.2144 -2 5 5 11 -13.333 34.2144 1 6 5 11 84.3017 13.5427 1 -2 6 11 3.49662 11.6652 1 -1 6 11 9.12195 8.52189 1 0 6 11 3.60156 7.96208 1 1 6 11 72.7201 10.6268 1 3 7 9 68.4483 48.5078 -2 2 6 11 68.4483 48.5078 1 3 6 11 -11.222 7.00254 1 4 6 11 76.7161 14.9503 1 5 6 11 27.0274 10.7775 1 6 6 11 16.8862 22.3688 1 0 7 11 7.07377 9.21709 1 1 7 11 102.334 13.4137 1 2 7 11 39.7332 11.9356 1 3 7 11 -16.337 8.25750 1 4 7 11 0.12703 12.3261 1 5 7 11 -11.705 12.2723 1 2 8 11 15.4166 9.31194 1 3 8 11 48.8312 9.73547 1 5 9 8 16.5498 53.8402 -2 4 8 11 16.5498 53.8402 1 -4 -6 12 4.15966 11.7449 1 -2 -4 14 156.076 64.2705 -2 -3 -6 12 156.076 64.2705 1 -2 -6 12 -5.4126 7.71983 1 -1 -6 12 1.36334 8.70734 1 0 -6 12 59.1716 11.7490 1 -5 -5 12 2.41923 10.9384 1 -4 -5 12 10.1548 11.0417 1 -3 -5 12 13.3194 8.45614 1 -2 -5 12 46.5148 7.67588 1 -1 -5 12 -0.9318 8.39816 1 0 -5 12 -2.0155 10.0591 1 1 -5 12 1.98296 9.98563 1 -5 -4 12 62.6913 12.5222 1 -4 -4 12 6.33034 9.39342 1 -3 -4 12 15.6414 7.31962 1 -2 -4 12 60.7705 9.40143 1 -1 -4 12 -0.7058 7.12705 1 0 -4 12 -11.495 6.79285 1 1 -4 12 -9.7638 8.37198 1 2 -4 12 76.4804 11.0850 1 3 -4 12 7.17919 10.4553 1 -6 -3 12 20.8378 12.8405 1 -5 -3 12 1.87831 7.95216 1 -4 -3 12 6.70979 8.60371 1 -3 -3 12 40.1202 8.97390 1 -2 -3 12 0.81929 6.86403 1 -1 -3 12 47.6370 8.83229 1 0 -3 12 211.458 16.3270 1 1 -3 12 33.8786 9.93047 1 2 -3 12 -7.1161 9.32698 1 3 -3 12 51.5240 13.4223 1 -6 -2 12 -41.116 26.6779 1 -5 -2 12 -4.2913 7.83431 1 -4 -2 12 12.1238 9.44342 1 -3 -2 12 19.5433 5.49357 1 -2 -2 12 116.550 10.2535 1 -1 -2 12 339.275 16.6425 1 0 -2 12 8.89788 6.98032 1 1 -2 12 8.21761 8.33815 1 2 -2 12 -0.1391 7.73819 1 3 -2 12 7.19020 8.67218 1 4 -2 12 216.796 17.3312 1 -6 -1 12 2.07309 12.3149 1 -5 -1 12 19.4542 10.2999 1 -4 -1 12 38.4388 9.09396 1 -3 -1 12 2.23247 3.66735 1 -2 -1 12 501.349 18.8967 1 -1 -1 12 18.4384 7.87848 1 0 -1 12 73.3805 8.62785 1 1 -1 12 86.0157 9.75039 1 2 -1 12 82.4016 10.0091 1 3 -1 12 9.01746 8.15668 1 4 -1 12 15.1159 8.58725 1 5 -1 12 132.343 13.2578 1 -5 0 12 103.153 12.7565 1 -4 0 12 -14.211 8.19044 1 -3 0 12 1.38363 3.35388 1 -2 0 12 68.5196 9.11795 1 -1 0 12 7.89863 7.44235 1 0 0 12 25.2757 6.04121 1 1 0 12 237.847 14.7317 1 2 0 12 262.954 14.0237 1 3 0 12 186.204 13.5091 1 4 0 12 24.1373 8.16471 1 5 0 12 15.4530 7.89339 1 -5 1 12 -3.9578 9.68871 1 -4 1 12 115.766 12.5340 1 -3 1 12 59.0994 8.57692 1 -2 1 12 291.128 16.1484 1 -1 1 12 870.467 28.5132 1 0 1 12 54.2193 8.58261 1 1 1 12 4.12001 6.88373 1 2 1 12 2.81732 6.61400 1 3 1 12 390.115 18.9472 1 4 1 12 2.47522 7.23287 1 5 1 12 31.7842 7.17776 1 6 1 12 39.7038 10.1492 1 -5 2 12 -3.3351 11.2819 1 -4 2 12 17.7849 7.92790 1 -3 2 12 17.0386 6.73928 1 -2 2 12 32.9840 6.89598 1 -1 2 12 191.265 15.2353 1 0 2 12 44.4024 10.4883 1 1 2 12 856.281 28.3650 1 2 2 12 109.370 10.8309 1 3 2 12 33.9693 6.49888 1 4 2 12 157.057 11.1763 1 5 2 12 -3.7601 7.79900 1 6 2 12 103.504 17.3407 1 -4 3 12 33.4611 8.80047 1 -3 3 12 521.927 20.2526 1 -2 3 12 147.425 12.6812 1 -1 3 12 -5.3803 10.3768 1 0 3 12 69.7720 15.0962 1 1 3 12 760.769 30.3395 1 2 3 12 28.6247 8.45986 1 3 3 12 32.3651 8.44547 1 4 3 12 20.6128 8.50108 1 5 3 12 88.8001 9.81196 1 6 3 12 44.5240 11.7797 1 -3 4 12 -2.9982 11.3432 1 -2 4 12 37.6761 9.01160 1 -1 4 12 882.323 29.3913 1 0 4 12 8.67565 9.04870 1 1 4 12 41.8201 12.5335 1 2 4 12 21.2507 8.47063 1 3 4 12 9.93818 6.77062 1 4 4 12 -1.2460 8.37434 1 6 5 10 -15.827 33.6996 -2 5 4 12 -15.827 33.6996 1 7 5 10 150.998 46.6196 -2 6 4 12 150.998 46.6196 1 -2 5 12 88.3696 12.7279 1 -1 5 12 56.1027 9.23049 1 0 5 12 31.5556 8.92431 1 1 5 12 -2.4990 8.25191 1 2 5 12 -4.5276 8.70695 1 3 5 12 230.449 19.8757 1 4 5 12 41.4523 12.2786 1 6 6 10 -47.087 44.8109 -2 5 5 12 -47.087 44.8109 1 6 5 12 -7.2541 10.0298 1 -1 6 12 -11.024 9.24065 1 0 6 12 1.21297 8.07896 1 1 6 12 203.317 15.1735 1 2 6 12 0.57047 8.26924 1 3 6 12 -3.7684 7.09401 1 5 7 10 80.8725 51.2781 -2 4 6 12 80.8725 51.2781 1 5 6 12 1.35310 11.3208 1 0 7 12 5.94790 10.9354 1 1 7 12 60.0564 11.0740 1 2 7 12 28.8857 12.5352 1 3 7 12 0.33152 8.31885 1 4 7 12 128.152 37.0837 1 -4 -5 13 -3.5694 10.0049 1 -3 -5 13 -4.1214 7.48785 1 -2 -5 13 -1.1205 10.1920 1 -1 -5 13 -9.7342 8.71198 1 0 -5 13 -3.2046 10.3718 1 -5 -4 13 -13.906 12.6337 1 -4 -4 13 -3.6984 10.4178 1 -3 -4 13 -7.3960 7.35699 1 -2 -4 13 31.9771 8.89539 1 -1 -4 13 24.1034 8.84497 1 0 -4 13 9.92797 7.85749 1 1 -4 13 -11.864 8.95844 1 2 -4 13 132.995 15.6805 1 -5 -3 13 22.2546 10.9844 1 -4 -3 13 139.628 14.8910 1 -3 -3 13 37.3747 12.2502 1 -2 -3 13 270.508 15.3761 1 -1 -3 13 219.332 14.2397 1 0 -3 13 31.3626 7.44006 1 1 -3 13 5.84296 8.03140 1 2 -3 13 26.9221 9.86649 1 3 -3 13 11.9642 10.4087 1 -5 -2 13 -8.7600 8.41933 1 -4 -2 13 20.2719 9.82280 1 -3 -2 13 278.191 13.0597 1 -2 -2 13 231.459 15.1197 1 -1 -2 13 537.602 22.6234 1 0 -2 13 3.06566 7.05932 1 1 -2 13 97.3636 9.82571 1 2 -2 13 5.15141 8.47752 1 3 -2 13 49.9836 13.2190 1 4 -2 13 326.191 25.1073 1 -4 1 14 147.177 40.7040 -2 -5 -1 13 147.177 40.7040 1 -4 -1 13 93.5876 14.5698 1 -3 -1 13 244.193 10.9876 1 -2 -1 13 7.39586 6.31683 1 -1 -1 13 24.7659 9.05258 1 0 -1 13 263.080 17.6438 1 1 -1 13 883.446 28.9690 1 2 -1 13 161.098 12.8130 1 3 -1 13 -3.3805 9.01227 1 4 -1 13 -1.3873 10.8180 1 -5 0 13 9.66539 10.5941 1 -4 0 13 -0.8427 8.25435 1 -3 0 13 147.858 8.10275 1 -2 0 13 47.4412 8.03838 1 -1 0 13 557.100 23.7942 1 0 0 13 82.8248 12.1421 1 1 0 13 -0.3528 7.88707 1 2 0 13 343.660 16.3695 1 3 0 13 2.39018 7.36198 1 4 0 13 3.77964 9.26149 1 5 0 13 58.5198 10.6333 1 -4 1 13 69.4775 10.9600 1 -3 1 13 -6.5198 6.49352 1 -2 1 13 22.2028 7.72764 1 -1 1 13 435.434 26.5849 1 0 1 13 9.92753 8.45890 1 1 1 13 1.18340 6.68289 1 2 1 13 3.70902 6.55057 1 3 1 13 335.080 16.9213 1 4 1 13 25.9651 8.17616 1 5 1 13 0.06169 7.68646 1 -4 2 13 -13.134 11.4046 1 -3 2 13 56.6982 9.04782 1 -2 2 13 -1.2878 8.74763 1 -1 2 13 19.4368 12.3454 1 0 2 13 48.1847 11.1246 1 1 2 13 43.8953 11.2249 1 2 2 13 0.77549 6.70735 1 3 2 13 -3.8461 6.27174 1 4 2 13 195.989 14.4923 1 5 2 13 55.4814 10.1206 1 -3 3 13 86.3015 11.0883 1 -2 3 13 45.8739 8.74109 1 -1 3 13 8.72230 8.53514 1 0 3 13 16.3063 8.79824 1 1 3 13 17.0190 11.7751 1 2 3 13 6.94397 9.04982 1 3 3 13 56.0481 7.72638 1 4 3 13 38.5792 10.6005 1 5 3 13 88.6846 13.3914 1 -3 4 13 55.0899 10.6632 1 -2 4 13 9.42169 8.13973 1 -1 4 13 10.9040 7.66324 1 0 4 13 -1.4300 8.93837 1 1 4 13 -2.5408 9.23511 1 2 4 13 189.293 15.0675 1 3 4 13 25.4496 11.6453 1 4 4 13 111.894 13.0847 1 5 4 13 11.7743 8.75588 1 -2 5 13 12.9040 14.1562 1 -1 5 13 40.0701 11.5706 1 0 5 13 45.1084 10.4360 1 1 5 13 24.2319 11.2613 1 2 5 13 0.29633 7.69210 1 3 5 13 215.271 19.4697 1 4 5 13 14.8632 12.6914 1 5 5 13 -8.9270 20.6604 1 0 6 13 42.3246 11.6653 1 1 6 13 8.01226 9.92411 1 2 6 13 -26.816 10.6328 1 3 6 13 125.394 12.7692 1 4 6 13 -13.589 18.0960 1 -3 -4 14 -10.611 7.64995 1 -2 -4 14 10.7056 9.23771 1 -1 -4 14 19.8069 10.1407 1 0 -4 14 -25.556 10.8018 1 1 -4 14 24.8974 14.4826 1 -4 -3 14 168.839 18.1989 1 -2 -1 15 -87.165 48.9725 -2 -3 -3 14 -87.165 48.9725 1 -2 -3 14 92.8754 11.0988 1 -1 -3 14 58.1228 9.45626 1 0 -3 14 -13.549 7.03318 1 1 -3 14 1.13349 8.99818 1 2 -3 14 -6.7087 9.93841 1 -4 -2 14 17.4746 14.4307 1 -3 -2 14 18.9355 5.56078 1 -2 -2 14 20.9670 7.12025 1 -1 -2 14 4.16322 8.28385 1 0 -2 14 446.301 18.4800 1 1 -2 14 -1.3083 7.95896 1 2 -2 14 29.4011 9.03198 1 3 -2 14 6.56480 11.6825 1 -4 -1 14 2.49172 12.9546 1 -3 -1 14 152.453 15.6252 1 -2 -1 14 6.84051 6.98968 1 -1 -1 14 235.124 15.7369 1 0 -1 14 9.22505 6.51196 1 1 -1 14 36.5213 7.91450 1 2 -1 14 -9.4061 6.53638 1 3 -1 14 -2.8761 8.35836 1 -4 0 14 145.095 19.1965 1 -3 0 14 187.746 9.21575 1 -2 0 14 195.144 12.7767 1 -1 0 14 27.9426 8.67233 1 0 0 14 -5.8972 6.67437 1 1 0 14 7.61682 6.58082 1 2 0 14 182.298 12.1710 1 3 0 14 -2.1071 8.37534 1 4 0 14 25.4520 12.7868 1 -4 1 14 11.6380 12.8420 1 -3 1 14 106.894 9.11779 1 -2 1 14 118.501 11.5651 1 -1 1 14 -5.5761 7.02754 1 0 1 14 117.075 12.0548 1 1 1 14 21.6939 7.90558 1 2 1 14 -0.5451 6.56436 1 3 1 14 93.9990 12.7753 1 4 1 14 162.146 14.2308 1 -3 2 14 10.0271 7.00174 1 -2 2 14 38.2363 8.40695 1 -1 2 14 21.0947 8.30139 1 0 2 14 85.5784 11.5864 1 1 2 14 -1.6847 7.52922 1 2 2 14 11.7577 7.38746 1 3 2 14 84.5050 10.6092 1 4 2 14 15.2977 9.18943 1 5 2 14 82.2103 12.6491 1 -3 3 14 3.52328 9.17666 1 -2 3 14 29.5105 8.93778 1 -1 3 14 -11.642 10.3778 1 0 3 14 90.7715 12.4728 1 1 3 14 399.780 21.8067 1 2 3 14 26.6695 8.35357 1 3 3 14 31.7823 7.49232 1 4 3 14 -16.670 9.07015 1 5 3 14 100.781 14.9278 1 -2 4 14 51.1680 10.7164 1 -1 4 14 6.73885 9.60447 1 0 4 14 19.5310 14.0266 1 1 4 14 -13.899 8.43300 1 2 4 14 72.6558 13.2596 1 3 4 14 85.0482 11.3425 1 4 4 14 -15.493 9.80710 1 -1 5 14 -18.220 10.9920 1 0 5 14 -4.3803 12.5771 1 1 5 14 20.4848 11.1436 1 2 5 14 2.37866 10.0852 1 3 5 14 76.5848 12.9158 1 4 5 14 -8.5395 11.1940 1 1 6 14 -24.553 16.0177 1 2 6 14 -7.1478 10.6446 1 3 6 14 6.92331 15.6608 1 -3 -3 15 124.455 18.6224 1 -2 -3 15 9.15956 11.5828 1 -1 -3 15 10.4933 8.66831 1 0 -3 15 -1.6174 8.19368 1 -3 -2 15 -12.490 4.57602 1 -2 -2 15 130.482 12.3995 1 -1 -2 15 1.34056 8.64048 1 0 -2 15 -11.132 8.13153 1 1 -2 15 -17.349 7.10980 1 2 -2 15 -27.113 10.4029 1 -3 -1 15 -2.1404 9.52285 1 -2 -1 15 79.8661 10.0085 1 -1 -1 15 -8.4764 6.94080 1 0 -1 15 -4.1519 7.86204 1 1 -1 15 98.0504 10.0321 1 2 -1 15 -5.7817 7.68692 1 -3 0 15 -21.396 10.5455 1 -2 0 15 29.2456 7.65685 1 -1 0 15 23.8146 9.34177 1 0 0 15 -0.4683 8.95683 1 1 0 15 -2.3710 8.28662 1 2 0 15 58.5787 9.10001 1 3 0 15 -13.625 8.23023 1 -3 1 15 -6.1800 12.4493 1 -2 1 15 4.40874 9.19322 1 -1 1 15 100.633 12.5672 1 0 1 15 -5.2924 8.84944 1 1 1 15 2.56881 8.74806 1 2 1 15 10.8704 7.81398 1 3 1 15 1.70892 8.99190 1 -2 2 15 -13.719 7.71427 1 -1 2 15 59.2950 10.8584 1 0 2 15 267.797 19.9786 1 1 2 15 2.58636 8.88596 1 2 2 15 12.6518 8.60421 1 3 2 15 123.709 15.3955 1 4 2 15 -14.514 10.3250 1 -2 3 15 -14.967 8.37131 1 -1 3 15 7.53690 11.1322 1 0 3 15 -9.1130 8.96294 1 1 3 15 138.910 14.3197 1 2 3 15 83.5154 11.0164 1 3 3 15 9.28053 8.36987 1 4 3 15 9.52819 11.9048 1 0 4 15 8.21793 12.5029 1 1 4 15 -5.3783 9.56471 1 2 4 15 83.1629 13.5968 1 3 4 15 -25.975 7.49353 1 1 5 15 53.3580 15.3952 1 2 5 15 139.589 17.1941 1 -1 -2 16 24.5948 13.2406 1 -2 -1 16 -16.470 11.6459 1 -1 -1 16 -17.149 9.20911 1 0 -1 16 -6.9886 10.7998 1 1 -1 16 46.7744 10.0222 1 -2 0 16 17.5890 12.0109 1 -1 0 16 -4.7164 7.87412 1 0 0 16 -13.035 8.94414 1 1 0 16 42.4213 9.40560 1 2 0 16 -10.607 8.94802 1 -1 1 16 49.4118 10.8298 1 0 1 16 17.3297 12.1349 1 1 1 16 10.3032 8.78869 1 2 1 16 84.0591 11.0622 1 -1 2 16 -3.1438 11.1827 1 0 2 16 28.6308 10.4355 1 1 2 16 3.99065 9.48120 1 2 2 16 -22.071 10.9441 1 0 3 16 15.0597 12.4767 1 1 3 16 -6.5245 9.30029 1 2 3 16 -18.824 10.4737 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 11184 _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 0.500000 1.000000 1.000000 0.0328(3) Uani 1 2 d S . P . . Cl1 Cl 0.77642(15) 0.74680(14) 1.03251(8) 0.0422(3) Uani 1 1 d . . . . . O1 O 0.6714(4) 0.3999(3) 0.62852(17) 0.0290(6) Uani 1 1 d . . . . . O2 O -0.1066(4) 0.9558(4) 0.55602(17) 0.0321(6) Uani 1 1 d . . . . . N1 N 0.6210(4) 0.5660(4) 0.6479(2) 0.0229(6) Uani 1 1 d . . . . . N2 N -0.0142(4) 0.8943(4) 0.6472(2) 0.0245(6) Uani 1 1 d . . . . . C2 C 0.6243(5) 0.7811(5) 0.7552(2) 0.0244(7) Uani 1 1 d . . . . . H2A H 0.665438 0.808374 0.816779 0.029 Uiso 1 1 calc R U . . . C5 C 0.5105(5) 0.6974(5) 0.5792(3) 0.0263(8) Uani 1 1 d . . . . . H5 H 0.471804 0.668193 0.517579 0.032 Uiso 1 1 calc R U . . . C8 C 0.0818(5) 0.7179(5) 0.6670(2) 0.0246(7) Uani 1 1 d . . . . . C10 C 0.1640(5) 0.7750(5) 0.8325(2) 0.0263(8) Uani 1 1 d . . . . . C3 C 0.5112(5) 0.9188(5) 0.6872(3) 0.0255(8) Uani 1 1 d . . . . . C1 C 0.6787(5) 0.6069(5) 0.7364(2) 0.0242(7) Uani 1 1 d . . . . . C9 C 0.1696(5) 0.6598(5) 0.7607(2) 0.0252(7) Uani 1 1 d . . . . . H9 H 0.236242 0.536576 0.776561 0.030 Uiso 1 1 calc R U . . . C4 C 0.4550(5) 0.8697(5) 0.5980(3) 0.0286(8) Uani 1 1 d . . . . . H4 H 0.376233 0.958846 0.549548 0.034 Uiso 1 1 calc R U . . . C12 C -0.0260(5) 1.0126(5) 0.7142(2) 0.0261(8) Uani 1 1 d . . . . . H12 H -0.095159 1.135142 0.697078 0.031 Uiso 1 1 calc R U . . . C11 C 0.0626(5) 0.9548(5) 0.8077(3) 0.0281(8) Uani 1 1 d . . . . . H11 H 0.054566 1.037678 0.855288 0.034 Uiso 1 1 calc R U . . . C14 C 0.2640(6) 0.7089(5) 0.9336(3) 0.0337(9) Uani 1 1 d . . . . . H14A H 0.393907 0.715831 0.932192 0.051 Uiso 1 1 calc R U . . . H14B H 0.281265 0.586156 0.948455 0.051 Uiso 1 1 calc R U . . . H14C H 0.182261 0.781641 0.985952 0.051 Uiso 1 1 calc R U . . . C13 C 0.0805(6) 0.6017(5) 0.5873(3) 0.0337(9) Uani 1 1 d . . . . . H13A H 0.147008 0.626287 0.526937 0.051 Uiso 1 1 calc R U . . . H13B H -0.056617 0.623876 0.570213 0.051 Uiso 1 1 calc R U . . . H13C H 0.150407 0.478102 0.611970 0.051 Uiso 1 1 calc R U . . . C6 C 0.7997(6) 0.4559(5) 0.8068(3) 0.0306(8) Uani 1 1 d . . . . . H6A H 0.727085 0.380961 0.823398 0.046 Uiso 1 1 calc R U . . . H6B H 0.826254 0.500457 0.868872 0.046 Uiso 1 1 calc R U . . . H6C H 0.925306 0.386865 0.774617 0.046 Uiso 1 1 calc R U . . . C7 C 0.4503(6) 1.1079(5) 0.7079(3) 0.0362(9) Uani 1 1 d . . . . . H7A H 0.473719 1.116301 0.779401 0.054 Uiso 1 1 calc R U . . . H7B H 0.309200 1.172805 0.692037 0.054 Uiso 1 1 calc R U . . . H7C H 0.528124 1.158587 0.665872 0.054 Uiso 1 1 calc R U . . . H2 H 0.000000 1.000000 0.500000 0.08(2) Uiso 1 2 d S . P . . 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 0.0337(7) 0.0312(7) 0.0325(7) -0.0047(5) -0.0067(5) -0.0111(6) Cl1 0.0396(6) 0.0365(6) 0.0415(6) -0.0071(4) -0.0116(4) -0.0045(5) O1 0.0365(15) 0.0204(13) 0.0298(13) -0.0030(10) -0.0032(10) -0.0104(11) O2 0.0287(14) 0.0454(17) 0.0216(12) 0.0083(11) -0.0091(10) -0.0153(13) N1 0.0244(15) 0.0241(16) 0.0202(14) 0.0011(11) -0.0019(11) -0.0100(13) N2 0.0244(15) 0.0283(17) 0.0208(14) 0.0042(11) -0.0048(11) -0.0113(13) C2 0.0219(17) 0.0259(19) 0.0236(17) -0.0006(13) -0.0032(13) -0.0078(15) C5 0.0231(18) 0.031(2) 0.0245(17) 0.0060(14) -0.0056(13) -0.0120(16) C8 0.0230(18) 0.0254(19) 0.0262(17) -0.0023(14) 0.0036(13) -0.0104(15) C10 0.0249(18) 0.032(2) 0.0243(17) 0.0031(14) -0.0031(13) -0.0149(16) C3 0.0218(18) 0.0242(19) 0.0296(18) 0.0020(14) 0.0006(13) -0.0087(15) C1 0.0239(18) 0.028(2) 0.0209(16) 0.0004(13) -0.0019(13) -0.0102(15) C9 0.0254(18) 0.0255(19) 0.0263(17) 0.0009(14) -0.0005(13) -0.0123(16) C4 0.0220(18) 0.034(2) 0.0286(18) 0.0082(15) -0.0038(13) -0.0117(16) C12 0.0270(19) 0.0210(18) 0.0288(18) -0.0009(14) -0.0005(14) -0.0081(15) C11 0.032(2) 0.030(2) 0.0236(17) -0.0047(14) 0.0003(14) -0.0128(17) C14 0.039(2) 0.040(2) 0.0241(18) 0.0040(15) -0.0075(15) -0.0191(19) C13 0.042(2) 0.036(2) 0.0287(19) -0.0078(15) 0.0028(16) -0.0206(19) C6 0.036(2) 0.027(2) 0.0249(18) 0.0009(14) -0.0084(15) -0.0087(17) C7 0.039(2) 0.032(2) 0.038(2) 0.0016(16) 0.0013(17) -0.0146(19) 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 Cl1 180.00(6) 2_677 . ? N2 O2 H2 109.2(2) . . ? O1 N1 C5 119.7(3) . . ? O1 N1 C1 120.3(3) . . ? C5 N1 C1 119.9(3) . . ? C8 N2 O2 118.8(3) . . ? C12 N2 O2 118.1(3) . . ? C12 N2 C8 123.1(3) . . ? C3 C2 H2A 118.8 . . ? C1 C2 H2A 118.8 . . ? C1 C2 C3 122.3(3) . . ? N1 C5 H5 119.6 . . ? C4 C5 N1 120.8(3) . . ? C4 C5 H5 119.6 . . ? N2 C8 C9 117.4(3) . . ? N2 C8 C13 117.7(3) . . ? C9 C8 C13 124.9(3) . . ? C9 C10 C11 117.6(3) . . ? C9 C10 C14 121.3(3) . . ? C11 C10 C14 121.0(3) . . ? C2 C3 C4 116.0(3) . . ? C2 C3 C7 122.4(3) . . ? C4 C3 C7 121.6(3) . . ? N1 C1 C2 119.4(3) . . ? N1 C1 C6 116.5(3) . . ? C2 C1 C6 124.1(3) . . ? C8 C9 C10 122.2(3) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C5 C4 C3 121.5(3) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? N2 C12 H12 120.2 . . ? N2 C12 C11 119.6(3) . . ? C11 C12 H12 120.2 . . ? C10 C11 H11 120.0 . . ? C12 C11 C10 120.1(3) . . ? C12 C11 H11 120.0 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 Cl1 2.2873(11) 2_677 ? Cl2 Cl1 2.2873(11) . ? O1 N1 1.318(4) . ? O2 N2 1.363(3) . ? O2 H2 1.211(2) . ? N1 C5 1.365(4) . ? N1 C1 1.366(4) . ? N2 C8 1.355(4) . ? N2 C12 1.346(4) . ? C2 H2A 0.9500 . ? C2 C3 1.392(5) . ? C2 C1 1.376(5) . ? C5 H5 0.9500 . ? C5 C4 1.360(5) . ? C8 C9 1.376(5) . ? C8 C13 1.484(5) . ? C10 C9 1.385(5) . ? C10 C11 1.393(5) . ? C10 C14 1.502(5) . ? C3 C4 1.400(5) . ? C3 C7 1.493(5) . ? C1 C6 1.488(5) . ? C9 H9 0.9500 . ? C4 H4 0.9500 . ? C12 H12 0.9500 . ? C12 C11 1.376(5) . ? C11 H11 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 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 _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 C5 C4 179.3(3) . . . . ? O1 N1 C1 C2 -179.9(3) . . . . ? O1 N1 C1 C6 0.4(5) . . . . ? O2 N2 C8 C9 -178.5(3) . . . . ? O2 N2 C8 C13 0.1(4) . . . . ? O2 N2 C12 C11 178.8(3) . . . . ? N1 C5 C4 C3 1.0(5) . . . . ? N2 C8 C9 C10 -0.8(5) . . . . ? N2 C12 C11 C10 0.1(5) . . . . ? C2 C3 C4 C5 -0.8(5) . . . . ? C5 N1 C1 C2 0.0(5) . . . . ? C5 N1 C1 C6 -179.7(3) . . . . ? C8 N2 C12 C11 0.1(5) . . . . ? C3 C2 C1 N1 0.2(5) . . . . ? C3 C2 C1 C6 179.9(3) . . . . ? C1 N1 C5 C4 -0.6(5) . . . . ? C1 C2 C3 C4 0.2(5) . . . . ? C1 C2 C3 C7 179.4(3) . . . . ? C9 C10 C11 C12 -0.6(5) . . . . ? C12 N2 C8 C9 0.3(5) . . . . ? C12 N2 C8 C13 178.9(3) . . . . ? C11 C10 C9 C8 1.0(5) . . . . ? C14 C10 C9 C8 -178.8(3) . . . . ? C14 C10 C11 C12 179.2(3) . . . . ? C13 C8 C9 C10 -179.3(3) . . . . ? C7 C3 C4 C5 -180.0(3) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.9043 2 0.0957