#------------------------------------------------------------------------------ #$Date: 2017-11-08 07:00:59 +0200 (Wed, 08 Nov 2017) $ #$Revision: 202942 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/04/47/7044702.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_7044702 loop_ _publ_author_name 'Sun, Yu-Ling' 'Shi, Chao' 'Zhang, Wen' _publ_section_title ; Distinct room-temperature dielectric transition in a perchlorate-based organic-inorganic hybrid perovskite ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/C7DT03798H _journal_year 2017 _chemical_formula_moiety 'Cl3 K O12, C5 H14 N2' _chemical_formula_sum 'C5 H14 Cl3 K N2 O12' _chemical_formula_weight 439.63 _space_group_crystal_system orthorhombic _space_group_IT_number 57 _space_group_name_Hall '-P 2c 2b' _space_group_name_H-M_alt 'P b c m' _symmetry_space_group_name_Hall '-P 2c 2b' _symmetry_space_group_name_H-M 'P b c m' _atom_sites_solution_hydrogens difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-10-31 deposited with the CCDC. 2017-11-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.739(11) _cell_length_b 9.967(11) _cell_length_c 14.350(15) _cell_measurement_reflns_used 4434 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.3968 _cell_measurement_theta_min 2.3683 _cell_volume 1536(3) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.888 _diffrn_measured_fraction_theta_max 0.856 _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_unetI/netI 0.0366 _diffrn_reflns_Laue_measured_fraction_full 0.888 _diffrn_reflns_Laue_measured_fraction_max 0.856 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 10597 _diffrn_reflns_point_group_measured_fraction_full 0.888 _diffrn_reflns_point_group_measured_fraction_max 0.856 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.374 _diffrn_reflns_theta_min 2.788 _exptl_absorpt_coefficient_mu 0.932 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.901 _exptl_crystal_description Prism _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.2000 _refine_diff_density_max 0.627 _refine_diff_density_min -0.713 _refine_diff_density_rms 0.104 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.247 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 143 _refine_ls_number_reflns 1556 _refine_ls_number_restraints 185 _refine_ls_restrained_S_all 1.259 _refine_ls_R_factor_all 0.1264 _refine_ls_R_factor_gt 0.1210 _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^)+(0.1404P)^2^+3.9824P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3235 _refine_ls_wR_factor_ref 0.3286 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1459 _reflns_number_total 1556 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7dt03798h2.cif _cod_data_source_block 1-378K _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7044702 _shelx_shelxl_version_number 2014/7 _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_res_file ; 1.res created by SHELXL-2014/7 TITL 1 in Pbcm New: Pbcm CELL 0.71073 10.7390 9.9670 14.3500 90.000 90.000 90.000 ZERR 4 0.0110 0.0110 0.0150 0.000 0.000 0.000 LATT 1 SYMM - X , - Y , 0.50000 + Z SYMM X , 0.50000 - Y , - Z SYMM - X , 0.50000 + Y , 0.50000 - Z SFAC C H Cl K N O UNIT 20 56 12 4 8 48 L.S. 50 ACTA BOND $H FMAP 2 PLAN 0 SIMU 0.02 0.04 3.8 $C $N SADI 0.001 C4 C1 C5 C3 DELU DFIX 1.5 0.1 N1 C2 C2 C3 C3 C5 C5 N2 N2 C4 C4 C1 C1 N1 CONF ISOR 0.01 O3 EQIV $1 x+1, -y+1/2, -z+1 HTAB C1 O8_$1 EQIV $2 x+1, y, z-1 HTAB C1 O5_$2 HTAB C1 O5_$1 EQIV $3 -x+1, y-1/2, z-1 HTAB C2 O1_$3 HTAB C2 O3_$3 EQIV $4 x, -y+1/2, -z+1 HTAB C3 O3_$4 EQIV $5 x, y, z-1 HTAB C3 O3_$5 HTAB C3 O4_$5 HTAB C3 O4_$4 HTAB C4 O8_$2 EQIV $6 -x+1, -y+1, -z+1 HTAB C4 O8_$6 HTAB C3 O1_$6 HTAB C5 O1_$6 EQIV $7 -x+1, y+1/2, z-1 HTAB C5 O4_$7 HTAB N1 O5_$3 HTAB N1 O6_$3 HTAB N1 O7_$2 HTAB N2 O6_$6 FREE Cl2 K1 FREE Cl3 K1 FREE Cl1 K1 FREE C3 H5A WGHT 0.140400 3.982400 FVAR 0.35150 K1 4 0.247053 0.214596 0.750000 10.50000 0.05651 0.05634 = 0.05266 0.00000 0.00000 0.00012 CL1 3 0.511402 0.453811 0.750000 10.50000 0.06770 0.05873 = 0.09919 0.00000 0.00000 -0.01741 CL2 3 0.246752 0.250000 1.000000 10.50000 0.05810 0.11769 = 0.04421 0.00458 0.00000 0.00000 CL3 3 -0.017980 0.449012 0.750000 10.50000 0.06474 0.04741 = 0.07353 0.00000 0.00000 0.01211 C1 1 0.895206 0.223050 -0.015749 10.50000 0.05777 0.16284 = 0.12281 -0.03668 0.01233 0.00834 AFIX 3 H1A 2 0.904646 0.157228 0.032580 10.50000 -1.20000 H1B 2 0.975576 0.234258 -0.043969 10.50000 -1.20000 AFIX 0 C2 1 0.661271 0.176891 -0.071787 10.50000 0.07641 0.16155 = 0.12711 -0.03723 -0.01680 -0.00938 AFIX 3 H2A 2 0.634032 0.206921 -0.131987 10.50000 -1.20000 H2B 2 0.633362 0.085861 -0.065297 10.50000 -1.20000 AFIX 0 C3 1 0.601066 0.250000 0.000000 10.50000 0.06312 0.17429 = 0.13702 -0.02164 0.00000 0.00000 AFIX 3 H3A 2 0.582496 0.189790 0.050330 10.50000 -1.20000 H3B 2 0.522716 0.272300 -0.028240 10.50000 -1.20000 AFIX 0 C4 1 0.865380 0.330939 0.029045 10.50000 0.05464 0.15683 = 0.11981 -0.03929 0.01317 -0.00872 AFIX 3 H4A 2 0.852921 0.397479 -0.018414 10.50000 -1.20000 H4B 2 0.935303 0.358899 0.065935 10.50000 -1.20000 AFIX 0 C5 1 0.646050 0.365319 0.023869 10.50000 0.06695 0.16081 = 0.12560 -0.03633 0.00031 0.01998 AFIX 3 H5A 2 0.586499 0.364389 0.073759 10.50000 -1.20000 H5B 2 0.620020 0.452619 -0.000791 10.50000 -1.20000 AFIX 0 N1 5 0.817234 0.156150 -0.077399 10.50000 0.08035 0.15976 = 0.12995 -0.04506 0.01071 -0.00247 AFIX 3 H1C 2 0.838184 0.068920 -0.081549 10.50000 -1.20000 H1D 2 0.839504 0.193980 -0.131860 10.50000 -1.20000 AFIX 0 N2 5 0.742450 0.334394 0.093606 10.50000 0.05348 0.15570 = 0.11287 -0.04604 0.00820 -0.00120 AFIX 3 H2C 2 0.743940 0.403914 0.133606 10.50000 -1.20000 H2D 2 0.740170 0.257714 0.126686 10.50000 -1.20000 AFIX 0 O1 6 0.500829 0.595259 0.750000 10.50000 0.13694 0.04040 = 0.16335 0.00000 0.00000 -0.02615 O2 6 0.639728 0.422093 0.750000 10.50000 0.06664 0.14044 = 0.17279 0.00000 0.00000 -0.00212 O3 6 0.452811 0.397777 0.828853 11.00000 0.10937 0.10432 = 0.13001 0.01423 0.02057 -0.02275 O4 6 0.324271 0.158922 0.948469 11.00000 0.08747 0.11793 = 0.06523 -0.00331 0.01053 0.00781 O5 6 0.170529 0.321063 0.934511 11.00000 0.08637 0.16090 = 0.06183 0.01813 -0.01123 0.01600 O6 6 0.114909 0.478178 0.750000 10.50000 0.07539 0.07515 = 0.07387 0.00000 0.00000 0.00324 O7 6 -0.033666 0.308445 0.750000 10.50000 0.09752 0.05209 = 0.13066 0.00000 0.00000 0.00024 O8 6 -0.074865 0.508325 0.830889 11.00000 0.08771 0.08596 = 0.08794 -0.00874 0.01768 0.02231 HKLF 4 REM 1 in Pbcm New: Pbcm REM R1 = 0.1210 for 1459 Fo > 4sig(Fo) and 0.1264 for all 1556 data REM 143 parameters refined using 185 restraints END WGHT 0.1385 4.1280 REM Highest difference peak 0.627, deepest hole -0.713, 1-sigma level 0.104 Q1 1 0.6085 0.3107 0.0396 11.00000 0.05 0.63 Q2 1 0.5150 0.4480 0.8680 11.00000 0.05 0.42 Q3 1 0.5405 0.4277 0.8528 11.00000 0.05 0.41 Q4 1 0.8933 0.3246 0.0388 11.00000 0.05 0.38 Q5 1 0.3766 0.4561 0.7945 11.00000 0.05 0.36 Q6 1 0.3257 0.1163 0.9954 11.00000 0.05 0.33 Q7 1 0.4030 0.4127 0.7500 10.50000 0.05 0.30 Q8 1 0.8227 0.3888 0.0104 11.00000 0.05 0.30 Q9 1 0.1564 0.3693 0.9862 11.00000 0.05 0.28 Q10 1 0.1804 0.3325 0.7500 10.50000 0.05 0.27 Q11 1 0.6587 0.3626 -0.0395 11.00000 0.05 0.26 Q12 1 -0.1185 0.3396 0.7500 10.50000 0.05 0.26 Q13 1 0.6795 0.1148 0.0745 11.00000 0.05 0.25 Q14 1 0.3366 0.3223 0.7500 10.50000 0.05 0.25 Q15 1 0.1471 0.1357 0.7500 10.50000 0.05 0.24 Q16 1 -0.0242 0.5143 0.8716 11.00000 0.05 0.23 Q17 1 0.1303 0.5192 0.7124 11.00000 0.05 0.23 Q18 1 0.5188 0.4714 0.7238 11.00000 0.05 0.22 Q19 1 -0.0014 0.4825 0.7092 11.00000 0.05 0.22 Q20 1 0.6317 0.4817 0.6859 11.00000 0.05 0.21 ; _shelx_res_checksum 10498 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z-1/2' '-x, y-1/2, z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy K1 K 0.24705(19) 0.2146(2) 0.7500 0.0552(8) Uani 1 2 d S TU P Cl1 Cl 0.5114(3) 0.4538(3) 0.7500 0.0752(10) Uani 1 2 d S TU P Cl2 Cl 0.2468(2) 0.2500 1.0000 0.0733(10) Uani 1 2 d S TU P Cl3 Cl -0.0180(3) 0.4490(2) 0.7500 0.0619(8) Uani 1 2 d S TU P C1 C 0.895(2) 0.223(3) -0.016(2) 0.114(5) Uani 0.5 1 d D U P H1A H 0.9046 0.1572 0.0326 0.137 Uiso 0.5 1 d R U P H1B H 0.9756 0.2343 -0.0440 0.137 Uiso 0.5 1 d R U P C2 C 0.661(3) 0.177(3) -0.072(2) 0.122(5) Uani 0.5 1 d D U P H2A H 0.6340 0.2069 -0.1320 0.146 Uiso 0.5 1 d R U P H2B H 0.6334 0.0859 -0.0653 0.146 Uiso 0.5 1 d R U P C3 C 0.6011(15) 0.2500 0.0000 0.125(4) Uani 1 2 d DS TU P H3A H 0.5825 0.1898 0.0503 0.150 Uiso 0.5 1 d R U P H3B H 0.5227 0.2723 -0.0282 0.150 Uiso 0.5 1 d R U P C4 C 0.865(2) 0.331(2) 0.029(2) 0.110(5) Uani 0.5 1 d D U P H4A H 0.8529 0.3975 -0.0184 0.133 Uiso 0.5 1 d R U P H4B H 0.9353 0.3589 0.0659 0.133 Uiso 0.5 1 d R U P C5 C 0.646(2) 0.365(2) 0.0239(19) 0.118(5) Uani 0.5 1 d D U P H5A H 0.5865 0.3644 0.0738 0.141 Uiso 0.5 1 d R U P H5B H 0.6200 0.4526 -0.0008 0.141 Uiso 0.5 1 d R U P N1 N 0.817(2) 0.156(2) -0.0774(16) 0.123(5) Uani 0.5 1 d D U P H1C H 0.8382 0.0689 -0.0815 0.148 Uiso 0.5 1 d R U P H1D H 0.8395 0.1940 -0.1319 0.148 Uiso 0.5 1 d R U P N2 N 0.7424(16) 0.334(3) 0.0936(16) 0.107(4) Uani 0.5 1 d D U P H2C H 0.7439 0.4039 0.1336 0.129 Uiso 0.5 1 d R U P H2D H 0.7402 0.2577 0.1267 0.129 Uiso 0.5 1 d R U P O1 O 0.5008(11) 0.5953(8) 0.7500 0.114(3) Uani 1 2 d S TU P O2 O 0.6397(10) 0.4221(13) 0.7500 0.127(4) Uani 1 2 d S TU P O3 O 0.4528(7) 0.3978(8) 0.8289(6) 0.115(2) Uani 1 1 d . U . O4 O 0.3243(6) 0.1589(7) 0.9485(4) 0.0902(19) Uani 1 1 d . U . O5 O 0.1705(6) 0.3211(8) 0.9345(4) 0.103(2) Uani 1 1 d . U . O6 O 0.1149(8) 0.4782(8) 0.7500 0.075(2) Uani 1 2 d S TU P O7 O -0.0337(9) 0.3084(8) 0.7500 0.093(2) Uani 1 2 d S TU P O8 O -0.0749(6) 0.5083(6) 0.8309(4) 0.0872(19) Uani 1 1 d . 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 K1 0.0565(18) 0.0563(12) 0.0527(12) 0.000 0.000 0.0001(9) Cl1 0.068(2) 0.0587(15) 0.099(2) 0.000 0.000 -0.0174(13) Cl2 0.058(2) 0.118(3) 0.0442(13) 0.0046(13) 0.000 0.000 Cl3 0.065(2) 0.0474(12) 0.0735(15) 0.000 0.000 0.0121(11) C1 0.058(9) 0.163(12) 0.123(11) -0.037(9) 0.012(7) 0.008(8) C2 0.076(10) 0.162(11) 0.127(11) -0.037(9) -0.017(7) -0.009(7) C3 0.063(9) 0.174(11) 0.137(10) -0.022(8) 0.000 0.000 C4 0.055(9) 0.157(11) 0.120(10) -0.039(9) 0.013(7) -0.009(7) C5 0.067(9) 0.161(11) 0.126(11) -0.036(9) 0.000(7) 0.020(7) N1 0.080(10) 0.160(10) 0.130(10) -0.045(9) 0.011(7) -0.002(7) N2 0.053(10) 0.156(10) 0.113(9) -0.046(8) 0.008(5) -0.001(6) O1 0.137(8) 0.040(4) 0.163(9) 0.000 0.000 -0.026(4) O2 0.067(6) 0.140(10) 0.173(11) 0.000 0.000 -0.002(6) O3 0.109(4) 0.104(5) 0.130(5) 0.014(4) 0.021(4) -0.023(4) O4 0.087(5) 0.118(5) 0.065(3) -0.003(3) 0.011(3) 0.008(3) O5 0.086(5) 0.161(7) 0.062(3) 0.018(4) -0.011(3) 0.016(4) O6 0.075(5) 0.075(5) 0.074(4) 0.000 0.000 0.003(4) O7 0.098(5) 0.052(4) 0.131(7) 0.000 0.000 0.000(4) O8 0.088(5) 0.086(4) 0.088(4) -0.009(3) 0.018(3) 0.022(3) 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' K K 0.2009 0.2494 '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 O1 K1 O5 113.41(14) 7_655 . O1 K1 O5 113.41(14) 7_655 6_557 O5 K1 O5 126.2(3) . 6_557 O1 K1 O6 142.1(3) 7_655 . O5 K1 O6 63.51(14) . . O5 K1 O6 63.51(14) 6_557 . O1 K1 O8 106.8(2) 7_655 4_546 O5 K1 O8 114.8(2) . 4_546 O5 K1 O8 74.3(2) 6_557 4_546 O6 K1 O8 108.1(2) . 4_546 O1 K1 O8 106.8(2) 7_655 7 O5 K1 O8 74.3(2) . 7 O5 K1 O8 114.8(2) 6_557 7 O6 K1 O8 108.1(2) . 7 O8 K1 O8 45.5(2) 4_546 7 O1 K1 O4 71.00(13) 7_655 . O5 K1 O4 45.57(19) . . O5 K1 O4 169.6(2) 6_557 . O6 K1 O4 107.00(14) . . O8 K1 O4 114.12(18) 4_546 . O8 K1 O4 71.22(18) 7 . O1 K1 O4 71.00(13) 7_655 6_557 O5 K1 O4 169.6(2) . 6_557 O5 K1 O4 45.57(19) 6_557 6_557 O6 K1 O4 107.00(14) . 6_557 O8 K1 O4 71.22(18) 4_546 6_557 O8 K1 O4 114.12(18) 7 6_557 O4 K1 O4 141.4(3) . 6_557 O1 K1 O3 65.3(2) 7_655 . O5 K1 O3 70.1(2) . . O5 K1 O3 108.3(2) 6_557 . O6 K1 O3 79.6(2) . . O8 K1 O3 172.1(2) 4_546 . O8 K1 O3 134.9(2) 7 . O4 K1 O3 64.24(19) . . O4 K1 O3 105.0(2) 6_557 . O1 K1 O3 65.3(2) 7_655 6_557 O5 K1 O3 108.3(2) . 6_557 O5 K1 O3 70.1(2) 6_557 6_557 O6 K1 O3 79.6(2) . 6_557 O8 K1 O3 134.9(2) 4_546 6_557 O8 K1 O3 172.1(2) 7 6_557 O4 K1 O3 105.0(2) . 6_557 O4 K1 O3 64.24(19) 6_557 6_557 O3 K1 O3 43.1(3) . 6_557 O1 K1 O7 173.5(2) 7_655 . O5 K1 O7 68.26(14) . . O5 K1 O7 68.26(14) 6_557 . O6 K1 O7 44.4(2) . . O8 K1 O7 67.3(2) 4_546 . O8 K1 O7 67.3(2) 7 . O4 K1 O7 108.48(13) . . O4 K1 O7 108.48(13) 6_557 . O3 K1 O7 120.6(2) . . O3 K1 O7 120.6(2) 6_557 . O1 K1 O2 43.6(3) 7_655 7_655 O5 K1 O2 115.88(15) . 7_655 O5 K1 O2 115.88(15) 6_557 7_655 O6 K1 O2 174.3(3) . 7_655 O8 K1 O2 66.7(2) 4_546 7_655 O8 K1 O2 66.7(2) 7 7_655 O4 K1 O2 74.01(14) . 7_655 O4 K1 O2 74.01(14) 6_557 7_655 O3 K1 O2 105.7(2) . 7_655 O3 K1 O2 105.7(2) 6_557 7_655 O7 K1 O2 129.9(3) . 7_655 O3 Cl1 O3 106.7(7) . 6_557 O3 Cl1 O2 110.3(5) . . O3 Cl1 O2 110.3(5) 6_557 . O3 Cl1 O1 111.0(4) . . O3 Cl1 O1 111.0(4) 6_557 . O2 Cl1 O1 107.5(7) . . O3 Cl1 K1 126.6(3) . 7_665 O3 Cl1 K1 126.6(3) 6_557 7_665 O2 Cl1 K1 58.0(5) . 7_665 O1 Cl1 K1 49.5(5) . 7_665 O5 Cl2 O5 110.4(6) 3_557 . O5 Cl2 O4 110.9(4) 3_557 . O5 Cl2 O4 107.8(4) . . O5 Cl2 O4 107.8(4) 3_557 3_557 O5 Cl2 O4 110.9(4) . 3_557 O4 Cl2 O4 109.2(6) . 3_557 O5 Cl2 K1 52.9(3) 3_557 3_557 O5 Cl2 K1 127.2(3) . 3_557 O4 Cl2 K1 125.0(3) . 3_557 O4 Cl2 K1 54.9(2) 3_557 3_557 O7 Cl3 O8 110.9(4) . . O7 Cl3 O8 110.9(4) . 6_557 O8 Cl3 O8 107.6(5) . 6_557 O7 Cl3 O6 108.4(5) . . O8 Cl3 O6 109.5(4) . . O8 Cl3 O6 109.5(4) 6_557 . O7 Cl3 K1 130.2(4) . 7_565 O8 Cl3 K1 53.8(3) . 7_565 O8 Cl3 K1 53.8(3) 6_557 7_565 O6 Cl3 K1 121.4(4) . 7_565 C4 C1 C1 145(6) 3 3 C4 C1 C4 135(6) 3 . C1 C1 C4 17(3) 3 . C4 C1 N1 29(4) 3 . C1 C1 N1 141(2) 3 . C4 C1 N1 125(3) . . C4 C1 H1A 72.6 3 . C1 C1 H1A 93.3 3 . C4 C1 H1A 103.6 . . N1 C1 H1A 101.3 . . C4 C1 H1B 114.4 3 . C1 C1 H1B 100.5 3 . C4 C1 H1B 109.6 . . N1 C1 H1B 109.2 . . H1A C1 H1B 106.8 . . C5 C2 N2 114(5) 3 3 C5 C2 C3 64(2) 3 . N2 C2 C3 137(3) 3 . C5 C2 N1 100(3) 3 . N2 C2 N1 17(2) 3 . C3 C2 N1 123.3(19) . . C5 C2 H2A 148.4 3 . N2 C2 H2A 91.2 3 . C3 C2 H2A 110.8 . . N1 C2 H2A 107.3 . . C5 C2 H2B 51.2 3 . N2 C2 H2B 102.1 3 . C3 C2 H2B 105.8 . . N1 C2 H2B 101.4 . . H2A C2 H2B 106.7 . . C5 C3 C5 136(3) . 3 C5 C3 C2 118.6(18) . . C5 C3 C2 34.9(17) 3 . C5 C3 C2 34.9(17) . 3 C5 C3 C2 118.6(18) 3 3 C2 C3 C2 126(2) . 3 C5 C3 H3A 115.7 . . C5 C3 H3A 73.8 3 . C2 C3 H3A 108.7 . . C2 C3 H3A 82.5 3 . C5 C3 H3B 103.5 . . C5 C3 H3B 114.9 3 . C2 C3 H3B 102.2 . . C2 C3 H3B 126.0 3 . H3A C3 H3B 106.3 . . C5 C3 H5A 37.8 . . C5 C3 H5A 149.9 3 . C2 C3 H5A 155.8 . . C2 C3 H5A 34.8 3 . H3A C3 H5A 85.7 . . H3B C3 H5A 91.7 . . C1 C4 N1 130(7) 3 3 C1 C4 C1 18(3) 3 . N1 C4 C1 132(3) 3 . C1 C4 N2 126(5) 3 . N1 C4 N2 20(2) 3 . C1 C4 N2 120(2) . . C1 C4 C4 30(4) 3 3 N1 C4 C4 120(3) 3 3 C1 C4 C4 14.8(18) . 3 N2 C4 C4 106.4(17) . 3 C1 C4 H4A 115.4 3 . N1 C4 H4A 112.3 3 . C1 C4 H4A 104.9 . . N2 C4 H4A 106.2 . . C4 C4 H4A 106.7 3 . C1 C4 H4B 91.0 3 . N1 C4 H4B 89.0 3 . C1 C4 H4B 108.8 . . N2 C4 H4B 108.5 . . C4 C4 H4B 120.7 3 . H4A C4 H4B 107.4 . . C2 C5 C3 81(3) 3 . C2 C5 N2 35(2) 3 . C3 C5 N2 105(2) . . C2 C5 H5A 60.3 3 . C3 C5 H5A 86.6 . . N2 C5 H5A 87.7 . . C2 C5 H5B 144.4 3 . C3 C5 H5B 125.9 . . N2 C5 H5B 129.2 . . H5A C5 H5B 95.0 . . N2 N1 C4 140(4) 3 3 N2 N1 C1 134(3) 3 . C4 N1 C1 21(3) 3 . N2 N1 C2 19(2) 3 . C4 N1 C2 122(3) 3 . C1 N1 C2 120.6(17) . . N2 N1 H1C 109.2 3 . C4 N1 H1C 92.7 3 . C1 N1 H1C 110.8 . . C2 N1 H1C 111.7 . . N2 N1 H1D 88.1 3 . C4 N1 H1D 118.0 3 . C1 N1 H1D 101.1 . . C2 N1 H1D 104.7 . . H1C N1 H1D 106.3 . . N1 N2 C2 144(4) 3 3 N1 N2 C5 117(3) 3 . C2 N2 C5 31(3) 3 . N1 N2 C4 20(2) 3 . C2 N2 C4 125(3) 3 . C5 N2 C4 101(2) . . N1 N2 H2C 94.2 3 . C2 N2 H2C 108.9 3 . C5 N2 H2C 106.5 . . C4 N2 H2C 111.6 . . N1 N2 H2D 105.5 3 . C2 N2 H2D 92.8 3 . C5 N2 H2D 121.1 . . C4 N2 H2D 107.9 . . H2C N2 H2D 108.5 . . Cl1 O1 K1 109.1(6) . 7_665 Cl1 O2 K1 99.7(6) . 7_665 Cl1 O3 K1 105.1(4) . . Cl2 O4 K1 102.1(3) . . Cl2 O5 K1 104.5(4) . . Cl3 O6 K1 106.9(4) . . Cl3 O7 K1 100.4(5) . . Cl3 O8 K1 103.4(3) . 7_565 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 K1 O1 2.957(11) 7_655 K1 O5 2.968(7) . K1 O5 2.969(7) 6_557 K1 O6 2.986(9) . K1 O8 2.999(7) 4_546 K1 O8 2.999(7) 7 K1 O4 3.018(7) . K1 O4 3.018(7) 6_557 K1 O3 3.082(8) . K1 O3 3.082(8) 6_557 K1 O7 3.156(10) . K1 O2 3.159(13) 7_655 Cl1 O3 1.410(7) . Cl1 O3 1.410(7) 6_557 Cl1 O2 1.414(11) . Cl1 O1 1.414(8) . Cl1 K1 3.672(4) 7_665 Cl2 O5 1.433(6) 3_557 Cl2 O5 1.433(6) . Cl2 O4 1.437(6) . Cl2 O4 1.437(6) 3_557 Cl2 K1 3.605(4) 3_557 Cl3 O7 1.411(8) . Cl3 O8 1.439(6) . Cl3 O8 1.439(6) 6_557 Cl3 O6 1.456(9) . Cl3 K1 3.614(4) 7_565 C1 C4 0.65(3) 3 C1 C1 0.70(4) 3 C1 C4 1.293(19) . C1 N1 1.39(3) . C1 H1A 0.9600 . C1 H1B 0.9599 . C2 C5 0.82(4) 3 C2 N2 0.93(3) 3 C2 C3 1.42(3) . C2 N1 1.69(3) . C2 H2A 0.9599 . C2 H2B 0.9600 . C3 C5 1.293(19) . C3 C5 1.293(19) 3 C3 C2 1.42(3) 3 C3 H3A 0.9600 . C3 H3B 0.9600 . C4 C1 0.65(3) 3 C4 N1 0.87(3) 3 C4 N2 1.61(3) . C4 C4 1.82(4) 3 C4 H4A 0.9600 . C4 H4B 0.9601 . C5 C2 0.82(4) 3 C5 N2 1.47(3) . C5 H5A 0.9600 . C5 H5B 0.9800 . N1 N2 0.84(2) 3 N1 C4 0.87(3) 3 N1 H1C 0.9000 . N1 H1D 0.9001 . N2 N1 0.84(2) 3 N2 C2 0.93(3) 3 N2 H2C 0.8999 . N2 H2D 0.9000 . O1 K1 2.957(11) 7_665 O2 K1 3.159(13) 7_665 O8 K1 2.999(7) 7_565 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C1 H1A O8 0.96 2.57 3.53(4) 176.5 3_656 C1 H1B O5 0.96 2.29 3.19(2) 157.6 1_654 C1 H1B O5 0.96 2.67 3.21(2) 115.6 3_656 C2 H2A O1 0.96 2.49 3.20(3) 130.5 7_654 C2 H2B O3 0.96 2.58 3.36(3) 137.8 7_654 C3 H3A O3 0.96 2.39 3.277(11) 153.6 3_556 C3 H3B O3 0.96 2.52 3.277(11) 136.1 1_554 C3 H3B O4 0.96 2.44 3.195(16) 135.8 1_554 C3 H3B O4 0.96 2.51 3.195(16) 127.9 3_556 C4 H4A O8 0.96 2.55 3.41(3) 149.2 1_654 C4 H4B O8 0.96 2.49 3.42(3) 162.5 5_666 C5 H5A O1 0.96 2.73 3.63(3) 156.8 5_666 C5 H5B O4 0.98 2.26 3.14(3) 148.0 7_664 N1 H1C O5 0.90 2.48 3.35(3) 161.0 7_654 N1 H1C O6 0.90 2.63 3.13(2) 116.2 7_654 N1 H1D O7 0.90 2.46 3.32(3) 160.3 1_654 N2 H2C O6 0.90 2.54 3.30(2) 141.7 5_666 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_4 C5 C2 C3 C5 131(3) 3 . N2 C2 C3 C5 33(6) 3 . N1 C2 C3 C5 46(3) . . N2 C2 C3 C5 -98(6) 3 3 N1 C2 C3 C5 -85(3) . 3 C5 C2 C3 C2 90(3) 3 3 N2 C2 C3 C2 -8(5) 3 3 N1 C2 C3 C2 5.0(16) . 3 C4 C1 C4 C1 133(22) 3 3 N1 C1 C4 C1 168(17) . 3 C4 C1 C4 N1 40(8) 3 3 C1 C1 C4 N1 -93(16) 3 3 N1 C1 C4 N1 75(6) . 3 C4 C1 C4 N2 20(7) 3 . C1 C1 C4 N2 -113(15) 3 . N1 C1 C4 N2 55(4) . . C1 C1 C4 C4 -133(22) 3 3 N1 C1 C4 C4 35(6) . 3 C5 C3 C5 C2 -74(3) 3 3 C2 C3 C5 C2 -112(4) . 3 C5 C3 C5 N2 -47.4(13) 3 . C2 C3 C5 N2 -86(2) . . C2 C3 C5 N2 26(2) 3 . C4 C1 N1 N2 117(9) 3 3 C1 C1 N1 N2 0(13) 3 3 C4 C1 N1 N2 -5(6) . 3 C1 C1 N1 C4 -117(14) 3 3 C4 C1 N1 C4 -122(9) . 3 C4 C1 N1 C2 100(8) 3 . C1 C1 N1 C2 -16(12) 3 . C4 C1 N1 C2 -22(4) . . C5 C2 N1 N2 146(10) 3 3 C3 C2 N1 N2 -148(9) . 3 C5 C2 N1 C4 -48(4) 3 3 N2 C2 N1 C4 166(10) 3 3 C3 C2 N1 C4 18(5) . 3 C5 C2 N1 C1 -72(4) 3 . N2 C2 N1 C1 141(9) 3 . C3 C2 N1 C1 -7(4) . . C2 C5 N2 N1 157(6) 3 3 C3 C5 N2 N1 108(3) . 3 C3 C5 N2 C2 -49(4) . 3 C2 C5 N2 C4 144(5) 3 . C3 C5 N2 C4 95(2) . . C1 C4 N2 N1 109(11) 3 3 C1 C4 N2 N1 130(8) . 3 C4 C4 N2 N1 135(8) 3 3 C1 C4 N2 C2 -84(8) 3 3 N1 C4 N2 C2 167(10) 3 3 C1 C4 N2 C2 -63(5) . 3 C4 C4 N2 C2 -58(5) 3 3 C1 C4 N2 C5 -105(6) 3 . N1 C4 N2 C5 146(8) 3 . C1 C4 N2 C5 -84(3) . . C4 C4 N2 C5 -79(3) 3 . O3 Cl1 O1 K1 120.7(4) . 7_665 O3 Cl1 O1 K1 -120.7(4) 6_557 7_665 O2 Cl1 O1 K1 0.0 . 7_665 O3 Cl1 O2 K1 -121.2(4) . 7_665 O3 Cl1 O2 K1 121.2(4) 6_557 7_665 O1 Cl1 O2 K1 0.0 . 7_665 O3 Cl1 O3 K1 -2.0(7) 6_557 . O2 Cl1 O3 K1 -121.7(5) . . O1 Cl1 O3 K1 119.2(5) . . K1 Cl1 O3 K1 173.73(15) 7_665 . O5 Cl2 O4 K1 121.5(3) 3_557 . O5 Cl2 O4 K1 0.6(4) . . O4 Cl2 O4 K1 -119.9(3) 3_557 . K1 Cl2 O4 K1 -179.91(9) 3_557 . O5 Cl2 O5 K1 -121.9(4) 3_557 . O4 Cl2 O5 K1 -0.7(4) . . O4 Cl2 O5 K1 118.8(4) 3_557 . K1 Cl2 O5 K1 179.91(9) 3_557 . O7 Cl3 O6 K1 0.0 . . O8 Cl3 O6 K1 121.1(3) . . O8 Cl3 O6 K1 -121.1(3) 6_557 . K1 Cl3 O6 K1 180.0 7_565 . O8 Cl3 O7 K1 -120.3(3) . . O8 Cl3 O7 K1 120.3(3) 6_557 . O6 Cl3 O7 K1 0.0 . . K1 Cl3 O7 K1 180.0 7_565 . O7 Cl3 O8 K1 -125.2(4) . 7_565 O8 Cl3 O8 K1 -3.8(6) 6_557 7_565 O6 Cl3 O8 K1 115.2(4) . 7_565