#------------------------------------------------------------------------------ #$Date: 2021-11-04 00:59:31 +0200 (Thu, 04 Nov 2021) $ #$Revision: 270272 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/91/7129192.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_7129192 loop_ _publ_author_name 'Benniston, A. C.' 'Sirbu, Dumitru' 'Tkachenko, Nikolai V.' 'Zeng, Lingli' 'Waddell, Paul G.' 'Botchway, Stanley W.' _publ_section_title ; Voltage-Induced Fluorescence Lifetime Imaging of a BODIPY Derivative in Giant Unilamellar Vesicles (GUVs) as Neuron Membrane Mimics ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D1CC03756K _journal_year 2021 _chemical_formula_moiety 'C H2 Cl2, C26 H28 B F2 N3' _chemical_formula_sum 'C27 H30 B Cl2 F2 N3' _chemical_formula_weight 516.25 _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 direct _audit_creation_date 2016-03-17 _audit_creation_method ; Olex2 1.2 (compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998) ; _audit_update_record ; 2021-06-23 deposited with the CCDC. 2021-11-01 downloaded from the CCDC. ; _cell_angle_alpha 85.621(5) _cell_angle_beta 75.257(6) _cell_angle_gamma 61.941(6) _cell_formula_units_Z 2 _cell_length_a 11.0740(7) _cell_length_b 11.1150(6) _cell_length_c 12.1059(9) _cell_measurement_reflns_used 4452 _cell_measurement_temperature 150.0(2) _cell_measurement_theta_max 66.6370 _cell_measurement_theta_min 3.7550 _cell_volume 1270.01(16) _computing_cell_refinement 'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)' _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 'XT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.0(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3968 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -99.00 -18.00 1.00 1.00 -- -41.59 125.00-120.00 81 2 \w 15.00 117.00 1.00 1.00 -- 41.59 38.00-150.00 102 3 \w 8.00 120.00 1.00 1.00 -- 41.59 77.00 90.00 112 4 \w -3.00 96.00 1.00 1.00 -- 41.59-125.00 0.00 99 5 \w 9.00 133.00 1.00 4.00 -- 93.50 -93.00-167.58 124 6 \w 9.00 133.00 1.00 4.00 -- 93.50 -93.00 78.60 124 7 \w 9.00 133.00 1.00 4.00 -- 93.50 -93.00 -74.89 124 8 \w 9.00 133.00 1.00 4.00 -- 93.50 -93.00 127.80 124 9 \w 9.00 133.00 1.00 4.00 -- 93.50 -93.00 -1.63 124 10 \w 4.00 178.00 1.00 4.00 -- 93.50 0.00-120.00 174 11 \w 63.00 168.00 1.00 4.00 -- 93.50 61.00 60.00 105 12 \w 63.00 168.00 1.00 4.00 -- 93.50 61.00 120.00 105 13 \w 66.00 168.00 1.00 4.00 -- 93.50 45.00 60.00 102 14 \w 16.00 119.00 1.00 4.00 -- 93.50 -30.00 150.00 103 15 \w 74.00 100.00 1.00 4.00 -- 93.50 -91.00-119.74 26 16 \w 66.00 146.00 1.00 4.00 -- 93.50 61.00 150.00 80 17 \w 19.00 55.00 1.00 4.00 -- 93.50 -45.00 -30.00 36 18 \w 96.00 121.00 1.00 4.00 -- 93.50 -45.00 -30.00 25 19 \w 64.00 123.00 1.00 4.00 -- 93.50 -61.00-180.00 59 20 \w 19.00 84.00 1.00 4.00 -- 93.50-125.00 0.00 65 21 \w 66.00 123.00 1.00 4.00 -- 93.50 -61.00 60.00 57 22 \w 91.00 139.00 1.00 4.00 -- 93.50 125.00 60.00 48 23 \w 38.00 81.00 1.00 4.00 -- 93.50 -94.00-150.00 43 24 \w 16.00 48.00 1.00 4.00 -- 93.50 -94.00-120.00 32 25 \w 60.00 123.00 1.00 4.00 -- 93.50 -93.00 58.58 63 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0031970000 _diffrn_orient_matrix_UB_12 0.0208993000 _diffrn_orient_matrix_UB_13 0.1233685000 _diffrn_orient_matrix_UB_21 -0.0999758000 _diffrn_orient_matrix_UB_22 0.1536990000 _diffrn_orient_matrix_UB_23 -0.0021254000 _diffrn_orient_matrix_UB_31 -0.1283772000 _diffrn_orient_matrix_UB_32 -0.0259353000 _diffrn_orient_matrix_UB_33 0.0462213000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_unetI/netI 0.0499 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 18190 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 66.936 _diffrn_reflns_theta_min 3.781 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance Ultra (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.596 _exptl_absorpt_correction_T_max 0.753 _exptl_absorpt_correction_T_min 0.489 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour green _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.350 _exptl_crystal_description plate _exptl_crystal_F_000 540 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.791 _refine_diff_density_min -0.626 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 318 _refine_ls_number_reflns 4498 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0497 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+1.0447P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1095 _refine_ls_wR_factor_ref 0.1251 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3431 _reflns_number_total 4498 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cc03756k2.cif _cod_data_source_block acb160009_sa _cod_database_code 7129192 _shelxl_version_number 2014/6 _chemical_oxdiff_formula 'C27 H30 B1 Cl2 F2 N3' _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. ; _reflns_odcompleteness_completeness 99.71 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C12(H12A,H12B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A, H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B) 2.b Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17), C21(H21) 2.c Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C13(H13A,H13B,H13C) ; _shelx_res_file ; TITL acb160009_sa_a.res in P-1 REM Old TITL acb160009_sa in P-1 #2 REM SHELXT solution in P-1 REM R1 0.169, Rweak 0.008, Alpha 0.038, Orientation as input REM Formula found by SHELXT: C11 B N3 F2 Cl2 CELL 1.54184 11.074 11.115 12.1059 85.621 75.257 61.941 ZERR 2 0.0007 0.0006 0.0009 0.005 0.006 0.006 LATT 1 SFAC C H B Cl F N UNIT 54 60 2 4 4 6 L.S. 4 0 0 PLAN 20 TEMP -123.1(2) BOND $H LIST 4 MORE -1 CONF fmap 2 53 acta 133 REM REM REM WGHT 0.035900 1.044700 FVAR 0.50083 CL1 4 0.161396 0.184555 0.845537 11.00000 0.05275 0.05961 = 0.04990 0.00898 -0.01387 -0.02979 CL2 4 0.449855 0.053369 0.873486 11.00000 0.07195 0.08515 = 0.07965 0.01489 -0.04330 -0.03392 F1 5 0.291804 0.951769 0.619075 11.00000 0.14047 0.04875 = 0.05224 0.01509 -0.05605 -0.05321 F2 5 0.474351 0.838482 0.467678 11.00000 0.03867 0.04947 = 0.12250 0.03554 -0.03963 -0.02642 N1 6 0.263611 1.024336 0.432201 11.00000 0.03107 0.03187 = 0.03559 0.00308 -0.00893 -0.01415 N2 6 0.269004 0.804561 0.498870 11.00000 0.02600 0.03059 = 0.02667 0.00464 -0.00992 -0.01301 N3 6 0.791745 0.354067 0.985481 11.00000 0.02993 0.04802 = 0.03257 0.00553 -0.01534 -0.01653 C1 1 0.152684 0.707319 0.439433 11.00000 0.02407 0.03529 = 0.02473 0.00171 -0.00518 -0.01319 C2 1 0.231951 0.618378 0.509065 11.00000 0.02465 0.03420 = 0.02611 0.00125 -0.00612 -0.01370 C3 1 0.302400 0.682065 0.547388 11.00000 0.02652 0.03029 = 0.02522 0.00101 -0.00616 -0.01176 C5 1 0.287556 1.134357 0.416042 11.00000 0.03837 0.03434 = 0.04194 -0.00003 -0.00278 -0.01861 AFIX 43 H5 2 0.349510 1.148877 0.448522 11.00000 -1.20000 AFIX 0 C6 1 0.208117 1.221829 0.345222 11.00000 0.04550 0.03375 = 0.04101 0.00751 -0.00417 -0.01822 AFIX 43 H6 2 0.205510 1.306141 0.320894 11.00000 -1.20000 AFIX 0 C7 1 0.132625 1.163699 0.316084 11.00000 0.04183 0.03584 = 0.03519 0.00822 -0.01069 -0.01323 AFIX 43 H7 2 0.069082 1.200672 0.268017 11.00000 -1.20000 AFIX 0 C8 1 0.124811 0.939812 0.372318 11.00000 0.02755 0.03500 = 0.02754 0.00305 -0.00948 -0.01098 AFIX 43 H8 2 0.058269 0.952039 0.330524 11.00000 -1.20000 AFIX 0 C9 1 0.176041 0.824852 0.432169 11.00000 0.02304 0.03274 = 0.02525 -0.00001 -0.00719 -0.01018 C10 1 0.167869 1.040514 0.370885 11.00000 0.03124 0.03266 = 0.02859 0.00227 -0.00618 -0.01091 C11 1 0.059747 0.690034 0.379192 11.00000 0.03317 0.04187 = 0.03364 0.00317 -0.01378 -0.01827 AFIX 137 H11A 2 -0.020975 0.779002 0.375617 11.00000 -1.50000 H11B 2 0.025696 0.628350 0.420872 11.00000 -1.50000 H11C 2 0.113357 0.651372 0.301442 11.00000 -1.50000 AFIX 0 C12 1 0.242259 0.480010 0.537034 11.00000 0.03831 0.03276 = 0.03726 0.00360 -0.01616 -0.01820 AFIX 23 H12A 2 0.342228 0.414011 0.533013 11.00000 -1.20000 H12B 2 0.212974 0.449957 0.478187 11.00000 -1.20000 AFIX 0 C13 1 0.152816 0.476174 0.654029 11.00000 0.03902 0.04328 = 0.04753 0.01503 -0.01540 -0.02523 AFIX 137 H13A 2 0.053045 0.538198 0.657853 11.00000 -1.50000 H13B 2 0.181580 0.504798 0.713116 11.00000 -1.50000 H13C 2 0.166092 0.383050 0.666631 11.00000 -1.50000 AFIX 0 C14 1 0.390766 0.640851 0.626099 11.00000 0.02864 0.03829 = 0.02870 0.00365 -0.01043 -0.01570 AFIX 43 H14 2 0.417494 0.705328 0.643809 11.00000 -1.20000 AFIX 0 C15 1 0.440223 0.521592 0.677776 11.00000 0.02654 0.03694 = 0.03216 0.00306 -0.00755 -0.01673 AFIX 43 H15 2 0.416687 0.455202 0.658802 11.00000 -1.20000 AFIX 0 C16 1 0.525870 0.484884 0.759516 11.00000 0.02154 0.03923 = 0.02657 0.00354 -0.00496 -0.01410 C17 1 0.564716 0.573567 0.800252 11.00000 0.02585 0.03317 = 0.02869 0.00769 -0.00426 -0.01150 AFIX 43 H17 2 0.533131 0.663218 0.773275 11.00000 -1.20000 AFIX 0 C18 1 0.647419 0.534962 0.878340 11.00000 0.02409 0.04112 = 0.02544 0.00204 -0.00298 -0.01601 C19 1 0.698453 0.399888 0.916549 11.00000 0.02226 0.04129 = 0.02275 0.00413 -0.00445 -0.01368 C20 1 0.656593 0.311196 0.878971 11.00000 0.02285 0.03884 = 0.02640 0.00364 -0.00531 -0.01276 C21 1 0.573174 0.354960 0.802483 11.00000 0.02588 0.03921 = 0.03214 0.00592 -0.00923 -0.01740 AFIX 43 H21 2 0.546559 0.293812 0.777789 11.00000 -1.20000 AFIX 0 C22 1 0.682792 0.633091 0.923456 11.00000 0.03748 0.04898 = 0.03540 -0.00046 -0.00597 -0.02503 AFIX 23 H22A 2 0.608975 0.683324 0.992952 11.00000 -1.20000 H22B 2 0.684779 0.700357 0.865445 11.00000 -1.20000 AFIX 0 C23 1 0.825636 0.557845 0.952175 11.00000 0.03635 0.06105 = 0.04508 -0.00875 -0.00728 -0.02797 AFIX 23 H23A 2 0.901307 0.515759 0.881524 11.00000 -1.20000 H23B 2 0.844425 0.622592 0.987720 11.00000 -1.20000 AFIX 0 C24 1 0.824009 0.448402 1.034243 11.00000 0.02925 0.06224 = 0.03761 -0.00520 -0.01309 -0.01815 AFIX 23 H24A 2 0.917363 0.397180 1.052029 11.00000 -1.20000 H24B 2 0.752293 0.491786 1.106565 11.00000 -1.20000 AFIX 0 C25 1 0.702420 0.169176 0.923899 11.00000 0.03231 0.03978 = 0.03991 0.01062 -0.00895 -0.01593 AFIX 23 H25A 2 0.627310 0.170771 0.989865 11.00000 -1.20000 H25B 2 0.716022 0.105603 0.863458 11.00000 -1.20000 AFIX 0 C26 1 0.838697 0.118482 0.960654 11.00000 0.03191 0.04150 = 0.04362 0.01295 -0.01221 -0.00956 AFIX 23 H26A 2 0.859016 0.032156 1.000024 11.00000 -1.20000 H26B 2 0.917929 0.100295 0.892601 11.00000 -1.20000 AFIX 0 C27 1 0.825187 0.224773 1.040344 11.00000 0.03079 0.05210 = 0.03792 0.01336 -0.01551 -0.01069 AFIX 23 H27A 2 0.749765 0.238431 1.110422 11.00000 -1.20000 H27B 2 0.914985 0.192233 1.062990 11.00000 -1.20000 AFIX 0 C28 1 0.343224 0.106436 0.779486 11.00000 0.04920 0.12813 = 0.04811 -0.00418 -0.01538 -0.04035 AFIX 23 H28A 2 0.366900 0.026509 0.731323 11.00000 -1.20000 H28B 2 0.364240 0.171699 0.728384 11.00000 -1.20000 AFIX 0 B4 3 0.327794 0.904924 0.507309 11.00000 0.04588 0.03429 = 0.04481 0.00863 -0.02362 -0.02200 HKLF 4 REM acb160009_sa_a.res in P-1 REM R1 = 0.0497 for 3431 Fo > 4sig(Fo) and 0.0712 for all 4498 data REM 318 parameters refined using 0 restraints END WGHT 0.0359 1.0447 REM Highest difference peak 0.791, deepest hole -0.626, 1-sigma level 0.052 Q1 1 0.4382 -0.0029 0.8373 11.00000 0.05 0.79 Q2 1 0.4421 0.1264 0.8355 11.00000 0.05 0.33 Q3 1 0.4227 0.8669 0.5464 11.00000 0.05 0.27 Q4 1 0.4482 0.6235 0.6971 11.00000 0.05 0.26 Q5 1 0.3655 0.1064 0.7073 11.00000 0.05 0.23 Q6 1 0.0803 0.6010 0.3552 11.00000 0.05 0.23 Q7 1 0.0385 0.7351 0.3062 11.00000 0.05 0.23 Q8 1 0.3306 0.0355 0.7977 11.00000 0.05 0.22 Q9 1 0.1861 1.0453 0.4376 11.00000 0.05 0.19 Q10 1 -0.0408 0.7382 0.4407 11.00000 0.05 0.19 Q11 1 0.2851 0.9832 0.4639 11.00000 0.05 0.19 Q12 1 0.5461 0.5486 0.7641 11.00000 0.05 0.18 Q13 1 0.3043 0.8452 0.5040 11.00000 0.05 0.18 Q14 1 0.6773 0.5636 0.9026 11.00000 0.05 0.17 Q15 1 0.2418 0.6599 0.5591 11.00000 0.05 0.17 Q16 1 0.6897 0.2297 0.8857 11.00000 0.05 0.16 Q17 1 0.2263 0.8209 0.4650 11.00000 0.05 0.16 Q18 1 0.1821 0.1861 0.9224 11.00000 0.05 0.16 Q19 1 0.1414 0.7756 0.4382 11.00000 0.05 0.16 Q20 1 0.5647 0.4239 0.7830 11.00000 0.05 0.16 ; _shelx_res_checksum 75222 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: ; _oxdiff_exptl_absorpt_empirical_full_max 1.490 _oxdiff_exptl_absorpt_empirical_full_min 0.798 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 Cl1 Cl 0.16140(8) 0.18456(8) 0.84554(7) 0.0528(2) Uani 1 1 d . . . . . Cl2 Cl 0.44985(11) 0.05337(11) 0.87349(9) 0.0757(3) Uani 1 1 d . . . . . F1 F 0.2918(3) 0.95177(19) 0.61908(17) 0.0709(6) Uani 1 1 d . . . . . F2 F 0.47435(18) 0.83848(18) 0.4677(2) 0.0656(6) Uani 1 1 d . . . . . N1 N 0.2636(2) 1.0243(2) 0.43220(18) 0.0330(5) Uani 1 1 d . . . . . N2 N 0.2690(2) 0.8046(2) 0.49887(17) 0.0273(4) Uani 1 1 d . . . . . N3 N 0.7917(2) 0.3541(2) 0.98548(19) 0.0362(5) Uani 1 1 d . . . . . C1 C 0.1527(2) 0.7073(2) 0.4394(2) 0.0285(5) Uani 1 1 d . . . . . C2 C 0.2320(2) 0.6184(2) 0.5091(2) 0.0284(5) Uani 1 1 d . . . . . C3 C 0.3024(2) 0.6821(2) 0.5474(2) 0.0280(5) Uani 1 1 d . . . . . C5 C 0.2876(3) 1.1344(3) 0.4160(2) 0.0389(6) Uani 1 1 d . . . . . H5 H 0.3495 1.1489 0.4485 0.047 Uiso 1 1 calc R . . . . C6 C 0.2081(3) 1.2218(3) 0.3452(2) 0.0419(6) Uani 1 1 d . . . . . H6 H 0.2055 1.3061 0.3209 0.050 Uiso 1 1 calc R . . . . C7 C 0.1326(3) 1.1637(3) 0.3161(2) 0.0398(6) Uani 1 1 d . . . . . H7 H 0.0691 1.2007 0.2680 0.048 Uiso 1 1 calc R . . . . C8 C 0.1248(3) 0.9398(3) 0.3723(2) 0.0311(5) Uani 1 1 d . . . . . H8 H 0.0583 0.9520 0.3305 0.037 Uiso 1 1 calc R . . . . C9 C 0.1760(2) 0.8249(2) 0.4322(2) 0.0279(5) Uani 1 1 d . . . . . C10 C 0.1679(3) 1.0405(3) 0.3709(2) 0.0328(5) Uani 1 1 d . . . . . C11 C 0.0597(3) 0.6900(3) 0.3792(2) 0.0349(6) Uani 1 1 d . . . . . H11A H -0.0210 0.7790 0.3756 0.052 Uiso 1 1 calc GR . . . . H11B H 0.0257 0.6283 0.4209 0.052 Uiso 1 1 calc GR . . . . H11C H 0.1134 0.6514 0.3014 0.052 Uiso 1 1 calc GR . . . . C12 C 0.2423(3) 0.4800(3) 0.5370(2) 0.0342(6) Uani 1 1 d . . . . . H12A H 0.3422 0.4140 0.5330 0.041 Uiso 1 1 calc R . . . . H12B H 0.2130 0.4500 0.4782 0.041 Uiso 1 1 calc R . . . . C13 C 0.1528(3) 0.4762(3) 0.6540(2) 0.0406(6) Uani 1 1 d . . . . . H13A H 0.0530 0.5382 0.6579 0.061 Uiso 1 1 calc GR . . . . H13B H 0.1816 0.5048 0.7131 0.061 Uiso 1 1 calc GR . . . . H13C H 0.1661 0.3831 0.6666 0.061 Uiso 1 1 calc GR . . . . C14 C 0.3908(3) 0.6409(3) 0.6261(2) 0.0313(5) Uani 1 1 d . . . . . H14 H 0.4175 0.7053 0.6438 0.038 Uiso 1 1 calc R . . . . C15 C 0.4402(3) 0.5216(3) 0.6778(2) 0.0311(5) Uani 1 1 d . . . . . H15 H 0.4167 0.4552 0.6588 0.037 Uiso 1 1 calc R . . . . C16 C 0.5259(2) 0.4849(3) 0.7595(2) 0.0295(5) Uani 1 1 d . . . . . C17 C 0.5647(2) 0.5736(3) 0.8003(2) 0.0311(5) Uani 1 1 d . . . . . H17 H 0.5331 0.6632 0.7733 0.037 Uiso 1 1 calc R . . . . C18 C 0.6474(2) 0.5350(3) 0.8783(2) 0.0306(5) Uani 1 1 d . . . . . C19 C 0.6985(2) 0.3999(3) 0.9165(2) 0.0296(5) Uani 1 1 d . . . . . C20 C 0.6566(2) 0.3112(3) 0.8790(2) 0.0303(5) Uani 1 1 d . . . . . C21 C 0.5732(3) 0.3550(3) 0.8025(2) 0.0313(5) Uani 1 1 d . . . . . H21 H 0.5466 0.2938 0.7778 0.038 Uiso 1 1 calc R . . . . C22 C 0.6828(3) 0.6331(3) 0.9235(2) 0.0391(6) Uani 1 1 d . . . . . H22A H 0.6090 0.6833 0.9930 0.047 Uiso 1 1 calc R . . . . H22B H 0.6848 0.7004 0.8654 0.047 Uiso 1 1 calc R . . . . C23 C 0.8256(3) 0.5578(3) 0.9522(3) 0.0452(7) Uani 1 1 d . . . . . H23A H 0.9013 0.5158 0.8815 0.054 Uiso 1 1 calc R . . . . H23B H 0.8444 0.6226 0.9877 0.054 Uiso 1 1 calc R . . . . C24 C 0.8240(3) 0.4484(3) 1.0342(2) 0.0429(7) Uani 1 1 d . . . . . H24A H 0.9174 0.3972 1.0520 0.052 Uiso 1 1 calc R . . . . H24B H 0.7523 0.4918 1.1066 0.052 Uiso 1 1 calc R . . . . C25 C 0.7024(3) 0.1692(3) 0.9239(2) 0.0382(6) Uani 1 1 d . . . . . H25A H 0.6273 0.1708 0.9899 0.046 Uiso 1 1 calc R . . . . H25B H 0.7160 0.1056 0.8635 0.046 Uiso 1 1 calc R . . . . C26 C 0.8387(3) 0.1185(3) 0.9607(3) 0.0422(7) Uani 1 1 d . . . . . H26A H 0.8590 0.0322 1.0000 0.051 Uiso 1 1 calc R . . . . H26B H 0.9179 0.1003 0.8926 0.051 Uiso 1 1 calc R . . . . C27 C 0.8252(3) 0.2248(3) 1.0403(2) 0.0431(7) Uani 1 1 d . . . . . H27A H 0.7498 0.2384 1.1104 0.052 Uiso 1 1 calc R . . . . H27B H 0.9150 0.1922 1.0630 0.052 Uiso 1 1 calc R . . . . C28 C 0.3432(4) 0.1064(5) 0.7795(3) 0.0744(12) Uani 1 1 d . . . . . H28A H 0.3669 0.0265 0.7313 0.089 Uiso 1 1 calc R . . . . H28B H 0.3642 0.1717 0.7284 0.089 Uiso 1 1 calc R . . . . B4 B 0.3278(4) 0.9049(3) 0.5073(3) 0.0382(7) Uani 1 1 d . . . . . 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 0.0527(4) 0.0596(5) 0.0499(4) 0.0090(3) -0.0139(3) -0.0298(4) Cl2 0.0719(6) 0.0851(7) 0.0797(6) 0.0149(5) -0.0433(5) -0.0339(5) F1 0.140(2) 0.0488(10) 0.0522(11) 0.0151(8) -0.0561(12) -0.0532(12) F2 0.0387(9) 0.0495(10) 0.1225(18) 0.0355(11) -0.0396(11) -0.0264(8) N1 0.0311(11) 0.0319(11) 0.0356(12) 0.0031(9) -0.0089(9) -0.0142(9) N2 0.0260(10) 0.0306(10) 0.0267(10) 0.0046(8) -0.0099(8) -0.0130(8) N3 0.0299(11) 0.0480(13) 0.0326(11) 0.0055(10) -0.0153(9) -0.0165(10) C1 0.0241(12) 0.0353(13) 0.0247(12) 0.0017(10) -0.0052(9) -0.0132(10) C2 0.0247(12) 0.0342(13) 0.0261(12) 0.0013(10) -0.0061(10) -0.0137(10) C3 0.0265(12) 0.0303(12) 0.0252(12) 0.0010(10) -0.0062(10) -0.0118(10) C5 0.0384(15) 0.0343(14) 0.0419(15) 0.0000(11) -0.0028(12) -0.0186(12) C6 0.0455(16) 0.0337(14) 0.0410(15) 0.0075(12) -0.0042(13) -0.0182(13) C7 0.0418(15) 0.0358(14) 0.0352(14) 0.0082(11) -0.0107(12) -0.0132(12) C8 0.0276(12) 0.0350(13) 0.0275(12) 0.0030(10) -0.0095(10) -0.0110(11) C9 0.0230(11) 0.0327(12) 0.0253(12) 0.0000(10) -0.0072(9) -0.0102(10) C10 0.0312(13) 0.0327(13) 0.0286(13) 0.0023(10) -0.0062(10) -0.0109(11) C11 0.0332(13) 0.0419(14) 0.0336(14) 0.0032(11) -0.0138(11) -0.0183(12) C12 0.0383(14) 0.0328(13) 0.0373(14) 0.0036(11) -0.0162(11) -0.0182(11) C13 0.0390(15) 0.0433(15) 0.0475(16) 0.0150(13) -0.0154(12) -0.0252(13) C14 0.0286(12) 0.0383(13) 0.0287(12) 0.0036(10) -0.0104(10) -0.0157(11) C15 0.0265(12) 0.0369(13) 0.0322(13) 0.0031(10) -0.0075(10) -0.0167(11) C16 0.0215(11) 0.0392(13) 0.0266(12) 0.0035(10) -0.0050(9) -0.0141(10) C17 0.0259(12) 0.0332(13) 0.0287(13) 0.0077(10) -0.0043(10) -0.0115(10) C18 0.0241(12) 0.0411(14) 0.0254(12) 0.0020(10) -0.0030(10) -0.0160(11) C19 0.0223(11) 0.0413(14) 0.0227(12) 0.0041(10) -0.0045(9) -0.0137(10) C20 0.0229(12) 0.0388(13) 0.0264(12) 0.0036(10) -0.0053(10) -0.0128(10) C21 0.0259(12) 0.0392(14) 0.0321(13) 0.0059(11) -0.0092(10) -0.0174(11) C22 0.0375(14) 0.0490(16) 0.0354(14) -0.0005(12) -0.0060(12) -0.0250(13) C23 0.0364(15) 0.0610(18) 0.0451(16) -0.0087(14) -0.0073(12) -0.0280(14) C24 0.0293(13) 0.0622(18) 0.0376(15) -0.0052(13) -0.0131(12) -0.0182(13) C25 0.0323(14) 0.0398(14) 0.0399(15) 0.0106(12) -0.0089(11) -0.0159(12) C26 0.0319(14) 0.0415(15) 0.0436(16) 0.0130(12) -0.0122(12) -0.0096(12) C27 0.0308(14) 0.0521(16) 0.0379(15) 0.0134(13) -0.0155(12) -0.0107(12) C28 0.049(2) 0.128(4) 0.048(2) -0.004(2) -0.0154(16) -0.040(2) B4 0.0459(18) 0.0343(15) 0.0448(18) 0.0086(13) -0.0236(15) -0.0220(14) 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' B B 0.0090 0.0039 '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' F F 0.0727 0.0534 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0168 0 0 -1 0.0288 1 1 0 0.1067 -1 -1 0 0.0607 1 2 -1 0.1050 -1 0 0 0.2302 1 0 0 0.1382 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 C5 N1 C10 107.8(2) . . ? C5 N1 B4 126.5(2) . . ? C10 N1 B4 125.7(2) . . ? C3 N2 C9 108.44(19) . . ? C3 N2 B4 127.8(2) . . ? C9 N2 B4 123.68(19) . . ? C19 N3 C24 120.7(2) . . ? C19 N3 C27 120.4(2) . . ? C27 N3 C24 116.1(2) . . ? C2 C1 C9 107.4(2) . . ? C2 C1 C11 128.3(2) . . ? C9 C1 C11 124.2(2) . . ? C1 C2 C3 107.2(2) . . ? C1 C2 C12 125.2(2) . . ? C3 C2 C12 127.6(2) . . ? N2 C3 C2 108.9(2) . . ? N2 C3 C14 119.3(2) . . ? C14 C3 C2 131.8(2) . . ? N1 C5 H5 125.2 . . ? N1 C5 C6 109.6(3) . . ? C6 C5 H5 125.2 . . ? C5 C6 H6 126.3 . . ? C5 C6 C7 107.3(2) . . ? C7 C6 H6 126.3 . . ? C6 C7 H7 126.4 . . ? C6 C7 C10 107.1(2) . . ? C10 C7 H7 126.4 . . ? C9 C8 H8 119.1 . . ? C9 C8 C10 121.8(2) . . ? C10 C8 H8 119.1 . . ? N2 C9 C1 107.96(19) . . ? C8 C9 N2 121.5(2) . . ? C8 C9 C1 130.5(2) . . ? N1 C10 C7 108.2(2) . . ? N1 C10 C8 119.6(2) . . ? C7 C10 C8 132.3(2) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 C12 H12A 108.7 . . ? C2 C12 H12B 108.7 . . ? C2 C12 C13 114.1(2) . . ? H12A C12 H12B 107.6 . . ? C13 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C3 C14 H14 116.2 . . ? C15 C14 C3 127.7(2) . . ? C15 C14 H14 116.2 . . ? C14 C15 H15 116.9 . . ? C14 C15 C16 126.2(2) . . ? C16 C15 H15 116.9 . . ? C17 C16 C15 123.9(2) . . ? C21 C16 C15 119.3(2) . . ? C21 C16 C17 116.8(2) . . ? C16 C17 H17 118.8 . . ? C18 C17 C16 122.5(2) . . ? C18 C17 H17 118.8 . . ? C17 C18 C19 119.1(2) . . ? C17 C18 C22 121.3(2) . . ? C19 C18 C22 119.6(2) . . ? N3 C19 C18 120.6(2) . . ? N3 C19 C20 120.4(2) . . ? C20 C19 C18 118.9(2) . . ? C19 C20 C25 120.0(2) . . ? C21 C20 C19 119.6(2) . . ? C21 C20 C25 120.3(2) . . ? C16 C21 H21 118.5 . . ? C20 C21 C16 123.0(2) . . ? C20 C21 H21 118.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? C18 C22 C23 110.6(2) . . ? H22A C22 H22B 108.1 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? C22 C23 H23A 109.9 . . ? C22 C23 H23B 109.9 . . ? H23A C23 H23B 108.3 . . ? C24 C23 C22 108.7(2) . . ? C24 C23 H23A 109.9 . . ? C24 C23 H23B 109.9 . . ? N3 C24 C23 111.1(2) . . ? N3 C24 H24A 109.4 . . ? N3 C24 H24B 109.4 . . ? C23 C24 H24A 109.4 . . ? C23 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C20 C25 H25A 109.4 . . ? C20 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? C26 C25 C20 111.2(2) . . ? C26 C25 H25A 109.4 . . ? C26 C25 H25B 109.4 . . ? C25 C26 H26A 109.7 . . ? C25 C26 H26B 109.7 . . ? H26A C26 H26B 108.2 . . ? C27 C26 C25 109.6(2) . . ? C27 C26 H26A 109.7 . . ? C27 C26 H26B 109.7 . . ? N3 C27 C26 110.9(2) . . ? N3 C27 H27A 109.5 . . ? N3 C27 H27B 109.5 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 108.0 . . ? Cl1 C28 H28A 108.7 . . ? Cl1 C28 H28B 108.7 . . ? Cl2 C28 Cl1 114.2(2) . . ? Cl2 C28 H28A 108.7 . . ? Cl2 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? F1 B4 F2 109.2(2) . . ? F1 B4 N1 110.2(2) . . ? F1 B4 N2 110.3(2) . . ? F2 B4 N1 109.8(2) . . ? F2 B4 N2 109.6(2) . . ? N1 B4 N2 107.7(2) . . ? 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 Cl1 C28 1.758(4) . ? Cl2 C28 1.721(4) . ? F1 B4 1.378(4) . ? F2 B4 1.393(4) . ? N1 C5 1.359(3) . ? N1 C10 1.381(3) . ? N1 B4 1.533(4) . ? N2 C3 1.360(3) . ? N2 C9 1.393(3) . ? N2 B4 1.553(3) . ? N3 C19 1.379(3) . ? N3 C24 1.459(4) . ? N3 C27 1.457(4) . ? C1 C2 1.375(3) . ? C1 C9 1.439(3) . ? C1 C11 1.489(3) . ? C2 C3 1.442(3) . ? C2 C12 1.506(3) . ? C3 C14 1.436(3) . ? C5 H5 0.9500 . ? C5 C6 1.381(4) . ? C6 H6 0.9500 . ? C6 C7 1.391(4) . ? C7 H7 0.9500 . ? C7 C10 1.399(4) . ? C8 H8 0.9500 . ? C8 C9 1.366(3) . ? C8 C10 1.406(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C13 1.518(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14 0.9500 . ? C14 C15 1.347(4) . ? C15 H15 0.9500 . ? C15 C16 1.448(3) . ? C16 C17 1.407(4) . ? C16 C21 1.394(4) . ? C17 H17 0.9500 . ? C17 C18 1.388(4) . ? C18 C19 1.420(4) . ? C18 C22 1.498(4) . ? C19 C20 1.414(4) . ? C20 C21 1.375(3) . ? C20 C25 1.517(4) . ? C21 H21 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 C23 1.521(4) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 C24 1.515(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C25 C26 1.515(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C26 C27 1.511(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? 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 N1 C5 C6 C7 -0.2(3) . . . . ? N2 C3 C14 C15 -176.5(2) . . . . ? N3 C19 C20 C21 -174.4(2) . . . . ? N3 C19 C20 C25 6.2(3) . . . . ? C1 C2 C3 N2 -1.7(3) . . . . ? C1 C2 C3 C14 175.7(3) . . . . ? C1 C2 C12 C13 -101.6(3) . . . . ? C2 C1 C9 N2 -0.4(3) . . . . ? C2 C1 C9 C8 178.4(3) . . . . ? C2 C3 C14 C15 6.3(5) . . . . ? C3 N2 C9 C1 -0.7(3) . . . . ? C3 N2 C9 C8 -179.6(2) . . . . ? C3 N2 B4 F1 -62.9(3) . . . . ? C3 N2 B4 F2 57.4(3) . . . . ? C3 N2 B4 N1 176.8(2) . . . . ? C3 C2 C12 C13 79.3(3) . . . . ? C3 C14 C15 C16 -178.0(2) . . . . ? C5 N1 C10 C7 0.0(3) . . . . ? C5 N1 C10 C8 179.7(2) . . . . ? C5 N1 B4 F1 59.5(4) . . . . ? C5 N1 B4 F2 -60.9(4) . . . . ? C5 N1 B4 N2 179.9(2) . . . . ? C5 C6 C7 C10 0.2(3) . . . . ? C6 C7 C10 N1 -0.1(3) . . . . ? C6 C7 C10 C8 -179.8(3) . . . . ? C9 N2 C3 C2 1.5(3) . . . . ? C9 N2 C3 C14 -176.3(2) . . . . ? C9 N2 B4 F1 121.0(3) . . . . ? C9 N2 B4 F2 -118.7(3) . . . . ? C9 N2 B4 N1 0.7(3) . . . . ? C9 C1 C2 C3 1.3(3) . . . . ? C9 C1 C2 C12 -178.0(2) . . . . ? C9 C8 C10 N1 -0.6(4) . . . . ? C9 C8 C10 C7 179.1(3) . . . . ? C10 N1 C5 C6 0.2(3) . . . . ? C10 N1 B4 F1 -118.8(3) . . . . ? C10 N1 B4 F2 120.8(3) . . . . ? C10 N1 B4 N2 1.6(4) . . . . ? C10 C8 C9 N2 2.8(4) . . . . ? C10 C8 C9 C1 -175.9(2) . . . . ? C11 C1 C2 C3 -179.5(2) . . . . ? C11 C1 C2 C12 1.2(4) . . . . ? C11 C1 C9 N2 -179.7(2) . . . . ? C11 C1 C9 C8 -0.8(4) . . . . ? C12 C2 C3 N2 177.5(2) . . . . ? C12 C2 C3 C14 -5.1(4) . . . . ? C14 C15 C16 C17 2.8(4) . . . . ? C14 C15 C16 C21 -177.7(2) . . . . ? C15 C16 C17 C18 -179.8(2) . . . . ? C15 C16 C21 C20 179.0(2) . . . . ? C16 C17 C18 C19 1.8(4) . . . . ? C16 C17 C18 C22 -177.8(2) . . . . ? C17 C16 C21 C20 -1.5(4) . . . . ? C17 C18 C19 N3 173.8(2) . . . . ? C17 C18 C19 C20 -3.7(3) . . . . ? C17 C18 C22 C23 -149.9(2) . . . . ? C18 C19 C20 C21 3.0(3) . . . . ? C18 C19 C20 C25 -176.4(2) . . . . ? C18 C22 C23 C24 -55.0(3) . . . . ? C19 N3 C24 C23 -35.3(3) . . . . ? C19 N3 C27 C26 39.5(3) . . . . ? C19 C18 C22 C23 30.5(3) . . . . ? C19 C20 C21 C16 -0.4(4) . . . . ? C19 C20 C25 C26 -26.2(3) . . . . ? C20 C25 C26 C27 51.1(3) . . . . ? C21 C16 C17 C18 0.8(3) . . . . ? C21 C20 C25 C26 154.5(2) . . . . ? C22 C18 C19 N3 -6.7(3) . . . . ? C22 C18 C19 C20 175.9(2) . . . . ? C22 C23 C24 N3 57.7(3) . . . . ? C24 N3 C19 C18 9.0(3) . . . . ? C24 N3 C19 C20 -173.6(2) . . . . ? C24 N3 C27 C26 -159.2(2) . . . . ? C25 C20 C21 C16 179.0(2) . . . . ? C25 C26 C27 N3 -58.0(3) . . . . ? C27 N3 C19 C18 169.5(2) . . . . ? C27 N3 C19 C20 -13.1(4) . . . . ? C27 N3 C24 C23 163.5(2) . . . . ? B4 N1 C5 C6 -178.4(3) . . . . ? B4 N1 C10 C7 178.5(3) . . . . ? B4 N1 C10 C8 -1.7(4) . . . . ? B4 N2 C3 C2 -175.1(2) . . . . ? B4 N2 C3 C14 7.1(4) . . . . ? B4 N2 C9 C1 176.1(2) . . . . ? B4 N2 C9 C8 -2.9(4) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.0004 -0.0003 1.0002 0.1234 -0.0022 0.0462 -0.0004 0.0003 -1.0002 -0.1234 0.0022 -0.0462 1.0002 1.0002 -0.0006 0.0240 0.0537 -0.1544 -1.0002 -1.0002 0.0006 -0.0240 -0.0537 0.1544 0.9998 2.0003 -1.0005 -0.0784 0.2096 -0.2265 -1.0002 -0.0003 0.0009 -0.0031 0.0999 0.1284 1.0002 0.0003 -0.0009 0.0031 -0.0999 -0.1284