#------------------------------------------------------------------------------ #$Date: 2022-11-24 10:54:53 +0200 (Thu, 24 Nov 2022) $ #$Revision: 279538 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106240.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_8106240 loop_ _publ_author_name 'Yun, Meng' 'Dong, Xiu-Yan' _publ_section_title ; Synthesis and crystal structure of 6-carboxy-1-(3,5-dicarboxyphenyl)-1H-benzo[d]imidazol-3-ium-5-carboxylate dihydrate, C18H12N2O8 ; _journal_issue 4 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 633 _journal_page_last 634 _journal_paper_doi 10.1515/ncrs-2017-0396 _journal_volume 233 _journal_year 2018 _chemical_formula_moiety 'C18 H12 N2 O8, 2(H2 O)' _chemical_formula_sum 'C18 H16 N2 O10' _chemical_formula_weight 420.33 _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 direct _cell_angle_alpha 66.892(3) _cell_angle_beta 86.069(3) _cell_angle_gamma 81.658(4) _cell_formula_units_Z 2 _cell_length_a 8.4592(10) _cell_length_b 9.8442(11) _cell_length_c 11.2565(12) _cell_measurement_reflns_used 2475 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 27.43 _cell_measurement_theta_min 2.27 _cell_volume 852.97(17) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'ShelXS-1997 (Sheldrick, 2008)' _diffrn_ambient_temperature 153.15 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_unetI/netI 0.0647 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 7338 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 27.483 _diffrn_reflns_theta_min 2.268 _exptl_absorpt_coefficient_mu 0.136 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.637 _exptl_crystal_description ; ; _exptl_crystal_F_000 436 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.367 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.066 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 287 _refine_ls_number_reflns 3876 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0609 _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^)+(0.0607P)^2^+0.8921P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1395 _refine_ls_wR_factor_ref 0.1557 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2732 _reflns_number_total 3876 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file suppl_ncrs-2017-0396_suppl.cif _cod_data_source_block zd_d2_0m_a_sq _cod_database_code 8106240 _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 0.976 _shelx_estimated_absorpt_t_min 0.971 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All O(H) groups, All O(H,H) groups 2. Restrained distances H9B-O9 0.84 with sigma of 0.02 O8-H8 0.84 with sigma of 0.02 O9-H9A 0.84 with sigma of 0.02 O10-H10D 0.84 with sigma of 0.02 O10-H10C 0.84 with sigma of 0.02 3.a Free rotating group: O9(H9A), O10(H10C,H10D) 3.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B) 3.c Aromatic/amide H refined with riding coordinates: N1(H1A), C14(H14), C16(H16), C12(H12), C9(H9), C3(H3), C6(H6A) 3.d Idealised tetrahedral OH refined as rotating group: O6(H6), O1(H1) ; _shelx_res_file ; 20170925lzd_d2_0m_a_sq.res created by SHELXL-2014/7 TITL 20170925lzd_d2_0m_a_sq_a.res in P-1 REM Old TITL 20170925lzd_d2_0m_a_sq in P-1 #2 REM SHELXT solution in P-1 REM R1 0.156, Rweak 0.011, Alpha 0.037, Orientation as input REM Formula found by SHELXT: C18 N4 O8 CELL 0.71073 8.4592 9.8442 11.2565 66.892 86.069 81.658 ZERR 2 0.001 0.0011 0.0012 0.003 0.003 0.004 LATT 1 SFAC C H N O UNIT 36 32 4 20 DFIX 0.84 H9b O9 DFIX 0.84 O8 H8 DFIX 0.84 O9 H9a DFIX 0.84 O10 H10d DFIX 0.84 O10 H10c L.S. 4 0 0 PLAN 20 SIZE 0.22 0.19 0.18 TEMP -120 BOND $H LIST 6 MORE -1 CONF fmap 2 53 acta 52 REM REM REM WGHT 0.060700 0.892100 FVAR 0.70557 O7 4 0.824351 0.214710 1.279236 11.00000 0.03505 0.02012 = 0.01548 0.00125 0.00262 0.00618 O6 4 0.473135 0.686737 1.142704 11.00000 0.03570 0.02620 = 0.01756 -0.00479 0.00041 0.01285 AFIX 147 H6 2 0.405009 0.752481 1.152960 11.00000 -1.50000 AFIX 0 O8 4 0.977838 0.156194 1.133173 11.00000 0.03764 0.02950 = 0.02008 -0.00264 -0.00306 0.01809 O3 4 0.132441 0.974188 0.325674 11.00000 0.03160 0.03585 = 0.02458 -0.01203 -0.00462 0.01678 O1 4 0.294395 0.473986 0.631430 11.00000 0.03085 0.02832 = 0.02864 -0.00303 -0.00583 -0.00446 AFIX 147 H1 2 0.221732 0.420741 0.640578 11.00000 -1.50000 AFIX 0 O5 4 0.459817 0.845376 0.936094 11.00000 0.04733 0.02495 = 0.02205 -0.00073 0.00075 0.01443 O4 4 0.244638 0.854207 0.204612 11.00000 0.03372 0.04525 = 0.02491 -0.01760 -0.00709 0.01528 O2 4 0.142053 0.633787 0.469001 11.00000 0.02801 0.03707 = 0.03048 -0.00725 -0.00493 0.00040 AFIX 6 O9 4 0.106152 0.280027 0.712094 11.00000 0.03558 0.03507 = 0.04442 -0.00526 -0.01266 -0.00411 H9A 2 0.132774 0.210686 0.787003 11.00000 -1.50000 AFIX 0 N2 3 0.796924 0.717061 0.600727 11.00000 0.02305 0.02227 = 0.01317 -0.00478 0.00077 0.00452 N1 3 0.773354 0.932782 0.437941 11.00000 0.02686 0.01992 = 0.01790 -0.00088 0.00100 0.00088 AFIX 43 H1A 2 0.795407 1.020081 0.382178 11.00000 -1.20000 AFIX 6 O10 4 0.219757 0.080957 0.934455 11.00000 0.07255 0.05267 = 0.03836 -0.00694 0.00112 0.02072 H10C 2 0.134941 0.055919 0.982031 11.00000 -1.50000 H10D 2 0.286798 0.001487 0.944578 11.00000 -1.50000 AFIX 0 C14 1 0.699074 0.487763 1.090266 11.00000 0.02098 0.01929 = 0.01334 -0.00347 -0.00101 0.00005 AFIX 43 H14 2 0.662317 0.464942 1.176778 11.00000 -1.20000 AFIX 0 C15 1 0.641311 0.621724 0.993391 11.00000 0.02139 0.01950 = 0.01806 -0.00713 -0.00081 -0.00027 C13 1 0.810721 0.386946 1.060739 11.00000 0.01961 0.01832 = 0.01773 -0.00474 -0.00285 0.00015 C17 1 0.872646 0.242905 1.167218 11.00000 0.02280 0.02027 = 0.01746 -0.00331 -0.00381 0.00190 C16 1 0.696860 0.655228 0.866517 11.00000 0.02569 0.01650 = 0.01712 -0.00209 -0.00451 0.00252 AFIX 43 H16 2 0.658490 0.747603 0.800392 11.00000 -1.20000 AFIX 0 C12 1 0.863701 0.419592 0.934192 11.00000 0.01911 0.02038 = 0.01949 -0.00785 -0.00159 0.00341 AFIX 43 H12 2 0.938537 0.349552 0.914191 11.00000 -1.20000 AFIX 0 C11 1 0.807705 0.554542 0.836351 11.00000 0.02042 0.01932 = 0.01291 -0.00285 -0.00162 -0.00121 C4 1 0.648066 0.735035 0.546813 11.00000 0.02341 0.02210 = 0.01373 -0.00719 0.00062 0.00583 C5 1 0.634412 0.872422 0.442140 11.00000 0.02410 0.02149 = 0.01681 -0.00574 0.00328 0.00155 C10 1 0.873325 0.583027 0.701798 11.00000 0.02475 0.02280 = 0.01598 -0.00141 -0.00277 0.00493 AFIX 23 H10A 2 0.988889 0.590410 0.701091 11.00000 -1.20000 H10B 2 0.862093 0.496186 0.680867 11.00000 -1.20000 AFIX 0 C9 1 0.867426 0.837900 0.531335 11.00000 0.02330 0.02665 = 0.02066 -0.01084 0.00267 0.00045 AFIX 43 H9 2 0.970972 0.853171 0.547208 11.00000 -1.20000 AFIX 0 C1 1 0.264641 0.598410 0.530892 11.00000 0.02302 0.02359 = 0.01797 -0.00650 0.00124 0.00463 C2 1 0.395890 0.693344 0.499496 11.00000 0.02424 0.02177 = 0.01766 -0.00708 0.00225 0.00483 C3 1 0.529502 0.644077 0.577838 11.00000 0.02611 0.02046 = 0.01509 -0.00390 0.00077 0.00162 AFIX 43 H3 2 0.538658 0.551442 0.649843 11.00000 -1.20000 AFIX 0 C18 1 0.516358 0.729977 1.021145 11.00000 0.02776 0.02042 = 0.01902 -0.00504 -0.00113 0.00174 C8 1 0.241691 0.886726 0.300706 11.00000 0.02412 0.02248 = 0.02032 -0.00437 -0.00141 0.00450 C6 1 0.503166 0.922379 0.361783 11.00000 0.02782 0.01972 = 0.01716 -0.00294 0.00061 0.00690 AFIX 43 H6A 2 0.495342 1.015002 0.289775 11.00000 -1.20000 AFIX 0 C7 1 0.383410 0.830527 0.391513 11.00000 0.02314 0.02321 = 0.01860 -0.00856 -0.00005 0.00728 H9B 2 0.025843 0.267943 0.679560 11.00000 0.05564 H8 2 1.023195 0.087765 1.198885 11.00000 0.06308 HKLF 4 REM 20170925lzd_d2_0m_a_sq_a.res in P-1 REM R1 = 0.0609 for 2732 Fo > 4sig(Fo) and 0.0938 for all 3876 data REM 287 parameters refined using 5 restraints END WGHT 0.0607 0.8920 REM Highest difference peak 0.367, deepest hole -0.270, 1-sigma level 0.066 Q1 1 0.1783 0.3396 0.6840 11.00000 0.05 0.37 Q2 1 0.8425 0.5607 0.7789 11.00000 0.05 0.35 Q3 1 0.7833 0.6183 0.8581 11.00000 0.05 0.34 Q4 1 0.8420 0.3169 1.1123 11.00000 0.05 0.31 Q5 1 0.8404 0.4951 0.8836 11.00000 0.05 0.29 Q6 1 0.7663 0.4398 1.0795 11.00000 0.05 0.29 Q7 1 0.6338 0.6179 0.9276 11.00000 0.05 0.29 Q8 1 0.7335 0.4226 1.0689 11.00000 0.05 0.28 Q9 1 0.4122 0.8932 0.4142 11.00000 0.05 0.28 Q10 1 0.7077 0.7065 0.6025 11.00000 0.05 0.28 Q11 1 0.6961 0.6434 0.9415 11.00000 0.05 0.27 Q12 1 0.4047 0.9235 0.2126 11.00000 0.05 0.27 Q13 1 0.1576 -0.0003 0.9450 11.00000 0.05 0.27 Q14 1 0.5408 0.8603 0.9778 11.00000 0.05 0.26 Q15 1 0.6351 0.8216 0.5154 11.00000 0.05 0.26 Q16 1 0.1142 0.0336 0.9585 11.00000 0.05 0.26 Q17 1 0.8014 0.1350 1.3374 11.00000 0.05 0.26 Q18 1 0.7964 0.7927 0.6110 11.00000 0.05 0.26 Q19 1 0.0870 0.8942 0.2974 11.00000 0.05 0.25 Q20 1 0.5978 0.6818 1.0089 11.00000 0.05 0.25 ; _shelx_res_checksum 19882 _shelx_hkl_file ; -1 0 0 20.70 1.00 1 0 0 17.80 1.20 -2 0 0 1186.88 44.70 2 0 0 1246.88 44.70 -3 0 0 2296.67 84.99 3 0 0 2341.57 84.99 -4 0 0 0.20 0.90 -5 0 0 34.10 3.10 -5 0 0 34.70 2.70 -6 0 0 227.58 9.50 -6 0 0 203.18 9.90 -7 0 0 8.40 2.50 -7 0 0 1.60 1.90 -8 0 0 200.78 9.70 -8 0 0 190.18 10.10 -9 0 0 12.50 3.60 -9 0 0 6.70 3.30 -10 0 0 8.80 4.40 -10 0 0 14.30 4.40 -10 1 0 13.30 4.50 -10 1 0 18.10 5.00 -9 1 0 0.00 3.30 -9 1 0 -2.50 3.10 -8 1 0 7.60 3.20 -8 1 0 6.20 2.90 -7 1 0 42.50 4.50 -7 1 0 52.29 4.20 -6 1 0 26.20 3.00 -6 1 0 28.40 3.10 -5 1 0 30.40 2.80 -5 1 0 25.00 2.40 -4 1 0 812.92 30.30 -4 1 0 784.62 30.00 3 -1 0 153.88 6.30 -3 1 0 156.08 6.30 -3 1 0 146.79 6.50 2 -1 0 33.00 1.70 2 -1 0 30.30 1.90 -2 1 0 30.30 1.70 -2 1 0 34.00 1.90 1 -1 0 3.50 0.50 1 -1 0 3.70 0.50 -1 1 0 2.80 0.50 -1 1 0 3.70 0.50 0 -1 0 65.79 2.70 -1 -1 0 44.20 2.20 -1 -1 0 43.80 1.90 1 1 0 44.40 2.20 -2 -1 0 518.85 19.90 2 1 0 546.95 19.90 -3 -1 0 18.30 1.50 3 1 0 20.30 1.70 -4 -1 0 20.80 1.90 -5 -1 0 460.85 18.10 -6 -1 0 103.39 5.40 -7 -1 0 104.09 5.90 -8 -1 0 348.77 16.00 -8 -1 0 362.66 15.50 -9 -1 0 53.89 6.20 -9 -1 0 54.89 5.80 -10 -1 0 11.60 4.40 -10 -1 0 26.00 4.80 -10 2 0 3.70 4.60 -10 2 0 -0.10 4.30 -9 2 0 4.50 3.70 -9 2 0 -4.00 3.10 -8 2 0 0.00 2.90 -8 2 0 3.70 2.60 -7 2 0 5.30 2.20 -7 2 0 2.70 2.30 -6 2 0 10.00 2.40 -6 2 0 8.60 2.10 -5 2 0 224.38 9.50 -5 2 0 219.48 9.70 -4 2 0 5.40 1.30 -4 2 0 8.90 1.60 3 -2 0 18.70 1.80 -3 2 0 21.10 1.90 -3 2 0 21.50 1.90 2 -2 0 219.78 8.70 2 -2 0 228.38 8.90 -2 2 0 225.98 8.80 -2 2 0 213.78 8.80 1 -2 0 14.70 1.10 1 -2 0 13.90 1.20 -1 2 0 13.60 1.10 -1 2 0 12.80 1.20 0 -2 0 367.96 14.20 0 -2 0 399.46 14.40 0 2 0 364.36 14.30 0 2 0 382.26 14.40 -1 -2 0 300.47 11.60 -1 -2 0 293.17 11.60 1 2 0 302.57 11.70 1 2 0 294.47 11.60 -2 -2 0 2217.58 81.19 -2 -2 0 2125.39 80.69 -2 -2 0 2266.27 80.99 -3 -2 0 78.89 3.80 -4 -2 0 304.07 12.20 -5 -2 0 11.80 1.80 -6 -2 0 7.60 2.10 -7 -2 0 72.79 5.00 -8 -2 0 44.30 4.50 -9 -2 0 2.50 3.00 -10 -2 0 -2.40 4.00 -10 -2 0 4.50 4.10 -10 3 0 1.50 4.50 -10 3 0 1.60 5.20 -9 3 0 -5.80 3.90 -9 3 0 7.80 4.00 -8 3 0 4.20 2.80 -8 3 0 -0.10 3.20 -7 3 0 5.10 2.50 -7 3 0 9.60 3.10 -6 3 0 57.69 4.50 -6 3 0 59.79 4.50 -5 3 0 68.29 4.30 -5 3 0 71.19 4.40 -4 3 0 233.68 10.00 -4 3 0 240.88 10.00 3 -3 0 443.46 16.80 -3 3 0 435.46 16.90 -3 3 0 421.06 16.80 2 -3 0 2.80 1.20 -2 3 0 2.50 0.90 -2 3 0 2.50 1.00 1 -3 0 15.90 1.50 1 -3 0 19.50 1.90 -1 3 0 17.10 1.50 -1 3 0 20.70 1.70 0 -3 0 8.40 1.30 0 -3 0 7.20 1.10 0 3 0 6.50 1.10 0 3 0 9.90 1.30 -1 -3 0 88.39 4.30 -1 -3 0 91.69 4.50 1 3 0 90.29 4.40 1 3 0 91.49 4.40 2 3 0 302.27 12.50 -3 -3 0 408.96 15.90 -4 -3 0 1.90 1.10 -5 -3 0 21.50 2.30 -6 -3 0 7.90 1.70 -7 -3 0 45.00 4.30 -8 -3 0 0.10 2.50 -9 -3 0 4.80 3.30 -10 -3 0 4.50 4.30 -9 4 0 4.10 3.70 -9 4 0 1.50 4.60 -8 4 0 82.99 7.50 -8 4 0 95.09 6.90 -7 4 0 13.90 3.70 -7 4 0 17.90 3.20 -6 4 0 79.89 5.70 -6 4 0 83.49 5.40 -5 4 0 0.00 1.60 -5 4 0 -3.30 1.80 -4 4 0 175.08 8.10 -4 4 0 177.08 8.00 -3 4 0 138.19 6.50 -3 4 0 141.99 6.50 2 -4 0 0.20 1.50 -2 4 0 -0.80 0.90 -2 4 0 -0.10 1.20 1 -4 0 615.04 23.50 -1 4 0 605.84 23.40 -1 4 0 618.54 23.50 0 -4 0 300.67 13.20 0 4 0 344.87 13.20 0 4 0 343.17 13.30 1 4 0 222.58 9.60 1 4 0 226.08 9.70 2 4 0 30.00 2.60 2 4 0 25.10 2.90 -3 -4 0 81.99 4.20 3 4 0 82.49 5.20 -4 -4 0 43.60 3.20 -5 -4 0 236.68 10.30 -6 -4 0 10.30 2.10 -8 -4 0 13.40 3.70 -9 -4 0 0.10 3.40 -10 -4 0 46.50 6.40 -9 5 0 3.80 5.20 -9 5 0 -0.80 4.30 -8 5 0 8.70 4.40 -8 5 0 4.50 3.30 -7 5 0 117.69 7.00 -7 5 0 100.09 7.40 -6 5 0 167.08 8.50 -6 5 0 168.08 9.20 -5 5 0 302.67 12.80 -5 5 0 289.97 13.00 -4 5 0 530.05 21.40 -4 5 0 547.45 21.40 -3 5 0 157.18 7.60 -3 5 0 167.58 7.60 -2 5 0 0.40 1.50 -2 5 0 2.40 1.30 -1 5 0 1220.68 45.50 -1 5 0 1192.58 45.30 0 5 0 60.59 3.80 0 5 0 56.89 3.90 1 5 0 8.10 1.90 1 5 0 5.30 1.70 2 5 0 6.40 2.00 2 5 0 5.70 2.10 -3 -5 0 1.80 1.10 3 5 0 2.40 1.90 -4 -5 0 57.09 3.80 -4 -5 0 57.09 3.70 -5 -5 0 53.79 4.00 -6 -5 0 2.30 1.90 -7 -5 0 42.20 4.30 -8 -5 0 22.90 3.80 -9 -5 0 3.80 4.10 -10 -5 0 25.10 5.80 -8 6 0 52.69 6.20 -8 6 0 46.80 6.30 -7 6 0 28.40 5.10 -7 6 0 30.90 4.60 -6 6 0 0.60 3.20 -6 6 0 -0.30 2.70 -5 6 0 137.59 7.40 -5 6 0 117.39 7.60 -4 6 0 31.10 3.70 -4 6 0 29.10 3.40 -3 6 0 80.79 5.20 -3 6 0 96.29 5.70 -2 6 0 36.50 3.60 -2 6 0 45.90 4.00 -1 6 0 431.76 17.10 -1 6 0 398.96 17.00 0 6 0 6.10 2.00 0 6 0 5.70 2.10 1 6 0 11.90 2.30 1 6 0 11.70 2.40 2 6 0 771.52 30.00 2 6 0 756.02 30.30 -3 -6 0 188.58 8.50 3 6 0 190.28 9.90 -4 -6 0 4.20 1.70 -5 -6 0 232.88 10.80 -6 -6 0 8.10 2.40 -7 -6 0 76.19 5.50 -8 -6 0 2.70 3.30 -9 -6 0 34.20 5.40 -10 -6 0 -1.10 5.60 -7 7 0 -3.00 3.70 -7 7 0 3.20 4.70 -6 7 0 45.60 5.00 -6 7 0 49.90 5.90 -5 7 0 23.20 4.10 -5 7 0 18.40 3.70 -4 7 0 17.80 3.70 -4 7 0 15.80 3.10 -3 7 0 192.38 9.70 -3 7 0 182.38 9.30 -2 7 0 311.87 14.10 -2 7 0 338.37 14.40 -1 7 0 31.50 4.20 -1 7 0 30.60 3.70 0 7 0 72.69 5.40 0 7 0 64.39 4.90 1 7 0 3.70 2.40 1 7 0 -0.70 2.20 2 7 0 21.30 3.00 2 7 0 9.60 3.10 -3 -7 0 108.29 5.80 3 7 0 97.89 7.40 -4 -7 0 18.10 2.70 4 7 0 26.00 4.70 -5 -7 0 3.20 2.60 -6 -7 0 -5.10 2.00 -7 -7 0 8.20 2.90 -8 -7 0 -2.30 3.20 -9 -7 0 39.00 6.60 -7 8 0 7.30 4.90 -6 8 0 14.80 4.40 -6 8 0 24.80 5.20 -5 8 0 128.09 9.00 -5 8 0 130.79 8.40 -4 8 0 16.30 4.10 -4 8 0 18.90 3.70 -3 8 0 74.99 5.90 -3 8 0 70.79 6.30 -2 8 0 1.60 3.00 -2 8 0 6.00 2.60 -1 8 0 12.30 3.20 -1 8 0 11.10 3.10 0 8 0 21.60 3.90 0 8 0 20.10 3.70 1 8 0 12.70 3.70 1 8 0 11.70 3.20 2 8 0 117.79 8.30 2 8 0 140.29 8.10 -3 -8 0 3.20 2.00 3 8 0 0.40 3.20 -4 -8 0 4.20 2.30 4 8 0 5.60 4.40 -5 -8 0 14.30 3.20 -6 -8 0 -3.70 2.50 -7 -8 0 4.70 3.30 -8 -8 0 11.30 4.50 -5 9 0 6.20 4.90 -5 9 0 4.70 4.50 -4 9 0 6.40 4.60 -4 9 0 2.10 3.60 -3 9 0 1.80 3.50 -3 9 0 -2.20 4.00 -2 9 0 161.28 9.90 -2 9 0 175.58 9.70 -1 9 0 4.80 3.70 -1 9 0 -2.00 3.20 0 9 0 104.49 7.80 0 9 0 99.59 7.60 1 9 0 -1.50 3.40 1 9 0 1.20 3.40 2 9 0 82.39 7.70 -3 -9 0 9.80 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4.80 -1 5 -5 2.40 2.40 -1 5 -5 1.50 3.00 -2 5 -5 0.20 3.10 -2 5 -5 2.70 2.30 -3 5 -5 103.79 6.10 -3 5 -5 93.69 8.00 -4 5 -5 9.80 2.60 -4 5 -5 12.50 4.20 -5 5 -5 10.40 4.50 -5 5 -5 8.40 2.90 -6 5 -5 3.70 4.90 -6 5 -5 6.20 2.90 -7 5 -5 5.70 3.60 -7 5 -5 3.70 6.00 -9 -4 5 13.20 4.50 -8 -4 5 3.30 3.30 -7 -4 5 19.30 3.70 -6 -4 5 26.20 3.60 4 4 -5 127.59 8.20 -4 -4 5 123.89 6.10 3 4 -5 232.38 12.00 -3 -4 5 249.18 10.10 2 4 -5 3.50 2.40 -2 -4 5 2.40 1.50 1 4 -5 41.90 4.90 1 4 -5 39.30 4.20 -1 -4 5 32.30 3.00 0 4 -5 2.60 2.40 0 4 -5 2.30 2.00 0 -4 5 1.00 1.80 -1 4 -5 1.60 2.50 -1 4 -5 0.90 1.90 -2 4 -5 382.26 17.00 -2 4 -5 387.86 15.60 -3 4 -5 14.30 3.60 -3 4 -5 14.00 2.40 -4 4 -5 10.80 3.60 -4 4 -5 8.50 2.10 -5 4 -5 3.50 3.70 -5 4 -5 5.00 2.20 -6 4 -5 18.80 4.80 -6 4 -5 20.40 3.20 -7 4 -5 26.20 5.60 -7 4 -5 18.50 3.50 -8 4 -5 0.50 3.70 -8 4 -5 16.50 6.20 -9 -3 5 9.30 4.00 -8 -3 5 7.60 3.20 -7 -3 5 15.90 3.40 -6 -3 5 104.99 6.20 4 3 -5 2.90 2.70 3 3 -5 3.70 2.30 -3 -3 5 10.20 1.80 -2 -3 5 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87.09 9.60 -6 4 11 11.50 5.60 -6 4 11 -1.80 4.20 -5 4 11 44.10 6.00 -5 4 11 47.10 6.00 -4 4 11 1.20 3.00 -4 4 11 1.20 4.00 3 -4 -11 24.90 4.20 -3 4 11 28.30 3.30 -3 4 11 17.70 4.60 2 -4 -11 4.30 3.80 -2 4 11 4.40 2.40 -2 4 11 2.80 3.30 1 -4 -11 21.00 4.40 -1 4 11 15.10 4.00 -1 4 11 18.10 2.60 0 -4 -11 0.00 3.30 0 4 11 -2.10 3.00 -1 -4 -11 126.19 8.30 1 4 11 121.49 8.20 -2 -4 -11 17.70 4.10 2 4 11 8.70 3.40 -3 -4 -11 0.10 3.80 3 4 11 1.70 3.70 -4 -4 -11 2.10 4.00 4 4 11 2.50 4.00 -5 -4 -11 94.19 8.50 5 4 11 95.49 9.50 -6 -4 -11 28.00 6.20 -7 -4 -11 65.39 8.50 -6 5 11 13.20 5.20 -5 5 11 -1.50 3.40 -5 5 11 4.30 4.60 -4 5 11 -1.00 3.60 -4 5 11 2.80 3.10 -3 5 11 32.50 5.20 -3 5 11 25.20 3.60 2 -5 -11 8.10 3.50 -2 5 11 -0.80 3.30 -2 5 11 -2.20 2.30 1 -5 -11 10.40 3.70 -1 5 11 10.00 2.80 -1 5 11 7.40 3.30 0 -5 -11 20.60 4.20 0 5 11 26.00 3.10 0 5 11 21.00 4.00 -1 -5 -11 7.00 3.30 1 5 11 5.40 3.40 -2 -5 -11 13.40 3.90 2 5 11 17.30 4.10 -3 -5 -11 13.00 4.20 3 5 11 8.80 3.80 -4 -5 -11 32.30 5.20 4 5 11 29.70 5.20 -5 -5 -11 28.30 5.40 5 5 11 23.80 6.00 -6 -5 -11 67.19 8.70 -7 -5 -11 14.40 6.10 -6 6 11 2.00 4.70 -5 6 11 2.80 3.90 -5 6 11 0.90 4.80 -4 6 11 26.40 5.50 -4 6 11 25.90 4.30 -3 6 11 1.30 3.80 -3 6 11 -1.30 3.00 -2 6 11 6.40 3.90 -2 6 11 0.60 2.80 1 -6 -11 2.30 3.20 -1 6 11 6.90 3.60 -1 6 11 6.70 3.20 0 -6 -11 158.88 8.60 0 6 11 142.29 9.20 0 6 11 148.39 8.00 -1 -6 -11 41.90 4.80 1 6 11 26.90 4.80 1 6 11 40.00 4.30 -2 -6 -11 -2.40 3.60 2 6 11 -2.90 3.60 2 6 11 5.50 3.40 -3 -6 -11 1.10 3.70 3 6 11 -4.40 3.40 -4 -6 -11 20.70 4.70 4 6 11 18.70 4.90 -5 -6 -11 9.60 4.80 5 6 11 5.60 4.90 -6 -6 -11 3.60 5.40 -7 -6 -11 23.40 6.70 -5 7 11 15.10 5.00 -5 7 11 19.50 6.30 -4 7 11 35.20 5.10 -4 7 11 26.60 5.60 -3 7 11 108.29 7.80 -3 7 11 114.39 9.10 -2 7 11 -3.10 3.20 -2 7 11 2.00 4.10 -1 7 11 7.70 3.70 -1 7 11 9.70 3.50 0 -7 -11 40.50 5.50 0 7 11 56.09 5.90 0 7 11 47.00 6.40 -1 -7 -11 20.00 4.30 1 7 11 17.80 4.20 1 7 11 23.30 4.80 -2 -7 -11 6.20 3.80 2 7 11 -1.90 4.10 2 7 11 5.30 3.90 -3 -7 -11 22.70 4.60 3 7 11 26.70 5.20 3 7 11 21.00 4.80 -4 -7 -11 -2.20 3.90 4 7 11 -1.00 4.40 -5 -7 -11 13.60 5.00 5 7 11 10.40 5.60 -6 -7 -11 -5.00 4.80 -7 -7 -11 10.20 6.10 -4 8 11 9.20 5.10 -4 8 11 -0.30 4.30 -3 8 11 113.89 8.80 -3 8 11 110.89 9.90 -2 8 11 26.60 5.70 -2 8 11 17.80 4.50 -1 8 11 -1.50 3.60 -1 8 11 -2.20 3.90 0 -8 -11 17.40 3.70 0 8 11 21.40 4.50 0 8 11 18.60 4.50 -1 -8 -11 248.48 12.00 1 8 11 261.47 13.20 1 8 11 248.18 13.10 -2 -8 -11 -7.60 3.50 2 8 11 -0.30 4.70 2 8 11 3.10 4.20 -3 -8 -11 -0.70 3.80 3 8 11 7.70 4.70 3 8 11 1.70 5.10 -4 -8 -11 5.80 4.30 4 8 11 -7.90 4.80 5 8 11 48.40 7.40 -6 -8 -11 -2.50 5.70 -7 -8 -11 20.40 7.30 -4 9 11 137.29 11.60 -4 9 11 112.19 10.70 -3 9 11 122.99 11.40 -3 9 11 131.89 10.30 -2 9 11 6.10 5.20 -2 9 11 2.20 4.70 -1 9 11 1.60 4.70 -1 9 11 5.70 4.70 0 9 11 64.19 8.10 0 9 11 43.50 6.10 -1 -9 -11 42.10 4.90 1 9 11 49.60 6.60 1 9 11 43.60 6.50 -2 -9 -11 4.30 4.20 2 9 11 5.70 4.70 2 9 11 1.60 5.40 -3 -9 -11 64.39 7.90 3 9 11 59.99 7.90 3 9 11 84.99 9.70 -4 -9 -11 24.30 5.40 4 9 11 11.30 6.30 4 9 11 17.40 7.50 -5 -9 -11 11.20 5.70 5 9 11 6.00 6.70 -6 -9 -11 -1.70 6.00 -2 10 11 6.10 5.60 -2 10 11 -4.00 5.40 -1 10 11 7.20 5.40 -1 10 11 3.60 5.60 0 10 11 26.60 6.70 0 10 11 20.00 6.10 1 10 11 12.80 6.40 1 10 11 27.80 6.10 -2 -10 -11 10.70 4.80 2 10 11 12.10 5.90 2 10 11 18.00 6.80 -3 -10 -11 31.70 5.60 3 10 11 17.80 7.30 3 10 11 24.20 7.00 -4 -10 -11 102.89 10.00 4 10 11 124.49 14.00 4 10 11 98.79 12.10 -5 -10 -11 5.20 5.90 5 10 11 14.60 7.40 -1 11 11 8.70 6.80 -1 11 11 9.20 7.20 0 11 11 4.20 6.20 0 11 11 -3.30 6.60 1 11 11 5.20 6.50 1 11 11 -4.70 7.20 2 11 11 11.80 7.90 2 11 11 12.10 6.30 -3 -11 -11 -9.50 5.00 3 11 11 13.70 8.50 3 11 11 7.40 7.10 4 11 11 1.60 7.60 2 2 -12 60.99 9.80 -2 -2 12 67.39 7.70 1 2 -12 30.90 8.40 0 2 -12 -17.70 7.20 0 -2 12 4.00 5.60 -1 2 -12 31.60 8.30 1 -2 12 29.40 6.60 -2 2 -12 115.29 12.20 2 -2 12 86.69 10.00 4 1 -12 8.00 7.60 3 1 -12 42.00 8.40 -3 -1 12 39.50 6.70 2 1 -12 1.40 6.60 -2 -1 12 0.70 4.70 1 1 -12 -9.80 6.40 -1 -1 12 8.80 4.90 0 1 -12 58.09 8.70 0 -1 12 32.40 6.00 -1 1 -12 8.10 6.70 1 -1 12 8.30 5.30 -2 1 -12 4.40 6.20 2 -1 12 0.20 5.30 -3 1 -12 37.30 8.10 4 0 -12 4.00 6.60 -4 0 12 1.30 5.30 3 0 -12 23.40 6.80 -3 0 12 16.70 5.50 2 0 -12 -0.30 5.90 -2 0 12 0.70 4.20 1 0 -12 107.39 11.10 -1 0 12 111.59 8.80 0 0 -12 32.20 6.80 0 0 12 24.70 5.20 -1 0 -12 48.00 7.40 1 0 12 43.40 6.20 -2 0 -12 42.30 7.20 2 0 12 33.40 5.90 -3 0 -12 5.00 6.00 3 0 12 4.20 5.50 -4 0 -12 26.80 7.50 -5 0 -12 -5.40 6.90 5 -1 -12 5.20 6.00 -5 1 12 -7.50 4.20 -5 1 12 -0.80 5.70 4 -1 -12 -1.30 5.70 -4 1 12 2.20 3.60 -4 1 12 -0.10 4.90 3 -1 -12 24.80 6.40 -3 1 12 28.90 5.70 2 -1 -12 -3.60 5.50 -2 1 12 5.80 4.50 1 -1 -12 5.10 5.60 -1 1 12 9.30 4.40 0 -1 -12 4.00 5.10 0 1 12 2.80 4.30 -1 -1 -12 24.20 5.50 1 1 12 7.10 4.60 -2 -1 -12 7.80 5.20 2 1 12 11.20 5.30 -3 -1 -12 8.40 5.80 3 1 12 13.10 5.70 -4 -1 -12 19.60 6.50 4 1 12 23.00 5.60 -5 -1 -12 124.59 12.40 -5 2 12 -3.00 3.80 -5 2 12 2.00 5.60 4 -2 -12 16.00 5.50 -4 2 12 15.40 3.70 -4 2 12 12.80 5.50 3 -2 -12 15.20 5.30 -3 2 12 7.60 3.20 -3 2 12 7.70 4.80 2 -2 -12 20.20 5.70 -2 2 12 24.40 5.20 1 -2 -12 -0.20 5.00 -1 2 12 3.10 4.00 0 -2 -12 66.49 7.10 0 2 12 42.10 5.80 -1 -2 -12 15.10 5.10 1 2 12 12.30 4.40 -2 -2 -12 30.90 5.70 2 2 12 24.80 5.10 -3 -2 -12 -3.80 5.00 3 2 12 3.50 4.70 -4 -2 -12 2.50 5.10 4 2 12 1.00 5.30 -5 -2 -12 38.30 7.60 -6 -2 -12 14.60 7.10 -5 3 12 1.10 4.80 -5 3 12 8.10 3.80 4 -3 -12 4.20 4.50 -4 3 12 0.00 3.20 -4 3 12 4.80 5.30 3 -3 -12 6.70 4.70 -3 3 12 -4.50 4.10 -3 3 12 4.30 2.60 2 -3 -12 13.10 5.00 -2 3 12 17.70 4.70 -2 3 12 14.40 2.80 1 -3 -12 29.10 5.40 -1 3 12 13.80 4.60 0 -3 -12 87.59 8.20 0 3 12 71.49 7.10 -1 -3 -12 81.19 8.60 1 3 12 79.49 7.70 -2 -3 -12 19.20 5.20 2 3 12 15.30 4.60 -3 -3 -12 10.20 4.90 3 3 12 5.20 4.80 -4 -3 -12 -2.60 4.90 4 3 12 3.00 4.70 -5 -3 -12 60.49 8.10 5 3 12 64.89 8.60 -6 -3 -12 45.30 7.90 -5 4 12 8.00 4.40 -5 4 12 10.80 5.50 -4 4 12 17.70 5.50 -4 4 12 11.60 3.50 3 -4 -12 5.20 4.60 -3 4 12 -0.20 2.90 -3 4 12 -0.80 4.40 2 -4 -12 37.80 5.60 -2 4 12 33.70 3.40 -2 4 12 23.80 4.90 1 -4 -12 7.90 4.20 -1 4 12 4.10 3.90 0 -4 -12 30.70 5.20 0 4 12 24.20 4.80 -1 -4 -12 118.69 9.10 1 4 12 103.79 8.50 -2 -4 -12 36.60 5.90 2 4 12 38.50 6.10 -3 -4 -12 29.70 5.60 3 4 12 22.90 5.50 -4 -4 -12 17.40 5.50 4 4 12 13.50 5.50 -5 -4 -12 16.30 6.10 5 4 12 6.40 6.30 -6 -4 -12 1.10 6.30 -5 5 12 5.80 5.30 -5 5 12 11.10 4.20 -4 5 12 4.20 3.50 -4 5 12 -1.80 4.80 -3 5 12 86.79 8.80 -3 5 12 69.19 6.40 2 -5 -12 6.50 4.40 -2 5 12 6.50 4.50 -2 5 12 3.90 3.00 1 -5 -12 40.70 5.80 -1 5 12 45.60 5.10 -1 5 12 39.60 5.70 0 -5 -12 0.70 4.00 0 5 12 -2.50 3.30 -1 -5 -12 8.30 4.30 1 5 12 4.50 3.80 -2 -5 -12 47.20 6.00 2 5 12 43.20 6.30 -3 -5 -12 17.40 4.90 3 5 12 16.20 5.60 -4 -5 -12 28.00 5.60 4 5 12 41.30 7.00 -5 -5 -12 64.59 8.00 5 5 12 53.59 8.70 -6 -5 -12 26.10 7.10 -5 6 12 15.30 5.60 -5 6 12 19.80 5.10 -4 6 12 9.10 5.40 -4 6 12 1.00 4.20 -3 6 12 32.40 4.40 -2 6 12 3.40 4.20 -2 6 12 4.40 3.50 1 -6 -12 20.20 4.50 -1 6 12 29.10 4.20 -1 6 12 17.20 4.90 0 -6 -12 28.60 5.00 0 6 12 26.20 4.20 0 6 12 18.40 4.60 -1 -6 -12 12.80 4.40 1 6 12 13.60 4.40 -2 -6 -12 -1.80 4.00 2 6 12 3.60 4.20 -3 -6 -12 16.20 5.00 3 6 12 9.10 4.80 -4 -6 -12 24.00 5.30 4 6 12 17.30 6.00 -5 -6 -12 6.40 5.60 5 6 12 -7.30 5.80 -6 -6 -12 1.00 5.90 -4 7 12 -0.20 5.50 -4 7 12 -4.80 4.40 -3 7 12 8.60 5.80 -3 7 12 7.90 4.10 -2 7 12 6.90 4.10 -2 7 12 -0.70 4.70 -1 7 12 4.80 3.90 -1 7 12 -0.20 4.60 0 -7 -12 29.90 4.80 0 7 12 26.40 5.30 0 7 12 37.80 5.00 -1 -7 -12 45.50 5.30 1 7 12 60.39 6.00 1 7 12 46.80 6.50 -2 -7 -12 13.80 4.50 2 7 12 7.30 4.70 2 7 12 9.20 4.90 -3 -7 -12 -8.50 4.20 3 7 12 5.30 5.00 -4 -7 -12 6.20 5.10 4 7 12 0.30 5.30 -5 -7 -12 0.50 5.60 5 7 12 4.20 5.90 -6 -7 -12 1.50 6.40 -3 8 12 98.89 9.30 -3 8 12 142.09 11.90 -2 8 12 -5.00 5.20 -2 8 12 0.40 4.30 -1 8 12 17.20 5.40 -1 8 12 11.80 4.70 0 8 12 28.30 5.60 0 8 12 19.80 5.20 -1 -8 -12 4.10 4.10 1 8 12 6.50 4.70 1 8 12 -4.00 5.50 -2 -8 -12 31.90 5.20 2 8 12 40.90 6.00 2 8 12 29.40 6.00 -3 -8 -12 0.60 4.90 3 8 12 -1.60 5.10 3 8 12 -2.30 6.00 -4 -8 -12 -0.50 5.00 4 8 12 3.10 5.90 -5 -8 -12 42.10 7.20 5 8 12 28.70 7.40 -6 -8 -12 -3.00 6.70 -3 9 12 -3.40 5.50 -3 9 12 13.90 7.10 -2 9 12 3.90 5.40 -2 9 12 15.40 6.70 -1 9 12 -2.70 4.80 -1 9 12 -5.40 5.60 0 9 12 18.80 5.70 0 9 12 14.90 5.80 -1 -9 -12 16.20 5.30 1 9 12 18.20 5.80 1 9 12 2.70 5.90 -2 -9 -12 2.30 4.70 2 9 12 12.00 6.60 2 9 12 4.50 5.60 -3 -9 -12 19.80 5.80 3 9 12 14.90 6.60 3 9 12 26.10 7.40 -4 -9 -12 -2.10 5.40 4 9 12 2.60 6.90 -5 -9 -12 0.10 6.30 5 9 12 12.70 8.40 -1 10 12 1.20 6.20 -1 10 12 1.60 7.10 0 10 12 2.20 6.50 0 10 12 17.70 6.50 1 10 12 16.90 7.00 1 10 12 13.40 6.50 -2 -10 -12 14.60 5.30 2 10 12 0.90 6.40 2 10 12 12.40 7.30 -3 -10 -12 278.87 14.90 3 10 12 284.47 17.50 3 10 12 308.07 18.20 -4 -10 -12 52.69 7.40 4 10 12 53.59 9.90 4 10 12 47.20 9.70 2 0 -13 3.60 7.90 -2 0 13 4.60 5.90 1 0 -13 33.60 8.40 -1 0 13 36.90 7.40 0 0 -13 101.19 12.90 0 0 13 72.19 9.40 -1 0 -13 15.40 7.40 1 0 13 15.00 6.10 -2 0 -13 71.59 10.00 2 0 13 81.49 10.60 3 -1 -13 36.20 8.10 -3 1 13 29.40 7.00 2 -1 -13 34.80 7.70 -2 1 13 41.30 6.70 1 -1 -13 9.70 6.80 -1 1 13 12.00 5.50 0 -1 -13 39.30 7.40 0 1 13 33.10 6.50 -1 -1 -13 64.99 8.80 1 1 13 51.99 7.90 -2 -1 -13 57.29 8.70 2 1 13 47.50 8.10 -3 -1 -13 5.60 7.20 3 1 13 -2.70 6.00 -4 -1 -13 7.70 7.40 4 -2 -13 13.80 6.50 -4 2 13 2.70 6.10 3 -2 -13 7.10 6.20 -3 2 13 1.90 5.80 2 -2 -13 36.70 7.00 -2 2 13 31.00 6.20 1 -2 -13 12.60 6.40 -1 2 13 13.00 5.00 0 -2 -13 11.40 6.10 0 2 13 0.20 5.00 -1 -2 -13 -4.40 5.30 1 2 13 -1.00 4.80 -2 -2 -13 -8.80 5.90 2 2 13 -2.50 5.10 -3 -2 -13 5.90 6.60 3 2 13 3.20 6.10 -4 -2 -13 -11.80 6.90 4 2 13 9.40 6.80 -4 3 13 14.60 6.30 3 -3 -13 23.80 6.20 -3 3 13 8.20 5.70 2 -3 -13 45.20 7.00 -2 3 13 26.40 6.40 1 -3 -13 38.00 6.90 -1 3 13 39.10 6.00 0 -3 -13 60.69 7.50 0 3 13 51.99 6.90 -1 -3 -13 86.29 10.20 1 3 13 101.39 9.30 -2 -3 -13 33.20 6.80 2 3 13 25.60 6.10 -3 -3 -13 -9.40 5.90 3 3 13 1.70 5.30 -4 -3 -13 15.60 6.90 4 3 13 17.20 7.20 -5 -3 -13 10.20 7.40 -4 4 13 4.00 3.80 -4 4 13 -4.60 6.30 -3 4 13 0.70 5.50 2 -4 -13 7.40 5.50 -2 4 13 4.40 5.70 1 -4 -13 9.30 5.40 -1 4 13 -2.40 4.80 0 -4 -13 34.20 6.20 0 4 13 24.30 5.20 -1 -4 -13 1.40 5.00 1 4 13 2.40 5.00 -2 -4 -13 -3.20 5.20 2 4 13 0.80 5.00 -3 -4 -13 64.39 7.80 3 4 13 71.09 9.70 -4 -4 -13 1.60 6.20 4 4 13 2.50 6.10 -5 -4 -13 47.50 8.60 5 4 13 53.29 9.10 -4 5 13 170.38 13.50 -4 5 13 142.29 9.30 -3 5 13 5.80 5.80 -3 5 13 10.20 3.80 2 -5 -13 -6.20 6.40 -2 5 13 2.20 4.90 1 -5 -13 -3.20 4.90 -1 5 13 7.50 5.00 0 -5 -13 5.60 4.60 0 5 13 1.40 4.50 -1 -5 -13 23.60 5.70 1 5 13 16.90 5.30 -2 -5 -13 23.00 5.40 2 5 13 19.40 6.00 -3 -5 -13 1.40 5.40 3 5 13 4.70 6.10 -4 -5 -13 11.10 6.30 4 5 13 3.50 6.20 -5 -5 -13 7.20 6.80 5 5 13 -5.10 6.80 -3 6 13 11.20 6.20 -3 6 13 7.60 4.30 -2 6 13 3.50 4.10 -2 6 13 0.20 5.00 1 -6 -13 -3.90 5.50 -1 6 13 9.00 5.30 0 -6 -13 16.80 5.40 0 6 13 29.40 6.30 -1 -6 -13 8.30 5.00 1 6 13 12.10 5.10 -2 -6 -13 27.80 5.60 2 6 13 15.40 5.50 -3 -6 -13 101.89 10.10 3 6 13 66.89 8.60 -4 -6 -13 9.60 6.20 4 6 13 6.70 6.90 -5 -6 -13 14.20 7.00 5 6 13 17.90 7.60 -3 7 13 20.20 5.00 -3 7 13 12.80 6.80 -2 7 13 20.50 6.60 -2 7 13 23.80 4.90 -1 7 13 9.30 4.80 -1 7 13 3.50 5.70 0 -7 -13 28.20 5.60 0 7 13 28.70 6.90 0 7 13 25.90 9.20 -1 -7 -13 5.30 5.00 1 7 13 8.20 5.20 -2 -7 -13 0.50 5.00 2 7 13 -6.70 5.30 -3 -7 -13 -2.40 5.30 3 7 13 8.80 6.10 -4 -7 -13 13.80 6.50 4 7 13 16.90 6.90 -5 -7 -13 13.70 6.90 5 7 13 2.50 7.20 -2 8 13 2.60 6.50 -2 8 13 9.40 5.30 -1 8 13 10.10 6.50 -1 8 13 18.40 5.40 0 8 13 34.30 6.30 0 8 13 21.90 6.60 -1 -8 -13 -2.70 5.10 1 8 13 10.30 8.80 1 8 13 7.90 5.90 -2 -8 -13 1.20 5.30 2 8 13 4.30 5.90 -3 -8 -13 -5.00 5.50 3 8 13 -4.00 6.60 -4 -8 -13 12.30 6.40 4 8 13 6.10 7.50 -1 9 13 -1.60 6.00 -1 9 13 8.00 7.00 0 9 13 9.50 6.00 0 9 13 5.40 6.40 1 9 13 19.10 7.10 1 9 13 7.60 6.60 -2 -9 -13 45.00 6.40 2 9 13 29.00 8.10 -3 -9 -13 4.00 6.00 3 9 13 1.20 7.30 1 -2 -14 12.80 7.90 -1 2 14 3.40 6.00 0 -2 -14 20.20 7.90 0 2 14 11.40 6.50 -1 -2 -14 7.20 7.80 1 2 14 12.90 6.80 -2 -2 -14 21.00 8.20 2 2 14 13.80 7.20 2 -3 -14 8.10 7.10 -2 3 14 14.60 6.40 1 -3 -14 10.90 7.30 -1 3 14 -8.80 5.10 0 -3 -14 -12.00 6.40 0 3 14 10.50 6.10 -1 -3 -14 161.28 13.50 1 3 14 152.28 12.50 -2 -3 -14 61.19 9.20 2 3 14 52.49 9.20 -3 -3 -14 42.80 8.80 3 3 14 65.49 9.20 2 -4 -14 -4.60 6.60 -2 4 14 2.60 6.10 1 -4 -14 -5.70 6.50 -1 4 14 4.90 5.60 0 -4 -14 16.90 6.70 0 4 14 9.60 6.00 -1 -4 -14 -2.30 6.40 1 4 14 16.60 6.30 -2 -4 -14 37.80 8.20 2 4 14 41.00 7.90 -3 -4 -14 -5.20 7.10 3 4 14 0.60 7.30 -2 5 14 -5.20 6.20 1 -5 -14 43.70 7.20 -1 5 14 38.20 8.20 0 -5 -14 81.89 10.60 0 5 14 71.29 9.00 -1 -5 -14 12.80 6.20 1 5 14 11.80 6.70 -2 -5 -14 20.10 6.80 2 5 14 13.30 6.60 -3 -5 -14 7.20 6.80 3 5 14 7.10 6.70 -2 6 14 5.80 7.10 -1 6 14 3.40 6.90 0 -6 -14 5.20 5.80 0 6 14 -14.10 5.60 -1 -6 -14 8.50 6.30 1 6 14 8.50 6.40 -2 -6 -14 -0.20 6.20 2 6 14 1.40 6.30 -3 -6 -14 5.70 6.80 3 6 14 3.30 7.30 -1 7 14 25.50 7.70 0 7 14 10.60 6.50 -1 -7 -14 5.30 5.90 1 7 14 -2.00 6.90 -2 -7 -14 30.10 6.80 2 7 14 23.30 7.30 -3 -7 -14 25.20 7.20 3 7 14 22.30 7.90 1 8 14 14.20 7.50 -2 -8 -14 5.20 6.60 2 8 14 -2.80 6.90 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 43796 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 O7 O 0.8244(2) 0.2147(2) 1.27924(16) 0.0273(5) Uani 1 1 d . . . . . O6 O 0.4731(2) 0.6867(2) 1.14270(17) 0.0295(5) Uani 1 1 d . . . . . H6 H 0.4050 0.7525 1.1530 0.044 Uiso 1 1 calc GR . . . . O8 O 0.9778(2) 0.1562(2) 1.13317(18) 0.0335(5) Uani 1 1 d D . . . . O3 O 0.1324(2) 0.9742(2) 0.32567(18) 0.0326(5) Uani 1 1 d . . . . . O1 O 0.2944(2) 0.4740(2) 0.63143(19) 0.0314(5) Uani 1 1 d . . . . . H1 H 0.2217 0.4207 0.6406 0.047 Uiso 1 1 calc GR . . . . O5 O 0.4598(3) 0.8454(2) 0.93609(18) 0.0362(5) Uani 1 1 d . . . . . O4 O 0.2446(2) 0.8542(2) 0.20461(19) 0.0352(5) Uani 1 1 d . . . . . O2 O 0.1421(2) 0.6338(2) 0.46900(19) 0.0339(5) Uani 1 1 d . . . . . O9 O 0.1062(3) 0.2800(3) 0.7121(2) 0.0410(6) Uani 1 1 d D . . . . H9A H 0.1328 0.2107 0.7870 0.061 Uiso 1 1 d DG . . . . N2 N 0.7969(3) 0.7171(2) 0.60073(19) 0.0210(5) Uani 1 1 d . . . . . N1 N 0.7734(3) 0.9328(2) 0.4379(2) 0.0241(5) Uani 1 1 d . . . . . H1A H 0.7954 1.0201 0.3822 0.029 Uiso 1 1 calc R . . . . O10 O 0.2198(4) 0.0810(3) 0.9345(2) 0.0610(8) Uani 1 1 d D . . . . H10C H 0.1349 0.0559 0.9820 0.092 Uiso 1 1 d DG . . . . H10D H 0.2868 0.0015 0.9446 0.092 Uiso 1 1 d DG . . . . C14 C 0.6991(3) 0.4878(3) 1.0903(2) 0.0190(5) Uani 1 1 d . . . . . H14 H 0.6623 0.4649 1.1768 0.023 Uiso 1 1 calc R . . . . C15 C 0.6413(3) 0.6217(3) 0.9934(2) 0.0199(5) Uani 1 1 d . . . . . C13 C 0.8107(3) 0.3869(3) 1.0607(2) 0.0194(5) Uani 1 1 d . . . . . C17 C 0.8726(3) 0.2429(3) 1.1672(2) 0.0217(6) Uani 1 1 d . . . . . C16 C 0.6969(3) 0.6552(3) 0.8665(2) 0.0215(5) Uani 1 1 d . . . . . H16 H 0.6585 0.7476 0.8004 0.026 Uiso 1 1 calc R . . . . C12 C 0.8637(3) 0.4196(3) 0.9342(2) 0.0202(5) Uani 1 1 d . . . . . H12 H 0.9385 0.3496 0.9142 0.024 Uiso 1 1 calc R . . . . C11 C 0.8077(3) 0.5545(3) 0.8364(2) 0.0187(5) Uani 1 1 d . . . . . C4 C 0.6481(3) 0.7350(3) 0.5468(2) 0.0207(5) Uani 1 1 d . . . . . C5 C 0.6344(3) 0.8724(3) 0.4421(2) 0.0220(6) Uani 1 1 d . . . . . C10 C 0.8733(3) 0.5830(3) 0.7018(2) 0.0238(6) Uani 1 1 d . . . . . H10A H 0.9889 0.5904 0.7011 0.029 Uiso 1 1 calc R . . . . H10B H 0.8621 0.4962 0.6809 0.029 Uiso 1 1 calc R . . . . C9 C 0.8674(3) 0.8379(3) 0.5313(2) 0.0236(6) Uani 1 1 d . . . . . H9 H 0.9710 0.8532 0.5472 0.028 Uiso 1 1 calc R . . . . C1 C 0.2646(3) 0.5984(3) 0.5309(2) 0.0229(6) Uani 1 1 d . . . . . C2 C 0.3959(3) 0.6933(3) 0.4995(2) 0.0224(6) Uani 1 1 d . . . . . C3 C 0.5295(3) 0.6441(3) 0.5778(2) 0.0220(6) Uani 1 1 d . . . . . H3 H 0.5387 0.5514 0.6498 0.026 Uiso 1 1 calc R . . . . C18 C 0.5164(3) 0.7300(3) 1.0211(2) 0.0237(6) Uani 1 1 d . . . . . C8 C 0.2417(3) 0.8867(3) 0.3007(2) 0.0243(6) Uani 1 1 d . . . . . C6 C 0.5032(3) 0.9224(3) 0.3618(2) 0.0240(6) Uani 1 1 d . . . . . H6A H 0.4953 1.0150 0.2898 0.029 Uiso 1 1 calc R . . . . C7 C 0.3834(3) 0.8305(3) 0.3915(2) 0.0226(6) Uani 1 1 d . . . . . H9B H 0.026(3) 0.268(4) 0.680(4) 0.056(12) Uiso 1 1 d D . . . . H8 H 1.023(4) 0.088(3) 1.199(3) 0.063(12) Uiso 1 1 d 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 O7 0.0350(11) 0.0201(9) 0.0155(9) 0.0012(7) 0.0026(8) 0.0062(8) O6 0.0357(11) 0.0262(10) 0.0176(9) -0.0048(8) 0.0004(8) 0.0128(8) O8 0.0376(12) 0.0295(11) 0.0201(10) -0.0026(9) -0.0031(9) 0.0181(9) O3 0.0316(11) 0.0358(11) 0.0246(10) -0.0120(9) -0.0046(8) 0.0168(9) O1 0.0308(11) 0.0283(11) 0.0286(11) -0.0030(9) -0.0058(9) -0.0045(8) O5 0.0473(13) 0.0249(10) 0.0220(10) -0.0007(8) 0.0007(9) 0.0144(9) O4 0.0337(11) 0.0452(13) 0.0249(10) -0.0176(10) -0.0071(8) 0.0153(10) O2 0.0280(11) 0.0371(12) 0.0305(11) -0.0072(9) -0.0049(9) 0.0004(9) O9 0.0356(13) 0.0351(13) 0.0444(14) -0.0053(10) -0.0127(11) -0.0041(10) N2 0.0231(11) 0.0223(11) 0.0132(10) -0.0048(9) 0.0008(8) 0.0045(9) N1 0.0269(12) 0.0199(11) 0.0179(11) -0.0009(9) 0.0010(9) 0.0009(9) O10 0.073(2) 0.0527(16) 0.0384(14) -0.0069(12) 0.0011(13) 0.0207(14) C14 0.0210(13) 0.0193(12) 0.0133(11) -0.0035(10) -0.0010(9) 0.0001(10) C15 0.0214(13) 0.0195(13) 0.0181(12) -0.0071(10) -0.0008(10) -0.0003(10) C13 0.0196(12) 0.0183(12) 0.0177(12) -0.0047(10) -0.0028(10) 0.0002(10) C17 0.0228(13) 0.0203(13) 0.0175(12) -0.0033(10) -0.0038(10) 0.0019(10) C16 0.0257(13) 0.0165(12) 0.0171(12) -0.0021(10) -0.0045(10) 0.0025(10) C12 0.0191(12) 0.0204(13) 0.0195(12) -0.0078(10) -0.0016(10) 0.0034(10) C11 0.0204(12) 0.0193(12) 0.0129(11) -0.0029(10) -0.0016(9) -0.0012(10) C4 0.0234(13) 0.0221(13) 0.0137(11) -0.0072(10) 0.0006(10) 0.0058(10) C5 0.0241(13) 0.0215(13) 0.0168(12) -0.0057(10) 0.0033(10) 0.0015(11) C10 0.0248(13) 0.0228(13) 0.0160(12) -0.0014(11) -0.0028(10) 0.0049(11) C9 0.0233(13) 0.0267(14) 0.0207(13) -0.0108(11) 0.0027(10) 0.0004(11) C1 0.0230(13) 0.0236(13) 0.0180(12) -0.0065(11) 0.0012(10) 0.0046(11) C2 0.0242(13) 0.0218(13) 0.0177(12) -0.0071(11) 0.0022(10) 0.0048(11) C3 0.0261(14) 0.0205(13) 0.0151(12) -0.0039(10) 0.0008(10) 0.0016(11) C18 0.0278(14) 0.0204(13) 0.0190(13) -0.0050(11) -0.0011(10) 0.0017(11) C8 0.0241(14) 0.0225(13) 0.0203(13) -0.0044(11) -0.0014(10) 0.0045(11) C6 0.0278(14) 0.0197(13) 0.0172(12) -0.0029(10) 0.0006(10) 0.0069(11) C7 0.0231(13) 0.0232(13) 0.0186(12) -0.0086(11) 0.0000(10) 0.0073(11) 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' 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 C18 O6 H6 109.5 . . C17 O8 H8 111(3) . . C1 O1 H1 109.5 . . H9A O9 H9B 114.6 . . C4 N2 C10 126.6(2) . . C9 N2 C4 107.6(2) . . C9 N2 C10 125.3(2) . . C5 N1 H1A 125.6 . . C9 N1 H1A 125.6 . . C9 N1 C5 108.7(2) . . H10C O10 H10D 109.5 . . C15 C14 H14 120.0 . . C15 C14 C13 120.0(2) . . C13 C14 H14 120.0 . . C14 C15 C16 119.7(2) . . C14 C15 C18 121.3(2) . . C16 C15 C18 119.0(2) . . C14 C13 C17 119.2(2) . . C12 C13 C14 120.1(2) . . C12 C13 C17 120.7(2) . . O7 C17 O8 124.0(2) . . O7 C17 C13 120.2(2) . . O8 C17 C13 115.7(2) . . C15 C16 H16 119.7 . . C11 C16 C15 120.5(2) . . C11 C16 H16 119.7 . . C13 C12 H12 119.8 . . C13 C12 C11 120.4(2) . . C11 C12 H12 119.8 . . C16 C11 C12 119.3(2) . . C16 C11 C10 123.5(2) . . C12 C11 C10 117.2(2) . . N2 C4 C5 106.5(2) . . C3 C4 N2 131.8(2) . . C3 C4 C5 121.7(2) . . N1 C5 C4 106.5(2) . . N1 C5 C6 131.6(2) . . C6 C5 C4 121.8(2) . . N2 C10 C11 115.0(2) . . N2 C10 H10A 108.5 . . N2 C10 H10B 108.5 . . C11 C10 H10A 108.5 . . C11 C10 H10B 108.5 . . H10A C10 H10B 107.5 . . N2 C9 H9 124.7 . . N1 C9 N2 110.7(2) . . N1 C9 H9 124.7 . . O1 C1 C2 113.1(2) . . O2 C1 O1 123.6(3) . . O2 C1 C2 123.3(2) . . C3 C2 C1 118.7(2) . . C3 C2 C7 121.2(3) . . C7 C2 C1 120.0(2) . . C4 C3 C2 117.3(2) . . C4 C3 H3 121.4 . . C2 C3 H3 121.4 . . O6 C18 C15 113.6(2) . . O5 C18 O6 124.4(2) . . O5 C18 C15 122.0(2) . . O3 C8 C7 115.5(2) . . O4 C8 O3 124.5(2) . . O4 C8 C7 119.7(2) . . C5 C6 H6A 121.5 . . C5 C6 C7 116.9(2) . . C7 C6 H6A 121.5 . . C2 C7 C8 123.0(2) . . C6 C7 C2 121.0(2) . . C6 C7 C8 115.9(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O7 C17 1.233(3) . O6 H6 0.8400 . O6 C18 1.306(3) . O8 C17 1.287(3) . O8 H8 0.849(19) . O3 C8 1.264(3) . O1 H1 0.8400 . O1 C1 1.306(3) . O5 C18 1.220(3) . O4 C8 1.241(3) . O2 C1 1.219(3) . O9 H9A 0.8702 . O9 H9B 0.838(19) . N2 C4 1.393(3) . N2 C10 1.459(3) . N2 C9 1.339(3) . N1 H1A 0.8800 . N1 C5 1.382(4) . N1 C9 1.319(3) . O10 H10C 0.8703 . O10 H10D 0.8699 . C14 H14 0.9500 . C14 C15 1.387(3) . C14 C13 1.390(3) . C15 C16 1.397(3) . C15 C18 1.497(3) . C13 C17 1.503(3) . C13 C12 1.389(3) . C16 H16 0.9500 . C16 C11 1.388(3) . C12 H12 0.9500 . C12 C11 1.394(3) . C11 C10 1.509(3) . C4 C5 1.398(3) . C4 C3 1.377(4) . C5 C6 1.387(4) . C10 H10A 0.9900 . C10 H10B 0.9900 . C9 H9 0.9500 . C1 C2 1.490(4) . C2 C3 1.390(4) . C2 C7 1.414(4) . C3 H3 0.9500 . C8 C7 1.523(4) . C6 H6A 0.9500 . C6 C7 1.392(4) . 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 O3 C8 C7 C2 95.0(3) . . . . O3 C8 C7 C6 -85.5(3) . . . . O1 C1 C2 C3 -1.1(3) . . . . O1 C1 C2 C7 178.7(2) . . . . O4 C8 C7 C2 -90.0(3) . . . . O4 C8 C7 C6 89.5(3) . . . . O2 C1 C2 C3 178.7(2) . . . . O2 C1 C2 C7 -1.5(4) . . . . N2 C4 C5 N1 -0.9(3) . . . . N2 C4 C5 C6 176.5(2) . . . . N2 C4 C3 C2 -177.1(2) . . . . N1 C5 C6 C7 177.8(2) . . . . C14 C15 C16 C11 0.9(4) . . . . C14 C15 C18 O6 1.6(4) . . . . C14 C15 C18 O5 -177.0(3) . . . . C14 C13 C17 O7 0.2(4) . . . . C14 C13 C17 O8 -178.8(2) . . . . C14 C13 C12 C11 1.2(4) . . . . C15 C14 C13 C17 179.6(2) . . . . C15 C14 C13 C12 -0.5(4) . . . . C15 C16 C11 C12 -0.3(4) . . . . C15 C16 C11 C10 -179.9(3) . . . . C13 C14 C15 C16 -0.6(4) . . . . C13 C14 C15 C18 177.6(2) . . . . C13 C12 C11 C16 -0.8(4) . . . . C13 C12 C11 C10 178.9(2) . . . . C17 C13 C12 C11 -178.9(2) . . . . C16 C15 C18 O6 179.7(2) . . . . C16 C15 C18 O5 1.2(4) . . . . C16 C11 C10 N2 -7.5(4) . . . . C12 C13 C17 O7 -179.7(3) . . . . C12 C13 C17 O8 1.3(4) . . . . C12 C11 C10 N2 172.9(2) . . . . C4 N2 C10 C11 -76.4(3) . . . . C4 N2 C9 N1 0.8(3) . . . . C4 C5 C6 C7 1.2(4) . . . . C5 N1 C9 N2 -1.4(3) . . . . C5 C4 C3 C2 0.9(4) . . . . C5 C6 C7 C2 0.4(4) . . . . C5 C6 C7 C8 -179.1(2) . . . . C10 N2 C4 C5 -171.7(2) . . . . C10 N2 C4 C3 6.6(4) . . . . C10 N2 C9 N1 172.7(2) . . . . C9 N2 C4 C5 0.0(3) . . . . C9 N2 C4 C3 178.3(3) . . . . C9 N2 C10 C11 113.3(3) . . . . C9 N1 C5 C4 1.4(3) . . . . C9 N1 C5 C6 -175.6(3) . . . . C1 C2 C3 C4 -179.5(2) . . . . C1 C2 C7 C8 -1.7(4) . . . . C1 C2 C7 C6 178.8(2) . . . . C3 C4 C5 N1 -179.3(2) . . . . C3 C4 C5 C6 -2.0(4) . . . . C3 C2 C7 C8 178.1(2) . . . . C3 C2 C7 C6 -1.4(4) . . . . C18 C15 C16 C11 -177.2(2) . . . . C7 C2 C3 C4 0.7(4) . . . .