#------------------------------------------------------------------------------ #$Date: 2016-05-31 15:26:35 +0300 (Tue, 31 May 2016) $ #$Revision: 183182 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119000.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_7119000 loop_ _publ_author_name 'Ryo Nozawa' 'Keitaro Yamamoto' 'Ichiro Hisaki' 'Ji-Young Shin' 'Hiroshi Shinokubo' _publ_section_title ; Ni^II^ tetrahydronorcorroles: antiaromatic porphyrinoids with saturated pyrrole units ; _journal_name_full Chem.Commun. _journal_page_first 7106 _journal_volume 52 _journal_year 2016 _chemical_formula_moiety 'C37 H33 N5 Ni' _chemical_formula_sum 'C37 H33 N5 Ni' _chemical_formula_weight 606.40 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yab' _space_group_name_H-M_alt 'P 1 21/a 1' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2016-01-08 deposited with the CCDC. 2016-05-03 downloaded from the CCDC. ; _cell_angle_alpha 90.0000 _cell_angle_beta 103.8436(4) _cell_angle_gamma 90.0000 _cell_formula_units_Z 2 _cell_length_a 7.08430(10) _cell_length_b 25.1223(2) _cell_length_c 8.23270(10) _cell_measurement_reflns_used 18840 _cell_measurement_temperature 100 _cell_measurement_theta_max 28.739 _cell_measurement_theta_min 3.802 _cell_volume 1422.65(3) _computing_cell_refinement HKL2000 _computing_data_collection DENZO _computing_data_reduction HKL2000 _computing_molecular_graphics 'CrystalStructure 4.1.1' _computing_publication_material 'CrystalStructure 4.1.1 (Rigaku, 2015)' _computing_structure_refinement 'SHELXL Version 2014/7 (Sheldrick, 2008)' _computing_structure_solution 'Superflip (Palatinus, et al., 2007)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_details '1.00 degrees, -1.0 sec, detector distance 74.98 mm' _diffrn_measurement_device_type 'CCD (MX225HE Rayonix)' _diffrn_measurement_method '\w scans' _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.80000 _diffrn_reflns_av_R_equivalents 0.073 _diffrn_reflns_Laue_measured_fraction_full 0.975 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 18840 _diffrn_reflns_point_group_measured_fraction_full 0.975 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_theta_full 28.685 _diffrn_reflns_theta_max 28.739 _diffrn_reflns_theta_min 3.802 _diffrn_standards_interval_count . _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.000 _exptl_absorpt_correction_type none _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 636.00 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.55 _refine_diff_density_min -0.56 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 208 _refine_ls_number_reflns 2532 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0589 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0253P)^2^+6.4079P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1381 _refine_ls_wR_factor_ref 0.1381 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2522 _reflns_number_total 2532 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file c6cc02918c2.cif _cod_data_source_block NorCor_CN _cod_database_code 7119000 _shelx_res_file ; shelxl.res created by SHELXL-2014/7 TITL Template texray.inf CELL 0.80000 7.08430 25.12230 8.23270 90.000 103.844 90.000 ZERR 2 0.00010 0.00020 0.00010 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, -Z SFAC C H N NI DISP C 0.004 0.002 9.49 DISP H 0.000 0.000 0.64 DISP N 0.008 0.004 19.35 DISP Ni 0.306 1.376 6204.76 UNIT 74 66 10 2 SHEL 99999.000000 0.831620 OMIT -1 3 1 OMIT -5 10 5 L.S. 30 FMAP 2 PLAN -25 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP 23.0 ACTA WGHT 0.025300 6.407900 FVAR 3.02226 NI1 4 0.500000 0.500000 0.500000 10.50000 0.01473 0.00694 = 0.01910 0.00380 0.00574 -0.00136 N1 3 0.700532 0.478254 0.659216 11.00000 0.02001 0.01044 = 0.01865 -0.00108 0.01055 -0.00264 N2 3 0.342980 0.446330 0.527916 11.00000 0.01912 0.00618 = 0.01710 0.00254 0.00729 0.00210 PART 1 N3 3 1.088668 0.372468 1.080116 10.50000 0.02672 0.01624 = 0.02204 0.00613 0.00584 -0.00111 PART 0 C1 1 0.868844 0.507680 0.680040 11.00000 0.01986 0.00964 = 0.01447 0.00072 0.00870 -0.00138 C2 1 1.008925 0.482148 0.805970 11.00000 0.01445 0.01488 = 0.01578 -0.00091 0.00372 -0.00132 AFIX 43 H2 2 1.137087 0.492820 0.847658 11.00000 -1.20000 AFIX 0 C3 1 0.918363 0.437397 0.856908 11.00000 0.01936 0.01220 = 0.01426 0.00150 0.00402 -0.00010 PART 2 AFIX 43 H3 2 0.976201 0.412911 0.938406 10.50000 -1.20000 AFIX 0 PART 0 C4 1 0.722500 0.436345 0.761364 11.00000 0.02032 0.00633 = 0.01779 -0.00198 0.00972 -0.00065 C5 1 0.557001 0.399654 0.757571 11.00000 0.01822 0.00669 = 0.01456 -0.00023 0.00868 -0.00157 C6 1 0.381672 0.404754 0.644035 11.00000 0.01978 0.00667 = 0.01406 -0.00001 0.00781 -0.00034 C7 1 0.198558 0.371016 0.613678 11.00000 0.02106 0.00899 = 0.01770 -0.00047 0.00570 -0.00294 AFIX 23 H7A 2 0.151110 0.368269 0.714544 11.00000 -1.20000 H7B 2 0.222882 0.335507 0.577114 11.00000 -1.20000 AFIX 0 C8 1 0.049199 0.401271 0.473119 11.00000 0.02010 0.00789 = 0.01753 -0.00078 0.00837 -0.00565 AFIX 23 H8A 2 0.003638 0.378768 0.375888 11.00000 -1.20000 H8B 2 -0.061609 0.413358 0.513157 11.00000 -1.20000 AFIX 0 C9 1 0.164066 0.447386 0.432927 11.00000 0.01726 0.00818 = 0.01659 -0.00149 0.00920 -0.00386 PART 1 C10 1 1.008299 0.401351 0.978563 10.50000 0.02215 0.01199 = 0.01449 -0.00130 0.00543 -0.00331 PART 0 C11 1 0.588067 0.356429 0.886187 11.00000 0.01541 0.01154 = 0.01354 0.00376 0.00470 -0.00283 C12 1 0.570755 0.368669 1.048975 11.00000 0.01823 0.01951 = 0.01863 0.00018 0.00665 -0.00505 C13 1 0.603433 0.328094 1.168366 11.00000 0.01681 0.03721 = 0.01369 0.00907 0.00531 -0.00094 AFIX 43 H13 2 0.592774 0.335825 1.276284 11.00000 -1.20000 AFIX 0 C14 1 0.650923 0.276996 1.131929 11.00000 0.01325 0.03274 = 0.03086 0.02195 0.00613 0.00234 C15 1 0.669689 0.265765 0.970976 11.00000 0.01668 0.01606 = 0.03872 0.01221 0.00722 0.00046 AFIX 43 H15 2 0.701306 0.231390 0.944922 11.00000 -1.20000 AFIX 0 C16 1 0.641971 0.305076 0.848219 11.00000 0.01681 0.01204 = 0.02086 0.00302 0.00410 -0.00179 C17 1 0.516819 0.423471 1.095296 11.00000 0.04087 0.02675 = 0.02328 -0.00797 0.01753 -0.00888 AFIX 137 H17A 2 0.379120 0.428481 1.055650 11.00000 -1.20000 H17B 2 0.584150 0.449545 1.045111 11.00000 -1.20000 H17C 2 0.552719 0.427410 1.214730 11.00000 -1.20000 AFIX 0 C18 1 0.679055 0.234283 1.263527 11.00000 0.02821 0.05581 = 0.05781 0.04919 0.02272 0.01867 AFIX 137 H18A 2 0.554553 0.221982 1.274877 11.00000 -1.20000 H18B 2 0.750845 0.248482 1.368432 11.00000 -1.20000 H18C 2 0.749725 0.205117 1.231277 11.00000 -1.20000 AFIX 0 C19 1 0.673353 0.292296 0.678839 11.00000 0.03184 0.01443 = 0.02598 -0.00213 0.00891 0.00300 AFIX 137 H19A 2 0.723114 0.256744 0.679111 11.00000 -1.20000 H19B 2 0.764947 0.316969 0.652177 11.00000 -1.20000 H19C 2 0.552103 0.294986 0.596713 11.00000 -1.20000 AFIX 0 HKLF 4 REM Template texray.inf REM R1 = 0.0589 for 2522 Fo > 4sig(Fo) and 0.0590 for all 2532 data REM 208 parameters refined using 0 restraints END WGHT 0.0268 6.3221 REM Instructions for potential hydrogen bonds EQIV $1 x-1, y, z-1 HTAB C8 N3_$1 REM Highest difference peak 0.551, deepest hole -0.561, 1-sigma level 0.093 Q1 1 0.3852 0.4977 0.3448 11.00000 0.05 0.55 Q2 1 0.3452 0.4989 0.4864 11.00000 0.05 0.53 Q3 1 0.8037 0.4986 0.5072 11.00000 0.05 0.49 Q4 1 0.4974 0.4503 0.4366 11.00000 0.05 0.36 Q5 1 0.6336 0.2489 1.3878 11.00000 0.05 0.35 Q6 1 0.2154 0.4985 0.3028 11.00000 0.05 0.35 Q7 1 0.9034 0.5004 0.5030 11.00000 0.05 0.34 Q8 1 0.5636 0.3756 0.8120 11.00000 0.05 0.31 Q9 1 0.0945 0.4262 0.4412 11.00000 0.05 0.31 Q10 1 0.3583 0.4391 0.9689 11.00000 0.05 0.31 Q11 1 0.3644 0.4394 0.7938 11.00000 0.05 0.31 Q12 1 0.6809 0.3313 0.8772 11.00000 0.05 0.30 Q13 1 0.6331 0.5729 0.4157 11.00000 0.05 0.30 Q14 1 1.1688 0.3410 1.1700 11.00000 0.05 0.29 Q15 1 0.6438 0.4367 1.1516 11.00000 0.05 0.29 Q16 1 -0.2597 0.4085 0.4679 11.00000 0.05 0.29 Q17 1 0.8784 0.5282 0.6263 11.00000 0.05 0.29 Q18 1 -0.0623 0.3998 0.3342 11.00000 0.05 0.29 Q19 1 0.8215 0.4550 0.8320 11.00000 0.05 0.29 Q20 1 0.4840 0.4599 0.9747 11.00000 0.05 0.29 Q21 1 0.3704 0.3510 0.5933 11.00000 0.05 0.28 Q22 1 0.6508 0.2213 0.6514 11.00000 0.05 0.28 Q23 1 0.3041 0.5353 0.2771 11.00000 0.05 0.28 Q24 1 0.4232 0.5328 0.4553 11.00000 0.05 0.27 Q25 1 0.7169 0.4724 0.8900 11.00000 0.05 0.27 ; _shelx_res_checksum 41963 _shelx_hkl_file ; 0 0 2 7317.80 174.40 0 0 4 1914.70 37.40 0 0 523008.30 361.00 0 0 622124.00 352.70 0 0 7 6741.50 115.90 0 0 8 6237.90 107.60 0 0 9 363.50 15.10 0 1 3 381.40 7.30 0 1 4 839.90 13.50 0 1 5 2730.20 39.70 0 1 6 1098.80 17.90 0 1 7 283.30 7.00 0 1 8 22.20 2.70 0 1 9 1109.90 22.20 0 2 420091.80 264.00 0 2 5 9260.40 110.80 0 2 6 9070.10 110.10 0 2 717386.70 202.40 0 2 8 1333.90 19.70 0 2 9 26.60 4.30 0 3 0 80.20 3.20 0 3 2 1537.40 20.70 0 3 4 5712.00 68.70 0 3 5 3067.40 41.80 0 3 6 543.40 10.60 0 3 7 5186.40 69.30 0 3 8 61.60 4.10 0 3 9 4288.70 69.70 0 4 2 959.10 13.80 0 4 3 5893.70 73.70 0 4 417685.10 205.90 0 4 511951.20 147.90 0 4 628622.30 326.60 0 4 7 1101.70 18.70 0 4 8 77.20 5.60 0 4 9 269.60 10.00 0 5 0 27.90 1.80 0 5 1 3019.80 38.90 0 5 2 4693.90 63.00 0 5 3 2950.50 40.40 0 5 4 662.00 11.50 0 5 5 255.70 7.20 0 5 6 4416.60 62.10 0 5 710417.10 133.30 0 5 8 345.80 7.50 0 5 9 1273.30 24.60 0 6 0 6066.80 119.00 0 6 2 407.10 8.70 0 6 314924.80 187.00 0 6 4 364.30 7.50 0 6 5 5133.10 71.00 0 6 622781.90 259.20 0 6 7 3865.90 53.00 0 6 8 414.90 9.70 0 6 9 3263.80 55.90 0 7 0 75.40 3.40 0 7 1 3549.20 45.60 0 7 2 4185.80 56.60 0 7 3 804.40 13.00 0 7 4 81.30 2.70 0 7 5 214.60 5.00 0 7 6 5136.80 67.20 0 7 7 530.90 10.40 0 7 8 1647.20 30.80 0 7 9 5.20 4.80 0 8 1 9509.60 110.80 0 8 218609.50 299.40 0 8 312051.90 141.00 0 8 4 9953.50 119.60 0 8 5 8496.00 103.60 0 8 6 4215.50 53.90 0 8 714178.10 158.60 0 8 8 1822.20 28.10 0 8 9 2442.50 40.10 0 9 0 5.10 1.30 0 9 1 1235.10 18.80 0 9 2 581.30 11.90 0 9 3 4137.70 57.50 0 9 4 2279.60 33.00 0 9 5 867.30 15.40 0 9 6 82.70 3.20 0 9 7 252.60 6.40 0 9 8 1155.70 20.50 0 9 9 668.80 12.50 0 10 127605.70 635.70 0 10 2 226.70 5.70 0 10 3 2039.70 32.30 0 10 4 7627.20 95.30 0 10 5 8396.50 117.50 0 10 625221.30 301.40 0 10 7 9990.50 123.60 0 10 8 2823.00 38.10 0 10 9 789.50 16.10 0 11 0 3.10 1.40 0 11 114176.30 165.10 0 11 2 5291.40 68.30 0 11 3 540.70 11.40 0 11 4 420.00 8.70 0 11 5 4728.70 66.90 0 11 6 1492.10 21.80 0 11 7 298.70 8.30 0 11 8 38.10 3.40 0 11 9 1774.50 37.70 0 12 011019.40 185.20 0 12 1 8099.60 99.60 0 12 2 2359.20 34.60 0 12 311219.40 143.80 0 12 412971.70 167.10 0 12 5 9435.70 124.60 0 12 6 9253.00 109.90 0 12 7 5081.50 64.00 0 12 8 3202.60 42.90 0 12 9 744.50 19.50 0 13 0 64.90 3.40 0 13 1 198.30 4.70 0 13 2 98.40 3.00 0 13 3 146.30 4.30 0 13 4 2552.00 41.60 0 13 5 983.20 16.30 0 13 612204.60 147.40 0 13 7 7.80 2.10 0 13 8 9.40 3.10 0 13 9 189.80 17.60 0 14 1 885.00 15.40 0 14 2 6792.40 86.80 0 14 310890.10 134.20 0 14 4 1094.00 19.40 0 14 517334.10 200.20 0 14 6 2133.50 31.50 0 14 7 2453.40 35.00 0 14 8 2425.20 36.10 0 14 9 177.30 14.00 0 15 0 82.80 4.10 0 15 1 1066.00 17.90 0 15 2 1599.00 25.90 0 15 3 9.70 1.40 0 15 4 562.00 11.20 0 15 5 552.00 11.80 0 15 6 1620.50 26.80 0 15 7 204.80 6.00 0 15 8 38.20 5.30 0 15 9 1292.30 38.70 0 16 026102.60 485.50 0 16 1 6783.50 86.00 0 16 214698.30 173.70 0 16 315026.90 177.70 0 16 4 4358.10 62.70 0 16 5 5744.60 75.70 0 16 6 1128.40 18.40 0 16 7 1005.40 23.00 0 16 8 423.20 11.20 0 17 0 30.40 2.60 0 17 1 2801.50 42.00 0 17 2 379.10 7.50 0 17 3 61.10 2.80 0 17 411722.20 139.50 0 17 5 5427.50 75.30 0 17 6 242.30 7.10 0 17 7 65.10 4.10 0 17 8 421.10 11.50 0 18 017765.20 302.30 0 18 124331.00 282.00 0 18 210891.60 133.70 0 18 321050.30 244.60 0 18 421770.70 250.90 0 18 5 2789.10 40.80 0 18 6 4603.80 56.30 0 18 7 366.30 9.30 0 18 8 2234.80 51.00 0 19 0 7.40 2.20 0 19 1 3357.70 50.10 0 19 2 1280.30 19.30 0 19 3 1283.20 22.30 0 19 4 1707.90 27.30 0 19 5 1489.50 26.00 0 19 6 760.40 15.40 0 19 7 23.10 3.50 0 19 8 18.60 7.10 0 20 016308.80 274.00 0 20 134455.70 395.30 0 20 212499.10 137.60 0 20 311372.20 136.00 0 20 417464.70 205.40 0 20 510532.20 130.20 0 20 6 6412.50 77.20 0 20 7 594.10 14.70 0 20 8 2073.80 40.80 0 21 0 29.80 3.00 0 21 1 8559.60 109.70 0 21 212413.30 152.40 0 21 3 296.90 6.80 0 21 4 20.40 2.20 0 21 5 96.50 4.10 0 21 6 16.80 2.70 0 21 7 38.80 4.80 0 21 8 46.60 14.40 0 22 014452.60 252.20 0 22 1 7765.20 98.60 0 22 226124.30 304.70 0 22 3 4100.10 58.00 0 22 4 6342.00 81.10 0 22 5 4377.70 58.50 0 22 6 922.80 15.60 0 22 7 1183.70 25.50 0 23 0 27.00 3.30 0 23 1 954.30 18.20 0 23 2 5188.60 73.70 0 23 3 123.30 4.30 0 23 4 114.60 4.00 0 23 5 58.40 3.70 0 23 6 1236.30 22.40 0 23 7 974.80 18.40 0 24 0 270.20 10.80 0 24 110842.20 143.60 0 24 2 8657.40 104.90 0 24 3 333.50 8.60 0 24 4 1018.30 19.50 0 24 5 3917.30 52.70 0 24 6 1769.10 31.70 0 25 0 9.40 2.80 0 25 1 409.50 9.60 0 25 2 2431.30 37.00 0 25 3 215.00 6.60 0 25 4 69.70 3.50 0 25 5 303.00 7.20 0 25 6 293.20 10.10 0 26 0 3934.60 81.80 0 26 1 64.80 3.70 0 26 2 5479.50 68.90 0 26 3 3983.20 53.60 0 26 4 2050.40 34.20 0 26 5 5004.60 79.60 0 26 6 504.10 14.90 0 27 0 4.90 3.80 0 27 1 4409.40 51.00 0 27 2 550.90 10.40 0 27 3 422.50 9.60 0 27 4 1304.80 26.60 0 27 5 82.30 7.50 0 27 6 356.60 23.70 0 28 0 600.10 23.60 0 28 1 917.60 17.40 0 28 2 834.00 14.90 0 28 3 3248.50 42.00 0 28 4 2800.00 51.30 0 28 5 6679.50 160.90 0 29 0 46.40 5.90 0 29 1 5235.80 67.10 0 29 2 723.50 14.90 0 29 3 161.40 8.20 0 29 4 27.50 8.20 0 30 018024.50 389.50 0 30 1 497.50 15.60 0 30 2 2145.00 55.40 0 30 3 503.20 30.30 1 0 -9 2.20 4.20 1 0 -8 9.80 3.90 1 0 -7 74.10 4.90 1 0 -6 11.00 3.30 1 0 -5 42.30 3.10 1 0 -4 147.70 5.70 1 0 -3 9.70 1.60 1 0 -2 7.50 1.90 1 0 -1 53.60 2.70 1 0 0 21.50 1.30 1 0 1 89.10 2.70 1 0 2 11.20 1.70 1 0 3 844.70 23.30 1 0 4 43.30 1.70 1 0 5 10.80 3.80 1 0 6 10.70 4.70 1 0 7 922.20 33.90 1 0 8 89.30 11.00 1 0 9 16.80 13.90 1 1 -9 1232.50 20.90 1 1 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-4 61.40 6.90 8 0 -3 2405.20 44.70 8 0 -2 25.90 7.80 8 0 -1 687.40 27.40 8 0 1 2136.10 83.30 8 1 -7 834.40 21.60 8 1 -6 243.70 11.20 8 1 -5 133.00 7.30 8 1 -4 21.80 6.60 8 1 -3 2.10 4.60 8 1 -2 2.60 3.10 8 1 -1 6.30 4.90 8 1 0 358.30 15.50 8 1 1 199.30 13.50 8 2 -7 342.50 18.30 8 2 -6 1871.90 36.70 8 2 -5 612.30 12.70 8 2 -4 5120.60 64.60 8 2 -3 78.10 7.10 8 2 -2 139.60 6.50 8 2 -1 959.20 21.60 8 2 0 4411.50 75.90 8 2 1 3166.80 59.30 8 3 -7 2124.70 41.00 8 3 -6 315.00 11.00 8 3 -5 287.80 12.80 8 3 -4 39.40 5.40 8 3 -3 415.30 9.20 8 3 -2 25.20 6.00 8 3 -1 883.00 21.80 8 3 0 1223.70 35.60 8 3 1 36.10 11.90 8 4 -7 1366.60 34.80 8 4 -6 764.10 26.60 8 4 -5 2413.30 52.50 8 4 -4 3075.10 50.60 8 4 -3 7244.40 86.00 8 4 -2 2103.30 37.80 8 4 -1 1429.70 26.70 8 4 0 5243.70 81.40 8 4 1 2874.10 61.90 8 5 -7 35.40 15.80 8 5 -6 29.80 14.10 8 5 -5 44.50 9.50 8 5 -4 5894.10 77.00 8 5 -3 1101.40 19.90 8 5 -2 14.80 4.40 8 5 -1 2033.90 37.90 8 5 0 2169.50 38.60 8 5 1 1015.90 28.30 8 6 -7 246.00 27.60 8 6 -6 2923.20 71.60 8 6 -5 4498.00 79.50 8 6 -412479.40 141.10 8 6 -3 5450.60 69.70 8 6 -2 178.20 8.60 8 6 -1 4160.40 65.60 8 6 0 5405.20 84.10 8 6 1 937.40 36.20 8 7 -6 229.70 27.00 8 7 -5 668.10 21.40 8 7 -4 2163.00 29.90 8 7 -3 219.60 7.90 8 7 -2 468.70 13.60 8 7 -1 107.40 9.00 8 7 0 672.70 16.60 8 7 1 143.10 10.40 8 8 -6 1912.30 38.00 8 8 -514722.00 230.60 8 8 -4 1948.50 33.90 8 8 -3 2754.50 41.30 8 8 -2 2522.70 49.50 8 8 -1 3123.80 53.30 8 8 0 474.90 12.50 8 8 1 3783.40 67.60 8 9 -5 3317.90 83.40 8 9 -4 1242.90 38.00 8 9 -3 654.30 18.20 8 9 -2 689.20 13.10 8 9 -1 144.20 10.00 8 9 0 1388.10 26.30 8 9 1 2.00 8.40 8 10 -5 2067.90 80.20 8 10 -4 1481.90 46.80 8 10 -3 1450.60 26.30 8 10 -2 3967.30 59.00 8 10 -1 3461.00 60.20 8 10 0 6198.30 82.40 8 10 1 159.30 14.80 8 11 -5 94.00 11.10 8 11 -4 84.60 11.20 8 11 -3 77.80 8.50 8 11 -2 1097.10 19.20 8 11 -1 178.00 8.90 8 11 0 1014.10 24.40 8 12 -5 1755.60 50.30 8 12 -4 2784.90 101.00 8 12 -3 633.40 25.30 8 12 -2 2888.40 52.10 8 12 -1 3608.40 56.80 8 12 0 6216.80 90.90 8 13 -4 564.60 33.90 8 13 -3 115.20 13.00 8 13 -2 402.20 16.00 8 13 -1 28.20 9.90 8 13 0 541.90 16.20 8 13 1 166.90 29.50 8 14 -4 3395.00 85.00 8 14 -3 2521.70 66.90 8 14 -2 3637.40 84.50 8 14 -1 1114.50 28.50 8 14 0 1948.00 39.40 8 14 1 3793.40 135.80 8 15 -3 590.60 43.50 8 15 -2 27.10 9.30 8 15 -1 235.00 11.40 8 15 0 221.40 20.10 8 16 -2 389.90 29.60 8 16 -1 2532.10 69.60 8 16 0 786.60 30.60 8 17 -1 64.70 10.50 9 1 -1 1705.30 51.80 9 1 0 1409.20 67.70 9 2 -1 171.30 16.10 9 2 0 403.40 33.90 9 3 -1 641.50 39.90 9 3 0 1026.40 38.40 9 4 -1 495.30 37.90 9 4 0 876.80 52.00 9 5 -1 794.80 26.60 9 5 0 233.20 27.10 9 6 -1 470.50 24.70 9 7 -1 1412.10 62.10 ; _shelx_hkl_checksum 52276 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,-Z 3 -X,-Y,-Z 4 -1/2+X,-1/2-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 Ni1 Ni 0.5000 0.5000 0.5000 0.0133(2) Uani 1 2 d S . P . . N1 N 0.7005(4) 0.47825(11) 0.6592(4) 0.0154(6) Uani 1 1 d . . . . . N2 N 0.3430(4) 0.44633(11) 0.5279(4) 0.0136(6) Uani 1 1 d . . . . . N3 N 1.0887(9) 0.3725(2) 1.0801(8) 0.0217(13) Uani 0.5 1 d . . P A 1 C1 C 0.8688(5) 0.50768(13) 0.6800(4) 0.0139(7) Uani 1 1 d . . . . . C2 C 1.0089(5) 0.48215(13) 0.8060(4) 0.0150(7) Uani 1 1 d . . . . . H2 H 1.1371 0.4928 0.8477 0.018 Uiso 1 1 calc R U . . . C3 C 0.9184(5) 0.43740(13) 0.8569(4) 0.0153(7) Uani 1 1 d . . . . . H3 H 0.9762 0.4129 0.9384 0.018 Uiso 0.5 1 calc R U P B 2 C4 C 0.7225(5) 0.43634(12) 0.7614(4) 0.0139(7) Uani 1 1 d . . . . . C5 C 0.5570(5) 0.39965(12) 0.7576(4) 0.0124(7) Uani 1 1 d . . . . . C6 C 0.3817(5) 0.40475(12) 0.6440(4) 0.0129(7) Uani 1 1 d . . . . . C7 C 0.1986(5) 0.37102(13) 0.6137(4) 0.0157(7) Uani 1 1 d . . . . . H7A H 0.1511 0.3683 0.7145 0.019 Uiso 1 1 calc R U . . . H7B H 0.2229 0.3355 0.5771 0.019 Uiso 1 1 calc R U . . . C8 C 0.0492(5) 0.40127(13) 0.4731(4) 0.0145(7) Uani 1 1 d . . . . . H8A H 0.0036 0.3788 0.3759 0.017 Uiso 1 1 calc R U . . . H8B H -0.0616 0.4134 0.5132 0.017 Uiso 1 1 calc R U . . . C9 C 0.1641(5) 0.44739(13) 0.4329(4) 0.0131(7) Uani 1 1 d . . . . . C10 C 1.0083(10) 0.4014(3) 0.9786(8) 0.0160(14) Uani 0.5 1 d . . P A 1 C11 C 0.5881(5) 0.35643(13) 0.8862(4) 0.0133(7) Uani 1 1 d . . . . . C12 C 0.5708(5) 0.36867(14) 1.0490(4) 0.0184(7) Uani 1 1 d . . . . . C13 C 0.6034(5) 0.32809(16) 1.1684(4) 0.0223(8) Uani 1 1 d . . . . . H13 H 0.5928 0.3358 1.2763 0.027 Uiso 1 1 calc R U . . . C14 C 0.6509(5) 0.27700(16) 1.1319(5) 0.0255(9) Uani 1 1 d . . . . . C15 C 0.6697(5) 0.26576(15) 0.9710(5) 0.0237(8) Uani 1 1 d . . . . . H15 H 0.7013 0.2314 0.9449 0.028 Uiso 1 1 calc R U . . . C16 C 0.6420(5) 0.30508(14) 0.8482(4) 0.0166(7) Uani 1 1 d . . . . . C17 C 0.5168(7) 0.42347(16) 1.0953(5) 0.0286(9) Uani 1 1 d . . . . . H17A H 0.3791 0.4285 1.0556 0.034 Uiso 1 1 calc R U . . . H17B H 0.5841 0.4495 1.0451 0.034 Uiso 1 1 calc R U . . . H17C H 0.5527 0.4274 1.2147 0.034 Uiso 1 1 calc R U . . . C18 C 0.6791(7) 0.2343(2) 1.2635(7) 0.0452(14) Uani 1 1 d . . . . . H18A H 0.5546 0.2220 1.2749 0.054 Uiso 1 1 calc R U . . . H18B H 0.7508 0.2485 1.3684 0.054 Uiso 1 1 calc R U . . . H18C H 0.7497 0.2051 1.2313 0.054 Uiso 1 1 calc R U . . . C19 C 0.6734(6) 0.29230(14) 0.6788(5) 0.0237(8) Uani 1 1 d . . . . . H19A H 0.7231 0.2567 0.6791 0.028 Uiso 1 1 calc R U . . . H19B H 0.7649 0.3170 0.6522 0.028 Uiso 1 1 calc R U . . . H19C H 0.5521 0.2950 0.5967 0.028 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0147(3) 0.0069(3) 0.0191(4) 0.0038(2) 0.0057(2) -0.0014(2) N1 0.0200(15) 0.0104(13) 0.0186(15) -0.0011(11) 0.0106(12) -0.0026(11) N2 0.0191(15) 0.0062(13) 0.0171(14) 0.0025(11) 0.0073(12) 0.0021(11) N3 0.027(3) 0.016(3) 0.022(3) 0.006(3) 0.006(3) -0.001(3) C1 0.0199(17) 0.0096(15) 0.0145(16) 0.0007(13) 0.0087(13) -0.0014(13) C2 0.0144(16) 0.0149(16) 0.0158(17) -0.0009(13) 0.0037(13) -0.0013(13) C3 0.0194(17) 0.0122(16) 0.0143(16) 0.0015(13) 0.0040(13) -0.0001(13) C4 0.0203(17) 0.0063(15) 0.0178(17) -0.0020(13) 0.0097(14) -0.0007(13) C5 0.0182(17) 0.0067(15) 0.0146(16) -0.0002(13) 0.0087(13) -0.0016(13) C6 0.0198(17) 0.0067(15) 0.0141(16) 0.0000(12) 0.0078(13) -0.0003(13) C7 0.0211(18) 0.0090(15) 0.0177(17) -0.0005(13) 0.0057(14) -0.0029(13) C8 0.0201(17) 0.0079(15) 0.0175(17) -0.0008(13) 0.0084(14) -0.0056(13) C9 0.0173(17) 0.0082(15) 0.0166(16) -0.0015(13) 0.0092(13) -0.0039(13) C10 0.022(4) 0.012(3) 0.014(3) -0.001(3) 0.005(3) -0.003(3) C11 0.0154(16) 0.0115(16) 0.0135(16) 0.0038(13) 0.0047(13) -0.0028(13) C12 0.0182(17) 0.0195(18) 0.0186(18) 0.0002(14) 0.0066(14) -0.0050(14) C13 0.0168(18) 0.037(2) 0.0137(17) 0.0091(16) 0.0053(14) -0.0009(16) C14 0.0133(17) 0.033(2) 0.031(2) 0.0220(18) 0.0061(15) 0.0023(16) C15 0.0167(17) 0.0161(18) 0.039(2) 0.0122(16) 0.0072(16) 0.0005(14) C16 0.0168(17) 0.0120(16) 0.0209(18) 0.0030(13) 0.0041(14) -0.0018(13) C17 0.041(2) 0.027(2) 0.023(2) -0.0080(16) 0.0175(18) -0.0089(18) C18 0.028(2) 0.056(3) 0.058(3) 0.049(3) 0.023(2) 0.019(2) C19 0.032(2) 0.0144(17) 0.026(2) -0.0021(15) 0.0089(16) 0.0030(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; N N 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Ni Ni 0.0000 0.0000 ; International Tables for Crystallography (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 N1 Ni1 N1 180.00(16) 3_666 . N1 Ni1 N2 85.11(13) 3_666 . N1 Ni1 N2 94.89(13) . . N1 Ni1 N2 94.89(13) 3_666 3_666 N1 Ni1 N2 85.11(13) . 3_666 N2 Ni1 N2 180.00(11) . 3_666 C4 N1 C1 112.2(3) . . C4 N1 Ni1 131.4(2) . . C1 N1 Ni1 116.3(2) . . C9 N2 C6 115.0(3) . . C9 N2 Ni1 116.4(2) . . C6 N2 Ni1 128.4(2) . . N1 C1 C2 106.5(3) . . N1 C1 C9 109.7(3) . 3_666 C2 C1 C9 143.8(3) . 3_666 C1 C2 C3 107.0(3) . . C1 C2 H2 126.5 . . C3 C2 H2 126.5 . . C10 C3 C2 125.0(4) . . C10 C3 C4 127.3(4) . . C2 C3 C4 107.7(3) . . C2 C3 H3 126.1 . . C4 C3 H3 126.1 . . N1 C4 C3 106.6(3) . . N1 C4 C5 120.3(3) . . C3 C4 C5 133.1(3) . . C6 C5 C4 122.6(3) . . C6 C5 C11 120.4(3) . . C4 C5 C11 117.0(3) . . C5 C6 N2 122.3(3) . . C5 C6 C7 131.2(3) . . N2 C6 C7 106.5(3) . . C6 C7 C8 104.5(3) . . C6 C7 H7A 110.9 . . C8 C7 H7A 110.9 . . C6 C7 H7B 110.9 . . C8 C7 H7B 110.9 . . H7A C7 H7B 108.9 . . C9 C8 C7 103.4(3) . . C9 C8 H8A 111.1 . . C7 C8 H8A 111.1 . . C9 C8 H8B 111.1 . . C7 C8 H8B 111.1 . . H8A C8 H8B 109.0 . . N2 C9 C1 112.4(3) . 3_666 N2 C9 C8 110.4(3) . . C1 C9 C8 137.2(3) 3_666 . N3 C10 C3 177.6(7) . . C16 C11 C12 120.2(3) . . C16 C11 C5 120.8(3) . . C12 C11 C5 118.9(3) . . C13 C12 C11 118.2(3) . . C13 C12 C17 120.0(3) . . C11 C12 C17 121.8(3) . . C14 C13 C12 122.3(3) . . C14 C13 H13 118.8 . . C12 C13 H13 118.8 . . C13 C14 C15 118.7(3) . . C13 C14 C18 120.3(4) . . C15 C14 C18 121.0(4) . . C14 C15 C16 121.2(4) . . C14 C15 H15 119.4 . . C16 C15 H15 119.4 . . C15 C16 C11 119.3(3) . . C15 C16 C19 119.8(3) . . C11 C16 C19 120.9(3) . . C12 C17 H17A 109.5 . . C12 C17 H17B 109.5 . . H17A C17 H17B 109.5 . . C12 C17 H17C 109.5 . . H17A C17 H17C 109.5 . . H17B C17 H17C 109.5 . . C14 C18 H18A 109.5 . . C14 C18 H18B 109.5 . . H18A C18 H18B 109.5 . . C14 C18 H18C 109.5 . . H18A C18 H18C 109.5 . . H18B C18 H18C 109.5 . . C16 C19 H19A 109.5 . . C16 C19 H19B 109.5 . . H19A C19 H19B 109.5 . . C16 C19 H19C 109.5 . . H19A C19 H19C 109.5 . . H19B C19 H19C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Ni1 N1 1.773(3) 3_666 Ni1 N1 1.773(3) . Ni1 N2 1.797(3) . Ni1 N2 1.797(3) 3_666 N1 C4 1.333(4) . N1 C1 1.378(4) . N2 C9 1.321(5) . N2 C6 1.398(4) . N3 C10 1.150(9) . C1 C2 1.407(5) . C1 C9 1.446(5) 3_666 C2 C3 1.407(5) . C2 H2 0.9300 . C3 C10 1.387(8) . C3 C4 1.422(5) . C3 H3 0.9300 . C4 C5 1.486(5) . C5 C6 1.370(5) . C5 C11 1.496(4) . C6 C7 1.519(5) . C7 C8 1.565(5) . C7 H7A 0.9700 . C7 H7B 0.9700 . C8 C9 1.498(4) . C8 H8A 0.9700 . C8 H8B 0.9700 . C9 C1 1.446(5) 3_666 C11 C16 1.402(5) . C11 C12 1.409(5) . C12 C13 1.396(5) . C12 C17 1.502(5) . C13 C14 1.378(6) . C13 H13 0.9300 . C14 C15 1.392(6) . C14 C18 1.504(5) . C15 C16 1.393(5) . C15 H15 0.9300 . C16 C19 1.498(5) . C17 H17A 0.9600 . C17 H17B 0.9600 . C17 H17C 0.9600 . C18 H18A 0.9600 . C18 H18B 0.9600 . C18 H18C 0.9600 . C19 H19A 0.9600 . C19 H19B 0.9600 . C19 H19C 0.9600 . 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 N2 Ni1 N1 C4 0.2(3) . . . . N2 Ni1 N1 C4 -179.8(3) 3_666 . . . N2 Ni1 N1 C1 177.1(2) . . . . N2 Ni1 N1 C1 -2.9(2) 3_666 . . . N1 Ni1 N2 C9 -2.3(2) 3_666 . . . N1 Ni1 N2 C9 177.7(2) . . . . N1 Ni1 N2 C6 -178.4(3) 3_666 . . . N1 Ni1 N2 C6 1.6(3) . . . . C4 N1 C1 C2 0.0(4) . . . . Ni1 N1 C1 C2 -177.4(2) . . . . C4 N1 C1 C9 -179.7(3) . . . 3_666 Ni1 N1 C1 C9 2.9(4) . . . 3_666 N1 C1 C2 C3 0.2(4) . . . . C9 C1 C2 C3 179.7(4) 3_666 . . . C1 C2 C3 C10 179.5(4) . . . . C1 C2 C3 C4 -0.3(4) . . . . C1 N1 C4 C3 -0.2(4) . . . . Ni1 N1 C4 C3 176.7(2) . . . . C1 N1 C4 C5 -179.9(3) . . . . Ni1 N1 C4 C5 -3.0(5) . . . . C10 C3 C4 N1 -179.4(5) . . . . C2 C3 C4 N1 0.3(4) . . . . C10 C3 C4 C5 0.2(7) . . . . C2 C3 C4 C5 180.0(3) . . . . N1 C4 C5 C6 4.5(5) . . . . C3 C4 C5 C6 -175.2(3) . . . . N1 C4 C5 C11 -174.7(3) . . . . C3 C4 C5 C11 5.6(5) . . . . C4 C5 C6 N2 -2.8(5) . . . . C11 C5 C6 N2 176.3(3) . . . . C4 C5 C6 C7 177.3(3) . . . . C11 C5 C6 C7 -3.6(5) . . . . C9 N2 C6 C5 -176.6(3) . . . . Ni1 N2 C6 C5 -0.4(5) . . . . C9 N2 C6 C7 3.4(4) . . . . Ni1 N2 C6 C7 179.5(2) . . . . C5 C6 C7 C8 176.5(3) . . . . N2 C6 C7 C8 -3.4(3) . . . . C6 C7 C8 C9 2.4(3) . . . . C6 N2 C9 C1 177.9(3) . . . 3_666 Ni1 N2 C9 C1 1.2(4) . . . 3_666 C6 N2 C9 C8 -1.8(4) . . . . Ni1 N2 C9 C8 -178.5(2) . . . . C7 C8 C9 N2 -0.5(4) . . . . C7 C8 C9 C1 179.9(4) . . . 3_666 C6 C5 C11 C16 84.2(4) . . . . C4 C5 C11 C16 -96.6(4) . . . . C6 C5 C11 C12 -98.6(4) . . . . C4 C5 C11 C12 80.6(4) . . . . C16 C11 C12 C13 -1.7(5) . . . . C5 C11 C12 C13 -178.9(3) . . . . C16 C11 C12 C17 178.9(3) . . . . C5 C11 C12 C17 1.7(5) . . . . C11 C12 C13 C14 -0.2(5) . . . . C17 C12 C13 C14 179.2(4) . . . . C12 C13 C14 C15 1.0(6) . . . . C12 C13 C14 C18 -178.2(4) . . . . C13 C14 C15 C16 0.2(6) . . . . C18 C14 C15 C16 179.4(4) . . . . C14 C15 C16 C11 -2.1(5) . . . . C14 C15 C16 C19 176.9(3) . . . . C12 C11 C16 C15 2.8(5) . . . . C5 C11 C16 C15 -180.0(3) . . . . C12 C11 C16 C19 -176.1(3) . . . . C5 C11 C16 C19 1.1(5) . . . .