#------------------------------------------------------------------------------ #$Date: 2024-09-25 04:20:10 +0300 (Wed, 25 Sep 2024) $ #$Revision: 294878 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249371.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_7249371 loop_ _publ_author_name 'Rajeev, Anjana' 'Muthuramalingam, Sethuraman' 'Sankaralingam, Muniyandi' _publ_section_title ; Selective synthesis of cyclic alcohols from cycloalkanes using nickel(ii) complexes of tetradentate amidate ligands ; _journal_issue 41 _journal_name_full 'RSC Advances' _journal_page_first 30440 _journal_page_last 30451 _journal_paper_doi 10.1039/D4RA05222F _journal_volume 14 _journal_year 2024 _chemical_formula_sum 'C23 H27 Cl2 N5 Ni O10' _chemical_formula_weight 663.10 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_update_record ; 2024-07-18 deposited with the CCDC. 2024-08-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.411(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 17.786(3) _cell_length_b 7.4291(13) _cell_length_c 21.345(4) _cell_measurement_reflns_used 9864 _cell_measurement_temperature 100.(2) _cell_measurement_theta_max 27.1019 _cell_measurement_theta_min 2.9097 _cell_volume 2764.6(8) _computing_cell_refinement 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_data_collection 'Bruker Instrument Service vV6.2.16' _computing_data_reduction 'SAINT V8.40B (Bruker AXS LLC, 2019)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 1365)' _computing_structure_refinement 'SHELXL-2019/1 (Sheldrick, 2019)' _computing_structure_solution 'XT, VERSION 2018/2' _diffrn_ambient_temperature 100.(2) _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'D8 QUEST ECO' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'doubly curved silicon crystal Bruker Triumph' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0822 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 97866 _diffrn_reflns_theta_full 25.24 _diffrn_reflns_theta_max 27.57 _diffrn_reflns_theta_min 2.98 _diffrn_source_type 'Ceramic x-ray tube' _exptl_absorpt_coefficient_mu 0.959 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). "Comparison of silver and molybdenum microfocus X-ray sources for single-crystal structure determination" J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985 ; _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1368 _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.728 _refine_diff_density_min -0.712 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 403 _refine_ls_number_reflns 6383 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0633 _refine_ls_R_factor_gt 0.0429 _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^)+(0.0345P)^2^+5.8383P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0942 _refine_ls_wR_factor_ref 0.1045 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5038 _reflns_number_total 6383 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ra05222f2.cif _cod_data_source_block MSAR12 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_database_code 7249371 _shelx_res_file ; TITL MSAR12_0m_a.res in P2(1)/c MSAR12_0m_a.res created by SHELXL-2019/1 at 13:19:08 on 19-Jun-2024 REM Old TITL MSAR12_0m in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.135, Rweak 0.008, Alpha 0.033 REM 0.813 for 456 systematic absences, Orientation as input REM Formula found by SHELXT: C32 Cl2 N4 Ni O2 CELL 0.71073 17.7864 7.4291 21.3449 90.000 101.411 90.000 ZERR 4.000 0.0027 0.0013 0.0036 0.000 0.005 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H CL N NI O UNIT 92 108 8 20 4 40 OMIT 2 0 0 OMIT -1 0 2 OMIT 1 0 2 OMIT -2 0 2 TEMP -173.150 SIZE 0.100 0.130 0.240 L.S. 10 BOND $h conf acta LIST 6 FMAP 2 eadp o5r o4" eadp o4r o3" eadp o4s o2' eadp o3s o3' eadp o2s o1' isor 0.01 o1' o3' PLAN 20 WGHT 0.034500 5.838300 FVAR 0.32415 0.82486 0.87930 NI1 5 0.708569 0.418082 0.393182 11.00000 0.01906 0.01896 = 0.02152 0.00086 0.00842 0.00222 O1 6 0.707938 0.551290 0.308174 11.00000 0.02691 0.02794 = 0.02136 -0.00107 0.01017 -0.00206 O28 6 0.711578 0.278814 0.477729 11.00000 0.02740 0.03443 = 0.02902 0.00947 0.00854 0.00456 N1 4 0.823822 0.488339 0.418558 11.00000 0.02284 0.02052 = 0.02226 0.00166 0.00725 0.00177 N2 4 0.755075 0.206736 0.348548 11.00000 0.02871 0.01818 = 0.03608 -0.00477 0.01583 -0.00126 N3 4 0.609815 0.270831 0.358005 11.00000 0.02301 0.03288 = 0.02250 0.00402 0.00648 -0.00300 N4 4 0.661977 0.631417 0.432303 11.00000 0.02328 0.02262 = 0.02674 0.00380 0.00995 0.00370 N5 4 0.760917 0.529592 0.220906 11.00000 0.03669 0.03590 = 0.02211 -0.00901 0.01264 -0.01335 AFIX 43 H5 2 0.782855 0.457433 0.197176 11.00000 -1.20000 AFIX 0 C1 1 0.853693 0.646918 0.440718 11.00000 0.03141 0.02349 = 0.01877 0.00071 0.00448 0.00146 AFIX 43 H1 2 0.820925 0.734242 0.453775 11.00000 -1.20000 AFIX 0 C2 1 0.930442 0.688454 0.445327 11.00000 0.03355 0.03303 = 0.01854 0.00279 -0.00119 -0.00951 AFIX 43 H2 2 0.950217 0.801376 0.461827 11.00000 -1.20000 AFIX 0 C3 1 0.977667 0.562137 0.425412 11.00000 0.02352 0.04308 = 0.02421 0.01127 0.00080 -0.00339 AFIX 43 H3 2 1.030364 0.588066 0.427264 11.00000 -1.20000 AFIX 0 H28A 2 0.685161 0.318969 0.497272 11.00000 -1.50000 H28B 2 0.753657 0.260040 0.499313 11.00000 -1.50000 C4 1 0.947835 0.399126 0.402966 11.00000 0.02187 0.03677 = 0.03386 0.00884 0.00812 0.00531 AFIX 43 H4 2 0.979507 0.310792 0.389047 11.00000 -1.20000 AFIX 0 C5 1 0.870800 0.365007 0.400866 11.00000 0.02399 0.02358 = 0.03130 0.00441 0.00983 0.00356 C6 1 0.835539 0.185049 0.383004 11.00000 0.02664 0.02287 = 0.05536 -0.00230 0.01711 0.00437 AFIX 23 H6A 2 0.865385 0.120797 0.355417 11.00000 -1.20000 H6B 2 0.836808 0.112209 0.422039 11.00000 -1.20000 AFIX 0 C7 1 0.707479 0.046891 0.354328 11.00000 0.03741 0.01893 = 0.04667 -0.00619 0.01895 -0.00743 AFIX 23 H7A 2 0.722460 -0.005039 0.397722 11.00000 -1.20000 H7B 2 0.715657 -0.045685 0.322990 11.00000 -1.20000 AFIX 0 C8 1 0.624232 0.100755 0.342134 11.00000 0.03474 0.03084 = 0.02464 0.00035 0.01090 -0.01059 C9 1 0.566353 -0.020691 0.318917 11.00000 0.04842 0.04392 = 0.02839 -0.00040 0.00905 -0.02101 AFIX 43 H9 2 0.578152 -0.139332 0.307338 11.00000 -1.20000 AFIX 0 C10 1 0.491126 0.034356 0.312958 11.00000 0.04287 0.06409 = 0.03503 0.00954 -0.00277 -0.02765 AFIX 43 H10 2 0.450219 -0.046453 0.297647 11.00000 -1.20000 AFIX 0 C11 1 0.476213 0.207827 0.329496 11.00000 0.02638 0.07271 = 0.04079 0.01621 -0.00292 -0.01103 AFIX 43 H11 2 0.424814 0.248017 0.325776 11.00000 -1.20000 AFIX 0 C12 1 0.536737 0.323341 0.351607 11.00000 0.02245 0.04740 = 0.03326 0.01117 0.00491 -0.00066 AFIX 43 H12 2 0.526070 0.443316 0.362548 11.00000 -1.20000 AFIX 0 C13 1 0.637486 0.732884 0.462442 11.00000 0.02261 0.02294 = 0.02943 0.00439 0.00990 0.00118 C14 1 0.607260 0.864863 0.501343 11.00000 0.03720 0.03089 = 0.03816 -0.00758 0.01556 0.00397 AFIX 137 H14A 2 0.582972 0.802617 0.532624 11.00000 -1.50000 H32B 2 0.569221 0.940418 0.473834 11.00000 -1.50000 H33C 2 0.649226 0.940458 0.523775 11.00000 -1.50000 AFIX 0 C15 1 0.750201 0.258850 0.281083 11.00000 0.04454 0.02991 = 0.03554 -0.01101 0.02495 -0.01034 AFIX 23 H15A 2 0.706764 0.194579 0.254123 11.00000 -1.20000 H15B 2 0.797826 0.221617 0.267254 11.00000 -1.20000 AFIX 0 C16 1 0.739119 0.459754 0.271142 11.00000 0.02555 0.03262 = 0.02001 -0.00525 0.00513 -0.00889 C17 1 0.751288 0.718278 0.201747 11.00000 0.02952 0.04279 = 0.01613 0.00319 0.00054 -0.00647 AFIX 23 H17A 2 0.710605 0.772417 0.221343 11.00000 -1.20000 H17B 2 0.734306 0.724878 0.154749 11.00000 -1.20000 AFIX 0 C18 1 0.824253 0.826333 0.221316 11.00000 0.02623 0.02680 = 0.01977 0.00012 0.00925 0.00168 C19 1 0.841955 0.961820 0.181979 11.00000 0.03105 0.03306 = 0.02403 0.00845 0.00966 0.00668 AFIX 43 H19 2 0.808515 0.985182 0.142280 11.00000 -1.20000 AFIX 0 C20 1 0.907735 1.063039 0.199999 11.00000 0.03530 0.03101 = 0.03297 0.01129 0.01791 0.00326 AFIX 43 H20 2 0.919124 1.156188 0.172839 11.00000 -1.20000 AFIX 0 C21 1 0.957212 1.029299 0.257548 11.00000 0.02420 0.02596 = 0.03386 -0.00028 0.01469 -0.00060 AFIX 43 H21 2 1.002691 1.098437 0.269724 11.00000 -1.20000 AFIX 0 C22 1 0.940174 0.894782 0.297149 11.00000 0.02416 0.02239 = 0.02726 -0.00027 0.00780 0.00223 AFIX 43 H22 2 0.973879 0.871518 0.336726 11.00000 -1.20000 AFIX 0 C23 1 0.873810 0.793503 0.279162 11.00000 0.02717 0.02187 = 0.02190 0.00191 0.00802 -0.00015 AFIX 43 H23 2 0.862217 0.701215 0.306568 11.00000 -1.20000 AFIX 0 CL1R 3 0.862980 0.028489 0.572136 11.00000 0.02423 0.03218 = 0.02494 -0.00476 0.00239 0.00419 O2R 6 0.799853 -0.073860 0.539473 11.00000 0.03413 0.03878 = 0.06449 -0.02485 -0.00461 -0.00052 part 1 31 O3R 6 0.852466 0.218791 0.552904 31.00000 0.03275 0.02824 = 0.04105 0.00824 -0.00350 -0.00609 O4R 6 0.867706 0.020274 0.639270 31.00000 0.04044 0.04457 = 0.02324 0.00539 0.00602 -0.00428 O5R 6 0.934436 -0.027752 0.556544 31.00000 0.02753 0.06672 = 0.05057 -0.02071 0.01264 0.00726 part 2 -31 O5" 6 0.859550 0.119257 0.520830 -31.00000 0.04031 0.07108 = 0.03676 0.03582 0.02042 0.01656 O3" 6 0.844881 0.106297 0.626153 -31.00000 0.04044 0.04457 = 0.02324 0.00539 0.00602 -0.00428 O4" 6 0.922971 -0.100180 0.588364 -31.00000 0.02753 0.06672 = 0.05057 -0.02071 0.01264 0.00726 part 0 CL1S 3 0.614283 0.334708 0.608748 11.00000 0.02565 0.03634 = 0.02932 -0.00061 0.00630 -0.00077 part 1 21 O2S 6 0.644203 0.462967 0.572337 21.00000 0.07455 0.03827 = 0.04389 0.01076 0.02831 -0.00193 O3S 6 0.538163 0.284316 0.582409 21.00000 0.03952 0.09375 = 0.07525 0.00456 -0.01775 -0.02364 O4S 6 0.615607 0.409028 0.672075 21.00000 0.04794 0.08753 = 0.02377 -0.00906 0.00532 0.02359 part 2 -21 O1' 6 0.588396 0.322322 0.532200 -21.00000 0.07455 0.03827 = 0.04389 0.01076 0.02831 -0.00193 O2' 6 0.639461 0.520269 0.620807 -21.00000 0.04794 0.08753 = 0.02377 -0.00906 0.00532 0.02359 O3' 6 0.540837 0.297438 0.624725 -21.00000 0.03952 0.09375 = 0.07525 0.00456 -0.01775 -0.02364 part 0 O5S 6 0.664066 0.183051 0.617803 11.00000 0.08366 0.05186 = 0.04592 0.00800 0.00060 0.03551 HKLF 4 REM MSAR12_0m_a.res in P2(1)/c REM wR2 = 0.1045, GooF = S = 1.034, Restrained GooF = 1.034 for all data REM R1 = 0.0429 for 5038 Fo > 4sig(Fo) and 0.0633 for all 6383 data REM 403 parameters refined using 12 restraints END WGHT 0.0345 5.8368 REM Highest difference peak 0.728, deepest hole -0.712, 1-sigma level 0.077 Q1 1 0.5977 0.4019 0.5386 11.00000 0.05 0.73 Q2 1 0.5871 0.2617 0.5335 11.00000 0.05 0.71 Q3 1 0.5723 0.3080 0.6453 11.00000 0.05 0.71 Q4 1 0.8338 -0.0591 0.5713 11.00000 0.05 0.66 Q5 1 0.5159 0.2965 0.6144 11.00000 0.05 0.66 Q6 1 0.5772 0.5410 0.5772 11.00000 0.05 0.60 Q7 1 0.6928 0.4069 0.5920 11.00000 0.05 0.60 Q8 1 0.6927 0.2955 0.6120 11.00000 0.05 0.59 Q9 1 0.6411 0.4994 0.6528 11.00000 0.05 0.55 Q10 1 0.7796 -0.1570 0.5625 11.00000 0.05 0.47 Q11 1 0.5394 0.4194 0.5640 11.00000 0.05 0.43 Q12 1 0.8495 0.8587 0.1988 11.00000 0.05 0.37 Q13 1 0.6037 0.1001 0.6010 11.00000 0.05 0.35 Q14 1 0.5585 0.8629 0.4885 11.00000 0.05 0.33 Q15 1 0.6253 0.3053 0.6706 11.00000 0.05 0.32 Q16 1 0.5309 0.0038 0.3255 11.00000 0.05 0.31 Q17 1 0.8927 -0.0999 0.6083 11.00000 0.05 0.31 Q18 1 0.6604 0.5702 0.4024 11.00000 0.05 0.31 Q19 1 0.7801 0.4499 0.4190 11.00000 0.05 0.30 Q20 1 0.7268 0.3512 0.2637 11.00000 0.05 0.30 ; _shelx_res_checksum 27187 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni1 0.70857(2) 0.41808(5) 0.39318(2) 0.01924(9) Uani d . . . 1.000000 . . O O1 0.70794(11) 0.5513(3) 0.30817(9) 0.0247(4) Uani d . . . 1.000000 . . O O28 0.71158(13) 0.2788(3) 0.47773(10) 0.0299(5) Uani d . . . 1.000000 . . N N1 0.82382(13) 0.4883(3) 0.41856(11) 0.0215(5) Uani d . . . 1.000000 . . N N2 0.75508(14) 0.2067(3) 0.34855(12) 0.0264(5) Uani d . . . 1.000000 . . N N3 0.60981(13) 0.2708(3) 0.35800(11) 0.0259(5) Uani d . . . 1.000000 . . N N4 0.66198(13) 0.6314(3) 0.43230(11) 0.0235(5) Uani d . . . 1.000000 . . N N5 0.76092(15) 0.5296(4) 0.22091(11) 0.0306(6) Uani d . . . 1.000000 . . H H5 0.782855 0.457433 0.197176 0.037000 Uiso calc U . R 1.000000 . . C C1 0.85369(16) 0.6469(4) 0.44072(13) 0.0246(6) Uani d . . . 1.000000 . . H H1 0.820925 0.734242 0.453775 0.030000 Uiso calc U . R 1.000000 . . C C2 0.93044(17) 0.6885(4) 0.44533(13) 0.0292(6) Uani d . . . 1.000000 . . H H2 0.950217 0.801376 0.461827 0.035000 Uiso calc U . R 1.000000 . . C C3 0.97767(17) 0.5621(4) 0.42541(14) 0.0308(7) Uani d . . . 1.000000 . . H H3 1.030364 0.588066 0.427264 0.037000 Uiso calc U . R 1.000000 . . H H28A 0.685(2) 0.319(6) 0.4973(19) 0.046000 Uiso d U . . 1.000000 . . H H28B 0.754(2) 0.260(6) 0.4993(18) 0.046000 Uiso d U . . 1.000000 . . C C4 0.94783(16) 0.3991(4) 0.40297(15) 0.0305(7) Uani d . . . 1.000000 . . H H4 0.979507 0.310792 0.389047 0.037000 Uiso calc U . R 1.000000 . . C C5 0.87080(16) 0.3650(4) 0.40087(14) 0.0257(6) Uani d . . . 1.000000 . . C C6 0.83554(17) 0.1850(4) 0.38300(17) 0.0337(7) Uani d . . . 1.000000 . . H H6A 0.865385 0.120797 0.355417 0.040000 Uiso calc U . R 1.000000 . . H H6B 0.836808 0.112209 0.422039 0.040000 Uiso calc U . R 1.000000 . . C C7 0.70748(18) 0.0469(4) 0.35433(17) 0.0329(7) Uani d . . . 1.000000 . . H H7A 0.722460 -0.005039 0.397722 0.039000 Uiso calc U . R 1.000000 . . H H7B 0.715657 -0.045685 0.322990 0.039000 Uiso calc U . R 1.000000 . . C C8 0.62423(17) 0.1008(4) 0.34213(14) 0.0294(6) Uani d . . . 1.000000 . . C C9 0.5664(2) -0.0207(5) 0.31892(15) 0.0400(8) Uani d . . . 1.000000 . . H H9 0.578152 -0.139332 0.307338 0.048000 Uiso calc U . R 1.000000 . . C C10 0.4911(2) 0.0344(6) 0.31296(17) 0.0488(10) Uani d . . . 1.000000 . . H H10 0.450219 -0.046453 0.297647 0.059000 Uiso calc U . R 1.000000 . . C C11 0.47621(19) 0.2078(6) 0.32950(17) 0.0479(10) Uani d . . . 1.000000 . . H H11 0.424814 0.248017 0.325776 0.058000 Uiso calc U . R 1.000000 . . C C12 0.53674(16) 0.3233(5) 0.35161(15) 0.0345(7) Uani d . . . 1.000000 . . H H12 0.526070 0.443316 0.362548 0.041000 Uiso calc U . R 1.000000 . . C C13 0.63749(15) 0.7329(4) 0.46244(14) 0.0243(6) Uani d . . . 1.000000 . . C C14 0.60726(19) 0.8649(4) 0.50134(16) 0.0343(7) Uani d . . . 1.000000 . . H H14A 0.582972 0.802617 0.532624 0.051000 Uiso calc U . R 1.000000 . . H H32B 0.569221 0.940418 0.473834 0.051000 Uiso calc U . R 1.000000 . . H H33C 0.649226 0.940458 0.523775 0.051000 Uiso calc U . R 1.000000 . . C C15 0.75020(19) 0.2588(4) 0.28108(15) 0.0343(7) Uani d . . . 1.000000 . . H H15A 0.706764 0.194579 0.254123 0.041000 Uiso calc U . R 1.000000 . . H H15B 0.797826 0.221617 0.267254 0.041000 Uiso calc U . R 1.000000 . . C C16 0.73912(16) 0.4598(4) 0.27114(13) 0.0260(6) Uani d . . . 1.000000 . . C C17 0.75129(17) 0.7183(4) 0.20175(13) 0.0300(7) Uani d . . . 1.000000 . . H H17A 0.710605 0.772417 0.221343 0.036000 Uiso calc U . R 1.000000 . . H H17B 0.734306 0.724878 0.154749 0.036000 Uiso calc U . R 1.000000 . . C C18 0.82425(16) 0.8263(4) 0.22132(13) 0.0236(6) Uani d . . . 1.000000 . . C C19 0.84195(17) 0.9618(4) 0.18198(14) 0.0288(6) Uani d . . . 1.000000 . . H H19 0.808515 0.985182 0.142280 0.035000 Uiso calc U . R 1.000000 . . C C20 0.90773(17) 1.0630(4) 0.20000(15) 0.0316(7) Uani d . . . 1.000000 . . H H20 0.919124 1.156188 0.172839 0.038000 Uiso calc U . R 1.000000 . . C C21 0.95721(16) 1.0293(4) 0.25755(14) 0.0268(6) Uani d . . . 1.000000 . . H H21 1.002691 1.098437 0.269724 0.032000 Uiso calc U . R 1.000000 . . C C22 0.94017(16) 0.8948(4) 0.29715(14) 0.0242(6) Uani d . . . 1.000000 . . H H22 0.973879 0.871518 0.336726 0.029000 Uiso calc U . R 1.000000 . . C C23 0.87381(15) 0.7935(4) 0.27916(13) 0.0232(6) Uani d . . . 1.000000 . . H H23 0.862217 0.701215 0.306568 0.028000 Uiso calc U . R 1.000000 . . Cl Cl1R 0.86298(4) 0.02849(10) 0.57214(3) 0.02745(16) Uani d . . . 1.000000 . . O O2R 0.79985(13) -0.0739(3) 0.53947(13) 0.0478(6) Uani d . . . 1.000000 . . O O3R 0.85247(15) 0.2188(4) 0.55290(14) 0.0355(7) Uani d . P . 0.879(5) A 1 O O4R 0.86771(16) 0.0203(4) 0.63927(12) 0.0361(7) Uani d . P . 0.879(5) A 1 O O5R 0.93444(15) -0.0278(5) 0.55654(16) 0.0476(9) Uani d . P . 0.879(5) A 1 O O5" 0.8596(12) 0.119(4) 0.5208(11) 0.048(7) Uani d . P . 0.121(5) A 2 O O3" 0.8449(13) 0.106(3) 0.6262(10) 0.0361(7) Uani d . P . 0.121(5) A 2 O O4" 0.9230(12) -0.100(4) 0.5884(12) 0.0476(9) Uani d . P . 0.121(5) A 2 Cl Cl1S 0.61428(4) 0.33471(11) 0.60875(3) 0.03032(17) Uani d . . . 1.000000 . . O O2S 0.6442(2) 0.4630(4) 0.57234(15) 0.0500(8) Uani d . P . 0.825(3) B 1 O O3S 0.5382(2) 0.2843(6) 0.5824(2) 0.0735(12) Uani d . P . 0.825(3) B 1 O O4S 0.61561(18) 0.4090(5) 0.67207(13) 0.0533(9) Uani d . P . 0.825(3) B 1 O O1' 0.5884(9) 0.322(2) 0.5322(7) 0.0500(8) Uani d U P . 0.175(3) B 2 O O2' 0.6395(8) 0.520(2) 0.6208(6) 0.0533(9) Uani d . P . 0.175(3) B 2 O O3' 0.5408(10) 0.297(3) 0.6247(11) 0.0735(12) Uani d U P . 0.175(3) B 2 O O5S 0.66407(18) 0.1831(4) 0.61780(13) 0.0622(8) Uani d . . . 1.000000 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Ni1 0.01906(17) 0.01896(17) 0.02152(17) 0.00222(13) 0.00842(13) 0.00086(14) O1 0.0269(10) 0.0279(11) 0.0214(9) -0.0021(8) 0.0102(8) -0.0011(8) O28 0.0274(11) 0.0344(12) 0.0290(11) 0.0046(10) 0.0085(9) 0.0095(9) N1 0.0228(11) 0.0205(11) 0.0223(11) 0.0018(9) 0.0072(9) 0.0017(9) N2 0.0287(12) 0.0182(12) 0.0361(13) -0.0013(10) 0.0158(10) -0.0048(10) N3 0.0230(11) 0.0329(14) 0.0225(12) -0.0030(10) 0.0065(9) 0.0040(10) N4 0.0233(11) 0.0226(12) 0.0267(12) 0.0037(9) 0.0099(10) 0.0038(10) N5 0.0367(14) 0.0359(14) 0.0221(12) -0.0134(11) 0.0126(10) -0.0090(11) C1 0.0314(14) 0.0235(14) 0.0188(13) 0.0015(12) 0.0045(11) 0.0007(11) C2 0.0336(15) 0.0330(17) 0.0185(13) -0.0095(13) -0.0012(12) 0.0028(12) C3 0.0235(14) 0.0431(19) 0.0242(14) -0.0034(13) 0.0008(11) 0.0113(13) C4 0.0219(13) 0.0368(17) 0.0339(16) 0.0053(13) 0.0081(12) 0.0088(14) C5 0.0240(13) 0.0236(14) 0.0313(15) 0.0036(11) 0.0098(12) 0.0044(12) C6 0.0266(15) 0.0229(15) 0.055(2) 0.0044(12) 0.0171(14) -0.0023(14) C7 0.0374(17) 0.0189(14) 0.0467(19) -0.0074(12) 0.0190(14) -0.0062(13) C8 0.0347(15) 0.0308(16) 0.0246(14) -0.0106(13) 0.0109(12) 0.0003(12) C9 0.048(2) 0.044(2) 0.0284(16) -0.0210(16) 0.0091(14) -0.0004(15) C10 0.043(2) 0.064(3) 0.0350(19) -0.0276(19) -0.0028(15) 0.0095(18) C11 0.0264(16) 0.073(3) 0.0408(19) -0.0110(17) -0.0029(14) 0.0162(19) C12 0.0225(14) 0.047(2) 0.0333(16) -0.0007(14) 0.0049(12) 0.0112(15) C13 0.0226(13) 0.0229(14) 0.0294(14) 0.0012(11) 0.0099(11) 0.0044(12) C14 0.0372(17) 0.0309(17) 0.0382(17) 0.0040(13) 0.0156(14) -0.0076(14) C15 0.0445(18) 0.0299(16) 0.0355(17) -0.0103(14) 0.0249(15) -0.0110(14) C16 0.0255(13) 0.0326(16) 0.0200(13) -0.0089(12) 0.0051(11) -0.0053(12) C17 0.0295(15) 0.0428(18) 0.0161(13) -0.0065(13) 0.0005(11) 0.0032(12) C18 0.0262(14) 0.0268(15) 0.0198(13) 0.0017(11) 0.0093(11) 0.0001(11) C19 0.0310(15) 0.0331(17) 0.0240(14) 0.0067(12) 0.0097(12) 0.0084(12) C20 0.0353(16) 0.0310(17) 0.0330(16) 0.0033(13) 0.0179(13) 0.0113(13) C21 0.0242(13) 0.0260(15) 0.0339(16) -0.0006(11) 0.0147(12) -0.0003(12) C22 0.0242(13) 0.0224(14) 0.0273(14) 0.0022(11) 0.0078(11) -0.0003(11) C23 0.0272(14) 0.0219(14) 0.0219(13) -0.0001(11) 0.0080(11) 0.0019(11) Cl1R 0.0242(3) 0.0322(4) 0.0249(3) 0.0042(3) 0.0024(3) -0.0048(3) O2R 0.0341(12) 0.0388(14) 0.0645(17) -0.0005(11) -0.0046(11) -0.0249(13) O3R 0.0327(14) 0.0282(14) 0.0411(16) -0.0061(11) -0.0035(12) 0.0082(13) O4R 0.0404(15) 0.0446(19) 0.0232(13) -0.0043(13) 0.0060(11) 0.0054(12) O5R 0.0275(13) 0.067(2) 0.0506(19) 0.0073(13) 0.0126(13) -0.0207(16) O5" 0.040(11) 0.071(18) 0.037(12) 0.017(11) 0.020(9) 0.036(12) O3" 0.0404(15) 0.0446(19) 0.0232(13) -0.0043(13) 0.0060(11) 0.0054(12) O4" 0.0275(13) 0.067(2) 0.0506(19) 0.0073(13) 0.0126(13) -0.0207(16) Cl1S 0.0256(3) 0.0363(4) 0.0293(4) -0.0008(3) 0.0063(3) -0.0006(3) O2S 0.075(2) 0.0383(17) 0.0439(17) -0.0019(15) 0.0283(16) 0.0108(13) O3S 0.0395(17) 0.094(3) 0.075(3) -0.0236(18) -0.018(2) 0.005(3) O4S 0.0479(17) 0.088(3) 0.0238(14) 0.0236(17) 0.0053(12) -0.0091(15) O1' 0.075(2) 0.0383(17) 0.0439(17) -0.0019(15) 0.0283(16) 0.0108(13) O2' 0.0479(17) 0.088(3) 0.0238(14) 0.0236(17) 0.0053(12) -0.0091(15) O3' 0.0395(17) 0.094(3) 0.075(3) -0.0236(18) -0.018(2) 0.005(3) O5S 0.084(2) 0.0519(17) 0.0459(15) 0.0355(16) 0.0006(14) 0.0080(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N4 Ni1 O1 . . 93.17(9) ? N4 Ni1 O28 . . 88.51(9) ? O1 Ni1 O28 . . 178.24(9) ? N4 Ni1 N3 . . 100.01(10) ? O1 Ni1 N3 . . 94.44(8) ? O28 Ni1 N3 . . 85.77(9) ? N4 Ni1 N1 . . 99.06(9) ? O1 Ni1 N1 . . 86.69(8) ? O28 Ni1 N1 . . 92.53(9) ? N3 Ni1 N1 . . 160.80(9) ? N4 Ni1 N2 . . 177.00(10) ? O1 Ni1 N2 . . 83.88(9) ? O28 Ni1 N2 . . 94.45(10) ? N3 Ni1 N2 . . 79.77(9) ? N1 Ni1 N2 . . 81.30(9) ? C16 O1 Ni1 . . 111.61(19) ? Ni1 O28 H28A . . 112.(3) ? Ni1 O28 H28B . . 116.(3) ? H28A O28 H28B . . 111.(4) ? C1 N1 C5 . . 118.3(2) ? C1 N1 Ni1 . . 127.88(19) ? C5 N1 Ni1 . . 113.03(19) ? C15 N2 C7 . . 111.6(2) ? C15 N2 C6 . . 112.1(2) ? C7 N2 C6 . . 112.6(2) ? C15 N2 Ni1 . . 107.17(18) ? C7 N2 Ni1 . . 106.30(17) ? C6 N2 Ni1 . . 106.60(18) ? C12 N3 C8 . . 118.5(3) ? C12 N3 Ni1 . . 128.1(2) ? C8 N3 Ni1 . . 113.29(19) ? C13 N4 Ni1 . . 169.0(2) ? C16 N5 C17 . . 124.7(3) ? C16 N5 H5 . . 117.700000 ? C17 N5 H5 . . 117.700000 ? N1 C1 C2 . . 122.5(3) ? N1 C1 H1 . . 118.700000 ? C2 C1 H1 . . 118.700000 ? C3 C2 C1 . . 118.6(3) ? C3 C2 H2 . . 120.700000 ? C1 C2 H2 . . 120.700000 ? C4 C3 C2 . . 119.4(3) ? C4 C3 H3 . . 120.300000 ? C2 C3 H3 . . 120.300000 ? C3 C4 C5 . . 119.0(3) ? C3 C4 H4 . . 120.500000 ? C5 C4 H4 . . 120.500000 ? N1 C5 C4 . . 122.2(3) ? N1 C5 C6 . . 115.4(2) ? C4 C5 C6 . . 122.3(3) ? N2 C6 C5 . . 110.2(2) ? N2 C6 H6A . . 109.600000 ? C5 C6 H6A . . 109.600000 ? N2 C6 H6B . . 109.600000 ? C5 C6 H6B . . 109.600000 ? H6A C6 H6B . . 108.100000 ? N2 C7 C8 . . 109.4(2) ? N2 C7 H7A . . 109.800000 ? C8 C7 H7A . . 109.800000 ? N2 C7 H7B . . 109.800000 ? C8 C7 H7B . . 109.800000 ? H7A C7 H7B . . 108.200000 ? N3 C8 C9 . . 122.5(3) ? N3 C8 C7 . . 115.8(3) ? C9 C8 C7 . . 121.6(3) ? C10 C9 C8 . . 118.6(4) ? C10 C9 H9 . . 120.700000 ? C8 C9 H9 . . 120.700000 ? C11 C10 C9 . . 119.1(3) ? C11 C10 H10 . . 120.500000 ? C9 C10 H10 . . 120.500000 ? C10 C11 C12 . . 119.5(3) ? C10 C11 H11 . . 120.300000 ? C12 C11 H11 . . 120.300000 ? N3 C12 C11 . . 121.9(3) ? N3 C12 H12 . . 119.100000 ? C11 C12 H12 . . 119.100000 ? N4 C13 C14 . . 179.0(3) ? C13 C14 H14A . . 109.500000 ? C13 C14 H32B . . 109.500000 ? H14A C14 H32B . . 109.500000 ? C13 C14 H33C . . 109.500000 ? H14A C14 H33C . . 109.500000 ? H32B C14 H33C . . 109.500000 ? N2 C15 C16 . . 112.1(2) ? N2 C15 H15A . . 109.200000 ? C16 C15 H15A . . 109.200000 ? N2 C15 H15B . . 109.200000 ? C16 C15 H15B . . 109.200000 ? H15A C15 H15B . . 107.900000 ? O1 C16 N5 . . 122.6(3) ? O1 C16 C15 . . 120.5(2) ? N5 C16 C15 . . 116.8(3) ? N5 C17 C18 . . 112.7(2) ? N5 C17 H17A . . 109.100000 ? C18 C17 H17A . . 109.100000 ? N5 C17 H17B . . 109.100000 ? C18 C17 H17B . . 109.100000 ? H17A C17 H17B . . 107.800000 ? C19 C18 C23 . . 119.0(3) ? C19 C18 C17 . . 120.2(3) ? C23 C18 C17 . . 120.7(2) ? C20 C19 C18 . . 120.6(3) ? C20 C19 H19 . . 119.700000 ? C18 C19 H19 . . 119.700000 ? C19 C20 C21 . . 120.2(3) ? C19 C20 H20 . . 119.900000 ? C21 C20 H20 . . 119.900000 ? C22 C21 C20 . . 119.7(3) ? C22 C21 H21 . . 120.100000 ? C20 C21 H21 . . 120.100000 ? C21 C22 C23 . . 120.0(3) ? C21 C22 H22 . . 120.000000 ? C23 C22 H22 . . 120.000000 ? C22 C23 C18 . . 120.4(3) ? C22 C23 H23 . . 119.800000 ? C18 C23 H23 . . 119.800000 ? O5" Cl1R O3" . . 121.0(15) ? O5" Cl1R O2R . . 87.9(12) ? O3" Cl1R O2R . . 110.0(9) ? O2R Cl1R O4R . . 110.84(17) ? O5" Cl1R O4" . . 118.0(14) ? O3" Cl1R O4" . . 111.4(13) ? O2R Cl1R O4" . . 104.0(10) ? O2R Cl1R O5R . . 112.34(16) ? O4R Cl1R O5R . . 110.03(18) ? O2R Cl1R O3R . . 109.43(15) ? O4R Cl1R O3R . . 107.53(18) ? O5R Cl1R O3R . . 106.47(19) ? O2S Cl1S O3S . . 113.6(2) ? O2S Cl1S O5S . . 108.65(19) ? O3S Cl1S O5S . . 111.5(2) ? O5S Cl1S O3' . . 112.6(10) ? O2S Cl1S O4S . . 108.6(2) ? O3S Cl1S O4S . . 108.0(2) ? O5S Cl1S O4S . . 106.20(17) ? O5S Cl1S O2' . . 124.4(6) ? O3' Cl1S O2' . . 113.7(11) ? O5S Cl1S O1' . . 97.9(6) ? O3' Cl1S O1' . . 98.0(10) ? O2' Cl1S O1' . . 104.5(7) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni1 N4 . 2.042(2) ? Ni1 O1 . 2.0649(19) ? Ni1 O28 . 2.072(2) ? Ni1 N3 . 2.079(2) ? Ni1 N1 . 2.081(2) ? Ni1 N2 . 2.090(2) ? O1 C16 . 1.252(3) ? O28 H28A . 0.75(4) ? O28 H28B . 0.81(4) ? N1 C1 . 1.340(4) ? N1 C5 . 1.344(3) ? N2 C15 . 1.477(4) ? N2 C7 . 1.478(4) ? N2 C6 . 1.483(4) ? N3 C12 . 1.338(4) ? N3 C8 . 1.346(4) ? N4 C13 . 1.133(4) ? N5 C16 . 1.317(4) ? N5 C17 . 1.461(4) ? N5 H5 . 0.880000 ? C1 C2 . 1.384(4) ? C1 H1 . 0.950000 ? C2 C3 . 1.381(4) ? C2 H2 . 0.950000 ? C3 C4 . 1.370(5) ? C3 H3 . 0.950000 ? C4 C5 . 1.385(4) ? C4 H4 . 0.950000 ? C5 C6 . 1.494(4) ? C6 H6A . 0.990000 ? C6 H6B . 0.990000 ? C7 C8 . 1.506(4) ? C7 H7A . 0.990000 ? C7 H7B . 0.990000 ? C8 C9 . 1.385(4) ? C9 C10 . 1.381(5) ? C9 H9 . 0.950000 ? C10 C11 . 1.376(6) ? C10 H10 . 0.950000 ? C11 C12 . 1.385(5) ? C11 H11 . 0.950000 ? C12 H12 . 0.950000 ? C13 C14 . 1.455(4) ? C14 H14A . 0.980000 ? C14 H32B . 0.980000 ? C14 H33C . 0.980000 ? C15 C16 . 1.515(4) ? C15 H15A . 0.990000 ? C15 H15B . 0.990000 ? C17 C18 . 1.513(4) ? C17 H17A . 0.990000 ? C17 H17B . 0.990000 ? C18 C19 . 1.386(4) ? C18 C23 . 1.389(4) ? C19 C20 . 1.380(4) ? C19 H19 . 0.950000 ? C20 C21 . 1.385(4) ? C20 H20 . 0.950000 ? C21 C22 . 1.381(4) ? C21 H21 . 0.950000 ? C22 C23 . 1.388(4) ? C22 H22 . 0.950000 ? C23 H23 . 0.950000 ? Cl1R O5" . 1.277(17) ? Cl1R O3" . 1.38(2) ? Cl1R O2R . 1.420(2) ? Cl1R O4R . 1.420(3) ? Cl1R O4" . 1.42(2) ? Cl1R O5R . 1.438(3) ? Cl1R O3R . 1.474(3) ? Cl1S O2S . 1.400(3) ? Cl1S O3S . 1.410(3) ? Cl1S O5S . 1.422(3) ? Cl1S O3' . 1.44(2) ? Cl1S O4S . 1.456(3) ? Cl1S O2' . 1.457(19) ? Cl1S O1' . 1.610(15) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C5 N1 C1 C2 . . . . 0.7(4) ? Ni1 N1 C1 C2 . . . . -168.2(2) ? N1 C1 C2 C3 . . . . 0.9(4) ? C1 C2 C3 C4 . . . . -1.2(4) ? C2 C3 C4 C5 . . . . -0.1(4) ? C1 N1 C5 C4 . . . . -2.1(4) ? Ni1 N1 C5 C4 . . . . 168.4(2) ? C1 N1 C5 C6 . . . . 174.0(3) ? Ni1 N1 C5 C6 . . . . -15.5(3) ? C3 C4 C5 N1 . . . . 1.8(4) ? C3 C4 C5 C6 . . . . -174.0(3) ? C15 N2 C6 C5 . . . . 78.4(3) ? C7 N2 C6 C5 . . . . -154.8(2) ? Ni1 N2 C6 C5 . . . . -38.6(3) ? N1 C5 C6 N2 . . . . 37.2(4) ? C4 C5 C6 N2 . . . . -146.7(3) ? C15 N2 C7 C8 . . . . -75.0(3) ? C6 N2 C7 C8 . . . . 157.8(2) ? Ni1 N2 C7 C8 . . . . 41.5(3) ? C12 N3 C8 C9 . . . . 0.7(4) ? Ni1 N3 C8 C9 . . . . 178.7(2) ? C12 N3 C8 C7 . . . . -176.3(3) ? Ni1 N3 C8 C7 . . . . 1.8(3) ? N2 C7 C8 N3 . . . . -29.7(4) ? N2 C7 C8 C9 . . . . 153.3(3) ? N3 C8 C9 C10 . . . . -1.2(5) ? C7 C8 C9 C10 . . . . 175.6(3) ? C8 C9 C10 C11 . . . . 0.7(5) ? C9 C10 C11 C12 . . . . 0.1(5) ? C8 N3 C12 C11 . . . . 0.2(4) ? Ni1 N3 C12 C11 . . . . -177.5(2) ? C10 C11 C12 N3 . . . . -0.6(5) ? C7 N2 C15 C16 . . . . 134.5(3) ? C6 N2 C15 C16 . . . . -98.1(3) ? Ni1 N2 C15 C16 . . . . 18.5(3) ? Ni1 O1 C16 N5 . . . . -164.5(2) ? Ni1 O1 C16 C15 . . . . 18.3(3) ? C17 N5 C16 O1 . . . . -0.6(4) ? C17 N5 C16 C15 . . . . 176.8(3) ? N2 C15 C16 O1 . . . . -26.2(4) ? N2 C15 C16 N5 . . . . 156.4(3) ? C16 N5 C17 C18 . . . . 100.6(3) ? N5 C17 C18 C19 . . . . 143.9(3) ? N5 C17 C18 C23 . . . . -37.1(4) ? C23 C18 C19 C20 . . . . -0.1(4) ? C17 C18 C19 C20 . . . . 178.9(3) ? C18 C19 C20 C21 . . . . 0.5(4) ? C19 C20 C21 C22 . . . . -0.5(4) ? C20 C21 C22 C23 . . . . 0.2(4) ? C21 C22 C23 C18 . . . . 0.1(4) ? C19 C18 C23 C22 . . . . -0.2(4) ? C17 C18 C23 C22 . . . . -179.2(3) ?