# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cu_wong0031wy_shelxl #TrackingRef 'C-5.cif' _iucr_refine_instructions_details ; TITL cu_wong0031wy CELL 1.54178 8.18950 8.59870 16.79880 92.215 102.812 105.961 ZERR 1 0.00020 0.00030 0.00050 0.002 0.002 0.002 LATT 1 SFAC C N O S NI H UNIT 46 8 2 4 1 50 SHEL 8.000000 0.84 L.S. 10 FMAP 2 PLAN -20 BOND $H EQIV $1_X-1,Y,Z HTAB HTAB O1 N2 HTAB O1 N1_$1 TEMP -173.0 ACTA SIZE 0.300 0.240 0.220 LIST 4 WGHT 0.076000 0.717300 FVAR 0.20751 0.63447 NI1 5 0.500000 0.500000 0.000000 10.50000 0.01620 0.02407 = 0.02004 0.00135 0.00234 0.00536 S1 4 0.360697 0.534069 0.092206 11.00000 0.01762 0.04185 = 0.02271 0.00004 0.00243 0.01054 S2 4 0.735522 0.510005 0.092983 11.00000 0.01812 0.03735 = 0.02125 0.00163 0.00237 0.01038 O1 3 0.167937 0.711865 0.246975 11.00000 0.02622 0.03686 = 0.06465 0.00904 0.01581 0.00987 H1 6 0.244735 0.650902 0.251192 11.00000 0.05594 H2 6 0.078011 0.649835 0.253399 11.00000 0.04829 N1 2 0.807222 0.568843 0.254636 11.00000 0.02088 0.03013 = 0.02224 0.00339 0.00186 0.00619 N2 2 0.466521 0.582852 0.254593 11.00000 0.02361 0.03240 = 0.02482 0.00137 0.00524 0.00799 N4 2 -0.095852 0.830900 -0.328234 11.00000 0.04742 0.04276 = 0.02915 0.00448 0.00553 0.01132 C1 1 0.511485 0.555098 0.185722 11.00000 0.02173 0.02052 = 0.02466 0.00202 0.00436 0.00305 C2 1 0.686115 0.547008 0.186548 11.00000 0.02083 0.02019 = 0.02251 0.00266 0.00388 0.00411 C3 1 0.591423 0.604274 0.326355 11.00000 0.02445 0.02750 = 0.02148 0.00248 0.00137 0.00478 C4 1 0.763566 0.599184 0.327374 11.00000 0.02577 0.02821 = 0.02383 0.00487 0.00636 0.00561 C5 1 0.888318 0.625434 0.401755 11.00000 0.02575 0.05078 = 0.02522 0.00469 -0.00054 0.00974 AFIX 43 H5 6 1.003189 0.620795 0.402451 11.00000 -1.20000 AFIX 0 C6 1 0.846184 0.657963 0.474043 11.00000 0.03653 0.06119 = 0.02082 0.00310 0.00003 0.00954 AFIX 43 H6 6 0.932196 0.676889 0.524496 11.00000 -1.20000 AFIX 0 C7 1 0.676274 0.663288 0.473499 11.00000 0.04099 0.05656 = 0.01989 0.00054 0.00519 0.00989 AFIX 43 H7 6 0.647959 0.685807 0.523741 11.00000 -1.20000 AFIX 0 C8 1 0.551626 0.636544 0.401777 11.00000 0.03204 0.04945 = 0.03027 0.00505 0.01106 0.01224 AFIX 43 H8 6 0.436851 0.639601 0.402434 11.00000 -1.20000 AFIX 0 C9 1 0.351906 1.097814 0.043580 11.00000 0.04140 0.03037 = 0.04307 0.00639 0.00619 -0.00142 AFIX 43 H9 6 0.444692 1.194592 0.064075 11.00000 -1.20000 AFIX 0 C10 1 0.282015 1.065405 -0.038187 11.00000 0.03407 0.02554 = 0.03178 0.00534 0.00503 0.00415 AFIX 43 H10 6 0.326304 1.139093 -0.074322 11.00000 -1.20000 AFIX 0 C11 1 0.143911 0.923068 -0.070193 11.00000 0.02329 0.02417 = 0.03388 0.00333 0.00668 0.00974 C12 1 0.090020 0.817300 -0.013437 11.00000 0.02415 0.02391 = 0.03492 0.00302 0.00574 0.00634 AFIX 43 H12 6 -0.000565 0.718343 -0.032297 11.00000 -1.20000 AFIX 0 C13 1 0.165330 0.854226 0.067967 11.00000 0.03411 0.02989 = 0.03214 0.00687 0.00611 0.00185 AFIX 43 H13 6 0.128264 0.779934 0.105309 11.00000 -1.20000 AFIX 0 SAME N3 C14' > C18' N3 2 0.292788 0.995679 0.096828 11.00000 0.04136 0.04105 = 0.02857 0.00359 0.00146 -0.00397 PART 1 C14 1 0.354718 1.050921 0.187128 21.00000 0.02161 0.02872 = 0.02847 -0.00166 0.00658 0.01049 AFIX 23 H14A 6 0.270083 0.989190 0.216717 21.00000 -1.20000 H14B 6 0.366074 1.168086 0.197066 21.00000 -1.20000 AFIX 0 C15 1 0.531383 1.020593 0.217020 21.00000 0.02644 0.09524 = 0.02721 -0.01116 0.00179 0.02662 AFIX 23 H15A 6 0.623340 1.106977 0.201574 21.00000 -1.20000 H15B 6 0.529171 0.914818 0.190645 21.00000 -1.20000 AFIX 0 C16 1 0.575733 1.019314 0.315153 21.00000 0.05396 0.06841 = 0.12565 0.02611 0.01567 0.01675 AFIX 23 H16A 6 0.474315 0.949278 0.332311 21.00000 -1.20000 H16B 6 0.677531 0.977540 0.333880 21.00000 -1.20000 AFIX 0 C17 1 0.614531 1.183890 0.349058 21.00000 0.12370 0.06169 = 0.13267 0.01885 0.08324 0.02756 AFIX 23 H17A 6 0.512470 1.225588 0.330971 21.00000 -1.20000 H17B 6 0.715550 1.254337 0.331779 21.00000 -1.20000 AFIX 0 C18 1 0.660754 1.179778 0.448624 21.00000 0.04820 0.09201 = 0.03663 -0.01503 -0.00393 0.01528 AFIX 33 H18A 6 0.560260 1.186914 0.469624 21.00000 -1.50000 H18B 6 0.762631 1.272052 0.474140 21.00000 -1.50000 H18C 6 0.687077 1.077903 0.461786 21.00000 -1.50000 AFIX 0 PART 2 C14' 1 0.419678 0.991152 0.179615 -21.00000 0.08322 0.06045 = 0.06100 0.00967 0.01270 0.00611 AFIX 23 H14C 6 0.363745 0.902003 0.209122 -21.00000 -1.20000 H14D 6 0.527612 0.971779 0.169771 -21.00000 -1.20000 AFIX 0 C15' 1 0.461845 1.145617 0.227983 -21.00000 0.26330 0.09051 = 0.08070 0.03875 0.02321 0.05864 AFIX 23 H15C 6 0.361451 1.154499 0.249689 -21.00000 -1.20000 H15D 6 0.493182 1.236668 0.194622 -21.00000 -1.20000 AFIX 0 C16' 1 0.630297 1.148070 0.303549 -21.00000 0.02181 0.04446 = 0.03629 -0.00791 0.01163 -0.00680 AFIX 23 H16C 6 0.702208 1.083371 0.286570 -21.00000 -1.20000 H16D 6 0.704991 1.260553 0.323404 -21.00000 -1.20000 AFIX 0 C17' 1 0.541012 1.070783 0.368185 -21.00000 0.03671 0.05727 = 0.01350 -0.01057 0.00464 -0.01898 AFIX 23 H17C 6 0.495950 0.951220 0.354880 -21.00000 -1.20000 H17D 6 0.441967 1.113634 0.371565 -21.00000 -1.20000 AFIX 0 C18' 1 0.688128 1.117483 0.453514 -21.00000 0.11700 0.08754 = 0.04714 0.02201 0.00281 -0.00483 AFIX 33 H18D 6 0.705283 1.230321 0.474326 -21.00000 -1.50000 H18E 6 0.798497 1.105669 0.444485 -21.00000 -1.50000 H18F 6 0.650173 1.044891 0.493681 -21.00000 -1.50000 AFIX 0 PART 0 C19 1 0.061359 0.890490 -0.158567 11.00000 0.02309 0.02813 = 0.03080 0.00376 0.00575 0.00878 C20 1 0.061565 1.017084 -0.208579 11.00000 0.03800 0.02785 = 0.03795 0.00725 0.00884 0.00858 AFIX 43 H20 6 0.115973 1.126832 -0.185588 11.00000 -1.20000 AFIX 0 C21 1 -0.016727 0.982318 -0.290565 11.00000 0.04426 0.03705 = 0.03212 0.01118 0.00614 0.01312 AFIX 43 H21 6 -0.015105 1.070677 -0.322924 11.00000 -1.20000 AFIX 0 C22 1 -0.093716 0.710507 -0.280056 11.00000 0.04617 0.03320 = 0.03614 0.00165 0.00583 0.00720 AFIX 43 H22 6 -0.146718 0.602012 -0.305182 11.00000 -1.20000 AFIX 0 C23 1 -0.020532 0.732354 -0.196988 11.00000 0.03301 0.02821 = 0.03270 0.00441 0.00467 0.00761 AFIX 43 H23 6 -0.025512 0.641510 -0.166195 11.00000 -1.20000 HKLF 4 REM cu_wong0031wy REM R1 = 0.0420 for 2983 Fo > 4sig(Fo) and 0.0435 for all 3173 data REM 331 parameters refined using 9 restraints END WGHT 0.0760 0.7173 REM Highest difference peak 0.525, deepest hole -0.323, 1-sigma level 0.064 Q1 1 0.6192 0.4987 0.0481 11.00000 0.05 0.52 Q2 1 0.3761 0.9653 0.0969 11.00000 0.05 0.42 Q3 1 0.5279 0.4023 0.0398 11.00000 0.05 0.35 Q4 1 0.4816 1.1417 0.3203 11.00000 0.05 0.34 Q5 1 0.5599 1.1131 0.2107 11.00000 0.05 0.31 Q6 1 0.4689 0.5363 0.1429 11.00000 0.05 0.28 Q7 1 0.4188 1.1198 0.2204 11.00000 0.05 0.27 Q8 1 0.6783 1.0852 0.3840 11.00000 0.05 0.27 Q9 1 0.2954 0.6175 0.0981 11.00000 0.05 0.26 Q10 1 0.3652 0.4416 0.0112 11.00000 0.05 0.26 Q11 1 0.5493 1.1284 0.4022 11.00000 0.05 0.26 Q12 1 0.7324 0.5297 0.2201 11.00000 0.05 0.22 Q13 1 0.4300 1.0037 0.2113 11.00000 0.05 0.22 Q14 1 0.4499 1.0103 0.3721 11.00000 0.05 0.21 Q15 1 0.2071 0.4992 0.0825 11.00000 0.05 0.21 Q16 1 0.2041 0.7112 0.3087 11.00000 0.05 0.21 Q17 1 0.4661 0.8561 0.1936 11.00000 0.05 0.21 Q18 1 0.9252 0.5966 0.5456 11.00000 0.05 0.20 Q19 1 0.3524 0.6403 0.0483 11.00000 0.05 0.20 Q20 1 0.5768 1.3055 0.3302 11.00000 0.05 0.20 ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H8 N4 Ni S4, 2(C15 H19 N2), 2(H2 O)' _chemical_formula_sum 'C46 H50 N8 Ni O2 S4' _chemical_formula_weight 933.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1895(2) _cell_length_b 8.5987(3) _cell_length_c 16.7988(5) _cell_angle_alpha 92.215(2) _cell_angle_beta 102.812(2) _cell_angle_gamma 105.961(2) _cell_volume 1102.75(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5563 _cell_measurement_theta_min 5.77 _cell_measurement_theta_max 66.55 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 490 _exptl_absorpt_coefficient_mu 2.793 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5085 _exptl_absorpt_correction_T_max 0.6958 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '\w and \f scans' _diffrn_measurement_method 'BRUKER APEX DUO' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 5563 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.77 _diffrn_reflns_theta_max 66.55 _reflns_number_total 3173 _reflns_number_gt 2983 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+0.7173P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3173 _refine_ls_number_parameters 331 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.5000 0.0000 0.02057(19) Uani 1 2 d S . . S1 S 0.36070(7) 0.53407(8) 0.09221(4) 0.0275(2) Uani 1 1 d . . . S2 S 0.73552(7) 0.51001(7) 0.09298(4) 0.0255(2) Uani 1 1 d . . . O1 O 0.1679(3) 0.7119(2) 0.24697(15) 0.0415(5) Uani 1 1 d . . . H1 H 0.245(5) 0.651(5) 0.251(2) 0.056(10) Uiso 1 1 d . . . H2 H 0.078(5) 0.650(4) 0.253(2) 0.048(10) Uiso 1 1 d . . . N1 N 0.8072(3) 0.5688(2) 0.25464(13) 0.0252(5) Uani 1 1 d . . . N2 N 0.4665(3) 0.5829(3) 0.25459(14) 0.0271(5) Uani 1 1 d . . . N4 N -0.0959(4) 0.8309(3) -0.32823(16) 0.0407(6) Uani 1 1 d . . . C1 C 0.5115(3) 0.5551(3) 0.18572(16) 0.0232(5) Uani 1 1 d . . . C2 C 0.6861(3) 0.5470(3) 0.18655(15) 0.0218(5) Uani 1 1 d . . . C3 C 0.5914(3) 0.6043(3) 0.32635(16) 0.0257(6) Uani 1 1 d . . . C4 C 0.7636(3) 0.5992(3) 0.32737(16) 0.0263(6) Uani 1 1 d . . . C5 C 0.8883(4) 0.6254(4) 0.40176(18) 0.0353(6) Uani 1 1 d . . . H5 H 1.0032 0.6208 0.4025 0.042 Uiso 1 1 calc R . . C6 C 0.8462(4) 0.6580(4) 0.47404(19) 0.0416(7) Uani 1 1 d . . . H6 H 0.9322 0.6769 0.5245 0.050 Uiso 1 1 calc R . . C7 C 0.6763(4) 0.6633(4) 0.47350(19) 0.0405(7) Uani 1 1 d . . . H7 H 0.6480 0.6858 0.5237 0.049 Uiso 1 1 calc R . . C8 C 0.5516(4) 0.6365(4) 0.40178(18) 0.0366(7) Uani 1 1 d . . . H8 H 0.4369 0.6396 0.4024 0.044 Uiso 1 1 calc R . . C9 C 0.3519(4) 1.0978(3) 0.0436(2) 0.0413(7) Uani 1 1 d . A . H9 H 0.4447 1.1946 0.0641 0.050 Uiso 1 1 calc R . . C10 C 0.2820(4) 1.0654(3) -0.03819(18) 0.0318(6) Uani 1 1 d . . . H10 H 0.3263 1.1391 -0.0743 0.038 Uiso 1 1 calc R . . C11 C 0.1439(3) 0.9231(3) -0.07019(17) 0.0266(6) Uani 1 1 d . . . C12 C 0.0900(3) 0.8173(3) -0.01344(17) 0.0280(6) Uani 1 1 d . . . H12 H -0.0006 0.7183 -0.0323 0.034 Uiso 1 1 calc R . . C13 C 0.1653(4) 0.8542(3) 0.06797(19) 0.0338(6) Uani 1 1 d . A . H13 H 0.1283 0.7799 0.1053 0.041 Uiso 1 1 calc R . . N3 N 0.2928(3) 0.9957(3) 0.09683(16) 0.0414(6) Uani 1 1 d D . . C14 C 0.3547(5) 1.0509(6) 0.1871(3) 0.0257(12) Uani 0.634(8) 1 d PD A 1 H14A H 0.2701 0.9892 0.2167 0.031 Uiso 0.634(8) 1 calc PR A 1 H14B H 0.3661 1.1681 0.1971 0.031 Uiso 0.634(8) 1 calc PR A 1 C15 C 0.5314(7) 1.0206(8) 0.2170(4) 0.0491(17) Uani 0.634(8) 1 d PD A 1 H15A H 0.6233 1.1070 0.2016 0.059 Uiso 0.634(8) 1 calc PR A 1 H15B H 0.5292 0.9148 0.1906 0.059 Uiso 0.634(8) 1 calc PR A 1 C16 C 0.5757(9) 1.0193(8) 0.3152(6) 0.083(3) Uani 0.634(8) 1 d PD A 1 H16A H 0.4743 0.9493 0.3323 0.100 Uiso 0.634(8) 1 calc PR A 1 H16B H 0.6775 0.9775 0.3339 0.100 Uiso 0.634(8) 1 calc PR A 1 C17 C 0.6145(13) 1.1839(9) 0.3491(6) 0.097(3) Uani 0.634(8) 1 d PD A 1 H17A H 0.5125 1.2256 0.3310 0.117 Uiso 0.634(8) 1 calc PR A 1 H17B H 0.7156 1.2543 0.3318 0.117 Uiso 0.634(8) 1 calc PR A 1 C18 C 0.6608(13) 1.1798(13) 0.4486(5) 0.063(3) Uani 0.634(8) 1 d PD A 1 H18A H 0.5603 1.1869 0.4696 0.094 Uiso 0.634(8) 1 calc PR A 1 H18B H 0.7626 1.2721 0.4741 0.094 Uiso 0.634(8) 1 calc PR A 1 H18C H 0.6871 1.0779 0.4618 0.094 Uiso 0.634(8) 1 calc PR A 1 C14' C 0.420(2) 0.9912(15) 0.1796(7) 0.072(4) Uani 0.366(8) 1 d PD A 2 H14C H 0.3637 0.9020 0.2091 0.086 Uiso 0.366(8) 1 calc PR A 2 H14D H 0.5276 0.9718 0.1698 0.086 Uiso 0.366(8) 1 calc PR A 2 C15' C 0.462(3) 1.1456(18) 0.2280(9) 0.146(10) Uani 0.366(8) 1 d PD A 2 H15C H 0.3615 1.1545 0.2497 0.175 Uiso 0.366(8) 1 calc PR A 2 H15D H 0.4932 1.2367 0.1946 0.175 Uiso 0.366(8) 1 calc PR A 2 C16' C 0.6303(10) 1.1481(11) 0.3035(6) 0.037(2) Uani 0.366(8) 1 d PD A 2 H16C H 0.7022 1.0834 0.2866 0.045 Uiso 0.366(8) 1 calc PR A 2 H16D H 0.7050 1.2606 0.3234 0.045 Uiso 0.366(8) 1 calc PR A 2 C17' C 0.5410(12) 1.0708(12) 0.3682(5) 0.043(3) Uani 0.366(8) 1 d PD A 2 H17C H 0.4960 0.9512 0.3549 0.052 Uiso 0.366(8) 1 calc PR A 2 H17D H 0.4420 1.1136 0.3716 0.052 Uiso 0.366(8) 1 calc PR A 2 C18' C 0.688(3) 1.117(2) 0.4535(10) 0.093(8) Uani 0.366(8) 1 d PD A 2 H18D H 0.7053 1.2303 0.4743 0.140 Uiso 0.366(8) 1 calc PR A 2 H18E H 0.7985 1.1057 0.4445 0.140 Uiso 0.366(8) 1 calc PR A 2 H18F H 0.6502 1.0449 0.4937 0.140 Uiso 0.366(8) 1 calc PR A 2 C19 C 0.0614(3) 0.8905(3) -0.15857(17) 0.0272(6) Uani 1 1 d . . . C20 C 0.0616(4) 1.0171(3) -0.20858(18) 0.0348(7) Uani 1 1 d . . . H20 H 0.1160 1.1268 -0.1856 0.042 Uiso 1 1 calc R . . C21 C -0.0167(4) 0.9823(3) -0.29056(19) 0.0378(7) Uani 1 1 d . . . H21 H -0.0151 1.0707 -0.3229 0.045 Uiso 1 1 calc R . . C22 C -0.0937(4) 0.7105(3) -0.28006(19) 0.0401(7) Uani 1 1 d . . . H22 H -0.1467 0.6020 -0.3052 0.048 Uiso 1 1 calc R . . C23 C -0.0205(4) 0.7324(3) -0.19699(18) 0.0321(6) Uani 1 1 d . . . H23 H -0.0255 0.6415 -0.1662 0.038 Uiso 1 1 calc R . . 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 0.0162(3) 0.0241(3) 0.0200(4) 0.0013(2) 0.0023(3) 0.0054(2) S1 0.0176(3) 0.0418(4) 0.0227(4) 0.0000(3) 0.0024(3) 0.0105(3) S2 0.0181(3) 0.0374(3) 0.0213(4) 0.0016(3) 0.0024(3) 0.0104(2) O1 0.0262(10) 0.0369(10) 0.0646(17) 0.0090(10) 0.0158(11) 0.0099(9) N1 0.0209(10) 0.0301(10) 0.0222(13) 0.0034(9) 0.0019(11) 0.0062(8) N2 0.0236(11) 0.0324(10) 0.0248(13) 0.0014(9) 0.0052(11) 0.0080(9) N4 0.0474(15) 0.0428(13) 0.0292(16) 0.0045(12) 0.0055(13) 0.0113(11) C1 0.0217(12) 0.0205(10) 0.0247(15) 0.0020(10) 0.0044(12) 0.0030(9) C2 0.0208(12) 0.0202(10) 0.0225(15) 0.0027(10) 0.0039(12) 0.0041(9) C3 0.0245(12) 0.0275(11) 0.0215(15) 0.0025(11) 0.0014(13) 0.0048(10) C4 0.0258(13) 0.0282(11) 0.0238(16) 0.0049(11) 0.0064(13) 0.0056(10) C5 0.0258(13) 0.0508(16) 0.0252(17) 0.0047(13) -0.0005(14) 0.0097(12) C6 0.0365(16) 0.0612(18) 0.0208(17) 0.0031(15) 0.0000(15) 0.0095(14) C7 0.0410(17) 0.0566(17) 0.0199(17) 0.0005(14) 0.0052(15) 0.0099(13) C8 0.0320(15) 0.0495(15) 0.0303(18) 0.0051(13) 0.0111(15) 0.0122(12) C9 0.0414(16) 0.0304(13) 0.043(2) 0.0064(13) 0.0062(16) -0.0014(12) C10 0.0341(14) 0.0255(11) 0.0318(18) 0.0053(12) 0.0050(14) 0.0041(10) C11 0.0233(12) 0.0242(11) 0.0339(17) 0.0033(11) 0.0067(13) 0.0097(9) C12 0.0242(12) 0.0239(11) 0.0349(18) 0.0030(11) 0.0057(13) 0.0063(9) C13 0.0341(14) 0.0299(12) 0.0321(19) 0.0069(12) 0.0061(15) 0.0018(11) N3 0.0414(14) 0.0410(13) 0.0286(16) 0.0036(11) 0.0015(13) -0.0040(11) C14 0.022(2) 0.029(2) 0.028(3) -0.002(2) 0.007(2) 0.0105(18) C15 0.026(3) 0.095(4) 0.027(4) -0.011(3) 0.002(3) 0.027(3) C16 0.054(4) 0.068(5) 0.126(9) 0.026(5) 0.016(5) 0.017(3) C17 0.124(8) 0.062(5) 0.133(9) 0.019(5) 0.083(8) 0.028(5) C18 0.048(4) 0.092(7) 0.037(5) -0.015(5) -0.004(4) 0.015(4) C14' 0.083(12) 0.060(7) 0.061(10) 0.010(7) 0.013(9) 0.006(7) C15' 0.26(3) 0.091(12) 0.081(14) 0.039(11) 0.023(17) 0.059(17) C16' 0.022(4) 0.044(5) 0.036(6) -0.008(4) 0.012(4) -0.007(3) C17' 0.037(5) 0.057(5) 0.014(5) -0.011(4) 0.005(4) -0.019(4) C18' 0.117(18) 0.088(13) 0.047(9) 0.022(9) 0.003(10) -0.005(10) C19 0.0231(12) 0.0281(12) 0.0308(17) 0.0038(11) 0.0057(13) 0.0088(10) C20 0.0380(15) 0.0279(12) 0.0379(19) 0.0072(12) 0.0088(15) 0.0086(11) C21 0.0443(16) 0.0371(14) 0.0321(18) 0.0112(13) 0.0061(15) 0.0131(12) C22 0.0462(17) 0.0332(13) 0.036(2) 0.0017(13) 0.0058(16) 0.0072(12) C23 0.0330(14) 0.0282(12) 0.0327(18) 0.0044(12) 0.0047(14) 0.0076(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S1 2.1723(6) . ? Ni1 S1 2.1723(6) 2_665 ? Ni1 S2 2.1748(6) 2_665 ? Ni1 S2 2.1748(6) . ? S1 C1 1.738(3) . ? S2 C2 1.746(2) . ? O1 H1 0.92(4) . ? O1 H2 0.81(4) . ? N1 C2 1.306(3) . ? N1 C4 1.382(3) . ? N2 C1 1.322(3) . ? N2 C3 1.366(4) . ? N4 C22 1.340(4) . ? N4 C21 1.344(4) . ? C1 C2 1.448(3) . ? C3 C8 1.412(4) . ? C3 C4 1.419(3) . ? C4 C5 1.393(4) . ? C5 C6 1.373(4) . ? C5 H5 0.9500 . ? C6 C7 1.403(4) . ? C6 H6 0.9500 . ? C7 C8 1.360(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 N3 1.351(4) . ? C9 C10 1.351(4) . ? C9 H9 0.9500 . ? C10 C11 1.409(4) . ? C10 H10 0.9500 . ? C11 C12 1.401(3) . ? C11 C19 1.469(4) . ? C12 C13 1.355(4) . ? C12 H12 0.9500 . ? C13 N3 1.355(4) . ? C13 H13 0.9500 . ? N3 C14 1.502(5) . ? N3 C14' 1.550(12) . ? C14 C15 1.519(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.609(10) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.428(10) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.635(12) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C14' C15' 1.443(15) . ? C14' H14C 0.9900 . ? C14' H14D 0.9900 . ? C15' C16' 1.649(16) . ? C15' H15C 0.9900 . ? C15' H15D 0.9900 . ? C16' C17' 1.515(9) . ? C16' H16C 0.9900 . ? C16' H16D 0.9900 . ? C17' C18' 1.610(16) . ? C17' H17C 0.9900 . ? C17' H17D 0.9900 . ? C18' H18D 0.9800 . ? C18' H18E 0.9800 . ? C18' H18F 0.9800 . ? C19 C23 1.398(4) . ? C19 C20 1.400(3) . ? C20 C21 1.367(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.374(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Ni1 S1 180.000(1) . 2_665 ? S1 Ni1 S2 87.89(2) . 2_665 ? S1 Ni1 S2 92.11(2) 2_665 2_665 ? S1 Ni1 S2 92.11(2) . . ? S1 Ni1 S2 87.89(2) 2_665 . ? S2 Ni1 S2 180.00(4) 2_665 . ? C1 S1 Ni1 105.04(8) . . ? C2 S2 Ni1 105.05(8) . . ? H1 O1 H2 105(3) . . ? C2 N1 C4 117.8(2) . . ? C1 N2 C3 117.4(2) . . ? C22 N4 C21 115.7(3) . . ? N2 C1 C2 121.2(2) . . ? N2 C1 S1 119.53(18) . . ? C2 C1 S1 119.26(18) . . ? N1 C2 C1 122.1(2) . . ? N1 C2 S2 119.47(17) . . ? C1 C2 S2 118.46(19) . . ? N2 C3 C8 119.9(2) . . ? N2 C3 C4 121.6(2) . . ? C8 C3 C4 118.4(3) . . ? N1 C4 C5 120.2(2) . . ? N1 C4 C3 119.9(2) . . ? C5 C4 C3 119.9(2) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 120.1(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.7(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C3 120.6(3) . . ? C7 C8 H8 119.7 . . ? C3 C8 H8 119.7 . . ? N3 C9 C10 121.5(3) . . ? N3 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C9 C10 C11 120.4(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 116.5(3) . . ? C12 C11 C19 122.6(2) . . ? C10 C11 C19 120.9(2) . . ? C13 C12 C11 120.9(2) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? N3 C13 C12 120.9(2) . . ? N3 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C9 N3 C13 119.7(3) . . ? C9 N3 C14 118.8(3) . . ? C13 N3 C14 121.1(3) . . ? C9 N3 C14' 118.9(5) . . ? C13 N3 C14' 114.7(5) . . ? C14 N3 C14' 32.7(6) . . ? N3 C14 C15 107.4(4) . . ? N3 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? N3 C14 H14B 110.2 . . ? C15 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? C14 C15 C16 110.0(4) . . ? C14 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? C14 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C17 C16 C15 106.3(7) . . ? C17 C16 H16A 110.5 . . ? C15 C16 H16A 110.5 . . ? C17 C16 H16B 110.5 . . ? C15 C16 H16B 110.5 . . ? H16A C16 H16B 108.7 . . ? C16 C17 C18 105.5(7) . . ? C16 C17 H17A 110.6 . . ? C18 C17 H17A 110.6 . . ? C16 C17 H17B 110.6 . . ? C18 C17 H17B 110.6 . . ? H17A C17 H17B 108.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15' C14' N3 108.2(11) . . ? C15' C14' H14C 110.1 . . ? N3 C14' H14C 110.1 . . ? C15' C14' H14D 110.1 . . ? N3 C14' H14D 110.1 . . ? H14C C14' H14D 108.4 . . ? C14' C15' C16' 105.1(12) . . ? C14' C15' H15C 110.7 . . ? C16' C15' H15C 110.7 . . ? C14' C15' H15D 110.7 . . ? C16' C15' H15D 110.7 . . ? H15C C15' H15D 108.8 . . ? C17' C16' C15' 101.9(9) . . ? C17' C16' H16C 111.4 . . ? C15' C16' H16C 111.4 . . ? C17' C16' H16D 111.4 . . ? C15' C16' H16D 111.4 . . ? H16C C16' H16D 109.2 . . ? C16' C17' C18' 106.0(11) . . ? C16' C17' H17C 110.5 . . ? C18' C17' H17C 110.5 . . ? C16' C17' H17D 110.5 . . ? C18' C17' H17D 110.5 . . ? H17C C17' H17D 108.7 . . ? C17' C18' H18D 109.5 . . ? C17' C18' H18E 109.5 . . ? H18D C18' H18E 109.5 . . ? C17' C18' H18F 109.5 . . ? H18D C18' H18F 109.5 . . ? H18E C18' H18F 109.5 . . ? C23 C19 C20 116.7(3) . . ? C23 C19 C11 121.9(2) . . ? C20 C19 C11 121.4(2) . . ? C21 C20 C19 119.8(3) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? N4 C21 C20 124.1(2) . . ? N4 C21 H21 118.0 . . ? C20 C21 H21 118.0 . . ? N4 C22 C23 124.8(3) . . ? N4 C22 H22 117.6 . . ? C23 C22 H22 117.6 . . ? C22 C23 C19 118.9(2) . . ? C22 C23 H23 120.6 . . ? C19 C23 H23 120.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N2 0.92(4) 2.05(4) 2.931(3) 162(3) . O1 H2 N1 0.81(4) 2.14(4) 2.905(3) 157(3) 1_455 _diffrn_measured_fraction_theta_max 0.819 _diffrn_reflns_theta_full 66.55 _diffrn_measured_fraction_theta_full 0.819 _refine_diff_density_max 0.525 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.064 # start Validation Reply Form _vrf_DIFF020_cu_wong0031wy_shelxl ; PROBLEM: _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. RESPONSE: The data was collected using CCD detector, no standards were collected ; _vrf_DIFF022_cu_wong0031wy_shelxl ; PROBLEM: _diffrn_standards_decay_% is missing Percentage decrease in standards intensity. RESPONSE: The data was collected using CCD detector, no standards were collected, thus no decay data was measured. ; _vrf_REFLT03_cu_wong0031wy_shelxl ; PROBLEM: Reflection count < 85% complete (theta max?) >From the CIF: _diffrn_reflns_theta_max 66.55 >From the CIF: _diffrn_reflns_theta_full 66.55 >From the CIF: _reflns_number_total 3173 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3872 Completeness (_total/calc) 81.95% RESPONSE: Copper instead of Mo radiation was used to collect data, which may be the reason for the low number of reflections collected. This may be due to the mis-calculation by the software used. ; _vrf_PLAT029_cu_wong0031wy_shelxl ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.819 RESPONSE: Copper instead of Mo radiation was used to collect data, which may be the reason for the low number of reflections collected. This may be due to the mis-calculation by the software used. ; _vrf_PLAT220_cu_wong0031wy_shelxl ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.6 Ratio RESPONSE: ; _vrf_PLAT230_cu_wong0031wy_shelxl ; PROBLEM: Hirshfeld Test Diff for C15 -- C16 .. 13.0 su Hirshfeld Test Diff for C17 -- C18 .. 9.9 su Hirshfeld Test Diff for C9 -- C10 .. 5.5 su RESPONSE: ; _vrf_PLAT911_cu_wong0031wy_shelxl ; PROBLEM: Missing # FCF Refl Between THmin & STh/L= 0.595 697 RESPONSE: ; _vrf_PLAT234_cu_wong0031wy_shelxl ; PROBLEM: Large Hirshfeld Difference N3 -- C14' .. 0.19 Ang. RESPONSE: ; _vrf_PLAT002_cu_wong0031wy_shelxl ; PROBLEM: Number of Distance or Angle Restraints on AtSite 11 RESPONSE: The pentyl group was disordered. ; _vrf_PLAT144_cu_wong0031wy_shelxl ; PROBLEM: su on alpha Small or Missing ................ 0.0000 Deg. RESPONSE: ; _vrf_PLAT242_cu_wong0031wy_shelxl ; PROBLEM: Check Low Ueq as Compared to Neighbors for C14 Check Low Ueq as Compared to Neighbors for C14' Check Low Ueq as Compared to Neighbors for C16' Check Low Ueq as Compared to Neighbors for C17' RESPONSE: ; _vrf_PLAT301_cu_wong0031wy_shelxl ; PROBLEM: Note: Main Residue Disorder ................... 12 Perc. RESPONSE: The pentyl group was found to be disordered. ; _vrf_PLAT860_cu_wong0031wy_shelxl ; PROBLEM: Note: Number of Least-Squares Restraints ....... 9 RESPONSE: Due to the disordered pentyl group, the corresponding C---C distances of the disordered groups were restrained to be similar. ; _vrf_PLAT909_cu_wong0031wy_shelxl ; PROBLEM: Percentage of Observed Data at Theta(Max) still 90 Perc. RESPONSE: ; _vrf_PLAT_cu_wong0031wy_shelxl ; PROBLEM: RESPONSE: ; # End Validation Reply Form #============================================================================ _database_code_depnum_ccdc_archive 'CCDC 923280' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_102511a_boyang #TrackingRef '- C6-1.cif' _audit_creation_date 2011-11-01 _audit_creation_method ; Olex2 1.1 (compiled 2011.08.18 svn.r1932, GUI svn.r3819) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H8 N4 Ni S4, 2(C16 H21 N2)' _chemical_formula_sum 'C48 H50 N8 Ni S4' _chemical_formula_weight 925.91 _chemical_melting_point ? _chemical_oxdiff_formula 'C11 H10 S O2' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 14.8356(2) _cell_length_b 10.8116(2) _cell_length_c 13.3564(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.7110(10) _cell_angle_gamma 90.00 _cell_volume 2137.83(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5615 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 71.5861 _cell_measurement_theta_min 3.3131 _exptl_absorpt_coefficient_mu 2.841 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84957 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 972 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_unetI/netI 0.0150 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8371 _diffrn_reflns_theta_full 66.99 _diffrn_reflns_theta_max 66.99 _diffrn_reflns_theta_min 5.07 _diffrn_ambient_temperature 133.0 _diffrn_detector_area_resol_mean 16.1270 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -18.00 26.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 37.0000 -90.0000 44 #__ type_ start__ end____ width___ exp.time_ 2 omega 36.00 68.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 37.0000 -90.0000 32 #__ type_ start__ end____ width___ exp.time_ 3 omega -37.00 -11.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 -37.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 4 omega -103.00 -22.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - -55.0000 125.0000 -180.0000 81 #__ type_ start__ end____ width___ exp.time_ 5 omega 44.00 116.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ frames - 55.0000 77.0000 -90.0000 72 #__ type_ start__ end____ width___ exp.time_ 6 omega -130.00 -81.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -149.0000 -17.0000 49 #__ type_ start__ end____ width___ exp.time_ 7 omega -113.00 -42.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - -64.0000 -50.0000 150.0000 71 #__ type_ start__ end____ width___ exp.time_ 8 omega 40.00 68.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 -150.0000 28 #__ type_ start__ end____ width___ exp.time_ 9 omega 37.00 66.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 90.0000 29 #__ type_ start__ end____ width___ exp.time_ 10 omega 97.00 124.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -7.0000 27 #__ type_ start__ end____ width___ exp.time_ 11 omega 41.00 67.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 12 omega 42.00 83.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 -30.0000 41 #__ type_ start__ end____ width___ exp.time_ 13 omega 38.00 72.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -150.0000 34 #__ type_ start__ end____ width___ exp.time_ 14 omega 39.00 65.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 15 omega 37.00 62.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 -60.0000 25 #__ type_ start__ end____ width___ exp.time_ 16 omega 37.00 71.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 120.0000 34 #__ type_ start__ end____ width___ exp.time_ 17 omega 89.00 169.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 50.0000 -120.0000 80 #__ type_ start__ end____ width___ exp.time_ 18 omega 40.00 76.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -50.0000 30.0000 36 #__ type_ start__ end____ width___ exp.time_ 19 omega 37.00 62.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -25.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 20 omega 107.00 146.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -145.0000 39 #__ type_ start__ end____ width___ exp.time_ 21 omega 38.00 67.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -7.0000 29 #__ type_ start__ end____ width___ exp.time_ 22 omega 40.00 136.00 1.0000 32.0000 omega____ theta____ kappa____ phi______ frames - 110.0000 -88.0000 -55.0000 96 ; _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0135471000 _diffrn_orient_matrix_UB_12 -0.1411500000 _diffrn_orient_matrix_UB_13 0.0031595000 _diffrn_orient_matrix_UB_21 0.0913017000 _diffrn_orient_matrix_UB_22 -0.0141296000 _diffrn_orient_matrix_UB_23 0.0608078000 _diffrn_orient_matrix_UB_31 -0.0481217000 _diffrn_orient_matrix_UB_32 0.0131606000 _diffrn_orient_matrix_UB_33 0.0982329000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3639 _reflns_number_total 3793 _reflns_odcompleteness_completeness 99.30 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.247 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 278 _refine_ls_number_reflns 3793 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0257 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.9548P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.0707 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.5000 0.5000 0.01746(10) Uani 1 2 d S . . S1 S 0.56805(2) 0.36399(3) 0.41269(3) 0.02092(10) Uani 1 1 d . . . S2 S 0.40569(2) 0.35555(3) 0.53923(3) 0.02119(10) Uani 1 1 d . . . N1 N 0.72064(8) 0.37572(11) 0.32084(9) 0.0219(3) Uani 1 1 d . . . N2 N 0.25508(8) 0.36832(11) 0.63619(9) 0.0222(3) Uani 1 1 d . . . N3 N 0.87570(10) 0.42613(15) -0.07102(11) 0.0399(4) Uani 1 1 d . . . N4 N 0.48538(8) 0.54785(11) 0.18987(8) 0.0208(2) Uani 1 1 d . . . C1 C 0.66327(9) 0.43876(13) 0.37184(10) 0.0195(3) Uani 1 1 d . . . C2 C 0.79428(9) 0.43952(14) 0.29039(10) 0.0224(3) Uani 1 1 d . . . C3 C 0.85882(10) 0.37648(16) 0.23613(11) 0.0283(3) Uani 1 1 d . . . H3 H 0.8520 0.2905 0.2231 0.034 Uiso 1 1 calc R . . C4 C 0.93128(10) 0.43922(17) 0.20230(12) 0.0321(4) Uani 1 1 d . . . H4 H 0.9740 0.3965 0.1651 0.039 Uiso 1 1 calc R . . C5 C 0.32441(9) 0.43107(13) 0.60606(10) 0.0197(3) Uani 1 1 d . . . C6 C 0.19401(9) 0.43330(14) 0.68884(10) 0.0227(3) Uani 1 1 d . . . C7 C 0.11819(10) 0.37188(15) 0.72388(12) 0.0285(3) Uani 1 1 d . . . H7 H 0.1094 0.2864 0.7099 0.034 Uiso 1 1 calc R . . C8 C 0.05720(10) 0.43415(17) 0.77782(12) 0.0319(4) Uani 1 1 d . . . H8 H 0.0069 0.3915 0.8018 0.038 Uiso 1 1 calc R . . C9 C 0.77165(11) 0.56851(15) -0.00173(12) 0.0313(3) Uani 1 1 d . . . H9 H 0.7551 0.6521 0.0093 0.038 Uiso 1 1 calc R . . C10 C 0.84780(12) 0.54072(18) -0.05166(14) 0.0407(4) Uani 1 1 d . . . H10 H 0.8828 0.6078 -0.0738 0.049 Uiso 1 1 calc R . . C11 C 0.82473(11) 0.33394(17) -0.03894(13) 0.0348(4) Uani 1 1 d . . . H11 H 0.8429 0.2514 -0.0515 0.042 Uiso 1 1 calc R . . C12 C 0.74695(10) 0.35175(15) 0.01159(12) 0.0287(3) Uani 1 1 d . . . H12 H 0.7128 0.2829 0.0319 0.034 Uiso 1 1 calc R . . C13 C 0.71957(10) 0.47186(14) 0.03213(10) 0.0231(3) Uani 1 1 d . . . C14 C 0.63849(10) 0.49653(13) 0.08768(10) 0.0208(3) Uani 1 1 d . . . C15 C 0.63012(9) 0.60666(13) 0.14114(10) 0.0213(3) Uani 1 1 d . . . H15 H 0.6773 0.6661 0.1427 0.026 Uiso 1 1 calc R . . C16 C 0.55404(10) 0.62926(13) 0.19136(10) 0.0219(3) Uani 1 1 d . . . H16 H 0.5497 0.7041 0.2280 0.026 Uiso 1 1 calc R . . C17 C 0.49147(10) 0.44036(13) 0.13949(10) 0.0229(3) Uani 1 1 d . . . H17 H 0.4430 0.3829 0.1389 0.028 Uiso 1 1 calc R . . C18 C 0.56672(10) 0.41286(13) 0.08904(11) 0.0232(3) Uani 1 1 d . . . H18 H 0.5700 0.3362 0.0547 0.028 Uiso 1 1 calc R . . C19 C 0.40410(10) 0.58345(14) 0.24392(11) 0.0248(3) Uani 1 1 d . . . H19A H 0.3701 0.6470 0.2037 0.030 Uiso 1 1 calc R . . H19B H 0.4248 0.6220 0.3086 0.030 Uiso 1 1 calc R . . C20 C 0.34044(10) 0.47913(14) 0.26481(11) 0.0246(3) Uani 1 1 d . . . H20A H 0.3739 0.4122 0.3016 0.029 Uiso 1 1 calc R . . H20B H 0.3139 0.4448 0.2008 0.029 Uiso 1 1 calc R . . C21 C 0.26562(10) 0.52778(14) 0.32737(11) 0.0251(3) Uani 1 1 d . . . H21A H 0.2930 0.5631 0.3906 0.030 Uiso 1 1 calc R . . H21B H 0.2330 0.5951 0.2901 0.030 Uiso 1 1 calc R . . C22 C 0.19869(10) 0.42806(15) 0.35213(12) 0.0295(3) Uani 1 1 d . . . H22A H 0.2320 0.3597 0.3872 0.035 Uiso 1 1 calc R . . H22B H 0.1705 0.3945 0.2886 0.035 Uiso 1 1 calc R . . C23 C 0.12454(10) 0.47165(15) 0.41695(12) 0.0285(3) Uani 1 1 d . . . H23A H 0.0882 0.5360 0.3803 0.034 Uiso 1 1 calc R . . H23B H 0.1523 0.5095 0.4790 0.034 Uiso 1 1 calc R . . C24 C 0.06269(11) 0.36667(16) 0.44495(14) 0.0363(4) Uani 1 1 d . . . H24A H 0.0327 0.3316 0.3839 0.054 Uiso 1 1 calc R . . H24B H 0.0171 0.3985 0.4883 0.054 Uiso 1 1 calc R . . H24C H 0.0984 0.3023 0.4807 0.054 Uiso 1 1 calc R . . 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 0.01593(17) 0.01814(18) 0.01870(17) 0.00007(12) 0.00423(12) 0.00064(12) S1 0.01906(17) 0.01936(18) 0.02507(18) -0.00196(12) 0.00713(13) -0.00088(12) S2 0.02026(18) 0.01916(18) 0.02486(18) -0.00062(12) 0.00695(13) 0.00030(12) N1 0.0200(6) 0.0250(6) 0.0211(6) 0.0008(5) 0.0046(5) 0.0017(5) N2 0.0196(6) 0.0248(6) 0.0226(6) 0.0028(5) 0.0039(5) -0.0008(5) N3 0.0332(8) 0.0492(9) 0.0389(8) -0.0122(7) 0.0155(6) -0.0055(7) N4 0.0212(6) 0.0215(6) 0.0199(6) 0.0030(5) 0.0022(5) 0.0011(5) C1 0.0179(6) 0.0235(7) 0.0171(6) 0.0021(5) 0.0016(5) 0.0014(5) C2 0.0187(6) 0.0304(8) 0.0183(6) 0.0034(6) 0.0025(5) 0.0020(6) C3 0.0241(7) 0.0349(9) 0.0265(8) -0.0006(6) 0.0063(6) 0.0049(6) C4 0.0220(7) 0.0475(10) 0.0279(8) 0.0014(7) 0.0097(6) 0.0063(7) C5 0.0177(6) 0.0248(7) 0.0167(6) 0.0022(5) 0.0011(5) 0.0016(5) C6 0.0188(7) 0.0300(8) 0.0193(7) 0.0043(6) 0.0019(5) 0.0003(6) C7 0.0232(7) 0.0337(9) 0.0290(8) 0.0058(6) 0.0055(6) -0.0030(6) C8 0.0210(7) 0.0455(10) 0.0300(8) 0.0083(7) 0.0077(6) -0.0017(7) C9 0.0339(8) 0.0297(8) 0.0316(8) 0.0007(7) 0.0112(7) -0.0035(7) C10 0.0400(10) 0.0414(10) 0.0431(10) -0.0023(8) 0.0207(8) -0.0097(8) C11 0.0290(8) 0.0384(9) 0.0377(9) -0.0140(7) 0.0064(7) -0.0014(7) C12 0.0244(7) 0.0297(8) 0.0324(8) -0.0050(6) 0.0042(6) -0.0027(6) C13 0.0222(7) 0.0284(7) 0.0186(6) -0.0005(6) 0.0010(5) -0.0015(6) C14 0.0222(7) 0.0231(7) 0.0171(6) 0.0041(5) 0.0002(5) 0.0010(5) C15 0.0213(7) 0.0214(7) 0.0209(7) 0.0025(5) -0.0006(5) -0.0023(5) C16 0.0254(7) 0.0195(7) 0.0206(7) 0.0017(5) 0.0000(5) -0.0002(5) C17 0.0239(7) 0.0215(7) 0.0234(7) 0.0012(6) 0.0022(5) -0.0028(6) C18 0.0265(7) 0.0205(7) 0.0228(7) -0.0006(5) 0.0031(6) -0.0006(6) C19 0.0238(7) 0.0227(7) 0.0288(7) 0.0012(6) 0.0081(6) 0.0032(6) C20 0.0227(7) 0.0263(7) 0.0251(7) -0.0016(6) 0.0049(6) -0.0010(6) C21 0.0227(7) 0.0260(7) 0.0272(7) 0.0004(6) 0.0048(6) 0.0025(6) C22 0.0251(7) 0.0312(8) 0.0331(8) -0.0058(7) 0.0089(6) -0.0022(6) C23 0.0234(7) 0.0324(8) 0.0301(8) 0.0025(6) 0.0060(6) 0.0050(6) C24 0.0292(8) 0.0400(10) 0.0411(9) 0.0002(7) 0.0145(7) 0.0003(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S1 2.1665(3) 3_666 ? Ni1 S1 2.1665(3) . ? Ni1 S2 2.1831(3) 3_666 ? Ni1 S2 2.1831(3) . ? S1 C1 1.7455(14) . ? S2 C5 1.7483(14) . ? N1 C1 1.3145(18) . ? N1 C2 1.3757(19) . ? N2 C5 1.3167(18) . ? N2 C6 1.3753(19) . ? N3 C10 1.337(2) . ? N3 C11 1.338(2) . ? N4 C16 1.3453(18) . ? N4 C17 1.3489(19) . ? N4 C19 1.4953(17) . ? C1 C5 1.447(2) 3_666 ? C2 C3 1.413(2) . ? C2 C6 1.411(2) 3_666 ? C3 H3 0.9500 . ? C3 C4 1.372(2) . ? C4 H4 0.9500 . ? C4 C8 1.403(3) 3_666 ? C5 C1 1.447(2) 3_666 ? C6 C2 1.411(2) 3_666 ? C6 C7 1.412(2) . ? C7 H7 0.9500 . ? C7 C8 1.370(2) . ? C8 C4 1.403(3) 3_666 ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C9 C10 1.382(2) . ? C9 C13 1.392(2) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C11 C12 1.387(2) . ? C12 H12 0.9500 . ? C12 C13 1.393(2) . ? C13 C14 1.478(2) . ? C14 C15 1.398(2) . ? C14 C18 1.398(2) . ? C15 H15 0.9500 . ? C15 C16 1.372(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C17 C18 1.373(2) . ? C18 H18 0.9500 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 C20 1.509(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 C21 1.525(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.517(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 C23 1.518(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 C24 1.521(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Ni1 S1 180.000(15) . 3_666 ? S1 Ni1 S2 91.613(13) . 3_666 ? S1 Ni1 S2 88.387(13) 3_666 3_666 ? S1 Ni1 S2 91.613(13) 3_666 . ? S1 Ni1 S2 88.387(13) . . ? S2 Ni1 S2 180.000(12) . 3_666 ? C1 S1 Ni1 105.58(5) . . ? C5 S2 Ni1 105.21(5) . . ? C1 N1 C2 116.51(13) . . ? C5 N2 C6 116.53(12) . . ? C10 N3 C11 116.09(14) . . ? C16 N4 C17 119.73(12) . . ? C16 N4 C19 117.25(12) . . ? C17 N4 C19 123.01(12) . . ? N1 C1 S1 119.08(11) . . ? N1 C1 C5 122.18(12) . 3_666 ? C5 C1 S1 118.73(10) 3_666 . ? N1 C2 C3 119.16(14) . . ? N1 C2 C6 121.36(13) . 3_666 ? C6 C2 C3 119.47(13) 3_666 . ? C2 C3 H3 119.9 . . ? C4 C3 C2 120.12(16) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 119.7 . . ? C3 C4 C8 120.57(14) . 3_666 ? C8 C4 H4 119.7 3_666 . ? N2 C5 S2 119.58(11) . . ? N2 C5 C1 121.97(12) . 3_666 ? C1 C5 S2 118.44(10) 3_666 . ? N2 C6 C2 121.43(13) . 3_666 ? N2 C6 C7 119.64(14) . . ? C2 C6 C7 118.93(13) 3_666 . ? C6 C7 H7 119.6 . . ? C8 C7 C6 120.72(15) . . ? C8 C7 H7 119.6 . . ? C4 C8 H8 119.9 3_666 . ? C7 C8 C4 120.18(14) . 3_666 ? C7 C8 H8 119.9 . . ? C10 C9 H9 120.6 . . ? C10 C9 C13 118.81(16) . . ? C13 C9 H9 120.6 . . ? N3 C10 C9 124.62(16) . . ? N3 C10 H10 117.7 . . ? C9 C10 H10 117.7 . . ? N3 C11 H11 118.1 . . ? N3 C11 C12 123.87(16) . . ? C12 C11 H11 118.1 . . ? C11 C12 H12 120.4 . . ? C11 C12 C13 119.18(15) . . ? C13 C12 H12 120.4 . . ? C9 C13 C12 117.42(14) . . ? C9 C13 C14 120.97(14) . . ? C12 C13 C14 121.62(14) . . ? C15 C14 C13 120.81(13) . . ? C15 C14 C18 116.84(13) . . ? C18 C14 C13 122.35(13) . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.30(13) . . ? C16 C15 H15 119.8 . . ? N4 C16 C15 121.50(13) . . ? N4 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? N4 C17 H17 119.5 . . ? N4 C17 C18 120.94(13) . . ? C18 C17 H17 119.5 . . ? C14 C18 H18 119.7 . . ? C17 C18 C14 120.68(14) . . ? C17 C18 H18 119.7 . . ? N4 C19 H19A 108.4 . . ? N4 C19 H19B 108.4 . . ? N4 C19 C20 115.52(12) . . ? H19A C19 H19B 107.5 . . ? C20 C19 H19A 108.4 . . ? C20 C19 H19B 108.4 . . ? C19 C20 H20A 109.8 . . ? C19 C20 H20B 109.8 . . ? C19 C20 C21 109.27(12) . . ? H20A C20 H20B 108.3 . . ? C21 C20 H20A 109.8 . . ? C21 C20 H20B 109.8 . . ? C20 C21 H21A 109.1 . . ? C20 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? C22 C21 C20 112.59(13) . . ? C22 C21 H21A 109.1 . . ? C22 C21 H21B 109.1 . . ? C21 C22 H22A 108.7 . . ? C21 C22 H22B 108.7 . . ? C21 C22 C23 114.36(13) . . ? H22A C22 H22B 107.6 . . ? C23 C22 H22A 108.7 . . ? C23 C22 H22B 108.7 . . ? C22 C23 H23A 109.1 . . ? C22 C23 H23B 109.1 . . ? C22 C23 C24 112.30(13) . . ? H23A C23 H23B 107.9 . . ? C24 C23 H23A 109.1 . . ? C24 C23 H23B 109.1 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _database_code_depnum_ccdc_archive 'CCDC 895905' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_022312a_boyang #TrackingRef '- C7-1.cif' _audit_creation_date 2012-02-24 _audit_creation_method ; Olex2 1.1 (compiled 2011.08.18 svn.r1932, GUI svn.r3819) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H8 N4 Ni S4, 2(C17 H23 N2), 2(H2 O)' _chemical_formula_sum 'C50 H58 N8 Ni O2 S4' _chemical_formula_weight 989.99 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 15.2630(3) _cell_length_b 9.2809(2) _cell_length_c 16.8903(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.097(2) _cell_angle_gamma 90.00 _cell_volume 2389.09(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5989 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 71.5654 _cell_measurement_theta_min 4.0097 _exptl_absorpt_coefficient_mu 2.609 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.64730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1044 _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_unetI/netI 0.0168 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 9078 _diffrn_reflns_theta_full 66.99 _diffrn_reflns_theta_max 66.99 _diffrn_reflns_theta_min 5.25 _diffrn_ambient_temperature 133(2) _diffrn_detector_area_resol_mean 16.1270 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'CU K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4057 _reflns_number_total 4246 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.464 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.055 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 302 _refine_ls_number_reflns 4246 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0307 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+1.0486P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0849 _refine_ls_wR_factor_ref 0.0859 _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.0000 0.0000 1.0000 0.01427(11) Uani 1 2 d S . . S2 S -0.13839(2) 0.01014(4) 1.02405(2) 0.01591(11) Uani 1 1 d . . . S1 S 0.00435(2) 0.23265(4) 1.01017(2) 0.02004(11) Uani 1 1 d . . . N1 N 0.24199(8) 0.19650(14) 0.92573(7) 0.0181(3) Uani 1 1 d . . . C14 C 0.92250(10) 0.45555(17) 0.86320(9) 0.0206(3) Uani 1 1 d . . . H14 H 0.9653 0.4742 0.9049 0.025 Uiso 1 1 calc R . . N4 N 0.94051(9) 0.48456(14) 0.78785(8) 0.0204(3) Uani 1 1 d . . . C10 C 0.68186(10) 0.22740(17) 0.90626(9) 0.0217(3) Uani 1 1 d . . . H10 H 0.7293 0.2175 0.9446 0.026 Uiso 1 1 calc R . . C22 C 1.21936(10) 0.30362(18) 0.68448(9) 0.0245(3) Uani 1 1 d . . . H22A H 1.2326 0.2427 0.7317 0.029 Uiso 1 1 calc R . . H22B H 1.1809 0.2474 0.6469 0.029 Uiso 1 1 calc R . . N3 N 0.53217(9) 0.17182(16) 0.86737(8) 0.0261(3) Uani 1 1 d . . . C2 C 0.10405(9) 0.28081(16) 0.97201(8) 0.0154(3) Uani 1 1 d . . . C12 C 0.61985(10) 0.31648(18) 0.78330(9) 0.0234(3) Uani 1 1 d . . . H12 H 0.6233 0.3699 0.7356 0.028 Uiso 1 1 calc R . . C5 C 0.30494(11) 0.62837(17) 0.88951(9) 0.0232(3) Uani 1 1 d . . . H5 H 0.3211 0.7264 0.8831 0.028 Uiso 1 1 calc R . . N2 N 0.12054(8) 0.41744(14) 0.95845(7) 0.0175(3) Uani 1 1 d . . . C11 C 0.69270(10) 0.30531(16) 0.83704(9) 0.0190(3) Uani 1 1 d . . . C4 C 0.22383(10) 0.59439(17) 0.91642(9) 0.0203(3) Uani 1 1 d . . . H4 H 0.1833 0.6690 0.9266 0.024 Uiso 1 1 calc R . . C9 C 0.60159(10) 0.16444(18) 0.91902(10) 0.0246(3) Uani 1 1 d . . . H9 H 0.5955 0.1132 0.9671 0.029 Uiso 1 1 calc R . . C16 C 0.77796(10) 0.37167(16) 0.81999(9) 0.0190(3) Uani 1 1 d . . . C15 C 0.84249(10) 0.39904(17) 0.88011(9) 0.0211(3) Uani 1 1 d . . . H15 H 0.8307 0.3782 0.9336 0.025 Uiso 1 1 calc R . . C8 C 0.26104(9) 0.33928(16) 0.91238(8) 0.0177(3) Uani 1 1 d . . . C25 C 1.43435(11) 0.2399(2) 0.57410(11) 0.0327(4) Uani 1 1 d . . . H25A H 1.4177 0.2995 0.5278 0.049 Uiso 1 1 calc R . . H25B H 1.4616 0.1506 0.5566 0.049 Uiso 1 1 calc R . . H25C H 1.4761 0.2928 0.6093 0.049 Uiso 1 1 calc R . . C3 C 0.20075(9) 0.44929(16) 0.92887(8) 0.0167(3) Uani 1 1 d . . . C7 C 0.34212(10) 0.37630(17) 0.88210(10) 0.0240(3) Uani 1 1 d . . . H7 H 0.3821 0.3027 0.8689 0.029 Uiso 1 1 calc R . . C17 C 0.79857(11) 0.40786(19) 0.74275(9) 0.0248(3) Uani 1 1 d . . . H17 H 0.7561 0.3947 0.7001 0.030 Uiso 1 1 calc R . . C19 C 1.03021(10) 0.52874(18) 0.76755(10) 0.0230(3) Uani 1 1 d . . . H19A H 1.0610 0.5741 0.8143 0.028 Uiso 1 1 calc R . . H19B H 1.0263 0.6004 0.7241 0.028 Uiso 1 1 calc R . . C18 C 0.87927(11) 0.4620(2) 0.72831(9) 0.0261(3) Uani 1 1 d . . . H18 H 0.8927 0.4842 0.6754 0.031 Uiso 1 1 calc R . . C21 C 1.16996(10) 0.43742(17) 0.70956(9) 0.0226(3) Uani 1 1 d . . . H21A H 1.1603 0.5024 0.6634 0.027 Uiso 1 1 calc R . . H21B H 1.2058 0.4897 0.7508 0.027 Uiso 1 1 calc R . . C20 C 1.08161(10) 0.39783(17) 0.74188(9) 0.0229(3) Uani 1 1 d . . . H20A H 1.0462 0.3451 0.7005 0.027 Uiso 1 1 calc R . . H20B H 1.0916 0.3325 0.7878 0.027 Uiso 1 1 calc R . . C13 C 0.54293(10) 0.2482(2) 0.80105(10) 0.0274(4) Uani 1 1 d . . . H13 H 0.4943 0.2558 0.7638 0.033 Uiso 1 1 calc R . . C23 C 1.30475(10) 0.33740(18) 0.64562(9) 0.0230(3) Uani 1 1 d . . . H23A H 1.3439 0.3912 0.6838 0.028 Uiso 1 1 calc R . . H23B H 1.2918 0.4006 0.5992 0.028 Uiso 1 1 calc R . . C6 C 0.36374(11) 0.51828(18) 0.87152(10) 0.0257(4) Uani 1 1 d . . . H6 H 0.4190 0.5423 0.8518 0.031 Uiso 1 1 calc R . . C24 C 1.35270(11) 0.20363(18) 0.61856(10) 0.0264(3) Uani 1 1 d . . . H24A H 1.3122 0.1458 0.5836 0.032 Uiso 1 1 calc R . . H24B H 1.3700 0.1441 0.6655 0.032 Uiso 1 1 calc R . . O1 O 0.37610(8) -0.01107(12) 0.88970(7) 0.0256(3) Uani 1 1 d D . . H1A H 0.4216(11) 0.034(2) 0.8848(12) 0.031 Uiso 1 1 d D . . H1B H 0.3381(12) 0.043(2) 0.9041(12) 0.031 Uiso 1 1 d D . . C1 C 0.16617(9) 0.16744(16) 0.95570(8) 0.0154(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.01377(19) 0.0134(2) 0.01563(19) 0.00069(12) 0.00063(13) -0.00039(12) S2 0.01471(19) 0.01355(19) 0.01952(19) 0.00133(12) 0.00143(14) 0.00038(12) S1 0.01663(19) 0.0145(2) 0.0295(2) -0.00005(14) 0.00654(14) 0.00021(12) N1 0.0162(6) 0.0172(6) 0.0208(6) 0.0011(5) 0.0007(5) 0.0004(5) C14 0.0209(7) 0.0224(8) 0.0180(7) -0.0032(6) -0.0039(6) 0.0010(6) N4 0.0185(7) 0.0212(7) 0.0212(6) -0.0009(5) -0.0009(5) -0.0012(5) C10 0.0211(8) 0.0216(8) 0.0220(7) -0.0003(6) -0.0031(6) 0.0017(6) C22 0.0241(8) 0.0254(8) 0.0243(8) -0.0011(6) 0.0027(6) -0.0046(6) N3 0.0193(6) 0.0295(8) 0.0296(7) -0.0019(6) 0.0028(5) -0.0003(5) C2 0.0155(7) 0.0167(7) 0.0138(6) -0.0009(5) -0.0004(5) -0.0014(5) C12 0.0193(7) 0.0314(9) 0.0193(7) -0.0004(6) -0.0007(6) 0.0016(6) C5 0.0270(8) 0.0191(8) 0.0232(7) 0.0020(6) -0.0015(6) -0.0071(6) N2 0.0190(6) 0.0157(6) 0.0176(6) -0.0006(5) -0.0003(5) -0.0008(5) C11 0.0190(7) 0.0182(7) 0.0198(7) -0.0045(6) 0.0002(6) 0.0018(6) C4 0.0251(8) 0.0166(7) 0.0190(7) -0.0009(6) -0.0015(6) -0.0010(6) C9 0.0245(8) 0.0232(8) 0.0262(8) 0.0027(6) 0.0024(6) 0.0016(6) C16 0.0189(7) 0.0177(7) 0.0202(7) -0.0024(6) -0.0005(6) 0.0027(6) C15 0.0227(7) 0.0246(8) 0.0156(7) -0.0016(6) -0.0010(6) 0.0005(6) C8 0.0183(7) 0.0169(7) 0.0177(7) 0.0015(6) -0.0019(5) -0.0016(6) C25 0.0261(9) 0.0404(10) 0.0318(9) 0.0010(8) 0.0028(7) 0.0054(7) C3 0.0183(7) 0.0178(7) 0.0138(6) -0.0007(5) -0.0020(5) -0.0017(6) C7 0.0189(7) 0.0225(8) 0.0308(8) 0.0026(6) 0.0024(6) 0.0003(6) C17 0.0231(8) 0.0323(8) 0.0184(7) -0.0004(6) -0.0051(6) -0.0037(7) C19 0.0187(8) 0.0247(8) 0.0254(8) 0.0006(6) 0.0005(6) -0.0041(6) C18 0.0258(8) 0.0349(9) 0.0172(7) 0.0016(7) -0.0019(6) -0.0050(7) C21 0.0224(8) 0.0246(8) 0.0209(7) 0.0000(6) 0.0009(6) -0.0036(6) C20 0.0230(8) 0.0236(8) 0.0220(7) -0.0018(6) 0.0011(6) -0.0041(6) C13 0.0185(8) 0.0389(10) 0.0245(8) -0.0024(7) -0.0020(6) 0.0012(7) C23 0.0209(7) 0.0248(8) 0.0234(7) 0.0014(6) 0.0006(6) -0.0025(6) C6 0.0203(8) 0.0273(8) 0.0297(8) 0.0045(7) 0.0028(6) -0.0062(6) C24 0.0257(8) 0.0269(8) 0.0264(8) 0.0012(7) 0.0000(6) 0.0010(7) O1 0.0206(6) 0.0202(6) 0.0362(7) -0.0051(5) 0.0045(5) -0.0005(4) C1 0.0157(7) 0.0161(7) 0.0140(6) -0.0005(5) -0.0024(5) -0.0011(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni1 S2 2.1744(3) . ? Ni1 S2 2.1744(3) 3_557 ? Ni1 S1 2.1667(4) 3_557 ? Ni1 S1 2.1667(4) . ? S2 C1 1.7403(15) 3_557 ? S1 C2 1.7426(14) . ? N1 C8 1.378(2) . ? N1 C1 1.3158(19) . ? C14 H14 0.9500 . ? C14 N4 1.344(2) . ? C14 C15 1.373(2) . ? N4 C19 1.487(2) . ? N4 C18 1.352(2) . ? C10 H10 0.9500 . ? C10 C11 1.392(2) . ? C10 C9 1.385(2) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 C21 1.525(2) . ? C22 C23 1.523(2) . ? N3 C9 1.337(2) . ? N3 C13 1.343(2) . ? C2 N2 1.315(2) . ? C2 C1 1.453(2) . ? C12 H12 0.9500 . ? C12 C11 1.401(2) . ? C12 C13 1.381(2) . ? C5 H5 0.9500 . ? C5 C4 1.378(2) . ? C5 C6 1.404(2) . ? N2 C3 1.3791(19) . ? C11 C16 1.482(2) . ? C4 H4 0.9500 . ? C4 C3 1.411(2) . ? C9 H9 0.9500 . ? C16 C15 1.399(2) . ? C16 C17 1.399(2) . ? C15 H15 0.9500 . ? C8 C3 1.412(2) . ? C8 C7 1.407(2) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C25 C24 1.527(2) . ? C7 H7 0.9500 . ? C7 C6 1.372(2) . ? C17 H17 0.9500 . ? C17 C18 1.364(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 C20 1.522(2) . ? C18 H18 0.9500 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C20 1.527(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C13 H13 0.9500 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 C24 1.524(2) . ? C6 H6 0.9500 . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? O1 H1A 0.819(15) . ? O1 H1B 0.813(15) . ? C1 S2 1.7403(15) 3_557 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S2 Ni1 S2 180.0 3_557 . ? S1 Ni1 S2 88.167(12) . . ? S1 Ni1 S2 91.833(12) 3_557 . ? S1 Ni1 S2 91.833(12) . 3_557 ? S1 Ni1 S2 88.167(12) 3_557 3_557 ? S1 Ni1 S1 180.0 . 3_557 ? C1 S2 Ni1 104.19(5) 3_557 . ? C2 S1 Ni1 104.47(5) . . ? C1 N1 C8 117.25(13) . . ? N4 C14 H14 119.9 . . ? N4 C14 C15 120.22(14) . . ? C15 C14 H14 119.9 . . ? C14 N4 C19 120.78(13) . . ? C14 N4 C18 120.32(14) . . ? C18 N4 C19 118.66(13) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C9 C10 C11 119.76(14) . . ? H22A C22 H22B 107.7 . . ? C21 C22 H22A 108.9 . . ? C21 C22 H22B 108.9 . . ? C23 C22 H22A 108.9 . . ? C23 C22 H22B 108.9 . . ? C23 C22 C21 113.55(13) . . ? C9 N3 C13 116.28(14) . . ? N2 C2 S1 119.39(11) . . ? N2 C2 C1 122.16(13) . . ? C1 C2 S1 118.44(11) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C13 C12 C11 118.67(15) . . ? C4 C5 H5 120.0 . . ? C4 C5 C6 120.06(15) . . ? C6 C5 H5 120.0 . . ? C2 N2 C3 116.85(13) . . ? C10 C11 C12 117.15(14) . . ? C10 C11 C16 121.64(13) . . ? C12 C11 C16 121.19(14) . . ? C5 C4 H4 119.9 . . ? C5 C4 C3 120.24(14) . . ? C3 C4 H4 119.9 . . ? C10 C9 H9 118.2 . . ? N3 C9 C10 123.59(15) . . ? N3 C9 H9 118.2 . . ? C15 C16 C11 121.70(13) . . ? C15 C16 C17 116.63(14) . . ? C17 C16 C11 121.66(13) . . ? C14 C15 C16 121.16(14) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? N1 C8 C3 121.16(13) . . ? N1 C8 C7 119.47(14) . . ? C7 C8 C3 119.37(14) . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? N2 C3 C4 119.50(14) . . ? N2 C3 C8 121.14(13) . . ? C4 C3 C8 119.35(14) . . ? C8 C7 H7 119.9 . . ? C6 C7 C8 120.27(15) . . ? C6 C7 H7 119.9 . . ? C16 C17 H17 119.8 . . ? C18 C17 C16 120.37(14) . . ? C18 C17 H17 119.8 . . ? N4 C19 H19A 109.7 . . ? N4 C19 H19B 109.7 . . ? N4 C19 C20 109.93(13) . . ? H19A C19 H19B 108.2 . . ? C20 C19 H19A 109.7 . . ? C20 C19 H19B 109.7 . . ? N4 C18 C17 121.26(15) . . ? N4 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C22 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? C22 C21 C20 111.28(13) . . ? H21A C21 H21B 108.0 . . ? C20 C21 H21A 109.4 . . ? C20 C21 H21B 109.4 . . ? C19 C20 C21 112.87(13) . . ? C19 C20 H20A 109.0 . . ? C19 C20 H20B 109.0 . . ? C21 C20 H20A 109.0 . . ? C21 C20 H20B 109.0 . . ? H20A C20 H20B 107.8 . . ? N3 C13 C12 124.52(15) . . ? N3 C13 H13 117.7 . . ? C12 C13 H13 117.7 . . ? C22 C23 H23A 108.9 . . ? C22 C23 H23B 108.9 . . ? C22 C23 C24 113.43(14) . . ? H23A C23 H23B 107.7 . . ? C24 C23 H23A 108.9 . . ? C24 C23 H23B 108.9 . . ? C5 C6 H6 119.7 . . ? C7 C6 C5 120.64(15) . . ? C7 C6 H6 119.7 . . ? C25 C24 H24A 109.1 . . ? C25 C24 H24B 109.1 . . ? C23 C24 C25 112.70(14) . . ? C23 C24 H24A 109.1 . . ? C23 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? H1A O1 H1B 110(2) . . ? N1 C1 S2 119.89(11) . 3_557 ? N1 C1 C2 121.40(13) . . ? C2 C1 S2 118.70(11) . 3_557 ? _database_code_depnum_ccdc_archive 'CCDC 895906'