Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Th. Kaden' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Jan M. Baumeister' ; ? # Address 2 ; ; ? # Footnote 2 ; 'C. Niamh McMahon' '' '' 'Markus Neuburger' '' '' 'Liselotte Siegfried' '' '' _publ_contact_author_name 'Thomas Kaden' _publ_contact_author_address ; Institut fur Anorganische Chemie University Spitalstrasse 51 Basel CH-4056 SWITZERLAND ; _publ_contact_author_email TH.KADEN@UNIBAS.CH _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Homo- and heteropolynuclear Ni2+ and Cu2+ complexes of polytopic ligands, consisting of a tren unit substituted with three 12-memebered tetraazamacrocycles ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' data_CuMac12_173k _database_code_depnum_ccdc_archive 'CCDC 654220' _audit_creation_date 06-09-08 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '3121704 siegfried_cu_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.5959(10) _cell_length_b 12.1317(10) _cell_length_c 14.2676(10) _cell_angle_alpha 90 _cell_angle_beta 104.341(9) _cell_angle_gamma 90 _cell_volume 2280.0(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126 1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C11 H30 Cl3 Cu1 N5 O13 # Dc = 1.78 Fooo = 1260.00 Mu = 13.82 M = 610.29 # Found Formula = C11 H30 Cl3 Cu1 N5 O13 # Dc = 1.78 FOOO = 1260.00 Mu = 13.82 M = 610.29 _chemical_formula_sum 'C11 H30 Cl3 Cu1 N5 O13' _chemical_formula_moiety 'C11 H30 Cu N5 O, 3(Cl O4)' _chemical_compound_source ? _chemical_formula_weight 610.29 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1260 _exptl_absorpt_coefficient_mu 1.382 # Sheldrick geometric approximatio 0.76 0.87 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.87 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 47840 _reflns_number_total 5774 _diffrn_reflns_av_R_equivalents 0.099 # Number of reflections with Friedels Law is 5774 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5780 _diffrn_reflns_theta_min 1.853 _diffrn_reflns_theta_max 28.505 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.505 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -18 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.48 _refine_diff_density_max 0.65 _refine_ls_number_reflns 3292 _refine_ls_number_restraints 7 _refine_ls_number_parameters 298 #_refine_ls_R_factor_ref 0.0332 _refine_ls_wR_factor_ref 0.0355 _refine_ls_goodness_of_fit_ref 1.0995 #_reflns_number_all 5741 _refine_ls_R_factor_all 0.0724 _refine_ls_wR_factor_all 0.0575 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 3292 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_gt 0.0355 _refine_ls_shift/su_max 0.000260 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 8.66 -4.25 6.33 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Cu1 Cu 0.00051(2) 0.25887(3) 0.29794(2) 0.0212 1.0000 Uani . . . . . . N1 N -0.03463(17) 0.4014(2) 0.21942(16) 0.0218 1.0000 Uani . . . . . . C1 C -0.0337(2) 0.3742(3) 0.1178(2) 0.0289 1.0000 Uani . . . . . . C2 C -0.0515(2) 0.2517(3) 0.09981(19) 0.0306 1.0000 Uani . . . . . . N2 N 0.02206(18) 0.1918(2) 0.17636(18) 0.0268 1.0000 Uani D U . . . . C3 C 0.0027(3) 0.0717(3) 0.1785(2) 0.0332 1.0000 Uani . . . . . . C4 C -0.0707(2) 0.0503(3) 0.2404(2) 0.0323 1.0000 Uani . . . . . . N3 N -0.02948(18) 0.1055(2) 0.33540(18) 0.0277 1.0000 Uani D U . . . . C5 C -0.1024(2) 0.1129(3) 0.3972(2) 0.0301 1.0000 Uani . . . . . . C6 C -0.1645(2) 0.2166(3) 0.3721(2) 0.0284 1.0000 Uani . . . . . . N4 N -0.09328(18) 0.3105(2) 0.37704(17) 0.0240 1.0000 Uani D U . . . . C7 C -0.1429(2) 0.4144(3) 0.3351(2) 0.0289 1.0000 Uani . . . . . . C8 C -0.1396(2) 0.4227(2) 0.2296(2) 0.0267 1.0000 Uani . . . . . . C9 C 0.0370(2) 0.4916(2) 0.2587(2) 0.0259 1.0000 Uani . . . . . . C10 C 0.0201(2) 0.5955(3) 0.1975(2) 0.0303 1.0000 Uani . . . . . . N5 N 0.08543(19) 0.6855(2) 0.24948(18) 0.0295 1.0000 Uani D U . . . . C11 C 0.0881(3) 0.7818(3) 0.1861(3) 0.0414 1.0000 Uani . . . . . . O1 O 0.15710(16) 0.2816(2) 0.37882(18) 0.0397 1.0000 Uani D U . . . . Cl11 Cl 0.25026(6) -0.04207(8) 0.40851(6) 0.0373 1.0000 Uani . . . . . . O11 O 0.3037(2) -0.0736(3) 0.5031(2) 0.0554 1.0000 Uani . . . . . . O12 O 0.14339(18) -0.0583(3) 0.39478(19) 0.0520 1.0000 Uani . . . . . . O13 O 0.2834(2) -0.1076(3) 0.3391(2) 0.0677 1.0000 Uani . . . . . . O14 O 0.2712(3) 0.0716(3) 0.3921(3) 0.0792 1.0000 Uani . . . . . . Cl21 Cl 0.11325(5) 0.25263(6) 0.62225(5) 0.0278 1.0000 Uani . . . . . . O21 O 0.11621(19) 0.2165(2) 0.71883(19) 0.0472 1.0000 Uani . . . . . . O22 O 0.1150(2) 0.1600(2) 0.5616(2) 0.0542 1.0000 Uani . . . . . . O23 O 0.02051(16) 0.3146(2) 0.58694(16) 0.0382 1.0000 Uani . . . . . . O24 O 0.19852(18) 0.3215(2) 0.6243(2) 0.0474 1.0000 Uani . . . . . . Cl31 Cl 0.28320(5) 0.56830(6) 0.44727(6) 0.0313 1.0000 Uani . . . . . . O31 O 0.1857(2) 0.5891(3) 0.4630(2) 0.0678 1.0000 Uani . . . . . . O32 O 0.28040(19) 0.6056(3) 0.3507(2) 0.0573 1.0000 Uani . . . . . . O33 O 0.3607(2) 0.6241(3) 0.5148(3) 0.0716 1.0000 Uani . . . . . . O34 O 0.3038(2) 0.4534(2) 0.4527(3) 0.0650 1.0000 Uani . . . . . . H1 H 0.0884 0.2009 0.1667 0.0379 1.0000 Uiso DR U . . . . H2 H 0.0293 0.0663 0.3691 0.0256 1.0000 Uiso DR U . . . . H3 H -0.0566 0.3244 0.4422 0.0251 1.0000 Uiso DR U . . . . H4 H 0.1537 0.6664 0.2806 0.0354 1.0000 Uiso DR U . . . . H5 H 0.0681 0.7089 0.3073 0.0360 1.0000 Uiso DR U . . . . H6 H 0.1817 0.2162 0.4133 0.0537 1.0000 Uiso DR U . . . . H7 H 0.1821 0.3440 0.4174 0.0511 1.0000 Uiso DR U . . . . H11 H 0.0310 0.3938 0.1069 0.0345 1.0000 Uiso R . . . . . H12 H -0.0863 0.4148 0.0742 0.0345 1.0000 Uiso R . . . . . H21 H -0.0416 0.2326 0.0375 0.0361 1.0000 Uiso R . . . . . H22 H -0.1195 0.2331 0.1022 0.0361 1.0000 Uiso R . . . . . H31 H 0.0654 0.0338 0.2053 0.0402 1.0000 Uiso R . . . . . H32 H -0.0259 0.0457 0.1140 0.0402 1.0000 Uiso R . . . . . H41 H -0.0768 -0.0275 0.2497 0.0382 1.0000 Uiso R . . . . . H42 H -0.1362 0.0802 0.2097 0.0382 1.0000 Uiso R . . . . . H51 H -0.0659 0.1150 0.4640 0.0363 1.0000 Uiso R . . . . . H52 H -0.1465 0.0499 0.3861 0.0363 1.0000 Uiso R . . . . . H61 H -0.2053 0.2276 0.4174 0.0349 1.0000 Uiso R . . . . . H62 H -0.2077 0.2107 0.3080 0.0349 1.0000 Uiso R . . . . . H71 H -0.1077 0.4760 0.3703 0.0362 1.0000 Uiso R . . . . . H72 H -0.2122 0.4147 0.3394 0.0362 1.0000 Uiso R . . . . . H81 H -0.1603 0.4954 0.2061 0.0323 1.0000 Uiso R . . . . . H82 H -0.1851 0.3693 0.1924 0.0323 1.0000 Uiso R . . . . . H91 H 0.1048 0.4658 0.2632 0.0307 1.0000 Uiso R . . . . . H92 H 0.0297 0.5097 0.3222 0.0307 1.0000 Uiso R . . . . . H101 H 0.0370 0.5815 0.1371 0.0354 1.0000 Uiso R . . . . . H102 H -0.0499 0.6172 0.1854 0.0354 1.0000 Uiso R . . . . . H111 H 0.1310 0.8379 0.2223 0.0487 1.0000 Uiso R . . . . . H112 H 0.1144 0.7594 0.1325 0.0487 1.0000 Uiso R . . . . . H113 H 0.0206 0.8104 0.1624 0.0487 1.0000 Uiso 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 Cu1 0.01810(15) 0.02433(18) 0.02074(15) -0.00018(15) 0.00386(11) 0.00063(14) N1 0.0187(10) 0.0254(12) 0.0210(11) 0.0017(9) 0.0043(9) 0.0005(9) C1 0.0283(14) 0.0375(17) 0.0205(14) 0.0018(12) 0.0054(11) -0.0001(12) C2 0.0298(14) 0.0407(17) 0.0197(13) -0.0034(14) 0.0029(10) -0.0002(14) N2 0.0236(11) 0.0305(13) 0.0267(12) -0.0015(11) 0.0069(10) 0.0031(10) C3 0.0378(17) 0.0285(16) 0.0342(16) -0.0093(13) 0.0103(14) 0.0033(13) C4 0.0325(15) 0.0257(15) 0.0373(17) -0.0058(13) 0.0057(13) -0.0069(13) N3 0.0243(12) 0.0244(12) 0.0328(13) 0.0019(11) 0.0041(10) 0.0019(10) C5 0.0295(15) 0.0302(15) 0.0312(16) 0.0049(13) 0.0086(12) -0.0039(13) C6 0.0229(14) 0.0336(16) 0.0308(15) 0.0018(12) 0.0106(11) -0.0045(12) N4 0.0246(12) 0.0258(12) 0.0223(12) 0.0007(10) 0.0069(9) -0.0007(10) C7 0.0273(14) 0.0274(16) 0.0358(16) 0.0001(12) 0.0148(12) 0.0032(12) C8 0.0184(13) 0.0288(15) 0.0335(16) 0.0058(12) 0.0075(11) 0.0017(11) C9 0.0242(13) 0.0291(15) 0.0236(14) 0.0006(12) 0.0040(11) -0.0038(11) C10 0.0286(15) 0.0296(15) 0.0304(16) 0.0036(13) 0.0028(12) -0.0044(12) N5 0.0264(13) 0.0334(14) 0.0271(13) 0.0020(11) 0.0035(10) -0.0049(10) C11 0.049(2) 0.0339(18) 0.0391(19) 0.0053(15) 0.0064(15) -0.0066(15) O1 0.0255(11) 0.0393(13) 0.0460(14) 0.0090(11) -0.0070(10) -0.0046(9) Cl11 0.0300(4) 0.0488(5) 0.0334(4) 0.0044(4) 0.0086(3) 0.0027(3) O11 0.0478(15) 0.0622(18) 0.0454(15) 0.0120(14) -0.0090(12) -0.0111(14) O12 0.0291(12) 0.083(2) 0.0449(14) 0.0033(14) 0.0113(11) 0.0070(13) O13 0.0433(16) 0.099(3) 0.067(2) -0.0233(19) 0.0248(14) -0.0006(16) O14 0.087(2) 0.056(2) 0.092(3) 0.0273(19) 0.018(2) -0.0035(18) Cl21 0.0214(3) 0.0287(3) 0.0309(3) 0.0021(3) 0.0021(2) 0.0022(3) O21 0.0413(13) 0.0587(17) 0.0397(13) 0.0170(12) 0.0064(11) -0.0008(12) O22 0.0545(16) 0.0431(15) 0.0593(17) -0.0143(13) 0.0033(13) 0.0147(13) O23 0.0254(11) 0.0504(15) 0.0340(12) -0.0031(11) -0.0015(9) 0.0140(10) O24 0.0311(12) 0.0464(15) 0.0638(17) 0.0124(13) 0.0103(12) -0.0066(11) Cl31 0.0237(3) 0.0355(4) 0.0325(4) -0.0030(3) 0.0028(3) 0.0000(3) O31 0.0370(14) 0.131(3) 0.0384(15) -0.0052(17) 0.0143(12) 0.0203(17) O32 0.0294(12) 0.091(2) 0.0515(16) 0.0272(16) 0.0103(11) -0.0003(14) O33 0.0588(18) 0.0489(18) 0.081(2) -0.0155(16) -0.0329(16) 0.0018(14) O34 0.0604(18) 0.0327(14) 0.090(2) 0.0025(15) -0.0047(16) 0.0002(13) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.026(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 . N1 . 2.052(2) yes Cu1 . N2 . 2.002(3) yes Cu1 . N3 . 2.006(3) yes Cu1 . N4 . 2.001(2) yes Cu1 . O1 . 2.173(2) yes N1 . C1 . 1.491(4) yes N1 . C8 . 1.493(3) yes N1 . C9 . 1.479(4) yes C1 . C2 . 1.516(5) yes C1 . H11 . 0.960 no C1 . H12 . 0.960 no C2 . N2 . 1.477(4) yes C2 . H21 . 0.960 no C2 . H22 . 0.960 no N2 . C3 . 1.483(4) yes N2 . H1 . 0.952 no C3 . C4 . 1.510(5) yes C3 . H31 . 0.960 no C3 . H32 . 0.960 no C4 . N3 . 1.491(4) yes C4 . H41 . 0.960 no C4 . H42 . 0.960 no N3 . C5 . 1.484(4) yes N3 . H2 . 0.952 no C5 . C6 . 1.508(4) yes C5 . H51 . 0.960 no C5 . H52 . 0.960 no C6 . N4 . 1.485(4) yes C6 . H61 . 0.960 no C6 . H62 . 0.960 no N4 . C7 . 1.484(4) yes N4 . H3 . 0.955 no C7 . C8 . 1.519(4) yes C7 . H71 . 0.960 no C7 . H72 . 0.960 no C8 . H81 . 0.960 no C8 . H82 . 0.960 no C9 . C10 . 1.519(4) yes C9 . H91 . 0.960 no C9 . H92 . 0.960 no C10 . N5 . 1.485(4) yes C10 . H101 . 0.960 no C10 . H102 . 0.960 no N5 . C11 . 1.483(4) yes N5 . H4 . 0.954 no N5 . H5 . 0.956 no C11 . H111 . 0.960 no C11 . H112 . 0.960 no C11 . H113 . 0.960 no O1 . H6 . 0.950 no O1 . H7 . 0.948 no Cl11 . O11 . 1.418(3) yes Cl11 . O12 . 1.431(2) yes Cl11 . O13 . 1.427(3) yes Cl11 . O14 . 1.439(3) yes Cl21 . O21 . 1.437(3) yes Cl21 . O22 . 1.422(3) yes Cl21 . O23 . 1.447(2) yes Cl21 . O24 . 1.423(2) yes Cl31 . O31 . 1.421(3) yes Cl31 . O32 . 1.442(3) yes Cl31 . O33 . 1.413(3) yes Cl31 . O34 . 1.421(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 . Cu1 . N2 . 86.19(10) yes N1 . Cu1 . N3 . 153.17(10) yes N2 . Cu1 . N3 . 86.40(11) yes N1 . Cu1 . N4 . 87.10(10) yes N2 . Cu1 . N4 . 150.02(10) yes N3 . Cu1 . N4 . 86.56(10) yes N1 . Cu1 . O1 . 104.36(9) yes N2 . Cu1 . O1 . 100.21(10) yes N3 . Cu1 . O1 . 102.32(9) yes N4 . Cu1 . O1 . 109.76(10) yes Cu1 . N1 . C1 . 106.68(18) yes Cu1 . N1 . C8 . 101.05(17) yes C1 . N1 . C8 . 111.9(2) yes Cu1 . N1 . C9 . 111.94(16) yes C1 . N1 . C9 . 111.7(2) yes C8 . N1 . C9 . 113.0(2) yes N1 . C1 . C2 . 110.0(2) yes N1 . C1 . H11 . 109.3 no C2 . C1 . H11 . 109.3 no N1 . C1 . H12 . 109.3 no C2 . C1 . H12 . 109.3 no H11 . C1 . H12 . 109.5 no C1 . C2 . N2 . 107.8(2) yes C1 . C2 . H21 . 109.9 no N2 . C2 . H21 . 109.9 no C1 . C2 . H22 . 109.9 no N2 . C2 . H22 . 109.9 no H21 . C2 . H22 . 109.5 no C2 . N2 . Cu1 . 102.90(18) yes C2 . N2 . C3 . 114.1(2) yes Cu1 . N2 . C3 . 108.46(19) yes C2 . N2 . H1 . 109.2 no Cu1 . N2 . H1 . 115.2 no C3 . N2 . H1 . 107.2 no N2 . C3 . C4 . 109.1(2) yes N2 . C3 . H31 . 109.6 no C4 . C3 . H31 . 109.6 no N2 . C3 . H32 . 109.6 no C4 . C3 . H32 . 109.6 no H31 . C3 . H32 . 109.5 no C3 . C4 . N3 . 107.5(2) yes C3 . C4 . H41 . 110.0 no N3 . C4 . H41 . 110.0 no C3 . C4 . H42 . 110.0 no N3 . C4 . H42 . 110.0 no H41 . C4 . H42 . 109.5 no C4 . N3 . Cu1 . 103.28(19) yes C4 . N3 . C5 . 114.3(2) yes Cu1 . N3 . C5 . 108.20(18) yes C4 . N3 . H2 . 108.4 no Cu1 . N3 . H2 . 113.4 no C5 . N3 . H2 . 109.3 no N3 . C5 . C6 . 109.0(2) yes N3 . C5 . H51 . 109.6 no C6 . C5 . H51 . 109.6 no N3 . C5 . H52 . 109.6 no C6 . C5 . H52 . 109.6 no H51 . C5 . H52 . 109.5 no C5 . C6 . N4 . 108.0(2) yes C5 . C6 . H61 . 109.8 no N4 . C6 . H61 . 109.8 no C5 . C6 . H62 . 109.8 no N4 . C6 . H62 . 109.8 no H61 . C6 . H62 . 109.5 no C6 . N4 . Cu1 . 103.42(18) yes C6 . N4 . C7 . 114.0(2) yes Cu1 . N4 . C7 . 109.12(18) yes C6 . N4 . H3 . 111.0 no Cu1 . N4 . H3 . 110.6 no C7 . N4 . H3 . 108.6 no N4 . C7 . C8 . 109.6(2) yes N4 . C7 . H71 . 109.5 no C8 . C7 . H71 . 109.5 no N4 . C7 . H72 . 109.5 no C8 . C7 . H72 . 109.5 no H71 . C7 . H72 . 109.5 no C7 . C8 . N1 . 110.4(2) yes C7 . C8 . H81 . 109.2 no N1 . C8 . H81 . 109.2 no C7 . C8 . H82 . 109.2 no N1 . C8 . H82 . 109.2 no H81 . C8 . H82 . 109.5 no N1 . C9 . C10 . 113.8(2) yes N1 . C9 . H91 . 108.4 no C10 . C9 . H91 . 108.4 no N1 . C9 . H92 . 108.4 no C10 . C9 . H92 . 108.4 no H91 . C9 . H92 . 109.5 no C9 . C10 . N5 . 109.7(2) yes C9 . C10 . H101 . 109.4 no N5 . C10 . H101 . 109.4 no C9 . C10 . H102 . 109.4 no N5 . C10 . H102 . 109.4 no H101 . C10 . H102 . 109.5 no C10 . N5 . C11 . 112.1(2) yes C10 . N5 . H4 . 116.5 no C11 . N5 . H4 . 107.9 no C10 . N5 . H5 . 113.9 no C11 . N5 . H5 . 110.0 no H4 . N5 . H5 . 95.2 no N5 . C11 . H111 . 109.5 no N5 . C11 . H112 . 109.5 no H111 . C11 . H112 . 109.5 no N5 . C11 . H113 . 109.5 no H111 . C11 . H113 . 109.5 no H112 . C11 . H113 . 109.5 no Cu1 . O1 . H6 . 110.0 no Cu1 . O1 . H7 . 124.9 no H6 . O1 . H7 . 109.7 no O11 . Cl11 . O12 . 110.90(17) yes O11 . Cl11 . O13 . 109.6(2) yes O12 . Cl11 . O13 . 108.25(18) yes O11 . Cl11 . O14 . 109.8(2) yes O12 . Cl11 . O14 . 110.1(2) yes O13 . Cl11 . O14 . 108.2(2) yes O21 . Cl21 . O22 . 109.97(18) yes O21 . Cl21 . O23 . 107.90(15) yes O22 . Cl21 . O23 . 110.05(15) yes O21 . Cl21 . O24 . 109.27(16) yes O22 . Cl21 . O24 . 109.92(18) yes O23 . Cl21 . O24 . 109.70(16) yes O31 . Cl31 . O32 . 106.86(17) yes O31 . Cl31 . O33 . 112.0(2) yes O32 . Cl31 . O33 . 109.9(2) yes O31 . Cl31 . O34 . 110.2(2) yes O32 . Cl31 . O34 . 108.6(2) yes O33 . Cl31 . O34 . 109.26(18) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N2 . H1 . O32 3_545 142 0.95 2.19 2.995(2) yes N3 . H2 . O12 . 158 0.95 2.13 3.034(2) yes N4 . H3 . O23 . 166 0.95 2.08 3.012(2) yes N5 . H4 . O32 . 170 0.95 1.91 2.856(2) yes N5 . H5 . O23 2_566 149 0.96 2.17 3.031(2) yes O1 . H6 . O14 . 137 0.95 2.20 2.964(2) yes O1 . H7 . O34 . 143 0.95 2.08 2.896(2) yes # Attachment 'NiMac12.cif' data_NiMac12_173k _database_code_depnum_ccdc_archive 'CCDC 654221' _audit_creation_date 06-11-08 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title '11081024 NiMac12_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.9858(1) _cell_length_b 7.9727(1) _cell_length_c 12.3989(2) _cell_angle_alpha 90 _cell_angle_beta 96.8678(8) _cell_angle_gamma 90 _cell_volume 881.90(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni 0.3393 1.1124 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421 1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C11 H28 Cl1 N5 Ni1 O4 # Dc = 1.46 Fooo = 444.00 Mu = 12.75 M = 388.54 # Found Formula = C11 H27 Cl2 N5 Ni1 O4 # Dc = 1.59 FOOO = 444.00 Mu = 14.28 M = 422.98 _chemical_formula_sum 'C11 H27 Cl2 N5 Ni1 O4' _chemical_formula_moiety 'C11 H27 Cl N5 Ni, Cl O4' _chemical_compound_source ? _chemical_formula_weight 422.98 _cell_measurement_reflns_used 5104 _cell_measurement_theta_min 1 _cell_measurement_theta_max 30 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.593 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 1.428 # Sheldrick geometric approximatio 0.87 0.90 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.90 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 173 _diffrn_reflns_number 9615 _reflns_number_total 5112 _diffrn_reflns_av_R_equivalents 0.021 # Number of reflections with Friedels Law is 2749 # Number of reflections without Friedels Law is 5112 # Theoretical number of reflections is about 2575 _diffrn_reflns_theta_min 1.654 _diffrn_reflns_theta_max 30.010 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.010 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.56 _refine_diff_density_max 0.87 _refine_ls_number_reflns 4567 _refine_ls_number_restraints 1 _refine_ls_number_parameters 209 #_refine_ls_R_factor_ref 0.0291 _refine_ls_wR_factor_ref 0.0353 _refine_ls_goodness_of_fit_ref 1.0409 #_reflns_number_all 5088 _refine_ls_R_factor_all 0.0344 _refine_ls_wR_factor_all 0.0361 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 4567 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_gt 0.0353 _refine_ls_shift/su_max 0.003556 _refine_ls_abs_structure_Flack 0.042(9) _refine_ls_abs_structure_details 'Flack (1983), 2363 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.934 0.481 0.707 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Ni1 Ni 0.14659(2) 0.38354(8) 0.699145(17) 0.0225 1.0000 Uani . . . . . . Cl1 Cl 0.08824(6) 0.65600(9) 0.61162(4) 0.0330 1.0000 Uani . . . . . . Cl2 Cl 0.33149(7) 0.30295(10) 0.19230(5) 0.0367 1.0000 Uani . . . . . . N1 N -0.05417(17) 0.2467(2) 0.64653(14) 0.0256 1.0000 Uani . . . . . . N2 N 0.0140(2) 0.4668(2) 0.81644(14) 0.0293 1.0000 Uani . . . . . . N3 N 0.3230(2) 0.4745(2) 0.81648(16) 0.0341 1.0000 Uani . . . . . . N4 N 0.2281(2) 0.1458(2) 0.75666(14) 0.0288 1.0000 Uani . . . . . . N5 N 0.25717(19) 0.3228(2) 0.56368(15) 0.0302 1.0000 Uani . . . . . . C1 C 0.0936(3) 0.0405(3) 0.76887(18) 0.0331 1.0000 Uani . . . . . . C2 C -0.0286(2) 0.0661(2) 0.67441(18) 0.0306 1.0000 Uani . . . . . . C3 C -0.1767(2) 0.3234(3) 0.6993(2) 0.0343 1.0000 Uani . . . . . . C4 C -0.1240(2) 0.3671(3) 0.81692(17) 0.0365 1.0000 Uani . . . . . . C5 C 0.1041(3) 0.4942(3) 0.92182(18) 0.0420 1.0000 Uani . . . . . . C6 C 0.2540(3) 0.5694(3) 0.8998(2) 0.0420 1.0000 Uani . . . . . . C7 C 0.4158(3) 0.3293(3) 0.8585(2) 0.0415 1.0000 Uani . . . . . . C8 C 0.3220(3) 0.1721(3) 0.86210(19) 0.0390 1.0000 Uani . . . . . . C9 C 0.3210(2) 0.0731(3) 0.67646(19) 0.0361 1.0000 Uani . . . . . . C10 C 0.2748(2) 0.1376(3) 0.56143(18) 0.0342 1.0000 Uani . . . . . . C11 C 0.3982(3) 0.4129(4) 0.5546(2) 0.0485 1.0000 Uani . . . . . . O1 O 0.1828(3) 0.2615(3) 0.1463(2) 0.0661 1.0000 Uani . . . . . . O2 O 0.3586(5) 0.2388(7) 0.2976(3) 0.1188 1.0000 Uani . . . . . . O3 O 0.4352(5) 0.2403(6) 0.1274(3) 0.1088 1.0000 Uani . . . . . . O4 O 0.3419(3) 0.4822(3) 0.1897(3) 0.0688 1.0000 Uani . . . . . . H1 H -0.0763 0.2514 0.5761 0.0378 1.0000 Uiso R . . . . . H2 H -0.0167 0.5680 0.7951 0.0423 1.0000 Uiso R . . . . . H3 H 0.3813 0.5443 0.7857 0.0491 1.0000 Uiso R . . . . . H5 H 0.1967 0.3495 0.5044 0.0440 1.0000 Uiso R . . . . . H11 H 0.1215 -0.0754 0.7706 0.0397 1.0000 Uiso R . . . . . H12 H 0.0571 0.0720 0.8374 0.0393 1.0000 Uiso R . . . . . H21 H 0.0003 0.0071 0.6107 0.0357 1.0000 Uiso R . . . . . H22 H -0.1194 0.0173 0.6932 0.0362 1.0000 Uiso R . . . . . H31 H -0.2605 0.2467 0.6946 0.0403 1.0000 Uiso R . . . . . H32 H -0.2070 0.4273 0.6612 0.0402 1.0000 Uiso R . . . . . H41 H -0.1005 0.2662 0.8610 0.0448 1.0000 Uiso R . . . . . H42 H -0.1973 0.4338 0.8480 0.0442 1.0000 Uiso R . . . . . H51 H 0.1203 0.3900 0.9631 0.0486 1.0000 Uiso R . . . . . H52 H 0.0534 0.5742 0.9641 0.0502 1.0000 Uiso R . . . . . H61 H 0.2403 0.6836 0.8775 0.0491 1.0000 Uiso R . . . . . H62 H 0.3223 0.5649 0.9656 0.0495 1.0000 Uiso R . . . . . H71 H 0.4651 0.3537 0.9293 0.0479 1.0000 Uiso R . . . . . H72 H 0.4923 0.3107 0.8109 0.0479 1.0000 Uiso R . . . . . H81 H 0.3894 0.0775 0.8808 0.0442 1.0000 Uiso R . . . . . H82 H 0.2526 0.1868 0.9173 0.0434 1.0000 Uiso R . . . . . H91 H 0.4238 0.1042 0.6981 0.0417 1.0000 Uiso R . . . . . H92 H 0.3066 -0.0486 0.6758 0.0430 1.0000 Uiso R . . . . . H101 H 0.1794 0.0875 0.5329 0.0414 1.0000 Uiso R . . . . . H102 H 0.3505 0.1070 0.5146 0.0410 1.0000 Uiso R . . . . . H111 H 0.4432 0.3713 0.4944 0.0738 1.0000 Uiso R . . . . . H112 H 0.4661 0.3946 0.6198 0.0736 1.0000 Uiso R . . . . . H113 H 0.3793 0.5330 0.5459 0.0740 1.0000 Uiso 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 0.02370(9) 0.01975(9) 0.02363(9) -0.00052(9) 0.00166(6) 0.00152(9) Cl1 0.0456(3) 0.02254(19) 0.0305(2) 0.00251(15) 0.00320(18) 0.00089(17) Cl2 0.0367(3) 0.0375(3) 0.0362(2) -0.0008(2) 0.00517(19) -0.0026(2) N1 0.0245(7) 0.0232(7) 0.0289(7) 0.0000(5) 0.0030(6) 0.0002(5) N2 0.0376(9) 0.0249(7) 0.0261(7) -0.0001(5) 0.0061(6) 0.0065(6) N3 0.0342(9) 0.0322(9) 0.0337(9) -0.0021(6) -0.0050(7) -0.0011(7) N4 0.0313(7) 0.0237(7) 0.0304(7) -0.0008(6) -0.0009(6) 0.0078(6) N5 0.0245(7) 0.0356(7) 0.0317(8) 0.0003(6) 0.0078(6) 0.0031(6) C1 0.0394(10) 0.0227(7) 0.0370(10) 0.0061(7) 0.0036(8) 0.0023(7) C2 0.0310(9) 0.0217(8) 0.0393(10) -0.0001(7) 0.0056(7) -0.0026(6) C3 0.0256(8) 0.0308(8) 0.0470(11) 0.0022(8) 0.0062(8) 0.0024(7) C4 0.0413(10) 0.0340(11) 0.0373(9) 0.0038(9) 0.0179(8) 0.0078(9) C5 0.0578(14) 0.0434(12) 0.0241(9) -0.0038(8) 0.0023(9) 0.0129(10) C6 0.0552(14) 0.0359(11) 0.0317(10) -0.0085(8) -0.0086(10) 0.0040(9) C7 0.0346(10) 0.0446(11) 0.0414(11) -0.0024(9) -0.0112(9) 0.0055(8) C8 0.0464(12) 0.0353(10) 0.0317(9) 0.0023(8) -0.0092(9) 0.0120(9) C9 0.0315(9) 0.0329(10) 0.0433(11) -0.0044(8) 0.0025(8) 0.0120(8) C10 0.0278(8) 0.0379(10) 0.0375(10) -0.0098(8) 0.0061(7) 0.0040(7) C11 0.0353(10) 0.061(2) 0.0526(13) -0.0068(12) 0.0184(9) -0.0095(11) O1 0.0582(13) 0.0516(12) 0.0828(18) 0.0157(11) -0.0148(12) -0.0215(10) O2 0.126(3) 0.168(4) 0.0524(16) 0.054(2) -0.0268(18) -0.046(3) O3 0.111(3) 0.122(3) 0.103(3) -0.003(2) 0.050(2) 0.066(2) O4 0.0480(12) 0.0433(12) 0.115(2) -0.0140(13) 0.0112(14) -0.0110(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.6767(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni1 . Cl1 . 2.4566(5) yes Ni1 . N1 . 2.1420(16) yes Ni1 . N2 . 2.0951(17) yes Ni1 . N3 . 2.1456(18) yes Ni1 . N4 . 2.1241(16) yes Ni1 . N5 . 2.1076(17) yes Cl2 . O1 . 1.427(2) yes Cl2 . O2 . 1.396(3) yes Cl2 . O3 . 1.394(3) yes Cl2 . O4 . 1.433(3) yes N1 . C2 . 1.492(2) yes N1 . C3 . 1.479(3) yes N1 . H1 . 0.873 no N2 . C4 . 1.473(3) yes N2 . C5 . 1.469(3) yes N2 . H2 . 0.883 no N3 . C6 . 1.476(3) yes N3 . C7 . 1.485(3) yes N3 . H3 . 0.882 no N4 . C1 . 1.494(3) yes N4 . C8 . 1.484(3) yes N4 . C9 . 1.490(3) yes N5 . C10 . 1.486(3) yes N5 . C11 . 1.473(3) yes N5 . H5 . 0.886 no C1 . C2 . 1.520(3) yes C1 . H11 . 0.957 no C1 . H12 . 0.979 no C2 . H21 . 0.980 no C2 . H22 . 0.957 no C3 . C4 . 1.519(3) yes C3 . H31 . 0.967 no C3 . H32 . 0.976 no C4 . H41 . 0.981 no C4 . H42 . 0.962 no C5 . C6 . 1.529(4) yes C5 . H51 . 0.978 no C5 . H52 . 0.972 no C6 . H61 . 0.955 no C6 . H62 . 0.961 no C7 . C8 . 1.514(4) yes C7 . H71 . 0.955 no C7 . H72 . 0.969 no C8 . H81 . 0.977 no C8 . H82 . 0.986 no C9 . C10 . 1.526(3) yes C9 . H91 . 0.963 no C9 . H92 . 0.979 no C10 . H101 . 0.973 no C10 . H102 . 0.976 no C11 . H111 . 0.950 no C11 . H112 . 0.964 no C11 . H113 . 0.976 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 . Ni1 . N1 . 100.85(5) yes Cl1 . Ni1 . N2 . 85.27(5) yes N1 . Ni1 . N2 . 81.05(7) yes Cl1 . Ni1 . N3 . 95.85(5) yes N1 . Ni1 . N3 . 154.91(7) yes N2 . Ni1 . N3 . 81.81(8) yes Cl1 . Ni1 . N4 . 169.76(5) yes N1 . Ni1 . N4 . 83.80(7) yes N2 . Ni1 . N4 . 104.56(7) yes N3 . Ni1 . N4 . 82.93(7) yes Cl1 . Ni1 . N5 . 86.97(5) yes N1 . Ni1 . N5 . 95.77(7) yes N2 . Ni1 . N5 . 170.90(7) yes N3 . Ni1 . N5 . 103.74(8) yes N4 . Ni1 . N5 . 83.46(7) yes O1 . Cl2 . O2 . 109.8(2) yes O1 . Cl2 . O3 . 110.2(2) yes O2 . Cl2 . O3 . 110.7(3) yes O1 . Cl2 . O4 . 106.42(16) yes O2 . Cl2 . O4 . 112.5(3) yes O3 . Cl2 . O4 . 107.1(3) yes Ni1 . N1 . C2 . 108.66(12) yes Ni1 . N1 . C3 . 107.42(12) yes C2 . N1 . C3 . 113.49(16) yes Ni1 . N1 . H1 . 111.5 no C2 . N1 . H1 . 106.5 no C3 . N1 . H1 . 109.4 no Ni1 . N2 . C4 . 112.39(13) yes Ni1 . N2 . C5 . 111.48(15) yes C4 . N2 . C5 . 116.83(19) yes Ni1 . N2 . H2 . 105.4 no C4 . N2 . H2 . 105.1 no C5 . N2 . H2 . 104.4 no Ni1 . N3 . C6 . 108.07(15) yes Ni1 . N3 . C7 . 108.22(14) yes C6 . N3 . C7 . 114.80(19) yes Ni1 . N3 . H3 . 110.4 no C6 . N3 . H3 . 107.6 no C7 . N3 . H3 . 107.8 no Ni1 . N4 . C1 . 106.54(12) yes Ni1 . N4 . C8 . 107.89(12) yes C1 . N4 . C8 . 111.83(18) yes Ni1 . N4 . C9 . 108.74(13) yes C1 . N4 . C9 . 111.93(16) yes C8 . N4 . C9 . 109.74(17) yes Ni1 . N5 . C10 . 107.74(13) yes Ni1 . N5 . C11 . 116.16(16) yes C10 . N5 . C11 . 112.89(18) yes Ni1 . N5 . H5 . 107.8 no C10 . N5 . H5 . 106.2 no C11 . N5 . H5 . 105.5 no N4 . C1 . C2 . 111.41(16) yes N4 . C1 . H11 . 109.3 no C2 . C1 . H11 . 108.1 no N4 . C1 . H12 . 107.6 no C2 . C1 . H12 . 110.4 no H11 . C1 . H12 . 110.0 no C1 . C2 . N1 . 112.65(16) yes C1 . C2 . H21 . 108.6 no N1 . C2 . H21 . 108.9 no C1 . C2 . H22 . 108.4 no N1 . C2 . H22 . 109.7 no H21 . C2 . H22 . 108.4 no N1 . C3 . C4 . 110.89(17) yes N1 . C3 . H31 . 109.1 no C4 . C3 . H31 . 110.7 no N1 . C3 . H32 . 108.4 no C4 . C3 . H32 . 107.9 no H31 . C3 . H32 . 109.7 no C3 . C4 . N2 . 106.59(16) yes C3 . C4 . H41 . 111.6 no N2 . C4 . H41 . 108.6 no C3 . C4 . H42 . 111.2 no N2 . C4 . H42 . 108.7 no H41 . C4 . H42 . 110.0 no N2 . C5 . C6 . 107.67(19) yes N2 . C5 . H51 . 111.8 no C6 . C5 . H51 . 110.3 no N2 . C5 . H52 . 109.5 no C6 . C5 . H52 . 108.6 no H51 . C5 . H52 . 109.0 no C5 . C6 . N3 . 112.14(19) yes C5 . C6 . H61 . 109.8 no N3 . C6 . H61 . 109.6 no C5 . C6 . H62 . 108.8 no N3 . C6 . H62 . 107.2 no H61 . C6 . H62 . 109.2 no N3 . C7 . C8 . 111.38(19) yes N3 . C7 . H71 . 110.0 no C8 . C7 . H71 . 109.9 no N3 . C7 . H72 . 108.4 no C8 . C7 . H72 . 109.2 no H71 . C7 . H72 . 107.9 no C7 . C8 . N4 . 110.52(19) yes C7 . C8 . H81 . 108.3 no N4 . C8 . H81 . 111.8 no C7 . C8 . H82 . 108.8 no N4 . C8 . H82 . 106.7 no H81 . C8 . H82 . 110.7 no N4 . C9 . C10 . 112.39(16) yes N4 . C9 . H91 . 108.0 no C10 . C9 . H91 . 108.6 no N4 . C9 . H92 . 107.9 no C10 . C9 . H92 . 107.8 no H91 . C9 . H92 . 112.3 no C9 . C10 . N5 . 109.57(17) yes C9 . C10 . H101 . 109.3 no N5 . C10 . H101 . 108.9 no C9 . C10 . H102 . 109.9 no N5 . C10 . H102 . 110.1 no H101 . C10 . H102 . 109.1 no N5 . C11 . H111 . 109.9 no N5 . C11 . H112 . 109.0 no H111 . C11 . H112 . 108.6 no N5 . C11 . H113 . 110.3 no H111 . C11 . H113 . 109.9 no H112 . C11 . H113 . 109.1 no