# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _publ_contact_author_name 'Deanna L. Zubris' _publ_contact_author_address ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; _publ_contact_author_email deanna.zubris@villanova.edu _publ_contact_author_phone 610-519-6120 _publ_contact_author_fax 610-519-7167 loop_ _publ_author_name _publ_author_address T.J.Dudley ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; J.E.Beck ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; E.E.P.Santos ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; K.A.Johnston ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; W.S.Kassel ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; ; W.G.Dougherty ; ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; W.J.Boyko ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; D.L.Zubris ;Department of Chemistry Villanova University 800 Lancaster Ave Villanova, PA 19085 ; data_zubr018 _database_code_depnum_ccdc_archive 'CCDC 840092' #TrackingRef '- zubr018.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 Br2 N2 Ni' _chemical_formula_weight 470.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.1735(8) _cell_length_b 10.4551(7) _cell_length_c 14.3322(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.5480(10) _cell_angle_gamma 90.00 _cell_volume 1793.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6507 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 33.07 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.744 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 5.536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4040 _exptl_absorpt_correction_T_max 0.6658 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17630 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 33.27 _reflns_number_total 6803 _reflns_number_gt 4895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0198P)^2^] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6803 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0555 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _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 0.03921(2) 1.06385(3) 0.120254(17) 0.01182(6) Uani 1 1 d . . . Br1 Br 0.043688(17) 1.13765(2) -0.046800(13) 0.01475(5) Uani 1 1 d . . . Br2 Br 0.224070(17) 1.14027(2) 0.182987(14) 0.02027(6) Uani 1 1 d . . . N1 N 0.01995(13) 0.99152(17) 0.24789(11) 0.0129(3) Uani 1 1 d . . . N2 N -0.08522(13) 1.17701(17) 0.15109(11) 0.0124(3) Uani 1 1 d . . . C1 C -0.06596(16) 1.0422(2) 0.28395(13) 0.0132(4) Uani 1 1 d . . . C2 C -0.09683(17) 0.9901(2) 0.36456(13) 0.0160(4) Uani 1 1 d . . . H2A H -0.1585 1.0241 0.3886 0.019 Uiso 1 1 calc R . . C3 C -0.03643(17) 0.8876(2) 0.40959(14) 0.0174(4) Uani 1 1 d . . . H3A H -0.0565 0.8510 0.4648 0.021 Uiso 1 1 calc R . . C4 C 0.05284(17) 0.8390(2) 0.37380(14) 0.0166(4) Uani 1 1 d . . . H4A H 0.0963 0.7704 0.4045 0.020 Uiso 1 1 calc R . . C5 C 0.07725(17) 0.8936(2) 0.29161(14) 0.0160(4) Uani 1 1 d . . . H5A H 0.1374 0.8595 0.2656 0.019 Uiso 1 1 calc R . . C6 C -0.11972(16) 1.1539(2) 0.22925(13) 0.0133(4) Uani 1 1 d . . . C7 C -0.20775(18) 1.2337(2) 0.26430(15) 0.0190(5) Uani 1 1 d . . . H7A H -0.2211 1.3101 0.2217 0.023 Uiso 1 1 calc R . . C8 C -0.1715(2) 1.2853(2) 0.36587(16) 0.0266(5) Uani 1 1 d . . . H8A H -0.0939 1.3146 0.3746 0.040 Uiso 1 1 calc R . . H8B H -0.1778 1.2171 0.4115 0.040 Uiso 1 1 calc R . . H8C H -0.2199 1.3569 0.3761 0.040 Uiso 1 1 calc R . . C9 C -0.31898(18) 1.1608(2) 0.25180(16) 0.0262(5) Uani 1 1 d . . . H9A H -0.3430 1.1381 0.1848 0.039 Uiso 1 1 calc R . . H9B H -0.3758 1.2151 0.2723 0.039 Uiso 1 1 calc R . . H9C H -0.3091 1.0828 0.2903 0.039 Uiso 1 1 calc R . . C10 C -0.12537(16) 1.2856(2) 0.09244(13) 0.0138(4) Uani 1 1 d . . . C11 C -0.07185(17) 1.4035(2) 0.11365(14) 0.0170(4) Uani 1 1 d . . . C12 C -0.10577(19) 1.5056(2) 0.05234(16) 0.0226(5) Uani 1 1 d . . . H12A H -0.0711 1.5867 0.0651 0.027 Uiso 1 1 calc R . . C13 C -0.18880(19) 1.4907(3) -0.02647(16) 0.0255(5) Uani 1 1 d . . . H13A H -0.2108 1.5613 -0.0674 0.031 Uiso 1 1 calc R . . C14 C -0.24010(18) 1.3730(2) -0.04606(14) 0.0230(5) Uani 1 1 d . . . H14A H -0.2972 1.3638 -0.1005 0.028 Uiso 1 1 calc R . . C15 C -0.20925(17) 1.2682(2) 0.01278(13) 0.0166(4) Uani 1 1 d . . . C16 C 0.01932(19) 1.4212(2) 0.19853(15) 0.0230(5) Uani 1 1 d . . . H16A H 0.0534 1.5057 0.1957 0.034 Uiso 1 1 calc R . . H16B H 0.0762 1.3549 0.1988 0.034 Uiso 1 1 calc R . . H16C H -0.0122 1.4147 0.2566 0.034 Uiso 1 1 calc R . . C17 C -0.26504(18) 1.1403(2) -0.01036(15) 0.0242(5) Uani 1 1 d . . . H17A H -0.2983 1.1373 -0.0780 0.036 Uiso 1 1 calc R . . H17B H -0.3236 1.1285 0.0275 0.036 Uiso 1 1 calc R . . H17C H -0.2094 1.0720 0.0043 0.036 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 0.01275(11) 0.01071(14) 0.01261(10) -0.00015(10) 0.00392(9) -0.00015(11) Br1 0.02021(10) 0.01092(11) 0.01421(8) 0.00011(8) 0.00602(7) -0.00311(9) Br2 0.01594(9) 0.02370(13) 0.02059(9) -0.00143(9) 0.00181(8) -0.00633(9) N1 0.0131(7) 0.0115(9) 0.0139(7) -0.0009(7) 0.0023(6) -0.0012(7) N2 0.0134(7) 0.0105(9) 0.0133(7) -0.0005(6) 0.0022(6) -0.0002(7) C1 0.0136(9) 0.0117(11) 0.0143(8) 0.0000(8) 0.0028(7) 0.0005(8) C2 0.0154(9) 0.0172(12) 0.0165(8) 0.0008(8) 0.0054(8) 0.0006(9) C3 0.0200(10) 0.0172(12) 0.0152(8) 0.0033(8) 0.0038(8) -0.0007(9) C4 0.0173(9) 0.0134(12) 0.0172(8) 0.0033(8) -0.0015(8) 0.0010(8) C5 0.0139(9) 0.0175(12) 0.0166(9) -0.0004(8) 0.0025(8) 0.0009(8) C6 0.0122(8) 0.0127(11) 0.0153(8) 0.0002(8) 0.0033(7) -0.0019(8) C7 0.0222(10) 0.0165(12) 0.0210(9) 0.0055(9) 0.0111(9) 0.0075(9) C8 0.0353(13) 0.0225(14) 0.0250(11) -0.0018(10) 0.0136(10) 0.0048(11) C9 0.0185(10) 0.0323(16) 0.0301(11) 0.0099(11) 0.0103(9) 0.0080(10) C10 0.0172(9) 0.0113(11) 0.0145(8) 0.0011(8) 0.0069(8) 0.0048(8) C11 0.0194(10) 0.0137(11) 0.0208(9) 0.0011(8) 0.0117(8) 0.0026(9) C12 0.0264(11) 0.0143(12) 0.0317(11) 0.0059(10) 0.0176(10) 0.0052(10) C13 0.0275(12) 0.0238(14) 0.0296(11) 0.0135(10) 0.0170(10) 0.0121(11) C14 0.0217(10) 0.0331(15) 0.0161(9) 0.0065(10) 0.0084(8) 0.0120(11) C15 0.0174(9) 0.0181(12) 0.0151(8) -0.0006(8) 0.0052(8) 0.0062(9) C16 0.0252(11) 0.0147(13) 0.0299(11) -0.0031(10) 0.0075(9) -0.0034(10) C17 0.0211(10) 0.0268(14) 0.0225(10) -0.0053(10) -0.0017(9) 0.0035(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 N1 2.0323(16) . ? Ni1 N2 2.0334(16) . ? Ni1 Br2 2.4022(3) . ? Ni1 Br1 2.4851(4) 3_575 ? Ni1 Br1 2.5256(3) . ? Br1 Ni1 2.4851(4) 3_575 ? N1 C5 1.330(3) . ? N1 C1 1.356(2) . ? N2 C6 1.289(2) . ? N2 C10 1.444(3) . ? C1 C2 1.390(3) . ? C1 C6 1.490(3) . ? C2 C3 1.390(3) . ? C3 C4 1.380(3) . ? C4 C5 1.389(3) . ? C6 C7 1.515(3) . ? C7 C9 1.535(3) . ? C7 C8 1.539(3) . ? C10 C15 1.397(3) . ? C10 C11 1.402(3) . ? C11 C12 1.396(3) . ? C11 C16 1.501(3) . ? C12 C13 1.380(3) . ? C13 C14 1.385(4) . ? C14 C15 1.392(3) . ? C15 C17 1.509(3) . ? 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 N1 Ni1 N2 78.91(6) . . ? N1 Ni1 Br2 92.37(5) . . ? N2 Ni1 Br2 114.16(5) . . ? N1 Ni1 Br1 87.77(5) . 3_575 ? N2 Ni1 Br1 108.93(5) . 3_575 ? Br2 Ni1 Br1 136.093(13) . 3_575 ? N1 Ni1 Br1 173.25(5) . . ? N2 Ni1 Br1 100.05(5) . . ? Br2 Ni1 Br1 94.122(11) . . ? Br1 Ni1 Br1 86.269(11) 3_575 . ? Ni1 Br1 Ni1 93.731(11) 3_575 . ? C5 N1 C1 119.72(16) . . ? C5 N1 Ni1 125.01(13) . . ? C1 N1 Ni1 114.95(13) . . ? C6 N2 C10 121.62(17) . . ? C6 N2 Ni1 116.99(14) . . ? C10 N2 Ni1 121.15(11) . . ? N1 C1 C2 120.56(18) . . ? N1 C1 C6 113.62(16) . . ? C2 C1 C6 125.82(17) . . ? C1 C2 C3 119.19(18) . . ? C4 C3 C2 119.76(18) . . ? C3 C4 C5 118.00(19) . . ? N1 C5 C4 122.73(18) . . ? N2 C6 C1 115.02(17) . . ? N2 C6 C7 123.18(18) . . ? C1 C6 C7 121.80(16) . . ? C6 C7 C9 110.48(19) . . ? C6 C7 C8 114.16(18) . . ? C9 C7 C8 112.20(17) . . ? C15 C10 C11 122.2(2) . . ? C15 C10 N2 119.48(19) . . ? C11 C10 N2 118.11(18) . . ? C12 C11 C10 117.6(2) . . ? C12 C11 C16 120.4(2) . . ? C10 C11 C16 121.99(19) . . ? C13 C12 C11 121.1(2) . . ? C12 C13 C14 120.1(2) . . ? C13 C14 C15 121.0(2) . . ? C10 C15 C14 117.9(2) . . ? C10 C15 C17 121.8(2) . . ? C14 C15 C17 120.3(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.714 _refine_diff_density_min -0.580 _refine_diff_density_rms 0.124