# Supplementary Material (ESI) for Energy & Environmental Science # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Energy Environ.Sci.' _journal_coden_Cambridge 1148 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Andrew Churchard' _publ_contact_author_email achurch@icm.edu.pl _publ_section_title ; Nickel macrocycles with complex hydrides new avenues for hydrogen storage research ; loop_ _publ_author_name 'Andrew Churchard' 'Michal KsaweryCyranski' 'Lukasz Dobrzycki' 'Armand Budzianowski' ; W.Grochala ; # Attachment '- cis.CIF' data_wg16 _database_code_depnum_ccdc_archive 'CCDC 773705' #TrackingRef '- cis.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H32 B2 N4 Ni' _chemical_formula_weight 288.73 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' B B 0.0013 0.0007 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 14.4512(7) _cell_length_b 9.4625(6) _cell_length_c 11.7824(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1611.18(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2205 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 28.30 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 1.191 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.890 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'KM4 CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12412 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0710 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.49 _reflns_number_total 1598 _reflns_number_gt 713 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1' _computing_publication_material SHELXTL-97 _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^)+(0.0486P)^2^+0.0000P] 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 1598 _refine_ls_number_parameters 148 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0943 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0873 _refine_ls_goodness_of_fit_ref 0.818 _refine_ls_restrained_S_all 0.818 _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 C1 C 0.2908(13) 1.038(2) 0.3888(19) 0.095(6) Uani 0.50 1 d PD A -1 H1B H 0.2923 1.0135 0.3070 0.114 Uiso 0.50 1 calc PR A -1 H1A H 0.3035 1.1399 0.3981 0.114 Uiso 0.50 1 calc PR A -1 C2 C 0.1999(13) 0.9966(18) 0.4424(15) 0.130(10) Uani 0.50 1 d PD A -1 H2A H 0.2003 1.0307 0.5218 0.155 Uiso 0.50 1 calc PR A -1 H2B H 0.1501 1.0481 0.4023 0.155 Uiso 0.50 1 calc PR A -1 C3 C 0.0872(12) 0.838(3) 0.5034(18) 0.085(5) Uani 0.50 1 d PD A -1 H3B H 0.0372 0.8781 0.4561 0.102 Uiso 0.50 1 calc PR A -1 H3A H 0.0900 0.8912 0.5755 0.102 Uiso 0.50 1 calc PR A -1 C4 C 0.0675(13) 0.683(3) 0.527(2) 0.087(6) Uani 0.50 1 d PD A -1 H4A H 0.0080 0.6814 0.5690 0.104 Uiso 0.50 1 calc PR A -1 H4B H 0.0553 0.6392 0.4526 0.104 Uiso 0.50 1 calc PR A -1 C5 C 0.1296(6) 0.5837(11) 0.5886(7) 0.107(3) Uani 0.50 1 d PD A -1 H5B H 0.1353 0.6151 0.6685 0.129 Uiso 0.50 1 calc PR A -1 H5A H 0.1007 0.4888 0.5890 0.129 Uiso 0.50 1 calc PR A -1 C6 C 0.2158(15) 0.4903(13) 0.4327(14) 0.097(8) Uani 0.50 1 d PD A -1 H6A H 0.1674 0.5293 0.3821 0.116 Uiso 0.50 1 calc PR A -1 H6B H 0.2023 0.3895 0.4481 0.116 Uiso 0.50 1 calc PR A -1 C7 C 0.3101(12) 0.5091(16) 0.383(2) 0.092(7) Uani 0.50 1 d PD A -1 H7B H 0.3557 0.4680 0.4367 0.110 Uiso 0.50 1 calc PR A -1 H7A H 0.3136 0.4544 0.3120 0.110 Uiso 0.50 1 calc PR A -1 C8 C 0.4357(12) 0.677(2) 0.3238(17) 0.106(8) Uani 0.50 1 d PD A -1 H8B H 0.4478 0.6252 0.2524 0.127 Uiso 0.50 1 calc PR A -1 H8A H 0.4778 0.6398 0.3830 0.127 Uiso 0.50 1 calc PR A -1 C9 C 0.4530(14) 0.831(3) 0.3068(16) 0.123(10) Uani 0.50 1 d PD A -1 H9B H 0.4079 0.8637 0.2491 0.147 Uiso 0.50 1 calc PR A -1 H9A H 0.5150 0.8397 0.2717 0.147 Uiso 0.50 1 calc PR A -1 C10 C 0.4498(6) 0.9380(10) 0.4022(7) 0.104(3) Uani 0.50 1 d PD A -1 H10A H 0.4945 0.9095 0.4617 0.125 Uiso 0.50 1 calc PR A -1 H10B H 0.4693 1.0313 0.3727 0.125 Uiso 0.50 1 calc PR A -1 N1 N 0.3561(4) 0.9514(7) 0.4539(6) 0.074(2) Uani 0.50 1 d PD A -1 H1N H 0.3690 0.9912 0.5214 0.111 Uiso 0.50 1 d PR A -1 N2 N 0.1755(4) 0.8484(7) 0.4440(5) 0.0676(19) Uani 0.50 1 d PD A -1 H2N H 0.1758 0.8045 0.3750 0.101 Uiso 0.50 1 d PR A -1 N3 N 0.2233(4) 0.5724(8) 0.5389(6) 0.086(2) Uani 0.50 1 d PD A -1 H3N H 0.2616 0.5630 0.5985 0.129 Uiso 0.50 1 d PR A -1 N4 N 0.3374(4) 0.6561(7) 0.3593(5) 0.0763(18) Uani 0.50 1 d PD A -1 H4N H 0.2947 0.6889 0.3103 0.114 Uiso 0.50 1 d PR A -1 Ni1 Ni 0.29616(4) 0.7500 0.50594(5) 0.0670(3) Uani 1 2 d S . . B1 B 0.3641(4) 0.7500 0.6733(5) 0.079(2) Uani 1 2 d SG A . H1BA H 0.2965 0.7946 0.6544 0.095 Uiso 0.50 1 d PG . . H1BB H 0.3951 0.7195 0.5852 0.095 Uiso 0.50 1 d PG . . H1BC H 0.4114 0.8326 0.7072 0.095 Uiso 0.50 1 d PG . . H1BD H 0.3622 0.6571 0.7248 0.095 Uiso 0.50 1 d PG . . B2 B 0.1924(3) 0.7500 0.1519(4) 0.0449(13) Uani 1 2 d S . . H2BA H 0.1555 0.7500 0.0616 0.054 Uiso 1 2 d SR . . H2BB H 0.2680 0.7500 0.1379 0.054 Uiso 1 2 d SR . . H2BC H 0.1732 0.8441 0.2030 0.054 Uiso 1 1 d 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 C1 0.178(18) 0.047(11) 0.061(7) 0.004(7) -0.027(9) -0.005(9) C2 0.104(14) 0.23(2) 0.059(11) -0.024(13) 0.009(9) 0.080(15) C3 0.065(8) 0.155(12) 0.036(7) -0.007(8) 0.016(6) -0.027(6) C4 0.069(9) 0.129(15) 0.062(11) -0.007(8) 0.014(7) -0.015(8) C5 0.072(6) 0.162(9) 0.088(6) 0.053(6) -0.035(5) -0.061(6) C6 0.14(2) 0.028(6) 0.118(17) -0.006(8) -0.043(13) 0.020(11) C7 0.111(13) 0.053(13) 0.111(12) -0.017(9) -0.030(10) 0.045(9) C8 0.068(10) 0.125(15) 0.125(14) -0.040(11) 0.001(9) -0.015(8) C9 0.054(7) 0.21(2) 0.108(11) -0.051(13) 0.008(7) -0.023(8) C10 0.074(6) 0.147(9) 0.091(7) -0.009(6) 0.020(5) -0.038(6) N1 0.057(4) 0.091(6) 0.074(5) -0.013(4) 0.012(3) -0.020(4) N2 0.059(4) 0.066(4) 0.077(4) 0.006(4) 0.011(3) -0.005(4) N3 0.075(5) 0.107(6) 0.076(4) 0.030(4) -0.037(4) -0.019(5) N4 0.061(4) 0.084(5) 0.084(5) -0.008(4) 0.005(3) 0.002(4) Ni1 0.0480(4) 0.0908(5) 0.0621(4) 0.000 0.0002(4) 0.000 B1 0.046(4) 0.121(6) 0.071(4) 0.000 -0.007(3) 0.000 B2 0.048(3) 0.041(3) 0.047(3) 0.000 0.009(2) 0.000 _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 C1 N1 1.465(17) . ? C1 C2 1.509(16) . ? C1 H1B 0.9900 . ? C1 H1A 0.9900 . ? C2 N2 1.446(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N2 1.459(14) . ? C3 C4 1.515(10) . ? C3 H3B 0.9900 . ? C3 H3A 0.9900 . ? C4 C5 1.488(17) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N3 1.478(9) . ? C5 H5B 0.9900 . ? C5 H5A 0.9900 . ? C6 N3 1.477(14) . ? C6 C7 1.492(16) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N4 1.474(15) . ? C7 H7B 0.9900 . ? C7 H7A 0.9900 . ? C8 N4 1.493(16) . ? C8 C9 1.495(12) . ? C8 H8B 0.9900 . ? C8 H8A 0.9900 . ? C9 C10 1.511(17) . ? C9 H9B 0.9900 . ? C9 H9A 0.9900 . ? C10 N1 1.491(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? N1 Ni1 2.182(7) . ? N1 H1N 0.8998 . ? N2 Ni1 2.107(6) . ? N2 H2N 0.9123 . ? N3 Ni1 2.021(7) . ? N3 H3N 0.8992 . ? N4 Ni1 2.033(6) . ? N4 H4N 0.9009 . ? Ni1 N3 2.021(7) 7_575 ? Ni1 N4 2.033(6) 7_575 ? Ni1 N2 2.107(6) 7_575 ? Ni1 N1 2.182(7) 7_575 ? Ni1 B1 2.202(6) . ? Ni1 H1BA 1.7998 . ? Ni1 H1BB 1.7326 . ? B1 H1BA 1.0871 . ? B1 H1BB 1.1661 . ? B1 H1BC 1.1125 . ? B1 H1BD 1.0688 . ? B2 H2BA 1.1905 . ? B2 H2BB 1.1051 . ? B2 H2BC 1.1106 . ? 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 C1 C2 101.4(14) . . ? N1 C1 H1B 111.5 . . ? C2 C1 H1B 111.5 . . ? N1 C1 H1A 111.5 . . ? C2 C1 H1A 111.5 . . ? H1B C1 H1A 109.3 . . ? N2 C2 C1 117.9(13) . . ? N2 C2 H2A 107.8 . . ? C1 C2 H2A 107.8 . . ? N2 C2 H2B 107.8 . . ? C1 C2 H2B 107.8 . . ? H2A C2 H2B 107.2 . . ? N2 C3 C4 108.8(17) . . ? N2 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? N2 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? H3B C3 H3A 108.3 . . ? C5 C4 C3 126(2) . . ? C5 C4 H4A 105.8 . . ? C3 C4 H4A 105.8 . . ? C5 C4 H4B 105.8 . . ? C3 C4 H4B 105.8 . . ? H4A C4 H4B 106.2 . . ? N3 C5 C4 114.0(8) . . ? N3 C5 H5B 108.8 . . ? C4 C5 H5B 108.8 . . ? N3 C5 H5A 108.8 . . ? C4 C5 H5A 108.8 . . ? H5B C5 H5A 107.7 . . ? N3 C6 C7 101.5(15) . . ? N3 C6 H6A 111.5 . . ? C7 C6 H6A 111.5 . . ? N3 C6 H6B 111.5 . . ? C7 C6 H6B 111.5 . . ? H6A C6 H6B 109.3 . . ? N4 C7 C6 115.7(11) . . ? N4 C7 H7B 108.4 . . ? C6 C7 H7B 108.4 . . ? N4 C7 H7A 108.4 . . ? C6 C7 H7A 108.4 . . ? H7B C7 H7A 107.4 . . ? N4 C8 C9 109.0(19) . . ? N4 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? N4 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? H8B C8 H8A 108.3 . . ? C8 C9 C10 123(2) . . ? C8 C9 H9B 106.5 . . ? C10 C9 H9B 106.5 . . ? C8 C9 H9A 106.5 . . ? C10 C9 H9A 106.5 . . ? H9B C9 H9A 106.5 . . ? N1 C10 C9 112.8(10) . . ? N1 C10 H10A 109.0 . . ? C9 C10 H10A 109.0 . . ? N1 C10 H10B 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C1 N1 C10 114.8(10) . . ? C1 N1 Ni1 112.2(9) . . ? C10 N1 Ni1 113.6(5) . . ? C1 N1 H1N 111.3 . . ? C10 N1 H1N 102.0 . . ? Ni1 N1 H1N 101.5 . . ? C2 N2 C3 106.7(13) . . ? C2 N2 Ni1 103.4(9) . . ? C3 N2 Ni1 121.8(11) . . ? C2 N2 H2N 115.4 . . ? C3 N2 H2N 113.6 . . ? Ni1 N2 H2N 95.9 . . ? C6 N3 C5 107.9(10) . . ? C6 N3 Ni1 108.2(7) . . ? C5 N3 Ni1 119.5(6) . . ? C6 N3 H3N 130.9 . . ? C5 N3 H3N 105.2 . . ? Ni1 N3 H3N 84.9 . . ? C7 N4 C8 115.7(12) . . ? C7 N4 Ni1 99.7(9) . . ? C8 N4 Ni1 117.3(10) . . ? C7 N4 H4N 105.4 . . ? C8 N4 H4N 115.3 . . ? Ni1 N4 H4N 101.1 . . ? N3 Ni1 N3 112.5(4) . 7_575 ? N3 Ni1 N4 132.8(3) . 7_575 ? N3 Ni1 N4 87.3(3) 7_575 7_575 ? N3 Ni1 N4 87.3(3) . . ? N3 Ni1 N4 132.8(3) 7_575 . ? N4 Ni1 N4 51.8(4) 7_575 . ? N3 Ni1 N2 43.0(3) . 7_575 ? N3 Ni1 N2 90.2(2) 7_575 7_575 ? N4 Ni1 N2 98.1(2) 7_575 7_575 ? N4 Ni1 N2 75.8(2) . 7_575 ? N3 Ni1 N2 90.2(2) . . ? N3 Ni1 N2 43.0(3) 7_575 . ? N4 Ni1 N2 75.8(2) 7_575 . ? N4 Ni1 N2 98.1(2) . . ? N2 Ni1 N2 52.4(4) 7_575 . ? N3 Ni1 N1 170.9(3) . . ? N3 Ni1 N1 62.3(3) 7_575 . ? N4 Ni1 N1 42.5(3) 7_575 . ? N4 Ni1 N1 91.5(3) . . ? N2 Ni1 N1 128.1(3) 7_575 . ? N2 Ni1 N1 81.1(2) . . ? N3 Ni1 N1 62.3(3) . 7_575 ? N3 Ni1 N1 170.9(3) 7_575 7_575 ? N4 Ni1 N1 91.5(3) 7_575 7_575 ? N4 Ni1 N1 42.5(3) . 7_575 ? N2 Ni1 N1 81.1(2) 7_575 7_575 ? N2 Ni1 N1 128.1(3) . 7_575 ? N1 Ni1 N1 121.8(3) . 7_575 ? N3 Ni1 B1 93.5(2) . . ? N3 Ni1 B1 93.5(2) 7_575 . ? N4 Ni1 B1 129.1(2) 7_575 . ? N4 Ni1 B1 129.1(2) . . ? N2 Ni1 B1 132.8(2) 7_575 . ? N2 Ni1 B1 132.8(2) . . ? N1 Ni1 B1 94.3(2) . . ? N1 Ni1 B1 94.3(2) 7_575 . ? B1 Ni1 H1BA 29.4 . . ? B1 Ni1 H1BB 31.7 . . ? H1BA Ni1 H1BB 60.8 . . ? Ni1 B1 H1BA 54.3 . . ? Ni1 B1 H1BB 51.3 . . ? H1BA B1 H1BB 105.1 . . ? Ni1 B1 H1BC 126.5 . . ? H1BA B1 H1BC 110.6 . . ? H1BB B1 H1BC 104.9 . . ? Ni1 B1 H1BD 119.8 . . ? H1BA B1 H1BD 114.3 . . ? H1BB B1 H1BD 108.1 . . ? H1BC B1 H1BD 113.0 . . ? H2BA B2 H2BB 108.1 . . ? H2BA B2 H2BC 111.9 . . ? H2BB B2 H2BC 109.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -56(2) . . . . ? N2 C3 C4 C5 55(3) . . . . ? C3 C4 C5 N3 -56(3) . . . . ? N3 C6 C7 N4 -60.2(17) . . . . ? N4 C8 C9 C10 66(3) . . . . ? C8 C9 C10 N1 -64(2) . . . . ? C2 C1 N1 C10 164.4(11) . . . . ? C2 C1 N1 Ni1 32.7(15) . . . . ? C9 C10 N1 C1 -78.9(16) . . . . ? C9 C10 N1 Ni1 52.2(12) . . . . ? C1 C2 N2 C3 178.0(17) . . . . ? C1 C2 N2 Ni1 48.5(17) . . . . ? C4 C3 N2 C2 -169(2) . . . . ? C4 C3 N2 Ni1 -51(2) . . . . ? C7 C6 N3 C5 170.7(9) . . . . ? C7 C6 N3 Ni1 40.0(11) . . . . ? C4 C5 N3 C6 -73.5(14) . . . . ? C4 C5 N3 Ni1 50.6(13) . . . . ? C6 C7 N4 C8 172.6(15) . . . . ? C6 C7 N4 Ni1 45.8(16) . . . . ? C9 C8 N4 C7 -177.9(17) . . . . ? C9 C8 N4 Ni1 -61(2) . . . . ? C6 N3 Ni1 N3 120.3(9) . . . 7_575 ? C5 N3 Ni1 N3 -3.6(8) . . . 7_575 ? C6 N3 Ni1 N4 11.9(10) . . . 7_575 ? C5 N3 Ni1 N4 -112.0(6) . . . 7_575 ? C6 N3 Ni1 N4 -15.5(9) . . . . ? C5 N3 Ni1 N4 -139.4(6) . . . . ? C6 N3 Ni1 N2 56.4(9) . . . 7_575 ? C5 N3 Ni1 N2 -67.4(5) . . . 7_575 ? C6 N3 Ni1 N2 82.6(9) . . . . ? C5 N3 Ni1 N2 -41.3(6) . . . . ? C6 N3 Ni1 N1 -51.5(9) . . . 7_575 ? C5 N3 Ni1 N1 -175.4(7) . . . 7_575 ? C6 N3 Ni1 B1 -144.5(9) . . . . ? C5 N3 Ni1 B1 91.6(6) . . . . ? C7 N4 Ni1 N3 -14.4(8) . . . . ? C8 N4 Ni1 N3 -140.1(10) . . . . ? C7 N4 Ni1 N3 -133.0(8) . . . 7_575 ? C8 N4 Ni1 N3 101.2(10) . . . 7_575 ? C7 N4 Ni1 N4 -168.9(8) . . . 7_575 ? C8 N4 Ni1 N4 65.4(10) . . . 7_575 ? C7 N4 Ni1 N2 -56.3(8) . . . 7_575 ? C8 N4 Ni1 N2 177.9(10) . . . 7_575 ? C7 N4 Ni1 N2 -104.1(8) . . . . ? C8 N4 Ni1 N2 130.1(10) . . . . ? C7 N4 Ni1 N1 174.6(8) . . . . ? C8 N4 Ni1 N1 48.9(10) . . . . ? C7 N4 Ni1 N1 36.0(8) . . . 7_575 ? C8 N4 Ni1 N1 -89.8(10) . . . 7_575 ? C7 N4 Ni1 B1 77.9(8) . . . . ? C8 N4 Ni1 B1 -47.9(10) . . . . ? C2 N2 Ni1 N3 164.0(8) . . . . ? C3 N2 Ni1 N3 44.4(11) . . . . ? C2 N2 Ni1 N3 40.0(8) . . . 7_575 ? C3 N2 Ni1 N3 -79.6(12) . . . 7_575 ? C2 N2 Ni1 N4 -61.5(8) . . . 7_575 ? C3 N2 Ni1 N4 178.9(12) . . . 7_575 ? C2 N2 Ni1 N4 -108.7(8) . . . . ? C3 N2 Ni1 N4 131.7(11) . . . . ? C2 N2 Ni1 N2 -173.8(7) . . . 7_575 ? C3 N2 Ni1 N2 66.6(11) . . . 7_575 ? C2 N2 Ni1 N1 -18.4(8) . . . . ? C3 N2 Ni1 N1 -138.0(11) . . . . ? C2 N2 Ni1 N1 -142.1(8) . . . 7_575 ? C3 N2 Ni1 N1 98.3(11) . . . 7_575 ? C2 N2 Ni1 B1 69.1(8) . . . . ? C3 N2 Ni1 B1 -50.5(12) . . . . ? C1 N1 Ni1 N3 -50.4(10) . . . 7_575 ? C10 N1 Ni1 N3 177.3(7) . . . 7_575 ? C1 N1 Ni1 N4 69.3(10) . . . 7_575 ? C10 N1 Ni1 N4 -63.0(6) . . . 7_575 ? C1 N1 Ni1 N4 88.6(10) . . . . ? C10 N1 Ni1 N4 -43.7(6) . . . . ? C1 N1 Ni1 N2 15.5(10) . . . 7_575 ? C10 N1 Ni1 N2 -116.8(6) . . . 7_575 ? C1 N1 Ni1 N2 -9.4(10) . . . . ? C10 N1 Ni1 N2 -141.7(6) . . . . ? C1 N1 Ni1 N1 120.2(10) . . . 7_575 ? C10 N1 Ni1 N1 -12.1(8) . . . 7_575 ? C1 N1 Ni1 B1 -142.0(10) . . . . ? C10 N1 Ni1 B1 85.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.326 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.044 # Attachment '- trans.CIF' data_wg1 _database_code_depnum_ccdc_archive 'CCDC 773706' #TrackingRef '- trans.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H32 B2 N4 Ni' _chemical_formula_weight 288.73 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' B B 0.0013 0.0007 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1397(5) _cell_length_b 12.8109(7) _cell_length_c 8.7041(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.948(6) _cell_angle_gamma 90.00 _cell_volume 748.36(8) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 1.282 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.79 _exptl_absorpt_correction_T_max 0.87 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'KM4 CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean 8.6479 _diffrn_standards_number '1 frame' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6841 _diffrn_reflns_av_R_equivalents 0.0130 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 28.58 _reflns_number_total 1820 _reflns_number_gt 1480 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET) (compiled Oct 25 2005,08:50:05) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 2.2' _computing_publication_material SHELXTL-97 _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^)+(0.0320P)^2^+0.0062P] 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 SHELXL _refine_ls_extinction_coef 0.0150(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1820 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0190 _refine_ls_wR_factor_ref 0.0511 _refine_ls_wR_factor_gt 0.0501 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.0000 0.0000 0.0000 0.00883(8) Uani 1 2 d S . . N1 N 0.27454(14) 0.03255(8) 0.17338(12) 0.0114(2) Uani 1 1 d . . . H1 H 0.355(2) 0.0321(11) 0.1240(17) 0.013(3) Uiso 1 1 d . . . N2 N -0.04732(13) 0.14976(8) -0.09319(12) 0.0122(2) Uani 1 1 d . . . H2 H 0.0151(19) 0.1509(11) -0.1529(16) 0.018(4) Uiso 1 1 d . . . C1 C 0.32261(16) -0.05599(9) 0.28983(13) 0.0148(3) Uani 1 1 d . . . H1A H 0.2497 -0.0487 0.3677 0.018 Uiso 1 1 calc R . . H1B H 0.4672 -0.0571 0.3527 0.018 Uiso 1 1 calc R . . C2 C 0.29365(17) 0.13498(9) 0.25416(14) 0.0158(2) Uani 1 1 d . . . H2A H 0.4323 0.1440 0.3295 0.019 Uiso 1 1 calc R . . H2B H 0.2046 0.1373 0.3198 0.019 Uiso 1 1 calc R . . C3 C 0.24084(16) 0.22444(9) 0.13108(15) 0.0163(2) Uani 1 1 d . . . H3A H 0.3172 0.2154 0.0560 0.020 Uiso 1 1 calc R . . H3B H 0.2853 0.2907 0.1911 0.020 Uiso 1 1 calc R . . C4 C 0.02036(16) 0.23470(9) 0.02871(14) 0.0162(3) Uani 1 1 d . . . H4A H -0.0596 0.2333 0.1019 0.019 Uiso 1 1 calc R . . H4B H -0.0024 0.3028 -0.0285 0.019 Uiso 1 1 calc R . . C5 C -0.26166(16) 0.15619(9) -0.19270(14) 0.0150(2) Uani 1 1 d . . . H5A H -0.2856 0.2166 -0.2679 0.018 Uiso 1 1 calc R . . H5B H -0.3417 0.1658 -0.1206 0.018 Uiso 1 1 calc R . . B1 B -0.2293(2) 0.02008(11) 0.21244(17) 0.0171(3) Uani 1 1 d . . . H3 H -0.106(2) 0.0409(13) 0.1541(19) 0.031 Uiso 1 1 d . . . H4 H -0.315(2) -0.0493(12) 0.1533(18) 0.031 Uiso 1 1 d . . . H5 H -0.320(2) 0.0901(12) 0.1942(17) 0.031 Uiso 1 1 d . . . H6 H -0.156(2) 0.0040(10) 0.337(2) 0.031 Uiso 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 0.00722(11) 0.00903(11) 0.01011(11) 0.00026(8) 0.00281(7) 0.00009(8) N1 0.0091(4) 0.0143(4) 0.0115(5) -0.0009(4) 0.0045(4) -0.0010(4) N2 0.0103(4) 0.0127(5) 0.0152(5) 0.0008(4) 0.0064(4) 0.0003(4) C1 0.0112(5) 0.0200(7) 0.0123(5) 0.0036(5) 0.0028(4) 0.0015(4) C2 0.0127(5) 0.0186(6) 0.0163(6) -0.0059(5) 0.0051(5) -0.0032(5) C3 0.0147(5) 0.0129(6) 0.0226(6) -0.0050(5) 0.0078(5) -0.0032(4) C4 0.0161(6) 0.0105(6) 0.0241(7) -0.0018(5) 0.0095(5) -0.0007(4) C5 0.0100(5) 0.0157(6) 0.0190(6) 0.0053(5) 0.0045(4) 0.0034(4) B1 0.0143(6) 0.0219(8) 0.0177(6) -0.0048(5) 0.0090(5) -0.0038(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 N2 2.0654(10) 3 ? Ni1 N2 2.0654(10) . ? Ni1 N1 2.0676(10) 3 ? Ni1 N1 2.0676(10) . ? Ni1 H3 1.829(15) . ? N1 C2 1.4728(16) . ? N1 C1 1.4814(15) . ? N1 H1 0.826(14) . ? N2 C4 1.4810(15) . ? N2 C5 1.4813(14) . ? N2 H2 0.792(13) . ? C1 C5 1.5169(16) 3 ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5257(17) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5272(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C1 1.5169(17) 3 ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? B1 H3 1.184(15) . ? B1 H4 1.101(15) . ? B1 H5 1.085(15) . ? B1 H6 1.054(18) . ? 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 N2 Ni1 N2 180.00(6) 3 . ? N2 Ni1 N1 94.97(4) 3 3 ? N2 Ni1 N1 85.03(4) . 3 ? N2 Ni1 N1 85.03(4) 3 . ? N2 Ni1 N1 94.97(4) . . ? N1 Ni1 N1 180.00(9) 3 . ? N2 Ni1 H3 91.8(5) 3 . ? N2 Ni1 H3 88.2(5) . . ? N1 Ni1 H3 93.7(5) 3 . ? N1 Ni1 H3 86.3(5) . . ? C2 N1 C1 113.17(9) . . ? C2 N1 Ni1 116.01(7) . . ? C1 N1 Ni1 106.60(7) . . ? C2 N1 H1 106.7(10) . . ? C1 N1 H1 108.1(10) . . ? Ni1 N1 H1 105.8(9) . . ? C4 N2 C5 113.42(9) . . ? C4 N2 Ni1 115.56(7) . . ? C5 N2 Ni1 106.21(7) . . ? C4 N2 H2 109.7(10) . . ? C5 N2 H2 108.4(10) . . ? Ni1 N2 H2 102.8(10) . . ? N1 C1 C5 108.13(9) . 3 ? N1 C1 H1A 110.1 . . ? C5 C1 H1A 110.1 3 . ? N1 C1 H1B 110.1 . . ? C5 C1 H1B 110.1 3 . ? H1A C1 H1B 108.4 . . ? N1 C2 C3 111.94(9) . . ? N1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? N1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 115.65(10) . . ? C2 C3 H3A 108.4 . . ? C4 C3 H3A 108.4 . . ? C2 C3 H3B 108.4 . . ? C4 C3 H3B 108.4 . . ? H3A C3 H3B 107.4 . . ? N2 C4 C3 111.98(9) . . ? N2 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? N2 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? N2 C5 C1 108.76(9) . 3 ? N2 C5 H5A 109.9 . . ? C1 C5 H5A 109.9 3 . ? N2 C5 H5B 109.9 . . ? C1 C5 H5B 109.9 3 . ? H5A C5 H5B 108.3 . . ? H3 B1 H4 110.8(10) . . ? H3 B1 H5 104.1(11) . . ? H4 B1 H5 113.1(11) . . ? H3 B1 H6 107.8(11) . . ? H4 B1 H6 109.0(10) . . ? H5 B1 H6 112.0(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Ni1 N1 C2 -141.63(8) 3 . . . ? N2 Ni1 N1 C2 38.37(8) . . . . ? N2 Ni1 N1 C1 -14.60(7) 3 . . . ? N2 Ni1 N1 C1 165.40(7) . . . . ? N1 Ni1 N2 C4 141.65(8) 3 . . . ? N1 Ni1 N2 C4 -38.35(8) . . . . ? N1 Ni1 N2 C5 14.92(7) 3 . . . ? N1 Ni1 N2 C5 -165.08(7) . . . . ? C2 N1 C1 C5 169.77(9) . . . 3 ? Ni1 N1 C1 C5 41.07(10) . . . 3 ? C1 N1 C2 C3 -179.32(9) . . . . ? Ni1 N1 C2 C3 -55.65(11) . . . . ? N1 C2 C3 C4 70.96(13) . . . . ? C5 N2 C4 C3 178.93(9) . . . . ? Ni1 N2 C4 C3 55.94(11) . . . . ? C2 C3 C4 N2 -71.24(13) . . . . ? C4 N2 C5 C1 -169.63(9) . . . 3 ? Ni1 N2 C5 C1 -41.63(10) . . . 3 ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.354 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.046