Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Richard Douthwaite' _publ_contact_author_address ; Department of Chemistry University of York Heslington York Yorkshire YO10 5DD UNITED KINGDOM ; _publ_section_title ; Synthesis of a neutral metal-organic network solid [(MeIm)Ni(BDC)] (where MeIm = methylimidazole and BDC = 1, 4-benzenedicarboxylate) in an ionic liquid solvent 1-methyl-3-propylimidazolium bromide ; loop_ _publ_author_address _publ_author_footnote ; Deparment of Chemistry University of York Heslington York YO10 4DD # Address 1 ; ; ? # footnote 1 ; _publ_contact_author_email red4@york.ac.uk _publ_contact_author_fax ' 01904 432516 ' _publ_contact_author_phone ' 01904 434183 ' _publ_requested_category CI _publ_requested_coeditor_name ' ' _publ_author_name R.E.A.Douthwaite data_compound1 _database_code_depnum_ccdc_archive 'CCDC 618884' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N2 Ni O4' _chemical_formula_sum 'C12 H10 N2 Ni O4' _chemical_formula_weight 304.93 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' O O 0.0106 0.0060 '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' N N 0.0061 0.0033 '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 7.6003(8) _cell_length_b 16.7695(17) _cell_length_c 9.7696(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.522(2) _cell_angle_gamma 90.00 _cell_volume 1220.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 1973 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 24.92 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 1.601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.867 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_process_details 'SADABS v2.03; (sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9580 _diffrn_reflns_av_R_equivalents 0.0418 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.04 _reflns_number_total 2143 _reflns_number_gt 1796 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0409P)^2^+0.7159P] 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 2143 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 C1 C -0.1085(4) 0.39965(17) 0.6632(3) 0.0203(7) Uani 1 1 d . . . C2 C -0.1624(4) 0.32939(17) 0.7419(3) 0.0223(7) Uani 1 1 d . . . C3 C -0.3438(4) 0.31159(18) 0.7326(3) 0.0271(7) Uani 1 1 d . . . H3 H -0.4318 0.3452 0.6840 0.033 Uiso 1 1 calc R . . C4 C -0.3914(4) 0.24372(18) 0.7962(3) 0.0270(7) Uani 1 1 d . . . H4 H -0.5123 0.2318 0.7896 0.032 Uiso 1 1 calc R . . C5 C -0.2621(4) 0.19295(17) 0.8699(3) 0.0235(7) Uani 1 1 d . . . C6 C -0.0806(4) 0.21144(17) 0.8807(3) 0.0256(7) Uani 1 1 d . . . H6 H 0.0075 0.1782 0.9305 0.031 Uiso 1 1 calc R . . C7 C -0.0330(4) 0.27953(18) 0.8169(3) 0.0279(8) Uani 1 1 d . . . H7 H 0.0878 0.2920 0.8245 0.034 Uiso 1 1 calc R . . C8 C -0.3168(4) 0.11779(17) 0.9332(3) 0.0243(7) Uani 1 1 d . . . C10 C 0.5223(4) 0.53075(18) 0.7635(3) 0.0263(7) Uani 1 1 d . . . H10 H 0.5720 0.4991 0.7029 0.032 Uiso 1 1 calc R . . C11 C 0.3342(5) 0.5959(2) 0.8561(4) 0.0379(9) Uani 1 1 d . . . H11 H 0.2279 0.6181 0.8719 0.045 Uiso 1 1 calc R . . C12 C 0.4982(5) 0.6065(2) 0.9379(4) 0.0460(10) Uani 1 1 d . . . H12 H 0.5250 0.6364 1.0195 0.055 Uiso 1 1 calc R . . C14 C 0.8116(5) 0.5601(3) 0.9286(4) 0.0522(11) Uani 1 1 d . . . H14A H 0.8601 0.5188 0.8790 0.078 Uiso 1 1 calc R . . H14B H 0.8365 0.5481 1.0266 0.078 Uiso 1 1 calc R . . H14C H 0.8658 0.6102 0.9133 0.078 Uiso 1 1 calc R . . N1 N 0.3491(3) 0.54743(15) 0.7470(3) 0.0241(6) Uani 1 1 d . . . N2 N 0.6163(4) 0.56504(17) 0.8777(3) 0.0327(7) Uani 1 1 d . . . Ni1 Ni 0.16000(5) 0.507170(19) 0.59180(4) 0.01703(14) Uani 1 1 d . . . O1 O 0.0466(3) 0.42750(12) 0.7047(2) 0.0259(5) Uani 1 1 d . . . O2 O -0.2232(3) 0.42397(12) 0.5609(2) 0.0267(5) Uani 1 1 d . . . O3 O -0.4737(3) 0.09219(12) 0.8851(2) 0.0296(5) Uani 1 1 d . . . O4 O -0.2061(3) 0.08477(12) 1.0282(2) 0.0281(5) 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 C1 0.0239(18) 0.0169(15) 0.0228(17) 0.0007(12) 0.0109(14) 0.0003(13) C2 0.0260(17) 0.0205(15) 0.0214(17) 0.0034(12) 0.0070(13) -0.0033(13) C3 0.0258(18) 0.0229(16) 0.0327(19) 0.0055(13) 0.0062(15) -0.0014(14) C4 0.0209(17) 0.0286(17) 0.0330(19) 0.0010(14) 0.0091(14) -0.0059(14) C5 0.0288(19) 0.0192(15) 0.0225(17) 0.0006(12) 0.0055(15) -0.0046(13) C6 0.0254(18) 0.0222(16) 0.0287(19) 0.0072(13) 0.0045(14) 0.0000(13) C7 0.0191(17) 0.0281(17) 0.037(2) 0.0052(14) 0.0059(15) -0.0071(14) C8 0.0305(19) 0.0171(15) 0.0284(19) -0.0005(13) 0.0135(15) -0.0037(14) C10 0.0259(18) 0.0256(16) 0.0274(18) 0.0001(13) 0.0053(14) -0.0028(14) C11 0.034(2) 0.045(2) 0.036(2) -0.0127(17) 0.0102(17) -0.0001(17) C12 0.048(3) 0.057(3) 0.031(2) -0.0193(19) 0.0032(18) -0.007(2) C14 0.031(2) 0.083(3) 0.037(2) 0.001(2) -0.0058(18) -0.006(2) N1 0.0246(15) 0.0257(14) 0.0222(15) -0.0016(11) 0.0050(12) -0.0029(11) N2 0.0266(16) 0.0429(17) 0.0263(16) -0.0023(13) -0.0003(13) -0.0047(13) Ni1 0.0185(2) 0.0132(2) 0.0199(2) 0.00079(15) 0.00511(15) -0.00039(16) O1 0.0283(13) 0.0241(11) 0.0264(12) 0.0068(9) 0.0080(10) -0.0073(10) O2 0.0248(12) 0.0282(12) 0.0277(13) 0.0110(9) 0.0065(10) -0.0002(9) O3 0.0294(13) 0.0239(11) 0.0372(14) 0.0019(10) 0.0106(11) -0.0102(10) O4 0.0318(13) 0.0221(11) 0.0311(13) 0.0069(10) 0.0080(11) -0.0036(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 C1 O2 1.256(4) . ? C1 O1 1.257(4) . ? C1 C2 1.508(4) . ? C2 C7 1.384(4) . ? C2 C3 1.395(4) . ? C3 C4 1.379(4) . ? C3 H3 0.9300 . ? C4 C5 1.388(4) . ? C4 H4 0.9300 . ? C5 C6 1.397(4) . ? C5 C8 1.499(4) . ? C6 C7 1.383(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 O4 1.251(4) . ? C8 O3 1.266(4) . ? C10 N1 1.324(4) . ? C10 N2 1.329(4) . ? C10 H10 0.9300 . ? C11 C12 1.351(5) . ? C11 N1 1.363(4) . ? C11 H11 0.9300 . ? C12 N2 1.359(5) . ? C12 H12 0.9300 . ? C14 N2 1.471(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? N1 Ni1 1.987(2) . ? Ni1 O4 2.013(2) 4_665 ? Ni1 O2 2.019(2) 3_566 ? Ni1 O1 2.031(2) . ? Ni1 O3 2.053(2) 2_456 ? Ni1 Ni1 2.7290(8) 3_566 ? O2 Ni1 2.019(2) 3_566 ? O3 Ni1 2.053(2) 2_446 ? O4 Ni1 2.013(2) 4_566 ? 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 O2 C1 O1 126.4(3) . . ? O2 C1 C2 116.3(3) . . ? O1 C1 C2 117.3(3) . . ? C7 C2 C3 119.6(3) . . ? C7 C2 C1 120.4(3) . . ? C3 C2 C1 120.0(3) . . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 121.1(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 119.3(3) . . ? C4 C5 C8 120.2(3) . . ? C6 C5 C8 120.4(3) . . ? C7 C6 C5 119.5(3) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 121.0(3) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? O4 C8 O3 124.7(3) . . ? O4 C8 C5 118.5(3) . . ? O3 C8 C5 116.8(3) . . ? N1 C10 N2 111.4(3) . . ? N1 C10 H10 124.3 . . ? N2 C10 H10 124.3 . . ? C12 C11 N1 109.2(3) . . ? C12 C11 H11 125.4 . . ? N1 C11 H11 125.4 . . ? C11 C12 N2 106.8(3) . . ? C11 C12 H12 126.6 . . ? N2 C12 H12 126.6 . . ? N2 C14 H14A 109.5 . . ? N2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C10 N1 C11 105.5(3) . . ? C10 N1 Ni1 124.8(2) . . ? C11 N1 Ni1 129.7(2) . . ? C10 N2 C12 107.1(3) . . ? C10 N2 C14 126.6(3) . . ? C12 N2 C14 126.3(3) . . ? N1 Ni1 O4 99.34(10) . 4_665 ? N1 Ni1 O2 97.28(10) . 3_566 ? O4 Ni1 O2 90.03(9) 4_665 3_566 ? N1 Ni1 O1 97.45(10) . . ? O4 Ni1 O1 87.67(9) 4_665 . ? O2 Ni1 O1 165.27(9) 3_566 . ? N1 Ni1 O3 95.15(10) . 2_456 ? O4 Ni1 O3 165.49(9) 4_665 2_456 ? O2 Ni1 O3 87.43(9) 3_566 2_456 ? O1 Ni1 O3 91.17(9) . 2_456 ? N1 Ni1 Ni1 160.93(8) . 3_566 ? O4 Ni1 Ni1 99.73(7) 4_665 3_566 ? O2 Ni1 Ni1 82.95(6) 3_566 3_566 ? O1 Ni1 Ni1 83.10(6) . 3_566 ? O3 Ni1 Ni1 65.78(6) 2_456 3_566 ? C1 O1 Ni1 122.76(19) . . ? C1 O2 Ni1 122.95(19) . 3_566 ? C8 O3 Ni1 144.5(2) . 2_446 ? C8 O4 Ni1 105.16(19) . 4_566 ? 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 O2 C1 C2 C7 154.9(3) . . . . ? O1 C1 C2 C7 -24.2(4) . . . . ? O2 C1 C2 C3 -21.3(4) . . . . ? O1 C1 C2 C3 159.6(3) . . . . ? C7 C2 C3 C4 -1.2(5) . . . . ? C1 C2 C3 C4 175.0(3) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C3 C4 C5 C8 -177.5(3) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C8 C5 C6 C7 177.5(3) . . . . ? C5 C6 C7 C2 -0.3(5) . . . . ? C3 C2 C7 C6 1.2(5) . . . . ? C1 C2 C7 C6 -175.0(3) . . . . ? C4 C5 C8 O4 -161.0(3) . . . . ? C6 C5 C8 O4 21.0(4) . . . . ? C4 C5 C8 O3 19.2(4) . . . . ? C6 C5 C8 O3 -158.8(3) . . . . ? N1 C11 C12 N2 0.8(4) . . . . ? N2 C10 N1 C11 0.9(4) . . . . ? N2 C10 N1 Ni1 -179.1(2) . . . . ? C12 C11 N1 C10 -1.0(4) . . . . ? C12 C11 N1 Ni1 178.9(3) . . . . ? N1 C10 N2 C12 -0.4(4) . . . . ? N1 C10 N2 C14 -179.6(3) . . . . ? C11 C12 N2 C10 -0.3(4) . . . . ? C11 C12 N2 C14 179.0(4) . . . . ? C10 N1 Ni1 O4 18.3(3) . . . 4_665 ? C11 N1 Ni1 O4 -161.6(3) . . . 4_665 ? C10 N1 Ni1 O2 -72.9(3) . . . 3_566 ? C11 N1 Ni1 O2 107.2(3) . . . 3_566 ? C10 N1 Ni1 O1 107.2(3) . . . . ? C11 N1 Ni1 O1 -72.7(3) . . . . ? C10 N1 Ni1 O3 -161.0(3) . . . 2_456 ? C11 N1 Ni1 O3 19.1(3) . . . 2_456 ? C10 N1 Ni1 Ni1 -162.38(18) . . . 3_566 ? C11 N1 Ni1 Ni1 17.7(5) . . . 3_566 ? O2 C1 O1 Ni1 -11.0(4) . . . . ? C2 C1 O1 Ni1 168.02(19) . . . . ? N1 Ni1 O1 C1 161.5(2) . . . . ? O4 Ni1 O1 C1 -99.4(2) 4_665 . . . ? O2 Ni1 O1 C1 -18.2(5) 3_566 . . . ? O3 Ni1 O1 C1 66.1(2) 2_456 . . . ? Ni1 Ni1 O1 C1 0.7(2) 3_566 . . . ? O1 C1 O2 Ni1 17.9(4) . . . 3_566 ? C2 C1 O2 Ni1 -161.12(19) . . . 3_566 ? O4 C8 O3 Ni1 5.3(6) . . . 2_446 ? C5 C8 O3 Ni1 -174.9(2) . . . 2_446 ? O3 C8 O4 Ni1 -4.6(4) . . . 4_566 ? C5 C8 O4 Ni1 175.7(2) . . . 4_566 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.401 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.074