Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2002 data_1 _database_code_CSD 192429 _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Douglas MacFarlane' 'G. Deacon' 'Craig M. Forsyth' 'Maria Forsyth' 'Jake Golding' 'Jennifer M. Pringle' _publ_contact_author_name 'Prof Douglas MacFarlane' _publ_contact_author_address ; Centre for Green Chemistry Monash University School of Chemistry PO Box 23 Victoria 3800 AUSTRALIA ; _publ_contact_author_email 'DOUGLAS.MACFARLANE@SCI.MONASH.EDU.AU' _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; Physical trends and structural features in organic salts of the thiocyanate anion ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-dimethylpyrrolidinium thiocyanate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H14 N2 S' _chemical_formula_weight 158.26 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' 'S' 'S' 0.1246 0.1234 '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)/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 8.4101(2) _cell_length_b 7.8090(2) _cell_length_c 13.6228(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.763(1) _cell_angle_gamma 90.00 _cell_volume 865.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'none' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method '1 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 'none' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12646 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2133 _reflns_number_gt 1486 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius BV, 1994)' _computing_cell_refinement 'DENZO-SMN (Otwinoski and Minor, 1993)' _computing_data_reduction 'DENZO-SMN (Otwinoski and Minor, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'POVRAY 3.0' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2133 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _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 S1 S 0.31602(4) 0.19217(5) 0.01073(3) 0.03392(16) Uani 1 1 d . . . N1 N 0.15283(16) 0.28083(15) 0.15958(10) 0.0326(3) Uani 1 1 d . . . C1 C 0.21958(16) 0.24513(18) 0.09725(10) 0.0249(3) Uani 1 1 d . . . N2 N -0.24499(13) 0.19243(13) -0.26414(8) 0.0219(3) Uani 1 1 d . . . C2 C -0.38851(17) 0.18117(19) -0.21667(11) 0.0253(3) Uani 1 1 d . . . C3 C -0.33569(18) 0.2884(2) -0.12011(11) 0.0295(3) Uani 1 1 d . . . C4 C -0.14646(18) 0.2759(2) -0.08871(11) 0.0291(3) Uani 1 1 d . . . C5 C -0.09865(17) 0.17590(19) -0.17250(11) 0.0253(3) Uani 1 1 d . . . C6 C -0.24947(19) 0.0529(2) -0.33997(12) 0.0296(3) Uani 1 1 d . . . C7 C -0.24204(19) 0.3624(2) -0.31481(12) 0.0269(3) Uani 1 1 d . . . H2A H -0.4790(19) 0.2202(18) -0.2645(11) 0.024(4) Uiso 1 1 d . . . H3A H -0.3753(19) 0.416(2) -0.1356(12) 0.047(5) Uiso 1 1 d . . . H4A H -0.0993(17) 0.392(2) -0.0818(11) 0.032(4) Uiso 1 1 d . . . H5A H -0.004(2) 0.217(2) -0.1911(12) 0.036(4) Uiso 1 1 d . . . H6A H -0.1556(17) 0.0659(19) -0.3646(10) 0.027(4) Uiso 1 1 d . . . H7A H -0.1475(17) 0.3630(18) -0.3437(11) 0.025(4) Uiso 1 1 d . . . H2B H -0.3948(16) 0.059(2) -0.2028(11) 0.027(4) Uiso 1 1 d . . . H3B H -0.386(2) 0.241(2) -0.0696(14) 0.041(4) Uiso 1 1 d . . . H4B H -0.108(2) 0.215(2) -0.0243(14) 0.038(4) Uiso 1 1 d . . . H5B H -0.0888(15) 0.0555(19) -0.1582(10) 0.022(3) Uiso 1 1 d . . . H6B H -0.2533(15) -0.054(2) -0.3070(10) 0.022(4) Uiso 1 1 d . . . H7B H -0.2337(15) 0.449(2) -0.2663(11) 0.028(4) Uiso 1 1 d . . . H6C H -0.3491(18) 0.070(2) -0.3941(12) 0.036(4) Uiso 1 1 d . . . H7C H -0.3387(18) 0.3727(19) -0.3660(12) 0.029(4) 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 S1 0.0312(2) 0.0437(3) 0.0281(2) -0.00118(16) 0.00983(16) 0.00292(16) N1 0.0330(7) 0.0342(8) 0.0316(7) -0.0009(6) 0.0101(6) -0.0023(5) C1 0.0231(7) 0.0230(7) 0.0260(8) 0.0028(6) 0.0013(6) -0.0031(6) N2 0.0232(6) 0.0218(6) 0.0209(6) 0.0008(4) 0.0057(5) -0.0012(4) C2 0.0192(7) 0.0314(8) 0.0260(8) 0.0020(6) 0.0068(6) -0.0007(6) C3 0.0268(8) 0.0370(9) 0.0261(8) -0.0007(6) 0.0094(6) 0.0006(6) C4 0.0272(8) 0.0348(9) 0.0242(8) 0.0002(6) 0.0045(6) 0.0004(6) C5 0.0211(7) 0.0283(8) 0.0251(8) 0.0019(6) 0.0032(6) 0.0014(6) C6 0.0339(8) 0.0272(8) 0.0289(8) -0.0043(7) 0.0101(7) -0.0023(7) C7 0.0309(8) 0.0248(8) 0.0251(8) 0.0033(6) 0.0072(7) -0.0016(6) _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 S1 C1 1.6448(15) . ? N1 C1 1.1649(18) . ? N2 C6 1.4952(18) . ? N2 C7 1.4989(18) . ? N2 C2 1.5101(18) . ? N2 C5 1.5187(17) . ? C2 C3 1.527(2) . ? C3 C4 1.542(2) . ? C4 C5 1.519(2) . ? 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 S1 178.92(13) . . ? C6 N2 C7 109.10(11) . . ? C6 N2 C2 111.79(11) . . ? C7 N2 C2 110.95(11) . . ? C6 N2 C5 112.24(10) . . ? C7 N2 C5 110.41(10) . . ? C2 N2 C5 102.23(10) . . ? N2 C2 C3 104.37(11) . . ? C2 C3 C4 104.90(12) . . ? C5 C4 C3 106.03(12) . . ? N2 C5 C4 105.05(11) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.274 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.047