# Supplementary Material (ESI) for Green Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Oelkers, Benjamin' ; Fachbereich Chemie Philipps-Universit\"at Marburg Hans-Meerwein-Stra\&se 35032 Marburg Germany ; 'Sundermeyer, J\"org' ; Fachbereich Chemie Philipps-Universit\"at Marburg Hans-Meerwein-Stra\&se 35032 Marburg Germany ; _publ_contact_author_address ; Philipps-Universit\"at Marburg Fachbereich Chemie Hans-Meerwein-Stra\&se 35032 Marburg ; _publ_contact_author_email jsu@staff.uni-marburg.de _publ_contact_author_name 'Professor J\"org Sundermeyer' #TrackingRef '- Me6GuaCl.cif' _publ_section_title ; Pentaalkylmethylguanidinium methylcarbonates - versatile precursors for the preparation of halide-free guanidinium-based ILs (GILs) ; data_Me6GuaCl _database_code_depnum_ccdc_archive 'CCDC 797179' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H18 N3, Cl' _chemical_formula_sum 'C7 H18 Cl N3' _chemical_formula_weight 179.69 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 13.622(3) _cell_length_b 7.8211(11) _cell_length_c 9.8987(17) _cell_angle_alpha 90.00 _cell_angle_beta 104.10(2) _cell_angle_gamma 90.00 _cell_volume 1022.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2571 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 25.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.324 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'STOE IPDS 1' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4051 _diffrn_reflns_av_R_equivalents 0.0638 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 25.96 _reflns_number_total 1080 _reflns_number_gt 745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE Expose' _computing_cell_refinement 'STOE Cell' _computing_data_reduction 'STOE Integrate' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1015P)^2^+1.6196P] 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 1080 _refine_ls_number_parameters 77 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0701 _refine_ls_wR_factor_ref 0.2320 _refine_ls_wR_factor_gt 0.2253 _refine_ls_goodness_of_fit_ref 1.257 _refine_ls_restrained_S_all 1.257 _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 0.5000 0.0000 0.0000 0.0368(18) Uani 1 4 d S . . C2 C 0.3969(4) -0.2607(6) -0.0474(5) 0.0556(12) Uani 1 1 d . . . H2A H 0.3828 -0.3209 0.0327 0.083 Uiso 1 1 calc R . . H2B H 0.4017 -0.3437 -0.1196 0.083 Uiso 1 1 calc R . . H2C H 0.3420 -0.1799 -0.0847 0.083 Uiso 1 1 calc R . . C3 C 0.3596(5) 0.0000 0.1137(6) 0.069(2) Uani 1 2 d S . . H3A H 0.3534 -0.0718 0.1923 0.103 Uiso 0.50 1 calc PR . . H3B H 0.2920 0.0268 0.0562 0.103 Uiso 0.50 1 calc PR . . H3C H 0.3947 0.1063 0.1488 0.103 Uiso 0.50 1 calc PR . . C11 C 0.0000 0.5000 0.5000 0.0295(16) Uani 1 4 d S . . C12 C 0.0646(4) 0.7627(6) 0.4177(5) 0.0595(13) Uani 1 1 d . . . H12A H 0.0977 0.6803 0.3688 0.089 Uiso 1 1 calc R . . H12B H 0.1161 0.8305 0.4820 0.089 Uiso 1 1 calc R . . H12C H 0.0213 0.8388 0.3499 0.089 Uiso 1 1 calc R . . C13 C 0.1854(4) 0.5000 0.5504(6) 0.070(2) Uani 1 2 d S . . H13A H 0.1740 0.3951 0.5985 0.105 Uiso 0.50 1 calc PR . . H13B H 0.2296 0.5768 0.6166 0.105 Uiso 0.50 1 calc PR . . H13C H 0.2176 0.4714 0.4749 0.105 Uiso 0.50 1 calc PR . . N1 N 0.5000 -0.1603(12) 0.0000 0.040(2) Uani 0.50 2 d SP . . N2 N 0.4213(4) -0.0978(8) 0.0238(6) 0.0347(14) Uani 0.50 1 d P . . N11 N 0.0000 0.6666(11) 0.5000 0.0350(19) Uani 0.50 2 d SP . . N12 N 0.0829(4) 0.5896(8) 0.4892(6) 0.0352(14) Uani 0.50 1 d P . . Cl1 Cl 0.18190(12) 0.0000 0.74894(15) 0.0586(7) Uani 1 2 d S . . 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 0.032(4) 0.055(6) 0.024(3) 0.000 0.008(3) 0.000 C2 0.074(3) 0.043(3) 0.047(2) -0.005(2) 0.009(2) -0.013(2) C3 0.043(3) 0.132(7) 0.037(3) 0.000 0.023(3) 0.000 C11 0.027(3) 0.040(5) 0.021(3) 0.000 0.005(3) 0.000 C12 0.086(3) 0.047(3) 0.046(2) 0.009(2) 0.017(2) -0.020(2) C13 0.024(3) 0.149(8) 0.037(3) 0.000 0.008(2) 0.000 N1 0.043(5) 0.031(6) 0.044(5) 0.000 0.008(4) 0.000 N2 0.034(3) 0.042(4) 0.032(3) -0.004(3) 0.015(2) -0.005(3) N11 0.036(4) 0.035(6) 0.038(4) 0.000 0.016(4) 0.000 N12 0.029(3) 0.044(3) 0.033(3) 0.004(3) 0.009(2) -0.008(3) Cl1 0.0484(9) 0.0900(14) 0.0340(8) 0.000 0.0036(6) 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 1.254(10) . ? C1 N2 1.384(6) . ? C2 N1 1.578(6) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N2 1.564(7) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C11 N11 1.303(9) . ? C11 N12 1.355(6) . ? C12 N11 1.534(6) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N12 1.548(8) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? N1 N2 1.252(7) . ? N1 C2 1.578(6) 2_655 ? N2 N2 1.530(13) 6 ? N11 N12 1.307(7) . ? N11 C12 1.534(6) 2_556 ? N12 N12 1.401(13) 6_565 ? 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 N1 180.0 5_655 . ? N1 C1 N2 123.6(3) . 5_655 ? N1 C1 N2 56.4(3) . . ? N2 C1 N2 180.0(6) 5_655 . ? N2 C1 N2 112.9(5) . 2_655 ? N2 C1 N2 67.1(5) . 6 ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N11 C11 N11 180.000(1) . 5_566 ? N11 C11 N12 121.1(3) . 5_566 ? N11 C11 N12 58.9(3) . . ? N12 C11 N12 117.7(6) 2_556 . ? N12 C11 N12 180.0(7) 5_566 . ? N12 C11 N12 62.3(6) . 6_565 ? N11 C12 H12A 109.5 . . ? N11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N12 C13 H13A 109.5 . . ? N12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 N1 N2 134.0(10) 2_655 . ? N2 N1 C1 67.0(5) . . ? N2 N1 C2 151.6(4) 2_655 . ? N2 N1 C2 60.6(3) . . ? C1 N1 C2 119.8(3) . . ? C2 N1 C2 120.3(7) . 2_655 ? N1 N2 C1 56.6(5) . . ? N1 N2 N2 113.0(5) . 6 ? C1 N2 N2 56.4(3) . 6 ? N1 N2 C3 154.3(5) . . ? C1 N2 C3 111.9(4) . . ? N2 N2 C3 60.7(2) 6 . ? C11 N11 N12 62.5(4) . . ? N12 N11 N12 125.1(9) 2_556 . ? N12 N11 C12 152.7(3) . 2_556 ? C11 N11 C12 119.3(4) . . ? N12 N11 C12 64.1(3) . . ? C12 N11 C12 121.3(7) 2_556 . ? N11 N12 C11 58.6(4) . . ? N11 N12 N12 117.5(4) . 6_565 ? C11 N12 N12 58.9(3) . 6_565 ? N11 N12 C13 153.1(5) . . ? C11 N12 C13 115.2(4) . . ? N12 N12 C13 63.1(2) 6_565 . ? 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 C1 N1 N2 0.0 5_655 . . 2_655 ? N2 C1 N1 N2 180.0 . . . 2_655 ? N2 C1 N1 N2 180.0 6 . . 2_655 ? N2 C1 N1 N2 180.0 5_655 . . . ? N2 C1 N1 N2 180.0 2_655 . . . ? N2 C1 N1 N2 0.0 6 . . . ? N2 C1 N1 C2 -149.1(3) 5_655 . . . ? N2 C1 N1 C2 30.9(3) . . . . ? N2 C1 N1 C2 -149.1(3) 2_655 . . . ? N2 C1 N1 C2 30.9(3) 6 . . . ? N2 C1 N1 C2 30.9(3) 5_655 . . 2_655 ? N2 C1 N1 C2 -149.1(3) . . . 2_655 ? N2 C1 N1 C2 30.9(3) 2_655 . . 2_655 ? N2 C1 N1 C2 -149.1(3) 6 . . 2_655 ? N2 N1 N2 C1 0.0 2_655 . . . ? C2 N1 N2 C1 -149.3(3) . . . . ? C2 N1 N2 C1 110.6(14) 2_655 . . . ? N2 N1 N2 N2 0.0 2_655 . . 6 ? C1 N1 N2 N2 0.0 . . . 6 ? C2 N1 N2 N2 -149.3(3) . . . 6 ? C2 N1 N2 N2 110.6(14) 2_655 . . 6 ? N2 N1 N2 C3 -69.9(13) 2_655 . . . ? C1 N1 N2 C3 -69.9(13) . . . . ? C2 N1 N2 C3 140.8(14) . . . . ? C2 N1 N2 C3 41(3) 2_655 . . . ? N1 C1 N2 N1 180.0 5_655 . . . ? N2 C1 N2 N1 0.0 2_655 . . . ? N2 C1 N2 N1 180.0 6 . . . ? N1 C1 N2 N2 0.0 5_655 . . 6 ? N1 C1 N2 N2 180.0 . . . 6 ? N2 C1 N2 N2 180.0 2_655 . . 6 ? N1 C1 N2 C3 -26.0(5) 5_655 . . . ? N1 C1 N2 C3 154.0(5) . . . . ? N2 C1 N2 C3 154.0(5) 2_655 . . . ? N2 C1 N2 C3 -26.0(5) 6 . . . ? N12 C11 N11 N12 0.0 5_566 . . 2_556 ? N12 C11 N11 N12 180.0 . . . 2_556 ? N12 C11 N11 N12 180.0 6_565 . . 2_556 ? N12 C11 N11 N12 180.0 2_556 . . . ? N12 C11 N11 N12 180.0 5_566 . . . ? N12 C11 N11 N12 0.0 6_565 . . . ? N12 C11 N11 C12 31.1(4) 2_556 . . 2_556 ? N12 C11 N11 C12 31.1(4) 5_566 . . 2_556 ? N12 C11 N11 C12 -148.9(4) . . . 2_556 ? N12 C11 N11 C12 -148.9(4) 6_565 . . 2_556 ? N12 C11 N11 C12 -148.9(4) 2_556 . . . ? N12 C11 N11 C12 -148.9(4) 5_566 . . . ? N12 C11 N11 C12 31.1(4) . . . . ? N12 C11 N11 C12 31.1(4) 6_565 . . . ? N12 N11 N12 C11 0.0 2_556 . . . ? C12 N11 N12 C11 101.4(14) 2_556 . . . ? C12 N11 N12 C11 -150.0(3) . . . . ? C11 N11 N12 N12 0.0 . . . 6_565 ? N12 N11 N12 N12 0.0 2_556 . . 6_565 ? C12 N11 N12 N12 101.4(14) 2_556 . . 6_565 ? C12 N11 N12 N12 -150.0(3) . . . 6_565 ? C11 N11 N12 C13 -84.1(12) . . . . ? N12 N11 N12 C13 -84.1(12) 2_556 . . . ? C12 N11 N12 C13 17(3) 2_556 . . . ? C12 N11 N12 C13 125.9(13) . . . . ? N11 C11 N12 N11 180.0 5_566 . . . ? N12 C11 N12 N11 180.0 6_565 . . . ? N11 C11 N12 N12 180.0 . . . 6_565 ? N11 C11 N12 N12 0.0 5_566 . . 6_565 ? N11 C11 N12 C13 150.2(6) . . . . ? N11 C11 N12 C13 -29.8(6) 5_566 . . . ? N12 C11 N12 C13 -29.8(6) 6_565 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.466 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.065 #===END