# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'A. Furstner' _publ_contact_author_address ; Max-Planck-Institut fur Kohlenforschung Kaiser-Wilhelm-Platz 1 Mulheim/Ruhr D-45470 GERMANY ; _publ_contact_author_email FUERSTNER@MPI-MUELHEIM.MPG.DE #_publ_requested_category ?FI ; full inorganic #_publ_requested_category ?FM ; full organometallic #_publ_requested_category ?FO ; full organic #?If CI, CM or CO remember to remove section "..._molecular_graphics" #_publ_requested_category ?CI ; electronic inorganic #_publ_requested_category ?CM ; electronic organometallic #_publ_requested_category ?CO ; electronic organic _publ_section_title ; Convenient, scalable and flexible method for the preparation of imidazolium salts with previously inaccessible substitution patterns ; loop_ _publ_author_name _publ_author_address 'A. Furstner' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'M. Alcarazo' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'V. Cesar' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; 'C.W. Lehmann' ; Max-Planck-Institut f\"ur Kohlenforschung Kaiser-Wilhelm-Platz 1 D-45470 M\"ulheim an der Ruhr Germany ; #===END data_5390 _database_code_depnum_ccdc_archive 'CCDC 602504' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source MeOH/Et2O _chemical_formula_moiety 'C15 H23 Cl N2 O5' _chemical_formula_sum 'C15 H23 Cl N2 O5' _chemical_formula_weight 346.80 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' O O 0.0106 0.0060 '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 P21/n _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.5277(4) _cell_length_b 8.3692(3) _cell_length_c 17.3259(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.388(2) _cell_angle_gamma 90.00 _cell_volume 1657.68(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 21720 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 31.51 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method none _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Scalepack, Otwinowski (1997)' _exptl_absorpt_correction_T_min 1 _exptl_absorpt_correction_T_max 1 _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.3 mm rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD \w-scan' _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 37427 _diffrn_reflns_av_R_equivalents 0.1096 _diffrn_reflns_av_sigmaI/netI 0.0827 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 31.49 _reflns_number_total 5490 _reflns_number_gt 2889 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect software (Nonius, 1998)' _computing_cell_refinement 'Denzo / Scalepack (Otwinowski 1997)' _computing_data_reduction 'Denzo / Scalepack (Otwinowski 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _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^)+(0.0659P)^2^+2.0427P] 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_number_reflns 5490 _refine_ls_number_parameters 245 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1600 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.2000 _refine_ls_wR_factor_gt 0.1667 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.002 _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 Cl1 Cl 0.71074(6) 0.27217(10) 0.98968(4) 0.0369(2) Uani 1 1 d . . . O1 O 0.8161(2) 0.2192(4) 1.03343(18) 0.0700(9) Uani 1 1 d . . . O2 O 0.7345(3) 0.3070(6) 0.91385(19) 0.1157(16) Uani 1 1 d . . . O3 O 0.62491(19) 0.1488(3) 0.98679(14) 0.0430(6) Uani 1 1 d . . . O4 O 0.6665(3) 0.4087(3) 1.0230(3) 0.1105(15) Uani 1 1 d . . . C1 C 0.1456(2) 0.7039(3) 0.48377(15) 0.0252(6) Uani 1 1 d . . . H1 H 0.0633 0.6992 0.4841 0.030 Uiso 1 1 calc R . . N2 N 0.19324(19) 0.7054(3) 0.41945(13) 0.0255(5) Uani 1 1 d . A . C3 C 0.3238(2) 0.7226(4) 0.43846(17) 0.0325(6) Uani 1 1 d . . . C3' C 0.3932(3) 0.5971(5) 0.4026(2) 0.0495(9) Uani 1 1 d . . . H3'1 H 0.3846 0.6120 0.3461 0.074 Uiso 1 1 calc R . . H3'2 H 0.3643 0.4909 0.4146 0.074 Uiso 1 1 calc R . . H3'3 H 0.4759 0.6064 0.4239 0.074 Uiso 1 1 calc R . . O3' O 0.3603(2) 0.8735(3) 0.41213(15) 0.0528(7) Uani 1 1 d . . . H3' H 0.3145 0.9450 0.4239 0.079 Uiso 1 1 calc R . . C4 C 0.3403(2) 0.7012(4) 0.52823(18) 0.0348(7) Uani 1 1 d . . . H4 H 0.3714 0.5914 0.5406 0.042 Uiso 1 1 calc R . . C4' C 0.4224(3) 0.8204(5) 0.5723(2) 0.0486(9) Uani 1 1 d . . . H4'1 H 0.3911 0.9286 0.5631 0.073 Uiso 1 1 calc R . . H4'2 H 0.4995 0.8134 0.5544 0.073 Uiso 1 1 calc R . . H4'3 H 0.4298 0.7966 0.6281 0.073 Uiso 1 1 calc R . . N5 N 0.21988(19) 0.7094(3) 0.54836(13) 0.0268(5) Uani 1 1 d . . . C7 C 0.1234(2) 0.7022(4) 0.33972(16) 0.0330(7) Uani 1 1 d D . . C8A C 0.1795(10) 0.624(2) 0.2787(6) 0.078(5) Uani 0.399(9) 1 d PD A 1 H8A1 H 0.2090 0.5192 0.2970 0.117 Uiso 0.399(9) 1 calc PR A 1 H8A2 H 0.2447 0.6901 0.2661 0.117 Uiso 0.399(9) 1 calc PR A 1 H8A3 H 0.1224 0.6108 0.2321 0.117 Uiso 0.399(9) 1 calc PR A 1 C9A C 0.0035(10) 0.6389(18) 0.3466(7) 0.054(4) Uani 0.399(9) 1 d PD A 1 H9A1 H -0.0394 0.6237 0.2945 0.082 Uiso 0.399(9) 1 calc PR A 1 H9A2 H -0.0386 0.7151 0.3757 0.082 Uiso 0.399(9) 1 calc PR A 1 H9A3 H 0.0102 0.5363 0.3742 0.082 Uiso 0.399(9) 1 calc PR A 1 C10A C 0.1051(11) 0.8871(10) 0.3183(6) 0.056(4) Uani 0.399(9) 1 d PD A 1 H10A H 0.1814 0.9375 0.3163 0.085 Uiso 0.399(9) 1 calc PR A 1 H10B H 0.0654 0.9400 0.3580 0.085 Uiso 0.399(9) 1 calc PR A 1 H10C H 0.0574 0.8972 0.2675 0.085 Uiso 0.399(9) 1 calc PR A 1 C8B C 0.1359(6) 0.5272(8) 0.3073(4) 0.0500(18) Uani 0.601(9) 1 d PD A 2 H8B1 H 0.0850 0.5152 0.2579 0.075 Uiso 0.601(9) 1 calc PR A 2 H8B2 H 0.1132 0.4496 0.3450 0.075 Uiso 0.601(9) 1 calc PR A 2 H8B3 H 0.2173 0.5084 0.2991 0.075 Uiso 0.601(9) 1 calc PR A 2 C9B C -0.0039(6) 0.7273(13) 0.3448(5) 0.050(2) Uani 0.601(9) 1 d PD A 2 H9B1 H -0.0475 0.7251 0.2923 0.075 Uiso 0.601(9) 1 calc PR A 2 H9B2 H -0.0151 0.8310 0.3690 0.075 Uiso 0.601(9) 1 calc PR A 2 H9B3 H -0.0325 0.6421 0.3763 0.075 Uiso 0.601(9) 1 calc PR A 2 C10B C 0.1699(6) 0.8164(8) 0.2844(3) 0.047(2) Uani 0.601(9) 1 d PD A 2 H10D H 0.2514 0.7896 0.2797 0.071 Uiso 0.601(9) 1 calc PR A 2 H10E H 0.1657 0.9256 0.3042 0.071 Uiso 0.601(9) 1 calc PR A 2 H10F H 0.1229 0.8085 0.2333 0.071 Uiso 0.601(9) 1 calc PR A 2 C11 C 0.1872(2) 0.7064(3) 0.62478(16) 0.0294(6) Uani 1 1 d . . . C12 C 0.0925(3) 0.7946(4) 0.64122(17) 0.0363(7) Uani 1 1 d . . . H12 H 0.0503 0.8589 0.6021 0.044 Uiso 1 1 calc R . . C13 C 0.0592(3) 0.7887(5) 0.71544(19) 0.0489(9) Uani 1 1 d . . . H13 H -0.0077 0.8463 0.7266 0.059 Uiso 1 1 calc R . . C14 C 0.1231(3) 0.6994(5) 0.77317(19) 0.0486(9) Uani 1 1 d . . . H14 H 0.1015 0.6979 0.8243 0.058 Uiso 1 1 calc R . . C15 C 0.2179(3) 0.6129(5) 0.75637(19) 0.0482(9) Uani 1 1 d . . . H15 H 0.2617 0.5516 0.7961 0.058 Uiso 1 1 calc R . . C16 C 0.2505(3) 0.6141(4) 0.68186(18) 0.0399(7) Uani 1 1 d . . . H16 H 0.3152 0.5524 0.6702 0.048 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 Cl1 0.0269(3) 0.0449(5) 0.0377(4) 0.0066(3) -0.0003(3) -0.0044(3) O1 0.0390(14) 0.093(2) 0.0713(19) 0.0069(16) -0.0177(13) 0.0038(14) O2 0.086(2) 0.210(5) 0.0506(18) 0.052(2) 0.0055(16) -0.049(3) O3 0.0391(13) 0.0360(12) 0.0547(14) -0.0077(11) 0.0091(10) -0.0061(10) O4 0.100(3) 0.0273(15) 0.207(5) -0.028(2) 0.030(3) 0.0036(16) C1 0.0239(13) 0.0215(13) 0.0302(14) 0.0015(11) 0.0029(10) -0.0014(10) N2 0.0243(11) 0.0251(12) 0.0272(11) 0.0024(9) 0.0035(8) -0.0007(9) C3 0.0224(13) 0.0374(16) 0.0377(16) 0.0003(13) 0.0041(11) -0.0033(12) C3' 0.0343(17) 0.061(2) 0.053(2) -0.0133(18) 0.0021(15) 0.0207(16) O3' 0.0507(15) 0.0471(15) 0.0604(16) 0.0059(13) 0.0068(12) -0.0183(12) C4 0.0250(14) 0.0403(18) 0.0386(16) 0.0006(14) 0.0022(12) -0.0013(12) C4' 0.0298(16) 0.068(3) 0.047(2) -0.0091(18) 0.0002(14) -0.0117(16) N5 0.0229(11) 0.0276(12) 0.0291(12) 0.0004(10) 0.0003(9) -0.0013(9) C7 0.0308(14) 0.0425(18) 0.0250(14) 0.0059(13) 0.0014(11) -0.0035(13) C8A 0.068(8) 0.113(14) 0.051(7) -0.040(8) 0.000(6) 0.031(8) C9A 0.053(6) 0.077(9) 0.027(5) 0.014(6) -0.017(4) -0.028(7) C10A 0.073(8) 0.039(5) 0.050(6) 0.013(4) -0.020(5) -0.007(5) C8B 0.064(4) 0.054(4) 0.029(3) -0.004(3) -0.005(3) -0.003(3) C9B 0.029(3) 0.087(7) 0.034(3) 0.014(4) 0.001(2) -0.001(4) C10B 0.048(4) 0.056(5) 0.036(3) 0.017(3) 0.000(3) -0.010(3) C11 0.0311(14) 0.0292(15) 0.0272(14) 0.0011(12) 0.0013(11) -0.0092(12) C12 0.0330(15) 0.0461(19) 0.0300(15) 0.0018(14) 0.0042(12) -0.0010(14) C13 0.048(2) 0.066(2) 0.0357(18) -0.0014(17) 0.0138(14) -0.0006(18) C14 0.060(2) 0.058(2) 0.0290(16) 0.0004(16) 0.0088(15) -0.0160(19) C15 0.059(2) 0.049(2) 0.0324(17) 0.0107(15) -0.0095(15) -0.0128(17) C16 0.0418(18) 0.0404(18) 0.0355(17) 0.0062(14) -0.0030(13) -0.0011(14) _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 Cl1 O4 1.406(3) . Y Cl1 O2 1.407(3) . Y Cl1 O1 1.418(3) . Y Cl1 O3 1.426(2) . Y C1 N2 1.305(3) . Y C1 N5 1.320(3) . Y C1 H1 0.9500 . N N2 C3 1.505(3) . Y N2 C7 1.507(3) . Y C3 O3' 1.425(4) . Y C3 C3' 1.502(4) . Y C3 C4 1.553(4) . Y C3' H3'1 0.9800 . N C3' H3'2 0.9800 . N C3' H3'3 0.9800 . N O3' H3' 0.8400 . N C4 N5 1.476(4) . Y C4 C4' 1.513(4) . Y C4 H4 1.0000 . N C4' H4'1 0.9800 . N C4' H4'2 0.9800 . N C4' H4'3 0.9800 . N N5 C11 1.422(4) . Y C7 C8A 1.463(9) . Y C7 C9B 1.496(7) . Y C7 C9A 1.499(10) . Y C7 C10B 1.500(6) . Y C7 C8B 1.582(7) . Y C7 C10A 1.599(8) . Y C8A H8A1 0.9800 . N C8A H8A2 0.9800 . N C8A H8A3 0.9800 . N C9A H9A1 0.9800 . N C9A H9A2 0.9800 . N C9A H9A3 0.9800 . N C10A H10A 0.9800 . N C10A H10B 0.9800 . N C10A H10C 0.9800 . N C8B H8B1 0.9800 . N C8B H8B2 0.9800 . N C8B H8B3 0.9800 . N C9B H9B1 0.9800 . N C9B H9B2 0.9800 . N C9B H9B3 0.9800 . N C10B H10D 0.9800 . N C10B H10E 0.9800 . N C10B H10F 0.9800 . N C11 C12 1.377(4) . Y C11 C16 1.386(4) . Y C12 C13 1.389(4) . Y C12 H12 0.9500 . N C13 C14 1.383(5) . Y C13 H13 0.9500 . N C14 C15 1.373(5) . Y C14 H14 0.9500 . N C15 C16 1.390(5) . Y C15 H15 0.9500 . N C16 H16 0.9500 . N 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 O4 Cl1 O2 109.9(3) . . Y O4 Cl1 O1 111.5(2) . . Y O2 Cl1 O1 107.9(2) . . Y O4 Cl1 O3 108.43(18) . . Y O2 Cl1 O3 109.6(2) . . Y O1 Cl1 O3 109.57(17) . . Y N2 C1 N5 115.2(2) . . Y N2 C1 H1 122.4 . . N N5 C1 H1 122.4 . . N C1 N2 C3 109.5(2) . . Y C1 N2 C7 123.3(2) . . Y C3 N2 C7 127.1(2) . . Y O3' C3 C3' 107.0(3) . . Y O3' C3 N2 110.0(2) . . Y C3' C3 N2 114.4(3) . . Y O3' C3 C4 114.8(3) . . Y C3' C3 C4 109.3(3) . . Y N2 C3 C4 101.4(2) . . Y C3 C3' H3'1 109.5 . . N C3 C3' H3'2 109.5 . . N H3'1 C3' H3'2 109.5 . . N C3 C3' H3'3 109.5 . . N H3'1 C3' H3'3 109.5 . . N H3'2 C3' H3'3 109.5 . . N C3 O3' H3' 109.5 . . N N5 C4 C4' 113.4(3) . . Y N5 C4 C3 103.5(2) . . Y C4' C4 C3 114.7(3) . . Y N5 C4 H4 108.3 . . N C4' C4 H4 108.3 . . N C3 C4 H4 108.3 . . N C4 C4' H4'1 109.5 . . N C4 C4' H4'2 109.5 . . N H4'1 C4' H4'2 109.5 . . N C4 C4' H4'3 109.5 . . N H4'1 C4' H4'3 109.5 . . N H4'2 C4' H4'3 109.5 . . N C1 N5 C11 124.6(2) . . Y C1 N5 C4 109.0(2) . . Y C11 N5 C4 126.1(2) . . Y C8A C7 C9B 129.3(6) . . Y C8A C7 C9A 113.4(8) . . Y C9B C7 C9A 28.8(5) . . Y C8A C7 C10B 66.1(8) . . Y C9B C7 C10B 112.5(4) . . Y C9A C7 C10B 133.3(5) . . Y C8A C7 N2 115.9(4) . . Y C9B C7 N2 110.9(4) . . Y C9A C7 N2 108.8(5) . . Y C10B C7 N2 112.4(3) . . Y C8A C7 C8B 42.3(7) . . Y C9B C7 C8B 106.6(5) . . Y C9A C7 C8B 80.1(6) . . Y C10B C7 C8B 107.9(4) . . Y N2 C7 C8B 106.2(3) . . Y C8A C7 C10A 108.8(8) . . Y C9B C7 C10A 77.1(5) . . Y C9A C7 C10A 105.4(7) . . Y C10B C7 C10A 44.1(5) . . Y N2 C7 C10A 103.6(4) . . Y C8B C7 C10A 146.0(5) . . Y C7 C8A H8A1 109.5 . . N C7 C8A H8A2 109.5 . . N C7 C8A H8A3 109.5 . . N C7 C9A H9A1 109.5 . . N C7 C9A H9A2 109.5 . . N C7 C9A H9A3 109.5 . . N C7 C10A H10A 109.5 . . N C7 C10A H10B 109.5 . . N C7 C10A H10C 109.5 . . N C7 C8B H8B1 109.5 . . N C7 C8B H8B2 109.5 . . N H8B1 C8B H8B2 109.5 . . N C7 C8B H8B3 109.5 . . N H8B1 C8B H8B3 109.5 . . N H8B2 C8B H8B3 109.5 . . N C7 C9B H9B1 109.5 . . N C7 C9B H9B2 109.5 . . N H9B1 C9B H9B2 109.5 . . N C7 C9B H9B3 109.5 . . N H9B1 C9B H9B3 109.5 . . N H9B2 C9B H9B3 109.5 . . N C7 C10B H10D 109.5 . . N C7 C10B H10E 109.5 . . N H10D C10B H10E 109.5 . . N C7 C10B H10F 109.5 . . N H10D C10B H10F 109.5 . . N H10E C10B H10F 109.5 . . N C12 C11 C16 120.6(3) . . Y C12 C11 N5 119.7(3) . . Y C16 C11 N5 119.7(3) . . Y C11 C12 C13 119.6(3) . . Y C11 C12 H12 120.2 . . N C13 C12 H12 120.2 . . N C14 C13 C12 120.2(3) . . Y C14 C13 H13 119.9 . . N C12 C13 H13 119.9 . . N C15 C14 C13 119.8(3) . . Y C15 C14 H14 120.1 . . N C13 C14 H14 120.1 . . N C14 C15 C16 120.7(3) . . Y C14 C15 H15 119.7 . . N C16 C15 H15 119.7 . . N C11 C16 C15 119.1(3) . . Y C11 C16 H16 120.4 . . N C15 C16 H16 120.4 . . N _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.75 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.551 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.070 #===END data_5429 _database_code_depnum_ccdc_archive 'CCDC 602505' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source CH2Cl2/Et2O _chemical_formula_moiety 'C24 H31 N2, Cl O4' _chemical_formula_sum 'C24 H31 Cl N2 O4' _chemical_formula_weight 446.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5248(2) _cell_length_b 9.5297(2) _cell_length_c 15.4459(4) _cell_angle_alpha 80.3070(10) _cell_angle_beta 88.7100(10) _cell_angle_gamma 60.7890(10) _cell_volume 1203.33(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 24652 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 68.03 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.234 _exptl_crystal_density_method none _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 1.659 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Scalepack, Otwinowski (1997)' _exptl_absorpt_correction_T_min 1 _exptl_absorpt_correction_T_max 1 _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'focusing multilayer optic' _diffrn_measurement_device_type 'Bruker AXS X8 Proteum' _diffrn_measurement_method 'CCD \o- and \w-scan' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 24652 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 68.03 _reflns_number_total 4125 _reflns_number_gt 3654 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'PROTEUM2 (Bruker AXS, 2004)' _computing_cell_refinement 'PROTEUM2 (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _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^)+(0.0488P)^2^+0.7645P] 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_number_reflns 4125 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.005 _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 -0.2463(2) 0.9007(2) 0.29177(11) 0.0187(4) Uani 1 1 d . . . H1 H -0.1474 0.8950 0.3011 0.022 Uiso 1 1 calc R . . C2 C -0.4725(2) 0.9434(2) 0.22772(12) 0.0226(4) Uani 1 1 d . . . H2 H -0.5541 0.9727 0.1851 0.027 Uiso 1 1 calc R . . C3 C -0.4668(2) 0.8822(2) 0.31354(12) 0.0227(4) Uani 1 1 d . . . H3 H -0.5438 0.8610 0.3413 0.027 Uiso 1 1 calc R . . C4 C -0.2939(2) 1.0218(2) 0.13252(11) 0.0182(4) Uani 1 1 d . . . C5 C -0.2362(2) 0.9249(2) 0.06752(12) 0.0199(4) Uani 1 1 d . . . C6 C -0.2041(2) 0.9941(2) -0.01185(12) 0.0222(4) Uani 1 1 d . . . H6 H -0.1673 0.9341 -0.0570 0.027 Uiso 1 1 calc R . . C7 C -0.2263(2) 1.1508(2) -0.02445(12) 0.0234(4) Uani 1 1 d . . . H7 H -0.2041 1.1951 -0.0778 0.028 Uiso 1 1 calc R . . C8 C -0.2814(2) 1.2421(2) 0.04182(12) 0.0235(4) Uani 1 1 d . . . H8 H -0.2947 1.3470 0.0325 0.028 Uiso 1 1 calc R . . C9 C -0.3175(2) 1.1804(2) 0.12232(12) 0.0208(4) Uani 1 1 d . . . C10 C -0.3798(2) 1.2849(2) 0.19365(12) 0.0261(4) Uani 1 1 d . . . H10 H -0.4090 1.2254 0.2421 0.031 Uiso 1 1 calc R . . C11 C -0.5303(3) 1.4482(2) 0.16033(14) 0.0357(5) Uani 1 1 d . . . H11A H -0.5037 1.5109 0.1144 0.054 Uiso 1 1 calc R . . H11B H -0.5706 1.5074 0.2079 0.054 Uiso 1 1 calc R . . H11C H -0.6114 1.4291 0.1377 0.054 Uiso 1 1 calc R . . C12 C -0.2477(3) 1.3117(3) 0.22978(15) 0.0385(5) Uani 1 1 d . . . H12A H -0.1544 1.2078 0.2508 0.058 Uiso 1 1 calc R . . H12B H -0.2867 1.3712 0.2773 0.058 Uiso 1 1 calc R . . H12C H -0.2194 1.3728 0.1838 0.058 Uiso 1 1 calc R . . C13 C -0.2043(2) 0.7497(2) 0.08126(12) 0.0227(4) Uani 1 1 d . . . H13 H -0.2333 0.7230 0.1406 0.027 Uiso 1 1 calc R . . C14 C -0.3080(3) 0.7291(2) 0.01537(14) 0.0299(5) Uani 1 1 d . . . H14A H -0.4198 0.8034 0.0206 0.045 Uiso 1 1 calc R . . H14B H -0.2892 0.6189 0.0276 0.045 Uiso 1 1 calc R . . H14C H -0.2798 0.7520 -0.0433 0.045 Uiso 1 1 calc R . . C15 C -0.0248(2) 0.6333(2) 0.07578(13) 0.0265(4) Uani 1 1 d . . . H15A H 0.0061 0.6564 0.0178 0.040 Uiso 1 1 calc R . . H15B H -0.0044 0.5226 0.0877 0.040 Uiso 1 1 calc R . . H15C H 0.0366 0.6479 0.1184 0.040 Uiso 1 1 calc R . . C16 C -0.2736(2) 0.7991(2) 0.44578(11) 0.0198(4) Uani 1 1 d . . . C17 C -0.2608(2) 0.9053(2) 0.49330(12) 0.0219(4) Uani 1 1 d . . . C18 C -0.2096(2) 0.8462(2) 0.58203(12) 0.0260(4) Uani 1 1 d . . . H18 H -0.1964 0.9127 0.6150 0.031 Uiso 1 1 calc R . . C19 C -0.1773(3) 0.6908(2) 0.62303(12) 0.0277(4) Uani 1 1 d . . . C20 C -0.1938(3) 0.5908(2) 0.57302(13) 0.0280(4) Uani 1 1 d . . . H20 H -0.1731 0.4871 0.6002 0.034 Uiso 1 1 calc R . . C21 C -0.2404(2) 0.6413(2) 0.48337(12) 0.0236(4) Uani 1 1 d . . . C22 C -0.3024(3) 1.0778(2) 0.45275(13) 0.0284(4) Uani 1 1 d . . . H22A H -0.3084 1.1370 0.4985 0.043 Uiso 1 1 calc R . . H22B H -0.4045 1.1309 0.4195 0.043 Uiso 1 1 calc R . . H22C H -0.2206 1.0752 0.4145 0.043 Uiso 1 1 calc R . . C23 C -0.1260(3) 0.6334(3) 0.71995(13) 0.0389(5) Uani 1 1 d . . . H23A H -0.2075 0.6180 0.7507 0.058 Uiso 1 1 calc R . . H23B H -0.1115 0.7139 0.7424 0.058 Uiso 1 1 calc R . . H23C H -0.0262 0.5319 0.7284 0.058 Uiso 1 1 calc R . . C24 C -0.2538(3) 0.5272(2) 0.43106(13) 0.0311(5) Uani 1 1 d . . . H24A H -0.3650 0.5567 0.4226 0.047 Uiso 1 1 calc R . . H24B H -0.1940 0.4169 0.4625 0.047 Uiso 1 1 calc R . . H24C H -0.2108 0.5356 0.3748 0.047 Uiso 1 1 calc R . . N1 N -0.33335(18) 0.95442(17) 0.21493(9) 0.0182(3) Uani 1 1 d . . . N2 N -0.32540(18) 0.85676(18) 0.35270(9) 0.0189(3) Uani 1 1 d . . . O1 O 0.20512(18) 0.94630(18) 0.23637(9) 0.0330(3) Uani 1 1 d . . . O2 O 0.06113(18) 0.9035(2) 0.35334(9) 0.0365(4) Uani 1 1 d . . . O3 O 0.32654(18) 0.70202(18) 0.33960(11) 0.0394(4) Uani 1 1 d . . . O4 O 0.11625(17) 0.75442(18) 0.23942(9) 0.0320(3) Uani 1 1 d . . . Cl1 Cl 0.17791(5) 0.82646(5) 0.29181(3) 0.02241(14) 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 0.0171(10) 0.0205(9) 0.0205(9) -0.0043(7) 0.0027(7) -0.0105(7) C2 0.0178(11) 0.0298(10) 0.0236(9) -0.0045(8) 0.0008(7) -0.0145(8) C3 0.0176(10) 0.0317(10) 0.0238(9) -0.0045(8) 0.0028(7) -0.0160(8) C4 0.0152(10) 0.0220(9) 0.0184(9) -0.0020(7) 0.0010(7) -0.0103(7) C5 0.0178(10) 0.0205(9) 0.0215(9) -0.0031(7) 0.0000(7) -0.0096(7) C6 0.0199(10) 0.0249(9) 0.0209(9) -0.0059(7) 0.0037(7) -0.0099(8) C7 0.0228(11) 0.0266(10) 0.0212(9) 0.0009(7) 0.0012(7) -0.0142(8) C8 0.0249(11) 0.0209(9) 0.0276(10) -0.0023(7) 0.0015(8) -0.0140(8) C9 0.0184(10) 0.0232(9) 0.0215(9) -0.0045(7) 0.0000(7) -0.0106(8) C10 0.0322(12) 0.0223(9) 0.0253(10) -0.0056(8) 0.0026(8) -0.0141(9) C11 0.0355(13) 0.0290(11) 0.0347(11) -0.0106(9) 0.0048(9) -0.0082(9) C12 0.0459(15) 0.0351(12) 0.0380(12) -0.0117(9) -0.0051(10) -0.0207(11) C13 0.0274(11) 0.0217(9) 0.0205(9) -0.0048(7) 0.0051(7) -0.0130(8) C14 0.0265(12) 0.0254(10) 0.0407(12) -0.0081(9) -0.0005(9) -0.0141(8) C15 0.0282(11) 0.0211(9) 0.0271(10) -0.0054(8) -0.0030(8) -0.0093(8) C16 0.0177(10) 0.0270(9) 0.0162(8) -0.0028(7) 0.0022(7) -0.0124(8) C17 0.0192(10) 0.0263(9) 0.0225(9) -0.0055(7) 0.0040(7) -0.0126(8) C18 0.0284(12) 0.0348(11) 0.0223(9) -0.0094(8) 0.0027(8) -0.0199(9) C19 0.0270(11) 0.0351(11) 0.0235(10) -0.0009(8) -0.0011(8) -0.0184(9) C20 0.0321(12) 0.0276(10) 0.0262(10) 0.0027(8) -0.0012(8) -0.0183(9) C21 0.0227(11) 0.0264(10) 0.0249(10) -0.0044(8) 0.0021(8) -0.0146(8) C22 0.0359(12) 0.0277(10) 0.0258(10) -0.0089(8) 0.0046(8) -0.0176(9) C23 0.0518(15) 0.0462(13) 0.0231(10) 0.0019(9) -0.0053(9) -0.0296(12) C24 0.0391(13) 0.0273(10) 0.0309(11) -0.0035(8) -0.0025(9) -0.0197(9) N1 0.0177(8) 0.0202(7) 0.0188(7) -0.0047(6) 0.0025(6) -0.0106(6) N2 0.0171(8) 0.0222(8) 0.0200(8) -0.0045(6) 0.0018(6) -0.0115(6) O1 0.0317(9) 0.0413(8) 0.0325(8) 0.0009(6) -0.0009(6) -0.0252(7) O2 0.0321(9) 0.0585(10) 0.0359(8) -0.0273(7) 0.0146(6) -0.0301(8) O3 0.0263(9) 0.0355(8) 0.0549(10) 0.0056(7) -0.0117(7) -0.0177(7) O4 0.0282(8) 0.0435(8) 0.0376(8) -0.0222(7) 0.0079(6) -0.0235(7) Cl1 0.0190(3) 0.0298(2) 0.0248(2) -0.00861(18) 0.00329(17) -0.01585(19) _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 N2 1.331(2) . Y C1 N1 1.336(2) . Y C1 H1 0.9300 . N C2 C3 1.346(3) . Y C2 N1 1.387(2) . Y C2 H2 0.9300 . N C3 N2 1.381(3) . Y C3 H3 0.9300 . N C4 C9 1.397(2) . Y C4 C5 1.398(2) . Y C4 N1 1.453(2) . Y C5 C6 1.393(2) . Y C5 C13 1.521(2) . Y C6 C7 1.381(3) . Y C6 H6 0.9300 . N C7 C8 1.382(3) . Y C7 H7 0.9300 . N C8 C9 1.393(3) . Y C8 H8 0.9300 . N C9 C10 1.523(2) . Y C10 C11 1.526(3) . Y C10 C12 1.534(3) . Y C10 H10 0.9800 . N C11 H11A 0.9600 . N C11 H11B 0.9600 . N C11 H11C 0.9600 . N C12 H12A 0.9600 . N C12 H12B 0.9600 . N C12 H12C 0.9600 . N C13 C15 1.528(3) . Y C13 C14 1.533(3) . Y C13 H13 0.9800 . N C14 H14A 0.9600 . N C14 H14B 0.9600 . N C14 H14C 0.9600 . N C15 H15A 0.9600 . N C15 H15B 0.9600 . N C15 H15C 0.9600 . N C16 C21 1.396(3) . Y C16 C17 1.397(3) . Y C16 N2 1.454(2) . Y C17 C18 1.391(3) . Y C17 C22 1.511(3) . Y C18 C19 1.391(3) . Y C18 H18 0.9300 . N C19 C20 1.390(3) . Y C19 C23 1.508(3) . Y C20 C21 1.393(3) . Y C20 H20 0.9300 . N C21 C24 1.512(3) . Y C22 H22A 0.9600 . N C22 H22B 0.9600 . N C22 H22C 0.9600 . N C23 H23A 0.9600 . N C23 H23B 0.9600 . N C23 H23C 0.9600 . N C24 H24A 0.9600 . N C24 H24B 0.9600 . N C24 H24C 0.9600 . N O1 Cl1 1.4333(14) . Y O2 Cl1 1.4387(14) . Y O3 Cl1 1.4384(15) . Y O4 Cl1 1.4398(14) . Y 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 C1 N1 108.30(16) . . Y N2 C1 H1 125.9 . . N N1 C1 H1 125.9 . . N C3 C2 N1 106.93(16) . . Y C3 C2 H2 126.5 . . N N1 C2 H2 126.5 . . N C2 C3 N2 107.33(16) . . Y C2 C3 H3 126.3 . . N N2 C3 H3 126.3 . . N C9 C4 C5 123.68(16) . . Y C9 C4 N1 118.15(15) . . Y C5 C4 N1 118.17(15) . . Y C6 C5 C4 117.04(16) . . Y C6 C5 C13 120.01(16) . . Y C4 C5 C13 122.93(15) . . Y C7 C6 C5 120.94(17) . . Y C7 C6 H6 119.5 . . N C5 C6 H6 119.5 . . N C6 C7 C8 120.37(17) . . Y C6 C7 H7 119.8 . . N C8 C7 H7 119.8 . . N C7 C8 C9 121.43(17) . . Y C7 C8 H8 119.3 . . N C9 C8 H8 119.3 . . N C8 C9 C4 116.54(16) . . Y C8 C9 C10 120.16(16) . . Y C4 C9 C10 123.29(16) . . Y C9 C10 C11 111.72(16) . . Y C9 C10 C12 110.64(17) . . Y C11 C10 C12 110.62(17) . . Y C9 C10 H10 107.9 . . N C11 C10 H10 107.9 . . N C12 C10 H10 107.9 . . N C10 C11 H11A 109.5 . . N C10 C11 H11B 109.5 . . N H11A C11 H11B 109.5 . . N C10 C11 H11C 109.5 . . N H11A C11 H11C 109.5 . . N H11B C11 H11C 109.5 . . N C10 C12 H12A 109.5 . . N C10 C12 H12B 109.5 . . N H12A C12 H12B 109.5 . . N C10 C12 H12C 109.5 . . N H12A C12 H12C 109.5 . . N H12B C12 H12C 109.5 . . N C5 C13 C15 109.78(15) . . Y C5 C13 C14 111.51(15) . . Y C15 C13 C14 111.48(15) . . Y C5 C13 H13 108.0 . . N C15 C13 H13 108.0 . . N C14 C13 H13 108.0 . . N C13 C14 H14A 109.5 . . N C13 C14 H14B 109.5 . . N H14A C14 H14B 109.5 . . N C13 C14 H14C 109.5 . . N H14A C14 H14C 109.5 . . N H14B C14 H14C 109.5 . . N C13 C15 H15A 109.5 . . N C13 C15 H15B 109.5 . . N H15A C15 H15B 109.5 . . N C13 C15 H15C 109.5 . . N H15A C15 H15C 109.5 . . N H15B C15 H15C 109.5 . . N C21 C16 C17 123.30(16) . . Y C21 C16 N2 118.52(16) . . Y C17 C16 N2 118.18(15) . . Y C18 C17 C16 116.87(17) . . Y C18 C17 C22 120.21(17) . . Y C16 C17 C22 122.91(16) . . Y C19 C18 C17 122.12(18) . . Y C19 C18 H18 118.9 . . N C17 C18 H18 118.9 . . N C20 C19 C18 118.69(17) . . Y C20 C19 C23 121.01(18) . . Y C18 C19 C23 120.30(18) . . Y C19 C20 C21 121.90(18) . . Y C19 C20 H20 119.1 . . N C21 C20 H20 119.1 . . N C20 C21 C16 117.08(17) . . Y C20 C21 C24 120.17(17) . . Y C16 C21 C24 122.75(17) . . Y C17 C22 H22A 109.5 . . N C17 C22 H22B 109.5 . . N H22A C22 H22B 109.5 . . N C17 C22 H22C 109.5 . . N H22A C22 H22C 109.5 . . N H22B C22 H22C 109.5 . . N C19 C23 H23A 109.5 . . N C19 C23 H23B 109.5 . . N H23A C23 H23B 109.5 . . N C19 C23 H23C 109.5 . . N H23A C23 H23C 109.5 . . N H23B C23 H23C 109.5 . . N C21 C24 H24A 109.5 . . N C21 C24 H24B 109.5 . . N H24A C24 H24B 109.5 . . N C21 C24 H24C 109.5 . . N H24A C24 H24C 109.5 . . N H24B C24 H24C 109.5 . . N C1 N1 C2 108.63(15) . . Y C1 N1 C4 125.87(15) . . Y C2 N1 C4 125.42(15) . . Y C1 N2 C3 108.81(15) . . Y C1 N2 C16 125.00(15) . . Y C3 N2 C16 126.13(15) . . Y O1 Cl1 O3 109.57(9) . . Y O1 Cl1 O2 109.47(9) . . Y O3 Cl1 O2 109.16(10) . . Y O1 Cl1 O4 110.05(9) . . Y O3 Cl1 O4 110.00(9) . . Y O2 Cl1 O4 108.56(8) . . Y _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 68.03 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.369 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.047 ############################################################################ # Attachment 'IMIDAZOLIUM SALTS-x-ray.CIF' data_5434 _database_code_depnum_ccdc_archive 'CCDC 602506' ############################################################################ _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_compound_source Acetonitrile/Ether _chemical_formula_moiety 'C17 H24 N O3, Cl O4' _chemical_formula_sum 'C17 H24 Cl N O7' _chemical_formula_weight 389.82 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' O O 0.0106 0.0060 '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 triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5374(10) _cell_length_b 10.5798(14) _cell_length_c 10.6445(14) _cell_angle_alpha 73.132(5) _cell_angle_beta 87.076(6) _cell_angle_gamma 69.773(5) _cell_volume 963.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 56166 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 33.73 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method none _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Scalepack, Otwinowski (1997)' _exptl_absorpt_correction_T_min 1 _exptl_absorpt_correction_T_max 1 _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.3 mm focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD \w-scan' _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 14693 _diffrn_reflns_av_R_equivalents 0.1008 _diffrn_reflns_av_sigmaI/netI 0.0912 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 27.75 _reflns_number_total 6512 _reflns_number_gt 4830 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect software (Nonius, 1998)' _computing_cell_refinement 'Denzo / Scalepack (Otwinowski 1997)' _computing_data_reduction 'Denzo / Scalepack (Otwinowski 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _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^)+(0.1040P)^2^+0.8197P] 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_number_reflns 6512 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0906 _refine_ls_wR_factor_ref 0.2343 _refine_ls_wR_factor_gt 0.2121 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.8960(2) 1.0610(2) 0.1816(2) 0.0259(4) Uani 1 1 d . . . H1 H 0.9958 1.0601 0.1835 0.031 Uiso 1 1 calc R . . C2 C 0.7011(2) 0.9859(2) 0.2132(2) 0.0260(4) Uani 1 1 d . . . H2 H 0.6626 0.9355 0.1647 0.031 Uiso 1 1 calc R . . C3 C 0.6442(2) 1.1446(2) 0.1487(2) 0.0250(4) Uani 1 1 d . . . H3A H 0.6014 1.1691 0.0585 0.037 Uiso 1 1 calc R . . H3B H 0.5683 1.1944 0.2012 0.037 Uiso 1 1 calc R . . C4 C 0.7882(2) 1.3164(2) 0.1246(2) 0.0243(4) Uani 1 1 d . . . C5 C 0.7788(2) 1.4009(2) -0.0059(2) 0.0256(4) Uani 1 1 d . . . C6 C 0.7807(3) 1.5363(2) -0.0242(2) 0.0297(5) Uani 1 1 d . . . H6 H 0.7730 1.5973 -0.1109 0.036 Uiso 1 1 calc R . . C7 C 0.7936(3) 1.5835(2) 0.0820(3) 0.0323(5) Uani 1 1 d . . . H7 H 0.7958 1.6758 0.0672 0.039 Uiso 1 1 calc R . . C8 C 0.8034(3) 1.4970(2) 0.2097(2) 0.0305(4) Uani 1 1 d . . . H8 H 0.8130 1.5307 0.2812 0.037 Uiso 1 1 calc R . . C9 C 0.7993(2) 1.3613(2) 0.2350(2) 0.0269(4) Uani 1 1 d . . . C10 C 0.8059(3) 1.2703(3) 0.3763(2) 0.0316(5) Uani 1 1 d . . . H10 H 0.7799 1.1870 0.3746 0.038 Uiso 1 1 calc R . . C11 C 0.6929(3) 1.3498(3) 0.4594(2) 0.0376(6) Uani 1 1 d . . . H11A H 0.5925 1.3864 0.4165 0.056 Uiso 1 1 calc R . . H11B H 0.7204 1.4281 0.4678 0.056 Uiso 1 1 calc R . . H11C H 0.6936 1.2854 0.5469 0.056 Uiso 1 1 calc R . . C12 C 0.9636(3) 1.2163(3) 0.4395(3) 0.0461(7) Uani 1 1 d . . . H12A H 1.0341 1.1621 0.3880 0.069 Uiso 1 1 calc R . . H12B H 0.9661 1.1558 0.5293 0.069 Uiso 1 1 calc R . . H12C H 0.9920 1.2963 0.4419 0.069 Uiso 1 1 calc R . . C13 C 0.7607(2) 1.3517(2) -0.1224(2) 0.0268(4) Uani 1 1 d . . . H13 H 0.7748 1.2492 -0.0891 0.032 Uiso 1 1 calc R . . C14 C 0.8778(3) 1.3690(3) -0.2235(3) 0.0337(5) Uani 1 1 d . . . H14A H 0.8653 1.3322 -0.2951 0.051 Uiso 1 1 calc R . . H14B H 0.9783 1.3170 -0.1810 0.051 Uiso 1 1 calc R . . H14C H 0.8649 1.4690 -0.2591 0.051 Uiso 1 1 calc R . . C15 C 0.6017(3) 1.4303(3) -0.1859(3) 0.0330(5) Uani 1 1 d . . . H15A H 0.5289 1.4144 -0.1204 0.050 Uiso 1 1 calc R . . H15B H 0.5897 1.3954 -0.2591 0.050 Uiso 1 1 calc R . . H15C H 0.5849 1.5313 -0.2189 0.050 Uiso 1 1 calc R . . C16 C 0.6897(3) 0.8186(2) 0.4116(2) 0.0296(5) Uani 1 1 d . . . C17 C 0.6253(4) 0.8058(3) 0.5435(3) 0.0445(7) Uani 1 1 d . . . H17A H 0.5158 0.8421 0.5329 0.067 Uiso 1 1 calc R . . H17B H 0.6582 0.8603 0.5885 0.067 Uiso 1 1 calc R . . H17C H 0.6596 0.7066 0.5959 0.067 Uiso 1 1 calc R . . N1 N 0.78301(19) 1.17689(18) 0.14800(18) 0.0232(3) Uani 1 1 d . . . O1 O 0.86540(17) 0.94547(16) 0.21274(17) 0.0270(3) Uani 1 1 d . . . O2 O 0.66295(18) 0.95906(16) 0.34506(16) 0.0278(3) Uani 1 1 d . . . O3 O 0.7557(2) 0.72642(18) 0.36513(19) 0.0355(4) Uani 1 1 d . . . O4 O 0.7675(2) 1.0285(3) 0.7108(2) 0.0464(6) Uani 1 1 d . . . O5 O 0.7931(2) 0.9697(3) 0.93928(19) 0.0422(5) Uani 1 1 d . . . O6 O 0.5630(2) 1.1240(2) 0.8289(3) 0.0522(6) Uani 1 1 d . . . O7 O 0.6435(2) 0.8851(2) 0.8401(2) 0.0428(5) Uani 1 1 d . . . Cl1 Cl 0.69031(6) 1.00226(6) 0.82981(5) 0.02764(15) 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 0.0237(8) 0.0225(9) 0.0288(10) -0.0061(7) 0.0023(7) -0.0059(7) C2 0.0253(8) 0.0231(9) 0.0264(9) -0.0056(7) 0.0025(7) -0.0059(7) C3 0.0231(8) 0.0216(8) 0.0285(9) -0.0050(7) 0.0001(7) -0.0073(7) C4 0.0249(8) 0.0207(8) 0.0265(9) -0.0060(7) -0.0001(7) -0.0073(7) C5 0.0259(9) 0.0217(8) 0.0253(9) -0.0039(7) 0.0009(7) -0.0058(7) C6 0.0330(10) 0.0227(9) 0.0299(10) -0.0036(8) 0.0009(8) -0.0084(8) C7 0.0370(11) 0.0239(9) 0.0353(11) -0.0074(9) 0.0015(9) -0.0107(8) C8 0.0364(11) 0.0249(9) 0.0321(11) -0.0109(8) -0.0023(8) -0.0103(8) C9 0.0291(9) 0.0246(9) 0.0251(9) -0.0065(7) -0.0018(7) -0.0070(7) C10 0.0408(12) 0.0272(10) 0.0231(9) -0.0057(8) -0.0032(8) -0.0077(9) C11 0.0419(13) 0.0359(12) 0.0274(11) -0.0060(9) -0.0005(9) -0.0067(10) C12 0.0423(14) 0.0475(16) 0.0340(13) -0.0075(12) -0.0075(11) -0.0004(12) C13 0.0295(9) 0.0231(9) 0.0242(9) -0.0045(7) -0.0002(7) -0.0066(7) C14 0.0342(11) 0.0348(11) 0.0313(11) -0.0111(9) 0.0065(9) -0.0102(9) C15 0.0296(10) 0.0344(11) 0.0321(11) -0.0082(9) -0.0013(8) -0.0083(9) C16 0.0325(10) 0.0219(9) 0.0305(10) -0.0048(8) 0.0023(8) -0.0073(8) C17 0.0555(16) 0.0304(12) 0.0355(13) -0.0017(10) 0.0143(12) -0.0083(11) N1 0.0232(7) 0.0205(7) 0.0234(8) -0.0047(6) 0.0008(6) -0.0059(6) O1 0.0247(7) 0.0206(6) 0.0321(8) -0.0057(6) 0.0033(6) -0.0052(5) O2 0.0318(7) 0.0209(7) 0.0266(7) -0.0050(6) 0.0044(6) -0.0061(6) O3 0.0432(9) 0.0231(7) 0.0360(9) -0.0073(7) 0.0033(7) -0.0076(7) O4 0.0379(10) 0.0588(13) 0.0328(9) 0.0019(9) 0.0034(7) -0.0175(9) O5 0.0317(8) 0.0640(14) 0.0330(9) -0.0190(9) 0.0016(7) -0.0152(9) O6 0.0287(9) 0.0407(11) 0.0907(18) -0.0327(12) 0.0015(10) -0.0050(8) O7 0.0385(9) 0.0293(9) 0.0604(13) -0.0059(9) -0.0029(9) -0.0169(7) Cl1 0.0248(2) 0.0267(2) 0.0308(3) -0.00800(19) 0.00298(17) -0.00868(17) _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 1.290(3) . Y C1 O1 1.300(3) . Y C1 H1 0.9500 . N C2 O2 1.404(3) . Y C2 O1 1.475(3) . Y C2 C3 1.524(3) . Y C2 H2 1.0000 . N C3 N1 1.476(3) . Y C3 H3A 0.9900 . N C3 H3B 0.9900 . N C4 C5 1.405(3) . Y C4 C9 1.410(3) . Y C4 N1 1.442(3) . Y C5 C6 1.395(3) . Y C5 C13 1.517(3) . Y C6 C7 1.388(4) . Y C6 H6 0.9500 . N C7 C8 1.388(3) . Y C7 H7 0.9500 . N C8 C9 1.396(3) . Y C8 H8 0.9500 . N C9 C10 1.523(3) . Y C10 C12 1.525(4) . Y C10 C11 1.536(4) . Y C10 H10 1.0000 . N C11 H11A 0.9800 . N C11 H11B 0.9800 . N C11 H11C 0.9800 . N C12 H12A 0.9800 . N C12 H12B 0.9800 . N C12 H12C 0.9800 . N C13 C14 1.531(3) . Y C13 C15 1.535(3) . Y C13 H13 1.0000 . N C14 H14A 0.9800 . N C14 H14B 0.9800 . N C14 H14C 0.9800 . N C15 H15A 0.9800 . N C15 H15B 0.9800 . N C15 H15C 0.9800 . N C16 O3 1.190(3) . Y C16 O2 1.386(3) . Y C16 C17 1.492(4) . Y C17 H17A 0.9800 . N C17 H17B 0.9800 . N C17 H17C 0.9800 . N O4 Cl1 1.437(2) . Y O5 Cl1 1.445(2) . Y O6 Cl1 1.430(2) . Y O7 Cl1 1.430(2) . Y 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 O1 116.2(2) . . Y N1 C1 H1 121.9 . . N O1 C1 H1 121.9 . . N O2 C2 O1 107.35(18) . . Y O2 C2 C3 108.71(18) . . Y O1 C2 C3 104.06(17) . . Y O2 C2 H2 112.1 . . N O1 C2 H2 112.1 . . N C3 C2 H2 112.1 . . N N1 C3 C2 101.48(16) . . Y N1 C3 H3A 111.5 . . N C2 C3 H3A 111.5 . . N N1 C3 H3B 111.5 . . N C2 C3 H3B 111.5 . . N H3A C3 H3B 109.3 . . N C5 C4 C9 123.7(2) . . Y C5 C4 N1 118.6(2) . . Y C9 C4 N1 117.74(18) . . Y C6 C5 C4 116.8(2) . . Y C6 C5 C13 120.76(19) . . Y C4 C5 C13 122.4(2) . . Y C7 C6 C5 121.2(2) . . Y C7 C6 H6 119.4 . . N C5 C6 H6 119.4 . . N C8 C7 C6 120.5(2) . . Y C8 C7 H7 119.7 . . N C6 C7 H7 119.7 . . N C7 C8 C9 121.2(2) . . Y C7 C8 H8 119.4 . . N C9 C8 H8 119.4 . . N C8 C9 C4 116.6(2) . . Y C8 C9 C10 119.9(2) . . Y C4 C9 C10 123.4(2) . . Y C9 C10 C12 110.8(2) . . Y C9 C10 C11 111.86(19) . . Y C12 C10 C11 110.2(2) . . Y C9 C10 H10 108.0 . . N C12 C10 H10 108.0 . . N C11 C10 H10 108.0 . . N C10 C11 H11A 109.5 . . N C10 C11 H11B 109.5 . . N H11A C11 H11B 109.5 . . N C10 C11 H11C 109.5 . . N H11A C11 H11C 109.5 . . N H11B C11 H11C 109.5 . . N C10 C12 H12A 109.5 . . N C10 C12 H12B 109.5 . . N H12A C12 H12B 109.5 . . N C10 C12 H12C 109.5 . . N H12A C12 H12C 109.5 . . N H12B C12 H12C 109.5 . . N C5 C13 C14 112.0(2) . . Y C5 C13 C15 109.99(19) . . Y C14 C13 C15 110.96(19) . . Y C5 C13 H13 107.9 . . N C14 C13 H13 107.9 . . N C15 C13 H13 107.9 . . N C13 C14 H14A 109.5 . . N C13 C14 H14B 109.5 . . N H14A C14 H14B 109.5 . . N C13 C14 H14C 109.5 . . N H14A C14 H14C 109.5 . . N H14B C14 H14C 109.5 . . N C13 C15 H15A 109.5 . . N C13 C15 H15B 109.5 . . N H15A C15 H15B 109.5 . . N C13 C15 H15C 109.5 . . N H15A C15 H15C 109.5 . . N H15B C15 H15C 109.5 . . N O3 C16 O2 122.2(2) . . Y O3 C16 C17 127.8(2) . . Y O2 C16 C17 110.0(2) . . Y C16 C17 H17A 109.5 . . N C16 C17 H17B 109.5 . . N H17A C17 H17B 109.5 . . N C16 C17 H17C 109.5 . . N H17A C17 H17C 109.5 . . N H17B C17 H17C 109.5 . . N C1 N1 C4 125.81(19) . . Y C1 N1 C3 109.38(19) . . Y C4 N1 C3 124.59(16) . . Y C1 O1 C2 107.23(16) . . Y C16 O2 C2 115.14(18) . . Y O6 Cl1 O7 109.90(13) . . Y O6 Cl1 O4 110.16(15) . . Y O7 Cl1 O4 109.08(15) . . Y O6 Cl1 O5 109.82(15) . . Y O7 Cl1 O5 109.81(14) . . Y O4 Cl1 O5 108.05(12) . . Y _diffrn_measured_fraction_theta_max 0.846 _diffrn_reflns_theta_full 27.75 _diffrn_measured_fraction_theta_full 0.835 _refine_diff_density_max 0.430 _refine_diff_density_min -1.036 _refine_diff_density_rms 0.074