Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Dr Peter Junk' _publ_contact_author_address ; School of Chemistry Monash University Clayton Victoria 3800 AUSTRALIA ; _publ_contact_author_email PETER.JUNK@SCI.MONASH.EDU.AU _publ_section_title ; Facile purification of the N-heterocyclic carbene precursor [IMesH][Cl] and chloride binding in the solvates [IMesH][Cl].acetone and [IMesH][Cl].H2O (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) ; loop_ _publ_author_name 'Peter Junk' 'Marcus L. Cole' data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 232053' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (IMesH)(Cl).H2O _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 Cl N2 O' _chemical_formula_weight 358.90 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' O O 0.0106 0.0060 '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 8.3198(17) _cell_length_b 15.400(3) _cell_length_c 15.635(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.40(3) _cell_angle_gamma 90.00 _cell_volume 1976.4(7) _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 'regular blocks' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9603 _exptl_absorpt_correction_T_max 0.9603 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _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 'Nonius Kappa CCD' _diffrn_measurement_method 'psi 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 16160 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 30.53 _reflns_number_total 5968 _reflns_number_gt 4699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction Nonius _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.0575P)^2^+0.3922P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5968 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1165 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.273 _refine_ls_shift/su_mean 0.043 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 1.02818(5) -0.02688(2) 0.21777(2) 0.04521(12) Uani 1 1 d . . . O1 O 1.32644(16) -0.02428(8) 0.37196(10) 0.0502(3) Uani 1 1 d . . . N1 N 0.70850(10) 0.18458(6) 0.14169(6) 0.01917(18) Uani 1 1 d . . . N2 N 0.83887(10) 0.20020(6) 0.27206(6) 0.02018(18) Uani 1 1 d . . . C1 C 0.79323(12) 0.14275(7) 0.20886(6) 0.01888(19) Uani 1 1 d . . . C2 C 0.70146(14) 0.27182(8) 0.16233(7) 0.0261(2) Uani 1 1 d . . . C3 C 0.78269(15) 0.28151(8) 0.24390(8) 0.0277(2) Uani 1 1 d . . . C4 C 0.64072(12) 0.14651(7) 0.05900(6) 0.0187(2) Uani 1 1 d . . . C5 C 0.74734(12) 0.12234(7) 0.00263(7) 0.0197(2) Uani 1 1 d . . . C6 C 0.67853(13) 0.09001(7) -0.07814(7) 0.0214(2) Uani 1 1 d . . . C7 C 0.50979(13) 0.08431(7) -0.10351(7) 0.0226(2) Uani 1 1 d . . . C8 C 0.40880(13) 0.10718(8) -0.04476(7) 0.0237(2) Uani 1 1 d . . . C9 C 0.47173(12) 0.13753(7) 0.03813(7) 0.0210(2) Uani 1 1 d . . . C10 C 0.92968(13) 0.13054(9) 0.02702(8) 0.0249(2) Uani 1 1 d . . . C11 C 0.44078(16) 0.05430(10) -0.19383(8) 0.0319(3) Uani 1 1 d . . . C12 C 0.35881(14) 0.15755(10) 0.10189(8) 0.0285(3) Uani 1 1 d . . . C13 C 0.93312(13) 0.17885(7) 0.35563(6) 0.0201(2) Uani 1 1 d . . . C14 C 0.85181(13) 0.14657(7) 0.42029(7) 0.0226(2) Uani 1 1 d . . . C15 C 0.94633(14) 0.12192(8) 0.49854(7) 0.0248(2) Uani 1 1 d . . . C16 C 1.11551(14) 0.13069(7) 0.51279(7) 0.0240(2) Uani 1 1 d . . . C17 C 1.19015(13) 0.16626(8) 0.44711(7) 0.0243(2) Uani 1 1 d . . . C18 C 1.10151(13) 0.19040(8) 0.36723(7) 0.0225(2) Uani 1 1 d . . . C19 C 0.66837(14) 0.13938(10) 0.40695(9) 0.0327(3) Uani 1 1 d . . . C20 C 1.21442(18) 0.10299(10) 0.59782(8) 0.0334(3) Uani 1 1 d . . . C21 C 1.18320(15) 0.22632(11) 0.29576(8) 0.0345(3) Uani 1 1 d . . . H1 H 0.8229(16) 0.0849(10) 0.2094(8) 0.022(3) Uiso 1 1 d . . . H1A H 1.307(3) 0.0230(18) 0.3967(17) 0.086(8) Uiso 1 1 d . . . H1B H 1.246(3) -0.0214(18) 0.3282(19) 0.093(9) Uiso 1 1 d . . . H2 H 0.6462(17) 0.3121(10) 0.1232(10) 0.030(4) Uiso 1 1 d . . . H3 H 0.805(2) 0.3316(12) 0.2780(11) 0.049(5) Uiso 1 1 d . . . H6 H 0.7477(19) 0.0708(10) -0.1157(10) 0.035(4) Uiso 1 1 d . . . H8 H 0.2926(19) 0.0996(10) -0.0608(10) 0.035(4) Uiso 1 1 d . . . H10A H 0.9726(18) 0.0879(10) 0.0721(10) 0.034(4) Uiso 1 1 d . . . H10B H 0.962(2) 0.1879(12) 0.0482(11) 0.044(4) Uiso 1 1 d . . . H10C H 0.981(2) 0.1199(10) -0.0197(11) 0.039(4) Uiso 1 1 d . . . H11A H 0.320(2) 0.0533(12) -0.2043(12) 0.049(5) Uiso 1 1 d . . . H11B H 0.477(2) -0.0068(15) -0.2044(12) 0.061(6) Uiso 1 1 d . . . H11C H 0.473(2) 0.0920(13) -0.2366(12) 0.053(5) Uiso 1 1 d . . . H12A H 0.269(3) 0.1979(16) 0.0762(15) 0.084(7) Uiso 1 1 d . . . H12B H 0.409(2) 0.1788(12) 0.1529(13) 0.054(5) Uiso 1 1 d . . . H12C H 0.301(2) 0.1060(13) 0.1154(12) 0.059(5) Uiso 1 1 d . . . H15 H 0.8933(18) 0.0967(10) 0.5453(10) 0.032(4) Uiso 1 1 d . . . H17 H 1.3074(19) 0.1738(10) 0.4561(10) 0.035(4) Uiso 1 1 d . . . H19A H 0.636(2) 0.1132(11) 0.4590(11) 0.041(4) Uiso 1 1 d . . . H19B H 0.623(2) 0.1060(12) 0.3556(12) 0.047(5) Uiso 1 1 d . . . H19C H 0.620(2) 0.1972(13) 0.3978(12) 0.053(5) Uiso 1 1 d . . . H20A H 1.239(3) 0.1524(17) 0.6390(17) 0.095(8) Uiso 1 1 d . . . H20B H 1.160(3) 0.0638(15) 0.6256(14) 0.067(6) Uiso 1 1 d . . . H20C H 1.320(3) 0.0799(14) 0.5906(14) 0.074(7) Uiso 1 1 d . . . H21A H 1.302(2) 0.2336(12) 0.3157(11) 0.050(5) Uiso 1 1 d . . . H21B H 1.139(2) 0.2853(13) 0.2778(11) 0.049(5) Uiso 1 1 d . . . H21C H 1.164(2) 0.1874(12) 0.2467(12) 0.048(5) 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 Cl1 0.0496(2) 0.0410(2) 0.0506(2) 0.01398(15) 0.02481(16) 0.02537(15) O1 0.0587(7) 0.0354(6) 0.0600(8) -0.0077(5) 0.0202(6) -0.0009(5) N1 0.0184(4) 0.0196(4) 0.0186(4) -0.0012(3) 0.0002(3) 0.0006(3) N2 0.0214(4) 0.0193(4) 0.0186(4) -0.0026(3) -0.0001(3) -0.0005(3) C1 0.0192(4) 0.0184(5) 0.0182(4) -0.0020(4) 0.0004(3) 0.0007(4) C2 0.0329(6) 0.0187(5) 0.0248(5) 0.0001(4) -0.0008(4) 0.0035(4) C3 0.0372(6) 0.0177(5) 0.0261(5) -0.0040(4) -0.0008(5) 0.0012(4) C4 0.0183(4) 0.0205(5) 0.0163(4) -0.0007(4) -0.0006(3) 0.0000(4) C5 0.0170(4) 0.0214(5) 0.0201(5) 0.0022(4) 0.0016(4) -0.0004(4) C6 0.0226(5) 0.0237(5) 0.0183(5) 0.0006(4) 0.0043(4) -0.0008(4) C7 0.0240(5) 0.0242(5) 0.0179(5) 0.0014(4) -0.0015(4) -0.0029(4) C8 0.0179(4) 0.0293(6) 0.0221(5) 0.0006(4) -0.0023(4) -0.0006(4) C9 0.0170(4) 0.0250(5) 0.0206(5) 0.0012(4) 0.0015(4) 0.0022(4) C10 0.0163(4) 0.0326(6) 0.0257(5) 0.0002(5) 0.0029(4) -0.0020(4) C11 0.0336(6) 0.0409(7) 0.0189(5) -0.0030(5) -0.0030(4) -0.0058(5) C12 0.0191(5) 0.0401(7) 0.0266(6) -0.0009(5) 0.0049(4) 0.0050(5) C13 0.0217(4) 0.0211(5) 0.0164(4) -0.0028(4) -0.0005(4) -0.0005(4) C14 0.0227(5) 0.0226(5) 0.0221(5) -0.0017(4) 0.0027(4) -0.0032(4) C15 0.0287(5) 0.0251(5) 0.0209(5) 0.0004(4) 0.0048(4) -0.0033(4) C16 0.0285(5) 0.0221(5) 0.0196(5) -0.0025(4) -0.0011(4) 0.0004(4) C17 0.0209(5) 0.0292(6) 0.0218(5) -0.0046(4) 0.0000(4) 0.0000(4) C18 0.0210(5) 0.0270(5) 0.0193(5) -0.0038(4) 0.0030(4) -0.0016(4) C19 0.0219(5) 0.0424(7) 0.0338(6) 0.0029(6) 0.0049(5) -0.0058(5) C20 0.0397(7) 0.0348(7) 0.0223(6) 0.0026(5) -0.0053(5) 0.0013(6) C21 0.0262(6) 0.0550(9) 0.0231(6) 0.0017(6) 0.0064(4) -0.0061(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 N1 C1 1.3316(13) . ? N1 C2 1.3852(15) . ? N1 C4 1.4475(13) . ? N2 C1 1.3346(13) . ? N2 C3 1.3832(15) . ? N2 C13 1.4476(14) . ? C2 C3 1.3506(17) . ? C4 C9 1.3973(14) . ? C4 C5 1.3990(14) . ? C5 C6 1.3909(15) . ? C5 C10 1.5079(14) . ? C6 C7 1.3979(15) . ? C7 C8 1.3878(16) . ? C7 C11 1.5075(16) . ? C8 C9 1.3966(15) . ? C9 C12 1.5091(15) . ? C13 C18 1.3944(14) . ? C13 C14 1.3964(15) . ? C14 C15 1.3947(16) . ? C14 C19 1.5103(16) . ? C15 C16 1.3953(16) . ? C16 C17 1.3959(16) . ? C16 C20 1.5064(16) . ? C17 C18 1.3932(15) . ? C18 C21 1.5048(16) . ? 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 C1 N1 C2 108.82(9) . . ? C1 N1 C4 125.96(9) . . ? C2 N1 C4 125.16(9) . . ? C1 N2 C3 108.90(9) . . ? C1 N2 C13 124.36(9) . . ? C3 N2 C13 126.73(9) . . ? N1 C1 N2 108.25(10) . . ? C3 C2 N1 107.07(10) . . ? C2 C3 N2 106.95(10) . . ? C9 C4 C5 122.95(9) . . ? C9 C4 N1 118.62(9) . . ? C5 C4 N1 118.41(9) . . ? C6 C5 C4 117.25(9) . . ? C6 C5 C10 120.50(10) . . ? C4 C5 C10 122.25(9) . . ? C5 C6 C7 121.71(10) . . ? C8 C7 C6 118.99(10) . . ? C8 C7 C11 121.25(10) . . ? C6 C7 C11 119.76(10) . . ? C7 C8 C9 121.56(10) . . ? C8 C9 C4 117.41(10) . . ? C8 C9 C12 120.12(10) . . ? C4 C9 C12 122.46(10) . . ? C18 C13 C14 123.12(10) . . ? C18 C13 N2 118.24(9) . . ? C14 C13 N2 118.64(9) . . ? C15 C14 C13 117.49(10) . . ? C15 C14 C19 120.90(10) . . ? C13 C14 C19 121.61(10) . . ? C14 C15 C16 121.56(10) . . ? C15 C16 C17 118.61(10) . . ? C15 C16 C20 120.33(11) . . ? C17 C16 C20 121.06(11) . . ? C18 C17 C16 122.02(10) . . ? C17 C18 C13 117.14(10) . . ? C17 C18 C21 121.78(10) . . ? C13 C18 C21 121.08(10) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.308 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.044 data_Compound_2 _database_code_depnum_ccdc_archive 'CCDC 232054' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (IMesH)(Cl).Acetone _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H31 Cl N2 O' _chemical_formula_weight 398.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3676(17) _cell_length_b 11.315(2) _cell_length_c 13.246(3) _cell_angle_alpha 70.27(3) _cell_angle_beta 80.10(3) _cell_angle_gamma 76.55(3) _cell_volume 1142.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.160 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9141 _exptl_absorpt_correction_T_max 0.9643 _exptl_absorpt_process_details 'performed as part of the DENZO-SMN package' _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 'Nonius Kappa CCD' _diffrn_measurement_method 'psi 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 15323 _diffrn_reflns_av_R_equivalents 0.0849 _diffrn_reflns_av_sigmaI/netI 0.0896 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 30.53 _reflns_number_total 6718 _reflns_number_gt 4607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement DENZO-SMN _computing_data_reduction Nonius _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed / POV-Ray' _computing_publication_material 'Microsoft Office 2000' _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^)+(0.1514P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6718 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1181 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2310 _refine_ls_wR_factor_gt 0.2048 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.054 _refine_ls_shift/su_mean 0.004 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 -0.09805(6) 0.16242(5) 0.26890(4) 0.03012(17) Uani 1 1 d . . . O1 O 0.3204(3) 0.7041(2) 0.22358(19) 0.0537(5) Uani 1 1 d . . . N1 N 0.3800(2) 0.21263(16) 0.27343(12) 0.0207(3) Uani 1 1 d . . . N2 N 0.2382(2) 0.40314(16) 0.21241(12) 0.0215(3) Uani 1 1 d . . . C1 C 0.2347(2) 0.27846(19) 0.24045(14) 0.0214(4) Uani 1 1 d . . . C2 C 0.4817(3) 0.2973(2) 0.26597(16) 0.0249(4) Uani 1 1 d . . . C3 C 0.3928(3) 0.4162(2) 0.22814(16) 0.0261(4) Uani 1 1 d . . . C4 C 0.4169(2) 0.07426(18) 0.31967(14) 0.0204(4) Uani 1 1 d . . . C5 C 0.3298(2) 0.01965(19) 0.41835(15) 0.0226(4) Uani 1 1 d . . . C6 C 0.3630(3) -0.1125(2) 0.46145(16) 0.0253(4) Uani 1 1 d . . . C7 C 0.4787(3) -0.1892(2) 0.40997(16) 0.0273(4) Uani 1 1 d . . . C8 C 0.5636(3) -0.1301(2) 0.31207(16) 0.0261(4) Uani 1 1 d . . . C9 C 0.5344(2) 0.0020(2) 0.26464(15) 0.0228(4) Uani 1 1 d . . . C10 C 0.2044(3) 0.0983(2) 0.47762(16) 0.0275(4) Uani 1 1 d . . . C11 C 0.5125(4) -0.3325(2) 0.4581(2) 0.0381(6) Uani 1 1 d . . . C12 C 0.6270(3) 0.0612(2) 0.15808(17) 0.0274(4) Uani 1 1 d . . . C13 C 0.1000(2) 0.50269(18) 0.17158(14) 0.0204(4) Uani 1 1 d . . . C14 C -0.0474(3) 0.5124(2) 0.23996(15) 0.0248(4) Uani 1 1 d . . . C15 C -0.1829(3) 0.6012(2) 0.19582(17) 0.0269(4) Uani 1 1 d . . . C16 C -0.1738(3) 0.6800(2) 0.08907(16) 0.0252(4) Uani 1 1 d . . . C17 C -0.0223(3) 0.6702(2) 0.02569(16) 0.0255(4) Uani 1 1 d . . . C18 C 0.1153(2) 0.5821(2) 0.06487(15) 0.0235(4) Uani 1 1 d . . . C19 C -0.0604(3) 0.4304(3) 0.35652(17) 0.0345(5) Uani 1 1 d . . . C20 C -0.3240(3) 0.7709(3) 0.0422(2) 0.0357(5) Uani 1 1 d . . . C21 C 0.2744(3) 0.5731(2) -0.00778(18) 0.0304(5) Uani 1 1 d . . . C22 C 0.1963(3) 0.7828(3) 0.2305(2) 0.0406(6) Uani 1 1 d . . . C23 C 0.0813(4) 0.7685(4) 0.3302(3) 0.0626(9) Uani 1 1 d . . . H23A H 0.1249 0.6909 0.3863 0.094 Uiso 1 1 calc R . . H23B H -0.0269 0.7621 0.3157 0.094 Uiso 1 1 calc R . . H23C H 0.0696 0.8430 0.3547 0.094 Uiso 1 1 calc R . . C24 C 0.1502(7) 0.8989(4) 0.1393(3) 0.1008(17) Uani 1 1 d . . . H24A H 0.2381 0.9030 0.0796 0.151 Uiso 1 1 calc R . . H24B H 0.1348 0.9748 0.1624 0.151 Uiso 1 1 calc R . . H24C H 0.0471 0.8959 0.1154 0.151 Uiso 1 1 calc R . . H1 H 0.144(3) 0.246(2) 0.2379(18) 0.021(5) Uiso 1 1 d . . . H2 H 0.599(3) 0.266(2) 0.2825(17) 0.017(5) Uiso 1 1 d . . . H3 H 0.410(4) 0.512(3) 0.211(2) 0.050(8) Uiso 1 1 d . . . H6 H 0.306(4) -0.157(3) 0.533(2) 0.045(8) Uiso 1 1 d . . . H8 H 0.650(3) -0.183(2) 0.2735(19) 0.024(6) Uiso 1 1 d . . . H10A H 0.193(4) 0.045(3) 0.552(3) 0.049(8) Uiso 1 1 d . . . H10B H 0.104(4) 0.123(3) 0.444(2) 0.042(8) Uiso 1 1 d . . . H10C H 0.231(4) 0.182(3) 0.472(2) 0.042(8) Uiso 1 1 d . . . H11A H 0.633(6) -0.366(4) 0.473(3) 0.085(13) Uiso 1 1 d . . . H11B H 0.443(4) -0.373(3) 0.524(3) 0.058(9) Uiso 1 1 d . . . H11C H 0.468(5) -0.363(4) 0.411(3) 0.072(11) Uiso 1 1 d . . . H12A H 0.557(4) 0.121(3) 0.111(3) 0.054(9) Uiso 1 1 d . . . H12B H 0.672(5) 0.006(4) 0.123(3) 0.081(12) Uiso 1 1 d . . . H12C H 0.699(5) 0.099(4) 0.170(3) 0.071(11) Uiso 1 1 d . . . H15 H -0.290(4) 0.611(3) 0.242(3) 0.055(9) Uiso 1 1 d . . . H17 H -0.012(3) 0.723(2) -0.0472(19) 0.025(6) Uiso 1 1 d . . . H19A H 0.054(4) 0.412(3) 0.385(2) 0.050(8) Uiso 1 1 d . . . H19B H -0.162(5) 0.472(4) 0.398(3) 0.066(10) Uiso 1 1 d . . . H19C H -0.083(4) 0.344(3) 0.364(2) 0.042(8) Uiso 1 1 d . . . H20A H -0.307(7) 0.849(6) 0.018(5) 0.13(2) Uiso 1 1 d . . . H20B H -0.372(6) 0.759(5) -0.008(4) 0.114(17) Uiso 1 1 d . . . H20C H -0.419(5) 0.797(4) 0.097(3) 0.074(11) Uiso 1 1 d . . . H21A H 0.249(4) 0.611(3) -0.080(2) 0.048(8) Uiso 1 1 d . . . H21B H 0.360(4) 0.596(3) 0.018(3) 0.050(8) Uiso 1 1 d . . . H21C H 0.331(4) 0.485(4) -0.005(3) 0.051(8) 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 Cl1 0.0268(3) 0.0373(3) 0.0258(3) -0.0052(2) -0.00149(18) -0.0128(2) O1 0.0489(11) 0.0431(12) 0.0791(14) -0.0373(11) -0.0015(10) -0.0043(9) N1 0.0235(7) 0.0213(8) 0.0194(7) -0.0082(6) -0.0010(6) -0.0063(6) N2 0.0241(8) 0.0209(8) 0.0209(7) -0.0083(6) -0.0014(6) -0.0048(6) C1 0.0247(9) 0.0210(9) 0.0188(8) -0.0061(7) -0.0004(7) -0.0065(7) C2 0.0266(9) 0.0269(10) 0.0239(9) -0.0072(8) -0.0024(7) -0.0112(8) C3 0.0292(10) 0.0246(10) 0.0271(9) -0.0084(8) -0.0028(8) -0.0097(8) C4 0.0228(8) 0.0183(9) 0.0213(8) -0.0074(7) -0.0038(7) -0.0036(7) C5 0.0278(9) 0.0225(10) 0.0198(8) -0.0085(7) -0.0031(7) -0.0058(8) C6 0.0317(10) 0.0239(10) 0.0210(8) -0.0062(7) -0.0026(7) -0.0074(8) C7 0.0348(10) 0.0225(10) 0.0266(9) -0.0089(8) -0.0048(8) -0.0062(8) C8 0.0304(10) 0.0253(10) 0.0260(9) -0.0137(8) -0.0021(8) -0.0037(8) C9 0.0258(9) 0.0242(10) 0.0220(8) -0.0104(7) -0.0038(7) -0.0060(8) C10 0.0332(11) 0.0259(11) 0.0214(9) -0.0082(8) 0.0034(8) -0.0053(9) C11 0.0547(16) 0.0213(11) 0.0350(12) -0.0083(9) -0.0007(11) -0.0041(11) C12 0.0298(10) 0.0320(11) 0.0232(9) -0.0122(8) 0.0002(8) -0.0078(9) C13 0.0217(8) 0.0190(9) 0.0213(8) -0.0080(7) -0.0019(7) -0.0027(7) C14 0.0293(10) 0.0232(10) 0.0215(8) -0.0087(7) 0.0012(7) -0.0042(8) C15 0.0276(9) 0.0262(10) 0.0283(9) -0.0136(8) -0.0004(8) -0.0015(8) C16 0.0272(9) 0.0239(10) 0.0278(9) -0.0135(8) -0.0049(7) -0.0013(8) C17 0.0309(10) 0.0232(10) 0.0230(9) -0.0077(8) -0.0028(7) -0.0051(8) C18 0.0262(9) 0.0235(10) 0.0231(9) -0.0087(7) -0.0008(7) -0.0083(8) C19 0.0391(12) 0.0331(13) 0.0230(9) -0.0077(9) 0.0044(9) 0.0020(10) C20 0.0338(11) 0.0345(13) 0.0379(12) -0.0138(10) -0.0108(10) 0.0042(10) C21 0.0279(10) 0.0327(12) 0.0256(10) -0.0043(9) 0.0028(8) -0.0071(9) C22 0.0467(14) 0.0367(14) 0.0467(14) -0.0236(11) 0.0029(11) -0.0137(11) C23 0.0589(19) 0.080(3) 0.0522(17) -0.0273(16) 0.0144(14) -0.0238(18) C24 0.130(4) 0.063(3) 0.067(2) -0.0073(19) 0.023(2) 0.020(3) _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 O1 C22 1.213(3) . ? N1 C1 1.329(3) . ? N1 C2 1.392(2) . ? N1 C4 1.454(2) . ? N2 C1 1.338(3) . ? N2 C3 1.393(3) . ? N2 C13 1.448(3) . ? C2 C3 1.350(3) . ? C4 C9 1.396(3) . ? C4 C5 1.399(3) . ? C5 C6 1.387(3) . ? C5 C10 1.505(3) . ? C6 C7 1.392(3) . ? C7 C8 1.397(3) . ? C7 C11 1.506(3) . ? C8 C9 1.392(3) . ? C9 C12 1.506(3) . ? C13 C18 1.399(3) . ? C13 C14 1.405(3) . ? C14 C15 1.392(3) . ? C14 C19 1.510(3) . ? C15 C16 1.394(3) . ? C16 C17 1.398(3) . ? C16 C20 1.503(3) . ? C17 C18 1.382(3) . ? C18 C21 1.507(3) . ? C22 C24 1.479(5) . ? C22 C23 1.479(4) . ? 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 C1 N1 C2 109.28(17) . . ? C1 N1 C4 123.92(16) . . ? C2 N1 C4 126.53(17) . . ? C1 N2 C3 108.58(17) . . ? C1 N2 C13 123.02(16) . . ? C3 N2 C13 128.39(17) . . ? N1 C1 N2 108.24(17) . . ? C3 C2 N1 106.66(18) . . ? C2 C3 N2 107.24(18) . . ? C9 C4 C5 122.99(18) . . ? C9 C4 N1 119.54(16) . . ? C5 C4 N1 117.47(17) . . ? C6 C5 C4 117.41(18) . . ? C6 C5 C10 119.95(17) . . ? C4 C5 C10 122.64(18) . . ? C5 C6 C7 122.03(18) . . ? C6 C7 C8 118.43(19) . . ? C6 C7 C11 121.16(19) . . ? C8 C7 C11 120.4(2) . . ? C9 C8 C7 122.01(19) . . ? C8 C9 C4 117.13(17) . . ? C8 C9 C12 120.10(19) . . ? C4 C9 C12 122.77(19) . . ? C18 C13 C14 122.35(18) . . ? C18 C13 N2 119.23(17) . . ? C14 C13 N2 118.38(17) . . ? C15 C14 C13 117.25(18) . . ? C15 C14 C19 120.75(18) . . ? C13 C14 C19 122.00(19) . . ? C14 C15 C16 122.07(19) . . ? C15 C16 C17 118.40(19) . . ? C15 C16 C20 120.87(19) . . ? C17 C16 C20 120.71(19) . . ? C18 C17 C16 121.88(18) . . ? C17 C18 C13 117.97(18) . . ? C17 C18 C21 119.74(18) . . ? C13 C18 C21 122.28(19) . . ? O1 C22 C24 121.9(3) . . ? O1 C22 C23 122.2(3) . . ? C24 C22 C23 115.8(3) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 30.53 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.936 _refine_diff_density_min -0.769 _refine_diff_density_rms 0.111