# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Dario Braga' 'Ulrich Baisch' 'Katia Rubini' _publ_contact_author_name 'Dario Braga' _publ_contact_author_email DARIO.BRAGA@UNIBO.IT _publ_section_title ; Remarkable structural similarities between organic co-crystals and a metal-organic coordination network - insights into hydrogen bonded aliphatic ammonium chlorides ; # Attachment 'Piperazinium_dichloride_hemihyrate.cif' data_ub043n_2 _database_code_depnum_ccdc_archive 'CCDC 696300' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'dipiperazinium tetrachloride monohydrate' ; _chemical_name_common ; 'dipiperazinium tetrachloride monohydrate' ; _chemical_formula_moiety '2(C4 H12 N2), H2 O, 4(Cl)' _chemical_formula_sum 'C8 H26 Cl4 N4 O' _chemical_formula_weight 336.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_space_group_name_H-M 'P n m a' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 11.6011(11) _cell_length_b 9.6530(8) _cell_length_c 13.9669(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1564.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200 _cell_measurement_reflns_used 1765 _cell_measurement_theta_min 2.5447 _cell_measurement_theta_max 28.8855 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3508 _exptl_crystal_size_mid 0.0787 _exptl_crystal_size_min 0.0329 _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.751 _exptl_absorpt_correction_T_min 0.875 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_measurement_device_type xcalibur _diffrn_measurement_device '95mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1340 _diffrn_reflns_number 5299 _diffrn_reflns_av_R_equivalents 0.0578 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 29.02 _diffrn_orient_matrix_UB_11 -0.0230008026 _diffrn_orient_matrix_UB_12 0.0263551432 _diffrn_orient_matrix_UB_13 -0.0428590105 _diffrn_orient_matrix_UB_21 -0.0202155303 _diffrn_orient_matrix_UB_22 -0.0546054986 _diffrn_orient_matrix_UB_23 -0.0179236353 _diffrn_orient_matrix_UB_31 -0.0662360849 _diffrn_orient_matrix_UB_32 0.0075368397 _diffrn_orient_matrix_UB_33 0.0202805561 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -41.00 53.80 1.2000 130.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.4392 45.0000 30.0000 0.0000 0.0000 79 #__ type_ start__ end____ width___ exp.time_ 2 omega -88.00 -35.20 1.2000 130.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.4392 -77.0000 270.0000 0.0000 0.0000 44 #__ type_ start__ end____ width___ exp.time_ 3 omega 11.00 42.20 1.2000 130.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -45.0000 30.0000 0.0000 0.0000 26 ; _reflns_number_total 1916 _reflns_number_gt 1160 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0419P)^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_number_reflns 1916 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.0920 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_restrained_S_all 0.888 _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 Cl1 Cl 0.63194(8) 0.2500 0.61447(6) 0.0270(2) Uani 1 2 d S . . Cl2 Cl 0.03684(8) 0.2500 0.35063(7) 0.0280(2) Uani 1 2 d S . . N21 N -0.1364(3) 0.2500 0.7304(2) 0.0232(7) Uani 1 2 d S . . N22 N 0.0176(3) 0.2500 0.5711(3) 0.0264(8) Uani 1 2 d S . . N11 N 0.3224(3) 0.2500 0.2805(2) 0.0276(8) Uani 1 2 d S . . N12 N 0.4274(3) 0.2500 0.4641(2) 0.0271(8) Uani 1 2 d S . . C11 C 0.4267(2) 0.1230(3) 0.4047(2) 0.0286(7) Uani 1 1 d . . . C12 C 0.3233(2) 0.1232(3) 0.3401(2) 0.0285(7) Uani 1 1 d . . . C21 C -0.0705(3) 0.1243(3) 0.70460(19) 0.0232(6) Uani 1 1 d . . . C22 C -0.0453(3) 0.1217(3) 0.59935(19) 0.0272(6) Uani 1 1 d . . . Cl3 Cl 0.24919(6) 0.06263(6) 0.59884(5) 0.0344(2) Uani 1 1 d . . . O3 O 0.1837(3) 0.2500 0.1226(2) 0.0345(8) Uani 1 2 d S . . H1 H -0.1123(19) 0.047(2) 0.7199(16) 0.014(7) Uiso 1 1 d . . . H2 H 0.326(2) 0.049(3) 0.2968(17) 0.019(7) Uiso 1 1 d . . . H3 H 0.007(2) 0.040(3) 0.5833(18) 0.027(7) Uiso 1 1 d . . . H4 H 0.002(2) 0.122(3) 0.7399(18) 0.034(8) Uiso 1 1 d . . . H5 H 0.024(3) 0.2500 0.514(3) 0.020(11) Uiso 1 2 d S . . H6 H 0.427(2) 0.051(3) 0.4494(18) 0.025(7) Uiso 1 1 d . . . H7 H 0.486(4) 0.2500 0.506(3) 0.036(12) Uiso 1 2 d S . . H8 H -0.112(2) 0.119(3) 0.5588(19) 0.032(8) Uiso 1 1 d . . . H9 H 0.251(2) 0.120(3) 0.3753(19) 0.037(8) Uiso 1 1 d . . . H10 H -0.148(3) 0.2500 0.791(3) 0.038(12) Uiso 1 2 d S . . H11 H -0.199(4) 0.2500 0.702(3) 0.040(13) Uiso 1 2 d S . . H12 H 0.087(4) 0.2500 0.598(3) 0.037(13) Uiso 1 2 d S . . H13 H 0.204(3) 0.181(3) 0.097(2) 0.050(10) Uiso 1 1 d . . . H14 H 0.498(2) 0.117(3) 0.3669(18) 0.029(8) Uiso 1 1 d . . . H16 H 0.378(4) 0.2500 0.238(3) 0.041(13) Uiso 1 2 d S . . H21 H 0.370(4) 0.2500 0.503(3) 0.043(14) Uiso 1 2 d S . . H23 H 0.262(4) 0.2500 0.243(3) 0.044(14) Uiso 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 Cl1 0.0274(5) 0.0294(5) 0.0241(5) 0.000 -0.0031(4) 0.000 Cl2 0.0294(5) 0.0319(5) 0.0226(5) 0.000 -0.0026(4) 0.000 N21 0.0205(19) 0.0327(19) 0.0165(17) 0.000 0.0010(15) 0.000 N22 0.028(2) 0.033(2) 0.018(2) 0.000 0.0030(16) 0.000 N11 0.0238(19) 0.041(2) 0.0185(16) 0.000 0.0000(16) 0.000 N12 0.024(2) 0.035(2) 0.0229(18) 0.000 -0.0077(17) 0.000 C11 0.0294(16) 0.0205(14) 0.0361(17) 0.0032(15) -0.0065(14) 0.0011(13) C12 0.0252(16) 0.0227(15) 0.0375(17) -0.0097(15) -0.0035(14) -0.0026(14) C21 0.0286(16) 0.0154(13) 0.0256(15) 0.0026(13) -0.0002(13) -0.0023(14) C22 0.0322(16) 0.0233(15) 0.0262(15) -0.0034(14) 0.0001(14) -0.0024(14) Cl3 0.0412(4) 0.0270(4) 0.0350(4) -0.0025(3) -0.0036(3) 0.0011(3) O3 0.0375(18) 0.0337(19) 0.0322(17) 0.000 -0.0031(14) 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 N21 C21 1.479(3) 7_565 ? N21 C21 1.479(3) . ? N21 H10 0.85(4) . ? N21 H11 0.82(4) . ? N22 C22 1.490(3) . ? N22 C22 1.490(3) 7_565 ? N22 H5 0.80(4) . ? N22 H12 0.88(4) . ? N11 C12 1.480(3) . ? N11 C12 1.480(3) 7_565 ? N11 H16 0.88(4) . ? N11 H23 0.87(4) . ? N12 C11 1.480(3) . ? N12 C11 1.480(3) 7_565 ? N12 H7 0.89(4) . ? N12 H21 0.86(4) . ? C11 C12 1.501(4) . ? C11 H6 0.94(3) . ? C11 H14 0.99(2) . ? C12 H2 0.94(2) . ? C12 H9 0.97(3) . ? C21 C22 1.499(4) . ? C21 H1 0.91(2) . ? C21 H4 0.97(3) . ? C22 H3 1.02(3) . ? C22 H8 0.96(3) . ? O3 H13 0.79(3) . ? 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 C21 N21 C21 110.3(3) 7_565 . ? C21 N21 H10 108.8(13) 7_565 . ? C21 N21 H10 108.8(13) . . ? C21 N21 H11 109.7(14) 7_565 . ? C21 N21 H11 109.7(14) . . ? H10 N21 H11 109(4) . . ? C22 N22 C22 112.4(3) . 7_565 ? C22 N22 H5 108.0(13) . . ? C22 N22 H5 108.0(13) 7_565 . ? C22 N22 H12 109.4(12) . . ? C22 N22 H12 109.4(12) 7_565 . ? H5 N22 H12 110(4) . . ? C12 N11 C12 111.6(3) . 7_565 ? C12 N11 H16 112.1(12) . . ? C12 N11 H16 112.1(12) 7_565 . ? C12 N11 H23 109.9(13) . . ? C12 N11 H23 109.9(13) 7_565 . ? H16 N11 H23 101(3) . . ? C11 N12 C11 111.9(3) . 7_565 ? C11 N12 H7 111.7(12) . . ? C11 N12 H7 111.7(12) 7_565 . ? C11 N12 H21 110.5(14) . . ? C11 N12 H21 110.5(13) 7_565 . ? H7 N12 H21 100(4) . . ? N12 C11 C12 109.9(3) . . ? N12 C11 H6 104.0(16) . . ? C12 C11 H6 113.9(16) . . ? N12 C11 H14 110.0(16) . . ? C12 C11 H14 110.6(15) . . ? H6 C11 H14 108(2) . . ? N11 C12 C11 110.2(3) . . ? N11 C12 H2 105.5(14) . . ? C11 C12 H2 111.1(15) . . ? N11 C12 H9 107.6(17) . . ? C11 C12 H9 112.5(16) . . ? H2 C12 H9 110(2) . . ? N21 C21 C22 110.7(2) . . ? N21 C21 H1 109.8(14) . . ? C22 C21 H1 108.6(14) . . ? N21 C21 H4 109.7(16) . . ? C22 C21 H4 109.1(15) . . ? H1 C21 H4 109(2) . . ? N22 C22 C21 110.0(2) . . ? N22 C22 H3 107.0(14) . . ? C21 C22 H3 110.2(14) . . ? N22 C22 H8 105.1(16) . . ? C21 C22 H8 115.1(15) . . ? H3 C22 H8 109(2) . . ? _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.428 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.082 # Attachment 'Piperazinium_dichloride_monohyrate.cif' data_043n_070308_5 _database_code_depnum_ccdc_archive 'CCDC 696301' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'piperazinium dichloride monohydrate' ; _chemical_name_common ; 'piperazinium dichloride monohydrate' ; _chemical_formula_moiety 'C4 H12 N2, H2 O, 2(Cl)' _chemical_formula_sum 'C4 H14 Cl2 N2 O' _chemical_formula_weight 177.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.1916(3) _cell_length_b 6.3108(2) _cell_length_c 13.4929(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.553(3) _cell_angle_gamma 90.00 _cell_volume 827.42(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4590 _cell_measurement_theta_min 3.1489 _cell_measurement_theta_max 29.3412 _exptl_absorpt_coefficient_mu 0.711 _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3074 _exptl_crystal_size_mid 0.2099 _exptl_crystal_size_min 0.0414 _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _diffrn_measurement_device_type xcalibur _diffrn_measurement_device '95mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1340 _diffrn_reflns_number 9549 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 29.47 _reflns_number_total 1052 _reflns_number_gt 787 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 -0.0114045098 _diffrn_orient_matrix_UB_12 -0.0476975938 _diffrn_orient_matrix_UB_13 0.0442112230 _diffrn_orient_matrix_UB_21 -0.0592250400 _diffrn_orient_matrix_UB_22 0.0638485545 _diffrn_orient_matrix_UB_23 -0.0068199775 _diffrn_orient_matrix_UB_31 -0.0408613331 _diffrn_orient_matrix_UB_32 -0.0791183565 _diffrn_orient_matrix_UB_33 -0.0320767880 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -43.00 9.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 0.0000 330.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 2 omega -89.00 -39.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 -45.0000 30.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 3 omega 5.00 51.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 0.0000 240.0000 0.0000 0.0000 46 #__ type_ start__ end____ width___ exp.time_ 4 omega -43.00 6.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 -45.0000 210.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 5 omega -89.00 6.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 -45.0000 120.0000 0.0000 0.0000 95 #__ type_ start__ end____ width___ exp.time_ 6 omega -39.00 13.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 -77.0000 150.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 7 omega 5.00 55.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 0.0000 180.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 8 omega -43.00 6.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 -45.0000 270.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 9 omega 5.00 54.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 45.0000 0.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 10 omega -48.00 4.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 77.0000 210.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 11 omega 5.00 54.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 45.0000 60.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 12 omega -48.00 5.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 77.0000 120.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 13 omega -84.00 -43.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5173 -45.0000 240.0000 0.0000 0.0000 41 #__ type_ start__ end____ width___ exp.time_ 14 omega 38.00 79.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -129.0000 86.0000 0.0000 0.0000 41 #__ type_ start__ end____ width___ exp.time_ 15 omega 38.00 78.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -129.0000 357.0000 0.0000 0.0000 40 #__ type_ start__ end____ width___ exp.time_ 16 omega -51.00 -17.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -77.0000 180.0000 0.0000 0.0000 34 #__ type_ start__ end____ width___ exp.time_ 17 omega -6.00 43.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -45.0000 240.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 18 omega -11.00 41.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 77.0000 30.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 19 omega 14.00 60.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -96.0000 36.0000 0.0000 0.0000 46 #__ type_ start__ end____ width___ exp.time_ 20 omega 6.00 48.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -87.0000 101.0000 0.0000 0.0000 42 #__ type_ start__ end____ width___ exp.time_ 21 omega 20.00 64.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -104.0000 237.0000 0.0000 0.0000 44 #__ type_ start__ end____ width___ exp.time_ 22 omega -51.00 37.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -77.0000 300.0000 0.0000 0.0000 88 #__ type_ start__ end____ width___ exp.time_ 23 omega 13.00 38.00 1.0000 75.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 77.0000 90.0000 0.0000 0.0000 25 ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0514P)^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_number_reflns 1052 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 Cl1 Cl 0.79893(4) 0.09521(7) 0.66353(3) 0.04130(18) Uani 1 1 d . . . N1 N 0.55067(15) 0.4117(2) 0.60227(10) 0.0310(3) Uani 1 1 d . . . C1 C 0.62655(17) 0.5834(3) 0.56830(13) 0.0332(4) Uani 1 1 d . . . C2 C 0.52860(17) 0.7184(3) 0.48735(13) 0.0340(4) Uani 1 1 d . . . O1 O 1.0000 0.5439(4) 0.7500 0.0724(7) Uani 1 2 d S . . H1A H 0.6932(19) 0.512(3) 0.5409(14) 0.037(5) Uiso 1 1 d . . . H1B H 0.671(2) 0.670(3) 0.6315(15) 0.047(5) Uiso 1 1 d . . . H2A H 0.461(2) 0.785(3) 0.5165(14) 0.040(5) Uiso 1 1 d . . . H2B H 0.579(2) 0.838(3) 0.4653(15) 0.043(5) Uiso 1 1 d . . . H1N H 0.496(2) 0.465(3) 0.6395(15) 0.042(5) Uiso 1 1 d . . . H2N H 0.610(2) 0.329(4) 0.6475(15) 0.052(6) Uiso 1 1 d . . . H1O H 1.064(2) 0.455(4) 0.7484(19) 0.063 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 0.0371(3) 0.0517(3) 0.0342(3) 0.00147(18) 0.00949(17) 0.01658(19) N1 0.0277(6) 0.0364(7) 0.0281(7) 0.0019(6) 0.0071(5) 0.0039(6) C1 0.0264(7) 0.0383(9) 0.0323(8) -0.0044(7) 0.0050(6) -0.0039(7) C2 0.0353(8) 0.0266(8) 0.0405(9) -0.0025(7) 0.0120(7) -0.0019(7) O1 0.0549(14) 0.0557(14) 0.112(2) 0.000 0.0333(15) 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 N1 C1 1.482(2) . ? N1 C2 1.483(2) 5_666 ? N1 H1N 0.91(2) . ? N1 H2N 0.89(2) . ? C1 C2 1.503(2) . ? C1 H1A 0.976(19) . ? C1 H1B 1.00(2) . ? C2 N1 1.483(2) 5_666 ? C2 H2A 0.98(2) . ? C2 H2B 1.01(2) . ? O1 H1O 0.86(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 C1 N1 C2 111.05(13) . 5_666 ? C1 N1 H1N 111.1(13) . . ? C2 N1 H1N 112.3(12) 5_666 . ? C1 N1 H2N 109.6(14) . . ? C2 N1 H2N 109.0(14) 5_666 . ? H1N N1 H2N 103.6(17) . . ? N1 C1 C2 110.20(13) . . ? N1 C1 H1A 105.4(11) . . ? C2 C1 H1A 111.9(11) . . ? N1 C1 H1B 106.4(12) . . ? C2 C1 H1B 109.9(12) . . ? H1A C1 H1B 112.8(15) . . ? N1 C2 C1 110.98(13) 5_666 . ? N1 C2 H2A 106.8(11) 5_666 . ? C1 C2 H2A 110.0(11) . . ? N1 C2 H2B 112.0(11) 5_666 . ? C1 C2 H2B 110.8(11) . . ? H2A C2 H2B 106.1(15) . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.336 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.048 # Attachment 'dace_dichloride.cif' data_043d_1 _database_code_depnum_ccdc_archive 'CCDC 696302' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-diammonio-cyclohexane dichloride' ; _chemical_name_common ; '1,2-diammonio-cyclohexane dichloride' ; _chemical_formula_moiety 'C6 H16 N2, 2(Cl)' _chemical_formula_sum 'C6 H16 Cl2 N2' _chemical_formula_weight 187.11 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_space_group_name_H-M 'P 1 21/n 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' 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 5.25760(10) _cell_length_b 14.8849(3) _cell_length_c 6.35470(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.850(2) _cell_angle_gamma 90.00 _cell_volume 489.981(16) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5192 _cell_measurement_theta_min 2.7266 _cell_measurement_theta_max 29.2953 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3190 _exptl_crystal_size_mid 0.2335 _exptl_crystal_size_min 0.0457 _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.601 _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_measurement_device_type xcalibur _diffrn_measurement_device '95mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1340 _diffrn_reflns_number 8998 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 29.39 _reflns_number_total 1208 _reflns_number_gt 993 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0456P)^2^+0.0071P] 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_number_reflns 1208 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 Cl1 Cl 0.03190(6) 0.84579(2) 0.53709(5) 0.03928(14) Uani 1 1 d . . . N1 N -0.5257(2) 0.84292(9) 0.2519(2) 0.0345(3) Uani 1 1 d . . . H1N H -0.637(3) 0.8429(9) 0.324(3) 0.046(4) Uiso 1 1 d . . . H2N H -0.527(3) 0.7940(11) 0.194(2) 0.037(4) Uiso 1 1 d . . . H3N H -0.387(3) 0.8521(8) 0.335(3) 0.036(4) Uiso 1 1 d . . . C1 C -0.5747(2) 0.91580(8) 0.09044(19) 0.0284(3) Uani 1 1 d . . . H1 H -0.727(2) 0.9006(9) 0.000(2) 0.032(3) Uiso 1 1 d . . . C2 C -0.3564(3) 0.91887(9) -0.0393(2) 0.0366(3) Uani 1 1 d . . . H2A H -0.193(3) 0.9282(9) 0.067(2) 0.044(4) Uiso 1 1 d . . . H2B H -0.352(3) 0.8626(10) -0.115(3) 0.044(4) Uiso 1 1 d . . . C3 C -0.3977(3) 0.99521(8) -0.1998(2) 0.0337(3) Uani 1 1 d . . . H3A H -0.263(3) 0.9974(8) -0.283(3) 0.044(4) Uiso 1 1 d . . . H3B H -0.554(3) 0.9841(9) -0.301(3) 0.040(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 Cl1 0.0382(2) 0.0407(2) 0.0411(2) 0.00221(13) 0.01291(14) -0.00250(13) N1 0.0361(6) 0.0344(6) 0.0354(6) 0.0003(5) 0.0129(5) 0.0000(5) C1 0.0267(6) 0.0323(6) 0.0270(6) -0.0020(5) 0.0068(5) -0.0010(5) C2 0.0409(7) 0.0342(7) 0.0395(7) 0.0003(5) 0.0206(6) 0.0069(5) C3 0.0391(7) 0.0368(7) 0.0287(6) -0.0031(5) 0.0154(6) 0.0010(5) _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 1.4852(16) . ? N1 H1N 0.802(18) . ? N1 H2N 0.817(17) . ? N1 H3N 0.835(16) . ? C1 C3 1.5141(16) 3_475 ? C1 C2 1.5243(16) . ? C1 H1 0.932(14) . ? C2 C3 1.5174(17) . ? C2 H2A 1.005(15) . ? C2 H2B 0.970(16) . ? C3 C1 1.5142(16) 3_475 ? C3 H3A 0.953(19) . ? C3 H3B 0.967(15) . ? 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 H1N 109.6(11) . . ? C1 N1 H2N 110.6(10) . . ? H1N N1 H2N 107.8(14) . . ? C1 N1 H3N 110.2(9) . . ? H1N N1 H3N 106.7(16) . . ? H2N N1 H3N 111.8(14) . . ? N1 C1 C3 109.92(10) . 3_475 ? N1 C1 C2 109.76(10) . . ? C3 C1 C2 111.23(10) 3_475 . ? N1 C1 H1 106.2(8) . . ? C3 C1 H1 110.9(8) 3_475 . ? C2 C1 H1 108.7(8) . . ? C3 C2 C1 110.58(10) . . ? C3 C2 H2A 110.8(8) . . ? C1 C2 H2A 106.1(8) . . ? C3 C2 H2B 109.0(9) . . ? C1 C2 H2B 109.3(9) . . ? H2A C2 H2B 111.2(13) . . ? C1 C3 C2 111.13(11) 3_475 . ? C1 C3 H3A 111.2(8) 3_475 . ? C2 C3 H3A 111.3(8) . . ? C1 C3 H3B 108.5(9) 3_475 . ? C2 C3 H3B 109.0(8) . . ? H3A C3 H3B 105.4(13) . . ? _diffrn_measured_fraction_theta_max 0.892 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.260 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.042 # Attachment 'dace_dichloride_bisDMSO.cif' data_ub043m_1 _database_code_depnum_ccdc_archive 'CCDC 696303' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,2-diammonio-cyclohexane dichloride mono-sulfoxide' ; _chemical_name_common ; '1,2-diammonio-cyclohexane dichloride mono-sulfoxide' ; _chemical_formula_moiety 'C6 H16 N2, 2(C2 H6 O S), 2(Cl)' _chemical_formula_sum 'C10 H28 Cl2 N2 O2 S2' _chemical_formula_weight 343.36 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' Cl Cl 0.1484 0.1585 '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' S S 0.1246 0.1234 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8630(6) _cell_length_b 8.2478(9) _cell_length_c 9.5959(9) _cell_angle_alpha 89.659(8) _cell_angle_beta 76.931(8) _cell_angle_gamma 75.820(9) _cell_volume 437.64(8) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4109 _cell_measurement_theta_min 2.5502 _cell_measurement_theta_max 29.4046 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.607 _exptl_absorpt_correction_T_min 0.772 _exptl_absorpt_correction_T_max 0.910 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET) (compiled Nov 29 2007,17:23:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET) (compiled Nov 29 2007,17:23:28) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET) (compiled Nov 29 2007,17:23:28) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.13 (release 29-11-2007 CrysAlis171 .NET) (compiled Nov 29 2007,17:23:28) ; _diffrn_measurement_device_type xcalibur _diffrn_measurement_device '95mm CCD camera (sapphire) on \k-goniostat' _diffrn_measurement_method 'omega scan' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1340 _diffrn_reflns_number 9199 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.5502 _diffrn_reflns_theta_max 29.4046 _diffrn_orient_matrix_UB_11 -0.0428873959 _diffrn_orient_matrix_UB_12 0.0879473189 _diffrn_orient_matrix_UB_13 0.0149608940 _diffrn_orient_matrix_UB_21 -0.0528181960 _diffrn_orient_matrix_UB_22 -0.0134870895 _diffrn_orient_matrix_UB_23 0.0721883971 _diffrn_orient_matrix_UB_31 0.1090401219 _diffrn_orient_matrix_UB_32 0.0015047110 _diffrn_orient_matrix_UB_33 0.0198551140 _reflns_number_total 2093 _reflns_number_gt 1483 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -40.00 12.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 -77.0000 0.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 2 omega -86.00 -8.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 143.0000 -22.0000 0.0000 0.0000 78 #__ type_ start__ end____ width___ exp.time_ 3 omega 5.00 55.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 0.0000 240.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 4 omega -48.00 5.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 77.0000 300.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 5 omega 5.00 55.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 0.0000 30.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 6 omega -41.00 9.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 45.0000 210.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 7 omega -88.00 12.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 -77.0000 210.0000 0.0000 0.0000 100 #__ type_ start__ end____ width___ exp.time_ 8 omega -89.00 5.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 -45.0000 60.0000 0.0000 0.0000 94 #__ type_ start__ end____ width___ exp.time_ 9 omega -79.00 -1.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 131.0000 78.0000 0.0000 0.0000 78 #__ type_ start__ end____ width___ exp.time_ 10 omega -41.00 -15.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 45.0000 30.0000 0.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 1.00 53.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 77.0000 60.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 12 omega -48.00 -7.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 77.0000 270.0000 0.0000 0.0000 41 #__ type_ start__ end____ width___ exp.time_ 13 omega -82.00 -39.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.5955 -45.0000 270.0000 0.0000 0.0000 43 #__ type_ start__ end____ width___ exp.time_ 14 omega 0.00 80.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.3142 77.0000 330.0000 0.0000 0.0000 80 #__ type_ start__ end____ width___ exp.time_ 15 omega 46.00 90.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.3142 45.0000 330.0000 0.0000 0.0000 44 #__ type_ start__ end____ width___ exp.time_ 16 omega 58.00 88.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.3142 77.0000 60.0000 0.0000 0.0000 30 #__ type_ start__ end____ width___ exp.time_ 17 omega -10.00 72.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.3142 -117.0000 333.0000 0.0000 0.0000 82 #__ type_ start__ end____ width___ exp.time_ 18 omega 2.00 28.00 1.0000 13.9000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.3142 77.0000 30.0000 0.0000 0.0000 26 ; _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^)+(0.0418P)^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_number_reflns 2093 _refine_ls_number_parameters 138 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 1.001 _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 Cl1 Cl 0.21714(8) 0.98670(6) 0.16967(5) 0.04030(15) Uani 1 1 d . . . N1 N 0.7972(3) 0.8247(2) 0.13855(19) 0.0335(4) Uani 1 1 d . . . C1 C 0.9318(3) 0.6770(2) 0.03977(17) 0.0275(4) Uani 1 1 d . . . C2 C 0.7575(3) 0.5949(2) -0.0095(2) 0.0335(4) Uani 1 1 d . . . C3 C 1.1029(3) 0.5560(2) 0.11161(19) 0.0324(4) Uani 1 1 d . . . H1N H 0.894(4) 0.888(2) 0.162(2) 0.049(6) Uiso 1 1 d . . . H2N H 0.712(4) 0.800(3) 0.225(2) 0.050(6) Uiso 1 1 d . . . H3N H 0.696(4) 0.890(3) 0.102(2) 0.043(6) Uiso 1 1 d . . . H1 H 1.021(3) 0.720(2) -0.0390(18) 0.027(4) Uiso 1 1 d . . . H2A H 0.662(3) 0.558(2) 0.0730(19) 0.030(4) Uiso 1 1 d . . . H2B H 0.645(3) 0.675(2) -0.051(2) 0.040(5) Uiso 1 1 d . . . H3A H 1.208(3) 0.615(2) 0.1430(18) 0.035(5) Uiso 1 1 d . . . H3B H 1.005(3) 0.524(2) 0.1943(19) 0.033(5) Uiso 1 1 d . . . S10 S 0.61941(8) 0.19164(6) 0.50071(5) 0.04162(15) Uani 1 1 d . . . O10 O 0.4097(2) 0.30087(19) 0.60783(14) 0.0536(4) Uani 1 1 d . . . C11 C 0.8717(4) 0.2742(4) 0.4980(3) 0.0592(7) Uani 1 1 d D . . C12 C 0.5729(5) 0.2551(4) 0.3294(3) 0.0576(6) Uani 1 1 d . . . H11A H 0.987(3) 0.228(3) 0.422(2) 0.068(7) Uiso 1 1 d D . . H11B H 0.826(4) 0.390(3) 0.486(3) 0.067(8) Uiso 1 1 d . . . H11C H 0.910(5) 0.252(3) 0.587(3) 0.096(9) Uiso 1 1 d . . . H12A H 0.453(5) 0.210(3) 0.309(3) 0.079(8) Uiso 1 1 d . . . H12B H 0.539(4) 0.378(3) 0.333(2) 0.069(8) Uiso 1 1 d . . . H12C H 0.698(4) 0.209(3) 0.263(2) 0.065(7) 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 0.0329(2) 0.0426(3) 0.0469(3) 0.0080(2) -0.0112(2) -0.0104(2) N1 0.0280(8) 0.0315(9) 0.0382(9) -0.0021(7) -0.0064(7) -0.0030(7) C1 0.0240(8) 0.0280(9) 0.0273(9) 0.0019(7) -0.0014(7) -0.0051(7) C2 0.0249(9) 0.0354(10) 0.0386(10) -0.0005(8) -0.0102(8) -0.0016(8) C3 0.0279(9) 0.0371(10) 0.0325(10) -0.0009(8) -0.0098(8) -0.0059(8) S10 0.0375(3) 0.0433(3) 0.0394(3) 0.0013(2) 0.0003(2) -0.0099(2) O10 0.0431(8) 0.0618(10) 0.0410(8) 0.0035(7) 0.0096(6) -0.0032(7) C11 0.0423(13) 0.081(2) 0.0531(15) -0.0136(14) -0.0046(11) -0.0195(13) C12 0.0497(14) 0.080(2) 0.0407(13) -0.0033(13) -0.0044(11) -0.0175(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 N1 C1 1.487(2) . ? N1 H1N 0.92(2) . ? N1 H2N 0.92(2) . ? N1 H3N 0.84(2) . ? C1 C2 1.512(2) . ? C1 C3 1.514(2) . ? C1 H1 0.936(17) . ? C2 C3 1.527(2) 2_765 ? C2 H2A 0.956(18) . ? C2 H2B 0.97(2) . ? C3 C2 1.527(2) 2_765 ? C3 H3A 0.969(15) . ? C3 H3B 0.944(18) . ? S10 O10 1.5088(14) . ? S10 C11 1.769(2) . ? S10 C12 1.781(2) . ? C11 H11A 0.885(16) . ? C11 H11B 0.94(2) . ? C11 H11C 0.94(3) . ? C12 H12A 0.93(2) . ? C12 H12B 0.98(2) . ? C12 H12C 0.86(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 C1 N1 H1N 113.8(12) . . ? C1 N1 H2N 114.6(13) . . ? H1N N1 H2N 104.9(17) . . ? C1 N1 H3N 111.0(13) . . ? H1N N1 H3N 106.0(19) . . ? H2N N1 H3N 105.7(18) . . ? N1 C1 C2 110.38(13) . . ? N1 C1 C3 110.01(14) . . ? C2 C1 C3 112.04(15) . . ? N1 C1 H1 105.4(10) . . ? C2 C1 H1 109.4(9) . . ? C3 C1 H1 109.4(10) . . ? C1 C2 C3 110.05(14) . 2_765 ? C1 C2 H2A 108.1(10) . . ? C3 C2 H2A 109.1(10) 2_765 . ? C1 C2 H2B 110.8(10) . . ? C3 C2 H2B 112.5(11) 2_765 . ? H2A C2 H2B 106.1(14) . . ? C1 C3 C2 109.92(14) . 2_765 ? C1 C3 H3A 108.8(10) . . ? C2 C3 H3A 112.8(9) 2_765 . ? C1 C3 H3B 106.0(11) . . ? C2 C3 H3B 111.5(11) 2_765 . ? H3A C3 H3B 107.5(14) . . ? O10 S10 C11 106.44(11) . . ? O10 S10 C12 105.37(11) . . ? C11 S10 C12 97.56(14) . . ? S10 C11 H11A 107.7(14) . . ? S10 C11 H11B 108.2(14) . . ? H11A C11 H11B 108(2) . . ? S10 C11 H11C 105.6(17) . . ? H11A C11 H11C 115(2) . . ? H11B C11 H11C 111(2) . . ? S10 C12 H12A 108.5(16) . . ? S10 C12 H12B 106.7(14) . . ? H12A C12 H12B 116(2) . . ? S10 C12 H12C 110.4(16) . . ? H12A C12 H12C 103(2) . . ? H12B C12 H12C 112(2) . . ? _diffrn_measured_fraction_theta_max 0.865 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.215 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.044 # Attachment 'dace_monochloride.cif' data_exp_85_abs _database_code_depnum_ccdc_archive 'CCDC 696304' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1-ammonio-2-amine-cyclohexane chloride' ; _chemical_name_common ; '1-ammonio-2-amine-cyclohexane chloride' ; _chemical_formula_moiety 'C6 H15 N2, Cl' _chemical_formula_sum 'C6 H15 Cl N2' _chemical_formula_weight 150.65 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_space_group_name_H-M 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' 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 7.4694(2) _cell_length_b 15.3118(3) _cell_length_c 8.0970(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.144(3) _cell_angle_gamma 90.00 _cell_volume 869.41(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8550 _cell_measurement_theta_min 2.6526 _cell_measurement_theta_max 29.2870 _diffrn_measurement_method 'omega scan' _diffrn_measurement_device_type xcalibur _diffrn_measurement_device '95mm CCD camera (sapphire) on \k-goniostat' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.1340 _diffrn_reflns_number 18139 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 29.38 _reflns_number_total 2180 _reflns_number_gt 1660 _reflns_threshold_expression >2sigma(I) _diffrn_orient_matrix_UB_11 0.0231436808 _diffrn_orient_matrix_UB_12 0.0333565008 _diffrn_orient_matrix_UB_13 -0.0500481577 _diffrn_orient_matrix_UB_21 -0.0287648353 _diffrn_orient_matrix_UB_22 -0.0275590081 _diffrn_orient_matrix_UB_23 -0.0750589341 _diffrn_orient_matrix_UB_31 -0.0942959358 _diffrn_orient_matrix_UB_32 0.0167074620 _diffrn_orient_matrix_UB_33 -0.0239174155 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 6.00 56.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 0.0000 30.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 2 omega -39.00 13.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 -77.0000 60.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 3 omega -9.00 56.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 0.0000 90.0000 0.0000 0.0000 65 #__ type_ start__ end____ width___ exp.time_ 4 omega -88.00 6.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 -45.0000 270.0000 0.0000 0.0000 94 #__ type_ start__ end____ width___ exp.time_ 5 omega -87.00 -35.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 -77.0000 90.0000 0.0000 0.0000 52 #__ type_ start__ end____ width___ exp.time_ 6 omega -87.00 -9.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 144.0000 -5.0000 0.0000 0.0000 78 #__ type_ start__ end____ width___ exp.time_ 7 omega -41.00 9.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 45.0000 0.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 8 omega 5.00 54.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 45.0000 120.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 9 omega -42.00 6.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 -45.0000 90.0000 0.0000 0.0000 48 #__ type_ start__ end____ width___ exp.time_ 10 omega -47.00 -3.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 77.0000 300.0000 0.0000 0.0000 44 #__ type_ start__ end____ width___ exp.time_ 11 omega -41.00 9.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 45.0000 240.0000 0.0000 0.0000 50 #__ type_ start__ end____ width___ exp.time_ 12 omega -38.00 13.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -17.2830 -77.0000 180.0000 0.0000 0.0000 51 #__ type_ start__ end____ width___ exp.time_ 13 omega 29.00 71.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -116.0000 11.0000 0.0000 0.0000 42 #__ type_ start__ end____ width___ exp.time_ 14 omega 41.00 90.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 45.0000 90.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 15 omega 5.00 54.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -86.0000 309.0000 0.0000 0.0000 49 #__ type_ start__ end____ width___ exp.time_ 16 omega 46.00 90.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 45.0000 0.0000 0.0000 0.0000 44 #__ type_ start__ end____ width___ exp.time_ 17 omega 36.00 78.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -127.0000 162.0000 0.0000 0.0000 42 #__ type_ start__ end____ width___ exp.time_ 18 omega 47.00 77.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 0.0000 150.0000 0.0000 0.0000 30 #__ type_ start__ end____ width___ exp.time_ 19 omega -4.00 21.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 45.0000 210.0000 0.0000 0.0000 25 #__ type_ start__ end____ width___ exp.time_ 20 omega -4.00 34.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 45.0000 330.0000 0.0000 0.0000 38 #__ type_ start__ end____ width___ exp.time_ 21 omega -51.00 -26.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 19.1580 -77.0000 210.0000 0.0000 0.0000 25 ; _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4252 _exptl_crystal_size_mid 0.3344 _exptl_crystal_size_min 0.1268 _exptl_crystal_density_diffrn 1.151 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.365 _exptl_absorpt_correction_T_min 0.891 _exptl_absorpt_correction_T_max 0.962 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0548P)^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_number_reflns 2180 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0893 _refine_ls_wR_factor_gt 0.0835 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Cl1 Cl 0.51020(5) 0.36348(2) 0.73284(4) 0.05187(15) Uani 1 1 d . . . N1 N 0.37155(14) 0.07535(8) 0.79900(16) 0.0408(3) Uani 1 1 d . . . H1N H 0.4083(19) 0.0857(9) 0.913(2) 0.048(4) Uiso 1 1 d . . . H2N H 0.3931(19) 0.0245(11) 0.7905(17) 0.047(4) Uiso 1 1 d . . . N2 N -0.41206(15) 0.16815(8) 0.64285(17) 0.0389(3) Uani 1 1 d . . . H4N H -0.4411(18) 0.1588(9) 0.530(2) 0.041(4) Uiso 1 1 d . . . H5N H -0.483(2) 0.1344(11) 0.692(2) 0.069(5) Uiso 1 1 d . . . H6N H -0.4360(18) 0.2217(11) 0.6568(17) 0.045(4) Uiso 1 1 d . . . C1 C 0.16641(16) 0.09378(8) 0.72024(16) 0.0339(3) Uani 1 1 d . . . H1 H 0.1360(16) 0.0863(8) 0.6010(16) 0.035(3) Uiso 1 1 d . . . C2 C 0.12721(18) 0.18740(8) 0.7587(2) 0.0416(3) Uani 1 1 d . . . H2A H 0.1649(17) 0.1922(9) 0.8843(18) 0.043(4) Uiso 1 1 d . . . H2B H 0.200(2) 0.2236(10) 0.7200(18) 0.050(4) Uiso 1 1 d . . . C3 C -0.08360(18) 0.20992(8) 0.6744(2) 0.0410(3) Uani 1 1 d . . . H3A H -0.1196(18) 0.2041(9) 0.5515(18) 0.042(4) Uiso 1 1 d . . . H3B H -0.1075(19) 0.2672(9) 0.6984(18) 0.047(4) Uiso 1 1 d . . . C4 C -0.20680(16) 0.14722(8) 0.73252(16) 0.0347(3) Uani 1 1 d . . . H4 H -0.1833(16) 0.1545(7) 0.8554(17) 0.032(3) Uiso 1 1 d . . . C5 C -0.16815(17) 0.05289(8) 0.6960(2) 0.0406(3) Uani 1 1 d . . . H5A H -0.2053(18) 0.0462(9) 0.5700(19) 0.047(4) Uiso 1 1 d . . . H5B H -0.242(2) 0.0165(10) 0.7353(18) 0.056(4) Uiso 1 1 d . . . C6 C 0.04283(18) 0.03127(9) 0.7802(2) 0.0415(3) Uani 1 1 d . . . H6A H 0.0808(19) 0.0367(9) 0.9060(18) 0.047(4) Uiso 1 1 d . . . H6B H 0.0695(18) -0.0281(11) 0.7568(17) 0.050(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 Cl1 0.0694(3) 0.0374(2) 0.0450(2) 0.00059(13) 0.01490(16) 0.00045(14) N1 0.0379(6) 0.0400(7) 0.0466(7) 0.0013(5) 0.0174(5) 0.0049(5) N2 0.0362(6) 0.0380(6) 0.0460(7) -0.0017(5) 0.0186(5) 0.0024(4) C1 0.0340(6) 0.0375(7) 0.0323(6) 0.0004(5) 0.0141(5) 0.0014(5) C2 0.0370(7) 0.0342(7) 0.0567(9) 0.0017(6) 0.0203(6) -0.0040(5) C3 0.0393(7) 0.0307(7) 0.0549(9) 0.0039(6) 0.0187(6) 0.0016(5) C4 0.0341(6) 0.0360(7) 0.0362(6) -0.0019(5) 0.0149(5) -0.0004(5) C5 0.0380(7) 0.0311(6) 0.0544(8) 0.0010(5) 0.0180(6) -0.0035(5) C6 0.0415(7) 0.0314(7) 0.0539(8) 0.0059(6) 0.0192(6) 0.0010(5) _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 1.4701(16) . ? N1 H1N 0.884(15) . ? N1 H2N 0.803(16) . ? N2 C4 1.4879(15) . ? N2 H4N 0.874(15) . ? N2 H5N 0.93(2) . ? N2 H6N 0.855(16) . ? C1 C2 1.5169(18) . ? C1 C6 1.5207(17) . ? C1 H1 0.920(12) . ? C2 C3 1.5245(18) . ? C2 H2A 0.960(13) . ? C2 H2B 0.903(15) . ? C3 C4 1.5127(17) . ? C3 H3A 0.942(14) . ? C3 H3B 0.929(14) . ? C4 C5 1.5218(17) . ? C4 H4 0.955(12) . ? C5 C6 1.5225(18) . ? C5 H5A 0.966(14) . ? C5 H5B 0.916(15) . ? C6 H6A 0.962(13) . ? C6 H6B 0.963(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 H1N 108.7(9) . . ? C1 N1 H2N 111.0(10) . . ? H1N N1 H2N 105.4(13) . . ? C4 N2 H4N 108.5(9) . . ? C4 N2 H5N 108.5(10) . . ? H4N N2 H5N 112.8(13) . . ? C4 N2 H6N 111.7(9) . . ? H4N N2 H6N 107.9(12) . . ? H5N N2 H6N 107.5(13) . . ? N1 C1 C2 109.78(10) . . ? N1 C1 C6 113.41(10) . . ? C2 C1 C6 110.35(10) . . ? N1 C1 H1 106.0(7) . . ? C2 C1 H1 109.8(8) . . ? C6 C1 H1 107.4(8) . . ? C1 C2 C3 111.37(10) . . ? C1 C2 H2A 106.4(8) . . ? C3 C2 H2A 109.8(8) . . ? C1 C2 H2B 109.1(9) . . ? C3 C2 H2B 110.9(9) . . ? H2A C2 H2B 109.2(11) . . ? C4 C3 C2 111.24(10) . . ? C4 C3 H3A 106.6(8) . . ? C2 C3 H3A 109.1(8) . . ? C4 C3 H3B 110.7(8) . . ? C2 C3 H3B 111.3(9) . . ? H3A C3 H3B 107.8(11) . . ? N2 C4 C3 110.28(10) . . ? N2 C4 C5 110.01(10) . . ? C3 C4 C5 111.44(10) . . ? N2 C4 H4 105.8(7) . . ? C3 C4 H4 109.6(7) . . ? C5 C4 H4 109.5(7) . . ? C4 C5 C6 110.83(10) . . ? C4 C5 H5A 107.5(8) . . ? C6 C5 H5A 109.1(8) . . ? C4 C5 H5B 109.3(9) . . ? C6 C5 H5B 111.6(9) . . ? H5A C5 H5B 108.3(11) . . ? C1 C6 C5 111.63(10) . . ? C1 C6 H6A 107.1(8) . . ? C5 C6 H6A 109.7(8) . . ? C1 C6 H6B 110.0(8) . . ? C5 C6 H6B 111.7(8) . . ? H6A C6 H6B 106.6(11) . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.169 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.045