# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Giancarlo Terraneo' _publ_contact_author_email gterraneo@chem.polimi.it loop_ _publ_author_name 'Lorenzo Meazza' 'Javier Marti-Rujas' 'Giancarlo Terraneo' 'Chiara Castiglioni' 'Alberto Milani' ; T.Pilati ; 'Pierangelo Metrangolo' 'Giuseppe Resnati' # Attachment 'JM044_CCDC_797580.CIF' data_jm044 _database_code_depnum_ccdc_archive 'CCDC 797580' #TrackingRef 'JM044_CCDC_797580.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H30 N2 2+, 2(Br 1-), 2(H2 O)' _chemical_formula_sum 'C12 H34 Br2 N2 O2' _chemical_formula_weight 398.23 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _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 7.3339(13) _cell_length_b 18.292(3) _cell_length_c 7.0915(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.824(4) _cell_angle_gamma 90.00 _cell_volume 900.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 9842 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 30.02 _exptl_crystal_description table _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 4.501 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.2766 _exptl_absorpt_correction_T_max 0.4005 _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 30772 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 30.24 _reflns_number_total 2604 _reflns_number_gt 2412 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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. H atoms were refined isotropically; all the other H atoms were calculated ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0202P)^2^+0.4646P] 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 2604 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0200 _refine_ls_R_factor_gt 0.0172 _refine_ls_wR_factor_ref 0.0453 _refine_ls_wR_factor_gt 0.0441 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 Br1 Br 0.308809(16) 0.367169(6) 0.167408(18) 0.01502(5) Uani 1 1 d . . . N1 N 0.64175(15) 0.12555(5) 0.28362(16) 0.01214(19) Uani 1 1 d . . . C1 C 0.76391(18) 0.11944(7) 0.14767(18) 0.0133(2) Uani 1 1 d . . . H1A H 0.8515 0.1621 0.1710 0.016 Uiso 1 1 calc R . . H1B H 0.6781 0.1217 0.0077 0.016 Uiso 1 1 calc R . . C2 C 0.88398(17) 0.04994(7) 0.17575(18) 0.0137(2) Uani 1 1 d . . . H2A H 0.8084 0.0081 0.1993 0.016 Uiso 1 1 calc R . . H2B H 1.0008 0.0552 0.2937 0.016 Uiso 1 1 calc R . . C3 C 0.94238(17) 0.03529(6) -0.00893(18) 0.0134(2) Uani 1 1 d . . . H3A H 0.8251 0.0322 -0.1271 0.016 Uiso 1 1 calc R . . H3B H 1.0207 0.0767 -0.0295 0.016 Uiso 1 1 calc R . . C4 C 0.5515(2) 0.19996(7) 0.2551(2) 0.0196(3) Uani 1 1 d . . . H4A H 0.4751 0.2066 0.1147 0.029 Uiso 1 1 calc R . . H4B H 0.6527 0.2373 0.2941 0.029 Uiso 1 1 calc R . . H4C H 0.4678 0.2047 0.3377 0.029 Uiso 1 1 calc R . . C5 C 0.76172(19) 0.11659(8) 0.49752(19) 0.0205(3) Uani 1 1 d . . . H5A H 0.6821 0.1257 0.5826 0.031 Uiso 1 1 calc R . . H5B H 0.8687 0.1515 0.5304 0.031 Uiso 1 1 calc R . . H5C H 0.8129 0.0667 0.5196 0.031 Uiso 1 1 calc R . . C6 C 0.48369(18) 0.06984(7) 0.2306(2) 0.0172(2) Uani 1 1 d . . . H6A H 0.4022 0.0768 0.3149 0.026 Uiso 1 1 calc R . . H6B H 0.5398 0.0207 0.2519 0.026 Uiso 1 1 calc R . . H6C H 0.4056 0.0756 0.0904 0.026 Uiso 1 1 calc R . . O1 O 0.03540(18) 0.22753(7) 0.9007(2) 0.0372(3) Uani 1 1 d . . . H1O H 0.131(4) 0.2639(15) 0.985(4) 0.066(8) Uiso 1 1 d . . . H2O H 0.132(5) 0.203(2) 0.823(5) 0.127(13) 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 Br1 0.01511(7) 0.01444(7) 0.01603(7) -0.00090(4) 0.00575(5) 0.00057(4) N1 0.0126(4) 0.0127(4) 0.0118(4) -0.0007(3) 0.0049(4) 0.0010(3) C1 0.0146(5) 0.0136(5) 0.0139(5) 0.0006(4) 0.0075(4) 0.0015(4) C2 0.0150(5) 0.0138(5) 0.0134(5) 0.0010(4) 0.0061(4) 0.0028(4) C3 0.0149(5) 0.0133(5) 0.0135(5) 0.0008(4) 0.0067(4) 0.0011(4) C4 0.0242(6) 0.0135(5) 0.0244(6) 0.0005(5) 0.0121(5) 0.0060(5) C5 0.0169(6) 0.0334(7) 0.0105(5) 0.0000(5) 0.0033(4) 0.0033(5) C6 0.0156(5) 0.0171(6) 0.0207(6) -0.0028(5) 0.0082(5) -0.0035(4) O1 0.0296(6) 0.0348(6) 0.0473(7) -0.0114(6) 0.0127(5) -0.0025(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 C5 1.4969(16) . ? N1 C6 1.4974(16) . ? N1 C4 1.4984(16) . ? N1 C1 1.5173(15) . ? C1 C2 1.5225(16) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5273(17) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C3 1.526(2) 3_755 ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O1 H1O 1.01(3) . ? O1 H2O 1.12(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 C5 N1 C6 109.52(10) . . ? C5 N1 C4 109.03(10) . . ? C6 N1 C4 108.17(10) . . ? C5 N1 C1 111.18(10) . . ? C6 N1 C1 111.00(9) . . ? C4 N1 C1 107.85(9) . . ? N1 C1 C2 114.43(10) . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1B 108.7 . . ? C2 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C1 C2 C3 110.17(9) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C3 C3 C2 112.24(12) 3_755 . ? C3 C3 H3A 109.2 3_755 . ? C2 C3 H3A 109.2 . . ? C3 C3 H3B 109.2 3_755 . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6A 109.5 . . ? N1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? H1O O1 H2O 97(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 53.96(14) . . . . ? C6 N1 C1 C2 -68.22(13) . . . . ? C4 N1 C1 C2 173.44(10) . . . . ? N1 C1 C2 C3 159.73(10) . . . . ? C1 C2 C3 C3 -178.11(12) . . . 3_755 ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.381 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.061 # Attachment 'JM048_CCDC_797581.CIF' data_jm048 _database_code_depnum_ccdc_archive 'CCDC 797581' #TrackingRef 'JM048_CCDC_797581.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H30 N2 2+, 2(H2O), 2(Cl 1-)' _chemical_formula_sum 'C12 H34 Cl2 N2 O2' _chemical_formula_weight 309.31 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4621(10) _cell_length_b 8.1058(11) _cell_length_c 8.4022(11) _cell_angle_alpha 94.013(10) _cell_angle_beta 116.002(12) _cell_angle_gamma 99.107(11) _cell_volume 445.42(10) _cell_formula_units_Z 1 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 7003 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 32.63 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.7972 _exptl_absorpt_correction_T_max 0.8932 _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 9178 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 32.70 _reflns_number_total 2997 _reflns_number_gt 2786 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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 'w=1/[\s^2^(Fo^2^)+(0.0262P)^2^+0.0907P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2997 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0628 _refine_ls_wR_factor_gt 0.0617 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.23619(3) 0.24012(2) 0.85883(2) 0.02205(6) Uani 1 1 d . . . N1 N 1.00902(9) 0.73351(7) 0.75802(8) 0.01492(11) Uani 1 1 d . . . C1 C 0.87102(10) 0.85286(8) 0.75601(9) 0.01391(11) Uani 1 1 d . . . H1A H 0.9576(15) 0.9608(12) 0.7948(13) 0.016(2) Uiso 1 1 d . . . H1B H 0.8255(15) 0.8221(13) 0.8421(13) 0.017(2) Uiso 1 1 d . . . C2 C 0.69109(10) 0.84858(8) 0.57493(9) 0.01547(12) Uani 1 1 d . . . H2A H 0.5908(16) 0.7432(13) 0.5390(14) 0.023(3) Uiso 1 1 d . . . H2B H 0.7342(16) 0.8585(13) 0.4786(14) 0.023(2) Uiso 1 1 d . . . C3 C 0.59169(10) 0.99681(9) 0.58801(9) 0.01596(12) Uani 1 1 d . . . H3A H 0.5477(16) 0.9884(13) 0.6836(14) 0.022(2) Uiso 1 1 d . . . H3B H 0.6941(16) 1.1039(14) 0.6241(14) 0.023(2) Uiso 1 1 d . . . C4 C 1.11430(12) 0.78374(10) 0.64667(10) 0.02081(14) Uani 1 1 d . . . H4A H 1.2100(17) 0.7126(14) 0.6648(15) 0.026(3) Uiso 1 1 d . . . H4B H 1.1837(17) 0.9020(15) 0.6897(15) 0.027(3) Uiso 1 1 d . . . H4C H 1.0141(17) 0.7664(13) 0.5252(15) 0.024(3) Uiso 1 1 d . . . C5 C 1.16825(12) 0.74813(12) 0.94854(10) 0.02437(16) Uani 1 1 d . . . H5A H 1.1023(17) 0.7186(15) 1.0190(16) 0.029(3) Uiso 1 1 d . . . H5B H 1.2449(18) 0.8622(15) 0.9846(16) 0.031(3) Uiso 1 1 d . . . H5C H 1.2554(18) 0.6703(15) 0.9533(16) 0.034(3) Uiso 1 1 d . . . C6 C 0.89138(12) 0.55434(9) 0.69185(11) 0.02226(14) Uani 1 1 d . . . H6A H 0.8156(17) 0.5304(15) 0.7558(16) 0.030(3) Uiso 1 1 d . . . H6B H 0.9887(18) 0.4847(15) 0.7121(16) 0.030(3) Uiso 1 1 d . . . H6C H 0.8019(16) 0.5430(14) 0.5647(15) 0.022(2) Uiso 1 1 d . . . O1 O 0.52660(10) 0.46226(8) 0.24115(8) 0.02593(12) Uani 1 1 d . . . H1O H 0.586(2) 0.5436(19) 0.2180(18) 0.044(4) Uiso 1 1 d . . . H2O H 0.449(2) 0.4011(18) 0.1362(19) 0.041(3) 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 0.02546(9) 0.01863(9) 0.01962(9) 0.00122(6) 0.01062(7) -0.00222(6) N1 0.0152(2) 0.0167(3) 0.0129(2) 0.00253(19) 0.0053(2) 0.0067(2) C1 0.0146(3) 0.0145(3) 0.0135(3) 0.0022(2) 0.0063(2) 0.0058(2) C2 0.0157(3) 0.0156(3) 0.0142(3) 0.0020(2) 0.0050(2) 0.0063(2) C3 0.0160(3) 0.0166(3) 0.0146(3) 0.0020(2) 0.0054(2) 0.0068(2) C4 0.0205(3) 0.0268(4) 0.0207(3) 0.0048(3) 0.0128(3) 0.0091(3) C5 0.0219(3) 0.0347(4) 0.0137(3) 0.0034(3) 0.0030(3) 0.0143(3) C6 0.0246(3) 0.0142(3) 0.0272(4) 0.0030(3) 0.0101(3) 0.0070(3) O1 0.0270(3) 0.0267(3) 0.0208(3) 0.0047(2) 0.0099(2) -0.0009(2) _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 C6 1.4982(10) . ? N1 C5 1.4998(10) . ? N1 C4 1.5016(9) . ? N1 C1 1.5163(8) . ? C1 C2 1.5184(9) . ? C1 H1A 0.941(10) . ? C1 H1B 0.956(10) . ? C2 C3 1.5301(9) . ? C2 H2A 0.972(11) . ? C2 H2B 0.997(11) . ? C3 C3 1.5235(13) 2_676 ? C3 H3A 0.995(11) . ? C3 H3B 0.990(11) . ? C4 H4A 0.956(11) . ? C4 H4B 0.974(12) . ? C4 H4C 0.947(11) . ? C5 H5A 0.942(12) . ? C5 H5B 0.957(12) . ? C5 H5C 0.966(12) . ? C6 H6A 0.945(12) . ? C6 H6B 0.954(12) . ? C6 H6C 0.968(11) . ? O1 H1O 0.820(15) . ? O1 H2O 0.871(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 C6 N1 C5 109.29(6) . . ? C6 N1 C4 110.05(6) . . ? C5 N1 C4 108.35(6) . . ? C6 N1 C1 111.04(5) . . ? C5 N1 C1 107.28(5) . . ? C4 N1 C1 110.73(5) . . ? N1 C1 C2 115.21(5) . . ? N1 C1 H1A 104.2(6) . . ? C2 C1 H1A 110.0(6) . . ? N1 C1 H1B 105.3(6) . . ? C2 C1 H1B 110.8(6) . . ? H1A C1 H1B 111.1(8) . . ? C1 C2 C3 108.48(5) . . ? C1 C2 H2A 111.4(6) . . ? C3 C2 H2A 109.3(6) . . ? C1 C2 H2B 111.7(6) . . ? C3 C2 H2B 108.9(6) . . ? H2A C2 H2B 106.9(9) . . ? C3 C3 C2 112.44(7) 2_676 . ? C3 C3 H3A 109.1(6) 2_676 . ? C2 C3 H3A 109.7(6) . . ? C3 C3 H3B 109.4(6) 2_676 . ? C2 C3 H3B 109.1(6) . . ? H3A C3 H3B 106.9(9) . . ? N1 C4 H4A 106.5(7) . . ? N1 C4 H4B 107.8(7) . . ? H4A C4 H4B 110.9(10) . . ? N1 C4 H4C 108.0(7) . . ? H4A C4 H4C 111.5(9) . . ? H4B C4 H4C 111.8(9) . . ? N1 C5 H5A 108.5(7) . . ? N1 C5 H5B 107.2(7) . . ? H5A C5 H5B 112.6(10) . . ? N1 C5 H5C 108.6(7) . . ? H5A C5 H5C 109.5(10) . . ? H5B C5 H5C 110.5(10) . . ? N1 C6 H6A 108.0(7) . . ? N1 C6 H6B 106.8(7) . . ? H6A C6 H6B 112.4(10) . . ? N1 C6 H6C 108.6(6) . . ? H6A C6 H6C 110.8(9) . . ? H6B C6 H6C 110.0(9) . . ? H1O O1 H2O 103.0(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C1 C2 -57.20(8) . . . . ? C5 N1 C1 C2 -176.57(6) . . . . ? C4 N1 C1 C2 65.38(7) . . . . ? N1 C1 C2 C3 -169.70(6) . . . . ? C1 C2 C3 C3 -179.89(7) . . . 2_676 ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.416 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.038 # Attachment 'MZ131_CCDC_797582.CIF' data_mz131 _database_code_depnum_ccdc_archive 'CCDC 797582' #TrackingRef 'MZ131_CCDC_797582.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H30 N2, 2+, 2(Br3, 1-)' _chemical_formula_sum 'C12 H30 Br6 N2' _chemical_formula_weight 681.84 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.450(4) _cell_length_b 7.3232(10) _cell_length_c 7.1474(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.31(2) _cell_angle_gamma 90.00 _cell_volume 1121.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1738 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 26.10 _exptl_crystal_description table _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.019 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 10.732 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.2642 _exptl_absorpt_correction_T_max 0.4061 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 7088 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 30.56 _reflns_number_total 1804 _reflns_number_gt 1036 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _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 'w=1/[\s^2^(Fo^2^)+(0.0291P)^2^+1.0449P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1804 _refine_ls_number_parameters 67 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0328 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.001 _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 Br1 Br 0.22223(3) 0.0000 -0.14219(7) 0.06362(19) Uani 1 2 d S . . Br2 Br 0.12476(2) 0.0000 0.07347(6) 0.05206(16) Uani 1 2 d S . . Br3 Br 0.03455(3) 0.0000 0.27610(9) 0.06861(19) Uani 1 2 d S . . N1 N 0.34414(16) 0.0000 0.3908(5) 0.0394(8) Uani 1 2 d S . . C1 C 0.37320(19) 0.0000 0.2014(6) 0.0405(10) Uani 1 2 d S . . H1 H 0.3596(14) 0.106(4) 0.133(4) 0.049 Uiso 1 1 d . . . C2 C 0.4428(2) 0.0000 0.2029(7) 0.0507(12) Uani 1 2 d S . . H2 H 0.4594(15) 0.098(4) 0.277(5) 0.061 Uiso 1 1 d . . . C3 C 0.4651(2) 0.0000 0.0043(7) 0.0510(12) Uani 1 2 d S . . H3 H 0.4509(15) 0.107(4) -0.061(5) 0.061 Uiso 1 1 d . . . C4 C 0.36258(16) 0.1664(5) 0.4995(5) 0.0610(9) Uani 1 1 d . . . H4A H 0.3507 0.2733 0.4289 0.091 Uiso 1 1 calc R . . H4B H 0.4069 0.1664 0.5234 0.091 Uiso 1 1 calc R . . H4C H 0.3420 0.1667 0.6163 0.091 Uiso 1 1 calc R . . C5 C 0.27470(19) 0.0000 0.3556(6) 0.0528(12) Uani 1 2 d S . . H5A H 0.2626 -0.1070 0.2856 0.079 Uiso 0.50 1 calc PR . . H5B H 0.2626 0.1071 0.2856 0.079 Uiso 0.50 1 calc PR . . H5C H 0.2545 0.0000 0.4730 0.079 Uiso 1 2 calc SR . . 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 Br1 0.0856(4) 0.0607(3) 0.0449(3) 0.000 0.0077(3) 0.000 Br2 0.0626(3) 0.0430(3) 0.0497(3) 0.000 -0.0093(2) 0.000 Br3 0.0610(3) 0.0627(4) 0.0823(4) 0.000 0.0040(3) 0.000 N1 0.0385(18) 0.042(2) 0.0382(17) 0.000 0.0040(15) 0.000 C1 0.039(2) 0.048(3) 0.035(2) 0.000 0.0089(18) 0.000 C2 0.033(2) 0.066(3) 0.053(3) 0.000 0.006(2) 0.000 C3 0.041(2) 0.057(3) 0.056(3) 0.000 0.014(2) 0.000 C4 0.065(2) 0.063(2) 0.0547(19) -0.0184(18) 0.0024(17) 0.0000(18) C5 0.037(2) 0.074(3) 0.049(3) 0.000 0.011(2) 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 Br1 Br2 2.6470(9) . ? Br2 Br3 2.4633(9) . ? N1 C4 1.490(4) . ? N1 C4 1.490(4) 6 ? N1 C5 1.501(5) . ? N1 C1 1.513(5) . ? C1 C2 1.493(6) . ? C1 H1 0.96(3) . ? C2 C3 1.516(7) . ? C2 H2 0.95(3) . ? C3 C3 1.501(9) 5_655 ? C3 H3 0.96(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 Br3 Br2 Br1 179.60(3) . . ? C4 N1 C4 109.7(4) . 6 ? C4 N1 C5 109.2(2) . . ? C4 N1 C5 109.2(2) 6 . ? C4 N1 C1 110.9(2) . . ? C4 N1 C1 110.9(2) 6 . ? C5 N1 C1 107.0(3) . . ? C2 C1 N1 116.2(4) . . ? C2 C1 H1 106.8(18) . . ? N1 C1 H1 109.3(19) . . ? C1 C2 C3 110.3(4) . . ? C1 C2 H2 111(2) . . ? C3 C2 H2 113(2) . . ? C3 C3 C2 113.0(5) 5_655 . ? C3 C3 H3 106(2) 5_655 . ? C2 C3 H3 110(2) . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 61.1(2) . . . . ? C4 N1 C1 C2 -61.1(2) 6 . . . ? C5 N1 C1 C2 180.0 . . . . ? N1 C1 C2 C3 180.0 . . . . ? C1 C2 C3 C3 180.0 . . . 5_655 ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.765 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.084 # Attachment 'MZ127_CCDC_797583.CIF' data_mz127 _database_code_depnum_ccdc_archive 'CCDC 797583' #TrackingRef 'MZ127_CCDC_797583.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H30 N2, 2(Cl I2 1-)' _chemical_formula_sum 'C12 H30 Cl2 I4 N2' _chemical_formula_weight 780.88 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 22.361(3) _cell_length_b 7.5412(12) _cell_length_c 7.1251(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.388(12) _cell_angle_gamma 90.00 _cell_volume 1201.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2980 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 29.38 _exptl_crystal_description table _exptl_crystal_colour purple _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 5.407 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.4418 _exptl_absorpt_correction_T_max 0.5568 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Bruker APEX-II CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 7261 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 30.47 _reflns_number_total 1910 _reflns_number_gt 1453 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SUPERFLIP (L. Palatinus and G. Chapuis (2007) J. Appl. Cryst 40, 786-790' ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _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 'w=1/[\s^2^(Fo^2^)+(0.0245P)^2^+1.5366P] 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 NOREF _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1910 _refine_ls_number_parameters 59 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0646 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.23310(6) 0.0000 -0.17392(15) 0.0731(3) Uani 0.9543(14) 2 d SP . . I1 I 0.23310(6) 0.0000 -0.17392(15) 0.0731(3) Uani 0.05 2 d SP . . I2 I 0.134900(13) 0.0000 0.04554(4) 0.05099(11) Uani 1 2 d S . . I3 I 0.035549(15) 0.0000 0.27675(5) 0.06509(14) Uani 0.9543(14) 2 d SP . . Cl3 Cl 0.035549(15) 0.0000 0.27675(5) 0.06509(14) Uani 0.05 2 d SP . . N1 N 0.34188(14) 0.0000 0.3716(4) 0.0437(7) Uani 1 2 d S . . C1 C 0.37314(18) 0.0000 0.1866(6) 0.0485(9) Uani 1 2 d S . . H1A H 0.3601 0.1036 0.1161 0.058 Uiso 0.50 1 calc PR . . H1B H 0.3601 -0.1036 0.1161 0.058 Uiso 0.50 1 calc PR . . C2 C 0.44085(19) 0.0000 0.1971(7) 0.0567(10) Uani 1 2 d S . . H2A H 0.4549 -0.1041 0.2649 0.068 Uiso 0.50 1 calc PR . . H2B H 0.4549 0.1041 0.2649 0.068 Uiso 0.50 1 calc PR . . C3 C 0.4661(2) 0.0000 0.0005(7) 0.0589(11) Uani 1 2 d S . . H3A H 0.4515 -0.1039 -0.0665 0.071 Uiso 0.50 1 calc PR . . H3B H 0.4515 0.1039 -0.0665 0.071 Uiso 0.50 1 calc PR . . C4 C 0.35720(16) 0.1611(5) 0.4826(5) 0.0676(9) Uani 1 1 d . . . H4A H 0.3472 0.2648 0.4105 0.101 Uiso 1 1 calc R . . H4B H 0.3993 0.1614 0.5128 0.101 Uiso 1 1 calc R . . H4C H 0.3351 0.1611 0.5964 0.101 Uiso 1 1 calc R . . C5 C 0.27556(19) 0.0000 0.3270(6) 0.0635(12) Uani 1 2 d S . . H5A H 0.2652 -0.1047 0.2567 0.095 Uiso 0.50 1 calc PR . . H5B H 0.2654 0.1032 0.2541 0.095 Uiso 0.50 1 calc PR . . H5C H 0.2539 0.0015 0.4417 0.095 Uiso 1 2 calc SR . . 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 0.0784(8) 0.0847(8) 0.0572(6) 0.000 0.0186(5) 0.000 I1 0.0784(8) 0.0847(8) 0.0572(6) 0.000 0.0186(5) 0.000 I2 0.05396(19) 0.04902(16) 0.04976(16) 0.000 -0.00372(11) 0.000 I3 0.0559(2) 0.0687(2) 0.0709(2) 0.000 0.00544(15) 0.000 Cl3 0.0559(2) 0.0687(2) 0.0709(2) 0.000 0.00544(15) 0.000 N1 0.0385(18) 0.0479(17) 0.0448(16) 0.000 0.0033(13) 0.000 C1 0.044(2) 0.051(2) 0.051(2) 0.000 0.0088(17) 0.000 C2 0.044(2) 0.059(3) 0.067(3) 0.000 0.0105(19) 0.000 C3 0.048(3) 0.055(2) 0.074(3) 0.000 0.020(2) 0.000 C4 0.069(2) 0.067(2) 0.0674(19) -0.0235(17) 0.0039(16) -0.0035(17) C5 0.039(2) 0.095(4) 0.057(2) 0.000 0.0037(18) 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 Cl1 I2 2.7265(11) . ? I2 I3 2.7976(6) . ? N1 C4 1.485(4) . ? N1 C4 1.485(4) 6 ? N1 C1 1.507(5) . ? N1 C5 1.509(5) . ? C1 C2 1.514(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.523(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C3 1.515(9) 5_655 ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 Cl1 I2 I3 178.92(3) . . ? C4 N1 C4 109.8(4) . 6 ? C4 N1 C1 111.1(2) . . ? C4 N1 C1 111.1(2) 6 . ? C4 N1 C5 109.0(2) . . ? C4 N1 C5 109.0(2) 6 . ? C1 N1 C5 106.9(3) . . ? N1 C1 C2 116.2(4) . . ? N1 C1 H1A 108.2 . . ? C2 C1 H1A 108.2 . . ? N1 C1 H1B 108.2 . . ? C2 C1 H1B 108.2 . . ? H1A C1 H1B 107.4 . . ? C1 C2 C3 110.3(4) . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C3 C3 C2 113.4(6) 5_655 . ? C3 C3 H3A 108.9 5_655 . ? C2 C3 H3A 108.9 . . ? C3 C3 H3B 108.9 5_655 . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 61.2(2) . . . . ? C4 N1 C1 C2 -61.2(2) 6 . . . ? C5 N1 C1 C2 180.0 . . . . ? N1 C1 C2 C3 180.0 . . . . ? C1 C2 C3 C3 180.0 . . . 5_655 ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.690 _refine_diff_density_min -0.652 _refine_diff_density_rms 0.083 data_jm042 _database_code_depnum_ccdc_archive 'CCDC 801987' #TrackingRef 'JM042_CCDC_801987.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C12 H30 N2 2+, 1.75(Br2 Cl 1-), 0.25(Br3 1-)' _chemical_formula_sum 'C12 H30 Br4.25 Cl1.75 N2' _chemical_formula_weight 604.04 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_space_group_name_Hall '-C 2y' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.800(3) _cell_length_b 7.2927(10) _cell_length_c 6.8951(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.743(12) _cell_angle_gamma 90.00 _cell_volume 1095.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6441 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 24.05 _exptl_crystal_description table _exptl_crystal_colour orange _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.14 _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 589 _exptl_absorpt_coefficient_mu 8.010 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.0970 _exptl_absorpt_correction_T_max 0.1660 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 18315 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0147 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 26.42 _reflns_number_total 1223 _reflns_number_gt 890 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SIR2002 (Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.) ; _computing_structure_refinement 'SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)' _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material SHELXTL _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^ > 2\s(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. The atoms Cl1/Br1 was restraint to have equal coordinates and ADPs, because their separation was much lower than data resolution, but their complementar population factor was refined. The same conditions were applied to the second disordered couple Br3/Cl3. ; _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^)+(0.0186P)^2^+1.4955P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1223 _refine_ls_number_parameters 60 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0563 _refine_ls_wR_factor_gt 0.0509 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 0.28126(4) 0.0000 1.14703(11) 0.0686(4) Uani 0.772(3) 2 d SP . . Br1 Br 0.28126(4) 0.0000 1.14703(11) 0.0686(4) Uani 0.228(3) 2 d SP . . Br2 Br 0.375340(19) 0.0000 0.93199(6) 0.05521(17) Uani 1 2 d S . . Br3 Br 0.46383(2) 0.0000 0.72450(8) 0.0733(2) Uani 0.898(4) 2 d SP . . Cl3 Cl 0.46383(2) 0.0000 0.72450(8) 0.0733(2) Uani 0.102(4) 2 d SP . . N1 N 0.15926(12) 0.0000 0.6104(4) 0.0407(7) Uani 1 2 d S . . C1 C 0.03458(15) 0.0000 0.9985(6) 0.0523(10) Uani 1 2 d S . . H1A H 0.0500 -0.1074 1.0671 0.063 Uiso 0.50 1 calc PR . . H1B H 0.0500 0.1074 1.0671 0.063 Uiso 0.50 1 calc PR . . C2 C 0.05896(15) 0.0000 0.7952(6) 0.0529(10) Uani 1 2 d S . . H2A H 0.0442 -0.1077 0.7257 0.064 Uiso 0.50 1 calc PR . . H2B H 0.0442 0.1077 0.7257 0.064 Uiso 0.50 1 calc PR . . C3 C 0.12819(15) 0.0000 0.8044(5) 0.0427(8) Uani 1 2 d S . . H3A H 0.1419 -0.1072 0.8767 0.051 Uiso 0.50 1 calc PR . . H3B H 0.1419 0.1072 0.8767 0.051 Uiso 0.50 1 calc PR . . C4 C 0.22691(15) 0.0000 0.6532(6) 0.0553(10) Uani 1 2 d S . . H4A H 0.2379 0.1075 0.7267 0.083 Uiso 0.50 1 calc PR . . H4B H 0.2483 0.0000 0.5336 0.083 Uiso 1 2 calc SR . . H4C H 0.2379 -0.1075 0.7267 0.083 Uiso 0.50 1 calc PR . . C5 C 0.14227(13) 0.1664(4) 0.4954(4) 0.0612(8) Uani 1 1 d . . . H5A H 0.1531 0.2741 0.5687 0.092 Uiso 1 1 calc R . . H5B H 0.0989 0.1660 0.4672 0.092 Uiso 1 1 calc R . . H5C H 0.1639 0.1661 0.3762 0.092 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 0.0904(7) 0.0655(6) 0.0502(5) 0.000 0.0072(4) 0.000 Br1 0.0904(7) 0.0655(6) 0.0502(5) 0.000 0.0072(4) 0.000 Br2 0.0677(3) 0.0437(2) 0.0535(3) 0.000 -0.01080(18) 0.000 Br3 0.0673(3) 0.0647(4) 0.0880(4) 0.000 0.0022(3) 0.000 Cl3 0.0673(3) 0.0647(4) 0.0880(4) 0.000 0.0022(3) 0.000 N1 0.0400(15) 0.0428(17) 0.0395(16) 0.000 0.0035(12) 0.000 C1 0.044(2) 0.054(2) 0.060(2) 0.000 0.0132(18) 0.000 C2 0.038(2) 0.064(3) 0.057(2) 0.000 0.0068(17) 0.000 C3 0.0435(19) 0.047(2) 0.0379(19) 0.000 0.0066(15) 0.000 C4 0.0378(19) 0.077(3) 0.051(2) 0.000 0.0069(16) 0.000 C5 0.0691(18) 0.0565(18) 0.0580(16) 0.0184(15) 0.0000(13) 0.0004(15) _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 Br2 2.5670(10) . ? Br2 Br3 2.4363(8) . ? N1 C5 1.490(3) . ? N1 C5 1.490(3) 6 ? N1 C4 1.495(4) . ? N1 C3 1.517(4) . ? C1 C1 1.509(7) 5_557 ? C1 C2 1.514(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.509(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 Br3 Br2 Cl1 179.32(3) . . ? C5 N1 C5 109.0(3) . 6 ? C5 N1 C4 109.44(18) . . ? C5 N1 C4 109.44(18) 6 . ? C5 N1 C3 111.03(18) . . ? C5 N1 C3 111.03(18) 6 . ? C4 N1 C3 106.9(3) . . ? C1 C1 C2 113.1(4) 5_557 . ? C1 C1 H1A 109.0 5_557 . ? C2 C1 H1A 109.0 . . ? C1 C1 H1B 109.0 5_557 . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 109.9(3) . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 N1 115.8(3) . . ? C2 C3 H3A 108.3 . . ? N1 C3 H3A 108.3 . . ? C2 C3 H3B 108.3 . . ? N1 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? N1 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 C1 C2 C3 180.0 5_557 . . . ? C1 C2 C3 N1 180.0 . . . . ? C5 N1 C3 C2 60.72(18) . . . . ? C5 N1 C3 C2 -60.72(18) 6 . . . ? C4 N1 C3 C2 180.0 . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.320 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.050