# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Robin Rogers' _publ_contact_author_email RDROGERS@AS.UA.EDU _publ_section_title ; A General Design Platform for Ionic Liquid Ions Based on Bridged Multi-Heterocycles with Flexible Symmetry and Charge ; loop_ _publ_author_name 'Robin Rogers' 'David B. Cordes' 'David M. Drab' 'C. Corey Hines' 'Julia L. Shamshina' 'Marcin Smiglak' # Attachment 'Drab-Rogers_Chem_Comm_XRD_structures_02-08-2010.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 765819' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Br0.80 Cl1.20 N6 Zn' _chemical_formula_weight 336.02 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' Zn Zn 0.2839 1.4301 '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 P2(1)/n 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 6.5163(4) _cell_length_b 9.5129(6) _cell_length_c 17.9703(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.9240(10) _cell_angle_gamma 90.00 _cell_volume 1103.32(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4069 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.06 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.023 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 658 _exptl_absorpt_coefficient_mu 5.389 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.69940 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7472 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2581 _reflns_number_gt 2200 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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 'calc w=1/[\s^2^(Fo^2^)+(0.0677P)^2^+7.6007P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2581 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1333 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Zn Zn 0.51763(8) 0.30437(5) 0.21457(3) 0.01421(17) Uani 1 1 d . . . Cl1 Cl 0.82626(14) 0.26536(12) 0.28430(6) 0.0424(3) Uani 0.60 1 d P . . Cl2 Cl 0.51489(14) 0.38340(10) 0.09463(5) 0.0326(2) Uani 0.60 1 d P . . Br1 Br 0.82626(14) 0.26536(12) 0.28430(6) 0.0424(3) Uani 0.40 1 d P . . Br2 Br 0.51489(14) 0.38340(10) 0.09463(5) 0.0326(2) Uani 0.40 1 d P . . N1A N 0.4372(6) 0.1094(4) 0.3891(2) 0.0150(7) Uani 1 1 d . . . N1B N 0.3315(6) 0.1325(4) 0.2119(2) 0.0157(7) Uani 1 1 d . . . N2B N 0.1760(6) 0.1164(4) 0.1544(2) 0.0190(8) Uani 1 1 d . . . N3A N 0.3262(7) 0.2694(4) 0.4581(2) 0.0229(9) Uani 1 1 d . . . N3B N 0.0629(6) 0.0096(4) 0.1672(2) 0.0193(8) Uani 1 1 d . . . N4B N 0.1420(6) -0.0467(4) 0.2345(2) 0.0142(7) Uani 1 1 d . . . C2A C 0.2780(8) 0.1900(5) 0.3967(3) 0.0195(9) Uani 1 1 d . . . H2A H 0.1501 0.1916 0.3642 0.023 Uiso 1 1 calc R . . C4A C 0.5243(9) 0.2358(6) 0.4901(3) 0.0251(11) Uani 1 1 d . . . H4A H 0.5978 0.2759 0.5343 0.030 Uiso 1 1 calc R . . C5B C 0.3063(7) 0.0297(5) 0.2606(2) 0.0125(8) Uani 1 1 d . . . C5A C 0.5947(8) 0.1355(6) 0.4469(3) 0.0221(10) Uani 1 1 d . . . H5A H 0.7268 0.0915 0.4548 0.027 Uiso 1 1 calc R . . C6 C 0.4489(7) 0.0002(5) 0.3314(2) 0.0161(9) Uani 1 1 d . . . H6A H 0.4129 -0.0920 0.3516 0.019 Uiso 1 1 calc R . . H6B H 0.5929 -0.0056 0.3199 0.019 Uiso 1 1 calc R . . C7 C 0.1927(11) 0.3783(6) 0.4843(4) 0.0359(14) Uani 1 1 d . . . H7A H 0.2427 0.4714 0.4718 0.054 Uiso 1 1 calc R . . H7B H 0.1962 0.3706 0.5388 0.054 Uiso 1 1 calc R . . H7C H 0.0502 0.3655 0.4596 0.054 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 Zn 0.0140(3) 0.0139(3) 0.0143(3) 0.00043(19) 0.00020(18) 0.00012(19) Cl1 0.0246(5) 0.0529(6) 0.0476(6) 0.0165(5) -0.0022(4) 0.0031(4) Cl2 0.0337(5) 0.0376(5) 0.0264(4) 0.0023(3) 0.0036(3) -0.0039(4) Br1 0.0246(5) 0.0529(6) 0.0476(6) 0.0165(5) -0.0022(4) 0.0031(4) Br2 0.0337(5) 0.0376(5) 0.0264(4) 0.0023(3) 0.0036(3) -0.0039(4) N1A 0.0178(18) 0.0170(18) 0.0094(16) -0.0012(14) -0.0007(14) -0.0005(14) N1B 0.0183(19) 0.0142(18) 0.0137(17) 0.0005(14) -0.0012(14) 0.0008(15) N2B 0.023(2) 0.019(2) 0.0125(18) 0.0027(15) -0.0053(15) -0.0038(16) N3A 0.035(2) 0.017(2) 0.019(2) -0.0012(16) 0.0092(17) -0.0005(17) N3B 0.023(2) 0.020(2) 0.0127(18) 0.0018(15) -0.0045(15) -0.0015(16) N4B 0.0183(19) 0.0137(17) 0.0094(16) 0.0002(14) -0.0021(14) -0.0008(14) C2A 0.021(2) 0.018(2) 0.019(2) -0.0004(18) -0.0006(18) -0.0003(18) C4A 0.031(3) 0.027(3) 0.015(2) -0.0026(19) -0.0053(19) -0.006(2) C5B 0.015(2) 0.0115(19) 0.0107(18) -0.0010(15) -0.0004(15) 0.0023(15) C5A 0.023(2) 0.025(2) 0.016(2) -0.0012(19) -0.0068(18) -0.002(2) C6 0.021(2) 0.013(2) 0.013(2) -0.0037(16) -0.0029(16) 0.0025(17) C7 0.053(4) 0.022(3) 0.038(3) -0.004(2) 0.025(3) 0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn N1B 2.033(4) . ? Zn N4B 2.047(4) 2 ? Zn Cl1 2.2489(10) . ? Zn Br1 2.2489(10) . ? Zn Cl2 2.2805(10) . ? Zn Br2 2.2805(10) . ? N1A C2A 1.313(6) . ? N1A C5A 1.379(6) . ? N1A C6 1.476(6) . ? N1B C5B 1.337(6) . ? N1B N2B 1.353(5) . ? N2B N3B 1.294(6) . ? N3A C2A 1.339(6) . ? N3A C4A 1.376(7) . ? N3A C7 1.471(7) . ? N3B N4B 1.357(5) . ? N4B C5B 1.326(6) . ? N4B Zn 2.047(4) 2_545 ? C4A C5A 1.349(7) . ? C5B C6 1.496(6) . ? 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 N1B Zn N4B 103.25(16) . 2 ? N1B Zn Cl1 111.42(11) . . ? N4B Zn Cl1 109.60(11) 2 . ? N1B Zn Br1 111.42(11) . . ? N4B Zn Br1 109.60(11) 2 . ? Cl1 Zn Br1 0.00(7) . . ? N1B Zn Cl2 108.42(11) . . ? N4B Zn Cl2 104.86(11) 2 . ? Cl1 Zn Cl2 118.09(4) . . ? Br1 Zn Cl2 118.09(4) . . ? N1B Zn Br2 108.42(11) . . ? N4B Zn Br2 104.86(11) 2 . ? Cl1 Zn Br2 118.09(4) . . ? Br1 Zn Br2 118.09(4) . . ? Cl2 Zn Br2 0.00(5) . . ? C2A N1A C5A 109.4(4) . . ? C2A N1A C6 127.1(4) . . ? C5A N1A C6 123.4(4) . . ? C5B N1B N2B 105.7(4) . . ? C5B N1B Zn 134.4(3) . . ? N2B N1B Zn 119.4(3) . . ? N3B N2B N1B 109.7(4) . . ? C2A N3A C4A 108.2(4) . . ? C2A N3A C7 125.4(5) . . ? C4A N3A C7 126.3(5) . . ? N2B N3B N4B 108.2(4) . . ? C5B N4B N3B 106.7(4) . . ? C5B N4B Zn 131.1(3) . 2_545 ? N3B N4B Zn 121.2(3) . 2_545 ? N1A C2A N3A 108.5(4) . . ? C5A C4A N3A 107.3(4) . . ? N4B C5B N1B 109.6(4) . . ? N4B C5B C6 125.1(4) . . ? N1B C5B C6 125.2(4) . . ? C4A C5A N1A 106.5(4) . . ? N1A C6 C5B 112.3(4) . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.182 _refine_diff_density_min -1.341 _refine_diff_density_rms 0.165 #END data_5 _database_code_depnum_ccdc_archive 'CCDC 765820' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H10 N7 Na O2' _chemical_formula_weight 223.19 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0435(8) _cell_length_b 8.2860(9) _cell_length_c 8.5121(10) _cell_angle_alpha 91.350(2) _cell_angle_beta 91.457(2) _cell_angle_gamma 105.267(2) _cell_volume 478.86(9) _cell_formula_units_Z 2 _cell_measurement_temperature 178(2) _cell_measurement_reflns_used 2480 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 28.30 _exptl_crystal_description elliptical _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9360 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 178(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3297 _diffrn_reflns_av_R_equivalents 0.0104 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2182 _reflns_number_gt 2031 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.2695P] 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 2182 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0332 _refine_ls_wR_factor_ref 0.0832 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Na1 Na 0.36223(8) 0.91628(6) -0.16959(6) 0.01994(14) Uani 1 1 d . . . O1 O 0.39170(17) 0.81175(15) -0.41861(12) 0.0279(2) Uani 1 1 d . . . H201 H 0.497(4) 0.822(3) -0.467(3) 0.049(6) Uiso 1 1 d . . . H101 H 0.307(4) 0.825(3) -0.483(3) 0.058(7) Uiso 1 1 d . . . O2 O 0.69566(15) 0.95284(13) -0.07514(11) 0.0207(2) Uani 1 1 d . . . H202 H 0.795(3) 0.998(3) -0.123(2) 0.039(5) Uiso 1 1 d . . . H102 H 0.711(3) 0.862(3) -0.057(3) 0.053(7) Uiso 1 1 d . . . N1 N 0.26190(18) 0.64854(14) -0.04044(14) 0.0230(3) Uani 1 1 d . . . N2 N 0.26371(18) 0.38845(14) 0.03240(13) 0.0221(2) Uani 1 1 d . . . N3 N 0.28388(16) 0.49373(13) 0.16029(13) 0.0181(2) Uani 1 1 d . . . N4 N 0.26072(17) 0.19505(15) 0.57623(13) 0.0215(2) Uani 1 1 d . . . N5 N 0.19671(17) 0.11302(14) 0.70815(13) 0.0210(2) Uani 1 1 d . . . N6 N 0.01268(17) 0.11166(14) 0.72726(13) 0.0204(2) Uani 1 1 d . . . N7 N -0.04970(16) 0.19249(14) 0.60892(13) 0.0208(2) Uani 1 1 d . . . C1 C 0.2818(2) 0.64587(16) 0.11480(16) 0.0218(3) Uani 1 1 d . . . H1A H 0.294(2) 0.736(2) 0.188(2) 0.023(4) Uiso 1 1 d . . . C2 C 0.2513(2) 0.48779(17) -0.08488(16) 0.0223(3) Uani 1 1 d . . . H2A H 0.233(2) 0.445(2) -0.192(2) 0.024(4) Uiso 1 1 d . . . C3 C 0.2971(2) 0.43282(17) 0.31908(16) 0.0216(3) Uani 1 1 d . . . H3A H 0.395(3) 0.371(2) 0.318(2) 0.030(4) Uiso 1 1 d . . . H3B H 0.344(3) 0.528(2) 0.386(2) 0.028(4) Uiso 1 1 d . . . C4 C 0.0985(2) 0.32583(19) 0.36582(16) 0.0225(3) Uani 1 1 d . . . H4A H 0.052(3) 0.238(2) 0.283(2) 0.035(5) Uiso 1 1 d . . . H4B H 0.005(3) 0.390(2) 0.369(2) 0.037(5) Uiso 1 1 d . . . C5 C 0.10591(19) 0.24092(15) 0.51867(15) 0.0172(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na1 0.0224(3) 0.0224(3) 0.0164(3) 0.00563(19) 0.0012(2) 0.0077(2) O1 0.0216(5) 0.0476(6) 0.0193(5) 0.0047(4) 0.0031(4) 0.0169(5) O2 0.0218(5) 0.0215(5) 0.0210(5) 0.0066(4) 0.0059(4) 0.0085(4) N1 0.0271(6) 0.0233(6) 0.0207(6) 0.0087(4) 0.0054(5) 0.0094(5) N2 0.0261(6) 0.0198(5) 0.0198(5) 0.0013(4) 0.0020(4) 0.0050(4) N3 0.0208(5) 0.0179(5) 0.0159(5) 0.0051(4) 0.0029(4) 0.0052(4) N4 0.0212(5) 0.0291(6) 0.0172(5) 0.0077(4) 0.0038(4) 0.0109(5) N5 0.0246(6) 0.0246(5) 0.0167(5) 0.0055(4) 0.0037(4) 0.0108(5) N6 0.0219(5) 0.0236(5) 0.0161(5) 0.0051(4) 0.0029(4) 0.0061(4) N7 0.0187(5) 0.0282(6) 0.0165(5) 0.0065(4) 0.0031(4) 0.0071(4) C1 0.0287(7) 0.0184(6) 0.0202(6) 0.0053(5) 0.0067(5) 0.0088(5) C2 0.0234(7) 0.0246(6) 0.0180(6) 0.0031(5) 0.0030(5) 0.0043(5) C3 0.0229(6) 0.0238(6) 0.0173(6) 0.0075(5) -0.0006(5) 0.0041(5) C4 0.0201(6) 0.0314(7) 0.0175(6) 0.0102(5) 0.0031(5) 0.0087(5) C5 0.0176(6) 0.0195(6) 0.0151(6) 0.0027(4) 0.0019(4) 0.0054(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 Na1 O1 2.3058(12) . ? Na1 O2 2.4024(11) . ? Na1 O2 2.4190(11) 2_675 ? Na1 N1 2.4410(12) . ? Na1 N5 2.4736(12) 1_564 ? Na1 Na1 3.4836(11) 2_675 ? O2 Na1 2.4190(11) 2_675 ? N1 C1 1.3266(18) . ? N1 C2 1.3584(18) . ? N2 C2 1.3244(17) . ? N2 N3 1.3595(16) . ? N3 C1 1.3310(16) . ? N3 C3 1.4631(16) . ? N4 C5 1.3317(17) . ? N4 N5 1.3515(15) . ? N5 N6 1.3077(16) . ? N5 Na1 2.4736(12) 1_546 ? N6 N7 1.3492(15) . ? N7 C5 1.3335(17) . ? C3 C4 1.5141(19) . ? C4 C5 1.4998(17) . ? 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 O1 Na1 O2 98.37(4) . . ? O1 Na1 O2 172.35(4) . 2_675 ? O2 Na1 O2 87.47(4) . 2_675 ? O1 Na1 N1 97.43(4) . . ? O2 Na1 N1 90.36(4) . . ? O2 Na1 N1 87.42(4) 2_675 . ? O1 Na1 N5 87.99(4) . 1_564 ? O2 Na1 N5 131.44(4) . 1_564 ? O2 Na1 N5 84.43(4) 2_675 1_564 ? N1 Na1 N5 136.74(5) . 1_564 ? O1 Na1 Na1 142.05(4) . 2_675 ? O2 Na1 Na1 43.93(3) . 2_675 ? O2 Na1 Na1 43.55(3) 2_675 2_675 ? N1 Na1 Na1 88.46(4) . 2_675 ? N5 Na1 Na1 112.90(4) 1_564 2_675 ? Na1 O2 Na1 92.53(4) . 2_675 ? C1 N1 C2 102.40(11) . . ? C1 N1 Na1 119.00(9) . . ? C2 N1 Na1 134.17(9) . . ? C2 N2 N3 102.39(11) . . ? C1 N3 N2 109.69(11) . . ? C1 N3 C3 129.44(12) . . ? N2 N3 C3 120.83(10) . . ? C5 N4 N5 104.79(11) . . ? N6 N5 N4 109.26(10) . . ? N6 N5 Na1 124.68(8) . 1_546 ? N4 N5 Na1 122.67(8) . 1_546 ? N5 N6 N7 109.58(10) . . ? C5 N7 N6 104.66(10) . . ? N1 C1 N3 110.76(12) . . ? N2 C2 N1 114.76(12) . . ? N3 C3 C4 110.36(11) . . ? C5 C4 C3 113.38(11) . . ? N4 C5 N7 111.71(11) . . ? N4 C5 C4 125.22(12) . . ? N7 C5 C4 122.94(11) . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.250 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.044 #END data_10 _database_code_depnum_ccdc_archive 'CCDC 765821' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 N10' _chemical_formula_weight 246.26 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.1144(9) _cell_length_b 25.233(4) _cell_length_c 7.1186(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.739(2) _cell_angle_gamma 90.00 _cell_volume 1062.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4080 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 23.22 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9265 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4766 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 23.22 _reflns_number_total 1509 _reflns_number_gt 1449 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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 'calc w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.4401P] 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 1509 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0832 _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 N1 N 0.5230(2) 0.33120(5) 0.07682(17) 0.0215(3) Uani 1 1 d . . . N2B N 0.9350(2) 0.41074(5) -0.59639(19) 0.0267(3) Uani 1 1 d . . . H H 1.001(3) 0.3776(9) -0.542(3) 0.050(6) Uiso 1 1 d . . . N2A N 0.1082(2) 0.26749(5) 0.1092(2) 0.0305(4) Uani 1 1 d . . . N3 N 0.6272(2) 0.39031(5) -0.10094(18) 0.0270(3) Uani 1 1 d . . . N3B N 1.0188(2) 0.43840(5) -0.7241(2) 0.0314(4) Uani 1 1 d . . . N3A N -0.0211(2) 0.22400(5) 0.0625(2) 0.0331(4) Uani 1 1 d . . . N4B N 0.8955(2) 0.48081(5) -0.7655(2) 0.0313(4) Uani 1 1 d . . . N4A N 0.1094(2) 0.18315(5) 0.0568(2) 0.0311(3) Uani 1 1 d . . . N5A N 0.3274(2) 0.19829(5) 0.0989(2) 0.0281(3) Uani 1 1 d . . . N5B N 0.7323(2) 0.48139(5) -0.66670(19) 0.0283(3) Uani 1 1 d . . . C1A C 0.3190(2) 0.24998(6) 0.1299(2) 0.0219(4) Uani 1 1 d . . . C1B C 0.7602(2) 0.43737(6) -0.5630(2) 0.0232(4) Uani 1 1 d . . . C2 C 0.6757(2) 0.34299(6) -0.0200(2) 0.0243(4) Uani 1 1 d . . . H2A H 0.7990 0.3212 -0.0296 0.029 Uiso 1 1 calc R . . C4 C 0.4360(3) 0.40929(6) -0.0556(2) 0.0302(4) Uani 1 1 d . . . H4A H 0.3632 0.4422 -0.0956 0.036 Uiso 1 1 calc R . . C5 C 0.3715(3) 0.37240(6) 0.0562(2) 0.0268(4) Uani 1 1 d . . . H5A H 0.2451 0.3745 0.1106 0.032 Uiso 1 1 calc R . . C6 C 0.5274(3) 0.28309(6) 0.1949(2) 0.0259(4) Uani 1 1 d . . . H6A H 0.5450 0.2935 0.3320 0.031 Uiso 1 1 calc R . . H6B H 0.6606 0.2615 0.1888 0.031 Uiso 1 1 calc R . . C7 C 0.7557(3) 0.41674(7) -0.2224(2) 0.0368(4) Uani 1 1 d . . . H7A H 0.8990 0.3974 -0.2129 0.044 Uiso 1 1 calc R . . H7B H 0.7936 0.4533 -0.1744 0.044 Uiso 1 1 calc R . . C8 C 0.6207(3) 0.41860(6) -0.4328(2) 0.0276(4) Uani 1 1 d . . . H8A H 0.5617 0.3828 -0.4739 0.033 Uiso 1 1 calc R . . H8B H 0.4898 0.4426 -0.4449 0.033 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 N1 0.0206(6) 0.0214(7) 0.0222(7) 0.0003(5) 0.0048(5) -0.0025(5) N2B 0.0280(7) 0.0235(7) 0.0300(7) 0.0016(6) 0.0098(6) 0.0033(6) N2A 0.0231(7) 0.0273(7) 0.0401(9) -0.0024(6) 0.0058(6) -0.0003(6) N3 0.0254(7) 0.0278(7) 0.0267(7) 0.0025(6) 0.0047(6) -0.0073(6) N3B 0.0320(8) 0.0329(8) 0.0317(8) 0.0000(6) 0.0127(6) -0.0001(6) N3A 0.0237(7) 0.0341(8) 0.0404(9) -0.0025(6) 0.0062(6) -0.0044(6) N4B 0.0353(8) 0.0286(8) 0.0315(8) 0.0022(6) 0.0109(6) -0.0021(6) N4A 0.0284(8) 0.0270(7) 0.0361(8) -0.0001(6) 0.0051(6) -0.0055(6) N5A 0.0257(7) 0.0236(7) 0.0347(8) 0.0016(6) 0.0069(6) -0.0004(5) N5B 0.0311(8) 0.0239(7) 0.0306(8) 0.0024(6) 0.0093(6) 0.0014(6) C1A 0.0218(8) 0.0230(8) 0.0211(8) 0.0028(6) 0.0058(6) 0.0005(6) C1B 0.0231(8) 0.0205(8) 0.0248(8) -0.0016(6) 0.0039(6) 0.0003(6) C2 0.0206(8) 0.0254(8) 0.0263(8) -0.0010(7) 0.0048(6) -0.0013(6) C4 0.0315(9) 0.0222(8) 0.0350(10) 0.0016(7) 0.0051(7) 0.0016(7) C5 0.0245(8) 0.0255(8) 0.0315(9) -0.0018(7) 0.0091(7) 0.0021(6) C6 0.0239(8) 0.0263(8) 0.0264(8) 0.0049(7) 0.0042(7) -0.0013(6) C7 0.0356(10) 0.0436(10) 0.0308(9) 0.0072(8) 0.0075(8) -0.0160(8) C8 0.0245(8) 0.0279(8) 0.0306(9) 0.0017(7) 0.0073(7) 0.0010(7) _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 C2 1.3275(19) . ? N1 C5 1.375(2) . ? N1 C6 1.4728(19) . ? N2B C1B 1.334(2) . ? N2B N3B 1.3460(19) . ? N2A C1A 1.335(2) . ? N2A N3A 1.3440(19) . ? N3 C2 1.326(2) . ? N3 C4 1.376(2) . ? N3 C7 1.468(2) . ? N3B N4B 1.2988(19) . ? N3A N4A 1.3105(19) . ? N4B N5B 1.3597(19) . ? N4A N5A 1.3450(19) . ? N5A C1A 1.326(2) . ? N5B C1B 1.321(2) . ? C1A C6 1.495(2) . ? C1B C8 1.487(2) . ? C4 C5 1.347(2) . ? C7 C8 1.515(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 C2 N1 C5 108.59(13) . . ? C2 N1 C6 124.59(12) . . ? C5 N1 C6 126.73(12) . . ? C1B N2B N3B 108.61(13) . . ? C1A N2A N3A 104.35(12) . . ? C2 N3 C4 108.71(13) . . ? C2 N3 C7 124.81(14) . . ? C4 N3 C7 126.47(14) . . ? N4B N3B N2B 106.39(12) . . ? N4A N3A N2A 108.98(12) . . ? N3B N4B N5B 110.56(12) . . ? N3A N4A N5A 110.28(12) . . ? C1A N5A N4A 103.79(12) . . ? C1B N5B N4B 105.83(12) . . ? N5A C1A N2A 112.60(13) . . ? N5A C1A C6 122.36(13) . . ? N2A C1A C6 124.89(14) . . ? N5B C1B N2B 108.61(13) . . ? N5B C1B C8 127.09(14) . . ? N2B C1B C8 124.28(14) . . ? N3 C2 N1 108.56(13) . . ? C5 C4 N3 106.98(14) . . ? C4 C5 N1 107.15(14) . . ? N1 C6 C1A 113.17(12) . . ? N3 C7 C8 110.94(13) . . ? C1B C8 C7 111.77(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 23.22 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.164 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.042 #END data_3 _database_code_depnum_ccdc_archive 'CCDC 765822' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H9 Cl N6' _chemical_formula_weight 200.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 29.128(5) _cell_length_b 5.2371(9) _cell_length_c 12.583(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.339(3) _cell_angle_gamma 90.00 _cell_volume 1867.7(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3395 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 28.25 _exptl_crystal_description fragment _exptl_crystal_colour colorles _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8502 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5782 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2210 _reflns_number_gt 1863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.8013P] 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 2210 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1189 _refine_ls_wR_factor_gt 0.1135 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.568383(15) 0.91922(8) 0.39673(3) 0.04381(17) Uani 1 1 d . . . N1 N 0.58337(5) 0.5680(3) 0.64232(12) 0.0466(4) Uani 1 1 d . . . N2 N 0.64664(5) 0.4883(3) 0.58937(12) 0.0400(3) Uani 1 1 d . . . N3 N 0.66496(6) 0.7086(3) 0.39395(12) 0.0441(4) Uani 1 1 d . . . H3N H 0.6315(9) 0.770(5) 0.395(2) 0.074(7) Uiso 1 1 d . . . N4 N 0.68779(6) 0.8139(3) 0.32346(13) 0.0524(4) Uani 1 1 d . . . N5 N 0.72771(6) 0.6967(4) 0.33713(14) 0.0528(4) Uani 1 1 d . . . N6 N 0.73173(6) 0.5152(3) 0.41606(13) 0.0505(4) Uani 1 1 d . . . C1 C 0.53464(9) 0.5573(7) 0.6553(2) 0.0858(9) Uani 1 1 d . . . H1A H 0.5202 0.4011 0.6245 0.129 Uiso 1 1 calc R . . H1B H 0.5172 0.6998 0.6183 0.129 Uiso 1 1 calc R . . H1C H 0.5346 0.5642 0.7315 0.129 Uiso 1 1 calc R . . C2 C 0.60199(7) 0.4187(4) 0.57919(15) 0.0441(4) Uani 1 1 d . . . H2A H 0.5867(7) 0.298(4) 0.5326(17) 0.048(5) Uiso 1 1 d . . . C3 C 0.65633(7) 0.6910(4) 0.66094(14) 0.0440(4) Uani 1 1 d . . . H3A H 0.6882(9) 0.762(5) 0.685(2) 0.067(7) Uiso 1 1 d . . . C4 C 0.61654(7) 0.7405(4) 0.69305(15) 0.0473(4) Uani 1 1 d . . . H4A H 0.6101(9) 0.869(5) 0.746(2) 0.074(7) Uiso 1 1 d . . . C5 C 0.68005(9) 0.3632(4) 0.5358(2) 0.0551(5) Uani 1 1 d . . . H5A H 0.6644(10) 0.209(6) 0.500(2) 0.085(9) Uiso 1 1 d . . . H5B H 0.7092(11) 0.305(6) 0.587(2) 0.091(9) Uiso 1 1 d . . . C6 C 0.69223(6) 0.5274(3) 0.44975(14) 0.0401(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0402(2) 0.0482(3) 0.0448(3) 0.00196(18) 0.01323(18) 0.00579(17) N1 0.0409(8) 0.0624(10) 0.0408(8) 0.0028(7) 0.0186(6) 0.0013(7) N2 0.0436(8) 0.0399(7) 0.0408(7) 0.0044(6) 0.0183(6) 0.0056(6) N3 0.0442(8) 0.0460(9) 0.0454(8) 0.0021(7) 0.0173(7) 0.0068(6) N4 0.0586(10) 0.0571(10) 0.0452(9) 0.0060(7) 0.0194(8) 0.0061(8) N5 0.0529(9) 0.0607(10) 0.0505(9) 0.0028(8) 0.0236(8) 0.0040(8) N6 0.0472(9) 0.0594(10) 0.0506(9) 0.0034(8) 0.0231(7) 0.0105(7) C1 0.0466(12) 0.137(3) 0.0825(18) -0.0057(17) 0.0334(12) -0.0042(14) C2 0.0482(10) 0.0465(10) 0.0390(9) -0.0016(8) 0.0132(8) -0.0061(8) C3 0.0448(10) 0.0482(10) 0.0392(9) -0.0004(7) 0.0105(7) -0.0017(8) C4 0.0547(11) 0.0533(11) 0.0369(9) -0.0057(8) 0.0167(8) 0.0026(8) C5 0.0651(13) 0.0474(11) 0.0638(13) 0.0101(10) 0.0373(11) 0.0198(10) C6 0.0420(9) 0.0403(9) 0.0411(9) -0.0033(7) 0.0158(7) 0.0073(7) _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 C2 1.317(2) . ? N1 C4 1.369(3) . ? N1 C1 1.466(3) . ? N2 C2 1.328(2) . ? N2 C3 1.378(2) . ? N2 C5 1.461(2) . ? N3 C6 1.329(2) . ? N3 N4 1.344(2) . ? N4 N5 1.291(2) . ? N5 N6 1.360(2) . ? N6 C6 1.316(2) . ? C3 C4 1.338(3) . ? C5 C6 1.488(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 C2 N1 C4 109.17(15) . . ? C2 N1 C1 126.0(2) . . ? C4 N1 C1 124.79(19) . . ? C2 N2 C3 108.82(15) . . ? C2 N2 C5 125.03(18) . . ? C3 N2 C5 126.11(17) . . ? C6 N3 N4 108.37(15) . . ? N5 N4 N3 106.54(16) . . ? N4 N5 N6 110.66(15) . . ? C6 N6 N5 105.47(15) . . ? N1 C2 N2 108.02(17) . . ? C4 C3 N2 106.61(17) . . ? C3 C4 N1 107.37(17) . . ? N2 C5 C6 111.86(16) . . ? N6 C6 N3 108.96(16) . . ? N6 C6 C5 125.37(17) . . ? N3 C6 C5 125.67(16) . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.398 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.057