# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1475 _publ_contact_author_name 'Xi Zhang' _publ_contact_author_email xi@mail.tsinghua.edu.cn _publ_contact_author_address ; ; loop_ _publ_author_name 'Xi Zhang' # Attachment '- exp_346.cif' data_exp_346 _database_code_depnum_ccdc_archive 'CCDC 890516' #TrackingRef '- exp_346.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H23 N6, Cl ' _chemical_formula_sum 'C11 H23 Cl N6' _chemical_formula_weight 274.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 4.4289(4) _cell_length_b 9.6455(18) _cell_length_c 17.6718(18) _cell_angle_alpha 101.395(8) _cell_angle_beta 95.279(8) _cell_angle_gamma 92.673(7) _cell_volume 735.27(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1328 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 26 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.885 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'CrysAlisPro (Oxford, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0971 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4647 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0778 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2901 _reflns_number_gt 2228 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford, 2011)' _computing_cell_refinement 'CrysAlisPro (Oxford, 2011)' _computing_data_reduction 'CrysAlisPro (Oxford, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 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^)+(0.0010P)^2^+1.5000P] 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 2901 _refine_ls_number_parameters 206 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1011 _refine_ls_R_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1406 _refine_ls_goodness_of_fit_ref 1.236 _refine_ls_restrained_S_all 1.289 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL exp_346 in P-1 CELL 0.71073 4.4289 9.6455 17.6718 101.395 95.279 92.673 ZERR 2.00 0.0004 0.0018 0.0018 0.008 0.008 0.007 LATT 1 SFAC C H N Cl UNIT 22 46 12 2 OMIT -2 52 EQIV $1 X, 1+Y, Z EQIV $2 -X, 1-Y, 1-Z HTAB N3 CL1_$1 HTAB N4 CL1 HTAB N5 CL1_$2 HTAB N6 CL1_$1 L.S. 4 ACTA BOND $H FMAP 2 PLAN 10 EXYZ C6 C6' EADP C6 C6' EXYZ C9 C9' EADP C9 C9' DFIX 1.53 0.01 C9 C10 C10 C11 C9' C10' C10' C11' C6 C7 C6 C7' WGHT 0.001000 1.500000 FVAR 0.30691 0.45020 CL1 4 0.369843 0.133756 0.596802 11.00000 0.02432 0.00908 = 0.05056 0.01094 0.00330 0.00058 N1 3 0.736061 0.695924 0.670733 11.00000 0.01750 0.01364 = 0.02198 0.00301 0.00172 -0.00298 N2 3 0.334140 0.568203 0.577309 11.00000 0.01934 0.00817 = 0.02322 0.00511 0.00037 -0.00088 N3 3 0.454247 0.810669 0.585183 11.00000 0.01899 0.00595 = 0.03335 0.00614 -0.00050 -0.00064 H3A 2 0.404079 0.879230 0.572985 11.00000 -1.20000 N4 3 0.621863 0.457897 0.658766 11.00000 0.02190 0.01333 = 0.02594 0.00843 -0.00403 -0.00285 H4C 2 0.536237 0.392178 0.636303 11.00000 -1.20000 N5 3 0.059223 0.692319 0.499369 11.00000 0.02244 0.00849 = 0.03079 0.00709 -0.00390 0.00081 H5C 2 -0.027097 0.620477 0.475605 11.00000 -1.20000 H5D 2 0.011539 0.766802 0.483490 11.00000 -1.20000 N6 3 0.843247 0.932623 0.671973 11.00000 0.02273 0.01389 = 0.03501 0.00293 0.00450 -0.00540 H6C 2 0.799931 0.995510 0.654118 11.00000 -1.20000 C1 1 0.562761 0.577275 0.634752 11.00000 0.01629 0.01469 = 0.02091 0.00565 0.00580 -0.00122 C2 1 0.281256 0.688419 0.553263 11.00000 0.01351 0.01101 = 0.02243 0.00281 0.00420 0.00063 C3 1 0.678207 0.811225 0.642953 11.00000 0.01578 0.01402 = 0.02673 0.00169 0.00660 -0.00112 C4 1 0.865542 0.440509 0.716428 11.00000 0.02004 0.03001 = 0.03544 0.01770 -0.00678 -0.00478 AFIX 23 H4A 2 1.025841 0.514080 0.719564 11.00000 -1.20000 H4B 2 0.949915 0.349740 0.699921 11.00000 -1.20000 AFIX 0 C5 1 0.759981 0.447657 0.796142 11.00000 0.03079 0.08629 = 0.03746 0.03956 -0.01104 -0.01855 AFIX 23 H5A 2 0.586157 0.380333 0.791284 11.00000 -1.20000 H5B 2 0.920973 0.417265 0.828943 11.00000 -1.20000 AFIX 0 PART 1 C6 1 0.672917 0.590269 0.836577 10.50000 0.03493 0.11299 = 0.02313 0.00914 0.00279 -0.00889 AFIX 3 H6A 2 0.506737 0.619849 0.805087 10.50000 -1.20000 H6B 2 0.844347 0.658720 0.840887 10.50000 -1.20000 AFIX 0 C7 1 0.585124 0.552074 0.913192 10.50000 0.04985 0.05759 = 0.02647 -0.00338 0.00572 -0.01619 AFIX 33 H7A 2 0.523552 0.635058 0.946273 10.50000 -1.50000 H7B 2 0.757063 0.517074 0.938927 10.50000 -1.50000 H7C 2 0.420360 0.480424 0.901846 10.50000 -1.50000 AFIX 0 PART 2 C6' 1 0.672917 0.590269 0.836577 10.50000 0.03493 0.11299 = 0.02313 0.00914 0.00279 -0.00889 AFIX 3 H6D 2 0.507894 0.617914 0.801692 10.50000 -1.20000 H6E 2 0.838903 0.655624 0.836732 10.50000 -1.20000 AFIX 0 C7' 1 0.573128 0.625312 0.919351 10.50000 0.05323 0.03428 = 0.02207 -0.00387 -0.00071 -0.00993 AFIX 33 H7D 2 0.531648 0.723553 0.931940 10.50000 -1.50000 H7E 2 0.732693 0.606528 0.955808 10.50000 -1.50000 H7F 2 0.393034 0.567632 0.921741 10.50000 -1.50000 AFIX 0 PART 0 C8 1 1.069727 0.949284 0.738083 11.00000 0.03798 0.03657 = 0.02701 0.00090 0.00105 -0.02317 AFIX 23 H8A 2 1.225995 1.020562 0.734039 11.00000 -1.20000 H8B 2 1.164855 0.860510 0.737291 11.00000 -1.20000 AFIX 0 PART 1 C9 1 0.937638 0.992002 0.813483 10.50000 0.06720 0.06319 = 0.03580 -0.00944 0.01731 -0.04692 AFIX 23 H9A 2 0.791548 1.061206 0.806027 10.50000 -1.20000 H9B 2 0.822505 0.909053 0.821554 10.50000 -1.20000 AFIX 0 C10 1 1.121155 1.049375 0.885190 10.50000 0.02750 0.04062 = 0.02878 0.01303 -0.00240 -0.00781 AFIX 23 H10A 2 1.254366 1.126115 0.876460 10.50000 -1.20000 H10B 2 1.249363 0.976190 0.897268 10.50000 -1.20000 AFIX 0 C11 1 0.962161 1.105046 0.956246 10.50000 0.04749 0.05663 = 0.03391 0.00914 0.00100 0.00638 AFIX 33 H11A 2 1.110925 1.139434 0.999785 10.50000 -1.50000 H11B 2 0.833917 1.030081 0.967306 10.50000 -1.50000 H11C 2 0.840833 1.180921 0.946699 10.50000 -1.50000 AFIX 0 PART 2 C9' 1 0.937638 0.992002 0.813483 10.50000 0.06720 0.06319 = 0.03580 -0.00944 0.01731 -0.04692 AFIX 23 H9C 2 0.747314 0.936202 0.810418 10.50000 -1.20000 H9D 2 1.074314 0.966324 0.853847 10.50000 -1.20000 AFIX 0 C10' 1 0.881750 1.135129 0.836940 10.50000 0.03205 0.01567 = 0.03133 -0.00055 0.00915 -0.00422 AFIX 23 H10C 2 0.727078 1.159350 0.800089 10.50000 -1.20000 H10D 2 1.065990 1.192734 0.835692 10.50000 -1.20000 AFIX 0 C11' 1 0.778418 1.171387 0.917547 10.50000 0.04262 0.02477 = 0.03843 0.00091 0.00690 0.00236 AFIX 33 H11D 2 0.746417 1.270698 0.930244 10.50000 -1.50000 H11E 2 0.931407 1.149030 0.954576 10.50000 -1.50000 H11F 2 0.592005 1.117390 0.918857 10.50000 -1.50000 PART 0 HKLF 4 REM exp_346 in P-1 REM R1 = 0.0772 for 2228 Fo > 4sig(Fo) and 0.1011 for all 2901 data REM 206 parameters refined using 6 restraints END ; 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 0.3698(2) 0.13376(10) 0.59680(7) 0.0274(3) Uani 1 1 d . . . N1 N 0.7361(7) 0.6959(3) 0.67073(19) 0.0179(7) Uani 1 1 d . . . N2 N 0.3341(7) 0.5682(3) 0.57731(19) 0.0168(7) Uani 1 1 d . . . N3 N 0.4542(7) 0.8107(3) 0.5852(2) 0.0194(8) Uani 1 1 d . . . H3A H 0.404(9) 0.879(5) 0.573(2) 0.023 Uiso 1 1 d . . . N4 N 0.6219(8) 0.4579(4) 0.6588(2) 0.0203(8) Uani 1 1 d . . . H4C H 0.536(10) 0.392(5) 0.636(3) 0.024 Uiso 1 1 d . . . N5 N 0.0592(8) 0.6923(4) 0.4994(2) 0.0206(8) Uani 1 1 d . . . H5C H -0.027(10) 0.620(5) 0.476(2) 0.025 Uiso 1 1 d . . . H5D H 0.012(9) 0.767(5) 0.483(2) 0.025 Uiso 1 1 d . . . N6 N 0.8432(8) 0.9326(4) 0.6720(2) 0.0243(8) Uani 1 1 d . D . H6C H 0.800(10) 0.996(5) 0.654(3) 0.029 Uiso 1 1 d . . . C1 C 0.5628(8) 0.5773(4) 0.6348(2) 0.0168(8) Uani 1 1 d . . . C2 C 0.2813(8) 0.6884(4) 0.5533(2) 0.0156(8) Uani 1 1 d . . . C3 C 0.6782(8) 0.8112(4) 0.6430(2) 0.0190(9) Uani 1 1 d . . . C4 C 0.8655(9) 0.4405(5) 0.7164(3) 0.0278(10) Uani 1 1 d . B . H4A H 1.0258 0.5141 0.7196 0.033 Uiso 1 1 calc R . . H4B H 0.9499 0.3497 0.6999 0.033 Uiso 1 1 calc R . . C5 C 0.7600(11) 0.4477(7) 0.7961(3) 0.0494(15) Uani 1 1 d . . . H5A H 0.5862 0.3803 0.7913 0.059 Uiso 1 1 calc R A 1 H5B H 0.9210 0.4173 0.8289 0.059 Uiso 1 1 calc R A 1 C6 C 0.6729(12) 0.5903(8) 0.8366(3) 0.0581(18) Uani 0.50 1 d PD B 1 H6A H 0.5067 0.6198 0.8051 0.070 Uiso 0.50 1 d PR B 1 H6B H 0.8443 0.6587 0.8409 0.070 Uiso 0.50 1 d PR B 1 C7 C 0.585(4) 0.5521(14) 0.9132(6) 0.047(4) Uani 0.50 1 d PD B 1 H7A H 0.5236 0.6351 0.9463 0.070 Uiso 0.50 1 calc PR B 1 H7B H 0.7571 0.5171 0.9389 0.070 Uiso 0.50 1 calc PR B 1 H7C H 0.4204 0.4804 0.9018 0.070 Uiso 0.50 1 calc PR B 1 C6' C 0.6729(12) 0.5903(8) 0.8366(3) 0.0581(18) Uani 0.50 1 d P B 2 H6D H 0.5079 0.6179 0.8017 0.070 Uiso 0.50 1 d PR B 2 H6E H 0.8389 0.6556 0.8367 0.070 Uiso 0.50 1 d PR B 2 C7' C 0.573(4) 0.6253(12) 0.9194(5) 0.039(3) Uani 0.50 1 d PD B 2 H7D H 0.5316 0.7236 0.9319 0.058 Uiso 0.50 1 calc PR B 2 H7E H 0.7327 0.6065 0.9558 0.058 Uiso 0.50 1 calc PR B 2 H7F H 0.3930 0.5676 0.9217 0.058 Uiso 0.50 1 calc PR B 2 C8 C 1.0697(10) 0.9493(5) 0.7381(3) 0.0356(12) Uani 1 1 d . . . H8A H 1.2260 1.0206 0.7340 0.043 Uiso 1 1 calc R C 1 H8B H 1.1649 0.8605 0.7373 0.043 Uiso 1 1 calc R C 1 C9 C 0.9376(13) 0.9920(6) 0.8135(3) 0.0590(19) Uani 0.50 1 d PD D 1 H9A H 0.7915 1.0612 0.8060 0.071 Uiso 0.50 1 calc PR D 1 H9B H 0.8225 0.9091 0.8216 0.071 Uiso 0.50 1 calc PR D 1 C10 C 1.1212(18) 1.0494(10) 0.8852(4) 0.032(2) Uani 0.50 1 d PD D 1 H10A H 1.2544 1.1261 0.8765 0.039 Uiso 0.50 1 calc PR D 1 H10B H 1.2494 0.9762 0.8973 0.039 Uiso 0.50 1 calc PR D 1 C11 C 0.962(2) 1.1050(12) 0.9562(5) 0.046(3) Uani 0.50 1 d PD D 1 H11A H 1.1109 1.1394 0.9998 0.069 Uiso 0.50 1 calc PR D 1 H11B H 0.8339 1.0301 0.9673 0.069 Uiso 0.50 1 calc PR D 1 H11C H 0.8408 1.1809 0.9467 0.069 Uiso 0.50 1 calc PR D 1 C9' C 0.9376(13) 0.9920(6) 0.8135(3) 0.0590(19) Uani 0.50 1 d PD D 2 H9C H 0.7473 0.9362 0.8104 0.071 Uiso 0.50 1 calc PR D 2 H9D H 1.0743 0.9663 0.8538 0.071 Uiso 0.50 1 calc PR D 2 C10' C 0.882(2) 1.1351(7) 0.8369(4) 0.027(2) Uani 0.50 1 d PD D 2 H10C H 0.7271 1.1593 0.8001 0.032 Uiso 0.50 1 calc PR D 2 H10D H 1.0660 1.1927 0.8357 0.032 Uiso 0.50 1 calc PR D 2 C11' C 0.778(2) 1.1714(10) 0.9175(5) 0.036(2) Uani 0.50 1 d PD D 2 H11D H 0.7464 1.2707 0.9302 0.054 Uiso 0.50 1 calc PR D 2 H11E H 0.9314 1.1490 0.9546 0.054 Uiso 0.50 1 calc PR D 2 H11F H 0.5920 1.1174 0.9189 0.054 Uiso 0.50 1 calc PR D 2 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 0.0243(5) 0.0091(5) 0.0506(7) 0.0109(4) 0.0033(5) 0.0006(4) N1 0.0175(16) 0.0136(17) 0.0220(18) 0.0030(14) 0.0017(14) -0.0030(13) N2 0.0193(16) 0.0082(15) 0.0232(18) 0.0051(13) 0.0004(14) -0.0009(13) N3 0.0190(17) 0.0060(16) 0.033(2) 0.0061(14) -0.0005(15) -0.0006(13) N4 0.0219(18) 0.0133(18) 0.026(2) 0.0084(15) -0.0040(15) -0.0028(14) N5 0.0224(19) 0.0085(17) 0.031(2) 0.0071(15) -0.0039(16) 0.0008(14) N6 0.0227(19) 0.0139(18) 0.035(2) 0.0029(16) 0.0045(17) -0.0054(15) C1 0.0163(19) 0.015(2) 0.021(2) 0.0056(16) 0.0058(17) -0.0012(15) C2 0.0135(18) 0.0110(19) 0.022(2) 0.0028(16) 0.0042(17) 0.0006(14) C3 0.016(2) 0.014(2) 0.027(2) 0.0017(16) 0.0066(18) -0.0011(15) C4 0.020(2) 0.030(2) 0.035(3) 0.018(2) -0.0068(19) -0.0048(18) C5 0.031(3) 0.086(5) 0.037(3) 0.040(3) -0.011(2) -0.019(3) C6 0.035(3) 0.113(6) 0.023(3) 0.009(3) 0.003(2) -0.009(3) C7 0.050(7) 0.058(9) 0.026(6) -0.003(7) 0.006(5) -0.016(8) C6' 0.035(3) 0.113(6) 0.023(3) 0.009(3) 0.003(2) -0.009(3) C7' 0.053(7) 0.034(7) 0.022(6) -0.004(5) -0.001(5) -0.010(7) C8 0.038(3) 0.037(3) 0.027(3) 0.001(2) 0.001(2) -0.023(2) C9 0.067(4) 0.063(4) 0.036(3) -0.009(3) 0.017(3) -0.047(3) C10 0.028(5) 0.041(6) 0.029(5) 0.013(4) -0.002(4) -0.008(4) C11 0.047(6) 0.057(7) 0.034(6) 0.009(5) 0.001(5) 0.006(5) C9' 0.067(4) 0.063(4) 0.036(3) -0.009(3) 0.017(3) -0.047(3) C10' 0.032(5) 0.016(4) 0.031(5) -0.001(4) 0.009(4) -0.004(4) C11' 0.043(6) 0.025(5) 0.038(6) 0.001(4) 0.007(5) 0.002(4) _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 C3 1.328(5) . ? N1 C1 1.358(5) . ? N2 C2 1.335(5) . ? N2 C1 1.353(5) . ? N3 C3 1.355(5) . ? N3 C2 1.367(5) . ? N3 H3A 0.77(4) . ? N4 C1 1.332(5) . ? N4 C4 1.454(5) . ? N4 H4C 0.74(4) . ? N5 C2 1.312(5) . ? N5 H5C 0.80(4) . ? N5 H5D 0.85(5) . ? N6 C3 1.335(5) . ? N6 C8 1.446(6) . ? N6 H6C 0.76(5) . ? C4 C5 1.514(6) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.504(8) . ? C5 C6' 1.504(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.549(9) . ? C6 C7' 1.545(9) . ? C6 H6A 0.9694 . ? C6 H6B 0.9700 . ? C6 H6D 0.9927 . ? C6 H6E 0.9453 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C7' H7D 0.9600 . ? C7' H7E 0.9600 . ? C7' H7F 0.9600 . ? C8 C9 1.495(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.437(7) . ? C9 C10' 1.401(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C9 H9D 0.9700 . ? C10 C11 1.514(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C10' C11' 1.516(8) . ? C10' H10C 0.9700 . ? C10' H10D 0.9700 . ? C11' H11D 0.9600 . ? C11' H11E 0.9600 . ? C11' H11F 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 C3 N1 C1 114.9(3) . . ? C2 N2 C1 115.7(3) . . ? C3 N3 C2 120.0(3) . . ? C3 N3 H3A 122(3) . . ? C2 N3 H3A 117(3) . . ? C1 N4 C4 126.3(3) . . ? C1 N4 H4C 116(4) . . ? C4 N4 H4C 117(4) . . ? C2 N5 H5C 120(3) . . ? C2 N5 H5D 124(3) . . ? H5C N5 H5D 115(4) . . ? C3 N6 C8 122.9(4) . . ? C3 N6 H6C 116(4) . . ? C8 N6 H6C 121(4) . . ? N4 C1 N2 116.6(3) . . ? N4 C1 N1 116.8(4) . . ? N2 C1 N1 126.5(3) . . ? N5 C2 N2 120.7(3) . . ? N5 C2 N3 118.6(4) . . ? N2 C2 N3 120.7(4) . . ? N1 C3 N6 120.0(4) . . ? N1 C3 N3 122.1(3) . . ? N6 C3 N3 118.0(4) . . ? N4 C4 C5 112.7(4) . . ? N4 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? N4 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 116.1(4) . . ? C6 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? C6 C5 H5B 108.3 . . ? C4 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C5 C6 C7 99.5(7) . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6A 114.6 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 116.6 . . ? H6A C6 H6B 107.8 . . ? C5 C6 C7' 125.5(7) . . ? C7' C6 H6D 106.4 . . ? C7' C6 H6E 105.4 . . ? C5 C6 H6D 106.2 . . ? C5 C6 H6E 106.8 . . ? H6D C6 H6E 104.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C7' H7E 109.5 . . ? C6 C7' H7D 109.5 . . ? C6 C7' H7F 109.5 . . ? H7D C7' H7E 109.5 . . ? H7D C7' H7F 109.5 . . ? H7E C7' H7F 109.5 . . ? N6 C8 C9 112.4(4) . . ? N6 C8 H8A 109.1 . . ? C9 C8 H8A 109.1 . . ? N6 C8 H8B 109.1 . . ? C9 C8 H8B 109.1 . . ? H8A C8 H8B 107.9 . . ? C10 C9 C8 122.7(5) . . ? C10 C9 H9A 106.7 . . ? C8 C9 H9A 106.7 . . ? C10 C9 H9B 106.7 . . ? C8 C9 H9B 106.7 . . ? H9A C9 H9B 106.6 . . ? C10' C9 C8 117.4(5) . . ? C8 C9 H9C 108.0 . . ? C8 C9 H9D 108.0 . . ? C10' C9 H9C 108.0 . . ? C10' C9 H9D 108.0 . . ? H9C C9 H9D 107.2 . . ? C9 C10 C11 118.3(7) . . ? C9 C10 H10A 107.7 . . ? C11 C10 H10A 107.7 . . ? C9 C10 H10B 107.7 . . ? C11 C10 H10B 107.7 . . ? H10A C10 H10B 107.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9' C10' C11' 113.7(7) . . ? C9' C10' H10C 108.8 . . ? C9' C10' H10D 108.8 . . ? C11' C10' H10C 108.8 . . ? C11' C10' H10D 108.8 . . ? H10C C10' H10D 107.7 . . ? C10' C11' H11D 109.5 . . ? C10' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C10' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A Cl1 0.77(4) 2.42(4) 3.125(3) 152(4) 1_565 N4 H4C Cl1 0.74(4) 2.51(4) 3.212(4) 159(5) . N5 H5D Cl1 0.85(5) 2.46(4) 3.185(4) 144(4) 2_566 N6 H6C Cl1 0.76(5) 2.62(5) 3.288(4) 148(4) 1_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.709 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.082