# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_jrba_0m _database_code_depnum_ccdc_archive 'CCDC 615639' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H48 Cl N3 O3' _chemical_formula_sum 'C21 H48 Cl N3 O3' _chemical_formula_weight 426.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 9.9248(6) _cell_length_b 10.1879(6) _cell_length_c 13.1210(7) _cell_angle_alpha 82.683(3) _cell_angle_beta 81.063(3) _cell_angle_gamma 88.233(3) _cell_volume 1299.84(13) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 9494 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 34.96 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.48 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8989 _exptl_absorpt_correction_T_max 0.9228 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 34404 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 34.96 _reflns_number_total 10109 _reflns_number_gt 8512 _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^)+(0.0566P)^2^+0.1590P] 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 10109 _refine_ls_number_parameters 293 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.10029(2) 0.66146(2) 0.663915(16) 0.02701(5) Uani 1 1 d . . . N2 N 0.31030(6) 0.70806(5) 0.08450(4) 0.01369(10) Uani 1 1 d . . . N1 N 0.47802(6) 0.77381(6) 0.30478(4) 0.01365(10) Uani 1 1 d . . . C3 C 0.27791(6) 0.89569(6) 0.21377(5) 0.01213(10) Uani 1 1 d . . . C1 C 0.38437(6) 0.80877(6) 0.24472(5) 0.01215(10) Uani 1 1 d . . . C11 C 0.48494(7) 0.83662(7) 0.39997(5) 0.01553(11) Uani 1 1 d . . . H11 H 0.4074 0.9014 0.4080 0.019 Uiso 1 1 calc R . . C22 C 0.28132(7) 0.78270(7) -0.01549(5) 0.01480(11) Uani 1 1 d . . . H22 H 0.1854 0.8174 -0.0055 0.018 Uiso 1 1 calc R . . N3 N 0.19611(6) 1.00071(5) 0.21980(4) 0.01340(10) Uani 1 1 d . . . C31 C 0.08627(6) 1.01361(6) 0.15310(5) 0.01471(11) Uani 1 1 d . . . H31 H 0.0995 0.9396 0.1091 0.018 Uiso 1 1 calc R . . C23 C 0.37906(8) 0.89971(8) -0.04553(6) 0.02160(13) Uani 1 1 d . . . H23A H 0.3599 0.9619 0.0062 0.032 Uiso 1 1 calc R . . H23B H 0.3664 0.9447 -0.1140 0.032 Uiso 1 1 calc R . . H23C H 0.4734 0.8673 -0.0479 0.032 Uiso 1 1 calc R . . C14 C 0.58010(7) 0.66807(7) 0.27772(5) 0.01523(11) Uani 1 1 d . . . H14 H 0.6456 0.6622 0.3289 0.018 Uiso 1 1 calc R . . C36 C 0.34555(7) 1.15715(7) 0.28047(6) 0.01828(12) Uani 1 1 d . . . H36A H 0.4091 1.0870 0.3014 0.027 Uiso 1 1 calc R . . H36B H 0.3449 1.2282 0.3244 0.027 Uiso 1 1 calc R . . H36C H 0.3745 1.1926 0.2076 0.027 Uiso 1 1 calc R . . C34 C 0.20193(7) 1.10042(6) 0.29304(5) 0.01418(11) Uani 1 1 d . . . H34 H 0.1406 1.1755 0.2723 0.017 Uiso 1 1 calc R . . C21 C 0.22570(8) 0.58824(7) 0.13133(6) 0.01847(12) Uani 1 1 d . . . H21 H 0.2366 0.5734 0.2064 0.022 Uiso 1 1 calc R . . C2 C 0.32083(6) 0.78822(6) 0.16127(5) 0.01248(10) Uani 1 1 d . . . C33 C -0.05566(7) 0.99810(8) 0.21846(6) 0.02173(14) Uani 1 1 d . . . H33A H -0.0597 0.9139 0.2641 0.033 Uiso 1 1 calc R . . H33B H -0.1246 0.9993 0.1724 0.033 Uiso 1 1 calc R . . H33C H -0.0735 1.0712 0.2607 0.033 Uiso 1 1 calc R . . C35 C 0.14494(7) 1.04567(8) 0.40505(5) 0.01966(13) Uani 1 1 d . . . H35A H 0.0490 1.0223 0.4091 0.029 Uiso 1 1 calc R . . H35B H 0.1520 1.1130 0.4510 0.029 Uiso 1 1 calc R . . H35C H 0.1973 0.9667 0.4267 0.029 Uiso 1 1 calc R . . C13 C 0.61802(7) 0.91371(8) 0.38865(6) 0.02133(13) Uani 1 1 d . . . H13A H 0.6958 0.8522 0.3821 0.032 Uiso 1 1 calc R . . H13B H 0.6182 0.9591 0.4502 0.032 Uiso 1 1 calc R . . H13C H 0.6250 0.9791 0.3265 0.032 Uiso 1 1 calc R . . C24 C 0.29873(9) 0.69450(8) -0.10299(6) 0.02349(14) Uani 1 1 d . . . H24A H 0.3892 0.6523 -0.1081 0.035 Uiso 1 1 calc R . . H24B H 0.2897 0.7485 -0.1690 0.035 Uiso 1 1 calc R . . H24C H 0.2285 0.6263 -0.0879 0.035 Uiso 1 1 calc R . . C32 C 0.09860(8) 1.14349(8) 0.07918(6) 0.02169(14) Uani 1 1 d . . . H32A H 0.0667 1.2173 0.1182 0.033 Uiso 1 1 calc R . . H32B H 0.0428 1.1390 0.0243 0.033 Uiso 1 1 calc R . . H32C H 0.1942 1.1571 0.0478 0.033 Uiso 1 1 calc R . . C12 C 0.46759(8) 0.73368(8) 0.49671(5) 0.02310(14) Uani 1 1 d . . . H12A H 0.3849 0.6826 0.4988 0.035 Uiso 1 1 calc R . . H12B H 0.4598 0.7786 0.5591 0.035 Uiso 1 1 calc R . . H12C H 0.5470 0.6739 0.4941 0.035 Uiso 1 1 calc R . . C15 C 0.66215(8) 0.70584(8) 0.16982(6) 0.02519(15) Uani 1 1 d . . . H15A H 0.6019 0.7078 0.1171 0.038 Uiso 1 1 calc R . . H15B H 0.7353 0.6404 0.1568 0.038 Uiso 1 1 calc R . . H15C H 0.7019 0.7935 0.1664 0.038 Uiso 1 1 calc R . . C16 C 0.51455(8) 0.53232(7) 0.28771(7) 0.02536(15) Uani 1 1 d . . . H16A H 0.4546 0.5162 0.3547 0.038 Uiso 1 1 calc R . . H16B H 0.5860 0.4638 0.2836 0.038 Uiso 1 1 calc R . . H16C H 0.4610 0.5299 0.2312 0.038 Uiso 1 1 calc R . . O1 O 0.13973(8) 0.69379(7) 0.41122(5) 0.03285(14) Uani 1 1 d D . . O2 O 0.13213(8) 0.35805(7) 0.61282(6) 0.03508(16) Uani 1 1 d D . . C26 C 0.27833(11) 0.46158(8) 0.08612(7) 0.03065(18) Uani 1 1 d . . . H26A H 0.2453 0.4587 0.0198 0.046 Uiso 1 1 calc R . . H26B H 0.2451 0.3843 0.1349 0.046 Uiso 1 1 calc R . . H26C H 0.3783 0.4607 0.0747 0.046 Uiso 1 1 calc R . . C25 C 0.07230(8) 0.61009(8) 0.12921(7) 0.02575(15) Uani 1 1 d . . . H25A H 0.0416 0.6893 0.1618 0.039 Uiso 1 1 calc R . . H25B H 0.0222 0.5331 0.1674 0.039 Uiso 1 1 calc R . . H25C H 0.0552 0.6218 0.0570 0.039 Uiso 1 1 calc R . . O3 O 0.18276(7) 0.42055(8) 0.39441(6) 0.03488(15) Uani 1 1 d D . . H3B H 0.1100(11) 0.3973(15) 0.3776(12) 0.052 Uiso 1 1 d D . . H1B H 0.1304(16) 0.6926(15) 0.4759(7) 0.052 Uiso 1 1 d D . . H2A H 0.1260(16) 0.4350(10) 0.6309(12) 0.052 Uiso 1 1 d D . . H3A H 0.178(3) 0.406(3) 0.4582(8) 0.052 Uiso 0.50 1 d PD . . H2B H 0.0528(15) 0.341(3) 0.606(2) 0.052 Uiso 0.50 1 d PD . . H1A H 0.150(3) 0.6133(12) 0.404(2) 0.052 Uiso 0.50 1 d PD . . H1C H 0.0622(16) 0.683(3) 0.397(2) 0.052 Uiso 0.50 1 d PD . . H3C H 0.177(3) 0.4994(13) 0.405(2) 0.052 Uiso 0.50 1 d PD . . H2C H 0.145(3) 0.369(3) 0.5480(8) 0.052 Uiso 0.50 1 d PD . . 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 0.02816(10) 0.02742(10) 0.02764(9) -0.00976(7) -0.00585(7) -0.00037(7) N2 0.0170(2) 0.0132(2) 0.0126(2) -0.00440(17) -0.00568(18) 0.00060(18) N1 0.0143(2) 0.0156(2) 0.0129(2) -0.00518(18) -0.00581(18) 0.00415(18) C3 0.0123(2) 0.0131(2) 0.0116(2) -0.00252(19) -0.00314(19) 0.00104(19) C1 0.0123(2) 0.0129(2) 0.0120(2) -0.00314(19) -0.00333(19) 0.00112(19) C11 0.0158(3) 0.0198(3) 0.0130(2) -0.0069(2) -0.0055(2) 0.0040(2) C22 0.0162(3) 0.0173(3) 0.0119(2) -0.0034(2) -0.0043(2) 0.0009(2) N3 0.0134(2) 0.0141(2) 0.0142(2) -0.00488(18) -0.00482(18) 0.00347(18) C31 0.0132(2) 0.0155(3) 0.0170(3) -0.0038(2) -0.0062(2) 0.0023(2) C23 0.0243(3) 0.0241(3) 0.0159(3) -0.0012(2) -0.0014(2) -0.0055(3) C14 0.0148(3) 0.0159(3) 0.0164(3) -0.0053(2) -0.0051(2) 0.0048(2) C36 0.0177(3) 0.0163(3) 0.0219(3) -0.0051(2) -0.0044(2) -0.0004(2) C34 0.0153(3) 0.0146(3) 0.0139(2) -0.0055(2) -0.0032(2) 0.0025(2) C21 0.0247(3) 0.0128(3) 0.0195(3) -0.0013(2) -0.0083(2) -0.0021(2) C2 0.0130(2) 0.0132(2) 0.0123(2) -0.00323(19) -0.00426(19) 0.00142(19) C33 0.0137(3) 0.0236(3) 0.0282(3) -0.0033(3) -0.0038(2) -0.0013(2) C35 0.0195(3) 0.0254(3) 0.0140(3) -0.0051(2) -0.0004(2) 0.0018(2) C13 0.0184(3) 0.0231(3) 0.0259(3) -0.0103(3) -0.0085(3) 0.0012(2) C24 0.0303(4) 0.0270(4) 0.0162(3) -0.0095(3) -0.0081(3) 0.0032(3) C32 0.0211(3) 0.0231(3) 0.0210(3) 0.0030(2) -0.0085(2) 0.0001(3) C12 0.0242(3) 0.0319(4) 0.0136(3) -0.0017(3) -0.0055(2) 0.0028(3) C15 0.0232(3) 0.0275(4) 0.0227(3) -0.0049(3) 0.0034(3) 0.0059(3) C16 0.0246(3) 0.0152(3) 0.0369(4) -0.0040(3) -0.0067(3) 0.0029(3) O1 0.0381(4) 0.0311(3) 0.0279(3) -0.0024(3) 0.0005(3) -0.0097(3) O2 0.0364(3) 0.0317(3) 0.0429(4) -0.0125(3) -0.0204(3) 0.0144(3) C26 0.0460(5) 0.0146(3) 0.0362(4) -0.0082(3) -0.0182(4) 0.0043(3) C25 0.0225(3) 0.0240(3) 0.0305(4) 0.0009(3) -0.0055(3) -0.0072(3) O3 0.0231(3) 0.0388(4) 0.0443(4) -0.0170(3) -0.0006(3) 0.0006(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 N2 C2 1.3928(8) . ? N2 C22 1.4940(8) . ? N2 C21 1.5115(9) . ? N1 C1 1.3219(7) . ? N1 C11 1.4856(8) . ? N1 C14 1.4938(8) . ? C3 N3 1.3260(8) . ? C3 C2 1.3881(8) . ? C3 C1 1.4316(9) . ? C1 C2 1.3861(8) . ? C11 C12 1.5312(10) . ? C11 C13 1.5352(10) . ? C11 H11 1.0000 . ? C22 C24 1.5320(9) . ? C22 C23 1.5330(10) . ? C22 H22 1.0000 . ? N3 C34 1.4928(8) . ? N3 C31 1.4932(8) . ? C31 C33 1.5325(10) . ? C31 C32 1.5338(10) . ? C31 H31 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C14 C16 1.5284(10) . ? C14 C15 1.5291(10) . ? C14 H14 1.0000 . ? C36 C34 1.5318(9) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C34 C35 1.5308(10) . ? C34 H34 1.0000 . ? C21 C26 1.5320(11) . ? C21 C25 1.5358(11) . ? C21 H21 1.0000 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? O1 H1C 0.832(10) . ? O1 H1B 0.837(9) . ? O1 H1A 0.838(10) . ? O1 H1B 0.837(9) . ? O1 H1A 0.838(10) . ? O1 H1C 0.832(10) . ? O2 H2C 0.834(10) . ? O2 H2B 0.832(10) . ? O2 H2A 0.845(9) . ? O2 H2A 0.845(9) . ? O2 H2B 0.832(10) . ? O2 H2C 0.834(10) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? O3 H3A 0.826(10) . ? O3 H3C 0.830(10) . ? O3 H3B 0.837(9) . ? O3 H3B 0.837(9) . ? O3 H3A 0.826(10) . ? O3 H3C 0.830(10) . ? 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 N2 C22 113.83(5) . . ? C2 N2 C21 109.57(5) . . ? C22 N2 C21 118.99(5) . . ? C1 N1 C11 121.78(5) . . ? C1 N1 C14 119.90(5) . . ? C11 N1 C14 118.33(5) . . ? N3 C3 C2 146.97(6) . . ? N3 C3 C1 154.12(6) . . ? C2 C3 C1 58.87(4) . . ? N1 C1 C2 149.58(6) . . ? N1 C1 C3 151.37(6) . . ? C2 C1 C3 59.00(4) . . ? N1 C11 C12 110.96(6) . . ? N1 C11 C13 110.62(6) . . ? C12 C11 C13 111.86(6) . . ? N1 C11 H11 107.7 . . ? C12 C11 H11 107.7 . . ? C13 C11 H11 107.7 . . ? N2 C22 C24 111.54(6) . . ? N2 C22 C23 108.83(5) . . ? C24 C22 C23 109.51(6) . . ? N2 C22 H22 109.0 . . ? C24 C22 H22 109.0 . . ? C23 C22 H22 109.0 . . ? C3 N3 C34 124.22(5) . . ? C3 N3 C31 116.91(5) . . ? C34 N3 C31 118.75(5) . . ? N3 C31 C33 111.59(5) . . ? N3 C31 C32 111.23(5) . . ? C33 C31 C32 111.95(6) . . ? N3 C31 H31 107.3 . . ? C33 C31 H31 107.3 . . ? C32 C31 H31 107.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N1 C14 C16 112.23(6) . . ? N1 C14 C15 110.69(6) . . ? C16 C14 C15 111.97(6) . . ? N1 C14 H14 107.2 . . ? C16 C14 H14 107.2 . . ? C15 C14 H14 107.2 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? N3 C34 C35 111.70(5) . . ? N3 C34 C36 110.95(5) . . ? C35 C34 C36 113.79(5) . . ? N3 C34 H34 106.6 . . ? C35 C34 H34 106.6 . . ? C36 C34 H34 106.6 . . ? N2 C21 C26 112.99(7) . . ? N2 C21 C25 113.38(6) . . ? C26 C21 C25 111.86(6) . . ? N2 C21 H21 106.0 . . ? C26 C21 H21 106.0 . . ? C25 C21 H21 106.0 . . ? C1 C2 C3 62.13(4) . . ? C1 C2 N2 146.69(6) . . ? C3 C2 N2 151.11(6) . . ? C31 C33 H33A 109.5 . . ? C31 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C31 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? H1C O1 H1B 106(2) . . ? H1C O1 H1A 83(3) . . ? H1B O1 H1A 102(2) . . ? H1C O1 H1B 106(2) . . ? H1A O1 H1B 102(2) . . ? H1C O1 H1A 83(3) . . ? H1B O1 H1A 102(2) . . ? H1B O1 H1A 102(2) . . ? H1B O1 H1C 106(2) . . ? H1A O1 H1C 83(3) . . ? H1B O1 H1C 106(2) . . ? H1A O1 H1C 83(3) . . ? H2C O2 H2B 84(3) . . ? H2C O2 H2A 105(2) . . ? H2B O2 H2A 104(2) . . ? H2C O2 H2A 105(2) . . ? H2B O2 H2A 104(2) . . ? H2C O2 H2B 84(3) . . ? H2A O2 H2B 104(2) . . ? H2A O2 H2B 104(2) . . ? H2B O2 H2C 84(3) . . ? H2A O2 H2C 105(2) . . ? H2A O2 H2C 105(2) . . ? H2B O2 H2C 84(3) . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? H3A O3 H3C 84(3) . . ? H3A O3 H3B 109(2) . . ? H3C O3 H3B 110(2) . . ? H3A O3 H3B 109(2) . . ? H3C O3 H3B 110(2) . . ? H3C O3 H3A 84(3) . . ? H3B O3 H3A 109(2) . . ? H3B O3 H3A 109(2) . . ? H3A O3 H3C 84(3) . . ? H3B O3 H3C 110(2) . . ? H3B O3 H3C 110(2) . . ? H3A O3 H3C 84(3) . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.451 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.050 # Information for phase 1 data_CDH_phase_1 _database_code_depnum_ccdc_archive 'CCDC 880874' #TrackingRef '- CDH_revised.cif' _pd_block_id 2007-05-23T14:48|CDH_phase1|Paula_M._B._Piccoli|| #============================================================================== # 7. CHEMICAL, STRUCTURAL AND CRYSTAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C21 H48 Cl N3 O3' _chemical_formula_sum 'C21 H48 Cl N3 O3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_iupac ? _chemical_formula_weight 426.07 #============================================================================== # CRYSTAL DATA _cell_measurement_reflns_used 10443 _cell_measurement_temperature 20 _exptl_crystal_description fragment _exptl_crystal_colour orange _exptl_crystal_size_max 3 _exptl_crystal_size_mid 2 _exptl_crystal_size_min 1 _exptl_crystal_size_rad 1.078 _exptl_crystal_density_diffrn 1.124 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu '1.858 + 1.490 x lambda cm^-1' _exptl_absorpt_correction_type Gaussian _exptl_absorpt_process_details '(IPNS ANVRED; local program' _exptl_absorpt_correction_T_min 0.1512 _exptl_absorpt_correction_T_max 0.6654 _exptl_special_details ; Neutron data Collection. Neutron diffraction data were obtained at the Intense Pulsed Neutron Source (IPNS; shut down in 2008) at Argonne National Laboratory using the time-of-flight Laue single-crystal diffractometer (SCD; currently located at the Los Alamos Lujan Neutron Scattering Center). At the IPNS, pulses of protons are were accelerated into a depleted uranium target 30 times a second to produce pulses of neutrons by the spallation process. Exploiting the pulsed nature of the source, neutron wavelengths are determined by time-of-flight based on the de Broglie equation lambda = (h/m).(t/l), where h is Planck's constant, m is the neutron mass, and t is the time-of-flight for a flight path l, so that the entire thermal spectrum of neutrons can be used. With two position-sensitive area detectors and a range of neutron wavelengths, a solid volume of reciprocal space is sampled with each stationary orientation of the sample and the detectors. The SCD has two 6Li-glass scintillation position-sensit A crystal with approximate dimensions of 3 x 2 x 1 mm3 and a weight of 5.9 mg, was wrapped in aluminum foil and glued to an aluminum pin that was mounted on the cold stage of a closed-cycle helium refrigerator. The crystal was then cooled under vacuum to 20 +- 1 K. For each setting of the diffractometer angles, data were stored in three-dimensional histogram form with coordinates x,y,t corresponding to horizontal and vertical detector positions and the time-of-flight, respectively. An auto-indexing algorithm was used to obtain an initial orientation matrix from the peaks in three preliminary histograms measured for 60 minutes each. This unit cell approximately matched the X-ray unit cell indicating that the neutron sample was the correct material. For intensity data collection, runs of 6 hours per histogram were initiated for the data set. Settings were arranged at chi and phi values suitable to cover at least one unique hemisphere of reciprocal space (Laue symmetry 1). With the above counting ti ; # EXPERIMENTAL DATA _diffrn_ambient_temperature ? _diffrn_radiation_type neutron _diffrn_radiation_wavelength 0.7-4.2 _diffrn_radiation_source 'Intense Pulsed Neutron Source' _diffrn_radiation_monochromator 'not applicable to TOF Laue technique' _diffrn_measurement_device_type 'IPNS single crystal diffractometer' _diffrn_measurement_method 'Time-of-flight Laue' _diffrn_reflns_number 10443 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_theta_min 'not applicable to TOF Laue technique' _diffrn_reflns_theta_max 'not applicable to TOF Laue technique' _diffrn_reflns_theta_full 'not applicable to TOF Laue technique' _diffrn_measured_fraction_theta_max 'not applicable to TOF Laue technique' _diffrn_measured_fraction_theta_full 'not applicable to TOF Laue technique' _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_reduction_process ? _diffrn_standards_number 'not applicable to TOF Laue technique' _diffrn_standards_decay_% 'not applicable to TOF Laue technique' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? #============================================================================== # 8. Phase information from GSAS _pd_phase_name 'cdh at 20 K' _cell_length_a 9.7710(20) _cell_length_b 10.1030(20) _cell_length_c 13.0300(20) _cell_angle_alpha 82.575(15) _cell_angle_beta 80.833(14) _cell_angle_gamma 88.339(15) _cell_volume 1259.2(4) _cell_formula_units_Z 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z -1 -x,-y,-z # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity Cl Cl1 0.10164(18) 0.66075(19) 0.66471(14) 1.0 Uani 0.01278 2 N N2 0.31148(18) 0.70928(17) 0.08359(13) 1.0 Uani 0.00814 2 N N1 0.47886(18) 0.77512(18) 0.30471(13) 1.0 Uani 0.00924 2 C C3 0.27937(25) 0.89731(24) 0.21312(19) 1.0 Uani 0.00866 2 C C1 0.38501(24) 0.81055(24) 0.24442(18) 1.0 Uani 0.00803 2 C C11 0.48498(26) 0.83791(25) 0.40046(19) 1.0 Uani 0.00917 2 H H11 0.3978(5) 0.9053(6) 0.4065(4) 1.0 Uani 0.02136 2 C C22 0.28194(26) 0.78341(25) -0.01683(19) 1.0 Uani 0.00895 2 H H22 0.1750(5) 0.8209(6) -0.0081(4) 1.0 Uani 0.02194 2 N N3 0.19637(18) 1.00319(18) 0.21854(14) 1.0 Uani 0.0084 2 C C31 0.08703(25) 1.01632(26) 0.15105(19) 1.0 Uani 0.00907 2 H H31 0.1062(6) 0.9333(6) 0.1037(4) 1.0 Uani 0.02012 2 C C23 0.37914(27) 0.90268(26) -0.04762(20) 1.0 Uani 0.00996 2 H H23A 0.3610(7) 0.9749(6) 0.0069(5) 1.0 Uani 0.02948 2 H H23B 0.3674(7) 0.9521(6) -0.1261(4) 1.0 Uani 0.03116 2 H H23C 0.4865(6) 0.8700(7) -0.0528(5) 1.0 Uani 0.0347 2 C C14 0.58107(25) 0.66878(25) 0.27742(19) 1.0 Uani 0.00967 2 H H14 0.6528(6) 0.6656(6) 0.3351(4) 1.0 Uani 0.02371 2 C C36 0.34633(26) 1.15940(27) 0.28100(21) 1.0 Uani 0.01008 2 H H36A 0.4206(6) 1.0850(6) 0.3039(5) 1.0 Uani 0.03144 2 H H36B 0.3456(6) 1.2399(6) 0.3284(5) 1.0 Uani 0.03308 2 H H36C 0.3830(6) 1.2013(7) 0.1993(5) 1.0 Uani 0.03055 2 C C34 0.20186(25) 1.10256(25) 0.29228(19) 1.0 Uani 0.00887 2 H H34 0.1342(5) 1.1846(6) 0.2677(4) 1.0 Uani 0.02079 2 C C21 0.22686(26) 0.58935(25) 0.13137(20) 1.0 Uani 0.01042 2 H H21 0.2417(6) 0.5751(5) 0.2130(4) 1.0 Uani 0.0213 2 C C2 0.32212(25) 0.79016(24) 0.16030(19) 1.0 Uani 0.00764 2 C C33 -0.05647(26) 0.99850(28) 0.21718(21) 1.0 Uani 0.01225 2 H H33A -0.0642(6) 0.9048(6) 0.2694(5) 1.0 Uani 0.03003 2 H H33B -0.1330(6) 1.0005(7) 0.1647(5) 1.0 Uani 0.03311 2 H H33C -0.0815(6) 1.0804(6) 0.2649(5) 1.0 Uani 0.02972 2 C C35 0.14251(28) 1.04785(28) 0.40471(20) 1.0 Uani 0.01187 2 H H35A 0.0371(7) 1.0184(7) 0.4098(5) 1.0 Uani 0.03349 2 H H35B 0.1470(7) 1.1247(7) 0.4559(4) 1.0 Uani 0.03449 2 H H35C 0.1965(6) 0.9580(6) 0.4337(5) 1.0 Uani 0.03012 2 C C13 0.61876(27) 0.91532(27) 0.38914(22) 1.0 Uani 0.01205 2 H H13A 0.7090(6) 0.8499(6) 0.3813(5) 1.0 Uani 0.02859 2 H H13B 0.6204(6) 0.9659(7) 0.4577(5) 1.0 Uani 0.03643 2 H H13C 0.6303(6) 0.9906(6) 0.3213(5) 1.0 Uani 0.03006 2 C C24 0.29876(28) 0.69426(27) -0.10371(20) 1.0 Uani 0.01113 2 H H24A 0.4001(6) 0.6476(7) -0.1115(5) 1.0 Uani 0.03214 2 H H24B 0.2892(7) 0.7543(6) -0.1788(4) 1.0 Uani 0.029 2 H H24C 0.2213(7) 0.6181(6) -0.0943(5) 1.0 Uani 0.03099 2 C C32 0.09833(27) 1.14613(26) 0.07838(21) 1.0 Uani 0.01072 2 H H32A 0.0592(7) 1.2300(6) 0.1185(5) 1.0 Uani 0.03115 2 H H32B 0.0391(7) 1.1402(6) 0.0144(5) 1.0 Uani 0.03169 2 H H32C 0.2057(7) 1.1656(7) 0.0412(5) 1.0 Uani 0.03343 2 C C12 0.46833(28) 0.73285(29) 0.49666(20) 1.0 Uani 0.01274 2 H H12A 0.3748(7) 0.6748(7) 0.5043(5) 1.0 Uani 0.03792 2 H H12B 0.4580(7) 0.7825(7) 0.5684(4) 1.0 Uani 0.03248 2 H H12C 0.5559(6) 0.6661(6) 0.4968(5) 1.0 Uani 0.03033 2 C C15 0.66477(29) 0.70610(29) 0.16888(21) 1.0 Uani 0.0136 2 H H15A 0.6005(7) 0.7108(7) 0.1081(5) 1.0 Uani 0.03369 2 H H15B 0.7451(7) 0.6322(7) 0.1552(5) 1.0 Uani 0.03407 2 H H15C 0.7128(7) 0.8032(6) 0.1636(5) 1.0 Uani 0.03688 2 C C16 0.51465(28) 0.53214(26) 0.28875(22) 1.0 Uani 0.01222 2 H H16A 0.4462(7) 0.5122(6) 0.3628(5) 1.0 Uani 0.03646 2 H H16B 0.5954(6) 0.4557(6) 0.2844(5) 1.0 Uani 0.03096 2 H H16C 0.4560(7) 0.5241(6) 0.2253(5) 1.0 Uani 0.03594 2 O O1 0.1414(4) 0.6962(4) 0.41008(28) 1.0 Uani 0.01729 2 O O2 0.1311(4) 0.3571(4) 0.61381(30) 1.0 Uani 0.01973 2 C C26 0.27920(30) 0.46106(27) 0.08606(23) 1.0 Uani 0.01435 2 H H26A 0.2439(7) 0.4488(6) 0.0136(5) 1.0 Uani 0.0359 2 H H26B 0.2415(7) 0.3783(6) 0.1418(5) 1.0 Uani 0.03515 2 H H26C 0.3933(6) 0.4590(6) 0.0725(5) 1.0 Uani 0.03289 2 C C25 0.07288(27) 0.60970(28) 0.12974(21) 1.0 Uani 0.01295 2 H H25A 0.0331(6) 0.6994(6) 0.1661(5) 1.0 Uani 0.03055 2 H H25B 0.0156(6) 0.5256(7) 0.1754(5) 1.0 Uani 0.03338 2 H H25C 0.0477(6) 0.6216(7) 0.0501(5) 1.0 Uani 0.03275 2 O O3 0.1819(4) 0.4212(4) 0.39522(32) 1.0 Uani 0.02046 2 H H3B 0.0973(7) 0.3943(7) 0.3743(6) 1.0 Uani 0.03547 2 H H1B 0.1330(7) 0.6964(7) 0.4869(5) 1.0 Uani 0.03196 2 H H2A 0.1241(7) 0.4462(7) 0.6343(5) 1.0 Uani 0.03444 2 H H3A 0.1767(16) 0.3957(12) 0.4634(13) 0.5 Uani 0.03699 2 H H2B 0.0467(15) 0.3299(14) 0.6133(11) 0.5 Uani 0.03462 2 H H1A 0.1573(13) 0.6094(16) 0.4021(8) 0.5 Uani 0.02834 2 H H1C 0.0518(15) 0.6878(13) 0.3985(10) 0.5 Uani 0.02886 2 H H3C 0.1765(12) 0.5077(15) 0.4010(10) 0.5 Uani 0.02784 2 H H2C 0.1501(13) 0.3736(17) 0.5414(11) 0.5 Uani 0.03943 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 Cl1 0.0128(8) 0.0002(7) -0.0019(6) 0.0164(9) -0.0041(7) 0.0098(8) N2 0.0086(8) 0.0002(6) -0.0027(6) 0.0087(8) -0.0019(6) 0.0079(7) N1 0.0081(8) 0.0018(6) -0.0039(6) 0.0122(8) -0.0023(6) 0.0084(8) C3 0.0112(11) 0.0034(9) -0.0036(8) 0.0081(11) -0.0013(9) 0.0073(10) C1 0.0074(10) 0.0020(9) -0.0022(8) 0.0091(11) -0.0009(8) 0.0078(10) C11 0.0094(11) -0.0005(9) -0.0029(8) 0.0103(11) -0.0027(9) 0.0087(10) H11 0.0161(25) 0.0010(22) -0.0023(20) 0.0274(30) -0.0055(23) 0.0210(26) C22 0.0105(11) 0.0019(9) -0.0016(8) 0.0090(11) 0.0000(9) 0.0071(10) H22 0.0132(24) 0.0118(22) -0.0058(20) 0.0329(32) -0.0064(23) 0.0209(26) N3 0.0082(7) 0.0032(6) -0.0042(6) 0.0089(8) -0.0025(6) 0.0091(7) C31 0.0078(10) 0.0033(9) -0.0020(8) 0.0109(11) -0.0004(9) 0.0084(10) H31 0.0244(27) 0.0080(22) -0.0072(20) 0.0229(27) -0.0074(21) 0.0153(23) C23 0.0109(11) -0.0027(9) 0.0000(9) 0.0099(12) 0.0015(9) 0.0080(11) H23A 0.043(4) -0.0044(26) -0.0004(27) 0.0170(27) -0.0051(24) 0.0279(31) H23B 0.049(4) -0.0125(29) -0.0073(25) 0.0290(32) 0.0129(23) 0.0129(25) H23C 0.0200(30) 0.0065(28) -0.0023(26) 0.042(4) -0.0019(31) 0.040(4) C14 0.0104(11) 0.0037(9) -0.0032(9) 0.0120(12) -0.0022(9) 0.0073(10) H14 0.0222(27) 0.0049(24) -0.0112(21) 0.0328(33) -0.0080(24) 0.0196(26) C36 0.0089(11) -0.0024(9) -0.0025(9) 0.0108(12) 0.0019(9) 0.0101(11) H36A 0.0172(28) 0.0029(25) -0.0138(26) 0.0304(34) 0.0055(29) 0.047(4) H36B 0.0257(31) -0.0065(27) -0.0002(27) 0.034(4) -0.0201(31) 0.042(4) H36C 0.0222(29) -0.0147(27) -0.0006(22) 0.047(4) 0.0026(27) 0.0208(29) C34 0.0090(11) 0.0018(9) -0.0025(8) 0.0099(11) -0.0025(9) 0.0084(10) H34 0.0149(24) 0.0042(21) -0.0001(20) 0.0248(28) -0.0044(22) 0.0219(27) C21 0.0116(11) 0.0006(9) -0.0045(9) 0.0086(11) -0.0006(9) 0.0117(12) H21 0.0302(30) -0.0054(23) -0.0034(21) 0.0187(26) -0.0025(21) 0.0154(24) C2 0.0073(10) 0.0004(8) -0.0026(8) 0.0081(10) -0.0011(8) 0.0079(10) C33 0.0094(12) 0.0017(10) -0.0017(9) 0.0154(13) -0.0019(10) 0.0119(12) H33A 0.0339(34) -0.0025(27) 0.0014(25) 0.0270(32) 0.0025(26) 0.0258(31) H33B 0.0281(32) 0.0059(28) -0.0212(27) 0.043(4) -0.0031(29) 0.0329(34) H33C 0.0278(31) 0.0075(26) -0.0092(26) 0.0298(33) -0.0153(28) 0.0354(35) C35 0.0119(12) -0.0003(10) -0.0008(9) 0.0151(13) 0.0007(10) 0.0078(11) H35A 0.0245(31) -0.0117(29) -0.0017(24) 0.051(4) 0.0036(29) 0.0233(31) H35B 0.045(4) -0.0127(32) 0.0039(25) 0.046(4) -0.0205(27) 0.0147(26) H35C 0.038(4) 0.0120(27) 0.0040(25) 0.0226(30) 0.0071(24) 0.0238(29) C13 0.0101(12) -0.0009(10) -0.0037(10) 0.0122(12) -0.0047(10) 0.0152(13) H13A 0.0116(25) 0.0006(24) -0.0022(24) 0.0342(35) -0.0120(29) 0.041(4) H13B 0.0303(34) -0.0061(32) -0.0074(27) 0.054(4) -0.0220(33) 0.0306(34) H13C 0.0298(32) -0.0036(27) -0.0072(23) 0.037(4) 0.0155(25) 0.0198(28) C24 0.0130(12) 0.0009(10) -0.0036(9) 0.0118(12) -0.0033(10) 0.0097(11) H24A 0.0211(30) 0.0095(27) -0.0002(25) 0.038(4) -0.0139(30) 0.038(4) H24B 0.043(4) 0.0026(28) -0.0061(25) 0.0283(32) -0.0028(24) 0.0161(26) H24C 0.041(4) -0.0075(28) 0.0029(27) 0.0231(31) -0.0047(26) 0.0271(32) C32 0.0084(11) -0.0009(9) -0.0023(9) 0.0111(12) 0.0002(10) 0.0124(12) H32A 0.043(4) 0.0090(27) -0.0045(28) 0.0181(28) -0.0103(26) 0.0329(34) H32B 0.047(4) 0.0056(30) -0.0184(27) 0.0339(34) -0.0020(26) 0.0182(28) H32C 0.0260(32) -0.0020(28) 0.0038(25) 0.038(4) 0.0099(28) 0.0299(33) C12 0.0113(12) -0.0003(10) -0.0028(9) 0.0177(14) -0.0005(10) 0.0093(11) H12A 0.0298(34) -0.0227(30) -0.0097(28) 0.045(4) 0.0105(31) 0.037(4) H12B 0.042(4) 0.0064(30) -0.0020(24) 0.043(4) -0.0134(26) 0.0141(26) H12C 0.0300(33) 0.0095(25) 0.0028(26) 0.0234(31) 0.0057(26) 0.0320(33) C15 0.0144(13) 0.0041(11) 0.0017(10) 0.0151(13) -0.0014(10) 0.0098(12) H15A 0.0315(34) 0.0049(30) -0.0039(25) 0.047(4) 0.0041(28) 0.0199(29) H15B 0.034(4) 0.0095(29) 0.0001(28) 0.033(4) -0.0079(29) 0.034(4) H15C 0.040(4) -0.0214(29) 0.0098(29) 0.0262(32) 0.0022(28) 0.039(4) C16 0.0123(12) 0.0017(9) -0.0047(10) 0.0087(12) -0.0012(10) 0.0163(13) H16A 0.036(4) -0.0127(28) 0.0174(28) 0.0294(34) 0.0031(28) 0.035(4) H16B 0.0276(32) 0.0106(24) -0.0073(29) 0.0140(26) -0.0101(27) 0.052(4) H16C 0.043(4) -0.0044(30) -0.0229(31) 0.0307(35) -0.0012(29) 0.039(4) O1 0.0204(18) -0.0063(15) 0.0003(13) 0.0178(17) 0.0019(13) 0.0121(15) O2 0.0187(17) 0.0063(15) -0.0091(14) 0.0261(20) -0.0067(15) 0.0171(17) C26 0.0187(14) 0.0051(10) -0.0053(11) 0.0095(12) -0.0048(10) 0.0163(13) H26A 0.054(4) 0.0067(31) -0.0173(31) 0.0265(33) -0.0123(28) 0.033(4) H26B 0.044(4) -0.0136(29) -0.0068(30) 0.0241(32) 0.0071(27) 0.035(4) H26C 0.0223(31) 0.0051(27) -0.0031(26) 0.036(4) -0.0165(30) 0.042(4) C25 0.0139(12) 0.0001(10) -0.0056(10) 0.0127(12) 0.0010(10) 0.0128(12) H25A 0.0283(32) 0.0084(25) 0.0035(26) 0.0255(31) -0.0151(28) 0.037(4) H25B 0.0253(31) -0.0118(27) -0.0073(26) 0.036(4) 0.0125(29) 0.036(4) H25C 0.0331(34) -0.0041(30) -0.0129(26) 0.044(4) -0.0004(28) 0.0231(31) O3 0.0149(17) -0.0010(15) -0.0011(14) 0.0259(21) -0.0089(17) 0.0216(19) H3B 0.0204(30) 0.0020(28) -0.0113(28) 0.043(4) -0.0163(34) 0.048(4) H1B 0.0366(35) -0.0059(29) 0.0011(25) 0.041(4) -0.0075(27) 0.0181(29) H2A 0.042(4) 0.0078(30) -0.0050(29) 0.0302(35) -0.0182(29) 0.034(4) H3A 0.057(9) -0.006(6) -0.003(7) 0.018(6) 0.008(6) 0.032(8) H2B 0.025(7) -0.014(6) -0.006(6) 0.037(8) -0.005(6) 0.043(8) H1A 0.036(7) 0.003(7) -0.004(4) 0.041(8) -0.007(5) 0.009(5) H1C 0.034(7) 0.007(6) -0.012(6) 0.030(7) -0.004(5) 0.025(6) H3C 0.022(6) 0.003(5) -0.008(5) 0.027(7) -0.007(6) 0.036(7) H2C 0.027(7) -0.021(7) 0.002(5) 0.076(11) -0.014(7) 0.017(6) loop_ _atom_type_symbol _atom_type_number_in_cell Cl 2.0 N 6.0 C 42.0 H 96.0 O 6.0 # MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 H3B 2.190(7) . -1_566 N Cl1 H1B 2.271(6) . 1_555 N Cl1 H2A 2.251(7) . 1_555 N N2 C22 1.4870(30) . 1_555 N N2 C21 1.4962(31) . 1_555 N N2 H21 2.060(6) . 1_555 N N2 C2 1.3880(29) . 1_555 N N1 C1 1.3130(29) . 1_555 N N1 C11 1.4809(30) . 1_555 N N1 H11 2.043(6) . 1_555 N N1 C14 1.4837(29) . 1_555 N C3 C1 1.4105(33) . 1_555 N C3 N3 1.3259(28) . 1_555 N C3 C2 1.3765(33) . 1_555 N C1 N1 1.3130(29) . 1_555 N C1 C3 1.4105(33) . 1_555 N C1 C2 1.3791(33) . 1_555 N C11 N1 1.4809(30) . 1_555 N C11 H11 1.075(6) . 1_555 N C11 C13 1.520(4) . 1_555 N C11 C12 1.525(4) . 1_555 N H11 N1 2.043(6) . 1_555 N H11 C11 1.075(6) . 1_555 N C22 N2 1.4870(30) . 1_555 N C22 H22 1.095(6) . 1_555 N C22 C23 1.528(4) . 1_555 N C22 C24 1.522(4) . 1_555 N H22 C22 1.095(6) . 1_555 N N3 C3 1.3259(28) . 1_555 N N3 C31 1.4810(30) . 1_555 N N3 H31 2.060(5) . 1_555 N N3 C34 1.4841(30) . 1_555 N C31 N3 1.4810(30) . 1_555 N C31 H31 1.099(6) . 1_555 N C31 C33 1.5266(35) . 1_555 N C31 C32 1.511(4) . 1_555 N H31 N3 2.060(5) . 1_555 N H31 C31 1.099(6) . 1_555 N C23 C22 1.528(4) . 1_555 N C23 H23A 1.075(7) . 1_555 N C23 H23B 1.100(6) . 1_555 N C23 H23C 1.085(7) . 1_555 N H23A C23 1.075(7) . 1_555 N H23A H23B 1.769(8) . 1_555 N H23A H23C 1.751(9) . 1_555 N H23B C23 1.100(6) . 1_555 N H23B H23A 1.769(8) . 1_555 N H23B H23C 1.746(9) . 1_555 N H23C C23 1.085(7) . 1_555 N H23C H23A 1.751(9) . 1_555 N H23C H23B 1.746(9) . 1_555 N C14 N1 1.4837(29) . 1_555 N C14 H14 1.103(6) . 1_555 N C14 C15 1.524(4) . 1_555 N C14 C16 1.522(4) . 1_555 N H14 C14 1.103(6) . 1_555 N C36 H36A 1.078(7) . 1_555 N C36 H36B 1.083(7) . 1_555 N C36 H36C 1.100(7) . 1_555 N C36 C34 1.518(4) . 1_555 N H36A C36 1.078(7) . 1_555 N H36A H36B 1.754(9) . 1_555 N H36A H36C 1.759(9) . 1_555 N H36B C36 1.083(7) . 1_555 N H36B H36A 1.754(9) . 1_555 N H36B H36C 1.755(9) . 1_555 N H36C C36 1.100(7) . 1_555 N H36C H36A 1.759(9) . 1_555 N H36C H36B 1.755(9) . 1_555 N C34 N3 1.4841(30) . 1_555 N C34 C36 1.518(4) . 1_555 N C34 H34 1.092(6) . 1_555 N C34 C35 1.525(4) . 1_555 N H34 C34 1.092(6) . 1_555 N C21 N2 1.4962(31) . 1_555 N C21 H21 1.087(6) . 1_555 N C21 C26 1.534(4) . 1_555 N C21 C25 1.516(4) . 1_555 N H21 N2 2.060(6) . 1_555 N H21 C21 1.087(6) . 1_555 N C2 N2 1.3880(29) . 1_555 N C2 C3 1.3765(33) . 1_555 N C2 C1 1.3791(33) . 1_555 N C33 C31 1.5266(35) . 1_555 N C33 H33A 1.089(7) . 1_555 N C33 H33B 1.089(7) . 1_555 N C33 H33C 1.097(7) . 1_555 N H33A C33 1.089(7) . 1_555 N H33A H33B 1.778(9) . 1_555 N H33A H33C 1.772(9) . 1_555 N H33B C33 1.089(7) . 1_555 N H33B H33A 1.778(9) . 1_555 N H33B H33C 1.765(9) . 1_555 N H33C C33 1.097(7) . 1_555 N H33C H33A 1.772(9) . 1_555 N H33C H33B 1.765(9) . 1_555 N C35 C34 1.525(4) . 1_555 N C35 H35A 1.070(8) . 1_555 N C35 H35B 1.093(7) . 1_555 N C35 H35C 1.092(7) . 1_555 N H35A C35 1.070(8) . 1_555 N H35A H35B 1.762(9) . 1_555 N H35A H35C 1.716(9) . 1_555 N H35B C35 1.093(7) . 1_555 N H35B H35A 1.762(9) . 1_555 N H35B H35C 1.786(9) . 1_555 N H35C C35 1.092(7) . 1_555 N H35C H35A 1.716(9) . 1_555 N H35C H35B 1.786(9) . 1_555 N C13 C11 1.520(4) . 1_555 N C13 H13A 1.087(7) . 1_555 N C13 H13B 1.087(7) . 1_555 N C13 H13C 1.082(7) . 1_555 N H13A C13 1.087(7) . 1_555 N H13A H13B 1.756(9) . 1_555 N H13A H13C 1.751(9) . 1_555 N H13B C13 1.087(7) . 1_555 N H13B H13A 1.756(9) . 1_555 N H13B H13C 1.750(9) . 1_555 N H13C C13 1.082(7) . 1_555 N H13C H13A 1.751(9) . 1_555 N H13C H13B 1.750(9) . 1_555 N C24 C22 1.522(4) . 1_555 N C24 H24A 1.080(7) . 1_555 N C24 H24B 1.098(7) . 1_555 N C24 H24C 1.077(7) . 1_555 N H24A C24 1.080(7) . 1_555 N H24A H24B 1.759(9) . 1_555 N H24A H24C 1.755(9) . 1_555 N H24B C24 1.098(7) . 1_555 N H24B H24A 1.759(9) . 1_555 N H24B H24C 1.724(9) . 1_555 N H24C C24 1.077(7) . 1_555 N H24C H24A 1.755(9) . 1_555 N H24C H24B 1.724(9) . 1_555 N C32 C31 1.511(4) . 1_555 N C32 H32A 1.081(7) . 1_555 N C32 H32B 1.096(7) . 1_555 N C32 H32C 1.095(7) . 1_555 N H32A C32 1.081(7) . 1_555 N H32A H32B 1.765(8) . 1_555 N H32A H32C 1.772(9) . 1_555 N H32B C32 1.096(7) . 1_555 N H32B H32A 1.765(8) . 1_555 N H32B H32C 1.751(9) . 1_555 N H32C C32 1.095(7) . 1_555 N H32C H32A 1.772(9) . 1_555 N H32C H32B 1.751(9) . 1_555 N C12 C11 1.525(4) . 1_555 N C12 H12A 1.084(7) . 1_555 N C12 H12B 1.107(7) . 1_555 N C12 H12C 1.074(7) . 1_555 N H12A C12 1.084(7) . 1_555 N H12A H12B 1.745(9) . 1_555 N H12A H12C 1.757(9) . 1_555 N H12B C12 1.107(7) . 1_555 N H12B H12A 1.745(9) . 1_555 N H12B H12C 1.761(8) . 1_555 N H12C C12 1.074(7) . 1_555 N H12C H12A 1.757(9) . 1_555 N H12C H12B 1.761(8) . 1_555 N C15 C14 1.524(4) . 1_555 N C15 H15A 1.083(8) . 1_555 N C15 H15B 1.078(7) . 1_555 N C15 H15C 1.089(7) . 1_555 N H15A C15 1.083(8) . 1_555 N H15A H15B 1.758(9) . 1_555 N H15A H15C 1.757(10) . 1_555 N H15B C15 1.078(7) . 1_555 N H15B H15A 1.758(9) . 1_555 N H15B H15C 1.762(9) . 1_555 N H15C C15 1.089(7) . 1_555 N H15C H15A 1.757(10) . 1_555 N H15C H15B 1.762(9) . 1_555 N C16 C14 1.522(4) . 1_555 N C16 H16A 1.082(7) . 1_555 N C16 H16B 1.088(6) . 1_555 N C16 H16C 1.090(8) . 1_555 N H16A C16 1.082(7) . 1_555 N H16A H16B 1.766(8) . 1_555 N H16A H16C 1.767(10) . 1_555 N H16B C16 1.088(6) . 1_555 N H16B H16A 1.766(8) . 1_555 N H16B H16C 1.751(9) . 1_555 N H16C C16 1.090(8) . 1_555 N H16C H16A 1.767(10) . 1_555 N H16C H16B 1.751(9) . 1_555 N O1 H1B 0.991(8) . 1_555 N O1 H2B 1.941(15) . -1_566 N O1 H1A 0.903(18) . 1_555 N O1 H1C 0.920(17) . 1_555 N O1 H3C 1.941(15) . 1_555 N O2 H2A 0.969(9) . 1_555 N O2 H3A 1.931(17) . 1_555 N O2 H2B 0.878(16) . 1_555 N O2 H1C 1.893(16) . -1_566 N O2 H2C 0.926(16) . 1_555 N C26 C21 1.534(4) . 1_555 N C26 H26A 1.077(8) . 1_555 N C26 H26B 1.067(8) . 1_555 N C26 H26C 1.100(7) . 1_555 N H26A C26 1.077(8) . 1_555 N H26A H26B 1.726(10) . 1_555 N H26A H26C 1.765(9) . 1_555 N H26B C26 1.067(8) . 1_555 N H26B H26A 1.726(10) . 1_555 N H26B H26C 1.770(9) . 1_555 N H26C C26 1.100(7) . 1_555 N H26C H26A 1.765(9) . 1_555 N H26C H26B 1.770(9) . 1_555 N C25 C21 1.516(4) . 1_555 N C25 H25A 1.108(7) . 1_555 N C25 H25B 1.086(7) . 1_555 N C25 H25C 1.095(7) . 1_555 N H25A C25 1.108(7) . 1_555 N H25A H25B 1.756(9) . 1_555 N H25A H25C 1.776(9) . 1_555 N H25B C25 1.086(7) . 1_555 N H25B H25A 1.756(9) . 1_555 N H25B H25C 1.775(9) . 1_555 N H25C C25 1.095(7) . 1_555 N H25C H25A 1.776(9) . 1_555 N H25C H25B 1.775(9) . 1_555 N O3 H3B 0.967(9) . 1_555 N O3 H3A 0.886(18) . 1_555 N O3 H1A 1.921(16) . 1_555 N O3 H3C 0.886(17) . 1_555 N O3 H2C 1.881(15) . 1_555 N H3B Cl1 2.190(7) . -1_566 N H3B O3 0.967(9) . 1_555 N H3B H3A 1.497(17) . 1_555 N H3B H3C 1.508(15) . 1_555 N H1B Cl1 2.271(6) . 1_555 N H1B O1 0.991(8) . 1_555 N H1B H1A 1.485(14) . 1_555 N H1B H1C 1.512(15) . 1_555 N H2A Cl1 2.251(7) . 1_555 N H2A O2 0.969(9) . 1_555 N H2A H2B 1.493(15) . 1_555 N H2A H2C 1.480(15) . 1_555 N H3A O2 1.931(17) . 1_555 N H3A O3 0.886(18) . 1_555 N H3A H3B 1.497(17) . 1_555 N H3A H3C 1.305(19) . 1_555 N H3A H2C 1.006(18) . 1_555 N H2B O1 1.941(15) . -1_566 N H2B O2 0.878(16) . 1_555 N H2B H2A 1.493(15) . 1_555 N H2B H1C 1.023(18) . -1_566 N H2B H2C 1.308(18) . 1_555 N H1A O1 0.903(18) . 1_555 N H1A O3 1.921(16) . 1_555 N H1A H1B 1.485(14) . 1_555 N H1A H1C 1.285(18) . 1_555 N H1A H3C 1.040(18) . 1_555 N H1C O1 0.920(17) . 1_555 N H1C O2 1.893(16) . -1_566 N H1C H1B 1.512(15) . 1_555 N H1C H2B 1.023(18) . -1_566 N H1C H1A 1.285(18) . 1_555 N H3C O1 1.941(15) . 1_555 N H3C O3 0.886(17) . 1_555 N H3C H3B 1.508(15) . 1_555 N H3C H3A 1.305(19) . 1_555 N H3C H1A 1.040(18) . 1_555 N H2C O2 0.926(16) . 1_555 N H2C O3 1.881(15) . 1_555 N H2C H2A 1.480(15) . 1_555 N H2C H3A 1.006(18) . 1_555 N H2C H2B 1.308(18) . 1_555 N 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H3B Cl1 H1B 76.15(26) -1_566 . 1_555 N H3B Cl1 H2A 73.82(25) -1_566 . 1_555 N H1B Cl1 H2A 81.93(25) 1_555 . 1_555 N C22 N2 C21 119.11(18) 1_555 . 1_555 N C22 N2 C2 114.01(18) 1_555 . 1_555 N C21 N2 C2 109.38(18) 1_555 . 1_555 N C1 N1 C11 121.66(19) 1_555 . 1_555 N C1 N1 C14 119.61(19) 1_555 . 1_555 N C11 N1 C14 118.73(18) 1_555 . 1_555 N C1 C3 N3 154.36(23) 1_555 . 1_555 N C1 C3 C2 59.30(16) 1_555 . 1_555 N N3 C3 C2 146.30(23) 1_555 . 1_555 N N1 C1 C3 151.51(23) 1_555 . 1_555 N N1 C1 C2 149.31(23) 1_555 . 1_555 N C3 C1 C2 59.12(17) 1_555 . 1_555 N N1 C11 H11 105.01(35) 1_555 . 1_555 N N1 C11 C13 110.49(20) 1_555 . 1_555 N N1 C11 C12 110.40(20) 1_555 . 1_555 N H11 C11 C13 109.9(4) 1_555 . 1_555 N H11 C11 C12 109.1(4) 1_555 . 1_555 N C13 C11 C12 111.77(22) 1_555 . 1_555 N N2 C22 H22 110.49(35) 1_555 . 1_555 N N2 C22 C23 109.05(19) 1_555 . 1_555 N N2 C22 C24 111.55(20) 1_555 . 1_555 N H22 C22 C23 108.3(4) 1_555 . 1_555 N H22 C22 C24 107.1(4) 1_555 . 1_555 N C23 C22 C24 110.27(21) 1_555 . 1_555 N C3 N3 C31 116.99(19) 1_555 . 1_555 N C3 N3 C34 123.81(19) 1_555 . 1_555 N C31 N3 C34 119.09(18) 1_555 . 1_555 N N3 C31 H31 105.01(33) 1_555 . 1_555 N N3 C31 C33 110.76(19) 1_555 . 1_555 N N3 C31 C32 111.74(21) 1_555 . 1_555 N H31 C31 C33 108.2(4) 1_555 . 1_555 N H31 C31 C32 108.7(4) 1_555 . 1_555 N C33 C31 C32 112.05(20) 1_555 . 1_555 N C22 C23 H23A 112.6(4) 1_555 . 1_555 N C22 C23 H23B 110.2(4) 1_555 . 1_555 N C22 C23 H23C 110.5(4) 1_555 . 1_555 N H23A C23 H23B 108.8(5) 1_555 . 1_555 N H23A C23 H23C 108.3(5) 1_555 . 1_555 N H23B C23 H23C 106.1(5) 1_555 . 1_555 N N1 C14 H14 104.91(33) 1_555 . 1_555 N N1 C14 C15 110.93(20) 1_555 . 1_555 N N1 C14 C16 112.55(20) 1_555 . 1_555 N H14 C14 C15 107.7(4) 1_555 . 1_555 N H14 C14 C16 108.2(4) 1_555 . 1_555 N C15 C14 C16 112.15(21) 1_555 . 1_555 N H36A C36 H36B 108.6(6) 1_555 . 1_555 N H36A C36 H36C 107.7(5) 1_555 . 1_555 N H36A C36 C34 112.2(4) 1_555 . 1_555 N H36B C36 H36C 107.1(5) 1_555 . 1_555 N H36B C36 C34 110.3(4) 1_555 . 1_555 N H36C C36 C34 110.8(4) 1_555 . 1_555 N N3 C34 C36 111.35(19) 1_555 . 1_555 N N3 C34 H34 105.34(34) 1_555 . 1_555 N N3 C34 C35 112.02(21) 1_555 . 1_555 N C36 C34 H34 107.0(4) 1_555 . 1_555 N C36 C34 C35 113.45(21) 1_555 . 1_555 N H34 C34 C35 107.15(34) 1_555 . 1_555 N N2 C21 H21 104.67(35) 1_555 . 1_555 N N2 C21 C26 113.36(21) 1_555 . 1_555 N N2 C21 C25 113.46(20) 1_555 . 1_555 N H21 C21 C26 106.3(4) 1_555 . 1_555 N H21 C21 C25 107.3(4) 1_555 . 1_555 N C26 C21 C25 111.08(22) 1_555 . 1_555 N N2 C2 C3 151.54(23) 1_555 . 1_555 N N2 C2 C1 146.78(22) 1_555 . 1_555 N C3 C2 C1 61.58(17) 1_555 . 1_555 N C31 C33 H33A 111.8(4) 1_555 . 1_555 N C31 C33 H33B 108.4(4) 1_555 . 1_555 N C31 C33 H33C 111.1(4) 1_555 . 1_555 N H33A C33 H33B 109.4(5) 1_555 . 1_555 N H33A C33 H33C 108.3(5) 1_555 . 1_555 N H33B C33 H33C 107.7(5) 1_555 . 1_555 N C34 C35 H35A 110.6(4) 1_555 . 1_555 N C34 C35 H35B 109.5(4) 1_555 . 1_555 N C34 C35 H35C 112.8(4) 1_555 . 1_555 N H35A C35 H35B 109.1(5) 1_555 . 1_555 N H35A C35 H35C 105.1(6) 1_555 . 1_555 N H35B C35 H35C 109.6(6) 1_555 . 1_555 N C11 C13 H13A 111.5(4) 1_555 . 1_555 N C11 C13 H13B 110.3(4) 1_555 . 1_555 N C11 C13 H13C 111.9(4) 1_555 . 1_555 N H13A C13 H13B 107.8(5) 1_555 . 1_555 N H13A C13 H13C 107.7(5) 1_555 . 1_555 N H13B C13 H13C 107.5(6) 1_555 . 1_555 N C22 C24 H24A 110.5(4) 1_555 . 1_555 N C22 C24 H24B 109.9(4) 1_555 . 1_555 N C22 C24 H24C 114.7(4) 1_555 . 1_555 N H24A C24 H24B 107.7(5) 1_555 . 1_555 N H24A C24 H24C 108.9(5) 1_555 . 1_555 N H24B C24 H24C 104.9(5) 1_555 . 1_555 N C31 C32 H32A 112.1(4) 1_555 . 1_555 N C31 C32 H32B 109.9(4) 1_555 . 1_555 N C31 C32 H32C 111.3(4) 1_555 . 1_555 N H32A C32 H32B 108.2(5) 1_555 . 1_555 N H32A C32 H32C 109.0(6) 1_555 . 1_555 N H32B C32 H32C 106.1(5) 1_555 . 1_555 N C11 C12 H12A 112.5(4) 1_555 . 1_555 N C11 C12 H12B 109.6(4) 1_555 . 1_555 N C11 C12 H12C 112.2(4) 1_555 . 1_555 N H12A C12 H12B 105.6(6) 1_555 . 1_555 N H12A C12 H12C 109.0(6) 1_555 . 1_555 N H12B C12 H12C 107.7(5) 1_555 . 1_555 N C14 C15 H15A 111.7(4) 1_555 . 1_555 N C14 C15 H15B 108.9(4) 1_555 . 1_555 N C14 C15 H15C 110.5(4) 1_555 . 1_555 N H15A C15 H15B 108.9(6) 1_555 . 1_555 N H15A C15 H15C 108.0(6) 1_555 . 1_555 N H15B C15 H15C 108.8(6) 1_555 . 1_555 N C14 C16 H16A 111.1(4) 1_555 . 1_555 N C14 C16 H16B 109.4(4) 1_555 . 1_555 N C14 C16 H16C 111.3(4) 1_555 . 1_555 N H16A C16 H16B 109.0(6) 1_555 . 1_555 N H16A C16 H16C 108.9(6) 1_555 . 1_555 N H16B C16 H16C 107.0(5) 1_555 . 1_555 N H1B O1 H1A 103.1(9) 1_555 . 1_555 N H1B O1 H1C 104.5(9) 1_555 . 1_555 N H1A O1 H1C 89.7(12) 1_555 . 1_555 N H2A O2 H2B 107.7(10) 1_555 . 1_555 N H2A O2 H2C 102.6(11) 1_555 . 1_555 N H2B O2 H2C 92.9(13) 1_555 . 1_555 N C21 C26 H26A 114.1(4) 1_555 . 1_555 N C21 C26 H26B 107.9(4) 1_555 . 1_555 N C21 C26 H26C 109.8(4) 1_555 . 1_555 N H26A C26 H26B 107.2(6) 1_555 . 1_555 N H26A C26 H26C 108.3(6) 1_555 . 1_555 N H26B C26 H26C 109.5(6) 1_555 . 1_555 N C21 C25 H25A 111.5(4) 1_555 . 1_555 N C21 C25 H25B 110.1(4) 1_555 . 1_555 N C21 C25 H25C 112.4(4) 1_555 . 1_555 N H25A C25 H25B 106.3(5) 1_555 . 1_555 N H25A C25 H25C 107.4(5) 1_555 . 1_555 N H25B C25 H25C 108.9(5) 1_555 . 1_555 N H3B O3 H3A 107.7(11) 1_555 . 1_555 N H3B O3 H3C 108.8(9) 1_555 . 1_555 N H3A O3 H3C 94.9(12) 1_555 . 1_555 N Cl1 H3B O3 176.3(6) -1_566 . 1_555 N Cl1 H3B H3A 143.2(7) -1_566 . 1_555 N Cl1 H3B H3C 143.8(6) -1_566 . 1_555 N O3 H3B H3A 34.3(7) 1_555 . 1_555 N O3 H3B H3C 33.8(7) 1_555 . 1_555 N H3A H3B H3C 51.5(7) 1_555 . 1_555 N Cl1 H1B O1 170.3(6) 1_555 . 1_555 N Cl1 H1B H1A 134.9(7) 1_555 . 1_555 N Cl1 H1B H1C 139.1(7) 1_555 . 1_555 N O1 H1B H1A 36.3(7) 1_555 . 1_555 N O1 H1B H1C 36.1(7) 1_555 . 1_555 N H1A H1B H1C 50.8(7) 1_555 . 1_555 N Cl1 H2A O2 173.8(6) 1_555 . 1_555 N Cl1 H2A H2B 143.6(7) 1_555 . 1_555 N Cl1 H2A H2C 136.7(8) 1_555 . 1_555 N O2 H2A H2B 34.1(7) 1_555 . 1_555 N O2 H2A H2C 37.7(8) 1_555 . 1_555 N H2B H2A H2C 52.2(8) 1_555 . 1_555 N O3 H3A H3B 38.0(8) 1_555 . 1_555 N O3 H3A H3C 42.6(10) 1_555 . 1_555 N O3 H3A H2C 168.0(20) 1_555 . 1_555 N H3B H3A H3C 64.7(10) 1_555 . 1_555 N H3B H3A H2C 132.4(15) 1_555 . 1_555 N H3C H3A H2C 132.2(18) 1_555 . 1_555 N O2 H2B H2A 38.2(7) 1_555 . 1_555 N O2 H2B H1C 169.4(19) 1_555 . -1_566 N O2 H2B H2C 45.0(10) 1_555 . 1_555 N H2A H2B H1C 136.5(15) 1_555 . -1_566 N H2A H2B H2C 63.4(9) 1_555 . 1_555 N H1C H2B H2C 126.3(17) -1_566 . 1_555 N O1 H1A H1B 40.5(6) 1_555 . 1_555 N O1 H1A H1C 45.7(10) 1_555 . 1_555 N O1 H1A H3C 174.1(15) 1_555 . 1_555 N H1B H1A H1C 65.7(9) 1_555 . 1_555 N H1B H1A H3C 133.6(13) 1_555 . 1_555 N H1C H1A H3C 136.2(16) 1_555 . 1_555 N O1 H1C H1B 39.4(6) 1_555 . 1_555 N O1 H1C H2B 175.2(17) 1_555 . -1_566 N O1 H1C H1A 44.6(10) 1_555 . 1_555 N H1B H1C H2B 140.2(15) 1_555 . -1_566 N H1B H1C H1A 63.5(9) 1_555 . 1_555 N H2B H1C H1A 130.8(16) -1_566 . 1_555 N O3 H3C H3B 37.4(6) 1_555 . 1_555 N O3 H3C H3A 42.6(11) 1_555 . 1_555 N O3 H3C H1A 171.4(16) 1_555 . 1_555 N H3B H3C H3A 63.8(10) 1_555 . 1_555 N H3B H3C H1A 134.2(13) 1_555 . 1_555 N H3A H3C H1A 141.6(16) 1_555 . 1_555 N O2 H2C H2A 39.7(7) 1_555 . 1_555 N O2 H2C H3A 175.7(18) 1_555 . 1_555 N O2 H2C H2B 42.1(10) 1_555 . 1_555 N H2A H2C H3A 137.6(17) 1_555 . 1_555 N H2A H2C H2B 64.4(9) 1_555 . 1_555 N H3A H2C H2B 142.0(17) 1_555 . 1_555 N _reflns_number_total 247 _reflns_limit_h_min -19 _reflns_limit_h_max -2 _reflns_limit_k_min -5 _reflns_limit_k_max 3 _reflns_limit_l_min -12 _reflns_limit_l_max -1 _reflns_d_resolution_high 0.500 _reflns_d_resolution_low 4.766