Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'Michael Watkinson' 'Andrew P. Lightfoot' 'Majid Motevalli' 'Sonia Pulacchini' 'K. Shastri' 'Kevin F. Sibbons' 'Hayley Wan' 'Andrew Whiting ' _publ_contact_author_name 'Dr Michael Watkinson' _publ_contact_author_address ; Dept of Chemistry Queen Mary, University of London Mile End Road London E1 4NS UNITED KINGDOM ; _publ_contact_author_email 'M.WATKINSON@QMUL.AC.UK ' _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Synthesis of C2-symmetric aza- and aza-oxamacrocyclic ligands derived from (1R,2R)-1,2-diaminocyclohexane and their applications in catalysis ; data_4sp73f _database_code_CSD 188705 _audit_creation_date 2002-06-13T10:38:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H80 Cu1 N8 O8' _chemical_formula_sum 'C10 H18 Cl2 Cu N2 O' _chemical_formula_weight 316.7 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 41' _symmetry_space_group_name_Hall 'I 4bw' _symmetry_Int_Tables_number 80 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-y, x+1/2, z+1/4' 'y+1/2, -x, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1, z+1' '-y+1/2, x+1, z+3/4' 'y+1, -x+1/2, z+5/4' _cell_length_a 26.629(4) _cell_length_b 26.629(4) _cell_length_c 7.506(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5322.5(18) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.208 _cell_measurement_theta_max 10.865 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour Green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2608 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.024 _exptl_absorpt_factor_muR 0.405 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.12 _exptl_absorpt_correction_T_max 0.589 _exptl_absorpt_correction_T_ave 0.6093 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.9924E-2 _diffrn_orient_matrix_ub_12 0.35858E-1 _diffrn_orient_matrix_ub_13 0.17991E-1 _diffrn_orient_matrix_ub_21 -0.36059E-1 _diffrn_orient_matrix_ub_22 -0.9292E-2 _diffrn_orient_matrix_ub_23 -0.17399E-1 _diffrn_orient_matrix_ub_31 -0.3387E-2 _diffrn_orient_matrix_ub_32 -0.6138E-2 _diffrn_orient_matrix_ub_33 0.130861 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 8 _diffrn_standards_decay_corr_max 1.094 _diffrn_standards_decay_corr_min 0.989 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -12 6 0 14 -2 0 _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_unetI/netI 0.1522 _diffrn_reflns_number 2688 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -2 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 24.96 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 2521 _reflns_number_gt 1122 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4/PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4/PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #---------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0000P)^2^+111.9695P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2521 _refine_ls_number_parameters 289 _refine_ls_number_restraints 105 _refine_ls_R_factor_all 0.2418 _refine_ls_R_factor_gt 0.0923 _refine_ls_wR_factor_ref 0.1971 _refine_ls_wR_factor_gt 0.1524 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.003 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0 _refine_diff_density_max 0.582 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.129 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 0.006 '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' 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 Cu1 Cu 0.92852(14) 0.25004(13) 0.0037(4) 0.0557(10) Uani 1 1 d U . . Cu2 Cu 0.07274(15) 0.24311(13) 0.8164(5) 0.0650(13) Uani 1 1 d U . . N1 N 0.9213(8) 0.2745(8) 0.257(4) 0.053(4) Uani 1 1 d U . . N2 N 0.9287(9) 0.3238(8) -0.060(4) 0.058(4) Uani 1 1 d U . . N3 N 0.0655(12) 0.1685(9) 0.872(5) 0.079(6) Uani 1 1 d U . . N4 N 0.0833(9) 0.2178(9) 0.559(4) 0.074(5) Uani 1 1 d U . . O1 O 0.8421(6) 0.2664(6) 0.003(3) 0.058(4) Uani 1 1 d U . . O2 O 0.1568(8) 0.2193(8) 0.812(5) 0.095(6) Uani 1 1 d U . . Cl1 Cl 0.9374(3) 0.2326(3) -0.2953(14) 0.077(3) Uani 1 1 d U . . Cl2 Cl 0.9316(3) 0.1695(2) 0.0911(15) 0.070(2) Uani 1 1 d U . . Cl3 Cl 0.0690(4) 0.3220(3) 0.720(2) 0.121(4) Uani 1 1 d U . . Cl4 Cl 0.0628(4) 0.2622(4) 1.104(2) 0.112(4) Uani 1 1 d U . . C1 C 0.8699(9) 0.2845(9) 0.304(4) 0.051(5) Uani 1 1 d U . . H1A H 0.8653 0.2756 0.4282 0.061 Uiso 1 1 calc R . . H1B H 0.8642 0.3204 0.2935 0.061 Uiso 1 1 calc R . . C2 C 0.8325(10) 0.2591(11) 0.202(4) 0.072(7) Uani 1 1 d U . . H2A H 0.7996 0.2722 0.2318 0.087 Uiso 1 1 calc R . . H2B H 0.833 0.2236 0.2298 0.087 Uiso 1 1 calc R . . C3 C 0.8342(10) 0.3191(10) -0.051(5) 0.077(8) Uani 1 1 d U . . H3A H 0.8054 0.3213 -0.1299 0.092 Uiso 1 1 calc R . . H3B H 0.8276 0.3396 0.053 0.092 Uiso 1 1 calc R . . C4 C 0.8787(10) 0.3372(9) -0.142(5) 0.073(7) Uani 1 1 d U . . H4A H 0.8766 0.3735 -0.1495 0.087 Uiso 1 1 calc R . . H4B H 0.8782 0.3243 -0.2628 0.087 Uiso 1 1 calc R . . C5 C 0.9374(10) 0.3539(9) 0.095(4) 0.050(6) Uani 1 1 d U . . H5 H 0.9052 0.3695 0.1264 0.06 Uiso 1 1 calc R . . C6 C 0.9737(12) 0.3948(9) 0.072(5) 0.083(9) Uani 1 1 d U . . H6A H 0.9631 0.4158 -0.0265 0.099 Uiso 1 1 calc R . . H6B H 1.0062 0.3807 0.0424 0.099 Uiso 1 1 calc R . . C7 C 0.9790(12) 0.4288(9) 0.248(5) 0.085(9) Uani 1 1 d U . . H7A H 1.0053 0.4535 0.2325 0.102 Uiso 1 1 calc R . . H7B H 0.9477 0.4463 0.2719 0.102 Uiso 1 1 calc R . . C8 C 0.9918(12) 0.3942(10) 0.403(6) 0.085(10) Uani 1 1 d U . . H8A H 1.0251 0.3804 0.3845 0.102 Uiso 1 1 calc R . . H8B H 0.9927 0.4139 0.5121 0.102 Uiso 1 1 calc R . . C9 C 0.9556(12) 0.3517(12) 0.428(5) 0.069(9) Uani 1 1 d U . . H9A H 0.9226 0.3644 0.459 0.083 Uiso 1 1 calc R . . H9B H 0.9669 0.3296 0.5227 0.083 Uiso 1 1 calc R . . C10 C 0.9532(9) 0.3229(8) 0.251(4) 0.051(5) Uani 1 1 d U . . H10 H 0.9877 0.3121 0.2257 0.061 Uiso 1 1 calc R . . C11 C 0.1138(15) 0.1417(11) 0.910(5) 0.121(13) Uani 1 1 d U . . H11A H 0.1095 0.1188 1.0092 0.145 Uiso 1 1 calc R . . H11B H 0.1243 0.1226 0.8065 0.145 Uiso 1 1 calc R . . C12 C 0.1516(15) 0.1802(12) 0.954(6) 0.127(11) Uani 1 1 d U . . H12A H 0.1838 0.164 0.9715 0.152 Uiso 1 1 calc R . . H12B H 0.1423 0.1963 1.0649 0.152 Uiso 1 1 calc R . . C13 C 0.1735(12) 0.2034(18) 0.650(6) 0.146(14) Uani 1 1 d U . . H13A H 0.1712 0.1671 0.6407 0.175 Uiso 1 1 calc R . . H13B H 0.2081 0.2133 0.6316 0.175 Uiso 1 1 calc R . . C14 C 0.1366(16) 0.2305(17) 0.501(7) 0.154(15) Uani 1 1 d U . . H14A H 0.1417 0.2666 0.5007 0.185 Uiso 1 1 calc R . . H14B H 0.1432 0.2175 0.383 0.185 Uiso 1 1 calc R . . C15 C 0.0685(10) 0.1635(9) 0.549(4) 0.058(6) Uani 1 1 d U . . H15 H 0.0997 0.144 0.5501 0.069 Uiso 1 1 calc R . . C16 C 0.0424(13) 0.1529(12) 0.368(6) 0.074(9) Uani 1 1 d U . . H16A H 0.0124 0.1731 0.3547 0.089 Uiso 1 1 calc R . . H16B H 0.065 0.1602 0.2694 0.089 Uiso 1 1 calc R . . C17 C 0.0296(18) 0.0981(15) 0.373(6) 0.123(16) Uani 1 1 d U . . H17A H 0.0109 0.0897 0.2659 0.148 Uiso 1 1 calc R . . H17B H 0.0605 0.0789 0.3707 0.148 Uiso 1 1 calc R . . C18 C 0.0018(14) 0.0839(12) 0.520(8) 0.118(13) Uani 1 1 d U . . H18A H -0.0069 0.0487 0.5072 0.141 Uiso 1 1 calc R . . H18B H -0.0293 0.1029 0.5201 0.141 Uiso 1 1 calc R . . C19 C 0.0275(13) 0.0911(9) 0.700(5) 0.079(9) Uani 1 1 d U . . H19A H 0.0573 0.0703 0.7101 0.095 Uiso 1 1 calc R . . H19B H 0.0049 0.0832 0.7976 0.095 Uiso 1 1 calc R . . C20 C 0.0418(11) 0.1492(10) 0.699(4) 0.061(7) Uani 1 1 d U . . H20 H 0.0096 0.1669 0.6901 0.074 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 Cu1 0.066(2) 0.0494(19) 0.051(3) -0.003(2) -0.001(2) 0.0068(18) Cu2 0.066(2) 0.051(2) 0.078(4) 0.002(2) 0.003(3) 0.0082(19) N1 0.062(9) 0.052(8) 0.045(8) 0.005(7) -0.002(10) -0.001(8) N2 0.076(10) 0.053(7) 0.046(10) 0.000(6) -0.001(11) -0.009(9) N3 0.141(15) 0.051(7) 0.044(11) 0.008(7) 0.025(14) -0.004(11) N4 0.101(14) 0.067(9) 0.054(9) 0.023(8) 0.006(11) -0.044(11) O1 0.056(7) 0.056(8) 0.063(10) -0.037(10) -0.013(7) 0.005(6) O2 0.075(9) 0.079(12) 0.130(19) -0.061(13) -0.017(10) 0.016(8) Cl1 0.096(6) 0.073(5) 0.063(5) -0.013(5) 0.012(5) 0.022(5) Cl2 0.101(6) 0.041(3) 0.069(6) -0.007(4) -0.012(6) 0.005(3) Cl3 0.144(8) 0.051(4) 0.167(11) 0.021(6) -0.078(9) -0.012(5) Cl4 0.155(9) 0.084(6) 0.096(7) -0.033(6) 0.058(8) -0.024(6) C1 0.068(11) 0.043(13) 0.042(13) -0.002(12) 0.007(9) -0.013(10) C2 0.066(9) 0.09(2) 0.057(13) -0.055(13) -0.007(11) 0.025(14) C3 0.071(10) 0.055(12) 0.10(2) -0.041(13) -0.027(15) 0.007(10) C4 0.094(16) 0.046(13) 0.08(2) -0.021(12) -0.022(12) 0.014(11) C5 0.058(15) 0.046(8) 0.046(12) 0.005(7) 0.006(12) 0.002(9) C6 0.10(2) 0.029(12) 0.115(19) -0.015(12) 0.03(2) -0.016(12) C7 0.12(2) 0.033(13) 0.11(2) -0.016(10) 0.03(2) -0.005(12) C8 0.09(2) 0.030(14) 0.13(2) -0.009(13) -0.01(2) -0.015(12) C9 0.070(19) 0.091(18) 0.046(13) 0.004(11) -0.009(16) -0.034(16) C10 0.047(12) 0.041(10) 0.064(13) 0.004(8) -0.025(14) 0.006(9) C11 0.22(3) 0.057(13) 0.09(3) 0.014(17) -0.07(2) 0.024(12) C12 0.18(2) 0.059(17) 0.14(3) -0.049(16) -0.09(3) 0.064(14) C13 0.053(12) 0.20(4) 0.19(3) -0.10(3) 0.049(16) -0.043(17) C14 0.17(3) 0.21(4) 0.089(19) -0.01(3) 0.072(16) -0.12(3) C15 0.078(18) 0.054(11) 0.040(11) 0.013(9) -0.010(11) -0.010(11) C16 0.08(2) 0.078(16) 0.064(15) -0.016(14) -0.028(16) 0.026(15) C17 0.18(4) 0.087(18) 0.10(2) -0.02(2) -0.08(3) 0.00(3) C18 0.12(3) 0.040(17) 0.19(3) -0.02(2) -0.04(3) -0.009(16) C19 0.10(2) 0.025(10) 0.11(2) 0.001(13) 0.046(18) 0.008(11) C20 0.068(17) 0.043(10) 0.074(14) 0.015(11) 0.013(12) -0.017(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cu1 N1 2.02(3) . ? Cu1 N2 2.02(2) . ? Cu1 Cl2 2.244(8) . ? Cu1 Cl1 2.303(11) . ? Cu1 O1 2.343(17) . ? Cu2 N3 2.04(2) . ? Cu2 N4 2.06(3) . ? Cu2 Cl3 2.225(9) . ? Cu2 Cl4 2.234(15) . ? Cu2 O2 2.33(2) . ? N1 C1 1.44(3) . ? N1 C10 1.55(3) . ? N2 C5 1.43(4) . ? N2 C4 1.51(3) . ? N3 C11 1.50(4) . ? N3 C20 1.53(4) . ? N4 C15 1.50(3) . ? N4 C14 1.52(4) . ? O1 C3 1.48(3) . ? O1 C2 1.52(4) . ? O2 C13 1.36(5) . ? O2 C12 1.50(5) . ? C1 C2 1.43(3) . ? C1 H1A 0.97 . ? C1 H1B 0.97 . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 C4 1.45(4) . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C5 C6 1.47(3) . ? C5 C10 1.49(4) . ? C5 H5 0.98 . ? C6 C7 1.61(5) . ? C6 H6A 0.97 . ? C6 H6B 0.97 . ? C7 C8 1.52(5) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? C8 C9 1.50(4) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C9 C10 1.53(5) . ? C9 H9A 0.97 . ? C9 H9B 0.97 . ? C10 H10 0.98 . ? C11 C12 1.47(4) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.65(6) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C20 1.38(4) . ? C15 C16 1.56(5) . ? C15 H15 0.98 . ? C16 C17 1.50(5) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C18 1.38(6) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C18 C19 1.53(5) . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? C19 C20 1.59(3) . ? C19 H19A 0.97 . ? C19 H19B 0.97 . ? C20 H20 0.98 . ? 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 N1 Cu1 N2 84.8(11) . . ? N1 Cu1 Cl2 92.1(7) . . ? N2 Cu1 Cl2 176.0(9) . . ? N1 Cu1 Cl1 172.8(7) . . ? N2 Cu1 Cl1 88.0(9) . . ? Cl2 Cu1 Cl1 95.1(4) . . ? N1 Cu1 O1 81.2(9) . . ? N2 Cu1 O1 79.7(8) . . ? Cl2 Cu1 O1 102.3(5) . . ? Cl1 Cu1 O1 97.8(7) . . ? N3 Cu2 N4 83.5(11) . . ? N3 Cu2 Cl3 169.3(10) . . ? N4 Cu2 Cl3 90.6(8) . . ? N3 Cu2 Cl4 90.7(10) . . ? N4 Cu2 Cl4 174.0(8) . . ? Cl3 Cu2 Cl4 95.4(5) . . ? N3 Cu2 O2 80.1(11) . . ? N4 Cu2 O2 76.5(11) . . ? Cl3 Cu2 O2 107.2(7) . . ? Cl4 Cu2 O2 100.9(9) . . ? C1 N1 C10 112.0(18) . . ? C1 N1 Cu1 113(2) . . ? C10 N1 Cu1 101.0(19) . . ? C5 N2 C4 110(2) . . ? C5 N2 Cu1 110.7(19) . . ? C4 N2 Cu1 108.9(16) . . ? C11 N3 C20 111(3) . . ? C11 N3 Cu2 115(2) . . ? C20 N3 Cu2 101.1(19) . . ? C15 N4 C14 116(3) . . ? C15 N4 Cu2 108.9(19) . . ? C14 N4 Cu2 109(3) . . ? C3 O1 C2 111(2) . . ? C3 O1 Cu1 108.4(15) . . ? C2 O1 Cu1 98.0(15) . . ? C13 O2 C12 117(3) . . ? C13 O2 Cu2 114(2) . . ? C12 O2 Cu2 95(2) . . ? C2 C1 N1 116(2) . . ? C2 C1 H1A 108.2 . . ? N1 C1 H1A 108.2 . . ? C2 C1 H1B 108.2 . . ? N1 C1 H1B 108.2 . . ? H1A C1 H1B 107.4 . . ? C1 C2 O1 111(2) . . ? C1 C2 H2A 109.6 . . ? O1 C2 H2A 109.5 . . ? C1 C2 H2B 109.6 . . ? O1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C4 C3 O1 109(2) . . ? C4 C3 H3A 109.8 . . ? O1 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? O1 C3 H3B 109.8 . . ? H3A C3 H3B 108.3 . . ? C3 C4 N2 117(3) . . ? C3 C4 H4A 108.1 . . ? N2 C4 H4A 108.1 . . ? C3 C4 H4B 108.1 . . ? N2 C4 H4B 108.1 . . ? H4A C4 H4B 107.3 . . ? N2 C5 C6 115(3) . . ? N2 C5 C10 112(2) . . ? C6 C5 C10 108(3) . . ? N2 C5 H5 106.9 . . ? C6 C5 H5 106.9 . . ? C10 C5 H5 106.9 . . ? C5 C6 C7 112(3) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 108(2) . . ? C8 C7 H7A 110.1 . . ? C6 C7 H7A 110.1 . . ? C8 C7 H7B 110.1 . . ? C6 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? C9 C8 C7 114(3) . . ? C9 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 107(3) . . ? C8 C9 H9A 110.3 . . ? C10 C9 H9A 110.3 . . ? C8 C9 H9B 110.3 . . ? C10 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? C5 C10 C9 115(2) . . ? C5 C10 N1 109(2) . . ? C9 C10 N1 115(2) . . ? C5 C10 H10 106 . . ? C9 C10 H10 106 . . ? N1 C10 H10 106 . . ? C12 C11 N3 107(2) . . ? C12 C11 H11A 110.2 . . ? N3 C11 H11A 110.3 . . ? C12 C11 H11B 110.2 . . ? N3 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C11 C12 O2 113(3) . . ? C11 C12 H12A 109 . . ? O2 C12 H12A 109 . . ? C11 C12 H12B 109 . . ? O2 C12 H12B 109 . . ? H12A C12 H12B 107.8 . . ? O2 C13 C14 106(3) . . ? O2 C13 H13A 110.6 . . ? C14 C13 H13A 110.6 . . ? O2 C13 H13B 110.6 . . ? C14 C13 H13B 110.6 . . ? H13A C13 H13B 108.7 . . ? N4 C14 C13 105(3) . . ? N4 C14 H14A 110.7 . . ? C13 C14 H14A 110.7 . . ? N4 C14 H14B 110.7 . . ? C13 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? C20 C15 N4 111(3) . . ? C20 C15 C16 116(2) . . ? N4 C15 C16 110(2) . . ? C20 C15 H15 106.6 . . ? N4 C15 H15 106.6 . . ? C16 C15 H15 106.6 . . ? C17 C16 C15 105(3) . . ? C17 C16 H16A 110.8 . . ? C15 C16 H16A 110.8 . . ? C17 C16 H16B 110.8 . . ? C15 C16 H16B 110.8 . . ? H16A C16 H16B 108.9 . . ? C18 C17 C16 114(4) . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17B 108.7 . . ? C16 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 116(3) . . ? C17 C18 H18A 108.4 . . ? C19 C18 H18A 108.4 . . ? C17 C18 H18B 108.4 . . ? C19 C18 H18B 108.4 . . ? H18A C18 H18B 107.4 . . ? C18 C19 C20 103(3) . . ? C18 C19 H19A 111.2 . . ? C20 C19 H19A 111.2 . . ? C18 C19 H19B 111.2 . . ? C20 C19 H19B 111.2 . . ? H19A C19 H19B 109.1 . . ? C15 C20 N3 113(2) . . ? C15 C20 C19 113(3) . . ? N3 C20 C19 115(3) . . ? C15 C20 H20 105 . . ? N3 C20 H20 105 . . ? C19 C20 H20 105 . . ? data_isp78 _database_code_CSD 195733 _audit_creation_date 2002-10-15T13:20:25-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H27 N3 O3 S1' _chemical_formula_sum 'C18 H27 N3 O3 S' _chemical_formula_weight 365.49 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41' _symmetry_space_group_name_Hall 'P 4w' _symmetry_Int_Tables_number 76 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 11.164(2) _cell_length_b 11.164(2) _cell_length_c 14.910(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1858.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 9.2875 _cell_measurement_theta_max 11.713 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_factor_muR 0.02 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_absorpt_correction_T_min 0.3585 _exptl_absorpt_correction_T_max 0.9807 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.078961 _diffrn_orient_matrix_ub_12 -0.041925 _diffrn_orient_matrix_ub_13 0.003378 _diffrn_orient_matrix_ub_21 -0.041236 _diffrn_orient_matrix_ub_22 -0.074495 _diffrn_orient_matrix_ub_23 0.020307 _diffrn_orient_matrix_ub_31 -0.008817 _diffrn_orient_matrix_ub_32 -0.025787 _diffrn_orient_matrix_ub_33 -0.063888 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3 _diffrn_standards_decay_corr_max 1.035 _diffrn_standards_decay_corr_min 0.988 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 8 -4 1 4 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_unetI/netI 0.2394 _diffrn_reflns_number 1553 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 23.05 _diffrn_reflns_theta_full 23.05 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 1351 _reflns_number_gt 682 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0767P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 1351 _refine_ls_number_parameters 215 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.2105 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.1818 _refine_ls_wR_factor_gt 0.1382 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(4) _refine_diff_density_max 0.316 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.073 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 S1 S 0.3477(4) 0.8494(4) 0.1023(2) 0.0403(10) Uani 1 1 d . . . N1 N 0.2246(10) 0.7970(11) 0.1438(6) 0.037(3) Uani 1 1 d . . . N2 N 0.0155(9) 0.7575(10) 0.2503(6) 0.026(3) Uani 1 1 d . . . N3 N -0.1466(10) 0.8822(10) 0.3679(7) 0.034(3) Uani 1 1 d . . . H3 H -0.1159 0.8542 0.418 0.041 Uiso 1 1 calc R . . O1 O 0.3166(9) 0.8936(9) 0.0128(5) 0.045(3) Uani 1 1 d . . . O2 O 0.4362(8) 0.7578(9) 0.1112(6) 0.048(3) Uani 1 1 d . . . O3 O -0.1815(10) 1.0540(9) 0.2880(6) 0.059(4) Uani 1 1 d . . . C1 C 0.3921(9) 0.9732(7) 0.1664(5) 0.036(4) Uani 1 1 d G . . C2 C 0.3398(8) 1.0850(8) 0.1543(5) 0.040(4) Uani 1 1 d G . . H2 H 0.2784 1.0953 0.1109 0.048 Uiso 1 1 calc R . . C3 C 0.3776(9) 1.1819(6) 0.2056(6) 0.038(4) Uani 1 1 d G . . H3' H 0.3419 1.2583 0.1972 0.046 Uiso 1 1 calc R . . C4 C 0.4675(9) 1.1669(7) 0.2691(6) 0.041(4) Uani 1 1 d G . . C5 C 0.5197(8) 1.0551(9) 0.2813(5) 0.037(4) Uani 1 1 d G . . H5 H 0.5811 1.0448 0.3247 0.044 Uiso 1 1 calc R . . C6 C 0.4820(8) 0.9582(7) 0.2299(6) 0.041(4) Uani 1 1 d G . . H6 H 0.5177 0.8817 0.2383 0.049 Uiso 1 1 calc R . . C7 C 0.2330(13) 0.7437(12) 0.2373(8) 0.040(4) Uani 1 1 d . . . H7A H 0.3018 0.688 0.2408 0.048 Uiso 1 1 calc R . . H7B H 0.245 0.8081 0.282 0.048 Uiso 1 1 calc R . . C8 C 0.1173(12) 0.6769(12) 0.2569(8) 0.032(3) Uani 1 1 d . . . H8A H 0.1076 0.6104 0.2136 0.038 Uiso 1 1 calc R . . H8B H 0.1207 0.6423 0.318 0.038 Uiso 1 1 calc R . . C9 C 0.0063(14) 0.8058(12) 0.1599(8) 0.038(4) Uani 1 1 d . . . H9A H -0.0644 0.859 0.1554 0.046 Uiso 1 1 calc R . . H9B H -0.0033 0.7399 0.1161 0.046 Uiso 1 1 calc R . . C10 C 0.1220(13) 0.8773(13) 0.1393(8) 0.037(4) Uani 1 1 d . . . H10A H 0.1166 0.9132 0.0787 0.045 Uiso 1 1 calc R . . H10B H 0.1316 0.9428 0.1835 0.045 Uiso 1 1 calc R . . C11 C -0.0966(12) 0.7028(12) 0.2833(7) 0.033(4) Uani 1 1 d . . . H11 H -0.0771 0.6628 0.3415 0.04 Uiso 1 1 calc R . . C12 C -0.1496(13) 0.6052(12) 0.2207(9) 0.037(4) Uani 1 1 d . . . H12A H -0.1649 0.6402 0.1608 0.044 Uiso 1 1 calc R . . H12B H -0.0906 0.5397 0.2134 0.044 Uiso 1 1 calc R . . C13 C -0.2669(12) 0.5536(12) 0.2583(10) 0.037(4) Uani 1 1 d . . . H13A H -0.3016 0.4977 0.2139 0.044 Uiso 1 1 calc R . . H13B H -0.249 0.5075 0.3134 0.044 Uiso 1 1 calc R . . C14 C -0.3565(14) 0.6480(13) 0.2796(10) 0.049(4) Uani 1 1 d . . . H14A H -0.428 0.6105 0.307 0.058 Uiso 1 1 calc R . . H14B H -0.3818 0.6881 0.2235 0.058 Uiso 1 1 calc R . . C15 C -0.3051(13) 0.7403(12) 0.3437(10) 0.043(4) Uani 1 1 d . . . H15A H -0.2855 0.7017 0.4016 0.051 Uiso 1 1 calc R . . H15B H -0.3652 0.8037 0.355 0.051 Uiso 1 1 calc R . . C16 C -0.1912(12) 0.7962(14) 0.3030(9) 0.037(4) Uani 1 1 d . . . H16 H -0.2125 0.8389 0.2463 0.045 Uiso 1 1 calc R . . C17 C -0.1489(11) 1.0017(14) 0.3568(10) 0.036(4) Uani 1 1 d . . . H17 H -0.1234 1.0497 0.4058 0.043 Uiso 1 1 calc R . . C18 C 0.5132(15) 1.2712(14) 0.3193(11) 0.062(5) Uani 1 1 d . . . H18A H 0.5804 1.3069 0.2866 0.093 Uiso 1 1 calc R . . H18B H 0.5403 1.2453 0.3787 0.093 Uiso 1 1 calc R . . H18C H 0.4491 1.3306 0.326 0.093 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 S1 0.035(2) 0.047(3) 0.0385(18) -0.006(2) 0.004(2) 0.001(2) N1 0.030(8) 0.051(9) 0.030(6) 0.000(6) -0.010(6) -0.004(7) N2 0.019(6) 0.043(7) 0.017(5) 0.001(5) -0.003(5) 0.012(6) N3 0.037(7) 0.037(8) 0.028(6) 0.000(6) 0.001(6) 0.000(7) O1 0.058(7) 0.058(7) 0.020(4) 0.008(5) 0.001(5) 0.009(6) O2 0.049(6) 0.049(6) 0.046(5) -0.013(6) -0.001(6) 0.032(6) O3 0.085(9) 0.055(7) 0.037(6) 0.010(6) -0.005(6) -0.022(7) C1 0.039(9) 0.022(8) 0.046(8) -0.011(7) -0.004(8) 0.001(8) C2 0.055(11) 0.023(9) 0.042(8) 0.004(7) 0.007(8) 0.007(9) C3 0.053(10) 0.024(9) 0.037(7) 0.002(7) 0.003(8) 0.009(9) C4 0.053(11) 0.029(9) 0.042(8) 0.005(8) 0.004(9) -0.011(9) C5 0.033(9) 0.048(10) 0.029(7) -0.002(8) 0.006(7) -0.002(9) C6 0.033(9) 0.065(12) 0.025(6) -0.010(8) 0.014(7) 0.002(9) C7 0.048(10) 0.039(9) 0.034(7) 0.012(7) 0.000(7) 0.012(9) C8 0.033(9) 0.035(9) 0.027(6) -0.008(7) 0.005(7) 0.007(9) C9 0.064(12) 0.031(9) 0.020(6) 0.011(6) 0.000(7) -0.001(9) C10 0.052(11) 0.033(9) 0.026(7) 0.012(7) -0.009(7) -0.012(9) C11 0.037(10) 0.041(9) 0.021(6) 0.004(7) 0.000(7) 0.010(9) C12 0.040(9) 0.028(8) 0.043(7) -0.002(7) -0.002(8) 0.001(9) C13 0.037(9) 0.033(9) 0.041(7) -0.007(7) -0.003(8) -0.004(8) C14 0.043(10) 0.037(9) 0.066(10) -0.009(9) 0.010(9) 0.002(9) C15 0.033(9) 0.036(9) 0.060(8) -0.022(9) -0.002(8) 0.004(8) C16 0.021(9) 0.060(11) 0.030(7) -0.015(8) 0.008(7) 0.007(10) C17 0.027(8) 0.043(10) 0.037(8) -0.016(9) 0.016(7) -0.009(8) C18 0.047(11) 0.058(12) 0.081(12) -0.010(10) 0.029(9) -0.024(10) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S1 O2 1.428(9) . ? S1 O1 1.465(8) . ? S1 N1 1.617(11) . ? S1 C1 1.752(8) . ? N1 C10 1.455(16) . ? N1 C7 1.520(15) . ? N2 C8 1.453(15) . ? N2 C9 1.455(14) . ? N2 C11 1.477(15) . ? N3 C17 1.344(17) . ? N3 C16 1.450(16) . ? N3 H3 0.88 . ? O3 C17 1.235(17) . ? C1 C2 1.39 . ? C1 C6 1.39 . ? C2 C3 1.39 . ? C2 H2 0.95 . ? C3 C4 1.39 . ? C3 H3 0.95 . ? C4 C5 1.39 . ? C4 C18 1.475(15) . ? C5 C6 1.39 . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 C8 1.520(18) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.548(19) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C16 1.513(17) . ? C11 C12 1.553(17) . ? C11 H11 1 . ? C12 C13 1.536(18) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C14 1.487(17) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.518(17) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 C16 1.540(19) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 H16 1 . ? C17 H17 0.95 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? 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 O2 S1 O1 119.3(6) . . ? O2 S1 N1 107.1(6) . . ? O1 S1 N1 105.6(6) . . ? O2 S1 C1 108.6(5) . . ? O1 S1 C1 107.4(5) . . ? N1 S1 C1 108.5(5) . . ? C10 N1 C7 109.4(10) . . ? C10 N1 S1 115.4(9) . . ? C7 N1 S1 116.1(9) . . ? C8 N2 C9 110.4(10) . . ? C8 N2 C11 112.6(10) . . ? C9 N2 C11 113.7(10) . . ? C17 N3 C16 124.6(12) . . ? C17 N3 H3 117.7 . . ? C16 N3 H3 117.7 . . ? C2 C1 C6 120 . . ? C2 C1 S1 121.3(5) . . ? C6 C1 S1 118.7(5) . . ? C3 C2 C1 120 . . ? C3 C2 H2 120 . . ? C1 C2 H2 120 . . ? C2 C3 C4 120 . . ? C2 C3 H3 120 . . ? C4 C3 H3 120 . . ? C3 C4 C5 120 . . ? C3 C4 C18 120.0(10) . . ? C5 C4 C18 119.8(10) . . ? C6 C5 C4 120 . . ? C6 C5 H5 120 . . ? C4 C5 H5 120 . . ? C5 C6 C1 120 . . ? C5 C6 H6 120 . . ? C1 C6 H6 120 . . ? C8 C7 N1 108.4(11) . . ? C8 C7 H7A 110 . . ? N1 C7 H7A 110 . . ? C8 C7 H7B 110 . . ? N1 C7 H7B 110 . . ? H7A C7 H7B 108.4 . . ? N2 C8 C7 110.4(11) . . ? N2 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? N2 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N2 C9 C10 108.4(11) . . ? N2 C9 H9A 110 . . ? C10 C9 H9A 110 . . ? N2 C9 H9B 110 . . ? C10 C9 H9B 110 . . ? H9A C9 H9B 108.4 . . ? N1 C10 C9 109.3(11) . . ? N1 C10 H10A 109.8 . . ? C9 C10 H10A 109.8 . . ? N1 C10 H10B 109.8 . . ? C9 C10 H10B 109.8 . . ? H10A C10 H10B 108.3 . . ? N2 C11 C16 111.8(11) . . ? N2 C11 C12 114.4(10) . . ? C16 C11 C12 109.5(11) . . ? N2 C11 H11 106.9 . . ? C16 C11 H11 106.9 . . ? C12 C11 H11 106.9 . . ? C13 C12 C11 111.6(11) . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 108 . . ? C14 C13 C12 112.7(12) . . ? C14 C13 H13A 109 . . ? C12 C13 H13A 109 . . ? C14 C13 H13B 109 . . ? C12 C13 H13B 109 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 111.2(13) . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C15 C14 H14B 109.4 . . ? H14A C14 H14B 108 . . ? C14 C15 C16 109.8(12) . . ? C14 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? C14 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N3 C16 C11 110.2(11) . . ? N3 C16 C15 106.8(10) . . ? C11 C16 C15 111.9(12) . . ? N3 C16 H16 109.3 . . ? C11 C16 H16 109.3 . . ? C15 C16 H16 109.3 . . ? O3 C17 N3 125.3(14) . . ? O3 C17 H17 117.4 . . ? N3 C17 H17 117.4 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 H3 O3 0.88 1.96 2.830(14) 170.3 3_665 # CIF produced by WinGX routine CIF_UPDATE # Created on 2002-10-15 at 12:27:57 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\wingx\files\archive.dat # CIF files read : src888 struct xabs2 data_src888 _database_code_CSD 195734 _audit_creation_date 2002-10-15T12:27:57-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H24 Cl2 N2 O2' _chemical_formula_sum 'C10 H24 Cl2 N2 O2' _chemical_formula_weight 275.21 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 7.9736(4) _cell_length_b 12.2913(6) _cell_length_c 14.1517(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1386.95(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3042 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 27.47 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.459 _exptl_absorpt_factor_muR 0.009 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56 Cubic fit to sin(theta)/lambda - 24 parameters ; _exptl_absorpt_correction_T_min 0.9075 _exptl_absorpt_correction_T_max 1.5446 _exptl_absorpt_correction_T_ave 1.0782 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0877 _diffrn_reflns_av_unetI/netI 0.1610 _diffrn_reflns_number 3042 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.972 _reflns_number_total 3042 _reflns_number_gt 1894 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'DIRDIF96 (Beurskens et al, 1996)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0289P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3042 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1171 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.083 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _refine_ls_shift/su_max 0.126 _refine_ls_shift/su_mean 0.01 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(9) _refine_diff_density_max 0.308 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.03634(13) 0.14683(7) 0.03879(7) 0.0281(3) Uani 1 1 d . . . Cl2 Cl 0.20233(13) 0.17020(7) -0.29195(7) 0.0270(3) Uani 1 1 d . . . N1 N 0.0129(4) 0.0145(2) -0.1471(3) 0.0192(8) Uani 1 1 d . . . N2 N 0.1819(5) -0.0800(3) -0.3216(2) 0.0211(8) Uani 1 1 d . . . O1 O -0.1478(3) 0.0165(2) -0.31703(18) 0.0258(7) Uani 1 1 d . . . O2 O -0.0555(5) 0.3897(3) 0.1177(3) 0.0366(8) Uani 1 1 d . . . C1 C 0.2349(5) -0.1082(3) -0.2226(3) 0.0187(9) Uani 1 1 d . . . H1 H 0.3269 -0.0574 -0.2037 0.022 Uiso 1 1 calc R . . C2 C 0.3044(6) -0.2237(3) -0.2208(3) 0.0253(10) Uani 1 1 d . . . H2A H 0.215 -0.2751 -0.24 0.03 Uiso 1 1 calc R . . H2B H 0.3969 -0.2297 -0.2672 0.03 Uiso 1 1 calc R . . C3 C 0.3689(5) -0.2553(3) -0.1236(3) 0.0271(10) Uani 1 1 d . . . H3A H 0.4063 -0.3321 -0.1244 0.033 Uiso 1 1 calc R . . H3B H 0.4666 -0.2093 -0.107 0.033 Uiso 1 1 calc R . . C4 C 0.2326(5) -0.2410(3) -0.0498(3) 0.0268(10) Uani 1 1 d . . . H4A H 0.2792 -0.2567 0.0136 0.032 Uiso 1 1 calc R . . H4B H 0.1411 -0.2935 -0.0621 0.032 Uiso 1 1 calc R . . C5 C 0.1623(5) -0.1259(3) -0.0514(3) 0.0223(10) Uani 1 1 d . . . H5A H 0.2518 -0.0736 -0.0345 0.027 Uiso 1 1 calc R . . H5B H 0.0716 -0.1194 -0.0039 0.027 Uiso 1 1 calc R . . C6 C 0.0931(5) -0.0983(3) -0.1496(3) 0.0200(9) Uani 1 1 d . . . H6 H 0.0042 -0.1526 -0.1658 0.024 Uiso 1 1 calc R . . C7 C -0.1779(5) 0.0135(3) -0.1504(3) 0.0282(11) Uani 1 1 d . . . H7A H -0.2209 -0.0313 -0.0976 0.034 Uiso 1 1 calc R . . H7B H -0.22 0.0886 -0.1417 0.034 Uiso 1 1 calc R . . C8 C -0.2448(5) -0.0314(3) -0.2428(3) 0.0281(11) Uani 1 1 d . . . H8A H -0.2338 -0.1116 -0.2442 0.034 Uiso 1 1 calc R . . H8B H -0.3648 -0.0124 -0.2503 0.034 Uiso 1 1 calc R . . C9 C -0.1037(5) -0.0556(3) -0.3925(3) 0.0261(10) Uani 1 1 d . . . H9A H -0.062 -0.0124 -0.4467 0.031 Uiso 1 1 calc R . . H9B H -0.205 -0.0954 -0.4134 0.031 Uiso 1 1 calc R . . C10 C 0.0307(5) -0.1373(3) -0.3629(3) 0.0231(9) Uani 1 1 d . . . H10A H -0.0165 -0.1879 -0.3154 0.028 Uiso 1 1 calc R . . H10B H 0.0656 -0.1806 -0.4185 0.028 Uiso 1 1 calc R . . H01 H 0.060(6) 0.055(3) -0.202(3) 0.060(15) Uiso 1 1 d . . . H02 H 0.285(5) -0.098(3) -0.366(3) 0.039(12) Uiso 1 1 d . . . H03 H -0.128(7) 0.364(5) 0.163(4) 0.09(2) Uiso 1 1 d . . . H04 H -0.034(6) 0.337(4) 0.088(4) 0.07(2) Uiso 1 1 d . . . H05 H 0.172(5) -0.007(4) -0.323(3) 0.036(13) Uiso 1 1 d . . . H06 H 0.035(5) 0.047(3) -0.082(3) 0.056(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0321(6) 0.0269(6) 0.0254(6) -0.0042(5) -0.0048(5) 0.0062(4) Cl2 0.0305(6) 0.0194(5) 0.0312(6) 0.0010(5) 0.0017(5) -0.0005(4) N1 0.023(2) 0.0167(17) 0.018(2) 0.0010(15) 0.0013(17) 0.0029(14) N2 0.027(2) 0.0167(19) 0.020(2) -0.0013(14) -0.0003(17) 0.0022(15) O1 0.0292(17) 0.0222(15) 0.0260(18) 0.0007(12) 0.0012(14) 0.0025(12) O2 0.042(2) 0.0277(19) 0.040(2) -0.0031(17) 0.0010(19) -0.0016(16) C1 0.018(2) 0.0198(18) 0.018(2) -0.0004(17) -0.0038(19) -0.0003(15) C2 0.033(3) 0.019(2) 0.024(3) -0.0044(17) -0.002(2) 0.0084(18) C3 0.028(3) 0.025(2) 0.028(3) 0.001(2) -0.002(2) 0.0082(18) C4 0.033(3) 0.023(2) 0.024(2) 0.004(2) -0.004(2) 0.0031(18) C5 0.026(2) 0.024(2) 0.018(2) 0.0014(18) 0.003(2) 0.0018(16) C6 0.021(2) 0.017(2) 0.022(2) -0.0024(17) 0.0044(19) 0.0008(16) C7 0.028(3) 0.024(2) 0.033(3) 0.0000(18) 0.005(2) 0.0040(19) C8 0.022(2) 0.026(2) 0.037(3) 0.0043(19) -0.001(2) -0.0024(17) C9 0.027(2) 0.028(2) 0.023(3) -0.002(2) -0.005(2) -0.0005(18) C10 0.024(2) 0.025(2) 0.020(2) -0.0014(17) 0.000(2) 0.0005(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C7 1.522(5) . ? N1 C6 1.527(4) . ? N1 H01 0.99(5) . ? N1 H06 1.02(5) . ? N2 C1 1.504(5) . ? N2 C10 1.514(5) . ? N2 H02 1.06(4) . ? N2 H05 0.90(4) . ? O1 C8 1.431(5) . ? O1 C9 1.432(5) . ? O2 H03 0.91(6) . ? O2 H04 0.79(5) . ? C1 C2 1.524(5) . ? C1 C6 1.537(5) . ? C1 H1 1 . ? C2 C3 1.520(5) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.517(5) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.522(5) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.534(5) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 H6 1 . ? C7 C8 1.516(5) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 C10 1.528(5) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? 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 C7 N1 C6 114.2(3) . . ? C7 N1 H01 111(3) . . ? C6 N1 H01 106(3) . . ? C7 N1 H06 102(2) . . ? C6 N1 H06 107(2) . . ? H01 N1 H06 116(3) . . ? C1 N2 C10 118.4(3) . . ? C1 N2 H02 107(2) . . ? C10 N2 H02 107(2) . . ? C1 N2 H05 106(2) . . ? C10 N2 H05 113(3) . . ? H02 N2 H05 105(3) . . ? C8 O1 C9 115.2(3) . . ? H03 O2 H04 103(5) . . ? N2 C1 C2 109.4(3) . . ? N2 C1 C6 113.7(3) . . ? C2 C1 C6 109.3(3) . . ? N2 C1 H1 108.1 . . ? C2 C1 H1 108.1 . . ? C6 C1 H1 108.1 . . ? C3 C2 C1 112.1(3) . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 110.5(3) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 111.2(3) . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108 . . ? C4 C5 C6 110.6(3) . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C5 109.3(3) . . ? N1 C6 C1 113.3(3) . . ? C5 C6 C1 109.1(3) . . ? N1 C6 H6 108.3 . . ? C5 C6 H6 108.3 . . ? C1 C6 H6 108.3 . . ? C8 C7 N1 112.4(3) . . ? C8 C7 H7A 109.1 . . ? N1 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? N1 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? O1 C8 C7 107.0(3) . . ? O1 C8 H8A 110.3 . . ? C7 C8 H8A 110.3 . . ? O1 C8 H8B 110.3 . . ? C7 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? O1 C9 C10 112.0(3) . . ? O1 C9 H9A 109.2 . . ? C10 C9 H9A 109.2 . . ? O1 C9 H9B 109.2 . . ? C10 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? N2 C10 C9 111.0(3) . . ? N2 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? N2 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108 . . ? 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 N1 H06 Cl1 1.02(5) 2.11(5) 3.099(4) 164(3) . N1 H01 Cl2 0.99(5) 2.22(5) 3.185(4) 164(4) . N1 H01 N2 0.99(5) 2.56(4) 3.043(5) 109(3) . N1 H01 O1 0.99(5) 2.37(4) 2.724(4) 100(3) . N2 H02 Cl1 1.06(4) 2.05(4) 3.103(4) 172(3) 4_554 N2 H05 Cl2 0.90(4) 2.24(4) 3.108(3) 163(3) . N2 H05 O1 0.90(4) 2.57(4) 2.884(5) 102(3) . O2 H04 Cl1 0.79(5) 2.51(6) 3.271(4) 163(5) . O2 H03 Cl2 0.91(6) 2.32(6) 3.217(4) 168(5) 2_455