# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_af009 _audit_creation_date 2013-03-04T17:07:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 2' _chemical_formula_moiety 'C10 H18 Cl2 N2' _chemical_formula_sum 'C10 H18 Cl2 N2' _chemical_formula_weight 237.16 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _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, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 13.29410(50) _cell_length_b 4.68840(20) _cell_length_c 21.03340(100) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1310.97 _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2575 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.464 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.7432 _exptl_absorpt_correction_T_max 0.7451 #----------------------------------------------------------------------------# # 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 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.474443E-1 _diffrn_orient_matrix_ub_12 0.157155 _diffrn_orient_matrix_ub_13 0.115575E-1 _diffrn_orient_matrix_ub_21 0.413234E-1 _diffrn_orient_matrix_ub_22 -0.137701 _diffrn_orient_matrix_ub_23 0.252032E-1 _diffrn_orient_matrix_ub_31 0.41227E-1 _diffrn_orient_matrix_ub_32 -0.42831E-1 _diffrn_orient_matrix_ub_33 -0.386213E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_unetI/netI 0.0733 _diffrn_reflns_number 5462 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 4.22 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.983 _reflns_number_total 2940 _reflns_number_gt 1788 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0497P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2940 _refine_ls_number_parameters 177 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0983 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1306 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.004 _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 0.21(11) _refine_diff_density_max 0.209 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # 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' 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 Cl12 Cl 0.07515(6) 0.0722(2) 0.31940(5) 0.0946(4) Uani 1 1 d . . . Cl7 Cl 0.34040(7) 0.1284(3) 0.57522(5) 0.1031(4) Uani 1 1 d . . . N1 N 0.30863(15) 0.2219(5) 0.31733(11) 0.0527(6) Uani 1 1 d . . . N4 N 0.44013(16) -0.0694(5) 0.44578(11) 0.0577(6) Uani 1 1 d . . . C2 C 0.3445(2) 0.0355(6) 0.35399(14) 0.0505(6) Uani 1 1 d . . . C10 C 0.2573(2) 0.1277(8) 0.25983(13) 0.0549(7) Uani 1 1 d . . . C5 C 0.5015(2) 0.0237(6) 0.49893(15) 0.0575(7) Uani 1 1 d . . . C3 C 0.40300(19) 0.1206(7) 0.41022(13) 0.0519(6) Uani 1 1 d . . . C13 C 0.3131(3) 0.2411(9) 0.20163(17) 0.0742(9) Uani 1 1 d D . . C6 C 0.4526(3) -0.0704(9) 0.55948(17) 0.0720(9) Uani 1 1 d . . . C8 C 0.6073(3) -0.1124(11) 0.4908(2) 0.0809(10) Uani 1 1 d D . . C9 C 0.6821(2) -0.0278(10) 0.54127(18) 0.0941(12) Uani 1 1 d . . . H9A H 0.7557(18) -0.136(3) 0.5319(3) 0.141 Uiso 1 1 calc R . . H9B H 0.6531(7) -0.0936(18) 0.5891(12) 0.141 Uiso 1 1 calc R . . H9C H 0.6929(4) 0.209(6) 0.54033(18) 0.141 Uiso 1 1 calc R . . C11 C 0.1505(3) 0.2382(10) 0.25957(18) 0.0739(9) Uani 1 1 d . . . C14 C 0.4152(3) 0.1000(10) 0.19160(18) 0.0970(12) Uani 1 1 d . . . H14A H 0.4459(9) 0.177(2) 0.1559(9) 0.145 Uiso 1 1 calc R . . H14B H 0.4065(3) -0.095(5) 0.1859(2) 0.145 Uiso 1 1 calc R . . H14C H 0.4554(11) 0.1315(12) 0.2269(9) 0.145 Uiso 1 1 calc R . . H2 H 0.339(2) -0.165(7) 0.3460(12) 0.054(7) Uiso 1 1 d . . . H10 H 0.2575(19) -0.066(7) 0.2565(11) 0.044(7) Uiso 1 1 d . . . H5 H 0.504(2) 0.227(8) 0.4993(16) 0.072(9) Uiso 1 1 d . . . H6A H 0.496(2) -0.031(7) 0.5996(15) 0.080(9) Uiso 1 1 d . . . H6B H 0.434(3) -0.246(8) 0.5579(15) 0.067(10) Uiso 1 1 d . . . H8B H 0.641(3) -0.024(8) 0.4536(13) 0.090(12) Uiso 1 1 d D . . H3 H 0.4122(19) 0.324(6) 0.4181(11) 0.048(7) Uiso 1 1 d . . . H13B H 0.266(3) 0.224(7) 0.1679(16) 0.093(12) Uiso 1 1 d . . . H13A H 0.324(3) 0.442(4) 0.2054(19) 0.116(15) Uiso 1 1 d D . . H11B H 0.147(3) 0.453(11) 0.272(2) 0.120(14) Uiso 1 1 d . . . H8A H 0.594(3) -0.309(12) 0.498(2) 0.133(17) Uiso 1 1 d . . . H11A H 0.116(3) 0.224(10) 0.218(2) 0.117(14) 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 Cl12 0.0645(5) 0.1191(8) 0.1004(7) -0.0213(6) 0.0103(5) -0.0188(5) Cl7 0.0810(6) 0.1330(9) 0.0954(7) 0.0165(7) 0.0167(5) -0.0023(6) N1 0.0511(12) 0.0547(13) 0.0521(13) -0.0023(12) -0.0022(11) -0.0039(10) N4 0.0553(13) 0.0573(14) 0.0604(13) 0.0010(12) -0.0093(11) -0.0079(12) C2 0.0454(13) 0.0503(16) 0.0559(16) 0.0005(13) 0.0016(12) -0.0028(12) C10 0.0585(16) 0.0529(18) 0.0533(16) -0.0032(14) -0.0074(13) -0.0047(14) C5 0.0576(15) 0.0498(16) 0.0651(18) 0.0008(14) -0.0133(14) -0.0082(13) C3 0.0428(13) 0.0577(18) 0.0551(17) -0.0001(14) 0.0018(11) -0.0037(13) C13 0.081(2) 0.087(3) 0.0546(19) 0.0061(18) -0.0032(17) -0.0148(19) C6 0.073(2) 0.068(2) 0.075(2) 0.0111(19) -0.0132(16) -0.0101(18) C8 0.0629(19) 0.081(3) 0.099(3) -0.006(2) -0.0176(19) -0.0005(19) C9 0.0590(19) 0.120(3) 0.103(3) -0.006(3) -0.0170(18) -0.001(2) C11 0.0595(18) 0.090(3) 0.072(2) -0.005(2) -0.0101(17) 0.0012(18) C14 0.090(2) 0.106(3) 0.095(3) 0.002(2) 0.029(2) -0.009(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl12 C11 1.787(4) . ? Cl7 C6 1.790(4) . ? N1 C2 1.259(3) . ? N1 C10 1.457(3) . ? N4 C3 1.264(4) . ? N4 C5 1.451(4) . ? C2 C3 1.471(4) . ? C2 H2 0.96(3) . ? C10 C11 1.511(5) . ? C10 C13 1.527(5) . ? C10 H10 0.91(3) . ? C5 C6 1.495(5) . ? C5 C8 1.554(5) . ? C5 H5 0.95(3) . ? C3 H3 0.98(3) . ? C13 C14 1.524(6) . ? C13 H13B 0.95(4) . ? C13 H13A 0.957(19) . ? C6 H6A 1.04(3) . ? C6 H6B 0.86(4) . ? C8 C9 1.508(5) . ? C8 H8B 0.996(18) . ? C8 H8A 0.95(5) . ? C9 H9A 1.1202 . ? C9 H9B 1.1202 . ? C9 H9C 1.1202 . ? C11 H11B 1.04(5) . ? C11 H11A 1.00(4) . ? C14 H14A 0.9273 . ? C14 H14B 0.9273 . ? C14 H14C 0.9273 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C10 118.4(2) . . ? C3 N4 C5 117.6(2) . . ? N1 C2 C3 120.3(3) . . ? N1 C2 H2 123.2(17) . . ? C3 C2 H2 116.4(16) . . ? N1 C10 C11 109.8(3) . . ? N1 C10 C13 109.4(3) . . ? C11 C10 C13 109.5(3) . . ? N1 C10 H10 111.5(15) . . ? C11 C10 H10 110.1(16) . . ? C13 C10 H10 106.5(15) . . ? N4 C5 C6 108.9(3) . . ? N4 C5 C8 107.5(3) . . ? C6 C5 C8 111.4(3) . . ? N4 C5 H5 109(2) . . ? C6 C5 H5 108(2) . . ? C8 C5 H5 112.4(19) . . ? N4 C3 C2 119.4(3) . . ? N4 C3 H3 122.7(14) . . ? C2 C3 H3 117.8(14) . . ? C14 C13 C10 113.1(3) . . ? C14 C13 H13B 117(2) . . ? C10 C13 H13B 104(2) . . ? C14 C13 H13A 108(3) . . ? C10 C13 H13A 110(3) . . ? H13B C13 H13A 104(3) . . ? C5 C6 Cl7 111.4(2) . . ? C5 C6 H6A 113.2(18) . . ? Cl7 C6 H6A 102.9(18) . . ? C5 C6 H6B 112(2) . . ? Cl7 C6 H6B 106(2) . . ? H6A C6 H6B 111(3) . . ? C9 C8 C5 114.3(3) . . ? C9 C8 H8B 98(2) . . ? C5 C8 H8B 109(2) . . ? C9 C8 H8A 106(3) . . ? C5 C8 H8A 102(3) . . ? H8B C8 H8A 128(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C10 C11 Cl12 112.0(3) . . ? C10 C11 H11B 112(3) . . ? Cl12 C11 H11B 103(2) . . ? C10 C11 H11A 114(2) . . ? Cl12 C11 H11A 110(2) . . ? H11B C11 H11A 105(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 N1 C2 C3 175.7(2) . . . . ? C2 N1 C10 C11 121.7(3) . . . . ? C2 N1 C10 C13 -118.1(3) . . . . ? C3 N4 C5 C6 117.9(3) . . . . ? C3 N4 C5 C8 -121.3(3) . . . . ? C5 N4 C3 C2 177.0(2) . . . . ? N1 C2 C3 N4 -178.6(3) . . . . ? N1 C10 C13 C14 69.7(4) . . . . ? C11 C10 C13 C14 -169.9(3) . . . . ? N4 C5 C6 Cl7 -70.9(3) . . . . ? C8 C5 C6 Cl7 170.7(3) . . . . ? N4 C5 C8 C9 177.8(3) . . . . ? C6 C5 C8 C9 -62.9(5) . . . . ? N1 C10 C11 Cl12 -68.7(3) . . . . ? C13 C10 C11 Cl12 171.1(3) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 960655' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_af409 _audit_creation_date 2012-12-03T13:21:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 3' _chemical_formula_moiety 'C20 H22 Cl2 N2' _chemical_formula_sum 'C20 H22 Cl2 N2' _chemical_formula_weight 361.3 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.62180(20) _cell_length_b 26.63630(110) _cell_length_c 6.83100(20) _cell_angle_alpha 90.0000 _cell_angle_beta 113.8983(20) _cell_angle_gamma 90.0000 _cell_volume 935.20(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 22688 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.225 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.35 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.983 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.133806 _diffrn_orient_matrix_ub_12 -0.24729E-1 _diffrn_orient_matrix_ub_13 0.66E-4 _diffrn_orient_matrix_ub_21 0.1401 _diffrn_orient_matrix_ub_22 -0.212354E-1 _diffrn_orient_matrix_ub_23 0.105546 _diffrn_orient_matrix_ub_31 -0.01792 _diffrn_orient_matrix_ub_32 0.186277E-1 _diffrn_orient_matrix_ub_33 0.120409 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_unetI/netI 0.0459 _diffrn_reflns_number 6597 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.971 _reflns_number_total 2908 _reflns_number_gt 2618 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0282P)^2^+0.4729P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 2908 _refine_ls_number_parameters 305 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0 _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 0.09(6) _refine_diff_density_max 0.24 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.05 #----------------------------------------------------------------------------# # 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' 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 Cl1 Cl 0.29214(17) 0.20097(3) -0.33576(11) 0.0383(2) Uani 1 1 d . . . Cl2 Cl 0.95965(17) 0.37633(4) 0.41225(12) 0.0453(2) Uani 1 1 d . . . C19 C 0.7216(7) 0.30693(14) 0.8425(5) 0.0336(7) Uani 1 1 d . . . C6 C -0.2661(6) 0.10875(12) -0.4997(4) 0.0285(7) Uani 1 1 d . . . C7 C 0.0653(6) 0.16808(12) -0.2533(4) 0.0257(6) Uani 1 1 d . . . C1 C -0.0064(6) 0.11859(11) -0.3708(4) 0.0247(6) Uani 1 1 d . . . C18 C 0.8301(6) 0.43168(13) 0.8079(5) 0.0322(7) Uani 1 1 d . . . C5 C -0.3344(6) 0.06393(13) -0.6140(5) 0.0318(7) Uani 1 1 d . . . C2 C 0.1798(6) 0.08299(12) -0.3561(5) 0.0290(6) Uani 1 1 d . . . C4 C -0.1494(7) 0.02924(13) -0.6012(5) 0.0341(8) Uani 1 1 d . . . N2 N 0.6945(5) 0.28170(10) 0.4938(4) 0.0345(6) Uani 1 1 d . . . C13 C 1.0208(6) 0.39754(12) 0.8178(4) 0.0285(6) Uani 1 1 d . . . C12 C 0.9637(6) 0.35352(13) 0.6654(4) 0.0309(7) Uani 1 1 d . . . C16 C 1.1377(7) 0.47674(15) 1.1080(5) 0.0378(8) Uani 1 1 d . . . C11 C 0.7141(6) 0.32565(13) 0.6271(5) 0.0316(7) Uani 1 1 d . . . C17 C 0.8886(7) 0.47111(13) 0.9537(5) 0.0359(8) Uani 1 1 d . . . C3 C 0.1094(7) 0.03865(13) -0.4699(5) 0.0335(7) Uani 1 1 d . . . C9 C 0.4448(6) 0.22669(13) 0.2155(4) 0.0318(7) Uani 1 1 d . . . C14 C 1.2702(6) 0.40324(13) 0.9760(4) 0.0347(7) Uani 1 1 d . . . C15 C 1.3290(7) 0.44312(15) 1.1200(5) 0.0401(8) Uani 1 1 d . . . C10 C 0.4808(6) 0.27367(13) 0.3362(4) 0.0304(7) Uani 1 1 d . . . N1 N 0.2194(5) 0.21311(10) 0.0855(3) 0.0322(6) Uani 1 1 d . . . C8 C 0.1874(6) 0.16313(12) -0.0080(4) 0.0266(6) Uani 1 1 d . . . C20 C 0.0069(7) 0.13384(15) 0.0658(5) 0.0349(8) Uani 1 1 d . . . H17 H 0.741(8) 0.4934(15) 0.947(6) 0.049(10) Uiso 1 1 d . . . H3 H 0.234(5) 0.0166(11) -0.457(4) 0.011(7) Uiso 1 1 d . . . H14 H 1.406(6) 0.3802(15) 0.981(5) 0.034(8) Uiso 1 1 d . . . H8 H 0.356(6) 0.1465(12) 0.037(5) 0.027(8) Uiso 1 1 d . . . H12 H 1.104(6) 0.3316(12) 0.712(5) 0.026(8) Uiso 1 1 d . . . H7 H -0.091(5) 0.1893(10) -0.302(4) 0.013(7) Uiso 1 1 d . . . H4 H -0.200(6) -0.0010(12) -0.675(4) 0.021(7) Uiso 1 1 d . . . H16 H 1.178(7) 0.5067(15) 1.202(6) 0.048(10) Uiso 1 1 d . . . H6 H -0.393(6) 0.1357(13) -0.514(5) 0.026(8) Uiso 1 1 d . . . H2 H 0.370(7) 0.0918(13) -0.269(6) 0.042(9) Uiso 1 1 d . . . H5 H -0.510(7) 0.0573(16) -0.698(6) 0.051(10) Uiso 1 1 d . . . H10 H 0.334(6) 0.2931(12) 0.304(5) 0.029(8) Uiso 1 1 d . . . H11 H 0.566(6) 0.3473(13) 0.566(5) 0.034(9) Uiso 1 1 d . . . H20A H -0.031(6) 0.0984(14) 0.010(5) 0.032(9) Uiso 1 1 d . . . H20B H 0.081(6) 0.1335(13) 0.227(5) 0.037(9) Uiso 1 1 d . . . H20C H -0.146(7) 0.1491(13) 0.013(5) 0.030(9) Uiso 1 1 d . . . H19A H 0.867(7) 0.2848(13) 0.906(5) 0.030(8) Uiso 1 1 d . . . H19C H 0.763(7) 0.3369(14) 0.947(5) 0.040(9) Uiso 1 1 d . . . H19B H 0.560(6) 0.2869(13) 0.819(5) 0.032(8) Uiso 1 1 d . . . H15 H 1.504(8) 0.4501(18) 1.214(6) 0.062(12) Uiso 1 1 d . . . H18 H 0.653(6) 0.4278(13) 0.708(5) 0.033(9) Uiso 1 1 d . . . H9 H 0.599(6) 0.2063(13) 0.250(5) 0.028(8) 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 0.0496(5) 0.0364(4) 0.0353(4) -0.0039(4) 0.0237(3) -0.0115(4) Cl2 0.0521(5) 0.0570(6) 0.0302(4) -0.0055(4) 0.0203(3) -0.0016(5) C19 0.0375(19) 0.0281(17) 0.0338(16) -0.0053(14) 0.0131(15) -0.0022(16) C6 0.0302(16) 0.0315(17) 0.0229(13) -0.0009(12) 0.0098(12) 0.0006(14) C7 0.0253(14) 0.0307(16) 0.0206(12) 0.0003(12) 0.0089(11) -0.0007(13) C1 0.0303(14) 0.0285(16) 0.0146(11) -0.0021(11) 0.0085(10) -0.0034(12) C18 0.0320(17) 0.0313(18) 0.0310(15) 0.0006(14) 0.0103(14) 0.0024(14) C5 0.0324(17) 0.0328(18) 0.0239(14) -0.0023(13) 0.0048(13) -0.0077(15) C2 0.0288(16) 0.0332(17) 0.0252(13) -0.0007(12) 0.0111(12) -0.0006(13) C4 0.049(2) 0.0312(19) 0.0239(14) -0.0065(14) 0.0166(14) -0.0094(17) N2 0.0341(14) 0.0333(15) 0.0289(12) -0.0094(11) 0.0052(11) -0.0001(12) C13 0.0321(15) 0.0296(16) 0.0232(12) -0.0017(12) 0.0106(11) -0.0018(13) C12 0.0289(15) 0.0368(19) 0.0247(13) -0.0053(13) 0.0084(12) 0.0037(14) C16 0.052(2) 0.0353(19) 0.0277(15) -0.0079(14) 0.0174(15) -0.0087(16) C11 0.0267(15) 0.0342(17) 0.0282(14) -0.0065(13) 0.0052(12) 0.0048(14) C17 0.048(2) 0.0291(18) 0.0349(16) 0.0008(14) 0.0210(15) 0.0031(16) C3 0.0407(18) 0.0324(19) 0.0314(15) -0.0002(13) 0.0188(14) 0.0073(15) C9 0.0349(17) 0.0356(19) 0.0220(13) -0.0011(13) 0.0084(13) 0.0021(14) C14 0.0300(17) 0.0399(19) 0.0289(14) -0.0074(14) 0.0063(13) 0.0010(15) C15 0.041(2) 0.041(2) 0.0321(16) -0.0102(15) 0.0083(15) -0.0054(17) C10 0.0306(16) 0.0327(18) 0.0253(13) -0.0033(13) 0.0086(12) 0.0016(14) N1 0.0333(14) 0.0380(17) 0.0198(10) -0.0075(10) 0.0051(10) 0.0002(11) C8 0.0270(15) 0.0302(16) 0.0179(12) -0.0040(11) 0.0042(11) -0.0012(13) C20 0.041(2) 0.042(2) 0.0212(14) -0.0026(14) 0.0117(14) -0.0049(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C7 1.815(3) . ? Cl2 C12 1.824(3) . ? C19 C11 1.538(4) . ? C19 H19A 0.96(4) . ? C19 H19C 1.03(4) . ? C19 H19B 1.01(3) . ? C6 C1 1.391(4) . ? C6 C5 1.393(4) . ? C6 H6 0.99(3) . ? C7 C1 1.511(4) . ? C7 C8 1.538(3) . ? C7 H7 0.98(3) . ? C1 C2 1.386(4) . ? C18 C17 1.392(5) . ? C18 C13 1.386(4) . ? C18 H18 0.96(3) . ? C5 C4 1.368(5) . ? C5 H5 0.94(4) . ? C2 C3 1.381(4) . ? C2 H2 1.02(4) . ? C4 C3 1.388(5) . ? C4 H4 0.93(3) . ? N2 C10 1.266(4) . ? N2 C11 1.460(4) . ? C13 C14 1.389(4) . ? C13 C12 1.514(4) . ? C12 C11 1.514(5) . ? C12 H12 0.93(3) . ? C16 C17 1.378(5) . ? C16 C15 1.376(5) . ? C16 H16 0.99(4) . ? C11 H11 0.96(3) . ? C17 H17 1.01(4) . ? C3 H3 0.89(3) . ? C9 N1 1.270(4) . ? C9 C10 1.466(4) . ? C9 H9 0.97(3) . ? C14 C15 1.394(5) . ? C14 H14 0.97(4) . ? C15 H15 0.95(4) . ? C10 H10 0.92(3) . ? N1 C8 1.456(4) . ? C8 C20 1.519(5) . ? C8 H8 0.98(3) . ? C20 H20A 1.01(4) . ? C20 H20B 1.01(3) . ? C20 H20C 0.88(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C19 H19A 108.9(19) . . ? C11 C19 H19C 108.9(19) . . ? H19A C19 H19C 104(3) . . ? C11 C19 H19B 110.0(17) . . ? H19A C19 H19B 107(3) . . ? H19C C19 H19B 117(3) . . ? C1 C6 C5 119.8(3) . . ? C1 C6 H6 117.1(18) . . ? C5 C6 H6 122.9(18) . . ? C1 C7 C8 114.2(2) . . ? C1 C7 Cl1 109.03(19) . . ? C8 C7 Cl1 108.7(2) . . ? C1 C7 H7 108.3(15) . . ? C8 C7 H7 111.1(14) . . ? Cl1 C7 H7 105.2(15) . . ? C6 C1 C2 119.0(3) . . ? C6 C1 C7 119.1(3) . . ? C2 C1 C7 121.8(3) . . ? C17 C18 C13 120.4(3) . . ? C17 C18 H18 118(2) . . ? C13 C18 H18 122(2) . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 120(3) . . ? C6 C5 H5 119(3) . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2 121(2) . . ? C1 C2 H2 118(2) . . ? C5 C4 C3 119.3(3) . . ? C5 C4 H4 119.5(19) . . ? C3 C4 H4 121.1(19) . . ? C10 N2 C11 118.2(3) . . ? C18 C13 C14 118.9(3) . . ? C18 C13 C12 122.0(3) . . ? C14 C13 C12 119.1(3) . . ? C13 C12 C11 114.9(2) . . ? C13 C12 Cl2 108.2(2) . . ? C11 C12 Cl2 110.2(2) . . ? C13 C12 H12 110(2) . . ? C11 C12 H12 111(2) . . ? Cl2 C12 H12 102.5(18) . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 118(2) . . ? C15 C16 H16 121(2) . . ? N2 C11 C12 109.3(2) . . ? N2 C11 C19 107.6(3) . . ? C12 C11 C19 109.2(2) . . ? N2 C11 H11 112(2) . . ? C12 C11 H11 111(2) . . ? C19 C11 H11 106.9(19) . . ? C16 C17 C18 120.1(3) . . ? C16 C17 H17 122(2) . . ? C18 C17 H17 118(2) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 121.5(18) . . ? C2 C3 H3 118.2(18) . . ? N1 C9 C10 120.5(3) . . ? N1 C9 H9 123.6(19) . . ? C10 C9 H9 115.8(19) . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H14 120(2) . . ? C13 C14 H14 119.4(19) . . ? C16 C15 C14 119.9(3) . . ? C16 C15 H15 119(3) . . ? C14 C15 H15 121(3) . . ? N2 C10 C9 119.3(3) . . ? N2 C10 H10 123.9(19) . . ? C9 C10 H10 116.0(19) . . ? C9 N1 C8 118.6(3) . . ? N1 C8 C20 107.7(2) . . ? N1 C8 C7 108.7(2) . . ? C20 C8 C7 110.0(2) . . ? N1 C8 H8 110.2(19) . . ? C20 C8 H8 110.8(19) . . ? C7 C8 H8 109.3(17) . . ? C8 C20 H20A 114.9(18) . . ? C8 C20 H20B 109(2) . . ? H20A C20 H20B 110(3) . . ? C8 C20 H20C 107(2) . . ? H20A C20 H20C 105(3) . . ? H20B C20 H20C 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C6 C1 C2 -1.0(4) . . . . ? C5 C6 C1 C7 178.1(3) . . . . ? C8 C7 C1 C6 117.3(3) . . . . ? Cl1 C7 C1 C6 -121.0(2) . . . . ? C8 C7 C1 C2 -63.6(3) . . . . ? Cl1 C7 C1 C2 58.1(3) . . . . ? C1 C6 C5 C4 0.1(4) . . . . ? C6 C1 C2 C3 0.9(4) . . . . ? C7 C1 C2 C3 -178.2(3) . . . . ? C6 C5 C4 C3 1.0(5) . . . . ? C17 C18 C13 C14 0.3(4) . . . . ? C17 C18 C13 C12 178.6(3) . . . . ? C18 C13 C12 C11 -43.8(4) . . . . ? C14 C13 C12 C11 134.6(3) . . . . ? C18 C13 C12 Cl2 79.8(3) . . . . ? C14 C13 C12 Cl2 -101.9(3) . . . . ? C10 N2 C11 C12 -133.1(3) . . . . ? C10 N2 C11 C19 108.4(3) . . . . ? C13 C12 C11 N2 -174.9(2) . . . . ? Cl2 C12 C11 N2 62.6(3) . . . . ? C13 C12 C11 C19 -57.3(4) . . . . ? Cl2 C12 C11 C19 -179.8(2) . . . . ? C15 C16 C17 C18 -0.7(5) . . . . ? C13 C18 C17 C16 0.6(5) . . . . ? C5 C4 C3 C2 -1.1(5) . . . . ? C1 C2 C3 C4 0.2(5) . . . . ? C18 C13 C14 C15 -1.1(5) . . . . ? C12 C13 C14 C15 -179.5(3) . . . . ? C17 C16 C15 C14 -0.2(5) . . . . ? C13 C14 C15 C16 1.1(5) . . . . ? C11 N2 C10 C9 -172.5(3) . . . . ? N1 C9 C10 N2 166.1(3) . . . . ? C10 C9 N1 C8 -171.5(3) . . . . ? C9 N1 C8 C20 117.0(3) . . . . ? C9 N1 C8 C7 -123.8(3) . . . . ? C1 C7 C8 N1 -173.5(2) . . . . ? Cl1 C7 C8 N1 64.6(3) . . . . ? C1 C7 C8 C20 -55.8(3) . . . . ? Cl1 C7 C8 C20 -177.7(2) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 960656' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_af402 _audit_creation_date 2013-09-11T14:49:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 3' _chemical_formula_moiety 'C20 H22 Cl2 N2' _chemical_formula_sum 'C20 H22 Cl2 N2' _chemical_formula_weight 359.28 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pcab _symmetry_space_group_name_Hall '-P 2bc 2ac' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y+1/2, z' '-x, -y+1/2, z+1/2' '-x, -y, -z' 'x-1/2, -y, -z-1/2' '-x-1/2, y-1/2, -z' 'x, y-1/2, -z-1/2' _cell_length_a 13.73710(4) _cell_length_b 6.92200(20) _cell_length_c 20.09850(59) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_volume 1911.069 _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 15366 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.994 _exptl_absorpt_correction_T_max 0.995 #----------------------------------------------------------------------------# # 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 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.615722E-1 _diffrn_orient_matrix_ub_12 -0.768109E-1 _diffrn_orient_matrix_ub_13 -0.22372E-2 _diffrn_orient_matrix_ub_21 -0.363116E-1 _diffrn_orient_matrix_ub_22 0.118055 _diffrn_orient_matrix_ub_23 -0.144108E-1 _diffrn_orient_matrix_ub_31 0.137675E-1 _diffrn_orient_matrix_ub_32 -0.321514E-1 _diffrn_orient_matrix_ub_33 -0.475698E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_unetI/netI 0.0308 _diffrn_reflns_number 17638 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.49 _diffrn_reflns_theta_max 27.54 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _reflns_number_total 2159 _reflns_number_gt 1534 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.25(13) _refine_ls_number_reflns 2159 _refine_ls_number_parameters 95 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2867 _refine_ls_R_factor_gt 0.2517 _refine_ls_wR_factor_ref 0.6407 _refine_ls_wR_factor_gt 0.6082 _refine_ls_goodness_of_fit_ref 2.986 _refine_ls_restrained_S_all 2.986 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.454 _refine_diff_density_min -1.204 _refine_diff_density_rms 0.208 #----------------------------------------------------------------------------# # 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 0.003 0.002 '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 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.148 0.159 '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 C9 C 0.5420(5) 0.4503(11) 0.4839(4) 0.065(2) Uani 1 1 d . . . H9 H 0.5984 0.5178 0.4734 0.078 Uiso 1 1 calc . . . C2 C 0.6686(7) -0.2527(15) 0.3464(5) 0.075(3) Uani 1 1 d . . . H2 H 0.6071 -0.3074 0.3513 0.09 Uiso 1 1 calc R . . C4 C 0.8332(7) -0.2841(15) 0.3102(4) 0.079(3) Uani 1 1 d . . . H4 H 0.8819 -0.3563 0.2898 0.095 Uiso 1 1 calc R . . C3 C 0.7416(7) -0.3548(13) 0.3150(5) 0.075(3) Uani 1 1 d . . . H3 H 0.7275 -0.475 0.2967 0.09 Uiso 1 1 calc R . . C1 C 0.6861(6) -0.0730(12) 0.3702(5) 0.078(3) Uani 1 1 d . . . C5 C 0.8536(6) -0.1037(15) 0.3360(4) 0.073(3) Uani 1 1 d . . . H5 H 0.9163 -0.0539 0.3337 0.087 Uiso 1 1 calc R . . C6 C 0.7803(6) 0.0017(13) 0.3651(5) 0.078(3) Uani 1 1 d . . . H6 H 0.7936 0.1244 0.3816 0.093 Uiso 1 1 calc R . . N1 N 0.5345(6) 0.2697(13) 0.4712(7) 0.111(4) Uani 1 1 d . . . C7 C 0.6046(7) 0.0486(13) 0.4038(8) 0.120(6) Uani 1 1 d . . . H7 H 0.5545 -0.0393 0.4207 0.144 Uiso 1 1 calc R . . C8 C 0.6282(7) 0.1727(14) 0.4518(5) 0.079(3) Uiso 1 1 d . . . H8 H 0.6761 0.2671 0.4361 0.095 Uiso 1 1 calc R . . C10 C 0.6690(3) 0.0528(6) 0.5127(2) 0.0263(15) Uiso 1 1 d . . . H10A H 0.6848 0.1391 0.5485 0.039 Uiso 1 1 calc R . . H10B H 0.7265 -0.0158 0.4993 0.039 Uiso 1 1 calc R . . H10C H 0.6206 -0.0377 0.5273 0.039 Uiso 1 1 calc R . . Cl1 Cl 0.5495(2) 0.1982(5) 0.32842(17) 0.1060(19) 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 C9 0.047(4) 0.054(4) 0.093(6) -0.021(4) 0.021(3) 0.006(3) C2 0.072(5) 0.070(5) 0.084(6) -0.007(4) 0.008(4) -0.004(4) C4 0.088(7) 0.091(7) 0.057(5) -0.006(4) 0.017(4) 0.022(5) C3 0.077(6) 0.072(5) 0.075(5) -0.015(4) -0.002(4) 0.017(4) C1 0.067(5) 0.051(4) 0.115(7) -0.010(4) 0.032(5) 0.009(3) C5 0.050(4) 0.087(6) 0.081(5) 0.007(5) 0.016(3) 0.011(4) C6 0.064(5) 0.053(4) 0.116(7) -0.020(4) 0.036(5) -0.006(3) N1 0.057(4) 0.085(6) 0.191(10) -0.065(6) 0.056(6) -0.016(3) C7 0.062(6) 0.053(5) 0.245(17) -0.042(7) 0.033(8) 0.001(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 N1 1.280(11) . ? C9 C9 1.490(13) 5_666 ? C9 H9 0.93 . ? C2 C1 1.354(14) . ? C2 C3 1.380(13) . ? C2 H2 0.93 . ? C4 C3 1.354(14) . ? C4 C5 1.381(15) . ? C4 H4 0.93 . ? C3 H3 0.93 . ? C1 C6 1.397(12) . ? C1 C7 1.555(12) . ? C5 C6 1.373(11) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? N1 C8 1.503(12) . ? C7 C8 1.332(16) . ? C7 Cl1 1.985(16) . ? C7 H7 0.98 . ? C8 C10 1.582(10) . ? C8 H8 0.98 . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? 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 C9 C9 118.4(9) . 5_666 ? N1 C9 H9 120.8 . . ? C9 C9 H9 120.8 5_666 . ? C1 C2 C3 120.2(9) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C3 C4 C5 119.2(8) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C3 C2 121.6(9) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C2 C1 C6 118.6(8) . . ? C2 C1 C7 121.5(8) . . ? C6 C1 C7 119.9(8) . . ? C6 C5 C4 119.5(8) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 120.9(8) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C9 N1 C8 114.8(7) . . ? C8 C7 C1 119.2(10) . . ? C8 C7 Cl1 108.0(8) . . ? C1 C7 Cl1 103.1(10) . . ? C8 C7 H7 108.7 . . ? C1 C7 H7 108.7 . . ? Cl1 C7 H7 108.7 . . ? C7 C8 N1 105.5(9) . . ? C7 C8 C10 108.0(9) . . ? N1 C8 C10 109.7(8) . . ? C7 C8 H8 111.1 . . ? N1 C8 H8 111.1 . . ? C10 C8 H8 111.1 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C4 C3 C2 -1.5(14) . . . . ? C1 C2 C3 C4 3.6(16) . . . . ? C3 C2 C1 C6 -3.1(16) . . . . ? C3 C2 C1 C7 177.9(11) . . . . ? C3 C4 C5 C6 -1.0(14) . . . . ? C4 C5 C6 C1 1.4(15) . . . . ? C2 C1 C6 C5 0.6(16) . . . . ? C7 C1 C6 C5 179.6(12) . . . . ? C9 C9 N1 C8 -168.3(11) 5_666 . . . ? C2 C1 C7 C8 148.8(12) . . . . ? C6 C1 C7 C8 -30.2(19) . . . . ? C2 C1 C7 Cl1 -91.7(11) . . . . ? C6 C1 C7 Cl1 89.4(12) . . . . ? C1 C7 C8 N1 178.0(10) . . . . ? Cl1 C7 C8 N1 61.0(10) . . . . ? C1 C7 C8 C10 -64.7(14) . . . . ? Cl1 C7 C8 C10 178.2(5) . . . . ? C9 N1 C8 C7 -141.2(13) . . . . ? C9 N1 C8 C10 102.7(12) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 960657' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_af172al _audit_creation_date 2013-06-29T21:58:08-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 10' _chemical_formula_moiety 'C11 H23 Al Cl N2, C H3 Al Cl3' _chemical_formula_sum 'C12 H26 Al2 Cl4 N2' _chemical_formula_weight 394.11 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6141(3) _cell_length_b 17.4168(5) _cell_length_c 21.0756(8) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 4263.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5181 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1648 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.631 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_T_max 0.862 #----------------------------------------------------------------------------# # 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 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.31155E-1 _diffrn_orient_matrix_ub_12 0.5143E-3 _diffrn_orient_matrix_ub_13 -0.442312E-1 _diffrn_orient_matrix_ub_21 -0.801889E-1 _diffrn_orient_matrix_ub_22 0.27486E-2 _diffrn_orient_matrix_ub_23 -0.171305E-1 _diffrn_orient_matrix_ub_31 0.3564E-2 _diffrn_orient_matrix_ub_32 0.573477E-1 _diffrn_orient_matrix_ub_33 0.12178E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.1047 _diffrn_reflns_av_unetI/netI 0.1194 _diffrn_reflns_number 8869 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.958 _diffrn_measured_fraction_theta_max 0.955 _reflns_number_total 4677 _reflns_number_gt 1948 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1191P)^2^+3.1453P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4677 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.212 _refine_ls_R_factor_gt 0.0876 _refine_ls_wR_factor_ref 0.2776 _refine_ls_wR_factor_gt 0.2039 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.516 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.064 #----------------------------------------------------------------------------# # 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' Al Al 0.0645 0.0514 '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' 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 Cl4 Cl 0.1455(2) 0.33109(14) 0.48151(13) 0.1140(8) Uani 1 1 d . . . Al2 Al 0.25232(16) 0.26867(10) 0.42165(9) 0.0586(5) Uani 1 1 d . . . N1 N 0.2201(4) 0.1586(3) 0.4262(2) 0.0545(11) Uani 1 1 d . . . N2 N 0.1758(4) 0.2628(3) 0.3383(2) 0.0598(12) Uani 1 1 d . . . C1 C 0.1688(5) 0.1364(3) 0.3755(3) 0.0616(15) Uani 1 1 d . . . H1 H 0.1479 0.0853 0.3698 0.074 Uiso 1 1 calc R . . C2 C 0.1441(5) 0.1938(3) 0.3269(3) 0.0637(15) Uani 1 1 d . . . H2 H 0.107 0.1809 0.2894 0.076 Uiso 1 1 calc R . . C3 C 0.1499(6) 0.3275(4) 0.2930(3) 0.0694(16) Uani 1 1 d . . . C4 C 0.2531(6) 0.1024(3) 0.4775(3) 0.0648(15) Uani 1 1 d . . . C5 C 0.2434(9) 0.3873(6) 0.3028(6) 0.126(4) Uani 1 1 d . . . H5A H 0.3121 0.3715 0.2812 0.189 Uiso 1 1 calc R . . H5B H 0.2591 0.3926 0.3473 0.189 Uiso 1 1 calc R . . H5C H 0.218 0.4357 0.2861 0.189 Uiso 1 1 calc R . . C6 C 0.0365(9) 0.3596(7) 0.3120(7) 0.139(5) Uani 1 1 d . . . H6A H 0.0368 0.3703 0.3567 0.209 Uiso 1 1 calc R . . H6B H -0.023 0.3231 0.3026 0.209 Uiso 1 1 calc R . . H6C H 0.0224 0.4062 0.2889 0.209 Uiso 1 1 calc R . . C7 C 0.1527(15) 0.3009(6) 0.2253(5) 0.147(5) Uani 1 1 d . . . H7A H 0.2211 0.2712 0.2182 0.22 Uiso 1 1 calc R . . H7B H 0.1526 0.3446 0.1976 0.22 Uiso 1 1 calc R . . H7C H 0.0862 0.2698 0.2169 0.22 Uiso 1 1 calc R . . C8 C 0.3674(8) 0.0674(6) 0.4573(5) 0.107(3) Uani 1 1 d . . . H8A H 0.3572 0.0395 0.4184 0.16 Uiso 1 1 calc R . . H8B H 0.3943 0.0331 0.4898 0.16 Uiso 1 1 calc R . . H8C H 0.4229 0.1075 0.451 0.16 Uiso 1 1 calc R . . C9 C 0.2648(10) 0.1476(5) 0.5378(4) 0.110(3) Uani 1 1 d . . . H9A H 0.1924 0.1712 0.5479 0.165 Uiso 1 1 calc R . . H9B H 0.3223 0.1866 0.5324 0.165 Uiso 1 1 calc R . . H9C H 0.2871 0.1139 0.5717 0.165 Uiso 1 1 calc R . . C10 C 0.1629(9) 0.0389(5) 0.4841(5) 0.109(3) Uani 1 1 d . . . H10A H 0.1642 0.0071 0.4469 0.164 Uiso 1 1 calc R . . H10B H 0.088 0.0616 0.4887 0.164 Uiso 1 1 calc R . . H10C H 0.18 0.0083 0.5208 0.164 Uiso 1 1 calc R . . C12 C 0.4189(4) 0.2893(3) 0.4163(3) 0.0483(12) Uani 1 1 d . . . H12A H 0.4311 0.3397 0.3991 0.072 Uiso 1 1 calc R . . H12B H 0.4545 0.2518 0.3893 0.072 Uiso 1 1 calc R . . H12C H 0.4522 0.2864 0.4579 0.072 Uiso 1 1 calc R . . Cl1 Cl 0.3731(2) 0.12193(16) 0.26857(10) 0.1078(8) Uani 1 1 d . . . Cl2 Cl 0.39668(18) 0.17285(12) 0.11127(11) 0.0932(7) Uani 1 1 d . . . Cl3 Cl 0.45997(18) -0.01060(10) 0.15866(11) 0.0917(7) Uani 1 1 d . . . Al1 Al 0.33998(17) 0.08188(11) 0.17320(10) 0.0686(6) Uani 1 1 d . . . C11 C 0.1802(6) 0.0515(5) 0.1616(4) 0.090(2) Uani 1 1 d . . . H11A H 0.1405 0.0902 0.1376 0.134 Uiso 1 1 calc R . . H11B H 0.1441 0.0457 0.2023 0.134 Uiso 1 1 calc R . . H11C H 0.1772 0.0036 0.1391 0.134 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 Cl4 0.1303(18) 0.1012(15) 0.1104(17) -0.0131(12) 0.0137(14) 0.0146(13) Al2 0.0597(10) 0.0506(9) 0.0655(11) 0.0005(8) -0.0026(8) -0.0039(7) N1 0.050(2) 0.053(2) 0.060(3) 0.000(2) -0.003(2) 0.0030(19) N2 0.056(3) 0.059(3) 0.064(3) 0.006(2) 0.002(2) 0.004(2) C1 0.062(3) 0.051(3) 0.072(4) -0.002(3) -0.011(3) -0.004(3) C2 0.066(4) 0.059(3) 0.066(4) 0.000(3) -0.011(3) -0.006(3) C3 0.072(4) 0.063(4) 0.073(4) 0.020(3) -0.003(3) 0.006(3) C4 0.071(4) 0.054(3) 0.069(4) 0.014(3) -0.015(3) -0.003(3) C5 0.128(7) 0.100(6) 0.151(9) 0.062(6) -0.028(7) -0.020(6) C6 0.109(7) 0.131(8) 0.178(11) 0.076(8) 0.025(7) 0.057(6) C7 0.261(15) 0.106(7) 0.074(6) 0.018(5) -0.023(7) 0.042(8) C8 0.097(6) 0.102(6) 0.120(7) 0.026(5) -0.007(5) 0.034(5) C9 0.178(9) 0.079(5) 0.072(5) 0.007(4) -0.021(5) 0.011(5) C10 0.126(7) 0.101(6) 0.101(6) 0.034(5) -0.030(5) -0.041(5) C12 0.029(2) 0.060(3) 0.055(3) 0.011(2) -0.009(2) -0.020(2) Cl1 0.1109(15) 0.1397(19) 0.0728(12) -0.0167(12) 0.0015(10) 0.0257(14) Cl2 0.0894(13) 0.0854(12) 0.1049(15) 0.0330(11) -0.0132(11) -0.0037(9) Cl3 0.1026(13) 0.0643(10) 0.1081(15) 0.0110(9) 0.0319(11) 0.0085(9) Al1 0.0673(11) 0.0681(11) 0.0703(12) 0.0030(9) 0.0079(9) -0.0002(9) C11 0.057(4) 0.099(5) 0.113(6) 0.003(5) 0.008(4) -0.016(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Cl4 Al2 2.077(3) . ? Al2 N1 1.956(5) . ? Al2 N2 1.971(5) . ? Al2 C12 1.971(5) . ? N1 C1 1.284(7) . ? N1 C4 1.508(7) . ? N2 C2 1.279(8) . ? N2 C3 1.507(8) . ? C1 C2 1.459(9) . ? C1 H1 0.93 . ? C2 H2 0.93 . ? C3 C6 1.485(12) . ? C3 C7 1.501(13) . ? C3 C5 1.518(12) . ? C4 C9 1.502(10) . ? C4 C8 1.521(11) . ? C4 C10 1.529(10) . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C8 H8A 0.96 . ? C8 H8B 0.96 . ? C8 H8C 0.96 . ? C9 H9A 0.96 . ? C9 H9B 0.96 . ? C9 H9C 0.96 . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? Cl1 Al1 2.162(3) . ? Cl2 Al1 2.156(3) . ? Cl3 Al1 2.152(3) . ? Al1 C11 1.945(7) . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? 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 Al2 N2 84.6(2) . . ? N1 Al2 C12 111.7(2) . . ? N2 Al2 C12 113.6(2) . . ? N1 Al2 Cl4 111.68(18) . . ? N2 Al2 Cl4 107.39(18) . . ? C12 Al2 Cl4 121.7(2) . . ? C1 N1 C4 121.3(5) . . ? C1 N1 Al2 110.1(4) . . ? C4 N1 Al2 128.5(4) . . ? C2 N2 C3 121.7(5) . . ? C2 N2 Al2 110.2(4) . . ? C3 N2 Al2 128.0(4) . . ? N1 C1 C2 117.9(5) . . ? N1 C1 H1 121 . . ? C2 C1 H1 121 . . ? N2 C2 C1 117.1(6) . . ? N2 C2 H2 121.4 . . ? C1 C2 H2 121.4 . . ? C6 C3 C7 113.0(9) . . ? C6 C3 N2 106.8(6) . . ? C7 C3 N2 111.5(6) . . ? C6 C3 C5 109.8(9) . . ? C7 C3 C5 109.0(9) . . ? N2 C3 C5 106.5(6) . . ? C9 C4 N1 106.8(5) . . ? C9 C4 C8 111.6(7) . . ? N1 C4 C8 106.3(6) . . ? C9 C4 C10 111.3(7) . . ? N1 C4 C10 111.1(5) . . ? C8 C4 C10 109.5(7) . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? Al2 C12 H12A 109.5 . . ? Al2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Al2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 Al1 Cl3 113.3(3) . . ? C11 Al1 Cl2 114.5(3) . . ? Cl3 Al1 Cl2 105.43(11) . . ? C11 Al1 Cl1 112.0(3) . . ? Cl3 Al1 Cl1 104.98(13) . . ? Cl2 Al1 Cl1 105.74(13) . . ? Al1 C11 H11A 109.5 . . ? Al1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? Al1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Al2 N1 C1 0.6(4) . . . . ? C12 Al2 N1 C1 -112.7(4) . . . . ? Cl4 Al2 N1 C1 107.2(4) . . . . ? N2 Al2 N1 C4 177.2(5) . . . . ? C12 Al2 N1 C4 63.9(5) . . . . ? Cl4 Al2 N1 C4 -76.2(5) . . . . ? N1 Al2 N2 C2 -0.6(4) . . . . ? C12 Al2 N2 C2 110.7(4) . . . . ? Cl4 Al2 N2 C2 -111.7(4) . . . . ? N1 Al2 N2 C3 176.7(5) . . . . ? C12 Al2 N2 C3 -72.0(5) . . . . ? Cl4 Al2 N2 C3 65.6(5) . . . . ? C4 N1 C1 C2 -177.5(5) . . . . ? Al2 N1 C1 C2 -0.6(6) . . . . ? C3 N2 C2 C1 -177.1(5) . . . . ? Al2 N2 C2 C1 0.4(7) . . . . ? N1 C1 C2 N2 0.1(9) . . . . ? C2 N2 C3 C6 89.8(9) . . . . ? Al2 N2 C3 C6 -87.2(8) . . . . ? C2 N2 C3 C7 -34.1(10) . . . . ? Al2 N2 C3 C7 148.9(8) . . . . ? C2 N2 C3 C5 -152.9(8) . . . . ? Al2 N2 C3 C5 30.1(8) . . . . ? C1 N1 C4 C9 -157.3(7) . . . . ? Al2 N1 C4 C9 26.5(8) . . . . ? C1 N1 C4 C8 83.4(7) . . . . ? Al2 N1 C4 C8 -92.8(7) . . . . ? C1 N1 C4 C10 -35.7(8) . . . . ? Al2 N1 C4 C10 148.1(6) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 960658' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_af315a _audit_creation_date 2012-12-12T13:14:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 11' _chemical_formula_moiety 'C28 H30 Al Cl4 N3' _chemical_formula_sum 'C28 H30 Al Cl4 N3' _chemical_formula_weight 577.33 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.988(10) _cell_length_b 23.822(20) _cell_length_c 9.334(50) _cell_angle_alpha 90.000(9) _cell_angle_beta 101.68 _cell_angle_gamma 90.000(9) _cell_volume 1521(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11037 _cell_measurement_theta_min 0.783 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_diffrn 1.26 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.439 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.847508 _exptl_absorpt_correction_T_max 1.0 #----------------------------------------------------------------------------# # 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 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.135747 _diffrn_orient_matrix_ub_12 0.10741E-2 _diffrn_orient_matrix_ub_13 0.130199E-1 _diffrn_orient_matrix_ub_21 0.376039E-1 _diffrn_orient_matrix_ub_22 -0.107996 _diffrn_orient_matrix_ub_23 -0.62333E-2 _diffrn_orient_matrix_ub_31 0.388829E-1 _diffrn_orient_matrix_ub_32 0.174473E-1 _diffrn_orient_matrix_ub_33 -0.394173E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_unetI/netI 0.056 _diffrn_reflns_number 13617 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.974 _reflns_number_total 6327 _reflns_number_gt 4427 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0650P)^2^+0.6828P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6327 _refine_ls_number_parameters 294 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0938 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1627 _refine_ls_wR_factor_gt 0.1446 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0 _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 -0.03(9) _refine_diff_density_max 0.415 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.042 #----------------------------------------------------------------------------# # 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' Al Al 0.0645 0.0514 '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 C1 C 0.8455(5) 0.23537(15) 0.7644(4) 0.0490(8) Uani 1 1 d D . . C2 C 0.9738(7) 0.23219(17) 0.5677(4) 0.0610(10) Uani 1 1 d D . . C3 C 0.8804(7) 0.18359(18) 0.5754(4) 0.0645(10) Uani 1 1 d . . . C4 C 0.6960(7) 0.13728(16) 0.7524(5) 0.0651(11) Uani 1 1 d . . . C5A C 0.8087(12) 0.0864(3) 0.7473(10) 0.0784(7) Uani 0.5 1 d PG A 1 C6A C 0.9579(12) 0.0811(3) 0.8700(8) 0.0784(7) Uani 0.5 1 d PG A 1 H6A H 0.9681 0.1067 0.9464 0.094 Uiso 0.5 1 calc PR A 1 C7A C 1.0921(10) 0.0375(3) 0.8785(7) 0.0784(7) Uani 0.5 1 d PG A 1 H7A H 1.1919 0.0339 0.9606 0.094 Uiso 0.5 1 calc PR A 1 C8A C 1.0769(9) -0.0007(2) 0.7643(8) 0.0784(7) Uani 0.5 1 d PG A 1 H8A H 1.1667 -0.0299 0.77 0.094 Uiso 0.5 1 calc PR A 1 C9A C 0.9277(10) 0.0046(2) 0.6416(7) 0.0784(7) Uani 0.5 1 d PG A 1 H9A H 0.9176 -0.021 0.5652 0.094 Uiso 0.5 1 calc PR A 1 C10A C 0.7936(10) 0.0482(3) 0.6331(8) 0.0784(7) Uani 0.5 1 d PG A 1 H10A H 0.6937 0.0517 0.551 0.094 Uiso 0.5 1 calc PR A 1 C5B C 0.8100(12) 0.0840(3) 0.7347(10) 0.0784(7) Uani 0.5 1 d PG A 2 C6B C 0.9809(11) 0.0667(3) 0.8280(7) 0.0784(7) Uani 0.5 1 d PG A 2 H6B H 1.0306 0.0872 0.9121 0.094 Uiso 0.5 1 calc PR A 2 C7B C 1.0776(8) 0.0189(3) 0.7955(7) 0.0784(7) Uani 0.5 1 d PG A 2 H7B H 1.1919 0.0073 0.8579 0.094 Uiso 0.5 1 calc PR A 2 C8B C 1.0033(9) -0.0118(2) 0.6698(8) 0.0784(7) Uani 0.5 1 d PG A 2 H8B H 1.068 -0.0438 0.6481 0.094 Uiso 0.5 1 calc PR A 2 C9B C 0.8324(10) 0.0055(3) 0.5765(7) 0.0784(7) Uani 0.5 1 d PG A 2 H9B H 0.7827 -0.015 0.4924 0.094 Uiso 0.5 1 calc PR A 2 C10B C 0.7358(10) 0.0534(3) 0.6090(9) 0.0784(7) Uani 0.5 1 d PG A 2 H10B H 0.6214 0.0649 0.5466 0.094 Uiso 0.5 1 calc PR A 2 C11 C 0.7815(6) 0.25342(16) 0.8972(4) 0.0540(9) Uani 1 1 d . . . C12 C 0.7247(7) 0.31834(18) 1.0692(4) 0.0662(11) Uani 1 1 d . . . C13 C 0.5956(4) 0.37002(10) 1.0433(3) 0.0625(10) Uani 1 1 d G . . C14 C 0.4560(6) 0.37802(15) 1.1285(4) 0.0950(16) Uani 1 1 d G . . H14 H 0.4362 0.3505 1.1947 0.114 Uiso 1 1 calc R . . C15 C 0.3462(5) 0.42709(18) 1.1146(5) 0.123(2) Uani 1 1 d G . . H15 H 0.2529 0.4324 1.1716 0.147 Uiso 1 1 calc R . . C16 C 0.3759(5) 0.46817(13) 1.0156(5) 0.1043(19) Uani 1 1 d G . . H16 H 0.3024 0.501 1.0063 0.125 Uiso 1 1 calc R . . C17 C 0.5154(6) 0.46017(11) 0.9304(4) 0.0905(15) Uani 1 1 d G . . H17 H 0.5353 0.4876 0.8642 0.109 Uiso 1 1 calc R . . C18 C 0.6252(5) 0.41109(12) 0.9443(3) 0.0752(12) Uani 1 1 d G . . H18 H 0.7186 0.4057 0.8873 0.09 Uiso 1 1 calc R . . C19 C 1.0510(5) 0.31892(15) 0.7245(4) 0.0538(8) Uani 1 1 d . . . H19 H 1.0811 0.3215 0.8315 0.065 Uiso 1 1 calc R . . C20 C 0.9204(4) 0.36770(9) 0.6681(3) 0.0576(9) Uani 1 1 d G . . C21 C 0.7414(4) 0.36251(12) 0.5718(3) 0.0686(11) Uani 1 1 d G . . H21 H 0.6967 0.3273 0.5371 0.082 Uiso 1 1 calc R . . C22 C 0.6291(5) 0.40994(17) 0.5276(4) 0.1038(18) Uani 1 1 d G . . H22 H 0.5093 0.4065 0.4632 0.125 Uiso 1 1 calc R . . C23 C 0.6958(7) 0.46256(13) 0.5795(5) 0.115(2) Uani 1 1 d G . . H23 H 0.6206 0.4943 0.5499 0.138 Uiso 1 1 calc R . . C24 C 0.8748(7) 0.46775(9) 0.6757(5) 0.110(2) Uani 1 1 d G . . H24 H 0.9195 0.503 0.7105 0.132 Uiso 1 1 calc R . . C25 C 0.9871(5) 0.42032(12) 0.7200(4) 0.0845(14) Uani 1 1 d G . . H25 H 1.1069 0.4238 0.7844 0.101 Uiso 1 1 calc R . . C26 C 1.2455(7) 0.3208(2) 0.6728(6) 0.0828(13) Uani 1 1 d . . . H26A H 1.3239 0.2891 0.7115 0.124 Uiso 1 1 calc R . . H26B H 1.3135 0.3548 0.7065 0.124 Uiso 1 1 calc R . . H26C H 1.2208 0.3197 0.5678 0.124 Uiso 1 1 calc R . . C27 C 0.4832(8) 0.1376(2) 0.6727(8) 0.1002(18) Uani 1 1 d . A . H27A H 0.4152 0.107 0.7072 0.15 Uiso 1 1 calc R . . H27B H 0.4767 0.1335 0.5695 0.15 Uiso 1 1 calc R . . H27C H 0.4235 0.1724 0.6911 0.15 Uiso 1 1 calc R . . N1 N 0.8017(5) 0.18539(12) 0.6988(3) 0.0563(7) Uani 1 1 d . A . N2 N 0.9540(5) 0.26406(12) 0.6857(3) 0.0518(7) Uani 1 1 d . . . N3 N 0.7904(5) 0.30360(13) 0.9343(3) 0.0589(8) Uani 1 1 d . . . Al1 Al 0.67804(19) 0.67748(5) 0.79778(13) 0.0679(3) Uani 1 1 d D . . Cl1 Cl 0.4804(4) 0.61041(8) 0.7704(2) 0.1485(9) Uani 1 1 d . B . Cl2A Cl 0.9739(8) 0.6598(3) 0.7706(6) 0.1015(17) Uani 0.5 1 d PDU B 1 Cl2B Cl 0.9225(15) 0.6369(4) 0.7561(11) 0.178(5) Uani 0.5 1 d PU B 2 Cl3 Cl 0.7114(2) 0.71016(7) 1.01300(14) 0.1030(5) Uani 1 1 d . B . Cl4 Cl 0.5800(2) 0.74206(5) 0.64276(14) 0.0894(4) Uani 1 1 d . B . C28 C 0.9067(9) 0.3284(3) 1.1891(5) 0.0972(17) Uani 1 1 d . . . H28A H 0.9853 0.2951 1.2025 0.146 Uiso 1 1 calc R . . H28B H 0.8675 0.3377 1.2791 0.146 Uiso 1 1 calc R . . H28C H 0.9811 0.3589 1.1609 0.146 Uiso 1 1 calc R . . H3 H 0.856(6) 0.1564(19) 0.509(5) 0.066(12) Uiso 1 1 d . . . H4 H 0.706(6) 0.1434(18) 0.862(5) 0.072(12) Uiso 1 1 d . . . H12 H 0.654(6) 0.2869(17) 1.099(4) 0.059(11) Uiso 1 1 d . . . H11 H 0.729(5) 0.2215(16) 0.953(4) 0.050(9) Uiso 1 1 d . . . H2 H 1.051(7) 0.2484(19) 0.501(5) 0.076(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0543(19) 0.0472(18) 0.0457(17) 0.0015(15) 0.0105(15) -0.0009(15) C2 0.081(3) 0.058(2) 0.050(2) 0.0004(17) 0.0253(19) -0.001(2) C3 0.096(3) 0.054(2) 0.048(2) -0.0121(19) 0.0247(19) 0.000(2) C4 0.093(3) 0.052(2) 0.056(2) -0.0049(17) 0.028(2) -0.011(2) C5A 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C6A 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C7A 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C8A 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C9A 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C10A 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C5B 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C6B 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C7B 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C8B 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C9B 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C10B 0.0833(17) 0.0556(14) 0.098(2) 0.0079(12) 0.0232(14) 0.0091(13) C11 0.061(2) 0.055(2) 0.0489(19) -0.0032(16) 0.0171(17) -0.0084(16) C12 0.090(3) 0.058(2) 0.060(2) -0.0076(19) 0.035(2) -0.007(2) C13 0.066(2) 0.066(2) 0.058(2) -0.0226(19) 0.0183(19) -0.0112(19) C14 0.098(4) 0.099(4) 0.103(4) -0.006(3) 0.056(3) 0.009(3) C15 0.109(5) 0.146(6) 0.128(5) -0.013(5) 0.060(4) 0.038(4) C16 0.091(4) 0.095(4) 0.117(5) -0.034(4) 0.000(3) 0.026(3) C17 0.104(4) 0.065(3) 0.101(4) -0.012(3) 0.019(3) 0.010(3) C18 0.079(3) 0.064(3) 0.088(3) -0.003(2) 0.030(3) 0.001(2) C19 0.058(2) 0.059(2) 0.0444(18) -0.0009(16) 0.0111(16) -0.0100(17) C20 0.070(2) 0.053(2) 0.054(2) 0.0018(16) 0.0246(18) -0.0064(18) C21 0.074(3) 0.073(3) 0.054(2) 0.001(2) 0.005(2) 0.010(2) C22 0.109(4) 0.115(5) 0.085(4) 0.020(3) 0.014(3) 0.032(4) C23 0.159(7) 0.075(4) 0.122(5) 0.032(3) 0.055(5) 0.028(4) C24 0.165(6) 0.057(3) 0.120(5) 0.005(3) 0.060(5) -0.006(3) C25 0.098(4) 0.064(3) 0.096(3) 0.001(2) 0.033(3) -0.023(3) C26 0.061(3) 0.095(3) 0.095(3) -0.004(3) 0.025(2) -0.011(2) C27 0.081(4) 0.077(3) 0.153(6) 0.019(3) 0.049(4) 0.002(3) N1 0.074(2) 0.0521(17) 0.0464(15) -0.0026(13) 0.0209(14) -0.0035(15) N2 0.0600(18) 0.0487(16) 0.0483(16) -0.0034(13) 0.0144(14) -0.0005(13) N3 0.075(2) 0.0545(18) 0.0532(17) -0.0033(14) 0.0272(15) 0.0009(15) Al1 0.0760(8) 0.0703(8) 0.0565(6) 0.0014(6) 0.0114(6) 0.0088(6) Cl1 0.1798(19) 0.1036(12) 0.1402(15) 0.0322(11) -0.0194(14) -0.0546(13) Cl2A 0.084(2) 0.142(5) 0.089(2) 0.030(2) 0.0434(15) 0.043(3) Cl2B 0.205(8) 0.148(7) 0.223(7) 0.053(5) 0.144(6) 0.091(6) Cl3 0.0995(9) 0.1400(12) 0.0639(7) -0.0223(7) 0.0034(6) 0.0164(9) Cl4 0.1093(10) 0.0759(7) 0.0783(7) 0.0125(6) 0.0081(7) 0.0072(6) C28 0.114(4) 0.110(4) 0.064(3) -0.009(3) 0.009(3) 0.040(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N2 1.344(5) . ? C1 N1 1.345(5) . ? C1 C11 1.465(5) . ? C2 C3 1.338(6) . ? C2 N2 1.368(5) . ? C2 H2 0.98(5) . ? C3 N1 1.373(5) . ? C3 H3 0.89(5) . ? C4 C5A 1.451(6) . ? C4 N1 1.503(5) . ? C4 C27 1.522(8) . ? C4 C5B 1.525(6) . ? C4 H4 1.02(5) . ? C5A C6A 1.39 . ? C5A C10A 1.39 . ? C6A C7A 1.39 . ? C6A H6A 0.93 . ? C7A C8A 1.39 . ? C7A H7A 0.93 . ? C8A C9A 1.39 . ? C8A H8A 0.93 . ? C9A C10A 1.39 . ? C9A H9A 0.93 . ? C10A H10A 0.93 . ? C5B C6B 1.39 . ? C5B C10B 1.39 . ? C6B C7B 1.39 . ? C6B H6B 0.93 . ? C7B C8B 1.39 . ? C7B H7B 0.93 . ? C8B C9B 1.39 . ? C8B H8B 0.93 . ? C9B C10B 1.39 . ? C9B H9B 0.93 . ? C10B H10B 0.93 . ? C11 N3 1.243(5) . ? C11 H11 1.03(4) . ? C12 N3 1.467(5) . ? C12 C13 1.517(5) . ? C12 C28 1.533(7) . ? C12 H12 0.97(4) . ? C13 C14 1.39 . ? C13 C18 1.39 . ? C14 C15 1.39 . ? C14 H14 0.93 . ? C15 C16 1.39 . ? C15 H15 0.93 . ? C16 C17 1.39 . ? C16 H16 0.93 . ? C17 C18 1.39 . ? C17 H17 0.93 . ? C18 H18 0.93 . ? C19 N2 1.483(5) . ? C19 C20 1.505(4) . ? C19 C26 1.532(6) . ? C19 H19 0.98 . ? C20 C21 1.39 . ? C20 C25 1.39 . ? C21 C22 1.39 . ? C21 H21 0.93 . ? C22 C23 1.39 . ? C22 H22 0.93 . ? C23 C24 1.39 . ? C23 H23 0.93 . ? C24 C25 1.39 . ? C24 H24 0.93 . ? C25 H25 0.93 . ? C26 H26A 0.96 . ? C26 H26B 0.96 . ? C26 H26C 0.96 . ? C27 H27A 0.96 . ? C27 H27B 0.96 . ? C27 H27C 0.96 . ? Al1 Cl2B 2.067(9) . ? Al1 Cl1 2.094(2) . ? Al1 Cl3 2.1227(18) . ? Al1 Cl4 2.1281(17) . ? Al1 Cl2A 2.175(6) . ? C28 H28A 0.96 . ? C28 H28B 0.96 . ? C28 H28C 0.96 . ? 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 N2 C1 N1 107.6(3) . . ? N2 C1 C11 128.0(3) . . ? N1 C1 C11 124.4(3) . . ? C3 C2 N2 107.9(3) . . ? C3 C2 H2 135(3) . . ? N2 C2 H2 117(3) . . ? C2 C3 N1 107.5(3) . . ? C2 C3 H3 128(3) . . ? N1 C3 H3 124(3) . . ? C5A C4 N1 108.6(5) . . ? C5A C4 C27 118.1(5) . . ? N1 C4 C27 109.4(4) . . ? C5A C4 C5B 4.2(6) . . ? N1 C4 C5B 107.2(5) . . ? C27 C4 C5B 115.5(5) . . ? C5A C4 H4 103(2) . . ? N1 C4 H4 107(2) . . ? C27 C4 H4 111(2) . . ? C5B C4 H4 107(2) . . ? C6A C5A C10A 120 . . ? C6A C5A C4 111.8(5) . . ? C10A C5A C4 128.0(5) . . ? C5A C6A C7A 120 . . ? C5A C6A H6A 120 . . ? C7A C6A H6A 120 . . ? C8A C7A C6A 120 . . ? C8A C7A H7A 120 . . ? C6A C7A H7A 120 . . ? C7A C8A C9A 120 . . ? C7A C8A H8A 120 . . ? C9A C8A H8A 120 . . ? C8A C9A C10A 120 . . ? C8A C9A H9A 120 . . ? C10A C9A H9A 120 . . ? C9A C10A C5A 120 . . ? C9A C10A H10A 120 . . ? C5A C10A H10A 120 . . ? C6B C5B C10B 120 . . ? C6B C5B C4 125.5(5) . . ? C10B C5B C4 114.5(5) . . ? C7B C6B C5B 120 . . ? C7B C6B H6B 120 . . ? C5B C6B H6B 120 . . ? C6B C7B C8B 120 . . ? C6B C7B H7B 120 . . ? C8B C7B H7B 120 . . ? C9B C8B C7B 120 . . ? C9B C8B H8B 120 . . ? C7B C8B H8B 120 . . ? C8B C9B C10B 120 . . ? C8B C9B H9B 120 . . ? C10B C9B H9B 120 . . ? C9B C10B C5B 120 . . ? C9B C10B H10B 120 . . ? C5B C10B H10B 120 . . ? N3 C11 C1 120.8(3) . . ? N3 C11 H11 125(2) . . ? C1 C11 H11 114(2) . . ? N3 C12 C13 109.7(3) . . ? N3 C12 C28 107.9(4) . . ? C13 C12 C28 111.6(3) . . ? N3 C12 H12 109(2) . . ? C13 C12 H12 110(2) . . ? C28 C12 H12 108(2) . . ? C14 C13 C18 120 . . ? C14 C13 C12 118.9(2) . . ? C18 C13 C12 120.9(2) . . ? C15 C14 C13 120 . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C16 C15 C14 120 . . ? C16 C15 H15 120 . . ? C14 C15 H15 120 . . ? C15 C16 C17 120 . . ? C15 C16 H16 120 . . ? C17 C16 H16 120 . . ? C18 C17 C16 120 . . ? C18 C17 H17 120 . . ? C16 C17 H17 120 . . ? C17 C18 C13 120 . . ? C17 C18 H18 120 . . ? C13 C18 H18 120 . . ? N2 C19 C20 112.3(3) . . ? N2 C19 C26 109.8(3) . . ? C20 C19 C26 112.4(3) . . ? N2 C19 H19 107.3 . . ? C20 C19 H19 107.3 . . ? C26 C19 H19 107.3 . . ? C21 C20 C25 120 . . ? C21 C20 C19 124.1(2) . . ? C25 C20 C19 115.9(2) . . ? C22 C21 C20 120 . . ? C22 C21 H21 120 . . ? C20 C21 H21 120 . . ? C21 C22 C23 120 . . ? C21 C22 H22 120 . . ? C23 C22 H22 120 . . ? C22 C23 C24 120 . . ? C22 C23 H23 120 . . ? C24 C23 H23 120 . . ? C25 C24 C23 120 . . ? C25 C24 H24 120 . . ? C23 C24 H24 120 . . ? C24 C25 C20 120 . . ? C24 C25 H25 120 . . ? C20 C25 H25 120 . . ? C19 C26 H26A 109.5 . . ? C19 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C19 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C4 C27 H27A 109.5 . . ? C4 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C4 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C1 N1 C3 108.4(3) . . ? C1 N1 C4 127.2(3) . . ? C3 N1 C4 124.2(3) . . ? C1 N2 C2 108.5(3) . . ? C1 N2 C19 126.5(3) . . ? C2 N2 C19 124.7(3) . . ? C11 N3 C12 117.6(3) . . ? Cl2B Al1 Cl1 99.8(3) . . ? Cl2B Al1 Cl3 114.4(3) . . ? Cl1 Al1 Cl3 109.80(10) . . ? Cl2B Al1 Cl4 112.0(3) . . ? Cl1 Al1 Cl4 110.79(8) . . ? Cl3 Al1 Cl4 109.69(8) . . ? Cl2B Al1 Cl2A 17.4(4) . . ? Cl1 Al1 Cl2A 117.2(2) . . ? Cl3 Al1 Cl2A 104.86(17) . . ? Cl4 Al1 Cl2A 104.11(16) . . ? C12 C28 H28A 109.5 . . ? C12 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C12 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 C2 C3 N1 0.2(5) . . . . ? N1 C4 C5A C6A 82.7(5) . . . . ? C27 C4 C5A C6A -152.1(4) . . . . ? C5B C4 C5A C6A 154(11) . . . . ? N1 C4 C5A C10A -91.1(7) . . . . ? C27 C4 C5A C10A 34.1(9) . . . . ? C5B C4 C5A C10A -20(10) . . . . ? C10A C5A C6A C7A 0 . . . . ? C4 C5A C6A C7A -174.4(8) . . . . ? C5A C6A C7A C8A 0 . . . . ? C6A C7A C8A C9A 0 . . . . ? C7A C8A C9A C10A 0 . . . . ? C8A C9A C10A C5A 0 . . . . ? C6A C5A C10A C9A 0 . . . . ? C4 C5A C10A C9A 173.4(9) . . . . ? C5A C4 C5B C6B -32(10) . . . . ? N1 C4 C5B C6B 78.5(7) . . . . ? C27 C4 C5B C6B -159.4(5) . . . . ? C5A C4 C5B C10B 152(10) . . . . ? N1 C4 C5B C10B -98.0(5) . . . . ? C27 C4 C5B C10B 24.1(7) . . . . ? C10B C5B C6B C7B 0 . . . . ? C4 C5B C6B C7B -176.3(9) . . . . ? C5B C6B C7B C8B 0 . . . . ? C6B C7B C8B C9B 0 . . . . ? C7B C8B C9B C10B 0 . . . . ? C8B C9B C10B C5B 0 . . . . ? C6B C5B C10B C9B 0 . . . . ? C4 C5B C10B C9B 176.7(8) . . . . ? N2 C1 C11 N3 15.1(6) . . . . ? N1 C1 C11 N3 -164.5(4) . . . . ? N3 C12 C13 C14 153.6(3) . . . . ? C28 C12 C13 C14 -87.0(4) . . . . ? N3 C12 C13 C18 -31.4(4) . . . . ? C28 C12 C13 C18 88.1(4) . . . . ? C18 C13 C14 C15 0 . . . . ? C12 C13 C14 C15 175.1(3) . . . . ? C13 C14 C15 C16 0 . . . . ? C14 C15 C16 C17 0 . . . . ? C15 C16 C17 C18 0 . . . . ? C16 C17 C18 C13 0 . . . . ? C14 C13 C18 C17 0 . . . . ? C12 C13 C18 C17 -175.0(3) . . . . ? N2 C19 C20 C21 -9.3(4) . . . . ? C26 C19 C20 C21 115.1(3) . . . . ? N2 C19 C20 C25 169.6(2) . . . . ? C26 C19 C20 C25 -65.9(4) . . . . ? C25 C20 C21 C22 0 . . . . ? C19 C20 C21 C22 178.9(3) . . . . ? C20 C21 C22 C23 0 . . . . ? C21 C22 C23 C24 0 . . . . ? C22 C23 C24 C25 0 . . . . ? C23 C24 C25 C20 0 . . . . ? C21 C20 C25 C24 0 . . . . ? C19 C20 C25 C24 -179.0(3) . . . . ? N2 C1 N1 C3 -1.5(4) . . . . ? C11 C1 N1 C3 178.2(4) . . . . ? N2 C1 N1 C4 175.1(4) . . . . ? C11 C1 N1 C4 -5.3(6) . . . . ? C2 C3 N1 C1 0.8(5) . . . . ? C2 C3 N1 C4 -175.9(4) . . . . ? C5A C4 N1 C1 -130.1(5) . . . . ? C27 C4 N1 C1 99.8(5) . . . . ? C5B C4 N1 C1 -134.3(5) . . . . ? C5A C4 N1 C3 45.9(6) . . . . ? C27 C4 N1 C3 -84.2(5) . . . . ? C5B C4 N1 C3 41.7(6) . . . . ? N1 C1 N2 C2 1.6(4) . . . . ? C11 C1 N2 C2 -178.0(4) . . . . ? N1 C1 N2 C19 -173.8(3) . . . . ? C11 C1 N2 C19 6.6(6) . . . . ? C3 C2 N2 C1 -1.1(5) . . . . ? C3 C2 N2 C19 174.4(3) . . . . ? C20 C19 N2 C1 -89.1(4) . . . . ? C26 C19 N2 C1 145.0(4) . . . . ? C20 C19 N2 C2 96.3(4) . . . . ? C26 C19 N2 C2 -29.6(5) . . . . ? C1 C11 N3 C12 -179.6(4) . . . . ? C13 C12 N3 C11 -134.6(4) . . . . ? C28 C12 N3 C11 103.7(5) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 960659' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_af201 _audit_creation_date 2013-08-10T21:04:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 14[AlCl4]' _chemical_formula_moiety 'C16 H30 N3, Al Cl4 ' _chemical_formula_sum 'C16 H30 Al Cl4 N3 ' _chemical_formula_weight 433.21 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9102(3) _cell_length_b 20.2966(5) _cell_length_c 21.7692(7) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4820.6(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5719 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.375 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.531 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. ; _exptl_absorpt_correction_T_min 0.8614 _exptl_absorpt_correction_T_max 0.862 #----------------------------------------------------------------------------# # 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 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.456383E-1 _diffrn_orient_matrix_ub_12 0.261313E-1 _diffrn_orient_matrix_ub_13 0.315184E-1 _diffrn_orient_matrix_ub_21 0.764448E-1 _diffrn_orient_matrix_ub_22 0.251107E-1 _diffrn_orient_matrix_ub_23 0.97057E-2 _diffrn_orient_matrix_ub_31 -0.217809E-1 _diffrn_orient_matrix_ub_32 0.333778E-1 _diffrn_orient_matrix_ub_33 -0.319773E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.1544 _diffrn_reflns_av_unetI/netI 0.1713 _diffrn_reflns_number 10069 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.974 _reflns_number_total 5386 _reflns_number_gt 2246 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0983P)^2^+3.5245P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5386 _refine_ls_number_parameters 279 _refine_ls_number_restraints 252 _refine_ls_R_factor_all 0.2139 _refine_ls_R_factor_gt 0.0881 _refine_ls_wR_factor_ref 0.2505 _refine_ls_wR_factor_gt 0.1997 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.379 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # 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' Al Al 0.0645 0.0514 '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' H H 0 0 '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 N1 N 0.6614(3) 0.40938(19) 0.49073(19) 0.0542(10) Uani 1 1 d D A . N2 N 0.5891(4) 0.3589(2) 0.41129(18) 0.0559(11) Uani 1 1 d D B . N3 N 0.6614(4) 0.5067(2) 0.3712(2) 0.0638(12) Uani 1 1 d U . . C1 C 0.5864(5) 0.3589(3) 0.5121(3) 0.0637(15) Uani 1 1 d D . . C2 C 0.5438(5) 0.3289(3) 0.4630(3) 0.0661(15) Uani 1 1 d D . . H2 H 0.4912 0.2928 0.4633 0.079 Uiso 1 1 calc R . . C3 C 0.6593(4) 0.4090(2) 0.4292(2) 0.0496(12) Uani 1 1 d . . . C4 C 0.7200(5) 0.4578(3) 0.3887(2) 0.0588(14) Uani 1 1 d . B . C5 C 0.7280(5) 0.4561(3) 0.5338(2) 0.0700(15) Uani 1 1 d DU . . C6 C 0.8508(5) 0.4747(4) 0.5090(3) 0.117(3) Uani 1 1 d D A . H6A H 0.8906 0.5041 0.5371 0.175 Uiso 1 1 calc R . . H6B H 0.8409 0.496 0.47 0.175 Uiso 1 1 calc R . . H6C H 0.8998 0.4357 0.504 0.175 Uiso 1 1 calc R . . C7A C 0.6534(15) 0.5159(8) 0.5534(7) 0.107(6) Uani 0.5 1 d PDU A 1 H7A1 H 0.5755 0.5017 0.569 0.161 Uiso 0.5 1 calc PR A 1 H7A2 H 0.641 0.5443 0.5187 0.161 Uiso 0.5 1 calc PR A 1 H7A3 H 0.6968 0.5394 0.5849 0.161 Uiso 0.5 1 calc PR A 1 C8A C 0.7493(18) 0.4129(8) 0.5902(6) 0.125(6) Uani 0.5 1 d PDU A 1 H8A1 H 0.6717 0.4003 0.6074 0.188 Uiso 0.5 1 calc PR A 1 H8A2 H 0.7955 0.4371 0.6201 0.188 Uiso 0.5 1 calc PR A 1 H8A3 H 0.7939 0.3741 0.5784 0.188 Uiso 0.5 1 calc PR A 1 C7B C 0.6448(13) 0.5177(8) 0.5279(7) 0.084(4) Uani 0.5 1 d PDU A 2 H7B1 H 0.5646 0.5076 0.5435 0.127 Uiso 0.5 1 calc PR A 2 H7B2 H 0.6386 0.5301 0.4855 0.127 Uiso 0.5 1 calc PR A 2 H7B3 H 0.6795 0.5533 0.551 0.127 Uiso 0.5 1 calc PR A 2 C8B C 0.7296(19) 0.4373(9) 0.6018(6) 0.121(6) Uani 0.5 1 d PDU A 2 H8B1 H 0.648 0.4265 0.6148 0.181 Uiso 0.5 1 calc PR A 2 H8B2 H 0.7596 0.4738 0.6255 0.181 Uiso 0.5 1 calc PR A 2 H8B3 H 0.7822 0.4 0.6077 0.181 Uiso 0.5 1 calc PR A 2 C9 C 0.5616(5) 0.3375(3) 0.3457(2) 0.0728(16) Uani 1 1 d . . . C10 C 0.6783(6) 0.3400(4) 0.3077(3) 0.099(2) Uani 1 1 d . B . H10A H 0.7384 0.3113 0.3255 0.149 Uiso 1 1 calc R . . H10B H 0.7093 0.3843 0.3072 0.149 Uiso 1 1 calc R . . H10C H 0.6609 0.3261 0.2665 0.149 Uiso 1 1 calc R . . C11 C 0.5155(8) 0.2652(3) 0.3488(3) 0.113(2) Uani 1 1 d . B . H11A H 0.4424 0.2633 0.3733 0.169 Uiso 1 1 calc R . . H11B H 0.5776 0.2381 0.3671 0.169 Uiso 1 1 calc R . . H11C H 0.4981 0.2497 0.3081 0.169 Uiso 1 1 calc R . . C12 C 0.4620(6) 0.3818(3) 0.3201(3) 0.090(2) Uani 1 1 d . B . H12A H 0.3907 0.3792 0.3458 0.135 Uiso 1 1 calc R . . H12B H 0.4413 0.3679 0.2792 0.135 Uiso 1 1 calc R . . H12C H 0.4909 0.4265 0.319 0.135 Uiso 1 1 calc R . . C13A C 0.7110(14) 0.5574(10) 0.3279(8) 0.082(3) Uani 0.5 1 d PDU B 1 C14A C 0.8285(12) 0.5376(7) 0.2970(7) 0.112(4) Uani 0.5 1 d PDU B 1 H14A H 0.815 0.4986 0.273 0.168 Uiso 0.5 1 calc PR B 1 H14B H 0.8899 0.5289 0.3275 0.168 Uiso 0.5 1 calc PR B 1 H14C H 0.8558 0.5726 0.2707 0.168 Uiso 0.5 1 calc PR B 1 C15A C 0.7249(14) 0.6186(8) 0.3666(7) 0.109(4) Uani 0.5 1 d PDU B 1 H15A H 0.6477 0.6292 0.3853 0.163 Uiso 0.5 1 calc PR B 1 H15B H 0.7507 0.6546 0.3411 0.163 Uiso 0.5 1 calc PR B 1 H15C H 0.785 0.611 0.398 0.163 Uiso 0.5 1 calc PR B 1 C16A C 0.6134(12) 0.5695(7) 0.2793(6) 0.101(4) Uani 0.5 1 d PDU B 1 H16A H 0.5377 0.5813 0.2988 0.151 Uiso 0.5 1 calc PR B 1 H16B H 0.6019 0.5301 0.2555 0.151 Uiso 0.5 1 calc PR B 1 H16C H 0.6392 0.6047 0.2527 0.151 Uiso 0.5 1 calc PR B 1 C13B C 0.7231(14) 0.5573(10) 0.3328(8) 0.084(3) Uani 0.5 1 d PDU B 2 C14B C 0.8594(11) 0.5654(7) 0.3433(8) 0.112(4) Uani 0.5 1 d PDU B 2 H14D H 0.874 0.5763 0.3856 0.169 Uiso 0.5 1 calc PR B 2 H14E H 0.89 0.6001 0.3175 0.169 Uiso 0.5 1 calc PR B 2 H14F H 0.9005 0.525 0.3334 0.169 Uiso 0.5 1 calc PR B 2 C15B C 0.6625(14) 0.6225(8) 0.3485(8) 0.114(4) Uani 0.5 1 d PDU B 2 H15D H 0.6799 0.6336 0.3905 0.171 Uiso 0.5 1 calc PR B 2 H15E H 0.5755 0.6187 0.343 0.171 Uiso 0.5 1 calc PR B 2 H15F H 0.6937 0.6563 0.322 0.171 Uiso 0.5 1 calc PR B 2 C16B C 0.6978(17) 0.5400(8) 0.2670(6) 0.128(4) Uani 0.5 1 d PDU B 2 H16D H 0.7371 0.499 0.2572 0.192 Uiso 0.5 1 calc PR B 2 H16E H 0.729 0.5741 0.2407 0.192 Uiso 0.5 1 calc PR B 2 H16F H 0.611 0.5358 0.2609 0.192 Uiso 0.5 1 calc PR B 2 Cl1 Cl 0.06146(16) 0.40601(7) 0.35131(7) 0.0833(5) Uani 1 1 d . . . Cl2 Cl -0.10387(16) 0.29431(10) 0.43934(10) 0.1098(7) Uani 1 1 d . . . Cl3 Cl 0.1092(3) 0.23694(9) 0.33638(9) 0.1417(10) Uani 1 1 d . . . Cl4 Cl 0.2026(2) 0.31698(11) 0.46721(12) 0.1436(10) Uani 1 1 d . . . Al1 Al 0.06758(15) 0.31394(8) 0.39855(8) 0.0653(5) Uani 1 1 d . . . H1 H 0.575(6) 0.359(3) 0.557(3) 0.10(2) Uiso 1 1 d D . . H4 H 0.805(6) 0.450(3) 0.382(3) 0.094(19) 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 N1 0.047(2) 0.055(2) 0.061(3) 0.005(2) -0.002(2) -0.005(2) N2 0.052(3) 0.056(3) 0.060(3) -0.001(2) -0.006(2) 0.001(2) N3 0.058(3) 0.066(3) 0.068(3) 0.011(2) 0.003(2) -0.002(2) C1 0.067(4) 0.069(4) 0.055(3) 0.007(3) -0.002(3) -0.007(3) C2 0.064(4) 0.059(3) 0.076(4) 0.009(3) 0.001(3) -0.010(3) C3 0.043(3) 0.056(3) 0.049(3) 0.001(2) 0.001(2) 0.006(3) C4 0.053(3) 0.067(4) 0.057(3) 0.003(3) 0.007(3) -0.001(3) C5 0.065(4) 0.087(4) 0.058(3) -0.014(3) -0.006(3) -0.015(3) C6 0.061(4) 0.165(7) 0.123(6) -0.050(6) 0.005(4) -0.036(4) C7A 0.103(9) 0.123(9) 0.096(12) -0.078(9) -0.026(8) -0.005(8) C8A 0.184(12) 0.126(13) 0.066(8) -0.006(9) -0.058(9) -0.069(10) C7B 0.092(8) 0.091(8) 0.071(10) -0.042(8) -0.017(8) -0.009(7) C8B 0.175(12) 0.116(12) 0.071(9) -0.011(9) -0.023(9) -0.051(10) C9 0.072(4) 0.079(4) 0.067(4) -0.018(3) -0.012(3) 0.001(3) C10 0.086(5) 0.134(6) 0.079(4) -0.037(4) 0.000(4) 0.005(4) C11 0.149(7) 0.088(5) 0.101(5) -0.030(4) -0.013(5) -0.022(5) C12 0.083(4) 0.116(5) 0.070(4) -0.010(4) -0.027(3) 0.009(4) C13A 0.085(6) 0.081(6) 0.079(6) 0.017(6) 0.018(6) -0.006(6) C14A 0.108(8) 0.115(8) 0.114(9) 0.062(7) 0.041(7) 0.006(8) C15A 0.107(9) 0.091(8) 0.128(9) 0.029(7) -0.006(8) -0.020(8) C16A 0.103(8) 0.107(8) 0.093(8) 0.042(7) -0.009(7) 0.015(7) C13B 0.086(7) 0.082(6) 0.084(7) 0.020(6) 0.016(6) 0.003(6) C14B 0.107(8) 0.096(8) 0.134(9) 0.039(8) 0.016(8) -0.013(7) C15B 0.105(9) 0.095(7) 0.141(9) 0.036(8) 0.015(8) 0.024(8) C16B 0.154(10) 0.134(9) 0.095(8) 0.032(8) 0.010(8) -0.030(9) Cl1 0.1025(12) 0.0630(9) 0.0843(10) 0.0176(8) -0.0041(9) 0.0008(8) Cl2 0.0663(10) 0.1219(15) 0.1414(17) 0.0531(13) 0.0178(10) 0.0112(10) Cl3 0.249(3) 0.0734(11) 0.1026(15) 0.0129(10) 0.0556(16) 0.0190(14) Cl4 0.1171(17) 0.1357(18) 0.178(2) 0.0667(15) -0.0822(15) -0.0402(14) Al1 0.0605(10) 0.0619(10) 0.0734(11) 0.0149(8) -0.0041(8) -0.0003(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.339(6) . ? N1 C1 1.391(6) . ? N1 C5 1.518(6) . ? N2 C3 1.333(6) . ? N2 C2 1.372(6) . ? N2 C9 1.522(6) . ? N3 C4 1.240(6) . ? N3 C13B 1.49(2) . ? N3 C13A 1.50(2) . ? C1 C2 1.315(7) . ? C1 H1 0.99(6) . ? C2 H2 0.93 . ? C3 C4 1.482(7) . ? C4 H4 0.95(6) . ? C5 C6 1.492(7) . ? C5 C7A 1.522(11) . ? C5 C8A 1.526(11) . ? C5 C8B 1.528(11) . ? C5 C7B 1.550(11) . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C7A H7A1 0.96 . ? C7A H7A2 0.96 . ? C7A H7A3 0.96 . ? C8A H8A1 0.96 . ? C8A H8A2 0.96 . ? C8A H8A3 0.96 . ? C7B H7B1 0.96 . ? C7B H7B2 0.96 . ? C7B H7B3 0.96 . ? C8B H8B1 0.96 . ? C8B H8B2 0.96 . ? C8B H8B3 0.96 . ? C9 C12 1.516(8) . ? C9 C10 1.519(8) . ? C9 C11 1.552(8) . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13A C14A 1.503(14) . ? C13A C15A 1.509(14) . ? C13A C16A 1.522(14) . ? C14A H14A 0.96 . ? C14A H14B 0.96 . ? C14A H14C 0.96 . ? C15A H15A 0.96 . ? C15A H15B 0.96 . ? C15A H15C 0.96 . ? C16A H16A 0.96 . ? C16A H16B 0.96 . ? C16A H16C 0.96 . ? C13B C16B 1.501(14) . ? C13B C14B 1.513(14) . ? C13B C15B 1.517(14) . ? C14B H14D 0.96 . ? C14B H14E 0.96 . ? C14B H14F 0.96 . ? C15B H15D 0.96 . ? C15B H15E 0.96 . ? C15B H15F 0.96 . ? C16B H16D 0.96 . ? C16B H16E 0.96 . ? C16B H16F 0.96 . ? Cl1 Al1 2.134(2) . ? Cl2 Al1 2.109(2) . ? Cl3 Al1 2.117(3) . ? Cl4 Al1 2.100(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C1 108.7(4) . . ? C3 N1 C5 128.9(4) . . ? C1 N1 C5 122.3(4) . . ? C3 N2 C2 107.8(4) . . ? C3 N2 C9 127.2(4) . . ? C2 N2 C9 125.0(4) . . ? C4 N3 C13B 119.5(7) . . ? C4 N3 C13A 123.9(7) . . ? C13B N3 C13A 6.5(10) . . ? C2 C1 N1 106.1(5) . . ? C2 C1 H1 140(4) . . ? N1 C1 H1 114(4) . . ? C1 C2 N2 109.5(5) . . ? C1 C2 H2 125.3 . . ? N2 C2 H2 125.3 . . ? N2 C3 N1 107.9(4) . . ? N2 C3 C4 126.4(4) . . ? N1 C3 C4 125.7(5) . . ? N3 C4 C3 119.1(5) . . ? N3 C4 H4 126(4) . . ? C3 C4 H4 114(4) . . ? C6 C5 N1 111.3(5) . . ? C6 C5 C7A 112.3(9) . . ? N1 C5 C7A 114.6(8) . . ? C6 C5 C8A 107.4(8) . . ? N1 C5 C8A 102.1(8) . . ? C7A C5 C8A 108.3(8) . . ? C6 C5 C8B 113.7(9) . . ? N1 C5 C8B 116.6(9) . . ? C7A C5 C8B 86.1(11) . . ? C8A C5 C8B 22.5(12) . . ? C6 C5 C7B 107.0(8) . . ? N1 C5 C7B 99.9(7) . . ? C7A C5 C7B 21.2(9) . . ? C8A C5 C7B 128.2(10) . . ? C8B C5 C7B 106.7(8) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7A H7A1 109.5 . . ? C5 C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C5 C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C5 C8A H8A1 109.5 . . ? C5 C8A H8A2 109.5 . . ? H8A1 C8A H8A2 109.5 . . ? C5 C8A H8A3 109.5 . . ? H8A1 C8A H8A3 109.5 . . ? H8A2 C8A H8A3 109.5 . . ? C5 C7B H7B1 109.5 . . ? C5 C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C5 C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? C5 C8B H8B1 109.5 . . ? C5 C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C5 C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? C12 C9 C10 112.4(5) . . ? C12 C9 N2 108.5(5) . . ? C10 C9 N2 109.6(4) . . ? C12 C9 C11 110.2(5) . . ? C10 C9 C11 109.1(5) . . ? N2 C9 C11 106.9(5) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C13A C14A 114.0(12) . . ? N3 C13A C15A 104.6(12) . . ? C14A C13A C15A 112.7(12) . . ? N3 C13A C16A 107.2(12) . . ? C14A C13A C16A 109.2(12) . . ? C15A C13A C16A 109.0(12) . . ? C13A C14A H14A 109.5 . . ? C13A C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? C13A C14A H14C 109.5 . . ? H14A C14A H14C 109.5 . . ? H14B C14A H14C 109.5 . . ? C13A C15A H15A 109.5 . . ? C13A C15A H15B 109.5 . . ? H15A C15A H15B 109.5 . . ? C13A C15A H15C 109.5 . . ? H15A C15A H15C 109.5 . . ? H15B C15A H15C 109.5 . . ? C13A C16A H16A 109.5 . . ? C13A C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? C13A C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? N3 C13B C16B 106.9(13) . . ? N3 C13B C14B 115.8(13) . . ? C16B C13B C14B 110.5(12) . . ? N3 C13B C15B 106.2(13) . . ? C16B C13B C15B 109.9(12) . . ? C14B C13B C15B 107.4(12) . . ? C13B C14B H14D 109.5 . . ? C13B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C13B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? C13B C15B H15D 109.5 . . ? C13B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C13B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C13B C16B H16D 109.5 . . ? C13B C16B H16E 109.5 . . ? H16D C16B H16E 109.5 . . ? C13B C16B H16F 109.5 . . ? H16D C16B H16F 109.5 . . ? H16E C16B H16F 109.5 . . ? Cl4 Al1 Cl2 109.17(12) . . ? Cl4 Al1 Cl3 109.04(13) . . ? Cl2 Al1 Cl3 108.66(12) . . ? Cl4 Al1 Cl1 109.84(10) . . ? Cl2 Al1 Cl1 109.92(10) . . ? Cl3 Al1 Cl1 110.19(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C1 C2 1.4(6) . . . . ? C5 N1 C1 C2 179.7(5) . . . . ? N1 C1 C2 N2 -0.3(6) . . . . ? C3 N2 C2 C1 -1.0(6) . . . . ? C9 N2 C2 C1 179.3(5) . . . . ? C2 N2 C3 N1 1.9(5) . . . . ? C9 N2 C3 N1 -178.4(4) . . . . ? C2 N2 C3 C4 -175.6(5) . . . . ? C9 N2 C3 C4 4.1(8) . . . . ? C1 N1 C3 N2 -2.1(5) . . . . ? C5 N1 C3 N2 179.8(4) . . . . ? C1 N1 C3 C4 175.5(5) . . . . ? C5 N1 C3 C4 -2.7(8) . . . . ? C13B N3 C4 C3 177.3(7) . . . . ? C13A N3 C4 C3 -177.0(8) . . . . ? N2 C3 C4 N3 84.8(7) . . . . ? N1 C3 C4 N3 -92.3(7) . . . . ? C3 N1 C5 C6 -37.7(7) . . . . ? C1 N1 C5 C6 144.4(5) . . . . ? C3 N1 C5 C7A 91.2(10) . . . . ? C1 N1 C5 C7A -86.7(10) . . . . ? C3 N1 C5 C8A -152.0(9) . . . . ? C1 N1 C5 C8A 30.1(9) . . . . ? C3 N1 C5 C8B -170.4(9) . . . . ? C1 N1 C5 C8B 11.7(10) . . . . ? C3 N1 C5 C7B 75.1(8) . . . . ? C1 N1 C5 C7B -102.8(8) . . . . ? C3 N2 C9 C12 -80.4(6) . . . . ? C2 N2 C9 C12 99.3(6) . . . . ? C3 N2 C9 C10 42.7(7) . . . . ? C2 N2 C9 C10 -137.7(5) . . . . ? C3 N2 C9 C11 160.8(5) . . . . ? C2 N2 C9 C11 -19.5(7) . . . . ? C4 N3 C13A C14A 11.9(14) . . . . ? C13B N3 C13A C14A 61(9) . . . . ? C4 N3 C13A C15A -111.5(9) . . . . ? C13B N3 C13A C15A -62(9) . . . . ? C4 N3 C13A C16A 132.8(9) . . . . ? C13B N3 C13A C16A -178(10) . . . . ? C4 N3 C13B C16B 94.0(11) . . . . ? C13A N3 C13B C16B -39(8) . . . . ? C4 N3 C13B C14B -29.6(14) . . . . ? C13A N3 C13B C14B -163(10) . . . . ? C4 N3 C13B C15B -148.8(9) . . . . ? C13A N3 C13B C15B 78(9) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 960660' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_aflores322 _audit_creation_date 2013-08-26T11:29:00-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 14[I3]' _chemical_formula_moiety 'C16 H30 N3, I3' _chemical_formula_sum 'C16 H30 I3 N3' _chemical_formula_weight 645.13 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.533(2) _cell_length_b 11.4237(13) _cell_length_c 18.787(2) _cell_angle_alpha 90 _cell_angle_beta 125.466(8) _cell_angle_gamma 90 _cell_volume 2365.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 14411 _cell_measurement_theta_min 0.814 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Fragment _exptl_crystal_colour Red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.544 _exptl_absorpt_correction_T_max 0.888 #----------------------------------------------------------------------------# # 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 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.552556E-1 _diffrn_orient_matrix_ub_12 0.579735E-1 _diffrn_orient_matrix_ub_13 -0.5403E-3 _diffrn_orient_matrix_ub_21 0.234011E-1 _diffrn_orient_matrix_ub_22 -0.447152E-1 _diffrn_orient_matrix_ub_23 -0.481356E-1 _diffrn_orient_matrix_ub_31 -0.449525E-1 _diffrn_orient_matrix_ub_32 0.479834E-1 _diffrn_orient_matrix_ub_33 -0.442042E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_unetI/netI 0.1527 _diffrn_reflns_number 4431 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.45 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.573 _diffrn_measured_fraction_theta_max 0.573 _reflns_number_total 3093 _reflns_number_gt 1598 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1434P)^2^+27.4624P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.010(3) _refine_ls_number_reflns 3093 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.205 _refine_ls_R_factor_gt 0.109 _refine_ls_wR_factor_ref 0.3658 _refine_ls_wR_factor_gt 0.2556 _refine_ls_goodness_of_fit_ref 1.15 _refine_ls_restrained_S_all 1.15 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.043 _refine_diff_density_min -1.596 _refine_diff_density_rms 0.205 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4205(14) 0.1245(12) 0.5700(11) 0.056(4) Uani 1 1 d . . . N3 N 0.2369(19) 0.1563(13) 0.4559(10) 0.068(6) Uani 1 1 d . . . N8 N 0.2840(16) -0.1245(14) 0.4978(11) 0.060(5) Uani 1 1 d . . . C2 C 0.313(2) 0.0822(15) 0.5204(13) 0.062(6) Uani 1 1 d . . . C4 C 0.310(2) 0.252(2) 0.4679(17) 0.070(6) Uani 1 1 d . . . H4 H 0.2846 0.3188 0.4327 0.084 Uiso 1 1 calc R . . C5 C 0.420(3) 0.2333(19) 0.5360(16) 0.074(7) Uani 1 1 d . . . H5 H 0.4856 0.2832 0.5584 0.089 Uiso 1 1 calc R . . C7 C 0.2767(17) -0.035(2) 0.5333(14) 0.065(6) Uani 1 1 d . . . H7 H 0.2485 -0.0416 0.5679 0.078 Uiso 1 1 calc R . . C9 C 0.247(3) -0.2427(19) 0.5071(17) 0.074(7) Uani 1 1 d . . . C10 C 0.361(3) -0.318(2) 0.549(2) 0.100(11) Uani 1 1 d . . . H10A H 0.4306 -0.2686 0.5734 0.151 Uiso 1 1 calc R . . H10B H 0.3544 -0.3684 0.5058 0.151 Uiso 1 1 calc R . . H10C H 0.3684 -0.3646 0.5946 0.151 Uiso 1 1 calc R . . C11 C 0.155(3) -0.291(2) 0.4149(16) 0.097(11) Uani 1 1 d . . . H11A H 0.1811 -0.2731 0.3782 0.146 Uiso 1 1 calc R . . H11B H 0.0772 -0.2564 0.3909 0.146 Uiso 1 1 calc R . . H11C H 0.1492 -0.3746 0.4178 0.146 Uiso 1 1 calc R . . C12 C 0.197(3) -0.244(2) 0.561(2) 0.097(10) Uani 1 1 d . . . H12A H 0.1267 -0.1942 0.5336 0.145 Uiso 1 1 calc R . . H12B H 0.2571 -0.2164 0.6185 0.145 Uiso 1 1 calc R . . H12C H 0.1739 -0.3226 0.5635 0.145 Uiso 1 1 calc R . . C13 C 0.535(2) 0.0709(19) 0.6495(13) 0.076(8) Uani 1 1 d . . . C14 C 0.509(3) 0.023(4) 0.7127(19) 0.112(12) Uani 1 1 d . . . H14A H 0.4731 -0.0535 0.6939 0.168 Uiso 1 1 calc R . . H14B H 0.4534 0.0744 0.7137 0.168 Uiso 1 1 calc R . . H14C H 0.583 0.0179 0.7703 0.168 Uiso 1 1 calc R . . C15 C 0.633(3) 0.158(2) 0.696(2) 0.107(12) Uani 1 1 d . . . H15A H 0.6139 0.2115 0.726 0.16 Uiso 1 1 calc R . . H15B H 0.6397 0.1997 0.6551 0.16 Uiso 1 1 calc R . . H15C H 0.7077 0.1188 0.7378 0.16 Uiso 1 1 calc R . . C16 C 0.578(2) -0.027(2) 0.6210(18) 0.087(8) Uani 1 1 d . . . H16A H 0.5133 -0.0818 0.5865 0.13 Uiso 1 1 calc R . . H16B H 0.6451 -0.0661 0.6715 0.13 Uiso 1 1 calc R . . H16C H 0.6039 0.0038 0.5866 0.13 Uiso 1 1 calc R . . C17 C 0.109(3) 0.142(2) 0.3815(16) 0.083(9) Uani 1 1 d . . . C18 C 0.042(3) 0.091(3) 0.4155(17) 0.093(10) Uani 1 1 d . . . H18A H 0.0642 0.0103 0.4299 0.139 Uiso 1 1 calc R . . H18B H -0.0434 0.0973 0.3717 0.139 Uiso 1 1 calc R . . H18C H 0.0635 0.133 0.467 0.139 Uiso 1 1 calc R . . C19 C 0.101(3) 0.062(3) 0.3149(19) 0.093(9) Uani 1 1 d . . . H19A H 0.1493 -0.0071 0.3438 0.14 Uiso 1 1 calc R . . H19B H 0.1312 0.101 0.286 0.14 Uiso 1 1 calc R . . H19C H 0.0182 0.0391 0.2727 0.14 Uiso 1 1 calc R . . C20 C 0.052(3) 0.259(2) 0.3424(17) 0.088(8) Uani 1 1 d . . . H20A H 0.09 0.2925 0.3169 0.131 Uiso 1 1 calc R . . H20B H 0.0635 0.3098 0.3872 0.131 Uiso 1 1 calc R . . H20C H -0.0328 0.2487 0.2981 0.131 Uiso 1 1 calc R . . I1 I 0.3040(2) 0.50876(14) 0.31412(13) 0.0960(9) Uani 1 1 d . . . I2 I 0.22607(15) 0.30277(11) 0.19745(10) 0.0743(8) Uani 1 1 d . . . I3 I 0.1469(2) 0.09755(14) 0.08708(13) 0.1003(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.036(9) 0.051(8) 0.063(9) -0.006(7) 0.019(8) -0.010(6) N3 0.077(13) 0.052(8) 0.038(8) -0.007(6) 0.013(8) -0.007(8) N8 0.040(9) 0.056(9) 0.058(9) 0.010(7) 0.013(8) 0.000(7) C2 0.058(13) 0.045(9) 0.061(11) 0.016(8) 0.022(10) 0.005(8) C4 0.066(16) 0.075(13) 0.091(17) 0.021(12) 0.058(15) 0.010(11) C5 0.077(18) 0.063(12) 0.074(14) 0.000(10) 0.039(14) -0.004(11) C7 0.026(9) 0.085(14) 0.065(12) 0.004(11) 0.015(10) -0.006(9) C9 0.075(16) 0.065(12) 0.091(16) -0.035(11) 0.053(14) -0.022(11) C10 0.070(18) 0.061(13) 0.11(2) 0.034(13) 0.017(16) 0.005(11) C11 0.08(2) 0.077(14) 0.071(15) -0.026(12) 0.010(15) -0.011(13) C12 0.13(3) 0.051(12) 0.11(2) 0.006(12) 0.07(2) -0.017(13) C13 0.068(16) 0.072(12) 0.049(11) -0.020(10) 0.012(11) -0.011(11) C14 0.045(14) 0.19(3) 0.075(17) 0.040(19) 0.021(13) 0.002(17) C15 0.053(16) 0.090(16) 0.11(2) -0.038(16) 0.010(15) -0.001(13) C16 0.026(10) 0.102(16) 0.099(18) 0.020(14) 0.017(11) 0.018(10) C17 0.061(16) 0.080(14) 0.071(14) 0.033(12) 0.017(13) -0.008(12) C18 0.059(16) 0.12(2) 0.064(14) -0.011(13) 0.018(13) 0.028(15) C19 0.062(16) 0.11(2) 0.087(17) -0.005(15) 0.033(14) 0.006(15) C20 0.072(18) 0.101(17) 0.075(15) 0.031(13) 0.035(14) 0.015(13) I1 0.0930(15) 0.0645(10) 0.1107(15) -0.0168(8) 0.0478(12) -0.0101(8) I2 0.0645(11) 0.0574(9) 0.0816(12) 0.0041(6) 0.0313(9) 0.0020(6) I3 0.0934(16) 0.0709(11) 0.0897(13) -0.0094(8) 0.0263(12) 0.0158(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.28(3) . ? N1 C5 1.39(3) . ? N1 C13 1.52(3) . ? N3 C2 1.34(2) . ? N3 C4 1.41(3) . ? N3 C17 1.47(3) . ? N8 C7 1.26(3) . ? N8 C9 1.48(3) . ? C2 C7 1.49(3) . ? C4 C5 1.29(3) . ? C4 H4 0.93 . ? C5 H5 0.93 . ? C7 H7 0.93 . ? C9 C12 1.51(5) . ? C9 C10 1.52(4) . ? C9 C11 1.54(3) . ? C10 H10A 0.96 . ? C10 H10B 0.96 . ? C10 H10C 0.96 . ? C11 H11A 0.96 . ? C11 H11B 0.96 . ? C11 H11C 0.96 . ? C12 H12A 0.96 . ? C12 H12B 0.96 . ? C12 H12C 0.96 . ? C13 C15 1.47(3) . ? C13 C16 1.50(4) . ? C13 C14 1.53(4) . ? C14 H14A 0.96 . ? C14 H14B 0.96 . ? C14 H14C 0.96 . ? C15 H15A 0.96 . ? C15 H15B 0.96 . ? C15 H15C 0.96 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 C18 1.49(5) . ? C17 C20 1.50(3) . ? C17 C19 1.51(4) . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? I1 I2 2.962(2) . ? I2 I3 2.892(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 107.4(17) . . ? C2 N1 C13 129.8(17) . . ? C5 N1 C13 122.7(18) . . ? C2 N3 C4 104.3(18) . . ? C2 N3 C17 130.8(18) . . ? C4 N3 C17 124.6(17) . . ? C7 N8 C9 123(2) . . ? N1 C2 N3 111.8(17) . . ? N1 C2 C7 124.1(16) . . ? N3 C2 C7 124(2) . . ? C5 C4 N3 109(2) . . ? C5 C4 H4 125.6 . . ? N3 C4 H4 125.6 . . ? C4 C5 N1 108(2) . . ? C4 C5 H5 126.1 . . ? N1 C5 H5 126.1 . . ? N8 C7 C2 121(2) . . ? N8 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? N8 C9 C12 113.5(19) . . ? N8 C9 C10 106(2) . . ? C12 C9 C10 111(3) . . ? N8 C9 C11 108(2) . . ? C12 C9 C11 111(3) . . ? C10 C9 C11 107(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C15 C13 C16 109(3) . . ? C15 C13 N1 111(2) . . ? C16 C13 N1 109.7(17) . . ? C15 C13 C14 108(2) . . ? C16 C13 C14 109(3) . . ? N1 C13 C14 110(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C17 C18 108(2) . . ? N3 C17 C20 111(2) . . ? C18 C17 C20 107(3) . . ? N3 C17 C19 109(3) . . ? C18 C17 C19 110(2) . . ? C20 C17 C19 112(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? I3 I2 I1 177.86(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 N3 -2(3) . . . . ? C13 N1 C2 N3 -179(2) . . . . ? C5 N1 C2 C7 179(2) . . . . ? C13 N1 C2 C7 1(4) . . . . ? C4 N3 C2 N1 2(3) . . . . ? C17 N3 C2 N1 176(3) . . . . ? C4 N3 C2 C7 -178(2) . . . . ? C17 N3 C2 C7 -5(5) . . . . ? C2 N3 C4 C5 -1(3) . . . . ? C17 N3 C4 C5 -176(3) . . . . ? N3 C4 C5 N1 0(3) . . . . ? C2 N1 C5 C4 1(3) . . . . ? C13 N1 C5 C4 178(2) . . . . ? C9 N8 C7 C2 -179.0(19) . . . . ? N1 C2 C7 N8 -90(3) . . . . ? N3 C2 C7 N8 90(3) . . . . ? C7 N8 C9 C12 2(3) . . . . ? C7 N8 C9 C10 -120(2) . . . . ? C7 N8 C9 C11 125(2) . . . . ? C2 N1 C13 C15 -170(3) . . . . ? C5 N1 C13 C15 14(4) . . . . ? C2 N1 C13 C16 70(4) . . . . ? C5 N1 C13 C16 -106(3) . . . . ? C2 N1 C13 C14 -50(4) . . . . ? C5 N1 C13 C14 134(3) . . . . ? C2 N3 C17 C18 46(4) . . . . ? C4 N3 C17 C18 -141(2) . . . . ? C2 N3 C17 C20 163(3) . . . . ? C4 N3 C17 C20 -24(4) . . . . ? C2 N3 C17 C19 -73(4) . . . . ? C4 N3 C17 C19 99(3) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 960661' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_rosalinda857 _audit_creation_date 2013-06-22T23:15:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common 'Compound 17' _chemical_formula_moiety 'C24 H30 Cl5 In N2 O, C4 H8 O' _chemical_formula_sum 'C28 H38 Cl5 In N2 O2' _chemical_formula_weight 726.67 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _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 6.9619(2) _cell_length_b 13.4095(5) _cell_length_c 35.1631(9) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 90.000 _cell_volume 3282.67(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 22094 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.47 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.933 _exptl_absorpt_correction_T_max 0.944 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.603981E-1 _diffrn_orient_matrix_ub_12 0.668545E-1 _diffrn_orient_matrix_ub_13 -0.3972E-2 _diffrn_orient_matrix_ub_21 -0.559208E-1 _diffrn_orient_matrix_ub_22 0.236639E-1 _diffrn_orient_matrix_ub_23 0.245917E-1 _diffrn_orient_matrix_ub_31 0.117716 _diffrn_orient_matrix_ub_32 -0.230603E-1 _diffrn_orient_matrix_ub_33 0.137202E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0877 _diffrn_reflns_av_unetI/netI 0.1974 _diffrn_reflns_number 14201 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.16 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 7082 _reflns_number_gt 3687 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7082 _refine_ls_number_parameters 428 _refine_ls_number_restraints 438 _refine_ls_R_factor_all 0.1719 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.1444 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0 _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 0.07(4) _refine_diff_density_max 0.899 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.128 #----------------------------------------------------------------------------# # 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' In In -0.7276 1.31 '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 C1 C -0.0606(13) 0.5618(7) 0.4499(2) 0.038(2) Uani 1 1 d D . . H1 H 0.073 0.5443 0.4442 0.045 Uiso 1 1 calc R A 1 C2 C -0.1812(14) 0.4681(6) 0.4424(2) 0.039(2) Uani 1 1 d D B . H2 H -0.3171 0.487 0.4414 0.046 Uiso 1 1 calc R . . C3 C -0.2465(13) 0.4340(6) 0.3798(2) 0.031(2) Uani 1 1 d D B . H3 H -0.3659 0.4622 0.3848 0.038 Uiso 1 1 calc R . . C4 C -0.2009(13) 0.3966(6) 0.3405(2) 0.031(2) Uani 1 1 d . B . H4 H -0.2911 0.4031 0.3212 0.038 Uiso 1 1 calc R . . C5 C 0.0049(14) 0.3301(7) 0.2936(2) 0.038(3) Uani 1 1 d . B . H5 H -0.1087 0.3439 0.278 0.046 Uiso 1 1 calc R . . C6 C 0.0482(13) 0.2187(7) 0.2912(2) 0.038(2) Uani 1 1 d . . . H6 H 0.1386 0.2025 0.3116 0.046 Uiso 1 1 calc R . . C7 C 0.1375(14) 0.1860(7) 0.2542(2) 0.037(2) Uani 1 1 d . . . C8 C 0.0298(15) 0.1868(7) 0.2207(3) 0.047(3) Uani 1 1 d . . . H8 H -0.0992 0.2048 0.2211 0.057 Uiso 1 1 calc R . . C9 C 0.1165(17) 0.1607(8) 0.1876(3) 0.060(4) Uani 1 1 d . . . H9 H 0.044 0.1595 0.1654 0.072 Uiso 1 1 calc R . . C10 C 0.3084(16) 0.1361(8) 0.1858(2) 0.053(3) Uani 1 1 d . . . H10 H 0.3666 0.1225 0.1626 0.064 Uiso 1 1 calc R . . C11 C 0.4127(14) 0.1320(7) 0.2192(3) 0.048(3) Uani 1 1 d . . . H11 H 0.5405 0.1119 0.2187 0.057 Uiso 1 1 calc R . . C12 C 0.3276(15) 0.1577(6) 0.2532(2) 0.043(2) Uani 1 1 d . . . H12 H 0.3989 0.1559 0.2755 0.051 Uiso 1 1 calc R . . C13 C -0.060(4) 0.611(2) 0.4884(5) 0.038(5) Uani 0.5 1 d PGU B 1 C14 C -0.224(3) 0.6569(18) 0.5026(6) 0.040(5) Uani 0.5 1 d PGU B 1 H14 H -0.3327 0.6622 0.4875 0.049 Uiso 0.5 1 calc PR B 1 C15 C -0.2245(19) 0.6947(14) 0.5394(6) 0.040(4) Uani 0.5 1 d PGU B 1 H15 H -0.3343 0.7253 0.5489 0.048 Uiso 0.5 1 calc PR B 1 C16 C -0.061(2) 0.6867(15) 0.5620(5) 0.041(5) Uani 0.5 1 d PGU B 1 H16 H -0.062 0.712 0.5866 0.049 Uiso 0.5 1 calc PR B 1 C17 C 0.103(2) 0.6409(19) 0.5478(6) 0.048(5) Uani 0.5 1 d PGU B 1 H17 H 0.2118 0.6355 0.5629 0.058 Uiso 0.5 1 calc PR B 1 C18 C 0.104(3) 0.603(2) 0.5110(6) 0.044(5) Uani 0.5 1 d PGU B 1 H18 H 0.2134 0.5724 0.5015 0.053 Uiso 0.5 1 calc PR B 1 C13A C -0.104(4) 0.600(2) 0.4902(5) 0.042(5) Uani 0.5 1 d PGU B 2 C14A C -0.284(3) 0.6356(18) 0.5001(6) 0.043(5) Uani 0.5 1 d PGU B 2 H14A H -0.3846 0.6328 0.4827 0.052 Uiso 0.5 1 calc PR B 2 C15A C -0.315(2) 0.6755(14) 0.5361(6) 0.048(5) Uani 0.5 1 d PGU B 2 H15A H -0.4359 0.6995 0.5427 0.057 Uiso 0.5 1 calc PR B 2 C16A C -0.165(2) 0.6797(15) 0.5621(5) 0.048(5) Uani 0.5 1 d PGU B 2 H16A H -0.1858 0.7064 0.5862 0.058 Uiso 0.5 1 calc PR B 2 C17A C 0.015(2) 0.6439(19) 0.5523(6) 0.051(5) Uani 0.5 1 d PGU B 2 H17A H 0.1156 0.6466 0.5697 0.061 Uiso 0.5 1 calc PR B 2 C18A C 0.046(3) 0.604(2) 0.5163(6) 0.045(5) Uani 0.5 1 d PGU B 2 H18A H 0.1669 0.58 0.5097 0.054 Uiso 0.5 1 calc PR B 2 C19 C -0.1537(15) 0.3913(6) 0.4740(2) 0.043(3) Uani 1 1 d . . . H19A H -0.2337 0.3344 0.4691 0.064 Uiso 1 1 calc R B . H19B H -0.1885 0.4203 0.4979 0.064 Uiso 1 1 calc R . . H19C H -0.0216 0.3708 0.4747 0.064 Uiso 1 1 calc R . . C20 C 0.1671(15) 0.3939(6) 0.2794(2) 0.047(3) Uani 1 1 d . . . H20A H 0.1306 0.4629 0.2808 0.071 Uiso 1 1 calc R . . H20B H 0.1954 0.3768 0.2535 0.071 Uiso 1 1 calc R . . H20C H 0.2788 0.3829 0.2948 0.071 Uiso 1 1 calc R . . C21 C 0.159(3) 0.1397(17) 0.4201(5) 0.046(4) Uani 0.5 1 d PDU C 1 H21A H 0.238 0.1616 0.4411 0.055 Uiso 0.5 1 calc PR C 1 H21B H 0.2391 0.1128 0.4 0.055 Uiso 0.5 1 calc PR C 1 C22 C 0.008(3) 0.067(2) 0.4324(6) 0.054(4) Uani 0.5 1 d PDU C 1 H22A H 0.0266 0.0542 0.4593 0.065 Uiso 0.5 1 calc PR C 1 H22B H 0.0306 0.0049 0.4192 0.065 Uiso 0.5 1 calc PR C 1 C23 C -0.205(3) 0.0947(14) 0.4267(5) 0.060(4) Uani 0.5 1 d PDU C 1 H23A H -0.2757 0.0442 0.4127 0.072 Uiso 0.5 1 calc PR C 1 H23B H -0.2702 0.1096 0.4504 0.072 Uiso 0.5 1 calc PR C 1 C21A C 0.122(3) 0.1510(19) 0.4333(6) 0.054(4) Uani 0.5 1 d PDU C 2 H21C H 0.1626 0.1877 0.4557 0.065 Uiso 0.5 1 calc PR C 2 H21D H 0.234 0.1203 0.422 0.065 Uiso 0.5 1 calc PR C 2 C22A C -0.020(3) 0.072(3) 0.4446(5) 0.056(4) Uani 0.5 1 d PDU C 2 H22C H -0.089 0.089 0.4677 0.068 Uiso 0.5 1 calc PR C 2 H22D H 0.0408 0.007 0.4477 0.068 Uiso 0.5 1 calc PR C 2 C23A C -0.154(3) 0.0753(11) 0.4082(5) 0.054(4) Uani 0.5 1 d PDU C 2 H23C H -0.0953 0.0431 0.3864 0.065 Uiso 0.5 1 calc PR C 2 H23D H -0.2791 0.0458 0.413 0.065 Uiso 0.5 1 calc PR C 2 O1 O 0.0333(8) 0.2188(5) 0.40629(17) 0.0449(18) Uani 1 1 d D . . C24 C -0.1667(15) 0.1869(7) 0.4032(3) 0.053(3) Uani 1 1 d D C . H24A H -0.1965 0.1732 0.3768 0.064 Uiso 1 1 calc R D 1 H24B H -0.2499 0.2404 0.4118 0.064 Uiso 1 1 calc R D 1 O2 O 0.241(3) 1.0018(11) 0.3374(5) 0.115(4) Uani 0.5 1 d PGU E 1 C25 C 0.194(3) 0.9403(16) 0.3059(5) 0.120(4) Uani 0.5 1 d PGU E 1 H25A H 0.0881 0.8964 0.3124 0.144 Uiso 0.5 1 calc PR E 1 H25B H 0.1553 0.9812 0.2844 0.144 Uiso 0.5 1 calc PR E 1 C26 C 0.359(3) 0.8835(16) 0.2964(5) 0.118(4) Uani 0.5 1 d PGU E 1 H26A H 0.3981 0.8976 0.2704 0.142 Uiso 0.5 1 calc PR E 1 H26B H 0.3309 0.8128 0.2984 0.142 Uiso 0.5 1 calc PR E 1 C27 C 0.508(2) 0.9098(18) 0.3220(7) 0.117(4) Uani 0.5 1 d PGU E 1 H27A H 0.5501 0.8515 0.3361 0.141 Uiso 0.5 1 calc PR E 1 H27B H 0.6173 0.9363 0.3081 0.141 Uiso 0.5 1 calc PR E 1 C28 C 0.435(3) 0.9829(15) 0.3474(5) 0.112(4) Uani 0.5 1 d PGU E 1 H28A H 0.5099 1.0437 0.3454 0.134 Uiso 0.5 1 calc PR E 1 H28B H 0.4427 0.9589 0.3734 0.134 Uiso 0.5 1 calc PR E 1 O2A O 0.163(2) 0.9105(14) 0.3232(5) 0.126(4) Uani 0.5 1 d PGU F 2 C25A C 0.254(3) 0.8940(16) 0.2876(4) 0.113(4) Uani 0.5 1 d PGU F 2 H25C H 0.2275 0.827 0.2787 0.136 Uiso 0.5 1 calc PR F 2 H25D H 0.206 0.9409 0.2688 0.136 Uiso 0.5 1 calc PR F 2 C27A C 0.455(3) 0.907(2) 0.2927(5) 0.116(4) Uani 0.5 1 d PGU F 2 H27C H 0.5225 0.8464 0.2861 0.14 Uiso 0.5 1 calc PR F 2 H27D H 0.501 0.9603 0.2763 0.14 Uiso 0.5 1 calc PR F 2 C26A C 0.488(2) 0.932(2) 0.3314(6) 0.120(4) Uani 0.5 1 d PGU F 2 H26C H 0.571 0.8826 0.3431 0.144 Uiso 0.5 1 calc PR F 2 H26D H 0.5496 0.9965 0.3332 0.144 Uiso 0.5 1 calc PR F 2 C28A C 0.307(3) 0.9339(15) 0.3502(4) 0.122(4) Uani 0.5 1 d PGU F 2 H28C H 0.2845 0.9995 0.3609 0.147 Uiso 0.5 1 calc PR F 2 H28D H 0.306 0.8856 0.3708 0.147 Uiso 0.5 1 calc PR F 2 Cl1 Cl -0.1327(4) 0.65435(17) 0.41499(5) 0.0473(7) Uani 1 1 d . B . Cl2 Cl -0.1732(4) 0.14965(19) 0.30021(6) 0.0531(7) Uani 1 1 d . . . Cl3 Cl 0.2720(3) 0.53046(17) 0.36599(7) 0.0450(7) Uani 1 1 d . . . Cl4 Cl 0.3333(4) 0.3756(2) 0.44806(5) 0.0479(6) Uani 1 1 d . . . Cl5 Cl 0.4168(3) 0.26582(19) 0.35658(6) 0.0430(6) Uani 1 1 d . . . In1 In 0.16973(9) 0.36549(5) 0.387003(15) 0.03326(19) Uani 1 1 d . B . N1 N -0.1257(10) 0.4274(5) 0.40572(19) 0.0300(19) Uani 1 1 d . . . N2 N -0.0408(10) 0.3566(5) 0.33380(16) 0.0289(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(6) 0.057(7) 0.033(5) 0.000(5) 0.001(4) 0.000(5) C2 0.018(5) 0.066(7) 0.032(5) -0.007(5) 0.005(5) 0.003(6) C3 0.030(5) 0.034(5) 0.030(5) 0.001(4) 0.002(4) 0.002(4) C4 0.033(6) 0.027(5) 0.035(5) 0.004(4) -0.011(4) 0.003(5) C5 0.042(7) 0.045(7) 0.027(5) -0.002(4) -0.001(5) 0.000(5) C6 0.026(6) 0.049(7) 0.040(5) -0.011(5) -0.001(5) -0.002(5) C7 0.033(7) 0.040(6) 0.039(5) -0.001(4) 0.006(5) -0.003(5) C8 0.042(7) 0.062(7) 0.038(6) -0.005(5) 0.008(5) -0.004(6) C9 0.071(10) 0.080(9) 0.029(5) -0.011(5) 0.001(5) -0.016(7) C10 0.063(8) 0.052(6) 0.045(6) -0.013(5) 0.025(6) -0.017(9) C11 0.047(6) 0.042(6) 0.054(6) -0.012(6) 0.013(5) 0.016(6) C12 0.036(6) 0.050(6) 0.042(5) -0.012(4) -0.007(6) 0.002(7) C13 0.044(12) 0.036(9) 0.036(7) 0.000(7) 0.015(8) -0.015(9) C14 0.054(13) 0.031(9) 0.037(7) 0.005(7) 0.014(8) -0.009(9) C15 0.050(12) 0.033(8) 0.037(7) -0.003(7) 0.013(9) -0.015(8) C16 0.053(13) 0.042(8) 0.029(7) 0.000(7) 0.023(9) -0.015(10) C17 0.055(13) 0.052(8) 0.037(8) 0.009(8) 0.002(9) -0.010(11) C18 0.051(12) 0.046(8) 0.036(8) 0.001(7) 0.008(8) -0.011(9) C13A 0.052(13) 0.033(8) 0.042(7) 0.005(7) 0.014(8) -0.017(9) C14A 0.057(12) 0.036(10) 0.038(7) -0.003(7) 0.008(8) -0.017(10) C15A 0.065(12) 0.037(9) 0.041(7) 0.005(7) 0.022(10) -0.009(10) C16A 0.066(13) 0.039(8) 0.040(8) 0.001(7) 0.015(11) -0.021(11) C17A 0.061(12) 0.053(8) 0.038(7) -0.003(7) 0.016(9) -0.018(10) C18A 0.055(13) 0.044(8) 0.037(8) -0.010(7) 0.011(8) -0.015(9) C19 0.053(7) 0.044(6) 0.031(4) -0.002(4) -0.009(5) -0.004(6) C20 0.052(7) 0.055(7) 0.036(5) 0.004(4) 0.005(6) 0.000(7) C21 0.051(8) 0.060(8) 0.026(9) 0.034(9) 0.008(8) 0.006(8) C22 0.057(8) 0.064(7) 0.042(9) 0.033(8) 0.009(7) 0.001(6) C23 0.061(8) 0.069(8) 0.049(9) 0.040(8) 0.009(8) -0.005(7) C21A 0.055(9) 0.064(8) 0.043(10) 0.035(8) 0.004(8) -0.001(7) C22A 0.060(8) 0.068(7) 0.042(9) 0.035(8) 0.009(7) -0.003(7) C23A 0.057(8) 0.063(8) 0.041(9) 0.030(8) 0.011(7) -0.001(7) O1 0.026(4) 0.048(4) 0.060(4) 0.019(3) -0.013(3) -0.008(3) C24 0.041(7) 0.052(6) 0.067(6) -0.003(5) -0.016(6) -0.005(7) O2 0.117(9) 0.115(8) 0.113(8) -0.035(7) -0.006(8) 0.006(8) C25 0.121(9) 0.116(8) 0.124(9) -0.027(7) -0.003(8) -0.002(9) C26 0.119(9) 0.115(8) 0.121(8) -0.042(6) 0.000(7) -0.001(8) C27 0.119(9) 0.115(8) 0.118(9) -0.041(7) -0.004(8) 0.000(9) C28 0.114(9) 0.113(9) 0.109(8) -0.036(7) -0.006(8) -0.003(9) O2A 0.124(9) 0.126(8) 0.128(8) -0.034(7) -0.002(7) -0.004(8) C25A 0.116(9) 0.110(8) 0.114(8) -0.040(7) -0.001(8) -0.003(9) C27A 0.120(9) 0.112(8) 0.118(8) -0.042(7) 0.005(8) 0.000(9) C26A 0.119(9) 0.122(8) 0.119(8) -0.034(7) -0.004(8) -0.001(8) C28A 0.123(9) 0.128(9) 0.115(8) -0.029(7) -0.005(8) 0.002(9) Cl1 0.066(2) 0.0458(15) 0.0307(11) 0.0029(10) -0.0018(12) -0.0002(15) Cl2 0.0423(15) 0.0656(18) 0.0513(13) -0.0096(12) 0.0089(14) -0.0115(18) Cl3 0.0346(15) 0.0464(16) 0.0538(14) 0.0044(12) 0.0037(12) -0.0049(13) Cl4 0.0337(13) 0.0744(17) 0.0358(11) -0.0026(12) -0.0113(12) -0.0051(19) Cl5 0.0308(14) 0.0520(16) 0.0462(14) -0.0096(12) -0.0004(12) 0.0077(12) In1 0.0245(3) 0.0434(4) 0.0318(3) -0.0002(3) -0.0011(3) -0.0010(4) N1 0.026(5) 0.031(4) 0.034(4) 0.005(3) 0.002(4) 0.001(4) N2 0.026(4) 0.034(4) 0.027(4) -0.004(4) -0.003(3) 0.012(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 C13 1.504(18) . ? C1 C13A 1.534(18) . ? C1 C2 1.535(10) . ? C1 Cl1 1.817(9) . ? C1 H1 0.98 . ? C2 N1 1.453(9) . ? C2 C19 1.526(10) . ? C2 H2 0.98 . ? C3 N1 1.242(9) . ? C3 C4 1.504(10) . ? C3 H3 0.93 . ? C4 N2 1.259(10) . ? C4 H4 0.93 . ? C5 N2 1.492(9) . ? C5 C20 1.502(12) . ? C5 C6 1.527(12) . ? C5 H5 0.98 . ? C6 C7 1.506(11) . ? C6 Cl2 1.825(9) . ? C6 H6 0.98 . ? C7 C12 1.377(12) . ? C7 C8 1.397(12) . ? C8 C9 1.357(12) . ? C8 H8 0.93 . ? C9 C10 1.378(13) . ? C9 H9 0.93 . ? C10 C11 1.381(12) . ? C10 H10 0.93 . ? C11 C12 1.377(11) . ? C11 H11 0.93 . ? C12 H12 0.93 . ? C13 C14 1.39 . ? C13 C18 1.39 . ? C14 C15 1.39 . ? C14 H14 0.93 . ? C15 C16 1.39 . ? C15 H15 0.93 . ? C16 C17 1.39 . ? C16 H16 0.93 . ? C17 C18 1.39 . ? C17 H17 0.93 . ? C18 H18 0.93 . ? C13A C14A 1.39 . ? C13A C18A 1.39 . ? C14A C15A 1.39 . ? C14A H14A 0.93 . ? C15A C16A 1.39 . ? C15A H15A 0.93 . ? C16A C17A 1.39 . ? C16A H16A 0.93 . ? C17A C18A 1.39 . ? C17A H17A 0.93 . ? C18A H18A 0.93 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? C21 O1 1.456(13) . ? C21 C22 1.497(14) . ? C21 H21A 0.97 . ? C21 H21B 0.97 . ? C22 C23 1.540(10) . ? C22 H22A 0.97 . ? C22 H22B 0.97 . ? C23 C24 1.510(13) . ? C23 H23A 0.97 . ? C23 H23B 0.97 . ? C21A O1 1.452(13) . ? C21A C22A 1.505(15) . ? C21A H21C 0.97 . ? C21A H21D 0.97 . ? C22A C23A 1.586(10) . ? C22A H22C 0.97 . ? C22A H22D 0.97 . ? C23A C24 1.510(14) . ? C23A H23C 0.97 . ? C23A H23D 0.97 . ? O1 C24 1.461(10) . ? O1 In1 2.287(6) . ? C24 H24A 0.97 . ? C24 H24B 0.97 . ? O2 C28 1.42 . ? O2 C25 1.42 . ? C25 C26 1.42 . ? C25 H25A 0.97 . ? C25 H25B 0.97 . ? C26 C27 1.42 . ? C26 H26A 0.97 . ? C26 H26B 0.97 . ? C27 C28 1.42 . ? C27 H27A 0.97 . ? C27 H27B 0.97 . ? C28 H28A 0.97 . ? C28 H28B 0.97 . ? O2A C28A 1.42 . ? O2A C25A 1.42 . ? C25A C27A 1.42 . ? C25A H25C 0.97 . ? C25A H25D 0.97 . ? C27A C26A 1.42 . ? C27A H27C 0.97 . ? C27A H27D 0.97 . ? C26A C28A 1.42 . ? C26A H26C 0.97 . ? C26A H26D 0.97 . ? C28A H28C 0.97 . ? C28A H28D 0.97 . ? Cl3 In1 2.438(2) . ? Cl4 In1 2.434(2) . ? Cl5 In1 2.427(2) . ? In1 N1 2.313(7) . ? In1 N2 2.380(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 C1 C13A 13.1(19) . . ? C13 C1 C2 121.1(13) . . ? C13A C1 C2 108.9(12) . . ? C13 C1 Cl1 108.0(13) . . ? C13A C1 Cl1 110.1(13) . . ? C2 C1 Cl1 106.9(6) . . ? C13 C1 H1 106.6 . . ? C13A C1 H1 117.1 . . ? C2 C1 H1 106.6 . . ? Cl1 C1 H1 106.6 . . ? N1 C2 C19 111.0(7) . . ? N1 C2 C1 108.4(7) . . ? C19 C2 C1 111.0(7) . . ? N1 C2 H2 108.8 . . ? C19 C2 H2 108.8 . . ? C1 C2 H2 108.8 . . ? N1 C3 C4 120.5(8) . . ? N1 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? N2 C4 C3 120.1(7) . . ? N2 C4 H4 120 . . ? C3 C4 H4 120 . . ? N2 C5 C20 109.8(7) . . ? N2 C5 C6 109.1(7) . . ? C20 C5 C6 113.0(8) . . ? N2 C5 H5 108.3 . . ? C20 C5 H5 108.3 . . ? C6 C5 H5 108.3 . . ? C7 C6 C5 114.4(7) . . ? C7 C6 Cl2 110.5(6) . . ? C5 C6 Cl2 108.7(7) . . ? C7 C6 H6 107.6 . . ? C5 C6 H6 107.6 . . ? Cl2 C6 H6 107.6 . . ? C12 C7 C8 119.7(9) . . ? C12 C7 C6 120.0(8) . . ? C8 C7 C6 120.3(9) . . ? C9 C8 C7 118.9(10) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 122.1(9) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C9 C10 C11 118.7(9) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 120.1(9) . . ? C12 C11 H11 120 . . ? C10 C11 H11 120 . . ? C11 C12 C7 120.4(9) . . ? C11 C12 H12 119.8 . . ? C7 C12 H12 119.8 . . ? C14 C13 C18 120 . . ? C14 C13 C1 120.9(15) . . ? C18 C13 C1 118.9(15) . . ? C15 C14 C13 120 . . ? C15 C14 H14 120 . . ? C13 C14 H14 120 . . ? C14 C15 C16 120 . . ? C14 C15 H15 120 . . ? C16 C15 H15 120 . . ? C15 C16 C17 120 . . ? C15 C16 H16 120 . . ? C17 C16 H16 120 . . ? C16 C17 C18 120 . . ? C16 C17 H17 120 . . ? C18 C17 H17 120 . . ? C17 C18 C13 120 . . ? C17 C18 H18 120 . . ? C13 C18 H18 120 . . ? C14A C13A C18A 120 . . ? C14A C13A C1 121.5(15) . . ? C18A C13A C1 118.4(15) . . ? C15A C14A C13A 120 . . ? C15A C14A H14A 120 . . ? C13A C14A H14A 120 . . ? C16A C15A C14A 120 . . ? C16A C15A H15A 120 . . ? C14A C15A H15A 120 . . ? C15A C16A C17A 120 . . ? C15A C16A H16A 120 . . ? C17A C16A H16A 120 . . ? C16A C17A C18A 120 . . ? C16A C17A H17A 120 . . ? C18A C17A H17A 120 . . ? C17A C18A C13A 120 . . ? C17A C18A H18A 120 . . ? C13A C18A H18A 120 . . ? C2 C19 H19A 109.5 . . ? C2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C5 C20 H20A 109.5 . . ? C5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C5 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 C22 98.6(18) . . ? O1 C21 H21A 112 . . ? C22 C21 H21A 112 . . ? O1 C21 H21B 112 . . ? C22 C21 H21B 112 . . ? H21A C21 H21B 109.7 . . ? C21 C22 C23 119(2) . . ? C21 C22 H22A 107.6 . . ? C23 C22 H22A 107.6 . . ? C21 C22 H22B 107.6 . . ? C23 C22 H22B 107.6 . . ? H22A C22 H22B 107.1 . . ? C24 C23 C22 95.6(16) . . ? C24 C23 H23A 112.6 . . ? C22 C23 H23A 112.6 . . ? C24 C23 H23B 112.6 . . ? C22 C23 H23B 112.6 . . ? H23A C23 H23B 110.1 . . ? O1 C21A C22A 109.8(18) . . ? O1 C21A H21C 109.7 . . ? C22A C21A H21C 109.7 . . ? O1 C21A H21D 109.7 . . ? C22A C21A H21D 109.7 . . ? H21C C21A H21D 108.2 . . ? C21A C22A C23A 98.7(18) . . ? C21A C22A H22C 112 . . ? C23A C22A H22C 112 . . ? C21A C22A H22D 112 . . ? C23A C22A H22D 112 . . ? H22C C22A H22D 109.7 . . ? C24 C23A C22A 99.1(16) . . ? C24 C23A H23C 112 . . ? C22A C23A H23C 112 . . ? C24 C23A H23D 112 . . ? C22A C23A H23D 112 . . ? H23C C23A H23D 109.6 . . ? C21A O1 C21 21.9(13) . . ? C21A O1 C24 105.6(12) . . ? C21 O1 C24 112.4(12) . . ? C21A O1 In1 123.8(12) . . ? C21 O1 In1 118.5(11) . . ? C24 O1 In1 128.8(5) . . ? O1 C24 C23A 103.2(12) . . ? O1 C24 C23 111.7(10) . . ? C23A C24 C23 30.2(10) . . ? O1 C24 H24A 109.3 . . ? C23A C24 H24A 86.3 . . ? C23 C24 H24A 109.3 . . ? O1 C24 H24B 109.3 . . ? C23A C24 H24B 137 . . ? C23 C24 H24B 109.3 . . ? H24A C24 H24B 107.9 . . ? C28 O2 C25 108 . . ? C26 C25 O2 108 . . ? C26 C25 H25A 110.1 . . ? O2 C25 H25A 110.1 . . ? C26 C25 H25B 110.1 . . ? O2 C25 H25B 110.1 . . ? H25A C25 H25B 108.4 . . ? C25 C26 C27 108 . . ? C25 C26 H26A 110.1 . . ? C27 C26 H26A 110.1 . . ? C25 C26 H26B 110.1 . . ? C27 C26 H26B 110.1 . . ? H26A C26 H26B 108.4 . . ? C28 C27 C26 108 . . ? C28 C27 H27A 110.1 . . ? C26 C27 H27A 110.1 . . ? C28 C27 H27B 110.1 . . ? C26 C27 H27B 110.1 . . ? H27A C27 H27B 108.4 . . ? C27 C28 O2 108 . . ? C27 C28 H28A 110.1 . . ? O2 C28 H28A 110.1 . . ? C27 C28 H28B 110.1 . . ? O2 C28 H28B 110.1 . . ? H28A C28 H28B 108.4 . . ? C28A O2A C25A 108 . . ? C27A C25A O2A 108 . . ? C27A C25A H25C 110.1 . . ? O2A C25A H25C 110.1 . . ? C27A C25A H25D 110.1 . . ? O2A C25A H25D 110.1 . . ? H25C C25A H25D 108.4 . . ? C26A C27A C25A 108 . . ? C26A C27A H27C 110.1 . . ? C25A C27A H27C 110.1 . . ? C26A C27A H27D 110.1 . . ? C25A C27A H27D 110.1 . . ? H27C C27A H27D 108.4 . . ? C28A C26A C27A 108 . . ? C28A C26A H26C 110.1 . . ? C27A C26A H26C 110.1 . . ? C28A C26A H26D 110.1 . . ? C27A C26A H26D 110.1 . . ? H26C C26A H26D 108.4 . . ? C26A C28A O2A 108 . . ? C26A C28A H28C 110.1 . . ? O2A C28A H28C 110.1 . . ? C26A C28A H28D 110.1 . . ? O2A C28A H28D 110.1 . . ? H28C C28A H28D 108.4 . . ? O1 In1 N1 81.7(2) . . ? O1 In1 N2 86.2(2) . . ? N1 In1 N2 72.2(2) . . ? O1 In1 Cl5 87.21(17) . . ? N1 In1 Cl5 162.37(18) . . ? N2 In1 Cl5 93.58(17) . . ? O1 In1 Cl4 88.90(16) . . ? N1 In1 Cl4 98.34(18) . . ? N2 In1 Cl4 169.87(17) . . ? Cl5 In1 Cl4 95.06(8) . . ? O1 In1 Cl3 172.42(16) . . ? N1 In1 Cl3 91.17(17) . . ? N2 In1 Cl3 89.25(18) . . ? Cl5 In1 Cl3 99.16(9) . . ? Cl4 In1 Cl3 94.58(9) . . ? C3 N1 C2 116.3(7) . . ? C3 N1 In1 114.8(6) . . ? C2 N1 In1 128.6(6) . . ? C4 N2 C5 117.9(7) . . ? C4 N2 In1 112.1(5) . . ? C5 N2 In1 128.7(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 C1 C2 N1 -169.3(14) . . . . ? C13A C1 C2 N1 -174.6(13) . . . . ? Cl1 C1 C2 N1 66.5(8) . . . . ? C13 C1 C2 C19 -47.1(16) . . . . ? C13A C1 C2 C19 -52.4(15) . . . . ? Cl1 C1 C2 C19 -171.3(6) . . . . ? N1 C3 C4 N2 1.3(12) . . . . ? N2 C5 C6 C7 -167.4(7) . . . . ? C20 C5 C6 C7 -44.9(11) . . . . ? N2 C5 C6 Cl2 68.5(8) . . . . ? C20 C5 C6 Cl2 -169.0(6) . . . . ? C5 C6 C7 C12 108.8(10) . . . . ? Cl2 C6 C7 C12 -128.1(8) . . . . ? C5 C6 C7 C8 -69.5(11) . . . . ? Cl2 C6 C7 C8 53.6(10) . . . . ? C12 C7 C8 C9 -0.9(14) . . . . ? C6 C7 C8 C9 177.4(9) . . . . ? C7 C8 C9 C10 -1.7(16) . . . . ? C8 C9 C10 C11 4.0(17) . . . . ? C9 C10 C11 C12 -3.6(16) . . . . ? C10 C11 C12 C7 1.1(15) . . . . ? C8 C7 C12 C11 1.2(14) . . . . ? C6 C7 C12 C11 -177.1(8) . . . . ? C13A C1 C13 C14 -44(9) . . . . ? C2 C1 C13 C14 -67(2) . . . . ? Cl1 C1 C13 C14 57.0(17) . . . . ? C13A C1 C13 C18 131(10) . . . . ? C2 C1 C13 C18 108.1(12) . . . . ? Cl1 C1 C13 C18 -128.2(10) . . . . ? C18 C13 C14 C15 0 . . . . ? C1 C13 C14 C15 175(2) . . . . ? C13 C14 C15 C16 0 . . . . ? C14 C15 C16 C17 0 . . . . ? C15 C16 C17 C18 0 . . . . ? C16 C17 C18 C13 0 . . . . ? C14 C13 C18 C17 0 . . . . ? C1 C13 C18 C17 -175(2) . . . . ? C13 C1 C13A C14A 135(11) . . . . ? C2 C1 C13A C14A -65.2(18) . . . . ? Cl1 C1 C13A C14A 51.7(17) . . . . ? C13 C1 C13A C18A -41(9) . . . . ? C2 C1 C13A C18A 119.0(10) . . . . ? Cl1 C1 C13A C18A -124.1(10) . . . . ? C18A C13A C14A C15A 0 . . . . ? C1 C13A C14A C15A -176(2) . . . . ? C13A C14A C15A C16A 0 . . . . ? C14A C15A C16A C17A 0 . . . . ? C15A C16A C17A C18A 0 . . . . ? C16A C17A C18A C13A 0 . . . . ? C14A C13A C18A C17A 0 . . . . ? C1 C13A C18A C17A 176(2) . . . . ? O1 C21 C22 C23 1(2) . . . . ? C21 C22 C23 C24 9(2) . . . . ? O1 C21A C22A C23A 24(2) . . . . ? C21A C22A C23A C24 -43(2) . . . . ? C22A C21A O1 C21 -107(6) . . . . ? C22A C21A O1 C24 4.7(19) . . . . ? C22A C21A O1 In1 170.4(12) . . . . ? C22 C21 O1 C21A 64(6) . . . . ? C22 C21 O1 C24 -11.4(15) . . . . ? C22 C21 O1 In1 174.6(10) . . . . ? C21A O1 C24 C23A -33.5(15) . . . . ? C21 O1 C24 C23A -11.5(14) . . . . ? In1 O1 C24 C23A 161.7(8) . . . . ? C21A O1 C24 C23 -3.2(16) . . . . ? C21 O1 C24 C23 18.9(16) . . . . ? In1 O1 C24 C23 -167.9(10) . . . . ? C22A C23A C24 O1 47.6(17) . . . . ? C22A C23A C24 C23 -63(2) . . . . ? C22 C23 C24 O1 -15.3(19) . . . . ? C22 C23 C24 C23A 63(2) . . . . ? C28 O2 C25 C26 0 . . . . ? O2 C25 C26 C27 0 . . . . ? C25 C26 C27 C28 0 . . . . ? C26 C27 C28 O2 0 . . . . ? C25 O2 C28 C27 0 . . . . ? C28A O2A C25A C27A 0 . . . . ? O2A C25A C27A C26A 0 . . . . ? C25A C27A C26A C28A 0 . . . . ? C27A C26A C28A O2A 0 . . . . ? C25A O2A C28A C26A 0 . . . . ? C21A O1 In1 N1 -127.1(13) . . . . ? C21 O1 In1 N1 -152.0(10) . . . . ? C24 O1 In1 N1 35.2(7) . . . . ? C21A O1 In1 N2 160.4(13) . . . . ? C21 O1 In1 N2 135.5(10) . . . . ? C24 O1 In1 N2 -37.4(7) . . . . ? C21A O1 In1 Cl5 66.6(13) . . . . ? C21 O1 In1 Cl5 41.7(10) . . . . ? C24 O1 In1 Cl5 -131.1(7) . . . . ? C21A O1 In1 Cl4 -28.5(13) . . . . ? C21 O1 In1 Cl4 -53.4(10) . . . . ? C24 O1 In1 Cl4 133.7(7) . . . . ? C21A O1 In1 Cl3 -146.0(15) . . . . ? C21 O1 In1 Cl3 -170.9(13) . . . . ? C24 O1 In1 Cl3 16.2(18) . . . . ? C4 C3 N1 C2 178.3(7) . . . . ? C4 C3 N1 In1 4.1(10) . . . . ? C19 C2 N1 C3 127.3(8) . . . . ? C1 C2 N1 C3 -110.5(9) . . . . ? C19 C2 N1 In1 -59.5(10) . . . . ? C1 C2 N1 In1 62.7(8) . . . . ? O1 In1 N1 C3 -93.7(6) . . . . ? N2 In1 N1 C3 -5.0(6) . . . . ? Cl5 In1 N1 C3 -42.3(10) . . . . ? Cl4 In1 N1 C3 178.6(6) . . . . ? Cl3 In1 N1 C3 83.8(6) . . . . ? O1 In1 N1 C2 93.0(6) . . . . ? N2 In1 N1 C2 -178.3(7) . . . . ? Cl5 In1 N1 C2 144.4(6) . . . . ? Cl4 In1 N1 C2 5.3(6) . . . . ? Cl3 In1 N1 C2 -89.5(6) . . . . ? C3 C4 N2 C5 -174.0(7) . . . . ? C3 C4 N2 In1 -5.7(9) . . . . ? C20 C5 N2 C4 113.1(9) . . . . ? C6 C5 N2 C4 -122.5(9) . . . . ? C20 C5 N2 In1 -52.9(9) . . . . ? C6 C5 N2 In1 71.5(9) . . . . ? O1 In1 N2 C4 88.0(6) . . . . ? N1 In1 N2 C4 5.6(6) . . . . ? Cl5 In1 N2 C4 175.0(6) . . . . ? Cl4 In1 N2 C4 26.5(15) . . . . ? Cl3 In1 N2 C4 -85.9(6) . . . . ? O1 In1 N2 C5 -105.3(7) . . . . ? N1 In1 N2 C5 172.3(7) . . . . ? Cl5 In1 N2 C5 -18.3(7) . . . . ? Cl4 In1 N2 C5 -166.8(8) . . . . ? Cl3 In1 N2 C5 80.8(7) . . . . ? # END of CIF _database_code_depnum_ccdc_archive 'CCDC 960662'