# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_shelx _database_code_depnum_ccdc_archive 'CCDC 876917' #TrackingRef 'archive.cif' _audit_creation_date 2011-07-14T10:34:46-00:00 _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_formula_moiety 'C20 H16 Cl3 N O3' _chemical_formula_sum 'C20 H16 Cl3 N O3' _chemical_formula_weight 424.69 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2312(3) _cell_length_b 9.9744(4) _cell_length_c 10.6797(4) _cell_angle_alpha 74.0757(16) _cell_angle_beta 79.2214(18) _cell_angle_gamma 74.1904(19) _cell_volume 903.11(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5222 _cell_measurement_theta_min 2 _cell_measurement_theta_max 30.034 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.53 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2007)' _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_T_max 0.941 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(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 -0.83584E-2 _diffrn_orient_matrix_ub_12 0.102465 _diffrn_orient_matrix_ub_13 -0.13603E-2 _diffrn_orient_matrix_ub_21 -0.112526 _diffrn_orient_matrix_ub_22 0.148251E-1 _diffrn_orient_matrix_ub_23 0.219075E-1 _diffrn_orient_matrix_ub_31 0.115442E-1 _diffrn_orient_matrix_ub_32 -0.279461E-1 _diffrn_orient_matrix_ub_33 0.956098E-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 0.0614 _diffrn_reflns_av_unetI/netI 0.0433 _diffrn_reflns_number 40097 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2 _diffrn_reflns_theta_max 29.83 _diffrn_reflns_theta_full 29.83 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 5178 _reflns_number_gt 4349 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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 'SIR92 (Giacovazzo et al, 1993)' _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^)+(0.0708P)^2^+0.3376P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_number_reflns 5178 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.122 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.075 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.087 #----------------------------------------------------------------------------# # 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 Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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' 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 0.62108(5) -0.09749(4) 0.88354(4) 0.02388(11) Uani 1 1 d . . . Cl2 Cl 0.30730(5) -0.10771(4) 0.90366(4) 0.02458(11) Uani 1 1 d . . . Cl3 Cl 0.52968(5) -0.20628(4) 0.69599(4) 0.02406(11) Uani 1 1 d . . . O9 O 0.20606(14) 0.42444(13) 0.44298(12) 0.0221(2) Uani 1 1 d . . . O14 O -0.16402(17) 0.15257(19) 0.80494(16) 0.0389(4) Uani 1 1 d . . . O15 O 0.35833(14) 0.08908(13) 0.60844(12) 0.0222(2) Uani 1 1 d . . . N1 N 0.45178(16) 0.18205(15) 0.74009(15) 0.0194(3) Uani 1 1 d . . . H1N H 0.496 0.162 0.8114 0.055(9) Uiso 1 1 calc R . . C1 C 0.41064(18) 0.33214(17) 0.66518(17) 0.0191(3) Uani 1 1 d . . . H1 H 0.4278 0.3342 0.5695 0.030(6) Uiso 1 1 calc R . . C2 C 0.5127(2) 0.41644(18) 0.69229(19) 0.0242(3) Uani 1 1 d . . . H2A H 0.6201 0.3688 0.6708 0.029(6) Uiso 1 1 calc R . . H2B H 0.4933 0.5141 0.6343 0.031(6) Uiso 1 1 calc R . . C3 C 0.4866(2) 0.42788(19) 0.8349(2) 0.0273(4) Uani 1 1 d . . . H3A H 0.5492 0.4894 0.8456 0.036(7) Uiso 1 1 calc R . . H3B H 0.5189 0.3314 0.8925 0.034(7) Uiso 1 1 calc R . . C4 C 0.3177(2) 0.49187(19) 0.8768(2) 0.0282(4) Uani 1 1 d . . . H4A H 0.3015 0.4846 0.9725 0.043(7) Uiso 1 1 calc R . . H4B H 0.2908 0.5947 0.8317 0.041(7) Uiso 1 1 calc R . . C4A C 0.2165(2) 0.41445(18) 0.84363(18) 0.0226(3) Uani 1 1 d . . . C5 C 0.1171(2) 0.3530(2) 0.93207(18) 0.0259(4) Uani 1 1 d . . . H5 H 0.1082 0.3616 1.0198 0.029(6) Uiso 1 1 calc R . . C6 C 0.0184(2) 0.2711(2) 0.90278(19) 0.0274(4) Uani 1 1 d . . . H6A H -0.0886 0.3114 0.9337 0.042(7) Uiso 1 1 calc R . . H6B H 0.0461 0.17 0.9524 0.032(6) Uiso 1 1 calc R . . C7 C 0.03159(18) 0.27519(18) 0.75909(17) 0.0208(3) Uani 1 1 d . . . C8 C 0.13107(18) 0.33744(17) 0.66860(16) 0.0181(3) Uani 1 1 d . . . C8A C 0.24163(18) 0.40550(16) 0.70186(16) 0.0182(3) Uani 1 1 d . . . H8A H 0.2244 0.5063 0.6476 0.029(6) Uiso 1 1 calc R . . C9 C 0.13236(17) 0.34943(17) 0.52557(16) 0.0179(3) Uani 1 1 d . . . C9A C 0.03681(18) 0.27260(17) 0.48614(17) 0.0199(3) Uani 1 1 d . . . C10 C 0.0470(2) 0.26864(19) 0.35478(19) 0.0240(3) Uani 1 1 d . . . H10 H 0.1166 0.313 0.2905 0.051(8) Uiso 1 1 calc R . . C11 C -0.0447(2) 0.1998(2) 0.3187(2) 0.0281(4) Uani 1 1 d . . . H11 H -0.0364 0.1955 0.2298 0.050(8) Uiso 1 1 calc R . . C12 C -0.1493(2) 0.1367(2) 0.4120(2) 0.0290(4) Uani 1 1 d . . . H12 H -0.213 0.091 0.3864 0.040(7) Uiso 1 1 calc R . . C13 C -0.1600(2) 0.1409(2) 0.5427(2) 0.0270(4) Uani 1 1 d . . . H13 H -0.2313 0.0981 0.6063 0.047(8) Uiso 1 1 calc R . . C13A C -0.06610(18) 0.20790(18) 0.58070(18) 0.0210(3) Uani 1 1 d . . . C14 C -0.07375(19) 0.2080(2) 0.72105(19) 0.0244(3) Uani 1 1 d . . . C15 C 0.42319(17) 0.07506(16) 0.70189(16) 0.0176(3) Uani 1 1 d . . . C16 C 0.47072(18) -0.07767(17) 0.79188(16) 0.0180(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0236(2) 0.02057(19) 0.0276(2) -0.00574(15) -0.00904(15) -0.00152(14) Cl2 0.0232(2) 0.02218(19) 0.0254(2) -0.00265(15) 0.00323(15) -0.00759(14) Cl3 0.0284(2) 0.01718(18) 0.0269(2) -0.00949(15) -0.00338(16) -0.00150(14) O9 0.0228(6) 0.0202(6) 0.0225(6) -0.0028(5) -0.0017(5) -0.0065(4) O14 0.0329(8) 0.0515(10) 0.0360(8) -0.0111(7) 0.0096(6) -0.0244(7) O15 0.0259(6) 0.0187(5) 0.0224(6) -0.0047(4) -0.0058(5) -0.0040(5) N1 0.0201(6) 0.0144(6) 0.0240(7) -0.0041(5) -0.0051(5) -0.0035(5) C1 0.0180(7) 0.0143(6) 0.0244(8) -0.0027(6) -0.0026(6) -0.0050(5) C2 0.0247(8) 0.0167(7) 0.0332(9) -0.0024(6) -0.0085(7) -0.0083(6) C3 0.0310(9) 0.0185(7) 0.0355(10) -0.0035(7) -0.0147(7) -0.0068(6) C4 0.0370(10) 0.0214(8) 0.0296(9) -0.0105(7) -0.0122(8) -0.0024(7) C4A 0.0251(8) 0.0195(7) 0.0232(8) -0.0080(6) -0.0065(6) 0.0002(6) C5 0.0276(8) 0.0268(8) 0.0217(8) -0.0082(7) -0.0037(7) -0.0007(7) C6 0.0262(8) 0.0312(9) 0.0222(8) -0.0065(7) 0.0035(7) -0.0064(7) C7 0.0168(7) 0.0201(7) 0.0234(8) -0.0061(6) 0.0004(6) -0.0020(5) C8 0.0182(7) 0.0151(6) 0.0206(7) -0.0048(5) -0.0023(6) -0.0028(5) C8A 0.0190(7) 0.0143(6) 0.0217(8) -0.0048(5) -0.0044(6) -0.0025(5) C9 0.0155(6) 0.0155(6) 0.0219(7) -0.0054(5) -0.0028(5) -0.0006(5) C9A 0.0157(7) 0.0167(7) 0.0273(8) -0.0072(6) -0.0039(6) -0.0011(5) C10 0.0231(8) 0.0211(7) 0.0276(9) -0.0067(6) -0.0058(7) -0.0021(6) C11 0.0276(9) 0.0260(8) 0.0328(10) -0.0118(7) -0.0106(7) -0.0002(7) C12 0.0238(8) 0.0223(8) 0.0458(11) -0.0134(8) -0.0137(8) -0.0016(6) C13 0.0173(7) 0.0236(8) 0.0408(11) -0.0085(7) -0.0042(7) -0.0049(6) C13A 0.0149(7) 0.0194(7) 0.0285(8) -0.0074(6) -0.0012(6) -0.0029(5) C14 0.0189(7) 0.0250(8) 0.0285(9) -0.0072(7) 0.0020(6) -0.0062(6) C15 0.0151(6) 0.0150(6) 0.0212(7) -0.0042(5) 0.0008(5) -0.0032(5) C16 0.0186(7) 0.0166(7) 0.0195(7) -0.0054(5) -0.0019(6) -0.0045(5) #----------------------------------------------------------------------------# # 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 C16 1.7823(16) . ? Cl2 C16 1.7796(17) . ? Cl3 C16 1.7672(16) . ? O9 C9 1.221(2) . ? O14 C14 1.226(2) . ? O15 C15 1.215(2) . ? N1 C15 1.345(2) . ? N1 C1 1.474(2) . ? N1 H1N 0.88 . ? C1 C2 1.532(2) . ? C1 C8A 1.559(2) . ? C1 H1 1 . ? C2 C3 1.528(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.547(3) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C4A 1.504(2) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C4A C5 1.332(3) . ? C4A C8A 1.512(2) . ? C5 C6 1.499(3) . ? C5 H5 0.95 . ? C6 C7 1.507(3) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.346(2) . ? C7 C14 1.487(2) . ? C8 C9 1.497(2) . ? C8 C8A 1.508(2) . ? C8A H8A 1 . ? C9 C9A 1.492(2) . ? C9A C13A 1.399(2) . ? C9A C10 1.399(2) . ? C10 C11 1.387(3) . ? C10 H10 0.95 . ? C11 C12 1.396(3) . ? C11 H11 0.95 . ? C12 C13 1.392(3) . ? C12 H12 0.95 . ? C13 C13A 1.400(2) . ? C13 H13 0.95 . ? C13A C14 1.488(3) . ? C15 C16 1.558(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 C15 N1 C1 121.42(14) . . ? C15 N1 H1N 119.3 . . ? C1 N1 H1N 119.3 . . ? N1 C1 C2 109.12(13) . . ? N1 C1 C8A 112.21(13) . . ? C2 C1 C8A 109.02(13) . . ? N1 C1 H1 108.8 . . ? C2 C1 H1 108.8 . . ? C8A C1 H1 108.8 . . ? C3 C2 C1 112.61(15) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 111.24(15) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108 . . ? C4A C4 C3 111.15(14) . . ? C4A C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C4A C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108 . . ? C5 C4A C4 123.31(17) . . ? C5 C4A C8A 122.19(16) . . ? C4 C4A C8A 114.44(16) . . ? C4A C5 C6 124.51(17) . . ? C4A C5 H5 117.7 . . ? C6 C5 H5 117.7 . . ? C5 C6 C7 113.29(16) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C14 121.10(16) . . ? C8 C7 C6 122.62(16) . . ? C14 C7 C6 116.27(15) . . ? C7 C8 C9 120.96(15) . . ? C7 C8 C8A 123.32(15) . . ? C9 C8 C8A 115.65(14) . . ? C8 C8A C4A 113.45(14) . . ? C8 C8A C1 113.21(13) . . ? C4A C8A C1 109.62(13) . . ? C8 C8A H8A 106.7 . . ? C4A C8A H8A 106.7 . . ? C1 C8A H8A 106.7 . . ? O9 C9 C9A 120.79(15) . . ? O9 C9 C8 120.60(15) . . ? C9A C9 C8 118.56(14) . . ? C13A C9A C10 120.15(16) . . ? C13A C9A C9 119.60(16) . . ? C10 C9A C9 120.22(16) . . ? C11 C10 C9A 119.78(18) . . ? C11 C10 H10 120.1 . . ? C9A C10 H10 120.1 . . ? C10 C11 C12 120.47(18) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 119.86(17) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C13A 120.17(18) . . ? C12 C13 H13 119.9 . . ? C13A C13 H13 119.9 . . ? C9A C13A C13 119.55(17) . . ? C9A C13A C14 120.23(15) . . ? C13 C13A C14 120.20(16) . . ? O14 C14 C7 120.05(18) . . ? O14 C14 C13A 121.00(17) . . ? C7 C14 C13A 118.95(15) . . ? O15 C15 N1 125.64(15) . . ? O15 C15 C16 118.58(14) . . ? N1 C15 C16 115.69(14) . . ? C15 C16 Cl3 109.81(11) . . ? C15 C16 Cl2 106.36(10) . . ? Cl3 C16 Cl2 110.51(9) . . ? C15 C16 Cl1 113.79(11) . . ? Cl3 C16 Cl1 107.80(8) . . ? Cl2 C16 Cl1 108.56(9) . . ? 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 C15 N1 C1 C2 -155.59(15) . . . . ? C15 N1 C1 C8A 83.47(19) . . . . ? N1 C1 C2 C3 -65.28(18) . . . . ? C8A C1 C2 C3 57.59(18) . . . . ? C1 C2 C3 C4 -54.70(19) . . . . ? C2 C3 C4 C4A 50.7(2) . . . . ? C3 C4 C4A C5 123.76(19) . . . . ? C3 C4 C4A C8A -53.4(2) . . . . ? C4 C4A C5 C6 -177.94(16) . . . . ? C8A C4A C5 C6 -1.0(3) . . . . ? C4A C5 C6 C7 -5.1(3) . . . . ? C5 C6 C7 C8 4.7(2) . . . . ? C5 C6 C7 C14 -174.42(14) . . . . ? C14 C7 C8 C9 3.9(2) . . . . ? C6 C7 C8 C9 -175.13(15) . . . . ? C14 C7 C8 C8A -179.23(14) . . . . ? C6 C7 C8 C8A 1.7(2) . . . . ? C7 C8 C8A C4A -7.5(2) . . . . ? C9 C8 C8A C4A 169.45(13) . . . . ? C7 C8 C8A C1 118.20(17) . . . . ? C9 C8 C8A C1 -64.80(18) . . . . ? C5 C4A C8A C8 7.1(2) . . . . ? C4 C4A C8A C8 -175.63(13) . . . . ? C5 C4A C8A C1 -120.49(17) . . . . ? C4 C4A C8A C1 56.74(18) . . . . ? N1 C1 C8A C8 -63.61(18) . . . . ? C2 C1 C8A C8 175.39(14) . . . . ? N1 C1 C8A C4A 64.16(17) . . . . ? C2 C1 C8A C4A -56.83(18) . . . . ? C7 C8 C9 O9 168.81(15) . . . . ? C8A C8 C9 O9 -8.3(2) . . . . ? C7 C8 C9 C9A -8.7(2) . . . . ? C8A C8 C9 C9A 174.19(13) . . . . ? O9 C9 C9A C13A -169.03(15) . . . . ? C8 C9 C9A C13A 8.5(2) . . . . ? O9 C9 C9A C10 9.2(2) . . . . ? C8 C9 C9A C10 -173.24(14) . . . . ? C13A C9A C10 C11 -0.3(2) . . . . ? C9 C9A C10 C11 -178.53(15) . . . . ? C9A C10 C11 C12 1.2(3) . . . . ? C10 C11 C12 C13 -1.0(3) . . . . ? C11 C12 C13 C13A -0.1(3) . . . . ? C10 C9A C13A C13 -0.8(2) . . . . ? C9 C9A C13A C13 177.43(14) . . . . ? C10 C9A C13A C14 178.07(15) . . . . ? C9 C9A C13A C14 -3.7(2) . . . . ? C12 C13 C13A C9A 1.0(2) . . . . ? C12 C13 C13A C14 -177.88(16) . . . . ? C8 C7 C14 O14 -179.60(17) . . . . ? C6 C7 C14 O14 -0.5(3) . . . . ? C8 C7 C14 C13A 1.1(2) . . . . ? C6 C7 C14 C13A -179.77(15) . . . . ? C9A C13A C14 O14 179.51(17) . . . . ? C13 C13A C14 O14 -1.6(3) . . . . ? C9A C13A C14 C7 -1.2(2) . . . . ? C13 C13A C14 C7 177.68(15) . . . . ? C1 N1 C15 O15 -2.7(3) . . . . ? C1 N1 C15 C16 -179.09(13) . . . . ? O15 C15 C16 Cl3 36.81(18) . . . . ? N1 C15 C16 Cl3 -146.55(12) . . . . ? O15 C15 C16 Cl2 -82.79(16) . . . . ? N1 C15 C16 Cl2 93.85(14) . . . . ? O15 C15 C16 Cl1 157.73(13) . . . . ? N1 C15 C16 Cl1 -25.62(18) . . . . ? _iucr_refine_instruction_details ; TITL C20 H16 Cl3 N O3 code svc_12 100K KappaCCD in P -1 CELL 0.71073 9.2312 9.9744 10.6797 74.0757 79.2214 74.1904 ZERR 2.00 0.0003 0.0004 0.0004 0.0016 0.0018 0.0019 LATT 1 SFAC CL O N C H UNIT 6 6 2 40 32 MERG 2 FMAP 2 PLAN 10 L.S. 10 ACTA LIST 4 BOND $H CONF TEMP -173 SIZE 0.05 0.31 0.35 WGHT 0.0708 0.3376 FVAR 0.55383 CL1 1 0.621088 -0.097485 0.883547 11.00000 0.02362 0.02055 = 0.02760 -0.00573 -0.00904 -0.00151 CL2 1 0.307299 -0.107703 0.903661 11.00000 0.02316 0.02214 = 0.02536 -0.00266 0.00324 -0.00758 CL3 1 0.529679 -0.206284 0.695995 11.00000 0.02839 0.01716 = 0.02685 -0.00949 -0.00337 -0.00151 O9 2 0.206054 0.424448 0.442993 11.00000 0.02265 0.02014 = 0.02240 -0.00280 -0.00171 -0.00646 O14 2 -0.164056 0.152578 0.804922 11.00000 0.03273 0.05116 = 0.03587 -0.01107 0.00948 -0.02422 O15 2 0.358340 0.089088 0.608450 11.00000 0.02594 0.01871 = 0.02219 -0.00474 -0.00571 -0.00405 N1 3 0.451733 0.182070 0.740048 11.00000 0.02014 0.01447 = 0.02387 -0.00399 -0.00549 -0.00340 AFIX 43 H1N 5 0.494940 0.162491 0.809714 11.00000 0.05 AFIX 0 C1 4 0.410654 0.332135 0.665205 11.00000 0.01808 0.01423 = 0.02428 -0.00257 -0.00258 -0.00494 AFIX 13 H1 5 0.427446 0.334180 0.571404 11.00000 0.05 AFIX 0 C2 4 0.512705 0.416431 0.692345 11.00000 0.02455 0.01661 = 0.03332 -0.00240 -0.00849 -0.00815 AFIX 23 H2A 5 0.617962 0.369710 0.671285 11.00000 0.05 H2B 5 0.493696 0.512120 0.635504 11.00000 0.05 AFIX 0 C3 4 0.486583 0.427885 0.834926 11.00000 0.03109 0.01847 = 0.03550 -0.00337 -0.01479 -0.00682 AFIX 23 H3A 5 0.547908 0.488182 0.845410 11.00000 0.05 H3B 5 0.518258 0.333402 0.891352 11.00000 0.05 AFIX 0 C4 4 0.317693 0.491840 0.876802 11.00000 0.03723 0.02131 = 0.02963 -0.01048 -0.01238 -0.00234 AFIX 23 H4A 5 0.301804 0.484751 0.970555 11.00000 0.05 H4B 5 0.291315 0.592561 0.832598 11.00000 0.05 AFIX 0 C4A 4 0.216469 0.414424 0.843645 11.00000 0.02510 0.01947 = 0.02317 -0.00797 -0.00662 0.00017 C5 4 0.117079 0.352958 0.932058 11.00000 0.02748 0.02677 = 0.02163 -0.00827 -0.00355 -0.00066 AFIX 43 H5 5 0.108318 0.361402 1.017894 11.00000 0.05 AFIX 0 C6 4 0.018380 0.271119 0.902754 11.00000 0.02616 0.03103 = 0.02220 -0.00646 0.00353 -0.00619 AFIX 23 H6A 5 -0.086410 0.310576 0.933091 11.00000 0.05 H6B 5 0.045544 0.172037 0.951311 11.00000 0.05 AFIX 0 C7 4 0.031563 0.275188 0.759085 11.00000 0.01683 0.02008 = 0.02340 -0.00608 0.00039 -0.00201 C8 4 0.131032 0.337445 0.668614 11.00000 0.01811 0.01508 = 0.02061 -0.00482 -0.00232 -0.00276 C8A 4 0.241665 0.405461 0.701903 11.00000 0.01896 0.01419 = 0.02163 -0.00482 -0.00434 -0.00242 AFIX 13 H8A 5 0.224735 0.504279 0.648751 11.00000 0.05 AFIX 0 C9 4 0.132370 0.349444 0.525565 11.00000 0.01539 0.01540 = 0.02190 -0.00543 -0.00283 -0.00056 C9A 4 0.036796 0.272603 0.486124 11.00000 0.01568 0.01669 = 0.02729 -0.00730 -0.00385 -0.00107 C10 4 0.047021 0.268619 0.354787 11.00000 0.02299 0.02104 = 0.02762 -0.00657 -0.00562 -0.00221 AFIX 43 H10 5 0.115149 0.312014 0.291885 11.00000 0.05 AFIX 0 C11 4 -0.044738 0.199769 0.318712 11.00000 0.02777 0.02599 = 0.03259 -0.01176 -0.01071 -0.00019 AFIX 43 H11 5 -0.036564 0.195574 0.231673 11.00000 0.05 AFIX 0 C12 4 -0.149284 0.136708 0.412043 11.00000 0.02372 0.02230 = 0.04598 -0.01346 -0.01378 -0.00161 AFIX 43 H12 5 -0.211657 0.092012 0.386982 11.00000 0.05 AFIX 0 C13 4 -0.159982 0.140865 0.542691 11.00000 0.01711 0.02356 = 0.04080 -0.00840 -0.00400 -0.00495 AFIX 43 H13 5 -0.229707 0.098975 0.604940 11.00000 0.05 AFIX 0 C13A 4 -0.066084 0.207927 0.580697 11.00000 0.01489 0.01927 = 0.02857 -0.00742 -0.00118 -0.00291 C14 4 -0.073741 0.208010 0.721059 11.00000 0.01887 0.02493 = 0.02860 -0.00731 0.00201 -0.00612 C15 4 0.423173 0.075053 0.701855 11.00000 0.01512 0.01493 = 0.02123 -0.00419 0.00066 -0.00312 C16 4 0.470719 -0.077669 0.791877 11.00000 0.01862 0.01664 = 0.01949 -0.00543 -0.00192 -0.00453 HKLF 4 END ; # END of CIF