# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 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_2i _database_code_depnum_ccdc_archive 'CCDC 924031' #TrackingRef 'web_deposit_cif_file_0_CharlesS.Yeung_1360436158.Brindle, Yeung, Jacobsen_Chemical Sciences Submission.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cl3 I N O' _chemical_formula_weight 494.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall P2ac2ab 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 6.25010(10) _cell_length_b 10.0275(2) _cell_length_c 30.1617(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1890.32(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9969 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 25.7 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 2.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6761 _exptl_absorpt_correction_T_max 0.7847 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker D8 goniometer with CCD area detector ; _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21519 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 25.69 _reflns_number_total 3605 _reflns_number_gt 3397 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0127P)^2^+0.6814P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.010(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 3605 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0241 _refine_ls_R_factor_gt 0.0206 _refine_ls_wR_factor_ref 0.0378 _refine_ls_wR_factor_gt 0.0371 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4423(4) 0.4675(3) 0.34526(9) 0.0140(6) Uani 1 1 d . . . H1 H 0.3799 0.4469 0.3732 0.017 Uiso 1 1 calc R . . C2 C 0.6067(5) 0.5593(2) 0.34357(8) 0.0134(5) Uani 1 1 d . . . C3 C 0.6970(5) 0.5881(3) 0.30244(9) 0.0155(6) Uani 1 1 d . . . H3 H 0.8109 0.6506 0.3006 0.019 Uiso 1 1 calc R . . C4 C 0.6236(5) 0.5275(3) 0.26430(8) 0.0177(6) Uani 1 1 d . . . H4 H 0.6864 0.5486 0.2365 0.021 Uiso 1 1 calc R . . C5 C 0.4581(4) 0.4355(3) 0.26659(9) 0.0163(6) Uani 1 1 d . . . H5 H 0.4081 0.3940 0.2402 0.020 Uiso 1 1 calc R . . C6 C 0.3642(4) 0.4035(2) 0.30721(8) 0.0140(6) Uani 1 1 d . . . C7 C 0.1860(5) 0.3066(3) 0.30970(9) 0.0147(6) Uani 1 1 d . . . C8 C 0.0322(5) 0.3015(3) 0.27622(9) 0.0173(7) Uani 1 1 d . . . H8 H 0.0425 0.3607 0.2517 0.021 Uiso 1 1 calc R . . C9 C -0.1354(5) 0.2114(3) 0.27821(10) 0.0228(7) Uani 1 1 d . . . H9 H -0.2377 0.2083 0.2549 0.027 Uiso 1 1 calc R . . C10 C -0.1542(4) 0.1259(3) 0.31395(9) 0.0231(6) Uani 1 1 d . . . H10 H -0.2700 0.0646 0.3154 0.028 Uiso 1 1 calc R . . C11 C -0.0039(5) 0.1298(3) 0.34767(9) 0.0228(6) Uani 1 1 d . . . H11 H -0.0170 0.0716 0.3724 0.027 Uiso 1 1 calc R . . C12 C 0.1657(5) 0.2187(3) 0.34535(9) 0.0177(7) Uani 1 1 d . . . H12 H 0.2696 0.2197 0.3683 0.021 Uiso 1 1 calc R . . C13 C 0.6905(4) 0.6292(3) 0.38478(8) 0.0163(6) Uani 1 1 d . . . C14 C 0.9186(5) 0.5801(3) 0.39580(9) 0.0218(7) Uani 1 1 d . . . H14A H 1.0074 0.5798 0.3686 0.026 Uiso 1 1 calc R . . H14B H 0.9860 0.6407 0.4177 0.026 Uiso 1 1 calc R . . C15 C 0.9048(5) 0.4416(3) 0.41454(9) 0.0234(6) Uani 1 1 d . . . H15A H 0.8437 0.3806 0.3921 0.028 Uiso 1 1 calc R . . H15B H 1.0500 0.4095 0.4222 0.028 Uiso 1 1 calc R . . C16 C 0.6024(5) 0.5247(3) 0.45227(8) 0.0159(6) Uani 1 1 d . . . C17 C 0.7010(5) 0.7805(3) 0.37842(9) 0.0184(6) Uani 1 1 d . . . H17A H 0.8074 0.8012 0.3551 0.022 Uiso 1 1 calc R . . H17B H 0.7507 0.8222 0.4063 0.022 Uiso 1 1 calc R . . C18 C 0.4720(5) 0.5079(3) 0.49453(9) 0.0170(6) Uani 1 1 d . . . N1 N 0.5479(3) 0.6077(2) 0.42318(7) 0.0138(5) Uani 1 1 d . . . O1 O 0.7711(3) 0.44141(19) 0.45389(6) 0.0219(5) Uani 1 1 d . . . Cl1 Cl 0.25657(11) 0.62124(8) 0.49702(2) 0.02225(15) Uani 1 1 d . . . Cl2 Cl 0.64049(12) 0.53634(7) 0.54100(2) 0.02439(17) Uani 1 1 d . . . Cl3 Cl 0.36888(13) 0.34293(7) 0.49709(2) 0.02702(17) Uani 1 1 d . . . I1 I 0.39849(3) 0.866543(18) 0.360162(6) 0.02235(5) 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 0.0139(16) 0.0141(12) 0.0138(13) 0.0031(11) 0.0024(11) 0.0039(12) C2 0.0117(14) 0.0145(12) 0.0140(12) 0.0001(10) -0.0019(13) 0.0051(14) C3 0.0154(15) 0.0143(14) 0.0169(14) 0.0024(11) 0.0030(12) -0.0003(11) C4 0.0200(17) 0.0214(14) 0.0118(13) 0.0012(11) 0.0047(14) 0.0032(15) C5 0.0172(17) 0.0163(14) 0.0155(14) 0.0001(12) -0.0022(12) 0.0023(12) C6 0.0122(15) 0.0140(13) 0.0160(13) -0.0011(10) -0.0018(12) 0.0060(11) C7 0.0157(16) 0.0130(13) 0.0155(14) -0.0046(11) 0.0017(12) 0.0041(11) C8 0.0188(17) 0.0166(14) 0.0163(15) -0.0021(12) 0.0020(12) 0.0013(12) C9 0.0207(19) 0.0224(15) 0.0252(16) -0.0035(12) -0.0073(14) 0.0009(14) C10 0.0200(16) 0.0196(14) 0.0297(15) -0.0052(14) 0.0014(12) -0.0021(15) C11 0.0305(16) 0.0166(13) 0.0213(15) 0.0012(14) 0.0045(12) 0.0015(15) C12 0.0171(17) 0.0187(14) 0.0172(14) -0.0015(11) -0.0015(12) 0.0033(12) C13 0.0149(14) 0.0210(14) 0.0131(13) 0.0017(14) 0.0007(10) -0.0021(14) C14 0.0146(16) 0.0332(15) 0.0174(14) 0.0006(12) 0.0002(14) -0.0015(14) C15 0.0168(16) 0.0332(16) 0.0203(15) -0.0002(12) 0.0022(15) 0.0083(16) C16 0.0147(15) 0.0167(13) 0.0164(13) -0.0030(11) -0.0028(14) -0.0010(15) C17 0.0176(16) 0.0230(15) 0.0146(14) -0.0002(12) 0.0009(12) -0.0031(13) C18 0.0178(16) 0.0190(14) 0.0140(14) 0.0022(12) -0.0052(12) -0.0016(12) N1 0.0141(13) 0.0152(12) 0.0119(10) -0.0006(10) -0.0005(9) -0.0006(9) O1 0.0234(12) 0.0235(11) 0.0188(11) 0.0053(9) 0.0018(9) 0.0077(10) Cl1 0.0237(4) 0.0275(4) 0.0155(3) 0.0005(3) 0.0015(3) 0.0073(4) Cl2 0.0223(5) 0.0380(4) 0.0128(3) 0.0020(3) -0.0050(3) -0.0046(3) Cl3 0.0258(4) 0.0200(4) 0.0353(4) 0.0056(3) -0.0005(3) -0.0067(3) I1 0.02820(10) 0.02048(8) 0.01836(8) 0.00430(9) 0.00806(9) 0.00615(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.381(4) . ? C1 C6 1.402(4) . ? C1 H1 0.9500 . ? C2 C3 1.393(4) . ? C2 C13 1.520(4) . ? C3 C4 1.380(4) . ? C3 H3 0.9500 . ? C4 C5 1.388(4) . ? C4 H4 0.9500 . ? C5 C6 1.396(4) . ? C5 H5 0.9500 . ? C6 C7 1.480(4) . ? C7 C8 1.395(4) . ? C7 C12 1.396(4) . ? C8 C9 1.385(4) . ? C8 H8 0.9500 . ? C9 C10 1.382(4) . ? C9 H9 0.9500 . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 C12 1.387(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 N1 1.478(3) . ? C13 C17 1.531(4) . ? C13 C14 1.544(4) . ? C14 C15 1.502(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 O1 1.452(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N1 1.256(3) . ? C16 O1 1.346(4) . ? C16 C18 1.523(4) . ? C17 I1 2.150(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 Cl1 1.764(3) . ? C18 Cl2 1.776(3) . ? C18 Cl3 1.777(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 C2 C1 C6 122.3(2) . . ? C2 C1 H1 118.9 . . ? C6 C1 H1 118.9 . . ? C1 C2 C3 118.2(2) . . ? C1 C2 C13 122.3(2) . . ? C3 C2 C13 119.5(2) . . ? C4 C3 C2 121.1(3) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 117.8(2) . . ? C5 C6 C7 120.8(2) . . ? C1 C6 C7 121.4(2) . . ? C8 C7 C12 118.2(3) . . ? C8 C7 C6 120.4(2) . . ? C12 C7 C6 121.5(2) . . ? C9 C8 C7 120.9(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.8(3) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 120.9(3) . . ? C11 C12 H12 119.5 . . ? C7 C12 H12 119.5 . . ? N1 C13 C2 111.4(2) . . ? N1 C13 C17 105.6(2) . . ? C2 C13 C17 111.7(2) . . ? N1 C13 C14 110.0(2) . . ? C2 C13 C14 110.3(2) . . ? C17 C13 C14 107.7(2) . . ? C15 C14 C13 108.9(3) . . ? C15 C14 H14A 109.9 . . ? C13 C14 H14A 109.9 . . ? C15 C14 H14B 109.9 . . ? C13 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? O1 C15 C14 110.0(2) . . ? O1 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? O1 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N1 C16 O1 130.5(3) . . ? N1 C16 C18 120.8(3) . . ? O1 C16 C18 108.7(2) . . ? C13 C17 I1 113.10(19) . . ? C13 C17 H17A 109.0 . . ? I1 C17 H17A 109.0 . . ? C13 C17 H17B 109.0 . . ? I1 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? C16 C18 Cl1 111.90(19) . . ? C16 C18 Cl2 109.0(2) . . ? Cl1 C18 Cl2 108.39(15) . . ? C16 C18 Cl3 109.50(19) . . ? Cl1 C18 Cl3 108.75(15) . . ? Cl2 C18 Cl3 109.28(15) . . ? C16 N1 C13 118.7(2) . . ? C16 O1 C15 114.9(2) . . ? 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 C6 C1 C2 C3 -0.2(4) . . . . ? C6 C1 C2 C13 179.7(3) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C13 C2 C3 C4 -179.4(3) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 C6 0.0(4) . . . . ? C4 C5 C6 C1 0.2(4) . . . . ? C4 C5 C6 C7 179.3(3) . . . . ? C2 C1 C6 C5 -0.1(4) . . . . ? C2 C1 C6 C7 -179.2(2) . . . . ? C5 C6 C7 C8 -36.4(4) . . . . ? C1 C6 C7 C8 142.6(3) . . . . ? C5 C6 C7 C12 143.9(3) . . . . ? C1 C6 C7 C12 -37.0(4) . . . . ? C12 C7 C8 C9 -0.3(4) . . . . ? C6 C7 C8 C9 -179.9(2) . . . . ? C7 C8 C9 C10 0.9(4) . . . . ? C8 C9 C10 C11 -0.5(4) . . . . ? C9 C10 C11 C12 -0.4(4) . . . . ? C10 C11 C12 C7 1.1(4) . . . . ? C8 C7 C12 C11 -0.7(4) . . . . ? C6 C7 C12 C11 178.9(2) . . . . ? C1 C2 C13 N1 -11.7(4) . . . . ? C3 C2 C13 N1 168.2(2) . . . . ? C1 C2 C13 C17 -129.6(3) . . . . ? C3 C2 C13 C17 50.3(3) . . . . ? C1 C2 C13 C14 110.7(3) . . . . ? C3 C2 C13 C14 -69.4(3) . . . . ? N1 C13 C14 C15 49.7(3) . . . . ? C2 C13 C14 C15 -73.6(3) . . . . ? C17 C13 C14 C15 164.3(2) . . . . ? C13 C14 C15 O1 -58.5(3) . . . . ? N1 C13 C17 I1 -64.8(2) . . . . ? C2 C13 C17 I1 56.4(3) . . . . ? C14 C13 C17 I1 177.70(17) . . . . ? N1 C16 C18 Cl1 -2.8(3) . . . . ? O1 C16 C18 Cl1 176.11(18) . . . . ? N1 C16 C18 Cl2 -122.7(3) . . . . ? O1 C16 C18 Cl2 56.3(3) . . . . ? N1 C16 C18 Cl3 117.8(2) . . . . ? O1 C16 C18 Cl3 -63.2(3) . . . . ? O1 C16 N1 C13 -4.3(4) . . . . ? C18 C16 N1 C13 174.4(2) . . . . ? C2 C13 N1 C16 103.0(3) . . . . ? C17 C13 N1 C16 -135.6(2) . . . . ? C14 C13 N1 C16 -19.7(3) . . . . ? N1 C16 O1 C15 -4.2(4) . . . . ? C18 C16 O1 C15 177.0(2) . . . . ? C14 C15 O1 C16 36.4(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.69 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.328 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.062 data_2l _database_code_depnum_ccdc_archive 'CCDC 924032' #TrackingRef 'web_deposit_cif_file_0_CharlesS.Yeung_1360436158.Brindle, Yeung, Jacobsen_Chemical Sciences Submission.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 Cl3 I N O2' _chemical_formula_weight 448.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 _symmetry_space_group_name_Hall C2y loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 25.646(3) _cell_length_b 6.3769(7) _cell_length_c 10.8278(11) _cell_angle_alpha 90.00 _cell_angle_beta 112.7660(10) _cell_angle_gamma 90.00 _cell_volume 1632.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5801 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 27.2 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 2.451 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5907 _exptl_absorpt_correction_T_max 0.6951 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker D8 goniometer with CCD area detector ; _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9229 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.14 _reflns_number_total 3530 _reflns_number_gt 3253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 3530 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0600 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.63107(13) 0.7636(11) 0.2318(3) 0.0198(7) Uani 1 1 d . . . H1 H 0.6124 0.7110 0.1435 0.024 Uiso 1 1 calc R . . C2 C 0.62412(16) 0.6598(7) 0.3396(4) 0.0223(9) Uani 1 1 d . . . C3 C 0.65055(17) 0.7352(8) 0.4676(4) 0.0251(13) Uani 1 1 d . . . H3 H 0.6464 0.6663 0.5410 0.030 Uiso 1 1 calc R . . C4 C 0.68324(19) 0.9132(8) 0.4870(4) 0.0327(11) Uani 1 1 d . . . H4 H 0.7014 0.9668 0.5752 0.039 Uiso 1 1 calc R . . C5 C 0.69060(17) 1.0165(8) 0.3830(4) 0.0280(9) Uani 1 1 d . . . H5 H 0.7133 1.1391 0.3998 0.034 Uiso 1 1 calc R . . C6 C 0.66429(15) 0.9390(7) 0.2523(4) 0.0196(8) Uani 1 1 d . . . C7 C 0.67340(16) 1.0502(6) 0.1359(4) 0.0204(8) Uani 1 1 d . . . C8 C 0.64870(14) 1.2722(11) 0.1158(3) 0.0247(7) Uani 1 1 d . . . H8A H 0.6603 1.3446 0.2032 0.030 Uiso 1 1 calc R . . H8B H 0.6631 1.3537 0.0578 0.030 Uiso 1 1 calc R . . C9 C 0.58486(15) 1.2579(11) 0.0512(4) 0.0281(9) Uani 1 1 d . . . H9A H 0.5704 1.1847 0.1122 0.034 Uiso 1 1 calc R . . H9B H 0.5684 1.4007 0.0346 0.034 Uiso 1 1 calc R . . C10 C 0.60183(15) 0.9852(7) -0.0747(4) 0.0199(8) Uani 1 1 d . . . C11 C 0.5802(2) 0.3774(9) 0.4083(5) 0.0398(12) Uani 1 1 d . . . H11A H 0.5556 0.2565 0.3701 0.060 Uiso 1 1 calc R . . H11B H 0.5616 0.4725 0.4498 0.060 Uiso 1 1 calc R . . H11C H 0.6161 0.3290 0.4762 0.060 Uiso 1 1 calc R . . C12 C 0.73676(16) 1.0692(6) 0.1662(4) 0.0226(9) Uani 1 1 d . . . H12A H 0.7548 1.1549 0.2481 0.027 Uiso 1 1 calc R . . H12B H 0.7417 1.1440 0.0913 0.027 Uiso 1 1 calc R . . C13 C 0.57584(16) 0.8637(7) -0.2052(4) 0.0233(9) Uani 1 1 d . . . N1 N 0.64805(13) 0.9263(5) 0.0130(3) 0.0191(7) Uani 1 1 d . . . O1 O 0.59070(12) 0.4862(5) 0.3040(3) 0.0275(7) Uani 1 1 d . . . O2 O 0.56784(12) 1.1443(5) -0.0745(3) 0.0302(7) Uani 1 1 d . . . Cl1 Cl 0.61757(5) 0.64935(19) -0.21131(10) 0.0316(3) Uani 1 1 d . . . Cl2 Cl 0.56702(5) 1.0334(2) -0.34161(11) 0.0390(3) Uani 1 1 d . . . Cl3 Cl 0.50896(4) 0.7703(3) -0.21910(10) 0.0432(3) Uani 1 1 d . . . I1 I 0.779116(9) 0.77262(4) 0.19456(2) 0.02678(8) 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 0.0192(14) 0.024(2) 0.0176(16) 0.002(3) 0.0090(12) 0.005(3) C2 0.0173(18) 0.027(2) 0.023(2) 0.0043(18) 0.0091(16) 0.0056(17) C3 0.0321(19) 0.029(4) 0.0169(18) 0.0058(19) 0.0127(16) 0.012(2) C4 0.038(2) 0.040(3) 0.014(2) 0.000(2) 0.0037(19) 0.009(2) C5 0.030(2) 0.025(2) 0.027(2) -0.003(2) 0.0097(18) -0.0015(19) C6 0.0154(17) 0.025(2) 0.0189(19) -0.0011(16) 0.0067(15) 0.0055(15) C7 0.0216(19) 0.020(2) 0.020(2) 0.0013(17) 0.0078(16) 0.0025(16) C8 0.0252(16) 0.0193(17) 0.0261(18) -0.001(3) 0.0059(14) 0.002(3) C9 0.0278(17) 0.022(2) 0.032(2) -0.007(3) 0.0088(15) 0.004(3) C10 0.0196(19) 0.021(2) 0.0173(19) -0.0014(17) 0.0049(16) -0.0035(16) C11 0.045(3) 0.043(3) 0.041(3) 0.020(2) 0.026(2) 0.003(2) C12 0.0216(19) 0.018(2) 0.027(2) 0.0029(17) 0.0090(17) 0.0011(16) C13 0.0197(19) 0.032(2) 0.019(2) -0.0004(17) 0.0083(16) 0.0014(16) N1 0.0186(15) 0.0213(18) 0.0189(17) 0.0005(14) 0.0090(14) -0.0026(13) O1 0.0292(15) 0.0331(18) 0.0253(15) 0.0077(14) 0.0162(13) 0.0002(13) O2 0.0236(15) 0.0309(17) 0.0295(16) -0.0063(15) 0.0029(13) 0.0052(13) Cl1 0.0358(6) 0.0369(7) 0.0222(5) -0.0063(5) 0.0112(4) 0.0024(5) Cl2 0.0401(6) 0.0502(8) 0.0222(5) 0.0094(5) 0.0071(5) 0.0005(6) Cl3 0.0278(4) 0.0634(7) 0.0439(6) -0.0214(10) 0.0197(4) -0.0209(9) I1 0.02370(11) 0.03121(14) 0.02906(13) 0.00680(18) 0.01419(9) 0.00642(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.371(7) . ? C1 C2 1.412(6) . ? C1 H1 0.9500 . ? C2 O1 1.361(5) . ? C2 C3 1.372(6) . ? C3 C4 1.378(7) . ? C3 H3 0.9500 . ? C4 C5 1.379(6) . ? C4 H4 0.9500 . ? C5 C6 1.401(6) . ? C5 H5 0.9500 . ? C6 C7 1.540(5) . ? C7 N1 1.465(5) . ? C7 C8 1.532(7) . ? C7 C12 1.533(5) . ? C8 C9 1.514(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O2 1.452(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N1 1.256(5) . ? C10 O2 1.338(5) . ? C10 C13 1.520(5) . ? C11 O1 1.438(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 I1 2.143(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 Cl1 1.753(4) . ? C13 Cl3 1.766(4) . ? C13 Cl2 1.774(4) . ? 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 C6 C1 C2 121.2(4) . . ? C6 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? O1 C2 C3 125.6(4) . . ? O1 C2 C1 114.4(4) . . ? C3 C2 C1 119.9(4) . . ? C2 C3 C4 118.5(4) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C3 C4 C5 122.4(4) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 119.5(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 118.5(4) . . ? C1 C6 C7 121.6(3) . . ? C5 C6 C7 119.9(4) . . ? N1 C7 C8 110.8(3) . . ? N1 C7 C12 107.4(3) . . ? C8 C7 C12 107.6(3) . . ? N1 C7 C6 109.9(3) . . ? C8 C7 C6 110.9(3) . . ? C12 C7 C6 110.2(3) . . ? C9 C8 C7 108.9(5) . . ? C9 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? C9 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O2 C9 C8 110.0(3) . . ? O2 C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? O2 C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? N1 C10 O2 130.6(4) . . ? N1 C10 C13 119.8(4) . . ? O2 C10 C13 109.6(3) . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C12 I1 113.4(3) . . ? C7 C12 H12A 108.9 . . ? I1 C12 H12A 108.9 . . ? C7 C12 H12B 108.9 . . ? I1 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C10 C13 Cl1 112.2(3) . . ? C10 C13 Cl3 108.3(3) . . ? Cl1 C13 Cl3 108.7(2) . . ? C10 C13 Cl2 109.4(3) . . ? Cl1 C13 Cl2 109.1(2) . . ? Cl3 C13 Cl2 109.1(2) . . ? C10 N1 C7 118.9(3) . . ? C2 O1 C11 117.3(4) . . ? C10 O2 C9 114.8(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 C6 C1 C2 O1 -178.9(4) . . . . ? C6 C1 C2 C3 0.5(6) . . . . ? O1 C2 C3 C4 179.8(4) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? C2 C3 C4 C5 -0.5(7) . . . . ? C3 C4 C5 C6 -0.2(7) . . . . ? C2 C1 C6 C5 -1.2(6) . . . . ? C2 C1 C6 C7 178.4(4) . . . . ? C4 C5 C6 C1 1.1(6) . . . . ? C4 C5 C6 C7 -178.5(4) . . . . ? C1 C6 C7 N1 -7.0(5) . . . . ? C5 C6 C7 N1 172.6(3) . . . . ? C1 C6 C7 C8 115.9(4) . . . . ? C5 C6 C7 C8 -64.5(5) . . . . ? C1 C6 C7 C12 -125.1(4) . . . . ? C5 C6 C7 C12 54.5(5) . . . . ? N1 C7 C8 C9 48.4(4) . . . . ? C12 C7 C8 C9 165.5(3) . . . . ? C6 C7 C8 C9 -73.9(4) . . . . ? C7 C8 C9 O2 -57.3(5) . . . . ? N1 C7 C12 I1 -59.7(4) . . . . ? C8 C7 C12 I1 -179.0(2) . . . . ? C6 C7 C12 I1 59.9(4) . . . . ? N1 C10 C13 Cl1 -0.2(5) . . . . ? O2 C10 C13 Cl1 -178.9(3) . . . . ? N1 C10 C13 Cl3 119.8(4) . . . . ? O2 C10 C13 Cl3 -58.9(4) . . . . ? N1 C10 C13 Cl2 -121.4(4) . . . . ? O2 C10 C13 Cl2 59.9(4) . . . . ? O2 C10 N1 C7 -3.9(6) . . . . ? C13 C10 N1 C7 177.7(3) . . . . ? C8 C7 N1 C10 -19.2(5) . . . . ? C12 C7 N1 C10 -136.5(4) . . . . ? C6 C7 N1 C10 103.7(4) . . . . ? C3 C2 O1 C11 2.9(6) . . . . ? C1 C2 O1 C11 -177.8(4) . . . . ? N1 C10 O2 C9 -5.3(7) . . . . ? C13 C10 O2 C9 173.2(4) . . . . ? C8 C9 O2 C10 36.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.981 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.089 data_5c _database_code_depnum_ccdc_archive 'CCDC 924033' #TrackingRef 'web_deposit_cif_file_0_CharlesS.Yeung_1360436158.Brindle, Yeung, Jacobsen_Chemical Sciences Submission.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 Cl4 F I N O' _chemical_formula_weight 472.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall P2ac2ab 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 9.9921(4) _cell_length_b 17.5041(6) _cell_length_c 18.6434(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3260.8(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9846 _cell_measurement_theta_min 5.05 _cell_measurement_theta_max 66.1 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.927 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 21.521 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0713 _exptl_absorpt_correction_T_max 0.5645 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'I\mS microfocus tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker D8 goniometer with CCD area detector ; _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 57065 _diffrn_reflns_av_R_equivalents 0.1018 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 66.81 _reflns_number_total 5723 _reflns_number_gt 4899 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+12.1441P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.018(9) _chemical_absolute_configuration ad _refine_ls_number_reflns 5723 _refine_ls_number_parameters 374 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.0678 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1442 _refine_ls_wR_factor_gt 0.1359 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7415(11) 0.5962(6) 0.4030(5) 0.051(2) Uani 1 1 d . . . H1 H 0.6813 0.5598 0.4228 0.061 Uiso 1 1 calc R . . C2 C 0.7725(13) 0.6600(6) 0.4409(5) 0.061(3) Uani 1 1 d . . . C3 C 0.8575(13) 0.7150(6) 0.4143(6) 0.064(3) Uani 1 1 d . . . H3 H 0.8775 0.7596 0.4414 0.077 Uiso 1 1 calc R . . C4 C 0.9115(11) 0.7041(5) 0.3493(6) 0.058(3) Uani 1 1 d . . . H4 H 0.9716 0.7411 0.3305 0.069 Uiso 1 1 calc R . . C5 C 0.8810(10) 0.6402(5) 0.3092(5) 0.046(2) Uani 1 1 d . . . H5 H 0.9180 0.6344 0.2626 0.056 Uiso 1 1 calc R . . C6 C 0.7960(9) 0.5838(5) 0.3368(5) 0.0406(19) Uani 1 1 d . . . C7 C 0.7509(9) 0.5146(5) 0.2916(4) 0.0405(19) Uani 1 1 d . . . C8 C 0.8566(9) 0.4972(5) 0.2341(5) 0.044(2) Uani 1 1 d . . . H8A H 0.9435 0.4890 0.2583 0.052 Uiso 1 1 calc R . . H8B H 0.8661 0.5428 0.2031 0.052 Uiso 1 1 calc R . . C9 C 0.6120(10) 0.5302(5) 0.2591(5) 0.045(2) Uani 1 1 d . . . H9A H 0.5789 0.4831 0.2355 0.054 Uiso 1 1 calc R . . H9B H 0.5487 0.5434 0.2980 0.054 Uiso 1 1 calc R . . C10 C 0.6149(10) 0.5955(6) 0.2039(5) 0.054(2) Uani 1 1 d . . . H10A H 0.6722 0.5811 0.1628 0.065 Uiso 1 1 calc R . . H10B H 0.6526 0.6421 0.2262 0.065 Uiso 1 1 calc R . . C11 C 0.8331(9) 0.4193(5) 0.3788(5) 0.042(2) Uani 1 1 d . . . C12 C 0.7935(11) 0.3566(5) 0.4345(6) 0.056(3) Uani 1 1 d . . . Cl2 Cl 0.9361(3) 0.31362(14) 0.47099(16) 0.0619(7) Uani 1 1 d . . . Cl3 Cl 0.6856(3) 0.28857(16) 0.39844(19) 0.0768(9) Uani 1 1 d . . . Cl4 Cl 0.7089(4) 0.4049(2) 0.50696(15) 0.0903(11) Uani 1 1 d . . . N1 N 0.7339(7) 0.4478(4) 0.3403(4) 0.0423(16) Uani 1 1 d . . . H1A H 0.6544 0.4264 0.3435 0.051 Uiso 1 1 calc R . . O1 O 0.9484(6) 0.4414(4) 0.3766(3) 0.0450(15) Uani 1 1 d . . . F1 F 0.7144(9) 0.6711(4) 0.5061(3) 0.088(2) Uani 1 1 d . . . Cl1 Cl 0.4481(3) 0.61355(14) 0.17380(14) 0.0610(6) Uani 1 1 d . . . I1 I 0.81798(8) 0.40125(5) 0.16734(4) 0.0687(2) Uani 1 1 d . . . C21 C 0.2301(11) 0.5948(7) 0.3632(5) 0.056(2) Uani 1 1 d . . . H21 H 0.1606 0.5633 0.3450 0.067 Uiso 1 1 calc R . . C22 C 0.2635(13) 0.6603(7) 0.3285(6) 0.064(3) Uani 1 1 d . . . C23 C 0.3632(13) 0.7074(7) 0.3546(8) 0.072(4) Uani 1 1 d . . . H23 H 0.3830 0.7540 0.3308 0.086 Uiso 1 1 calc R . . C24 C 0.4306(14) 0.6880(7) 0.4121(8) 0.072(3) Uani 1 1 d . . . H24 H 0.5018 0.7192 0.4288 0.087 Uiso 1 1 calc R . . C25 C 0.3973(12) 0.6212(5) 0.4486(6) 0.055(3) Uani 1 1 d . . . H25 H 0.4446 0.6079 0.4909 0.066 Uiso 1 1 calc R . . C26 C 0.2968(10) 0.5743(5) 0.4241(5) 0.049(2) Uani 1 1 d . . . C27 C 0.2549(9) 0.5011(5) 0.4652(4) 0.0395(19) Uani 1 1 d . . . C28 C 0.1166(11) 0.5144(5) 0.4983(5) 0.047(2) Uani 1 1 d . . . H28A H 0.0855 0.4658 0.5198 0.056 Uiso 1 1 calc R . . H28B H 0.0534 0.5279 0.4594 0.056 Uiso 1 1 calc R . . C29 C 0.3569(11) 0.4765(5) 0.5212(5) 0.049(2) Uani 1 1 d U . . H29A H 0.4469 0.4784 0.4990 0.059 Uiso 1 1 calc R . . H29B H 0.3557 0.5142 0.5607 0.059 Uiso 1 1 calc R . . C30 C 0.3375(10) 0.3983(6) 0.5529(6) 0.059(2) Uani 1 1 d U . . H30A H 0.3524 0.3599 0.5148 0.070 Uiso 1 1 calc R . . H30B H 0.2433 0.3936 0.5688 0.070 Uiso 1 1 calc R . . Cl5 Cl 0.4399(4) 0.3768(2) 0.62422(15) 0.0854(10) Uani 1 1 d U . . C31 C 0.3320(9) 0.4122(5) 0.3723(4) 0.0368(18) Uani 1 1 d D . . N2 N 0.2323(7) 0.4388(4) 0.4121(4) 0.0382(15) Uani 1 1 d . A . H2 H 0.1517 0.4193 0.4071 0.046 Uiso 1 1 calc R . . O2 O 0.4487(6) 0.4316(4) 0.3760(3) 0.0445(14) Uani 1 1 d . A . F2 F 0.1972(9) 0.6813(5) 0.2698(4) 0.094(2) Uani 1 1 d . . . C32 C 0.2935(18) 0.3420(8) 0.3231(8) 0.0487(17) Uani 0.530(6) 1 d PDU A 1 Cl6 Cl 0.428(3) 0.319(3) 0.266(2) 0.0525(16) Uani 0.530(6) 1 d PDU A 1 Cl7 Cl 0.1564(7) 0.3680(5) 0.2658(4) 0.082(2) Uani 0.530(6) 1 d PDU A 1 Cl8 Cl 0.2498(9) 0.2634(4) 0.3754(4) 0.0739(15) Uani 0.530(6) 1 d PDU A 1 C32B C 0.285(2) 0.3544(9) 0.3127(9) 0.0487(17) Uani 0.470(6) 1 d PD A 2 Cl6B Cl 0.423(3) 0.312(3) 0.271(3) 0.0525(16) Uani 0.470(6) 1 d PD A 2 Cl7B Cl 0.1972(8) 0.4089(6) 0.2463(4) 0.082(2) Uani 0.470(6) 1 d PD A 2 Cl8B Cl 0.1807(10) 0.2837(4) 0.3472(4) 0.0739(15) Uani 0.470(6) 1 d PD A 2 I2 I 0.10727(8) 0.60090(4) 0.57820(4) 0.0664(2) 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 0.074(6) 0.037(4) 0.041(5) 0.002(4) 0.005(4) 0.000(5) C2 0.089(9) 0.062(6) 0.033(5) -0.007(4) -0.003(5) 0.017(6) C3 0.096(9) 0.046(5) 0.050(6) -0.011(5) -0.027(6) 0.012(6) C4 0.060(6) 0.039(5) 0.074(7) -0.002(5) 0.002(6) -0.010(5) C5 0.052(5) 0.042(5) 0.045(5) 0.001(4) 0.006(4) -0.002(5) C6 0.049(5) 0.032(4) 0.042(4) 0.001(3) -0.002(4) 0.006(4) C7 0.045(5) 0.041(4) 0.036(4) 0.002(4) 0.005(4) -0.001(4) C8 0.045(5) 0.038(5) 0.048(5) -0.003(4) 0.002(4) -0.004(4) C9 0.047(5) 0.040(4) 0.048(5) 0.000(4) -0.002(4) 0.004(4) C10 0.061(6) 0.051(5) 0.050(5) 0.015(5) -0.006(4) 0.011(6) C11 0.042(5) 0.044(5) 0.041(4) -0.002(4) 0.003(4) 0.005(4) C12 0.052(6) 0.040(5) 0.076(7) 0.014(5) -0.009(5) 0.007(5) Cl2 0.0575(15) 0.0492(13) 0.0789(17) 0.0142(12) -0.0209(13) 0.0023(12) Cl3 0.0664(16) 0.0567(15) 0.107(2) 0.0317(15) -0.0277(17) -0.0164(15) Cl4 0.109(3) 0.107(2) 0.0547(14) 0.0261(17) 0.0111(15) 0.044(2) N1 0.038(4) 0.039(4) 0.049(4) 0.003(3) -0.005(3) -0.001(3) O1 0.039(3) 0.046(3) 0.050(4) -0.002(3) -0.005(3) 0.001(3) F1 0.143(7) 0.075(4) 0.047(3) -0.015(3) 0.010(4) 0.012(5) Cl1 0.0715(15) 0.0555(14) 0.0560(13) 0.0034(11) -0.0161(12) 0.0100(13) I1 0.0678(4) 0.0645(4) 0.0738(5) -0.0339(4) -0.0056(4) 0.0067(4) C21 0.062(6) 0.052(6) 0.054(5) 0.003(5) 0.007(5) 0.011(6) C22 0.078(8) 0.058(6) 0.056(6) 0.017(5) 0.008(6) 0.020(6) C23 0.068(8) 0.044(6) 0.102(10) 0.005(6) 0.040(7) 0.004(6) C24 0.079(8) 0.050(6) 0.088(9) -0.009(6) 0.028(7) 0.003(6) C25 0.072(7) 0.033(4) 0.060(6) -0.011(4) 0.015(5) -0.003(5) C26 0.056(6) 0.036(4) 0.055(5) -0.005(4) 0.016(5) 0.001(4) C27 0.043(5) 0.039(5) 0.037(4) -0.005(4) 0.001(4) -0.003(4) C28 0.059(6) 0.038(4) 0.043(5) -0.006(4) 0.008(4) -0.004(5) C29 0.061(6) 0.045(5) 0.040(4) -0.012(4) 0.006(4) -0.006(4) C30 0.054(6) 0.055(5) 0.067(6) 0.014(5) 0.026(4) 0.004(6) Cl5 0.111(3) 0.098(2) 0.0475(14) 0.0117(14) -0.0230(15) -0.016(2) C31 0.040(5) 0.035(4) 0.035(4) -0.002(3) 0.003(3) 0.007(4) N2 0.037(4) 0.038(4) 0.039(4) -0.012(3) 0.003(3) -0.002(3) O2 0.042(4) 0.043(3) 0.049(4) 0.000(3) 0.007(3) 0.002(3) F2 0.098(6) 0.098(5) 0.085(5) 0.029(4) 0.007(5) 0.014(5) C32 0.052(5) 0.049(5) 0.045(6) -0.007(3) 0.006(2) 0.008(5) Cl6 0.059(2) 0.053(6) 0.045(4) -0.007(2) 0.0088(11) 0.011(3) Cl7 0.067(3) 0.119(6) 0.059(3) -0.043(3) -0.016(3) 0.033(4) Cl8 0.104(5) 0.047(3) 0.070(4) -0.0168(19) 0.033(3) -0.020(3) C32B 0.052(5) 0.049(5) 0.045(6) -0.007(3) 0.006(2) 0.008(5) Cl6B 0.059(2) 0.053(6) 0.045(4) -0.007(2) 0.0088(11) 0.011(3) Cl7B 0.067(3) 0.119(6) 0.059(3) -0.043(3) -0.016(3) 0.033(4) Cl8B 0.104(5) 0.047(3) 0.070(4) -0.0168(19) 0.033(3) -0.020(3) I2 0.0835(5) 0.0525(4) 0.0632(4) -0.0213(3) 0.0224(4) -0.0067(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.358(14) . ? C1 C6 1.366(13) . ? C1 H1 0.9500 . ? C2 F1 1.361(12) . ? C2 C3 1.376(17) . ? C3 C4 1.340(16) . ? C3 H3 0.9500 . ? C4 C5 1.381(14) . ? C4 H4 0.9500 . ? C5 C6 1.401(13) . ? C5 H5 0.9500 . ? C6 C7 1.543(12) . ? C7 N1 1.490(11) . ? C7 C8 1.535(12) . ? C7 C9 1.539(13) . ? C8 I1 2.125(9) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.537(12) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 Cl1 1.788(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O1 1.217(11) . ? C11 N1 1.323(12) . ? C11 C12 1.561(13) . ? C12 Cl3 1.742(11) . ? C12 Cl2 1.749(10) . ? C12 Cl4 1.803(12) . ? N1 H1A 0.8800 . ? C21 C22 1.357(16) . ? C21 C26 1.366(15) . ? C21 H21 0.9500 . ? C22 F2 1.332(13) . ? C22 C23 1.382(18) . ? C23 C24 1.31(2) . ? C23 H23 0.9500 . ? C24 C25 1.392(16) . ? C24 H24 0.9500 . ? C25 C26 1.375(14) . ? C25 H25 0.9500 . ? C26 C27 1.549(12) . ? C27 N2 1.491(10) . ? C27 C29 1.522(13) . ? C27 C28 1.532(13) . ? C28 I2 2.126(8) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.503(14) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 Cl5 1.720(11) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 O2 1.216(11) . ? C31 N2 1.326(10) . ? C31 C32B 1.575(17) . ? C31 C32 1.581(16) . ? N2 H2 0.8800 . ? C32 Cl8 1.742(15) . ? C32 Cl6 1.759(14) . ? C32 Cl7 1.796(15) . ? C32B Cl8B 1.738(16) . ? C32B Cl6B 1.754(15) . ? C32B Cl7B 1.790(16) . ? 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 C1 C6 120.7(10) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C1 C2 F1 119.0(11) . . ? C1 C2 C3 121.9(9) . . ? F1 C2 C3 119.1(10) . . ? C4 C3 C2 118.4(9) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C5 121.1(10) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 120.4(9) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 117.5(8) . . ? C1 C6 C7 120.2(8) . . ? C5 C6 C7 121.9(8) . . ? N1 C7 C8 110.4(7) . . ? N1 C7 C9 106.0(7) . . ? C8 C7 C9 112.4(7) . . ? N1 C7 C6 108.4(7) . . ? C8 C7 C6 109.7(7) . . ? C9 C7 C6 109.9(7) . . ? C7 C8 I1 116.2(6) . . ? C7 C8 H8A 108.2 . . ? I1 C8 H8A 108.2 . . ? C7 C8 H8B 108.2 . . ? I1 C8 H8B 108.2 . . ? H8A C8 H8B 107.4 . . ? C10 C9 C7 112.2(8) . . ? C10 C9 H9A 109.2 . . ? C7 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? C7 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C9 C10 Cl1 108.9(7) . . ? C9 C10 H10A 109.9 . . ? Cl1 C10 H10A 109.9 . . ? C9 C10 H10B 109.9 . . ? Cl1 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? O1 C11 N1 124.8(9) . . ? O1 C11 C12 119.1(8) . . ? N1 C11 C12 115.9(8) . . ? C11 C12 Cl3 112.4(7) . . ? C11 C12 Cl2 110.8(7) . . ? Cl3 C12 Cl2 111.1(5) . . ? C11 C12 Cl4 106.7(6) . . ? Cl3 C12 Cl4 108.6(6) . . ? Cl2 C12 Cl4 107.0(6) . . ? C11 N1 C7 122.8(8) . . ? C11 N1 H1A 118.6 . . ? C7 N1 H1A 118.6 . . ? C22 C21 C26 119.9(11) . . ? C22 C21 H21 120.1 . . ? C26 C21 H21 120.1 . . ? F2 C22 C21 120.1(12) . . ? F2 C22 C23 118.9(11) . . ? C21 C22 C23 120.9(11) . . ? C24 C23 C22 120.2(11) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 119.6(13) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C26 C25 C24 121.0(12) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C21 C26 C25 118.3(9) . . ? C21 C26 C27 119.8(9) . . ? C25 C26 C27 121.9(9) . . ? N2 C27 C29 110.4(7) . . ? N2 C27 C28 104.0(7) . . ? C29 C27 C28 111.7(7) . . ? N2 C27 C26 108.6(7) . . ? C29 C27 C26 113.1(8) . . ? C28 C27 C26 108.5(7) . . ? C27 C28 I2 115.5(6) . . ? C27 C28 H28A 108.4 . . ? I2 C28 H28A 108.4 . . ? C27 C28 H28B 108.4 . . ? I2 C28 H28B 108.4 . . ? H28A C28 H28B 107.5 . . ? C30 C29 C27 116.2(8) . . ? C30 C29 H29A 108.2 . . ? C27 C29 H29A 108.2 . . ? C30 C29 H29B 108.2 . . ? C27 C29 H29B 108.2 . . ? H29A C29 H29B 107.4 . . ? C29 C30 Cl5 115.2(8) . . ? C29 C30 H30A 108.5 . . ? Cl5 C30 H30A 108.5 . . ? C29 C30 H30B 108.5 . . ? Cl5 C30 H30B 108.5 . . ? H30A C30 H30B 107.5 . . ? O2 C31 N2 126.2(8) . . ? O2 C31 C32B 120.5(10) . . ? N2 C31 C32B 113.2(10) . . ? O2 C31 C32 118.9(9) . . ? N2 C31 C32 114.5(10) . . ? C31 N2 C27 121.0(7) . . ? C31 N2 H2 119.5 . . ? C27 N2 H2 119.5 . . ? C31 C32 Cl8 110.4(10) . . ? C31 C32 Cl6 110(3) . . ? Cl8 C32 Cl6 110.5(11) . . ? C31 C32 Cl7 109.5(10) . . ? Cl8 C32 Cl7 110.0(9) . . ? Cl6 C32 Cl7 106.4(14) . . ? C31 C32B Cl8B 112.1(11) . . ? C31 C32B Cl6B 110(3) . . ? Cl8B C32B Cl6B 109.6(15) . . ? C31 C32B Cl7B 107.0(10) . . ? Cl8B C32B Cl7B 110.1(10) . . ? Cl6B C32B Cl7B 107.5(13) . . ? 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 C6 C1 C2 F1 178.8(9) . . . . ? C6 C1 C2 C3 1.0(17) . . . . ? C1 C2 C3 C4 -0.6(17) . . . . ? F1 C2 C3 C4 -178.4(10) . . . . ? C2 C3 C4 C5 1.1(17) . . . . ? C3 C4 C5 C6 -2.1(16) . . . . ? C2 C1 C6 C5 -1.9(14) . . . . ? C2 C1 C6 C7 -174.8(9) . . . . ? C4 C5 C6 C1 2.4(14) . . . . ? C4 C5 C6 C7 175.2(9) . . . . ? C1 C6 C7 N1 -39.8(11) . . . . ? C5 C6 C7 N1 147.6(8) . . . . ? C1 C6 C7 C8 -160.4(8) . . . . ? C5 C6 C7 C8 27.0(11) . . . . ? C1 C6 C7 C9 75.6(10) . . . . ? C5 C6 C7 C9 -97.0(10) . . . . ? N1 C7 C8 I1 58.7(9) . . . . ? C9 C7 C8 I1 -59.4(9) . . . . ? C6 C7 C8 I1 178.1(6) . . . . ? N1 C7 C9 C10 -176.9(7) . . . . ? C8 C7 C9 C10 -56.2(10) . . . . ? C6 C7 C9 C10 66.2(9) . . . . ? C7 C9 C10 Cl1 -176.1(6) . . . . ? O1 C11 C12 Cl3 -138.6(8) . . . . ? N1 C11 C12 Cl3 45.6(10) . . . . ? O1 C11 C12 Cl2 -13.7(11) . . . . ? N1 C11 C12 Cl2 170.5(7) . . . . ? O1 C11 C12 Cl4 102.4(9) . . . . ? N1 C11 C12 Cl4 -73.4(9) . . . . ? O1 C11 N1 C7 -3.5(14) . . . . ? C12 C11 N1 C7 172.0(8) . . . . ? C8 C7 N1 C11 59.5(11) . . . . ? C9 C7 N1 C11 -178.6(8) . . . . ? C6 C7 N1 C11 -60.7(11) . . . . ? C26 C21 C22 F2 -178.8(9) . . . . ? C26 C21 C22 C23 -0.8(16) . . . . ? F2 C22 C23 C24 -179.6(11) . . . . ? C21 C22 C23 C24 2.5(18) . . . . ? C22 C23 C24 C25 -2.8(17) . . . . ? C23 C24 C25 C26 1.6(16) . . . . ? C22 C21 C26 C25 -0.3(15) . . . . ? C22 C21 C26 C27 177.7(9) . . . . ? C24 C25 C26 C21 -0.1(14) . . . . ? C24 C25 C26 C27 -178.0(9) . . . . ? C21 C26 C27 N2 43.9(11) . . . . ? C25 C26 C27 N2 -138.2(9) . . . . ? C21 C26 C27 C29 166.9(8) . . . . ? C25 C26 C27 C29 -15.2(12) . . . . ? C21 C26 C27 C28 -68.5(10) . . . . ? C25 C26 C27 C28 109.4(10) . . . . ? N2 C27 C28 I2 180.0(5) . . . . ? C29 C27 C28 I2 60.8(9) . . . . ? C26 C27 C28 I2 -64.5(8) . . . . ? N2 C27 C29 C30 -46.5(11) . . . . ? C28 C27 C29 C30 68.8(10) . . . . ? C26 C27 C29 C30 -168.4(8) . . . . ? C27 C29 C30 Cl5 -171.7(7) . . . . ? O2 C31 N2 C27 3.4(14) . . . . ? C32B C31 N2 C27 -172.4(9) . . . . ? C32 C31 N2 C27 175.6(9) . . . . ? C29 C27 N2 C31 -60.3(10) . . . . ? C28 C27 N2 C31 179.7(7) . . . . ? C26 C27 N2 C31 64.3(10) . . . . ? O2 C31 C32 Cl8 108.5(12) . . . . ? N2 C31 C32 Cl8 -64.3(13) . . . . ? C32B C31 C32 Cl8 -150(7) . . . . ? O2 C31 C32 Cl6 -13.7(16) . . . . ? N2 C31 C32 Cl6 173.5(11) . . . . ? C32B C31 C32 Cl6 88(6) . . . . ? O2 C31 C32 Cl7 -130.2(10) . . . . ? N2 C31 C32 Cl7 57.0(12) . . . . ? C32B C31 C32 Cl7 -29(6) . . . . ? O2 C31 C32B Cl8B 134.4(11) . . . . ? N2 C31 C32B Cl8B -49.5(14) . . . . ? C32 C31 C32B Cl8B 50(6) . . . . ? O2 C31 C32B Cl6B 12.0(16) . . . . ? N2 C31 C32B Cl6B -172.0(12) . . . . ? C32 C31 C32B Cl6B -73(6) . . . . ? O2 C31 C32B Cl7B -104.7(13) . . . . ? N2 C31 C32B Cl7B 71.3(12) . . . . ? C32 C31 C32B Cl7B 171(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O2 0.88 2.14 2.940(10) 150.1 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 66.81 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.286 _refine_diff_density_min -0.647 _refine_diff_density_rms 0.131 data_7a _database_code_depnum_ccdc_archive 'CCDC 924034' #TrackingRef 'web_deposit_cif_file_0_CharlesS.Yeung_1360436158.Brindle, Yeung, Jacobsen_Chemical Sciences Submission.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H11 Cl3 N2 O' _chemical_formula_weight 317.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall P2ac2ab 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 11.2235(16) _cell_length_b 11.7597(17) _cell_length_c 20.531(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2709.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9976 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.2 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.668 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8892 _exptl_absorpt_correction_T_max 0.9485 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; Bruker D8 goniometer with CCD area detector ; _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 32256 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.11 _reflns_number_total 5996 _reflns_number_gt 5337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; # start Validation Reply Form _vrf_PLAT431_CSY-2-69 ; PROBLEM: Short Inter HL..A Contact Cl4 .. N4 2.94 Ang. RESPONSE: There are strong intermolecular interacation between CF3 and CN groups. ; # end Validation Reply Form _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^)+(0.0264P)^2^+0.1914P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 5996 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0608 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C21 C 0.24034(19) 0.2199(2) 0.29345(11) 0.0170(5) Uani 1 1 d . . . H21 H 0.2332 0.1436 0.3081 0.020 Uiso 1 1 calc R . . C22 C 0.2379(2) 0.2430(2) 0.22715(11) 0.0212(5) Uani 1 1 d . . . H22 H 0.2286 0.1825 0.1969 0.025 Uiso 1 1 calc R . . C23 C 0.2489(2) 0.3540(2) 0.20483(12) 0.0207(5) Uani 1 1 d . . . H23 H 0.2483 0.3697 0.1594 0.025 Uiso 1 1 calc R . . C24 C 0.26086(19) 0.4414(2) 0.24939(12) 0.0199(5) Uani 1 1 d . . . H24 H 0.2673 0.5177 0.2345 0.024 Uiso 1 1 calc R . . C25 C 0.2635(2) 0.41877(19) 0.31577(12) 0.0171(5) Uani 1 1 d . . . H25 H 0.2725 0.4795 0.3459 0.020 Uiso 1 1 calc R . . C26 C 0.25309(19) 0.30724(19) 0.33862(11) 0.0141(5) Uani 1 1 d . . . C27 C 0.26581(18) 0.27920(18) 0.40966(11) 0.0124(4) Uani 1 1 d . . . C28 C 0.2047(2) 0.17176(19) 0.43307(11) 0.0158(5) Uani 1 1 d . . . H28A H 0.1245 0.1669 0.4132 0.019 Uiso 1 1 calc R . . H28B H 0.2511 0.1048 0.4185 0.019 Uiso 1 1 calc R . . C29 C 0.1929(2) 0.16888(18) 0.50631(11) 0.0160(5) Uani 1 1 d . . . H29A H 0.1455 0.1018 0.5196 0.019 Uiso 1 1 calc R . . H29B H 0.2727 0.1630 0.5266 0.019 Uiso 1 1 calc R . . C30 C 0.20173(17) 0.37069(17) 0.51614(11) 0.0108(4) Uani 1 1 d . . . C31 C 0.37573(19) 0.31643(19) 0.44468(11) 0.0149(5) Uani 1 1 d . . . H31A H 0.4044 0.2685 0.4811 0.018 Uiso 1 1 calc R . . H31B H 0.4394 0.3531 0.4187 0.018 Uiso 1 1 calc R . . C32 C 0.10785(18) 0.46903(18) 0.51834(11) 0.0124(4) Uani 1 1 d . . . C33 C 0.28982(19) 0.38583(19) 0.57073(11) 0.0143(5) Uani 1 1 d . . . N3 N 0.26360(15) 0.38011(15) 0.45422(9) 0.0117(4) Uani 1 1 d . . . N4 N 0.35932(17) 0.39076(18) 0.61135(10) 0.0219(5) Uani 1 1 d . . . O2 O 0.13441(12) 0.27215(12) 0.52783(7) 0.0128(3) Uani 1 1 d . . . Cl4 Cl 0.01050(4) 0.45406(4) 0.45152(3) 0.01442(12) Uani 1 1 d . . . Cl5 Cl 0.18103(5) 0.60256(5) 0.51294(3) 0.01567(12) Uani 1 1 d . . . Cl6 Cl 0.02678(5) 0.46534(5) 0.59218(3) 0.01714(12) Uani 1 1 d . . . C1 C 0.72350(19) 0.63521(17) 0.53284(11) 0.0139(5) Uani 1 1 d . . . H1 H 0.7954 0.6430 0.5568 0.017 Uiso 1 1 calc R . . C2 C 0.7275(2) 0.62070(18) 0.46562(11) 0.0165(5) Uani 1 1 d . . . H2 H 0.8022 0.6195 0.4439 0.020 Uiso 1 1 calc R . . C3 C 0.6231(2) 0.6080(2) 0.43002(11) 0.0179(5) Uani 1 1 d . . . H3 H 0.6264 0.5978 0.3841 0.021 Uiso 1 1 calc R . . C4 C 0.5143(2) 0.6102(2) 0.46165(11) 0.0182(5) Uani 1 1 d . . . H4 H 0.4427 0.6013 0.4375 0.022 Uiso 1 1 calc R . . C5 C 0.50967(19) 0.62538(18) 0.52900(11) 0.0172(5) Uani 1 1 d . . . H5 H 0.4347 0.6270 0.5505 0.021 Uiso 1 1 calc R . . C6 C 0.6142(2) 0.63827(18) 0.56511(11) 0.0127(5) Uani 1 1 d . . . C7 C 0.60142(18) 0.65957(19) 0.63714(11) 0.0122(5) Uani 1 1 d . . . C8 C 0.5632(2) 0.77986(19) 0.65436(11) 0.0169(5) Uani 1 1 d . . . H8A H 0.6108 0.8349 0.6288 0.020 Uiso 1 1 calc R . . H8B H 0.4783 0.7904 0.6427 0.020 Uiso 1 1 calc R . . C9 C 0.5800(2) 0.8033(2) 0.72647(11) 0.0183(5) Uani 1 1 d . . . H9A H 0.5615 0.8838 0.7362 0.022 Uiso 1 1 calc R . . H9B H 0.5259 0.7546 0.7524 0.022 Uiso 1 1 calc R . . C10 C 0.73224(18) 0.66401(18) 0.73758(11) 0.0132(4) Uani 1 1 d . . . C11 C 0.56520(19) 0.56376(19) 0.67939(11) 0.0149(5) Uani 1 1 d . . . H11A H 0.5471 0.4901 0.6582 0.018 Uiso 1 1 calc R . . H11B H 0.5160 0.5813 0.7181 0.018 Uiso 1 1 calc R . . C12 C 0.87208(19) 0.66147(18) 0.73935(11) 0.0132(4) Uani 1 1 d . . . C13 C 0.6897(2) 0.5994(2) 0.79668(11) 0.0168(5) Uani 1 1 d . . . N1 N 0.69217(15) 0.60301(16) 0.67951(9) 0.0123(4) Uani 1 1 d . . . N2 N 0.65387(18) 0.5501(2) 0.84016(10) 0.0275(5) Uani 1 1 d . . . O1 O 0.70284(12) 0.77876(12) 0.74293(8) 0.0167(3) Uani 1 1 d . . . Cl1 Cl 0.92255(5) 0.73295(5) 0.81014(3) 0.02225(13) Uani 1 1 d . . . Cl2 Cl 0.92808(5) 0.73124(5) 0.66954(3) 0.01861(13) Uani 1 1 d . . . Cl3 Cl 0.92221(5) 0.51894(5) 0.74149(3) 0.01694(12) 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 C21 0.0149(11) 0.0156(12) 0.0206(13) -0.0015(10) 0.0032(10) -0.0001(10) C22 0.0174(11) 0.0274(14) 0.0187(13) -0.0070(11) 0.0030(10) 0.0008(10) C23 0.0176(12) 0.0306(14) 0.0140(13) 0.0024(11) 0.0009(10) 0.0025(11) C24 0.0184(11) 0.0218(12) 0.0196(14) 0.0035(11) 0.0039(10) 0.0007(9) C25 0.0184(11) 0.0157(12) 0.0171(13) -0.0024(10) 0.0011(10) 0.0008(9) C26 0.0093(10) 0.0143(11) 0.0188(13) -0.0015(10) 0.0037(9) 0.0000(9) C27 0.0108(10) 0.0114(11) 0.0150(12) -0.0022(10) 0.0022(9) 0.0015(9) C28 0.0171(11) 0.0100(11) 0.0202(13) 0.0000(10) 0.0015(9) 0.0000(9) C29 0.0161(11) 0.0095(11) 0.0223(14) 0.0021(10) 0.0023(10) 0.0016(9) C30 0.0116(10) 0.0086(10) 0.0122(11) 0.0014(9) -0.0008(9) -0.0004(8) C31 0.0112(10) 0.0183(12) 0.0153(12) 0.0012(10) 0.0039(9) 0.0023(9) C32 0.0145(10) 0.0126(11) 0.0102(11) -0.0006(9) 0.0010(8) -0.0008(8) C33 0.0163(11) 0.0103(11) 0.0163(12) 0.0019(10) 0.0030(9) -0.0011(9) N3 0.0105(8) 0.0131(9) 0.0114(9) -0.0022(8) 0.0004(7) -0.0004(7) N4 0.0209(10) 0.0225(12) 0.0223(12) 0.0013(10) -0.0051(9) -0.0024(9) O2 0.0130(7) 0.0085(7) 0.0170(9) 0.0005(7) 0.0034(6) -0.0015(6) Cl4 0.0128(2) 0.0164(3) 0.0141(3) 0.0005(2) -0.0032(2) 0.0004(2) Cl5 0.0193(3) 0.0100(3) 0.0177(3) 0.0000(2) -0.0019(2) -0.0015(2) Cl6 0.0192(3) 0.0190(3) 0.0133(3) 0.0000(2) 0.0048(2) 0.0034(2) C1 0.0158(11) 0.0106(11) 0.0153(13) 0.0012(9) -0.0019(9) 0.0019(9) C2 0.0220(11) 0.0107(11) 0.0170(13) 0.0003(10) 0.0032(10) 0.0019(9) C3 0.0294(12) 0.0132(12) 0.0110(12) 0.0011(10) -0.0031(10) 0.0027(10) C4 0.0216(12) 0.0177(12) 0.0155(12) 0.0024(10) -0.0062(10) -0.0022(10) C5 0.0152(11) 0.0168(12) 0.0195(13) 0.0036(10) -0.0004(10) -0.0009(9) C6 0.0202(11) 0.0069(11) 0.0108(12) 0.0022(9) -0.0020(9) -0.0008(9) C7 0.0116(11) 0.0143(11) 0.0107(12) 0.0003(9) -0.0022(8) -0.0011(9) C8 0.0165(11) 0.0168(12) 0.0173(12) 0.0008(10) -0.0007(9) 0.0033(10) C9 0.0164(11) 0.0190(12) 0.0195(13) -0.0017(10) -0.0006(10) 0.0065(10) C10 0.0133(10) 0.0166(11) 0.0096(11) -0.0023(10) -0.0018(9) 0.0024(9) C11 0.0120(10) 0.0187(12) 0.0139(12) 0.0016(9) -0.0020(9) -0.0025(9) C12 0.0145(10) 0.0152(11) 0.0100(11) -0.0024(10) -0.0018(9) 0.0009(9) C13 0.0128(10) 0.0239(13) 0.0139(12) -0.0024(11) -0.0016(9) 0.0029(10) N1 0.0124(9) 0.0129(9) 0.0115(10) 0.0007(8) -0.0025(7) -0.0007(8) N2 0.0239(11) 0.0410(14) 0.0177(12) 0.0066(11) 0.0041(9) 0.0022(10) O1 0.0154(7) 0.0133(8) 0.0214(9) -0.0036(7) -0.0036(7) 0.0032(6) Cl1 0.0205(3) 0.0279(3) 0.0184(3) -0.0080(3) -0.0068(2) 0.0002(3) Cl2 0.0176(3) 0.0202(3) 0.0180(3) 0.0033(2) 0.0020(2) -0.0047(2) Cl3 0.0163(2) 0.0177(3) 0.0169(3) 0.0012(2) 0.0006(2) 0.0035(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C21 C22 1.388(3) . ? C21 C26 1.391(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(3) . ? C22 H22 0.9500 . ? C23 C24 1.382(3) . ? C23 H23 0.9500 . ? C24 C25 1.389(3) . ? C24 H24 0.9500 . ? C25 C26 1.398(3) . ? C25 H25 0.9500 . ? C26 C27 1.502(3) . ? C27 C31 1.493(3) . ? C27 N3 1.499(3) . ? C27 C28 1.516(3) . ? C28 C29 1.510(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 O2 1.449(2) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 O2 1.404(2) . ? C30 N3 1.453(3) . ? C30 C33 1.505(3) . ? C30 C32 1.565(3) . ? C31 N3 1.478(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 Cl4 1.763(2) . ? C32 Cl6 1.768(2) . ? C32 Cl5 1.776(2) . ? C33 N4 1.144(3) . ? C1 C2 1.391(3) . ? C1 C6 1.395(3) . ? C1 H1 0.9500 . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C4 H4 0.9500 . ? C5 C6 1.396(3) . ? C5 H5 0.9500 . ? C6 C7 1.507(3) . ? C7 C11 1.479(3) . ? C7 N1 1.496(3) . ? C7 C8 1.520(3) . ? C8 C9 1.518(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O1 1.448(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O1 1.393(3) . ? C10 N1 1.462(3) . ? C10 C13 1.509(3) . ? C10 C12 1.570(3) . ? C11 N1 1.498(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 Cl2 1.767(2) . ? C12 Cl3 1.769(2) . ? C12 Cl1 1.772(2) . ? C13 N2 1.138(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 C22 C21 C26 120.8(2) . . ? C22 C21 H21 119.6 . . ? C26 C21 H21 119.6 . . ? C21 C22 C23 120.4(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 119.3(2) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C25 120.6(2) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C24 C25 C26 120.5(2) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 118.5(2) . . ? C21 C26 C27 119.7(2) . . ? C25 C26 C27 121.6(2) . . ? C31 C27 N3 59.18(13) . . ? C31 C27 C26 118.78(19) . . ? N3 C27 C26 114.67(18) . . ? C31 C27 C28 117.75(19) . . ? N3 C27 C28 117.32(18) . . ? C26 C27 C28 116.60(19) . . ? C29 C28 C27 111.98(19) . . ? C29 C28 H28A 109.2 . . ? C27 C28 H28A 109.2 . . ? C29 C28 H28B 109.2 . . ? C27 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? O2 C29 C28 108.94(18) . . ? O2 C29 H29A 109.9 . . ? C28 C29 H29A 109.9 . . ? O2 C29 H29B 109.9 . . ? C28 C29 H29B 109.9 . . ? H29A C29 H29B 108.3 . . ? O2 C30 N3 118.01(17) . . ? O2 C30 C33 108.90(17) . . ? N3 C30 C33 109.19(16) . . ? O2 C30 C32 104.04(16) . . ? N3 C30 C32 106.90(16) . . ? C33 C30 C32 109.47(17) . . ? N3 C31 C27 60.58(14) . . ? N3 C31 H31A 117.7 . . ? C27 C31 H31A 117.7 . . ? N3 C31 H31B 117.7 . . ? C27 C31 H31B 117.7 . . ? H31A C31 H31B 114.8 . . ? C30 C32 Cl4 108.73(15) . . ? C30 C32 Cl6 110.67(15) . . ? Cl4 C32 Cl6 110.23(11) . . ? C30 C32 Cl5 109.89(14) . . ? Cl4 C32 Cl5 109.05(12) . . ? Cl6 C32 Cl5 108.25(12) . . ? N4 C33 C30 175.8(2) . . ? C30 N3 C31 118.98(17) . . ? C30 N3 C27 118.80(17) . . ? C31 N3 C27 60.24(13) . . ? C30 O2 C29 113.33(15) . . ? C2 C1 C6 120.2(2) . . ? C2 C1 H1 119.9 . . ? C6 C1 H1 119.9 . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 119.0(2) . . ? C1 C6 C7 123.63(19) . . ? C5 C6 C7 117.37(19) . . ? C11 C7 N1 60.48(13) . . ? C11 C7 C6 118.36(19) . . ? N1 C7 C6 115.61(18) . . ? C11 C7 C8 119.67(19) . . ? N1 C7 C8 118.10(18) . . ? C6 C7 C8 114.19(18) . . ? C9 C8 C7 111.14(19) . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? O1 C9 C8 108.07(17) . . ? O1 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? O1 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? O1 C10 N1 117.81(18) . . ? O1 C10 C13 110.44(18) . . ? N1 C10 C13 108.14(17) . . ? O1 C10 C12 104.67(17) . . ? N1 C10 C12 108.47(17) . . ? C13 C10 C12 106.73(18) . . ? C7 C11 N1 60.31(13) . . ? C7 C11 H11A 117.7 . . ? N1 C11 H11A 117.7 . . ? C7 C11 H11B 117.7 . . ? N1 C11 H11B 117.7 . . ? H11A C11 H11B 114.9 . . ? C10 C12 Cl2 109.14(15) . . ? C10 C12 Cl3 109.67(15) . . ? Cl2 C12 Cl3 110.31(12) . . ? C10 C12 Cl1 109.24(15) . . ? Cl2 C12 Cl1 109.35(12) . . ? Cl3 C12 Cl1 109.11(12) . . ? N2 C13 C10 177.6(2) . . ? C10 N1 C7 117.74(17) . . ? C10 N1 C11 116.43(17) . . ? C7 N1 C11 59.21(13) . . ? C10 O1 C9 113.56(16) . . ? 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 C26 C21 C22 C23 0.4(3) . . . . ? C21 C22 C23 C24 -0.8(3) . . . . ? C22 C23 C24 C25 0.9(3) . . . . ? C23 C24 C25 C26 -0.6(3) . . . . ? C22 C21 C26 C25 -0.1(3) . . . . ? C22 C21 C26 C27 -174.9(2) . . . . ? C24 C25 C26 C21 0.2(3) . . . . ? C24 C25 C26 C27 174.9(2) . . . . ? C21 C26 C27 C31 120.3(2) . . . . ? C25 C26 C27 C31 -54.4(3) . . . . ? C21 C26 C27 N3 -172.73(18) . . . . ? C25 C26 C27 N3 12.6(3) . . . . ? C21 C26 C27 C28 -30.1(3) . . . . ? C25 C26 C27 C28 155.3(2) . . . . ? C31 C27 C28 C29 45.6(3) . . . . ? N3 C27 C28 C29 -22.1(3) . . . . ? C26 C27 C28 C29 -163.72(18) . . . . ? C27 C28 C29 O2 53.8(2) . . . . ? C26 C27 C31 N3 103.1(2) . . . . ? C28 C27 C31 N3 -106.9(2) . . . . ? O2 C30 C32 Cl4 -66.87(18) . . . . ? N3 C30 C32 Cl4 58.71(18) . . . . ? C33 C30 C32 Cl4 176.86(14) . . . . ? O2 C30 C32 Cl6 54.34(19) . . . . ? N3 C30 C32 Cl6 179.92(13) . . . . ? C33 C30 C32 Cl6 -61.93(19) . . . . ? O2 C30 C32 Cl5 173.85(14) . . . . ? N3 C30 C32 Cl5 -60.58(19) . . . . ? C33 C30 C32 Cl5 57.6(2) . . . . ? O2 C30 N3 C31 -77.7(2) . . . . ? C33 C30 N3 C31 47.3(2) . . . . ? C32 C30 N3 C31 165.65(17) . . . . ? O2 C30 N3 C27 -7.8(3) . . . . ? C33 C30 N3 C27 117.25(19) . . . . ? C32 C30 N3 C27 -124.41(18) . . . . ? C27 C31 N3 C30 108.5(2) . . . . ? C31 C27 N3 C30 -108.8(2) . . . . ? C26 C27 N3 C30 141.12(18) . . . . ? C28 C27 N3 C30 -1.2(3) . . . . ? C26 C27 N3 C31 -110.1(2) . . . . ? C28 C27 N3 C31 107.6(2) . . . . ? N3 C30 O2 C29 41.7(2) . . . . ? C33 C30 O2 C29 -83.4(2) . . . . ? C32 C30 O2 C29 159.91(17) . . . . ? C28 C29 O2 C30 -65.2(2) . . . . ? C6 C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 C4 0.2(3) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? C2 C1 C6 C7 -176.8(2) . . . . ? C4 C5 C6 C1 -0.3(3) . . . . ? C4 C5 C6 C7 177.3(2) . . . . ? C1 C6 C7 C11 -108.9(2) . . . . ? C5 C6 C7 C11 73.6(3) . . . . ? C1 C6 C7 N1 -40.2(3) . . . . ? C5 C6 C7 N1 142.4(2) . . . . ? C1 C6 C7 C8 101.8(2) . . . . ? C5 C6 C7 C8 -75.6(2) . . . . ? C11 C7 C8 C9 44.5(3) . . . . ? N1 C7 C8 C9 -25.7(3) . . . . ? C6 C7 C8 C9 -166.71(18) . . . . ? C7 C8 C9 O1 54.8(2) . . . . ? C6 C7 C11 N1 105.0(2) . . . . ? C8 C7 C11 N1 -107.5(2) . . . . ? O1 C10 C12 Cl2 -65.12(19) . . . . ? N1 C10 C12 Cl2 61.5(2) . . . . ? C13 C10 C12 Cl2 177.77(15) . . . . ? O1 C10 C12 Cl3 173.94(14) . . . . ? N1 C10 C12 Cl3 -59.5(2) . . . . ? C13 C10 C12 Cl3 56.8(2) . . . . ? O1 C10 C12 Cl1 54.4(2) . . . . ? N1 C10 C12 Cl1 -179.03(14) . . . . ? C13 C10 C12 Cl1 -62.7(2) . . . . ? O1 C10 N1 C7 -12.8(3) . . . . ? C13 C10 N1 C7 113.2(2) . . . . ? C12 C10 N1 C7 -131.40(19) . . . . ? O1 C10 N1 C11 -80.2(2) . . . . ? C13 C10 N1 C11 45.8(2) . . . . ? C12 C10 N1 C11 161.21(18) . . . . ? C11 C7 N1 C10 -105.8(2) . . . . ? C6 C7 N1 C10 144.71(19) . . . . ? C8 C7 N1 C10 4.2(3) . . . . ? C6 C7 N1 C11 -109.5(2) . . . . ? C8 C7 N1 C11 110.0(2) . . . . ? C7 C11 N1 C10 108.0(2) . . . . ? N1 C10 O1 C9 45.1(2) . . . . ? C13 C10 O1 C9 -79.8(2) . . . . ? C12 C10 O1 C9 165.71(17) . . . . ? C8 C9 O1 C10 -66.5(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.11 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.277 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.053