# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics # This journal is © The Owner Societies 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_added_by_encifer _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 N3 O, 0.5(C2 H4 Cl4)' _chemical_formula_sum 'C20 H19 Cl2 N3 O' _chemical_formula_weight 388.28 _chemical_absolute_configuration ; Friedel pairs were averaged for the refinement ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 _symmetry_space_group_name_Hall 'F 2 -2d' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' _cell_length_a 29.305(1) _cell_length_b 35.039(2) _cell_length_c 7.0828(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7272.7(5) _cell_formula_units_Z 16 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5432 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3232 _exptl_absorpt_coefficient_mu 0.372 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.557 _exptl_absorpt_correction_T_max 0.588 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; Poor crystals (poorly diffracting, solvent loss?). The solvent CHCl2 is poorly resolved - modelled as two 1/2 weight molecules disordered about a special position: bond length & geometry constraints and a common isotropic displacement parameter for the non-H atoms of these disordered moities (JED). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 6815 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1795 _reflns_number_gt 1470 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(7) _refine_ls_number_reflns 1795 _refine_ls_number_parameters 232 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.1159 _refine_ls_wR_factor_ref 0.3462 _refine_ls_wR_factor_gt 0.3237 _refine_ls_goodness_of_fit_ref 1.568 _refine_ls_restrained_S_all 1.569 _refine_ls_shift/su_max 0.000 _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 O1 O 0.15892(15) 0.02172(12) 0.3551(7) 0.0547(13) Uani 1 1 d . . . N1 N 0.3818(2) -0.1282(2) 0.3817(12) 0.084(2) Uani 1 1 d . . . N2 N 0.0852(2) 0.1791(2) 0.3194(10) 0.077(2) Uani 1 1 d . . . N3 N 0.2326(3) 0.1777(2) 0.4205(19) 0.108(4) Uani 1 1 d . . . C1 C 0.4298(3) -0.1143(4) 0.3871(18) 0.109(4) Uani 1 1 d . . . H1A H 0.4329 -0.0948 0.4857 0.163 Uiso 1 1 calc R . . H1B H 0.4378 -0.1032 0.2645 0.163 Uiso 1 1 calc R . . H1C H 0.4503 -0.1357 0.4146 0.163 Uiso 1 1 calc R . . C2 C 0.3734(4) -0.1681(3) 0.3621(14) 0.101(4) Uani 1 1 d . . . H2A H 0.3489 -0.1722 0.2701 0.151 Uiso 1 1 calc R . . H2B H 0.3643 -0.1788 0.4844 0.151 Uiso 1 1 calc R . . H2C H 0.4013 -0.1809 0.3183 0.151 Uiso 1 1 calc R . . C3 C 0.3478(3) -0.1022(2) 0.3727(10) 0.0628(19) Uani 1 1 d . . . C4 C 0.3564(2) -0.0625(2) 0.3785(11) 0.0654(19) Uani 1 1 d . . . H4 H 0.3871 -0.0538 0.3825 0.078 Uiso 1 1 calc R . . C5 C 0.3215(2) -0.03593(19) 0.3784(10) 0.0555(17) Uani 1 1 d . . . H5 H 0.3287 -0.0095 0.3861 0.067 Uiso 1 1 calc R . . C6 C 0.2759(2) -0.04722(18) 0.3671(8) 0.0511(16) Uani 1 1 d . . . C7 C 0.2673(2) -0.08612(19) 0.3525(10) 0.0549(16) Uani 1 1 d . . . H7 H 0.2366 -0.0944 0.3395 0.066 Uiso 1 1 calc R . . C8 C 0.3022(3) -0.1138(2) 0.3559(10) 0.0607(18) Uani 1 1 d . . . H8 H 0.2949 -0.1402 0.3470 0.073 Uiso 1 1 calc R . . C9 C 0.2376(2) -0.02170(16) 0.3647(9) 0.0468(14) Uani 1 1 d . . . H9 H 0.2084 -0.0328 0.3461 0.056 Uiso 1 1 calc R . . C10 C 0.2391(2) 0.01688(16) 0.3863(8) 0.0451(14) Uani 1 1 d . . . H10 H 0.2677 0.0287 0.4094 0.054 Uiso 1 1 calc R . . C11 C 0.19825(19) 0.04083(15) 0.3754(8) 0.0423(13) Uani 1 1 d . . . C12 C 0.1996(2) 0.07954(16) 0.3864(9) 0.0472(14) Uani 1 1 d . . . H12 H 0.2279 0.0923 0.4047 0.057 Uiso 1 1 calc R . . C13 C 0.1586(2) 0.10077(17) 0.3703(9) 0.0480(15) Uani 1 1 d . . . C14 C 0.1184(2) 0.07918(18) 0.3488(10) 0.0531(16) Uani 1 1 d . . . H14 H 0.0900 0.0921 0.3370 0.064 Uiso 1 1 calc R . . C15 C 0.1190(2) 0.04115(19) 0.3446(11) 0.0604(18) Uani 1 1 d . . . C16 C 0.0796(3) 0.0154(3) 0.313(2) 0.100(4) Uani 1 1 d . . . H16A H 0.0514 0.0305 0.3095 0.150 Uiso 1 1 calc R . . H16B H 0.0778 -0.0031 0.4164 0.150 Uiso 1 1 calc R . . H16C H 0.0834 0.0019 0.1931 0.150 Uiso 1 1 calc R . . C17 C 0.1586(2) 0.14064(17) 0.3717(10) 0.0536(16) Uani 1 1 d . . . C18 C 0.1999(3) 0.1625(2) 0.3964(15) 0.072(2) Uani 1 1 d . . . C19 C 0.1182(3) 0.16218(19) 0.3429(10) 0.0588(18) Uani 1 1 d . . . C01 C -0.0301(13) 0.0139(10) 0.743(11) 0.223(4) Uiso 0.50 1 d PD A -1 H01A H -0.0585 0.0096 0.6699 0.268 Uiso 0.50 1 calc PR A -1 H01B H -0.0383 0.0239 0.8690 0.268 Uiso 0.50 1 calc PR A -1 Cl1 Cl 0.0063(5) 0.0463(4) 0.622(3) 0.223(4) Uiso 0.50 1 d PD A -1 Cl1' Cl 0.0017(7) -0.0296(4) 0.764(3) 0.223(4) Uiso 0.50 1 d PD A -1 C02 C -0.0092(7) -0.0068(12) 0.864(10) 0.223(4) Uiso 0.50 1 d PD B -2 H02A H -0.0075 -0.0119 1.0015 0.268 Uiso 0.50 1 calc PR B -2 H02B H -0.0070 -0.0316 0.7978 0.268 Uiso 0.50 1 calc PR B -2 Cl2 Cl -0.0617(5) 0.0137(5) 0.814(3) 0.223(4) Uiso 0.50 1 d PD B -2 Cl2' Cl 0.0367(5) 0.0211(5) 0.800(3) 0.223(4) Uiso 0.50 1 d PD B -2 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 O1 0.052(2) 0.053(2) 0.060(3) 0.005(2) -0.0095(19) 0.0004(19) N1 0.076(4) 0.093(5) 0.084(5) -0.014(4) -0.012(4) 0.034(4) N2 0.086(5) 0.074(4) 0.071(4) 0.002(3) 0.007(3) 0.027(4) N3 0.084(5) 0.054(4) 0.185(11) -0.020(5) 0.025(6) -0.014(4) C1 0.080(6) 0.155(9) 0.091(6) -0.010(7) 0.003(6) 0.065(6) C2 0.157(10) 0.077(6) 0.068(5) -0.015(4) -0.030(6) 0.057(6) C3 0.073(5) 0.070(4) 0.046(3) -0.003(3) -0.006(3) 0.023(3) C4 0.048(3) 0.087(5) 0.061(4) -0.016(4) 0.000(3) 0.010(3) C5 0.058(4) 0.056(4) 0.053(3) 0.000(3) -0.008(3) 0.005(3) C6 0.054(3) 0.059(4) 0.040(3) 0.004(3) 0.002(3) 0.015(3) C7 0.051(3) 0.055(3) 0.059(4) 0.003(3) -0.002(3) 0.005(3) C8 0.074(4) 0.055(4) 0.053(4) -0.001(3) -0.004(3) 0.013(3) C9 0.045(3) 0.047(3) 0.049(3) -0.003(3) 0.000(2) -0.004(2) C10 0.049(3) 0.046(3) 0.041(3) -0.003(2) 0.004(2) -0.002(2) C11 0.048(3) 0.043(3) 0.036(3) -0.001(3) 0.000(2) 0.003(2) C12 0.049(3) 0.049(3) 0.044(3) 0.000(3) 0.004(2) 0.007(2) C13 0.051(3) 0.053(3) 0.041(3) 0.002(3) 0.008(2) 0.009(3) C14 0.050(3) 0.057(4) 0.052(4) -0.001(3) -0.002(3) 0.011(3) C15 0.058(4) 0.052(4) 0.072(4) 0.013(3) -0.014(3) 0.001(3) C16 0.048(4) 0.078(5) 0.173(12) 0.027(7) -0.022(5) -0.009(3) C17 0.061(4) 0.052(3) 0.048(3) -0.010(3) 0.008(3) 0.013(3) C18 0.078(5) 0.042(3) 0.096(6) -0.011(4) 0.022(4) 0.006(3) C19 0.073(5) 0.048(3) 0.055(4) 0.001(3) 0.015(3) 0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.341(7) . ? O1 C15 1.357(8) . ? N1 C3 1.355(10) . ? N1 C2 1.427(14) . ? N1 C1 1.489(14) . ? N2 C19 1.147(9) . ? N3 C18 1.109(11) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C8 1.402(11) . ? C3 C4 1.413(12) . ? C4 C5 1.384(9) . ? C4 H4 0.9500 . ? C5 C6 1.397(9) . ? C5 H5 0.9500 . ? C6 C7 1.390(10) . ? C6 C9 1.434(8) . ? C7 C8 1.410(10) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.361(8) . ? C9 H9 0.9500 . ? C10 C11 1.464(8) . ? C10 H10 0.9500 . ? C11 C12 1.359(8) . ? C12 C13 1.419(8) . ? C12 H12 0.9500 . ? C13 C17 1.397(9) . ? C13 C14 1.407(9) . ? C14 C15 1.333(9) . ? C14 H14 0.9500 . ? C15 C16 1.482(10) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C19 1.419(9) . ? C17 C18 1.442(11) . ? C01 Cl1 1.78(2) . ? C01 Cl1' 1.79(2) . ? C01 H01A 0.9900 . ? C01 H01B 0.9900 . ? C02 Cl2' 1.72(2) . ? C02 Cl2 1.73(2) . ? C02 H02A 0.9900 . ? C02 H02B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O1 C15 119.8(4) . . ? C3 N1 C2 121.9(8) . . ? C3 N1 C1 118.4(8) . . ? C2 N1 C1 119.1(7) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 109.5 . . ? N1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C8 120.6(7) . . ? N1 C3 C4 121.9(7) . . ? C8 C3 C4 117.4(6) . . ? C5 C4 C3 121.9(7) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 121.1(6) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 117.1(5) . . ? C7 C6 C9 118.0(6) . . ? C5 C6 C9 124.9(6) . . ? C6 C7 C8 122.8(6) . . ? C6 C7 H7 118.6 . . ? C8 C7 H7 118.6 . . ? C3 C8 C7 119.5(7) . . ? C3 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C10 C9 C6 126.4(6) . . ? C10 C9 H9 116.8 . . ? C6 C9 H9 116.8 . . ? C9 C10 C11 122.5(5) . . ? C9 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? O1 C11 C12 122.0(5) . . ? O1 C11 C10 115.0(4) . . ? C12 C11 C10 123.0(5) . . ? C11 C12 C13 119.6(5) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C17 C13 C14 122.7(5) . . ? C17 C13 C12 121.5(6) . . ? C14 C13 C12 115.8(5) . . ? C15 C14 C13 122.0(6) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 O1 120.7(6) . . ? C14 C15 C16 127.0(6) . . ? O1 C15 C16 112.1(6) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 C19 122.0(6) . . ? C13 C17 C18 122.3(6) . . ? C19 C17 C18 115.7(5) . . ? N3 C18 C17 176.1(9) . . ? N2 C19 C17 178.9(8) . . ? Cl1 C01 Cl1' 105.7(15) . . ? Cl1 C01 H01A 110.6 . . ? Cl1' C01 H01A 110.6 . . ? Cl1 C01 H01B 110.6 . . ? Cl1' C01 H01B 110.6 . . ? H01A C01 H01B 108.7 . . ? Cl2' C02 Cl2 113.8(17) . . ? Cl2' C02 H02A 108.8 . . ? Cl2 C02 H02A 108.8 . . ? Cl2' C02 H02B 108.8 . . ? Cl2 C02 H02B 108.8 . . ? H02A C02 H02B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.772 _refine_diff_density_min -0.783 _refine_diff_density_rms 0.103 _database_code_depnum_ccdc_archive 'CCDC 936745' ####################################################################### # # 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_added_by_encifer _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H16 N2 O2, 2(C H Cl3)' _chemical_formula_sum 'C26 H18 Cl6 N2 O2' _chemical_formula_weight 603.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6826(3) _cell_length_b 10.3721(6) _cell_length_c 12.1384(9) _cell_angle_alpha 70.264(2) _cell_angle_beta 89.299(2) _cell_angle_gamma 82.447(3) _cell_volume 667.18(7) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4197 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 22.46 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 306 _exptl_absorpt_coefficient_mu 0.672 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.502 _exptl_absorpt_correction_T_max 0.895 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 4389 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 22.46 _reflns_number_total 1704 _reflns_number_gt 1308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0717P)^2^+0.0249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1704 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1177 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _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 O1 O 0.5106(3) 0.06629(18) 0.80646(16) 0.0454(5) Uani 1 1 d . . . N1 N 0.4529(5) -0.1487(2) 0.8260(2) 0.0543(7) Uani 1 1 d . . . C1 C 0.9860(6) 0.3320(3) 0.6207(3) 0.0574(8) Uani 1 1 d . . . H1 H 0.9717 0.4237 0.6221 0.069 Uiso 1 1 calc R . . C2 C 1.1717(6) 0.2845(4) 0.5621(3) 0.0631(9) Uani 1 1 d . . . H2 H 1.2841 0.3433 0.5234 0.076 Uiso 1 1 calc R . . C3 C 1.1899(6) 0.1511(4) 0.5612(3) 0.0617(9) Uani 1 1 d . . . H3 H 1.3149 0.1184 0.5206 0.074 Uiso 1 1 calc R . . C4 C 1.0299(5) 0.0646(3) 0.6181(3) 0.0555(9) Uani 1 1 d . . . H4 H 1.0464 -0.0275 0.6176 0.067 Uiso 1 1 calc R . . C5 C 0.8423(5) 0.1120(3) 0.6770(2) 0.0455(8) Uani 1 1 d . . . C6 C 0.8241(6) 0.2470(3) 0.6763(3) 0.0517(8) Uani 1 1 d . . . H6 H 0.6972 0.2811 0.7150 0.062 Uiso 1 1 calc R . . C7 C 0.6764(5) 0.0187(3) 0.7400(2) 0.0467(7) Uani 1 1 d . . . C8 C 0.6391(6) -0.1108(3) 0.7526(3) 0.0555(9) Uani 1 1 d . . . H8 H 0.7282 -0.1684 0.7161 0.067 Uiso 1 1 calc R . . C9 C 0.3832(5) -0.0400(3) 0.8556(2) 0.0455(8) Uani 1 1 d . . . C10 C 0.1888(5) -0.0195(3) 0.9299(2) 0.0461(7) Uani 1 1 d . . . C11 C 0.0508(5) -0.1251(3) 0.9810(3) 0.0479(8) Uani 1 1 d . . . H11 H 0.0851 -0.2107 0.9676 0.058 Uiso 1 1 calc R . . C12 C 0.1344(5) 0.1061(3) 0.9494(3) 0.0481(8) Uani 1 1 d . . . H12 H 0.2257 0.1790 0.9143 0.058 Uiso 1 1 calc R . . Cl3 Cl 0.51846(15) 0.58610(8) 0.11096(10) 0.0772(4) Uani 1 1 d . . . Cl2 Cl 0.99222(15) 0.45006(11) 0.16452(11) 0.0933(4) Uani 1 1 d . . . Cl1 Cl 0.6403(2) 0.38180(13) 0.33834(9) 0.1077(5) Uani 1 1 d . . . C13 C 0.6933(5) 0.4301(3) 0.1882(3) 0.0529(8) Uani 1 1 d . . . H13 H 0.6537 0.3563 0.1585 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0578(12) 0.0359(11) 0.0428(12) -0.0130(9) -0.0051(10) -0.0080(9) N1 0.0712(17) 0.0367(14) 0.0544(17) -0.0140(12) -0.0099(14) -0.0078(12) C1 0.069(2) 0.0511(18) 0.051(2) -0.0141(16) 0.0007(17) -0.0106(16) C2 0.063(2) 0.068(2) 0.050(2) -0.0078(17) -0.0058(16) -0.0138(17) C3 0.054(2) 0.076(2) 0.051(2) -0.0192(18) -0.0017(16) -0.0008(18) C4 0.064(2) 0.0528(18) 0.0497(19) -0.0212(16) -0.0144(17) 0.0042(17) C5 0.0554(18) 0.0441(18) 0.0352(17) -0.0126(14) -0.0107(14) -0.0014(14) C6 0.063(2) 0.0462(19) 0.0445(18) -0.0137(15) 0.0018(15) -0.0085(15) C7 0.0571(18) 0.0396(17) 0.0422(18) -0.0138(14) -0.0122(14) -0.0012(14) C8 0.067(2) 0.0433(19) 0.055(2) -0.0160(16) -0.0106(17) -0.0019(15) C9 0.0573(18) 0.0339(16) 0.0427(18) -0.0084(14) -0.0136(15) -0.0086(14) C10 0.0588(18) 0.0383(16) 0.0378(17) -0.0071(13) -0.0141(15) -0.0086(14) C11 0.0605(19) 0.0339(16) 0.0504(19) -0.0138(14) -0.0116(15) -0.0096(14) C12 0.0613(19) 0.0371(16) 0.0450(18) -0.0103(14) -0.0097(15) -0.0125(14) Cl3 0.0600(6) 0.0541(6) 0.1194(9) -0.0340(5) -0.0143(5) -0.0006(4) Cl2 0.0497(6) 0.0935(8) 0.1307(10) -0.0346(7) 0.0106(5) 0.0016(5) Cl1 0.1549(11) 0.1221(10) 0.0627(7) -0.0331(6) 0.0236(7) -0.0742(8) C13 0.0585(19) 0.0432(17) 0.062(2) -0.0232(15) 0.0067(15) -0.0112(14) _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 O1 C9 1.360(3) . ? O1 C7 1.382(3) . ? N1 C9 1.308(4) . ? N1 C8 1.385(4) . ? C1 C6 1.369(4) . ? C1 C2 1.394(4) . ? C1 H1 0.9500 . ? C2 C3 1.378(5) . ? C2 H2 0.9500 . ? C3 C4 1.375(5) . ? C3 H3 0.9500 . ? C4 C5 1.404(4) . ? C4 H4 0.9500 . ? C5 C6 1.388(4) . ? C5 C7 1.461(4) . ? C6 H6 0.9500 . ? C7 C8 1.344(4) . ? C8 H8 0.9500 . ? C9 C10 1.457(4) . ? C10 C12 1.396(4) . ? C10 C11 1.399(4) . ? C11 C12 1.377(4) 2_557 ? C11 H11 0.9500 . ? C12 C11 1.377(4) 2_557 ? C12 H12 0.9500 . ? Cl3 C13 1.749(3) . ? Cl2 C13 1.746(3) . ? Cl1 C13 1.753(3) . ? C13 H13 1.0000 . ? 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 C9 O1 C7 105.2(2) . . ? C9 N1 C8 104.1(3) . . ? C6 C1 C2 120.3(3) . . ? C6 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 121.0(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 118.4(3) . . ? C6 C5 C7 121.6(3) . . ? C4 C5 C7 120.0(3) . . ? C1 C6 C5 121.1(3) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C8 C7 O1 106.7(3) . . ? C8 C7 C5 135.9(3) . . ? O1 C7 C5 117.5(2) . . ? C7 C8 N1 110.7(3) . . ? C7 C8 H8 124.7 . . ? N1 C8 H8 124.7 . . ? N1 C9 O1 113.3(3) . . ? N1 C9 C10 128.5(3) . . ? O1 C9 C10 118.1(2) . . ? C12 C10 C11 119.0(3) . . ? C12 C10 C9 120.8(3) . . ? C11 C10 C9 120.1(3) . . ? C12 C11 C10 120.5(3) 2_557 . ? C12 C11 H11 119.8 2_557 . ? C10 C11 H11 119.8 . . ? C11 C12 C10 120.5(3) 2_557 . ? C11 C12 H12 119.8 2_557 . ? C10 C12 H12 119.8 . . ? Cl2 C13 Cl3 108.88(16) . . ? Cl2 C13 Cl1 109.94(18) . . ? Cl3 C13 Cl1 110.67(16) . . ? Cl2 C13 H13 109.1 . . ? Cl3 C13 H13 109.1 . . ? Cl1 C13 H13 109.1 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 22.46 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.242 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 936746'