# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email chsgk@bath.ac.uk _publ_contact_author_name 'Gabriele Kociok-Kohn' loop_ _publ_author_name 'Joseph C. Allen' 'Gabriele Kociok-Kohn' 'Christopher G. Frost' data_k10cgf2 _database_code_depnum_ccdc_archive 'CCDC 836829' #TrackingRef 'web_deposit_cif_file_0_Dr.GabrieleKociok-Kohn_1311683920.k10cgf2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H11 Cl O2' _chemical_formula_sum 'C15 H11 Cl O2' _chemical_formula_weight 258.69 _chemical_absolute_configuration ad 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.4561(2) _cell_length_b 7.8785(3) _cell_length_c 14.0005(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.132(2) _cell_angle_gamma 90.00 _cell_volume 601.82(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8756 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8872 _exptl_absorpt_correction_T_max 0.9700 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method '158 2.0 degree images with \w scans' _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7942 _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2727 _reflns_number_gt 2366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinski & Minor, 1997)' _computing_data_reduction ; DENZO-SCALEPACK Z. Otwinowski and W. Minor, " Processing of X-ray Diffraction Data Collected in Oscillation Mode ", Methods in Enzymology, Volume 276: Macromolecular Crystallography, part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. ; _computing_structure_solution ; SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) J. Appl. Cryst. 32, 115-119 ; _computing_structure_refinement ; SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). Sheldrick, G.M., Instit\"ut f\"ur Anorganische Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998 ; _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _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^)+(0.0464P)^2^+0.0855P] 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 -0.17(7) _refine_ls_number_reflns 2727 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0975 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Cl Cl 0.43829(11) 0.68758(8) -0.13952(4) 0.04048(17) Uani 1 1 d . . . O1 O 0.4686(3) 0.3471(2) 0.33477(13) 0.0383(4) Uani 1 1 d . . . O2 O 0.3840(3) 0.6093(2) 0.37477(11) 0.0303(3) Uani 1 1 d . . . C1 C 0.3070(4) 0.6636(3) -0.02784(15) 0.0272(4) Uani 1 1 d . . . C2 C 0.4132(4) 0.7418(3) 0.04983(17) 0.0294(5) Uani 1 1 d . . . H2 H 0.5597 0.8056 0.0425 0.035 Uiso 1 1 calc R . . C3 C 0.3044(4) 0.7266(3) 0.13891(16) 0.0281(5) Uani 1 1 d . . . H3 H 0.3764 0.7813 0.1925 0.034 Uiso 1 1 calc R . . C4 C 0.0910(3) 0.6320(2) 0.15060(15) 0.0230(4) Uani 1 1 d . . . C5 C -0.0133(4) 0.5556(3) 0.07126(17) 0.0282(5) Uani 1 1 d . . . H5 H -0.1597 0.4916 0.0784 0.034 Uiso 1 1 calc R . . C6 C 0.0927(4) 0.5707(3) -0.01896(18) 0.0312(5) Uani 1 1 d . . . H6 H 0.0195 0.5184 -0.0731 0.037 Uiso 1 1 calc R . . C7 C -0.0281(3) 0.6075(3) 0.24876(16) 0.0250(4) Uani 1 1 d . . . H7 H -0.2091 0.5976 0.2390 0.030 Uiso 1 1 calc R . . C8 C 0.0614(4) 0.4432(3) 0.29668(17) 0.0282(5) Uani 1 1 d . . . H8A H -0.0507 0.4141 0.3497 0.034 Uiso 1 1 calc R . . H8B H 0.0551 0.3496 0.2496 0.034 Uiso 1 1 calc R . . C9 C 0.3179(4) 0.4577(3) 0.33506(16) 0.0285(5) Uani 1 1 d . . . C10 C 0.2184(4) 0.7458(3) 0.37748(15) 0.0263(4) Uani 1 1 d . . . C11 C 0.2735(4) 0.8748(3) 0.44108(17) 0.0321(5) Uani 1 1 d . . . H11 H 0.4138 0.8674 0.4811 0.039 Uiso 1 1 calc R . . C12 C 0.1204(4) 1.0150(3) 0.44534(18) 0.0354(5) Uani 1 1 d . . . H12 H 0.1567 1.1054 0.4880 0.042 Uiso 1 1 calc R . . C13 C -0.0851(4) 1.0235(3) 0.38752(19) 0.0357(5) Uani 1 1 d . . . H13 H -0.1925 1.1181 0.3918 0.043 Uiso 1 1 calc R . . C14 C -0.1342(4) 0.8941(3) 0.32345(18) 0.0303(5) Uani 1 1 d . . . H14 H -0.2741 0.9021 0.2832 0.036 Uiso 1 1 calc R . . C15 C 0.0173(4) 0.7522(3) 0.31675(16) 0.0258(4) 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 Cl 0.0487(3) 0.0396(3) 0.0331(3) 0.0000(3) 0.0072(2) 0.0023(3) O1 0.0364(8) 0.0365(10) 0.0420(10) 0.0034(7) -0.0014(7) 0.0117(7) O2 0.0244(7) 0.0323(8) 0.0340(9) -0.0004(7) -0.0057(6) 0.0036(6) C1 0.0303(9) 0.0225(11) 0.0290(10) 0.0026(9) 0.0020(8) 0.0052(9) C2 0.0254(9) 0.0271(11) 0.0357(13) 0.0048(9) -0.0012(9) -0.0032(8) C3 0.0253(10) 0.0285(12) 0.0303(11) 0.0002(9) -0.0056(8) -0.0064(8) C4 0.0211(8) 0.0186(10) 0.0293(11) 0.0024(8) -0.0040(8) 0.0010(7) C5 0.0250(10) 0.0238(10) 0.0357(13) -0.0034(9) -0.0015(9) -0.0053(8) C6 0.0338(11) 0.0252(11) 0.0346(13) -0.0053(9) -0.0054(9) -0.0009(8) C7 0.0185(8) 0.0246(10) 0.0317(11) 0.0034(9) -0.0015(8) -0.0015(8) C8 0.0287(10) 0.0226(10) 0.0333(12) 0.0036(9) 0.0002(9) -0.0026(8) C9 0.0305(10) 0.0301(11) 0.0250(11) 0.0050(9) 0.0022(9) 0.0022(9) C10 0.0240(9) 0.0276(10) 0.0273(11) 0.0023(8) 0.0035(8) -0.0019(8) C11 0.0303(10) 0.0400(12) 0.0261(11) -0.0027(10) 0.0025(9) -0.0068(9) C12 0.0427(12) 0.0298(12) 0.0336(13) -0.0050(9) 0.0110(10) -0.0101(10) C13 0.0363(12) 0.0267(11) 0.0443(14) -0.0006(10) 0.0111(11) -0.0001(9) C14 0.0272(10) 0.0241(11) 0.0396(13) 0.0042(9) 0.0004(9) -0.0008(8) C15 0.0231(9) 0.0255(10) 0.0289(11) 0.0044(8) 0.0018(8) -0.0034(8) _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 Cl C1 1.732(2) . ? O1 C9 1.198(3) . ? O2 C9 1.365(3) . ? O2 C10 1.405(2) . ? C1 C2 1.376(3) . ? C1 C6 1.385(3) . ? C2 C3 1.388(3) . ? C2 H2 0.9500 . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(3) . ? C4 C7 1.534(3) . ? C5 C6 1.395(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C15 1.505(3) . ? C7 C8 1.537(3) . ? C7 H7 1.0000 . ? C8 C9 1.502(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C10 C11 1.384(3) . ? C10 C15 1.387(3) . ? C11 C12 1.386(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(4) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 C15 1.393(3) . ? C14 H14 0.9500 . ? 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 O2 C10 120.73(16) . . ? C2 C1 C6 121.30(19) . . ? C2 C1 Cl 119.34(16) . . ? C6 C1 Cl 119.32(17) . . ? C1 C2 C3 119.42(19) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C2 C3 C4 120.75(19) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 118.72(19) . . ? C5 C4 C7 119.36(17) . . ? C3 C4 C7 121.91(18) . . ? C4 C5 C6 121.25(19) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.5(2) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C15 C7 C4 113.70(17) . . ? C15 C7 C8 108.06(17) . . ? C4 C7 C8 111.25(17) . . ? C15 C7 H7 107.9 . . ? C4 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? C9 C8 C7 112.76(17) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? O1 C9 O2 117.2(2) . . ? O1 C9 C8 125.6(2) . . ? O2 C9 C8 117.22(18) . . ? C11 C10 C15 122.5(2) . . ? C11 C10 O2 116.16(19) . . ? C15 C10 O2 121.27(19) . . ? C10 C11 C12 118.9(2) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? C13 C12 C11 120.1(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 119.9(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 121.4(2) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C10 C15 C14 117.2(2) . . ? C10 C15 C7 119.24(18) . . ? C14 C15 C7 123.60(19) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.255 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.079