# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 #TrackingRef '- DiOHCHD.cif' _publ_contact_author_name 'Dr. Harinath Chakrapani' _publ_contact_author_address ;Department of Chemistry, Medeleev Block, Indian Institute of Science Education and Research, Pune - 411008, Maharashtra, India. ; _publ_contact_author_email harinath@iiserpune.ac.in _publ_contact_author_phone 00912025908090 loop_ _publ_author_name _publ_author_address H.Chakrapani ;Department of Chemistry, Medeleev Block, Indian Institute of Science Education and Research, Pune - 411008, Maharashtra, India. ; 'Allimuthu T. Dharmaraja' ;Department of Chemistry, Medeleev Block, Indian Institute of Science Education and Research, Pune - 411008, Maharashtra, India. ; data_a1 _database_code_depnum_ccdc_archive 'CCDC 893408' #TrackingRef '- DiOHCHD.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Anthraquinone Derivative' _chemical_melting_point '133-135 C' _chemical_formula_moiety 'C16 H14 O4' _chemical_formula_sum 'C16 H14 O4' _chemical_formula_weight 270.28 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4103(8) _cell_length_b 9.9437(12) _cell_length_c 10.5905(13) _cell_angle_alpha 113.766(2) _cell_angle_beta 90.148(2) _cell_angle_gamma 97.772(2) _cell_volume 610.93(13) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 225 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10902 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.68 _reflns_number_total 3103 _reflns_number_gt 2825 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0635P)^2^+0.1391P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.119(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3103 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.514 _refine_ls_shift/su_mean 0.120 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 0.85454(12) 0.56992(10) 0.08318(9) 0.0355(2) Uani 1 1 d . . . H11 H 0.8304 0.4789 0.0464 0.053 Uiso 1 1 calc R . . O4 O 0.02654(13) 0.56526(9) 0.34847(9) 0.0352(2) Uani 1 1 d . . . O3 O 0.65093(12) 0.31265(9) 0.03717(8) 0.0330(2) Uani 1 1 d . . . C2 C 0.21542(19) 0.03927(11) 0.17002(12) 0.0353(3) Uani 1 1 d . . . H2A H 0.1586 -0.0115 0.0749 0.042 Uiso 1 1 calc R . . H2B H 0.2621 -0.0336 0.1986 0.042 Uiso 1 1 calc R . . C3 C 0.04369(18) 0.11376(12) 0.26324(12) 0.0346(3) Uani 1 1 d . . . H3A H -0.0883 0.0906 0.2086 0.042 Uiso 1 1 calc R . . H3B H 0.0219 0.0761 0.3344 0.042 Uiso 1 1 calc R . . C7 C 0.47194(17) 0.24882(13) 0.33156(12) 0.0332(2) Uani 1 1 d . . . H4 H 0.6083 0.2580 0.3674 0.040 Uiso 1 1 calc R . . C1 C 0.40366(16) 0.15920(11) 0.18122(11) 0.0291(2) Uani 1 1 d . . . H1 H 0.5206 0.1140 0.1293 0.035 Uiso 1 1 calc R . . C6 C 0.32263(15) 0.26630(10) 0.12415(10) 0.0229(2) Uani 1 1 d . . . H8 H 0.2592 0.2049 0.0308 0.027 Uiso 1 1 calc R . . C5 C 0.14460(14) 0.33882(10) 0.21283(10) 0.0229(2) Uani 1 1 d . . . H5 H 0.0142 0.3036 0.1531 0.028 Uiso 1 1 calc R . . C9 C 0.17035(15) 0.50660(11) 0.27859(10) 0.0244(2) Uani 1 1 d . . . C10 C 0.35868(15) 0.59765(10) 0.26287(9) 0.0238(2) Uani 1 1 d . . . C16 C 0.37879(18) 0.75294(11) 0.33058(11) 0.0302(2) Uani 1 1 d . . . O2 O 0.22833(15) 0.82369(9) 0.40776(9) 0.0409(2) Uani 1 1 d . . . H12 H 0.1265 0.7626 0.4045 0.061 Uiso 1 1 calc R . . C13 C 0.69915(16) 0.62213(11) 0.16636(10) 0.0278(2) Uani 1 1 d . . . C11 C 0.52234(14) 0.53099(10) 0.18021(9) 0.0230(2) Uani 1 1 d . . . C15 C 0.5637(2) 0.84101(12) 0.32043(12) 0.0372(3) Uani 1 1 d . . . H13 H 0.5799 0.9437 0.3685 0.045 Uiso 1 1 calc R . . C14 C 0.71949(19) 0.77676(12) 0.24060(12) 0.0360(3) Uani 1 1 d . . . H14 H 0.8411 0.8364 0.2353 0.043 Uiso 1 1 calc R . . C12 C 0.50889(15) 0.36940(11) 0.11013(10) 0.0234(2) Uani 1 1 d . . . C4 C 0.11206(15) 0.28323(11) 0.33063(10) 0.0265(2) Uani 1 1 d . . . H6 H 0.0064 0.3327 0.3922 0.032 Uiso 1 1 calc R . . C8 C 0.32150(17) 0.31365(12) 0.40874(11) 0.0308(2) Uani 1 1 d . . . H8A H 0.3437 0.3728 0.5029 0.037 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 0.0293(4) 0.0415(4) 0.0361(4) 0.0183(4) 0.0066(3) -0.0015(3) O4 0.0358(4) 0.0365(4) 0.0384(4) 0.0171(3) 0.0143(3) 0.0164(3) O3 0.0317(4) 0.0334(4) 0.0352(4) 0.0135(3) 0.0130(3) 0.0100(3) C2 0.0436(6) 0.0228(5) 0.0399(6) 0.0137(4) 0.0038(5) 0.0026(4) C3 0.0337(5) 0.0276(5) 0.0407(6) 0.0150(4) 0.0027(4) -0.0052(4) C7 0.0290(5) 0.0387(6) 0.0387(6) 0.0239(5) -0.0051(4) 0.0015(4) C1 0.0304(5) 0.0268(5) 0.0350(5) 0.0161(4) 0.0062(4) 0.0093(4) C6 0.0255(4) 0.0210(4) 0.0216(4) 0.0082(3) 0.0017(3) 0.0035(3) C5 0.0201(4) 0.0250(4) 0.0236(4) 0.0100(3) 0.0004(3) 0.0024(3) C9 0.0262(4) 0.0278(5) 0.0224(4) 0.0120(4) 0.0028(3) 0.0088(3) C10 0.0285(5) 0.0224(4) 0.0209(4) 0.0090(3) 0.0001(3) 0.0049(3) C16 0.0418(6) 0.0242(5) 0.0238(5) 0.0078(4) -0.0004(4) 0.0078(4) O2 0.0531(5) 0.0275(4) 0.0385(4) 0.0070(3) 0.0082(4) 0.0150(4) C13 0.0277(5) 0.0316(5) 0.0254(5) 0.0146(4) -0.0009(4) -0.0008(4) C11 0.0245(4) 0.0240(4) 0.0211(4) 0.0104(4) -0.0004(3) 0.0021(3) C15 0.0526(7) 0.0221(5) 0.0321(5) 0.0086(4) -0.0052(5) -0.0022(4) C14 0.0406(6) 0.0304(5) 0.0344(6) 0.0150(4) -0.0055(4) -0.0091(4) C12 0.0249(4) 0.0255(4) 0.0210(4) 0.0102(3) 0.0022(3) 0.0052(3) C4 0.0265(4) 0.0264(5) 0.0268(5) 0.0122(4) 0.0055(4) 0.0007(3) C8 0.0371(5) 0.0312(5) 0.0251(5) 0.0147(4) -0.0036(4) -0.0020(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 O1 C13 1.3467(13) . ? O1 H11 0.8200 . ? O4 C9 1.2405(12) . ? O3 C12 1.2392(12) . ? C2 C3 1.5401(16) . ? C2 C1 1.5455(15) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.5396(14) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C7 C8 1.3272(16) . ? C7 C1 1.5060(16) . ? C7 H4 0.9300 . ? C1 C6 1.5608(13) . ? C1 H1 0.9800 . ? C6 C12 1.5137(13) . ? C6 C5 1.5449(13) . ? C6 H8 0.9800 . ? C5 C9 1.5113(13) . ? C5 C4 1.5593(13) . ? C5 H5 0.9800 . ? C9 C10 1.4601(14) . ? C10 C16 1.4030(14) . ? C10 C11 1.4253(13) . ? C16 O2 1.3481(13) . ? C16 C15 1.4072(16) . ? O2 H12 0.8200 . ? C13 C11 1.3991(13) . ? C13 C14 1.4037(15) . ? C11 C12 1.4632(13) . ? C15 C14 1.3642(17) . ? C15 H13 0.9300 . ? C14 H14 0.9300 . ? C4 C8 1.5036(14) . ? C4 H6 0.9800 . ? C8 H8A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 H11 109.5 . . ? C3 C2 C1 109.23(8) . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? C4 C3 C2 109.59(8) . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3B 109.8 . . ? C2 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C8 C7 C1 114.47(9) . . ? C8 C7 H4 122.8 . . ? C1 C7 H4 122.8 . . ? C7 C1 C2 108.82(9) . . ? C7 C1 C6 107.44(8) . . ? C2 C1 C6 107.45(8) . . ? C7 C1 H1 111.0 . . ? C2 C1 H1 111.0 . . ? C6 C1 H1 111.0 . . ? C12 C6 C5 117.21(8) . . ? C12 C6 C1 109.19(8) . . ? C5 C6 C1 108.88(8) . . ? C12 C6 H8 107.0 . . ? C5 C6 H8 107.0 . . ? C1 C6 H8 107.0 . . ? C9 C5 C6 117.49(7) . . ? C9 C5 C4 107.59(8) . . ? C6 C5 C4 109.32(7) . . ? C9 C5 H5 107.3 . . ? C6 C5 H5 107.3 . . ? C4 C5 H5 107.3 . . ? O4 C9 C10 120.68(9) . . ? O4 C9 C5 117.69(9) . . ? C10 C9 C5 121.62(8) . . ? C16 C10 C11 119.64(9) . . ? C16 C10 C9 119.42(9) . . ? C11 C10 C9 120.95(8) . . ? O2 C16 C10 122.88(10) . . ? O2 C16 C15 117.45(9) . . ? C10 C16 C15 119.66(10) . . ? C16 O2 H12 109.5 . . ? O1 C13 C11 123.47(9) . . ? O1 C13 C14 116.73(9) . . ? C11 C13 C14 119.79(10) . . ? C13 C11 C10 119.22(9) . . ? C13 C11 C12 119.56(9) . . ? C10 C11 C12 121.23(8) . . ? C14 C15 C16 120.45(10) . . ? C14 C15 H13 119.8 . . ? C16 C15 H13 119.8 . . ? C15 C14 C13 121.08(10) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? O3 C12 C11 120.69(9) . . ? O3 C12 C6 117.85(8) . . ? C11 C12 C6 121.46(8) . . ? C8 C4 C3 107.93(9) . . ? C8 C4 C5 107.93(8) . . ? C3 C4 C5 107.99(8) . . ? C8 C4 H6 111.0 . . ? C3 C4 H6 110.9 . . ? C5 C4 H6 110.9 . . ? C7 C8 C4 114.15(9) . . ? C7 C8 H8A 122.9 . . ? C4 C8 H8A 122.9 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.68 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.321 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.046