# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name 'Koichi Tanaka' 'Shigeru Ohbu' 'Atsushi Yamamoto' _publ_contact_author_name 'Prof Koichi Tanaka' _publ_contact_author_address ; Department of Applied Chemistry, Fa Matsuyama JAPAN ; _publ_contact_author_email KTANAKA@ENG.EHIME-U.AC.JP _publ_section_title ; Photochromism of a new hydroperoxy-biindenylidene in its inclusion crystals ; _publ_contact_letter ; This CIF is aimed for Cambridge Structural Database. The original paper will be submitted. Journal: Chem. Comm. Title: Photochromism of a new hydroperoxy-biindenyliden in inclusion crystals Authors: Tanaka, K., Yamamoto, Y. & Ohba, S. Compound No.: (3.CH2CL2) ; #------------------------------------------------------------------------------ data_III _database_code_CSD 209591 _audit_creation_date 'Sat Feb 1 14:24:06 2003' _audit_creation_method 'by teXsan' _audit_update_record ? _publ_section_abstract ; In the title compound, C~30~H~20~F~2~O~4~.CH~3~OH two indene rings make an angle of 20.2(1)\%. The peroxo O-O bond distance is 1.454(3) \%A. ; _publ_section_comment ; One of the indene rings is not planar, the dihedral angle between C29/C30/C31 and C29/C37/C32/C31 being 13.1(1)\%. The two indene rings bend with each other, and the dihedral angle between the phenyl rings C17-C22 and C32-C37 is 20.2(1)\%. The dihedral angle between the two fluorophenyl rings is 11.6(1)\%. There is intramolecular O5-H5...O6 hydrogen bond. There is also intermolecular hydrogen bond, O4-H4...O5 (3/2-x, y-1/2, 3/2-z), which form zigzag chain along b. ; _publ_section_exptl_prep ; The colourless crystals were grown from a methanol solution. ; _publ_section_exptl_refinement ; The methanol molecule shows positional disorder. Two possible positions having different orientations were assumed with 65% and 35% probabilities for O7A-C38A and O7B-C38B, respectively. The O7B, C38A and C38B were refined isotropically to avoid divergence, and the methanol H atoms were not introduced. The hydroxyl and peroxyl H atoms were located from difference syntheses and ride on the parent atoms. The other H-atoms were positioned geometrically and fixed with U~iso~(H) = 1.2U~eq~(parent atom). ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Molecular Structure Corporation (2001). TEXSAN. Version 1.11. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA. Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan. Sheldrick, G. M. (1997). SHELXL97. University of Gottingen, Germany. ; _publ_section_figure_captions ; Fig. 1. A view of the molecular structure of (I), showing 50% displacement ellipsoids for non-H atoms. The occupation factor of O7A and C38A is 65%. The minor part of the disordered methanol (the O7B and C38B atoms) has been omitted for clarity. Fig. 2. Projection of the crystal structure of (I) along c. The methanol has been omitted for clarity. ; # CHEMICAL DATA _chemical_formula_sum 'C31 H24 F2 O5 ' _chemical_formula_moiety 'C30 H20 F2 O4, C H4 O' _chemical_formula_weight 514.52 _chemical_melting_point ? #------------------------------------------------------------------------------ _exptl_crystal_F_000 1072 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 18.717(5) _cell_length_b 11.939(3) _cell_length_c 11.695(3) _cell_angle_alpha 90 _cell_angle_beta 98.51(2) _cell_angle_gamma 90 _cell_volume 2584.6(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.1 _cell_measurement_theta_max 14.0 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.3 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 6832 _diffrn_reflns_av_R_equivalents 0.007 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max 27.50 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.7 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5939 _reflns_number_gt 3625 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1985 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 5939 _refine_ls_number_parameters 348 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.1042P)^2^+0.6922P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_diff_density_max 0.41 _refine_diff_density_min -0.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.4335(1) 0.3621(2) 0.4306(2) 0.1084(8) Uani 1.00 d . . . F2 F 0.3725(1) 0.5121(2) 0.7227(3) 0.137(1) Uani 1.00 d . . . O3 O 0.61941(9) 0.0088(1) 0.7267(1) 0.0490(4) Uani 1.00 d . . . O4 O 0.6736(1) -0.0529(2) 0.8037(2) 0.0686(5) Uani 1.00 d . . . O5 O 0.7856(1) 0.3013(2) 0.8446(2) 0.0647(5) Uani 1.00 d . . . O6 O 0.74283(9) 0.2688(2) 1.0510(1) 0.0607(5) Uani 1.00 d . . . O7A O 0.6554(3) -0.0603(5) 1.0328(4) 0.129(2) Uani 0.65 d P . . O7B O 0.7111(6) -0.0773(10) 1.118(1) 0.12368(4) Uiso 0.35 d P . . C8 C 0.4854(2) 0.3011(3) 0.4985(3) 0.0689(8) Uani 1.00 d . . . C9 C 0.4729(1) 0.1926(3) 0.5159(2) 0.0628(7) Uani 1.00 d . . . C10 C 0.5258(1) 0.1309(2) 0.5850(2) 0.0512(6) Uani 1.00 d . . . C11 C 0.5899(1) 0.1811(2) 0.6335(2) 0.0422(5) Uani 1.00 d . . . C12 C 0.5998(2) 0.2927(2) 0.6125(3) 0.0636(7) Uani 1.00 d . . . C13 C 0.5472(2) 0.3544(3) 0.5436(3) 0.0806(9) Uani 1.00 d . . . C14 C 0.6504(1) 0.1160(2) 0.7060(2) 0.0392(4) Uani 1.00 d . . . C15 C 0.6817(1) 0.1724(2) 0.8206(2) 0.0377(4) Uani 1.00 d . . . C16 C 0.7628(1) 0.1882(2) 0.8247(2) 0.0435(5) Uani 1.00 d . . . C17 C 0.7767(1) 0.1500(2) 0.7079(2) 0.0445(5) Uani 1.00 d . . . C18 C 0.8413(1) 0.1557(2) 0.6624(2) 0.0577(6) Uani 1.00 d . . . C19 C 0.8426(2) 0.1153(3) 0.5520(3) 0.0655(7) Uani 1.00 d . . . C20 C 0.7814(2) 0.0682(3) 0.4885(2) 0.0658(7) Uani 1.00 d . . . C21 C 0.7171(1) 0.0636(2) 0.5335(2) 0.0543(6) Uani 1.00 d . . . C22 C 0.7158(1) 0.1062(2) 0.6433(2) 0.0428(5) Uani 1.00 d . . . C23 C 0.4194(2) 0.4314(3) 0.7688(3) 0.0826(10) Uani 1.00 d . . . C24 C 0.3982(2) 0.3235(4) 0.7564(3) 0.0780(9) Uani 1.00 d . . . C25 C 0.4465(1) 0.2396(3) 0.8036(2) 0.0616(7) Uani 1.00 d . . . C26 C 0.5145(1) 0.2680(2) 0.8593(2) 0.0480(5) Uani 1.00 d . . . C27 C 0.5328(2) 0.3800(3) 0.8705(3) 0.0730(8) Uani 1.00 d . . . C28 C 0.4852(2) 0.4637(3) 0.8247(4) 0.086(1) Uani 1.00 d . . . C29 C 0.5657(1) 0.1771(2) 0.9141(2) 0.0430(5) Uani 1.00 d . . . C30 C 0.6454(1) 0.1971(2) 0.9074(2) 0.0396(5) Uani 1.00 d . . . C31 C 0.6817(1) 0.2306(2) 1.0253(2) 0.0455(5) Uani 1.00 d . . . C32 C 0.6303(1) 0.2070(2) 1.1050(2) 0.0487(5) Uani 1.00 d . . . C33 C 0.6414(2) 0.2136(3) 1.2254(2) 0.0619(7) Uani 1.00 d . . . C34 C 0.5848(2) 0.1853(3) 1.2826(2) 0.0682(8) Uani 1.00 d . . . C35 C 0.5190(2) 0.1531(3) 1.2214(2) 0.0681(8) Uani 1.00 d . . . C36 C 0.5079(1) 0.1474(2) 1.1023(2) 0.0571(6) Uani 1.00 d . . . C37 C 0.5647(1) 0.1742(2) 1.0438(2) 0.0452(5) Uani 1.00 d . . . C38A C 0.7294(9) -0.092(1) 1.071(1) 0.20221(8) Uiso 0.65 d P . . C38B C 0.700(1) -0.073(2) 1.227(2) 0.17881(9) Uiso 0.35 d P . . H4 H 0.6935 -0.0982 0.7661 0.0686 Uiso 1.00 calc . . . H5 H 0.7750 0.3227 0.9066 0.0647 Uiso 1.00 calc . . . H9 H 0.4290 0.1585 0.4820 0.0754 Uiso 1.00 calc . . . H10 H 0.5178 0.0538 0.5990 0.0614 Uiso 1.00 calc . . . H12 H 0.6433 0.3283 0.6457 0.0763 Uiso 1.00 calc . . . H13 H 0.5543 0.4315 0.5285 0.0967 Uiso 1.00 calc . . . H16 H 0.7880 0.1413 0.8828 0.0522 Uiso 1.00 calc . . . H18 H 0.8835 0.1866 0.7062 0.0692 Uiso 1.00 calc . . . H19 H 0.8860 0.1198 0.5190 0.0786 Uiso 1.00 calc . . . H20 H 0.7836 0.0388 0.4136 0.0790 Uiso 1.00 calc . . . H21 H 0.6750 0.0321 0.4902 0.0652 Uiso 1.00 calc . . . H24 H 0.3517 0.3047 0.7168 0.0936 Uiso 1.00 calc . . . H25 H 0.4324 0.1632 0.7971 0.0739 Uiso 1.00 calc . . . H27 H 0.5789 0.4004 0.9105 0.0876 Uiso 1.00 calc . . . H28 H 0.4981 0.5406 0.8321 0.1035 Uiso 1.00 calc . . . H29 H 0.5513 0.1064 0.8812 0.0516 Uiso 1.00 calc . . . H33 H 0.6866 0.2368 1.2665 0.0742 Uiso 1.00 calc . . . H34 H 0.5908 0.1879 1.3646 0.0819 Uiso 1.00 calc . . . H35 H 0.4805 0.1343 1.2625 0.0817 Uiso 1.00 calc . . . H36 H 0.4624 0.1258 1.0614 0.0686 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.092(1) 0.106(2) 0.110(2) 0.034(1) -0.042(1) 0.004(1) F2 0.104(2) 0.142(2) 0.155(2) 0.064(2) -0.009(2) 0.037(2) O3 0.0537(9) 0.0375(8) 0.0558(9) -0.0044(7) 0.0081(7) -0.0004(7) O4 0.099(2) 0.046(1) 0.059(1) 0.0117(10) 0.007(1) 0.0065(8) O5 0.070(1) 0.063(1) 0.066(1) -0.0296(9) 0.0260(10) -0.0158(9) O6 0.0457(9) 0.087(1) 0.0471(9) -0.0174(9) 0.0003(7) -0.0060(9) O7A 0.101(3) 0.169(5) 0.115(4) 0.020(3) 0.010(3) 0.021(3) C8 0.061(2) 0.081(2) 0.057(2) 0.021(1) -0.016(1) -0.007(1) C9 0.045(1) 0.087(2) 0.053(1) 0.000(1) -0.005(1) -0.008(1) C10 0.045(1) 0.062(1) 0.046(1) -0.005(1) 0.0025(10) -0.005(1) C11 0.040(1) 0.047(1) 0.039(1) 0.0037(9) 0.0032(8) -0.0049(9) C12 0.062(2) 0.048(1) 0.073(2) -0.003(1) -0.018(1) 0.001(1) C13 0.091(2) 0.051(2) 0.089(2) 0.012(2) -0.021(2) 0.007(1) C14 0.039(1) 0.038(1) 0.040(1) -0.0025(8) 0.0064(8) -0.0006(8) C15 0.038(1) 0.035(1) 0.040(1) -0.0006(8) 0.0031(8) 0.0036(8) C16 0.039(1) 0.046(1) 0.046(1) -0.0041(9) 0.0071(9) 0.0017(9) C17 0.042(1) 0.045(1) 0.047(1) 0.0035(10) 0.0085(9) 0.0053(9) C18 0.045(1) 0.070(2) 0.060(1) 0.000(1) 0.014(1) 0.002(1) C19 0.059(2) 0.082(2) 0.061(2) 0.009(1) 0.026(1) 0.005(1) C20 0.075(2) 0.074(2) 0.051(1) 0.012(1) 0.021(1) -0.002(1) C21 0.061(1) 0.059(1) 0.044(1) 0.002(1) 0.009(1) -0.003(1) C22 0.045(1) 0.042(1) 0.043(1) 0.0029(9) 0.0088(9) 0.0031(9) C23 0.074(2) 0.098(3) 0.075(2) 0.035(2) 0.010(2) 0.015(2) C24 0.045(1) 0.122(3) 0.063(2) 0.015(2) -0.005(1) -0.005(2) C25 0.042(1) 0.088(2) 0.054(1) 0.002(1) 0.002(1) -0.008(1) C26 0.038(1) 0.066(2) 0.040(1) 0.003(1) 0.0078(9) -0.002(1) C27 0.058(2) 0.066(2) 0.091(2) 0.005(1) -0.004(1) 0.007(2) C28 0.076(2) 0.070(2) 0.112(3) 0.015(2) 0.009(2) 0.011(2) C29 0.038(1) 0.051(1) 0.041(1) -0.0047(9) 0.0062(9) -0.0045(9) C30 0.036(1) 0.043(1) 0.039(1) -0.0022(9) 0.0019(8) 0.0013(9) C31 0.042(1) 0.052(1) 0.041(1) -0.0022(10) 0.0025(9) -0.0015(10) C32 0.047(1) 0.057(1) 0.042(1) -0.003(1) 0.0065(9) -0.0014(10) C33 0.061(2) 0.082(2) 0.042(1) -0.003(1) 0.004(1) -0.002(1) C34 0.072(2) 0.093(2) 0.042(1) 0.000(2) 0.015(1) 0.005(1) C35 0.072(2) 0.082(2) 0.056(2) -0.004(2) 0.028(1) 0.010(1) C36 0.049(1) 0.068(2) 0.055(1) -0.007(1) 0.012(1) 0.003(1) C37 0.044(1) 0.048(1) 0.044(1) -0.0014(10) 0.0098(9) 0.0005(10) #------------------------------------------------------------------------------ _computing_data_collection ; WinAFC Diffractometer Control Software (Rigaku, 1999) ; _computing_cell_refinement ; WinAFC Diffractometer Control Software (Rigaku, 1999) ; _computing_data_reduction ;TEXSAN (Molecular Structure Corporation, 2001) ; _computing_structure_solution ;SIR92 (Altomare et al., 1994) ; _computing_structure_refinement ;SHELXL97 (Sheldrick, 1997) ; _computing_publication_material TEXSAN _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C8 1.370(4) . . yes F2 C23 1.359(5) . . yes O3 O4 1.454(3) . . yes O3 C14 1.440(3) . . yes O4 H4 0.820 . . no O5 C16 1.425(3) . . yes O5 H5 0.820 . . no O6 C31 1.227(3) . . yes O7A C38A 1.44(2) . . yes O7B C38B 1.33(3) . . yes C8 C9 1.336(5) . . yes C8 C13 1.357(4) . . yes C9 C10 1.392(4) . . yes C9 H9 0.950 . . no C10 C11 1.385(3) . . yes C10 H10 0.950 . . no C11 C12 1.372(4) . . yes C11 C14 1.523(3) . . yes C12 C13 1.388(4) . . yes C12 H12 0.950 . . no C13 H13 0.950 . . no C14 C15 1.537(3) . . yes C14 C22 1.521(3) . . yes C15 C16 1.523(3) . . yes C15 C30 1.336(3) . . yes C16 C17 1.500(3) . . yes C16 H16 0.950 . . no C17 C18 1.393(4) . . yes C17 C22 1.375(3) . . yes C18 C19 1.382(4) . . yes C18 H18 0.950 . . no C19 C20 1.390(4) . . yes C19 H19 0.950 . . no C20 C21 1.383(4) . . yes C20 H20 0.950 . . no C21 C22 1.384(3) . . yes C21 H21 0.950 . . no C23 C24 1.349(6) . . yes C23 C28 1.361(5) . . yes C24 C25 1.406(5) . . yes C24 H24 0.950 . . no C25 C26 1.383(3) . . yes C25 H25 0.950 . . no C26 C27 1.382(4) . . yes C26 C29 1.525(3) . . yes C27 C28 1.392(5) . . yes C27 H27 0.950 . . no C28 H28 0.950 . . no C29 C30 1.523(3) . . yes C29 C37 1.520(3) . . yes C29 H29 0.950 . . no C30 C31 1.498(3) . . yes C31 C32 1.463(4) . . yes C32 C33 1.395(3) . . yes C32 C37 1.383(3) . . yes C33 C34 1.377(4) . . yes C33 H33 0.950 . . no C34 C35 1.383(4) . . yes C34 H34 0.950 . . no C35 C36 1.379(4) . . yes C35 H35 0.950 . . no C36 C37 1.384(4) . . yes C36 H36 0.950 . . no #------------------------------------------------------------------------------ ## O7A O7B 1.34(1) . . yes ## O7B C38A 0.70(2) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 O3 C14 107.0(2) . . . yes O3 O4 H4 109.5 . . . no C16 O5 H5 109.5 . . . no F1 C8 C9 118.5(3) . . . yes F1 C8 C13 117.8(3) . . . yes C9 C8 C13 123.7(3) . . . yes C8 C9 C10 118.4(2) . . . yes C8 C9 H9 120.8 . . . no C10 C9 H9 120.8 . . . no C9 C10 C11 120.5(2) . . . yes C9 C10 H10 119.8 . . . no C11 C10 H10 119.8 . . . no C10 C11 C12 118.6(2) . . . yes C10 C11 C14 122.4(2) . . . yes C12 C11 C14 119.1(2) . . . yes C11 C12 C13 121.1(2) . . . yes C11 C12 H12 119.5 . . . no C13 C12 H12 119.4 . . . no C8 C13 C12 117.8(3) . . . yes C8 C13 H13 121.1 . . . no C12 C13 H13 121.1 . . . no O3 C14 C11 105.2(2) . . . yes O3 C14 C15 110.7(2) . . . yes O3 C14 C22 112.7(2) . . . yes C11 C14 C15 114.7(2) . . . yes C11 C14 C22 110.8(2) . . . yes C15 C14 C22 103.0(2) . . . yes C14 C15 C16 109.3(2) . . . yes C14 C15 C30 126.1(2) . . . yes C16 C15 C30 124.4(2) . . . yes O5 C16 C15 113.4(2) . . . yes O5 C16 C17 110.4(2) . . . yes O5 C16 H16 109.7 . . . no C15 C16 C17 104.0(2) . . . yes C15 C16 H16 109.7 . . . no C17 C16 H16 109.7 . . . no C16 C17 C18 127.7(2) . . . yes C16 C17 C22 112.0(2) . . . yes C18 C17 C22 120.3(2) . . . yes C17 C18 C19 118.5(2) . . . yes C17 C18 H18 120.7 . . . no C19 C18 H18 120.8 . . . no C18 C19 C20 120.9(3) . . . yes C18 C19 H19 119.6 . . . no C20 C19 H19 119.6 . . . no C19 C20 C21 120.5(3) . . . yes C19 C20 H20 119.7 . . . no C21 C20 H20 119.7 . . . no C20 C21 C22 118.3(2) . . . yes C20 C21 H21 120.8 . . . no C22 C21 H21 120.8 . . . no C14 C22 C17 111.5(2) . . . yes C14 C22 C21 126.9(2) . . . yes C17 C22 C21 121.5(2) . . . yes F2 C23 C24 118.1(3) . . . yes F2 C23 C28 118.4(3) . . . yes C24 C23 C28 123.5(3) . . . yes C23 C24 C25 118.5(3) . . . yes C23 C24 H24 120.8 . . . no C25 C24 H24 120.8 . . . no C24 C25 C26 120.3(3) . . . yes C24 C25 H25 119.9 . . . no C26 C25 H25 119.9 . . . no C25 C26 C27 118.6(2) . . . yes C25 C26 C29 120.1(2) . . . yes C27 C26 C29 121.2(2) . . . yes C26 C27 C28 121.5(3) . . . yes C26 C27 H27 119.3 . . . no C28 C27 H27 119.2 . . . no C23 C28 C27 117.6(3) . . . yes C23 C28 H28 121.2 . . . no C27 C28 H28 121.2 . . . no C26 C29 C30 115.2(2) . . . yes C26 C29 C37 109.7(2) . . . yes C26 C29 H29 109.8 . . . no C30 C29 C37 102.2(2) . . . yes C30 C29 H29 109.8 . . . no C37 C29 H29 109.8 . . . no C15 C30 C29 128.1(2) . . . yes C15 C30 C31 123.0(2) . . . yes C29 C30 C31 108.0(2) . . . yes O6 C31 C30 127.2(2) . . . yes O6 C31 C32 126.4(2) . . . yes C30 C31 C32 106.4(2) . . . yes C31 C32 C33 128.2(2) . . . yes C31 C32 C37 110.0(2) . . . yes C33 C32 C37 121.8(2) . . . yes C32 C33 C34 117.7(2) . . . yes C32 C33 H33 121.1 . . . no C34 C33 H33 121.1 . . . no C33 C34 C35 120.5(2) . . . yes C33 C34 H34 119.8 . . . no C35 C34 H34 119.8 . . . no C34 C35 C36 121.7(3) . . . yes C34 C35 H35 119.1 . . . no C36 C35 H35 119.1 . . . no C35 C36 C37 118.5(2) . . . yes C35 C36 H36 120.8 . . . no C37 C36 H36 120.8 . . . no C29 C37 C32 111.6(2) . . . yes C29 C37 C36 128.5(2) . . . yes C32 C37 C36 119.8(2) . . . yes #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O5 H5 O6 . . . 0.82 1.98 2.681(2) 143 yes O4 H4 O5 . . 2_646 0.82 1.85 2.648(3) 164 yes #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_II _database_code_CSD 209592 _audit_creation_date 'Fri Feb 7 16:02:23 2003' _audit_creation_method 'by teXsan' _audit_update_record ? _publ_section_abstract ; In the title compound, C~30~H~20~F~2~O~4~.C~2~H~3~N two indene rings make an angle of 24.5(1)\%. The peroxo O-O bond distance is 1.447(2) \%A. ; _publ_section_comment ; One of the indene rings is not planar, the dihedral angle between C29/C30/C31 and C29/C37/C32/C31 being 13.2(1)\%. The two indene rings bend with each other, and the dihedral angle between the phenyl rings C17-C22 and C32-C37 is 24.5(1)\%. The dihedral angle between the two fluorophenyl rings is 7.6(1)\%. There is intramolecular O5-H5...O6 hydrogen bond. There is also intermolecular hydrogen bond, O4-H4...O5 (3/2-x, y-1/2, 1/2-z), which form zigzag chain along b. ; _publ_section_exptl_prep ; The colourless crystals were grown from an acetonitrile solution. ; _publ_section_exptl_refinement ; The hydroxyl and peroxyl H atoms were located from difference syntheses and ride on the parent atoms. The other H-atoms were positioned geometrically and fixed with U~iso~(H) = 1.2U~eq~(parent atom). The positional parameters of the acetonitrile H atoms were calculated based on a suitable peak in difference synthesis. ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Molecular Structure Corporation (2001). TEXSAN. Version 1.11. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA. Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan. Sheldrick, G. M. (1997). SHELXL97. University of Gottingen, Germany. ; _publ_section_figure_captions ; Fig. 1. A view of the molecular structure of (I), showing 50% displacement ellipsoids for non-H atoms. Fig. 2. Projection of the crystal structure of (I) along c. ; #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C32 H23 F2 N O4 ' _chemical_formula_moiety 'C30 H20 F2 O4, C2 H3 N' _chemical_formula_weight 523.53 _chemical_melting_point ? #------------------------------------------------------------------------------ _exptl_crystal_F_000 1088 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 21.239(1) _cell_length_b 11.972(1) _cell_length_c 10.217(1) _cell_angle_alpha 90 _cell_angle_beta 92.746(8) _cell_angle_gamma 90 _cell_volume 2594.9(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.8 _cell_measurement_theta_max 13.0 _cell_measurement_temperature 297 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.4 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.340 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w _diffrn_reflns_number 6867 _diffrn_reflns_av_R_equivalents 0.010 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max 27.5 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.3 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5971 _reflns_number_gt 4103 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1344 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 5971 _refine_ls_number_parameters 354 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.0608P)^2^+0.5252P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_diff_density_max 0.19 _refine_diff_density_min -0.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.77494(8) 0.4136(2) 0.8704(1) 0.1101(6) Uani 1.00 d . . . F2 F 0.94362(8) 0.4878(1) 0.8641(1) 0.0940(5) Uani 1.00 d . . . O3 O 0.81324(5) 0.04317(9) 0.4649(1) 0.0414(3) Uani 1.00 d . . . O4 O 0.82269(6) -0.0260(1) 0.3514(1) 0.0537(3) Uani 1.00 d . . . O5 O 0.77949(6) 0.3400(1) 0.1640(2) 0.0652(4) Uani 1.00 d . . . O6 O 0.90506(6) 0.3091(1) 0.1161(1) 0.0546(3) Uani 1.00 d . . . N7 N 0.8900(3) 0.0536(3) -0.0386(4) 0.197(2) Uani 1.00 d . . . C8 C 0.77625(9) 0.3480(2) 0.7617(2) 0.0674(6) Uani 1.00 d . . . C9 C 0.7831(1) 0.2373(3) 0.7771(2) 0.0766(7) Uani 1.00 d . . . C10 C 0.7866(1) 0.1710(2) 0.6663(2) 0.0609(5) Uani 1.00 d . . . C11 C 0.78275(7) 0.2184(1) 0.5431(2) 0.0385(3) Uani 1.00 d . . . C12 C 0.7742(1) 0.3318(2) 0.5319(2) 0.0592(5) Uani 1.00 d . . . C13 C 0.7708(1) 0.3982(2) 0.6429(3) 0.0722(6) Uani 1.00 d . . . C14 C 0.78703(6) 0.1479(1) 0.4202(1) 0.0338(3) Uani 1.00 d . . . C15 C 0.82669(7) 0.2008(1) 0.3152(1) 0.0334(3) Uani 1.00 d . . . C16 C 0.78543(7) 0.2235(1) 0.1920(2) 0.0416(3) Uani 1.00 d . . . C17 C 0.72227(7) 0.1775(1) 0.2244(2) 0.0415(3) Uani 1.00 d . . . C18 C 0.66715(8) 0.1763(2) 0.1452(2) 0.0551(4) Uani 1.00 d . . . C19 C 0.61332(8) 0.1317(2) 0.1948(2) 0.0602(5) Uani 1.00 d . . . C20 C 0.61381(8) 0.0886(2) 0.3208(2) 0.0556(4) Uani 1.00 d . . . C21 C 0.66874(7) 0.0904(1) 0.4001(2) 0.0461(4) Uani 1.00 d . . . C22 C 0.72258(7) 0.1348(1) 0.3500(1) 0.0371(3) Uani 1.00 d . . . C23 C 0.94185(9) 0.4159(2) 0.7612(2) 0.0598(5) Uani 1.00 d . . . C24 C 0.9419(1) 0.3045(2) 0.7860(2) 0.0643(5) Uani 1.00 d . . . C25 C 0.93944(9) 0.2312(2) 0.6807(2) 0.0535(4) Uani 1.00 d . . . C26 C 0.93714(7) 0.2697(1) 0.5531(2) 0.0396(3) Uani 1.00 d . . . C27 C 0.93755(9) 0.3839(2) 0.5327(2) 0.0517(4) Uani 1.00 d . . . C28 C 0.93988(9) 0.4582(2) 0.6372(2) 0.0598(5) Uani 1.00 d . . . C29 C 0.93499(7) 0.1877(1) 0.4388(2) 0.0389(3) Uani 1.00 d . . . C30 C 0.88858(7) 0.2193(1) 0.3257(1) 0.0352(3) Uani 1.00 d . . . C31 C 0.92574(7) 0.2616(1) 0.2148(2) 0.0397(3) Uani 1.00 d . . . C32 C 0.99218(7) 0.2338(1) 0.2480(2) 0.0434(4) Uani 1.00 d . . . C33 C 1.04412(9) 0.2474(2) 0.1717(2) 0.0559(5) Uani 1.00 d . . . C34 C 1.10185(9) 0.2103(2) 0.2216(2) 0.0667(6) Uani 1.00 d . . . C35 C 1.10733(9) 0.1612(2) 0.3446(2) 0.0654(5) Uani 1.00 d . . . C36 C 1.05598(8) 0.1502(2) 0.4218(2) 0.0547(4) Uani 1.00 d . . . C37 C 0.99759(7) 0.1872(1) 0.3723(2) 0.0424(3) Uani 1.00 d . . . C38 C 0.9047(2) -0.0066(3) 0.0375(4) 0.113(1) Uani 1.00 d . . . C39 C 0.9233(3) -0.0828(4) 0.1347(4) 0.165(2) Uani 1.00 d . . . H4 H 0.7936 -0.0707 0.3421 0.0537 Uiso 1.00 calc . . . H5 H 0.8117 0.3623 0.1313 0.0652 Uiso 1.00 calc . . . H9 H 0.7852 0.2050 0.8622 0.0921 Uiso 1.00 calc . . . H10 H 0.7916 0.0924 0.6753 0.0729 Uiso 1.00 calc . . . H12 H 0.7705 0.3651 0.4475 0.0706 Uiso 1.00 calc . . . H13 H 0.7646 0.4766 0.6354 0.0862 Uiso 1.00 calc . . . H16 H 0.8013 0.1851 0.1193 0.0496 Uiso 1.00 calc . . . H18 H 0.6665 0.2053 0.0587 0.0659 Uiso 1.00 calc . . . H19 H 0.5753 0.1308 0.1417 0.0722 Uiso 1.00 calc . . . H20 H 0.5763 0.0574 0.3530 0.0666 Uiso 1.00 calc . . . H21 H 0.6693 0.0617 0.4870 0.0551 Uiso 1.00 calc . . . H24 H 0.9435 0.2773 0.8736 0.0771 Uiso 1.00 calc . . . H25 H 0.9393 0.1530 0.6966 0.0636 Uiso 1.00 calc . . . H27 H 0.9363 0.4120 0.4455 0.0615 Uiso 1.00 calc . . . H28 H 0.9400 0.5365 0.6226 0.0716 Uiso 1.00 calc . . . H29 H 0.9258 0.1147 0.4694 0.0462 Uiso 1.00 calc . . . H33 H 1.0400 0.2813 0.0876 0.0668 Uiso 1.00 calc . . . H34 H 1.1381 0.2184 0.1714 0.0800 Uiso 1.00 calc . . . H35 H 1.1473 0.1343 0.3765 0.0782 Uiso 1.00 calc . . . H36 H 1.0606 0.1180 0.5069 0.0652 Uiso 1.00 calc . . . H39A H 0.8943 -0.1454 0.1357 0.1866 Uiso 1.00 calc . . . H39B H 0.9644 -0.1130 0.1213 0.1866 Uiso 1.00 calc . . . H39C H 0.9242 -0.0498 0.2203 0.1866 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.105(1) 0.144(2) 0.0809(9) 0.015(1) 0.0050(8) -0.068(1) F2 0.111(1) 0.107(1) 0.0645(8) -0.0172(9) 0.0110(7) -0.0392(8) O3 0.0426(6) 0.0373(6) 0.0440(6) 0.0021(4) -0.0025(4) 0.0068(5) O4 0.0502(7) 0.0407(7) 0.0707(8) 0.0000(5) 0.0079(6) -0.0096(6) O5 0.0442(7) 0.0623(8) 0.089(1) 0.0066(6) 0.0024(7) 0.0411(7) O6 0.0498(7) 0.0694(8) 0.0450(7) 0.0039(6) 0.0054(5) 0.0179(6) N7 0.335(6) 0.098(2) 0.154(3) 0.050(3) -0.043(4) 0.007(2) C8 0.049(1) 0.098(2) 0.056(1) 0.000(1) 0.0050(8) -0.034(1) C9 0.086(2) 0.106(2) 0.0384(10) 0.006(1) 0.0030(9) -0.010(1) C10 0.074(1) 0.068(1) 0.0407(9) -0.0004(10) 0.0020(9) -0.0017(9) C11 0.0295(7) 0.0476(9) 0.0383(8) -0.0035(6) 0.0012(6) -0.0031(7) C12 0.070(1) 0.052(1) 0.056(1) 0.0097(9) 0.0110(9) -0.0070(9) C13 0.073(1) 0.060(1) 0.085(2) 0.007(1) 0.018(1) -0.024(1) C14 0.0312(7) 0.0347(7) 0.0352(7) 0.0005(5) -0.0008(5) 0.0036(6) C15 0.0355(7) 0.0318(7) 0.0326(7) 0.0023(5) -0.0008(5) -0.0002(6) C16 0.0396(8) 0.0483(9) 0.0364(8) 0.0048(7) -0.0034(6) 0.0080(7) C17 0.0380(8) 0.0430(9) 0.0427(8) 0.0035(6) -0.0064(6) -0.0003(7) C18 0.0473(10) 0.065(1) 0.0509(10) 0.0028(8) -0.0154(8) 0.0041(9) C19 0.0400(9) 0.065(1) 0.073(1) -0.0016(8) -0.0207(8) -0.002(1) C20 0.0343(8) 0.052(1) 0.080(1) -0.0041(7) -0.0050(8) 0.0021(10) C21 0.0386(8) 0.0433(9) 0.0562(10) -0.0009(7) -0.0006(7) 0.0055(8) C22 0.0343(7) 0.0350(7) 0.0414(8) 0.0018(6) -0.0038(6) -0.0004(6) C23 0.050(1) 0.080(1) 0.050(1) -0.0123(9) 0.0042(8) -0.0204(10) C24 0.067(1) 0.090(2) 0.0360(9) -0.010(1) -0.0004(8) -0.0022(10) C25 0.055(1) 0.062(1) 0.0427(9) -0.0068(8) -0.0030(7) 0.0071(8) C26 0.0295(7) 0.0524(9) 0.0366(8) -0.0044(6) -0.0021(6) 0.0023(7) C27 0.058(1) 0.054(1) 0.0431(9) -0.0067(8) -0.0009(7) 0.0010(8) C28 0.062(1) 0.057(1) 0.060(1) -0.0071(9) 0.0018(9) -0.0094(9) C29 0.0362(7) 0.0409(8) 0.0392(8) -0.0026(6) -0.0037(6) 0.0045(6) C30 0.0368(7) 0.0345(7) 0.0339(7) -0.0007(6) -0.0011(6) 0.0009(6) C31 0.0406(8) 0.0405(8) 0.0381(8) -0.0015(6) 0.0034(6) 0.0010(6) C32 0.0376(8) 0.0466(9) 0.0463(9) -0.0007(7) 0.0043(6) -0.0044(7) C33 0.0465(10) 0.069(1) 0.053(1) -0.0020(8) 0.0105(8) -0.0051(9) C34 0.0397(10) 0.088(2) 0.073(1) 0.0031(10) 0.0137(9) -0.013(1) C35 0.0384(9) 0.082(1) 0.076(1) 0.0114(9) -0.0023(9) -0.014(1) C36 0.0427(9) 0.063(1) 0.058(1) 0.0062(8) -0.0061(8) -0.0031(9) C37 0.0388(8) 0.0437(9) 0.0444(8) 0.0004(6) -0.0004(6) -0.0037(7) C38 0.164(3) 0.073(2) 0.101(2) 0.030(2) 0.001(2) -0.009(2) C39 0.238(5) 0.156(4) 0.106(3) 0.102(4) 0.065(3) 0.036(3) #------------------------------------------------------------------------------ _computing_data_collection ; WinAFC Diffractometer Control Software (Rigaku, 1999) ; _computing_cell_refinement ; WinAFC Diffractometer Control Software (Rigaku, 1999) ; _computing_data_reduction ; TEXSAN (Molecular Structure Corporation, 2001) ; _computing_structure_solution ; SIR92 (Altomare et al., 1994) ; _computing_structure_refinement ; SHELXL97 (Sheldrick, 1997) ; _computing_publication_material TEXSAN _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C8 1.362(3) . . yes F2 C23 1.358(3) . . yes O3 O4 1.447(2) . . yes O3 C14 1.437(2) . . yes O4 H4 0.820 . . no O5 C16 1.428(2) . . yes O5 H5 0.820 . . no O6 C31 1.221(2) . . yes N7 C38 1.095(5) . . yes C8 C9 1.341(4) . . yes C8 C13 1.355(3) . . yes C9 C10 1.387(3) . . yes C9 H9 0.951 . . no C10 C11 1.379(3) . . yes C10 H10 0.951 . . no C11 C12 1.373(3) . . yes C11 C14 1.520(2) . . yes C12 C13 1.389(3) . . yes C12 H12 0.951 . . no C13 H13 0.951 . . no C14 C15 1.532(2) . . yes C14 C22 1.523(2) . . yes C15 C16 1.523(2) . . yes C15 C30 1.332(2) . . yes C16 C17 1.502(2) . . yes C16 H16 0.950 . . no C17 C18 1.391(2) . . yes C17 C22 1.381(2) . . yes C18 C19 1.380(3) . . yes C18 H18 0.949 . . no C19 C20 1.387(3) . . yes C19 H19 0.950 . . no C20 C21 1.388(2) . . yes C20 H20 0.952 . . no C21 C22 1.381(2) . . yes C21 H21 0.951 . . no C23 C24 1.358(3) . . yes C23 C28 1.363(3) . . yes C24 C25 1.388(3) . . yes C24 H24 0.951 . . no C25 C26 1.382(2) . . yes C25 H25 0.951 . . no C26 C27 1.383(3) . . yes C26 C29 1.525(2) . . yes C27 C28 1.389(3) . . yes C27 H27 0.951 . . no C28 H28 0.949 . . no C29 C30 1.530(2) . . yes C29 C37 1.522(2) . . yes C29 H29 0.951 . . no C30 C31 1.499(2) . . yes C31 C32 1.474(2) . . yes C32 C33 1.391(3) . . yes C32 C37 1.386(2) . . yes C33 C34 1.379(3) . . yes C33 H33 0.950 . . no C34 C35 1.387(3) . . yes C34 H34 0.951 . . no C35 C36 1.383(3) . . yes C35 H35 0.950 . . no C36 C37 1.390(2) . . yes C36 H36 0.951 . . no C38 C39 1.392(6) . . yes C39 H39A 0.970 . . no C39 H39B 0.961 . . no C39 H39C 0.959 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 O3 C14 108.09(10) . . . yes O3 O4 H4 109.5 . . . no C16 O5 H5 109.5 . . . no F1 C8 C9 118.8(2) . . . yes F1 C8 C13 118.1(2) . . . yes C9 C8 C13 123.2(2) . . . yes C8 C9 C10 118.6(2) . . . yes C8 C9 H9 120.7 . . . no C10 C9 H9 120.7 . . . no C9 C10 C11 120.4(2) . . . yes C9 C10 H10 119.8 . . . no C11 C10 H10 119.8 . . . no C10 C11 C12 119.0(2) . . . yes C10 C11 C14 121.5(2) . . . yes C12 C11 C14 119.5(1) . . . yes C11 C12 C13 120.6(2) . . . yes C11 C12 H12 119.7 . . . no C13 C12 H12 119.7 . . . no C8 C13 C12 118.2(2) . . . yes C8 C13 H13 121.0 . . . no C12 C13 H13 120.8 . . . no O3 C14 C11 105.0(1) . . . yes O3 C14 C15 111.5(1) . . . yes O3 C14 C22 112.7(1) . . . yes C11 C14 C15 113.9(1) . . . yes C11 C14 C22 111.0(1) . . . yes C15 C14 C22 103.0(1) . . . yes C14 C15 C16 109.8(1) . . . yes C14 C15 C30 125.9(1) . . . yes C16 C15 C30 124.3(1) . . . yes O5 C16 C15 112.4(1) . . . yes O5 C16 C17 109.4(1) . . . yes O5 C16 H16 110.3 . . . no C15 C16 C17 103.7(1) . . . yes C15 C16 H16 110.4 . . . no C17 C16 H16 110.4 . . . no C16 C17 C18 127.7(2) . . . yes C16 C17 C22 112.1(1) . . . yes C18 C17 C22 120.2(1) . . . yes C17 C18 C19 118.6(2) . . . yes C17 C18 H18 120.8 . . . no C19 C18 H18 120.6 . . . no C18 C19 C20 121.1(2) . . . yes C18 C19 H19 119.3 . . . no C20 C19 H19 119.6 . . . no C19 C20 C21 120.3(2) . . . yes C19 C20 H20 119.8 . . . no C21 C20 H20 119.9 . . . no C20 C21 C22 118.5(2) . . . yes C20 C21 H21 120.8 . . . no C22 C21 H21 120.7 . . . no C14 C22 C17 111.3(1) . . . yes C14 C22 C21 127.3(1) . . . yes C17 C22 C21 121.3(1) . . . yes F2 C23 C24 118.6(2) . . . yes F2 C23 C28 118.9(2) . . . yes C24 C23 C28 122.6(2) . . . yes C23 C24 C25 118.5(2) . . . yes C23 C24 H24 120.8 . . . no C25 C24 H24 120.8 . . . no C24 C25 C26 121.3(2) . . . yes C24 C25 H25 119.4 . . . no C26 C25 H25 119.3 . . . no C25 C26 C27 118.2(2) . . . yes C25 C26 C29 120.4(2) . . . yes C27 C26 C29 121.4(1) . . . yes C26 C27 C28 121.1(2) . . . yes C26 C27 H27 119.4 . . . no C28 C27 H27 119.5 . . . no C23 C28 C27 118.4(2) . . . yes C23 C28 H28 120.9 . . . no C27 C28 H28 120.7 . . . no C26 C29 C30 114.4(1) . . . yes C26 C29 C37 110.5(1) . . . yes C26 C29 H29 109.9 . . . no C30 C29 C37 102.0(1) . . . yes C30 C29 H29 109.9 . . . no C37 C29 H29 109.9 . . . no C15 C30 C29 128.1(1) . . . yes C15 C30 C31 123.3(1) . . . yes C29 C30 C31 108.1(1) . . . yes O6 C31 C30 126.9(1) . . . yes O6 C31 C32 126.7(1) . . . yes C30 C31 C32 106.4(1) . . . yes C31 C32 C33 128.4(2) . . . yes C31 C32 C37 109.8(1) . . . yes C33 C32 C37 121.8(1) . . . yes C32 C33 C34 118.0(2) . . . yes C32 C33 H33 121.0 . . . no C34 C33 H33 121.0 . . . no C33 C34 C35 120.4(2) . . . yes C33 C34 H34 119.8 . . . no C35 C34 H34 119.8 . . . no C34 C35 C36 121.6(2) . . . yes C34 C35 H35 119.3 . . . no C36 C35 H35 119.2 . . . no C35 C36 C37 118.4(2) . . . yes C35 C36 H36 120.7 . . . no C37 C36 H36 120.9 . . . no C29 C37 C32 111.8(1) . . . yes C29 C37 C36 128.4(2) . . . yes C32 C37 C36 119.7(2) . . . yes N7 C38 C39 179.7(5) . . . yes C38 C39 H39A 110.9 . . . no C38 C39 H39B 112.0 . . . no C38 C39 H39C 111.9 . . . no H39A C39 H39B 106.9 . . . no H39A C39 H39C 107.1 . . . no H39B C39 H39C 107.8 . . . no #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O4 H4 O5 . . 2_645 0.82 1.88 2.698(2) 172 yes O5 H5 O6 . . . 0.82 2.10 2.759(2) 138 yes data_I _database_code_CSD 209593 _publ_section_abstract ; In the title compound, C~30~H~20~F~2~O~4~.CH~2~Cl~2~ two indene rings make an angle of 27.0(1)\%. The peroxo O-O bond distance is 1.447(2) \%A. ; _publ_section_comment ; One of the indene rings is not planar, the dihedral angle between C30/C31/C32 and C30/C38/C33/C32 being 13.5(1)\%. The two indene rings bend with each other, and the dihedral angle between the phenyl rings C18-C23 and C33-C38 is 27.0(1)\%. The dihedral angle between the two fluorophenyl rings is 5.5(1)\%. There is intramolecular O7-H7...O8 hydrogen bond. There is also intermolecular hydrogen bond, O6-H6...O7 (3/2-x, y-1/2, 3/2-z), which form zigzag chain along b. ; _publ_section_exptl_prep ; The colourless crystals were grown from a dichloromethane solution. ; _publ_section_exptl_refinement ; The dichloromethane molecule shows orientational disorder. The occupation factors of C39A and C39B are 70% and 30%, respectively. One of the Cl atoms bonded to C39A has two possible possitions. In total, three combinations Cl1A-C39A-Cl2A, Cl1A-C39A-Cl2C, and Cl1B-C39B-Cl2B were assumed with the possibility ratio of 50%, 20%, and 30%, respectively. All the non-H atoms except for C39B were refined anisotropically. The H atoms of the dichloromethane were not introduced. The hydroxyl and peroxyl H atoms were located from difference syntheses and ride on the parent atoms. The other H-atoms were positioned geometrically and fixed with U~iso~(H) = 1.2U~eq~(parent atom). ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Molecular Structure Corporation (2001). TEXSAN. Version 1.11. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Rigaku (1999). WinAFC Diffractometer Control Software. Rigaku Corporation, Tokyo, Japan. Sheldrick, G. M. (1997). SHELXL97. University of Gottingen, Germany. ; _publ_section_figure_captions ; Fig. 1. A view of the molecular structure of (I), showing 50% displacement ellipsoids for non-H atoms. Fig. 2. Projection of the crystal structure of (I) along c. ; _audit_creation_date 'Wed Feb 19 12:20:55 2003' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C31 H22 Cl2 F2 O4 ' _chemical_formula_moiety 'C30 H20 F2 O4, C H2 Cl2' _chemical_formula_weight 567.42 _chemical_melting_point ? #------------------------------------------------------------------------------ _exptl_crystal_F_000 1168 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 21.462(4) _cell_length_b 12.138(3) _cell_length_c 10.296(3) _cell_angle_alpha 90 _cell_angle_beta 93.233(19) _cell_angle_gamma 90 _cell_volume 2677.9(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.2 _cell_measurement_theta_max 12.7 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.893 _exptl_absorpt_correction_T_max 0.916 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w _diffrn_reflns_number 7049 _diffrn_reflns_av_R_equivalents 0.0071 _diffrn_reflns_theta_min ? _diffrn_reflns_theta_max 27.49 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.0 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 6134 _reflns_number_gt 3658 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1642 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 6134 _refine_ls_number_parameters 385 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.0749P)^2^+0.6997P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0000 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_diff_density_max 0.37 _refine_diff_density_min -0.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Cl Cl 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.6307(2) 0.0297(4) 1.0270(4) 0.147(1) Uani 0.70 d P . . Cl1B Cl 0.6124(6) 0.0476(8) 1.0275(9) 0.168(5) Uani 0.30 d P . . Cl2A Cl 0.5416(3) -0.0437(4) 0.8375(7) 0.181(2) Uani 0.50 d P . . Cl2B Cl 0.5935(4) -0.1448(3) 0.8737(5) 0.133(2) Uani 0.30 d P . . Cl2C Cl 0.5534(5) -0.1006(9) 0.849(1) 0.116(3) Uani 0.20 d P . . F3 F 0.72904(9) 0.3904(2) 0.1075(2) 0.0968(6) Uani 1.00 d . . . F4 F 0.5587(1) 0.4927(2) 0.1313(2) 0.1058(7) Uani 1.00 d . . . O5 O 0.68762(7) 0.0459(1) 0.5304(1) 0.0430(3) Uani 1.00 d . . . O6 O 0.67782(8) -0.0187(1) 0.6456(2) 0.0562(4) Uani 1.00 d . . . O7 O 0.72107(8) 0.3496(2) 0.8126(2) 0.0664(5) Uani 1.00 d . . . O8 O 0.59710(8) 0.3120(2) 0.8686(2) 0.0612(5) Uani 1.00 d . . . C9 C 0.7262(1) 0.3322(3) 0.2201(3) 0.0611(7) Uani 1.00 d . . . C10 C 0.7271(1) 0.2209(3) 0.2132(2) 0.0668(7) Uani 1.00 d . . . C11 C 0.7225(1) 0.1617(2) 0.3275(2) 0.0560(6) Uani 1.00 d . . . C12 C 0.71810(9) 0.2149(2) 0.4452(2) 0.0389(4) Uani 1.00 d . . . C13 C 0.7187(1) 0.3285(2) 0.4469(2) 0.0546(6) Uani 1.00 d . . . C14 C 0.7226(1) 0.3880(2) 0.3332(3) 0.0652(7) Uani 1.00 d . . . C15 C 0.71374(9) 0.1504(2) 0.5711(2) 0.0361(4) Uani 1.00 d . . . C16 C 0.67464(9) 0.2059(2) 0.6723(2) 0.0364(4) Uani 1.00 d . . . C17 C 0.7155(1) 0.2333(2) 0.7929(2) 0.0452(5) Uani 1.00 d . . . C18 C 0.7781(1) 0.1860(2) 0.7646(2) 0.0470(5) Uani 1.00 d . . . C19 C 0.8325(1) 0.1855(3) 0.8443(3) 0.0669(7) Uani 1.00 d . . . C20 C 0.8853(1) 0.1376(3) 0.7993(3) 0.0752(8) Uani 1.00 d . . . C21 C 0.8849(1) 0.0908(2) 0.6765(3) 0.0668(7) Uani 1.00 d . . . C22 C 0.8307(1) 0.0919(2) 0.5960(2) 0.0525(5) Uani 1.00 d . . . C23 C 0.77746(9) 0.1391(2) 0.6421(2) 0.0416(5) Uani 1.00 d . . . C24 C 0.5604(1) 0.4203(3) 0.2319(3) 0.0670(7) Uani 1.00 d . . . C25 C 0.5634(1) 0.3115(3) 0.2052(2) 0.0688(8) Uani 1.00 d . . . C26 C 0.5656(1) 0.2377(2) 0.3085(2) 0.0564(6) Uani 1.00 d . . . C27 C 0.56509(9) 0.2739(2) 0.4362(2) 0.0441(5) Uani 1.00 d . . . C28 C 0.5615(1) 0.3863(2) 0.4581(2) 0.0543(6) Uani 1.00 d . . . C29 C 0.5591(1) 0.4605(2) 0.3561(3) 0.0675(7) Uani 1.00 d . . . C30 C 0.56720(9) 0.1918(2) 0.5488(2) 0.0426(5) Uani 1.00 d . . . C31 C 0.61322(9) 0.2236(2) 0.6610(2) 0.0386(4) Uani 1.00 d . . . C32 C 0.5766(1) 0.2650(2) 0.7705(2) 0.0446(5) Uani 1.00 d . . . C33 C 0.5111(1) 0.2358(2) 0.7371(2) 0.0483(5) Uani 1.00 d . . . C34 C 0.4597(1) 0.2474(2) 0.8131(3) 0.0606(6) Uani 1.00 d . . . C35 C 0.4029(1) 0.2082(3) 0.7628(3) 0.0725(8) Uani 1.00 d . . . C36 C 0.3976(1) 0.1597(3) 0.6412(3) 0.0716(8) Uani 1.00 d . . . C37 C 0.4482(1) 0.1514(2) 0.5639(3) 0.0608(6) Uani 1.00 d . . . C38 C 0.5056(1) 0.1900(2) 0.6135(2) 0.0464(5) Uani 1.00 d . . . C39A C 0.6202(4) -0.0681(7) 0.9118(6) 0.127(2) Uani 0.70 d P . . C39B C 0.5812(9) -0.006(2) 0.899(2) 0.11383(6) Uiso 0.30 d P . . H6 H 0.7054 -0.0653 0.6550 0.0562 Uiso 1.00 calc . . . H7 H 0.6901 0.3725 0.8470 0.0664 Uiso 1.00 calc . . . H10 H 0.7310 0.1845 0.1325 0.0797 Uiso 1.00 calc . . . H11 H 0.7225 0.0834 0.3249 0.0668 Uiso 1.00 calc . . . H13 H 0.7167 0.3662 0.5274 0.0648 Uiso 1.00 calc . . . H14 H 0.7226 0.4664 0.3342 0.0781 Uiso 1.00 calc . . . H17 H 0.6998 0.1989 0.8674 0.0538 Uiso 1.00 calc . . . H19 H 0.8333 0.2179 0.9285 0.0802 Uiso 1.00 calc . . . H20 H 0.9227 0.1368 0.8533 0.0896 Uiso 1.00 calc . . . H21 H 0.9216 0.0578 0.6474 0.0794 Uiso 1.00 calc . . . H22 H 0.8302 0.0607 0.5114 0.0623 Uiso 1.00 calc . . . H25 H 0.5641 0.2861 0.1181 0.0818 Uiso 1.00 calc . . . H26 H 0.5672 0.1610 0.2913 0.0671 Uiso 1.00 calc . . . H28 H 0.5605 0.4128 0.5447 0.0643 Uiso 1.00 calc . . . H29 H 0.5570 0.5375 0.3718 0.0804 Uiso 1.00 calc . . . H30 H 0.5765 0.1202 0.5181 0.0509 Uiso 1.00 calc . . . H34 H 0.4638 0.2808 0.8966 0.0718 Uiso 1.00 calc . . . H35 H 0.3670 0.2145 0.8125 0.0868 Uiso 1.00 calc . . . H36 H 0.3583 0.1316 0.6092 0.0850 Uiso 1.00 calc . . . H37 H 0.4438 0.1200 0.4794 0.0722 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1A 0.153(2) 0.141(3) 0.143(3) -0.061(2) -0.033(2) 0.021(2) Cl1B 0.29(1) 0.088(3) 0.135(6) -0.047(5) 0.093(7) -0.062(4) Cl2A 0.128(3) 0.171(5) 0.235(5) -0.009(3) -0.055(3) -0.040(4) Cl2B 0.223(6) 0.068(2) 0.116(3) -0.010(3) 0.081(4) -0.009(2) Cl2C 0.097(5) 0.115(7) 0.134(6) -0.009(5) -0.001(5) -0.068(6) F3 0.111(1) 0.114(2) 0.066(1) -0.019(1) 0.0097(9) 0.043(1) F4 0.134(2) 0.116(2) 0.069(1) 0.025(1) 0.017(1) 0.043(1) O5 0.0479(8) 0.0364(8) 0.0443(8) -0.0031(6) -0.0003(6) -0.0039(6) O6 0.057(1) 0.0435(9) 0.069(1) 0.0018(7) 0.0079(8) 0.0141(8) O7 0.052(1) 0.063(1) 0.084(1) -0.0070(8) 0.0043(9) -0.0380(10) O8 0.0555(10) 0.078(1) 0.0512(9) -0.0045(9) 0.0079(7) -0.0204(9) C9 0.055(1) 0.078(2) 0.051(1) -0.007(1) 0.007(1) 0.023(1) C10 0.076(2) 0.084(2) 0.041(1) -0.003(2) 0.011(1) 0.001(1) C11 0.071(2) 0.053(1) 0.045(1) 0.006(1) 0.009(1) -0.001(1) C12 0.0338(10) 0.045(1) 0.0383(10) 0.0006(8) 0.0018(8) 0.0016(9) C13 0.065(1) 0.047(1) 0.052(1) -0.011(1) 0.013(1) 0.000(1) C14 0.072(2) 0.053(1) 0.071(2) -0.014(1) 0.012(1) 0.016(1) C15 0.0343(10) 0.035(1) 0.0387(10) -0.0012(8) 0.0008(8) -0.0026(8) C16 0.039(1) 0.0348(10) 0.0349(9) -0.0022(8) -0.0001(8) -0.0005(8) C17 0.044(1) 0.052(1) 0.040(1) -0.0057(9) -0.0014(9) -0.0072(9) C18 0.040(1) 0.051(1) 0.048(1) -0.0028(9) -0.0042(9) -0.003(1) C19 0.053(1) 0.087(2) 0.059(1) -0.002(1) -0.015(1) -0.015(1) C20 0.046(1) 0.091(2) 0.086(2) 0.005(1) -0.024(1) -0.009(2) C21 0.039(1) 0.069(2) 0.091(2) 0.005(1) -0.006(1) -0.010(2) C22 0.041(1) 0.052(1) 0.064(1) 0.0022(10) 0.001(1) -0.008(1) C23 0.039(1) 0.039(1) 0.046(1) -0.0018(8) -0.0031(9) -0.0017(9) C24 0.062(2) 0.085(2) 0.055(1) 0.013(1) 0.006(1) 0.022(1) C25 0.069(2) 0.099(2) 0.039(1) 0.002(2) 0.002(1) 0.002(1) C26 0.054(1) 0.069(2) 0.046(1) 0.000(1) -0.0019(10) -0.008(1) C27 0.0342(10) 0.057(1) 0.041(1) 0.0044(9) -0.0001(8) -0.0018(10) C28 0.060(1) 0.056(1) 0.047(1) 0.012(1) 0.004(1) 0.000(1) C29 0.070(2) 0.063(2) 0.070(2) 0.016(1) 0.012(1) 0.012(1) C30 0.040(1) 0.043(1) 0.044(1) 0.0026(9) -0.0045(8) -0.0051(9) C31 0.041(1) 0.037(1) 0.0380(10) 0.0007(8) 0.0011(8) -0.0019(8) C32 0.046(1) 0.047(1) 0.041(1) 0.0019(9) 0.0041(9) -0.0012(9) C33 0.042(1) 0.051(1) 0.052(1) 0.0001(10) 0.0049(9) 0.007(1) C34 0.050(1) 0.075(2) 0.057(1) 0.002(1) 0.013(1) 0.008(1) C35 0.043(1) 0.099(2) 0.076(2) -0.002(1) 0.013(1) 0.020(2) C36 0.043(1) 0.095(2) 0.077(2) -0.013(1) -0.003(1) 0.017(2) C37 0.047(1) 0.070(2) 0.065(2) -0.008(1) -0.006(1) 0.006(1) C38 0.041(1) 0.049(1) 0.049(1) -0.0007(9) -0.0013(9) 0.0058(10) C39A 0.187(8) 0.099(5) 0.098(4) -0.018(5) 0.046(5) -0.007(4) #------------------------------------------------------------------------------ _computing_data_collection ; WinAFC Diffractometer Control Software (Rigaku, 1999) ; _computing_cell_refinement ; WinAFC Diffractometer Control Software (Rigaku, 1999) ; _computing_data_reduction ; TEXSAN (Molecular Structure Corporation, 2001) ; _computing_structure_solution ; SIR92 (Altomare et al., 1994) ; _computing_structure_refinement ; SHELXL97 (Sheldrick, 1997) ; _computing_publication_material TEXSAN _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1A C39A 1.684(9) . . yes Cl1B C39B 1.59(2) . . yes Cl2A C39A 1.84(1) . . yes Cl2B C39B 1.73(2) . . yes Cl2C C39A 1.59(1) . . yes F3 C9 1.362(3) . . yes F4 C24 1.357(4) . . yes O5 O6 1.447(2) . . yes O5 C15 1.439(2) . . yes O6 H6 0.820 . . no O7 C17 1.430(3) . . yes O7 H7 0.820 . . no O8 C32 1.221(3) . . yes C9 C10 1.353(4) . . yes C9 C14 1.353(4) . . yes C10 C11 1.387(4) . . yes C10 H10 0.950 . . no C11 C12 1.382(3) . . yes C11 H11 0.950 . . no C12 C13 1.378(3) . . yes C12 C15 1.521(3) . . yes C13 C14 1.382(4) . . yes C13 H13 0.950 . . no C14 H14 0.952 . . no C15 C16 1.531(3) . . yes C15 C23 1.520(3) . . yes C16 C17 1.516(3) . . yes C16 C31 1.334(3) . . yes C17 C18 1.505(3) . . yes C17 H17 0.951 . . no C18 C19 1.389(3) . . yes C18 C23 1.383(3) . . yes C19 C20 1.376(4) . . yes C19 H19 0.952 . . no C20 C21 1.386(4) . . yes C20 H20 0.951 . . no C21 C22 1.389(3) . . yes C21 H21 0.949 . . no C22 C23 1.386(3) . . yes C22 H22 0.949 . . no C24 C25 1.350(5) . . yes C24 C29 1.370(4) . . yes C25 C26 1.390(4) . . yes C25 H25 0.949 . . no C26 C27 1.388(3) . . yes C26 H26 0.948 . . no C27 C28 1.385(3) . . yes C27 C30 1.527(3) . . yes C28 C29 1.383(4) . . yes C28 H28 0.950 . . no C29 H29 0.950 . . no C30 C31 1.526(3) . . yes C30 C38 1.515(3) . . yes C30 H30 0.950 . . no C31 C32 1.498(3) . . yes C32 C33 1.471(3) . . yes C33 C34 1.395(4) . . yes C33 C38 1.388(3) . . yes C34 C35 1.383(4) . . yes C34 H34 0.949 . . no C35 C36 1.383(4) . . yes C35 H35 0.950 . . no C36 C37 1.386(4) . . yes C36 H36 0.951 . . no C37 C38 1.387(3) . . yes C37 H37 0.949 . . no #------------------------------------------------------------------------------ # Cl1A Cl1B 0.45(1) . . yes # Cl1A C39B 1.70(2) . . yes # Cl1B C39A 1.86(1) . . yes # Cl2A Cl2B 1.685(8) . . yes # Cl2A Cl2C 0.74(1) . . yes # Cl2A C39B 1.13(2) . . yes # Cl2B Cl2C 1.03(1) . . yes # Cl2B C39A 1.15(1) . . yes # Cl2C C39B 1.38(2) . . yes # C39A C39B 1.13(2) . . yes 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 O5 C15 108.2(1) . . . yes O5 O6 H6 109.5 . . . no C17 O7 H7 109.5 . . . no F3 C9 C10 118.1(2) . . . yes F3 C9 C14 118.7(3) . . . yes C10 C9 C14 123.2(3) . . . yes C9 C10 C11 118.1(2) . . . yes C9 C10 H10 120.9 . . . no C11 C10 H10 121.0 . . . no C10 C11 C12 120.9(2) . . . yes C10 C11 H11 119.6 . . . no C12 C11 H11 119.5 . . . no C11 C12 C13 118.6(2) . . . yes C11 C12 C15 121.1(2) . . . yes C13 C12 C15 120.3(2) . . . yes C12 C13 C14 120.8(2) . . . yes C12 C13 H13 119.5 . . . no C14 C13 H13 119.6 . . . no C9 C14 C13 118.4(2) . . . yes C9 C14 H14 120.7 . . . no C13 C14 H14 120.9 . . . no O5 C15 C12 104.3(2) . . . yes O5 C15 C16 111.5(2) . . . yes O5 C15 C23 112.7(2) . . . yes C12 C15 C16 114.6(2) . . . yes C12 C15 C23 111.0(2) . . . yes C16 C15 C23 103.0(2) . . . yes C15 C16 C17 109.9(2) . . . yes C15 C16 C31 126.0(2) . . . yes C17 C16 C31 124.1(2) . . . yes O7 C17 C16 111.8(2) . . . yes O7 C17 C18 109.6(2) . . . yes O7 C17 H17 110.4 . . . no C16 C17 C18 103.9(2) . . . yes C16 C17 H17 110.4 . . . no C18 C17 H17 110.5 . . . no C17 C18 C19 128.1(2) . . . yes C17 C18 C23 111.7(2) . . . yes C19 C18 C23 120.2(2) . . . yes C18 C19 C20 118.9(3) . . . yes C18 C19 H19 120.5 . . . no C20 C19 H19 120.6 . . . no C19 C20 C21 121.1(2) . . . yes C19 C20 H20 119.5 . . . no C21 C20 H20 119.4 . . . no C20 C21 C22 120.2(2) . . . yes C20 C21 H21 119.9 . . . no C22 C21 H21 120.0 . . . no C21 C22 C23 118.6(2) . . . yes C21 C22 H22 120.6 . . . no C23 C22 H22 120.8 . . . no C15 C23 C18 111.4(2) . . . yes C15 C23 C22 127.5(2) . . . yes C18 C23 C22 121.1(2) . . . yes F4 C24 C25 118.5(2) . . . yes F4 C24 C29 118.7(3) . . . yes C25 C24 C29 122.8(3) . . . yes C24 C25 C26 118.3(2) . . . yes C24 C25 H25 120.9 . . . no C26 C25 H25 120.8 . . . no C25 C26 C27 121.3(2) . . . yes C25 C26 H26 119.3 . . . no C27 C26 H26 119.4 . . . no C26 C27 C28 118.0(2) . . . yes C26 C27 C30 120.7(2) . . . yes C28 C27 C30 121.3(2) . . . yes C27 C28 C29 121.2(2) . . . yes C27 C28 H28 119.4 . . . no C29 C28 H28 119.4 . . . no C24 C29 C28 118.4(3) . . . yes C24 C29 H29 120.9 . . . no C28 C29 H29 120.8 . . . no C27 C30 C31 113.5(2) . . . yes C27 C30 C38 110.7(2) . . . yes C27 C30 H30 110.1 . . . no C31 C30 C38 102.4(2) . . . yes C31 C30 H30 110.1 . . . no C38 C30 H30 109.8 . . . no C16 C31 C30 128.3(2) . . . yes C16 C31 C32 123.1(2) . . . yes C30 C31 C32 108.0(2) . . . yes O8 C32 C31 126.8(2) . . . yes O8 C32 C33 127.0(2) . . . yes C31 C32 C33 106.2(2) . . . yes C32 C33 C34 128.3(2) . . . yes C32 C33 C38 110.0(2) . . . yes C34 C33 C38 121.7(2) . . . yes C33 C34 C35 117.6(2) . . . yes C33 C34 H34 121.0 . . . no C35 C34 H34 121.3 . . . no C34 C35 C36 120.7(3) . . . yes C34 C35 H35 119.6 . . . no C36 C35 H35 119.7 . . . no C35 C36 C37 121.6(2) . . . yes C35 C36 H36 119.4 . . . no C37 C36 H36 119.0 . . . no C36 C37 C38 118.2(2) . . . yes C36 C37 H37 120.8 . . . no C38 C37 H37 121.0 . . . no C30 C38 C33 111.5(2) . . . yes C30 C38 C37 128.4(2) . . . yes C33 C38 C37 120.1(2) . . . yes Cl1A C39A Cl2A 105.3(5) . . . yes Cl1A C39A Cl2C 122.9(7) . . . yes Cl1B C39B Cl2B 117(1) . . . yes #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O6 H6 O7 . . 2_646 0.82 1.90 2.710(2) 169 yes O7 H7 O8 . . . 0.82 2.15 2.792(3) 135 yes O7 H7 F3 . . 1_556 0.82 2.77 3.072(2) 104 no