# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Amitabha Sarkar' 'Vedavati G. Puranik' 'Suresh Kumar Tipparaju' _publ_contact_author_name 'Prof Amitabha Sarkar' _publ_contact_author_address ; Department of Organic Chemistry Indian Association for the Cultivation of Science Jadavpur Kolkata 700 032 INDIA ; _publ_contact_author_email OCAS@MAHENDRA.IACS.RES.IN _publ_section_title ; Chelation-control in nucleophilic addition to Cr(CO)3-complexed aryl aldehydes ; data_3a _database_code_CSD 203336 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Arene chromium complex' _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 Cr O6' _chemical_formula_sum 'C14 H16 Cr O6' _chemical_formula_weight 332.27 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' Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic' _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0987(10) _cell_length_b 8.0844(6) _cell_length_c 23.252(2) _cell_angle_alpha 90.0 _cell_angle_beta 99.511(11) _cell_angle_gamma 90.0 _cell_volume 1501.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 18 _exptl_crystal_description cubic _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.785 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q-scan _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% <4% _diffrn_reflns_number 2649 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 24.91 _reflns_number_total 2649 _reflns_number_gt 2028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software' _computing_data_reduction 'NRCVAX (PC Version) Gabe, E. J. et al., 1989)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, L and Pritzkow, H, 1994)' _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^)+(0.0605P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2649 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0527 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cr Cr 0.98735(4) 0.74126(5) 0.365230(16) 0.03729(15) Uani 1 1 d . . . O1 O 1.3190(2) 0.9011(3) 0.36049(11) 0.0820(7) Uani 1 1 d . . . O2 O 0.9168(4) 0.7445(3) 0.23479(11) 0.1043(10) Uani 1 1 d . . . O3 O 0.8593(3) 1.0865(3) 0.36573(12) 0.0909(8) Uani 1 1 d . . . O6 O 0.5904(3) 0.6639(3) 0.48256(9) 0.0580(6) Uani 1 1 d . . . O4 O 0.5958(2) 0.5062(2) 0.29197(7) 0.0544(5) Uani 1 1 d . . . O5 O 0.49208(18) 0.4833(2) 0.37973(7) 0.0453(4) Uani 1 1 d . . . C1 C 1.1919(3) 0.8372(4) 0.36241(13) 0.0546(7) Uani 1 1 d . . . C2 C 0.9446(4) 0.7435(4) 0.28504(13) 0.0617(8) Uani 1 1 d . . . C3 C 0.9063(3) 0.9528(4) 0.36507(13) 0.0540(7) Uani 1 1 d . . . C4 C 0.8229(3) 0.6750(3) 0.42963(10) 0.0367(5) Uani 1 1 d . . . C5 C 0.9916(3) 0.6732(4) 0.45806(12) 0.0464(6) Uani 1 1 d . . . C6 C 1.1139(3) 0.5808(4) 0.43566(13) 0.0538(7) Uani 1 1 d . . . C7 C 1.0683(3) 0.4832(3) 0.38639(13) 0.0517(7) Uani 1 1 d . . . C8 C 0.9034(3) 0.4816(3) 0.35811(12) 0.0444(6) Uani 1 1 d . . . C9 C 0.7781(3) 0.5767(3) 0.37885(10) 0.0362(5) Uani 1 1 d . . . C10 C 0.6896(3) 0.7742(3) 0.45454(12) 0.0450(6) Uani 1 1 d . . . C11 C 0.5980(3) 0.5731(3) 0.34721(10) 0.0397(5) Uani 1 1 d . . . C12 C 0.4389(5) 0.5307(6) 0.25410(16) 0.0762(10) Uani 1 1 d . . . C13 C 0.5287(5) 0.3119(4) 0.38690(18) 0.0654(9) Uani 1 1 d . . . C14 C 0.7563(5) 0.9019(5) 0.49904(17) 0.0680(9) Uani 1 1 d . . . H5 H 1.023(3) 0.742(3) 0.4887(12) 0.046(8) Uiso 1 1 d . . . H6 H 1.221(4) 0.588(3) 0.4553(12) 0.062(8) Uiso 1 1 d . . . H7 H 1.146(4) 0.430(3) 0.3747(12) 0.052(8) Uiso 1 1 d . . . H8 H 0.876(3) 0.417(3) 0.3239(11) 0.041(7) Uiso 1 1 d . . . H10 H 0.626(3) 0.823(3) 0.4241(10) 0.029(6) Uiso 1 1 d . . . H11A H 0.551(3) 0.682(3) 0.3437(8) 0.023(5) Uiso 1 1 d . . . H12A H 0.347(6) 0.471(6) 0.2688(19) 0.129(16) Uiso 1 1 d . . . H12B H 0.399(5) 0.651(5) 0.2559(16) 0.099(13) Uiso 1 1 d . . . H12C H 0.446(5) 0.486(4) 0.2157(17) 0.096(12) Uiso 1 1 d . . . H13A H 0.516(5) 0.268(5) 0.3524(18) 0.098(14) Uiso 1 1 d . . . H13B H 0.472(5) 0.266(4) 0.4156(16) 0.088(12) Uiso 1 1 d . . . H13C H 0.647(7) 0.296(5) 0.4094(19) 0.135(18) Uiso 1 1 d . . . H14A H 0.670(4) 0.963(4) 0.5074(13) 0.070(10) Uiso 1 1 d . . . H14B H 0.817(4) 0.983(4) 0.4825(14) 0.077(11) Uiso 1 1 d . . . H14C H 0.816(4) 0.849(4) 0.5329(15) 0.079(11) Uiso 1 1 d . . . H6O H 0.552(4) 0.604(4) 0.4622(12) 0.050(10) Uiso 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 Cr 0.0245(2) 0.0423(2) 0.0468(2) 0.00756(17) 0.01112(15) 0.00274(16) O1 0.0363(11) 0.0854(16) 0.128(2) 0.0235(14) 0.0253(12) -0.0065(10) O2 0.138(3) 0.125(2) 0.0514(14) 0.0127(13) 0.0186(15) -0.0132(19) O3 0.0860(17) 0.0494(14) 0.144(2) 0.0177(13) 0.0395(16) 0.0221(12) O6 0.0436(11) 0.0822(15) 0.0536(12) -0.0147(12) 0.0243(10) -0.0133(11) O4 0.0470(10) 0.0727(12) 0.0437(10) -0.0079(9) 0.0082(8) -0.0052(9) O5 0.0301(8) 0.0556(11) 0.0532(10) -0.0059(8) 0.0153(8) -0.0058(7) C1 0.0355(14) 0.0584(17) 0.0717(18) 0.0120(14) 0.0144(13) 0.0049(13) C2 0.0646(19) 0.0666(19) 0.0572(18) 0.0110(15) 0.0195(15) -0.0057(15) C3 0.0398(14) 0.0539(18) 0.0715(18) 0.0144(14) 0.0186(13) 0.0026(13) C4 0.0260(11) 0.0460(13) 0.0404(12) 0.0056(10) 0.0116(10) 0.0008(10) C5 0.0297(13) 0.0643(17) 0.0443(14) 0.0091(13) 0.0032(11) -0.0026(12) C6 0.0263(13) 0.0703(19) 0.0644(18) 0.0266(15) 0.0063(13) 0.0076(12) C7 0.0359(14) 0.0473(15) 0.077(2) 0.0145(14) 0.0252(14) 0.0146(13) C8 0.0408(14) 0.0383(13) 0.0590(16) 0.0022(12) 0.0227(12) 0.0040(11) C9 0.0275(11) 0.0386(12) 0.0448(13) 0.0043(10) 0.0124(10) 0.0003(9) C10 0.0346(13) 0.0564(16) 0.0454(14) -0.0034(12) 0.0109(11) 0.0019(12) C11 0.0293(12) 0.0474(14) 0.0438(13) -0.0046(11) 0.0101(10) -0.0028(11) C12 0.062(2) 0.108(3) 0.0523(19) -0.006(2) -0.0082(17) -0.010(2) C13 0.073(2) 0.0547(18) 0.077(2) -0.0029(17) 0.038(2) -0.0090(16) C14 0.059(2) 0.078(2) 0.070(2) -0.0252(19) 0.0186(19) -0.0032(19) _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 Cr C3 1.832(3) . ? Cr C2 1.839(3) . ? Cr C1 1.840(3) . ? Cr C8 2.204(3) . ? Cr C6 2.205(3) . ? Cr C7 2.217(3) . ? Cr C9 2.218(2) . ? Cr C5 2.222(3) . ? Cr C4 2.228(2) . ? O1 C1 1.159(3) . ? O2 C2 1.153(4) . ? O3 C3 1.147(3) . ? O6 C10 1.428(3) . ? O6 H6O 0.71(3) . ? O4 C11 1.391(3) . ? O4 C12 1.435(4) . ? O5 C13 1.420(4) . ? O5 C11 1.432(3) . ? C4 C5 1.416(3) . ? C4 C9 1.420(3) . ? C4 C10 1.533(3) . ? C5 C6 1.407(4) . ? C5 H5 0.91(3) . ? C6 C7 1.390(4) . ? C6 H6 0.92(3) . ? C7 C8 1.387(4) . ? C7 H7 0.84(3) . ? C8 C9 1.419(3) . ? C8 H8 0.95(2) . ? C9 C11 1.522(3) . ? C10 C14 1.498(4) . ? C10 H10 0.90(2) . ? C11 H11A 0.96(2) . ? C12 H12A 1.00(5) . ? C12 H12B 1.03(4) . ? C12 H12C 0.97(4) . ? C13 H13A 0.87(4) . ? C13 H13B 0.95(4) . ? C13 H13C 1.02(5) . ? C14 H14A 0.90(3) . ? C14 H14B 0.94(4) . ? C14 H14C 0.95(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 Cr C2 88.93(13) . . ? C3 Cr C1 86.04(12) . . ? C2 Cr C1 88.82(13) . . ? C3 Cr C8 141.54(11) . . ? C2 Cr C8 85.95(12) . . ? C1 Cr C8 131.84(11) . . ? C3 Cr C6 132.33(13) . . ? C2 Cr C6 138.19(13) . . ? C1 Cr C6 87.93(11) . . ? C8 Cr C6 66.11(11) . . ? C3 Cr C7 166.29(12) . . ? C2 Cr C7 103.50(13) . . ? C1 Cr C7 99.77(11) . . ? C8 Cr C7 36.57(10) . . ? C6 Cr C7 36.63(11) . . ? C3 Cr C9 106.15(10) . . ? C2 Cr C9 97.50(11) . . ? C1 Cr C9 166.29(10) . . ? C8 Cr C9 37.45(9) . . ? C6 Cr C9 79.24(9) . . ? C7 Cr C9 66.97(9) . . ? C3 Cr C5 100.44(12) . . ? C2 Cr C5 163.17(13) . . ? C1 Cr C5 105.63(11) . . ? C8 Cr C5 78.00(11) . . ? C6 Cr C5 37.06(10) . . ? C7 Cr C5 66.10(11) . . ? C9 Cr C5 66.57(9) . . ? C3 Cr C4 88.40(10) . . ? C2 Cr C4 130.58(11) . . ? C1 Cr C4 140.09(11) . . ? C8 Cr C4 67.05(9) . . ? C6 Cr C4 67.37(9) . . ? C7 Cr C4 79.16(9) . . ? C9 Cr C4 37.24(8) . . ? C5 Cr C4 37.11(8) . . ? C10 O6 H6O 110(2) . . ? C11 O4 C12 112.8(2) . . ? C13 O5 C11 115.1(2) . . ? O1 C1 Cr 178.5(3) . . ? O2 C2 Cr 179.5(3) . . ? O3 C3 Cr 178.3(3) . . ? C5 C4 C9 118.5(2) . . ? C5 C4 C10 120.9(2) . . ? C9 C4 C10 120.5(2) . . ? C5 C4 Cr 71.23(14) . . ? C9 C4 Cr 70.99(12) . . ? C10 C4 Cr 131.64(17) . . ? C6 C5 C4 121.1(3) . . ? C6 C5 Cr 70.79(16) . . ? C4 C5 Cr 71.65(14) . . ? C6 C5 H5 119.8(18) . . ? C4 C5 H5 118.7(18) . . ? Cr C5 H5 124.7(16) . . ? C7 C6 C5 119.9(3) . . ? C7 C6 Cr 72.19(16) . . ? C5 C6 Cr 72.15(15) . . ? C7 C6 H6 123.3(18) . . ? C5 C6 H6 116.8(18) . . ? Cr C6 H6 128.3(18) . . ? C8 C7 C6 120.0(3) . . ? C8 C7 Cr 71.20(15) . . ? C6 C7 Cr 71.18(16) . . ? C8 C7 H7 123.4(19) . . ? C6 C7 H7 116.5(19) . . ? Cr C7 H7 128.2(18) . . ? C7 C8 C9 121.3(3) . . ? C7 C8 Cr 72.23(16) . . ? C9 C8 Cr 71.79(14) . . ? C7 C8 H8 118.4(15) . . ? C9 C8 H8 120.3(15) . . ? Cr C8 H8 128.0(15) . . ? C8 C9 C4 119.1(2) . . ? C8 C9 C11 120.5(2) . . ? C4 C9 C11 120.38(19) . . ? C8 C9 Cr 70.76(14) . . ? C4 C9 Cr 71.76(13) . . ? C11 C9 Cr 129.55(16) . . ? O6 C10 C14 106.3(2) . . ? O6 C10 C4 109.3(2) . . ? C14 C10 C4 115.2(2) . . ? O6 C10 H10 110.2(15) . . ? C14 C10 H10 109.7(15) . . ? C4 C10 H10 106.2(15) . . ? O4 C11 O5 111.91(19) . . ? O4 C11 C9 108.60(19) . . ? O5 C11 C9 111.39(19) . . ? O4 C11 H11A 109.6(12) . . ? O5 C11 H11A 104.1(13) . . ? C9 C11 H11A 111.1(13) . . ? O4 C12 H12A 111(2) . . ? O4 C12 H12B 111(2) . . ? H12A C12 H12B 101(3) . . ? O4 C12 H12C 110(2) . . ? H12A C12 H12C 107(3) . . ? H12B C12 H12C 117(3) . . ? O5 C13 H13A 108(3) . . ? O5 C13 H13B 111(2) . . ? H13A C13 H13B 119(3) . . ? O5 C13 H13C 110(3) . . ? H13A C13 H13C 112(4) . . ? H13B C13 H13C 96(3) . . ? C10 C14 H14A 109(2) . . ? C10 C14 H14B 110(2) . . ? H14A C14 H14B 101(3) . . ? C10 C14 H14C 110(2) . . ? H14A C14 H14C 112(3) . . ? H14B C14 H14C 115(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 Cr C1 O1 -6(10) . . . . ? C2 Cr C1 O1 83(10) . . . . ? C8 Cr C1 O1 166(100) . . . . ? C6 Cr C1 O1 -139(10) . . . . ? C7 Cr C1 O1 -174(100) . . . . ? C9 Cr C1 O1 -159(10) . . . . ? C5 Cr C1 O1 -106(10) . . . . ? C4 Cr C1 O1 -89(10) . . . . ? C3 Cr C2 O2 -94(43) . . . . ? C1 Cr C2 O2 180(100) . . . . ? C8 Cr C2 O2 48(43) . . . . ? C6 Cr C2 O2 94(43) . . . . ? C7 Cr C2 O2 80(43) . . . . ? C9 Cr C2 O2 12(43) . . . . ? C5 Cr C2 O2 30(43) . . . . ? C4 Cr C2 O2 -7(43) . . . . ? C2 Cr C3 O3 -121(9) . . . . ? C1 Cr C3 O3 -32(9) . . . . ? C8 Cr C3 O3 157(9) . . . . ? C6 Cr C3 O3 51(9) . . . . ? C7 Cr C3 O3 83(9) . . . . ? C9 Cr C3 O3 141(9) . . . . ? C5 Cr C3 O3 73(9) . . . . ? C4 Cr C3 O3 108(9) . . . . ? C3 Cr C4 C5 -109.72(19) . . . . ? C2 Cr C4 C5 163.06(19) . . . . ? C1 Cr C4 C5 -27.8(2) . . . . ? C8 Cr C4 C5 100.69(18) . . . . ? C6 Cr C4 C5 28.14(17) . . . . ? C7 Cr C4 C5 64.49(18) . . . . ? C9 Cr C4 C5 130.5(2) . . . . ? C3 Cr C4 C9 119.77(15) . . . . ? C2 Cr C4 C9 32.6(2) . . . . ? C1 Cr C4 C9 -158.34(17) . . . . ? C8 Cr C4 C9 -29.82(14) . . . . ? C6 Cr C4 C9 -102.36(16) . . . . ? C7 Cr C4 C9 -66.02(15) . . . . ? C5 Cr C4 C9 -130.5(2) . . . . ? C3 Cr C4 C10 5.4(2) . . . . ? C2 Cr C4 C10 -81.8(3) . . . . ? C1 Cr C4 C10 87.3(3) . . . . ? C8 Cr C4 C10 -144.2(2) . . . . ? C6 Cr C4 C10 143.3(2) . . . . ? C7 Cr C4 C10 179.6(2) . . . . ? C9 Cr C4 C10 -114.4(3) . . . . ? C5 Cr C4 C10 115.1(3) . . . . ? C9 C4 C5 C6 2.1(4) . . . . ? C10 C4 C5 C6 179.3(2) . . . . ? Cr C4 C5 C6 -52.8(2) . . . . ? C9 C4 C5 Cr 54.86(19) . . . . ? C10 C4 C5 Cr -127.9(2) . . . . ? C3 Cr C5 C6 -153.14(18) . . . . ? C2 Cr C5 C6 83.9(4) . . . . ? C1 Cr C5 C6 -64.4(2) . . . . ? C8 Cr C5 C6 66.07(18) . . . . ? C7 Cr C5 C6 29.58(17) . . . . ? C9 Cr C5 C6 103.65(19) . . . . ? C4 Cr C5 C6 133.8(3) . . . . ? C3 Cr C5 C4 73.10(18) . . . . ? C2 Cr C5 C4 -49.8(5) . . . . ? C1 Cr C5 C4 161.87(16) . . . . ? C8 Cr C5 C4 -67.68(16) . . . . ? C6 Cr C5 C4 -133.8(3) . . . . ? C7 Cr C5 C4 -104.18(18) . . . . ? C9 Cr C5 C4 -30.10(14) . . . . ? C4 C5 C6 C7 -3.0(4) . . . . ? Cr C5 C6 C7 -56.2(2) . . . . ? C4 C5 C6 Cr 53.2(2) . . . . ? C3 Cr C6 C7 167.80(16) . . . . ? C2 Cr C6 C7 -23.6(2) . . . . ? C1 Cr C6 C7 -109.47(17) . . . . ? C8 Cr C6 C7 28.78(15) . . . . ? C9 Cr C6 C7 65.68(16) . . . . ? C5 Cr C6 C7 130.9(2) . . . . ? C4 Cr C6 C7 102.68(17) . . . . ? C3 Cr C6 C5 36.9(2) . . . . ? C2 Cr C6 C5 -154.4(2) . . . . ? C1 Cr C6 C5 119.68(19) . . . . ? C8 Cr C6 C5 -102.08(18) . . . . ? C7 Cr C6 C5 -130.9(2) . . . . ? C9 Cr C6 C5 -65.18(17) . . . . ? C4 Cr C6 C5 -28.18(16) . . . . ? C5 C6 C7 C8 2.3(4) . . . . ? Cr C6 C7 C8 -53.9(2) . . . . ? C5 C6 C7 Cr 56.2(2) . . . . ? C3 Cr C7 C8 91.1(5) . . . . ? C2 Cr C7 C8 -63.53(19) . . . . ? C1 Cr C7 C8 -154.67(18) . . . . ? C6 Cr C7 C8 132.4(2) . . . . ? C9 Cr C7 C8 28.97(15) . . . . ? C5 Cr C7 C8 102.46(18) . . . . ? C4 Cr C7 C8 65.90(16) . . . . ? C3 Cr C7 C6 -41.3(5) . . . . ? C2 Cr C7 C6 164.10(17) . . . . ? C1 Cr C7 C6 72.96(18) . . . . ? C8 Cr C7 C6 -132.4(2) . . . . ? C9 Cr C7 C6 -103.40(17) . . . . ? C5 Cr C7 C6 -29.91(15) . . . . ? C4 Cr C7 C6 -66.47(15) . . . . ? C6 C7 C8 C9 -0.8(4) . . . . ? Cr C7 C8 C9 -54.6(2) . . . . ? C6 C7 C8 Cr 53.8(2) . . . . ? C3 Cr C8 C7 -157.6(2) . . . . ? C2 Cr C8 C7 119.24(19) . . . . ? C1 Cr C8 C7 34.5(2) . . . . ? C6 Cr C8 C7 -28.82(16) . . . . ? C9 Cr C8 C7 -132.9(2) . . . . ? C5 Cr C8 C7 -65.87(17) . . . . ? C4 Cr C8 C7 -103.18(18) . . . . ? C3 Cr C8 C9 -24.8(3) . . . . ? C2 Cr C8 C9 -107.91(17) . . . . ? C1 Cr C8 C9 167.32(16) . . . . ? C6 Cr C8 C9 104.03(16) . . . . ? C7 Cr C8 C9 132.9(2) . . . . ? C5 Cr C8 C9 66.98(15) . . . . ? C4 Cr C8 C9 29.67(14) . . . . ? C7 C8 C9 C4 -0.2(4) . . . . ? Cr C8 C9 C4 -54.97(19) . . . . ? C7 C8 C9 C11 -179.9(2) . . . . ? Cr C8 C9 C11 125.2(2) . . . . ? C7 C8 C9 Cr 54.8(2) . . . . ? C5 C4 C9 C8 -0.5(3) . . . . ? C10 C4 C9 C8 -177.7(2) . . . . ? Cr C4 C9 C8 54.49(19) . . . . ? C5 C4 C9 C11 179.3(2) . . . . ? C10 C4 C9 C11 2.1(3) . . . . ? Cr C4 C9 C11 -125.7(2) . . . . ? C5 C4 C9 Cr -55.0(2) . . . . ? C10 C4 C9 Cr 127.8(2) . . . . ? C3 Cr C9 C8 164.26(16) . . . . ? C2 Cr C9 C8 73.20(18) . . . . ? C1 Cr C9 C8 -43.7(5) . . . . ? C6 Cr C9 C8 -64.55(16) . . . . ? C7 Cr C9 C8 -28.34(16) . . . . ? C5 Cr C9 C8 -101.14(17) . . . . ? C4 Cr C9 C8 -131.1(2) . . . . ? C3 Cr C9 C4 -64.60(16) . . . . ? C2 Cr C9 C4 -155.66(15) . . . . ? C1 Cr C9 C4 87.5(5) . . . . ? C8 Cr C9 C4 131.1(2) . . . . ? C6 Cr C9 C4 66.60(15) . . . . ? C7 Cr C9 C4 102.81(16) . . . . ? C5 Cr C9 C4 30.00(14) . . . . ? C3 Cr C9 C11 50.1(2) . . . . ? C2 Cr C9 C11 -40.9(2) . . . . ? C1 Cr C9 C11 -157.8(4) . . . . ? C8 Cr C9 C11 -114.1(3) . . . . ? C6 Cr C9 C11 -178.7(2) . . . . ? C7 Cr C9 C11 -142.5(2) . . . . ? C5 Cr C9 C11 144.7(2) . . . . ? C4 Cr C9 C11 114.7(3) . . . . ? C5 C4 C10 O6 -103.1(3) . . . . ? C9 C4 C10 O6 74.1(3) . . . . ? Cr C4 C10 O6 165.12(17) . . . . ? C5 C4 C10 C14 16.5(4) . . . . ? C9 C4 C10 C14 -166.3(3) . . . . ? Cr C4 C10 C14 -75.3(3) . . . . ? C12 O4 C11 O5 69.6(3) . . . . ? C12 O4 C11 C9 -167.0(3) . . . . ? C13 O5 C11 O4 56.9(3) . . . . ? C13 O5 C11 C9 -64.9(3) . . . . ? C8 C9 C11 O4 -16.0(3) . . . . ? C4 C9 C11 O4 164.2(2) . . . . ? Cr C9 C11 O4 73.4(3) . . . . ? C8 C9 C11 O5 107.7(2) . . . . ? C4 C9 C11 O5 -72.1(3) . . . . ? Cr C9 C11 O5 -162.86(15) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.91 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.365 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.055 data_3a_b _database_code_CSD 203337 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Arene chromium complex' _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 Cr O6 ' _chemical_formula_sum 'C14 H16 Cr O6' _chemical_formula_weight 332.27 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' Cr Cr 0.3209 0.6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.6389(13) _cell_length_b 8.9939(11) _cell_length_c 13.7401(14) _cell_angle_alpha 90.0 _cell_angle_beta 113.594(7) _cell_angle_gamma 90.0 _cell_volume 1544.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4 _cell_measurement_theta_max 18 _exptl_crystal_description rectangular _exptl_crystal_colour 'Pale yellow' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.763 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q-scan _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% <4% _diffrn_reflns_number 2710 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 24.90 _reflns_number_total 2710 _reflns_number_gt 2369 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD-4 Software' _computing_data_reduction 'NRCVAX (PC Version) Gabe, E. J. et al., 1989)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, L and Pritzkow, H, 1994)' _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^)+(0.0546P)^2^+0.3172P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2710 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0861 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cr Cr 0.48716(2) 1.14721(3) 0.19291(2) 0.03186(13) Uani 1 1 d . . . O1 O 0.32046(17) 1.2554(2) -0.01303(14) 0.0759(6) Uani 1 1 d . . . O2 O 0.41309(17) 1.36970(19) 0.31166(17) 0.0699(5) Uani 1 1 d . . . O3 O 0.63019(19) 1.3888(2) 0.1754(2) 0.0927(7) Uani 1 1 d . . . O4 O 0.28677(12) 0.89810(18) -0.01198(11) 0.0489(4) Uani 1 1 d . . . O5 O 0.28735(13) 0.71988(16) 0.11140(13) 0.0511(4) Uani 1 1 d . . . O6 O 0.38716(15) 1.0435(2) 0.40821(14) 0.0552(5) Uani 1 1 d . . . C1 C 0.38421(19) 1.2130(2) 0.06592(17) 0.0460(5) Uani 1 1 d . . . C2 C 0.44016(17) 1.2824(2) 0.26571(17) 0.0447(5) Uani 1 1 d . . . C3 C 0.5758(2) 1.2950(3) 0.1816(2) 0.0540(6) Uani 1 1 d . . . C4 C 0.44397(14) 0.9553(2) 0.27277(14) 0.0337(4) Uani 1 1 d . . . C5 C 0.54993(16) 1.0018(2) 0.33541(16) 0.0394(4) Uani 1 1 d . . . C6 C 0.62759(16) 1.0122(3) 0.29294(17) 0.0438(5) Uani 1 1 d . . . C7 C 0.60034(16) 0.9732(2) 0.18570(17) 0.0407(5) Uani 1 1 d . . . C8 C 0.49625(15) 0.9283(2) 0.12203(15) 0.0349(4) Uani 1 1 d . . . C9 C 0.41609(14) 0.92069(19) 0.16449(14) 0.0316(4) Uani 1 1 d . . . C10 C 0.36654(17) 0.9363(3) 0.32675(16) 0.0434(5) Uani 1 1 d . . . C11 C 0.30408(17) 0.8716(2) 0.09379(16) 0.0375(4) Uani 1 1 d . . . C12 C 0.1766(3) 0.8891(6) -0.0829(3) 0.0823(11) Uani 1 1 d . . . C13 C 0.3561(3) 0.6180(3) 0.0897(3) 0.0741(9) Uani 1 1 d . . . C14 C 0.3823(3) 0.7829(3) 0.3780(3) 0.0642(7) Uani 1 1 d . . . H5 H 0.5633(17) 1.030(2) 0.4015(18) 0.044(6) Uiso 1 1 d . . . H6 H 0.6952(19) 1.040(2) 0.3347(18) 0.045(6) Uiso 1 1 d . . . H7 H 0.6475(18) 0.981(3) 0.1626(18) 0.046(6) Uiso 1 1 d . . . H8 H 0.4773(15) 0.901(2) 0.0512(17) 0.030(5) Uiso 1 1 d . . . H10 H 0.291(2) 0.944(3) 0.2755(19) 0.052(6) Uiso 1 1 d . . . H11 H 0.2521(17) 0.920(2) 0.1070(16) 0.035(5) Uiso 1 1 d . . . H12A H 0.141(3) 0.962(5) -0.068(3) 0.106(16) Uiso 1 1 d . . . H12B H 0.154(3) 0.800(5) -0.077(3) 0.104(13) Uiso 1 1 d . . . H12C H 0.167(3) 0.913(5) -0.153(4) 0.123(14) Uiso 1 1 d . . . H13A H 0.365(3) 0.634(3) 0.021(3) 0.089(11) Uiso 1 1 d . . . H13B H 0.432(3) 0.626(4) 0.139(3) 0.089(11) Uiso 1 1 d . . . H13C H 0.334(3) 0.529(4) 0.094(3) 0.099(11) Uiso 1 1 d . . . H14A H 0.453(2) 0.778(3) 0.436(2) 0.069(8) Uiso 1 1 d . . . H14B H 0.363(2) 0.707(4) 0.326(2) 0.071(9) Uiso 1 1 d . . . H14C H 0.337(3) 0.771(3) 0.409(3) 0.081(9) Uiso 1 1 d . . . H6O H 0.353(2) 1.096(3) 0.387(2) 0.048(9) Uiso 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 Cr 0.03204(19) 0.03159(19) 0.03337(19) -0.00203(12) 0.01456(14) -0.00313(12) O1 0.0939(14) 0.0589(11) 0.0498(10) 0.0086(8) 0.0024(10) 0.0218(10) O2 0.0857(13) 0.0537(10) 0.0836(13) -0.0158(9) 0.0478(11) 0.0100(9) O3 0.0974(16) 0.0772(13) 0.1261(19) -0.0163(13) 0.0684(15) -0.0468(13) O4 0.0479(8) 0.0559(9) 0.0367(7) 0.0015(6) 0.0105(6) -0.0166(7) O5 0.0630(9) 0.0349(8) 0.0638(10) -0.0024(7) 0.0343(8) -0.0164(7) O6 0.0589(11) 0.0717(12) 0.0425(9) 0.0048(8) 0.0280(8) 0.0256(10) C1 0.0569(13) 0.0333(10) 0.0455(12) -0.0020(9) 0.0180(11) 0.0019(10) C2 0.0469(12) 0.0400(11) 0.0485(12) -0.0014(10) 0.0205(10) -0.0013(9) C3 0.0571(14) 0.0501(13) 0.0636(14) -0.0070(11) 0.0335(12) -0.0135(11) C4 0.0361(10) 0.0337(10) 0.0358(10) 0.0071(8) 0.0189(8) 0.0076(8) C5 0.0406(10) 0.0474(11) 0.0304(10) 0.0030(9) 0.0143(8) 0.0073(9) C6 0.0294(10) 0.0549(13) 0.0437(11) 0.0017(10) 0.0110(9) 0.0051(9) C7 0.0368(10) 0.0474(12) 0.0455(11) 0.0021(9) 0.0245(9) 0.0038(9) C8 0.0419(10) 0.0323(9) 0.0366(10) -0.0010(8) 0.0222(8) 0.0002(8) C9 0.0382(10) 0.0246(8) 0.0358(9) 0.0018(7) 0.0189(8) 0.0007(7) C10 0.0403(11) 0.0581(13) 0.0381(10) 0.0051(10) 0.0226(9) 0.0048(10) C11 0.0415(11) 0.0327(10) 0.0419(11) -0.0009(8) 0.0205(9) -0.0069(8) C12 0.0625(19) 0.104(3) 0.0562(18) 0.0082(18) -0.0012(15) -0.030(2) C13 0.098(3) 0.0340(13) 0.101(2) -0.0046(14) 0.051(2) -0.0061(14) C14 0.085(2) 0.0626(17) 0.0666(18) 0.0112(14) 0.0526(17) -0.0032(15) _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 Cr C2 1.845(2) . ? Cr C1 1.845(2) . ? Cr C3 1.845(2) . ? Cr C6 2.219(2) . ? Cr C8 2.2216(19) . ? Cr C5 2.222(2) . ? Cr C9 2.2225(18) . ? Cr C7 2.228(2) . ? Cr C4 2.2467(18) . ? O1 C1 1.150(3) . ? O2 C2 1.157(3) . ? O3 C3 1.149(3) . ? O4 C11 1.396(2) . ? O4 C12 1.429(3) . ? O5 C11 1.420(2) . ? O5 C13 1.426(4) . ? O6 C10 1.418(3) . ? O6 H6O 0.65(3) . ? C4 C9 1.415(3) . ? C4 C5 1.417(3) . ? C4 C10 1.524(2) . ? C5 C6 1.402(3) . ? C5 H5 0.89(2) . ? C6 C7 1.412(3) . ? C6 H6 0.90(2) . ? C7 C8 1.396(3) . ? C7 H7 0.83(2) . ? C8 C9 1.432(2) . ? C8 H8 0.93(2) . ? C9 C11 1.511(3) . ? C10 C14 1.524(4) . ? C10 H10 0.99(2) . ? C11 H11 0.91(2) . ? C12 H12A 0.89(4) . ? C12 H12B 0.88(4) . ? C12 H12C 0.94(4) . ? C13 H13A 1.01(4) . ? C13 H13B 0.98(4) . ? C13 H13C 0.87(4) . ? C14 H14A 0.98(3) . ? C14 H14B 0.95(3) . ? C14 H14C 0.88(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 Cr C1 90.20(9) . . ? C2 Cr C3 87.29(10) . . ? C1 Cr C3 88.03(11) . . ? C2 Cr C6 115.21(9) . . ? C1 Cr C6 154.49(9) . . ? C3 Cr C6 90.81(10) . . ? C2 Cr C8 156.09(8) . . ? C1 Cr C8 91.39(8) . . ? C3 Cr C8 116.60(9) . . ? C6 Cr C8 66.48(8) . . ? C2 Cr C5 90.30(9) . . ? C1 Cr C5 154.30(9) . . ? C3 Cr C5 117.66(10) . . ? C6 Cr C5 36.81(7) . . ? C8 Cr C5 78.18(8) . . ? C2 Cr C9 118.53(8) . . ? C1 Cr C9 90.82(8) . . ? C3 Cr C9 154.16(9) . . ? C6 Cr C9 79.33(8) . . ? C8 Cr C9 37.60(6) . . ? C5 Cr C9 66.56(7) . . ? C2 Cr C7 152.17(9) . . ? C1 Cr C7 117.49(9) . . ? C3 Cr C7 90.75(10) . . ? C6 Cr C7 37.03(8) . . ? C8 Cr C7 36.57(8) . . ? C5 Cr C7 66.18(7) . . ? C9 Cr C7 67.01(7) . . ? C2 Cr C4 91.47(8) . . ? C1 Cr C4 117.32(9) . . ? C3 Cr C4 154.63(10) . . ? C6 Cr C4 66.87(7) . . ? C8 Cr C4 66.73(7) . . ? C5 Cr C4 36.98(8) . . ? C9 Cr C4 36.91(7) . . ? C7 Cr C4 78.68(7) . . ? C11 O4 C12 113.2(2) . . ? C11 O5 C13 114.71(19) . . ? C10 O6 H6O 105(3) . . ? O1 C1 Cr 179.3(2) . . ? O2 C2 Cr 178.1(2) . . ? O3 C3 Cr 178.7(2) . . ? C9 C4 C5 118.88(16) . . ? C9 C4 C10 122.70(17) . . ? C5 C4 C10 118.33(17) . . ? C9 C4 Cr 70.62(10) . . ? C5 C4 Cr 70.55(11) . . ? C10 C4 Cr 133.81(13) . . ? C6 C5 C4 121.57(18) . . ? C6 C5 Cr 71.49(12) . . ? C4 C5 Cr 72.47(11) . . ? C6 C5 H5 121.8(14) . . ? C4 C5 H5 116.5(14) . . ? Cr C5 H5 125.7(14) . . ? C5 C6 C7 119.37(19) . . ? C5 C6 Cr 71.70(11) . . ? C7 C6 Cr 71.83(12) . . ? C5 C6 H6 120.2(14) . . ? C7 C6 H6 120.4(14) . . ? Cr C6 H6 130.5(14) . . ? C8 C7 C6 120.18(18) . . ? C8 C7 Cr 71.46(11) . . ? C6 C7 Cr 71.14(12) . . ? C8 C7 H7 122.5(16) . . ? C6 C7 H7 117.3(16) . . ? Cr C7 H7 127.9(17) . . ? C7 C8 C9 120.61(18) . . ? C7 C8 Cr 71.96(12) . . ? C9 C8 Cr 71.24(10) . . ? C7 C8 H8 121.1(12) . . ? C9 C8 H8 118.3(12) . . ? Cr C8 H8 130.3(12) . . ? C4 C9 C8 119.34(17) . . ? C4 C9 C11 121.14(16) . . ? C8 C9 C11 119.49(16) . . ? C4 C9 Cr 72.47(10) . . ? C8 C9 Cr 71.17(10) . . ? C11 C9 Cr 129.66(13) . . ? O6 C10 C4 110.53(18) . . ? O6 C10 C14 107.7(2) . . ? C4 C10 C14 109.26(18) . . ? O6 C10 H10 109.5(14) . . ? C4 C10 H10 111.6(14) . . ? C14 C10 H10 108.1(14) . . ? O4 C11 O5 111.69(16) . . ? O4 C11 C9 108.99(15) . . ? O5 C11 C9 111.17(17) . . ? O4 C11 H11 107.7(13) . . ? O5 C11 H11 103.7(13) . . ? C9 C11 H11 113.4(13) . . ? O4 C12 H12A 109(3) . . ? O4 C12 H12B 107(3) . . ? H12A C12 H12B 115(4) . . ? O4 C12 H12C 112(3) . . ? H12A C12 H12C 102(3) . . ? H12B C12 H12C 113(3) . . ? O5 C13 H13A 115.7(19) . . ? O5 C13 H13B 114(2) . . ? H13A C13 H13B 99(3) . . ? O5 C13 H13C 107(2) . . ? H13A C13 H13C 112(3) . . ? H13B C13 H13C 109(3) . . ? C10 C14 H14A 109.0(17) . . ? C10 C14 H14B 110.8(18) . . ? H14A C14 H14B 118(3) . . ? C10 C14 H14C 110(2) . . ? H14A C14 H14C 105(3) . . ? H14B C14 H14C 104(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 Cr C1 O1 59(18) . . . . ? C3 Cr C1 O1 -28(18) . . . . ? C6 Cr C1 O1 -116(18) . . . . ? C8 Cr C1 O1 -144(18) . . . . ? C5 Cr C1 O1 151(18) . . . . ? C9 Cr C1 O1 178(100) . . . . ? C7 Cr C1 O1 -118(18) . . . . ? C4 Cr C1 O1 151(18) . . . . ? C1 Cr C2 O2 -102(6) . . . . ? C3 Cr C2 O2 -14(6) . . . . ? C6 Cr C2 O2 76(6) . . . . ? C8 Cr C2 O2 164(6) . . . . ? C5 Cr C2 O2 104(6) . . . . ? C9 Cr C2 O2 167(6) . . . . ? C7 Cr C2 O2 73(6) . . . . ? C4 Cr C2 O2 141(6) . . . . ? C2 Cr C3 O3 -5(13) . . . . ? C1 Cr C3 O3 86(13) . . . . ? C6 Cr C3 O3 -120(13) . . . . ? C8 Cr C3 O3 176(100) . . . . ? C5 Cr C3 O3 -94(13) . . . . ? C9 Cr C3 O3 173(100) . . . . ? C7 Cr C3 O3 -157(13) . . . . ? C4 Cr C3 O3 -92(13) . . . . ? C2 Cr C4 C9 139.60(12) . . . . ? C1 Cr C4 C9 48.62(13) . . . . ? C3 Cr C4 C9 -133.6(2) . . . . ? C6 Cr C4 C9 -103.51(12) . . . . ? C8 Cr C4 C9 -30.29(10) . . . . ? C5 Cr C4 C9 -131.86(16) . . . . ? C7 Cr C4 C9 -66.63(11) . . . . ? C2 Cr C4 C5 -88.55(13) . . . . ? C1 Cr C4 C5 -179.52(12) . . . . ? C3 Cr C4 C5 -1.8(2) . . . . ? C6 Cr C4 C5 28.35(12) . . . . ? C8 Cr C4 C5 101.57(12) . . . . ? C9 Cr C4 C5 131.86(16) . . . . ? C7 Cr C4 C5 65.23(12) . . . . ? C2 Cr C4 C10 22.5(2) . . . . ? C1 Cr C4 C10 -68.5(2) . . . . ? C3 Cr C4 C10 109.2(3) . . . . ? C6 Cr C4 C10 139.4(2) . . . . ? C8 Cr C4 C10 -147.4(2) . . . . ? C5 Cr C4 C10 111.0(2) . . . . ? C9 Cr C4 C10 -117.1(2) . . . . ? C7 Cr C4 C10 176.2(2) . . . . ? C9 C4 C5 C6 -0.8(3) . . . . ? C10 C4 C5 C6 175.72(19) . . . . ? Cr C4 C5 C6 -54.21(18) . . . . ? C9 C4 C5 Cr 53.36(15) . . . . ? C10 C4 C5 Cr -130.07(17) . . . . ? C2 Cr C5 C6 -134.74(14) . . . . ? C1 Cr C5 C6 134.2(2) . . . . ? C3 Cr C5 C6 -47.64(16) . . . . ? C8 Cr C5 C6 66.37(13) . . . . ? C9 Cr C5 C6 104.04(14) . . . . ? C7 Cr C5 C6 29.93(13) . . . . ? C4 Cr C5 C6 133.22(18) . . . . ? C2 Cr C5 C4 92.04(12) . . . . ? C1 Cr C5 C4 1.0(2) . . . . ? C3 Cr C5 C4 179.14(12) . . . . ? C6 Cr C5 C4 -133.22(18) . . . . ? C8 Cr C5 C4 -66.85(11) . . . . ? C9 Cr C5 C4 -29.18(11) . . . . ? C7 Cr C5 C4 -103.28(13) . . . . ? C4 C5 C6 C7 -1.1(3) . . . . ? Cr C5 C6 C7 -55.74(18) . . . . ? C4 C5 C6 Cr 54.65(18) . . . . ? C2 Cr C6 C5 51.73(16) . . . . ? C1 Cr C6 C5 -133.8(2) . . . . ? C3 Cr C6 C5 139.12(14) . . . . ? C8 Cr C6 C5 -102.05(14) . . . . ? C9 Cr C6 C5 -64.92(13) . . . . ? C7 Cr C6 C5 -130.7(2) . . . . ? C4 Cr C6 C5 -28.47(12) . . . . ? C2 Cr C6 C7 -177.56(13) . . . . ? C1 Cr C6 C7 -3.1(3) . . . . ? C3 Cr C6 C7 -90.17(14) . . . . ? C8 Cr C6 C7 28.66(12) . . . . ? C5 Cr C6 C7 130.7(2) . . . . ? C9 Cr C6 C7 65.79(13) . . . . ? C4 Cr C6 C7 102.24(14) . . . . ? C5 C6 C7 C8 1.6(3) . . . . ? Cr C6 C7 C8 -54.04(18) . . . . ? C5 C6 C7 Cr 55.67(18) . . . . ? C2 Cr C7 C8 137.16(18) . . . . ? C1 Cr C7 C8 -49.05(15) . . . . ? C3 Cr C7 C8 -137.22(13) . . . . ? C6 Cr C7 C8 132.43(18) . . . . ? C5 Cr C7 C8 102.67(13) . . . . ? C9 Cr C7 C8 29.23(11) . . . . ? C4 Cr C7 C8 66.01(12) . . . . ? C2 Cr C7 C6 4.7(2) . . . . ? C1 Cr C7 C6 178.52(13) . . . . ? C3 Cr C7 C6 90.35(15) . . . . ? C8 Cr C7 C6 -132.43(18) . . . . ? C5 Cr C7 C6 -29.77(13) . . . . ? C9 Cr C7 C6 -103.21(14) . . . . ? C4 Cr C7 C6 -66.42(13) . . . . ? C6 C7 C8 C9 -0.3(3) . . . . ? Cr C7 C8 C9 -54.15(16) . . . . ? C6 C7 C8 Cr 53.89(18) . . . . ? C2 Cr C8 C7 -128.5(2) . . . . ? C1 Cr C8 C7 137.92(13) . . . . ? C3 Cr C8 C7 49.43(15) . . . . ? C6 Cr C8 C7 -28.99(12) . . . . ? C5 Cr C8 C7 -65.77(12) . . . . ? C9 Cr C8 C7 -132.54(17) . . . . ? C4 Cr C8 C7 -102.78(13) . . . . ? C2 Cr C8 C9 4.1(3) . . . . ? C1 Cr C8 C9 -89.53(12) . . . . ? C3 Cr C8 C9 -178.03(13) . . . . ? C6 Cr C8 C9 103.55(12) . . . . ? C5 Cr C8 C9 66.78(11) . . . . ? C7 Cr C8 C9 132.54(17) . . . . ? C4 Cr C8 C9 29.76(10) . . . . ? C5 C4 C9 C8 2.2(3) . . . . ? C10 C4 C9 C8 -174.21(17) . . . . ? Cr C4 C9 C8 55.53(15) . . . . ? C5 C4 C9 C11 -179.57(17) . . . . ? C10 C4 C9 C11 4.0(3) . . . . ? Cr C4 C9 C11 -126.24(17) . . . . ? C5 C4 C9 Cr -53.33(16) . . . . ? C10 C4 C9 Cr 130.26(18) . . . . ? C7 C8 C9 C4 -1.7(3) . . . . ? Cr C8 C9 C4 -56.17(15) . . . . ? C7 C8 C9 C11 -179.94(18) . . . . ? Cr C8 C9 C11 125.58(16) . . . . ? C7 C8 C9 Cr 54.48(17) . . . . ? C2 Cr C9 C4 -47.52(13) . . . . ? C1 Cr C9 C4 -138.19(12) . . . . ? C3 Cr C9 C4 134.6(2) . . . . ? C6 Cr C9 C4 65.49(11) . . . . ? C8 Cr C9 C4 130.59(16) . . . . ? C5 Cr C9 C4 29.23(11) . . . . ? C7 Cr C9 C4 102.11(12) . . . . ? C2 Cr C9 C8 -178.11(12) . . . . ? C1 Cr C9 C8 91.22(13) . . . . ? C3 Cr C9 C8 4.1(3) . . . . ? C6 Cr C9 C8 -65.10(11) . . . . ? C5 Cr C9 C8 -101.37(12) . . . . ? C7 Cr C9 C8 -28.48(11) . . . . ? C4 Cr C9 C8 -130.59(16) . . . . ? C2 Cr C9 C11 68.76(19) . . . . ? C1 Cr C9 C11 -21.91(18) . . . . ? C3 Cr C9 C11 -109.1(3) . . . . ? C6 Cr C9 C11 -178.23(18) . . . . ? C8 Cr C9 C11 -113.1(2) . . . . ? C5 Cr C9 C11 145.50(18) . . . . ? C7 Cr C9 C11 -141.61(18) . . . . ? C4 Cr C9 C11 116.3(2) . . . . ? C9 C4 C10 O6 -148.94(18) . . . . ? C5 C4 C10 O6 34.6(2) . . . . ? Cr C4 C10 O6 -55.0(2) . . . . ? C9 C4 C10 C14 92.7(2) . . . . ? C5 C4 C10 C14 -83.7(3) . . . . ? Cr C4 C10 C14 -173.30(19) . . . . ? C12 O4 C11 O5 70.8(3) . . . . ? C12 O4 C11 C9 -166.0(3) . . . . ? C13 O5 C11 O4 60.9(3) . . . . ? C13 O5 C11 C9 -61.1(3) . . . . ? C4 C9 C11 O4 158.08(17) . . . . ? C8 C9 C11 O4 -23.7(2) . . . . ? Cr C9 C11 O4 65.6(2) . . . . ? C4 C9 C11 O5 -78.4(2) . . . . ? C8 C9 C11 O5 99.8(2) . . . . ? Cr C9 C11 O5 -170.90(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.90 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.210 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.055 ##END