# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_sri14_m _database_code_depnum_ccdc_archive 'CCDC 749765' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; trans-2-(4-(4-chlorophenyl) cyclohexyl)-3-hydroxynaphthalene-1,4-dione ; _chemical_name_common Atovaquone _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 Cl O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C22 H19 Cl O3' _chemical_formula_iupac ? _chemical_formula_weight 366.82 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 12.548(2) _cell_length_b 5.2674(9) _cell_length_c 27.842(5) _cell_angle_alpha 90 _cell_angle_beta 92.573(3) _cell_angle_gamma 90 _cell_volume 1838.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 340 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.89 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.226 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9393 _exptl_absorpt_correction_T_max 0.9955 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 16438 _diffrn_reflns_av_R_equivalents 0.0947 _diffrn_reflns_av_sigmaI/netI 0.0783 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3204 # number of observed reflections (> n sig(I)) _reflns_number_gt 1567 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0499P)^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 3204 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1781 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.1427 _refine_ls_wR_factor_gt 0.1182 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.254 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.037 #=============================================================================== # 9. 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.42559(10) 0.2917(3) 0.11869(4) 0.1044(5) Uani 1 1 d . . . C4 C 0.7017(3) 0.3126(7) 0.22872(13) 0.0513(9) Uani 1 1 d . . . O3 O 0.9308(2) 0.8025(5) 0.43547(10) 0.0682(8) Uani 1 1 d . . . C15 C 1.1848(3) 0.2962(7) 0.42276(13) 0.0545(10) Uani 1 1 d . . . O1 O 1.0936(2) 0.1370(5) 0.35443(10) 0.0790(9) Uani 1 1 d . . . C13 C 1.0059(3) 0.4771(7) 0.39105(13) 0.0502(10) Uani 1 1 d . . . O2 O 1.0938(2) 0.7978(5) 0.49890(9) 0.0786(9) Uani 1 1 d . . . C22 C 1.0098(3) 0.6373(7) 0.42889(12) 0.0507(10) Uani 1 1 d . . . C21 C 1.0986(3) 0.6468(7) 0.46590(14) 0.0575(10) Uani 1 1 d . . . C20 C 1.1879(3) 0.4688(7) 0.46104(14) 0.0570(10) Uani 1 1 d . . . C3 C 0.6938(4) 0.1343(8) 0.19268(17) 0.0700(13) Uani 1 1 d . . . C10 C 0.9142(3) 0.4811(7) 0.35413(13) 0.0550(11) Uani 1 1 d . . . C7 C 0.7923(3) 0.3144(7) 0.26567(14) 0.0554(10) Uani 1 1 d . . . C5 C 0.6199(4) 0.4888(9) 0.22933(17) 0.0694(13) Uani 1 1 d . . . C1 C 0.5317(3) 0.3024(9) 0.16120(14) 0.0637(11) Uani 1 1 d . . . C11 C 0.9492(4) 0.5511(9) 0.30392(15) 0.0570(12) Uani 1 1 d . . . C8 C 0.7563(4) 0.2523(9) 0.31629(15) 0.0629(12) Uani 1 1 d . . . C17 C 1.3527(5) 0.1328(11) 0.4510(2) 0.0939(17) Uani 1 1 d . . . C2 C 0.6099(4) 0.1268(9) 0.15904(17) 0.0760(13) Uani 1 1 d . . . C14 C 1.0935(3) 0.2927(7) 0.38691(13) 0.0550(10) Uani 1 1 d . . . C12 C 0.8549(4) 0.5596(8) 0.26773(16) 0.0596(12) Uani 1 1 d . . . C16 C 1.2683(4) 0.1297(9) 0.41800(18) 0.0740(13) Uani 1 1 d . . . C6 C 0.5358(4) 0.4853(9) 0.19572(18) 0.0727(13) Uani 1 1 d . . . C19 C 1.2730(4) 0.4706(10) 0.49415(17) 0.0823(14) Uani 1 1 d . . . C9 C 0.8481(4) 0.2399(9) 0.35285(17) 0.0671(12) Uani 1 1 d . . . C18 C 1.3555(5) 0.3009(13) 0.4889(2) 0.1013(19) Uani 1 1 d . . . H8A H 0.702(3) 0.377(6) 0.3247(12) 0.068(12) Uiso 1 1 d . . . H7A H 0.846(2) 0.174(6) 0.2570(10) 0.054(10) Uiso 1 1 d . . . H9E H 0.823(2) 0.228(5) 0.3853(12) 0.050(10) Uiso 1 1 d . . . H11E H 0.983(3) 0.710(7) 0.3056(12) 0.071(12) Uiso 1 1 d . . . H10A H 0.863(3) 0.609(6) 0.3650(12) 0.068(12) Uiso 1 1 d . . . H12A H 0.802(3) 0.689(7) 0.2763(14) 0.093(15) Uiso 1 1 d . . . H9A H 0.902(3) 0.097(7) 0.3438(12) 0.077(13) Uiso 1 1 d . . . H5 H 0.624(3) 0.611(7) 0.2534(13) 0.073(13) Uiso 1 1 d . . . H3 H 0.747(3) 0.024(6) 0.1905(12) 0.062(13) Uiso 1 1 d . . . H3O H 0.949(4) 0.898(9) 0.4610(17) 0.13(2) Uiso 1 1 d . . . H8E H 0.720(3) 0.098(6) 0.3138(11) 0.064(12) Uiso 1 1 d . . . H18 H 1.414(3) 0.309(7) 0.5087(14) 0.088(16) Uiso 1 1 d . . . H17 H 1.412(3) 0.007(8) 0.4470(14) 0.104(15) Uiso 1 1 d . . . H19 H 1.279(3) 0.609(6) 0.5195(13) 0.067(12) Uiso 1 1 d . . . H6 H 0.481(3) 0.609(7) 0.1958(12) 0.072(13) Uiso 1 1 d . . . H16 H 1.258(3) 0.006(8) 0.3889(16) 0.121(18) Uiso 1 1 d . . . H11A H 0.995(3) 0.431(7) 0.2930(13) 0.073(14) Uiso 1 1 d . . . H12E H 0.876(2) 0.607(6) 0.2371(12) 0.050(10) Uiso 1 1 d . . . H2 H 0.606(3) -0.010(8) 0.1333(15) 0.107(15) 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 Cl1 0.0813(9) 0.1525(13) 0.0785(8) -0.0063(8) -0.0064(7) -0.0175(8) C4 0.051(3) 0.047(2) 0.057(2) 0.003(2) 0.007(2) 0.002(2) O3 0.086(2) 0.0654(18) 0.0529(17) -0.0126(15) 0.0031(15) 0.0273(17) C15 0.067(3) 0.046(2) 0.052(2) 0.009(2) 0.019(2) 0.007(2) O1 0.089(2) 0.0696(19) 0.079(2) -0.0268(16) 0.0117(17) 0.0132(16) C13 0.063(3) 0.045(2) 0.045(2) 0.0014(18) 0.021(2) -0.001(2) O2 0.105(2) 0.078(2) 0.0524(17) -0.0201(15) -0.0006(16) 0.0207(17) C22 0.065(3) 0.047(2) 0.042(2) 0.0083(19) 0.015(2) 0.009(2) C21 0.076(3) 0.053(3) 0.044(2) 0.008(2) 0.014(2) 0.002(2) C20 0.062(3) 0.064(3) 0.045(2) 0.018(2) 0.006(2) 0.010(2) C3 0.083(4) 0.056(3) 0.072(3) -0.003(2) 0.015(3) 0.013(3) C10 0.064(3) 0.052(3) 0.050(3) -0.007(2) 0.008(2) 0.000(2) C7 0.060(3) 0.043(2) 0.064(3) -0.003(2) 0.013(2) -0.003(2) C5 0.064(3) 0.066(3) 0.078(3) -0.016(3) -0.001(3) 0.004(3) C1 0.060(3) 0.071(3) 0.061(3) 0.000(2) 0.012(2) -0.003(3) C11 0.074(3) 0.044(3) 0.054(3) -0.003(2) 0.016(3) -0.008(3) C8 0.060(3) 0.057(3) 0.072(3) 0.011(2) 0.010(3) -0.003(3) C17 0.095(4) 0.103(4) 0.085(4) 0.016(3) 0.026(4) 0.046(4) C2 0.095(4) 0.072(3) 0.061(3) -0.015(3) 0.003(3) -0.001(3) C14 0.068(3) 0.048(2) 0.051(2) -0.005(2) 0.021(2) -0.003(2) C12 0.076(3) 0.059(3) 0.044(3) 0.003(2) 0.007(3) -0.009(3) C16 0.073(3) 0.077(3) 0.073(3) 0.016(3) 0.012(3) 0.022(3) C6 0.058(3) 0.069(3) 0.092(4) -0.004(3) 0.005(3) 0.012(3) C19 0.088(4) 0.095(4) 0.064(3) 0.002(3) 0.006(3) 0.020(3) C9 0.076(3) 0.067(3) 0.059(3) 0.015(2) 0.015(3) -0.003(3) C18 0.081(4) 0.142(6) 0.079(4) 0.021(4) -0.010(4) 0.023(4) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 Cl1 C1 1.742(4) . ? C4 C3 1.375(5) . ? C4 C5 1.384(5) . ? C4 C7 1.499(5) . ? O3 C22 1.338(4) . ? O3 H3O 0.89(5) . ? C15 C16 1.377(5) . ? C15 C20 1.400(5) . ? C15 C14 1.486(5) . ? O1 C14 1.221(4) . ? C13 C22 1.349(4) . ? C13 C14 1.475(5) . ? C13 C10 1.508(5) . ? O2 C21 1.219(4) . ? C22 C21 1.484(5) . ? C21 C20 1.472(5) . ? C20 C19 1.378(6) . ? C3 C2 1.378(6) . ? C3 H3 0.89(3) . ? C10 C9 1.517(5) . ? C10 C11 1.529(5) . ? C10 H10A 0.99(3) . ? C7 C12 1.511(5) . ? C7 C8 1.535(5) . ? C7 H7A 1.04(3) . ? C5 C6 1.379(6) . ? C5 H5 0.93(3) . ? C1 C2 1.352(6) . ? C1 C6 1.360(5) . ? C11 C12 1.520(5) . ? C11 H11E 0.94(4) . ? C11 H11A 0.92(4) . ? C8 C9 1.504(5) . ? C8 H8A 0.98(3) . ? C8 H8E 0.93(3) . ? C17 C16 1.370(6) . ? C17 C18 1.377(7) . ? C17 H17 1.00(4) . ? C2 H2 1.02(4) . ? C12 H12A 0.98(4) . ? C12 H12E 0.94(3) . ? C16 H16 1.04(4) . ? C6 H6 0.95(3) . ? C19 C18 1.381(7) . ? C19 H19 1.02(3) . ? C9 H9E 0.97(3) . ? C9 H9A 1.05(4) . ? C18 H18 0.89(4) . ? 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 C4 C5 116.0(4) . . ? C3 C4 C7 122.2(4) . . ? C5 C4 C7 121.8(4) . . ? C22 O3 H3O 109(3) . . ? C16 C15 C20 119.4(4) . . ? C16 C15 C14 119.6(4) . . ? C20 C15 C14 120.9(4) . . ? C22 C13 C14 118.2(4) . . ? C22 C13 C10 121.6(4) . . ? C14 C13 C10 120.3(3) . . ? O3 C22 C13 120.9(4) . . ? O3 C22 C21 114.9(3) . . ? C13 C22 C21 124.3(4) . . ? O2 C21 C20 123.2(4) . . ? O2 C21 C22 119.0(4) . . ? C20 C21 C22 117.8(4) . . ? C19 C20 C15 120.5(4) . . ? C19 C20 C21 120.3(4) . . ? C15 C20 C21 119.2(4) . . ? C4 C3 C2 122.9(5) . . ? C4 C3 H3 118(2) . . ? C2 C3 H3 119(2) . . ? C13 C10 C9 113.8(3) . . ? C13 C10 C11 112.7(3) . . ? C9 C10 C11 111.1(3) . . ? C13 C10 H10A 106.6(19) . . ? C9 C10 H10A 102.6(19) . . ? C11 C10 H10A 109.4(19) . . ? C4 C7 C12 114.1(3) . . ? C4 C7 C8 112.5(3) . . ? C12 C7 C8 108.8(3) . . ? C4 C7 H7A 108.4(16) . . ? C12 C7 H7A 106.2(17) . . ? C8 C7 H7A 106.4(17) . . ? C6 C5 C4 121.9(5) . . ? C6 C5 H5 121(2) . . ? C4 C5 H5 117(2) . . ? C2 C1 C6 120.8(4) . . ? C2 C1 Cl1 118.8(4) . . ? C6 C1 Cl1 120.4(4) . . ? C12 C11 C10 111.5(4) . . ? C12 C11 H11E 110(2) . . ? C10 C11 H11E 109(2) . . ? C12 C11 H11A 106(2) . . ? C10 C11 H11A 110(2) . . ? H11E C11 H11A 110(3) . . ? C9 C8 C7 112.5(4) . . ? C9 C8 H8A 113(2) . . ? C7 C8 H8A 108(2) . . ? C9 C8 H8E 111(2) . . ? C7 C8 H8E 106(2) . . ? H8A C8 H8E 105(3) . . ? C16 C17 C18 120.9(5) . . ? C16 C17 H17 118(2) . . ? C18 C17 H17 121(2) . . ? C1 C2 C3 119.0(5) . . ? C1 C2 H2 120(2) . . ? C3 C2 H2 121(2) . . ? O1 C14 C13 121.8(4) . . ? O1 C14 C15 118.6(4) . . ? C13 C14 C15 119.6(3) . . ? C7 C12 C11 112.8(4) . . ? C7 C12 H12A 104(2) . . ? C11 C12 H12A 112(2) . . ? C7 C12 H12E 111.1(19) . . ? C11 C12 H12E 111.5(19) . . ? H12A C12 H12E 105(3) . . ? C17 C16 C15 119.7(5) . . ? C17 C16 H16 126(2) . . ? C15 C16 H16 114(2) . . ? C1 C6 C5 119.5(5) . . ? C1 C6 H6 119(2) . . ? C5 C6 H6 122(2) . . ? C20 C19 C18 119.1(5) . . ? C20 C19 H19 120(2) . . ? C18 C19 H19 120(2) . . ? C8 C9 C10 112.4(4) . . ? C8 C9 H9E 111.4(18) . . ? C10 C9 H9E 103.2(18) . . ? C8 C9 H9A 110.4(19) . . ? C10 C9 H9A 104.7(19) . . ? H9E C9 H9A 114(3) . . ? C17 C18 C19 120.2(5) . . ? C17 C18 H18 120(3) . . ? C19 C18 H18 120(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 C14 C13 C22 O3 -177.6(3) . . . . ? C10 C13 C22 O3 1.4(5) . . . . ? C14 C13 C22 C21 2.3(5) . . . . ? C10 C13 C22 C21 -178.7(3) . . . . ? O3 C22 C21 O2 0.4(5) . . . . ? C13 C22 C21 O2 -179.5(3) . . . . ? O3 C22 C21 C20 179.6(3) . . . . ? C13 C22 C21 C20 -0.3(5) . . . . ? C16 C15 C20 C19 -0.9(5) . . . . ? C14 C15 C20 C19 179.9(4) . . . . ? C16 C15 C20 C21 179.9(3) . . . . ? C14 C15 C20 C21 0.7(5) . . . . ? O2 C21 C20 C19 -1.4(6) . . . . ? C22 C21 C20 C19 179.5(4) . . . . ? O2 C21 C20 C15 177.9(3) . . . . ? C22 C21 C20 C15 -1.3(5) . . . . ? C5 C4 C3 C2 -0.4(6) . . . . ? C7 C4 C3 C2 178.6(4) . . . . ? C22 C13 C10 C9 -115.2(4) . . . . ? C14 C13 C10 C9 63.8(5) . . . . ? C22 C13 C10 C11 117.2(4) . . . . ? C14 C13 C10 C11 -63.8(5) . . . . ? C3 C4 C7 C12 122.4(4) . . . . ? C5 C4 C7 C12 -58.6(5) . . . . ? C3 C4 C7 C8 -113.0(4) . . . . ? C5 C4 C7 C8 66.0(5) . . . . ? C3 C4 C5 C6 -0.1(6) . . . . ? C7 C4 C5 C6 -179.2(4) . . . . ? C13 C10 C11 C12 -178.7(4) . . . . ? C9 C10 C11 C12 52.3(5) . . . . ? C4 C7 C8 C9 176.8(4) . . . . ? C12 C7 C8 C9 -55.8(5) . . . . ? C6 C1 C2 C3 0.5(6) . . . . ? Cl1 C1 C2 C3 -179.8(3) . . . . ? C4 C3 C2 C1 0.2(7) . . . . ? C22 C13 C14 O1 177.8(3) . . . . ? C10 C13 C14 O1 -1.2(5) . . . . ? C22 C13 C14 C15 -2.8(5) . . . . ? C10 C13 C14 C15 178.2(3) . . . . ? C16 C15 C14 O1 1.6(5) . . . . ? C20 C15 C14 O1 -179.2(3) . . . . ? C16 C15 C14 C13 -177.8(3) . . . . ? C20 C15 C14 C13 1.3(5) . . . . ? C4 C7 C12 C11 -177.4(4) . . . . ? C8 C7 C12 C11 56.1(5) . . . . ? C10 C11 C12 C7 -55.7(5) . . . . ? C18 C17 C16 C15 -0.2(7) . . . . ? C20 C15 C16 C17 0.7(6) . . . . ? C14 C15 C16 C17 179.9(4) . . . . ? C2 C1 C6 C5 -1.0(6) . . . . ? Cl1 C1 C6 C5 179.3(3) . . . . ? C4 C5 C6 C1 0.8(6) . . . . ? C15 C20 C19 C18 0.5(6) . . . . ? C21 C20 C19 C18 179.7(4) . . . . ? C7 C8 C9 C10 55.3(6) . . . . ? C13 C10 C9 C8 179.0(4) . . . . ? C11 C10 C9 C8 -52.6(5) . . . . ? C16 C17 C18 C19 -0.2(8) . . . . ? C20 C19 C18 C17 0.1(8) . . . . ? data_sri4_m1 _database_code_depnum_ccdc_archive 'CCDC 749766' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; trans-2-(4-(4-chlorophenyl) cyclohexyl)-3-hydroxynaphthalene-1,4-dione ; _chemical_name_common Atovaquone _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 Cl O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C22 H19 Cl O3' _chemical_formula_iupac ? _chemical_formula_weight 366.82 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 5.9369(7) _cell_length_b 18.358(2) _cell_length_c 16.6699(18) _cell_angle_alpha 90 _cell_angle_beta 97.334(2) _cell_angle_gamma 90 _cell_volume 1801.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 340 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.231 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9863 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 18409 _diffrn_reflns_av_R_equivalents 0.0777 _diffrn_reflns_av_sigmaI/netI 0.0652 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3514 # number of observed reflections (> n sig(I)) _reflns_number_gt 1864 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0339P)^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 3514 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1274 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.165 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.035 #=============================================================================== # 9. 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.66596(14) 0.09957(5) 0.26428(5) 0.0949(3) Uani 1 1 d . . . O3 O 0.0079(3) 0.03743(10) 0.87621(11) 0.0601(5) Uani 1 1 d . . . O2 O 0.2448(3) 0.04058(10) 1.02325(10) 0.0635(5) Uani 1 1 d . . . O1 O 0.5544(3) 0.19112(11) 0.78747(11) 0.0755(6) Uani 1 1 d . . . C15 C 0.6057(4) 0.15983(13) 0.92538(15) 0.0445(6) Uani 1 1 d . . . C13 C 0.2637(4) 0.11790(13) 0.82747(14) 0.0437(6) Uani 1 1 d . . . C10 C 0.1221(4) 0.11813(14) 0.74488(14) 0.0456(7) Uani 1 1 d . . . C4 C -0.1752(4) 0.12960(12) 0.49294(15) 0.0436(6) Uani 1 1 d . . . C7 C -0.0081(4) 0.13709(14) 0.56897(15) 0.0473(7) Uani 1 1 d . . . C5 C -0.3870(4) 0.09833(14) 0.49414(17) 0.0520(7) Uani 1 1 d . . . C3 C -0.1218(5) 0.15273(14) 0.41836(16) 0.0515(7) Uani 1 1 d . . . C20 C 0.5280(4) 0.12111(12) 0.98796(15) 0.0440(6) Uani 1 1 d . . . C9 C 0.2224(5) 0.06939(18) 0.68465(17) 0.0565(8) Uani 1 1 d . . . C21 C 0.3195(4) 0.07739(13) 0.97137(15) 0.0466(6) Uani 1 1 d . . . C12 C -0.0953(5) 0.18738(16) 0.63134(17) 0.0515(7) Uani 1 1 d . . . C14 C 0.4779(4) 0.15805(14) 0.84187(15) 0.0480(7) Uani 1 1 d . . . C6 C -0.5386(5) 0.08937(15) 0.42467(17) 0.0525(7) Uani 1 1 d . . . C22 C 0.1987(4) 0.07843(13) 0.88818(15) 0.0445(6) Uani 1 1 d . . . C1 C -0.4773(5) 0.11238(14) 0.35247(15) 0.0534(7) Uani 1 1 d . . . C16 C 0.8039(5) 0.20034(15) 0.9398(2) 0.0590(8) Uani 1 1 d . . . C8 C 0.0589(6) 0.06355(16) 0.60664(18) 0.0557(8) Uani 1 1 d . . . C2 C -0.2719(5) 0.14419(16) 0.34876(18) 0.0593(8) Uani 1 1 d . . . C19 C 0.6489(5) 0.12306(17) 1.06559(18) 0.0629(8) Uani 1 1 d . . . C11 C 0.0677(5) 0.19289(15) 0.70936(17) 0.0542(8) Uani 1 1 d . . . C18 C 0.8435(5) 0.16393(18) 1.0791(2) 0.0721(10) Uani 1 1 d . . . C17 C 0.9201(6) 0.20236(18) 1.0171(2) 0.0722(9) Uani 1 1 d . . . H12E H -0.127(3) 0.2370(12) 0.6086(13) 0.053(7) Uiso 1 1 d . . . H12A H -0.244(4) 0.1672(11) 0.6455(12) 0.052(7) Uiso 1 1 d . . . H7A H 0.129(4) 0.1607(12) 0.5518(13) 0.062(8) Uiso 1 1 d . . . H11A H 0.207(4) 0.2157(13) 0.6961(14) 0.065(9) Uiso 1 1 d . . . H8A H -0.079(4) 0.0392(14) 0.6185(14) 0.077(10) Uiso 1 1 d . . . H18 H 0.928(4) 0.1658(13) 1.1298(15) 0.067(8) Uiso 1 1 d . . . H5 H -0.424(3) 0.0816(11) 0.5428(12) 0.040(7) Uiso 1 1 d . . . H10A H -0.026(4) 0.1003(12) 0.7545(13) 0.063(8) Uiso 1 1 d . . . H16 H 0.852(4) 0.2252(13) 0.8918(14) 0.065(9) Uiso 1 1 d . . . H2 H -0.221(4) 0.1591(13) 0.3016(15) 0.063(8) Uiso 1 1 d . . . H19 H 0.588(4) 0.0938(12) 1.1053(14) 0.060(9) Uiso 1 1 d . . . H3 H 0.025(4) 0.1769(13) 0.4158(14) 0.070(8) Uiso 1 1 d . . . H6 H -0.675(4) 0.0664(13) 0.4270(15) 0.076(9) Uiso 1 1 d . . . H9A H 0.374(4) 0.0922(13) 0.6743(15) 0.082(10) Uiso 1 1 d . . . H17 H 1.065(5) 0.2305(15) 1.0255(16) 0.098(11) Uiso 1 1 d . . . H8E H 0.124(4) 0.0327(13) 0.5673(14) 0.066(8) Uiso 1 1 d . . . H11E H -0.003(4) 0.2255(14) 0.7462(15) 0.077(9) Uiso 1 1 d . . . H9E H 0.242(4) 0.0217(15) 0.7095(15) 0.083(10) Uiso 1 1 d . . . H3O H -0.013(5) 0.0194(14) 0.9264(16) 0.089(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 Cl1 0.0832(6) 0.1297(8) 0.0624(5) -0.0071(5) -0.0270(4) 0.0077(5) O3 0.0617(13) 0.0644(13) 0.0521(12) 0.0102(10) -0.0002(10) -0.0178(10) O2 0.0700(13) 0.0697(13) 0.0510(11) 0.0166(10) 0.0084(10) -0.0035(11) O1 0.0566(12) 0.1043(16) 0.0643(13) 0.0213(12) 0.0032(10) -0.0232(11) C15 0.0403(15) 0.0404(15) 0.0519(17) -0.0060(13) 0.0030(13) 0.0074(12) C13 0.0434(15) 0.0448(16) 0.0421(15) -0.0008(12) 0.0028(12) 0.0000(12) C10 0.0429(16) 0.0539(18) 0.0392(15) 0.0044(13) 0.0017(12) -0.0054(14) C4 0.0403(15) 0.0419(15) 0.0466(16) -0.0009(12) -0.0018(12) 0.0023(12) C7 0.0438(15) 0.0523(17) 0.0442(16) 0.0022(14) -0.0003(13) -0.0067(14) C5 0.0530(18) 0.0591(18) 0.0436(17) 0.0036(15) 0.0053(14) -0.0016(14) C3 0.0476(17) 0.0517(17) 0.0543(19) 0.0096(14) 0.0023(14) -0.0030(14) C20 0.0459(15) 0.0386(15) 0.0455(16) -0.0062(12) -0.0024(12) 0.0087(12) C9 0.062(2) 0.0499(19) 0.0534(19) -0.0035(15) -0.0074(16) 0.0113(16) C21 0.0538(17) 0.0417(16) 0.0443(16) 0.0030(12) 0.0060(13) 0.0110(13) C12 0.0553(19) 0.0420(18) 0.0540(18) -0.0017(14) -0.0052(15) 0.0035(15) C14 0.0405(15) 0.0527(17) 0.0499(17) 0.0055(13) 0.0031(13) -0.0006(13) C6 0.0450(17) 0.0558(18) 0.0553(19) -0.0045(15) 0.0009(14) -0.0040(14) C22 0.0450(16) 0.0422(16) 0.0452(16) -0.0006(12) 0.0015(12) -0.0020(13) C1 0.0562(18) 0.0549(18) 0.0455(17) -0.0004(14) -0.0072(14) 0.0094(15) C16 0.0461(18) 0.0559(19) 0.071(2) -0.0028(17) -0.0068(16) 0.0018(15) C8 0.066(2) 0.052(2) 0.0455(18) -0.0081(15) -0.0055(15) 0.0089(17) C2 0.062(2) 0.066(2) 0.0500(19) 0.0155(16) 0.0084(16) 0.0034(16) C19 0.065(2) 0.064(2) 0.057(2) -0.0076(17) -0.0027(17) 0.0098(17) C11 0.062(2) 0.0454(19) 0.0513(19) -0.0049(15) -0.0083(16) 0.0069(16) C18 0.061(2) 0.076(2) 0.071(2) -0.022(2) -0.0239(19) 0.0104(18) C17 0.052(2) 0.068(2) 0.092(3) -0.012(2) -0.008(2) 0.0000(18) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 Cl1 C1 1.747(2) . ? O3 C22 1.353(3) . ? O3 H3O 0.92(3) . ? O2 C21 1.224(3) . ? O1 C14 1.226(3) . ? C15 C16 1.387(3) . ? C15 C20 1.389(3) . ? C15 C14 1.498(3) . ? C13 C22 1.341(3) . ? C13 C14 1.463(3) . ? C13 C10 1.519(3) . ? C10 C11 1.513(3) . ? C10 C9 1.522(3) . ? C10 H10A 0.97(2) . ? C4 C5 1.384(3) . ? C4 C3 1.388(3) . ? C4 C7 1.513(3) . ? C7 C8 1.520(3) . ? C7 C12 1.529(3) . ? C7 H7A 1.00(2) . ? C5 C6 1.383(3) . ? C5 H5 0.920(19) . ? C3 C2 1.379(4) . ? C3 H3 0.98(2) . ? C20 C19 1.398(3) . ? C20 C21 1.471(3) . ? C9 C8 1.524(4) . ? C9 H9A 1.03(3) . ? C9 H9E 0.97(3) . ? C21 C22 1.478(3) . ? C12 C11 1.522(3) . ? C12 H12E 1.00(2) . ? C12 H12A 1.01(2) . ? C6 C1 1.368(3) . ? C6 H6 0.92(2) . ? C1 C2 1.361(4) . ? C16 C17 1.382(4) . ? C16 H16 0.99(2) . ? C8 H8A 0.97(2) . ? C8 H8E 0.98(2) . ? C2 H2 0.92(2) . ? C19 C18 1.372(4) . ? C19 H19 0.96(2) . ? C11 H11A 0.98(2) . ? C11 H11E 0.99(2) . ? C18 C17 1.376(4) . ? C18 H18 0.93(2) . ? C17 H17 1.00(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 C22 O3 H3O 105.8(18) . . ? C16 C15 C20 120.0(2) . . ? C16 C15 C14 119.4(3) . . ? C20 C15 C14 120.6(2) . . ? C22 C13 C14 118.5(2) . . ? C22 C13 C10 120.4(2) . . ? C14 C13 C10 121.1(2) . . ? C11 C10 C13 115.0(2) . . ? C11 C10 C9 110.9(2) . . ? C13 C10 C9 112.2(2) . . ? C11 C10 H10A 102.6(13) . . ? C13 C10 H10A 104.9(13) . . ? C9 C10 H10A 110.4(14) . . ? C5 C4 C3 116.9(2) . . ? C5 C4 C7 121.7(2) . . ? C3 C4 C7 121.5(2) . . ? C4 C7 C8 112.0(2) . . ? C4 C7 C12 112.4(2) . . ? C8 C7 C12 110.4(2) . . ? C4 C7 H7A 105.7(13) . . ? C8 C7 H7A 109.0(13) . . ? C12 C7 H7A 107.0(13) . . ? C6 C5 C4 122.2(3) . . ? C6 C5 H5 119.6(13) . . ? C4 C5 H5 118.1(13) . . ? C2 C3 C4 121.4(3) . . ? C2 C3 H3 119.7(14) . . ? C4 C3 H3 118.8(14) . . ? C15 C20 C19 120.1(3) . . ? C15 C20 C21 119.4(2) . . ? C19 C20 C21 120.6(3) . . ? C10 C9 C8 110.1(2) . . ? C10 C9 H9A 107.1(14) . . ? C8 C9 H9A 111.2(14) . . ? C10 C9 H9E 106.5(15) . . ? C8 C9 H9E 109.3(16) . . ? H9A C9 H9E 112(2) . . ? O2 C21 C20 122.7(2) . . ? O2 C21 C22 119.6(2) . . ? C20 C21 C22 117.7(2) . . ? C11 C12 C7 112.8(2) . . ? C11 C12 H12E 109.4(13) . . ? C7 C12 H12E 110.9(13) . . ? C11 C12 H12A 107.7(12) . . ? C7 C12 H12A 108.6(12) . . ? H12E C12 H12A 107.3(18) . . ? O1 C14 C13 121.6(2) . . ? O1 C14 C15 119.0(2) . . ? C13 C14 C15 119.3(2) . . ? C1 C6 C5 118.8(3) . . ? C1 C6 H6 120.9(16) . . ? C5 C6 H6 120.2(16) . . ? C13 C22 O3 120.4(2) . . ? C13 C22 C21 124.3(2) . . ? O3 C22 C21 115.3(2) . . ? C2 C1 C6 120.9(3) . . ? C2 C1 Cl1 120.1(2) . . ? C6 C1 Cl1 119.0(2) . . ? C17 C16 C15 119.2(3) . . ? C17 C16 H16 125.3(14) . . ? C15 C16 H16 115.5(14) . . ? C7 C8 C9 113.2(2) . . ? C7 C8 H8A 108.0(15) . . ? C9 C8 H8A 108.6(15) . . ? C7 C8 H8E 109.9(14) . . ? C9 C8 H8E 110.5(14) . . ? H8A C8 H8E 106(2) . . ? C1 C2 C3 119.8(3) . . ? C1 C2 H2 124.1(15) . . ? C3 C2 H2 116.1(15) . . ? C18 C19 C20 119.3(3) . . ? C18 C19 H19 125.2(15) . . ? C20 C19 H19 115.5(15) . . ? C10 C11 C12 110.8(2) . . ? C10 C11 H11A 109.4(14) . . ? C12 C11 H11A 107.5(14) . . ? C10 C11 H11E 113.2(14) . . ? C12 C11 H11E 107.3(14) . . ? H11A C11 H11E 109(2) . . ? C19 C18 C17 120.6(3) . . ? C19 C18 H18 121.1(16) . . ? C17 C18 H18 118.3(16) . . ? C18 C17 C16 120.9(3) . . ? C18 C17 H17 121.5(17) . . ? C16 C17 H17 117.6(17) . . ? 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 C22 C13 C10 C11 130.1(3) . . . . ? C14 C13 C10 C11 -52.4(3) . . . . ? C22 C13 C10 C9 -101.8(3) . . . . ? C14 C13 C10 C9 75.7(3) . . . . ? C5 C4 C7 C8 61.2(3) . . . . ? C3 C4 C7 C8 -117.8(3) . . . . ? C5 C4 C7 C12 -63.8(3) . . . . ? C3 C4 C7 C12 117.2(3) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C7 C4 C5 C6 -178.2(2) . . . . ? C5 C4 C3 C2 -0.7(4) . . . . ? C7 C4 C3 C2 178.3(2) . . . . ? C16 C15 C20 C19 0.2(3) . . . . ? C14 C15 C20 C19 179.9(2) . . . . ? C16 C15 C20 C21 -179.0(2) . . . . ? C14 C15 C20 C21 0.7(3) . . . . ? C11 C10 C9 C8 -57.3(3) . . . . ? C13 C10 C9 C8 172.5(2) . . . . ? C15 C20 C21 O2 178.1(2) . . . . ? C19 C20 C21 O2 -1.0(4) . . . . ? C15 C20 C21 C22 -1.5(3) . . . . ? C19 C20 C21 C22 179.3(2) . . . . ? C4 C7 C12 C11 177.7(2) . . . . ? C8 C7 C12 C11 51.9(3) . . . . ? C22 C13 C14 O1 175.0(2) . . . . ? C10 C13 C14 O1 -2.5(4) . . . . ? C22 C13 C14 C15 -5.9(3) . . . . ? C10 C13 C14 C15 176.6(2) . . . . ? C16 C15 C14 O1 1.8(4) . . . . ? C20 C15 C14 O1 -177.9(2) . . . . ? C16 C15 C14 C13 -177.3(2) . . . . ? C20 C15 C14 C13 3.0(3) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C14 C13 C22 O3 -176.5(2) . . . . ? C10 C13 C22 O3 1.1(4) . . . . ? C14 C13 C22 C21 5.3(4) . . . . ? C10 C13 C22 C21 -177.1(2) . . . . ? O2 C21 C22 C13 178.7(2) . . . . ? C20 C21 C22 C13 -1.6(3) . . . . ? O2 C21 C22 O3 0.4(3) . . . . ? C20 C21 C22 O3 -179.91(19) . . . . ? C5 C6 C1 C2 -0.6(4) . . . . ? C5 C6 C1 Cl1 178.8(2) . . . . ? C20 C15 C16 C17 -0.9(4) . . . . ? C14 C15 C16 C17 179.4(2) . . . . ? C4 C7 C8 C9 -178.5(3) . . . . ? C12 C7 C8 C9 -52.3(4) . . . . ? C10 C9 C8 C7 55.5(4) . . . . ? C6 C1 C2 C3 0.8(4) . . . . ? Cl1 C1 C2 C3 -178.6(2) . . . . ? C4 C3 C2 C1 -0.1(4) . . . . ? C15 C20 C19 C18 0.5(4) . . . . ? C21 C20 C19 C18 179.6(2) . . . . ? C13 C10 C11 C12 -173.8(2) . . . . ? C9 C10 C11 C12 57.4(3) . . . . ? C7 C12 C11 C10 -55.1(4) . . . . ? C20 C19 C18 C17 -0.4(4) . . . . ? C19 C18 C17 C16 -0.4(5) . . . . ? C15 C16 C17 C18 1.0(4) . . . . ? data_sri12 _database_code_depnum_ccdc_archive 'CCDC 749767' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; cis -2-(4-(4-chlorophenyl)cyclohexyl)-3-hydroxynaphthalene-1,4-dione ; _chemical_name_common cis-Atovaquone _chemical_melting_point ? _chemical_formula_moiety 'C22 H19 Cl O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C22 H19 Cl O3' _chemical_formula_iupac ? _chemical_formula_weight 366.82 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 13.2516(10) _cell_length_b 10.9285(9) _cell_length_c 12.6302(10) _cell_angle_alpha 90 _cell_angle_beta 95.450(1) _cell_angle_gamma 90 _cell_volume 1820.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 420 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.89 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.229 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9519 _exptl_absorpt_correction_T_max 0.9902 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 18281 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3572 # number of observed reflections (> n sig(I)) _reflns_number_gt 2805 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0526P)^2^+0.3804P] 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 3572 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.160 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.032 #=============================================================================== # 9. 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.07535(4) 0.10512(6) 0.70502(6) 0.1004(2) Uani 1 1 d . . . C15 C -0.32630(10) -0.63658(14) 0.32144(12) 0.0472(4) Uani 1 1 d . . . C21 C -0.16104(10) -0.58008(14) 0.41579(12) 0.0481(4) Uani 1 1 d . . . O3 O -0.14340(9) -0.38822(12) 0.50625(11) 0.0678(4) Uani 1 1 d . . . C20 C -0.22345(10) -0.66357(13) 0.34567(12) 0.0459(3) Uani 1 1 d . . . C10 C -0.35262(11) -0.31692(15) 0.45900(13) 0.0516(4) Uani 1 1 d . . . C4 C -0.24029(12) -0.02895(14) 0.59402(12) 0.0509(4) Uani 1 1 d . . . C19 C -0.18153(13) -0.76638(15) 0.30312(14) 0.0577(4) Uani 1 1 d . . . C3 C -0.17948(13) -0.09068(15) 0.67193(13) 0.0537(4) Uani 1 1 d . . . C14 C -0.37126(10) -0.52393(14) 0.36344(12) 0.0495(4) Uani 1 1 d . . . C13 C -0.30622(10) -0.43565(14) 0.42671(12) 0.0467(3) Uani 1 1 d . . . C22 C -0.20720(10) -0.46462(14) 0.44976(12) 0.0492(4) Uani 1 1 d . . . C16 C -0.38533(13) -0.71515(16) 0.25539(14) 0.0595(4) Uani 1 1 d . . . C2 C -0.08220(13) -0.05162(16) 0.70521(15) 0.0593(4) Uani 1 1 d . . . C17 C -0.34321(15) -0.81714(17) 0.21344(17) 0.0691(5) Uani 1 1 d . . . C1 C -0.04479(13) 0.05139(16) 0.66035(15) 0.0634(5) Uani 1 1 d . . . C8 C -0.35890(15) -0.08780(17) 0.43396(14) 0.0616(4) Uani 1 1 d . . . C7 C -0.34814(12) -0.06593(16) 0.55464(14) 0.0572(4) Uani 1 1 d . . . C9 C -0.30762(14) -0.20626(16) 0.40633(14) 0.0548(4) Uani 1 1 d . . . C18 C -0.24158(15) -0.84251(18) 0.23642(16) 0.0679(5) Uani 1 1 d . . . C12 C -0.39090(14) -0.17627(18) 0.60962(16) 0.0629(5) Uani 1 1 d . . . C6 C -0.10262(17) 0.11498(18) 0.58334(17) 0.0748(5) Uani 1 1 d . . . C11 C -0.34655(14) -0.29919(17) 0.57991(14) 0.0573(4) Uani 1 1 d . . . C5 C -0.19904(16) 0.07501(17) 0.55138(16) 0.0685(5) Uani 1 1 d . . . O2 O -0.07234(8) -0.60128(11) 0.44636(10) 0.0646(3) Uani 1 1 d . . . O1 O -0.46143(8) -0.50425(12) 0.34306(12) 0.0781(4) Uani 1 1 d . . . H10A H -0.4228(12) -0.3221(14) 0.4321(12) 0.050(4) Uiso 1 1 d . . . H3O H -0.0876(17) -0.4175(19) 0.5097(17) 0.084(7) Uiso 1 1 d . . . H2 H -0.0395(14) -0.0951(17) 0.7592(15) 0.073(5) Uiso 1 1 d . . . H16 H -0.4535(14) -0.6965(16) 0.2408(14) 0.062(5) Uiso 1 1 d . . . H3 H -0.2042(12) -0.1629(16) 0.7046(13) 0.056(4) Uiso 1 1 d . . . H9E H -0.3124(13) -0.2184(16) 0.3331(16) 0.065(5) Uiso 1 1 d . . . H19 H -0.1121(14) -0.7824(16) 0.3200(13) 0.066(5) Uiso 1 1 d . . . H7E H -0.3901(12) 0.0035(16) 0.5725(13) 0.057(4) Uiso 1 1 d . . . H8E H -0.3308(14) -0.0170(18) 0.3960(15) 0.071(5) Uiso 1 1 d . . . H11E H -0.3838(13) -0.3665(17) 0.6109(14) 0.065(5) Uiso 1 1 d . . . H12E H -0.4612(16) -0.1788(18) 0.5893(15) 0.073(6) Uiso 1 1 d . . . H17 H -0.3844(14) -0.8694(18) 0.1669(15) 0.071(5) Uiso 1 1 d . . . H18 H -0.2151(15) -0.914(2) 0.2072(16) 0.081(6) Uiso 1 1 d . . . H5 H -0.2404(14) 0.1221(18) 0.4979(16) 0.077(6) Uiso 1 1 d . . . H6 H -0.0743(17) 0.189(2) 0.5529(18) 0.102(7) Uiso 1 1 d . . . H9A H -0.2353(13) -0.2010(14) 0.4279(12) 0.051(4) Uiso 1 1 d . . . H11A H -0.2752(13) -0.3085(14) 0.6093(12) 0.049(4) Uiso 1 1 d . . . H12A H -0.3855(13) -0.1644(16) 0.6888(15) 0.062(5) Uiso 1 1 d . . . H8A H -0.4299(15) -0.0903(16) 0.4091(14) 0.070(5) 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 Cl1 0.0697(4) 0.0842(4) 0.1453(6) -0.0060(4) 0.0003(3) -0.0177(3) C15 0.0400(7) 0.0461(8) 0.0538(8) 0.0107(7) -0.0041(6) -0.0083(6) C21 0.0355(7) 0.0524(9) 0.0548(9) 0.0073(7) -0.0045(6) -0.0008(6) O3 0.0378(6) 0.0701(8) 0.0913(9) -0.0239(7) -0.0163(6) 0.0033(6) C20 0.0402(7) 0.0436(8) 0.0524(8) 0.0095(6) -0.0030(6) -0.0045(6) C10 0.0343(7) 0.0585(9) 0.0607(10) -0.0020(7) -0.0020(6) 0.0018(6) C4 0.0594(9) 0.0475(8) 0.0464(8) -0.0036(7) 0.0087(7) 0.0086(7) C19 0.0501(9) 0.0517(9) 0.0699(11) 0.0038(8) -0.0012(8) 0.0004(7) C3 0.0584(10) 0.0486(9) 0.0547(9) 0.0027(7) 0.0088(7) 0.0035(7) C14 0.0332(7) 0.0517(9) 0.0618(10) 0.0105(7) -0.0054(6) -0.0044(6) C13 0.0359(7) 0.0513(8) 0.0519(8) 0.0038(7) -0.0014(6) -0.0008(6) C22 0.0364(7) 0.0542(9) 0.0548(9) -0.0021(7) -0.0067(6) -0.0031(6) C16 0.0452(9) 0.0566(10) 0.0737(11) 0.0066(8) -0.0096(8) -0.0134(8) C2 0.0585(10) 0.0538(10) 0.0650(11) -0.0022(8) 0.0019(8) 0.0076(8) C17 0.0688(12) 0.0551(11) 0.0802(13) -0.0036(9) -0.0099(9) -0.0186(9) C1 0.0621(10) 0.0539(10) 0.0754(12) -0.0095(9) 0.0120(9) -0.0024(8) C8 0.0629(11) 0.0601(11) 0.0591(10) 0.0036(8) -0.0083(8) 0.0105(9) C7 0.0539(9) 0.0571(10) 0.0607(10) -0.0026(8) 0.0059(7) 0.0155(8) C9 0.0594(10) 0.0603(10) 0.0442(9) 0.0003(8) 0.0017(7) 0.0051(8) C18 0.0719(12) 0.0510(10) 0.0797(13) -0.0055(9) 0.0008(9) -0.0044(9) C12 0.0492(10) 0.0789(13) 0.0625(11) -0.0044(9) 0.0151(8) 0.0042(9) C6 0.0900(14) 0.0565(11) 0.0783(13) 0.0068(10) 0.0095(11) -0.0140(10) C11 0.0522(10) 0.0609(10) 0.0602(10) 0.0050(8) 0.0129(8) -0.0040(8) C5 0.0854(13) 0.0545(10) 0.0639(11) 0.0097(9) -0.0014(9) 0.0004(9) O2 0.0366(6) 0.0641(7) 0.0889(9) -0.0047(6) -0.0165(5) 0.0055(5) O1 0.0336(6) 0.0708(8) 0.1251(11) -0.0081(7) -0.0168(6) 0.0006(5) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 Cl1 C1 1.7399(19) . ? C15 C16 1.386(2) . ? C15 C20 1.3996(19) . ? C15 C14 1.487(2) . ? C21 O2 1.2240(16) . ? C21 C20 1.470(2) . ? C21 C22 1.483(2) . ? O3 C22 1.3440(18) . ? O3 H3O 0.80(2) . ? C20 C19 1.384(2) . ? C10 C13 1.508(2) . ? C10 C9 1.528(2) . ? C10 C11 1.534(2) . ? C10 H10A 0.962(16) . ? C4 C3 1.386(2) . ? C4 C5 1.391(2) . ? C4 C7 1.523(2) . ? C19 C18 1.381(2) . ? C19 H19 0.941(18) . ? C3 C2 1.385(2) . ? C3 H3 0.962(18) . ? C14 O1 1.2174(17) . ? C14 C13 1.477(2) . ? C13 C22 1.3544(19) . ? C16 C17 1.375(3) . ? C16 H16 0.927(17) . ? C2 C1 1.374(3) . ? C2 H2 0.969(19) . ? C17 C18 1.379(3) . ? C17 H17 0.95(2) . ? C1 C6 1.369(3) . ? C8 C9 1.518(2) . ? C8 C7 1.536(2) . ? C8 H8E 1.000(19) . ? C8 H8A 0.96(2) . ? C7 C12 1.527(3) . ? C7 H7E 0.980(17) . ? C9 H9E 0.931(19) . ? C9 H9A 0.973(16) . ? C18 H18 0.95(2) . ? C12 C11 1.527(3) . ? C12 H12E 0.94(2) . ? C12 H12A 1.005(18) . ? C6 C5 1.374(3) . ? C6 H6 0.98(2) . ? C11 H11E 0.987(19) . ? C11 H11A 0.988(16) . ? C5 H5 0.98(2) . ? 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 C16 C15 C20 118.90(15) . . ? C16 C15 C14 120.34(14) . . ? C20 C15 C14 120.75(13) . . ? O2 C21 C20 122.74(14) . . ? O2 C21 C22 118.67(13) . . ? C20 C21 C22 118.58(12) . . ? C22 O3 H3O 108.1(15) . . ? C19 C20 C15 120.30(14) . . ? C19 C20 C21 120.93(13) . . ? C15 C20 C21 118.77(14) . . ? C13 C10 C9 112.15(13) . . ? C13 C10 C11 113.18(13) . . ? C9 C10 C11 110.34(14) . . ? C13 C10 H10A 105.0(9) . . ? C9 C10 H10A 107.3(9) . . ? C11 C10 H10A 108.5(9) . . ? C3 C4 C5 116.67(16) . . ? C3 C4 C7 124.54(15) . . ? C5 C4 C7 118.78(15) . . ? C18 C19 C20 119.77(16) . . ? C18 C19 H19 121.4(11) . . ? C20 C19 H19 118.9(11) . . ? C2 C3 C4 121.80(16) . . ? C2 C3 H3 117.9(10) . . ? C4 C3 H3 120.3(10) . . ? O1 C14 C13 120.63(15) . . ? O1 C14 C15 119.29(14) . . ? C13 C14 C15 120.05(12) . . ? C22 C13 C14 117.85(14) . . ? C22 C13 C10 123.67(13) . . ? C14 C13 C10 118.45(12) . . ? O3 C22 C13 121.11(15) . . ? O3 C22 C21 115.22(12) . . ? C13 C22 C21 123.67(13) . . ? C17 C16 C15 120.50(16) . . ? C17 C16 H16 121.7(11) . . ? C15 C16 H16 117.8(11) . . ? C1 C2 C3 119.30(17) . . ? C1 C2 H2 118.9(11) . . ? C3 C2 H2 121.8(11) . . ? C16 C17 C18 120.40(17) . . ? C16 C17 H17 119.6(11) . . ? C18 C17 H17 120.0(11) . . ? C6 C1 C2 120.62(18) . . ? C6 C1 Cl1 119.49(15) . . ? C2 C1 Cl1 119.85(15) . . ? C9 C8 C7 111.06(14) . . ? C9 C8 H8E 110.7(11) . . ? C7 C8 H8E 110.6(11) . . ? C9 C8 H8A 110.2(11) . . ? C7 C8 H8A 108.9(11) . . ? H8E C8 H8A 105.2(15) . . ? C4 C7 C12 116.00(14) . . ? C4 C7 C8 111.18(14) . . ? C12 C7 C8 108.96(15) . . ? C4 C7 H7E 104.8(10) . . ? C12 C7 H7E 105.3(9) . . ? C8 C7 H7E 110.4(10) . . ? C8 C9 C10 111.91(14) . . ? C8 C9 H9E 111.1(11) . . ? C10 C9 H9E 109.1(11) . . ? C8 C9 H9A 109.6(9) . . ? C10 C9 H9A 109.9(9) . . ? H9E C9 H9A 105.0(14) . . ? C17 C18 C19 120.13(19) . . ? C17 C18 H18 118.3(12) . . ? C19 C18 H18 121.6(12) . . ? C7 C12 C11 114.50(14) . . ? C7 C12 H12E 107.4(12) . . ? C11 C12 H12E 107.5(12) . . ? C7 C12 H12A 110.9(10) . . ? C11 C12 H12A 111.4(10) . . ? H12E C12 H12A 104.5(15) . . ? C1 C6 C5 119.30(18) . . ? C1 C6 H6 119.0(14) . . ? C5 C6 H6 121.7(14) . . ? C12 C11 C10 111.76(15) . . ? C12 C11 H11E 109.8(10) . . ? C10 C11 H11E 108.7(10) . . ? C12 C11 H11A 112.0(9) . . ? C10 C11 H11A 108.6(9) . . ? H11E C11 H11A 105.7(13) . . ? C6 C5 C4 122.30(18) . . ? C6 C5 H5 118.8(11) . . ? C4 C5 H5 118.9(11) . . ? 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 C16 C15 C20 C19 0.8(2) . . . . ? C14 C15 C20 C19 -177.70(14) . . . . ? C16 C15 C20 C21 -179.97(14) . . . . ? C14 C15 C20 C21 1.6(2) . . . . ? O2 C21 C20 C19 -5.7(2) . . . . ? C22 C21 C20 C19 173.55(14) . . . . ? O2 C21 C20 C15 175.08(14) . . . . ? C22 C21 C20 C15 -5.7(2) . . . . ? C15 C20 C19 C18 0.0(2) . . . . ? C21 C20 C19 C18 -179.21(16) . . . . ? C5 C4 C3 C2 -0.5(2) . . . . ? C7 C4 C3 C2 -179.28(15) . . . . ? C16 C15 C14 O1 3.2(2) . . . . ? C20 C15 C14 O1 -178.33(15) . . . . ? C16 C15 C14 C13 -175.12(14) . . . . ? C20 C15 C14 C13 3.3(2) . . . . ? O1 C14 C13 C22 177.84(16) . . . . ? C15 C14 C13 C22 -3.8(2) . . . . ? O1 C14 C13 C10 -4.1(2) . . . . ? C15 C14 C13 C10 174.26(13) . . . . ? C9 C10 C13 C22 63.8(2) . . . . ? C11 C10 C13 C22 -61.9(2) . . . . ? C9 C10 C13 C14 -114.18(15) . . . . ? C11 C10 C13 C14 120.18(15) . . . . ? C14 C13 C22 O3 179.46(14) . . . . ? C10 C13 C22 O3 1.5(2) . . . . ? C14 C13 C22 C21 -0.5(2) . . . . ? C10 C13 C22 C21 -178.48(14) . . . . ? O2 C21 C22 O3 4.6(2) . . . . ? C20 C21 C22 O3 -174.61(14) . . . . ? O2 C21 C22 C13 -175.40(15) . . . . ? C20 C21 C22 C13 5.4(2) . . . . ? C20 C15 C16 C17 -0.7(2) . . . . ? C14 C15 C16 C17 177.73(16) . . . . ? C4 C3 C2 C1 0.3(3) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C3 C2 C1 C6 -0.2(3) . . . . ? C3 C2 C1 Cl1 177.44(13) . . . . ? C3 C4 C7 C12 2.4(2) . . . . ? C5 C4 C7 C12 -176.38(15) . . . . ? C3 C4 C7 C8 -122.85(17) . . . . ? C5 C4 C7 C8 58.4(2) . . . . ? C9 C8 C7 C4 72.95(19) . . . . ? C9 C8 C7 C12 -56.1(2) . . . . ? C7 C8 C9 C10 59.5(2) . . . . ? C13 C10 C9 C8 176.63(13) . . . . ? C11 C10 C9 C8 -56.20(18) . . . . ? C16 C17 C18 C19 0.9(3) . . . . ? C20 C19 C18 C17 -0.9(3) . . . . ? C4 C7 C12 C11 -73.0(2) . . . . ? C8 C7 C12 C11 53.3(2) . . . . ? C2 C1 C6 C5 0.2(3) . . . . ? Cl1 C1 C6 C5 -177.36(16) . . . . ? C7 C12 C11 C10 -52.0(2) . . . . ? C13 C10 C11 C12 178.05(13) . . . . ? C9 C10 C11 C12 51.44(18) . . . . ? C1 C6 C5 C4 -0.5(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C7 C4 C5 C6 179.44(18) . . . . ? data_sri7_2m _database_code_depnum_ccdc_archive 'CCDC 749768' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; trans- 2-(4-tert-butylcyclohexyl)-3-hydroxynaphthalene-1,4-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H15 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C20 H15 O3' _chemical_formula_iupac ? _chemical_formula_weight 303.32 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.9504(7) _cell_length_b 12.4798(15) _cell_length_c 12.9769(16) _cell_angle_alpha 107.582(2) _cell_angle_beta 100.950(2) _cell_angle_gamma 103.635(2) _cell_volume 856.55(18) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 320 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.89 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 0.079 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9829 _exptl_absorpt_correction_T_max 0.9969 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 8284 _diffrn_reflns_av_R_equivalents 0.0830 _diffrn_reflns_av_sigmaI/netI 0.1006 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.99 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2988 # number of observed reflections (> n sig(I)) _reflns_number_gt 1537 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.1771P)^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 2988 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1535 _refine_ls_R_factor_gt 0.0930 _refine_ls_wR_factor_ref 0.2959 _refine_ls_wR_factor_gt 0.2532 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.403 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.071 #=============================================================================== # 9. 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C13 C 0.1106(6) 0.1761(3) 0.3910(3) 0.0495(9) Uani 1 1 d . . . C20 C 0.4930(7) 0.3637(3) 0.5816(3) 0.0541(10) Uani 1 1 d . . . C21 C 0.2779(7) 0.3847(3) 0.5256(3) 0.0534(10) Uani 1 1 d . . . C15 C 0.5172(7) 0.2509(3) 0.5426(3) 0.0533(10) Uani 1 1 d . . . O1 O 0.3640(5) 0.0590(2) 0.4072(2) 0.0756(10) Uani 1 1 d . . . O2 O 0.2480(5) 0.4822(2) 0.5556(2) 0.0744(10) Uani 1 1 d . . . C14 C 0.3306(7) 0.1539(3) 0.4437(3) 0.0529(10) Uani 1 1 d . . . C10 C -0.0821(7) 0.0768(3) 0.2956(3) 0.0556(10) Uani 1 1 d . . . C22 C 0.0948(7) 0.2853(3) 0.4306(3) 0.0525(10) Uani 1 1 d . . . O3 O -0.0972(5) 0.3122(3) 0.3829(3) 0.0717(9) Uani 1 1 d . . . C16 C 0.7168(7) 0.2283(4) 0.5946(4) 0.0633(11) Uani 1 1 d . . . C7 C -0.3248(7) -0.1599(3) 0.1148(3) 0.0612(11) Uani 1 1 d . . . C11 C -0.1814(9) -0.0341(3) 0.3217(4) 0.0659(12) Uani 1 1 d . . . C19 C 0.6715(9) 0.4542(4) 0.6721(4) 0.0728(12) Uani 1 1 d . . . C4 C -0.5244(7) -0.2610(4) 0.0162(3) 0.0643(11) Uani 1 1 d . . . C9 C -0.0087(9) 0.0407(4) 0.1873(3) 0.0688(13) Uani 1 1 d . . . C12 C -0.3895(9) -0.1253(4) 0.2238(4) 0.0721(13) Uani 1 1 d . . . C8 C -0.2191(9) -0.0542(4) 0.0900(4) 0.0803(14) Uani 1 1 d . . . H8A H -0.3441 -0.0195 0.0721 0.096 Uiso 1 1 calc R . . H8B H -0.1627 -0.0785 0.0239 0.096 Uiso 1 1 calc R . . C18 C 0.8689(9) 0.4285(5) 0.7234(4) 0.0840(15) Uani 1 1 d . . . C17 C 0.8929(9) 0.3191(4) 0.6850(4) 0.0761(13) Uani 1 1 d . . . C1 C -0.7420(11) -0.2256(6) -0.0203(7) 0.162(4) Uani 1 1 d . . . C2 C -0.6118(17) -0.3674(5) 0.0488(6) 0.176(4) Uani 1 1 d . . . C3 C -0.4339(13) -0.2992(8) -0.0872(6) 0.193(4) Uani 1 1 d . . . H18 H 1.013(8) 0.501(4) 0.795(4) 0.088(13) Uiso 1 1 d . . . H3O H -0.101(7) 0.384(4) 0.419(3) 0.075(13) Uiso 1 1 d . . . H19 H 0.652(7) 0.541(4) 0.697(3) 0.076(12) Uiso 1 1 d . . . H16 H 0.731(6) 0.155(3) 0.569(3) 0.045(10) Uiso 1 1 d . . . H9A H 0.136(10) 0.007(5) 0.201(4) 0.112(18) Uiso 1 1 d . . . H17 H 1.038(9) 0.294(4) 0.726(4) 0.102(15) Uiso 1 1 d . . . H12E H -0.442(10) -0.189(5) 0.247(4) 0.115(19) Uiso 1 1 d . . . H10A H -0.210(8) 0.095(3) 0.285(3) 0.070(13) Uiso 1 1 d . . . H11A H -0.039(9) -0.074(4) 0.339(4) 0.094(15) Uiso 1 1 d . . . H12A H -0.528(10) -0.095(4) 0.213(4) 0.108(18) Uiso 1 1 d . . . H9E H 0.006(9) 0.113(5) 0.172(4) 0.103(17) Uiso 1 1 d . . . H7A H -0.160(10) -0.190(5) 0.132(4) 0.119(17) Uiso 1 1 d . . . H11E H -0.243(8) -0.020(4) 0.388(4) 0.092(14) 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 C13 0.049(2) 0.044(2) 0.057(2) 0.0196(17) 0.0143(18) 0.0159(17) C20 0.059(2) 0.047(2) 0.054(2) 0.0183(18) 0.0170(19) 0.0119(18) C21 0.062(2) 0.043(2) 0.058(2) 0.0170(18) 0.023(2) 0.0188(18) C15 0.053(2) 0.056(2) 0.053(2) 0.0223(19) 0.0171(19) 0.0161(18) O1 0.0725(19) 0.0556(17) 0.086(2) 0.0093(15) 0.0036(16) 0.0336(15) O2 0.082(2) 0.0451(16) 0.089(2) 0.0135(15) 0.0189(17) 0.0241(15) C14 0.056(2) 0.044(2) 0.056(2) 0.0150(18) 0.0163(19) 0.0155(18) C10 0.048(2) 0.051(2) 0.065(3) 0.0175(19) 0.0089(19) 0.0202(19) C22 0.055(2) 0.046(2) 0.059(2) 0.0210(19) 0.0183(19) 0.0176(18) O3 0.0719(19) 0.0476(17) 0.085(2) 0.0131(15) 0.0055(16) 0.0278(15) C16 0.058(3) 0.063(3) 0.068(3) 0.025(2) 0.013(2) 0.021(2) C7 0.054(2) 0.059(2) 0.056(3) 0.012(2) 0.012(2) 0.0051(19) C11 0.077(3) 0.052(2) 0.055(3) 0.010(2) 0.021(2) 0.005(2) C19 0.075(3) 0.056(3) 0.070(3) 0.012(2) 0.014(2) 0.009(2) C4 0.054(2) 0.061(2) 0.067(3) 0.015(2) 0.013(2) 0.0126(19) C9 0.069(3) 0.066(3) 0.053(3) 0.020(2) 0.010(2) -0.002(2) C12 0.076(3) 0.061(3) 0.072(3) 0.020(2) 0.029(3) 0.007(2) C8 0.082(3) 0.074(3) 0.062(3) 0.021(2) 0.013(2) -0.003(2) C18 0.070(3) 0.073(3) 0.078(3) 0.015(3) 0.000(3) 0.002(3) C17 0.065(3) 0.076(3) 0.073(3) 0.024(3) 0.002(2) 0.013(2) C1 0.073(4) 0.100(4) 0.216(8) -0.018(5) -0.061(5) 0.029(3) C2 0.263(11) 0.057(3) 0.122(5) 0.024(3) -0.033(6) -0.025(5) C3 0.105(5) 0.223(8) 0.108(5) -0.074(5) 0.045(4) -0.041(5) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 C13 C22 1.337(5) . ? C13 C14 1.485(5) . ? C13 C10 1.499(5) . ? C20 C19 1.394(6) . ? C20 C15 1.396(5) . ? C20 C21 1.468(5) . ? C21 O2 1.227(4) . ? C21 C22 1.474(5) . ? C15 C16 1.384(5) . ? C15 C14 1.494(5) . ? O1 C14 1.214(4) . ? C10 C9 1.521(6) . ? C10 C11 1.534(6) . ? C10 H10A 0.85(4) . ? C22 O3 1.356(4) . ? O3 H3O 0.88(5) . ? C16 C17 1.389(6) . ? C16 H16 0.90(3) . ? C7 C8 1.478(6) . ? C7 C12 1.500(6) . ? C7 C4 1.543(5) . ? C7 H7A 1.14(5) . ? C11 C12 1.519(6) . ? C11 H11A 1.10(5) . ? C11 H11E 0.99(5) . ? C19 C18 1.391(7) . ? C19 H19 1.07(4) . ? C4 C1 1.503(7) . ? C4 C2 1.521(7) . ? C4 C3 1.526(7) . ? C9 C8 1.537(6) . ? C9 H9A 1.05(6) . ? C9 H9E 0.97(5) . ? C12 H12E 0.95(5) . ? C12 H12A 0.99(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C18 C17 1.356(7) . ? C18 H18 1.11(5) . ? C17 H17 1.08(5) . ? 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 C22 C13 C14 118.0(3) . . ? C22 C13 C10 122.8(3) . . ? C14 C13 C10 119.2(3) . . ? C19 C20 C15 120.0(4) . . ? C19 C20 C21 121.0(4) . . ? C15 C20 C21 118.9(3) . . ? O2 C21 C20 121.8(4) . . ? O2 C21 C22 119.7(4) . . ? C20 C21 C22 118.5(3) . . ? C16 C15 C20 120.2(4) . . ? C16 C15 C14 119.2(4) . . ? C20 C15 C14 120.7(3) . . ? O1 C14 C13 121.4(3) . . ? O1 C14 C15 119.2(3) . . ? C13 C14 C15 119.4(3) . . ? C13 C10 C9 113.4(3) . . ? C13 C10 C11 115.0(3) . . ? C9 C10 C11 109.0(4) . . ? C13 C10 H10A 109(3) . . ? C9 C10 H10A 111(3) . . ? C11 C10 H10A 98(3) . . ? C13 C22 O3 120.7(4) . . ? C13 C22 C21 124.4(3) . . ? O3 C22 C21 114.9(3) . . ? C22 O3 H3O 115(3) . . ? C15 C16 C17 119.2(4) . . ? C15 C16 H16 120(2) . . ? C17 C16 H16 121(2) . . ? C8 C7 C12 110.7(4) . . ? C8 C7 C4 115.3(3) . . ? C12 C7 C4 114.5(3) . . ? C8 C7 H7A 100(3) . . ? C12 C7 H7A 106(3) . . ? C4 C7 H7A 109(3) . . ? C12 C11 C10 111.0(4) . . ? C12 C11 H11A 109(2) . . ? C10 C11 H11A 110(2) . . ? C12 C11 H11E 106(3) . . ? C10 C11 H11E 115(3) . . ? H11A C11 H11E 106(3) . . ? C18 C19 C20 118.5(4) . . ? C18 C19 H19 123(2) . . ? C20 C19 H19 118(2) . . ? C1 C4 C2 106.6(6) . . ? C1 C4 C3 106.4(5) . . ? C2 C4 C3 109.0(6) . . ? C1 C4 C7 112.7(4) . . ? C2 C4 C7 111.0(4) . . ? C3 C4 C7 110.9(4) . . ? C10 C9 C8 111.2(4) . . ? C10 C9 H9A 109(3) . . ? C8 C9 H9A 109(3) . . ? C10 C9 H9E 99(3) . . ? C8 C9 H9E 105(3) . . ? H9A C9 H9E 123(4) . . ? C7 C12 C11 113.2(4) . . ? C7 C12 H12E 114(3) . . ? C11 C12 H12E 105(3) . . ? C7 C12 H12A 108(3) . . ? C11 C12 H12A 110(3) . . ? H12E C12 H12A 105(4) . . ? C7 C8 C9 113.8(4) . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C17 C18 C19 121.4(5) . . ? C17 C18 H18 120(2) . . ? C19 C18 H18 118(2) . . ? C18 C17 C16 120.7(5) . . ? C18 C17 H17 124(3) . . ? C16 C17 H17 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 C19 C20 C21 O2 0.5(6) . . . . ? C15 C20 C21 O2 -179.4(3) . . . . ? C19 C20 C21 C22 -179.7(3) . . . . ? C15 C20 C21 C22 0.4(5) . . . . ? C19 C20 C15 C16 0.8(6) . . . . ? C21 C20 C15 C16 -179.3(3) . . . . ? C19 C20 C15 C14 -178.4(3) . . . . ? C21 C20 C15 C14 1.5(5) . . . . ? C22 C13 C14 O1 -175.0(4) . . . . ? C10 C13 C14 O1 4.2(6) . . . . ? C22 C13 C14 C15 3.8(5) . . . . ? C10 C13 C14 C15 -176.9(3) . . . . ? C16 C15 C14 O1 -4.0(5) . . . . ? C20 C15 C14 O1 175.2(4) . . . . ? C16 C15 C14 C13 177.2(3) . . . . ? C20 C15 C14 C13 -3.7(5) . . . . ? C22 C13 C10 C9 108.9(5) . . . . ? C14 C13 C10 C9 -70.3(5) . . . . ? C22 C13 C10 C11 -124.7(4) . . . . ? C14 C13 C10 C11 56.0(5) . . . . ? C14 C13 C22 O3 177.4(3) . . . . ? C10 C13 C22 O3 -1.9(6) . . . . ? C14 C13 C22 C21 -2.0(5) . . . . ? C10 C13 C22 C21 178.8(3) . . . . ? O2 C21 C22 C13 179.7(4) . . . . ? C20 C21 C22 C13 -0.2(5) . . . . ? O2 C21 C22 O3 0.3(5) . . . . ? C20 C21 C22 O3 -179.5(3) . . . . ? C20 C15 C16 C17 -0.6(6) . . . . ? C14 C15 C16 C17 178.6(4) . . . . ? C13 C10 C11 C12 175.1(4) . . . . ? C9 C10 C11 C12 -56.3(5) . . . . ? C15 C20 C19 C18 -1.4(6) . . . . ? C21 C20 C19 C18 178.7(4) . . . . ? C8 C7 C4 C1 -63.3(6) . . . . ? C12 C7 C4 C1 67.0(6) . . . . ? C8 C7 C4 C2 177.2(5) . . . . ? C12 C7 C4 C2 -52.5(7) . . . . ? C8 C7 C4 C3 55.9(7) . . . . ? C12 C7 C4 C3 -173.9(6) . . . . ? C13 C10 C9 C8 -175.4(4) . . . . ? C11 C10 C9 C8 55.2(5) . . . . ? C8 C7 C12 C11 -53.1(6) . . . . ? C4 C7 C12 C11 174.4(4) . . . . ? C10 C11 C12 C7 56.2(6) . . . . ? C12 C7 C8 C9 52.2(6) . . . . ? C4 C7 C8 C9 -175.8(4) . . . . ? C10 C9 C8 C7 -54.9(6) . . . . ? C20 C19 C18 C17 1.8(7) . . . . ? C19 C18 C17 C16 -1.6(8) . . . . ? C15 C16 C17 C18 1.0(7) . . . . ? data_sri20_m _database_code_depnum_ccdc_archive 'CCDC 749769' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; 2-cyclohexyl-3-hydroxynaphthalene-1,4-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H16 O3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H16 O3' _chemical_formula_iupac ? _chemical_formula_weight 256.29 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 14.401(3) _cell_length_b 5.3279(9) _cell_length_c 17.393(3) _cell_angle_alpha 90 _cell_angle_beta 98.926(3) _cell_angle_gamma 90 _cell_volume 1318.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 430 _cell_measurement_theta_min 0.97 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.088 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9886 _exptl_absorpt_correction_T_max 0.9947 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 9080 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2334 # number of observed reflections (> n sig(I)) _reflns_number_gt 1479 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0632P)^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 2334 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1395 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.156 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.035 #=============================================================================== # 9. 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.98693(10) 0.2157(3) 0.94409(9) 0.0657(5) Uani 1 1 d . . . O3 O 0.86426(11) 0.1404(3) 1.03995(9) 0.0628(5) Uani 1 1 d . . . C21 C 0.91749(13) 0.3532(4) 0.93449(11) 0.0479(5) Uani 1 1 d . . . C13 C 0.77121(13) 0.4787(3) 0.98424(11) 0.0450(5) Uani 1 1 d . . . O1 O 0.68074(11) 0.7834(3) 0.90931(9) 0.0708(5) Uani 1 1 d . . . C14 C 0.75431(14) 0.6649(4) 0.92085(11) 0.0478(5) Uani 1 1 d . . . C20 C 0.90391(14) 0.5474(4) 0.87384(11) 0.0472(5) Uani 1 1 d . . . C22 C 0.84697(14) 0.3264(4) 0.98717(11) 0.0477(5) Uani 1 1 d . . . C15 C 0.82510(13) 0.7006(4) 0.86813(11) 0.0462(5) Uani 1 1 d . . . C10 C 0.70105(14) 0.4655(4) 1.04004(12) 0.0503(6) Uani 1 1 d . . . C16 C 0.81320(17) 0.8875(4) 0.81175(13) 0.0589(6) Uani 1 1 d . . . C19 C 0.96828(17) 0.5758(5) 0.82311(14) 0.0646(7) Uani 1 1 d . . . C9 C 0.74362(18) 0.5038(6) 1.12463(14) 0.0645(7) Uani 1 1 d . . . C17 C 0.87770(19) 0.9181(5) 0.76230(15) 0.0698(7) Uani 1 1 d . . . C11 C 0.64070(19) 0.2305(5) 1.02961(17) 0.0668(7) Uani 1 1 d . . . C8 C 0.6683(2) 0.5040(6) 1.17697(18) 0.0714(8) Uani 1 1 d . . . C12 C 0.56641(19) 0.2301(6) 1.08279(17) 0.0749(8) Uani 1 1 d . . . C18 C 0.9543(2) 0.7624(5) 0.76735(15) 0.0759(8) Uani 1 1 d . . . C7 C 0.6089(2) 0.2707(5) 1.16665(16) 0.0739(8) Uani 1 1 d . . . H19 H 1.0234(17) 0.457(4) 0.8317(13) 0.079(7) Uiso 1 1 d . . . H17 H 0.8712(16) 1.047(4) 0.7264(14) 0.075(8) Uiso 1 1 d . . . H11E H 0.6099(18) 0.225(4) 0.9729(16) 0.093(8) Uiso 1 1 d . . . H7A H 0.6513(17) 0.117(5) 1.1824(13) 0.082(8) Uiso 1 1 d . . . H18 H 1.0003(17) 0.782(4) 0.7317(14) 0.083(8) Uiso 1 1 d . . . H8A H 0.6253(17) 0.652(5) 1.1623(13) 0.079(8) Uiso 1 1 d . . . H12A H 0.5212(19) 0.378(5) 1.0690(14) 0.092(9) Uiso 1 1 d . . . H11A H 0.6819(19) 0.090(5) 1.0425(14) 0.093(9) Uiso 1 1 d . . . H7E H 0.5596(17) 0.278(4) 1.1995(14) 0.072(7) Uiso 1 1 d . . . H10A H 0.6552(14) 0.619(4) 1.0249(11) 0.062(6) Uiso 1 1 d . . . H3O H 0.917(2) 0.066(5) 1.0350(14) 0.091(9) Uiso 1 1 d . . . H9E H 0.7796(17) 0.655(5) 1.1308(13) 0.079(7) Uiso 1 1 d . . . H12E H 0.526(2) 0.080(5) 1.0751(15) 0.111(10) Uiso 1 1 d . . . H8E H 0.694(2) 0.531(5) 1.2296(16) 0.106(10) Uiso 1 1 d . . . H16 H 0.7626(16) 0.987(4) 0.8115(11) 0.064(7) Uiso 1 1 d . . . H9A H 0.7892(19) 0.362(5) 1.1418(14) 0.095(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 O2 0.0513(9) 0.0704(10) 0.0783(12) 0.0107(8) 0.0188(8) 0.0177(8) O3 0.0550(10) 0.0665(11) 0.0696(11) 0.0202(8) 0.0181(8) 0.0175(8) C21 0.0396(11) 0.0487(12) 0.0551(14) -0.0057(10) 0.0063(10) 0.0019(10) C13 0.0400(11) 0.0448(11) 0.0496(13) -0.0062(9) 0.0054(9) 0.0018(9) O1 0.0658(10) 0.0817(12) 0.0666(11) 0.0083(8) 0.0152(8) 0.0312(9) C14 0.0460(12) 0.0481(12) 0.0481(13) -0.0085(10) 0.0034(9) 0.0066(10) C20 0.0444(11) 0.0483(12) 0.0492(13) -0.0002(10) 0.0077(10) -0.0019(10) C22 0.0459(12) 0.0468(12) 0.0500(13) 0.0025(10) 0.0061(9) 0.0014(10) C15 0.0446(12) 0.0461(12) 0.0460(12) -0.0029(9) 0.0012(9) -0.0007(10) C10 0.0446(12) 0.0532(13) 0.0544(14) -0.0014(10) 0.0114(10) 0.0043(10) C16 0.0586(15) 0.0554(14) 0.0611(16) 0.0018(11) 0.0048(12) 0.0034(12) C19 0.0535(14) 0.0706(16) 0.0719(17) 0.0074(13) 0.0167(12) 0.0005(12) C9 0.0642(16) 0.0718(18) 0.0597(16) -0.0160(13) 0.0170(13) -0.0154(15) C17 0.0722(18) 0.0723(17) 0.0639(17) 0.0187(14) 0.0078(13) -0.0087(14) C11 0.0594(16) 0.0722(18) 0.0709(19) -0.0150(14) 0.0168(13) -0.0143(14) C8 0.0777(18) 0.0759(19) 0.0657(19) -0.0133(15) 0.0268(15) -0.0077(16) C12 0.0577(16) 0.082(2) 0.088(2) -0.0045(16) 0.0197(14) -0.0178(16) C18 0.0698(17) 0.089(2) 0.0732(19) 0.0155(15) 0.0259(14) -0.0072(15) C7 0.0779(18) 0.0708(18) 0.080(2) 0.0051(15) 0.0342(16) 0.0013(15) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 O2 C21 1.230(2) . ? O3 C22 1.348(2) . ? O3 H3O 0.88(3) . ? C21 C20 1.469(3) . ? C21 C22 1.477(3) . ? C13 C22 1.354(3) . ? C13 C14 1.475(3) . ? C13 C10 1.507(3) . ? O1 C14 1.223(2) . ? C14 C15 1.485(3) . ? C20 C19 1.384(3) . ? C20 C15 1.389(3) . ? C15 C16 1.390(3) . ? C10 C9 1.517(3) . ? C10 C11 1.519(3) . ? C10 H10A 1.06(2) . ? C16 C17 1.370(3) . ? C16 H16 0.90(2) . ? C19 C18 1.382(3) . ? C19 H19 1.01(2) . ? C9 C8 1.520(3) . ? C9 H9E 0.96(3) . ? C9 H9A 1.01(3) . ? C17 C18 1.372(4) . ? C17 H17 0.92(2) . ? C11 C12 1.519(3) . ? C11 H11E 1.02(3) . ? C11 H11A 0.96(3) . ? C8 C7 1.504(4) . ? C8 H8A 1.01(3) . ? C8 H8E 0.94(3) . ? C12 C7 1.507(4) . ? C12 H12A 1.03(3) . ? C12 H12E 0.99(3) . ? C18 H18 0.98(3) . ? C7 H7A 1.03(3) . ? C7 H7E 0.98(2) . ? 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 C22 O3 H3O 109.8(16) . . ? O2 C21 C20 122.14(18) . . ? O2 C21 C22 118.77(18) . . ? C20 C21 C22 119.07(17) . . ? C22 C13 C14 118.00(17) . . ? C22 C13 C10 124.35(19) . . ? C14 C13 C10 117.61(17) . . ? O1 C14 C13 120.53(18) . . ? O1 C14 C15 119.53(19) . . ? C13 C14 C15 119.88(17) . . ? C19 C20 C15 120.7(2) . . ? C19 C20 C21 120.48(19) . . ? C15 C20 C21 118.79(17) . . ? O3 C22 C13 121.93(18) . . ? O3 C22 C21 114.93(17) . . ? C13 C22 C21 123.13(19) . . ? C16 C15 C20 118.8(2) . . ? C16 C15 C14 120.41(18) . . ? C20 C15 C14 120.80(18) . . ? C13 C10 C9 114.06(17) . . ? C13 C10 C11 112.96(17) . . ? C9 C10 C11 111.4(2) . . ? C13 C10 H10A 104.9(11) . . ? C9 C10 H10A 106.2(10) . . ? C11 C10 H10A 106.5(11) . . ? C17 C16 C15 120.4(2) . . ? C17 C16 H16 123.6(13) . . ? C15 C16 H16 115.9(13) . . ? C18 C19 C20 119.2(2) . . ? C18 C19 H19 125.6(13) . . ? C20 C19 H19 115.2(13) . . ? C10 C9 C8 111.2(2) . . ? C10 C9 H9E 110.7(14) . . ? C8 C9 H9E 110.9(14) . . ? C10 C9 H9A 109.3(15) . . ? C8 C9 H9A 108.3(15) . . ? H9E C9 H9A 106(2) . . ? C16 C17 C18 120.3(3) . . ? C16 C17 H17 120.3(15) . . ? C18 C17 H17 119.3(15) . . ? C10 C11 C12 111.9(2) . . ? C10 C11 H11E 107.1(14) . . ? C12 C11 H11E 110.4(15) . . ? C10 C11 H11A 107.0(16) . . ? C12 C11 H11A 109.0(16) . . ? H11E C11 H11A 112(2) . . ? C7 C8 C9 111.9(2) . . ? C7 C8 H8A 107.4(14) . . ? C9 C8 H8A 108.4(14) . . ? C7 C8 H8E 111.7(17) . . ? C9 C8 H8E 112.1(17) . . ? H8A C8 H8E 105(2) . . ? C7 C12 C11 111.7(2) . . ? C7 C12 H12A 105.2(14) . . ? C11 C12 H12A 109.7(14) . . ? C7 C12 H12E 113.0(16) . . ? C11 C12 H12E 112.3(16) . . ? H12A C12 H12E 104(2) . . ? C17 C18 C19 120.5(2) . . ? C17 C18 H18 120.6(14) . . ? C19 C18 H18 118.9(14) . . ? C8 C7 C12 111.9(2) . . ? C8 C7 H7A 108.8(13) . . ? C12 C7 H7A 106.1(13) . . ? C8 C7 H7E 110.4(13) . . ? C12 C7 H7E 110.3(14) . . ? H7A C7 H7E 109.2(18) . . ? 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 C22 C13 C14 O1 170.19(18) . . . . ? C10 C13 C14 O1 -7.9(3) . . . . ? C22 C13 C14 C15 -6.9(3) . . . . ? C10 C13 C14 C15 174.99(17) . . . . ? O2 C21 C20 C19 2.3(3) . . . . ? C22 C21 C20 C19 -179.42(19) . . . . ? O2 C21 C20 C15 -178.02(18) . . . . ? C22 C21 C20 C15 0.2(3) . . . . ? C14 C13 C22 O3 -175.58(17) . . . . ? C10 C13 C22 O3 2.4(3) . . . . ? C14 C13 C22 C21 5.6(3) . . . . ? C10 C13 C22 C21 -176.40(18) . . . . ? O2 C21 C22 O3 -2.9(3) . . . . ? C20 C21 C22 O3 178.77(16) . . . . ? O2 C21 C22 C13 175.94(18) . . . . ? C20 C21 C22 C13 -2.4(3) . . . . ? C19 C20 C15 C16 -1.6(3) . . . . ? C21 C20 C15 C16 178.76(18) . . . . ? C19 C20 C15 C14 177.97(19) . . . . ? C21 C20 C15 C14 -1.7(3) . . . . ? O1 C14 C15 C16 7.5(3) . . . . ? C13 C14 C15 C16 -175.41(18) . . . . ? O1 C14 C15 C20 -172.09(19) . . . . ? C13 C14 C15 C20 5.0(3) . . . . ? C22 C13 C10 C9 59.0(3) . . . . ? C14 C13 C10 C9 -123.0(2) . . . . ? C22 C13 C10 C11 -69.5(3) . . . . ? C14 C13 C10 C11 108.5(2) . . . . ? C20 C15 C16 C17 0.6(3) . . . . ? C14 C15 C16 C17 -179.0(2) . . . . ? C15 C20 C19 C18 1.3(4) . . . . ? C21 C20 C19 C18 -179.1(2) . . . . ? C13 C10 C9 C8 176.5(2) . . . . ? C11 C10 C9 C8 -54.2(3) . . . . ? C15 C16 C17 C18 0.7(4) . . . . ? C13 C10 C11 C12 -176.2(2) . . . . ? C9 C10 C11 C12 53.9(3) . . . . ? C10 C9 C8 C7 54.8(4) . . . . ? C10 C11 C12 C7 -53.6(4) . . . . ? C16 C17 C18 C19 -1.1(4) . . . . ? C20 C19 C18 C17 0.1(4) . . . . ? C9 C8 C7 C12 -54.6(4) . . . . ? C11 C12 C7 C8 53.9(4) . . . . ? data_sri11_m _database_code_depnum_ccdc_archive 'CCDC 749770' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; trans -2-(4-(4-chlorophenyl)cyclohexyl)-3-chloronaphthalene-1,4-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Cl2 O2' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C22 H18 Cl2 O2' _chemical_formula_iupac ? _chemical_formula_weight 385.26 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 10.3671(11) _cell_length_b 7.0515(7) _cell_length_c 25.102(2) _cell_angle_alpha 90 _cell_angle_beta 99.777(2) _cell_angle_gamma 90 _cell_volume 1808.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 360 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.97 _cell_special_details ; ; _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.373 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9531 _exptl_absorpt_correction_T_max 0.9856 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 13553 _diffrn_reflns_av_R_equivalents 0.0858 _diffrn_reflns_av_sigmaI/netI 0.0908 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 26.00 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3542 # number of observed reflections (> n sig(I)) _reflns_number_gt 1802 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0341P)^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 3542 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1457 _refine_ls_R_factor_gt 0.0635 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.233 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.048 #=============================================================================== # 9. 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.74443(9) 0.78569(14) 0.01798(4) 0.0586(3) Uani 1 1 d . . . Cl2 Cl 1.44823(10) 0.61281(15) 0.39147(4) 0.0726(4) Uani 1 1 d . . . O1 O 0.5031(2) 0.6088(4) 0.16893(10) 0.0606(8) Uani 1 1 d . . . C15 C 0.3708(3) 0.6459(5) 0.08413(14) 0.0409(9) Uani 1 1 d . . . C13 C 0.6215(3) 0.6683(4) 0.09821(13) 0.0379(9) Uani 1 1 d . . . C22 C 0.6095(3) 0.7269(4) 0.04656(13) 0.0397(9) Uani 1 1 d . . . C20 C 0.3628(3) 0.7038(4) 0.03068(14) 0.0400(9) Uani 1 1 d . . . C10 C 0.7514(3) 0.6499(5) 0.13525(15) 0.0422(9) Uani 1 1 d . . . C7 C 0.9283(3) 0.6292(5) 0.24156(14) 0.0428(10) Uani 1 1 d . . . C14 C 0.4987(3) 0.6360(5) 0.12060(15) 0.0454(9) Uani 1 1 d . . . C1 C 1.2977(3) 0.6163(5) 0.34810(15) 0.0465(10) Uani 1 1 d . . . C21 C 0.4827(3) 0.7494(4) 0.00896(15) 0.0428(9) Uani 1 1 d . . . C4 C 1.0576(3) 0.6237(5) 0.27924(13) 0.0404(9) Uani 1 1 d . . . C2 C 1.2941(4) 0.6254(6) 0.29340(17) 0.0577(12) Uani 1 1 d . . . C5 C 1.0661(4) 0.6150(5) 0.33457(15) 0.0484(10) Uani 1 1 d . . . O2 O 0.4794(2) 0.8008(4) -0.03743(10) 0.0664(8) Uani 1 1 d . . . C6 C 1.1841(4) 0.6100(5) 0.36901(16) 0.0546(11) Uani 1 1 d . . . C9 C 0.7750(4) 0.8217(6) 0.17297(17) 0.0482(11) Uani 1 1 d . . . C12 C 0.9071(4) 0.4601(6) 0.20325(16) 0.0468(10) Uani 1 1 d . . . C16 C 0.2571(4) 0.6029(6) 0.10411(17) 0.0539(11) Uani 1 1 d . . . C8 C 0.9085(4) 0.8123(6) 0.20906(16) 0.0459(10) Uani 1 1 d . . . C3 C 1.1746(4) 0.6303(6) 0.25963(17) 0.0568(12) Uani 1 1 d . . . C11 C 0.7732(4) 0.4642(6) 0.16707(17) 0.0494(11) Uani 1 1 d . . . C18 C 0.1288(4) 0.6818(6) 0.0183(2) 0.0656(13) Uani 1 1 d . . . C19 C 0.2406(4) 0.7221(5) -0.00191(17) 0.0531(11) Uani 1 1 d . . . C17 C 0.1373(4) 0.6223(6) 0.0710(2) 0.0639(12) Uani 1 1 d . . . H15A H 0.821(3) 0.655(4) 0.1151(10) 0.033(9) Uiso 1 1 d . . . H8A H 0.977(3) 0.819(4) 0.1874(11) 0.042(10) Uiso 1 1 d . . . H7A H 0.860(3) 0.626(4) 0.2617(11) 0.036(9) Uiso 1 1 d . . . H5 H 0.993(3) 0.604(4) 0.3486(12) 0.045(11) Uiso 1 1 d . . . H17 H 0.060(3) 0.594(5) 0.0858(13) 0.064(12) Uiso 1 1 d . . . H9E H 0.768(3) 0.938(5) 0.1516(12) 0.064(12) Uiso 1 1 d . . . H6 H 1.191(3) 0.603(5) 0.4064(13) 0.064(12) Uiso 1 1 d . . . H16 H 0.270(3) 0.562(4) 0.1403(12) 0.051(11) Uiso 1 1 d . . . H18 H 0.046(3) 0.704(4) -0.0029(13) 0.059(11) Uiso 1 1 d . . . H12A H 0.975(3) 0.454(5) 0.1804(12) 0.066(12) Uiso 1 1 d . . . H11E H 0.762(3) 0.355(4) 0.1418(12) 0.049(10) Uiso 1 1 d . . . H2 H 1.368(3) 0.636(4) 0.2805(12) 0.044(11) Uiso 1 1 d . . . H19 H 0.239(3) 0.763(5) -0.0388(14) 0.068(12) Uiso 1 1 d . . . H3 H 1.175(3) 0.639(5) 0.2232(13) 0.059(12) Uiso 1 1 d . . . H8ER H 0.920(3) 0.920(4) 0.2337(11) 0.044(10) Uiso 1 1 d . . . H9A H 0.713(3) 0.823(4) 0.1954(12) 0.052(11) Uiso 1 1 d . . . H12E H 0.920(3) 0.338(5) 0.2241(12) 0.055(11) Uiso 1 1 d . . . H11A H 0.708(3) 0.451(4) 0.1877(11) 0.045(11) 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 Cl1 0.0536(6) 0.0746(7) 0.0507(6) 0.0140(5) 0.0175(5) -0.0052(5) Cl2 0.0630(7) 0.0814(8) 0.0631(7) -0.0070(6) -0.0189(5) -0.0010(6) O1 0.0529(16) 0.092(2) 0.0388(16) 0.0130(15) 0.0123(13) 0.0002(14) C15 0.038(2) 0.044(2) 0.041(2) -0.0022(18) 0.0074(18) -0.0008(17) C13 0.043(2) 0.039(2) 0.032(2) -0.0016(17) 0.0077(17) -0.0030(16) C22 0.044(2) 0.037(2) 0.039(2) -0.0021(18) 0.0103(18) -0.0036(17) C20 0.044(2) 0.034(2) 0.041(2) -0.0013(18) 0.0034(18) -0.0008(17) C10 0.038(2) 0.049(3) 0.041(2) 0.002(2) 0.0113(19) -0.0008(18) C7 0.038(2) 0.054(3) 0.037(2) -0.002(2) 0.0072(19) 0.0006(19) C14 0.053(2) 0.047(2) 0.037(2) 0.0056(19) 0.012(2) 0.0007(18) C1 0.051(2) 0.045(2) 0.041(2) -0.0025(19) -0.002(2) -0.0024(18) C21 0.054(2) 0.040(2) 0.034(2) 0.0022(18) 0.0066(19) -0.0032(18) C4 0.047(2) 0.042(2) 0.032(2) -0.0017(18) 0.0075(18) 0.0017(17) C2 0.044(3) 0.076(3) 0.053(3) 0.005(2) 0.010(2) 0.006(2) C5 0.049(3) 0.061(3) 0.037(3) 0.000(2) 0.012(2) -0.006(2) O2 0.0632(18) 0.097(2) 0.0375(16) 0.0172(15) 0.0049(13) -0.0058(15) C6 0.070(3) 0.062(3) 0.030(3) -0.003(2) 0.002(2) -0.006(2) C9 0.049(3) 0.043(3) 0.051(3) 0.006(2) 0.006(2) 0.002(2) C12 0.049(3) 0.047(3) 0.042(3) 0.002(2) 0.002(2) 0.007(2) C16 0.050(3) 0.061(3) 0.052(3) 0.004(2) 0.012(2) -0.003(2) C8 0.051(3) 0.048(3) 0.039(3) -0.005(2) 0.008(2) -0.003(2) C3 0.052(3) 0.085(3) 0.033(3) 0.001(2) 0.008(2) 0.008(2) C11 0.052(3) 0.047(3) 0.048(3) -0.004(2) 0.004(2) 0.001(2) C18 0.048(3) 0.071(3) 0.073(4) 0.004(3) -0.003(3) -0.004(2) C19 0.055(3) 0.054(3) 0.047(3) 0.001(2) 0.002(2) 0.000(2) C17 0.043(3) 0.075(3) 0.075(3) -0.003(3) 0.014(3) -0.001(2) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 Cl1 C22 1.728(3) . ? Cl2 C1 1.745(3) . ? O1 C14 1.221(4) . ? C15 C16 1.390(5) . ? C15 C20 1.391(4) . ? C15 C14 1.479(4) . ? C13 C22 1.346(4) . ? C13 C14 1.494(4) . ? C13 C10 1.507(4) . ? C22 C21 1.491(4) . ? C20 C19 1.392(4) . ? C20 C21 1.475(4) . ? C10 C11 1.531(5) . ? C10 C9 1.531(5) . ? C10 H15A 0.95(3) . ? C7 C4 1.504(4) . ? C7 C8 1.522(5) . ? C7 C12 1.524(5) . ? C7 H7A 0.94(3) . ? C1 C2 1.369(5) . ? C1 C6 1.369(5) . ? C21 O2 1.215(3) . ? C4 C5 1.378(4) . ? C4 C3 1.385(5) . ? C2 C3 1.378(5) . ? C2 H2 0.88(3) . ? C5 C6 1.373(5) . ? C5 H5 0.89(3) . ? C6 H6 0.93(3) . ? C9 C8 1.521(5) . ? C9 H9E 0.97(3) . ? C9 H9A 0.92(3) . ? C12 C11 1.525(5) . ? C12 H12A 0.98(3) . ? C12 H12E 1.01(3) . ? C16 C17 1.379(5) . ? C16 H16 0.94(3) . ? C8 H8A 0.96(3) . ? C8 H8ER 0.97(3) . ? C3 H3 0.92(3) . ? C11 H11E 0.99(3) . ? C11 H11A 0.93(3) . ? C18 C19 1.372(5) . ? C18 C17 1.376(5) . ? C18 H18 0.94(3) . ? C19 H19 0.97(3) . ? C17 H17 0.96(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 C16 C15 C20 119.8(3) . . ? C16 C15 C14 119.5(3) . . ? C20 C15 C14 120.7(3) . . ? C22 C13 C14 117.6(3) . . ? C22 C13 C10 123.2(3) . . ? C14 C13 C10 119.0(3) . . ? C13 C22 C21 124.7(3) . . ? C13 C22 Cl1 121.6(3) . . ? C21 C22 Cl1 113.6(3) . . ? C15 C20 C19 119.6(3) . . ? C15 C20 C21 120.3(3) . . ? C19 C20 C21 120.1(3) . . ? C13 C10 C11 115.7(3) . . ? C13 C10 C9 110.2(3) . . ? C11 C10 C9 111.1(3) . . ? C13 C10 H15A 110.3(16) . . ? C11 C10 H15A 104.8(17) . . ? C9 C10 H15A 104.0(17) . . ? C4 C7 C8 112.6(3) . . ? C4 C7 C12 113.2(3) . . ? C8 C7 C12 109.5(3) . . ? C4 C7 H7A 109.6(17) . . ? C8 C7 H7A 105.2(18) . . ? C12 C7 H7A 106.3(18) . . ? O1 C14 C15 120.0(3) . . ? O1 C14 C13 120.5(3) . . ? C15 C14 C13 119.4(3) . . ? C2 C1 C6 120.5(4) . . ? C2 C1 Cl2 119.7(3) . . ? C6 C1 Cl2 119.8(3) . . ? O2 C21 C20 122.1(3) . . ? O2 C21 C22 121.1(3) . . ? C20 C21 C22 116.8(3) . . ? C5 C4 C3 116.7(4) . . ? C5 C4 C7 122.2(3) . . ? C3 C4 C7 121.1(3) . . ? C1 C2 C3 119.1(4) . . ? C1 C2 H2 120(2) . . ? C3 C2 H2 121(2) . . ? C6 C5 C4 122.3(4) . . ? C6 C5 H5 118(2) . . ? C4 C5 H5 119(2) . . ? C1 C6 C5 119.3(4) . . ? C1 C6 H6 118(2) . . ? C5 C6 H6 123(2) . . ? C8 C9 C10 111.6(3) . . ? C8 C9 H9E 110.0(18) . . ? C10 C9 H9E 109.5(19) . . ? C8 C9 H9A 107(2) . . ? C10 C9 H9A 110(2) . . ? H9E C9 H9A 109(3) . . ? C7 C12 C11 112.4(3) . . ? C7 C12 H12A 111(2) . . ? C11 C12 H12A 109.0(19) . . ? C7 C12 H12E 110.5(17) . . ? C11 C12 H12E 110.7(18) . . ? H12A C12 H12E 103(3) . . ? C17 C16 C15 119.5(4) . . ? C17 C16 H16 125.0(19) . . ? C15 C16 H16 115.5(19) . . ? C9 C8 C7 112.5(3) . . ? C9 C8 H8A 110.1(17) . . ? C7 C8 H8A 107.3(18) . . ? C9 C8 H8ER 110.1(17) . . ? C7 C8 H8ER 109.3(17) . . ? H8A C8 H8ER 107(2) . . ? C2 C3 C4 122.1(4) . . ? C2 C3 H3 117(2) . . ? C4 C3 H3 121(2) . . ? C12 C11 C10 111.4(3) . . ? C12 C11 H11E 111.0(17) . . ? C10 C11 H11E 109.8(17) . . ? C12 C11 H11A 110.3(19) . . ? C10 C11 H11A 109(2) . . ? H11E C11 H11A 105(3) . . ? C19 C18 C17 119.9(4) . . ? C19 C18 H18 120(2) . . ? C17 C18 H18 120(2) . . ? C18 C19 C20 120.4(4) . . ? C18 C19 H19 123(2) . . ? C20 C19 H19 117(2) . . ? C18 C17 C16 120.9(4) . . ? C18 C17 H17 121(2) . . ? C16 C17 H17 118(2) . . ? 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 C14 C13 C22 C21 -4.3(5) . . . . ? C10 C13 C22 C21 -179.1(3) . . . . ? C14 C13 C22 Cl1 175.1(2) . . . . ? C10 C13 C22 Cl1 0.3(5) . . . . ? C16 C15 C20 C19 1.4(5) . . . . ? C14 C15 C20 C19 -176.4(3) . . . . ? C16 C15 C20 C21 -179.9(3) . . . . ? C14 C15 C20 C21 2.3(5) . . . . ? C22 C13 C10 C11 -132.5(4) . . . . ? C14 C13 C10 C11 52.8(5) . . . . ? C22 C13 C10 C9 100.5(4) . . . . ? C14 C13 C10 C9 -74.3(4) . . . . ? C16 C15 C14 O1 -7.2(5) . . . . ? C20 C15 C14 O1 170.6(3) . . . . ? C16 C15 C14 C13 175.5(3) . . . . ? C20 C15 C14 C13 -6.6(5) . . . . ? C22 C13 C14 O1 -169.7(3) . . . . ? C10 C13 C14 O1 5.3(5) . . . . ? C22 C13 C14 C15 7.5(5) . . . . ? C10 C13 C14 C15 -177.5(3) . . . . ? C15 C20 C21 O2 -179.8(3) . . . . ? C19 C20 C21 O2 -1.1(5) . . . . ? C15 C20 C21 C22 1.0(4) . . . . ? C19 C20 C21 C22 179.7(3) . . . . ? C13 C22 C21 O2 -179.1(3) . . . . ? Cl1 C22 C21 O2 1.4(4) . . . . ? C13 C22 C21 C20 0.1(5) . . . . ? Cl1 C22 C21 C20 -179.4(2) . . . . ? C8 C7 C4 C5 116.9(4) . . . . ? C12 C7 C4 C5 -118.3(4) . . . . ? C8 C7 C4 C3 -62.1(5) . . . . ? C12 C7 C4 C3 62.7(5) . . . . ? C6 C1 C2 C3 0.7(6) . . . . ? Cl2 C1 C2 C3 -179.2(3) . . . . ? C3 C4 C5 C6 -1.0(6) . . . . ? C7 C4 C5 C6 180.0(4) . . . . ? C2 C1 C6 C5 -0.7(6) . . . . ? Cl2 C1 C6 C5 179.3(3) . . . . ? C4 C5 C6 C1 0.9(6) . . . . ? C13 C10 C9 C8 -177.2(3) . . . . ? C11 C10 C9 C8 53.3(5) . . . . ? C4 C7 C12 C11 177.6(3) . . . . ? C8 C7 C12 C11 -55.9(5) . . . . ? C20 C15 C16 C17 -1.4(5) . . . . ? C14 C15 C16 C17 176.4(3) . . . . ? C10 C9 C8 C7 -55.5(5) . . . . ? C4 C7 C8 C9 -177.2(3) . . . . ? C12 C7 C8 C9 55.9(4) . . . . ? C1 C2 C3 C4 -0.9(6) . . . . ? C5 C4 C3 C2 1.0(6) . . . . ? C7 C4 C3 C2 -180.0(4) . . . . ? C7 C12 C11 C10 55.6(5) . . . . ? C13 C10 C11 C12 -179.9(3) . . . . ? C9 C10 C11 C12 -53.3(5) . . . . ? C17 C18 C19 C20 -0.3(6) . . . . ? C15 C20 C19 C18 -0.6(5) . . . . ? C21 C20 C19 C18 -179.3(3) . . . . ? C19 C18 C17 C16 0.2(7) . . . . ? C15 C16 C17 C18 0.6(6) . . . . ? data_sri2_m _database_code_depnum_ccdc_archive 'CCDC 749771' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; cis-2-(4-(4-chlorophenyl) cyclohexyl) -3-chloronaphthalene-1,4-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Cl2 O2' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C22 H18 Cl2 O2' _chemical_formula_iupac ? _chemical_formula_weight 385.26 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 5.9770(18) _cell_length_b 12.226(4) _cell_length_c 13.103(4) _cell_angle_alpha 103.814(5) _cell_angle_beta 90.038(4) _cell_angle_gamma 95.271(6) _cell_volume 925.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 450 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.364 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9407 _exptl_absorpt_correction_T_max 0.9542 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 6683 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 3241 # number of observed reflections (> n sig(I)) _reflns_number_gt 2141 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0728P)^2^+0.3873P] 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 3241 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1556 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.495 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.042 #=============================================================================== # 9. 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C8 C -0.1431(7) 0.5353(3) 0.8514(3) 0.0753(10) Uani 1 1 d . . . H8A H -0.264(6) 0.500(3) 0.885(3) 0.092(11) Uiso 1 1 d . . . H8E H -0.052(6) 0.479(3) 0.818(3) 0.084(12) Uiso 1 1 d . . . C9 C -0.0080(6) 0.6244(3) 0.9347(3) 0.0616(8) Uani 1 1 d . . . H9A H 0.113(5) 0.666(2) 0.901(2) 0.060(8) Uiso 1 1 d . . . H9E H 0.070(5) 0.587(3) 0.984(3) 0.079(10) Uiso 1 1 d . . . Cl2 Cl 0.33884(19) 0.69571(9) 0.42832(7) 0.1025(4) Uani 1 1 d . . . Cl1 Cl -0.3638(2) 0.70680(11) 1.20940(8) 0.1094(5) Uani 1 1 d . . . O1 O 0.2104(4) 0.8741(2) 0.99396(15) 0.0769(7) Uani 1 1 d . . . C13 C -0.0564(5) 0.7894(3) 1.0905(2) 0.0554(7) Uani 1 1 d . . . C21 C -0.0294(6) 0.8670(3) 1.2864(2) 0.0729(10) Uani 1 1 d . . . C14 C 0.1454(5) 0.8675(3) 1.0809(2) 0.0569(7) Uani 1 1 d . . . O2 O -0.1168(5) 0.8704(3) 1.37063(18) 0.1061(10) Uani 1 1 d . . . C4 C -0.0956(4) 0.6208(3) 0.6910(2) 0.0536(7) Uani 1 1 d . . . C10 C -0.1616(5) 0.7104(3) 0.9935(2) 0.0602(8) Uani 1 1 d . . . H10 H -0.283(5) 0.661(2) 1.016(2) 0.062(8) Uiso 1 1 d . . . C1 C 0.1716(6) 0.6679(3) 0.5302(2) 0.0662(9) Uani 1 1 d . . . C15 C 0.2680(5) 0.9350(3) 1.1768(2) 0.0595(8) Uani 1 1 d . . . C22 C -0.1315(5) 0.7925(3) 1.1882(2) 0.0647(9) Uani 1 1 d . . . C5 C 0.0927(5) 0.5654(3) 0.6602(3) 0.0666(9) Uani 1 1 d . . . H5 H 0.131(5) 0.508(3) 0.693(3) 0.077(10) Uiso 1 1 d . . . C7 C -0.2556(5) 0.5856(3) 0.7711(3) 0.0668(9) Uani 1 1 d . . . H7 H -0.357(5) 0.528(2) 0.733(2) 0.060(8) Uiso 1 1 d . . . C6 C 0.2254(6) 0.5892(4) 0.5804(3) 0.0746(10) Uani 1 1 d . . . H6 H 0.348(6) 0.549(3) 0.565(3) 0.092(12) Uiso 1 1 d . . . C3 C -0.1416(7) 0.7007(3) 0.6389(3) 0.0824(11) Uani 1 1 d . . . H3 H -0.269(7) 0.733(4) 0.649(3) 0.113(15) Uiso 1 1 d . . . C11 C -0.2650(6) 0.7670(4) 0.9145(3) 0.0714(10) Uani 1 1 d . . . H11E H -0.366(6) 0.820(3) 0.954(3) 0.084(10) Uiso 1 1 d . . . H11A H -0.151(5) 0.807(2) 0.889(2) 0.061(9) Uiso 1 1 d . . . C19 C 0.3033(9) 0.9977(4) 1.3657(3) 0.0874(12) Uani 1 1 d . . . H19 H 0.235(6) 0.995(3) 1.426(3) 0.090(12) Uiso 1 1 d . . . C2 C -0.0100(7) 0.7251(4) 0.5590(3) 0.0877(12) Uani 1 1 d . . . H2 H -0.057(7) 0.781(4) 0.531(3) 0.112(15) Uiso 1 1 d . . . C12 C -0.3961(6) 0.6784(4) 0.8294(3) 0.0800(11) Uani 1 1 d . . . H12E H -0.461(5) 0.717(3) 0.779(3) 0.070(10) Uiso 1 1 d . . . H12A H -0.526(7) 0.645(3) 0.858(3) 0.108(13) Uiso 1 1 d . . . C17 C 0.5867(8) 1.0597(3) 1.2578(3) 0.0874(11) Uani 1 1 d . . . H17 H 0.743(8) 1.105(4) 1.252(4) 0.133(17) Uiso 1 1 d . . . C18 C 0.5010(10) 1.0582(4) 1.3556(4) 0.0977(14) Uani 1 1 d . . . H18 H 0.584(6) 1.101(3) 1.414(3) 0.103(13) Uiso 1 1 d . . . C20 C 0.1833(6) 0.9350(3) 1.2765(2) 0.0680(9) Uani 1 1 d . . . C16 C 0.4694(6) 0.9985(3) 1.1689(3) 0.0709(9) Uani 1 1 d . . . H16 H 0.525(5) 0.999(3) 1.102(3) 0.077(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 C8 0.093(3) 0.068(2) 0.063(2) 0.0208(19) 0.016(2) -0.011(2) C9 0.069(2) 0.066(2) 0.0570(19) 0.0286(16) 0.0076(16) 0.0051(16) Cl2 0.1256(9) 0.1051(8) 0.0620(6) 0.0042(5) 0.0447(5) -0.0235(6) Cl1 0.1159(8) 0.1329(10) 0.0856(7) 0.0447(6) 0.0513(6) -0.0062(7) O1 0.0774(14) 0.1069(18) 0.0428(12) 0.0216(11) 0.0149(10) -0.0208(13) C13 0.0555(17) 0.072(2) 0.0458(16) 0.0248(15) 0.0162(13) 0.0124(14) C21 0.099(3) 0.087(2) 0.0443(18) 0.0280(17) 0.0252(17) 0.034(2) C14 0.0632(18) 0.0677(19) 0.0431(16) 0.0194(14) 0.0157(13) 0.0075(14) O2 0.131(2) 0.150(3) 0.0463(14) 0.0352(15) 0.0360(14) 0.0298(19) C4 0.0467(16) 0.0652(19) 0.0429(15) 0.0059(14) 0.0009(12) -0.0067(13) C10 0.0522(17) 0.081(2) 0.0490(17) 0.0238(16) 0.0156(13) -0.0047(15) C1 0.075(2) 0.071(2) 0.0442(17) 0.0049(16) 0.0132(15) -0.0151(17) C15 0.074(2) 0.0595(19) 0.0470(17) 0.0150(14) 0.0079(14) 0.0126(16) C22 0.071(2) 0.078(2) 0.0524(18) 0.0283(16) 0.0273(15) 0.0160(16) C5 0.0573(19) 0.090(3) 0.0576(19) 0.0275(18) 0.0018(15) 0.0098(17) C7 0.0531(18) 0.084(2) 0.0555(19) 0.0113(17) 0.0040(15) -0.0192(17) C6 0.056(2) 0.096(3) 0.066(2) 0.007(2) 0.0168(16) 0.0080(19) C3 0.075(2) 0.091(3) 0.095(3) 0.041(2) 0.033(2) 0.027(2) C11 0.058(2) 0.101(3) 0.057(2) 0.0153(19) 0.0138(16) 0.026(2) C19 0.137(4) 0.079(3) 0.047(2) 0.0113(19) 0.003(2) 0.026(3) C2 0.100(3) 0.090(3) 0.086(3) 0.043(2) 0.030(2) 0.019(2) C12 0.0425(18) 0.135(3) 0.063(2) 0.025(2) 0.0084(16) 0.007(2) C17 0.112(3) 0.067(2) 0.078(3) 0.010(2) -0.015(2) 0.002(2) C18 0.145(4) 0.071(3) 0.068(3) 0.000(2) -0.027(3) 0.010(3) C20 0.098(2) 0.067(2) 0.0430(17) 0.0159(15) 0.0109(16) 0.0254(18) C16 0.087(2) 0.066(2) 0.060(2) 0.0147(17) 0.0005(19) 0.0038(18) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 C8 C9 1.516(5) . ? C8 C7 1.524(5) . ? C8 H8A 0.97(4) . ? C8 H8E 0.95(4) . ? C9 C10 1.527(4) . ? C9 H9A 1.01(3) . ? C9 H9E 1.01(3) . ? Cl2 C1 1.747(3) . ? Cl1 C22 1.725(3) . ? O1 C14 1.222(3) . ? C13 C22 1.349(4) . ? C13 C14 1.493(4) . ? C13 C10 1.498(4) . ? C21 O2 1.214(3) . ? C21 C20 1.478(5) . ? C21 C22 1.482(5) . ? C14 C15 1.479(4) . ? C4 C3 1.366(5) . ? C4 C5 1.378(4) . ? C4 C7 1.530(4) . ? C10 C11 1.534(5) . ? C10 H10 0.99(3) . ? C1 C6 1.349(5) . ? C1 C2 1.350(5) . ? C15 C16 1.389(5) . ? C15 C20 1.401(4) . ? C5 C6 1.382(5) . ? C5 H5 0.94(3) . ? C7 C12 1.529(5) . ? C7 H7 0.93(3) . ? C6 H6 0.92(4) . ? C3 C2 1.381(5) . ? C3 H3 0.89(4) . ? C11 C12 1.515(5) . ? C11 H11E 0.99(4) . ? C11 H11A 0.91(3) . ? C19 C18 1.359(6) . ? C19 C20 1.392(5) . ? C19 H19 0.89(4) . ? C2 H2 0.91(4) . ? C12 H12E 1.00(3) . ? C12 H12A 0.96(4) . ? C17 C16 1.377(5) . ? C17 C18 1.385(6) . ? C17 H17 1.05(5) . ? C18 H18 0.93(4) . ? C16 H16 0.94(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 C9 C8 C7 112.5(3) . . ? C9 C8 H8A 109(2) . . ? C7 C8 H8A 106(2) . . ? C9 C8 H8E 111(2) . . ? C7 C8 H8E 111(2) . . ? H8A C8 H8E 108(3) . . ? C8 C9 C10 109.8(3) . . ? C8 C9 H9A 110.5(16) . . ? C10 C9 H9A 107.9(16) . . ? C8 C9 H9E 109.8(19) . . ? C10 C9 H9E 111.8(19) . . ? H9A C9 H9E 107(2) . . ? C22 C13 C14 117.3(3) . . ? C22 C13 C10 123.3(3) . . ? C14 C13 C10 119.4(2) . . ? O2 C21 C20 122.2(4) . . ? O2 C21 C22 121.1(4) . . ? C20 C21 C22 116.7(2) . . ? O1 C14 C15 120.4(3) . . ? O1 C14 C13 119.9(3) . . ? C15 C14 C13 119.7(2) . . ? C3 C4 C5 116.1(3) . . ? C3 C4 C7 122.2(3) . . ? C5 C4 C7 121.4(3) . . ? C13 C10 C9 114.3(3) . . ? C13 C10 C11 115.6(3) . . ? C9 C10 C11 108.6(2) . . ? C13 C10 H10 107.7(17) . . ? C9 C10 H10 102.0(17) . . ? C11 C10 H10 107.6(17) . . ? C6 C1 C2 120.0(3) . . ? C6 C1 Cl2 119.6(3) . . ? C2 C1 Cl2 120.3(3) . . ? C16 C15 C20 119.3(3) . . ? C16 C15 C14 120.2(3) . . ? C20 C15 C14 120.5(3) . . ? C13 C22 C21 125.2(3) . . ? C13 C22 Cl1 121.6(3) . . ? C21 C22 Cl1 113.2(2) . . ? C4 C5 C6 121.6(3) . . ? C4 C5 H5 120(2) . . ? C6 C5 H5 119(2) . . ? C8 C7 C12 108.7(3) . . ? C8 C7 C4 114.3(3) . . ? C12 C7 C4 114.8(3) . . ? C8 C7 H7 106.1(17) . . ? C12 C7 H7 106.3(17) . . ? C4 C7 H7 105.9(17) . . ? C1 C6 C5 120.2(3) . . ? C1 C6 H6 124(2) . . ? C5 C6 H6 116(2) . . ? C4 C3 C2 122.7(4) . . ? C4 C3 H3 121(3) . . ? C2 C3 H3 116(3) . . ? C12 C11 C10 109.9(3) . . ? C12 C11 H11E 110(2) . . ? C10 C11 H11E 107(2) . . ? C12 C11 H11A 113.1(19) . . ? C10 C11 H11A 107.9(19) . . ? H11E C11 H11A 109(3) . . ? C18 C19 C20 119.9(4) . . ? C18 C19 H19 126(3) . . ? C20 C19 H19 114(3) . . ? C1 C2 C3 119.4(4) . . ? C1 C2 H2 126(3) . . ? C3 C2 H2 114(3) . . ? C11 C12 C7 113.5(3) . . ? C11 C12 H12E 108.8(19) . . ? C7 C12 H12E 109.9(18) . . ? C11 C12 H12A 111(2) . . ? C7 C12 H12A 110(2) . . ? H12E C12 H12A 103(3) . . ? C16 C17 C18 119.3(4) . . ? C16 C17 H17 120(3) . . ? C18 C17 H17 120(3) . . ? C19 C18 C17 121.4(4) . . ? C19 C18 H18 121(3) . . ? C17 C18 H18 117(3) . . ? C19 C20 C15 119.5(4) . . ? C19 C20 C21 120.5(3) . . ? C15 C20 C21 120.0(3) . . ? C17 C16 C15 120.6(4) . . ? C17 C16 H16 120(2) . . ? C15 C16 H16 119(2) . . ? 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 C7 C8 C9 C10 59.7(4) . . . . ? C22 C13 C14 O1 -174.6(3) . . . . ? C10 C13 C14 O1 6.9(4) . . . . ? C22 C13 C14 C15 6.4(4) . . . . ? C10 C13 C14 C15 -172.1(3) . . . . ? C22 C13 C10 C9 -116.1(3) . . . . ? C14 C13 C10 C9 62.2(4) . . . . ? C22 C13 C10 C11 116.7(3) . . . . ? C14 C13 C10 C11 -64.9(3) . . . . ? C8 C9 C10 C13 169.0(3) . . . . ? C8 C9 C10 C11 -60.4(4) . . . . ? O1 C14 C15 C16 -6.0(5) . . . . ? C13 C14 C15 C16 173.0(3) . . . . ? O1 C14 C15 C20 174.5(3) . . . . ? C13 C14 C15 C20 -6.5(4) . . . . ? C14 C13 C22 C21 -0.1(5) . . . . ? C10 C13 C22 C21 178.3(3) . . . . ? C14 C13 C22 Cl1 179.8(2) . . . . ? C10 C13 C22 Cl1 -1.8(4) . . . . ? O2 C21 C22 C13 174.6(3) . . . . ? C20 C21 C22 C13 -6.0(5) . . . . ? O2 C21 C22 Cl1 -5.2(4) . . . . ? C20 C21 C22 Cl1 174.1(2) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C7 C4 C5 C6 173.5(3) . . . . ? C9 C8 C7 C12 -54.4(4) . . . . ? C9 C8 C7 C4 75.3(4) . . . . ? C3 C4 C7 C8 -156.3(3) . . . . ? C5 C4 C7 C8 30.1(4) . . . . ? C3 C4 C7 C12 -29.7(5) . . . . ? C5 C4 C7 C12 156.7(3) . . . . ? C2 C1 C6 C5 1.3(5) . . . . ? Cl2 C1 C6 C5 -179.1(3) . . . . ? C4 C5 C6 C1 -0.4(5) . . . . ? C5 C4 C3 C2 0.5(6) . . . . ? C7 C4 C3 C2 -173.4(4) . . . . ? C13 C10 C11 C12 -171.2(2) . . . . ? C9 C10 C11 C12 58.9(3) . . . . ? C6 C1 C2 C3 -1.2(6) . . . . ? Cl2 C1 C2 C3 179.2(3) . . . . ? C4 C3 C2 C1 0.3(7) . . . . ? C10 C11 C12 C7 -56.9(4) . . . . ? C8 C7 C12 C11 53.4(4) . . . . ? C4 C7 C12 C11 -76.1(4) . . . . ? C20 C19 C18 C17 0.4(6) . . . . ? C16 C17 C18 C19 -0.1(6) . . . . ? C18 C19 C20 C15 0.0(6) . . . . ? C18 C19 C20 C21 178.8(3) . . . . ? C16 C15 C20 C19 -0.5(5) . . . . ? C14 C15 C20 C19 179.0(3) . . . . ? C16 C15 C20 C21 -179.3(3) . . . . ? C14 C15 C20 C21 0.2(4) . . . . ? O2 C21 C20 C19 6.4(5) . . . . ? C22 C21 C20 C19 -173.0(3) . . . . ? O2 C21 C20 C15 -174.8(3) . . . . ? C22 C21 C20 C15 5.8(4) . . . . ? C18 C17 C16 C15 -0.5(6) . . . . ? C20 C15 C16 C17 0.8(5) . . . . ? C14 C15 C16 C17 -178.7(3) . . . . ? data_sri1_m _database_code_depnum_ccdc_archive 'CCDC 749772' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; cis-2-(4-(4-chlorophenyl)cyclohexyl)-3-nitronaphthalene-1,4-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Cl N O4' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C22 H18 Cl N O4' _chemical_formula_iupac ? _chemical_formula_weight 395.82 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 11.7512(16) _cell_length_b 12.7998(18) _cell_length_c 13.985(2) _cell_angle_alpha 75.766(3) _cell_angle_beta 67.022(2) _cell_angle_gamma 83.020(3) _cell_volume 1876.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 292(2) _cell_measurement_reflns_used 450 _cell_measurement_theta_min 0.98 _cell_measurement_theta_max 27.98 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.17 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.233 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'SADABS, (Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9313 _exptl_absorpt_correction_T_max 0.9615 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 292(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? # number of measured reflections (redundant set) _diffrn_reflns_number 13653 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0767 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 6565 # number of observed reflections (> n sig(I)) _reflns_number_gt 3091 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0414P)^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 6565 _refine_ls_number_parameters 649 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1346 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.188 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.037 #=============================================================================== # 9. 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 0.06547(8) 0.70587(8) 0.08025(7) 0.0798(3) Uani 1 1 d . . . Cl1 Cl -0.45833(9) 0.68527(9) 0.07887(8) 0.1073(5) Uani 1 1 d . . . C13 C 0.0862(3) 0.7823(2) -0.5824(2) 0.0425(8) Uani 1 1 d . . . N1 N 0.2797(2) 0.7066(2) -0.69271(19) 0.0483(7) Uani 1 1 d . . . O4 O -0.0974(2) 0.86930(18) -0.48901(17) 0.0716(7) Uani 1 1 d . . . C22 C 0.1744(3) 0.7855(2) -0.6789(2) 0.0429(8) Uani 1 1 d . . . O7 O 0.3926(2) 0.89406(18) -0.49965(17) 0.0696(7) Uani 1 1 d . . . C21 C 0.1799(3) 0.8603(3) -0.7792(2) 0.0489(8) Uani 1 1 d . . . O3 O 0.2698(2) 0.85912(18) -0.86082(17) 0.0714(7) Uani 1 1 d . . . N2 N 0.7622(3) 0.7339(2) -0.7177(2) 0.0564(8) Uani 1 1 d . . . C10 C 0.0879(3) 0.7017(3) -0.4842(2) 0.0461(9) Uani 1 1 d . . . C14 C -0.0181(3) 0.8633(2) -0.5750(3) 0.0483(8) Uani 1 1 d . . . C35 C 0.5702(3) 0.8054(2) -0.6003(2) 0.0417(8) Uani 1 1 d . . . C36 C 0.4647(3) 0.8869(2) -0.5885(3) 0.0488(8) Uani 1 1 d . . . O8 O 0.7402(2) 0.88886(19) -0.88076(17) 0.0805(8) Uani 1 1 d . . . C32 C 0.5774(3) 0.7231(3) -0.5055(2) 0.0431(8) Uani 1 1 d . . . C44 C 0.6545(3) 0.8110(2) -0.6987(2) 0.0456(8) Uani 1 1 d . . . C37 C 0.4501(3) 0.9548(2) -0.6852(2) 0.0475(8) Uani 1 1 d . . . C43 C 0.6530(3) 0.8865(3) -0.7971(2) 0.0546(9) Uani 1 1 d . . . C9 C -0.0181(3) 0.6232(3) -0.4345(3) 0.0502(9) Uani 1 1 d . . . H9A H -0.097(2) 0.666(2) -0.4034(19) 0.042(8) Uiso 1 1 d . . . H9E H -0.031(2) 0.595(2) -0.488(2) 0.059(10) Uiso 1 1 d . . . C4 C -0.1049(3) 0.6126(2) -0.1834(2) 0.0425(8) Uani 1 1 d . . . C20 C 0.0714(3) 0.9327(2) -0.7729(2) 0.0478(8) Uani 1 1 d . . . C11 C 0.0971(4) 0.7502(3) -0.3983(3) 0.0523(9) Uani 1 1 d . . . H11E H 0.163(3) 0.799(2) -0.425(2) 0.060(10) Uiso 1 1 d . . . H11A H 0.019(3) 0.793(2) -0.366(2) 0.057(10) Uiso 1 1 d . . . C15 C -0.0237(3) 0.9343(2) -0.6740(2) 0.0458(8) Uani 1 1 d . . . O2 O 0.3686(2) 0.72867(19) -0.67900(19) 0.0719(7) Uani 1 1 d . . . C26 C 0.3994(3) 0.6322(3) -0.1992(2) 0.0422(8) Uani 1 1 d . . . C42 C 0.5406(3) 0.9547(2) -0.7858(3) 0.0501(9) Uani 1 1 d . . . C23 C 0.1931(3) 0.6801(3) -0.0290(2) 0.0512(9) Uani 1 1 d . . . C38 C 0.3427(4) 1.0179(3) -0.6753(3) 0.0576(10) Uani 1 1 d . . . H38 H 0.277(3) 1.018(3) -0.605(3) 0.092(13) Uiso 1 1 d . . . C29 C 0.5156(3) 0.5959(3) -0.2834(3) 0.0511(9) Uani 1 1 d . . . C27 C 0.2959(3) 0.5699(3) -0.1532(3) 0.0507(9) Uani 1 1 d . . . O1 O 0.2692(2) 0.6255(2) -0.7169(2) 0.0862(9) Uani 1 1 d . . . C31 C 0.4664(3) 0.6504(3) -0.4507(3) 0.0506(9) Uani 1 1 d . . . H31A H 0.395(2) 0.691(2) -0.416(2) 0.047(9) Uiso 1 1 d . . . H31E H 0.449(2) 0.622(2) -0.502(2) 0.057(10) Uiso 1 1 d . . . C8 C 0.0050(4) 0.5336(3) -0.3495(3) 0.0583(10) Uani 1 1 d . . . C16 C -0.1269(4) 1.0014(3) -0.6704(3) 0.0585(10) Uani 1 1 d . . . C34 C 0.6190(3) 0.6780(3) -0.3383(3) 0.0572(10) Uani 1 1 d . . . H34E H 0.636(2) 0.710(2) -0.285(2) 0.047(9) Uiso 1 1 d . . . H34A H 0.697(3) 0.638(2) -0.373(2) 0.063(10) Uiso 1 1 d . . . O5 O 0.7538(2) 0.6561(2) -0.7491(2) 0.0868(9) Uani 1 1 d . . . C6 C -0.3247(3) 0.5924(3) -0.0857(3) 0.0651(11) Uani 1 1 d . . . H6 H -0.404(3) 0.559(2) -0.073(2) 0.083(12) Uiso 1 1 d . . . C12 C 0.1175(3) 0.6611(3) -0.3117(3) 0.0616(11) Uani 1 1 d . . . H12E H 0.125(3) 0.692(2) -0.254(2) 0.066(11) Uiso 1 1 d . . . H12A H 0.197(3) 0.622(2) -0.343(2) 0.084(12) Uiso 1 1 d . . . C7 C 0.0169(3) 0.5769(3) -0.2617(3) 0.0524(9) Uani 1 1 d . . . O6 O 0.8488(2) 0.7515(2) -0.6999(2) 0.0934(9) Uani 1 1 d . . . C28 C 0.1927(3) 0.5936(3) -0.0686(3) 0.0544(10) Uani 1 1 d . . . H28 H 0.130(3) 0.547(2) -0.043(2) 0.046(9) Uiso 1 1 d . . . C30 C 0.4900(4) 0.5575(3) -0.3684(3) 0.0573(10) Uani 1 1 d . . . H30A H 0.565(3) 0.516(2) -0.404(2) 0.071(11) Uiso 1 1 d . . . H30E H 0.423(3) 0.507(2) -0.336(2) 0.058(10) Uiso 1 1 d . . . C1 C -0.3238(3) 0.6591(3) -0.0236(3) 0.0637(11) Uani 1 1 d . . . C33 C 0.5970(4) 0.7689(3) -0.4222(3) 0.0525(9) Uani 1 1 d . . . H33E H 0.671(3) 0.816(2) -0.459(2) 0.059(9) Uiso 1 1 d . . . H33A H 0.527(3) 0.814(2) -0.391(2) 0.059(10) Uiso 1 1 d . . . C39 C 0.3256(4) 1.0785(3) -0.7650(3) 0.0681(11) Uani 1 1 d . . . H39 H 0.248(3) 1.119(2) -0.755(2) 0.058(10) Uiso 1 1 d . . . C40 C 0.4153(5) 1.0773(3) -0.8641(4) 0.0761(13) Uani 1 1 d . . . C5 C -0.2155(3) 0.5693(3) -0.1649(3) 0.0545(9) Uani 1 1 d . . . H5 H -0.223(3) 0.517(3) -0.204(3) 0.091(13) Uiso 1 1 d . . . C3 C -0.1086(4) 0.6810(3) -0.1201(3) 0.0654(11) Uani 1 1 d . . . C41 C 0.5222(4) 1.0170(3) -0.8752(3) 0.0664(11) Uani 1 1 d . . . H41 H 0.585(3) 1.015(2) -0.938(2) 0.052(10) Uiso 1 1 d . . . C24 C 0.2922(3) 0.7444(3) -0.0730(3) 0.0643(11) Uani 1 1 d . . . H24 H 0.291(3) 0.804(2) -0.043(2) 0.072(11) Uiso 1 1 d . . . C19 C 0.0620(4) 0.9987(3) -0.8647(3) 0.0661(11) Uani 1 1 d . . . H19 H 0.129(3) 0.993(2) -0.928(3) 0.077(12) Uiso 1 1 d . . . C2 C -0.2168(4) 0.7037(3) -0.0401(3) 0.0746(13) Uani 1 1 d . . . H2 H -0.212(3) 0.744(3) 0.003(3) 0.093(15) Uiso 1 1 d . . . C18 C -0.0412(5) 1.0634(3) -0.8594(4) 0.0773(12) Uani 1 1 d . . . H18 H -0.050(3) 1.105(3) -0.925(3) 0.099(13) Uiso 1 1 d . . . C17 C -0.1358(4) 1.0651(3) -0.7615(4) 0.0713(12) Uani 1 1 d . . . H17 H -0.211(3) 1.105(2) -0.761(2) 0.067(11) Uiso 1 1 d . . . C25 C 0.3938(3) 0.7207(3) -0.1577(3) 0.0611(10) Uani 1 1 d . . . H25 H 0.467(3) 0.766(2) -0.190(2) 0.081(11) Uiso 1 1 d . . . H10 H 0.159(2) 0.6573(19) -0.5064(18) 0.036(8) Uiso 1 1 d . . . H8E H -0.063(3) 0.476(3) -0.318(3) 0.087(12) Uiso 1 1 d . . . H40 H 0.405(2) 1.119(2) -0.925(2) 0.059(10) Uiso 1 1 d . . . H32 H 0.646(3) 0.677(2) -0.532(2) 0.052(9) Uiso 1 1 d . . . H7 H 0.045(2) 0.517(2) -0.219(2) 0.042(8) Uiso 1 1 d . . . H29 H 0.548(2) 0.535(2) -0.242(2) 0.049(8) Uiso 1 1 d . . . H8A H 0.084(3) 0.492(2) -0.383(2) 0.079(11) Uiso 1 1 d . . . H3 H -0.034(3) 0.715(2) -0.131(2) 0.068(11) Uiso 1 1 d . . . H16 H -0.190(2) 0.998(2) -0.604(2) 0.047(9) Uiso 1 1 d . . . H27 H 0.292(2) 0.509(2) -0.176(2) 0.046(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 Cl2 0.0662(6) 0.0868(7) 0.0530(6) -0.0093(5) 0.0048(5) 0.0139(5) Cl1 0.0843(8) 0.1067(9) 0.0633(7) 0.0011(6) 0.0220(6) 0.0329(6) C13 0.0348(18) 0.047(2) 0.0401(19) -0.0126(16) -0.0063(15) 0.0000(15) N1 0.0366(17) 0.059(2) 0.0407(16) -0.0184(14) -0.0009(13) 0.0007(16) O4 0.0594(16) 0.0885(18) 0.0441(14) -0.0167(13) -0.0028(12) 0.0283(13) C22 0.0379(19) 0.048(2) 0.0387(19) -0.0169(16) -0.0068(15) 0.0034(16) O7 0.0613(15) 0.0862(18) 0.0412(14) -0.0173(12) -0.0034(12) 0.0243(13) C21 0.051(2) 0.055(2) 0.036(2) -0.0118(17) -0.0089(17) -0.0090(18) O3 0.0625(16) 0.0881(18) 0.0396(14) -0.0130(12) 0.0056(12) -0.0011(13) N2 0.049(2) 0.059(2) 0.0512(18) -0.0233(15) -0.0009(15) -0.0031(17) C10 0.037(2) 0.053(2) 0.035(2) -0.0096(17) -0.0032(16) 0.0083(18) C14 0.041(2) 0.053(2) 0.043(2) -0.0105(17) -0.0086(17) 0.0038(17) C35 0.0369(19) 0.045(2) 0.0408(19) -0.0169(16) -0.0075(15) -0.0020(15) C36 0.046(2) 0.053(2) 0.040(2) -0.0153(17) -0.0060(17) -0.0008(17) O8 0.0813(18) 0.0847(19) 0.0427(15) -0.0105(13) 0.0107(14) -0.0055(14) C32 0.034(2) 0.052(2) 0.0377(19) -0.0134(17) -0.0068(16) 0.0047(17) C44 0.040(2) 0.047(2) 0.041(2) -0.0171(16) -0.0014(16) -0.0015(16) C37 0.057(2) 0.039(2) 0.041(2) -0.0103(16) -0.0115(17) -0.0033(17) C43 0.065(3) 0.052(2) 0.036(2) -0.0148(17) 0.0002(18) -0.0128(19) C9 0.054(2) 0.053(2) 0.042(2) -0.0153(19) -0.0132(19) -0.0054(19) C4 0.040(2) 0.046(2) 0.0323(18) -0.0008(15) -0.0088(15) 0.0029(16) C20 0.057(2) 0.043(2) 0.043(2) -0.0054(16) -0.0180(18) -0.0057(17) C11 0.045(2) 0.064(3) 0.046(2) -0.0082(19) -0.0132(18) -0.016(2) C15 0.052(2) 0.041(2) 0.043(2) -0.0128(16) -0.0136(17) -0.0006(16) O2 0.0476(15) 0.0848(19) 0.0867(19) -0.0278(14) -0.0236(14) -0.0007(14) C26 0.040(2) 0.048(2) 0.0338(18) -0.0030(16) -0.0146(15) 0.0048(17) C42 0.064(2) 0.038(2) 0.043(2) -0.0094(17) -0.0131(18) -0.0057(17) C23 0.048(2) 0.054(2) 0.041(2) -0.0043(18) -0.0121(17) 0.0102(19) C38 0.069(3) 0.048(2) 0.056(3) -0.013(2) -0.024(2) 0.004(2) C29 0.051(2) 0.057(2) 0.043(2) -0.0090(18) -0.0218(18) 0.0125(19) C27 0.060(3) 0.048(2) 0.046(2) -0.0092(18) -0.0227(19) 0.001(2) O1 0.0709(18) 0.0727(19) 0.126(2) -0.0606(18) -0.0295(16) 0.0139(14) C31 0.053(2) 0.058(2) 0.042(2) -0.0161(19) -0.0134(19) -0.009(2) C8 0.061(3) 0.046(2) 0.050(2) -0.0113(19) -0.002(2) 0.002(2) C16 0.062(3) 0.051(2) 0.059(3) -0.014(2) -0.021(2) 0.008(2) C34 0.038(2) 0.088(3) 0.050(2) -0.024(2) -0.0166(19) 0.004(2) O5 0.082(2) 0.076(2) 0.107(2) -0.0541(17) -0.0230(16) 0.0105(15) C6 0.044(3) 0.085(3) 0.053(3) -0.005(2) -0.012(2) 0.000(2) C12 0.041(2) 0.090(3) 0.045(2) -0.003(2) -0.0137(19) -0.003(2) C7 0.048(2) 0.056(2) 0.037(2) 0.0022(18) -0.0086(17) 0.0066(18) O6 0.0460(16) 0.112(2) 0.133(3) -0.0612(19) -0.0252(17) 0.0008(16) C28 0.043(2) 0.059(3) 0.048(2) 0.006(2) -0.0126(19) -0.007(2) C30 0.068(3) 0.047(2) 0.048(2) -0.0157(19) -0.009(2) 0.001(2) C1 0.050(2) 0.068(3) 0.041(2) 0.008(2) 0.0008(18) 0.017(2) C33 0.043(2) 0.068(3) 0.047(2) -0.015(2) -0.0128(19) -0.012(2) C39 0.081(3) 0.053(3) 0.073(3) -0.018(2) -0.032(3) 0.008(2) C40 0.121(4) 0.051(3) 0.063(3) -0.003(2) -0.047(3) 0.000(3) C5 0.043(2) 0.075(3) 0.041(2) -0.0137(19) -0.0110(18) -0.0024(19) C3 0.053(3) 0.071(3) 0.068(3) -0.026(2) -0.010(2) -0.007(2) C41 0.089(3) 0.053(3) 0.048(3) -0.012(2) -0.014(2) -0.004(2) C24 0.060(3) 0.064(3) 0.063(3) -0.029(2) -0.008(2) -0.005(2) C19 0.080(3) 0.058(3) 0.052(3) -0.005(2) -0.019(2) -0.005(2) C2 0.085(4) 0.066(3) 0.061(3) -0.026(2) -0.011(3) 0.013(2) C18 0.109(4) 0.057(3) 0.065(3) -0.003(2) -0.041(3) 0.006(3) C17 0.083(3) 0.055(3) 0.082(3) -0.011(2) -0.045(3) 0.018(2) C25 0.050(2) 0.067(3) 0.060(2) -0.026(2) -0.006(2) -0.003(2) #=============================================================================== # 10. MOLECULAR GEOMETRY _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 Cl2 C23 1.741(3) . ? Cl1 C1 1.733(3) . ? C13 C22 1.338(4) . ? C13 C14 1.494(4) . ? C13 C10 1.506(4) . ? N1 O1 1.202(3) . ? N1 O2 1.209(3) . ? N1 C22 1.482(4) . ? O4 C14 1.214(3) . ? C22 C21 1.473(4) . ? O7 C36 1.218(3) . ? C21 O3 1.217(3) . ? C21 C20 1.469(4) . ? N2 O6 1.196(3) . ? N2 O5 1.210(3) . ? N2 C44 1.486(4) . ? C10 C11 1.524(4) . ? C10 C9 1.527(4) . ? C10 H10 0.94(2) . ? C14 C15 1.478(4) . ? C35 C44 1.336(4) . ? C35 C32 1.501(4) . ? C35 C36 1.505(4) . ? C36 C37 1.477(4) . ? O8 C43 1.215(3) . ? C32 C31 1.523(4) . ? C32 C33 1.527(4) . ? C32 H32 0.94(3) . ? C44 C43 1.480(4) . ? C37 C38 1.391(4) . ? C37 C42 1.394(4) . ? C43 C42 1.468(4) . ? C9 C8 1.519(4) . ? C9 H9A 1.01(2) . ? C9 H9E 0.98(3) . ? C4 C3 1.377(4) . ? C4 C5 1.380(4) . ? C4 C7 1.523(4) . ? C20 C19 1.389(4) . ? C20 C15 1.402(4) . ? C11 C12 1.519(5) . ? C11 H11E 0.95(3) . ? C11 H11A 1.01(3) . ? C15 C16 1.390(4) . ? C26 C25 1.378(4) . ? C26 C27 1.379(4) . ? C26 C29 1.525(4) . ? C42 C41 1.387(4) . ? C23 C24 1.355(4) . ? C23 C28 1.356(4) . ? C38 C39 1.377(5) . ? C38 H38 0.99(3) . ? C29 C30 1.532(4) . ? C29 C34 1.534(4) . ? C29 H29 0.99(3) . ? C27 C28 1.389(5) . ? C27 H27 0.92(3) . ? C31 C30 1.520(5) . ? C31 H31A 0.96(3) . ? C31 H31E 0.97(3) . ? C8 C7 1.524(5) . ? C8 H8E 1.04(3) . ? C8 H8A 1.01(3) . ? C16 C17 1.367(5) . ? C16 H16 0.93(3) . ? C34 C33 1.513(5) . ? C34 H34E 1.02(3) . ? C34 H34A 1.00(3) . ? C6 C1 1.362(5) . ? C6 C5 1.385(5) . ? C6 H6 1.00(3) . ? C12 C7 1.530(4) . ? C12 H12E 1.02(3) . ? C12 H12A 0.99(3) . ? C7 H7 0.95(2) . ? C28 H28 0.91(3) . ? C30 H30A 0.99(3) . ? C30 H30E 0.97(3) . ? C1 C2 1.358(5) . ? C33 H33E 1.00(3) . ? C33 H33A 0.96(3) . ? C39 C40 1.377(5) . ? C39 H39 0.97(3) . ? C40 C41 1.367(5) . ? C40 H40 0.94(3) . ? C5 H5 0.99(3) . ? C3 C2 1.382(5) . ? C3 H3 0.97(3) . ? C41 H41 0.91(3) . ? C24 C25 1.380(5) . ? C24 H24 0.95(3) . ? C19 C18 1.370(5) . ? C19 H19 0.94(3) . ? C2 H2 0.91(3) . ? C18 C17 1.389(5) . ? C18 H18 0.98(3) . ? C17 H17 0.96(3) . ? C25 H25 0.99(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 C22 C13 C14 116.7(3) . . ? C22 C13 C10 123.2(3) . . ? C14 C13 C10 120.1(3) . . ? O1 N1 O2 125.4(3) . . ? O1 N1 C22 116.7(3) . . ? O2 N1 C22 117.9(3) . . ? C13 C22 C21 127.1(3) . . ? C13 C22 N1 119.7(3) . . ? C21 C22 N1 113.2(3) . . ? O3 C21 C20 123.8(3) . . ? O3 C21 C22 120.4(3) . . ? C20 C21 C22 115.8(3) . . ? O6 N2 O5 125.0(3) . . ? O6 N2 C44 118.6(3) . . ? O5 N2 C44 116.4(3) . . ? C13 C10 C11 115.0(3) . . ? C13 C10 C9 114.2(3) . . ? C11 C10 C9 109.5(3) . . ? C13 C10 H10 106.5(14) . . ? C11 C10 H10 106.8(15) . . ? C9 C10 H10 103.9(15) . . ? O4 C14 C15 120.9(3) . . ? O4 C14 C13 120.2(3) . . ? C15 C14 C13 118.9(3) . . ? C44 C35 C32 123.1(3) . . ? C44 C35 C36 116.2(3) . . ? C32 C35 C36 120.7(3) . . ? O7 C36 C37 121.8(3) . . ? O7 C36 C35 119.2(3) . . ? C37 C36 C35 118.9(3) . . ? C35 C32 C31 113.0(3) . . ? C35 C32 C33 115.0(3) . . ? C31 C32 C33 108.8(3) . . ? C35 C32 H32 106.1(16) . . ? C31 C32 H32 105.5(17) . . ? C33 C32 H32 107.7(16) . . ? C35 C44 C43 126.9(3) . . ? C35 C44 N2 119.9(3) . . ? C43 C44 N2 113.2(3) . . ? C38 C37 C42 119.8(3) . . ? C38 C37 C36 119.1(3) . . ? C42 C37 C36 121.1(3) . . ? O8 C43 C42 123.8(3) . . ? O8 C43 C44 120.4(3) . . ? C42 C43 C44 115.8(3) . . ? C8 C9 C10 109.9(3) . . ? C8 C9 H9A 111.3(14) . . ? C10 C9 H9A 107.4(14) . . ? C8 C9 H9E 111.9(17) . . ? C10 C9 H9E 111.9(17) . . ? H9A C9 H9E 104(2) . . ? C3 C4 C5 116.7(3) . . ? C3 C4 C7 121.6(3) . . ? C5 C4 C7 121.4(3) . . ? C19 C20 C15 119.8(3) . . ? C19 C20 C21 120.3(3) . . ? C15 C20 C21 119.9(3) . . ? C12 C11 C10 109.9(3) . . ? C12 C11 H11E 108.0(17) . . ? C10 C11 H11E 113.1(17) . . ? C12 C11 H11A 109.1(15) . . ? C10 C11 H11A 110.5(16) . . ? H11E C11 H11A 106(2) . . ? C16 C15 C20 118.8(3) . . ? C16 C15 C14 119.9(3) . . ? C20 C15 C14 121.3(3) . . ? C25 C26 C27 116.2(3) . . ? C25 C26 C29 123.5(3) . . ? C27 C26 C29 120.1(3) . . ? C41 C42 C37 119.6(3) . . ? C41 C42 C43 120.3(3) . . ? C37 C42 C43 120.1(3) . . ? C24 C23 C28 120.3(3) . . ? C24 C23 Cl2 120.7(3) . . ? C28 C23 Cl2 118.9(3) . . ? C39 C38 C37 119.8(4) . . ? C39 C38 H38 120(2) . . ? C37 C38 H38 121(2) . . ? C26 C29 C30 113.5(3) . . ? C26 C29 C34 115.2(3) . . ? C30 C29 C34 109.1(3) . . ? C26 C29 H29 103.1(15) . . ? C30 C29 H29 109.2(15) . . ? C34 C29 H29 106.2(15) . . ? C26 C27 C28 122.1(4) . . ? C26 C27 H27 121.8(18) . . ? C28 C27 H27 116.1(17) . . ? C30 C31 C32 110.1(3) . . ? C30 C31 H31A 108.8(16) . . ? C32 C31 H31A 109.3(16) . . ? C30 C31 H31E 109.6(17) . . ? C32 C31 H31E 111.2(17) . . ? H31A C31 H31E 108(2) . . ? C9 C8 C7 112.1(3) . . ? C9 C8 H8E 111.3(18) . . ? C7 C8 H8E 110.9(18) . . ? C9 C8 H8A 109.7(17) . . ? C7 C8 H8A 108.6(18) . . ? H8E C8 H8A 104(2) . . ? C17 C16 C15 120.8(4) . . ? C17 C16 H16 122.3(18) . . ? C15 C16 H16 116.8(17) . . ? C33 C34 C29 114.1(3) . . ? C33 C34 H34E 109.2(15) . . ? C29 C34 H34E 112.3(15) . . ? C33 C34 H34A 108.4(16) . . ? C29 C34 H34A 107.4(17) . . ? H34E C34 H34A 105(2) . . ? C1 C6 C5 119.6(4) . . ? C1 C6 H6 119.6(19) . . ? C5 C6 H6 120.7(19) . . ? C11 C12 C7 113.2(3) . . ? C11 C12 H12E 111.2(17) . . ? C7 C12 H12E 109.5(17) . . ? C11 C12 H12A 109.3(18) . . ? C7 C12 H12A 106.7(19) . . ? H12E C12 H12A 107(2) . . ? C4 C7 C8 114.6(3) . . ? C4 C7 C12 114.9(3) . . ? C8 C7 C12 109.0(3) . . ? C4 C7 H7 103.9(15) . . ? C8 C7 H7 105.7(15) . . ? C12 C7 H7 107.9(15) . . ? C23 C28 C27 119.4(4) . . ? C23 C28 H28 125.3(18) . . ? C27 C28 H28 115.2(18) . . ? C31 C30 C29 112.6(3) . . ? C31 C30 H30A 109.3(17) . . ? C29 C30 H30A 105.8(17) . . ? C31 C30 H30E 111.8(17) . . ? C29 C30 H30E 110.9(17) . . ? H30A C30 H30E 106(2) . . ? C2 C1 C6 120.2(4) . . ? C2 C1 Cl1 119.4(4) . . ? C6 C1 Cl1 120.3(3) . . ? C34 C33 C32 110.0(3) . . ? C34 C33 H33E 109.8(16) . . ? C32 C33 H33E 108.0(16) . . ? C34 C33 H33A 111.5(17) . . ? C32 C33 H33A 110.0(17) . . ? H33E C33 H33A 107(2) . . ? C38 C39 C40 120.0(4) . . ? C38 C39 H39 117.6(18) . . ? C40 C39 H39 122.4(17) . . ? C41 C40 C39 121.0(4) . . ? C41 C40 H40 118.7(18) . . ? C39 C40 H40 120.3(18) . . ? C4 C5 C6 121.8(4) . . ? C4 C5 H5 123(2) . . ? C6 C5 H5 115(2) . . ? C4 C3 C2 122.0(4) . . ? C4 C3 H3 120.4(18) . . ? C2 C3 H3 117.5(19) . . ? C40 C41 C42 119.9(4) . . ? C40 C41 H41 124.3(19) . . ? C42 C41 H41 115.8(19) . . ? C23 C24 C25 119.7(4) . . ? C23 C24 H24 118.9(19) . . ? C25 C24 H24 121.3(19) . . ? C18 C19 C20 120.3(4) . . ? C18 C19 H19 124(2) . . ? C20 C19 H19 115(2) . . ? C1 C2 C3 119.7(4) . . ? C1 C2 H2 122(2) . . ? C3 C2 H2 118(2) . . ? C19 C18 C17 120.0(4) . . ? C19 C18 H18 120(2) . . ? C17 C18 H18 120(2) . . ? C16 C17 C18 120.2(4) . . ? C16 C17 H17 121.0(19) . . ? C18 C17 H17 118.3(19) . . ? C26 C25 C24 122.3(4) . . ? C26 C25 H25 117.3(18) . . ? C24 C25 H25 120.4(19) . . ? 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 C14 C13 C22 C21 -0.1(5) . . . . ? C10 C13 C22 C21 179.4(3) . . . . ? C14 C13 C22 N1 -179.0(3) . . . . ? C10 C13 C22 N1 0.4(5) . . . . ? O1 N1 C22 C13 93.1(4) . . . . ? O2 N1 C22 C13 -87.0(4) . . . . ? O1 N1 C22 C21 -86.1(3) . . . . ? O2 N1 C22 C21 93.9(3) . . . . ? C13 C22 C21 O3 175.2(3) . . . . ? N1 C22 C21 O3 -5.8(4) . . . . ? C13 C22 C21 C20 -5.5(5) . . . . ? N1 C22 C21 C20 173.6(3) . . . . ? C22 C13 C10 C11 116.9(4) . . . . ? C14 C13 C10 C11 -63.7(4) . . . . ? C22 C13 C10 C9 -115.3(3) . . . . ? C14 C13 C10 C9 64.1(4) . . . . ? C22 C13 C14 O4 -175.5(3) . . . . ? C10 C13 C14 O4 5.0(5) . . . . ? C22 C13 C14 C15 5.4(4) . . . . ? C10 C13 C14 C15 -174.1(3) . . . . ? C44 C35 C36 O7 -171.7(3) . . . . ? C32 C35 C36 O7 8.7(4) . . . . ? C44 C35 C36 C37 9.3(4) . . . . ? C32 C35 C36 C37 -170.3(3) . . . . ? C44 C35 C32 C31 -119.7(3) . . . . ? C36 C35 C32 C31 59.9(4) . . . . ? C44 C35 C32 C33 114.5(4) . . . . ? C36 C35 C32 C33 -66.0(4) . . . . ? C32 C35 C44 C43 177.8(3) . . . . ? C36 C35 C44 C43 -1.8(5) . . . . ? C32 C35 C44 N2 -0.6(5) . . . . ? C36 C35 C44 N2 179.8(3) . . . . ? O6 N2 C44 C35 -81.1(4) . . . . ? O5 N2 C44 C35 97.8(4) . . . . ? O6 N2 C44 C43 100.3(4) . . . . ? O5 N2 C44 C43 -80.8(3) . . . . ? O7 C36 C37 C38 -8.9(5) . . . . ? C35 C36 C37 C38 170.0(3) . . . . ? O7 C36 C37 C42 172.6(3) . . . . ? C35 C36 C37 C42 -8.5(4) . . . . ? C35 C44 C43 O8 174.4(3) . . . . ? N2 C44 C43 O8 -7.2(4) . . . . ? C35 C44 C43 C42 -6.5(5) . . . . ? N2 C44 C43 C42 171.9(3) . . . . ? C13 C10 C9 C8 169.6(3) . . . . ? C11 C10 C9 C8 -59.8(4) . . . . ? O3 C21 C20 C19 5.7(5) . . . . ? C22 C21 C20 C19 -173.6(3) . . . . ? O3 C21 C20 C15 -175.1(3) . . . . ? C22 C21 C20 C15 5.6(4) . . . . ? C13 C10 C11 C12 -171.5(3) . . . . ? C9 C10 C11 C12 58.4(4) . . . . ? C19 C20 C15 C16 0.8(5) . . . . ? C21 C20 C15 C16 -178.4(3) . . . . ? C19 C20 C15 C14 178.6(3) . . . . ? C21 C20 C15 C14 -0.7(5) . . . . ? O4 C14 C15 C16 -6.5(5) . . . . ? C13 C14 C15 C16 172.6(3) . . . . ? O4 C14 C15 C20 175.9(3) . . . . ? C13 C14 C15 C20 -5.1(4) . . . . ? C38 C37 C42 C41 -0.4(5) . . . . ? C36 C37 C42 C41 178.1(3) . . . . ? C38 C37 C42 C43 -178.6(3) . . . . ? C36 C37 C42 C43 -0.1(5) . . . . ? O8 C43 C42 C41 8.2(5) . . . . ? C44 C43 C42 C41 -170.9(3) . . . . ? O8 C43 C42 C37 -173.6(3) . . . . ? C44 C43 C42 C37 7.3(4) . . . . ? C42 C37 C38 C39 1.0(5) . . . . ? C36 C37 C38 C39 -177.6(3) . . . . ? C25 C26 C29 C30 -140.1(3) . . . . ? C27 C26 C29 C30 46.2(4) . . . . ? C25 C26 C29 C34 -13.3(4) . . . . ? C27 C26 C29 C34 173.0(3) . . . . ? C25 C26 C27 C28 -1.1(5) . . . . ? C29 C26 C27 C28 173.1(3) . . . . ? C35 C32 C31 C30 170.1(3) . . . . ? C33 C32 C31 C30 -60.8(4) . . . . ? C10 C9 C8 C7 59.0(4) . . . . ? C20 C15 C16 C17 -0.1(5) . . . . ? C14 C15 C16 C17 -177.8(3) . . . . ? C26 C29 C34 C33 -77.4(4) . . . . ? C30 C29 C34 C33 51.6(4) . . . . ? C10 C11 C12 C7 -56.7(4) . . . . ? C3 C4 C7 C8 -160.7(3) . . . . ? C5 C4 C7 C8 25.9(4) . . . . ? C3 C4 C7 C12 -33.2(4) . . . . ? C5 C4 C7 C12 153.4(3) . . . . ? C9 C8 C7 C4 75.7(4) . . . . ? C9 C8 C7 C12 -54.7(4) . . . . ? C11 C12 C7 C4 -76.3(4) . . . . ? C11 C12 C7 C8 53.9(4) . . . . ? C24 C23 C28 C27 1.5(5) . . . . ? Cl2 C23 C28 C27 -177.5(2) . . . . ? C26 C27 C28 C23 -0.5(5) . . . . ? C32 C31 C30 C29 58.7(4) . . . . ? C26 C29 C30 C31 77.7(4) . . . . ? C34 C29 C30 C31 -52.3(4) . . . . ? C5 C6 C1 C2 0.8(5) . . . . ? C5 C6 C1 Cl1 -177.8(3) . . . . ? C29 C34 C33 C32 -56.3(4) . . . . ? C35 C32 C33 C34 -172.8(3) . . . . ? C31 C32 C33 C34 59.3(4) . . . . ? C37 C38 C39 C40 -0.6(6) . . . . ? C38 C39 C40 C41 -0.3(6) . . . . ? C3 C4 C5 C6 -0.9(5) . . . . ? C7 C4 C5 C6 172.8(3) . . . . ? C1 C6 C5 C4 -0.3(5) . . . . ? C5 C4 C3 C2 1.6(5) . . . . ? C7 C4 C3 C2 -172.1(3) . . . . ? C39 C40 C41 C42 0.9(6) . . . . ? C37 C42 C41 C40 -0.5(5) . . . . ? C43 C42 C41 C40 177.7(3) . . . . ? C28 C23 C24 C25 -0.8(5) . . . . ? Cl2 C23 C24 C25 178.2(3) . . . . ? C15 C20 C19 C18 -1.5(5) . . . . ? C21 C20 C19 C18 177.7(3) . . . . ? C6 C1 C2 C3 -0.1(6) . . . . ? Cl1 C1 C2 C3 178.5(3) . . . . ? C4 C3 C2 C1 -1.1(6) . . . . ? C20 C19 C18 C17 1.5(6) . . . . ? C15 C16 C17 C18 0.0(6) . . . . ? C19 C18 C17 C16 -0.7(6) . . . . ? C27 C26 C25 C24 1.8(5) . . . . ? C29 C26 C25 C24 -172.2(3) . . . . ? C23 C24 C25 C26 -0.9(6) . . . . ? #===END