data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Xiaoming Feng' _publ_contact_author_email XMFENG@SCU.EDU.CN _publ_section_title ; Highly Enantioselective alpha-Chlorination of beta-Ketoesters Catalyzed by N,N'-Dioxide Using NCS as the Chlorine Source ; loop_ _publ_author_name 'Xiaoming Feng' 'Yunfei Cai' 'Xiaolei Hu' 'Lili Lin' 'Xiaohua Liu' ; Ke Shen ; 'Jun Wang' 'Wentao Wang' # Attachment 'CD4.CIF' data_cd4 _database_code_depnum_ccdc_archive 'CCDC 752601' #TrackingRef 'CD4.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 Br Cl O3' _chemical_formula_weight 437.75 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.9369(14) _cell_length_b 7.2436(14) _cell_length_c 36.835(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1850.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 4022 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 27.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 2.384 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5985 _exptl_absorpt_correction_T_max 0.6736 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12953 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.86 _reflns_number_total 4334 _reflns_number_gt 3497 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear(Rigaku/MSC Inc.,2005)' _computing_cell_refinement crystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0527P)^2^+1.2845P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.035(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.055(15) _chemical_absolute_configuration ad _refine_ls_number_reflns 4334 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1510 _refine_ls_wR_factor_gt 0.1357 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.02199(8) 0.85073(8) 0.186466(18) 0.0638(2) Uani 1 d . . . Cl1 Cl 0.1729(2) 1.0251(2) 0.39292(6) 0.0766(5) Uani 1 d . . . O1 O -0.0003(5) 0.8210(5) 0.33282(12) 0.0580(10) Uani 1 d . . . O2 O 0.4801(6) 0.7638(6) 0.40281(13) 0.0731(13) Uani 1 d . . . O3 O 0.3986(5) 0.5989(5) 0.35268(10) 0.0487(8) Uani 1 d . . . C1 C 0.3050(7) 0.9162(8) 0.35722(19) 0.0598(16) Uani 1 d . . . C2 C 0.1638(6) 0.8697(7) 0.32603(17) 0.0560(14) Uani 1 d . . . C3 C 0.2330(6) 0.8882(6) 0.28784(17) 0.0502(13) Uani 1 d . . . C4 C 0.1001(6) 0.8587(7) 0.26026(17) 0.0526(13) Uani 1 d . . . H4 H -0.0278 0.8212 0.2658 0.063 Uiso 1 calc R . . C5 C 0.1568(7) 0.8849(7) 0.22431(17) 0.0545(14) Uani 1 d . . . C6 C 0.3441(7) 0.9404(8) 0.2162(2) 0.0596(15) Uani 1 d . . . H6 H 0.3812 0.9611 0.1918 0.071 Uiso 1 calc R . . C7 C 0.4757(7) 0.9653(7) 0.24384(19) 0.0621(16) Uani 1 d . . . H7 H 0.6042 0.9996 0.2380 0.074 Uiso 1 calc R . . C8 C 0.4248(6) 0.9412(7) 0.2804(2) 0.0611(17) Uani 1 d . . . C9 C 0.5658(6) 0.9701(7) 0.3107(2) 0.0656(17) Uani 1 d . . . H9A H 0.6676 1.0568 0.3027 0.079 Uiso 1 calc R . . H9B H 0.6279 0.8511 0.3169 0.079 Uiso 1 calc R . . C10 C 0.4650(8) 1.0478(8) 0.3445(2) 0.0697(18) Uani 1 d . . . H10A H 0.4086 1.1699 0.3387 0.084 Uiso 1 calc R . . H10B H 0.5604 1.0646 0.3642 0.084 Uiso 1 calc R . . C11 C 0.3957(7) 0.7379(8) 0.37084(18) 0.0556(14) Uani 1 d . . . C12 C 0.5968(7) 0.6216(9) 0.42090(15) 0.0558(15) Uani 1 d . . . C13 C 0.7814(7) 0.5840(8) 0.39990(14) 0.0500(13) Uani 1 d . . . H13A H 0.8510 0.7011 0.3954 0.060 Uiso 1 calc R . . H13B H 0.7506 0.5271 0.3762 0.060 Uiso 1 calc R . . C14 C 0.9090(7) 0.4517(9) 0.42254(12) 0.0519(15) Uani 1 d . . . H14 H 1.0306 0.4252 0.4089 0.062 Uiso 1 calc R . . C15 C 0.8013(7) 0.2753(9) 0.42843(14) 0.0546(15) Uani 1 d . . . H15A H 0.8832 0.1879 0.4422 0.066 Uiso 1 calc R . . H15B H 0.7705 0.2186 0.4047 0.066 Uiso 1 calc R . . C16 C 0.6152(7) 0.3107(11) 0.44940(14) 0.065(2) Uani 1 d . . . H16 H 0.5457 0.1917 0.4536 0.078 Uiso 1 calc R . . C17 C 0.4871(7) 0.4430(9) 0.42719(14) 0.0554(14) Uani 1 d . . . H17A H 0.4535 0.3858 0.4036 0.067 Uiso 1 calc R . . H17B H 0.3662 0.4686 0.4405 0.067 Uiso 1 calc R . . C18 C 0.6645(8) 0.4003(14) 0.48537(13) 0.097(3) Uani 1 d . . . H18A H 0.7461 0.3156 0.4998 0.117 Uiso 1 calc R . . H18B H 0.5446 0.4240 0.4992 0.117 Uiso 1 calc R . . C19 C 0.7710(8) 0.5810(13) 0.47932(16) 0.091(3) Uani 1 d . . . H19 H 0.8009 0.6395 0.5032 0.110 Uiso 1 calc R . . C20 C 0.9587(8) 0.5432(12) 0.45868(14) 0.072(2) Uani 1 d . . . H20A H 1.0284 0.6604 0.4543 0.087 Uiso 1 calc R . . H20B H 1.0429 0.4609 0.4731 0.087 Uiso 1 calc R . . C21 C 0.6453(9) 0.7107(13) 0.4568(2) 0.095(3) Uani 1 d . . . H21A H 0.5251 0.7389 0.4701 0.113 Uiso 1 calc R . . H21B H 0.7148 0.8280 0.4525 0.113 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0462(3) 0.0376(3) 0.1076(5) 0.0123(3) 0.0026(3) -0.0070(2) Cl1 0.0425(7) 0.0533(10) 0.1341(14) -0.0305(10) 0.0036(9) 0.0033(6) O1 0.0256(15) 0.041(2) 0.107(3) 0.0036(18) 0.0002(18) -0.0066(15) O2 0.042(2) 0.056(3) 0.121(3) -0.035(2) -0.029(2) 0.0054(19) O3 0.0371(17) 0.036(2) 0.073(2) -0.0030(16) -0.0034(16) 0.0012(14) C1 0.028(2) 0.035(3) 0.117(5) -0.018(3) -0.004(3) -0.0010(19) C2 0.0209(18) 0.025(2) 0.123(5) 0.002(3) -0.002(2) -0.0002(18) C3 0.0236(19) 0.019(2) 0.108(4) -0.002(2) 0.008(2) -0.0014(15) C4 0.0206(18) 0.023(2) 0.114(4) 0.006(3) 0.001(2) 0.0016(18) C5 0.032(2) 0.025(3) 0.106(4) 0.006(3) 0.009(3) 0.0003(18) C6 0.033(2) 0.030(3) 0.116(5) 0.008(3) 0.014(3) -0.001(2) C7 0.027(2) 0.025(2) 0.134(5) 0.012(3) 0.016(3) -0.0007(19) C8 0.022(2) 0.020(2) 0.142(6) -0.003(3) 0.004(3) -0.0009(17) C9 0.020(2) 0.030(3) 0.148(6) 0.001(3) 0.000(3) -0.0062(16) C10 0.032(2) 0.032(3) 0.145(6) -0.015(3) -0.010(3) -0.007(2) C11 0.026(2) 0.037(3) 0.104(4) -0.014(3) -0.011(3) -0.0026(19) C12 0.025(2) 0.071(4) 0.071(3) -0.029(3) -0.011(2) 0.002(2) C13 0.027(2) 0.059(4) 0.063(3) -0.003(3) -0.001(2) -0.010(2) C14 0.0204(19) 0.092(5) 0.043(2) -0.009(3) -0.0010(18) -0.001(2) C15 0.030(2) 0.081(4) 0.052(3) 0.008(3) -0.007(2) 0.000(2) C16 0.032(2) 0.112(6) 0.052(3) 0.018(3) -0.005(2) -0.012(3) C17 0.019(2) 0.088(4) 0.059(3) -0.006(3) -0.002(2) -0.007(2) C18 0.031(3) 0.226(11) 0.035(2) -0.001(4) 0.000(2) -0.009(5) C19 0.029(3) 0.186(10) 0.059(3) -0.054(5) -0.003(2) 0.003(4) C20 0.027(2) 0.136(7) 0.053(3) -0.025(3) -0.005(2) -0.005(3) C21 0.034(3) 0.146(8) 0.104(5) -0.080(5) -0.016(3) 0.014(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C5 1.882(6) . ? Cl1 C1 1.787(6) . ? O1 C2 1.218(6) . ? O2 C11 1.328(7) . ? O2 C12 1.470(7) . ? O3 C11 1.209(7) . ? C1 C11 1.522(8) . ? C1 C10 1.536(8) . ? C1 C2 1.547(8) . ? C2 C3 1.493(8) . ? C3 C4 1.388(7) . ? C3 C8 1.412(6) . ? C4 C5 1.394(8) . ? C4 H4 0.9500 . ? C5 C6 1.393(7) . ? C6 C7 1.378(9) . ? C6 H6 0.9500 . ? C7 C8 1.402(9) . ? C7 H7 0.9500 . ? C8 C9 1.500(9) . ? C9 C10 1.533(9) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C12 C21 1.508(7) . ? C12 C17 1.518(8) . ? C12 C13 1.521(7) . ? C13 C14 1.548(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.496(9) . ? C14 C20 1.526(7) . ? C14 H14 1.0000 . ? C15 C16 1.527(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C18 1.514(8) . ? C16 C17 1.542(8) . ? C16 H16 1.0000 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.519(12) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C21 1.528(11) . ? C19 C20 1.533(8) . ? C19 H19 1.0000 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? 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 C11 O2 C12 123.1(4) . . ? C11 C1 C10 109.2(4) . . ? C11 C1 C2 108.8(4) . . ? C10 C1 C2 111.4(6) . . ? C11 C1 Cl1 110.1(5) . . ? C10 C1 Cl1 108.8(4) . . ? C2 C1 Cl1 108.5(3) . . ? O1 C2 C3 121.3(5) . . ? O1 C2 C1 120.2(6) . . ? C3 C2 C1 118.5(4) . . ? C4 C3 C8 121.7(6) . . ? C4 C3 C2 117.5(4) . . ? C8 C3 C2 120.7(6) . . ? C3 C4 C5 119.1(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 120.3(6) . . ? C6 C5 Br1 119.7(5) . . ? C4 C5 Br1 120.0(4) . . ? C7 C6 C5 119.9(6) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 121.7(5) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C7 C8 C3 117.3(6) . . ? C7 C8 C9 122.2(5) . . ? C3 C8 C9 120.5(6) . . ? C8 C9 C10 111.0(4) . . ? C8 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C1 110.5(5) . . ? C9 C10 H10A 109.6 . . ? C1 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C1 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O3 C11 O2 126.9(6) . . ? O3 C11 C1 122.1(5) . . ? O2 C11 C1 110.8(5) . . ? O2 C12 C21 102.7(5) . . ? O2 C12 C17 113.0(4) . . ? C21 C12 C17 110.1(6) . . ? O2 C12 C13 111.0(5) . . ? C21 C12 C13 109.5(4) . . ? C17 C12 C13 110.3(5) . . ? C12 C13 C14 108.5(4) . . ? C12 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? C12 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? C15 C14 C20 110.9(5) . . ? C15 C14 C13 108.8(4) . . ? C20 C14 C13 109.3(5) . . ? C15 C14 H14 109.3 . . ? C20 C14 H14 109.3 . . ? C13 C14 H14 109.3 . . ? C14 C15 C16 110.6(5) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C18 C16 C15 108.9(4) . . ? C18 C16 C17 109.2(6) . . ? C15 C16 C17 108.9(4) . . ? C18 C16 H16 110.0 . . ? C15 C16 H16 110.0 . . ? C17 C16 H16 110.0 . . ? C12 C17 C16 108.8(4) . . ? C12 C17 H17A 109.9 . . ? C16 C17 H17A 109.9 . . ? C12 C17 H17B 109.9 . . ? C16 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? C16 C18 C19 110.5(5) . . ? C16 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C18 C19 C21 109.4(5) . . ? C18 C19 C20 109.4(7) . . ? C21 C19 C20 109.0(6) . . ? C18 C19 H19 109.7 . . ? C21 C19 H19 109.7 . . ? C20 C19 H19 109.7 . . ? C14 C20 C19 108.5(4) . . ? C14 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? C14 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C12 C21 C19 109.9(6) . . ? C12 C21 H21A 109.7 . . ? C19 C21 H21A 109.7 . . ? C12 C21 H21B 109.7 . . ? C19 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? 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 C11 C1 C2 O1 83.8(6) . . . . ? C10 C1 C2 O1 -155.8(5) . . . . ? Cl1 C1 C2 O1 -36.0(6) . . . . ? C11 C1 C2 C3 -97.0(6) . . . . ? C10 C1 C2 C3 23.5(6) . . . . ? Cl1 C1 C2 C3 143.2(4) . . . . ? O1 C2 C3 C4 3.8(7) . . . . ? C1 C2 C3 C4 -175.4(5) . . . . ? O1 C2 C3 C8 -178.8(5) . . . . ? C1 C2 C3 C8 2.0(7) . . . . ? C8 C3 C4 C5 -1.0(7) . . . . ? C2 C3 C4 C5 176.4(5) . . . . ? C3 C4 C5 C6 -0.2(8) . . . . ? C3 C4 C5 Br1 -178.7(4) . . . . ? C4 C5 C6 C7 1.6(8) . . . . ? Br1 C5 C6 C7 -179.9(4) . . . . ? C5 C6 C7 C8 -1.9(8) . . . . ? C6 C7 C8 C3 0.7(8) . . . . ? C6 C7 C8 C9 -179.2(5) . . . . ? C4 C3 C8 C7 0.7(7) . . . . ? C2 C3 C8 C7 -176.6(4) . . . . ? C4 C3 C8 C9 -179.3(4) . . . . ? C2 C3 C8 C9 3.3(7) . . . . ? C7 C8 C9 C10 146.2(5) . . . . ? C3 C8 C9 C10 -33.7(7) . . . . ? C8 C9 C10 C1 58.7(7) . . . . ? C11 C1 C10 C9 66.9(7) . . . . ? C2 C1 C10 C9 -53.3(6) . . . . ? Cl1 C1 C10 C9 -172.9(4) . . . . ? C12 O2 C11 O3 1.3(9) . . . . ? C12 O2 C11 C1 -173.5(5) . . . . ? C10 C1 C11 O3 -101.6(6) . . . . ? C2 C1 C11 O3 20.2(7) . . . . ? Cl1 C1 C11 O3 139.0(5) . . . . ? C10 C1 C11 O2 73.5(7) . . . . ? C2 C1 C11 O2 -164.7(5) . . . . ? Cl1 C1 C11 O2 -45.9(5) . . . . ? C11 O2 C12 C21 -175.6(6) . . . . ? C11 O2 C12 C17 -57.1(7) . . . . ? C11 O2 C12 C13 67.4(6) . . . . ? O2 C12 C13 C14 173.2(4) . . . . ? C21 C12 C13 C14 60.5(7) . . . . ? C17 C12 C13 C14 -60.8(5) . . . . ? C12 C13 C14 C15 60.4(6) . . . . ? C12 C13 C14 C20 -60.9(6) . . . . ? C20 C14 C15 C16 59.1(6) . . . . ? C13 C14 C15 C16 -61.1(5) . . . . ? C14 C15 C16 C18 -58.3(7) . . . . ? C14 C15 C16 C17 60.6(6) . . . . ? O2 C12 C17 C16 -174.7(4) . . . . ? C21 C12 C17 C16 -60.5(6) . . . . ? C13 C12 C17 C16 60.4(6) . . . . ? C18 C16 C17 C12 59.8(6) . . . . ? C15 C16 C17 C12 -59.0(6) . . . . ? C15 C16 C18 C19 59.2(8) . . . . ? C17 C16 C18 C19 -59.6(6) . . . . ? C16 C18 C19 C21 58.8(7) . . . . ? C16 C18 C19 C20 -60.5(7) . . . . ? C15 C14 C20 C19 -58.9(8) . . . . ? C13 C14 C20 C19 61.0(8) . . . . ? C18 C19 C20 C14 58.9(7) . . . . ? C21 C19 C20 C14 -60.6(8) . . . . ? O2 C12 C21 C19 -179.2(5) . . . . ? C17 C12 C21 C19 60.3(6) . . . . ? C13 C12 C21 C19 -61.1(8) . . . . ? C18 C19 C21 C12 -58.6(7) . . . . ? C20 C19 C21 C12 60.9(8) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.614 _refine_diff_density_min -1.495 _refine_diff_density_rms 0.078