# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jinxing Ye' _publ_contact_author_email yejx@ecust.edu.cn loop_ _publ_author_name 'Huicai Huang' 'Kailong Zhu' 'Wenbin Wu' 'Zhichao Jin' 'Jinxing Ye' data_dm1197 _database_code_depnum_ccdc_archive 'CCDC 824362' #TrackingRef 'dm1197.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 Br N O3' _chemical_formula_weight 428.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.773(3) _cell_length_b 6.0463(13) _cell_length_c 13.400(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.851(3) _cell_angle_gamma 90.00 _cell_volume 1034.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3906 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 28.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.007 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3890 _exptl_absorpt_correction_T_max 0.8559 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7395 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4172 _reflns_number_gt 3639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0983P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(12) _chemical_absolute_configuration ad _refine_ls_number_reflns 4172 _refine_ls_number_parameters 246 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.960 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.12769(3) 0.25737(11) 1.12472(2) 0.07726(18) Uani 1 1 d . . . N1 N 0.3323(2) 0.4851(5) 0.7119(3) 0.0565(7) Uani 1 1 d . . . O1 O 0.2001(2) 0.5892(4) 0.5995(2) 0.0699(7) Uani 1 1 d . . . O2 O 0.32529(18) 0.1151(3) 0.68710(19) 0.0486(5) Uani 1 1 d . . . O3 O -0.0532(2) -0.1421(6) 0.6540(3) 0.0780(8) Uani 1 1 d . . . C1 C 0.2520(3) 0.4491(5) 0.6410(3) 0.0535(8) Uani 1 1 d . . . C2 C 0.2397(2) 0.2020(5) 0.6251(2) 0.0464(7) Uani 1 1 d . . . C3 C 0.3692(2) 0.2903(5) 0.7317(2) 0.0497(7) Uani 1 1 d . . . C4 C 0.4570(2) 0.2415(7) 0.7995(3) 0.0583(7) Uani 1 1 d . . . C5 C 0.4959(4) 0.4018(8) 0.8625(4) 0.0795(13) Uani 1 1 d . . . H5 H 0.4651 0.5411 0.8641 0.095 Uiso 1 1 calc R . . C6 C 0.5819(5) 0.3538(12) 0.9242(6) 0.1042(19) Uani 1 1 d . . . H6 H 0.6086 0.4617 0.9670 0.125 Uiso 1 1 calc R . . C7 C 0.6259(4) 0.1547(10) 0.9220(6) 0.103(2) Uani 1 1 d . . . H7 H 0.6831 0.1257 0.9636 0.123 Uiso 1 1 calc R . . C8 C 0.5893(4) -0.0089(10) 0.8601(6) 0.102(2) Uani 1 1 d . . . H8 H 0.6218 -0.1465 0.8588 0.122 Uiso 1 1 calc R . . C9 C 0.5023(3) 0.0346(8) 0.7990(5) 0.0795(13) Uani 1 1 d . . . H9 H 0.4748 -0.0759 0.7580 0.095 Uiso 1 1 calc R . . C10 C 0.2584(3) 0.1302(6) 0.5169(3) 0.0572(8) Uani 1 1 d . . . H10A H 0.2049 0.1957 0.4740 0.069 Uiso 1 1 calc R . . H10B H 0.2514 -0.0292 0.5123 0.069 Uiso 1 1 calc R . . C11 C 0.3673(4) 0.1981(9) 0.4787(4) 0.0843(13) Uani 1 1 d . . . H11A H 0.3714 0.3580 0.4741 0.101 Uiso 1 1 calc R . . H11B H 0.4210 0.1483 0.5254 0.101 Uiso 1 1 calc R . . C12 C 0.3859(5) 0.0970(18) 0.3772(4) 0.115(3) Uani 1 1 d . . . H12A H 0.3839 -0.0613 0.3824 0.172 Uiso 1 1 calc R . . H12B H 0.4531 0.1424 0.3536 0.172 Uiso 1 1 calc R . . H12C H 0.3323 0.1457 0.3312 0.172 Uiso 1 1 calc R . . C13 C 0.1384(2) 0.1044(5) 0.6677(2) 0.0436(6) Uani 1 1 d . . . H13 H 0.1424 -0.0561 0.6583 0.052 Uiso 1 1 calc R . . C14 C 0.1327(2) 0.1442(5) 0.7793(2) 0.0414(6) Uani 1 1 d . . . C15 C 0.1656(3) -0.0208(6) 0.8454(3) 0.0504(7) Uani 1 1 d . . . H15 H 0.1891 -0.1549 0.8202 0.060 Uiso 1 1 calc R . . C16 C 0.1639(3) 0.0106(6) 0.9477(3) 0.0565(8) Uani 1 1 d . . . H16 H 0.1846 -0.1019 0.9911 0.068 Uiso 1 1 calc R . . C17 C 0.1308(2) 0.2126(6) 0.9842(2) 0.0517(7) Uani 1 1 d . . . C18 C 0.0968(3) 0.3772(7) 0.9218(3) 0.0597(8) Uani 1 1 d . . . H18 H 0.0733 0.5108 0.9477 0.072 Uiso 1 1 calc R . . C19 C 0.0977(3) 0.3425(5) 0.8192(3) 0.0513(7) Uani 1 1 d . . . H19 H 0.0744 0.4541 0.7766 0.062 Uiso 1 1 calc R . . C20 C 0.0384(3) 0.1826(7) 0.6124(3) 0.0585(8) Uani 1 1 d . . . H20A H 0.0275 0.3386 0.6257 0.070 Uiso 1 1 calc R . . H20B H 0.0473 0.1646 0.5411 0.070 Uiso 1 1 calc R . . C21 C -0.0562(3) 0.0545(8) 0.6446(3) 0.0605(9) Uani 1 1 d . . . C22 C -0.1533(3) 0.1819(12) 0.6655(5) 0.0995(18) Uani 1 1 d . . . H22A H -0.2053 0.0843 0.6919 0.149 Uiso 1 1 calc R . . H22B H -0.1794 0.2474 0.6048 0.149 Uiso 1 1 calc R . . H22C H -0.1378 0.2962 0.7132 0.149 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0764(2) 0.1117(4) 0.0437(2) -0.0135(2) -0.00162(14) -0.0229(2) N1 0.0657(17) 0.0388(14) 0.0655(19) -0.0063(13) 0.0148(14) -0.0008(12) O1 0.0839(17) 0.0410(13) 0.0849(19) 0.0098(13) 0.0114(15) 0.0120(12) O2 0.0528(11) 0.0337(10) 0.0596(14) -0.0052(9) 0.0049(10) 0.0010(8) O3 0.0764(17) 0.079(2) 0.078(2) 0.0003(16) 0.0038(14) -0.0181(15) C1 0.0624(18) 0.0363(16) 0.062(2) 0.0021(14) 0.0188(15) 0.0028(14) C2 0.0545(14) 0.0375(16) 0.0473(15) -0.0039(11) 0.0077(12) 0.0059(12) C3 0.0513(14) 0.0401(16) 0.0580(16) -0.0081(13) 0.0141(12) -0.0039(13) C4 0.0542(14) 0.0544(18) 0.0664(19) -0.0055(18) 0.0077(13) -0.0087(16) C5 0.074(3) 0.062(2) 0.102(4) -0.016(2) -0.011(2) -0.004(2) C6 0.092(4) 0.097(4) 0.123(5) -0.019(3) -0.035(3) -0.018(3) C7 0.070(3) 0.084(4) 0.152(6) 0.009(3) -0.038(3) -0.014(3) C8 0.068(3) 0.078(3) 0.158(6) -0.010(4) -0.033(3) 0.007(2) C9 0.061(2) 0.065(2) 0.112(4) -0.014(2) -0.019(2) 0.0063(18) C10 0.072(2) 0.0509(18) 0.0492(18) -0.0035(14) 0.0168(15) 0.0025(15) C11 0.085(3) 0.089(3) 0.079(3) -0.005(2) 0.039(2) -0.006(2) C12 0.106(4) 0.157(7) 0.082(4) -0.012(4) 0.046(4) 0.006(4) C13 0.0540(15) 0.0365(13) 0.0403(15) -0.0021(11) 0.0043(11) -0.0002(11) C14 0.0427(13) 0.0384(14) 0.0431(15) -0.0008(11) 0.0022(11) 0.0012(11) C15 0.0595(16) 0.0419(15) 0.0498(18) 0.0003(13) -0.0010(13) 0.0062(13) C16 0.0581(17) 0.061(2) 0.0502(19) 0.0075(15) -0.0090(14) 0.0037(15) C17 0.0458(12) 0.070(2) 0.0398(14) -0.0066(14) 0.0001(10) -0.0102(14) C18 0.0634(19) 0.0603(19) 0.056(2) -0.0135(16) 0.0110(15) 0.0046(16) C19 0.0642(18) 0.0431(17) 0.0468(17) 0.0030(12) 0.0070(14) 0.0137(14) C20 0.0624(18) 0.069(2) 0.0443(16) 0.0055(14) -0.0028(14) 0.0029(16) C21 0.0559(17) 0.089(3) 0.0365(16) 0.0068(16) -0.0060(13) -0.0070(18) C22 0.060(2) 0.128(5) 0.110(4) 0.024(3) 0.004(2) 0.013(3) _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 C17 1.904(3) . ? N1 C3 1.294(5) . ? N1 C1 1.405(5) . ? O1 C1 1.206(5) . ? O2 C3 1.335(4) . ? O2 C2 1.461(4) . ? O3 C21 1.196(6) . ? C1 C2 1.517(5) . ? C2 C10 1.535(5) . ? C2 C13 1.540(4) . ? C3 C4 1.464(5) . ? C4 C5 1.373(6) . ? C4 C9 1.378(6) . ? C5 C6 1.396(8) . ? C5 H5 0.9300 . ? C6 C7 1.329(9) . ? C6 H6 0.9300 . ? C7 C8 1.368(9) . ? C7 H7 0.9300 . ? C8 C9 1.396(7) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.545(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.513(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.517(4) . ? C13 C20 1.541(4) . ? C13 H13 0.9800 . ? C14 C19 1.390(4) . ? C14 C15 1.395(4) . ? C15 C16 1.384(5) . ? C15 H15 0.9300 . ? C16 C17 1.384(5) . ? C16 H16 0.9300 . ? C17 C18 1.366(5) . ? C18 C19 1.391(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.504(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.490(7) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 N1 C1 104.9(3) . . ? C3 O2 C2 106.0(2) . . ? O1 C1 N1 126.4(3) . . ? O1 C1 C2 124.9(4) . . ? N1 C1 C2 108.7(3) . . ? O2 C2 C1 101.5(3) . . ? O2 C2 C10 108.1(3) . . ? C1 C2 C10 113.2(3) . . ? O2 C2 C13 106.1(2) . . ? C1 C2 C13 114.2(3) . . ? C10 C2 C13 112.6(3) . . ? N1 C3 O2 118.8(3) . . ? N1 C3 C4 125.7(3) . . ? O2 C3 C4 115.5(3) . . ? C5 C4 C9 119.8(4) . . ? C5 C4 C3 120.4(4) . . ? C9 C4 C3 119.8(4) . . ? C4 C5 C6 119.4(5) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 120.3(5) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 121.9(5) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C7 C8 C9 118.7(5) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C4 C9 C8 119.9(5) . . ? C4 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C2 C10 C11 113.0(3) . . ? C2 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C2 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C10 110.1(4) . . ? C12 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? C12 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C2 111.0(2) . . ? C14 C13 C20 111.9(2) . . ? C2 C13 C20 113.6(3) . . ? C14 C13 H13 106.6 . . ? C2 C13 H13 106.6 . . ? C20 C13 H13 106.6 . . ? C19 C14 C15 117.9(3) . . ? C19 C14 C13 122.5(3) . . ? C15 C14 C13 119.6(3) . . ? C16 C15 C14 121.5(3) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C17 C16 C15 118.7(3) . . ? C17 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C18 C17 C16 121.5(3) . . ? C18 C17 Br1 119.3(3) . . ? C16 C17 Br1 119.1(3) . . ? C17 C18 C19 119.2(3) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C14 C19 C18 121.2(3) . . ? C14 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C21 C20 C13 111.6(3) . . ? C21 C20 H20A 109.3 . . ? C13 C20 H20A 109.3 . . ? C21 C20 H20B 109.3 . . ? C13 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? O3 C21 C22 121.3(4) . . ? O3 C21 C20 121.1(4) . . ? C22 C21 C20 117.5(4) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C1 O1 -176.8(4) . . . . ? C3 N1 C1 C2 3.8(4) . . . . ? C3 O2 C2 C1 3.2(3) . . . . ? C3 O2 C2 C10 122.6(3) . . . . ? C3 O2 C2 C13 -116.4(3) . . . . ? O1 C1 C2 O2 176.2(3) . . . . ? N1 C1 C2 O2 -4.3(3) . . . . ? O1 C1 C2 C10 60.6(5) . . . . ? N1 C1 C2 C10 -119.9(3) . . . . ? O1 C1 C2 C13 -70.1(5) . . . . ? N1 C1 C2 C13 109.4(3) . . . . ? C1 N1 C3 O2 -1.7(4) . . . . ? C1 N1 C3 C4 177.9(3) . . . . ? C2 O2 C3 N1 -1.2(4) . . . . ? C2 O2 C3 C4 179.2(3) . . . . ? N1 C3 C4 C5 12.1(6) . . . . ? O2 C3 C4 C5 -168.4(4) . . . . ? N1 C3 C4 C9 -166.8(4) . . . . ? O2 C3 C4 C9 12.7(5) . . . . ? C9 C4 C5 C6 1.0(8) . . . . ? C3 C4 C5 C6 -177.9(5) . . . . ? C4 C5 C6 C7 0.0(11) . . . . ? C5 C6 C7 C8 0.0(13) . . . . ? C6 C7 C8 C9 -1.1(12) . . . . ? C5 C4 C9 C8 -2.0(8) . . . . ? C3 C4 C9 C8 176.9(5) . . . . ? C7 C8 C9 C4 2.0(10) . . . . ? O2 C2 C10 C11 -54.6(4) . . . . ? C1 C2 C10 C11 57.0(4) . . . . ? C13 C2 C10 C11 -171.4(3) . . . . ? C2 C10 C11 C12 172.6(5) . . . . ? O2 C2 C13 C14 51.7(3) . . . . ? C1 C2 C13 C14 -59.2(4) . . . . ? C10 C2 C13 C14 169.7(3) . . . . ? O2 C2 C13 C20 178.8(3) . . . . ? C1 C2 C13 C20 67.8(4) . . . . ? C10 C2 C13 C20 -63.2(4) . . . . ? C2 C13 C14 C19 82.5(4) . . . . ? C20 C13 C14 C19 -45.4(4) . . . . ? C2 C13 C14 C15 -96.1(3) . . . . ? C20 C13 C14 C15 135.9(3) . . . . ? C19 C14 C15 C16 -0.2(5) . . . . ? C13 C14 C15 C16 178.5(3) . . . . ? C14 C15 C16 C17 -1.4(5) . . . . ? C15 C16 C17 C18 2.2(5) . . . . ? C15 C16 C17 Br1 179.8(3) . . . . ? C16 C17 C18 C19 -1.5(5) . . . . ? Br1 C17 C18 C19 -179.0(3) . . . . ? C15 C14 C19 C18 1.0(5) . . . . ? C13 C14 C19 C18 -177.7(3) . . . . ? C17 C18 C19 C14 -0.2(5) . . . . ? C14 C13 C20 C21 -63.2(4) . . . . ? C2 C13 C20 C21 170.2(3) . . . . ? C13 C20 C21 O3 -44.1(5) . . . . ? C13 C20 C21 C22 135.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.473 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.155