# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_cd21198 _database_code_depnum_ccdc_archive 'CCDC 918753' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 Cl3 N O3' _chemical_formula_weight 452.74 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' Cl Cl 0.1484 0.1585 '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 8.5901(8) _cell_length_b 13.7587(13) _cell_length_c 9.4392(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.242(2) _cell_angle_gamma 90.00 _cell_volume 1032.60(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4066 _cell_measurement_theta_min 5.469 _cell_measurement_theta_max 55.958 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.358 _exptl_crystal_size_mid 0.311 _exptl_crystal_size_min 0.257 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.468 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.85964 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5629 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3234 _reflns_number_gt 3153 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0442P)^2^+0.1579P] 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 SHELXL _refine_ls_extinction_coef 0.063(4) _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 -0.09(5) _chemical_absolute_configuration ad _refine_ls_number_reflns 3234 _refine_ls_number_parameters 268 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.07497(9) 0.48728(6) 0.78324(9) 0.0753(2) Uani 1 1 d . . . Cl2 Cl 0.89716(10) 0.39538(6) 0.94998(7) 0.0682(2) Uani 1 1 d . . . Cl3 Cl 0.73168(10) 0.43080(7) 0.62566(8) 0.0807(3) Uani 1 1 d . . . N1 N 0.6522(2) 1.04953(15) 0.6473(2) 0.0438(4) Uani 1 1 d D . . O1 O 0.80849(18) 1.19248(12) 0.75355(17) 0.0437(3) Uani 1 1 d . . . O2 O 1.14323(17) 1.19888(12) 0.73454(16) 0.0435(3) Uani 1 1 d . . . O3 O 1.3424(2) 1.11093(16) 0.6955(2) 0.0612(5) Uani 1 1 d . . . C1 C 1.0623(2) 1.11020(17) 0.7556(2) 0.0379(4) Uani 1 1 d . . . H1 H 1.1485 1.0639 0.8160 0.045 Uiso 1 1 calc R . . C2 C 0.9548(3) 1.13869(18) 0.8442(2) 0.0421(5) Uani 1 1 d . . . H2A H 0.9202 1.0804 0.8822 0.050 Uiso 1 1 calc R . . H2B H 1.0216 1.1776 0.9318 0.050 Uiso 1 1 calc R . . C3 C 0.7072(2) 1.14159(17) 0.6164(2) 0.0421(5) Uani 1 1 d . . . H3 H 0.6077 1.1812 0.5617 0.050 Uiso 1 1 calc R . . C4 C 0.8077(3) 1.13083(19) 0.5153(2) 0.0452(5) Uani 1 1 d . . . H4A H 0.8482 1.1937 0.4973 0.054 Uiso 1 1 calc R . . H4B H 0.7387 1.1027 0.4174 0.054 Uiso 1 1 calc R . . C5 C 0.9555(2) 1.06386(16) 0.6011(2) 0.0387(4) Uani 1 1 d . . . H5 H 1.0246 1.0542 0.5401 0.046 Uiso 1 1 calc R . . C6 C 0.8895(2) 0.96801(16) 0.6288(2) 0.0390(4) Uani 1 1 d . . . C7 C 0.9794(2) 0.88091(17) 0.6338(2) 0.0421(5) Uani 1 1 d . . . H7 H 1.0761 0.8832 0.6118 0.050 Uiso 1 1 calc R . . C8 C 0.9286(3) 0.79466(19) 0.6698(2) 0.0461(5) Uani 1 1 d . . . H8 H 0.9883 0.7384 0.6690 0.055 Uiso 1 1 calc R . . C9 C 0.7840(3) 0.78951(17) 0.7091(2) 0.0406(4) Uani 1 1 d . . . C10 C 0.6896(2) 0.87636(16) 0.7043(2) 0.0374(4) Uani 1 1 d . . . C11 C 0.7430(2) 0.96560(16) 0.6579(2) 0.0367(4) Uani 1 1 d . . . C12 C 0.7369(3) 0.70277(18) 0.7578(2) 0.0465(5) Uani 1 1 d . . . H12 H 0.7948 0.6460 0.7554 0.056 Uiso 1 1 calc R . . C13 C 0.6057(3) 0.69875(19) 0.8100(2) 0.0456(5) Uani 1 1 d . . . C14 C 0.5134(2) 0.78486(18) 0.8083(2) 0.0430(5) Uani 1 1 d . . . C15 C 0.5555(2) 0.87064(17) 0.7533(2) 0.0407(5) Uani 1 1 d . . . H15 H 0.4921 0.9261 0.7491 0.049 Uiso 1 1 calc R . . C16 C 0.5637(3) 0.6115(2) 0.8705(3) 0.0564(6) Uani 1 1 d . . . H16 H 0.6209 0.5542 0.8702 0.068 Uiso 1 1 calc R . . C17 C 0.4414(3) 0.6119(2) 0.9281(3) 0.0606(7) Uani 1 1 d . . . H17 H 0.4176 0.5552 0.9696 0.073 Uiso 1 1 calc R . . C18 C 0.3505(3) 0.6965(2) 0.9261(3) 0.0598(7) Uani 1 1 d . . . H18 H 0.2659 0.6953 0.9650 0.072 Uiso 1 1 calc R . . C19 C 0.3843(3) 0.7802(2) 0.8682(3) 0.0524(6) Uani 1 1 d . . . H19 H 0.3222 0.8357 0.8675 0.063 Uiso 1 1 calc R . . C20 C 1.2878(2) 1.18919(19) 0.7117(2) 0.0450(5) Uani 1 1 d . . . C21 C 1.3683(3) 1.2843(2) 0.7108(3) 0.0575(6) Uani 1 1 d . . . H21A H 1.4879 1.2759 0.7454 0.086 Uiso 1 1 calc R . . H21B H 1.3430 1.3285 0.7777 0.086 Uiso 1 1 calc R . . H21C H 1.3263 1.3101 0.6087 0.086 Uiso 1 1 calc R . . C22 C 0.9206(3) 0.40109(19) 0.7736(2) 0.0492(5) Uani 1 1 d . . . H22 H 0.9574 0.3373 0.7520 0.059 Uiso 1 1 calc R . . H1A H 0.574(2) 1.0477(19) 0.669(3) 0.039(6) Uiso 1 1 d 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 0.0713(4) 0.0738(5) 0.0864(5) 0.0001(4) 0.0364(4) -0.0209(4) Cl2 0.0971(5) 0.0635(4) 0.0505(3) -0.0014(3) 0.0352(3) -0.0095(4) Cl3 0.0714(4) 0.0954(6) 0.0583(4) 0.0050(3) 0.0053(3) -0.0057(4) N1 0.0310(8) 0.0466(11) 0.0609(11) -0.0002(8) 0.0253(8) 0.0029(8) O1 0.0416(7) 0.0412(9) 0.0537(8) -0.0023(7) 0.0241(6) 0.0039(6) O2 0.0351(7) 0.0466(9) 0.0521(8) 0.0004(7) 0.0203(6) 0.0009(6) O3 0.0418(8) 0.0706(13) 0.0799(11) -0.0088(10) 0.0331(8) 0.0037(8) C1 0.0324(9) 0.0424(12) 0.0399(9) 0.0027(8) 0.0148(7) 0.0031(8) C2 0.0428(10) 0.0483(12) 0.0392(10) -0.0014(8) 0.0202(8) -0.0002(9) C3 0.0333(9) 0.0454(12) 0.0480(11) 0.0051(9) 0.0159(8) 0.0089(8) C4 0.0398(10) 0.0581(15) 0.0377(10) 0.0060(9) 0.0148(8) 0.0038(10) C5 0.0344(9) 0.0487(12) 0.0371(9) -0.0010(8) 0.0181(8) 0.0043(8) C6 0.0333(9) 0.0495(13) 0.0344(9) -0.0056(8) 0.0130(7) 0.0014(8) C7 0.0340(9) 0.0531(14) 0.0436(10) -0.0076(9) 0.0198(8) 0.0056(9) C8 0.0404(10) 0.0495(13) 0.0497(11) -0.0059(10) 0.0186(8) 0.0096(10) C9 0.0373(9) 0.0435(12) 0.0391(9) -0.0047(9) 0.0123(7) 0.0038(9) C10 0.0296(9) 0.0462(12) 0.0338(8) -0.0052(8) 0.0090(7) 0.0015(8) C11 0.0303(9) 0.0426(12) 0.0360(9) -0.0056(8) 0.0114(7) 0.0032(8) C12 0.0419(11) 0.0447(12) 0.0491(11) -0.0052(10) 0.0130(9) 0.0037(10) C13 0.0398(10) 0.0483(13) 0.0402(10) 0.0007(9) 0.0056(8) -0.0028(10) C14 0.0321(9) 0.0563(14) 0.0377(9) -0.0021(9) 0.0100(7) -0.0045(9) C15 0.0321(9) 0.0454(13) 0.0431(9) -0.0031(8) 0.0127(7) 0.0043(8) C16 0.0520(13) 0.0532(15) 0.0546(13) 0.0067(11) 0.0097(10) -0.0054(11) C17 0.0585(14) 0.0647(17) 0.0509(12) 0.0109(12) 0.0117(11) -0.0147(13) C18 0.0489(13) 0.081(2) 0.0511(12) 0.0033(12) 0.0203(10) -0.0133(13) C19 0.0414(11) 0.0665(17) 0.0508(12) 0.0012(11) 0.0190(9) -0.0035(11) C20 0.0302(9) 0.0619(15) 0.0425(10) 0.0008(10) 0.0133(8) 0.0009(10) C21 0.0436(11) 0.0701(18) 0.0584(13) 0.0010(12) 0.0188(10) -0.0091(12) C22 0.0596(13) 0.0430(12) 0.0457(10) -0.0026(9) 0.0208(9) -0.0051(10) _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 1.755(2) . ? Cl2 C22 1.753(2) . ? Cl3 C22 1.742(2) . ? N1 C11 1.376(3) . ? N1 C3 1.420(3) . ? N1 H1A 0.777(17) . ? O1 C2 1.430(3) . ? O1 C3 1.439(3) . ? O2 C20 1.345(2) . ? O2 C1 1.454(3) . ? O3 C20 1.207(3) . ? C1 C2 1.514(3) . ? C1 C5 1.537(3) . ? C1 H1 0.9800 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.518(3) . ? C3 H3 0.9800 . ? C4 C5 1.529(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.497(3) . ? C5 H5 0.9800 . ? C6 C11 1.386(3) . ? C6 C7 1.417(3) . ? C7 C8 1.351(3) . ? C7 H7 0.9300 . ? C8 C9 1.426(3) . ? C8 H8 0.9300 . ? C9 C12 1.393(3) . ? C9 C10 1.435(3) . ? C10 C15 1.397(3) . ? C10 C11 1.436(3) . ? C12 C13 1.391(3) . ? C12 H12 0.9300 . ? C13 C14 1.422(3) . ? C13 C16 1.433(3) . ? C14 C15 1.391(3) . ? C14 C19 1.424(3) . ? C15 H15 0.9300 . ? C16 C17 1.353(4) . ? C16 H16 0.9300 . ? C17 C18 1.398(4) . ? C17 H17 0.9300 . ? C18 C19 1.352(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.482(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22 0.9800 . ? 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 N1 C3 122.70(16) . . ? C11 N1 H1A 119(2) . . ? C3 N1 H1A 118.2(19) . . ? C2 O1 C3 112.43(16) . . ? C20 O2 C1 117.16(17) . . ? O2 C1 C2 106.33(17) . . ? O2 C1 C5 111.30(15) . . ? C2 C1 C5 111.17(15) . . ? O2 C1 H1 109.3 . . ? C2 C1 H1 109.3 . . ? C5 C1 H1 109.3 . . ? O1 C2 C1 112.67(16) . . ? O1 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? O1 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? N1 C3 O1 112.62(17) . . ? N1 C3 C4 110.78(19) . . ? O1 C3 C4 108.60(17) . . ? N1 C3 H3 108.2 . . ? O1 C3 H3 108.2 . . ? C4 C3 H3 108.2 . . ? C3 C4 C5 106.34(16) . . ? C3 C4 H4A 110.5 . . ? C5 C4 H4A 110.5 . . ? C3 C4 H4B 110.5 . . ? C5 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? C6 C5 C4 109.29(17) . . ? C6 C5 C1 109.22(16) . . ? C4 C5 C1 109.30(18) . . ? C6 C5 H5 109.7 . . ? C4 C5 H5 109.7 . . ? C1 C5 H5 109.7 . . ? C11 C6 C7 119.8(2) . . ? C11 C6 C5 119.20(18) . . ? C7 C6 C5 120.86(17) . . ? C8 C7 C6 121.82(18) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C7 C8 C9 120.3(2) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C12 C9 C8 121.2(2) . . ? C12 C9 C10 119.50(19) . . ? C8 C9 C10 119.2(2) . . ? C15 C10 C9 118.02(19) . . ? C15 C10 C11 123.22(18) . . ? C9 C10 C11 118.66(17) . . ? N1 C11 C6 119.83(19) . . ? N1 C11 C10 120.16(16) . . ? C6 C11 C10 119.97(18) . . ? C13 C12 C9 121.7(2) . . ? C13 C12 H12 119.1 . . ? C9 C12 H12 119.1 . . ? C12 C13 C14 119.1(2) . . ? C12 C13 C16 122.3(2) . . ? C14 C13 C16 118.6(2) . . ? C15 C14 C13 119.25(18) . . ? C15 C14 C19 122.5(2) . . ? C13 C14 C19 118.2(2) . . ? C14 C15 C10 122.32(19) . . ? C14 C15 H15 118.8 . . ? C10 C15 H15 118.8 . . ? C17 C16 C13 120.5(3) . . ? C17 C16 H16 119.7 . . ? C13 C16 H16 119.7 . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17 119.6 . . ? C18 C17 H17 119.6 . . ? C19 C18 C17 120.7(2) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C18 C19 C14 121.2(3) . . ? C18 C19 H19 119.4 . . ? C14 C19 H19 119.4 . . ? O3 C20 O2 122.4(2) . . ? O3 C20 C21 125.6(2) . . ? O2 C20 C21 112.0(2) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Cl3 C22 Cl2 111.40(14) . . ? Cl3 C22 Cl1 109.83(14) . . ? Cl2 C22 Cl1 109.70(12) . . ? Cl3 C22 H22 108.6 . . ? Cl2 C22 H22 108.6 . . ? Cl1 C22 H22 108.6 . . ? 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 C20 O2 C1 C2 155.90(16) . . . . ? C20 O2 C1 C5 -82.9(2) . . . . ? C3 O1 C2 C1 55.6(2) . . . . ? O2 C1 C2 O1 72.4(2) . . . . ? C5 C1 C2 O1 -48.9(3) . . . . ? C11 N1 C3 O1 -90.1(2) . . . . ? C11 N1 C3 C4 31.7(3) . . . . ? C2 O1 C3 N1 58.5(2) . . . . ? C2 O1 C3 C4 -64.6(2) . . . . ? N1 C3 C4 C5 -58.2(2) . . . . ? O1 C3 C4 C5 65.9(2) . . . . ? C3 C4 C5 C6 59.4(2) . . . . ? C3 C4 C5 C1 -60.0(2) . . . . ? O2 C1 C5 C6 174.25(15) . . . . ? C2 C1 C5 C6 -67.4(2) . . . . ? O2 C1 C5 C4 -66.22(19) . . . . ? C2 C1 C5 C4 52.1(2) . . . . ? C4 C5 C6 C11 -34.9(2) . . . . ? C1 C5 C6 C11 84.6(2) . . . . ? C4 C5 C6 C7 148.49(18) . . . . ? C1 C5 C6 C7 -92.0(2) . . . . ? C11 C6 C7 C8 -1.5(3) . . . . ? C5 C6 C7 C8 175.05(19) . . . . ? C6 C7 C8 C9 -2.0(3) . . . . ? C7 C8 C9 C12 -175.02(19) . . . . ? C7 C8 C9 C10 2.3(3) . . . . ? C12 C9 C10 C15 1.7(3) . . . . ? C8 C9 C10 C15 -175.68(17) . . . . ? C12 C9 C10 C11 178.22(17) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C3 N1 C11 C6 -4.0(3) . . . . ? C3 N1 C11 C10 173.79(18) . . . . ? C7 C6 C11 N1 -177.48(17) . . . . ? C5 C6 C11 N1 5.9(3) . . . . ? C7 C6 C11 C10 4.7(3) . . . . ? C5 C6 C11 C10 -171.92(16) . . . . ? C15 C10 C11 N1 -5.8(3) . . . . ? C9 C10 C11 N1 177.85(17) . . . . ? C15 C10 C11 C6 172.01(17) . . . . ? C9 C10 C11 C6 -4.3(3) . . . . ? C8 C9 C12 C13 173.89(19) . . . . ? C10 C9 C12 C13 -3.4(3) . . . . ? C9 C12 C13 C14 2.3(3) . . . . ? C9 C12 C13 C16 -175.5(2) . . . . ? C12 C13 C14 C15 0.6(3) . . . . ? C16 C13 C14 C15 178.44(19) . . . . ? C12 C13 C14 C19 -177.36(19) . . . . ? C16 C13 C14 C19 0.5(3) . . . . ? C13 C14 C15 C10 -2.3(3) . . . . ? C19 C14 C15 C10 175.56(18) . . . . ? C9 C10 C15 C14 1.1(3) . . . . ? C11 C10 C15 C14 -175.21(17) . . . . ? C12 C13 C16 C17 176.2(2) . . . . ? C14 C13 C16 C17 -1.6(3) . . . . ? C13 C16 C17 C18 1.7(4) . . . . ? C16 C17 C18 C19 -0.8(4) . . . . ? C17 C18 C19 C14 -0.3(4) . . . . ? C15 C14 C19 C18 -177.5(2) . . . . ? C13 C14 C19 C18 0.4(3) . . . . ? C1 O2 C20 O3 6.4(3) . . . . ? C1 O2 C20 C21 -173.04(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O3 0.777(17) 2.267(19) 2.987(2) 154(3) 1_455 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.192 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.045