# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_12ma23_0ma _database_code_depnum_ccdc_archive 'CCDC 912553' #TrackingRef '12ma23_0ma.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H30 N4 O4' _chemical_formula_weight 414.50 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' _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.0891(6) _cell_length_b 12.3368(5) _cell_length_c 14.0775(6) _cell_angle_alpha 90.00 _cell_angle_beta 117.2680(10) _cell_angle_gamma 90.00 _cell_volume 2174.96(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9875 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.87 _exptl_crystal_description Columnar _exptl_crystal_colour Pale-Orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9843 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _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 ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29092 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.46 _reflns_number_total 5405 _reflns_number_gt 3025 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0573P)^2^+0.3104P] 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_number_reflns 5405 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0978 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1413 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.87918(17) 0.11652(14) 0.36174(14) 0.1186(6) Uani 1 1 d . . . O2 O 0.78445(14) 0.22302(14) 0.40498(14) 0.1075(5) Uani 1 1 d . . . O3 O 1.03565(15) 0.23935(13) 0.15139(17) 0.1186(6) Uani 1 1 d . . . O4 O 1.01665(12) 0.40050(13) 0.09068(13) 0.0950(5) Uani 1 1 d . . . N1 N 0.87194(11) 0.52866(12) 0.09854(11) 0.0667(4) Uani 1 1 d . . . H1 H 0.9185 0.5254 0.0751 0.080 Uiso 1 1 calc R . . N2 N 0.80109(11) 0.61495(12) 0.07103(11) 0.0616(4) Uani 1 1 d . . . N3 N 0.83542(14) 0.20344(15) 0.35665(13) 0.0788(5) Uani 1 1 d . . . N4 N 0.99636(12) 0.32909(15) 0.13919(13) 0.0730(4) Uani 1 1 d . . . C1 C 0.42747(19) 0.8748(2) -0.47113(16) 0.0989(7) Uani 1 1 d . . . H1A H 0.4815 0.9031 -0.4878 0.148 Uiso 1 1 calc R . . H1B H 0.3777 0.9312 -0.4784 0.148 Uiso 1 1 calc R . . H1C H 0.3905 0.8166 -0.5192 0.148 Uiso 1 1 calc R . . C2 C 0.47920(14) 0.83274(16) -0.35689(14) 0.0731(5) Uani 1 1 d . . . H2 H 0.4230 0.7992 -0.3442 0.088 Uiso 1 1 calc R . . C3 C 0.52738(14) 0.92394(15) -0.27659(14) 0.0668(5) Uani 1 1 d . . . H3A H 0.4717 0.9754 -0.2862 0.080 Uiso 1 1 calc R . . H3B H 0.5801 0.9615 -0.2907 0.080 Uiso 1 1 calc R . . C4 C 0.58064(13) 0.88439(13) -0.16018(13) 0.0578(4) Uani 1 1 d . . . C5 C 0.66860(12) 0.80087(12) -0.14587(12) 0.0513(4) Uani 1 1 d . . . H5 H 0.7168 0.8381 -0.1678 0.062 Uiso 1 1 calc R . . C6 C 0.73472(13) 0.77916(13) -0.02471(13) 0.0572(4) Uani 1 1 d . . . H6 H 0.6832 0.7660 0.0027 0.069 Uiso 1 1 calc R . . C7 C 0.80817(13) 0.68432(15) 0.00817(13) 0.0630(4) Uani 1 1 d . . . H7 H 0.8584 0.6761 -0.0170 0.076 Uiso 1 1 calc R . . C8 C 0.86673(12) 0.45038(13) 0.16228(12) 0.0545(4) Uani 1 1 d . . . C9 C 0.80014(13) 0.46290(14) 0.21254(13) 0.0614(4) Uani 1 1 d . . . H9 H 0.7618 0.5269 0.2021 0.074 Uiso 1 1 calc R . . C10 C 0.79054(13) 0.38487(15) 0.27507(13) 0.0637(4) Uani 1 1 d . . . H10 H 0.7470 0.3959 0.3077 0.076 Uiso 1 1 calc R . . C11 C 0.84610(13) 0.28821(14) 0.29025(13) 0.0590(4) Uani 1 1 d . . . C12 C 0.79624(14) 0.88300(15) 0.03092(13) 0.0667(5) Uani 1 1 d . . . H12 H 0.8219 0.8727 0.1078 0.080 Uiso 1 1 calc R . . C13 C 0.72306(17) 0.98000(15) -0.00116(15) 0.0718(5) Uani 1 1 d . . . C14 C 0.7636(2) 1.07819(19) 0.06961(18) 0.1050(8) Uani 1 1 d . . . H14A H 0.7089 1.1327 0.0459 0.158 Uiso 1 1 calc R . . H14B H 0.8255 1.1062 0.0661 0.158 Uiso 1 1 calc R . . H14C H 0.7822 1.0583 0.1420 0.158 Uiso 1 1 calc R . . C15 C 0.62937(16) 0.97828(15) -0.08669(15) 0.0713(5) Uani 1 1 d . . . H15 H 0.5896 1.0419 -0.1030 0.086 Uiso 1 1 calc R . . C16 C 0.49358(14) 0.83670(18) -0.13408(16) 0.0780(5) Uani 1 1 d . . . H16A H 0.5256 0.8138 -0.0608 0.117 Uiso 1 1 calc R . . H16B H 0.4605 0.7757 -0.1797 0.117 Uiso 1 1 calc R . . H16C H 0.4406 0.8911 -0.1456 0.117 Uiso 1 1 calc R . . C17 C 0.62166(13) 0.70488(13) -0.22292(13) 0.0586(4) Uani 1 1 d . . . H17 H 0.5701 0.6675 -0.2057 0.070 Uiso 1 1 calc R . . C18 C 0.56270(15) 0.74770(15) -0.33712(14) 0.0698(5) Uani 1 1 d . . . H18A H 0.6150 0.7776 -0.3568 0.084 Uiso 1 1 calc R . . H18B H 0.5287 0.6870 -0.3843 0.084 Uiso 1 1 calc R . . C19 C 0.70302(17) 0.62203(17) -0.22101(17) 0.0847(6) Uani 1 1 d . . . H19A H 0.6697 0.5748 -0.2817 0.127 Uiso 1 1 calc R . . H19B H 0.7289 0.5801 -0.1565 0.127 Uiso 1 1 calc R . . H19C H 0.7617 0.6591 -0.2237 0.127 Uiso 1 1 calc R . . C20 C 0.89462(14) 0.90526(18) 0.01449(16) 0.0821(6) Uani 1 1 d . . . H20A H 0.8728 0.9167 -0.0601 0.123 Uiso 1 1 calc R . . H20B H 0.9422 0.8443 0.0393 0.123 Uiso 1 1 calc R . . H20C H 0.9306 0.9688 0.0540 0.123 Uiso 1 1 calc R . . C21 C 0.92406(12) 0.35198(14) 0.18322(12) 0.0561(4) Uani 1 1 d . . . C22 C 0.91291(13) 0.27190(14) 0.24581(13) 0.0606(4) Uani 1 1 d . . . H22 H 0.9507 0.2073 0.2576 0.073 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 O1 0.1609(17) 0.0824(11) 0.1255(14) 0.0303(10) 0.0768(13) 0.0259(11) O2 0.1052(12) 0.1204(13) 0.1209(13) 0.0325(10) 0.0726(11) 0.0103(10) O3 0.1271(14) 0.0850(10) 0.1870(18) -0.0001(11) 0.1092(14) 0.0319(10) O4 0.0874(10) 0.1076(12) 0.1175(12) 0.0162(10) 0.0707(9) 0.0260(9) N1 0.0598(8) 0.0786(10) 0.0710(9) 0.0118(8) 0.0381(7) 0.0188(8) N2 0.0570(8) 0.0697(9) 0.0622(8) 0.0076(7) 0.0309(7) 0.0141(7) N3 0.0754(11) 0.0832(12) 0.0699(10) 0.0076(9) 0.0266(9) -0.0001(9) N4 0.0575(9) 0.0771(11) 0.0869(11) -0.0114(9) 0.0353(8) 0.0130(8) C1 0.0957(15) 0.1061(17) 0.0700(13) 0.0097(12) 0.0166(11) 0.0046(14) C2 0.0619(11) 0.0809(13) 0.0673(11) 0.0068(9) 0.0217(9) -0.0031(10) C3 0.0590(10) 0.0661(11) 0.0736(11) 0.0091(9) 0.0288(9) 0.0087(9) C4 0.0520(9) 0.0614(10) 0.0650(10) 0.0006(8) 0.0310(8) 0.0039(8) C5 0.0472(8) 0.0566(9) 0.0557(9) 0.0026(7) 0.0283(7) -0.0010(7) C6 0.0534(9) 0.0668(10) 0.0595(9) 0.0065(8) 0.0329(8) 0.0047(8) C7 0.0551(9) 0.0802(12) 0.0607(10) 0.0078(9) 0.0325(8) 0.0081(9) C8 0.0453(8) 0.0656(10) 0.0484(8) -0.0026(7) 0.0178(7) 0.0079(8) C9 0.0591(10) 0.0700(11) 0.0576(9) 0.0032(8) 0.0289(8) 0.0177(9) C10 0.0549(10) 0.0787(12) 0.0581(10) 0.0023(9) 0.0263(8) 0.0091(9) C11 0.0516(9) 0.0639(10) 0.0526(9) -0.0019(8) 0.0163(7) -0.0015(8) C12 0.0651(11) 0.0820(12) 0.0512(9) -0.0023(8) 0.0250(8) -0.0068(10) C13 0.0856(13) 0.0680(11) 0.0686(11) -0.0102(9) 0.0412(11) -0.0074(10) C14 0.134(2) 0.0877(15) 0.0942(16) -0.0273(13) 0.0533(15) -0.0193(15) C15 0.0786(13) 0.0628(11) 0.0778(12) -0.0035(9) 0.0403(11) 0.0104(10) C16 0.0613(11) 0.0989(14) 0.0874(13) 0.0107(11) 0.0458(10) 0.0117(10) C17 0.0557(9) 0.0560(9) 0.0674(10) -0.0009(8) 0.0311(8) -0.0041(8) C18 0.0724(12) 0.0692(11) 0.0635(11) -0.0055(9) 0.0274(9) -0.0105(10) C19 0.0845(14) 0.0808(13) 0.0888(14) -0.0176(11) 0.0397(11) 0.0102(11) C20 0.0586(11) 0.1005(15) 0.0766(12) 0.0016(11) 0.0218(9) -0.0121(10) C21 0.0452(8) 0.0648(10) 0.0538(9) -0.0111(8) 0.0189(7) 0.0035(8) C22 0.0502(9) 0.0600(10) 0.0589(10) -0.0094(8) 0.0140(8) 0.0058(8) _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 O1 N3 1.223(2) . ? O2 N3 1.218(2) . ? O3 N4 1.214(2) . ? O4 N4 1.226(2) . ? N1 C8 1.343(2) . ? N1 N2 1.3877(19) . ? N1 H1 0.8600 . ? N2 C7 1.267(2) . ? N3 C11 1.456(2) . ? N4 C21 1.442(2) . ? C1 C2 1.521(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C18 1.504(3) . ? C2 C3 1.517(3) . ? C2 H2 0.9800 . ? C3 C4 1.536(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C15 1.494(2) . ? C4 C16 1.549(2) . ? C4 C5 1.552(2) . ? C5 C17 1.536(2) . ? C5 C6 1.547(2) . ? C5 H5 0.9800 . ? C6 C7 1.488(2) . ? C6 C12 1.544(2) . ? C6 H6 0.9800 . ? C7 H7 0.9300 . ? C8 C21 1.412(2) . ? C8 C9 1.419(2) . ? C9 C10 1.352(2) . ? C9 H9 0.9300 . ? C10 C11 1.388(2) . ? C10 H10 0.9300 . ? C11 C22 1.363(2) . ? C12 C13 1.508(3) . ? C12 C20 1.531(3) . ? C12 H12 0.9800 . ? C13 C15 1.318(3) . ? C13 C14 1.505(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.527(2) . ? C17 C19 1.527(2) . ? C17 H17 0.9800 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.380(2) . ? C22 H22 0.9300 . ? 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 C8 N1 N2 119.06(14) . . ? C8 N1 H1 120.5 . . ? N2 N1 H1 120.5 . . ? C7 N2 N1 115.86(14) . . ? O2 N3 O1 123.47(19) . . ? O2 N3 C11 118.48(18) . . ? O1 N3 C11 118.04(19) . . ? O3 N4 O4 121.77(17) . . ? O3 N4 C21 118.93(19) . . ? O4 N4 C21 119.31(16) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C18 C2 C3 109.54(14) . . ? C18 C2 C1 112.89(18) . . ? C3 C2 C1 111.65(17) . . ? C18 C2 H2 107.5 . . ? C3 C2 H2 107.5 . . ? C1 C2 H2 107.5 . . ? C2 C3 C4 113.11(15) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C15 C4 C3 109.71(15) . . ? C15 C4 C16 107.03(14) . . ? C3 C4 C16 108.71(14) . . ? C15 C4 C5 109.78(13) . . ? C3 C4 C5 108.67(13) . . ? C16 C4 C5 112.90(14) . . ? C17 C5 C6 119.48(13) . . ? C17 C5 C4 111.12(12) . . ? C6 C5 C4 107.44(13) . . ? C17 C5 H5 106.0 . . ? C6 C5 H5 106.0 . . ? C4 C5 H5 106.0 . . ? C7 C6 C12 110.22(14) . . ? C7 C6 C5 117.43(14) . . ? C12 C6 C5 109.28(13) . . ? C7 C6 H6 106.4 . . ? C12 C6 H6 106.4 . . ? C5 C6 H6 106.4 . . ? N2 C7 C6 118.81(15) . . ? N2 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? N1 C8 C21 123.80(15) . . ? N1 C8 C9 120.39(15) . . ? C21 C8 C9 115.80(15) . . ? C10 C9 C8 122.22(16) . . ? C10 C9 H9 118.9 . . ? C8 C9 H9 118.9 . . ? C9 C10 C11 119.62(16) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C22 C11 C10 121.03(16) . . ? C22 C11 N3 119.01(17) . . ? C10 C11 N3 119.94(17) . . ? C13 C12 C20 110.77(16) . . ? C13 C12 C6 111.02(14) . . ? C20 C12 C6 114.14(15) . . ? C13 C12 H12 106.8 . . ? C20 C12 H12 106.8 . . ? C6 C12 H12 106.8 . . ? C15 C13 C14 122.4(2) . . ? C15 C13 C12 121.49(16) . . ? C14 C13 C12 116.15(18) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 C4 126.53(17) . . ? C13 C15 H15 116.7 . . ? C4 C15 H15 116.7 . . ? C4 C16 H16A 109.5 . . ? C4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C19 106.98(15) . . ? C18 C17 C5 109.11(13) . . ? C19 C17 C5 115.27(14) . . ? C18 C17 H17 108.4 . . ? C19 C17 H17 108.4 . . ? C5 C17 H17 108.4 . . ? C2 C18 C17 116.00(15) . . ? C2 C18 H18A 108.3 . . ? C17 C18 H18A 108.3 . . ? C2 C18 H18B 108.3 . . ? C17 C18 H18B 108.3 . . ? H18A C18 H18B 107.4 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C12 C20 H20A 109.5 . . ? C12 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C12 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C8 121.81(15) . . ? C22 C21 N4 116.34(16) . . ? C8 C21 N4 121.85(16) . . ? C11 C22 C21 119.48(16) . . ? C11 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.46 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.170 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.028