# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'B. Ramachary Dhevalapally' _publ_contact_author_email RAMSC@UOHYD.ERNET.IN _publ_section_title ; High-yielding Synthesis of Nefopam Analogues (Functionalized Benzoxazocines) by Sequential One-pot Cascade Operations ; loop_ _publ_author_name 'B. Ramachary Dhevalapally' 'Vidadala V Narayana' 'M. Shiva Prasad' 'Kinthada Ramakumar' # Attachment 'DBR-7ha cif file.txt' data_dbr7ha _database_code_depnum_ccdc_archive 'CCDC 637091' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H25 N O3' _chemical_formula_weight 399.47 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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)/c 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 14.2321(13) _cell_length_b 13.8619(13) _cell_length_c 11.2976(11) _cell_angle_alpha 90.00 _cell_angle_beta 105.460(2) _cell_angle_gamma 90.00 _cell_volume 2148.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 5417 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 24.89 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9686 _exptl_absorpt_correction_T_max 0.9952 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 22021 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 26.05 _reflns_number_total 4240 _reflns_number_gt 3108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0560P)^2^+1.1904P] 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 4240 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1082 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _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 0.22878(15) 0.45246(14) 0.5263(2) 0.0605(6) Uani 1 1 d . . . O2 O 0.34942(18) 0.02350(16) 0.42694(19) 0.0657(7) Uani 1 1 d . . . O3 O 0.31279(15) 0.01095(13) 0.60562(18) 0.0504(5) Uani 1 1 d . . . N1 N 0.11650(16) 0.33793(16) 0.32483(19) 0.0397(5) Uani 1 1 d . . . C1 C 0.21556(18) 0.19956(18) 0.4186(2) 0.0338(6) Uani 1 1 d . . . C2 C 0.29291(18) 0.16231(18) 0.5121(2) 0.0332(6) Uani 1 1 d . . . C3 C 0.34601(18) 0.22193(19) 0.6074(2) 0.0356(6) Uani 1 1 d . . . C4 C 0.31988(19) 0.3181(2) 0.6075(3) 0.0425(7) Uani 1 1 d . . . H4 H 0.3549 0.3583 0.6697 0.051 Uiso 1 1 calc R . . C5 C 0.24292(19) 0.35593(19) 0.5175(3) 0.0405(6) Uani 1 1 d . . . C6 C 0.19052(18) 0.29697(18) 0.4226(2) 0.0348(6) Uani 1 1 d . . . C7 C 0.1469(2) 0.4075(2) 0.2459(3) 0.0565(8) Uani 1 1 d . . . H7A H 0.1165 0.3908 0.1610 0.068 Uiso 1 1 calc R . . H7B H 0.2169 0.4025 0.2590 0.068 Uiso 1 1 calc R . . C8 C 0.1222(3) 0.5094(3) 0.2667(4) 0.0691(10) Uani 1 1 d . . . H8 H 0.1111 0.5507 0.1996 0.083 Uiso 1 1 calc R . . C9 C 0.1146(3) 0.5463(2) 0.3705(4) 0.0683(10) Uani 1 1 d . . . H9 H 0.0959 0.6107 0.3694 0.082 Uiso 1 1 calc R . . C10 C 0.1331(2) 0.4944(2) 0.4903(3) 0.0551(8) Uani 1 1 d . . . H10A H 0.1260 0.5392 0.5532 0.066 Uiso 1 1 calc R . . H10B H 0.0848 0.4439 0.4837 0.066 Uiso 1 1 calc R . . C11 C 0.1592(2) 0.1368(2) 0.3147(3) 0.0479(7) Uani 1 1 d . . . H11A H 0.1053 0.1076 0.3372 0.072 Uiso 1 1 calc R . . H11B H 0.2013 0.0874 0.2982 0.072 Uiso 1 1 calc R . . H11C H 0.1353 0.1756 0.2425 0.072 Uiso 1 1 calc R . . C12 C 0.32117(19) 0.05915(19) 0.5074(2) 0.0384(6) Uani 1 1 d . . . C13 C 0.3576(3) -0.0842(2) 0.6256(3) 0.0707(10) Uani 1 1 d . . . H13A H 0.4159 -0.0856 0.5966 0.085 Uiso 1 1 calc R . . H13B H 0.3126 -0.1326 0.5810 0.085 Uiso 1 1 calc R . . C14 C 0.3825(3) -0.1045(3) 0.7577(3) 0.0802(12) Uani 1 1 d . . . H14A H 0.4274 -0.0566 0.8009 0.120 Uiso 1 1 calc R . . H14B H 0.4120 -0.1671 0.7731 0.120 Uiso 1 1 calc R . . H14C H 0.3244 -0.1030 0.7855 0.120 Uiso 1 1 calc R . . C15 C 0.42967(18) 0.18571(19) 0.7070(2) 0.0364(6) Uani 1 1 d . . . C16 C 0.50536(19) 0.13172(19) 0.6831(2) 0.0398(6) Uani 1 1 d . . . H16 H 0.5044 0.1173 0.6024 0.048 Uiso 1 1 calc R . . C17 C 0.5813(2) 0.0997(2) 0.7778(3) 0.0480(7) Uani 1 1 d . . . H17 H 0.6310 0.0632 0.7606 0.058 Uiso 1 1 calc R . . C18 C 0.5844(2) 0.1210(3) 0.8972(3) 0.0608(9) Uani 1 1 d . . . H18 H 0.6358 0.0991 0.9609 0.073 Uiso 1 1 calc R . . C19 C 0.5114(2) 0.1749(3) 0.9223(3) 0.0701(11) Uani 1 1 d . . . H19 H 0.5139 0.1902 1.0032 0.084 Uiso 1 1 calc R . . C20 C 0.4344(2) 0.2067(2) 0.8286(3) 0.0534(8) Uani 1 1 d . . . H20 H 0.3849 0.2425 0.8471 0.064 Uiso 1 1 calc R . . C21 C 0.01840(19) 0.32241(19) 0.3153(2) 0.0388(6) Uani 1 1 d . . . C22 C -0.0112(2) 0.2687(2) 0.4034(3) 0.0455(7) Uani 1 1 d . . . H22 H 0.0357 0.2431 0.4697 0.055 Uiso 1 1 calc R . . C23 C -0.1083(2) 0.2527(2) 0.3942(3) 0.0585(9) Uani 1 1 d . . . H23 H -0.1258 0.2160 0.4538 0.070 Uiso 1 1 calc R . . C24 C -0.1789(2) 0.2896(3) 0.2996(4) 0.0685(10) Uani 1 1 d . . . H24 H -0.2443 0.2783 0.2941 0.082 Uiso 1 1 calc R . . C25 C -0.1521(2) 0.3439(3) 0.2122(3) 0.0682(10) Uani 1 1 d . . . H25 H -0.2000 0.3697 0.1473 0.082 Uiso 1 1 calc R . . C26 C -0.0547(2) 0.3607(2) 0.2193(3) 0.0566(8) Uani 1 1 d . . . H26 H -0.0380 0.3978 0.1594 0.068 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 0.0502(13) 0.0289(11) 0.0884(16) -0.0104(10) -0.0059(11) 0.0025(9) O2 0.0963(18) 0.0541(14) 0.0504(13) -0.0071(10) 0.0258(12) 0.0275(12) O3 0.0621(13) 0.0342(11) 0.0571(13) 0.0073(9) 0.0200(10) 0.0097(9) N1 0.0401(13) 0.0337(13) 0.0443(13) 0.0078(10) 0.0099(10) 0.0026(10) C1 0.0344(14) 0.0327(14) 0.0356(14) 0.0014(11) 0.0114(11) -0.0019(11) C2 0.0355(14) 0.0302(14) 0.0371(14) -0.0002(11) 0.0155(11) 0.0028(11) C3 0.0321(14) 0.0372(15) 0.0394(15) -0.0018(12) 0.0127(12) 0.0011(11) C4 0.0376(16) 0.0385(16) 0.0470(16) -0.0084(13) 0.0038(13) -0.0031(12) C5 0.0387(15) 0.0274(14) 0.0546(17) -0.0004(12) 0.0113(13) 0.0011(12) C6 0.0306(14) 0.0331(15) 0.0414(15) 0.0040(12) 0.0109(11) 0.0008(11) C7 0.058(2) 0.056(2) 0.0599(19) 0.0198(16) 0.0227(16) 0.0049(16) C8 0.075(2) 0.045(2) 0.083(3) 0.0281(19) 0.014(2) -0.0015(17) C9 0.066(2) 0.0275(17) 0.099(3) 0.0060(18) 0.001(2) 0.0076(15) C10 0.0517(19) 0.0320(16) 0.077(2) -0.0099(15) 0.0090(16) 0.0101(14) C11 0.0484(17) 0.0427(17) 0.0478(17) -0.0087(13) 0.0045(14) 0.0060(14) C12 0.0411(16) 0.0374(16) 0.0349(15) -0.0044(12) 0.0073(12) 0.0024(12) C13 0.102(3) 0.0341(17) 0.070(2) 0.0081(16) 0.013(2) 0.0159(18) C14 0.086(3) 0.058(2) 0.082(3) 0.020(2) -0.003(2) 0.009(2) C15 0.0326(14) 0.0347(15) 0.0413(15) -0.0028(11) 0.0090(12) 0.0004(11) C16 0.0375(15) 0.0415(16) 0.0420(15) -0.0061(12) 0.0134(12) -0.0019(12) C17 0.0336(15) 0.0490(18) 0.0608(19) -0.0049(15) 0.0116(14) 0.0088(13) C18 0.0494(19) 0.076(2) 0.0485(19) -0.0007(17) -0.0009(14) 0.0231(17) C19 0.062(2) 0.105(3) 0.0397(17) -0.0058(18) 0.0072(16) 0.030(2) C20 0.0462(18) 0.071(2) 0.0428(17) -0.0087(15) 0.0116(14) 0.0218(16) C21 0.0400(16) 0.0307(15) 0.0408(15) -0.0048(12) 0.0024(12) 0.0040(12) C22 0.0408(16) 0.0377(16) 0.0557(18) 0.0010(13) 0.0089(14) 0.0017(13) C23 0.0459(19) 0.0440(19) 0.088(2) -0.0031(17) 0.0222(18) -0.0009(15) C24 0.0412(19) 0.051(2) 0.109(3) -0.018(2) 0.012(2) -0.0045(16) C25 0.046(2) 0.058(2) 0.079(2) -0.0124(19) -0.0200(17) 0.0164(17) C26 0.056(2) 0.0497(19) 0.0556(19) 0.0001(15) -0.0010(15) 0.0083(15) _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 C5 1.361(3) . ? O1 C10 1.436(3) . ? O2 C12 1.194(3) . ? O3 C12 1.328(3) . ? O3 C13 1.457(4) . ? N1 C21 1.388(3) . ? N1 C6 1.425(3) . ? N1 C7 1.455(3) . ? C1 C6 1.400(4) . ? C1 C2 1.405(3) . ? C1 C11 1.508(4) . ? C2 C3 1.407(3) . ? C2 C12 1.490(4) . ? C3 C4 1.384(4) . ? C3 C15 1.490(3) . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.396(4) . ? C7 C8 1.488(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.310(5) . ? C8 H8 0.9300 . ? C9 C10 1.493(5) . ? C9 H9 0.9300 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C13 C14 1.466(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.389(4) . ? C15 C16 1.396(4) . ? C16 C17 1.376(4) . ? C16 H16 0.9300 . ? C17 C18 1.371(4) . ? C17 H17 0.9300 . ? C18 C19 1.368(4) . ? C18 H18 0.9300 . ? C19 C20 1.377(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C26 1.392(4) . ? C21 C22 1.395(4) . ? C22 C23 1.376(4) . ? C22 H22 0.9300 . ? C23 C24 1.356(5) . ? C23 H23 0.9300 . ? C24 C25 1.374(5) . ? C24 H24 0.9300 . ? C25 C26 1.388(5) . ? C25 H25 0.9300 . ? C26 H26 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 C5 O1 C10 121.7(2) . . ? C12 O3 C13 116.9(2) . . ? C21 N1 C6 121.2(2) . . ? C21 N1 C7 120.8(2) . . ? C6 N1 C7 117.4(2) . . ? C6 C1 C2 119.0(2) . . ? C6 C1 C11 119.6(2) . . ? C2 C1 C11 121.4(2) . . ? C1 C2 C3 120.9(2) . . ? C1 C2 C12 119.4(2) . . ? C3 C2 C12 119.7(2) . . ? C4 C3 C2 118.5(2) . . ? C4 C3 C15 119.0(2) . . ? C2 C3 C15 122.5(2) . . ? C5 C4 C3 121.6(2) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? O1 C5 C4 115.0(2) . . ? O1 C5 C6 124.9(2) . . ? C4 C5 C6 119.9(2) . . ? C5 C6 C1 120.1(2) . . ? C5 C6 N1 119.7(2) . . ? C1 C6 N1 120.1(2) . . ? N1 C7 C8 114.3(3) . . ? N1 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 126.2(3) . . ? C9 C8 H8 116.9 . . ? C7 C8 H8 116.9 . . ? C8 C9 C10 125.9(3) . . ? C8 C9 H9 117.1 . . ? C10 C9 H9 117.1 . . ? O1 C10 C9 112.2(3) . . ? O1 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? O1 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O2 C12 O3 123.5(3) . . ? O2 C12 C2 125.0(3) . . ? O3 C12 C2 111.6(2) . . ? O3 C13 C14 108.0(3) . . ? O3 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? O3 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? 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 . . ? C20 C15 C16 117.9(2) . . ? C20 C15 C3 119.6(2) . . ? C16 C15 C3 122.5(2) . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 C16 120.5(3) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C19 C18 C17 119.7(3) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C20 120.6(3) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C15 120.8(3) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? N1 C21 C26 121.9(3) . . ? N1 C21 C22 121.1(2) . . ? C26 C21 C22 117.0(3) . . ? C23 C22 C21 121.3(3) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C24 C23 C22 121.2(3) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C25 118.9(3) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C24 C25 C26 121.0(3) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C26 C21 120.6(3) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.248 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.041 # Attachment 'DBR-12aa cif file.txt' data_dbr12aa _database_code_depnum_ccdc_archive 'CCDC 637092' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H30 N2 O5' _chemical_formula_weight 522.58 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9791(7) _cell_length_b 15.0018(8) _cell_length_c 13.9935(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.8270(10) _cell_angle_gamma 90.00 _cell_volume 2723.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6719 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 25.96 _exptl_crystal_description Block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9696 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 19684 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.05 _reflns_number_total 5359 _reflns_number_gt 3670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0563P)^2^+0.3571P] 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 5359 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 O1 O 0.12935(9) 0.16997(8) 0.83202(8) 0.0539(3) Uani 1 1 d . . . O2 O 0.37469(10) 0.39140(10) 0.58690(10) 0.0671(4) Uani 1 1 d . . . O3 O 0.10594(13) 0.58210(11) 0.61442(11) 0.0883(5) Uani 1 1 d . . . O4 O -0.32173(11) 0.17392(12) 0.63424(12) 0.0836(5) Uani 1 1 d . . . O5 O -0.34516(10) 0.22876(10) 0.77969(9) 0.0634(4) Uani 1 1 d . . . N1 N 0.08681(10) 0.22637(9) 0.64771(9) 0.0435(3) Uani 1 1 d . . . N2 N 0.24500(11) 0.49550(9) 0.57840(10) 0.0494(4) Uani 1 1 d . . . C1 C -0.17599(13) 0.19733(12) 0.74100(12) 0.0466(4) Uani 1 1 d . . . C2 C -0.09813(13) 0.21382(11) 0.67615(12) 0.0436(4) Uani 1 1 d . . . C3 C 0.00415(13) 0.20638(11) 0.70943(11) 0.0423(4) Uani 1 1 d . . . C4 C 0.02706(13) 0.18154(12) 0.80381(12) 0.0462(4) Uani 1 1 d . . . C5 C -0.05032(15) 0.16789(13) 0.86689(13) 0.0560(5) Uani 1 1 d . . . H5 H -0.0346 0.1530 0.9302 0.067 Uiso 1 1 calc R . . C6 C -0.15109(15) 0.17649(13) 0.83556(14) 0.0555(5) Uani 1 1 d . . . H6 H -0.2036 0.1682 0.8784 0.067 Uiso 1 1 calc R . . C7 C 0.17044(16) 0.24458(13) 0.88633(13) 0.0596(5) Uani 1 1 d . . . H7A H 0.2421 0.2332 0.9040 0.071 Uiso 1 1 calc R . . H7B H 0.1326 0.2511 0.9446 0.071 Uiso 1 1 calc R . . C8 C 0.16267(14) 0.32910(13) 0.82960(12) 0.0511(5) Uani 1 1 d . . . C9 C 0.21108(13) 0.33033(11) 0.73265(12) 0.0459(4) Uani 1 1 d . . . H9 H 0.2614 0.2818 0.7303 0.055 Uiso 1 1 calc R . . C10 C 0.12843(14) 0.31572(11) 0.65206(12) 0.0443(4) Uani 1 1 d . . . H10A H 0.0723 0.3573 0.6611 0.053 Uiso 1 1 calc R . . H10B H 0.1585 0.3295 0.5912 0.053 Uiso 1 1 calc R . . C11 C 0.26889(13) 0.41995(12) 0.72343(12) 0.0486(4) Uani 1 1 d . . . H11 H 0.3276 0.4213 0.7693 0.058 Uiso 1 1 calc R . . C12 C 0.20029(14) 0.50066(12) 0.73970(13) 0.0538(5) Uani 1 1 d . . . H12 H 0.2435 0.5466 0.7706 0.065 Uiso 1 1 calc R . . C13 C 0.10764(16) 0.48553(14) 0.80340(15) 0.0653(6) Uani 1 1 d . . . H13A H 0.1024 0.5353 0.8472 0.078 Uiso 1 1 calc R . . H13B H 0.0451 0.4842 0.7635 0.078 Uiso 1 1 calc R . . C14 C 0.11533(15) 0.40084(14) 0.85969(14) 0.0606(5) Uani 1 1 d . . . H14 H 0.0851 0.3988 0.9190 0.073 Uiso 1 1 calc R . . C15 C 0.17400(16) 0.53262(13) 0.63983(15) 0.0575(5) Uani 1 1 d . . . C16 C 0.30693(14) 0.43180(12) 0.62424(13) 0.0488(4) Uani 1 1 d . . . C17 C -0.28714(15) 0.19819(13) 0.71037(15) 0.0549(5) Uani 1 1 d . . . C18 C -0.45560(15) 0.22905(16) 0.76279(18) 0.0749(6) Uani 1 1 d . . . H18A H -0.4825 0.1688 0.7643 0.090 Uiso 1 1 calc R . . H18B H -0.4730 0.2550 0.7009 0.090 Uiso 1 1 calc R . . C19 C -0.49917(17) 0.2832(2) 0.84013(18) 0.0932(8) Uani 1 1 d . . . H19A H -0.4779 0.2587 0.9010 0.140 Uiso 1 1 calc R . . H19B H -0.5730 0.2826 0.8340 0.140 Uiso 1 1 calc R . . H19C H -0.4748 0.3434 0.8356 0.140 Uiso 1 1 calc R . . C20 C -0.12156(15) 0.24174(13) 0.57462(12) 0.0564(5) Uani 1 1 d . . . H20A H -0.0628 0.2717 0.5498 0.085 Uiso 1 1 calc R . . H20B H -0.1797 0.2813 0.5727 0.085 Uiso 1 1 calc R . . H20C H -0.1372 0.1900 0.5365 0.085 Uiso 1 1 calc R . . C21 C 0.13501(13) 0.15903(11) 0.59749(11) 0.0437(4) Uani 1 1 d . . . C22 C 0.22527(15) 0.17404(13) 0.54794(13) 0.0577(5) Uani 1 1 d . . . H22 H 0.2572 0.2295 0.5515 0.069 Uiso 1 1 calc R . . C23 C 0.26726(18) 0.10716(16) 0.49391(15) 0.0734(6) Uani 1 1 d . . . H23 H 0.3268 0.1186 0.4607 0.088 Uiso 1 1 calc R . . C24 C 0.22305(19) 0.02400(16) 0.48808(16) 0.0757(7) Uani 1 1 d . . . H24 H 0.2516 -0.0205 0.4510 0.091 Uiso 1 1 calc R . . C25 C 0.13574(18) 0.00800(14) 0.53827(15) 0.0685(6) Uani 1 1 d . . . H25 H 0.1057 -0.0483 0.5359 0.082 Uiso 1 1 calc R . . C26 C 0.09209(15) 0.07392(12) 0.59208(13) 0.0539(5) Uani 1 1 d . . . H26 H 0.0329 0.0615 0.6254 0.065 Uiso 1 1 calc R . . C27 C 0.25309(15) 0.51742(11) 0.47906(13) 0.0508(5) Uani 1 1 d . . . C28 C 0.34529(16) 0.54854(13) 0.44728(14) 0.0618(5) Uani 1 1 d . . . H28 H 0.4005 0.5568 0.4904 0.074 Uiso 1 1 calc R . . C29 C 0.3566(2) 0.56755(15) 0.35241(17) 0.0784(7) Uani 1 1 d . . . H29 H 0.4196 0.5877 0.3311 0.094 Uiso 1 1 calc R . . C30 C 0.2760(2) 0.55701(18) 0.28975(18) 0.0869(7) Uani 1 1 d . . . H30 H 0.2835 0.5709 0.2256 0.104 Uiso 1 1 calc R . . C31 C 0.1839(2) 0.52607(18) 0.32028(18) 0.0879(7) Uani 1 1 d . . . H31 H 0.1291 0.5189 0.2766 0.105 Uiso 1 1 calc R . . C32 C 0.17098(17) 0.50497(15) 0.41636(17) 0.0709(6) Uani 1 1 d . . . H32 H 0.1085 0.4831 0.4372 0.085 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 0.0507(8) 0.0587(8) 0.0518(7) 0.0088(6) -0.0068(6) 0.0007(6) O2 0.0582(8) 0.0768(10) 0.0673(9) 0.0066(7) 0.0165(7) 0.0148(7) O3 0.0996(12) 0.0817(11) 0.0843(11) 0.0094(9) 0.0165(9) 0.0427(10) O4 0.0615(9) 0.1149(14) 0.0737(10) -0.0265(9) -0.0065(8) 0.0005(9) O5 0.0458(8) 0.0782(10) 0.0666(9) -0.0025(7) 0.0102(6) 0.0002(7) N1 0.0487(8) 0.0405(8) 0.0415(8) -0.0019(6) 0.0054(6) -0.0021(6) N2 0.0511(9) 0.0451(8) 0.0522(9) -0.0005(7) 0.0051(7) -0.0015(7) C1 0.0473(10) 0.0451(10) 0.0476(10) 0.0003(8) 0.0021(8) 0.0017(8) C2 0.0508(10) 0.0391(9) 0.0409(9) -0.0017(7) 0.0005(8) 0.0008(8) C3 0.0467(10) 0.0398(9) 0.0405(9) -0.0008(7) 0.0030(8) -0.0009(8) C4 0.0486(10) 0.0436(10) 0.0462(10) 0.0066(8) -0.0019(8) 0.0005(8) C5 0.0615(13) 0.0632(13) 0.0433(10) 0.0149(9) 0.0018(9) -0.0045(10) C6 0.0531(12) 0.0614(12) 0.0526(11) 0.0079(9) 0.0114(9) -0.0023(9) C7 0.0603(12) 0.0739(14) 0.0440(10) 0.0050(10) -0.0066(9) -0.0087(10) C8 0.0519(11) 0.0606(12) 0.0406(10) -0.0029(9) -0.0021(8) -0.0087(9) C9 0.0459(10) 0.0451(10) 0.0467(10) -0.0012(8) 0.0003(8) 0.0013(8) C10 0.0511(10) 0.0413(10) 0.0408(9) -0.0005(8) 0.0050(8) 0.0001(8) C11 0.0452(10) 0.0517(11) 0.0488(10) -0.0038(8) -0.0012(8) -0.0021(8) C12 0.0595(12) 0.0474(11) 0.0546(11) -0.0103(9) 0.0025(9) -0.0054(9) C13 0.0693(13) 0.0645(14) 0.0629(13) -0.0160(10) 0.0137(11) 0.0052(11) C14 0.0641(13) 0.0720(14) 0.0462(11) -0.0083(10) 0.0110(9) -0.0069(11) C15 0.0627(12) 0.0431(11) 0.0671(13) -0.0054(9) 0.0091(10) 0.0028(10) C16 0.0440(10) 0.0483(11) 0.0543(11) -0.0011(9) 0.0029(9) -0.0047(9) C17 0.0526(12) 0.0530(12) 0.0591(12) -0.0009(10) 0.0042(10) -0.0012(9) C18 0.0476(12) 0.0843(16) 0.0933(17) 0.0082(13) 0.0087(11) -0.0031(11) C19 0.0616(15) 0.126(2) 0.0935(18) 0.0100(16) 0.0257(13) 0.0168(14) C20 0.0576(12) 0.0679(13) 0.0436(10) 0.0022(9) -0.0022(9) 0.0043(10) C21 0.0496(10) 0.0456(10) 0.0353(9) -0.0022(7) -0.0055(8) 0.0043(8) C22 0.0618(12) 0.0586(12) 0.0533(11) -0.0051(9) 0.0087(9) 0.0014(10) C23 0.0744(15) 0.0825(17) 0.0642(14) -0.0101(12) 0.0174(11) 0.0136(13) C24 0.0947(18) 0.0720(16) 0.0602(13) -0.0199(11) -0.0017(12) 0.0240(13) C25 0.0878(16) 0.0515(12) 0.0652(13) -0.0106(10) -0.0120(12) 0.0074(11) C26 0.0607(12) 0.0485(11) 0.0520(11) -0.0043(9) -0.0051(9) 0.0010(9) C27 0.0593(12) 0.0398(10) 0.0532(11) -0.0017(8) 0.0010(9) -0.0005(9) C28 0.0726(14) 0.0555(12) 0.0573(12) 0.0012(10) 0.0025(10) -0.0157(10) C29 0.0957(18) 0.0744(16) 0.0657(15) 0.0087(12) 0.0110(14) -0.0161(13) C30 0.113(2) 0.0868(18) 0.0611(15) 0.0102(13) 0.0033(15) 0.0060(16) C31 0.0948(19) 0.0981(19) 0.0687(16) -0.0052(14) -0.0290(14) 0.0131(16) C32 0.0626(13) 0.0752(15) 0.0742(15) -0.0044(12) -0.0074(12) 0.0031(11) _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 C4 1.384(2) . ? O1 C7 1.445(2) . ? O2 C16 1.201(2) . ? O3 C15 1.199(2) . ? O4 C17 1.199(2) . ? O5 C17 1.329(2) . ? O5 C18 1.445(2) . ? N1 C21 1.391(2) . ? N1 C3 1.430(2) . ? N1 C10 1.446(2) . ? N2 C16 1.392(2) . ? N2 C15 1.396(2) . ? N2 C27 1.436(2) . ? C1 C6 1.388(3) . ? C1 C2 1.402(2) . ? C1 C17 1.492(3) . ? C2 C3 1.397(2) . ? C2 C20 1.503(2) . ? C3 C4 1.395(2) . ? C4 C5 1.373(2) . ? C5 C6 1.372(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.498(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C14 1.315(3) . ? C8 C9 1.513(2) . ? C9 C11 1.547(2) . ? C9 C10 1.547(2) . ? C9 H9 0.9800 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.499(2) . ? C11 C12 1.524(2) . ? C11 H11 0.9800 . ? C12 C15 1.506(3) . ? C12 C13 1.536(3) . ? C12 H12 0.9800 . ? C13 C14 1.496(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14 0.9300 . ? C18 C19 1.480(3) . ? 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 C26 1.394(2) . ? C21 C22 1.398(2) . ? C22 C23 1.379(3) . ? C22 H22 0.9300 . ? C23 C24 1.374(3) . ? C23 H23 0.9300 . ? C24 C25 1.373(3) . ? C24 H24 0.9300 . ? C25 C26 1.376(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C32 1.371(3) . ? C27 C28 1.372(3) . ? C28 C29 1.370(3) . ? C28 H28 0.9300 . ? C29 C30 1.352(3) . ? C29 H29 0.9300 . ? C30 C31 1.364(3) . ? C30 H30 0.9300 . ? C31 C32 1.397(3) . ? C31 H31 0.9300 . ? C32 H32 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 C4 O1 C7 112.79(14) . . ? C17 O5 C18 117.63(16) . . ? C21 N1 C3 120.73(14) . . ? C21 N1 C10 121.42(13) . . ? C3 N1 C10 117.09(13) . . ? C16 N2 C15 111.90(15) . . ? C16 N2 C27 122.99(14) . . ? C15 N2 C27 125.10(16) . . ? C6 C1 C2 120.42(16) . . ? C6 C1 C17 118.01(16) . . ? C2 C1 C17 121.53(16) . . ? C3 C2 C1 117.84(15) . . ? C3 C2 C20 119.92(15) . . ? C1 C2 C20 122.21(16) . . ? C4 C3 C2 120.56(15) . . ? C4 C3 N1 119.10(15) . . ? C2 C3 N1 120.32(14) . . ? C5 C4 O1 120.83(15) . . ? C5 C4 C3 120.67(17) . . ? O1 C4 C3 118.49(15) . . ? C6 C5 C4 119.32(17) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 121.10(16) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? O1 C7 C8 111.07(15) . . ? O1 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? O1 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C14 C8 C7 123.19(17) . . ? C14 C8 C9 119.26(17) . . ? C7 C8 C9 117.55(16) . . ? C8 C9 C11 107.56(14) . . ? C8 C9 C10 110.71(14) . . ? C11 C9 C10 112.90(14) . . ? C8 C9 H9 108.5 . . ? C11 C9 H9 108.5 . . ? C10 C9 H9 108.5 . . ? N1 C10 C9 114.30(14) . . ? N1 C10 H10A 108.7 . . ? C9 C10 H10A 108.7 . . ? N1 C10 H10B 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C16 C11 C12 104.80(15) . . ? C16 C11 C9 110.81(14) . . ? C12 C11 C9 113.00(14) . . ? C16 C11 H11 109.4 . . ? C12 C11 H11 109.4 . . ? C9 C11 H11 109.4 . . ? C15 C12 C11 103.31(14) . . ? C15 C12 C13 115.28(17) . . ? C11 C12 C13 116.17(15) . . ? C15 C12 H12 107.2 . . ? C11 C12 H12 107.2 . . ? C13 C12 H12 107.2 . . ? C14 C13 C12 112.99(16) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C8 C14 C13 123.37(17) . . ? C8 C14 H14 118.3 . . ? C13 C14 H14 118.3 . . ? O3 C15 N2 123.98(19) . . ? O3 C15 C12 127.96(18) . . ? N2 C15 C12 108.05(16) . . ? O2 C16 N2 124.46(17) . . ? O2 C16 C11 127.62(17) . . ? N2 C16 C11 107.80(15) . . ? O4 C17 O5 123.27(19) . . ? O4 C17 C1 125.71(18) . . ? O5 C17 C1 111.01(17) . . ? O5 C18 C19 106.39(19) . . ? O5 C18 H18A 110.5 . . ? C19 C18 H18A 110.5 . . ? O5 C18 H18B 110.5 . . ? C19 C18 H18B 110.5 . . ? H18A C18 H18B 108.6 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C2 C20 H20A 109.5 . . ? C2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N1 C21 C26 120.48(16) . . ? N1 C21 C22 122.08(16) . . ? C26 C21 C22 117.40(16) . . ? C23 C22 C21 120.45(19) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C24 C23 C22 121.4(2) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C25 C24 C23 118.6(2) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 121.0(2) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C26 C21 121.14(19) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? C32 C27 C28 120.48(19) . . ? C32 C27 N2 120.59(17) . . ? C28 C27 N2 118.91(17) . . ? C29 C28 C27 120.4(2) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C30 C29 C28 120.0(2) . . ? C30 C29 H29 120.0 . . ? C28 C29 H29 120.0 . . ? C29 C30 C31 120.3(2) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? C30 C31 C32 120.8(2) . . ? C30 C31 H31 119.6 . . ? C32 C31 H31 119.6 . . ? C27 C32 C31 118.0(2) . . ? C27 C32 H32 121.0 . . ? C31 C32 H32 121.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.199 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.032