# Electronic Supplementary Material (ESI) for Chemical Communications # 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_5racr _database_code_depnum_ccdc_archive 'CCDC 919797' #TrackingRef 'web_deposit_cif_file_0_AlinaRaskosova_1358325003.5racr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H17 N O' _chemical_formula_sum 'C21 H17 N O' _chemical_formula_weight 299.36 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6160(5) _cell_length_b 12.2924(6) _cell_length_c 12.6394(6) _cell_angle_alpha 77.384(4) _cell_angle_beta 72.856(4) _cell_angle_gamma 72.749(4) _cell_volume 1489.62(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 37104 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 29.59 _exptl_crystal_description fragment _exptl_crystal_colour brown _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.42 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'long fine focus sealed X-ray tube' _diffrn_radiation_monochromator 'planar graphite' _diffrn_radiation_collimation '0.5 mm diameter monocapillary' _diffrn_measurement_device 'Stoe IPDS-2t diffractometer' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 20471 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6831 _reflns_number_gt 5861 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON, 1990' _computing_publication_material 'PLATON, 1990' _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^)+(0.0526P)^2^+0.2883P] 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 6831 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0984 _refine_ls_wR_factor_gt 0.0954 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.04809(7) 0.13492(6) 0.74668(6) 0.01965(16) Uani 1 1 d . . . N1 N 0.35800(9) 0.20605(8) 0.47231(8) 0.02029(19) Uani 1 1 d . . . C1 C 0.11052(10) 0.18910(9) 0.63785(8) 0.0162(2) Uani 1 1 d . . . C2 C 0.20649(10) 0.25192(9) 0.65115(9) 0.0169(2) Uani 1 1 d . . . C3 C 0.32518(10) 0.26059(9) 0.56638(9) 0.0175(2) Uani 1 1 d . . . C4 C 0.30641(10) 0.11124(9) 0.48047(9) 0.0181(2) Uani 1 1 d . . . C5 C 0.18646(10) 0.09879(9) 0.56115(9) 0.0173(2) Uani 1 1 d . . . C6 C 0.13456(11) 0.00575(9) 0.56670(9) 0.0205(2) Uani 1 1 d . . . H6 H 0.0536 -0.0029 0.6217 0.025 Uiso 1 1 calc R . . C7 C 0.19835(12) -0.07489(9) 0.49362(10) 0.0228(2) Uani 1 1 d . . . H7 H 0.1604 -0.1370 0.4972 0.027 Uiso 1 1 calc R . . C8 C 0.31834(12) -0.06343(10) 0.41526(10) 0.0230(2) Uani 1 1 d . . . H8 H 0.3634 -0.1186 0.3654 0.028 Uiso 1 1 calc R . . C9 C 0.37321(11) 0.02769(10) 0.40893(9) 0.0220(2) Uani 1 1 d . . . H9 H 0.4564 0.0336 0.3559 0.026 Uiso 1 1 calc R . . C10 C 0.46932(12) 0.22758(11) 0.37725(10) 0.0255(2) Uani 1 1 d . . . H10A H 0.4716 0.3084 0.3669 0.038 Uiso 1 1 calc R . . H10B H 0.4556 0.2109 0.3097 0.038 Uiso 1 1 calc R . . H10C H 0.5557 0.1779 0.3912 0.038 Uiso 1 1 calc R . . C11 C 0.40785(11) 0.32480(9) 0.57919(9) 0.0204(2) Uani 1 1 d . . . H11 H 0.4894 0.3302 0.5237 0.024 Uiso 1 1 calc R . . C12 C 0.37171(11) 0.38031(9) 0.67187(10) 0.0225(2) Uani 1 1 d . . . H12 H 0.4279 0.4246 0.6786 0.027 Uiso 1 1 calc R . . C13 C 0.25401(11) 0.37196(10) 0.75542(10) 0.0225(2) Uani 1 1 d . . . H13 H 0.2296 0.4100 0.8191 0.027 Uiso 1 1 calc R . . C14 C 0.17308(11) 0.30729(9) 0.74413(9) 0.0200(2) Uani 1 1 d . . . H14 H 0.0930 0.3006 0.8011 0.024 Uiso 1 1 calc R . . C15 C -0.00961(10) 0.27160(8) 0.59807(9) 0.0160(2) Uani 1 1 d . . . C16 C -0.12970(10) 0.25449(9) 0.67197(9) 0.0178(2) Uani 1 1 d . . . C17 C -0.09757(11) 0.16316(9) 0.76639(9) 0.0210(2) Uani 1 1 d . . . H17A H -0.1419 0.1921 0.8390 0.025 Uiso 1 1 calc R . . H17B H -0.1289 0.0948 0.7667 0.025 Uiso 1 1 calc R . . C18 C -0.25436(11) 0.31821(9) 0.65197(9) 0.0207(2) Uani 1 1 d . . . H18 H -0.3371 0.3053 0.7014 0.025 Uiso 1 1 calc R . . C19 C -0.25529(11) 0.40124(9) 0.55790(10) 0.0226(2) Uani 1 1 d . . . H19 H -0.3398 0.4454 0.5428 0.027 Uiso 1 1 calc R . . C20 C -0.13449(11) 0.42076(9) 0.48538(9) 0.0210(2) Uani 1 1 d . . . H20 H -0.1372 0.4793 0.4225 0.025 Uiso 1 1 calc R . . C21 C -0.00980(11) 0.35508(9) 0.50451(9) 0.0185(2) Uani 1 1 d . . . H21 H 0.0731 0.3671 0.4548 0.022 Uiso 1 1 calc R . . O2 O 0.70843(7) 0.34615(7) 0.18939(6) 0.02001(16) Uani 1 1 d . . . N2 N 0.57676(9) 0.33765(8) -0.02787(8) 0.01894(18) Uani 1 1 d . . . C22 C 0.78309(10) 0.28391(9) 0.09231(8) 0.0161(2) Uani 1 1 d . . . C23 C 0.70847(10) 0.19682(9) 0.09192(8) 0.0164(2) Uani 1 1 d . . . C24 C 0.60207(10) 0.23023(9) 0.03758(9) 0.0172(2) Uani 1 1 d . . . C25 C 0.67573(10) 0.40036(9) -0.06410(9) 0.0177(2) Uani 1 1 d . . . C26 C 0.78246(10) 0.37311(9) -0.01070(9) 0.0173(2) Uani 1 1 d . . . C27 C 0.88068(11) 0.43658(9) -0.04765(10) 0.0219(2) Uani 1 1 d . . . H27 H 0.9527 0.4178 -0.0115 0.026 Uiso 1 1 calc R . . C28 C 0.87562(12) 0.52605(10) -0.13556(10) 0.0269(2) Uani 1 1 d . . . H28 H 0.9433 0.5684 -0.1597 0.032 Uiso 1 1 calc R . . C29 C 0.77019(13) 0.55289(10) -0.18778(10) 0.0264(2) Uani 1 1 d . . . H29 H 0.7655 0.6145 -0.2480 0.032 Uiso 1 1 calc R . . C30 C 0.67185(12) 0.49154(9) -0.15373(9) 0.0229(2) Uani 1 1 d . . . H30 H 0.6008 0.5110 -0.1911 0.027 Uiso 1 1 calc R . . C31 C 0.45877(11) 0.37082(10) -0.07480(10) 0.0225(2) Uani 1 1 d . . . H31A H 0.4761 0.3256 -0.1349 0.034 Uiso 1 1 calc R . . H31B H 0.4418 0.4529 -0.1050 0.034 Uiso 1 1 calc R . . H31C H 0.3790 0.3563 -0.0161 0.034 Uiso 1 1 calc R . . C32 C 0.52232(11) 0.15300(10) 0.04979(9) 0.0207(2) Uani 1 1 d . . . H32 H 0.4486 0.1751 0.0152 0.025 Uiso 1 1 calc R . . C33 C 0.55051(11) 0.04514(10) 0.11183(9) 0.0220(2) Uani 1 1 d . . . H33 H 0.4954 -0.0060 0.1198 0.026 Uiso 1 1 calc R . . C34 C 0.65825(11) 0.01055(9) 0.16264(9) 0.0216(2) Uani 1 1 d . . . H34 H 0.6783 -0.0642 0.2039 0.026 Uiso 1 1 calc R . . C35 C 0.73595(11) 0.08681(9) 0.15214(9) 0.0190(2) Uani 1 1 d . . . H35 H 0.8097 0.0636 0.1868 0.023 Uiso 1 1 calc R . . C36 C 0.92192(10) 0.22966(9) 0.11523(9) 0.0166(2) Uani 1 1 d . . . C37 C 0.92207(10) 0.24731(9) 0.21926(9) 0.0170(2) Uani 1 1 d . . . C38 C 0.78388(11) 0.31518(9) 0.27289(9) 0.0197(2) Uani 1 1 d . . . H38A H 0.7397 0.2681 0.3396 0.024 Uiso 1 1 calc R . . H38B H 0.7905 0.3848 0.2961 0.024 Uiso 1 1 calc R . . C39 C 1.03823(11) 0.20389(9) 0.26004(9) 0.0196(2) Uani 1 1 d . . . H39 H 1.0376 0.2155 0.3321 0.024 Uiso 1 1 calc R . . C40 C 1.15506(11) 0.14314(9) 0.19258(10) 0.0221(2) Uani 1 1 d . . . H40 H 1.2360 0.1139 0.2182 0.026 Uiso 1 1 calc R . . C41 C 1.15474(11) 0.12467(10) 0.08771(10) 0.0229(2) Uani 1 1 d . . . H41 H 1.2354 0.0825 0.0428 0.028 Uiso 1 1 calc R . . C42 C 1.03804(11) 0.16713(9) 0.04797(9) 0.0211(2) Uani 1 1 d . . . H42 H 1.0374 0.1539 -0.0231 0.025 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 0.0169(4) 0.0224(4) 0.0159(4) 0.0016(3) -0.0016(3) -0.0048(3) N1 0.0177(4) 0.0255(5) 0.0172(4) -0.0043(3) 0.0006(3) -0.0085(3) C1 0.0156(5) 0.0180(5) 0.0132(5) -0.0005(4) -0.0014(4) -0.0052(4) C2 0.0144(4) 0.0177(5) 0.0174(5) -0.0012(4) -0.0050(4) -0.0024(4) C3 0.0146(5) 0.0189(5) 0.0176(5) -0.0014(4) -0.0051(4) -0.0018(4) C4 0.0165(5) 0.0206(5) 0.0166(5) -0.0019(4) -0.0051(4) -0.0032(4) C5 0.0156(5) 0.0181(5) 0.0170(5) -0.0022(4) -0.0044(4) -0.0020(4) C6 0.0184(5) 0.0207(5) 0.0213(5) -0.0018(4) -0.0043(4) -0.0045(4) C7 0.0250(5) 0.0194(5) 0.0250(6) -0.0034(4) -0.0089(4) -0.0042(4) C8 0.0238(5) 0.0226(5) 0.0212(5) -0.0074(4) -0.0072(4) 0.0011(4) C9 0.0180(5) 0.0270(5) 0.0185(5) -0.0053(4) -0.0027(4) -0.0021(4) C10 0.0212(5) 0.0343(6) 0.0196(5) -0.0041(4) 0.0018(4) -0.0112(5) C11 0.0143(5) 0.0230(5) 0.0229(5) -0.0016(4) -0.0051(4) -0.0040(4) C12 0.0187(5) 0.0234(5) 0.0284(6) -0.0034(4) -0.0116(4) -0.0043(4) C13 0.0218(5) 0.0262(5) 0.0209(5) -0.0059(4) -0.0092(4) -0.0024(4) C14 0.0179(5) 0.0231(5) 0.0175(5) -0.0027(4) -0.0048(4) -0.0026(4) C15 0.0146(5) 0.0175(5) 0.0172(5) -0.0055(4) -0.0039(4) -0.0038(4) C16 0.0170(5) 0.0176(5) 0.0188(5) -0.0057(4) -0.0020(4) -0.0046(4) C17 0.0167(5) 0.0227(5) 0.0203(5) -0.0014(4) -0.0001(4) -0.0054(4) C18 0.0146(5) 0.0230(5) 0.0249(5) -0.0085(4) -0.0020(4) -0.0046(4) C19 0.0183(5) 0.0216(5) 0.0302(6) -0.0073(4) -0.0107(4) -0.0010(4) C20 0.0247(5) 0.0193(5) 0.0221(5) -0.0020(4) -0.0108(4) -0.0058(4) C21 0.0189(5) 0.0209(5) 0.0173(5) -0.0036(4) -0.0045(4) -0.0067(4) O2 0.0163(3) 0.0256(4) 0.0166(4) -0.0073(3) -0.0040(3) -0.0002(3) N2 0.0165(4) 0.0212(4) 0.0196(4) -0.0019(3) -0.0077(3) -0.0031(3) C22 0.0132(4) 0.0197(5) 0.0143(5) -0.0039(4) -0.0024(3) -0.0023(4) C23 0.0131(4) 0.0212(5) 0.0137(4) -0.0041(4) -0.0008(4) -0.0038(4) C24 0.0142(4) 0.0205(5) 0.0154(5) -0.0045(4) -0.0019(4) -0.0025(4) C25 0.0174(5) 0.0183(5) 0.0163(5) -0.0049(4) -0.0030(4) -0.0023(4) C26 0.0166(5) 0.0180(5) 0.0162(5) -0.0033(4) -0.0031(4) -0.0028(4) C27 0.0179(5) 0.0220(5) 0.0244(5) -0.0029(4) -0.0039(4) -0.0046(4) C28 0.0231(5) 0.0236(5) 0.0300(6) 0.0002(5) -0.0005(5) -0.0088(4) C29 0.0310(6) 0.0223(5) 0.0205(5) 0.0023(4) -0.0034(4) -0.0054(4) C30 0.0260(5) 0.0230(5) 0.0185(5) -0.0021(4) -0.0080(4) -0.0025(4) C31 0.0179(5) 0.0274(5) 0.0227(5) -0.0044(4) -0.0095(4) -0.0013(4) C32 0.0157(5) 0.0269(5) 0.0206(5) -0.0061(4) -0.0040(4) -0.0055(4) C33 0.0193(5) 0.0248(5) 0.0226(5) -0.0065(4) 0.0000(4) -0.0094(4) C34 0.0214(5) 0.0200(5) 0.0201(5) -0.0020(4) -0.0011(4) -0.0051(4) C35 0.0165(5) 0.0224(5) 0.0165(5) -0.0029(4) -0.0031(4) -0.0032(4) C36 0.0142(4) 0.0182(5) 0.0178(5) -0.0008(4) -0.0044(4) -0.0055(4) C37 0.0164(5) 0.0173(5) 0.0180(5) -0.0006(4) -0.0035(4) -0.0076(4) C38 0.0184(5) 0.0239(5) 0.0176(5) -0.0050(4) -0.0050(4) -0.0045(4) C39 0.0209(5) 0.0220(5) 0.0190(5) 0.0001(4) -0.0077(4) -0.0094(4) C40 0.0159(5) 0.0239(5) 0.0268(6) 0.0027(4) -0.0090(4) -0.0064(4) C41 0.0151(5) 0.0255(5) 0.0241(5) -0.0023(4) -0.0022(4) -0.0025(4) C42 0.0180(5) 0.0255(5) 0.0183(5) -0.0036(4) -0.0033(4) -0.0040(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 O1 C17 1.4374(12) . ? O1 C1 1.4488(12) . ? N1 C3 1.3963(14) . ? N1 C4 1.4005(14) . ? N1 C10 1.4560(13) . ? C1 C2 1.5123(14) . ? C1 C15 1.5152(14) . ? C1 C5 1.5167(14) . ? C2 C14 1.3896(15) . ? C2 C3 1.4074(14) . ? C3 C11 1.4036(15) . ? C4 C5 1.4024(14) . ? C4 C9 1.4040(15) . ? C5 C6 1.3902(15) . ? C6 C7 1.3883(15) . ? C6 H6 0.9500 . ? C7 C8 1.3875(16) . ? C7 H7 0.9500 . ? C8 C9 1.3859(16) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3833(16) . ? C11 H11 0.9500 . ? C12 C13 1.3920(16) . ? C12 H12 0.9500 . ? C13 C14 1.3847(16) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.3832(14) . ? C15 C21 1.3863(14) . ? C16 C18 1.3873(15) . ? C16 C17 1.4929(15) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.3878(16) . ? C18 H18 0.9500 . ? C19 C20 1.3913(16) . ? C19 H19 0.9500 . ? C20 C21 1.3900(15) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? O2 C38 1.4291(13) . ? O2 C22 1.4819(12) . ? N2 C24 1.3941(13) . ? N2 C25 1.3965(13) . ? N2 C31 1.4549(13) . ? C22 C26 1.5083(14) . ? C22 C23 1.5104(14) . ? C22 C36 1.5117(14) . ? C23 C35 1.3930(15) . ? C23 C24 1.4054(14) . ? C24 C32 1.4063(15) . ? C25 C26 1.4065(14) . ? C25 C30 1.4095(15) . ? C26 C27 1.3966(15) . ? C27 C28 1.3833(16) . ? C27 H27 0.9500 . ? C28 C29 1.3852(18) . ? C28 H28 0.9500 . ? C29 C30 1.3799(17) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.3824(16) . ? C32 H32 0.9500 . ? C33 C34 1.3881(16) . ? C33 H33 0.9500 . ? C34 C35 1.3843(15) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C36 C37 1.3792(15) . ? C36 C42 1.3924(14) . ? C37 C39 1.3911(14) . ? C37 C38 1.4975(14) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 C40 1.3886(16) . ? C39 H39 0.9500 . ? C40 C41 1.3939(17) . ? C40 H40 0.9500 . ? C41 C42 1.3886(15) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? 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 C17 O1 C1 111.58(8) . . ? C3 N1 C4 118.94(9) . . ? C3 N1 C10 120.27(9) . . ? C4 N1 C10 119.02(9) . . ? O1 C1 C2 109.28(8) . . ? O1 C1 C15 103.45(8) . . ? C2 C1 C15 111.72(8) . . ? O1 C1 C5 109.84(8) . . ? C2 C1 C5 110.55(8) . . ? C15 C1 C5 111.76(8) . . ? C14 C2 C3 119.87(10) . . ? C14 C2 C1 119.82(9) . . ? C3 C2 C1 120.20(9) . . ? N1 C3 C11 121.66(9) . . ? N1 C3 C2 119.90(9) . . ? C11 C3 C2 118.45(10) . . ? N1 C4 C5 119.92(9) . . ? N1 C4 C9 120.96(9) . . ? C5 C4 C9 119.12(10) . . ? C6 C5 C4 119.36(10) . . ? C6 C5 C1 120.33(9) . . ? C4 C5 C1 120.24(9) . . ? C7 C6 C5 121.48(10) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C8 C7 C6 118.97(10) . . ? C8 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? C9 C8 C7 120.70(10) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C4 120.31(10) . . ? C8 C9 H9 119.8 . . ? C4 C9 H9 119.8 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C3 120.66(10) . . ? C12 C11 H11 119.7 . . ? C3 C11 H11 119.7 . . ? C11 C12 C13 120.79(10) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 118.84(10) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C2 121.38(10) . . ? C13 C14 H14 119.3 . . ? C2 C14 H14 119.3 . . ? C16 C15 C21 121.37(10) . . ? C16 C15 C1 109.71(9) . . ? C21 C15 C1 128.92(9) . . ? C15 C16 C18 120.53(10) . . ? C15 C16 C17 109.25(9) . . ? C18 C16 C17 130.23(10) . . ? O1 C17 C16 105.11(8) . . ? O1 C17 H17A 110.7 . . ? C16 C17 H17A 110.7 . . ? O1 C17 H17B 110.7 . . ? C16 C17 H17B 110.7 . . ? H17A C17 H17B 108.8 . . ? C19 C18 C16 118.38(10) . . ? C19 C18 H18 120.8 . . ? C16 C18 H18 120.8 . . ? C18 C19 C20 121.06(10) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C21 C20 C19 120.36(10) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C15 C21 C20 118.27(10) . . ? C15 C21 H21 120.9 . . ? C20 C21 H21 120.9 . . ? C38 O2 C22 110.96(7) . . ? C24 N2 C25 119.99(9) . . ? C24 N2 C31 117.94(9) . . ? C25 N2 C31 120.94(9) . . ? O2 C22 C26 106.50(8) . . ? O2 C22 C23 108.19(8) . . ? C26 C22 C23 110.83(8) . . ? O2 C22 C36 102.81(8) . . ? C26 C22 C36 114.48(8) . . ? C23 C22 C36 113.30(8) . . ? C35 C23 C24 119.38(9) . . ? C35 C23 C22 120.99(9) . . ? C24 C23 C22 119.42(9) . . ? N2 C24 C23 120.57(9) . . ? N2 C24 C32 120.64(9) . . ? C23 C24 C32 118.78(10) . . ? N2 C25 C26 119.96(9) . . ? N2 C25 C30 121.59(10) . . ? C26 C25 C30 118.44(10) . . ? C27 C26 C25 119.40(10) . . ? C27 C26 C22 120.24(9) . . ? C25 C26 C22 120.10(9) . . ? C28 C27 C26 121.62(11) . . ? C28 C27 H27 119.2 . . ? C26 C27 H27 119.2 . . ? C27 C28 C29 118.85(10) . . ? C27 C28 H28 120.6 . . ? C29 C28 H28 120.6 . . ? C30 C29 C28 121.01(10) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C29 C30 C25 120.68(10) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? N2 C31 H31A 109.5 . . ? N2 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N2 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 C32 C24 120.46(10) . . ? C33 C32 H32 119.8 . . ? C24 C32 H32 119.8 . . ? C32 C33 C34 120.86(10) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? C35 C34 C33 118.91(10) . . ? C35 C34 H34 120.5 . . ? C33 C34 H34 120.5 . . ? C34 C35 C23 121.55(10) . . ? C34 C35 H35 119.2 . . ? C23 C35 H35 119.2 . . ? C37 C36 C42 120.94(10) . . ? C37 C36 C22 110.39(9) . . ? C42 C36 C22 128.65(10) . . ? C36 C37 C39 121.14(10) . . ? C36 C37 C38 109.20(9) . . ? C39 C37 C38 129.65(10) . . ? O2 C38 C37 105.55(8) . . ? O2 C38 H38A 110.6 . . ? C37 C38 H38A 110.6 . . ? O2 C38 H38B 110.6 . . ? C37 C38 H38B 110.6 . . ? H38A C38 H38B 108.8 . . ? C40 C39 C37 118.21(10) . . ? C40 C39 H39 120.9 . . ? C37 C39 H39 120.9 . . ? C39 C40 C41 120.67(10) . . ? C39 C40 H40 119.7 . . ? C41 C40 H40 119.7 . . ? C42 C41 C40 120.86(10) . . ? C42 C41 H41 119.6 . . ? C40 C41 H41 119.6 . . ? C41 C42 C36 118.17(10) . . ? C41 C42 H42 120.9 . . ? C36 C42 H42 120.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.281 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.045