# 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_LC573 #TrackingRef 'web_deposit_cif_file_0_LaurentChabaud_1307605975.LC573.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N O4' _chemical_formula_sum 'C16 H15 N O4' _chemical_formula_weight 285.29 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_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 8.86900(10) _cell_length_b 15.2039(2) _cell_length_c 21.8583(15) _cell_angle_alpha 90.00 _cell_angle_beta 93.444(7) _cell_angle_gamma 90.00 _cell_volume 2942.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2849 _cell_measurement_theta_min 6.6 _cell_measurement_theta_max 67.7 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.771 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.819 _exptl_absorpt_process_details 'FS_ABSCOR (Rigaku, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku rapid II RAXIS conversion' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_type 'RAPID II large area curved imaging plate detector ' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12944 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 6.63 _diffrn_reflns_theta_max 68.21 _diffrn_measurement_details ; scan: Number of images: 36 Slice: 20.0000 - 200.0000 Image width: 5.0000 Exp time: 240.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 270.0000 XTD: 127.4000 2theta: 0.0000 scan: Number of images: 20 Slice: 20.0000 - 120.0000 Image width: 5.0000 Exp time: 240.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 90.0000 XTD: 127.4000 2theta: 0.0000 scan: Number of images: 6 Slice: 40.0000 - 70.0000 Image width: 5.0000 Exp time: 240.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 127.4000 2theta: 0.0000 scan: Number of images: 6 Slice: 60.0000 - 90.0000 Image width: 5.0000 Exp time: 240.0000 Rotation axis: Omega Omega: 0.0000 Chi: 30.0000 Phi: 0.0000 XTD: 127.4000 2theta: 0.0000 ; _diffrn_orient_matrix_UB_11 -0.017570 _diffrn_orient_matrix_UB_12 -0.059033 _diffrn_orient_matrix_UB_13 -0.019360 _diffrn_orient_matrix_UB_21 0.111308 _diffrn_orient_matrix_UB_22 -0.011179 _diffrn_orient_matrix_UB_23 0.002588 _diffrn_orient_matrix_UB_31 -0.007704 _diffrn_orient_matrix_UB_32 -0.026877 _diffrn_orient_matrix_UB_33 0.041446 _diffrn_orient_matrix_type FS_PROCESS _reflns_number_total 5084 _reflns_number_gt 3004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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. 4 outlier reflections were omitted (Delta(F^2^)/esd above 9) using OMIT instruction in SHELXL-97 refinement program. ; _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^)+(0.0684P)^2^+1.7292P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00100(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5080 _refine_ls_number_parameters 384 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0957 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1920 _refine_ls_wR_factor_gt 0.1293 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.150 _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 C1 C 0.0337(5) 0.3530(2) -0.10785(16) 0.0644(10) Uani 1 1 d . . . C2 C -0.1109(4) 0.3392(2) -0.08067(16) 0.0634(10) Uani 1 1 d . . . H2 H -0.2021 0.3463 -0.1053 0.076 Uiso 1 1 calc R . . C3 C -0.1169(4) 0.3170(2) -0.02231(16) 0.0580(9) Uani 1 1 d . . . H3 H -0.2134 0.3128 -0.0059 0.070 Uiso 1 1 calc R . . C4 C 0.0194(3) 0.2982(2) 0.01926(13) 0.0468(8) Uani 1 1 d . . . C5 C 0.1621(4) 0.3289(2) -0.00846(15) 0.0532(8) Uani 1 1 d . . . C6 C 0.1697(4) 0.3516(2) -0.06750(15) 0.0596(9) Uani 1 1 d . . . H6 H 0.2642 0.3667 -0.0829 0.072 Uiso 1 1 calc R . . N7 N 0.0043(3) 0.33512(18) 0.08003(12) 0.0546(7) Uani 1 1 d . . . C8 C 0.0588(4) 0.2835(2) 0.12659(15) 0.0533(8) Uani 1 1 d . . . C9 C 0.0954(4) 0.1954(2) 0.10178(14) 0.0556(9) Uani 1 1 d . . . H9A H 0.0492 0.1484 0.1258 0.067 Uiso 1 1 calc R . . H9B H 0.2061 0.1863 0.1035 0.067 Uiso 1 1 calc R . . C10 C 0.0299(3) 0.1940(2) 0.03483(13) 0.0448(7) Uani 1 1 d . . . C11 C 0.1273(3) 0.1499(2) -0.00892(14) 0.0500(8) Uani 1 1 d . . . H11 H 0.2324 0.1625 -0.0060 0.060 Uiso 1 1 calc R . . C12 C 0.0760(3) 0.0941(2) -0.05172(14) 0.0487(8) Uani 1 1 d . . . H12 H 0.1439 0.0705 -0.0794 0.058 Uiso 1 1 calc R . . C13 C -0.0821(4) 0.0680(2) -0.05735(13) 0.0486(8) Uani 1 1 d . . . C14 C -0.1773(4) 0.0987(2) -0.00978(14) 0.0512(8) Uani 1 1 d . . . H14 H -0.2777 0.0772 -0.0087 0.061 Uiso 1 1 calc R . . C15 C -0.1262(3) 0.1562(2) 0.03211(14) 0.0508(8) Uani 1 1 d . . . H15 H -0.1926 0.1745 0.0622 0.061 Uiso 1 1 calc R . . O16 O 0.0377(3) 0.3697(2) -0.16297(11) 0.0951(10) Uani 1 1 d . . . O17 O -0.1323(3) 0.02073(18) -0.09964(10) 0.0680(7) Uani 1 1 d . . . O18 O 0.2795(3) 0.32764(18) 0.03357(10) 0.0685(7) Uani 1 1 d . . . C19 C -0.0200(6) 0.4288(3) 0.0887(2) 0.0912(14) Uani 1 1 d . . . H19A H -0.0509 0.4393 0.1304 0.137 Uiso 1 1 calc R . . H19B H -0.0994 0.4494 0.0591 0.137 Uiso 1 1 calc R . . H19C H 0.0739 0.4607 0.0826 0.137 Uiso 1 1 calc R . . O20 O 0.0770(3) 0.30730(19) 0.18025(11) 0.0742(8) Uani 1 1 d . . . C21 C 0.4278(4) 0.3488(4) 0.0132(2) 0.1068(18) Uani 1 1 d . . . H21A H 0.4523 0.3087 -0.0199 0.160 Uiso 1 1 calc R . . H21B H 0.5033 0.3426 0.0475 0.160 Uiso 1 1 calc R . . H21C H 0.4281 0.4095 -0.0019 0.160 Uiso 1 1 calc R . . O116 O 0.4763(3) 0.5979(2) 0.13780(11) 0.0860(9) Uani 1 1 d . . . O117 O 0.7215(4) 0.2260(3) 0.15217(16) 0.1529(19) Uani 1 1 d U . . O120 O 0.4534(2) 0.38332(18) 0.45121(9) 0.0647(7) Uani 1 1 d . . . O118 O 0.2343(2) 0.46738(16) 0.30205(9) 0.0576(6) Uani 1 1 d . . . C101 C 0.4812(4) 0.5626(3) 0.18887(15) 0.0614(9) Uani 1 1 d . . . C102 C 0.6248(4) 0.5477(3) 0.22337(15) 0.0623(10) Uani 1 1 d . . . H102 H 0.7147 0.5712 0.2084 0.075 Uiso 1 1 calc R . . C103 C 0.6327(4) 0.5020(2) 0.27518(14) 0.0543(8) Uani 1 1 d . . . H103 H 0.7277 0.4977 0.2975 0.065 Uiso 1 1 calc R . . C104 C 0.4994(3) 0.4567(2) 0.30033(12) 0.0458(8) Uani 1 1 d . . . C105 C 0.3529(3) 0.4917(2) 0.27039(14) 0.0503(8) Uani 1 1 d . . . C106 C 0.3452(4) 0.5377(2) 0.21774(14) 0.0588(9) Uani 1 1 d . . . H106 H 0.2495 0.5539 0.1993 0.071 Uiso 1 1 calc R . . N107 N 0.5023(3) 0.46417(18) 0.36690(10) 0.0462(6) Uani 1 1 d . . . C108 C 0.4646(3) 0.3897(2) 0.39551(14) 0.0509(8) Uani 1 1 d . . . C109 C 0.4398(4) 0.3178(2) 0.34951(14) 0.0553(9) Uani 1 1 d . . . H10A H 0.3305 0.3065 0.3411 0.066 Uiso 1 1 calc R . . H10B H 0.4891 0.2627 0.3643 0.066 Uiso 1 1 calc R . . C110 C 0.5119(3) 0.3519(2) 0.29162(13) 0.0480(8) Uani 1 1 d . . . C111 C 0.4302(4) 0.3213(2) 0.23386(15) 0.0604(9) Uani 1 1 d . . . H111 H 0.3244 0.3311 0.2288 0.072 Uiso 1 1 calc R . . C112 C 0.4977(5) 0.2815(3) 0.18948(17) 0.0771(12) Uani 1 1 d . . . H112 H 0.4395 0.2652 0.1533 0.093 Uiso 1 1 calc R . . C113 C 0.6599(5) 0.2615(3) 0.19411(19) 0.0891(15) Uani 1 1 d U . . C114 C 0.7425(4) 0.2841(3) 0.25131(18) 0.0713(11) Uani 1 1 d . . . H114 H 0.8463 0.2689 0.2571 0.086 Uiso 1 1 calc R . . C115 C 0.6757(4) 0.3252(2) 0.29532(15) 0.0553(9) Uani 1 1 d . . . H115 H 0.7347 0.3390 0.3318 0.066 Uiso 1 1 calc R . . C116 C 0.5096(4) 0.5491(2) 0.39666(15) 0.0596(9) Uani 1 1 d . . . H11A H 0.4190 0.5831 0.3843 0.089 Uiso 1 1 calc R . . H11B H 0.5995 0.5807 0.3847 0.089 Uiso 1 1 calc R . . H11C H 0.5154 0.5410 0.4412 0.089 Uiso 1 1 calc R . . C121 C 0.0858(4) 0.4929(3) 0.27758(16) 0.0742(12) Uani 1 1 d . . . H12A H 0.0828 0.5567 0.2715 0.111 Uiso 1 1 calc R . . H12B H 0.0105 0.4759 0.3064 0.111 Uiso 1 1 calc R . . H12C H 0.0635 0.4632 0.2383 0.111 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 C1 0.083(3) 0.061(2) 0.0487(19) 0.0061(17) 0.0012(18) -0.001(2) C2 0.060(2) 0.067(3) 0.062(2) 0.0090(19) -0.0056(17) 0.0005(19) C3 0.0492(19) 0.060(2) 0.065(2) 0.0057(18) 0.0040(15) 0.0076(17) C4 0.0477(18) 0.0462(18) 0.0472(17) -0.0055(14) 0.0087(13) -0.0010(15) C5 0.0461(18) 0.059(2) 0.0542(19) 0.0030(16) 0.0002(14) -0.0067(16) C6 0.062(2) 0.064(2) 0.0537(19) 0.0056(17) 0.0070(16) -0.0096(19) N7 0.0698(19) 0.0437(16) 0.0508(15) -0.0069(13) 0.0069(13) 0.0046(15) C8 0.0453(18) 0.067(2) 0.0478(18) -0.0077(17) 0.0046(14) -0.0082(17) C9 0.058(2) 0.060(2) 0.0486(18) 0.0009(16) 0.0001(15) -0.0009(18) C10 0.0420(16) 0.051(2) 0.0420(16) -0.0002(14) 0.0046(12) -0.0008(15) C11 0.0401(17) 0.057(2) 0.0537(18) -0.0029(16) 0.0071(14) 0.0030(16) C12 0.0420(17) 0.057(2) 0.0475(17) -0.0019(15) 0.0083(13) 0.0018(16) C13 0.0480(18) 0.058(2) 0.0394(16) -0.0027(15) -0.0001(13) 0.0003(16) C14 0.0418(17) 0.063(2) 0.0492(17) -0.0006(17) 0.0074(13) -0.0022(16) C15 0.0422(17) 0.064(2) 0.0474(17) -0.0051(16) 0.0137(13) -0.0030(16) O16 0.102(2) 0.125(3) 0.0571(16) 0.0230(17) -0.0033(14) -0.0141(19) O17 0.0625(15) 0.089(2) 0.0518(13) -0.0171(13) -0.0001(11) -0.0106(14) O18 0.0537(14) 0.094(2) 0.0580(14) 0.0046(13) 0.0005(11) -0.0218(14) C19 0.124(4) 0.061(3) 0.090(3) -0.014(2) 0.012(3) 0.016(3) O20 0.0701(17) 0.098(2) 0.0545(14) -0.0210(14) 0.0019(12) -0.0105(15) C21 0.055(3) 0.177(5) 0.088(3) 0.023(3) 0.002(2) -0.043(3) O116 0.0847(19) 0.111(2) 0.0622(16) 0.0382(16) 0.0069(13) -0.0052(17) O117 0.109(3) 0.229(5) 0.128(3) -0.118(3) 0.070(2) -0.057(3) O120 0.0525(13) 0.101(2) 0.0416(12) 0.0079(13) 0.0092(9) -0.0073(13) O118 0.0377(12) 0.0857(18) 0.0497(12) 0.0134(12) 0.0044(9) 0.0042(12) C101 0.065(2) 0.069(2) 0.0507(19) 0.0168(18) 0.0080(16) -0.0022(19) C102 0.052(2) 0.077(3) 0.058(2) 0.0161(19) 0.0079(16) -0.0097(19) C103 0.0459(18) 0.063(2) 0.0538(19) 0.0055(17) 0.0052(14) -0.0069(17) C104 0.0391(16) 0.063(2) 0.0359(15) 0.0038(15) 0.0045(12) -0.0026(15) C105 0.0397(17) 0.067(2) 0.0449(17) 0.0024(16) 0.0060(13) -0.0015(16) C106 0.0511(19) 0.076(3) 0.0495(18) 0.0114(18) 0.0055(15) -0.0014(18) N107 0.0456(14) 0.0562(17) 0.0371(13) -0.0045(12) 0.0051(10) -0.0030(13) C108 0.0374(16) 0.073(2) 0.0434(17) 0.0052(17) 0.0094(13) -0.0005(16) C109 0.055(2) 0.057(2) 0.0550(19) -0.0019(17) 0.0123(15) -0.0071(17) C110 0.0498(18) 0.053(2) 0.0419(16) -0.0061(15) 0.0067(13) -0.0021(16) C111 0.056(2) 0.069(2) 0.056(2) -0.0090(18) 0.0016(16) -0.0135(19) C112 0.074(3) 0.103(3) 0.054(2) -0.024(2) 0.0099(18) -0.026(2) C113 0.084(3) 0.107(4) 0.081(3) -0.041(3) 0.041(2) -0.034(3) C114 0.059(2) 0.079(3) 0.078(2) -0.024(2) 0.0192(19) -0.004(2) C115 0.0485(19) 0.067(2) 0.0515(18) -0.0086(17) 0.0072(14) 0.0071(17) C116 0.065(2) 0.060(2) 0.0534(19) -0.0129(17) 0.0023(16) 0.0008(19) C121 0.0374(19) 0.125(4) 0.060(2) 0.013(2) 0.0025(15) 0.008(2) _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 C1 O16 1.234(4) . ? C1 C6 1.451(5) . ? C1 C2 1.460(5) . ? C2 C3 1.324(5) . ? C2 H2 0.9500 . ? C3 C4 1.496(4) . ? C3 H3 0.9500 . ? C4 N7 1.456(4) . ? C4 C5 1.509(4) . ? C4 C10 1.622(4) . ? C5 C6 1.341(4) . ? C5 O18 1.347(4) . ? C6 H6 0.9500 . ? N7 C8 1.351(4) . ? N7 C19 1.454(4) . ? C8 O20 1.229(4) . ? C8 C9 1.489(5) . ? C9 C10 1.542(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.487(4) . ? C10 C15 1.497(4) . ? C11 C12 1.323(4) . ? C11 H11 0.9500 . ? C12 C13 1.455(4) . ? C12 H12 0.9500 . ? C13 O17 1.233(3) . ? C13 C14 1.455(4) . ? C14 C15 1.326(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? O18 C21 1.450(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? O116 C101 1.237(4) . ? O117 C113 1.221(4) . ? O120 C108 1.231(3) . ? O118 C105 1.345(3) . ? O118 C121 1.444(4) . ? C101 C106 1.445(4) . ? C101 C102 1.458(5) . ? C102 C103 1.327(4) . ? C102 H102 0.9500 . ? C103 C104 1.501(4) . ? C103 H103 0.9500 . ? C104 N107 1.458(3) . ? C104 C105 1.516(4) . ? C104 C110 1.610(4) . ? C105 C106 1.345(4) . ? C106 H106 0.9500 . ? N107 C108 1.346(4) . ? N107 C116 1.445(4) . ? C108 C109 1.493(4) . ? C109 C110 1.542(4) . ? C109 H10A 0.9900 . ? C109 H10B 0.9900 . ? C110 C111 1.491(4) . ? C110 C115 1.505(4) . ? C111 C112 1.317(5) . ? C111 H111 0.9500 . ? C112 C113 1.468(6) . ? C112 H112 0.9500 . ? C113 C114 1.452(5) . ? C114 C115 1.318(4) . ? C114 H114 0.9500 . ? C115 H115 0.9500 . ? C116 H11A 0.9800 . ? C116 H11B 0.9800 . ? C116 H11C 0.9800 . ? C121 H12A 0.9800 . ? C121 H12B 0.9800 . ? C121 H12C 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 O16 C1 C6 121.7(4) . . ? O16 C1 C2 120.3(3) . . ? C6 C1 C2 118.0(3) . . ? C3 C2 C1 121.1(3) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 123.8(3) . . ? C2 C3 H3 118.1 . . ? C4 C3 H3 118.1 . . ? N7 C4 C3 111.4(3) . . ? N7 C4 C5 111.9(3) . . ? C3 C4 C5 111.3(3) . . ? N7 C4 C10 101.1(2) . . ? C3 C4 C10 110.4(3) . . ? C5 C4 C10 110.4(2) . . ? C6 C5 O18 125.3(3) . . ? C6 C5 C4 123.9(3) . . ? O18 C5 C4 110.7(3) . . ? C5 C6 C1 120.0(3) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C8 N7 C19 121.3(3) . . ? C8 N7 C4 114.5(3) . . ? C19 N7 C4 121.3(3) . . ? O20 C8 N7 124.6(3) . . ? O20 C8 C9 126.4(3) . . ? N7 C8 C9 108.9(3) . . ? C8 C9 C10 106.3(3) . . ? C8 C9 H9A 110.5 . . ? C10 C9 H9A 110.5 . . ? C8 C9 H9B 110.5 . . ? C10 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? C11 C10 C15 112.0(3) . . ? C11 C10 C9 114.6(3) . . ? C15 C10 C9 109.8(2) . . ? C11 C10 C4 109.5(2) . . ? C15 C10 C4 109.0(2) . . ? C9 C10 C4 101.5(2) . . ? C12 C11 C10 123.7(3) . . ? C12 C11 H11 118.1 . . ? C10 C11 H11 118.1 . . ? C11 C12 C13 121.6(3) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? O17 C13 C12 121.7(3) . . ? O17 C13 C14 121.6(3) . . ? C12 C13 C14 116.7(3) . . ? C15 C14 C13 121.1(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C10 123.9(3) . . ? C14 C15 H15 118.1 . . ? C10 C15 H15 118.1 . . ? C5 O18 C21 117.7(3) . . ? N7 C19 H19A 109.5 . . ? N7 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N7 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O18 C21 H21A 109.5 . . ? O18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C105 O118 C121 117.3(2) . . ? O116 C101 C106 121.5(3) . . ? O116 C101 C102 121.1(3) . . ? C106 C101 C102 117.3(3) . . ? C103 C102 C101 121.5(3) . . ? C103 C102 H102 119.2 . . ? C101 C102 H102 119.2 . . ? C102 C103 C104 123.4(3) . . ? C102 C103 H103 118.3 . . ? C104 C103 H103 118.3 . . ? N107 C104 C103 111.3(2) . . ? N107 C104 C105 111.5(2) . . ? C103 C104 C105 110.8(3) . . ? N107 C104 C110 101.4(2) . . ? C103 C104 C110 110.5(3) . . ? C105 C104 C110 111.1(3) . . ? C106 C105 O118 125.6(3) . . ? C106 C105 C104 123.4(3) . . ? O118 C105 C104 111.0(3) . . ? C105 C106 C101 120.6(3) . . ? C105 C106 H106 119.7 . . ? C101 C106 H106 119.7 . . ? C108 N107 C116 123.3(3) . . ? C108 N107 C104 114.1(3) . . ? C116 N107 C104 121.1(3) . . ? O120 C108 N107 124.2(3) . . ? O120 C108 C109 126.3(3) . . ? N107 C108 C109 109.5(3) . . ? C108 C109 C110 104.8(3) . . ? C108 C109 H10A 110.8 . . ? C110 C109 H10A 110.8 . . ? C108 C109 H10B 110.8 . . ? C110 C109 H10B 110.8 . . ? H10A C109 H10B 108.9 . . ? C111 C110 C115 112.3(3) . . ? C111 C110 C109 112.7(3) . . ? C115 C110 C109 108.2(3) . . ? C111 C110 C104 112.0(3) . . ? C115 C110 C104 109.5(3) . . ? C109 C110 C104 101.6(2) . . ? C112 C111 C110 123.2(3) . . ? C112 C111 H111 118.4 . . ? C110 C111 H111 118.4 . . ? C111 C112 C113 122.1(4) . . ? C111 C112 H112 119.0 . . ? C113 C112 H112 119.0 . . ? O117 C113 C114 121.7(4) . . ? O117 C113 C112 121.4(4) . . ? C114 C113 C112 116.9(3) . . ? C115 C114 C113 121.0(4) . . ? C115 C114 H114 119.5 . . ? C113 C114 H114 119.5 . . ? C114 C115 C110 124.3(3) . . ? C114 C115 H115 117.8 . . ? C110 C115 H115 117.8 . . ? N107 C116 H11A 109.5 . . ? N107 C116 H11B 109.5 . . ? H11A C116 H11B 109.5 . . ? N107 C116 H11C 109.5 . . ? H11A C116 H11C 109.5 . . ? H11B C116 H11C 109.5 . . ? O118 C121 H12A 109.5 . . ? O118 C121 H12B 109.5 . . ? H12A C121 H12B 109.5 . . ? O118 C121 H12C 109.5 . . ? H12A C121 H12C 109.5 . . ? H12B C121 H12C 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 O16 C1 C2 C3 176.7(4) . . . . ? C6 C1 C2 C3 -7.0(6) . . . . ? C1 C2 C3 C4 -4.4(6) . . . . ? C2 C3 C4 N7 139.6(4) . . . . ? C2 C3 C4 C5 14.0(5) . . . . ? C2 C3 C4 C10 -108.9(4) . . . . ? N7 C4 C5 C6 -139.3(4) . . . . ? C3 C4 C5 C6 -13.9(5) . . . . ? C10 C4 C5 C6 109.0(4) . . . . ? N7 C4 C5 O18 42.6(4) . . . . ? C3 C4 C5 O18 167.9(3) . . . . ? C10 C4 C5 O18 -69.1(3) . . . . ? O18 C5 C6 C1 -178.0(3) . . . . ? C4 C5 C6 C1 4.1(6) . . . . ? O16 C1 C6 C5 -176.7(4) . . . . ? C2 C1 C6 C5 7.0(5) . . . . ? C3 C4 N7 C8 140.8(3) . . . . ? C5 C4 N7 C8 -93.9(3) . . . . ? C10 C4 N7 C8 23.5(3) . . . . ? C3 C4 N7 C19 -58.2(4) . . . . ? C5 C4 N7 C19 67.0(4) . . . . ? C10 C4 N7 C19 -175.5(3) . . . . ? C19 N7 C8 O20 8.1(5) . . . . ? C4 N7 C8 O20 169.0(3) . . . . ? C19 N7 C8 C9 -170.7(3) . . . . ? C4 N7 C8 C9 -9.8(4) . . . . ? O20 C8 C9 C10 171.5(3) . . . . ? N7 C8 C9 C10 -9.7(3) . . . . ? C8 C9 C10 C11 140.3(3) . . . . ? C8 C9 C10 C15 -92.8(3) . . . . ? C8 C9 C10 C4 22.4(3) . . . . ? N7 C4 C10 C11 -148.1(3) . . . . ? C3 C4 C10 C11 93.9(3) . . . . ? C5 C4 C10 C11 -29.6(3) . . . . ? N7 C4 C10 C15 89.1(3) . . . . ? C3 C4 C10 C15 -28.9(3) . . . . ? C5 C4 C10 C15 -152.4(3) . . . . ? N7 C4 C10 C9 -26.6(3) . . . . ? C3 C4 C10 C9 -144.7(3) . . . . ? C5 C4 C10 C9 91.9(3) . . . . ? C15 C10 C11 C12 10.1(4) . . . . ? C9 C10 C11 C12 135.9(3) . . . . ? C4 C10 C11 C12 -110.9(3) . . . . ? C10 C11 C12 C13 -3.0(5) . . . . ? C11 C12 C13 O17 175.1(3) . . . . ? C11 C12 C13 C14 -6.4(5) . . . . ? O17 C13 C14 C15 -173.5(3) . . . . ? C12 C13 C14 C15 8.0(5) . . . . ? C13 C14 C15 C10 -0.2(5) . . . . ? C11 C10 C15 C14 -8.4(5) . . . . ? C9 C10 C15 C14 -136.8(3) . . . . ? C4 C10 C15 C14 112.9(3) . . . . ? C6 C5 O18 C21 -2.8(6) . . . . ? C4 C5 O18 C21 175.3(3) . . . . ? O116 C101 C102 C103 -173.0(4) . . . . ? C106 C101 C102 C103 9.3(6) . . . . ? C101 C102 C103 C104 4.5(6) . . . . ? C102 C103 C104 N107 -141.4(3) . . . . ? C102 C103 C104 C105 -16.8(5) . . . . ? C102 C103 C104 C110 106.8(4) . . . . ? C121 O118 C105 C106 -0.1(5) . . . . ? C121 O118 C105 C104 -177.5(3) . . . . ? N107 C104 C105 C106 141.6(3) . . . . ? C103 C104 C105 C106 17.1(5) . . . . ? C110 C104 C105 C106 -106.1(4) . . . . ? N107 C104 C105 O118 -41.0(4) . . . . ? C103 C104 C105 O118 -165.5(3) . . . . ? C110 C104 C105 O118 71.4(3) . . . . ? O118 C105 C106 C101 177.9(3) . . . . ? C104 C105 C106 C101 -5.1(5) . . . . ? O116 C101 C106 C105 173.4(4) . . . . ? C102 C101 C106 C105 -8.9(6) . . . . ? C103 C104 N107 C108 -137.9(3) . . . . ? C105 C104 N107 C108 97.9(3) . . . . ? C110 C104 N107 C108 -20.4(3) . . . . ? C103 C104 N107 C116 55.9(4) . . . . ? C105 C104 N107 C116 -68.3(4) . . . . ? C110 C104 N107 C116 173.4(3) . . . . ? C116 N107 C108 O120 -10.6(5) . . . . ? C104 N107 C108 O120 -176.5(3) . . . . ? C116 N107 C108 C109 169.5(3) . . . . ? C104 N107 C108 C109 3.6(4) . . . . ? O120 C108 C109 C110 -163.9(3) . . . . ? N107 C108 C109 C110 15.9(3) . . . . ? C108 C109 C110 C111 -146.6(3) . . . . ? C108 C109 C110 C115 88.7(3) . . . . ? C108 C109 C110 C104 -26.5(3) . . . . ? N107 C104 C110 C111 148.3(2) . . . . ? C103 C104 C110 C111 -93.6(3) . . . . ? C105 C104 C110 C111 29.7(3) . . . . ? N107 C104 C110 C115 -86.4(3) . . . . ? C103 C104 C110 C115 31.6(3) . . . . ? C105 C104 C110 C115 155.0(2) . . . . ? N107 C104 C110 C109 27.8(3) . . . . ? C103 C104 C110 C109 145.9(3) . . . . ? C105 C104 C110 C109 -90.8(3) . . . . ? C115 C110 C111 C112 -4.8(5) . . . . ? C109 C110 C111 C112 -127.3(4) . . . . ? C104 C110 C111 C112 118.9(4) . . . . ? C110 C111 C112 C113 1.8(6) . . . . ? C111 C112 C113 O117 -178.7(5) . . . . ? C111 C112 C113 C114 2.8(7) . . . . ? O117 C113 C114 C115 177.6(5) . . . . ? C112 C113 C114 C115 -3.9(6) . . . . ? C113 C114 C115 C110 0.5(6) . . . . ? C111 C110 C115 C114 3.7(5) . . . . ? C109 C110 C115 C114 128.7(4) . . . . ? C104 C110 C115 C114 -121.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 68.21 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.236 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.059 #===END _database_code_depnum_ccdc_archive 'CCDC 828700'