# 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_ss015 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H14 Br N O3' _chemical_formula_weight 384.22 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' Br Br -0.2901 2.4595 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.3964(9) _cell_length_b 7.3357(6) _cell_length_c 20.4793(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.585(5) _cell_angle_gamma 90.00 _cell_volume 1664.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3273 _cell_measurement_theta_min 2.9517 _cell_measurement_theta_max 32.5522 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 2.486 _exptl_absorpt_correction_T_min 0.6918 _exptl_absorpt_correction_T_max 0.8651 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15880 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 27.50 _reflns_number_total 7267 _reflns_number_gt 4574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0515P)^2^+1.6072P] 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 RIDING _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.43(3) _refine_ls_number_reflns 7267 _refine_ls_number_parameters 436 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0988 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1596 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Br1 Br 0.62468(6) 0.3752(5) 0.02695(2) 0.0759(3) Uani 1 1 d . . . Br2 Br 0.87371(6) 0.8731(3) 0.07769(2) 0.0628(2) Uani 1 1 d . . . O1 O 0.3620(3) -0.1317(19) -0.35392(16) 0.0543(11) Uani 1 1 d . . . O2 O 0.5474(3) 0.3656(17) -0.44411(14) 0.0501(11) Uani 1 1 d . . . O3 O 0.7394(3) 0.376(2) -0.38517(17) 0.0774(16) Uani 1 1 d . . . O4 O 1.0280(3) 1.3736(16) -0.23368(16) 0.0552(10) Uani 1 1 d . . . O5 O 0.8407(3) 0.8837(15) -0.38765(14) 0.0450(10) Uani 1 1 d . . . O6 O 0.6545(4) 0.860(3) -0.36958(19) 0.105(3) Uani 1 1 d . . . N1 N 0.3731(7) 0.5250(12) -0.3507(4) 0.0329(18) Uani 1 1 d . . . H1 H 0.3968 0.6366 -0.3468 0.039 Uiso 1 1 calc R . . N2 N 1.0298(8) 0.7243(11) -0.2462(4) 0.0357(19) Uani 1 1 d . . . H2 H 1.0046 0.6134 -0.2507 0.043 Uiso 1 1 calc R . . C1 C 0.2527(9) 0.2750(12) -0.3673(4) 0.031(2) Uani 1 1 d . . . C2 C 0.1420(10) 0.1778(14) -0.3850(6) 0.040(3) Uani 1 1 d . . . H2 H 0.1416 0.0511 -0.3860 0.048 Uiso 1 1 calc R . . C3 C 0.0358(12) 0.2739(16) -0.4008(6) 0.049(3) Uani 1 1 d . . . H3 H -0.0374 0.2119 -0.4115 0.059 Uiso 1 1 calc R . . C4 C 0.0371(10) 0.4639(16) -0.4008(5) 0.041(3) Uani 1 1 d . . . H4 H -0.0361 0.5259 -0.4124 0.050 Uiso 1 1 calc R . . C5 C 0.1426(11) 0.5639(15) -0.3843(5) 0.039(3) Uani 1 1 d . . . H5 H 0.1418 0.6906 -0.3834 0.047 Uiso 1 1 calc R . . C6 C 0.2487(9) 0.4678(11) -0.3693(5) 0.027(2) Uani 1 1 d . . . C7 C 0.4452(4) 0.3831(16) -0.34069(19) 0.0278(10) Uani 1 1 d . . . C8 C 0.3720(9) 0.2183(11) -0.3509(4) 0.0239(19) Uani 1 1 d . . . C9 C 0.4216(6) 0.0427(8) -0.3428(3) 0.0364(13) Uani 1 1 d . . . H9 H 0.5052 0.0379 -0.3281 0.044 Uiso 1 1 calc R . . C10 C 0.5780(4) 0.377(2) -0.3273(2) 0.0398(12) Uani 1 1 d . . . C11 C 0.6565(4) 0.372(2) -0.2676(2) 0.0476(13) Uani 1 1 d . . . H11 H 0.7366 0.3632 -0.2703 0.057 Uiso 1 1 calc R . . C12 C 0.6409(4) 0.376(2) -0.1990(2) 0.0384(11) Uani 1 1 d . . . C13 C 0.5306(4) 0.3767(19) -0.1811(2) 0.0386(11) Uani 1 1 d . . . H13 H 0.4596 0.3773 -0.2146 0.046 Uiso 1 1 calc R . . C14 C 0.5242(4) 0.3760(19) -0.1143(2) 0.0407(11) Uani 1 1 d . . . H14 H 0.4498 0.3774 -0.1031 0.049 Uiso 1 1 calc R . . C15 C 0.6296(5) 0.373(2) -0.0649(2) 0.0504(14) Uani 1 1 d . . . C16 C 0.7403(5) 0.386(2) -0.0802(2) 0.061(2) Uani 1 1 d . . . H16 H 0.8102 0.3970 -0.0463 0.073 Uiso 1 1 calc R . . C17 C 0.7464(5) 0.383(3) -0.1474(2) 0.0531(17) Uani 1 1 d . . . H17 H 0.8212 0.3854 -0.1582 0.064 Uiso 1 1 calc R . . C18 C 0.6327(5) 0.385(2) -0.3874(2) 0.0492(18) Uani 1 1 d . . . C19 C 0.5898(5) 0.371(3) -0.5059(2) 0.0609(19) Uani 1 1 d . . . H19A H 0.6080 0.4949 -0.5154 0.091 Uiso 1 1 calc R . . H19B H 0.5281 0.3246 -0.5424 0.091 Uiso 1 1 calc R . . H19C H 0.6612 0.2980 -0.5008 0.091 Uiso 1 1 calc R . . C20 C 1.1521(9) 0.9685(11) -0.2244(5) 0.030(2) Uani 1 1 d . . . C21 C 1.2614(9) 1.0700(14) -0.2074(5) 0.038(2) Uani 1 1 d . . . H21 H 1.2615 1.1968 -0.2087 0.045 Uiso 1 1 calc R . . C22 C 1.3643(10) 0.9741(14) -0.1895(5) 0.039(2) Uani 1 1 d . . . H22 H 1.4375 1.0355 -0.1773 0.047 Uiso 1 1 calc R . . C23 C 1.3633(10) 0.7847(15) -0.1888(5) 0.040(2) Uani 1 1 d . . . H23 H 1.4361 0.7221 -0.1763 0.048 Uiso 1 1 calc R . . C24 C 1.2547(10) 0.6855(13) -0.2065(5) 0.035(2) Uani 1 1 d . . . H24 H 1.2548 0.5588 -0.2048 0.042 Uiso 1 1 calc R . . C25 C 1.1496(9) 0.7802(12) -0.2260(5) 0.031(2) Uani 1 1 d . . . C26 C 0.9578(4) 0.8803(17) -0.25801(18) 0.0284(10) Uani 1 1 d . . . C27 C 1.0291(9) 1.0298(12) -0.2464(4) 0.0264(19) Uani 1 1 d . . . C28 C 0.9759(6) 1.2059(10) -0.2505(3) 0.0451(16) Uani 1 1 d . . . H28 H 0.8926 1.2080 -0.2672 0.054 Uiso 1 1 calc R . . C29 C 0.8251(4) 0.881(2) -0.2761(2) 0.0413(13) Uani 1 1 d . . . C30 C 0.7571(4) 0.875(2) -0.2307(2) 0.0490(13) Uani 1 1 d . . . H30 H 0.6743 0.8718 -0.2490 0.059 Uiso 1 1 calc R . . C31 C 0.7916(4) 0.873(2) -0.1572(2) 0.0411(11) Uani 1 1 d . . . C32 C 0.7010(5) 0.864(2) -0.1242(2) 0.0536(17) Uani 1 1 d . . . H32 H 0.6220 0.8479 -0.1487 0.064 Uiso 1 1 calc R . . C33 C 0.7240(5) 0.879(3) -0.0545(3) 0.0635(19) Uani 1 1 d . . . H33 H 0.6605 0.8948 -0.0336 0.076 Uiso 1 1 calc R . . C34 C 0.8392(5) 0.870(2) -0.0173(2) 0.0434(12) Uani 1 1 d . . . C35 C 0.9302(5) 0.874(4) -0.0489(3) 0.100(3) Uani 1 1 d . . . H35 H 1.0095 0.8872 -0.0243 0.120 Uiso 1 1 calc R . . C36 C 0.9052(5) 0.857(4) -0.1195(3) 0.090(4) Uani 1 1 d . . . H36 H 0.9681 0.8353 -0.1403 0.108 Uiso 1 1 calc R . . C37 C 0.7615(5) 0.884(2) -0.3487(2) 0.057(2) Uani 1 1 d . . . C38 C 0.7889(6) 0.887(3) -0.4595(2) 0.059(2) Uani 1 1 d . . . H38A H 0.7631 0.7661 -0.4746 0.088 Uiso 1 1 calc R . . H38B H 0.8485 0.9280 -0.4823 0.088 Uiso 1 1 calc R . . H38C H 0.7209 0.9678 -0.4691 0.088 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 Br1 0.0602(4) 0.1402(7) 0.0242(2) -0.0013(9) 0.0037(2) -0.0024(12) Br2 0.0588(4) 0.0991(5) 0.0305(2) 0.0017(9) 0.0105(2) 0.0036(11) O1 0.039(2) 0.087(3) 0.0380(17) -0.005(6) 0.0119(15) -0.012(6) O2 0.0296(18) 0.097(3) 0.0226(14) 0.006(4) 0.0040(12) 0.008(5) O3 0.025(2) 0.172(5) 0.0354(18) -0.019(7) 0.0075(15) -0.021(7) O4 0.050(2) 0.072(3) 0.0390(17) -0.006(5) 0.0004(16) -0.018(6) O5 0.0339(19) 0.073(3) 0.0260(14) 0.004(4) 0.0030(13) -0.001(5) O6 0.022(2) 0.252(9) 0.0346(19) -0.011(7) -0.0046(15) 0.025(8) N1 0.023(4) 0.044(4) 0.028(4) 0.008(3) -0.001(3) 0.001(4) N2 0.035(5) 0.036(4) 0.036(4) -0.006(4) 0.009(4) -0.007(4) C1 0.026(5) 0.050(5) 0.013(4) -0.003(3) 0.001(4) -0.008(4) C2 0.026(6) 0.046(6) 0.048(7) 0.008(4) 0.010(5) -0.007(5) C3 0.035(7) 0.065(8) 0.046(7) -0.003(5) 0.007(5) -0.014(5) C4 0.022(6) 0.068(7) 0.034(6) 0.001(5) 0.006(4) 0.004(5) C5 0.039(6) 0.055(6) 0.019(5) 0.004(4) -0.001(4) 0.004(5) C6 0.020(5) 0.028(4) 0.033(5) -0.002(3) 0.009(4) -0.003(4) C7 0.026(2) 0.034(3) 0.0213(17) -0.003(4) 0.0017(15) -0.007(5) C8 0.032(5) 0.022(4) 0.020(4) 0.008(3) 0.009(4) 0.003(4) C9 0.042(4) 0.033(3) 0.031(3) 0.006(2) 0.002(2) 0.002(3) C10 0.027(2) 0.068(3) 0.0238(19) 0.011(6) 0.0042(17) 0.009(7) C11 0.025(2) 0.085(4) 0.033(2) 0.005(7) 0.0063(18) 0.009(7) C12 0.026(2) 0.059(3) 0.028(2) -0.005(6) 0.0007(17) -0.006(6) C13 0.027(2) 0.057(3) 0.029(2) -0.011(6) 0.0001(17) -0.002(7) C14 0.036(3) 0.056(3) 0.028(2) -0.010(6) 0.0045(18) -0.001(7) C15 0.047(3) 0.073(4) 0.027(2) 0.014(7) 0.000(2) 0.004(8) C16 0.038(3) 0.109(6) 0.029(2) 0.002(7) -0.006(2) -0.012(8) C17 0.026(3) 0.096(5) 0.034(2) 0.007(7) 0.0003(19) 0.008(7) C18 0.030(3) 0.085(5) 0.032(2) 0.024(6) 0.0054(19) 0.003(6) C19 0.048(3) 0.111(5) 0.025(2) 0.015(8) 0.011(2) 0.025(9) C20 0.030(6) 0.036(5) 0.021(4) -0.008(3) 0.005(4) -0.010(4) C21 0.021(5) 0.050(5) 0.043(6) 0.008(4) 0.007(4) -0.015(4) C22 0.025(6) 0.050(6) 0.042(6) -0.004(4) 0.009(5) -0.007(5) C23 0.021(5) 0.063(7) 0.032(5) -0.004(4) -0.003(4) 0.002(4) C24 0.035(6) 0.038(5) 0.030(5) 0.006(4) 0.006(4) -0.003(4) C25 0.020(5) 0.047(5) 0.025(5) -0.010(4) 0.000(4) -0.002(4) C26 0.027(2) 0.034(3) 0.0231(18) 0.000(4) 0.0033(15) -0.008(5) C27 0.021(5) 0.030(4) 0.022(4) 0.001(4) -0.007(3) 0.000(4) C28 0.039(4) 0.057(4) 0.036(3) -0.001(3) 0.000(3) 0.000(3) C29 0.025(2) 0.069(4) 0.027(2) 0.003(6) -0.0019(17) 0.001(7) C30 0.020(2) 0.089(4) 0.034(2) -0.001(8) -0.0021(17) 0.002(8) C31 0.020(2) 0.070(3) 0.031(2) -0.004(7) 0.0019(17) -0.003(7) C32 0.021(2) 0.094(5) 0.045(3) -0.015(7) 0.006(2) 0.004(7) C33 0.040(3) 0.112(6) 0.042(3) 0.022(8) 0.018(2) 0.013(9) C34 0.038(3) 0.056(3) 0.036(2) -0.002(7) 0.009(2) -0.004(7) C35 0.030(3) 0.237(11) 0.032(3) 0.027(12) 0.002(2) 0.029(13) C36 0.027(3) 0.218(13) 0.028(3) 0.017(10) 0.013(2) -0.007(11) C37 0.033(3) 0.104(6) 0.032(2) -0.027(6) 0.004(2) -0.020(7) C38 0.061(4) 0.086(6) 0.026(2) 0.000(6) 0.003(2) 0.006(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 Br1 C15 1.895(5) . ? Br2 C34 1.891(4) . ? O1 C9 1.441(14) . ? O2 C18 1.336(6) . ? O2 C19 1.458(5) . ? O3 C18 1.208(6) . ? O4 C28 1.374(13) . ? O5 C37 1.337(6) . ? O5 C38 1.451(5) . ? O6 C37 1.207(7) . ? N1 C7 1.312(13) . ? N1 C6 1.441(12) . ? N1 H1 0.8600 . ? N2 C25 1.392(13) . ? N2 C26 1.395(14) . ? N2 H2 0.8600 . ? C1 C8 1.386(13) . ? C1 C6 1.415(6) . ? C1 C2 1.419(14) . ? C2 C3 1.372(17) . ? C2 H2 0.9300 . ? C3 C4 1.394(8) . ? C3 H3 0.9300 . ? C4 C5 1.381(16) . ? C4 H4 0.9300 . ? C5 C6 1.371(14) . ? C5 H5 0.9300 . ? C7 C8 1.456(13) . ? C7 C10 1.474(6) . ? C8 C9 1.401(11) . ? C9 H9 0.9300 . ? C10 C11 1.336(6) . ? C10 C18 1.505(6) . ? C11 C12 1.458(6) . ? C11 H11 0.9300 . ? C12 C13 1.390(6) . ? C12 C17 1.401(6) . ? C13 C14 1.386(6) . ? C13 H13 0.9300 . ? C14 C15 1.377(6) . ? C14 H14 0.9300 . ? C15 C16 1.372(8) . ? C16 C17 1.394(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.383(6) . ? C20 C21 1.422(13) . ? C20 C27 1.440(14) . ? C21 C22 1.343(14) . ? C21 H21 0.9300 . ? C22 C23 1.389(7) . ? C22 H22 0.9300 . ? C23 C24 1.408(14) . ? C23 H23 0.9300 . ? C24 C25 1.361(14) . ? C24 H24 0.9300 . ? C26 C27 1.352(14) . ? C26 C29 1.471(6) . ? C27 C28 1.421(12) . ? C28 H28 0.9300 . ? C29 C30 1.344(6) . ? C29 C37 1.493(6) . ? C30 C31 1.463(6) . ? C30 H30 0.9300 . ? C31 C36 1.348(8) . ? C31 C32 1.362(7) . ? C32 C33 1.392(7) . ? C32 H32 0.9300 . ? C33 C34 1.356(7) . ? C33 H33 0.9300 . ? C34 C35 1.347(7) . ? C35 C36 1.411(8) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? 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 C18 O2 C19 115.4(4) . . ? C37 O5 C38 115.7(4) . . ? C7 N1 C6 110.6(8) . . ? C7 N1 H1 124.7 . . ? C6 N1 H1 124.7 . . ? C25 N2 C26 107.8(8) . . ? C25 N2 H2 126.1 . . ? C26 N2 H2 126.1 . . ? C8 C1 C6 109.2(10) . . ? C8 C1 C2 132.3(9) . . ? C6 C1 C2 118.3(11) . . ? C3 C2 C1 118.9(10) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 120.3(14) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 122.6(14) . . ? C5 C4 H4 118.7 . . ? C3 C4 H4 118.7 . . ? C6 C5 C4 117.0(10) . . ? C6 C5 H5 121.5 . . ? C4 C5 H5 121.5 . . ? C5 C6 C1 122.8(11) . . ? C5 C6 N1 132.1(9) . . ? C1 C6 N1 105.1(10) . . ? N1 C7 C8 108.6(4) . . ? N1 C7 C10 129.2(11) . . ? C8 C7 C10 122.0(11) . . ? C1 C8 C9 130.5(8) . . ? C1 C8 C7 106.4(7) . . ? C9 C8 C7 123.0(8) . . ? C8 C9 O1 129.5(7) . . ? C8 C9 H9 115.3 . . ? O1 C9 H9 115.3 . . ? C11 C10 C7 127.5(4) . . ? C11 C10 C18 115.7(4) . . ? C7 C10 C18 116.8(4) . . ? C10 C11 C12 132.5(4) . . ? C10 C11 H11 113.8 . . ? C12 C11 H11 113.8 . . ? C13 C12 C17 118.1(4) . . ? C13 C12 C11 125.2(4) . . ? C17 C12 C11 116.7(4) . . ? C14 C13 C12 121.3(4) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C15 C14 C13 119.1(5) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C16 C15 C14 121.4(4) . . ? C16 C15 Br1 118.0(4) . . ? C14 C15 Br1 120.3(4) . . ? C15 C16 C17 119.1(5) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C16 C17 C12 120.8(5) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? O3 C18 O2 123.2(5) . . ? O3 C18 C10 125.0(4) . . ? O2 C18 C10 110.5(4) . . ? O2 C19 H19A 109.5 . . ? O2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 122.8(12) . . ? C25 C20 C27 106.9(10) . . ? C21 C20 C27 130.2(9) . . ? C22 C21 C20 116.8(9) . . ? C22 C21 H21 121.6 . . ? C20 C21 H21 121.6 . . ? C21 C22 C23 121.2(12) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C22 C23 C24 121.5(12) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C25 C24 C23 118.2(9) . . ? C25 C24 H24 120.9 . . ? C23 C24 H24 120.9 . . ? C24 C25 C20 119.4(11) . . ? C24 C25 N2 132.2(9) . . ? C20 C25 N2 108.3(11) . . ? C27 C26 N2 109.3(4) . . ? C27 C26 C29 125.6(12) . . ? N2 C26 C29 125.0(11) . . ? C26 C27 C28 119.8(8) . . ? C26 C27 C20 107.6(8) . . ? C28 C27 C20 132.3(8) . . ? O4 C28 C27 130.2(7) . . ? O4 C28 H28 114.9 . . ? C27 C28 H28 114.9 . . ? C30 C29 C26 123.5(4) . . ? C30 C29 C37 117.8(4) . . ? C26 C29 C37 118.7(4) . . ? C29 C30 C31 130.8(4) . . ? C29 C30 H30 114.6 . . ? C31 C30 H30 114.6 . . ? C36 C31 C32 116.7(5) . . ? C36 C31 C30 125.5(5) . . ? C32 C31 C30 117.4(4) . . ? C31 C32 C33 121.6(5) . . ? C31 C32 H32 119.2 . . ? C33 C32 H32 119.2 . . ? C34 C33 C32 119.8(5) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C35 C34 C33 118.8(5) . . ? C35 C34 Br2 119.8(4) . . ? C33 C34 Br2 121.2(4) . . ? C34 C35 C36 119.9(6) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C31 C36 C35 121.0(6) . . ? C31 C36 H36 119.5 . . ? C35 C36 H36 119.5 . . ? O6 C37 O5 123.8(5) . . ? O6 C37 C29 124.3(6) . . ? O5 C37 C29 110.9(4) . . ? O5 C38 H38A 109.5 . . ? O5 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O5 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 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 C8 C1 C2 C3 -178.1(10) . . . . ? C6 C1 C2 C3 -2.7(17) . . . . ? C1 C2 C3 C4 2(2) . . . . ? C2 C3 C4 C5 -1(2) . . . . ? C3 C4 C5 C6 1.7(19) . . . . ? C4 C5 C6 C1 -3.0(17) . . . . ? C4 C5 C6 N1 179.6(9) . . . . ? C8 C1 C6 C5 179.9(7) . . . . ? C2 C1 C6 C5 3.5(19) . . . . ? C8 C1 C6 N1 -2.1(13) . . . . ? C2 C1 C6 N1 -178.5(7) . . . . ? C7 N1 C6 C5 179.7(9) . . . . ? C7 N1 C6 C1 2.0(11) . . . . ? C6 N1 C7 C8 -1.1(6) . . . . ? C6 N1 C7 C10 173.6(5) . . . . ? C6 C1 C8 C9 179.9(9) . . . . ? C2 C1 C8 C9 -4.4(16) . . . . ? C6 C1 C8 C7 1.5(11) . . . . ? C2 C1 C8 C7 177.2(9) . . . . ? N1 C7 C8 C1 -0.2(5) . . . . ? C10 C7 C8 C1 -175.4(5) . . . . ? N1 C7 C8 C9 -178.8(8) . . . . ? C10 C7 C8 C9 6.0(9) . . . . ? C1 C8 C9 O1 5.0(12) . . . . ? C7 C8 C9 O1 -176.9(5) . . . . ? N1 C7 C10 C11 94.0(18) . . . . ? C8 C7 C10 C11 -91.9(18) . . . . ? N1 C7 C10 C18 -83.3(14) . . . . ? C8 C7 C10 C18 90.7(13) . . . . ? C7 C10 C11 C12 -3(3) . . . . ? C18 C10 C11 C12 174.8(17) . . . . ? C10 C11 C12 C13 4(3) . . . . ? C10 C11 C12 C17 -174.9(18) . . . . ? C17 C12 C13 C14 -3(2) . . . . ? C11 C12 C13 C14 178.1(15) . . . . ? C12 C13 C14 C15 -1(2) . . . . ? C13 C14 C15 C16 5(2) . . . . ? C13 C14 C15 Br1 179.3(11) . . . . ? C14 C15 C16 C17 -7(3) . . . . ? Br1 C15 C16 C17 179.3(13) . . . . ? C15 C16 C17 C12 3(3) . . . . ? C13 C12 C17 C16 1(3) . . . . ? C11 C12 C17 C16 -179.4(16) . . . . ? C19 O2 C18 O3 -13(2) . . . . ? C19 O2 C18 C10 180.0(13) . . . . ? C11 C10 C18 O3 5(3) . . . . ? C7 C10 C18 O3 -177.6(17) . . . . ? C11 C10 C18 O2 171.8(15) . . . . ? C7 C10 C18 O2 -10.6(19) . . . . ? C25 C20 C21 C22 -3.2(17) . . . . ? C27 C20 C21 C22 -178.8(10) . . . . ? C20 C21 C22 C23 1.1(18) . . . . ? C21 C22 C23 C24 0(2) . . . . ? C22 C23 C24 C25 1.5(18) . . . . ? C23 C24 C25 C20 -3.5(16) . . . . ? C23 C24 C25 N2 180.0(10) . . . . ? C21 C20 C25 C24 5(2) . . . . ? C27 C20 C25 C24 -179.0(7) . . . . ? C21 C20 C25 N2 -178.2(7) . . . . ? C27 C20 C25 N2 -1.7(14) . . . . ? C26 N2 C25 C24 177.6(10) . . . . ? C26 N2 C25 C20 0.8(11) . . . . ? C25 N2 C26 C27 0.6(6) . . . . ? C25 N2 C26 C29 -176.0(6) . . . . ? N2 C26 C27 C28 -175.6(8) . . . . ? C29 C26 C27 C28 0.9(10) . . . . ? N2 C26 C27 C20 -1.6(6) . . . . ? C29 C26 C27 C20 174.9(5) . . . . ? C25 C20 C27 C26 2.1(11) . . . . ? C21 C20 C27 C26 178.2(9) . . . . ? C25 C20 C27 C28 175.0(10) . . . . ? C21 C20 C27 C28 -8.8(16) . . . . ? C26 C27 C28 O4 171.7(6) . . . . ? C20 C27 C28 O4 -0.6(14) . . . . ? C27 C26 C29 C30 -90.2(18) . . . . ? N2 C26 C29 C30 85.7(18) . . . . ? C27 C26 C29 C37 91.0(15) . . . . ? N2 C26 C29 C37 -93.0(14) . . . . ? C26 C29 C30 C31 2(3) . . . . ? C37 C29 C30 C31 -179.2(15) . . . . ? C29 C30 C31 C36 -7(3) . . . . ? C29 C30 C31 C32 -179.2(19) . . . . ? C36 C31 C32 C33 14(3) . . . . ? C30 C31 C32 C33 -173.8(15) . . . . ? C31 C32 C33 C34 -12(3) . . . . ? C32 C33 C34 C35 9(3) . . . . ? C32 C33 C34 Br2 -175.6(13) . . . . ? C33 C34 C35 C36 -10(3) . . . . ? Br2 C34 C35 C36 175.0(19) . . . . ? C32 C31 C36 C35 -14(3) . . . . ? C30 C31 C36 C35 174(2) . . . . ? C34 C35 C36 C31 13(4) . . . . ? C38 O5 C37 O6 11(3) . . . . ? C38 O5 C37 C29 180.0(13) . . . . ? C30 C29 C37 O6 -9(3) . . . . ? C26 C29 C37 O6 169.5(19) . . . . ? C30 C29 C37 O5 -178.0(16) . . . . ? C26 C29 C37 O5 1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.469 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 952075' ####################################################################### # # 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_ss016 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 N O4' _chemical_formula_weight 321.32 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 Orthorhombic _symmetry_space_group_name_H-M 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3019(5) _cell_length_b 16.7028(18) _cell_length_c 20.7326(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3221.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3931 _cell_measurement_theta_min 2.9368 _cell_measurement_theta_max 32.4644 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_min 0.9788 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Micro-Focus (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23304 _diffrn_reflns_av_R_equivalents 0.0988 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2829 _reflns_number_gt 2194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0864P)^2^+2.1392P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2829 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1796 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 -0.0966(2) 0.11779(11) 0.30986(9) 0.0440(5) Uani 1 1 d . . . O2 O 0.69700(19) 0.16079(11) 0.49439(9) 0.0431(5) Uani 1 1 d . . . O3 O 0.6279(2) 0.13909(14) 0.59585(9) 0.0556(6) Uani 1 1 d . . . O4 O 0.3405(2) -0.05931(10) 0.63930(9) 0.0429(5) Uani 1 1 d . . . N1 N 0.2712(2) 0.20789(12) 0.59197(9) 0.0358(5) Uani 1 1 d . . . H1 H 0.2782 0.2553 0.5738 0.043 Uiso 1 1 calc R . . C1 C 0.0220(3) 0.11877(14) 0.34837(13) 0.0373(6) Uani 1 1 d . . . C2 C 0.1545(3) 0.12093(16) 0.31830(13) 0.0417(7) Uani 1 1 d . . . H2 H 0.1606 0.1187 0.2726 0.050 Uiso 1 1 calc R . . C3 C 0.2776(3) 0.12634(16) 0.35479(13) 0.0407(6) Uani 1 1 d . . . H3 H 0.3682 0.1273 0.3336 0.049 Uiso 1 1 calc R . . C4 C 0.2734(3) 0.13056(15) 0.42234(12) 0.0374(6) Uani 1 1 d . . . C5 C 0.1377(3) 0.12505(15) 0.45165(13) 0.0395(6) Uani 1 1 d . . . H5 H 0.1308 0.1256 0.4974 0.047 Uiso 1 1 calc R . . C6 C 0.0141(3) 0.11881(16) 0.41504(13) 0.0404(6) Uani 1 1 d . . . H6 H -0.0767 0.1145 0.4357 0.048 Uiso 1 1 calc R . . C7 C 0.4103(3) 0.14020(15) 0.45540(12) 0.0363(6) Uani 1 1 d . . . H7 H 0.4903 0.1444 0.4271 0.044 Uiso 1 1 calc R . . C8 C 0.4459(3) 0.14437(14) 0.51831(12) 0.0358(6) Uani 1 1 d . . . C9 C 0.6026(3) 0.14997(15) 0.53384(12) 0.0378(6) Uani 1 1 d . . . C10 C 0.7776(4) 0.1390(3) 0.61529(17) 0.0762(12) Uani 1 1 d . . . H10A H 0.8242 0.0901 0.5996 0.114 Uiso 1 1 calc R . . H10B H 0.7837 0.1410 0.6624 0.114 Uiso 1 1 calc R . . H10C H 0.8261 0.1858 0.5969 0.114 Uiso 1 1 calc R . . C11 C 0.3434(3) 0.14143(15) 0.57265(12) 0.0349(6) Uani 1 1 d . . . C12 C 0.3053(3) 0.07781(14) 0.61296(11) 0.0332(6) Uani 1 1 d . . . C13 C 0.3676(3) 0.00051(15) 0.60633(12) 0.0379(6) Uani 1 1 d . . . H13 H 0.4372 -0.0058 0.5732 0.045 Uiso 1 1 calc R . . C14 C 0.2037(3) 0.10842(14) 0.65938(11) 0.0334(6) Uani 1 1 d . . . C15 C 0.1300(3) 0.07626(16) 0.71234(12) 0.0387(6) Uani 1 1 d . . . H15 H 0.1412 0.0216 0.7239 0.046 Uiso 1 1 calc R . . C16 C 0.0405(3) 0.12607(16) 0.74738(12) 0.0417(7) Uani 1 1 d . . . H16 H -0.0115 0.1046 0.7828 0.050 Uiso 1 1 calc R . . C17 C 0.0243(3) 0.20692(16) 0.73211(12) 0.0420(7) Uani 1 1 d . . . H17 H -0.0375 0.2395 0.7575 0.050 Uiso 1 1 calc R . . C18 C 0.0968(3) 0.24014(16) 0.68087(12) 0.0398(6) Uani 1 1 d . . . H18 H 0.0873 0.2953 0.6706 0.048 Uiso 1 1 calc R . . C19 C 0.1844(3) 0.18996(15) 0.64472(11) 0.0342(6) Uani 1 1 d . . . H101 H -0.180(4) 0.103(2) 0.3319(17) 0.073(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0409(11) 0.0466(12) 0.0445(11) 0.0067(8) -0.0054(9) -0.0064(9) O2 0.0411(11) 0.0469(12) 0.0414(11) 0.0074(8) 0.0055(8) -0.0023(8) O3 0.0409(12) 0.0869(16) 0.0389(11) 0.0100(10) -0.0057(8) -0.0130(10) O4 0.0487(12) 0.0303(10) 0.0498(11) 0.0067(8) 0.0066(8) 0.0013(8) N1 0.0444(13) 0.0263(11) 0.0368(11) 0.0025(9) 0.0027(9) 0.0007(9) C1 0.0419(15) 0.0287(13) 0.0415(14) 0.0047(10) -0.0020(11) -0.0025(10) C2 0.0445(16) 0.0480(16) 0.0327(14) 0.0021(11) 0.0006(11) -0.0057(12) C3 0.0409(15) 0.0437(16) 0.0374(14) 0.0018(11) 0.0051(12) -0.0022(11) C4 0.0438(15) 0.0311(13) 0.0371(14) 0.0034(10) 0.0020(11) -0.0002(11) C5 0.0448(15) 0.0407(15) 0.0329(14) 0.0013(11) 0.0019(11) 0.0016(11) C6 0.0383(15) 0.0407(15) 0.0421(15) 0.0008(11) 0.0044(11) -0.0003(11) C7 0.0415(15) 0.0320(13) 0.0355(14) 0.0039(10) 0.0045(11) 0.0011(11) C8 0.0426(15) 0.0286(13) 0.0364(13) 0.0015(10) 0.0027(11) 0.0000(10) C9 0.0448(15) 0.0320(14) 0.0364(14) 0.0019(10) 0.0001(12) -0.0036(11) C10 0.045(2) 0.131(4) 0.052(2) 0.021(2) -0.0128(15) -0.019(2) C11 0.0389(14) 0.0318(13) 0.0341(13) -0.0015(10) -0.0017(11) -0.0005(10) C12 0.0367(14) 0.0289(13) 0.0339(13) 0.0000(10) 0.0003(10) 0.0005(10) C13 0.0401(15) 0.0354(15) 0.0382(13) 0.0018(11) 0.0040(11) 0.0003(11) C14 0.0380(14) 0.0304(13) 0.0319(13) 0.0005(10) -0.0015(10) -0.0001(10) C15 0.0435(15) 0.0352(14) 0.0374(14) -0.0001(11) 0.0033(11) -0.0039(11) C16 0.0458(16) 0.0450(16) 0.0344(14) -0.0009(11) 0.0044(11) -0.0028(12) C17 0.0410(15) 0.0455(16) 0.0396(14) -0.0079(11) 0.0030(11) 0.0041(12) C18 0.0457(15) 0.0317(13) 0.0419(14) -0.0031(11) -0.0024(12) 0.0032(11) C19 0.0375(14) 0.0331(14) 0.0321(13) -0.0010(10) -0.0010(10) -0.0006(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.361(3) . ? O1 H101 0.94(4) . ? O2 C9 1.213(3) . ? O3 C9 1.320(3) . ? O3 C10 1.450(4) . ? O4 C13 1.237(3) . ? N1 C11 1.358(3) . ? N1 C19 1.392(3) . ? N1 H1 0.8800 . ? C1 C2 1.382(4) . ? C1 C6 1.384(4) . ? C2 C3 1.376(4) . ? C2 H2 0.9500 . ? C3 C4 1.403(4) . ? C3 H3 0.9500 . ? C4 C5 1.404(4) . ? C4 C7 1.455(4) . ? C5 C6 1.382(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.347(4) . ? C7 H7 0.9500 . ? C8 C11 1.476(3) . ? C8 C9 1.496(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.398(3) . ? C12 C13 1.422(3) . ? C12 C14 1.443(3) . ? C13 H13 0.9500 . ? C14 C15 1.402(3) . ? C14 C19 1.407(3) . ? C15 C16 1.383(4) . ? C15 H15 0.9500 . ? C16 C17 1.395(4) . ? C16 H16 0.9500 . ? C17 C18 1.375(4) . ? C17 H17 0.9500 . ? C18 C19 1.388(4) . ? C18 H18 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 C1 O1 H101 113(2) . . ? C9 O3 C10 116.2(2) . . ? C11 N1 C19 110.1(2) . . ? C11 N1 H1 125.0 . . ? C19 N1 H1 125.0 . . ? O1 C1 C2 117.3(2) . . ? O1 C1 C6 122.9(2) . . ? C2 C1 C6 119.8(2) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.9(3) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 117.0(2) . . ? C3 C4 C7 116.8(2) . . ? C5 C4 C7 126.2(2) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 120.3(2) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C8 C7 C4 132.6(2) . . ? C8 C7 H7 113.7 . . ? C4 C7 H7 113.7 . . ? C7 C8 C11 125.3(2) . . ? C7 C8 C9 116.8(2) . . ? C11 C8 C9 117.8(2) . . ? O2 C9 O3 123.3(2) . . ? O2 C9 C8 124.7(2) . . ? O3 C9 C8 112.0(2) . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N1 C11 C12 108.6(2) . . ? N1 C11 C8 121.2(2) . . ? C12 C11 C8 130.2(2) . . ? C11 C12 C13 122.0(2) . . ? C11 C12 C14 107.2(2) . . ? C13 C12 C14 130.8(2) . . ? O4 C13 C12 126.7(2) . . ? O4 C13 H13 116.7 . . ? C12 C13 H13 116.7 . . ? C15 C14 C19 118.5(2) . . ? C15 C14 C12 135.0(2) . . ? C19 C14 C12 106.4(2) . . ? C16 C15 C14 118.4(2) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C15 C16 C17 121.9(2) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 120.9(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 117.5(2) . . ? C17 C18 H18 121.3 . . ? C19 C18 H18 121.3 . . ? C18 C19 N1 129.4(2) . . ? C18 C19 C14 122.9(2) . . ? N1 C19 C14 107.7(2) . . ? 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 O1 C1 C2 C3 176.5(2) . . . . ? C6 C1 C2 C3 -2.6(4) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 3.0(4) . . . . ? C2 C3 C4 C7 -177.0(2) . . . . ? C3 C4 C5 C6 -2.4(4) . . . . ? C7 C4 C5 C6 177.7(2) . . . . ? C4 C5 C6 C1 -0.7(4) . . . . ? O1 C1 C6 C5 -175.8(2) . . . . ? C2 C1 C6 C5 3.3(4) . . . . ? C3 C4 C7 C8 -178.2(3) . . . . ? C5 C4 C7 C8 1.8(5) . . . . ? C4 C7 C8 C11 -1.5(4) . . . . ? C4 C7 C8 C9 176.6(2) . . . . ? C10 O3 C9 O2 -1.2(4) . . . . ? C10 O3 C9 C8 176.7(3) . . . . ? C7 C8 C9 O2 9.5(4) . . . . ? C11 C8 C9 O2 -172.3(2) . . . . ? C7 C8 C9 O3 -168.5(2) . . . . ? C11 C8 C9 O3 9.8(3) . . . . ? C19 N1 C11 C12 -0.2(3) . . . . ? C19 N1 C11 C8 -178.6(2) . . . . ? C7 C8 C11 N1 -82.3(3) . . . . ? C9 C8 C11 N1 99.6(3) . . . . ? C7 C8 C11 C12 99.6(3) . . . . ? C9 C8 C11 C12 -78.4(3) . . . . ? N1 C11 C12 C13 -177.6(2) . . . . ? C8 C11 C12 C13 0.6(4) . . . . ? N1 C11 C12 C14 0.0(3) . . . . ? C8 C11 C12 C14 178.2(2) . . . . ? C11 C12 C13 O4 -179.6(3) . . . . ? C14 C12 C13 O4 3.4(5) . . . . ? C11 C12 C14 C15 -178.0(3) . . . . ? C13 C12 C14 C15 -0.7(5) . . . . ? C11 C12 C14 C19 0.2(3) . . . . ? C13 C12 C14 C19 177.5(3) . . . . ? C19 C14 C15 C16 0.6(4) . . . . ? C12 C14 C15 C16 178.7(3) . . . . ? C14 C15 C16 C17 -1.3(4) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 C19 0.9(4) . . . . ? C17 C18 C19 N1 -178.4(2) . . . . ? C17 C18 C19 C14 -1.5(4) . . . . ? C11 N1 C19 C18 177.6(3) . . . . ? C11 N1 C19 C14 0.3(3) . . . . ? C15 C14 C19 C18 0.8(4) . . . . ? C12 C14 C19 C18 -177.8(2) . . . . ? C15 C14 C19 N1 178.2(2) . . . . ? C12 C14 C19 N1 -0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.244 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 952076'