# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_bb _audit_creation_date 2013-10-18 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C19 H17 N O2)' _chemical_formula_sum 'C38 H34 N2 O4' _chemical_formula_weight 582.67 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7792(8) _cell_length_b 25.118(2) _cell_length_c 14.2371(13) _cell_angle_alpha 90.00 _cell_angle_beta 103.655(2) _cell_angle_gamma 90.00 _cell_volume 3050.8(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1758 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 23.28 _cell_measurement_theta_min 2.52 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_correction_T_min 0.9678 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 1232 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.13 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1058 _diffrn_reflns_av_unetI/netI 0.1120 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 23261 _diffrn_reflns_theta_full 25.35 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_min 1.62 _diffrn_ambient_temperature 296.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _reflns_number_gt 2905 _reflns_number_total 5573 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 0.377 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.056 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 401 _refine_ls_number_reflns 5573 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1335 _refine_ls_R_factor_gt 0.0581 _refine_ls_restrained_S_all 0.981 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1180 _refine_ls_wR_factor_ref 0.1505 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.3710(3) 0.54390(8) 0.77625(16) 0.0360(6) Uani 1 1 d . . . O2 O 0.1372(3) 0.58460(7) 0.73246(15) 0.0334(6) Uani 1 1 d . . . O3 O -0.3779(3) 0.20149(7) 0.67642(15) 0.0290(5) Uani 1 1 d . . . O4 O -0.1398(3) 0.16341(7) 0.72050(15) 0.0289(5) Uani 1 1 d . . . N1 N 0.1106(3) 0.41737(9) 0.61447(17) 0.0246(6) Uani 1 1 d . . . N2 N -0.1185(3) 0.33033(8) 0.83609(17) 0.0213(6) Uani 1 1 d . . . C1 C 0.2150(5) 0.63311(12) 0.7732(3) 0.0437(10) Uani 1 1 d . . . H1A H 0.2831 0.6453 0.7339 0.066 Uiso 1 1 calc R . . H1B H 0.2754 0.6263 0.8375 0.066 Uiso 1 1 calc R . . H1C H 0.1379 0.6600 0.7751 0.066 Uiso 1 1 calc R . . C2 C 0.2328(4) 0.54198(11) 0.7356(2) 0.0252(8) Uani 1 1 d . . . C3 C 0.1500(4) 0.49629(11) 0.6863(2) 0.0223(7) Uani 1 1 d . . . C4 C -0.0129(4) 0.48885(11) 0.6516(2) 0.0245(7) Uani 1 1 d . . . H4 H -0.0907 0.5128 0.6579 0.029 Uiso 1 1 calc R . . C5 C -0.0366(4) 0.43992(11) 0.6068(2) 0.0223(7) Uani 1 1 d . . . C6 C -0.1844(4) 0.41359(11) 0.5607(2) 0.0244(7) Uani 1 1 d . . . C7 C -0.3027(4) 0.44227(13) 0.4993(2) 0.0323(8) Uani 1 1 d . . . H7 H -0.2883 0.4783 0.4890 0.039 Uiso 1 1 calc R . . C8 C -0.4410(4) 0.41802(14) 0.4534(2) 0.0414(9) Uani 1 1 d . . . H8 H -0.5184 0.4377 0.4119 0.050 Uiso 1 1 calc R . . C9 C -0.4656(4) 0.36472(14) 0.4686(2) 0.0397(9) Uani 1 1 d . . . H9 H -0.5587 0.3483 0.4373 0.048 Uiso 1 1 calc R . . C10 C -0.3498(4) 0.33595(13) 0.5311(2) 0.0345(9) Uani 1 1 d . . . H10 H -0.3664 0.3002 0.5424 0.041 Uiso 1 1 calc R . . C11 C -0.2109(4) 0.35954(11) 0.5767(2) 0.0271(8) Uani 1 1 d . . . H11 H -0.1342 0.3397 0.6183 0.033 Uiso 1 1 calc R . . C12 C 0.1414(4) 0.36810(11) 0.5707(2) 0.0245(8) Uani 1 1 d . . . C13 C 0.0905(4) 0.36129(12) 0.4717(2) 0.0294(8) Uani 1 1 d . . . H13 H 0.0354 0.3882 0.4333 0.035 Uiso 1 1 calc R . . C14 C 0.1229(4) 0.31392(13) 0.4306(2) 0.0329(8) Uani 1 1 d . . . H14 H 0.0886 0.3090 0.3643 0.039 Uiso 1 1 calc R . . C15 C 0.2051(4) 0.27416(12) 0.4869(2) 0.0325(8) Uani 1 1 d . . . H15 H 0.2270 0.2426 0.4584 0.039 Uiso 1 1 calc R . . C16 C 0.2556(4) 0.28101(12) 0.5860(2) 0.0331(9) Uani 1 1 d . . . H16 H 0.3121 0.2542 0.6240 0.040 Uiso 1 1 calc R . . C17 C 0.2217(4) 0.32788(11) 0.6285(2) 0.0277(8) Uani 1 1 d . . . H17 H 0.2527 0.3323 0.6952 0.033 Uiso 1 1 calc R . . C18 C 0.2264(4) 0.45150(11) 0.6620(2) 0.0231(7) Uani 1 1 d . . . C19 C 0.3947(4) 0.44053(12) 0.6741(2) 0.0354(9) Uani 1 1 d . . . H19A H 0.4342 0.4226 0.7344 0.053 Uiso 1 1 calc R . . H19B H 0.4501 0.4735 0.6737 0.053 Uiso 1 1 calc R . . H19C H 0.4095 0.4184 0.6220 0.053 Uiso 1 1 calc R . . C20 C -0.2100(4) 0.11392(11) 0.6798(3) 0.0356(9) Uani 1 1 d . . . H20A H -0.2628 0.1194 0.6133 0.053 Uiso 1 1 calc R . . H20B H -0.2840 0.1020 0.7153 0.053 Uiso 1 1 calc R . . H20C H -0.1297 0.0875 0.6837 0.053 Uiso 1 1 calc R . . C21 C -0.2400(4) 0.20456(11) 0.7153(2) 0.0218(7) Uani 1 1 d . . . C22 C -0.1588(4) 0.25141(10) 0.7644(2) 0.0200(7) Uani 1 1 d . . . C23 C 0.0039(4) 0.25818(10) 0.8014(2) 0.0219(7) Uani 1 1 d . . . H23 H 0.0811 0.2337 0.7968 0.026 Uiso 1 1 calc R . . C24 C 0.0287(4) 0.30700(10) 0.8453(2) 0.0205(7) Uani 1 1 d . . . C25 C 0.1763(4) 0.33394(10) 0.8895(2) 0.0207(7) Uani 1 1 d . . . C26 C 0.2027(4) 0.38725(11) 0.8683(2) 0.0233(7) Uani 1 1 d . . . H26 H 0.1245 0.4064 0.8263 0.028 Uiso 1 1 calc R . . C27 C 0.3432(4) 0.41142(12) 0.9091(2) 0.0271(8) Uani 1 1 d . . . H27 H 0.3588 0.4468 0.8943 0.033 Uiso 1 1 calc R . . C28 C 0.4621(4) 0.38399(12) 0.9721(2) 0.0288(8) Uani 1 1 d . . . H28 H 0.5567 0.4006 0.9998 0.035 Uiso 1 1 calc R . . C29 C 0.4369(4) 0.33131(12) 0.9927(2) 0.0314(8) Uani 1 1 d . . . H29 H 0.5156 0.3124 1.0347 0.038 Uiso 1 1 calc R . . C30 C 0.2963(4) 0.30637(12) 0.9517(2) 0.0293(8) Uani 1 1 d . . . H30 H 0.2819 0.2708 0.9660 0.035 Uiso 1 1 calc R . . C31 C -0.1459(4) 0.37948(10) 0.8814(2) 0.0220(7) Uani 1 1 d . . . C32 C -0.0921(4) 0.38513(12) 0.9809(2) 0.0255(8) Uani 1 1 d . . . H32 H -0.0414 0.3571 1.0182 0.031 Uiso 1 1 calc R . . C33 C -0.1150(4) 0.43301(12) 1.0234(3) 0.0365(9) Uani 1 1 d . . . H33 H -0.0772 0.4375 1.0896 0.044 Uiso 1 1 calc R . . C34 C -0.1933(4) 0.47395(13) 0.9685(3) 0.0381(10) Uani 1 1 d . . . H34 H -0.2079 0.5060 0.9978 0.046 Uiso 1 1 calc R . . C35 C -0.2503(4) 0.46786(11) 0.8702(3) 0.0377(9) Uani 1 1 d . . . H35 H -0.3061 0.4953 0.8336 0.045 Uiso 1 1 calc R . . C36 C -0.2238(4) 0.42040(11) 0.8259(2) 0.0281(8) Uani 1 1 d . . . H36 H -0.2586 0.4164 0.7594 0.034 Uiso 1 1 calc R . . C37 C -0.2336(4) 0.29682(10) 0.7869(2) 0.0198(7) Uani 1 1 d . . . C38 C -0.4014(4) 0.30953(12) 0.7709(2) 0.0298(8) Uani 1 1 d . . . H38A H -0.4345 0.3294 0.7120 0.045 Uiso 1 1 calc R . . H38B H -0.4185 0.3304 0.8240 0.045 Uiso 1 1 calc R . . H38C H -0.4607 0.2771 0.7663 0.045 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 0.0288(17) 0.0271(12) 0.0465(16) -0.0023(11) -0.0025(13) -0.0010(11) O2 0.0350(16) 0.0206(11) 0.0381(14) -0.0073(10) -0.0043(12) 0.0038(11) O3 0.0237(15) 0.0258(11) 0.0355(14) -0.0047(10) 0.0030(12) 0.0001(10) O4 0.0243(14) 0.0177(11) 0.0414(14) -0.0085(9) 0.0012(11) -0.0005(10) N1 0.0258(17) 0.0220(13) 0.0249(15) 0.0002(11) 0.0038(13) -0.0014(12) N2 0.0222(16) 0.0151(12) 0.0250(15) -0.0005(11) 0.0024(13) -0.0034(11) C1 0.048(3) 0.0217(18) 0.053(2) -0.0087(16) -0.005(2) -0.0023(17) C2 0.028(2) 0.0238(17) 0.0230(18) 0.0045(14) 0.0037(16) 0.0020(16) C3 0.023(2) 0.0202(15) 0.0216(17) 0.0026(13) 0.0018(15) -0.0006(14) C4 0.027(2) 0.0209(16) 0.0253(18) 0.0010(13) 0.0064(16) 0.0000(14) C5 0.021(2) 0.0239(16) 0.0211(18) 0.0042(13) 0.0034(15) 0.0023(14) C6 0.022(2) 0.0277(17) 0.0236(18) -0.0017(14) 0.0048(15) -0.0065(15) C7 0.027(2) 0.0343(18) 0.033(2) 0.0104(16) 0.0024(17) -0.0033(16) C8 0.029(2) 0.060(2) 0.030(2) 0.0108(18) -0.0040(18) -0.0044(19) C9 0.029(2) 0.057(2) 0.034(2) -0.0108(18) 0.0095(19) -0.0157(19) C10 0.031(2) 0.0339(19) 0.042(2) -0.0087(17) 0.017(2) -0.0086(17) C11 0.026(2) 0.0277(17) 0.0289(19) -0.0033(14) 0.0089(17) -0.0017(15) C12 0.025(2) 0.0248(16) 0.0240(18) -0.0008(14) 0.0066(16) -0.0035(14) C13 0.025(2) 0.0383(19) 0.0233(19) 0.0011(15) 0.0025(16) -0.0003(16) C14 0.029(2) 0.045(2) 0.0236(19) -0.0070(16) 0.0040(17) -0.0044(17) C15 0.034(2) 0.0305(18) 0.034(2) -0.0088(16) 0.0109(18) -0.0047(16) C16 0.039(2) 0.0254(17) 0.033(2) 0.0011(15) 0.0044(18) -0.0006(16) C17 0.030(2) 0.0270(17) 0.0257(19) 0.0003(14) 0.0047(16) -0.0043(15) C18 0.019(2) 0.0244(16) 0.0248(18) 0.0042(14) 0.0026(15) -0.0019(14) C19 0.034(2) 0.0332(18) 0.039(2) -0.0004(15) 0.0089(19) 0.0004(16) C20 0.033(2) 0.0139(15) 0.056(2) -0.0116(15) 0.0038(19) -0.0019(15) C21 0.023(2) 0.0198(16) 0.0222(18) -0.0010(13) 0.0052(16) -0.0011(14) C22 0.022(2) 0.0172(15) 0.0206(17) 0.0016(12) 0.0049(15) -0.0001(13) C23 0.023(2) 0.0155(15) 0.0265(18) 0.0038(13) 0.0040(15) 0.0056(13) C24 0.022(2) 0.0157(15) 0.0241(18) 0.0015(13) 0.0055(15) 0.0023(13) C25 0.023(2) 0.0188(15) 0.0218(17) -0.0031(13) 0.0092(15) 0.0008(14) C26 0.025(2) 0.0218(16) 0.0237(18) 0.0000(13) 0.0076(16) -0.0001(14) C27 0.028(2) 0.0215(16) 0.035(2) -0.0030(15) 0.0132(17) -0.0027(15) C28 0.020(2) 0.0310(18) 0.035(2) -0.0075(15) 0.0059(17) -0.0038(15) C29 0.021(2) 0.0321(18) 0.038(2) 0.0015(16) 0.0006(17) 0.0028(15) C30 0.027(2) 0.0228(17) 0.036(2) -0.0023(15) 0.0032(17) -0.0017(15) C31 0.022(2) 0.0146(15) 0.0311(19) -0.0023(13) 0.0087(16) 0.0000(13) C32 0.016(2) 0.0311(17) 0.0293(19) -0.0028(14) 0.0053(16) -0.0007(14) C33 0.029(2) 0.042(2) 0.041(2) -0.0188(18) 0.0133(19) -0.0107(17) C34 0.030(2) 0.0289(19) 0.058(3) -0.0217(18) 0.017(2) -0.0052(16) C35 0.036(3) 0.0171(17) 0.061(3) -0.0014(16) 0.013(2) -0.0003(15) C36 0.031(2) 0.0177(16) 0.0355(19) -0.0046(14) 0.0087(17) -0.0041(14) C37 0.022(2) 0.0172(15) 0.0186(17) 0.0024(13) 0.0012(14) 0.0018(13) C38 0.027(2) 0.0276(17) 0.034(2) -0.0034(15) 0.0055(17) 0.0004(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 C2 1.215(4) . ? O2 C1 1.449(4) . ? O2 C2 1.355(4) . ? O3 C21 1.209(4) . ? O4 C20 1.446(3) . ? O4 C21 1.348(3) . ? N1 C5 1.391(4) . ? N1 C12 1.439(3) . ? N1 C18 1.379(4) . ? N2 C24 1.397(4) . ? N2 C31 1.440(3) . ? N2 C37 1.373(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.448(4) . ? C3 C4 1.411(4) . ? C3 C18 1.395(4) . ? C4 H4 0.9300 . ? C4 C5 1.378(4) . ? C5 C6 1.466(4) . ? C6 C7 1.390(4) . ? C6 C11 1.405(4) . ? C7 H7 0.9300 . ? C7 C8 1.377(5) . ? C8 H8 0.9300 . ? C8 C9 1.381(4) . ? C9 H9 0.9300 . ? C9 C10 1.386(5) . ? C10 H10 0.9300 . ? C10 C11 1.373(4) . ? C11 H11 0.9300 . ? C12 C13 1.385(4) . ? C12 C17 1.386(4) . ? C13 H13 0.9300 . ? C13 C14 1.384(4) . ? C14 H14 0.9300 . ? C14 C15 1.373(4) . ? C15 H15 0.9300 . ? C15 C16 1.386(4) . ? C16 H16 0.9300 . ? C16 C17 1.388(4) . ? C17 H17 0.9300 . ? C18 C19 1.472(4) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.465(4) . ? C22 C23 1.411(4) . ? C22 C37 1.390(4) . ? C23 H23 0.9300 . ? C23 C24 1.370(4) . ? C24 C25 1.465(4) . ? C25 C26 1.404(4) . ? C25 C30 1.391(4) . ? C26 H26 0.9300 . ? C26 C27 1.374(4) . ? C27 H27 0.9300 . ? C27 C28 1.388(4) . ? C28 H28 0.9300 . ? C28 C29 1.385(4) . ? C29 H29 0.9300 . ? C29 C30 1.385(4) . ? C30 H30 0.9300 . ? C31 C32 1.389(4) . ? C31 C36 1.376(4) . ? C32 H32 0.9300 . ? C32 C33 1.382(4) . ? C33 H33 0.9300 . ? C33 C34 1.374(5) . ? C34 H34 0.9300 . ? C34 C35 1.379(5) . ? C35 H35 0.9300 . ? C35 C36 1.393(4) . ? C36 H36 0.9300 . ? C37 C38 1.472(4) . ? 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 C2 O2 C1 114.9(3) . . ? C21 O4 C20 115.2(3) . . ? C5 N1 C12 125.6(3) . . ? C18 N1 C5 110.4(2) . . ? C18 N1 C12 123.7(3) . . ? C24 N2 C31 124.5(3) . . ? C37 N2 C24 110.1(2) . . ? C37 N2 C31 125.0(3) . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 121.7(3) . . ? O1 C2 C3 126.3(3) . . ? O2 C2 C3 112.0(3) . . ? C4 C3 C2 128.8(3) . . ? C18 C3 C2 122.9(3) . . ? C18 C3 C4 108.3(3) . . ? C3 C4 H4 126.0 . . ? C5 C4 C3 108.0(3) . . ? C5 C4 H4 126.0 . . ? N1 C5 C6 124.0(3) . . ? C4 C5 N1 106.9(3) . . ? C4 C5 C6 129.1(3) . . ? C7 C6 C5 119.9(3) . . ? C7 C6 C11 118.4(3) . . ? C11 C6 C5 121.7(3) . . ? C6 C7 H7 119.6 . . ? C8 C7 C6 120.9(3) . . ? C8 C7 H7 119.6 . . ? C7 C8 H8 119.8 . . ? C7 C8 C9 120.5(3) . . ? C9 C8 H8 119.8 . . ? C8 C9 H9 120.4 . . ? C8 C9 C10 119.2(3) . . ? C10 C9 H9 120.4 . . ? C9 C10 H10 119.6 . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.6 . . ? C6 C11 H11 119.9 . . ? C10 C11 C6 120.2(3) . . ? C10 C11 H11 119.9 . . ? C13 C12 N1 119.9(3) . . ? C13 C12 C17 120.7(3) . . ? C17 C12 N1 119.4(3) . . ? C12 C13 H13 120.4 . . ? C14 C13 C12 119.1(3) . . ? C14 C13 H13 120.4 . . ? C13 C14 H14 119.6 . . ? C15 C14 C13 120.7(3) . . ? C15 C14 H14 119.6 . . ? C14 C15 H15 120.0 . . ? C14 C15 C16 120.0(3) . . ? C16 C15 H15 120.0 . . ? C15 C16 H16 120.0 . . ? C15 C16 C17 120.0(3) . . ? C17 C16 H16 120.0 . . ? C12 C17 C16 119.4(3) . . ? C12 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? N1 C18 C3 106.3(3) . . ? N1 C18 C19 123.0(3) . . ? C3 C18 C19 130.5(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? O4 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 O4 123.1(3) . . ? O3 C21 C22 126.2(3) . . ? O4 C21 C22 110.6(3) . . ? C23 C22 C21 127.6(3) . . ? C37 C22 C21 124.5(3) . . ? C37 C22 C23 107.8(3) . . ? C22 C23 H23 125.8 . . ? C24 C23 C22 108.4(3) . . ? C24 C23 H23 125.8 . . ? N2 C24 C25 123.4(2) . . ? C23 C24 N2 106.8(3) . . ? C23 C24 C25 129.7(3) . . ? C26 C25 C24 121.5(3) . . ? C30 C25 C24 120.2(3) . . ? C30 C25 C26 118.2(3) . . ? C25 C26 H26 119.7 . . ? C27 C26 C25 120.5(3) . . ? C27 C26 H26 119.7 . . ? C26 C27 H27 119.4 . . ? C26 C27 C28 121.1(3) . . ? C28 C27 H27 119.4 . . ? C27 C28 H28 120.7 . . ? C29 C28 C27 118.6(3) . . ? C29 C28 H28 120.7 . . ? C28 C29 H29 119.5 . . ? C28 C29 C30 120.9(3) . . ? C30 C29 H29 119.5 . . ? C25 C30 H30 119.7 . . ? C29 C30 C25 120.6(3) . . ? C29 C30 H30 119.7 . . ? C32 C31 N2 119.5(3) . . ? C36 C31 N2 119.7(3) . . ? C36 C31 C32 120.8(3) . . ? C31 C32 H32 120.5 . . ? C33 C32 C31 119.0(3) . . ? C33 C32 H32 120.5 . . ? C32 C33 H33 119.8 . . ? C34 C33 C32 120.5(3) . . ? C34 C33 H33 119.8 . . ? C33 C34 H34 119.8 . . ? C33 C34 C35 120.5(3) . . ? C35 C34 H34 119.8 . . ? C34 C35 H35 120.2 . . ? C34 C35 C36 119.6(3) . . ? C36 C35 H35 120.2 . . ? C31 C36 C35 119.5(3) . . ? C31 C36 H36 120.2 . . ? C35 C36 H36 120.2 . . ? N2 C37 C22 106.8(3) . . ? N2 C37 C38 122.3(2) . . ? C22 C37 C38 130.7(3) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38B 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 O1 C2 C3 C4 168.8(3) . . . . ? O1 C2 C3 C18 -13.8(5) . . . . ? O2 C2 C3 C4 -11.0(4) . . . . ? O2 C2 C3 C18 166.4(3) . . . . ? O3 C21 C22 C23 -172.7(3) . . . . ? O3 C21 C22 C37 10.7(5) . . . . ? O4 C21 C22 C23 8.7(4) . . . . ? O4 C21 C22 C37 -167.9(3) . . . . ? N1 C5 C6 C7 -136.8(3) . . . . ? N1 C5 C6 C11 43.3(4) . . . . ? N1 C12 C13 C14 179.2(3) . . . . ? N1 C12 C17 C16 -178.0(3) . . . . ? N2 C24 C25 C26 -44.0(4) . . . . ? N2 C24 C25 C30 138.0(3) . . . . ? N2 C31 C32 C33 178.2(3) . . . . ? N2 C31 C36 C35 179.9(3) . . . . ? C1 O2 C2 O1 5.2(4) . . . . ? C1 O2 C2 C3 -174.9(2) . . . . ? C2 C3 C4 C5 177.9(3) . . . . ? C2 C3 C18 N1 -178.6(3) . . . . ? C2 C3 C18 C19 -3.1(5) . . . . ? C3 C4 C5 N1 0.4(3) . . . . ? C3 C4 C5 C6 178.9(3) . . . . ? C4 C3 C18 N1 -0.8(3) . . . . ? C4 C3 C18 C19 174.7(3) . . . . ? C4 C5 C6 C7 44.9(4) . . . . ? C4 C5 C6 C11 -135.1(3) . . . . ? C5 N1 C12 C13 56.4(4) . . . . ? C5 N1 C12 C17 -123.5(3) . . . . ? C5 N1 C18 C3 1.1(3) . . . . ? C5 N1 C18 C19 -174.9(3) . . . . ? C5 C6 C7 C8 178.5(3) . . . . ? C5 C6 C11 C10 -179.0(3) . . . . ? C6 C7 C8 C9 0.9(5) . . . . ? C7 C6 C11 C10 1.1(4) . . . . ? C7 C8 C9 C10 0.4(5) . . . . ? C8 C9 C10 C11 -1.0(5) . . . . ? C9 C10 C11 C6 0.2(4) . . . . ? C11 C6 C7 C8 -1.6(4) . . . . ? C12 N1 C5 C4 -174.7(2) . . . . ? C12 N1 C5 C6 6.7(4) . . . . ? C12 N1 C18 C3 175.0(3) . . . . ? C12 N1 C18 C19 -1.0(4) . . . . ? C12 C13 C14 C15 -0.4(5) . . . . ? C13 C12 C17 C16 2.0(5) . . . . ? C13 C14 C15 C16 0.6(5) . . . . ? C14 C15 C16 C17 0.6(5) . . . . ? C15 C16 C17 C12 -1.9(5) . . . . ? C17 C12 C13 C14 -0.9(5) . . . . ? C18 N1 C5 C4 -0.9(3) . . . . ? C18 N1 C5 C6 -179.6(3) . . . . ? C18 N1 C12 C13 -116.6(3) . . . . ? C18 N1 C12 C17 63.5(4) . . . . ? C18 C3 C4 C5 0.3(3) . . . . ? C20 O4 C21 O3 -2.6(4) . . . . ? C20 O4 C21 C22 176.0(2) . . . . ? C21 C22 C23 C24 -177.4(3) . . . . ? C21 C22 C37 N2 177.3(2) . . . . ? C21 C22 C37 C38 1.3(5) . . . . ? C22 C23 C24 N2 0.4(3) . . . . ? C22 C23 C24 C25 -176.1(3) . . . . ? C23 C22 C37 N2 0.2(3) . . . . ? C23 C22 C37 C38 -175.9(3) . . . . ? C23 C24 C25 C26 132.0(3) . . . . ? C23 C24 C25 C30 -46.0(4) . . . . ? C24 N2 C31 C32 -54.6(4) . . . . ? C24 N2 C31 C36 124.9(3) . . . . ? C24 N2 C37 C22 0.1(3) . . . . ? C24 N2 C37 C38 176.6(3) . . . . ? C24 C25 C26 C27 -178.7(3) . . . . ? C24 C25 C30 C29 179.1(3) . . . . ? C25 C26 C27 C28 0.0(4) . . . . ? C26 C25 C30 C29 1.0(4) . . . . ? C26 C27 C28 C29 0.4(4) . . . . ? C27 C28 C29 C30 -0.1(4) . . . . ? C28 C29 C30 C25 -0.7(5) . . . . ? C30 C25 C26 C27 -0.7(4) . . . . ? C31 N2 C24 C23 173.0(2) . . . . ? C31 N2 C24 C25 -10.2(4) . . . . ? C31 N2 C37 C22 -173.2(2) . . . . ? C31 N2 C37 C38 3.3(4) . . . . ? C31 C32 C33 C34 1.6(5) . . . . ? C32 C31 C36 C35 -0.6(5) . . . . ? C32 C33 C34 C35 0.1(5) . . . . ? C33 C34 C35 C36 -2.0(5) . . . . ? C34 C35 C36 C31 2.3(5) . . . . ? C36 C31 C32 C33 -1.3(5) . . . . ? C37 N2 C24 C23 -0.3(3) . . . . ? C37 N2 C24 C25 176.4(2) . . . . ? C37 N2 C31 C32 117.8(3) . . . . ? C37 N2 C31 C36 -62.7(4) . . . . ? C37 C22 C23 C24 -0.4(3) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 972540'