# 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_2467 _audit_creation_method 'SHELXL-2012 & ZCIF' _chemical_name_systematic ; Organic compound, XXU ; _chemical_name_common ? _chemical_formula_moiety 'C20 H19 N O3' _chemical_formula_sum 'C20 H19 N O3' _chemical_formula_weight 321.36 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4622(11) _cell_length_b 12.7512(13) _cell_length_c 13.6245(14) _cell_angle_alpha 102.7775(16) _cell_angle_beta 103.9647(16) _cell_angle_gamma 102.1013(16) _cell_volume 1652.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9550 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 30.5 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.292 _exptl_crystal_F_000 680 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.09 _exptl_absorpt_coefficient_mu 0.087 _shelx_estimated_absorpt_T_min 0.954 _shelx_estimated_absorpt_T_max 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.947 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'sealed tube' _diffrn_measurement_device_type 'Bruker Smart Apex II diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 20066 _diffrn_reflns_av_unetI/netI 0.0275 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.980 _diffrn_reflns_theta_max 27.500 _diffrn_reflns_theta_full 26.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 7602 _reflns_number_gt 6333 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Apex2 (Bruker, 2010)' _computing_cell_refinement Apex2 _computing_data_reduction 'Apex2, Saint' _computing_structure_solution 'ShelXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'ShelXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material 'Apex2, SHELXL-2012' _refine_special_details ; H atoms were positioned from geometric consideration and refined as riding on the attached atom with orientation of CH3 group optimized. Uiso of H atoms were constrained to be 20% (50% in CH3 groups) larger than Ueqv of the attached atom. Although H atom in NH2 groups were located from difference Fourier map and freely refined including Uiso. Phenyl ring (C14A - C19A) is disordered in two alternative orientations in about 3:2 ratio and was refined with geometry and atomic displacement parameters to be similar using SAME and SIMU instructions. Alternative orientations of the phenyl ring are at 14.7(4) degrees to each other (see _geom_special_details). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+0.9793P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 7602 _refine_ls_number_parameters 497 _refine_ls_number_restraints 192 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0769 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.001 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1A C 0.58838(12) 0.27997(9) 0.65953(9) 0.0184(2) Uani 1 1 d . . . . . C2A C 0.64186(12) 0.39610(9) 0.70245(9) 0.0183(2) Uani 1 1 d . . . . . N2A N 0.58020(12) 0.46574(9) 0.74504(9) 0.0222(2) Uani 1 1 d . . . . . H21A H 0.4929(16) 0.4379(12) 0.7422(11) 0.025(4) Uiso 1 1 d . . . . . H22A H 0.6222(17) 0.5392(14) 0.7706(13) 0.038(4) Uiso 1 1 d . . . . . C3A C 0.78867(12) 0.43711(9) 0.70060(10) 0.0196(2) Uani 1 1 d . . . . . C4A C 0.81745(13) 0.32714(10) 0.64771(11) 0.0229(3) Uani 1 1 d . . . . . H4A1 H 0.8403 0.3320 0.5821 0.028 Uiso 1 1 calc R U . . . H4A2 H 0.8954 0.3136 0.6961 0.028 Uiso 1 1 calc R U . . . C5A C 0.68805(12) 0.23353(9) 0.62294(9) 0.0181(2) Uani 1 1 d . . . . . O5A O 0.67768(9) 0.13554(7) 0.57677(7) 0.02164(18) Uani 1 1 d . . . . . C11A C 0.45261(12) 0.22274(10) 0.65972(9) 0.0199(2) Uani 1 1 d . . . . . O11A O 0.36954(9) 0.27155(7) 0.68072(8) 0.0281(2) Uani 1 1 d . . . . . O12A O 0.42730(9) 0.11052(7) 0.63677(7) 0.02217(19) Uani 1 1 d . . . . . C13A C 0.29396(13) 0.04915(11) 0.63965(11) 0.0263(3) Uani 1 1 d . . . . . H13A H 0.2643 -0.0261 0.5883 0.032 Uiso 1 1 calc R U . A 1 H13B H 0.2252 0.0892 0.6185 0.032 Uiso 1 1 calc R U . A 1 C14A C 0.29995(13) 0.03728(11) 0.74784(11) 0.0266(3) Uani 0.586(12) 1 d D U P B 1 C15A C 0.3173(14) 0.1247(5) 0.8355(5) 0.0338(17) Uani 0.586(12) 1 d D U P B 1 H15A H 0.3303 0.1987 0.8295 0.041 Uiso 0.586(12) 1 calc R U P B 1 C16A C 0.3161(17) 0.1063(6) 0.9317(5) 0.0374(12) Uani 0.586(12) 1 d D U P B 1 H16A H 0.3325 0.1673 0.9919 0.045 Uiso 0.586(12) 1 calc R U P B 1 C17A C 0.2909(7) -0.0019(5) 0.9389(5) 0.0472(12) Uani 0.586(12) 1 d D U P B 1 H17A H 0.2887 -0.0156 1.0043 0.057 Uiso 0.586(12) 1 calc R U P B 1 C18A C 0.2689(8) -0.0900(4) 0.8521(5) 0.0531(12) Uani 0.586(12) 1 d D U P B 1 H18A H 0.2511 -0.1641 0.8581 0.064 Uiso 0.586(12) 1 calc R U P B 1 C19A C 0.2725(7) -0.0723(3) 0.7559(5) 0.0387(11) Uani 0.586(12) 1 d D U P B 1 H19A H 0.2565 -0.1338 0.6961 0.046 Uiso 0.586(12) 1 calc R U P B 1 C14C C 0.29995(13) 0.03728(11) 0.74784(11) 0.0266(3) Uani 0.414(12) 1 d D U P B 2 C15C C 0.3065(18) 0.1306(7) 0.8276(7) 0.0238(15) Uani 0.414(12) 1 d D U P B 2 H15C H 0.3033 0.1990 0.8115 0.029 Uiso 0.414(12) 1 calc R U P B 2 C16C C 0.318(2) 0.1251(9) 0.9294(8) 0.0388(17) Uani 0.414(12) 1 d D U P B 2 H16C H 0.3166 0.1883 0.9812 0.047 Uiso 0.414(12) 1 calc R U P B 2 C17C C 0.3303(10) 0.0288(8) 0.9569(7) 0.0525(17) Uani 0.414(12) 1 d D U P B 2 H17C H 0.3399 0.0261 1.0274 0.063 Uiso 0.414(12) 1 calc R U P B 2 C18C C 0.3287(11) -0.0633(7) 0.8805(6) 0.0541(15) Uani 0.414(12) 1 d D U P B 2 H18C H 0.3358 -0.1304 0.8980 0.065 Uiso 0.414(12) 1 calc R U P B 2 C19C C 0.3169(10) -0.0580(6) 0.7785(6) 0.0426(15) Uani 0.414(12) 1 d D U P B 2 H19C H 0.3203 -0.1209 0.7277 0.051 Uiso 0.414(12) 1 calc R U P B 2 C31A C 0.88178(13) 0.48928(11) 0.81590(10) 0.0259(3) Uani 1 1 d . . . . . H31A H 0.8652 0.4362 0.8567 0.039 Uiso 1 1 calc R U . . . H31B H 0.8611 0.5583 0.8470 0.039 Uiso 1 1 calc R U . . . H31C H 0.9781 0.5064 0.8172 0.039 Uiso 1 1 calc R U . . . C32A C 0.80455(13) 0.52079(10) 0.63591(10) 0.0217(3) Uani 1 1 d . . . . . C33A C 0.93500(15) 0.57003(13) 0.63326(14) 0.0385(4) Uani 1 1 d . . . . . H33A H 1.0115 0.5520 0.6723 0.046 Uiso 1 1 calc R U . . . C34A C 0.95602(17) 0.64506(13) 0.57468(14) 0.0420(4) Uani 1 1 d . . . . . H34A H 1.0461 0.6773 0.5737 0.050 Uiso 1 1 calc R U . . . C35A C 0.84631(17) 0.67269(11) 0.51806(11) 0.0336(3) Uani 1 1 d . . . . . H35A H 0.8604 0.7250 0.4790 0.040 Uiso 1 1 calc R U . . . C36A C 0.71590(16) 0.62370(12) 0.51866(11) 0.0344(3) Uani 1 1 d . . . . . H36A H 0.6397 0.6417 0.4792 0.041 Uiso 1 1 calc R U . . . C37A C 0.69521(14) 0.54783(11) 0.57692(11) 0.0289(3) Uani 1 1 d . . . . . H37A H 0.6047 0.5142 0.5761 0.035 Uiso 1 1 calc R U . . . C1B C 0.61288(12) 0.79137(9) 0.71216(10) 0.0191(2) Uani 1 1 d . . . . . C2B C 0.65808(12) 0.88504(9) 0.67899(10) 0.0194(2) Uani 1 1 d . . . . . N2B N 0.58539(12) 0.91867(9) 0.60565(9) 0.0228(2) Uani 1 1 d . . . . . H21B H 0.4971(16) 0.8806(12) 0.5723(12) 0.026(4) Uiso 1 1 d . . . . . H22B H 0.6173(17) 0.9827(14) 0.5947(13) 0.040(4) Uiso 1 1 d . . . . . C3B C 0.80725(12) 0.94854(10) 0.74027(10) 0.0212(2) Uani 1 1 d . . . . . C4B C 0.85530(13) 0.86388(10) 0.79655(11) 0.0264(3) Uani 1 1 d . . . . . H4B1 H 0.9162 0.8293 0.7629 0.032 Uiso 1 1 calc R U . . . H4B2 H 0.9060 0.9020 0.8719 0.032 Uiso 1 1 calc R U . . . C5B C 0.72598(13) 0.77532(9) 0.78578(10) 0.0197(2) Uani 1 1 d . . . . . O5B O 0.72696(9) 0.70243(7) 0.83236(7) 0.02410(19) Uani 1 1 d . . . . . C11B C 0.47007(13) 0.72650(9) 0.67639(10) 0.0197(2) Uani 1 1 d . . . . . O11B O 0.38073(9) 0.73597(7) 0.60522(7) 0.0266(2) Uani 1 1 d . . . . . O12B O 0.44365(9) 0.65527(7) 0.73377(7) 0.02448(19) Uani 1 1 d . . . . . C13B C 0.30038(13) 0.60056(10) 0.71480(11) 0.0247(3) Uani 1 1 d . . . . . H13C H 0.2621 0.5454 0.6440 0.030 Uiso 1 1 calc R U . . . H13D H 0.2473 0.6563 0.7184 0.030 Uiso 1 1 calc R U . . . C14B C 0.29293(13) 0.54261(10) 0.79922(10) 0.0227(3) Uani 1 1 d . . . . . C15B C 0.36883(15) 0.59643(11) 0.90416(11) 0.0320(3) Uani 1 1 d . . . . . H15B H 0.4281 0.6699 0.9228 0.038 Uiso 1 1 calc R U . . . C16B C 0.35853(17) 0.54360(13) 0.98163(12) 0.0381(3) Uani 1 1 d . . . . . H16B H 0.4114 0.5807 1.0530 0.046 Uiso 1 1 calc R U . . . C17B C 0.27128(16) 0.43664(13) 0.95545(13) 0.0366(3) Uani 1 1 d . . . . . H17B H 0.2639 0.4007 1.0087 0.044 Uiso 1 1 calc R U . . . C18B C 0.19546(15) 0.38293(12) 0.85182(13) 0.0342(3) Uani 1 1 d . . . . . H18B H 0.1351 0.3099 0.8337 0.041 Uiso 1 1 calc R U . . . C19B C 0.20680(14) 0.43509(11) 0.77349(11) 0.0270(3) Uani 1 1 d . . . . . H19B H 0.1554 0.3970 0.7020 0.032 Uiso 1 1 calc R U . . . C31B C 0.89032(14) 0.97605(11) 0.66548(11) 0.0287(3) Uani 1 1 d . . . . . H31D H 0.8569 1.0296 0.6319 0.043 Uiso 1 1 calc R U . . . H31E H 0.8795 0.9073 0.6111 0.043 Uiso 1 1 calc R U . . . H31F H 0.9875 1.0087 0.7059 0.043 Uiso 1 1 calc R U . . . C32B C 0.81653(13) 1.05722(10) 0.82139(10) 0.0212(2) Uani 1 1 d . . . . . C33B C 0.94465(14) 1.11763(11) 0.89415(11) 0.0286(3) Uani 1 1 d . . . . . H33B H 1.0222 1.0906 0.8920 0.034 Uiso 1 1 calc R U . . . C34B C 0.96007(15) 1.21636(11) 0.96946(11) 0.0332(3) Uani 1 1 d . . . . . H34B H 1.0476 1.2560 1.0186 0.040 Uiso 1 1 calc R U . . . C35B C 0.84799(16) 1.25720(11) 0.97315(11) 0.0323(3) Uani 1 1 d . . . . . H35B H 0.8584 1.3251 1.0242 0.039 Uiso 1 1 calc R U . . . C36B C 0.72064(15) 1.19807(11) 0.90173(11) 0.0299(3) Uani 1 1 d . . . . . H36B H 0.6434 1.2255 0.9040 0.036 Uiso 1 1 calc R U . . . C37B C 0.70503(13) 1.09862(10) 0.82655(10) 0.0241(3) Uani 1 1 d . . . . . H37B H 0.6170 1.0587 0.7783 0.029 Uiso 1 1 calc R U . . . 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 C1A 0.0210(6) 0.0162(5) 0.0188(6) 0.0070(4) 0.0061(5) 0.0049(4) C2A 0.0218(6) 0.0181(5) 0.0171(6) 0.0084(5) 0.0056(5) 0.0066(4) N2A 0.0250(6) 0.0168(5) 0.0276(6) 0.0069(4) 0.0112(5) 0.0071(4) C3A 0.0204(6) 0.0153(5) 0.0232(6) 0.0058(5) 0.0068(5) 0.0049(4) C4A 0.0218(6) 0.0165(5) 0.0305(7) 0.0051(5) 0.0096(5) 0.0050(5) C5A 0.0223(6) 0.0170(5) 0.0161(6) 0.0080(4) 0.0047(5) 0.0055(4) O5A 0.0275(5) 0.0145(4) 0.0239(5) 0.0056(3) 0.0091(4) 0.0061(3) C11A 0.0237(6) 0.0186(5) 0.0196(6) 0.0094(5) 0.0068(5) 0.0057(5) O11A 0.0261(5) 0.0244(4) 0.0434(6) 0.0172(4) 0.0173(4) 0.0110(4) O12A 0.0239(4) 0.0163(4) 0.0272(5) 0.0070(3) 0.0114(4) 0.0025(3) C13A 0.0226(6) 0.0221(6) 0.0310(7) 0.0065(5) 0.0094(5) -0.0011(5) C14A 0.0246(6) 0.0266(6) 0.0364(7) 0.0151(6) 0.0167(6) 0.0083(5) C15A 0.037(3) 0.0275(19) 0.038(3) 0.0154(17) 0.0103(19) 0.0060(17) C16A 0.048(2) 0.044(3) 0.0307(18) 0.0166(16) 0.0241(16) 0.014(3) C17A 0.068(3) 0.047(3) 0.047(2) 0.0318(19) 0.034(2) 0.019(2) C18A 0.083(3) 0.0349(18) 0.058(3) 0.0288(17) 0.035(2) 0.018(2) C19A 0.055(3) 0.0288(15) 0.046(2) 0.0198(14) 0.0272(19) 0.0149(15) C14C 0.0246(6) 0.0266(6) 0.0364(7) 0.0151(6) 0.0167(6) 0.0083(5) C15C 0.028(3) 0.029(3) 0.023(2) 0.0140(19) 0.015(2) 0.010(2) C16C 0.043(3) 0.040(3) 0.042(3) 0.022(2) 0.018(2) 0.012(3) C17C 0.070(4) 0.054(4) 0.044(3) 0.028(2) 0.029(3) 0.012(3) C18C 0.078(4) 0.046(3) 0.056(3) 0.036(2) 0.027(3) 0.025(3) C19C 0.058(4) 0.033(2) 0.052(3) 0.019(2) 0.028(2) 0.024(2) C31A 0.0252(7) 0.0237(6) 0.0254(7) 0.0050(5) 0.0039(5) 0.0064(5) C32A 0.0270(6) 0.0161(5) 0.0230(6) 0.0050(5) 0.0096(5) 0.0058(5) C33A 0.0285(7) 0.0405(8) 0.0545(10) 0.0285(8) 0.0143(7) 0.0086(6) C34A 0.0377(9) 0.0394(8) 0.0548(10) 0.0254(8) 0.0203(8) 0.0029(7) C35A 0.0542(9) 0.0229(6) 0.0287(7) 0.0117(6) 0.0189(7) 0.0089(6) C36A 0.0447(9) 0.0365(8) 0.0279(7) 0.0164(6) 0.0110(6) 0.0158(7) C37A 0.0298(7) 0.0315(7) 0.0265(7) 0.0127(6) 0.0084(6) 0.0064(6) C1B 0.0224(6) 0.0151(5) 0.0207(6) 0.0062(4) 0.0066(5) 0.0057(4) C2B 0.0240(6) 0.0152(5) 0.0192(6) 0.0040(4) 0.0074(5) 0.0056(4) N2B 0.0261(6) 0.0164(5) 0.0229(6) 0.0091(4) 0.0024(5) 0.0020(4) C3B 0.0207(6) 0.0174(5) 0.0256(6) 0.0092(5) 0.0055(5) 0.0042(5) C4B 0.0220(6) 0.0214(6) 0.0362(8) 0.0142(5) 0.0044(6) 0.0058(5) C5B 0.0239(6) 0.0151(5) 0.0206(6) 0.0041(4) 0.0074(5) 0.0068(4) O5B 0.0283(5) 0.0181(4) 0.0267(5) 0.0110(4) 0.0051(4) 0.0069(3) C11B 0.0252(6) 0.0144(5) 0.0206(6) 0.0054(4) 0.0079(5) 0.0062(4) O11B 0.0252(5) 0.0249(4) 0.0263(5) 0.0114(4) 0.0017(4) 0.0023(4) O12B 0.0203(4) 0.0244(4) 0.0331(5) 0.0168(4) 0.0089(4) 0.0052(3) C13B 0.0197(6) 0.0242(6) 0.0317(7) 0.0122(5) 0.0084(5) 0.0040(5) C14B 0.0219(6) 0.0226(6) 0.0302(7) 0.0109(5) 0.0135(5) 0.0096(5) C15B 0.0386(8) 0.0261(7) 0.0323(8) 0.0098(6) 0.0122(6) 0.0074(6) C16B 0.0497(9) 0.0418(8) 0.0284(8) 0.0133(7) 0.0149(7) 0.0176(7) C17B 0.0462(9) 0.0419(8) 0.0427(9) 0.0275(7) 0.0281(7) 0.0226(7) C18B 0.0360(8) 0.0278(7) 0.0495(9) 0.0204(7) 0.0223(7) 0.0101(6) C19B 0.0251(7) 0.0249(6) 0.0345(7) 0.0107(6) 0.0133(6) 0.0071(5) C31B 0.0280(7) 0.0256(6) 0.0356(8) 0.0113(6) 0.0139(6) 0.0066(5) C32B 0.0237(6) 0.0172(5) 0.0215(6) 0.0094(5) 0.0053(5) 0.0012(5) C33B 0.0238(7) 0.0258(6) 0.0326(7) 0.0103(6) 0.0041(6) 0.0028(5) C34B 0.0312(7) 0.0255(7) 0.0301(7) 0.0062(6) -0.0017(6) -0.0045(6) C35B 0.0435(8) 0.0214(6) 0.0252(7) 0.0041(5) 0.0053(6) 0.0036(6) C36B 0.0352(8) 0.0272(7) 0.0268(7) 0.0063(5) 0.0074(6) 0.0112(6) C37B 0.0249(6) 0.0228(6) 0.0217(6) 0.0073(5) 0.0034(5) 0.0037(5) _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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 10.1224 (0.0100) x - 2.3431 (0.0670) y - 0.0624 (0.0450) z = 2.8856 (0.0333) * 0.0167 (0.0049) C14A_a * -0.0179 (0.0086) C15A_a * 0.0072 (0.0092) C16A_a * 0.0047 (0.0060) C17A_a * -0.0056 (0.0039) C18A_a * -0.0050 (0.0040) C19A_a -0.0651 (0.0087) C13A Rms deviation of fitted atoms = 0.0110 9.7933 (0.0266) x + 0.8884 (0.0924) y - 1.2795 (0.0610) z = 2.0388 (0.0464) Angle to previous plane (with approximate esd) = 14.709 ( 0.410 ) * -0.0250 (0.0064) C14C_b * 0.0201 (0.0116) C15C_b * -0.0061 (0.0133) C16C_b * -0.0032 (0.0090) C17C_b * -0.0024 (0.0055) C18C_b * 0.0166 (0.0058) C19C_b 0.0652 (0.0116) C13A Rms deviation of fitted atoms = 0.0151 ; 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 C1A C2A 1.3997(16) . ? C1A C5A 1.4373(17) . ? C1A C11A 1.4554(16) . ? C2A N2A 1.3170(16) . ? C2A C3A 1.5234(16) . ? N2A H21A 0.896(15) . ? N2A H22A 0.895(17) . ? C3A C32A 1.5347(16) . ? C3A C31A 1.5449(17) . ? C3A C4A 1.5527(16) . ? C4A C5A 1.5150(16) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A O5A 1.2374(14) . ? C11A O11A 1.2218(15) . ? C11A O12A 1.3485(14) . ? O12A C13A 1.4637(14) . ? C13A C14A 1.5025(19) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A C15A 1.387(5) . ? C14A C19A 1.401(4) . ? C15A C16A 1.383(5) . ? C15A H15A 0.9500 . ? C16A C17A 1.379(5) . ? C16A H16A 0.9500 . ? C17A C18A 1.374(5) . ? C17A H17A 0.9500 . ? C18A C19A 1.386(5) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? C31A H31A 0.9800 . ? C31A H31B 0.9800 . ? C31A H31C 0.9800 . ? C32A C37A 1.3849(18) . ? C32A C33A 1.3902(19) . ? C33A C34A 1.391(2) . ? C33A H33A 0.9500 . ? C34A C35A 1.378(2) . ? C34A H34A 0.9500 . ? C35A C36A 1.379(2) . ? C35A H35A 0.9500 . ? C36A C37A 1.3955(18) . ? C36A H36A 0.9500 . ? C37A H37A 0.9500 . ? C1B C2B 1.3998(16) . ? C1B C5B 1.4380(17) . ? C1B C11B 1.4513(17) . ? C2B N2B 1.3115(16) . ? C2B C3B 1.5266(17) . ? N2B H21B 0.899(16) . ? N2B H22B 0.874(17) . ? C3B C32B 1.5380(17) . ? C3B C31B 1.5409(18) . ? C3B C4B 1.5537(16) . ? C4B C5B 1.5224(17) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B O5B 1.2362(14) . ? C11B O11B 1.2207(15) . ? C11B O12B 1.3511(14) . ? O12B C13B 1.4474(15) . ? C13B C14B 1.5067(17) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C19B 1.3897(17) . ? C14B C15B 1.391(2) . ? C15B C16B 1.385(2) . ? C15B H15B 0.9500 . ? C16B C17B 1.388(2) . ? C16B H16B 0.9500 . ? C17B C18B 1.377(2) . ? C17B H17B 0.9500 . ? C18B C19B 1.3919(19) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? C31B H31D 0.9800 . ? C31B H31E 0.9800 . ? C31B H31F 0.9800 . ? C32B C37B 1.3877(18) . ? C32B C33B 1.4003(18) . ? C33B C34B 1.388(2) . ? C33B H33B 0.9500 . ? C34B C35B 1.386(2) . ? C34B H34B 0.9500 . ? C35B C36B 1.385(2) . ? C35B H35B 0.9500 . ? C36B C37B 1.3935(18) . ? C36B H36B 0.9500 . ? C37B H37B 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 C2A C1A C5A 109.73(10) . . ? C2A C1A C11A 121.15(11) . . ? C5A C1A C11A 129.08(10) . . ? N2A C2A C1A 126.52(11) . . ? N2A C2A C3A 121.14(10) . . ? C1A C2A C3A 112.27(10) . . ? C2A N2A H21A 117.7(9) . . ? C2A N2A H22A 120.5(11) . . ? H21A N2A H22A 121.5(14) . . ? C2A C3A C32A 112.89(10) . . ? C2A C3A C31A 108.05(10) . . ? C32A C3A C31A 111.03(10) . . ? C2A C3A C4A 102.46(9) . . ? C32A C3A C4A 110.64(10) . . ? C31A C3A C4A 111.48(10) . . ? C5A C4A C3A 106.82(10) . . ? C5A C4A H4A1 110.4 . . ? C3A C4A H4A1 110.4 . . ? C5A C4A H4A2 110.4 . . ? C3A C4A H4A2 110.4 . . ? H4A1 C4A H4A2 108.6 . . ? O5A C5A C1A 129.25(11) . . ? O5A C5A C4A 122.06(11) . . ? C1A C5A C4A 108.68(10) . . ? O11A C11A O12A 122.69(11) . . ? O11A C11A C1A 123.36(11) . . ? O12A C11A C1A 113.94(10) . . ? C11A O12A C13A 116.17(10) . . ? O12A C13A C14A 111.53(11) . . ? O12A C13A H13A 109.3 . . ? C14A C13A H13A 109.3 . . ? O12A C13A H13B 109.3 . . ? C14A C13A H13B 109.3 . . ? H13A C13A H13B 108.0 . . ? C15A C14A C19A 118.9(4) . . ? C15A C14A C13A 124.8(3) . . ? C19A C14A C13A 116.0(2) . . ? C16A C15A C14A 121.3(5) . . ? C16A C15A H15A 119.3 . . ? C14A C15A H15A 119.3 . . ? C17A C16A C15A 119.1(5) . . ? C17A C16A H16A 120.4 . . ? C15A C16A H16A 120.4 . . ? C18A C17A C16A 120.4(4) . . ? C18A C17A H17A 119.8 . . ? C16A C17A H17A 119.8 . . ? C17A C18A C19A 121.0(4) . . ? C17A C18A H18A 119.5 . . ? C19A C18A H18A 119.5 . . ? C18A C19A C14A 119.2(4) . . ? C18A C19A H19A 120.4 . . ? C14A C19A H19A 120.4 . . ? C3A C31A H31A 109.5 . . ? C3A C31A H31B 109.5 . . ? H31A C31A H31B 109.5 . . ? C3A C31A H31C 109.5 . . ? H31A C31A H31C 109.5 . . ? H31B C31A H31C 109.5 . . ? C37A C32A C33A 117.69(12) . . ? C37A C32A C3A 123.59(11) . . ? C33A C32A C3A 118.68(12) . . ? C32A C33A C34A 121.49(14) . . ? C32A C33A H33A 119.3 . . ? C34A C33A H33A 119.3 . . ? C35A C34A C33A 120.05(14) . . ? C35A C34A H34A 120.0 . . ? C33A C34A H34A 120.0 . . ? C34A C35A C36A 119.33(13) . . ? C34A C35A H35A 120.3 . . ? C36A C35A H35A 120.3 . . ? C35A C36A C37A 120.41(14) . . ? C35A C36A H36A 119.8 . . ? C37A C36A H36A 119.8 . . ? C32A C37A C36A 121.01(13) . . ? C32A C37A H37A 119.5 . . ? C36A C37A H37A 119.5 . . ? C2B C1B C5B 109.90(10) . . ? C2B C1B C11B 122.10(11) . . ? C5B C1B C11B 127.97(10) . . ? N2B C2B C1B 126.42(12) . . ? N2B C2B C3B 121.82(10) . . ? C1B C2B C3B 111.76(10) . . ? C2B N2B H21B 119.7(9) . . ? C2B N2B H22B 121.2(11) . . ? H21B N2B H22B 118.5(14) . . ? C2B C3B C32B 110.88(10) . . ? C2B C3B C31B 111.28(11) . . ? C32B C3B C31B 109.64(10) . . ? C2B C3B C4B 101.93(9) . . ? C32B C3B C4B 110.76(10) . . ? C31B C3B C4B 112.16(11) . . ? C5B C4B C3B 106.30(10) . . ? C5B C4B H4B1 110.5 . . ? C3B C4B H4B1 110.5 . . ? C5B C4B H4B2 110.5 . . ? C3B C4B H4B2 110.5 . . ? H4B1 C4B H4B2 108.7 . . ? O5B C5B C1B 129.10(11) . . ? O5B C5B C4B 122.73(11) . . ? C1B C5B C4B 108.14(10) . . ? O11B C11B O12B 122.43(11) . . ? O11B C11B C1B 125.19(11) . . ? O12B C11B C1B 112.34(10) . . ? C11B O12B C13B 115.91(10) . . ? O12B C13B C14B 107.01(10) . . ? O12B C13B H13C 110.3 . . ? C14B C13B H13C 110.3 . . ? O12B C13B H13D 110.3 . . ? C14B C13B H13D 110.3 . . ? H13C C13B H13D 108.6 . . ? C19B C14B C15B 118.93(12) . . ? C19B C14B C13B 120.19(12) . . ? C15B C14B C13B 120.86(11) . . ? C16B C15B C14B 120.45(13) . . ? C16B C15B H15B 119.8 . . ? C14B C15B H15B 119.8 . . ? C15B C16B C17B 120.28(15) . . ? C15B C16B H16B 119.9 . . ? C17B C16B H16B 119.9 . . ? C18B C17B C16B 119.63(13) . . ? C18B C17B H17B 120.2 . . ? C16B C17B H17B 120.2 . . ? C17B C18B C19B 120.31(13) . . ? C17B C18B H18B 119.8 . . ? C19B C18B H18B 119.8 . . ? C14B C19B C18B 120.40(14) . . ? C14B C19B H19B 119.8 . . ? C18B C19B H19B 119.8 . . ? C3B C31B H31D 109.5 . . ? C3B C31B H31E 109.5 . . ? H31D C31B H31E 109.5 . . ? C3B C31B H31F 109.5 . . ? H31D C31B H31F 109.5 . . ? H31E C31B H31F 109.5 . . ? C37B C32B C33B 118.21(12) . . ? C37B C32B C3B 123.66(11) . . ? C33B C32B C3B 118.13(12) . . ? C34B C33B C32B 121.03(13) . . ? C34B C33B H33B 119.5 . . ? C32B C33B H33B 119.5 . . ? C35B C34B C33B 120.13(13) . . ? C35B C34B H34B 119.9 . . ? C33B C34B H34B 119.9 . . ? C36B C35B C34B 119.38(13) . . ? C36B C35B H35B 120.3 . . ? C34B C35B H35B 120.3 . . ? C35B C36B C37B 120.47(13) . . ? C35B C36B H36B 119.8 . . ? C37B C36B H36B 119.8 . . ? C32B C37B C36B 120.77(12) . . ? C32B C37B H37B 119.6 . . ? C36B C37B H37B 119.6 . . ? 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 C5A C1A C2A N2A -178.80(11) . . . . ? C11A C1A C2A N2A -0.94(19) . . . . ? C5A C1A C2A C3A -1.75(14) . . . . ? C11A C1A C2A C3A 176.11(10) . . . . ? N2A C2A C3A C32A -62.96(15) . . . . ? C1A C2A C3A C32A 119.81(11) . . . . ? N2A C2A C3A C31A 60.21(14) . . . . ? C1A C2A C3A C31A -117.02(11) . . . . ? N2A C2A C3A C4A 178.02(11) . . . . ? C1A C2A C3A C4A 0.79(13) . . . . ? C2A C3A C4A C5A 0.40(12) . . . . ? C32A C3A C4A C5A -120.18(11) . . . . ? C31A C3A C4A C5A 115.74(11) . . . . ? C2A C1A C5A O5A -176.78(12) . . . . ? C11A C1A C5A O5A 5.6(2) . . . . ? C2A C1A C5A C4A 1.96(14) . . . . ? C11A C1A C5A C4A -175.68(12) . . . . ? C3A C4A C5A O5A 177.43(11) . . . . ? C3A C4A C5A C1A -1.43(13) . . . . ? C2A C1A C11A O11A 12.01(19) . . . . ? C5A C1A C11A O11A -170.59(12) . . . . ? C2A C1A C11A O12A -166.63(11) . . . . ? C5A C1A C11A O12A 10.78(18) . . . . ? O11A C11A O12A C13A -0.79(17) . . . . ? C1A C11A O12A C13A 177.86(10) . . . . ? C11A O12A C13A C14A -89.20(13) . . . . ? O12A C13A C14A C15A 69.2(7) . . . . ? O12A C13A C14A C19A -117.2(3) . . . . ? C19A C14A C15A C16A 3.9(15) . . . . ? C13A C14A C15A C16A 177.3(10) . . . . ? C14A C15A C16A C17A -3(2) . . . . ? C15A C16A C17A C18A 0.8(17) . . . . ? C16A C17A C18A C19A 0.4(10) . . . . ? C17A C18A C19A C14A 0.5(7) . . . . ? C15A C14A C19A C18A -2.6(8) . . . . ? C13A C14A C19A C18A -176.6(3) . . . . ? C2A C3A C32A C37A -6.00(17) . . . . ? C31A C3A C32A C37A -127.51(13) . . . . ? C4A C3A C32A C37A 108.15(14) . . . . ? C2A C3A C32A C33A 176.06(12) . . . . ? C31A C3A C32A C33A 54.55(16) . . . . ? C4A C3A C32A C33A -69.79(15) . . . . ? C37A C32A C33A C34A 0.8(2) . . . . ? C3A C32A C33A C34A 178.89(14) . . . . ? C32A C33A C34A C35A 0.4(3) . . . . ? C33A C34A C35A C36A -1.2(2) . . . . ? C34A C35A C36A C37A 0.7(2) . . . . ? C33A C32A C37A C36A -1.3(2) . . . . ? C3A C32A C37A C36A -179.27(12) . . . . ? C35A C36A C37A C32A 0.6(2) . . . . ? C5B C1B C2B N2B 173.85(12) . . . . ? C11B C1B C2B N2B -8.0(2) . . . . ? C5B C1B C2B C3B -6.86(14) . . . . ? C11B C1B C2B C3B 171.32(11) . . . . ? N2B C2B C3B C32B 74.24(15) . . . . ? C1B C2B C3B C32B -105.09(11) . . . . ? N2B C2B C3B C31B -48.09(16) . . . . ? C1B C2B C3B C31B 132.59(11) . . . . ? N2B C2B C3B C4B -167.83(12) . . . . ? C1B C2B C3B C4B 12.84(14) . . . . ? C2B C3B C4B C5B -13.58(13) . . . . ? C32B C3B C4B C5B 104.44(12) . . . . ? C31B C3B C4B C5B -132.70(11) . . . . ? C2B C1B C5B O5B 179.74(12) . . . . ? C11B C1B C5B O5B 1.7(2) . . . . ? C2B C1B C5B C4B -2.56(14) . . . . ? C11B C1B C5B C4B 179.38(12) . . . . ? C3B C4B C5B O5B -171.56(11) . . . . ? C3B C4B C5B C1B 10.56(14) . . . . ? C2B C1B C11B O11B 10.62(19) . . . . ? C5B C1B C11B O11B -171.54(12) . . . . ? C2B C1B C11B O12B -167.03(11) . . . . ? C5B C1B C11B O12B 10.81(18) . . . . ? O11B C11B O12B C13B -7.31(17) . . . . ? C1B C11B O12B C13B 170.42(10) . . . . ? C11B O12B C13B C14B -169.96(10) . . . . ? O12B C13B C14B C19B -137.39(12) . . . . ? O12B C13B C14B C15B 44.33(16) . . . . ? C19B C14B C15B C16B 0.0(2) . . . . ? C13B C14B C15B C16B 178.27(13) . . . . ? C14B C15B C16B C17B -0.6(2) . . . . ? C15B C16B C17B C18B 0.4(2) . . . . ? C16B C17B C18B C19B 0.5(2) . . . . ? C15B C14B C19B C18B 0.9(2) . . . . ? C13B C14B C19B C18B -177.44(12) . . . . ? C17B C18B C19B C14B -1.1(2) . . . . ? C2B C3B C32B C37B -8.58(16) . . . . ? C31B C3B C32B C37B 114.70(13) . . . . ? C4B C3B C32B C37B -120.99(13) . . . . ? C2B C3B C32B C33B 171.34(11) . . . . ? C31B C3B C32B C33B -65.38(14) . . . . ? C4B C3B C32B C33B 58.93(14) . . . . ? C37B C32B C33B C34B -0.06(19) . . . . ? C3B C32B C33B C34B -179.98(12) . . . . ? C32B C33B C34B C35B -0.5(2) . . . . ? C33B C34B C35B C36B 0.6(2) . . . . ? C34B C35B C36B C37B -0.2(2) . . . . ? C33B C32B C37B C36B 0.45(18) . . . . ? C3B C32B C37B C36B -179.63(12) . . . . ? C35B C36B C37B C32B -0.3(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2B H21B O5A 0.899(16) 2.319(15) 3.0612(14) 139.9(12) 2_666 N2B H21B O11B 0.899(16) 2.184(15) 2.8121(14) 126.4(12) . N2A H21A O11A 0.896(15) 2.101(15) 2.7525(15) 128.9(12) . N2B H22B O5A 0.874(17) 2.006(17) 2.8775(13) 174.2(16) 1_565 N2A H22A O5B 0.895(17) 2.016(17) 2.9101(14) 176.6(15) . _refine_diff_density_max 0.336 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.040 _diffrn_radiation_monochromator graphite _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 0.0289316 _diffrn_orient_matrix_UB_12 0.0662905 _diffrn_orient_matrix_UB_13 0.0636534 _diffrn_orient_matrix_UB_21 0.0977927 _diffrn_orient_matrix_UB_22 -0.0007633 _diffrn_orient_matrix_UB_23 0.0110577 _diffrn_orient_matrix_UB_31 0.0106055 _diffrn_orient_matrix_UB_32 0.0511165 _diffrn_orient_matrix_UB_33 -0.0453587 _diffrn_measurement_specimen_support 'MiTeGen loop' _diffrn_detector 'CCD area detector' _iucr_refine_instructions_details 'Available on request' _database_code_depnum_ccdc_archive 'CCDC 965494'