Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Anders Hallberg' _publ_contact_author_address ; Department of medicinal chemistry Organic pharmaceutical chemistry BMC, Box 574 Uppsala SE-75123 SWEDEN ; _publ_contact_author_email ANDERS.HALLBERG@ORGFARM.UU.SE _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; September 10, 2005 Dear Sir/Madam, Please consider the CIF submission for publication in This CIF file has passed the CHECKCIF routines and gives a satisfactory PRINTCIF file. ; _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _publ_section_title ; Variations of the P2 group in HIV-1 protease inhibitors containing a tertiary alcohol in the transition-state mimicking scaffold ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; Crystals suitable for X-ray structure analysis were obtained by slow evaporation from an EtOH/dioxane (1 : 1) solution at temperature 273-275 K. ; _publ_section_exptl_refinement ; H-atom parameters constrained ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Beurskens, P.T., Beurskens, G., Bosman, W.P., de Gelder, R. S. Garc\'ia-Granda, S., Gould, R.O. & Smits, J.M.M. (1996). The DIRDIF96 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. Waasmaier, D. & Kirfel, A. (1995). Acta Cryst. A51, 416-431. ; _publ_section_figure_captions ; ; _publ_section_table_legends ; ; _publ_section_acknowledgements ; ; loop_ _publ_author_name 'A. Hallberg' 'Jenny Ekegren' 'Johan Gising' 'Mats Larhed' 'Bertil Samuelsson' 'Hans Wallberg' data_I _database_code_depnum_ccdc_archive 'CCDC 607406' _audit_creation_date 'October 24, 2005' _audit_creation_method maXus # start Validation Reply Form _vrf_PLAT220_I ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.49 Ratio RESPONSE: There are large thermal motion for ethanol molecule. ; _vrf_PLAT222_I ; PROBLEM: Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.27 Ratio RESPONSE: There are large thermal motion for ethanol molecule. ; _vrf_PLAT242_I ; PROBLEM: Check Low Ueq as Compared to Neighbors for O15 RESPONSE: There is an intermolecular hydrogen bond at O15 ; _vrf_PLAT331_I ; PROBLEM: Small Average Phenyl C-C Dist. C25 -C30 1.36 Ang. RESPONSE: There is large e.s.d. for C25-C30 bond length. ; _vrf_PLAT360_I ; PROBLEM: Short C(sp3)-C(sp3) Bond C46 - C47 ... 1.31 Ang. RESPONSE: There is large e.s.d. for C46-C47 bond length. ; # end Validation Reply Form _chemical_compound_source 'synthesised by authors' _chemical_absolute_configuration rmad _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _cell_measurement_temperature 293(2) _refine_ls_hydrogen_treatment constr # Submission details _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _computing_data_collection 'KappaCCD (Nonius, 1999)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _chemical_name_common ; ((1S)-1-(N'-(4-Bromo-benzyl)-N'-((2S)-2-((1S)-2,2-dimethyl-1- methylcarbamoyl-propylcarbamoyl)-2-hydroxy-3-phenyl-propyl) - hydrazinocarbonyl)-2,2-dimethyl-propyl)-carbamic acid methyl ester ethanol solvate ; _chemical_formula_moiety 'C34 H52 Br N5 O7 ' _chemical_formula_sum 'C34 H52 Br N5 O7' _chemical_formula_weight 722.72 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.6340(3) _cell_length_b 12.1440(4) _cell_length_c 15.9560(8) _cell_angle_alpha 90.00 _cell_angle_beta 108.1020(14) _cell_angle_gamma 90.00 _cell_volume 1958.56(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 1.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.711 _exptl_absorpt_correction_T_max 0.936 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8473 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0917 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 27.40 _reflns_number_total 8463 _reflns_number_gt 4316 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0875P)^2^+1.6011P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _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 0.006(9) _refine_ls_number_reflns 8463 _refine_ls_number_parameters 408 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1755 _refine_ls_R_factor_gt 0.0830 _refine_ls_wR_factor_ref 0.2307 _refine_ls_wR_factor_gt 0.1804 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.064 _refine_ls_shift/su_mean 0.007 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1847(12) 1.0929(8) 1.4436(6) 0.131(4) Uani 1 d . . . N2 N 0.2227(7) 1.0039(5) 1.3955(4) 0.089(2) Uani 1 d . . . C3 C 0.1974(7) 1.0108(5) 1.3081(5) 0.0677(18) Uani 1 d . . . C4 C 0.2437(6) 0.9133(5) 1.2645(4) 0.0627(16) Uani 1 d . . . N5 N 0.1359(5) 0.8926(4) 1.1812(3) 0.0598(13) Uani 1 d . . . C6 C 0.0790(6) 0.7940(5) 1.1595(4) 0.0519(14) Uani 1 d . . . C7 C -0.0516(6) 0.7963(4) 1.0843(4) 0.0505(13) Uani 1 d . . . C8 C -0.0514(6) 0.7154(4) 1.0121(4) 0.0530(14) Uani 1 d . . . N9 N 0.0391(5) 0.7528(4) 0.9647(3) 0.0505(11) Uani 1 d . . . N10 N -0.0235(5) 0.7681(4) 0.8734(3) 0.0553(12) Uani 1 d . . . C11 C -0.0542(6) 0.8717(5) 0.8424(4) 0.0528(14) Uani 1 d . . . C12 C -0.1145(7) 0.8841(5) 0.7431(4) 0.0642(17) Uani 1 d . . . N13 N -0.2058(6) 0.9752(4) 0.7283(3) 0.0683(15) Uani 1 d . . . C14 C -0.3316(9) 0.9677(7) 0.6806(6) 0.094(2) Uani 1 d . . . O15 O -0.3959(7) 1.0633(6) 0.6841(5) 0.128(3) Uani 1 d . . . C16 C -0.5346(13) 1.0628(13) 0.6436(12) 0.228(10) Uani 1 d . . . O17 O 0.1372(5) 1.0891(4) 1.2640(3) 0.0818(14) Uani 1 d . . . C18 C 0.3772(7) 0.9346(7) 1.2497(5) 0.082(2) Uani 1 d . . . C19 C 0.3726(10) 1.0317(8) 1.1889(7) 0.113(3) Uani 1 d . . . C20 C 0.4150(9) 0.8322(8) 1.2076(7) 0.103(3) Uani 1 d . . . C21 C 0.4817(9) 0.9537(13) 1.3396(6) 0.142(4) Uani 1 d . . . O22 O 0.1217(4) 0.7081(3) 1.1986(3) 0.0648(11) Uani 1 d . . . O23 O -0.0777(4) 0.9059(3) 1.0491(2) 0.0541(9) Uani 1 d . . . C24 C -0.1634(7) 0.7668(5) 1.1223(4) 0.0588(15) Uani 1 d . . . C25 C -0.1690(7) 0.8404(5) 1.1990(4) 0.0618(16) Uani 1 d . . . C26 C -0.1129(11) 0.8109(8) 1.2826(6) 0.114(3) Uani 1 d . . . C27 C -0.1125(14) 0.8826(11) 1.3528(6) 0.146(5) Uani 1 d . . . C28 C -0.1671(11) 0.9829(9) 1.3330(8) 0.118(4) Uani 1 d . . . C29 C -0.2240(10) 1.0137(8) 1.2502(8) 0.101(3) Uani 1 d . . . C30 C -0.2231(7) 0.9445(7) 1.1841(5) 0.0807(19) Uani 1 d . . . C31 C 0.1613(7) 0.6907(5) 0.9807(5) 0.0673(17) Uani 1 d . . . C32 C 0.2700(7) 0.7550(6) 0.9597(4) 0.0636(16) Uani 1 d . . . C33 C 0.3728(8) 0.6995(6) 0.9437(5) 0.081(2) Uani 1 d . . . C34 C 0.4744(8) 0.7548(8) 0.9229(6) 0.095(3) Uani 1 d . . . C35 C 0.4722(7) 0.8680(8) 0.9205(5) 0.082(2) Uani 1 d . . . C36 C 0.3726(7) 0.9242(7) 0.9383(5) 0.0777(19) Uani 1 d . . . C37 C 0.2737(7) 0.8677(6) 0.9599(5) 0.0706(18) Uani 1 d . . . Br38 Br 0.60615(10) 0.9426(1) 0.88943(8) 0.1342(5) Uani 1 d . . . O39 O -0.0350(4) 0.9532(3) 0.8906(3) 0.0617(10) Uani 1 d . . . C40 C -0.0085(8) 0.8990(6) 0.6947(4) 0.0734(19) Uani 1 d . . . C41 C 0.0680(10) 1.0038(6) 0.7246(6) 0.096(3) Uani 1 d . . . C42 C -0.0816(10) 0.9063(8) 0.5942(5) 0.109(3) Uani 1 d . . . C43 C 0.0857(9) 0.7999(7) 0.7119(5) 0.086(2) Uani 1 d . . . O44 O -0.3851(6) 0.8867(5) 0.6393(5) 0.122(2) Uani 1 d . . . O45 O -0.6218(8) 0.8361(6) 0.5117(5) 0.085(2) Uiso 1 d . . . C46 C -0.6698(16) 0.7341(13) 0.5362(10) 0.118(5) Uiso 1 d . . . C47 C -0.785(2) 0.7057(17) 0.4823(13) 0.136(8) Uiso 1 d . . . H1A H 0.2096 1.0775 1.5053 0.157 Uiso 1 d R . . H1B H 0.0910 1.1052 1.4211 0.157 Uiso 1 d R . . H1C H 0.2286 1.1619 1.4359 0.157 Uiso 1 d R . . H2 H 0.2996 0.9509 1.4280 0.107 Uiso 1 d R . . H4 H 0.2569 0.8503 1.3037 0.075 Uiso 1 d R . . H5 H 0.0948 0.9374 1.1246 0.072 Uiso 1 d R . . H8A H -0.1396 0.7097 0.9705 0.064 Uiso 1 d R . . H8B H -0.0239 0.6437 1.0363 0.064 Uiso 1 d R . . H10 H -0.0430 0.7054 0.8349 0.066 Uiso 1 d R . . H12 H -0.1654 0.8181 0.7214 0.077 Uiso 1 d R . . H13 H -0.1972 1.0395 0.7556 0.082 Uiso 1 d R . . H16A H -0.5718 1.1343 0.6494 0.273 Uiso 1 d R . . H16B H -0.5780 1.0085 0.6696 0.273 Uiso 1 d R . . H16C H -0.5560 1.0466 0.5813 0.273 Uiso 1 d R . . H19A H 0.4552 1.0459 1.1815 0.135 Uiso 1 d R . . H19B H 0.3473 1.0998 1.2166 0.135 Uiso 1 d R . . H19C H 0.3049 1.0232 1.1334 0.135 Uiso 1 d R . . H20A H 0.4978 0.8428 1.1966 0.124 Uiso 1 d R . . H20B H 0.3477 0.8151 1.1526 0.124 Uiso 1 d R . . H20C H 0.4229 0.7699 1.2469 0.124 Uiso 1 d R . . H21A H 0.5675 0.9681 1.3356 0.170 Uiso 1 d R . . H21B H 0.4879 0.8892 1.3782 0.170 Uiso 1 d R . . H21C H 0.4574 1.0158 1.3717 0.170 Uiso 1 d R . . H23 H -0.0750 0.9311 0.9914 0.065 Uiso 1 d R . . H24A H -0.2482 0.7737 1.0761 0.071 Uiso 1 d R . . H24B H -0.1544 0.6918 1.1429 0.071 Uiso 1 d R . . H26 H -0.0705 0.7387 1.2965 0.137 Uiso 1 d R . . H27 H -0.0717 0.8606 1.4143 0.176 Uiso 1 d R . . H28 H -0.1626 1.0308 1.3812 0.142 Uiso 1 d R . . H29 H -0.2677 1.0853 1.2371 0.121 Uiso 1 d R . . H30 H -0.2628 0.9686 1.1239 0.097 Uiso 1 d R . . H31A H 0.1935 0.6696 1.0428 0.081 Uiso 1 d R . . H31B H 0.1449 0.6241 0.9461 0.081 Uiso 1 d R . . H33 H 0.3744 0.6201 0.9466 0.097 Uiso 1 d R . . H34 H 0.5449 0.7146 0.9123 0.114 Uiso 1 d R . . H36 H 0.3736 1.0028 0.9384 0.093 Uiso 1 d R . . H37 H 0.2047 0.9091 0.9738 0.085 Uiso 1 d R . . H41A H 0.1336 1.0146 0.6957 0.116 Uiso 1 d R . . H41B H 0.1102 1.0032 0.7876 0.116 Uiso 1 d R . . H41C H 0.0069 1.0658 0.7106 0.116 Uiso 1 d R . . H42A H -0.1292 0.8394 0.5728 0.130 Uiso 1 d R . . H42B H -0.0181 0.9179 0.5623 0.130 Uiso 1 d R . . H42C H -0.1426 0.9671 0.5816 0.130 Uiso 1 d R . . H43A H 0.0340 0.7330 0.6919 0.103 Uiso 1 d R . . H43B H 0.1308 0.7929 0.7737 0.103 Uiso 1 d R . . H43C H 0.1478 0.8074 0.6802 0.103 Uiso 1 d R . . H45 H -0.5340 0.8513 0.5536 0.162 Uiso 1 d R . . H46A H -0.6064 0.6762 0.5374 0.202 Uiso 1 calc R . . H46B H -0.6765 0.7412 0.5952 0.202 Uiso 1 calc R . . H47A H -0.8249 0.6401 0.4963 0.271 Uiso 1 d R . . H47B H -0.7870 0.7017 0.4212 0.271 Uiso 1 d R . . H47C H -0.8529 0.7666 0.4815 0.271 Uiso 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.166(10) 0.109(7) 0.086(6) -0.018(5) -0.008(6) 0.044(7) N2 0.122(6) 0.073(4) 0.052(4) -0.010(3) -0.003(4) 0.016(3) C3 0.070(4) 0.052(4) 0.063(5) 0.007(3) -0.006(3) -0.002(3) C4 0.068(4) 0.052(3) 0.056(4) 0.014(3) 0.003(3) -0.008(3) N5 0.066(3) 0.057(3) 0.046(3) 0.006(2) 0.001(2) -0.007(2) C6 0.059(4) 0.044(3) 0.050(3) 0.003(2) 0.014(3) -0.005(3) C7 0.057(3) 0.044(3) 0.047(3) 0.002(2) 0.010(3) 0.005(2) C8 0.064(4) 0.038(3) 0.055(4) -0.003(2) 0.015(3) -0.006(2) N9 0.063(3) 0.044(2) 0.042(3) -0.0012(19) 0.013(2) 0.002(2) N10 0.083(4) 0.037(3) 0.046(3) -0.0006(19) 0.019(3) -0.004(2) C11 0.065(4) 0.043(3) 0.051(4) 0.002(3) 0.018(3) -0.005(2) C12 0.089(5) 0.045(3) 0.052(4) -0.005(3) 0.012(3) -0.006(3) N13 0.092(4) 0.053(3) 0.049(3) -0.002(2) 0.007(3) 0.002(3) C14 0.094(6) 0.083(6) 0.076(5) -0.010(4) -0.016(5) 0.002(5) O15 0.106(5) 0.102(4) 0.129(5) -0.033(4) -0.032(4) 0.036(4) C16 0.114(10) 0.192(14) 0.276(19) -0.105(14) -0.088(12) 0.052(10) O17 0.097(4) 0.055(3) 0.073(3) 0.008(2) -0.005(3) 0.003(2) C18 0.062(4) 0.085(5) 0.087(5) 0.001(4) 0.007(4) -0.011(4) C19 0.101(7) 0.103(6) 0.136(9) 0.027(6) 0.038(6) -0.027(5) C20 0.068(5) 0.121(7) 0.118(7) 0.026(6) 0.025(5) 0.011(5) C21 0.077(6) 0.232(13) 0.092(6) 0.001(8) -0.009(5) -0.063(8) O22 0.071(3) 0.048(2) 0.064(3) 0.010(2) 0.005(2) 0.0019(19) O23 0.064(2) 0.049(2) 0.048(2) 0.0072(16) 0.0150(19) 0.0060(18) C24 0.070(4) 0.056(3) 0.052(4) 0.003(3) 0.021(3) -0.006(3) C25 0.065(4) 0.064(4) 0.059(4) 0.000(3) 0.022(3) 0.005(3) C26 0.175(10) 0.108(6) 0.065(6) 0.005(5) 0.046(6) 0.057(7) C27 0.190(12) 0.183(11) 0.058(5) -0.008(6) 0.026(6) 0.079(10) C28 0.109(7) 0.133(9) 0.113(8) -0.058(7) 0.033(6) 0.017(6) C29 0.108(7) 0.088(6) 0.130(9) -0.021(6) 0.071(7) -0.008(5) C30 0.091(5) 0.083(5) 0.083(5) 0.009(4) 0.048(4) 0.012(4) C31 0.074(4) 0.058(4) 0.067(4) 0.002(3) 0.018(4) 0.014(3) C32 0.064(4) 0.063(4) 0.065(4) -0.009(3) 0.021(3) 0.004(3) C33 0.076(5) 0.070(4) 0.090(6) -0.022(4) 0.016(4) 0.001(4) C34 0.061(5) 0.115(7) 0.111(7) -0.038(5) 0.031(5) -0.001(4) C35 0.056(4) 0.119(7) 0.071(5) -0.015(4) 0.021(4) -0.007(4) C36 0.066(4) 0.083(5) 0.083(5) -0.002(4) 0.021(4) -0.004(4) C37 0.059(4) 0.070(4) 0.081(5) -0.004(3) 0.020(4) 0.002(3) Br38 0.0888(6) 0.1847(12) 0.1419(9) -0.0296(8) 0.0543(6) -0.0474(7) O39 0.089(3) 0.041(2) 0.055(2) -0.0015(19) 0.022(2) 0.006(2) C40 0.115(6) 0.065(4) 0.051(4) 0.000(3) 0.041(4) 0.001(4) C41 0.133(8) 0.069(5) 0.111(7) -0.011(4) 0.074(6) -0.024(4) C42 0.166(9) 0.104(6) 0.059(5) 0.015(4) 0.039(5) 0.005(6) C43 0.113(6) 0.080(5) 0.082(5) -0.005(4) 0.056(5) 0.005(4) O44 0.101(5) 0.097(4) 0.124(5) -0.035(4) -0.029(4) 0.000(3) _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 Br38 C35 1.880(8) . ? O39 C11 1.231(7) . ? N13 C14 1.321(10) . ? N13 C12 1.442(8) . ? N13 H13 0.8848 . ? N9 N10 1.413(6) . ? N9 C31 1.455(8) . ? N9 C8 1.469(7) . ? O23 C7 1.438(6) . ? O23 H23 0.9794 . ? O17 C3 1.236(7) . ? C7 C8 1.515(7) . ? C7 C6 1.528(8) . ? C7 C24 1.535(9) . ? O22 C6 1.228(6) . ? N10 C11 1.353(7) . ? N10 H10 0.9599 . ? N5 C6 1.338(7) . ? N5 C4 1.482(8) . ? N5 H5 1.0286 . ? C41 C40 1.506(10) . ? C41 H41A 0.9572 . ? C41 H41B 0.9658 . ? C41 H41C 0.9742 . ? C37 C32 1.369(9) . ? C37 C36 1.386(10) . ? C37 H37 0.9701 . ? C12 C11 1.521(8) . ? C12 C40 1.563(10) . ? C12 H12 0.9689 . ? C30 C29 1.351(11) . ? C30 C25 1.378(10) . ? C30 H30 0.9664 . ? C40 C43 1.535(11) . ? C40 C42 1.551(10) . ? C25 C26 1.329(10) . ? C25 C24 1.532(9) . ? C32 C33 1.374(10) . ? C32 C31 1.516(9) . ? C4 C3 1.530(9) . ? C4 C18 1.531(10) . ? C4 H4 0.9714 . ? C24 H24A 0.9746 . ? C24 H24B 0.9620 . ? N2 C3 1.339(9) . ? N2 C1 1.454(11) . ? N2 H2 1.0429 . ? C8 H8A 0.9682 . ? C8 H8B 0.9613 . ? C36 C35 1.362(10) . ? C36 H36 0.9538 . ? C33 C34 1.397(12) . ? C33 H33 0.9646 . ? C31 H31A 0.9766 . ? C31 H31B 0.9639 . ? C19 C18 1.518(12) . ? C19 H19A 0.9373 . ? C19 H19B 1.0123 . ? C19 H19C 0.9576 . ? O15 C14 1.357(10) . ? O15 C16 1.415(13) . ? C43 H43A 0.9784 . ? C43 H43B 0.9565 . ? C43 H43C 0.9528 . ? C35 C34 1.375(12) . ? C14 O44 1.222(9) . ? C34 H34 0.9539 . ? C18 C20 1.526(13) . ? C18 C21 1.536(11) . ? C1 H1A 0.9563 . ? C1 H1B 0.9603 . ? C1 H1C 0.9855 . ? C29 C28 1.324(14) . ? C29 H29 0.9772 . ? C42 H42A 0.9622 . ? C42 H42B 0.9750 . ? C42 H42C 0.9621 . ? C26 C27 1.418(13) . ? C26 H26 0.9795 . ? C28 C27 1.344(15) . ? C28 H28 0.9539 . ? C21 H21A 0.9513 . ? C21 H21B 0.9859 . ? C21 H21C 0.9890 . ? C27 H27 0.9783 . ? C20 H20A 0.9574 . ? C20 H20B 0.9674 . ? C20 H20C 0.9700 . ? C16 H16A 0.9711 . ? C16 H16B 0.9693 . ? C16 H16C 0.9678 . ? O45 C46 1.439(16) . ? O45 H45 0.9823 . ? C46 C47 1.31(2) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 H47A 0.9603 . ? C47 H47B 0.9705 . ? C47 H47C 1.0308 . ? 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 C14 N13 C12 123.5(6) . . ? C14 N13 H13 106.0 . . ? C12 N13 H13 129.4 . . ? N10 N9 C31 111.0(4) . . ? N10 N9 C8 113.4(4) . . ? C31 N9 C8 116.2(5) . . ? C7 O23 H23 126.8 . . ? O23 C7 C8 110.4(4) . . ? O23 C7 C6 110.0(4) . . ? C8 C7 C6 111.7(5) . . ? O23 C7 C24 107.0(4) . . ? C8 C7 C24 109.5(4) . . ? C6 C7 C24 108.2(5) . . ? C11 N10 N9 118.8(4) . . ? C11 N10 H10 121.7 . . ? N9 N10 H10 119.6 . . ? C6 N5 C4 123.1(5) . . ? C6 N5 H5 102.2 . . ? C4 N5 H5 134.2 . . ? C40 C41 H41A 111.5 . . ? C40 C41 H41B 110.8 . . ? H41A C41 H41B 109.2 . . ? C40 C41 H41C 108.9 . . ? H41A C41 H41C 108.5 . . ? H41B C41 H41C 107.8 . . ? O22 C6 N5 124.3(5) . . ? O22 C6 C7 121.1(5) . . ? N5 C6 C7 114.5(5) . . ? C32 C37 C36 121.2(7) . . ? C32 C37 H37 119.7 . . ? C36 C37 H37 119.1 . . ? N13 C12 C11 106.9(5) . . ? N13 C12 C40 112.4(5) . . ? C11 C12 C40 113.0(6) . . ? N13 C12 H12 107.6 . . ? C11 C12 H12 107.4 . . ? C40 C12 H12 109.2 . . ? C29 C30 C25 122.7(8) . . ? C29 C30 H30 118.6 . . ? C25 C30 H30 118.7 . . ? C41 C40 C43 110.3(7) . . ? C41 C40 C42 109.1(7) . . ? C43 C40 C42 108.6(6) . . ? C41 C40 C12 110.1(5) . . ? C43 C40 C12 110.5(5) . . ? C42 C40 C12 108.1(7) . . ? O39 C11 N10 123.0(5) . . ? O39 C11 C12 120.4(5) . . ? N10 C11 C12 116.6(5) . . ? C26 C25 C30 117.0(7) . . ? C26 C25 C24 121.8(6) . . ? C30 C25 C24 121.0(6) . . ? C37 C32 C33 117.8(7) . . ? C37 C32 C31 122.5(6) . . ? C33 C32 C31 119.6(6) . . ? N5 C4 C3 105.7(5) . . ? N5 C4 C18 112.7(5) . . ? C3 C4 C18 112.6(5) . . ? N5 C4 H4 111.2 . . ? C3 C4 H4 108.6 . . ? C18 C4 H4 106.1 . . ? C25 C24 C7 114.0(5) . . ? C25 C24 H24A 107.3 . . ? C7 C24 H24A 109.2 . . ? C25 C24 H24B 107.7 . . ? C7 C24 H24B 110.4 . . ? H24A C24 H24B 108.1 . . ? C3 N2 C1 120.3(6) . . ? C3 N2 H2 115.4 . . ? C1 N2 H2 120.1 . . ? N9 C8 C7 110.3(4) . . ? N9 C8 H8A 108.6 . . ? C7 C8 H8A 109.8 . . ? N9 C8 H8B 108.7 . . ? C7 C8 H8B 110.7 . . ? H8A C8 H8B 108.7 . . ? O17 C3 N2 122.8(7) . . ? O17 C3 C4 121.3(6) . . ? N2 C3 C4 115.9(5) . . ? C35 C36 C37 120.2(8) . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 120.2 . . ? C32 C33 C34 121.8(7) . . ? C32 C33 H33 119.0 . . ? C34 C33 H33 119.3 . . ? N9 C31 C32 113.3(5) . . ? N9 C31 H31A 109.0 . . ? C32 C31 H31A 108.0 . . ? N9 C31 H31B 109.9 . . ? C32 C31 H31B 108.7 . . ? H31A C31 H31B 107.8 . . ? C18 C19 H19A 112.2 . . ? C18 C19 H19B 108.4 . . ? H19A C19 H19B 107.0 . . ? C18 C19 H19C 111.8 . . ? H19A C19 H19C 111.6 . . ? H19B C19 H19C 105.4 . . ? C14 O15 C16 116.4(8) . . ? C40 C43 H43A 108.9 . . ? C40 C43 H43B 110.2 . . ? H43A C43 H43B 108.2 . . ? C40 C43 H43C 110.5 . . ? H43A C43 H43C 108.5 . . ? H43B C43 H43C 110.4 . . ? C36 C35 C34 120.1(7) . . ? C36 C35 Br38 121.0(7) . . ? C34 C35 Br38 118.8(6) . . ? O44 C14 N13 125.8(8) . . ? O44 C14 O15 123.7(8) . . ? N13 C14 O15 110.5(7) . . ? C35 C34 C33 118.7(7) . . ? C35 C34 H34 121.0 . . ? C33 C34 H34 120.3 . . ? C19 C18 C20 108.2(7) . . ? C19 C18 C21 110.5(8) . . ? C20 C18 C21 108.7(8) . . ? C19 C18 C4 112.5(6) . . ? C20 C18 C4 108.3(6) . . ? C21 C18 C4 108.5(7) . . ? N2 C1 H1A 111.4 . . ? N2 C1 H1B 110.3 . . ? H1A C1 H1B 109.8 . . ? N2 C1 H1C 110.3 . . ? H1A C1 H1C 107.7 . . ? H1B C1 H1C 107.3 . . ? C28 C29 C30 119.4(9) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C40 C42 H42A 111.0 . . ? C40 C42 H42B 110.0 . . ? H42A C42 H42B 108.1 . . ? C40 C42 H42C 110.5 . . ? H42A C42 H42C 109.1 . . ? H42B C42 H42C 108.1 . . ? C25 C26 C27 121.2(9) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 118.8 . . ? C29 C28 C27 121.4(9) . . ? C29 C28 H28 121.6 . . ? C27 C28 H28 117.0 . . ? C18 C21 H21A 113.3 . . ? C18 C21 H21B 110.7 . . ? H21A C21 H21B 108.0 . . ? C18 C21 H21C 111.6 . . ? H21A C21 H21C 107.8 . . ? H21B C21 H21C 105.1 . . ? C28 C27 C26 118.4(10) . . ? C28 C27 H27 120.5 . . ? C26 C27 H27 121.1 . . ? C18 C20 H20A 110.8 . . ? C18 C20 H20B 110.6 . . ? H20A C20 H20B 109.1 . . ? C18 C20 H20C 109.4 . . ? H20A C20 H20C 108.9 . . ? H20B C20 H20C 108.0 . . ? O15 C16 H16A 110.5 . . ? O15 C16 H16B 112.0 . . ? H16A C16 H16B 107.8 . . ? O15 C16 H16C 110.4 . . ? H16A C16 H16C 107.9 . . ? H16B C16 H16C 108.1 . . ? C46 O45 H45 108.6 . . ? C47 C46 O45 112.8(16) . . ? C47 C46 H46A 109.1 . . ? O45 C46 H46A 109.0 . . ? C47 C46 H46B 108.9 . . ? O45 C46 H46B 109.0 . . ? H46A C46 H46B 107.8 . . ? C46 C47 H47A 117.3 . . ? C46 C47 H47B 113.5 . . ? H47A C47 H47B 108.6 . . ? C46 C47 H47C 109.2 . . ? H47A C47 H47C 103.8 . . ? H47B C47 H47C 103.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.496 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.050