# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 #TrackingRef '- Nafribccdc.cif' #------------------ AUDIT DETAILS -------------------------------------------# #============================================================================== # # SUBMISSION DETAILS _publ_contact_author_name 'Resende, Jackson A. L. C.' # Name of author for correspondence _publ_contact_author_address ;Departmento de Qu\'imica In\^organica Universidade Federal Fluminense Niter\'oi, RJ, Brasil ; # Address of author for correspondence _publ_contact_author_email jresende@id.uff.br _publ_contact_author_fax +55(21)2629-2159 _publ_contact_author_phone +55(21)2629-5873 _publ_contact_letter ; Submission dated :2011-09-27 Please consider this CIF for submission to the Cambridge Crystallographic Data Centre. I certify that all authors have seen and approved of this submission, that all have made significant scientific contributions to the work reported, and that all share responsibility and accountability for the results. This CIF is submitted as a personal communication This CIF is submitted as part of a journal submission Organic & Biomolecular Chemistry Resende, Jackson A. L. C. ; #============================================================================== # # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis of Carbohydrate-based Naphthoquinones and Their Substituted Phenylhydrazono Derivatives as Anticancer Agents ; _publ_section_title_footnote . # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address _publ_author_footnote _publ_author_email V.R.Campos ; Departamento de Qu\'imica Org\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . . 'E.A.Dos Santos' ; Departamento de Fisiologia e Farmacologia Universidade Federal do Cear\'a CEP60431-970, Fortaleza, CE Brasil ; . . V.F.Ferreira ; Departamento de Qu\'imica Org\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . . R.Montenegro ; Instituto de Ci\^encias Biol\'ogicas Universidade Federal do Par\'a, Bel\'em, PA Brasil ; . . ; M.C.B.V.de Souza ; ; Departamento de Qu\'imica Org\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . . L.V.Costa-Lotufo ; Departamento de Fisiologia e Farmacologia Universidade Federal do Cear\'a CEP60431-970, Fortaleza, CE Brasil ; . . 'M.O.de Moraes' ; Departamento de Fisiologia e Farmacologia Universidade Federal do Cear\'a CEP60431-970, Fortaleza, CE Brasil ; . . A.K.P.Regufe ; Departamento de Qu\'imica Org\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . . A.K.Jordao ; Departamento de Qu\'imica Org\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . . ; A.d.C.Pinto ; ; Departamento de Qu\'imica Org\^anica, Universidade Federal do Rio de Janeiro, 21941-590, Rio de Janeiro, RJ Brasil ; . . J.A.L.C.Resende ; Departamento de Qu\'imica Inorg\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . . A.C.Cunha ; Departamento de Qu\'imica Org\^anica Instituto de Qu\'imica Universidade Federal Fluminense Niter\'oi, RJ Brasil ; . . data_nafrib_br_ph _database_code_depnum_ccdc_archive 'CCDC 889649' #TrackingRef '- Nafribccdc.cif' _audit_creation_date 2012-05-19 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ; ? 2012-07-02 # Formatted by publCIF ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_moiety 'C25 H26 Br N3 O5' _chemical_formula_sum 'C25 H26 Br N3 O5' _chemical_formula_weight 528.4 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 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' _cell_length_a 5.8640(2) _cell_length_b 15.2666(18) _cell_length_c 26.181(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2343.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9799 _cell_measurement_theta_min 2.7662 _cell_measurement_theta_max 29.4579 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.3871 _exptl_crystal_size_mid 0.1393 _exptl_crystal_size_min 0.0734 _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 2 1 0.054 0 -2 -1 0.0194 1 0 0 0.2 0 -1 3 0.0622 0 1 -3 0.0622 -1 1 0 0.162 0 1 3 0.0696 0 1 -1 0.0418 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.796 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_T_max 0.894 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 -0.0035399714 _diffrn_orient_matrix_ub_12 -0.0225053831 _diffrn_orient_matrix_ub_13 0.023680861 _diffrn_orient_matrix_ub_21 -0.0068739217 _diffrn_orient_matrix_ub_22 0.0405905897 _diffrn_orient_matrix_ub_23 0.0130713471 _diffrn_orient_matrix_ub_31 -0.1207865692 _diffrn_orient_matrix_ub_32 -0.0016504163 _diffrn_orient_matrix_ub_33 -0.0014379164 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_unetI/netI 0.0455 _diffrn_reflns_number 18215 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4782 _reflns_number_gt 3855 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0314P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4782 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0568 _refine_ls_goodness_of_fit_ref 0.95 _refine_ls_restrained_S_all 0.95 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(6) _refine_diff_density_max 0.434 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' 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 0.0653(3) 0.12679(10) 0.95442(6) 0.0286(4) Uani 1 1 d . . . N1 N -0.0705(3) 0.08484(12) 0.85302(7) 0.0225(4) Uani 1 1 d . . . N2 N -0.1977(3) 0.05258(12) 0.88995(7) 0.0241(4) Uani 1 1 d . . . H2A H -0.1639 0.0639 0.922 0.029 Uiso 1 1 calc R . . N3 N 0.6785(3) 0.29387(11) 0.88921(7) 0.0247(5) Uani 1 1 d . . . H3A H 0.7378 0.3172 0.8615 0.03 Uiso 1 1 d R . . C1 C 0.1087(4) 0.13282(14) 0.86451(9) 0.0213(5) Uani 1 1 d . . . C2 C 0.1795(4) 0.15374(14) 0.91663(9) 0.0228(6) Uani 1 1 d . . . C3 C 0.3750(4) 0.20717(14) 0.92298(9) 0.0242(5) Uani 1 1 d . . . H3 H 0.4217 0.2217 0.9567 0.029 Uiso 1 1 calc R . . C4 C 0.4999(5) 0.23888(11) 0.88278(7) 0.0212(4) Uani 1 1 d . . . C5 C 0.5763(4) 0.23775(15) 0.78840(9) 0.0284(6) Uani 1 1 d . . . H5 H 0.7119 0.2705 0.7939 0.034 Uiso 1 1 calc R . . C6 C 0.5154(6) 0.21437(13) 0.73928(8) 0.0311(5) Uani 1 1 d . . . H6 H 0.6099 0.23 0.7113 0.037 Uiso 1 1 calc R . . C7 C 0.3163(4) 0.16818(14) 0.73116(9) 0.0289(6) Uani 1 1 d . . . H7 H 0.272 0.1535 0.6973 0.035 Uiso 1 1 calc R . . C8 C 0.1824(4) 0.14341(14) 0.77132(9) 0.0256(6) Uani 1 1 d . . . H8 H 0.046 0.1117 0.765 0.031 Uiso 1 1 calc R . . C9 C 0.2428(4) 0.16402(13) 0.82165(9) 0.0209(5) Uani 1 1 d . . . C10 C 0.4416(4) 0.21402(13) 0.82995(8) 0.0210(5) Uani 1 1 d . . . C11 C 0.7813(4) 0.31795(14) 0.93752(9) 0.0245(5) Uani 1 1 d . . . H11A H 0.9265 0.2856 0.9415 0.029 Uiso 1 1 calc R . . H11B H 0.6786 0.2998 0.9656 0.029 Uiso 1 1 calc R . . C12 C 0.8279(4) 0.41518(13) 0.94222(8) 0.0206(5) Uani 1 1 d . . . H12 H 0.8888 0.4268 0.9773 0.025 Uiso 1 1 calc R . . C13 C 0.6220(4) 0.47203(13) 0.93429(9) 0.0225(5) Uani 1 1 d . . . H13 H 0.4755 0.4398 0.9396 0.027 Uiso 1 1 calc R . . C14 C 0.6447(4) 0.50922(15) 0.88036(9) 0.0270(6) Uani 1 1 d . . . H14 H 0.527 0.4847 0.8567 0.032 Uiso 1 1 calc R . . C15 C 0.8864(4) 0.48561(14) 0.86347(9) 0.0231(5) Uani 1 1 d . . . H15 H 0.9711 0.54 0.8538 0.028 Uiso 1 1 calc R . . C16 C 0.5550(4) 0.61963(14) 0.93657(9) 0.0247(6) Uani 1 1 d . . . C17 C 0.2983(4) 0.62511(17) 0.94037(12) 0.0417(7) Uani 1 1 d . . . H17A H 0.2309 0.5698 0.9288 0.063 Uiso 1 1 calc R . . H17B H 0.243 0.6731 0.9188 0.063 Uiso 1 1 calc R . . H17C H 0.2544 0.636 0.9759 0.063 Uiso 1 1 calc R . . C18 C 0.6695(4) 0.70193(14) 0.95377(11) 0.0363(7) Uani 1 1 d . . . H18A H 0.6282 0.714 0.9894 0.054 Uiso 1 1 calc R . . H18B H 0.6202 0.7508 0.9322 0.054 Uiso 1 1 calc R . . H18C H 0.8352 0.695 0.9511 0.054 Uiso 1 1 calc R . . C19 C 1.0956(4) 0.41162(19) 0.79970(11) 0.0382(7) Uani 1 1 d . . . H19A H 1.1668 0.4673 0.79 0.057 Uiso 1 1 calc R . . H19B H 1.0805 0.3743 0.7694 0.057 Uiso 1 1 calc R . . H19C H 1.1909 0.382 0.8252 0.057 Uiso 1 1 calc R . . O11 O 0.9949(3) 0.44504(9) 0.90550(5) 0.0249(3) Uani 1 1 d . . . O12 O 0.8743(3) 0.42813(11) 0.82091(6) 0.0275(4) Uani 1 1 d . . . O13 O 0.6405(3) 0.54870(9) 0.96563(6) 0.0248(4) Uani 1 1 d . . . O14 O 0.6234(4) 0.60109(10) 0.88590(6) 0.0441(5) Uani 1 1 d . . . C20 C -0.3859(4) 0.00042(13) 0.87825(9) 0.0226(5) Uani 1 1 d . . . C21 C -0.5128(5) -0.03408(13) 0.91818(8) 0.0267(5) Uani 1 1 d . . . H21 H -0.4718 -0.0214 0.9525 0.032 Uiso 1 1 calc R . . C22 C -0.6987(4) -0.08684(15) 0.90813(10) 0.0283(6) Uani 1 1 d . . . H22 H -0.7869 -0.11 0.9354 0.034 Uiso 1 1 calc R . . C23 C -0.7549(4) -0.10555(14) 0.85859(9) 0.0248(6) Uani 1 1 d . . . C24 C -0.6335(4) -0.07003(15) 0.81853(9) 0.0264(5) Uani 1 1 d . . . H24 H -0.6774 -0.0821 0.7843 0.032 Uiso 1 1 calc R . . C25 C -0.4487(4) -0.01704(14) 0.82814(9) 0.0247(6) Uani 1 1 d . . . H25 H -0.3644 0.0075 0.8006 0.03 Uiso 1 1 calc R . . Br Br -1.00429(5) -0.180908(14) 0.844652(9) 0.03525(8) Uani 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 0.0353(10) 0.0281(8) 0.0225(9) -0.0001(7) 0.0058(7) -0.0011(7) N1 0.0263(10) 0.0197(9) 0.0214(11) 0.0000(8) 0.0010(8) 0.0050(8) N2 0.0291(11) 0.0243(10) 0.0189(11) -0.0005(8) 0.0031(9) 0.0035(9) N3 0.0356(11) 0.0206(10) 0.0178(11) -0.0022(8) 0.0018(9) -0.0023(9) C1 0.0268(12) 0.0146(11) 0.0226(14) -0.0009(9) 0.0023(10) 0.0060(10) C2 0.0287(13) 0.0179(11) 0.0218(14) -0.0005(9) 0.0028(11) 0.0071(10) C3 0.0341(13) 0.0232(12) 0.0151(13) -0.0060(9) -0.0017(11) 0.0025(11) C4 0.0292(11) 0.0142(9) 0.0202(12) -0.0016(8) -0.0021(15) 0.0050(14) C5 0.0349(14) 0.0218(12) 0.0284(15) -0.0039(10) 0.0038(11) -0.0056(10) C6 0.0457(15) 0.0295(11) 0.0181(13) -0.0033(9) 0.0054(15) -0.0053(15) C7 0.0416(14) 0.0261(13) 0.0190(14) -0.0051(11) -0.0022(12) -0.0005(12) C8 0.0310(14) 0.0217(12) 0.0240(15) -0.0030(10) -0.0027(12) 0.0003(11) C9 0.0285(12) 0.0128(11) 0.0214(14) -0.0019(9) 0.0008(10) 0.0064(9) C10 0.0290(14) 0.0143(10) 0.0196(13) -0.0018(8) 0.0012(9) 0.0054(9) C11 0.0333(12) 0.0189(11) 0.0214(13) -0.0032(10) -0.0047(10) 0.0010(11) C12 0.0282(12) 0.0193(11) 0.0143(13) -0.0032(9) -0.0011(10) -0.0013(10) C13 0.0301(13) 0.0163(11) 0.0210(14) -0.0078(9) -0.0002(11) -0.0022(10) C14 0.0316(14) 0.0290(13) 0.0205(14) -0.0055(10) -0.0043(11) 0.0092(11) C15 0.0288(13) 0.0200(12) 0.0207(14) -0.0026(9) -0.0011(10) 0.0003(11) C16 0.0321(16) 0.0199(11) 0.0220(14) 0.0015(9) -0.0010(11) 0.0075(10) C17 0.0327(15) 0.0300(15) 0.062(2) -0.0147(14) -0.0048(15) 0.0037(13) C18 0.0316(13) 0.0211(13) 0.0561(19) 0.0018(12) 0.0031(13) -0.0010(11) C19 0.0323(14) 0.0411(16) 0.0413(18) -0.0106(13) 0.0108(13) -0.0015(13) O11 0.0237(7) 0.0253(7) 0.0256(8) -0.0001(6) -0.0043(9) 0.0007(10) O12 0.0302(9) 0.0287(9) 0.0237(10) -0.0071(8) 0.0026(7) 0.0006(8) O13 0.0390(9) 0.0149(7) 0.0206(9) -0.0022(7) -0.0019(8) 0.0036(7) O14 0.0809(14) 0.0283(9) 0.0230(10) 0.0082(8) 0.0137(9) 0.0272(9) C20 0.0234(12) 0.0156(11) 0.0290(15) -0.0021(10) 0.0016(11) 0.0067(10) C21 0.0328(12) 0.0243(11) 0.0229(12) -0.0028(9) 0.0048(14) 0.0055(15) C22 0.0293(13) 0.0244(12) 0.0312(16) 0.0056(11) 0.0075(12) 0.0029(11) C23 0.0226(12) 0.0190(12) 0.0328(16) -0.0015(10) 0.0025(11) 0.0036(10) C24 0.0289(13) 0.0257(13) 0.0247(14) -0.0026(11) 0.0021(11) 0.0046(11) C25 0.0261(14) 0.0227(12) 0.0254(14) 0.0034(9) 0.0047(10) 0.0026(10) Br 0.02805(11) 0.02946(11) 0.04824(16) 0.00194(11) 0.00359(16) -0.00259(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 1.263(3) . ? N1 C1 1.316(3) . ? N1 N2 1.317(2) . ? N2 C20 1.395(3) . ? N2 H2A 0.88 . ? N3 C4 1.353(3) . ? N3 C11 1.448(3) . ? N3 H3A 0.88 . ? C1 C9 1.451(3) . ? C1 C2 1.462(3) . ? C2 C3 1.417(3) . ? C3 C4 1.371(3) . ? C3 H3 0.95 . ? C4 C10 1.474(3) . ? C5 C6 1.381(3) . ? C5 C10 1.392(3) . ? C5 H5 0.95 . ? C6 C7 1.380(4) . ? C6 H6 0.95 . ? C7 C8 1.366(3) . ? C7 H7 0.95 . ? C8 C9 1.400(3) . ? C8 H8 0.95 . ? C9 C10 1.410(3) . ? C11 C12 1.514(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 O11 1.446(3) . ? C12 C13 1.501(3) . ? C12 H12 1 . ? C13 O13 1.434(2) . ? C13 C14 1.528(3) . ? C13 H13 1 . ? C14 O14 1.415(3) . ? C14 C15 1.528(3) . ? C14 H14 1 . ? C15 O11 1.414(3) . ? C15 O12 1.420(3) . ? C15 H15 1 . ? C16 O14 1.415(3) . ? C16 O13 1.415(2) . ? C16 C18 1.494(3) . ? C16 C17 1.511(3) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C19 O12 1.434(3) . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C20 C21 1.387(3) . ? C20 C25 1.388(3) . ? C21 C22 1.380(3) . ? C21 H21 0.95 . ? C22 C23 1.368(3) . ? C22 H22 0.95 . ? C23 C24 1.379(3) . ? C23 Br 1.896(2) . ? C24 C25 1.376(3) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? 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 N1 N2 119.53(19) . . ? N1 N2 C20 120.0(2) . . ? N1 N2 H2A 120 . . ? C20 N2 H2A 120 . . ? C4 N3 C11 126.02(19) . . ? C4 N3 H3A 117 . . ? C11 N3 H3A 117 . . ? N1 C1 C9 116.0(2) . . ? N1 C1 C2 124.2(2) . . ? C9 C1 C2 119.8(2) . . ? O1 C2 C3 121.6(2) . . ? O1 C2 C1 120.6(2) . . ? C3 C2 C1 117.7(2) . . ? C4 C3 C2 123.1(2) . . ? C4 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? N3 C4 C3 122.5(2) . . ? N3 C4 C10 117.12(19) . . ? C3 C4 C10 120.4(2) . . ? C6 C5 C10 120.9(2) . . ? C6 C5 H5 119.6 . . ? C10 C5 H5 119.6 . . ? C7 C6 C5 119.6(2) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.1(2) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C8 C9 C10 118.4(2) . . ? C8 C9 C1 121.1(2) . . ? C10 C9 C1 120.4(2) . . ? C5 C10 C9 119.3(2) . . ? C5 C10 C4 122.3(2) . . ? C9 C10 C4 118.4(2) . . ? N3 C11 C12 113.25(19) . . ? N3 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N3 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? O11 C12 C13 105.70(17) . . ? O11 C12 C11 112.16(18) . . ? C13 C12 C11 114.23(18) . . ? O11 C12 H12 108.2 . . ? C13 C12 H12 108.2 . . ? C11 C12 H12 108.2 . . ? O13 C13 C12 109.39(18) . . ? O13 C13 C14 102.65(17) . . ? C12 C13 C14 105.82(18) . . ? O13 C13 H13 112.8 . . ? C12 C13 H13 112.8 . . ? C14 C13 H13 112.8 . . ? O14 C14 C13 105.42(18) . . ? O14 C14 C15 110.2(2) . . ? C13 C14 C15 105.11(19) . . ? O14 C14 H14 111.9 . . ? C13 C14 H14 111.9 . . ? C15 C14 H14 111.9 . . ? O11 C15 O12 111.25(17) . . ? O11 C15 C14 107.19(19) . . ? O12 C15 C14 109.05(18) . . ? O11 C15 H15 109.8 . . ? O12 C15 H15 109.8 . . ? C14 C15 H15 109.8 . . ? O14 C16 O13 104.51(16) . . ? O14 C16 C18 108.88(19) . . ? O13 C16 C18 108.80(18) . . ? O14 C16 C17 110.8(2) . . ? O13 C16 C17 111.1(2) . . ? C18 C16 C17 112.4(2) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O12 C19 H19A 109.5 . . ? O12 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O12 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 O11 C12 110.51(18) . . ? C15 O12 C19 111.54(18) . . ? C16 O13 C13 106.87(16) . . ? C16 O14 C14 108.63(17) . . ? C21 C20 C25 119.8(2) . . ? C21 C20 N2 118.4(2) . . ? C25 C20 N2 121.8(2) . . ? C22 C21 C20 120.1(2) . . ? C22 C21 H21 120 . . ? C20 C21 H21 120 . . ? C23 C22 C21 119.5(2) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 120.9(2) . . ? C22 C23 Br 119.67(18) . . ? C24 C23 Br 119.38(18) . . ? C25 C24 C23 119.9(2) . . ? C25 C24 H24 120 . . ? C23 C24 H24 120 . . ? C24 C25 C20 119.7(2) . . ? C24 C25 H25 120.2 . . ? C20 C25 H25 120.2 . . ? 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 C1 N1 N2 C20 -178.95(18) . . . . ? N2 N1 C1 C9 178.52(18) . . . . ? N2 N1 C1 C2 0.0(3) . . . . ? N1 C1 C2 O1 -1.2(3) . . . . ? C9 C1 C2 O1 -179.68(19) . . . . ? N1 C1 C2 C3 -179.24(19) . . . . ? C9 C1 C2 C3 2.3(3) . . . . ? O1 C2 C3 C4 -178.7(2) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C11 N3 C4 C3 8.4(3) . . . . ? C11 N3 C4 C10 -172.0(2) . . . . ? C2 C3 C4 N3 176.2(2) . . . . ? C2 C3 C4 C10 -3.5(3) . . . . ? C10 C5 C6 C7 1.1(4) . . . . ? C5 C6 C7 C8 -1.8(4) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? C7 C8 C9 C10 2.3(3) . . . . ? C7 C8 C9 C1 -175.9(2) . . . . ? N1 C1 C9 C8 -0.1(3) . . . . ? C2 C1 C9 C8 178.53(19) . . . . ? N1 C1 C9 C10 -178.32(18) . . . . ? C2 C1 C9 C10 0.3(3) . . . . ? C6 C5 C10 C9 1.2(3) . . . . ? C6 C5 C10 C4 -179.2(2) . . . . ? C8 C9 C10 C5 -2.9(3) . . . . ? C1 C9 C10 C5 175.37(19) . . . . ? C8 C9 C10 C4 177.45(19) . . . . ? C1 C9 C10 C4 -4.3(3) . . . . ? N3 C4 C10 C5 6.7(3) . . . . ? C3 C4 C10 C5 -173.7(2) . . . . ? N3 C4 C10 C9 -173.72(18) . . . . ? C3 C4 C10 C9 5.9(3) . . . . ? C4 N3 C11 C12 -135.0(2) . . . . ? N3 C11 C12 O11 -64.4(2) . . . . ? N3 C11 C12 C13 55.8(3) . . . . ? O11 C12 C13 O13 -88.9(2) . . . . ? C11 C12 C13 O13 147.34(18) . . . . ? O11 C12 C13 C14 21.1(2) . . . . ? C11 C12 C13 C14 -102.7(2) . . . . ? O13 C13 C14 O14 -12.3(2) . . . . ? C12 C13 C14 O14 -126.92(19) . . . . ? O13 C13 C14 C15 104.20(19) . . . . ? C12 C13 C14 C15 -10.5(2) . . . . ? O14 C14 C15 O11 109.0(2) . . . . ? C13 C14 C15 O11 -4.1(2) . . . . ? O14 C14 C15 O12 -130.46(19) . . . . ? C13 C14 C15 O12 116.42(19) . . . . ? O12 C15 O11 C12 -101.0(2) . . . . ? C14 C15 O11 C12 18.2(2) . . . . ? C13 C12 O11 C15 -24.9(2) . . . . ? C11 C12 O11 C15 100.1(2) . . . . ? O11 C15 O12 C19 -68.6(3) . . . . ? C14 C15 O12 C19 173.3(2) . . . . ? O14 C16 O13 C13 -35.8(2) . . . . ? C18 C16 O13 C13 -151.96(19) . . . . ? C17 C16 O13 C13 83.8(2) . . . . ? C12 C13 O13 C16 141.38(18) . . . . ? C14 C13 O13 C16 29.3(2) . . . . ? O13 C16 O14 C14 27.4(2) . . . . ? C18 C16 O14 C14 143.5(2) . . . . ? C17 C16 O14 C14 -92.3(2) . . . . ? C13 C14 O14 C16 -9.1(3) . . . . ? C15 C14 O14 C16 -122.0(2) . . . . ? N1 N2 C20 C21 178.54(19) . . . . ? N1 N2 C20 C25 -1.8(3) . . . . ? C25 C20 C21 C22 1.1(3) . . . . ? N2 C20 C21 C22 -179.2(2) . . . . ? C20 C21 C22 C23 0.7(3) . . . . ? C21 C22 C23 C24 -2.3(3) . . . . ? C21 C22 C23 Br 178.06(17) . . . . ? C22 C23 C24 C25 2.0(3) . . . . ? Br C23 C24 C25 -178.35(16) . . . . ? C23 C24 C25 C20 -0.1(3) . . . . ? C21 C20 C25 C24 -1.4(3) . . . . ? N2 C20 C25 C24 178.95(19) . . . . ? 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 N3 H3A O12 0.88 2.15 2.952(3) 150.6 . N2 H2A O1 0.88 1.86 2.552(2) 134.5 . C7 H7 O14 0.95 2.4 3.251(3) 148.8 4_646 C11 H11B O1 0.99 2.47 3.212(3) 131.8 3_557 C17 H17A O11 0.98 2.43 3.399(3) 169 1_455 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF # Attachment '- Nafxilo_ccdc.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2012-05-19 at 15:49:21 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\crystal\wingx\files\archive.reqdat # CIF files read : 14naftoqxilbrph 14naftoquixilobrph2 struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_14naftoqxilbrph _database_code_depnum_ccdc_archive 'CCDC 889650' #TrackingRef '- Nafxilo_ccdc.cif' _audit_creation_date 2012-05-19 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ; ? 2012-07-02 # Formatted by publCIF ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ? _chemical_formula_moiety 'C24 H24 Br1 N3 O5' _chemical_formula_sum 'C24 H24 Br N3 O5' _chemical_formula_weight 514.37 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.1446(3) _cell_length_b 13.3386(10) _cell_length_c 33.974(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2331.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3019 _cell_measurement_theta_min 2.6044 _cell_measurement_theta_max 66.4771 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.2475 _exptl_crystal_size_mid 0.146 _exptl_crystal_size_min 0.0255 _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 2 1 0.0692 1 -1 -4 0.073 -1 1 4 0.073 0 0 1 0.0206 0 -2 -1 0.0692 0 0 -1 0.0049 _exptl_special_details ? #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.66417 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 10.4186 _diffrn_orient_matrix_ub_11 0.2512561 _diffrn_orient_matrix_ub_12 0.0375516 _diffrn_orient_matrix_ub_13 0.019889 _diffrn_orient_matrix_ub_21 -0.0709666 _diffrn_orient_matrix_ub_22 -0.0584599 _diffrn_orient_matrix_ub_23 0.0376822 _diffrn_orient_matrix_ub_31 0.1470249 _diffrn_orient_matrix_ub_32 -0.092392 _diffrn_orient_matrix_ub_33 -0.0157287 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_unetI/netI 0.047 _diffrn_reflns_number 13099 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.6 _diffrn_reflns_theta_max 66.49 _diffrn_reflns_theta_full 66.49 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 2404 _reflns_number_gt 1947 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0550P)^2^+2.8378P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2404 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.50(5) _refine_diff_density_max 0.703 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.07 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Br Br 1.2971(2) 0.45864(7) -0.03615(3) 0.0703(3) Uani 1 1 d . . . O14 O -0.3280(10) 0.1837(3) 0.39495(13) 0.0434(11) Uani 1 1 d . B . N2 N 0.6377(12) 0.3414(4) 0.10445(16) 0.0432(14) Uani 1 1 d . . . H2A H 0.518 0.3846 0.1118 0.052 Uiso 1 1 calc R . . O12 O -0.0669(10) 0.0407(3) 0.31246(13) 0.0447(11) Uani 1 1 d . . . H12O H -0.0975 -0.0157 0.3224 0.067 Uiso 1 1 calc R . . O11 O 0.0747(10) 0.2435(3) 0.33041(15) 0.0466(12) Uani 1 1 d . . . C16 C -0.2038(15) 0.2676(5) 0.4144(2) 0.0448(16) Uani 1 1 d . . . C4 C 0.1786(15) 0.1852(4) 0.21894(18) 0.0373(15) Uani 1 1 d . . . N1 N 0.6601(12) 0.2541(4) 0.12321(15) 0.0390(13) Uani 1 1 d . . . N3 N 0.0439(13) 0.1645(4) 0.25134(17) 0.0445(15) Uani 1 1 d . . . H3A H 0.0739 0.1065 0.2628 0.053 Uiso 1 1 calc R . . O1 O 0.2544(11) 0.3860(3) 0.14797(13) 0.0486(13) Uani 1 1 d . . . C6 C 0.6028(15) -0.0439(5) 0.2111(2) 0.0467(17) Uani 1 1 d . . . H6 H 0.6292 -0.1056 0.2245 0.056 Uiso 1 1 calc R . . C12 C -0.1692(14) 0.2178(4) 0.31321(17) 0.0344(14) Uani 1 1 d . . . H12 H -0.3034 0.2657 0.3232 0.041 Uiso 1 1 calc R . . C1 C 0.4970(14) 0.2350(4) 0.15188(19) 0.0359(15) Uani 1 1 d . . . C9 C 0.5325(13) 0.1370(4) 0.17227(18) 0.0327(14) Uani 1 1 d . . . C11 C -0.1495(15) 0.2298(5) 0.2694(2) 0.0433(18) Uani 1 1 d . . . H11A H -0.3213 0.2155 0.2575 0.052 Uiso 1 1 calc R . . H11B H -0.105 0.3003 0.2633 0.052 Uiso 1 1 calc R . . C2 C 0.2930(16) 0.3020(4) 0.16568(17) 0.0390(16) Uani 1 1 d . . . C5 C 0.4170(15) 0.0217(4) 0.2245(2) 0.0406(16) Uani 1 1 d . . . H5 H 0.3158 0.005 0.2469 0.049 Uiso 1 1 calc R . . C10 C 0.3752(14) 0.1141(4) 0.20501(19) 0.0360(16) Uani 1 1 d . . . C23 C 1.0965(16) 0.4215(6) 0.0090(2) 0.0511(19) Uani 1 1 d . . . C7 C 0.7524(14) -0.0212(4) 0.1784(2) 0.0428(17) Uani 1 1 d . . . H7 H 0.878 -0.0678 0.1691 0.051 Uiso 1 1 calc R . . C8 C 0.7189(16) 0.0693(5) 0.15917(19) 0.0434(17) Uani 1 1 d . . . H8 H 0.8235 0.0852 0.137 0.052 Uiso 1 1 calc R . . C25 C 1.0053(16) 0.3063(5) 0.0607(2) 0.0463(18) Uani 1 1 d . . . H25 H 1.0417 0.2457 0.0743 0.056 Uiso 1 1 calc R . . C21 C 0.7523(15) 0.4560(5) 0.0533(2) 0.0526(19) Uani 1 1 d . . . H21 H 0.6161 0.4987 0.0619 0.063 Uiso 1 1 calc R . . C22 C 0.9042(16) 0.4822(5) 0.0209(2) 0.0504(19) Uani 1 1 d . . . H22 H 0.8715 0.543 0.0073 0.061 Uiso 1 1 calc R . . C3 C 0.1434(14) 0.2745(4) 0.19828(19) 0.0369(16) Uani 1 1 d . . . H3 H 0.0107 0.3191 0.2068 0.044 Uiso 1 1 calc R . . C14 C -0.1379(14) 0.1303(5) 0.37271(19) 0.0411(17) Uani 1 1 d . . . H14 H -0.0843 0.0664 0.3858 0.049 Uiso 1 1 calc R B . C20 C 0.8038(16) 0.3651(5) 0.07299(19) 0.0414(16) Uani 1 1 d . . . C13 C -0.2264(14) 0.1140(4) 0.33065(17) 0.0365(15) Uani 1 1 d . B . H13 H -0.4151 0.0964 0.329 0.044 Uiso 1 1 calc R . . C24 C 1.1571(17) 0.3328(5) 0.0289(2) 0.0500(18) Uani 1 1 d . . . H24 H 1.2987 0.2921 0.0208 0.06 Uiso 1 1 calc R . . C15 C 0.0853(15) 0.2043(6) 0.3692(2) 0.0491(19) Uani 1 1 d . B . H15 H 0.251 0.1656 0.3717 0.059 Uiso 1 1 calc R A 1 C171 C -0.238(4) 0.2532(11) 0.4579(4) 0.071(5) Uani 0.665(17) 1 d P B 1 H17A H -0.4227 0.2593 0.4646 0.106 Uiso 0.665(17) 1 calc PR B 1 H17B H -0.1386 0.3043 0.4721 0.106 Uiso 0.665(17) 1 calc PR B 1 H17C H -0.1757 0.1864 0.4654 0.106 Uiso 0.665(17) 1 calc PR B 1 O131 O 0.055(5) 0.260(5) 0.4033(15) 0.049(9) Uani 0.58(14) 1 d P B 1 C181 C -0.341(3) 0.3654(10) 0.4000(4) 0.049(3) Uani 0.665(17) 1 d P B 1 H18A H -0.5236 0.3646 0.4083 0.073 Uiso 0.665(17) 1 calc PR B 1 H18B H -0.3323 0.3692 0.3712 0.073 Uiso 0.665(17) 1 calc PR B 1 H18C H -0.2539 0.4239 0.4114 0.073 Uiso 0.665(17) 1 calc PR B 1 C172 C -0.066(9) 0.237(2) 0.4539(8) 0.071(5) Uani 0.335(17) 1 d P B 2 H17D H -0.1978 0.2149 0.473 0.106 Uiso 0.335(17) 1 calc PR B 2 H17E H 0.0291 0.2941 0.4645 0.106 Uiso 0.335(17) 1 calc PR B 2 H17F H 0.0548 0.1814 0.4489 0.106 Uiso 0.335(17) 1 calc PR B 2 O132 O 0.013(9) 0.297(6) 0.390(2) 0.043(13) Uani 0.42(14) 1 d P B 2 C182 C -0.369(7) 0.349(2) 0.4187(9) 0.049(3) Uani 0.335(17) 1 d P B 2 H18D H -0.521 0.3285 0.4343 0.073 Uiso 0.335(17) 1 calc PR B 2 H18E H -0.4269 0.3717 0.3928 0.073 Uiso 0.335(17) 1 calc PR B 2 H18F H -0.2779 0.4031 0.4322 0.073 Uiso 0.335(17) 1 calc PR B 2 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 Br 0.0693(6) 0.0817(6) 0.0600(5) 0.0258(5) 0.0121(5) -0.0017(6) O14 0.039(3) 0.042(2) 0.049(3) -0.010(2) 0.011(2) -0.002(2) N2 0.050(4) 0.030(3) 0.050(3) 0.003(2) 0.008(3) 0.003(3) O12 0.065(3) 0.020(2) 0.050(3) -0.001(2) 0.016(2) 0.000(2) O11 0.043(3) 0.030(2) 0.067(3) -0.004(2) -0.007(3) -0.009(2) C16 0.041(4) 0.045(4) 0.049(4) -0.014(3) 0.005(4) -0.006(4) C4 0.047(4) 0.024(3) 0.041(3) -0.006(3) 0.001(3) 0.004(3) N1 0.051(4) 0.028(3) 0.038(3) 0.000(2) 0.003(3) 0.003(3) N3 0.061(4) 0.023(3) 0.050(3) 0.005(2) 0.015(3) 0.013(3) O1 0.071(4) 0.024(2) 0.050(3) 0.0071(19) 0.010(3) 0.011(3) C6 0.060(4) 0.020(3) 0.060(4) 0.006(3) 0.007(4) 0.006(4) C12 0.037(4) 0.027(3) 0.039(3) -0.005(2) -0.002(3) 0.004(3) C1 0.046(4) 0.026(3) 0.036(3) 0.000(3) 0.003(3) 0.000(3) C9 0.040(4) 0.022(3) 0.036(3) -0.003(3) -0.005(3) 0.004(3) C11 0.051(5) 0.027(3) 0.052(4) -0.001(3) 0.005(4) 0.008(3) C2 0.058(4) 0.023(3) 0.036(3) -0.002(2) -0.002(4) 0.009(3) C5 0.053(4) 0.023(3) 0.046(4) 0.000(3) 0.005(3) 0.002(3) C10 0.048(4) 0.020(3) 0.039(3) 0.000(3) -0.002(3) -0.001(3) C23 0.054(5) 0.053(4) 0.046(4) 0.010(3) 0.006(4) -0.013(4) C7 0.043(4) 0.024(3) 0.062(4) 0.000(3) 0.004(3) 0.006(3) C8 0.051(4) 0.032(3) 0.047(4) -0.004(3) 0.007(4) 0.000(3) C25 0.057(5) 0.035(4) 0.047(4) 0.003(3) 0.003(4) 0.003(4) C21 0.058(5) 0.044(4) 0.056(4) 0.012(3) -0.001(4) 0.006(4) C22 0.056(5) 0.040(4) 0.056(4) 0.016(3) 0.003(4) -0.004(4) C3 0.041(4) 0.026(3) 0.044(4) -0.002(3) 0.003(3) 0.007(3) C14 0.049(4) 0.036(3) 0.038(4) -0.001(3) 0.005(3) 0.013(3) C20 0.047(4) 0.036(3) 0.041(4) 0.004(3) 0.000(4) -0.006(4) C13 0.041(4) 0.027(3) 0.041(3) -0.004(3) 0.008(3) 0.000(3) C24 0.058(5) 0.046(4) 0.046(4) 0.007(3) 0.006(4) 0.001(4) C15 0.035(4) 0.062(5) 0.051(4) -0.025(4) -0.001(3) 0.006(4) C171 0.109(15) 0.062(7) 0.041(5) -0.012(5) -0.005(10) 0.015(10) O131 0.025(6) 0.065(16) 0.056(13) -0.022(14) -0.009(7) 0.000(8) C181 0.061(7) 0.032(6) 0.054(9) 0.002(6) -0.012(9) 0.002(5) C172 0.109(15) 0.062(7) 0.041(5) -0.012(5) -0.005(10) 0.015(10) O132 0.027(10) 0.05(2) 0.05(2) -0.027(16) -0.004(11) -0.004(11) C182 0.061(7) 0.032(6) 0.054(9) 0.002(6) -0.012(9) 0.002(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Br C23 1.915(7) . ? O14 C14 1.426(8) . ? O14 C16 1.448(8) . ? N2 N1 1.333(7) . ? N2 C20 1.404(9) . ? N2 H2A 0.88 . ? O12 C13 1.418(7) . ? O12 H12O 0.84 . ? O11 C15 1.419(9) . ? O11 C12 1.426(8) . ? C16 C182 1.38(3) . ? C16 O131 1.39(2) . ? C16 O132 1.44(4) . ? C16 C171 1.502(15) . ? C16 C181 1.562(15) . ? C16 C172 1.57(3) . ? C4 N3 1.330(8) . ? C4 C3 1.395(9) . ? C4 C10 1.465(9) . ? N1 C1 1.310(8) . ? N3 C11 1.458(9) . ? N3 H3A 0.88 . ? O1 C2 1.288(7) . ? C6 C5 1.374(10) . ? C6 C7 1.386(9) . ? C6 H6 0.95 . ? C12 C11 1.501(9) . ? C12 C13 1.534(8) . ? C12 H12 1 . ? C1 C2 1.455(9) . ? C1 C9 1.491(8) . ? C9 C8 1.391(9) . ? C9 C10 1.409(9) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C2 C3 1.398(9) . ? C5 C10 1.414(8) . ? C5 H5 0.95 . ? C23 C22 1.340(11) . ? C23 C24 1.398(10) . ? C7 C8 1.383(9) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C25 C20 1.366(10) . ? C25 C24 1.378(10) . ? C25 H25 0.95 . ? C21 C22 1.393(10) . ? C21 C20 1.410(9) . ? C21 H21 0.95 . ? C22 H22 0.95 . ? C3 H3 0.95 . ? C14 C13 1.515(9) . ? C14 C15 1.519(11) . ? C14 H14 1 . ? C13 H13 1 . ? C24 H24 0.95 . ? C15 O131 1.385(18) . ? C15 O132 1.48(4) . ? C15 H15 1 . ? C171 H17A 0.98 . ? C171 H17B 0.98 . ? C171 H17C 0.98 . ? C181 H18A 0.98 . ? C181 H18B 0.98 . ? C181 H18C 0.98 . ? C172 H17D 0.98 . ? C172 H17E 0.98 . ? C172 H17F 0.98 . ? C182 H18D 0.98 . ? C182 H18E 0.98 . ? C182 H18F 0.98 . ? 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 O14 C16 109.0(5) . . ? N1 N2 C20 120.5(6) . . ? N1 N2 H2A 119.7 . . ? C20 N2 H2A 119.7 . . ? C13 O12 H12O 109.5 . . ? C15 O11 C12 109.0(5) . . ? C182 C16 O131 133(3) . . ? C182 C16 O132 109(4) . . ? O131 C16 O132 28.5(11) . . ? C182 C16 O14 112.4(15) . . ? O131 C16 O14 104.1(11) . . ? O132 C16 O14 107.1(9) . . ? C182 C16 C171 85.5(13) . . ? O131 C16 C171 112(3) . . ? O132 C16 C171 133(3) . . ? O14 C16 C171 107.3(8) . . ? C182 C16 C181 26.3(12) . . ? O131 C16 C181 114(3) . . ? O132 C16 C181 87(4) . . ? O14 C16 C181 107.7(7) . . ? C171 C16 C181 111.2(9) . . ? C182 C16 C172 112.9(16) . . ? O131 C16 C172 77(3) . . ? O132 C16 C172 102(4) . . ? O14 C16 C172 112.6(14) . . ? C171 C16 C172 34.7(13) . . ? C181 C16 C172 133.6(13) . . ? N3 C4 C3 121.8(6) . . ? N3 C4 C10 119.5(5) . . ? C3 C4 C10 118.7(6) . . ? C1 N1 N2 118.0(6) . . ? C4 N3 C11 125.4(5) . . ? C4 N3 H3A 117.3 . . ? C11 N3 H3A 117.3 . . ? C5 C6 C7 120.8(6) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? O11 C12 C11 108.7(6) . . ? O11 C12 C13 103.2(5) . . ? C11 C12 C13 119.5(5) . . ? O11 C12 H12 108.3 . . ? C11 C12 H12 108.3 . . ? C13 C12 H12 108.3 . . ? N1 C1 C2 125.6(6) . . ? N1 C1 C9 115.9(6) . . ? C2 C1 C9 118.5(6) . . ? C8 C9 C10 120.5(6) . . ? C8 C9 C1 120.4(6) . . ? C10 C9 C1 119.1(6) . . ? N3 C11 C12 113.6(6) . . ? N3 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N3 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? O1 C2 C3 120.9(6) . . ? O1 C2 C1 119.7(6) . . ? C3 C2 C1 119.5(5) . . ? C6 C5 C10 120.4(6) . . ? C6 C5 H5 119.8 . . ? C10 C5 H5 119.8 . . ? C9 C10 C5 118.1(6) . . ? C9 C10 C4 120.7(5) . . ? C5 C10 C4 121.2(6) . . ? C22 C23 C24 122.0(7) . . ? C22 C23 Br 118.9(6) . . ? C24 C23 Br 119.1(6) . . ? C8 C7 C6 120.0(6) . . ? C8 C7 H7 120 . . ? C6 C7 H7 120 . . ? C7 C8 C9 120.1(6) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C20 C25 C24 121.5(7) . . ? C20 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C22 C21 C20 119.0(7) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C23 C22 C21 120.1(7) . . ? C23 C22 H22 120 . . ? C21 C22 H22 120 . . ? C4 C3 C2 123.4(6) . . ? C4 C3 H3 118.3 . . ? C2 C3 H3 118.3 . . ? O14 C14 C13 111.4(6) . . ? O14 C14 C15 103.6(5) . . ? C13 C14 C15 104.2(5) . . ? O14 C14 H14 112.3 . . ? C13 C14 H14 112.3 . . ? C15 C14 H14 112.3 . . ? C25 C20 N2 124.4(6) . . ? C25 C20 C21 119.4(7) . . ? N2 C20 C21 116.1(7) . . ? O12 C13 C14 109.6(5) . . ? O12 C13 C12 110.0(5) . . ? C14 C13 C12 100.2(5) . . ? O12 C13 H13 112.1 . . ? C14 C13 H13 112.1 . . ? C12 C13 H13 112.1 . . ? C25 C24 C23 118.0(7) . . ? C25 C24 H24 121 . . ? C23 C24 H24 121 . . ? O131 C15 O11 125(3) . . ? O131 C15 O132 28.0(9) . . ? O11 C15 O132 97(4) . . ? O131 C15 C14 101.5(15) . . ? O11 C15 C14 106.5(6) . . ? O132 C15 C14 108.5(10) . . ? O131 C15 H15 107.6 . . ? O11 C15 H15 107.6 . . ? O132 C15 H15 127.3 . . ? C14 C15 H15 107.6 . . ? C16 C171 H17A 109.5 . . ? C16 C171 H17B 109.5 . . ? H17A C171 H17B 109.5 . . ? C16 C171 H17C 109.5 . . ? H17A C171 H17C 109.5 . . ? H17B C171 H17C 109.5 . . ? C15 O131 C16 111.9(15) . . ? C16 C181 H18A 109.5 . . ? C16 C181 H18B 109.5 . . ? H18A C181 H18B 109.5 . . ? C16 C181 H18C 109.5 . . ? H18A C181 H18C 109.5 . . ? H18B C181 H18C 109.5 . . ? C16 C172 H17D 109.5 . . ? C16 C172 H17E 109.5 . . ? H17D C172 H17E 109.5 . . ? C16 C172 H17F 109.5 . . ? H17D C172 H17F 109.5 . . ? H17E C172 H17F 109.5 . . ? C16 O132 C15 104(4) . . ? C16 C182 H18D 109.5 . . ? C16 C182 H18E 109.5 . . ? H18D C182 H18E 109.5 . . ? C16 C182 H18F 109.5 . . ? H18D C182 H18F 109.5 . . ? H18E C182 H18F 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 C14 O14 C16 C182 148.5(15) . . . . ? C14 O14 C16 O131 -1(3) . . . . ? C14 O14 C16 O132 29(4) . . . . ? C14 O14 C16 C171 -119.3(9) . . . . ? C14 O14 C16 C181 120.9(8) . . . . ? C14 O14 C16 C172 -82.7(17) . . . . ? C20 N2 N1 C1 -178.7(6) . . . . ? C3 C4 N3 C11 -0.7(11) . . . . ? C10 C4 N3 C11 177.4(6) . . . . ? C15 O11 C12 C11 -162.4(5) . . . . ? C15 O11 C12 C13 -34.5(6) . . . . ? N2 N1 C1 C2 -0.9(10) . . . . ? N2 N1 C1 C9 -179.2(6) . . . . ? N1 C1 C9 C8 -3.8(9) . . . . ? C2 C1 C9 C8 177.7(6) . . . . ? N1 C1 C9 C10 176.0(6) . . . . ? C2 C1 C9 C10 -2.5(9) . . . . ? C4 N3 C11 C12 -150.0(7) . . . . ? O11 C12 C11 N3 61.6(7) . . . . ? C13 C12 C11 N3 -56.3(9) . . . . ? N1 C1 C2 O1 3.4(11) . . . . ? C9 C1 C2 O1 -178.3(6) . . . . ? N1 C1 C2 C3 -175.9(6) . . . . ? C9 C1 C2 C3 2.3(10) . . . . ? C7 C6 C5 C10 -0.1(11) . . . . ? C8 C9 C10 C5 1.4(10) . . . . ? C1 C9 C10 C5 -178.4(6) . . . . ? C8 C9 C10 C4 179.9(6) . . . . ? C1 C9 C10 C4 0.2(9) . . . . ? C6 C5 C10 C9 -1.2(10) . . . . ? C6 C5 C10 C4 -179.7(7) . . . . ? N3 C4 C10 C9 -175.9(6) . . . . ? C3 C4 C10 C9 2.3(10) . . . . ? N3 C4 C10 C5 2.6(10) . . . . ? C3 C4 C10 C5 -179.1(6) . . . . ? C5 C6 C7 C8 1.2(11) . . . . ? C6 C7 C8 C9 -1.0(10) . . . . ? C10 C9 C8 C7 -0.3(10) . . . . ? C1 C9 C8 C7 179.5(6) . . . . ? C24 C23 C22 C21 -2.1(12) . . . . ? Br C23 C22 C21 178.8(6) . . . . ? C20 C21 C22 C23 -0.2(12) . . . . ? N3 C4 C3 C2 175.6(7) . . . . ? C10 C4 C3 C2 -2.6(10) . . . . ? O1 C2 C3 C4 -179.1(7) . . . . ? C1 C2 C3 C4 0.2(10) . . . . ? C16 O14 C14 C13 -129.0(6) . . . . ? C16 O14 C14 C15 -17.5(7) . . . . ? C24 C25 C20 N2 178.4(7) . . . . ? C24 C25 C20 C21 -1.2(11) . . . . ? N1 N2 C20 C25 -4.0(10) . . . . ? N1 N2 C20 C21 175.6(6) . . . . ? C22 C21 C20 C25 1.8(11) . . . . ? C22 C21 C20 N2 -177.8(7) . . . . ? O14 C14 C13 O12 -165.6(5) . . . . ? C15 C14 C13 O12 83.3(6) . . . . ? O14 C14 C13 C12 78.7(7) . . . . ? C15 C14 C13 C12 -32.4(7) . . . . ? O11 C12 C13 O12 -74.6(6) . . . . ? C11 C12 C13 O12 46.1(9) . . . . ? O11 C12 C13 C14 40.8(6) . . . . ? C11 C12 C13 C14 161.5(6) . . . . ? C20 C25 C24 C23 -1.0(11) . . . . ? C22 C23 C24 C25 2.7(12) . . . . ? Br C23 C24 C25 -178.2(6) . . . . ? C12 O11 C15 O131 -104.0(12) . . . . ? C12 O11 C15 O132 -98.4(14) . . . . ? C12 O11 C15 C14 13.4(7) . . . . ? O14 C14 C15 O131 29(3) . . . . ? C13 C14 C15 O131 145(3) . . . . ? O14 C14 C15 O11 -103.3(6) . . . . ? C13 C14 C15 O11 13.4(7) . . . . ? O14 C14 C15 O132 1(4) . . . . ? C13 C14 C15 O132 117(4) . . . . ? O11 C15 O131 C16 88(5) . . . . ? O132 C15 O131 C16 76(5) . . . . ? C14 C15 O131 C16 -32(6) . . . . ? C182 C16 O131 C15 -119(4) . . . . ? O132 C16 O131 C15 -79(5) . . . . ? O14 C16 O131 C15 21(6) . . . . ? C171 C16 O131 C15 137(4) . . . . ? C181 C16 O131 C15 -96(5) . . . . ? C172 C16 O131 C15 132(6) . . . . ? C182 C16 O132 C15 -149(4) . . . . ? O131 C16 O132 C15 61(5) . . . . ? O14 C16 O132 C15 -27(6) . . . . ? C171 C16 O132 C15 109(2) . . . . ? C181 C16 O132 C15 -134(5) . . . . ? C172 C16 O132 C15 92(5) . . . . ? O131 C15 O132 C16 -64(4) . . . . ? O11 C15 O132 C16 126(5) . . . . ? C14 C15 O132 C16 16(6) . . . . ? 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 N2 H2A O1 0.88 1.83 2.536(7) 135.8 . N3 H3A O12 0.88 2.03 2.713(7) 133.2 . O12 H12O O1 0.84 1.84 2.645(6) 160.3 3_545 C7 H7 O11 0.95 2.53 3.275(7) 135.6 3_645 C15 H15 O14 1 2.32 3.154(9) 140.5 1_655 # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF