# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef 'archive_jb87.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2011-02-15 _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 ? #------------------ AUTHOR DETAILS -------------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Molins, E.' _publ_contact_author_address ; Department of Crystallography ICMAB-CSIC Campus UAB Bellaterra, ES ; _publ_contact_author_email elies.molins@icmab.es _publ_contact_author_fax +(34)935805729 _publ_contact_author_phone +(34)935801853 # Insert blank lines between references _publ_section_references ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. Blessing, R. H. (1987) Cryst. Rev. 1, 3-58. Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397. Bruker (2007) APEX2 (Version 2.1-4), SAINT (version 7.34A), SADABS (version 2007/4), BrukerAXS Inc, Madison, Wisconsin, USA. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Flack H. D. & Bernardinelli, G. (71999). Acta Cryst. A55, 908-915. Flack H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148. Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580 LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968) Acta Cryst, A24, 351-359 Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr. 34, 824-828 Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr. 35, 281. ABSCOR: Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. APEX, APEX2, SMART, SAINT, SAINT-Plus: Bruker (2007). Program name(s). Bruker AXS Inc., Madison, Wisconsin, USA. [Older versions (pre-1997) should refer to Siemens Analytical X-ray Instruments Inc. instead of Bruker AXS.] CAD-4 Software: Enraf-Nonius (1989). CAD-4 Software (or CAD-4 EXPRESS). Enraf-Nonius, Delft, The Netherlands. Cambridge Structural Database: Allen, F. R. (2002). Acta Cryst. B58, 380-388. CAMERON: Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England. CrysAlis CCD, CrysAlis RED and associated programs: Oxford Diffraction (2006). Program name(s). Oxford Diffraction Ltd, Abingdon, England. CRYSTALS: Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. COLLECT: Nonius [or Hooft, R. W. W.] (1998). COLLECT. Nonius BV, Delft, The Netherlands. DENZO/SCALEPACK: Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press. DIAMOND: Brandenburg, K. [or Brandenburg, K. & Putz, H., or Brandenburg, K. & Berndt, M.] (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. DIF4 and REDU4: Stoe & Cie (1991). Program name(s). Stoe & Cie, Darmstadt, Germany. DIFABS: Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158 - 166. DIRAX: Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96. DIRDIF99: Beurskens, P.T., Beurskens, G., de Gelder, R., Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. enCIFer: Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338. EVALCCD: Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229. JANA2000: Petricek, V. & Dusek, M. (2000). JANA2000. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic. Mercury: Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457. Mogul: Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133-2144. ORTEPII: Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. ORTEPIII: Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. PARST: Nardelli, M. (1995). J. Appl. Cryst. 28, 659. PLATON: Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. PROCESS: Rigaku (1996). PROCESS. Rigaku Corporation, Tokyo, Japan. PROCESS-AUTO: Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. publCIF: Westrip, S. P. (2008). publCIF. In preparation. SADABS, TWINABS: Bruker (2001). Program name. Bruker AXS Inc., Madison, Wisconsin, USA. or Sheldrick, G. M. (1996). Program name. University of G ttingen, Germany. SHELX Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. SIR92: Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. SIR97: Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. SIR2002: Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. SUPERFLIP Palatinus, L. & Chapuis, G. (2007) J. Appl. Cryst. 40, 786-790. TEXSAN: Molecular Structure Corporation & Rigaku (2000). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. WinGX: Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. X-AREA, X-RED, X-RED32, X-SHAPE: Stoe & Cie (2002). Program name(s). Stoe & Cie GmbH, Darmstadt, Germany. XCAD4: Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. XSCANS: Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _publ_requested_category FO loop_ _publ_author_name 'Vladislav Semak' 'Carmen Escolano' 'Elies Molins' 'Joan Bosch' 'Mercedes Amat' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_jb87 _database_code_depnum_ccdc_archive 'CCDC 861638' #TrackingRef 'archive_jb87.cif' _audit_creation_date 2011-02-15T12:25:22-00:00 _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 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H25 N1 O2' _chemical_formula_sum 'C18 H25 N O2' _chemical_formula_weight 287.39 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.938(3) _cell_length_b 23.823(4) _cell_length_c 9.277(3) _cell_angle_alpha 90 _cell_angle_beta 104.96(3) _cell_angle_gamma 90 _cell_volume 1694.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 12.1 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.024 _exptl_crystal_density_diffrn 1.126 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166 ; _exptl_absorpt_correction_T_min 0.7774 _exptl_absorpt_correction_T_max 0.9983 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 0.069463 _diffrn_orient_matrix_ub_12 0.025334 _diffrn_orient_matrix_ub_13 0.079312 _diffrn_orient_matrix_ub_21 0.001098 _diffrn_orient_matrix_ub_22 -0.029584 _diffrn_orient_matrix_ub_23 0.076725 _diffrn_orient_matrix_ub_31 0.110276 _diffrn_orient_matrix_ub_32 -0.015646 _diffrn_orient_matrix_ub_33 -0.016653 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled \w scans' _diffrn_standards_number 1 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -7 0 _diffrn_reflns_av_unetI/netI 0.0906 _diffrn_reflns_number 3691 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 26.97 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3691 _reflns_number_gt 1335 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _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^)+(0.0607P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3691 _refine_ls_number_parameters 210 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.1709 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1479 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_restrained_S_all 0.888 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.149 _refine_diff_density_min -0.114 _refine_diff_density_rms 0.031 #----------------------------------------------------------------------------# # 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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 O2 O 0.5781(2) 0.25120(8) 0.3440(2) 0.0796(6) Uani 1 1 d . . . O8 O 0.2238(2) 0.14598(7) 0.3330(2) 0.0711(6) Uani 1 1 d . . . H8 H 0.1807 0.1763 0.3458 0.107 Uiso 1 1 calc R . . N1 N 0.5458(2) 0.16299(8) 0.2535(2) 0.0520(5) Uani 1 1 d . . . C2 C 0.6287(3) 0.20166(12) 0.3503(3) 0.0589(7) Uani 1 1 d . . . C3 C 0.7840(3) 0.18394(13) 0.4734(3) 0.0784(9) Uani 1 1 d . . . H3A H 0.8867 0.2009 0.4533 0.094 Uiso 1 1 calc R . . H3B H 0.7705 0.2002 0.5656 0.094 Uiso 1 1 calc R . . C4 C 0.8207(4) 0.12275(14) 0.5004(3) 0.0833(9) Uani 1 1 d . . . H4A H 0.8357 0.115 0.6057 0.1 Uiso 1 1 calc R . . H4B H 0.9296 0.1138 0.4766 0.1 Uiso 1 1 calc R . . C5 C 0.6792(3) 0.08467(12) 0.4106(3) 0.0638(7) Uani 1 1 d . . . H5 H 0.5794 0.0879 0.4541 0.077 Uiso 1 1 calc R . . C6 C 0.6193(3) 0.10656(10) 0.2517(3) 0.0556(7) Uani 1 1 d . B . H6 H 0.5246 0.0821 0.198 0.067 Uiso 1 1 calc R . . C7 C 0.3761(3) 0.17668(10) 0.1496(3) 0.0540(6) Uani 1 1 d . . . H7 H 0.351 0.2157 0.1708 0.065 Uiso 1 1 calc R . . C8 C 0.2312(3) 0.14159(10) 0.1836(3) 0.0611(7) Uani 1 1 d . . . H8A H 0.1204 0.1535 0.119 0.073 Uiso 1 1 calc R . . H8B H 0.2487 0.1026 0.1614 0.073 Uiso 1 1 calc R . . C9 C 0.3863(3) 0.17579(11) -0.0114(3) 0.0577(7) Uani 1 1 d . . . C10 C 0.3014(4) 0.13765(12) -0.1139(3) 0.0742(8) Uani 1 1 d . . . H10 H 0.2333 0.1102 -0.0855 0.089 Uiso 1 1 calc R . . C11 C 0.3149(4) 0.13907(15) -0.2610(4) 0.0900(10) Uani 1 1 d . . . H11 H 0.2547 0.1131 -0.3301 0.108 Uiso 1 1 calc R . . C12 C 0.4161(5) 0.17854(17) -0.3028(4) 0.0927(10) Uani 1 1 d . . . H12 H 0.4268 0.179 -0.4003 0.111 Uiso 1 1 calc R . . C13 C 0.5020(4) 0.21742(15) -0.2031(4) 0.0941(10) Uani 1 1 d . . . H13 H 0.5708 0.2447 -0.2318 0.113 Uiso 1 1 calc R . . C14 C 0.4853(4) 0.21568(13) -0.0580(3) 0.0781(8) Uani 1 1 d . . . H14 H 0.5431 0.2424 0.01 0.094 Uiso 1 1 calc R . . C51 C 0.7321(4) 0.02305(12) 0.4207(3) 0.0843(9) Uani 1 1 d . . . H51A H 0.6418 0.0016 0.3525 0.101 Uiso 1 1 calc R . . H51B H 0.8385 0.0191 0.3886 0.101 Uiso 1 1 calc R . . C52 C 0.7614(4) -0.00145(15) 0.5765(4) 0.1102(12) Uani 1 1 d . . . H52A H 0.8556 0.018 0.6436 0.165 Uiso 1 1 calc R . . H52B H 0.7899 -0.0406 0.5745 0.165 Uiso 1 1 calc R . . H52C H 0.6572 0.0027 0.6098 0.165 Uiso 1 1 calc R . . C61 C 0.7618(4) 0.10561(13) 0.1649(3) 0.0811(9) Uani 1 1 d D . . H61A H 0.7357 0.1354 0.0913 0.097 Uiso 1 1 calc R A 1 H61B H 0.872 0.115 0.2346 0.097 Uiso 1 1 calc R A 1 C62 C 0.7875(14) 0.0544(4) 0.0885(10) 0.101(3) Uani 0.5 1 d PDU B 1 H62 H 0.846 0.0245 0.1439 0.122 Uiso 0.5 1 calc PR B 1 C63 C 0.731(2) 0.0495(7) -0.0547(10) 0.216(9) Uani 0.5 1 d PD B 1 H63A H 0.6725 0.0791 -0.1112 0.259 Uiso 0.5 1 calc PR B 1 H63B H 0.7491 0.0162 -0.1011 0.259 Uiso 0.5 1 calc PR B 1 C62D C 0.7221(16) 0.0662(7) 0.0434(16) 0.181(8) Uani 0.5 1 d PDU B 2 H62D H 0.6122 0.0685 -0.0228 0.218 Uiso 0.5 1 calc PR B 2 C63D C 0.8240(18) 0.0286(4) 0.0188(16) 0.171(5) Uani 0.5 1 d PDU B 2 H63C H 0.9351 0.0248 0.0823 0.206 Uiso 0.5 1 calc PR B 2 H63D H 0.7877 0.0047 -0.0627 0.206 Uiso 0.5 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 O2 0.0825(13) 0.0593(12) 0.1003(16) -0.0205(12) 0.0295(11) -0.0158(11) O8 0.0758(13) 0.0700(14) 0.0757(14) 0.0131(10) 0.0347(10) 0.0123(10) N1 0.0498(11) 0.0531(13) 0.0529(13) -0.0041(11) 0.0128(10) -0.0040(10) C2 0.0605(16) 0.0591(18) 0.0641(18) -0.0109(16) 0.0285(14) -0.0132(15) C3 0.0698(18) 0.099(3) 0.0630(19) -0.0079(18) 0.0118(16) -0.0300(17) C4 0.0769(19) 0.094(2) 0.073(2) 0.0047(18) 0.0069(16) -0.0044(19) C5 0.0495(14) 0.0707(19) 0.0713(19) 0.0095(16) 0.0154(14) 0.0026(14) C6 0.0519(14) 0.0532(16) 0.0614(18) -0.0038(13) 0.0139(13) 0.0013(12) C7 0.0533(15) 0.0517(15) 0.0568(16) 0.0020(13) 0.0141(12) 0.0018(13) C8 0.0517(15) 0.0593(17) 0.0716(19) -0.0002(14) 0.0148(14) 0.0037(12) C9 0.0556(15) 0.0591(17) 0.0553(17) 0.0006(14) 0.0086(13) 0.0006(13) C10 0.0757(19) 0.081(2) 0.064(2) -0.0054(17) 0.0146(16) -0.0088(16) C11 0.090(2) 0.100(3) 0.070(2) -0.0177(19) 0.0013(18) -0.003(2) C12 0.091(2) 0.121(3) 0.064(2) 0.004(2) 0.0155(19) 0.010(2) C13 0.098(2) 0.117(3) 0.067(2) 0.020(2) 0.023(2) -0.017(2) C14 0.090(2) 0.083(2) 0.059(2) 0.0057(16) 0.0159(16) -0.0192(17) C51 0.0692(18) 0.081(2) 0.104(3) 0.024(2) 0.0236(17) 0.0158(17) C52 0.100(3) 0.110(3) 0.123(3) 0.047(2) 0.033(2) 0.022(2) C61 0.080(2) 0.095(2) 0.075(2) -0.0044(18) 0.0326(17) 0.0106(18) C62 0.107(8) 0.110(7) 0.103(8) 0.007(6) 0.057(6) 0.069(6) C63 0.202(13) 0.33(2) 0.092(9) -0.085(11) -0.009(8) 0.141(12) C62D 0.099(8) 0.304(19) 0.127(11) -0.081(12) 0.003(7) 0.096(9) C63D 0.209(14) 0.152(11) 0.179(12) -0.030(10) 0.097(11) 0.022(10) #----------------------------------------------------------------------------# # 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 O2 C2 1.243(3) . ? O8 C8 1.406(3) . ? N1 C2 1.335(3) . ? N1 C6 1.467(3) . ? N1 C7 1.477(3) . ? C2 C3 1.508(4) . ? C3 C4 1.495(4) . ? C4 C5 1.515(4) . ? C5 C6 1.519(3) . ? C5 C51 1.523(4) . ? C6 C61 1.549(3) . ? C7 C9 1.516(3) . ? C7 C8 1.519(3) . ? C9 C10 1.361(3) . ? C9 C14 1.372(3) . ? C10 C11 1.397(4) . ? C11 C12 1.356(4) . ? C12 C13 1.361(4) . ? C13 C14 1.387(4) . ? C51 C52 1.520(4) . ? C61 C62D 1.439(8) . ? C61 C62 1.451(7) . ? C62 C63 1.293(8) . ? C62D C63D 1.266(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 120.7(2) . . ? C2 N1 C7 119.7(2) . . ? C6 N1 C7 119.57(19) . . ? O2 C2 N1 121.8(3) . . ? O2 C2 C3 119.5(3) . . ? N1 C2 C3 118.7(3) . . ? C4 C3 C2 119.1(2) . . ? C3 C4 C5 114.0(2) . . ? C4 C5 C6 109.3(2) . . ? C4 C5 C51 112.9(2) . . ? C6 C5 C51 113.7(2) . . ? N1 C6 C5 109.20(19) . . ? N1 C6 C61 111.4(2) . . ? C5 C6 C61 114.3(2) . . ? N1 C7 C9 111.59(19) . . ? N1 C7 C8 110.78(19) . . ? C9 C7 C8 115.7(2) . . ? O8 C8 C7 113.0(2) . . ? C10 C9 C14 117.5(3) . . ? C10 C9 C7 123.7(2) . . ? C14 C9 C7 118.8(2) . . ? C9 C10 C11 121.2(3) . . ? C12 C11 C10 119.8(3) . . ? C11 C12 C13 120.5(3) . . ? C12 C13 C14 118.8(3) . . ? C9 C14 C13 122.2(3) . . ? C52 C51 C5 113.6(3) . . ? C62D C61 C6 112.0(7) . . ? C62 C61 C6 118.7(5) . . ? C63 C62 C61 121.5(9) . . ? C63D C62D C61 125.6(11) . . ? 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 C6 N1 C2 O2 172.7(2) . . . . ? C7 N1 C2 O2 -8.8(3) . . . . ? C6 N1 C2 C3 -9.6(3) . . . . ? C7 N1 C2 C3 169.0(2) . . . . ? O2 C2 C3 C4 166.8(3) . . . . ? N1 C2 C3 C4 -11.0(4) . . . . ? C2 C3 C4 C5 -7.7(4) . . . . ? C3 C4 C5 C6 43.0(3) . . . . ? C3 C4 C5 C51 170.7(2) . . . . ? C2 N1 C6 C5 46.4(3) . . . . ? C7 N1 C6 C5 -132.1(2) . . . . ? C2 N1 C6 C61 -80.9(3) . . . . ? C7 N1 C6 C61 100.6(2) . . . . ? C4 C5 C6 N1 -61.7(3) . . . . ? C51 C5 C6 N1 171.09(19) . . . . ? C4 C5 C6 C61 63.9(3) . . . . ? C51 C5 C6 C61 -63.3(3) . . . . ? C2 N1 C7 C9 115.4(2) . . . . ? C6 N1 C7 C9 -66.0(3) . . . . ? C2 N1 C7 C8 -114.2(2) . . . . ? C6 N1 C7 C8 64.4(3) . . . . ? N1 C7 C8 O8 54.3(3) . . . . ? C9 C7 C8 O8 -177.5(2) . . . . ? N1 C7 C9 C10 113.5(3) . . . . ? C8 C7 C9 C10 -14.3(4) . . . . ? N1 C7 C9 C14 -67.0(3) . . . . ? C8 C7 C9 C14 165.2(2) . . . . ? C14 C9 C10 C11 0.1(4) . . . . ? C7 C9 C10 C11 179.6(3) . . . . ? C9 C10 C11 C12 0.9(5) . . . . ? C10 C11 C12 C13 -1.2(5) . . . . ? C11 C12 C13 C14 0.5(5) . . . . ? C10 C9 C14 C13 -0.9(4) . . . . ? C7 C9 C14 C13 179.6(3) . . . . ? C12 C13 C14 C9 0.6(5) . . . . ? C4 C5 C51 C52 64.8(3) . . . . ? C6 C5 C51 C52 -169.9(2) . . . . ? N1 C6 C61 C62D -122.4(8) . . . . ? C5 C6 C61 C62D 113.1(8) . . . . ? N1 C6 C61 C62 -149.9(5) . . . . ? C5 C6 C61 C62 85.6(5) . . . . ? C62D C61 C62 C63 23(2) . . . . ? C6 C61 C62 C63 103.8(13) . . . . ? C62 C61 C62D C63D -18.1(14) . . . . ? C6 C61 C62D C63D -128.7(18) . . . . ? # END of CIF