data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Fernando Cossio' _publ_contact_author_address ; Organic Chemistry I University of the Basque Country (UPV/EHU) Facultad de Quimica, P. O. Box 1072 Edificio Korta, Avda. de Tolosa, 72 San Sebastian - Donostia Gipuzkoa 20018 SPAIN ; _publ_contact_author_email FP.COSSIO@EHU.ES _publ_section_title ; Regiochemistry of the microwave-assisted reaction between aromatic amines and alpha-bromoketones to yield substituted 1H-Indoles ; _publ_requested_category FO loop_ _publ_author_name 'Fernando Cossio' 'Eneko Aldaba' 'Ana Arrieta' 'Jose L. Pizarro' 'Yosu Vara' data_fc9abs _database_code_depnum_ccdc_archive 'CCDC 605924' _audit_creation_date 2005-03-30T17:09:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C72 H76 N4 O16' _chemical_formula_weight 1253.37 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.5050(10) _cell_length_b 10.7366(7) _cell_length_c 10.6755(10) _cell_angle_alpha 90 _cell_angle_beta 100.855(7) _cell_angle_gamma 90 _cell_volume 1632.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 31.8517 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.20974 _exptl_crystal_size_mid 0.10778 _exptl_crystal_size_min 0.02684 _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_type 'numeric analytical' _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.24 beta (release 23.09.2004 CrysAlis171 .NET) (compiled Sep 23 2004,08:58:26) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _exptl_absorpt_correction_T_min 0.97472 _exptl_absorpt_correction_T_max 0.99431 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 8.3504 _diffrn_orient_matrix_ub_11 -0.0226544536 _diffrn_orient_matrix_ub_12 0.0588227688 _diffrn_orient_matrix_ub_13 -0.0065694168 _diffrn_orient_matrix_ub_21 0.0443369295 _diffrn_orient_matrix_ub_22 0.0300453766 _diffrn_orient_matrix_ub_23 0.0102234536 _diffrn_orient_matrix_ub_31 -0.0004850723 _diffrn_orient_matrix_ub_32 -0.0011944617 _diffrn_orient_matrix_ub_33 -0.0665514037 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_unetI/netI 0.0478 _diffrn_reflns_number 11596 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 3308 _reflns_number_gt 2269 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.24 beta (release 23.09.2004 CrysAlis171 .NET) (compiled Sep 23 2004,08:58:26) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.24 beta (release 23.09.2004 CrysAlis171 .NET) (compiled Sep 23 2004,08:58:26) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.24 beta (release 23.09.2004 CrysAlis171 .NET) (compiled Sep 23 2004,08:58:26) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0620P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3308 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1363 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.162 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # 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' 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' H H 0 0 '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 C1 C 0.46193(13) 0.41141(18) 0.61644(17) 0.0428(5) Uani 1 1 d . . . C2 C 0.36884(15) 0.4448(2) 0.6106(2) 0.0541(6) Uani 1 1 d . . . H2 H 0.3536 0.5114 0.6585 0.065 Uiso 1 1 calc R . . C3 C 0.29928(15) 0.3785(2) 0.5335(2) 0.0613(6) Uani 1 1 d . . . C4 C 0.32139(15) 0.2796(2) 0.4622(2) 0.0604(6) Uani 1 1 d . . . H4 H 0.2742 0.2347 0.4103 0.072 Uiso 1 1 calc R . . C5 C 0.41372(14) 0.24828(19) 0.46893(19) 0.0508(5) Uani 1 1 d . . . H5 H 0.428 0.1818 0.42 0.061 Uiso 1 1 calc R . . C6 C 0.48720(12) 0.31153(17) 0.54572(16) 0.0392(5) Uani 1 1 d . . . C7 C 0.58337(13) 0.26936(17) 0.55005(16) 0.0398(5) Uani 1 1 d . . . C8 C 0.61509(14) 0.18192(17) 0.47490(18) 0.0419(5) Uani 1 1 d . . . C9 C 0.71175(13) 0.16487(17) 0.52012(17) 0.0417(5) Uani 1 1 d . . . C10 C 0.73866(14) 0.24515(18) 0.62390(19) 0.0468(5) Uani 1 1 d . . . C11 C 0.83005(14) 0.2525(2) 0.6932(2) 0.0600(6) Uani 1 1 d . . . H11 H 0.8462 0.3065 0.7619 0.072 Uiso 1 1 calc R . . C12 C 0.89447(15) 0.1761(2) 0.6547(2) 0.0649(7) Uani 1 1 d . . . C13 C 0.87099(14) 0.0934(2) 0.5513(2) 0.0571(6) Uani 1 1 d . . . H13 H 0.9168 0.0421 0.5286 0.068 Uiso 1 1 calc R . . C14 C 0.78084(14) 0.08831(18) 0.48410(18) 0.0464(5) Uani 1 1 d . . . C15 C 0.51392(17) 0.57477(19) 0.7675(2) 0.0606(6) Uani 1 1 d . . . H15A H 0.479 0.6367 0.7135 0.091 Uiso 1 1 calc R . . H15B H 0.5715 0.6104 0.8122 0.091 Uiso 1 1 calc R . . H15C H 0.4774 0.5458 0.828 0.091 Uiso 1 1 calc R . . C16 C 0.1779(2) 0.5045(3) 0.5935(3) 0.1077(11) Uani 1 1 d . . . H16A H 0.1993 0.4892 0.6829 0.162 Uiso 1 1 calc R . . H16B H 0.1108 0.512 0.5762 0.162 Uiso 1 1 calc R . . H16C H 0.2054 0.5803 0.5699 0.162 Uiso 1 1 calc R . . C17 C 1.01798(18) 0.2550(4) 0.8142(3) 0.1313(15) Uani 1 1 d . . . H17A H 1.0108 0.3385 0.7818 0.197 Uiso 1 1 calc R . . H17B H 1.0828 0.2398 0.8498 0.197 Uiso 1 1 calc R . . H17C H 0.981 0.2444 0.8792 0.197 Uiso 1 1 calc R . . C18 C 0.81453(19) -0.0744(2) 0.3464(3) 0.0784(7) Uani 1 1 d . . . H18A H 0.8668 -0.0312 0.3232 0.118 Uiso 1 1 calc R . . H18B H 0.7836 -0.1231 0.2754 0.118 Uiso 1 1 calc R . . H18C H 0.8366 -0.1283 0.4175 0.118 Uiso 1 1 calc R . . N1 N 0.65936(11) 0.30756(16) 0.64009(16) 0.0462(4) Uani 1 1 d . . . O1 O 0.53438(9) 0.47284(12) 0.69174(12) 0.0521(4) Uani 1 1 d . . . O2 O 0.20508(11) 0.40348(18) 0.52179(19) 0.0898(6) Uani 1 1 d . . . O3 O 0.98752(11) 0.1699(2) 0.71390(18) 0.0998(7) Uani 1 1 d . . . O4 O 0.75001(10) 0.01397(14) 0.38097(13) 0.0599(4) Uani 1 1 d . . . H1 H 0.6556(15) 0.368(2) 0.692(2) 0.063(7) Uiso 1 1 d . . . H8 H 0.5751(14) 0.1384(17) 0.4017(18) 0.055(6) Uiso 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 C1 0.0419(11) 0.0454(11) 0.0408(10) 0.0064(9) 0.0067(9) 0.0055(9) C2 0.0539(13) 0.0547(13) 0.0549(12) 0.0020(11) 0.0136(11) 0.0129(11) C3 0.0400(12) 0.0692(15) 0.0738(15) 0.0086(13) 0.0083(11) 0.0115(11) C4 0.0427(13) 0.0671(14) 0.0676(14) 0.0016(12) 0.0006(11) -0.0002(11) C5 0.0448(13) 0.0521(13) 0.0534(12) -0.0006(10) 0.0037(10) 0.0054(10) C6 0.0389(11) 0.0422(11) 0.0358(10) 0.0049(9) 0.0057(8) 0.0038(9) C7 0.0412(11) 0.0407(11) 0.0365(10) 0.0036(9) 0.0053(9) 0.0006(9) C8 0.0430(11) 0.0427(11) 0.0393(10) -0.0024(9) 0.0055(9) 0.0024(9) C9 0.0430(11) 0.0436(11) 0.0396(10) 0.0025(9) 0.0106(9) 0.0041(9) C10 0.0408(11) 0.0528(12) 0.0475(11) -0.0033(10) 0.0100(9) 0.0049(9) C11 0.0423(13) 0.0762(16) 0.0579(13) -0.0194(11) 0.0002(10) 0.0046(11) C12 0.0387(12) 0.0883(18) 0.0660(14) -0.0115(13) 0.0053(11) 0.0128(12) C13 0.0455(13) 0.0673(14) 0.0603(13) -0.0083(12) 0.0148(11) 0.0152(11) C14 0.0473(12) 0.0496(11) 0.0434(11) -0.0027(10) 0.0115(9) 0.0057(10) C15 0.0778(16) 0.0492(12) 0.0543(13) -0.0103(11) 0.0116(12) 0.0143(11) C16 0.0605(17) 0.123(2) 0.146(3) -0.008(2) 0.0342(18) 0.0364(18) C17 0.0427(15) 0.200(4) 0.136(3) -0.084(3) -0.0238(16) 0.0152(19) C18 0.0791(17) 0.0735(16) 0.0846(17) -0.0254(14) 0.0206(14) 0.0216(14) N1 0.0387(10) 0.0530(10) 0.0457(10) -0.0118(9) 0.0044(8) 0.0070(8) O1 0.0523(8) 0.0504(8) 0.0512(8) -0.0118(7) 0.0033(7) 0.0097(7) O2 0.0430(10) 0.1061(14) 0.1182(15) -0.0074(12) 0.0101(9) 0.0176(10) O3 0.0394(9) 0.1420(17) 0.1088(14) -0.0488(13) -0.0096(9) 0.0244(10) O4 0.0554(9) 0.0639(9) 0.0608(9) -0.0170(8) 0.0117(7) 0.0139(8) #----------------------------------------------------------------------------# # 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 C1 O1 1.367(2) . ? C1 C2 1.387(3) . ? C1 C6 1.399(3) . ? C2 C3 1.374(3) . ? C3 O2 1.375(3) . ? C3 C4 1.379(3) . ? C4 C5 1.370(3) . ? C5 C6 1.393(3) . ? C6 C7 1.459(3) . ? C7 C8 1.370(3) . ? C7 N1 1.381(2) . ? C8 C9 1.406(3) . ? C9 C10 1.400(3) . ? C9 C14 1.405(3) . ? C10 N1 1.370(2) . ? C10 C11 1.393(3) . ? C11 C12 1.363(3) . ? C12 O3 1.380(3) . ? C12 C13 1.408(3) . ? C13 C14 1.369(3) . ? C14 O4 1.365(2) . ? C15 O1 1.425(2) . ? C16 O2 1.425(3) . ? C17 O3 1.413(3) . ? C18 O4 1.429(3) . ? 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 O1 C1 C2 122.41(18) . . ? O1 C1 C6 115.89(16) . . ? C2 C1 C6 121.69(19) . . ? C3 C2 C1 119.5(2) . . ? C2 C3 O2 124.0(2) . . ? C2 C3 C4 120.55(19) . . ? O2 C3 C4 115.5(2) . . ? C5 C4 C3 119.1(2) . . ? C4 C5 C6 122.9(2) . . ? C5 C6 C1 116.23(17) . . ? C5 C6 C7 119.24(17) . . ? C1 C6 C7 124.51(17) . . ? C8 C7 N1 107.40(17) . . ? C8 C7 C6 128.23(17) . . ? N1 C7 C6 124.25(16) . . ? C7 C8 C9 108.14(17) . . ? C10 C9 C14 118.03(17) . . ? C10 C9 C8 107.63(16) . . ? C14 C9 C8 134.34(18) . . ? N1 C10 C11 130.02(18) . . ? N1 C10 C9 106.58(17) . . ? C11 C10 C9 123.39(18) . . ? C12 C11 C10 116.36(19) . . ? C11 C12 O3 123.9(2) . . ? C11 C12 C13 122.49(19) . . ? O3 C12 C13 113.57(19) . . ? C14 C13 C12 120.14(19) . . ? O4 C14 C13 125.55(18) . . ? O4 C14 C9 114.87(17) . . ? C13 C14 C9 119.58(18) . . ? C10 N1 C7 110.24(16) . . ? C1 O1 C15 119.04(16) . . ? C3 O2 C16 118.0(2) . . ? C12 O3 C17 117.06(18) . . ? C14 O4 C18 117.72(17) . . ?