# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email WENTRUP@UQ.EDU.AU _publ_contact_author_name 'Prof Curt Wentrup' _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_address ; Brisbane 4072 AUSTRALIA ; _publ_section_title ; Diazepins.2.Synthesis of 1,3-diazepines and ring contraction to cyanopyrroles ; loop_ _publ_author_name 'Curt Wentrup' 'Paul V. Bernhardt' 'Ales Reisinger' data_cw17298 _database_code_CSD 218060 _audit_creation_date 2003-08-20T12:19:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C6 H7 Cl1 N4 O1' _chemical_formula_structural 'C6 H7 CL N4 O' _chemical_formula_sum 'C7 H7 Cl N4 O' _chemical_formula_weight 198.62 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.792(1) _cell_length_b 10.213(2) _cell_length_c 11.809(3) _cell_angle_alpha 105.66(2) _cell_angle_beta 94.91(3) _cell_angle_gamma 102.04(2) _cell_volume 874.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.787 _cell_measurement_theta_max 14.048 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.508 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.399 _exptl_absorpt_factor_muR 0.039 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.917 _exptl_absorpt_correction_T_max 0.9588 _exptl_absorpt_correction_T_ave 0.9334 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 296(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 0.75463E-1 _diffrn_orient_matrix_ub_12 0.74551E-1 _diffrn_orient_matrix_ub_13 -0.26687E-1 _diffrn_orient_matrix_ub_21 -0.109091 _diffrn_orient_matrix_ub_22 0.24029E-1 _diffrn_orient_matrix_ub_23 -0.31111E-1 _diffrn_orient_matrix_ub_31 0.5172E-2 _diffrn_orient_matrix_ub_32 0.06959 _diffrn_orient_matrix_ub_33 0.79047E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 1 _diffrn_standards_decay_corr_max 1.009 _diffrn_standards_decay_corr_min 0.963 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 -2 2 0 5 -5 -1 1 5 _diffrn_reflns_number 3313 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_unetI/netI 0.0821 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3068 _reflns_number_gt 1429 _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)' #----------------------------------------------------------------------------# # 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^)+(0.0546P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.015(2) _refine_ls_number_reflns 3068 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1401 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.196 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.057 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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 N1 N 0.1817(4) 0.4136(3) 0.8017(3) 0.0580(8) Uani 1 1 d . . . N2 N 0.1193(4) 0.5171(3) 0.7763(3) 0.0628(9) Uani 1 1 d . . . N3 N 0.0825(4) 0.4980(3) 0.6620(3) 0.0639(9) Uani 1 1 d . . . N4 N 0.1261(4) 0.3753(3) 0.6100(3) 0.0504(8) Uani 1 1 d . . . O1 O 0.2947(3) 0.1514(2) 0.7520(2) 0.0604(7) Uani 1 1 d . . . Cl1 Cl 0.15313(17) 0.10715(12) 0.31013(8) 0.0825(4) Uani 1 1 d . . . C5 C 0.1110(5) 0.3136(4) 0.4897(3) 0.0569(10) Uani 1 1 d . . . H5 H 0.0688 0.3524 0.4335 0.068 Uiso 1 1 calc R . . C6 C 0.1622(5) 0.1922(4) 0.4596(3) 0.0541(10) Uani 1 1 d . . . C7 C 0.2251(5) 0.1310(4) 0.5429(3) 0.0533(10) Uani 1 1 d . . . H7 H 0.2583 0.0467 0.5175 0.064 Uiso 1 1 calc R . . C8 C 0.2367(5) 0.1961(4) 0.6610(3) 0.0518(10) Uani 1 1 d . . . C8A C 0.1850(5) 0.3243(4) 0.6963(3) 0.0455(9) Uani 1 1 d . . . C9 C 0.3437(6) 0.0187(4) 0.7190(3) 0.0647(11) Uani 1 1 d . . . H9A H 0.4452 0.0256 0.677 0.078 Uiso 1 1 calc R . . H9B H 0.2458 -0.0537 0.6676 0.078 Uiso 1 1 calc R . . C10 C 0.3887(6) -0.0157(5) 0.8319(4) 0.0847(14) Uani 1 1 d . . . H10A H 0.4866 0.0562 0.8816 0.127 Uiso 1 1 calc R . . H10B H 0.4206 -0.1041 0.8134 0.127 Uiso 1 1 calc R . . H10C H 0.2876 -0.0212 0.8731 0.127 Uiso 1 1 calc R . . N1' N -0.2936(4) 0.2161(3) 0.5819(3) 0.0577(9) Uani 1 1 d . . . N2' N -0.3435(4) 0.2541(3) 0.4854(3) 0.0655(9) Uani 1 1 d . . . N3' N -0.3913(4) 0.3721(3) 0.5139(3) 0.0640(9) Uani 1 1 d . . . N4' N -0.3711(4) 0.4147(3) 0.6353(2) 0.0488(8) Uani 1 1 d . . . C5' C -0.4021(5) 0.5349(4) 0.7062(3) 0.0552(10) Uani 1 1 d . . . H5' H -0.4437 0.5988 0.6748 0.066 Uiso 1 1 calc R . . C6' C -0.3690(5) 0.5549(4) 0.8237(3) 0.0533(10) Uani 1 1 d . . . C7' C -0.3061(5) 0.4596(4) 0.8731(3) 0.0542(10) Uani 1 1 d . . . H7' H -0.2851 0.4779 0.9552 0.065 Uiso 1 1 calc R . . C8' C -0.2762(5) 0.3403(4) 0.8000(3) 0.0509(10) Uani 1 1 d . . . C8A' C -0.3103(5) 0.3180(4) 0.6754(3) 0.0466(9) Uani 1 1 d . . . C9' C -0.1457(5) 0.2694(4) 0.9559(3) 0.0619(11) Uani 1 1 d . . . H9'1 H -0.2418 0.2751 1.0026 0.074 Uiso 1 1 calc R . . H9'2 H -0.057 0.3577 0.9842 0.074 Uiso 1 1 calc R . . C10' C -0.0662(6) 0.1527(5) 0.9672(3) 0.0724(12) Uani 1 1 d . . . H10D H -0.1551 0.0659 0.9389 0.109 Uiso 1 1 calc R . . H10E H -0.021 0.1684 1.0492 0.109 Uiso 1 1 calc R . . H10F H 0.029 0.1484 0.9209 0.109 Uiso 1 1 calc R . . O1' O -0.2117(3) 0.2406(2) 0.8314(2) 0.0594(7) Uani 1 1 d . . . Cl1' Cl -0.40665(15) 0.70242(11) 0.91993(9) 0.0752(4) 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 N1 0.069(2) 0.057(2) 0.0446(18) 0.0052(16) 0.0068(15) 0.0219(18) N2 0.075(2) 0.058(2) 0.054(2) 0.0059(17) 0.0124(18) 0.0240(19) N3 0.078(2) 0.060(2) 0.057(2) 0.0102(17) 0.0112(18) 0.0306(19) N4 0.054(2) 0.0484(18) 0.0477(19) 0.0073(16) 0.0084(15) 0.0176(16) O1 0.0808(19) 0.0573(16) 0.0457(15) 0.0120(13) 0.0057(13) 0.0280(15) Cl1 0.1124(10) 0.0869(8) 0.0406(6) 0.0001(5) 0.0090(6) 0.0332(7) C5 0.067(3) 0.063(3) 0.040(2) 0.0116(19) 0.0063(19) 0.021(2) C6 0.063(3) 0.058(2) 0.036(2) 0.0062(18) 0.0071(18) 0.013(2) C7 0.063(3) 0.047(2) 0.047(2) 0.0042(18) 0.0088(19) 0.019(2) C8 0.055(3) 0.051(2) 0.047(2) 0.011(2) 0.0071(18) 0.013(2) C8A 0.050(2) 0.046(2) 0.040(2) 0.0101(18) 0.0072(17) 0.0129(19) C9 0.080(3) 0.056(2) 0.064(3) 0.016(2) 0.014(2) 0.028(2) C10 0.114(4) 0.084(3) 0.079(3) 0.042(3) 0.020(3) 0.046(3) N1' 0.073(2) 0.0544(19) 0.0461(19) 0.0107(16) 0.0087(16) 0.0211(18) N2' 0.083(3) 0.066(2) 0.045(2) 0.0087(17) 0.0063(17) 0.027(2) N3' 0.085(3) 0.067(2) 0.0410(19) 0.0097(17) 0.0088(17) 0.028(2) N4' 0.053(2) 0.0515(18) 0.0418(18) 0.0130(15) 0.0050(14) 0.0153(16) C5' 0.061(3) 0.047(2) 0.056(3) 0.008(2) 0.005(2) 0.021(2) C6' 0.056(3) 0.048(2) 0.053(2) 0.0055(19) 0.0059(19) 0.016(2) C7' 0.063(3) 0.056(2) 0.039(2) 0.0068(18) 0.0046(18) 0.014(2) C8' 0.052(2) 0.052(2) 0.044(2) 0.0107(19) 0.0023(18) 0.010(2) C8A' 0.053(2) 0.044(2) 0.041(2) 0.0083(18) 0.0058(17) 0.0147(19) C9' 0.073(3) 0.072(3) 0.041(2) 0.017(2) 0.000(2) 0.020(2) C10' 0.085(3) 0.092(3) 0.053(2) 0.031(2) 0.007(2) 0.038(3) O1' 0.0808(19) 0.0572(15) 0.0426(14) 0.0121(12) 0.0021(13) 0.0281(15) Cl1' 0.0920(9) 0.0640(7) 0.0657(7) 0.0011(5) 0.0129(6) 0.0340(6) #----------------------------------------------------------------------------# # 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 N1 C8A 1.336(4) . ? N1 N2 1.342(4) . ? N2 N3 1.309(4) . ? N3 N4 1.364(4) . ? N4 C8A 1.351(4) . ? N4 C5 1.374(4) . ? O1 C8 1.355(4) . ? O1 C9 1.445(4) . ? Cl1 C6 1.732(3) . ? C5 C6 1.347(5) . ? C6 C7 1.406(5) . ? C7 C8 1.359(4) . ? C8 C8A 1.416(5) . ? C9 C10 1.500(5) . ? N1' C8A' 1.335(4) . ? N1' N2' 1.351(4) . ? N2' N3' 1.301(4) . ? N3' N4' 1.365(4) . ? N4' C8A' 1.355(4) . ? N4' C5' 1.368(4) . ? C5' C6' 1.341(5) . ? C6' C7' 1.408(5) . ? C6' Cl1' 1.722(4) . ? C7' C8' 1.368(5) . ? C8' O1' 1.345(4) . ? C8' C8A' 1.419(4) . ? C9' O1' 1.445(4) . ? C9' C10' 1.483(5) . ? 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 C8A N1 N2 105.2(3) . . ? N3 N2 N1 113.0(3) . . ? N2 N3 N4 104.6(3) . . ? C8A N4 N3 108.7(3) . . ? C8A N4 C5 125.8(3) . . ? N3 N4 C5 125.5(3) . . ? C8 O1 C9 116.1(3) . . ? C6 C5 N4 114.6(3) . . ? C5 C6 C7 123.7(3) . . ? C5 C6 Cl1 118.5(3) . . ? C7 C6 Cl1 117.8(3) . . ? C8 C7 C6 119.4(3) . . ? O1 C8 C7 126.6(3) . . ? O1 C8 C8A 114.7(3) . . ? C7 C8 C8A 118.7(3) . . ? N1 C8A N4 108.4(3) . . ? N1 C8A C8 133.7(3) . . ? N4 C8A C8 117.9(3) . . ? O1 C9 C10 107.1(3) . . ? C8A' N1' N2' 105.5(3) . . ? N3' N2' N1' 112.3(3) . . ? N2' N3' N4' 105.6(3) . . ? C8A' N4' N3' 108.1(3) . . ? C8A' N4' C5' 124.9(3) . . ? N3' N4' C5' 127.0(3) . . ? C6' C5' N4' 115.8(3) . . ? C5' C6' C7' 123.0(3) . . ? C5' C6' Cl1' 119.1(3) . . ? C7' C6' Cl1' 117.8(3) . . ? C8' C7' C6' 119.9(3) . . ? O1' C8' C7' 127.9(3) . . ? O1' C8' C8A' 114.4(3) . . ? C7' C8' C8A' 117.6(3) . . ? N1' C8A' N4' 108.5(3) . . ? N1' C8A' C8' 132.8(3) . . ? N4' C8A' C8' 118.7(3) . . ? O1' C9' C10' 107.2(3) . . ? C8' O1' C9' 116.8(3) . . ? #===END data_1411ar1 _database_code_CSD 218061 _audit_creation_date 2003-08-20T15:26:43-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H17 N3 O1' _chemical_formula_structural 'C10 H17 N3 O' _chemical_formula_sum 'C10 H17 N3 O' _chemical_formula_weight 195.27 _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 11.185(2) _cell_length_b 8.1266(4) _cell_length_c 12.711(3) _cell_angle_alpha 90 _cell_angle_beta 107.343(9) _cell_angle_gamma 90 _cell_volume 1102.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.102 _cell_measurement_theta_max 14.234 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.17 _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_factor_muR 0 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 1 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9343 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_correction_T_ave 0.9678 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 296(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 0.74943E-1 _diffrn_orient_matrix_ub_12 0.16684E-1 _diffrn_orient_matrix_ub_13 0.65596E-1 _diffrn_orient_matrix_ub_21 -0.54992E-1 _diffrn_orient_matrix_ub_22 -0.2482E-2 _diffrn_orient_matrix_ub_23 0.49255E-1 _diffrn_orient_matrix_ub_31 0.11429E-1 _diffrn_orient_matrix_ub_32 -0.12194 _diffrn_orient_matrix_ub_33 0.7929E-2 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 2 _diffrn_standards_decay_corr_max 1.03 _diffrn_standards_decay_corr_min 0.968 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 0 7 -6 -1 -1 -2 -4 3 _diffrn_reflns_number 3648 _diffrn_reflns_av_R_equivalents 0.002 _diffrn_reflns_av_unetI/netI 0.0132 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 1939 _reflns_number_gt 1510 _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)' #----------------------------------------------------------------------------# # 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^)+(0.0559P)^2^+0.3197P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 1939 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1066 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.206 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # 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 N1 N 0.69003(14) -0.15250(17) 0.66573(12) 0.0502(4) Uani 1 1 d . . . C2 C 0.70742(15) -0.0433(2) 0.74234(13) 0.0442(4) Uani 1 1 d . . . N3 N 0.70294(13) -0.05194(18) 0.84807(11) 0.0483(4) Uani 1 1 d . . . C4 C 0.61491(16) -0.1355(2) 0.87250(13) 0.0450(4) Uani 1 1 d . . . C5 C 0.50634(16) -0.2016(2) 0.78207(15) 0.0568(5) Uani 1 1 d . . . H5A H 0.4415 -0.2422 0.8118 0.068 Uiso 1 1 calc R . . H5B H 0.4709 -0.1164 0.7283 0.068 Uiso 1 1 calc R . . C6 C 0.55796(19) -0.3380(2) 0.73042(16) 0.0594(5) Uani 1 1 d . . . H6 H 0.5309 -0.4455 0.7342 0.071 Uiso 1 1 calc R . . C7 C 0.64247(19) -0.3060(2) 0.67911(16) 0.0574(5) Uani 1 1 d . . . H7 H 0.6729 -0.3953 0.6491 0.069 Uiso 1 1 calc R . . O8 O 0.75354(12) 0.10616(15) 0.72620(9) 0.0543(4) Uani 1 1 d . . . C9 C 0.77388(16) 0.1418(2) 0.62104(13) 0.0476(4) Uani 1 1 d . . . H9 H 0.8083 0.0446 0.5948 0.057 Uiso 1 1 calc R . . C10 C 0.86856(19) 0.2787(3) 0.64398(17) 0.0617(5) Uani 1 1 d . . . H10A H 0.9445 0.2425 0.697 0.093 Uiso 1 1 calc R . . H10B H 0.8359 0.3722 0.6726 0.093 Uiso 1 1 calc R . . H10C H 0.8857 0.309 0.5769 0.093 Uiso 1 1 calc R . . C11 C 0.65315(18) 0.1914(3) 0.53759(16) 0.0625(5) Uani 1 1 d . . . H11A H 0.595 0.1014 0.5252 0.094 Uiso 1 1 calc R . . H11B H 0.6688 0.2199 0.4696 0.094 Uiso 1 1 calc R . . H11C H 0.6185 0.2847 0.5646 0.094 Uiso 1 1 calc R . . N12 N 0.62423(14) -0.16224(19) 0.97870(12) 0.0533(4) Uani 1 1 d . . . C13 C 0.73169(19) -0.1009(3) 1.06516(15) 0.0633(5) Uani 1 1 d . . . H13A H 0.7036 -0.0282 1.1124 0.095 Uiso 1 1 calc R . . H13B H 0.7863 -0.0423 1.0326 0.095 Uiso 1 1 calc R . . H13C H 0.7761 -0.1917 1.1075 0.095 Uiso 1 1 calc R . . C14 C 0.53379(19) -0.2532(3) 1.01747(18) 0.0673(6) Uani 1 1 d . . . H14A H 0.577 -0.3298 1.0734 0.101 Uiso 1 1 calc R . . H14B H 0.4781 -0.3121 0.957 0.101 Uiso 1 1 calc R . . H14C H 0.4864 -0.178 1.0476 0.101 Uiso 1 1 calc 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 N1 0.0635(9) 0.0380(8) 0.0472(8) -0.0042(6) 0.0133(7) -0.0003(7) C2 0.0496(9) 0.0394(9) 0.0409(9) 0.0021(7) 0.0093(7) -0.0042(7) N3 0.0596(9) 0.0456(8) 0.0380(7) 0.0002(6) 0.0119(6) -0.0127(7) C4 0.0511(9) 0.0366(9) 0.0447(9) 0.0043(7) 0.0103(7) -0.0002(7) C5 0.0466(10) 0.0599(12) 0.0567(11) 0.0075(9) 0.0045(8) -0.0052(9) C6 0.0660(12) 0.0402(10) 0.0582(11) 0.0032(8) -0.0024(9) -0.0126(9) C7 0.0709(12) 0.0348(9) 0.0582(11) -0.0047(8) 0.0070(10) 0.0042(9) O8 0.0812(9) 0.0440(7) 0.0422(6) -0.0043(5) 0.0252(6) -0.0167(6) C9 0.0594(10) 0.0467(10) 0.0416(9) 0.0006(7) 0.0225(8) -0.0022(8) C10 0.0632(12) 0.0614(12) 0.0648(12) 0.0070(10) 0.0254(10) -0.0091(10) C11 0.0633(12) 0.0663(13) 0.0574(11) 0.0070(10) 0.0174(9) -0.0023(10) N12 0.0596(9) 0.0538(9) 0.0478(8) 0.0067(7) 0.0181(7) -0.0106(7) C13 0.0711(12) 0.0762(14) 0.0412(9) 0.0010(9) 0.0145(9) -0.0111(11) C14 0.0698(13) 0.0687(14) 0.0694(13) 0.0143(10) 0.0298(11) -0.0078(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 N1 C2 1.288(2) . ? N1 C7 1.387(2) . ? C2 O8 1.359(2) . ? C2 N3 1.362(2) . ? N3 C4 1.307(2) . ? C4 N12 1.340(2) . ? C4 C5 1.501(2) . ? C5 C6 1.490(3) . ? C6 C7 1.324(3) . ? O8 C9 1.4504(19) . ? C9 C11 1.502(3) . ? C9 C10 1.503(3) . ? N12 C14 1.453(2) . ? N12 C13 1.454(2) . ? 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 C7 120.26(16) . . ? N1 C2 O8 118.68(15) . . ? N1 C2 N3 131.99(16) . . ? O8 C2 N3 108.79(13) . . ? C4 N3 C2 120.87(14) . . ? N3 C4 N12 119.05(15) . . ? N3 C4 C5 119.91(15) . . ? N12 C4 C5 121.03(16) . . ? C6 C5 C4 105.82(15) . . ? C7 C6 C5 119.87(17) . . ? C6 C7 N1 126.39(18) . . ? C2 O8 C9 119.25(13) . . ? O8 C9 C11 110.45(14) . . ? O8 C9 C10 105.32(14) . . ? C11 C9 C10 111.79(16) . . ? C4 N12 C14 124.84(16) . . ? C4 N12 C13 120.29(15) . . ? C14 N12 C13 114.86(15) . . ? #===END data_1420ar2 _database_code_CSD 218062 _audit_creation_date 2003-08-20T16:34:20-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C25 H38 N6' _chemical_formula_structural 'C25 H38 N6' _chemical_formula_sum 'C25 H38 N6' _chemical_formula_weight 422.61 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9884(9) _cell_length_b 11.953(1) _cell_length_c 12.2879(8) _cell_angle_alpha 65.573(6) _cell_angle_beta 79.700(6) _cell_angle_gamma 63.521(6) _cell_volume 1315.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.322 _cell_measurement_theta_max 13.267 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.067 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 460 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_factor_muR 0 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 2 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.9501 _exptl_absorpt_correction_T_max 0.9988 _exptl_absorpt_correction_T_ave 0.9669 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 296(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 -0.38257E-1 _diffrn_orient_matrix_ub_12 0.53091E-1 _diffrn_orient_matrix_ub_13 0.52535E-1 _diffrn_orient_matrix_ub_21 -0.06044 _diffrn_orient_matrix_ub_22 -0.48146E-1 _diffrn_orient_matrix_ub_23 0.38726E-1 _diffrn_orient_matrix_ub_31 0.72255E-1 _diffrn_orient_matrix_ub_32 -0.71174E-1 _diffrn_orient_matrix_ub_33 0.61072E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 6 _diffrn_standards_decay_corr_max 1.115 _diffrn_standards_decay_corr_min 0.978 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 4 7 1 -4 3 2 -1 4 _diffrn_reflns_number 4922 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_unetI/netI 0.0297 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4622 _reflns_number_gt 2840 _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)' #----------------------------------------------------------------------------# # 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^)+(0.0940P)^2^+0.3557P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 4622 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0987 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1826 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.336 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.04 #----------------------------------------------------------------------------# # 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' 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 N1A N -0.14872(18) 0.82595(18) 0.26699(15) 0.0532(5) Uani 1 1 d . A . H1A H -0.2175 0.8933 0.2248 0.064 Uiso 1 1 d R . . N2A N -0.1872(2) 0.90548(19) 0.42565(18) 0.0623(5) Uani 1 1 d . . . N12A N 0.1448(2) 0.5842(2) 0.6007(2) 0.0789(7) Uani 1 1 d . . . C2A C -0.1128(2) 0.8100(2) 0.37457(19) 0.0490(5) Uani 1 1 d . A . C3A C 0.0025(2) 0.6902(2) 0.41107(19) 0.0495(5) Uani 1 1 d . . . C4A C 0.0335(2) 0.6348(2) 0.3225(2) 0.0535(6) Uani 1 1 d . A . H4A H 0.1029 0.5523 0.3254 0.064 Uiso 1 1 d R . . C5A C -0.0609(2) 0.7210(2) 0.23368(19) 0.0515(5) Uani 1 1 d . . . C6A C -0.2857(3) 0.8744(3) 0.5173(2) 0.0708(7) Uani 1 1 d . A . H6A H -0.3538 0.9598 0.5225 0.085 Uiso 1 1 d R . . C7A C -0.2219(4) 0.7825(4) 0.6411(3) 0.1123(12) Uani 1 1 d . . . H7A1 H -0.1761 0.8226 0.6627 0.168 Uiso 1 1 d R A . H7A2 H -0.1575 0.6966 0.6392 0.168 Uiso 1 1 d R . . H7A3 H -0.2909 0.7701 0.6989 0.168 Uiso 1 1 d R . . C8A C -0.3630(3) 0.8176(4) 0.4816(4) 0.1120(12) Uani 1 1 d . . . H8A1 H -0.4041 0.8759 0.404 0.168 Uiso 1 1 d R A . H8A2 H -0.4322 0.8056 0.5393 0.168 Uiso 1 1 d R . . H8A3 H -0.299 0.7315 0.4798 0.168 Uiso 1 1 d R . . C9A1 C -0.1255(5) 0.9863(5) 0.4262(4) 0.0648(15) Uiso 0.616(8) 1 d P A 1 H9A1 H -0.0513 0.9315 0.4851 0.078 Uiso 0.616(8) 1 d PR A 1 C9A2 C -0.1983(7) 1.0429(7) 0.3638(6) 0.061(2) Uiso 0.384(8) 1 d P A 2 H9A2 H -0.2731 1.0945 0.3056 0.073 Uiso 0.384(8) 1 d PR A 2 C10A C -0.0670(4) 1.0431(3) 0.3000(3) 0.0943(10) Uani 1 1 d . . . H10A H -0.0031 0.9697 0.2775 0.141 Uiso 0.616(8) 1 d PR A 1 H10B H -0.0222 1.0952 0.3021 0.141 Uiso 0.616(8) 1 d PR A 1 H10C H -0.1401 1.0997 0.2427 0.141 Uiso 0.616(8) 1 d PR A 1 H10D H -0.0481 1.0015 0.2432 0.141 Uiso 0.384(8) 1 d PR A 2 H10E H 0.0064 0.9937 0.3568 0.141 Uiso 0.384(8) 1 d PR A 2 H10F H -0.0764 1.1346 0.2591 0.141 Uiso 0.384(8) 1 d PR A 2 C11A C -0.2258(3) 1.1098(3) 0.4551(3) 0.0956(10) Uani 1 1 d . . . H11A H -0.2648 1.0801 0.5324 0.143 Uiso 0.616(8) 1 d PR A 1 H11B H -0.2968 1.1654 0.3958 0.143 Uiso 0.616(8) 1 d PR A 1 H11C H -0.1789 1.1609 0.4552 0.143 Uiso 0.616(8) 1 d PR A 1 H11D H -0.3087 1.1097 0.4965 0.143 Uiso 0.384(8) 1 d PR A 2 H11E H -0.235 1.2011 0.4139 0.143 Uiso 0.384(8) 1 d PR A 2 H11F H -0.1522 1.0602 0.5117 0.143 Uiso 0.384(8) 1 d PR A 2 C12A C 0.0800(2) 0.6331(2) 0.5169(2) 0.0577(6) Uani 1 1 d . A . N1B N -0.27335(18) 0.65798(19) 0.17229(15) 0.0542(5) Uani 1 1 d . A . H1B H -0.2371 0.595 0.2392 0.065 Uiso 1 1 d R . . N2B N -0.4761(2) 0.6187(2) 0.19043(18) 0.0648(6) Uani 1 1 d . . . N12B N -0.6171(3) 0.9156(3) -0.1224(2) 0.1012(9) Uani 1 1 d . . . C2B C -0.3964(2) 0.6892(2) 0.1303(2) 0.0541(6) Uani 1 1 d . A . C3B C -0.4147(2) 0.7948(2) 0.0212(2) 0.0600(6) Uani 1 1 d . . . C4B C -0.3004(3) 0.8258(2) -0.0012(2) 0.0632(7) Uani 1 1 d . A . H4B H -0.2862 0.893 -0.0681 0.076 Uiso 1 1 d R . . C5B C -0.2137(2) 0.7390(2) 0.09355(19) 0.0546(6) Uani 1 1 d . . . C6B C -0.5760(3) 0.6675(3) 0.2750(3) 0.0793(8) Uani 1 1 d . B . H6B1 H -0.6354 0.6199 0.2982 0.095 Uiso 0.521(9) 1 d PR B 1 C7B1 C -0.6635(9) 0.8172(9) 0.2343(8) 0.123(3) Uiso 0.521(9) 1 d P B 1 H7B1 H -0.7124 0.8458 0.1633 0.185 Uiso 0.521(9) 1 d PR B 1 H7B2 H -0.6076 0.8653 0.2173 0.185 Uiso 0.521(9) 1 d PR B 1 H7B3 H -0.7269 0.8356 0.296 0.185 Uiso 0.521(9) 1 d PR B 1 C8B1 C -0.5023(7) 0.6312(9) 0.3919(7) 0.091(2) Uiso 0.521(9) 1 d P B 1 H8B1 H -0.4443 0.5364 0.4239 0.136 Uiso 0.521(9) 1 d PR B 1 H8B2 H -0.569 0.654 0.4502 0.136 Uiso 0.521(9) 1 d PR B 1 H8B3 H -0.4486 0.682 0.3723 0.136 Uiso 0.521(9) 1 d PR B 1 C7B2 C -0.7023(8) 0.7815(8) 0.1957(7) 0.097(3) Uiso 0.479(9) 1 d P B 2 H7B4 H -0.7324 0.7446 0.1552 0.145 Uiso 0.479(9) 1 d PR B 2 H7B5 H -0.6785 0.8522 0.1378 0.145 Uiso 0.479(9) 1 d PR B 2 H7B6 H -0.7741 0.8177 0.2452 0.145 Uiso 0.479(9) 1 d PR B 2 C8B2 C -0.5261(9) 0.7176(12) 0.3410(9) 0.115(3) Uiso 0.479(9) 1 d P B 2 H8B4 H -0.4487 0.6454 0.3892 0.172 Uiso 0.479(9) 1 d PR B 2 H8B5 H -0.5968 0.7536 0.3913 0.172 Uiso 0.479(9) 1 d PR B 2 H8B6 H -0.5003 0.7876 0.2845 0.172 Uiso 0.479(9) 1 d PR B 2 C9B1 C -0.4219(5) 0.4786(5) 0.2140(5) 0.0678(16) Uiso 0.614(8) 1 d P C 1 H9B1 H -0.3666 0.4278 0.2871 0.081 Uiso 0.614(8) 1 d PR C 1 C9B2 C -0.4766(8) 0.5305(8) 0.1375(7) 0.070(3) Uiso 0.386(8) 1 d P C 2 H9B2 H -0.5324 0.5845 0.0646 0.084 Uiso 0.386(8) 1 d PR C 2 C10B C -0.3334(4) 0.4471(4) 0.1093(3) 0.1051(11) Uani 1 1 d . . . H10G H -0.2614 0.4758 0.0968 0.158 Uiso 0.614(8) 1 d PR C 1 H10H H -0.388 0.4943 0.0382 0.158 Uiso 0.614(8) 1 d PR C 1 H10I H -0.2952 0.3517 0.1278 0.158 Uiso 0.614(8) 1 d PR C 1 H10J H -0.2941 0.5059 0.0529 0.158 Uiso 0.386(8) 1 d PR C 2 H10K H -0.3357 0.3886 0.0755 0.158 Uiso 0.386(8) 1 d PR C 2 H10L H -0.2794 0.3937 0.1812 0.158 Uiso 0.386(8) 1 d PR C 2 C11B C -0.5338(4) 0.4298(4) 0.2286(4) 0.1087(12) Uani 1 1 d . . . H11G H -0.5919 0.4475 0.2933 0.163 Uiso 0.614(8) 1 d PR C 1 H11H H -0.4934 0.3346 0.2457 0.163 Uiso 0.614(8) 1 d PR C 1 H11I H -0.5863 0.4772 0.1561 0.163 Uiso 0.614(8) 1 d PR C 1 H11J H -0.6249 0.4796 0.249 0.163 Uiso 0.386(8) 1 d PR C 2 H11K H -0.4781 0.3766 0.2994 0.163 Uiso 0.386(8) 1 d PR C 2 H11L H -0.5344 0.3715 0.1937 0.163 Uiso 0.386(8) 1 d PR C 2 C12B C -0.5280(3) 0.8603(3) -0.0573(2) 0.0737(8) Uani 1 1 d . C . C13 C -0.0724(2) 0.7185(3) 0.1140(2) 0.0601(6) Uani 1 1 d . A . C14 C 0.0300(3) 0.5820(3) 0.1090(3) 0.0855(9) Uani 1 1 d . . . H14A H 0.1194 0.5704 0.1214 0.128 Uiso 1 1 d R A . H14B H 0.0259 0.5794 0.0327 0.128 Uiso 1 1 d R . . H14C H 0.0103 0.5107 0.171 0.128 Uiso 1 1 d R . . C15 C -0.0406(3) 0.8335(4) 0.0155(2) 0.0936(10) Uani 1 1 d . . . H15A H 0.0494 0.8196 0.0289 0.14 Uiso 1 1 d R A . H15B H -0.1049 0.9191 0.0181 0.14 Uiso 1 1 d R . . H15C H -0.045 0.8325 -0.0614 0.14 Uiso 1 1 d R . . H6B2 H -0.609(7) 0.588(7) 0.335(6) 0.112 Uiso 0.479(9) 1 d P 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 N1A 0.0442(10) 0.0517(11) 0.0479(10) -0.0089(9) -0.0174(8) -0.0094(9) N2A 0.0643(12) 0.0534(11) 0.0640(12) -0.0215(10) 0.0051(10) -0.0227(10) N12A 0.0765(15) 0.0771(15) 0.0668(14) -0.0060(11) -0.0357(12) -0.0245(12) C2A 0.0463(11) 0.0453(12) 0.0468(12) -0.0097(10) -0.0107(9) -0.0148(10) C3A 0.0435(11) 0.0468(12) 0.0482(12) -0.0085(10) -0.0153(9) -0.0133(10) C4A 0.0434(12) 0.0498(12) 0.0603(14) -0.0179(11) -0.0109(10) -0.0122(10) C5A 0.0453(12) 0.0567(13) 0.0505(12) -0.0170(11) -0.0065(10) -0.0201(11) C6A 0.0617(15) 0.0664(16) 0.0745(17) -0.0255(14) 0.0049(13) -0.0211(13) C7A 0.118(3) 0.128(3) 0.0676(19) -0.0117(19) 0.0084(19) -0.057(2) C8A 0.074(2) 0.143(3) 0.143(3) -0.068(3) 0.024(2) -0.061(2) C10A 0.113(3) 0.083(2) 0.097(2) -0.0304(18) 0.018(2) -0.059(2) C11A 0.097(2) 0.081(2) 0.125(3) -0.057(2) 0.007(2) -0.0368(18) C12A 0.0536(13) 0.0508(13) 0.0599(14) -0.0100(11) -0.0164(12) -0.0183(11) N1B 0.0505(10) 0.0580(11) 0.0423(10) -0.0065(9) -0.0172(8) -0.0176(9) N2B 0.0645(13) 0.0681(13) 0.0634(12) -0.0222(11) -0.0019(10) -0.0303(11) N12B 0.0934(18) 0.0883(18) 0.0957(18) -0.0187(15) -0.0580(16) -0.0094(15) C2B 0.0501(12) 0.0538(13) 0.0526(13) -0.0138(11) -0.0158(10) -0.0168(11) C3B 0.0618(14) 0.0556(14) 0.0520(13) -0.0095(11) -0.0252(11) -0.0162(12) C4B 0.0746(16) 0.0601(14) 0.0476(13) -0.0045(11) -0.0166(12) -0.0302(13) C5B 0.0573(13) 0.0611(14) 0.0425(12) -0.0139(11) -0.0104(10) -0.0234(12) C6B 0.0575(16) 0.082(2) 0.094(2) -0.0347(17) -0.0009(15) -0.0238(15) C10B 0.113(3) 0.089(2) 0.128(3) -0.058(2) 0.018(2) -0.044(2) C11B 0.115(3) 0.100(2) 0.135(3) -0.042(2) 0.012(2) -0.070(2) C12B 0.0773(17) 0.0602(15) 0.0681(16) -0.0119(13) -0.0357(15) -0.0137(14) C13 0.0545(13) 0.0798(17) 0.0483(13) -0.0225(12) -0.0023(10) -0.0305(13) C14 0.0619(16) 0.122(3) 0.085(2) -0.0648(19) 0.0010(14) -0.0252(17) C15 0.100(2) 0.138(3) 0.0587(16) -0.0188(17) 0.0020(16) -0.080(2) #----------------------------------------------------------------------------# # 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 N1A C2A 1.360(3) . ? N1A C5A 1.370(3) . ? N2A C2A 1.394(3) . ? N2A C9A1 1.409(5) . ? N2A C9A2 1.453(7) . ? N2A C6A 1.467(3) . ? N12A C12A 1.141(3) . ? C2A C3A 1.383(3) . ? C3A C4A 1.414(3) . ? C3A C12A 1.424(3) . ? C4A C5A 1.360(3) . ? C5A C13 1.512(3) . ? C6A C8A 1.507(4) . ? C6A C7A 1.525(4) . ? C9A1 C11A 1.537(5) . ? C9A1 C10A 1.562(5) . ? C9A2 C10A 1.514(7) . ? C9A2 C11A 1.547(7) . ? N1B C5B 1.367(3) . ? N1B C2B 1.369(3) . ? N2B C2B 1.391(3) . ? N2B C9B1 1.419(5) . ? N2B C9B2 1.452(7) . ? N2B C6B 1.465(4) . ? N12B C12B 1.141(3) . ? C2B C3B 1.379(3) . ? C3B C4B 1.414(3) . ? C3B C12B 1.424(3) . ? C4B C5B 1.363(3) . ? C5B C13 1.510(3) . ? C6B C8B2 1.474(9) . ? C6B C7B1 1.508(9) . ? C6B C7B2 1.559(8) . ? C6B C8B1 1.580(7) . ? C9B1 C11B 1.535(5) . ? C9B1 C10B 1.540(6) . ? C9B2 C10B 1.511(8) . ? C9B2 C11B 1.551(8) . ? C13 C14 1.534(4) . ? C13 C15 1.542(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A N1A C5A 111.33(17) . . ? C2A N2A C9A1 116.5(2) . . ? C2A N2A C9A2 119.7(3) . . ? C9A1 N2A C9A2 40.7(3) . . ? C2A N2A C6A 116.1(2) . . ? C9A1 N2A C6A 121.5(2) . . ? C9A2 N2A C6A 121.1(3) . . ? N1A C2A C3A 106.02(19) . . ? N1A C2A N2A 121.32(19) . . ? C3A C2A N2A 132.6(2) . . ? C2A C3A C4A 107.94(18) . . ? C2A C3A C12A 126.7(2) . . ? C4A C3A C12A 125.34(19) . . ? C5A C4A C3A 107.71(19) . . ? C4A C5A N1A 106.99(19) . . ? C4A C5A C13 130.9(2) . . ? N1A C5A C13 122.02(19) . . ? N2A C6A C8A 111.5(2) . . ? N2A C6A C7A 113.1(2) . . ? C8A C6A C7A 111.0(3) . . ? N2A C9A1 C11A 112.8(3) . . ? N2A C9A1 C10A 110.1(3) . . ? C11A C9A1 C10A 106.2(3) . . ? N2A C9A2 C10A 110.5(5) . . ? N2A C9A2 C11A 109.8(5) . . ? C10A C9A2 C11A 108.1(5) . . ? C9A2 C10A C9A1 37.8(3) . . ? C9A1 C11A C9A2 37.7(3) . . ? N12A C12A C3A 177.9(3) . . ? C5B N1B C2B 111.41(18) . . ? C2B N2B C9B1 118.9(2) . . ? C2B N2B C9B2 114.3(3) . . ? C9B1 N2B C9B2 41.1(3) . . ? C2B N2B C6B 117.2(2) . . ? C9B1 N2B C6B 117.2(3) . . ? C9B2 N2B C6B 126.1(3) . . ? N1B C2B C3B 105.6(2) . . ? N1B C2B N2B 123.3(2) . . ? C3B C2B N2B 131.0(2) . . ? C2B C3B C4B 108.43(19) . . ? C2B C3B C12B 126.1(2) . . ? C4B C3B C12B 125.5(2) . . ? C5B C4B C3B 107.5(2) . . ? C4B C5B N1B 107.0(2) . . ? C4B C5B C13 130.8(2) . . ? N1B C5B C13 122.05(19) . . ? N2B C6B C8B2 112.7(4) . . ? N2B C6B C7B1 117.5(4) . . ? C8B2 C6B C7B1 74.2(5) . . ? N2B C6B C7B2 104.2(4) . . ? C8B2 C6B C7B2 111.8(5) . . ? C7B1 C6B C7B2 37.8(4) . . ? N2B C6B C8B1 110.3(3) . . ? C8B2 C6B C8B1 34.1(4) . . ? C7B1 C6B C8B1 104.8(5) . . ? C7B2 C6B C8B1 139.3(4) . . ? N2B C9B1 C11B 112.1(3) . . ? N2B C9B1 C10B 110.6(3) . . ? C11B C9B1 C10B 106.1(3) . . ? N2B C9B2 C10B 110.5(5) . . ? N2B C9B2 C11B 109.5(5) . . ? C10B C9B2 C11B 106.8(5) . . ? C9B2 C10B C9B1 38.6(3) . . ? C9B1 C11B C9B2 38.1(3) . . ? N12B C12B C3B 177.8(3) . . ? C5B C13 C5A 111.41(19) . . ? C5B C13 C14 108.9(2) . . ? C5A C13 C14 109.4(2) . . ? C5B C13 C15 109.0(2) . . ? C5A C13 C15 108.2(2) . . ? C14 C13 C15 109.9(2) . . ? #===END