# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/487 data_General #============================================================================== _audit_creation_method 'by teXsan' #============================================================================== # SUBMISSION DETAILS _publ_contact_author_name ' Dr. Hidemitsu Uno ' _publ_contact_author_address ; Advanced Instrumentation Center for Chemical Analysis Ehime University Matsuyama 790-8577 Japan ; _publ_contact_author_phone ' 81(89927)9663 ' _publ_contact_author_fax ' 81(89927)9670 ' _publ_contact_author_email ' uno@dpc.ehime-u.ac.jp ' _publ_requested_journal ' J. Chem. Soc., Perkin Trans. 1' #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and structures of pyrroles fused with rigid bicyclic ring systems at \b-positions ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' Hidemitsu Uno ' ; Corresponding author ; ; Advanced Instrumentation Center for Chemical Analysis Ehime University Matsuyama 790-8577 Japan ; ' Satoshi Ito ' ; ? ; ; Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan ; ' Hikaru Watanabe ' ; ? ; ; Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan ; ' Miho Nagai ' ; ? ; ; Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan ; ' Akiko Kobayashi ' ; ? ; ; Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan ; ' Takashi Murashima ' ; ? ; ; Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan ; ' Noboru Ono ' ; ? ; ; Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan ; #============================================================================== data_2 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H15 N O2 ' _chemical_formula_moiety 'C13 H15 N O2 ' _chemical_formula_weight 217.27 _chemical_melting_point 402-403 #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x, y, z 1/2-x, 1/2+y, 1/2-z -x, -y, -z 1/2+x,1/2-y,1/2+z _cell_length_a 8.389(2) _cell_length_b 6.518(2) _cell_length_c 20.846(3) _cell_angle_alpha 90 _cell_angle_beta 90.71(1) _cell_angle_gamma 90 _cell_volume 1139.7(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.0 _cell_measurement_theta_max 13.0 _cell_measurement_temperature 298.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.266 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_T_max 0.997 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 3104 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.5364 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.5364 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.13 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 1.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). The NH hydrogen atom is refined isotopically and others are placed at calculated positions. ; _reflns_number_total 892 _reflns_number_gt 1239 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.2512 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1653 _refine_ls_number_parameters 151 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.20000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.26 _refine_diff_density_min -0.23 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.00(1) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O -0.0822(4) 0.8098(5) 0.8697(2) 0.0554(10) Uani 1.00 d . . . O(2) O -0.2157(4) 0.6865(5) 0.7843(2) 0.066(1) Uani 1.00 d . . . N(1) N 0.0083(5) 0.3628(6) 0.7766(2) 0.052(1) Uani 1.00 d . . . C(1) C 0.1357(6) 0.2353(7) 0.7837(2) 0.052(1) Uani 1.00 d . . . C(2) C 0.2281(5) 0.3103(6) 0.8328(2) 0.043(1) Uani 1.00 d . . . C(3) C 0.1545(4) 0.4858(6) 0.8565(2) 0.037(1) Uani 1.00 d . . . C(4) C 0.0169(4) 0.5183(6) 0.8213(2) 0.039(1) Uani 1.00 d . . . C(5) C 0.3811(5) 0.2563(7) 0.8672(2) 0.053(1) Uani 1.00 d . . . C(6) C 0.4861(5) 0.4464(9) 0.8654(3) 0.063(2) Uani 1.00 d . . . C(7) C 0.4135(6) 0.6182(8) 0.8886(3) 0.068(2) Uani 1.00 d . . . C(8) C 0.2437(5) 0.5812(7) 0.9122(2) 0.052(1) Uani 1.00 d . . . C(9) C 0.3380(6) 0.2269(8) 0.9375(2) 0.060(2) Uani 1.00 d . . . C(10) C 0.2607(6) 0.4102(8) 0.9634(2) 0.058(1) Uani 1.00 d . . . C(11) C -0.1049(5) 0.6757(7) 0.8220(2) 0.045(1) Uani 1.00 d . . . C(12) C -0.1988(6) 0.9737(8) 0.8748(3) 0.064(2) Uani 1.00 d . . . C(13) C -0.1463(6) 1.1111(9) 0.9265(3) 0.069(2) Uani 1.00 d . . . H(1) H -0.068(5) 0.348(7) 0.756(2) 0.049(10) Uiso 1.00 calc . . . H(2) H 0.1563 0.1158 0.7592 0.0622 Uiso 1.00 calc . . . H(3) H 0.4316 0.1392 0.8495 0.0643 Uiso 1.00 calc . . . H(4) H 0.5921 0.4457 0.8497 0.0765 Uiso 1.00 calc . . . H(5) H 0.4637 0.7489 0.8899 0.0824 Uiso 1.00 calc . . . H(6) H 0.1939 0.7017 0.9281 0.0630 Uiso 1.00 calc . . . H(7) H 0.4323 0.1999 0.9617 0.0719 Uiso 1.00 calc . . . H(8) H 0.2672 0.1137 0.9410 0.0719 Uiso 1.00 calc . . . H(9) H 0.3227 0.4608 0.9984 0.0695 Uiso 1.00 calc . . . H(10) H 0.1575 0.3739 0.9781 0.0695 Uiso 1.00 calc . . . H(11) H -0.3002 0.9180 0.8845 0.0725 Uiso 1.00 calc . . . H(12) H -0.2053 1.0472 0.8355 0.0725 Uiso 1.00 calc . . . H(13) H -0.2240 1.2148 0.9326 0.0794 Uiso 1.00 calc . . . H(14) H -0.0477 1.1726 0.9153 0.0794 Uiso 1.00 calc . . . H(15) H -0.1327 1.0348 0.9650 0.0794 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.052(2) 0.051(2) 0.063(2) 0.016(1) -0.017(1) -0.004(2) O(2) 0.050(2) 0.069(2) 0.078(2) 0.006(2) -0.032(2) 0.003(2) N(1) 0.050(2) 0.058(2) 0.046(2) -0.003(2) -0.022(2) -0.006(2) C(1) 0.060(3) 0.048(3) 0.046(3) 0.007(2) -0.007(2) -0.007(2) C(2) 0.040(2) 0.046(2) 0.043(2) 0.003(2) -0.001(2) -0.001(2) C(3) 0.038(2) 0.035(2) 0.040(2) 0.001(2) -0.007(2) 0.004(2) C(4) 0.035(2) 0.041(2) 0.040(2) -0.005(2) -0.008(2) 0.001(2) C(5) 0.045(3) 0.052(3) 0.062(3) 0.014(2) -0.007(2) 0.002(2) C(6) 0.034(2) 0.081(4) 0.076(3) 0.004(2) -0.012(2) 0.023(3) C(7) 0.057(3) 0.057(3) 0.089(4) -0.019(3) -0.034(3) 0.021(3) C(8) 0.057(3) 0.039(2) 0.060(3) 0.005(2) -0.026(2) -0.007(2) C(9) 0.058(3) 0.060(3) 0.060(3) 0.006(2) -0.013(2) 0.015(3) C(10) 0.059(3) 0.069(3) 0.044(2) 0.005(2) -0.018(2) 0.000(2) C(11) 0.039(2) 0.044(2) 0.051(3) -0.006(2) -0.012(2) 0.014(2) C(12) 0.055(3) 0.054(3) 0.082(4) 0.015(2) -0.014(3) 0.003(3) C(13) 0.071(3) 0.065(3) 0.072(4) 0.018(3) -0.002(3) 0.001(3) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(11) 1.336(5) . . yes O(1) C(12) 1.452(5) . . yes O(2) C(11) 1.212(5) . . yes N(1) C(1) 1.361(6) . . yes N(1) C(4) 1.377(5) . . yes C(1) C(2) 1.366(6) . . yes C(2) C(3) 1.393(6) . . yes C(2) C(5) 1.505(6) . . yes C(3) C(4) 1.377(5) . . yes C(3) C(8) 1.508(5) . . yes C(4) C(11) 1.449(6) . . yes C(5) C(6) 1.520(7) . . yes C(5) C(9) 1.526(8) . . yes C(6) C(7) 1.365(8) . . yes C(7) C(8) 1.532(8) . . yes C(8) C(10) 1.547(6) . . yes C(9) C(10) 1.466(7) . . yes C(12) C(13) 1.465(8) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(11) O(1) C(12) 116.5(3) . 1_555 1_555 yes C(1) N(1) C(4) 109.9(3) . 1_555 1_555 yes N(1) C(1) C(2) 107.5(4) . 1_555 1_555 yes C(1) C(2) C(3) 108.1(4) . 1_555 1_555 yes C(1) C(2) C(5) 138.2(4) . 1_555 1_555 yes C(3) C(2) C(5) 113.7(4) . 1_555 1_555 yes C(2) C(3) C(4) 108.0(3) . 1_555 1_555 yes C(2) C(3) C(8) 113.2(3) . 1_555 1_555 yes C(4) C(3) C(8) 138.8(4) . 1_555 1_555 yes N(1) C(4) C(3) 106.5(3) . 1_555 1_555 yes N(1) C(4) C(11) 119.8(3) . 1_555 1_555 yes C(3) C(4) C(11) 133.7(4) . 1_555 1_555 yes C(2) C(5) C(6) 106.8(4) . 1_555 1_555 yes C(2) C(5) C(9) 106.0(4) . 1_555 1_555 yes C(6) C(5) C(9) 105.6(4) . 1_555 1_555 yes C(5) C(6) C(7) 113.5(4) . 1_555 1_555 yes C(6) C(7) C(8) 113.9(4) . 1_555 1_555 yes C(3) C(8) C(7) 105.7(4) . 1_555 1_555 yes C(3) C(8) C(10) 105.9(3) . 1_555 1_555 yes C(7) C(8) C(10) 104.9(4) . 1_555 1_555 yes C(5) C(9) C(10) 111.2(4) . 1_555 1_555 yes C(8) C(10) C(9) 111.8(4) . 1_555 1_555 yes O(1) C(11) O(2) 123.1(4) . 1_555 1_555 yes O(1) C(11) C(4) 112.2(3) . 1_555 1_555 yes O(2) C(11) C(4) 124.8(4) . 1_555 1_555 yes O(1) C(12) C(13) 107.9(4) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 O(1) C(11) C(4) N(1) 177.5(4) 1_555 1_555 1_555 1_555 yes O(1) C(11) C(4) C(3) -4.7(7) 1_555 1_555 1_555 1_555 yes O(2) C(11) O(1) C(12) 0.0(7) 1_555 1_555 1_555 1_555 yes O(2) C(11) C(4) N(1) -2.2(7) 1_555 1_555 1_555 1_555 yes O(2) C(11) C(4) C(3) 175.6(5) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) 0.7(5) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(5) -179.9(5) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(2) 0.0(5) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(8) -178.8(5) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) 0.5(5) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(11) 178.8(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) -0.4(5) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(8) 178.7(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(6) 126.8(6) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(9) -120.9(6) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) -0.7(5) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(11) -178.0(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(7) 54.8(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(10) -56.1(5) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(6) C(7) 53.7(6) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(9) C(10) -56.5(5) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(6) -53.8(5) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(9) 58.5(5) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(7) C(6) -55.3(5) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(10) C(9) 55.6(5) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(5) -180.0(4) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(7) -126.5(5) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(10) 122.6(5) 1_555 1_555 1_555 1_555 yes C(4) C(11) O(1) C(12) -179.7(4) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(3) C(8) -0.9(5) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) 1.0(6) 1_555 1_555 1_555 1_555 yes C(5) C(9) C(10) C(8) 0.3(5) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(9) C(10) 56.6(5) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(8) C(10) 56.4(5) 1_555 1_555 1_555 1_555 yes C(7) C(6) C(5) C(9) -58.9(5) 1_555 1_555 1_555 1_555 yes C(7) C(8) C(10) C(9) -55.9(5) 1_555 1_555 1_555 1_555 yes C(8) C(3) C(4) C(11) 3.2(9) 1_555 1_555 1_555 1_555 yes C(11) O(1) C(12) C(13) -175.8(4) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(2) N(1) 2.980(5) . 2_456 ? O(2) C(6) 3.416(6) . 1_455 ? #============================================================================== # End of CIF #============================================================================== data_4 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H16 I N O2 ' _chemical_formula_moiety 'C13 H16 I N O2 ' _chemical_formula_weight 345.18 _chemical_melting_point 435-436 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x, y, z -x, -y, -z _cell_length_a 10.366(1) _cell_length_b 13.730(2) _cell_length_c 9.686(1) _cell_angle_alpha 90.01(1) _cell_angle_beta 89.997(9) _cell_angle_gamma 89.943(9) _cell_volume 1378.7(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.87 _cell_measurement_theta_max 12.97 _cell_measurement_temperature 298.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.663 _exptl_absorpt_coefficient_mu 2.287 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 0.999 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 6686 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_theta_max 27.51 _diffrn_measured_fraction_theta_max 1.0545 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 1.0545 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 4.08 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). The NH hydrogen atoms are refined isotopically and others are placed at calculated positions. ; _reflns_number_total 6675 _reflns_number_gt 4683 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1101 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 6675 _refine_ls_number_parameters 316 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0008 _refine_diff_density_max 0.54 _refine_diff_density_min -0.68 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.0187(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'I' 'I' -0.474 1.812 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I(1) I 0.60251(3) -0.05039(3) 0.19953(4) 0.0702(1) Uani 1.00 d . . . I(2) I 0.89743(3) 0.55042(3) -0.30054(3) 0.0699(1) Uani 1.00 d . . . O(1) O 1.1570(3) 0.1676(2) 0.2546(3) 0.0586(9) Uani 1.00 d . . . O(2) O 1.1158(3) 0.0780(3) 0.0675(3) 0.070(1) Uani 1.00 d . . . O(3) O 0.3425(3) 0.3320(2) -0.2453(3) 0.0586(9) Uani 1.00 d . . . O(4) O 0.3842(3) 0.4216(2) -0.4320(3) 0.0683(10) Uani 1.00 d . . . N(1) N 0.8667(3) 0.0393(2) 0.1738(3) 0.0392(8) Uani 1.00 d . . . N(2) N 0.6332(3) 0.4609(2) -0.3258(3) 0.0402(8) Uani 1.00 d . . . C(1) C 0.7589(4) 0.0337(3) 0.2544(4) 0.0408(10) Uani 1.00 d . . . C(2) C 0.7772(4) 0.0905(3) 0.3699(4) 0.0401(9) Uani 1.00 d . . . C(3) C 0.9012(3) 0.1307(2) 0.3593(3) 0.0374(9) Uani 1.00 d . . . C(4) C 0.9560(3) 0.0983(2) 0.2372(3) 0.0378(9) Uani 1.00 d . . . C(5) C 0.7077(4) 0.1148(3) 0.4993(4) 0.054(1) Uani 1.00 d . . . C(6) C 0.7006(5) 0.2262(4) 0.5100(5) 0.069(2) Uani 1.00 d . . . C(7) C 0.8359(5) 0.2722(3) 0.4986(5) 0.062(1) Uani 1.00 d . . . C(8) C 0.9392(4) 0.1917(3) 0.4818(4) 0.046(1) Uani 1.00 d . . . C(9) C 0.7941(5) 0.0780(4) 0.6180(4) 0.067(1) Uani 1.00 d . . . C(10) C 0.9293(5) 0.1240(3) 0.6090(4) 0.058(1) Uani 1.00 d . . . C(11) C 1.0813(4) 0.1128(3) 0.1757(4) 0.044(1) Uani 1.00 d . . . C(12) C 1.2900(5) 0.1808(5) 0.2123(5) 0.082(2) Uani 1.00 d . . . C(13) C 1.3682(6) 0.1937(5) 0.3355(7) 0.101(2) Uani 1.00 d . . . C(14) C 0.7406(4) 0.4664(3) -0.2458(4) 0.0410(10) Uani 1.00 d . . . C(15) C 0.7227(4) 0.4095(3) -0.1306(4) 0.0405(9) Uani 1.00 d . . . C(16) C 0.5990(3) 0.3692(2) -0.1410(3) 0.0371(9) Uani 1.00 d . . . C(17) C 0.5436(4) 0.4015(2) -0.2623(3) 0.0384(9) Uani 1.00 d . . . C(18) C 0.7926(4) 0.3854(3) -0.0002(4) 0.054(1) Uani 1.00 d . . . C(19) C 0.7057(5) 0.4219(4) 0.1187(4) 0.067(1) Uani 1.00 d . . . C(20) C 0.5709(5) 0.3758(3) 0.1090(4) 0.060(1) Uani 1.00 d . . . C(21) C 0.5608(4) 0.3077(3) -0.0185(4) 0.044(1) Uani 1.00 d . . . C(22) C 0.7989(5) 0.2734(4) 0.0110(5) 0.069(2) Uani 1.00 d . . . C(23) C 0.6647(5) 0.2284(3) -0.0019(5) 0.063(1) Uani 1.00 d . . . C(24) C 0.4184(4) 0.3867(3) -0.3248(4) 0.044(1) Uani 1.00 d . . . C(25) C 0.2098(5) 0.3195(5) -0.2875(5) 0.082(2) Uani 1.00 d . . . C(26) C 0.1319(6) 0.3061(5) -0.1651(7) 0.104(2) Uani 1.00 d . . . H(1) H 0.882(3) 0.012(2) 0.105(3) 0.024(8) Uiso 1.00 calc . . . H(2) H 0.627(3) 0.483(2) -0.395(3) 0.026(9) Uiso 1.00 calc . . . H(3) H 0.6247 0.0862 0.5019 0.0649 Uiso 1.00 calc . . . H(4) H 0.6480 0.2503 0.4385 0.0839 Uiso 1.00 calc . . . H(5) H 0.6652 0.2430 0.5972 0.0839 Uiso 1.00 calc . . . H(6) H 0.8380 0.3134 0.4195 0.0750 Uiso 1.00 calc . . . H(7) H 0.8536 0.3088 0.5787 0.0750 Uiso 1.00 calc . . . H(8) H 1.0229 0.2182 0.4717 0.0551 Uiso 1.00 calc . . . H(9) H 0.7556 0.0945 0.7041 0.0799 Uiso 1.00 calc . . . H(10) H 0.8018 0.0088 0.6122 0.0799 Uiso 1.00 calc . . . H(11) H 0.9920 0.0741 0.6012 0.0693 Uiso 1.00 calc . . . H(12) H 0.9448 0.1611 0.6900 0.0693 Uiso 1.00 calc . . . H(13) H 1.3188 0.1256 0.1624 0.0987 Uiso 1.00 calc . . . H(14) H 1.2970 0.2373 0.1554 0.0987 Uiso 1.00 calc . . . H(15) H 1.3523 0.1423 0.3993 0.1184 Uiso 1.00 calc . . . H(16) H 1.4580 0.1930 0.3117 0.1184 Uiso 1.00 calc . . . H(17) H 1.3489 0.2543 0.3787 0.1184 Uiso 1.00 calc . . . H(18) H 0.8757 0.4140 0.0028 0.0648 Uiso 1.00 calc . . . H(19) H 0.7436 0.4054 0.2046 0.0803 Uiso 1.00 calc . . . H(20) H 0.6973 0.4911 0.1126 0.0803 Uiso 1.00 calc . . . H(21) H 0.5554 0.3389 0.1903 0.0720 Uiso 1.00 calc . . . H(22) H 0.5082 0.4259 0.1014 0.0720 Uiso 1.00 calc . . . H(23) H 0.4768 0.2807 -0.0288 0.0533 Uiso 1.00 calc . . . H(24) H 0.8519 0.2488 -0.0599 0.0840 Uiso 1.00 calc . . . H(25) H 0.8336 0.2565 0.0986 0.0840 Uiso 1.00 calc . . . H(26) H 0.6467 0.1917 0.0787 0.0755 Uiso 1.00 calc . . . H(27) H 0.6632 0.1871 -0.0804 0.0755 Uiso 1.00 calc . . . H(28) H 0.1807 0.3762 -0.3348 0.0982 Uiso 1.00 calc . . . H(29) H 0.2018 0.2646 -0.3457 0.0982 Uiso 1.00 calc . . . H(30) H 0.1561 0.3521 -0.0952 0.1228 Uiso 1.00 calc . . . H(31) H 0.0433 0.3130 -0.1846 0.1228 Uiso 1.00 calc . . . H(32) H 0.1466 0.2417 -0.1276 0.1228 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I(1) 0.0514(2) 0.0779(2) 0.0811(2) -0.0221(2) 0.0030(1) -0.0206(2) I(2) 0.0512(2) 0.0776(2) 0.0809(2) -0.0220(2) -0.0010(1) 0.0228(2) O(1) 0.044(2) 0.077(2) 0.055(2) -0.019(1) 0.009(1) -0.015(1) O(2) 0.063(2) 0.096(2) 0.051(2) -0.021(2) 0.017(1) -0.026(2) O(3) 0.046(2) 0.076(2) 0.054(2) -0.019(1) -0.004(1) 0.016(1) O(4) 0.062(2) 0.093(2) 0.050(2) -0.021(2) -0.016(1) 0.025(2) N(1) 0.040(2) 0.042(2) 0.035(2) -0.001(1) 0.002(1) -0.005(1) N(2) 0.043(2) 0.043(2) 0.034(2) -0.003(1) 0.003(1) 0.007(1) C(1) 0.038(2) 0.042(2) 0.042(2) 0.002(2) -0.004(1) -0.002(1) C(2) 0.039(2) 0.041(2) 0.040(2) 0.005(2) 0.001(1) -0.001(1) C(3) 0.041(2) 0.036(2) 0.036(2) 0.002(1) -0.003(1) 0.000(1) C(4) 0.038(2) 0.038(2) 0.037(2) -0.002(1) -0.003(1) 0.002(1) C(5) 0.048(2) 0.062(2) 0.052(2) 0.001(2) 0.009(2) -0.010(2) C(6) 0.066(3) 0.069(3) 0.072(3) 0.022(2) 0.007(2) -0.024(2) C(7) 0.078(3) 0.045(2) 0.063(3) 0.008(2) -0.003(2) -0.015(2) C(8) 0.051(2) 0.044(2) 0.044(2) -0.001(2) -0.006(2) -0.009(2) C(9) 0.081(3) 0.080(3) 0.040(2) -0.006(3) 0.008(2) 0.000(2) C(10) 0.068(3) 0.065(3) 0.040(2) 0.003(2) -0.006(2) -0.002(2) C(11) 0.043(2) 0.049(2) 0.040(2) -0.004(2) 0.001(2) 0.000(2) C(12) 0.050(3) 0.121(5) 0.074(3) -0.030(3) 0.014(2) -0.014(3) C(13) 0.058(3) 0.132(5) 0.114(5) -0.030(3) -0.012(3) 0.012(4) C(14) 0.039(2) 0.040(2) 0.043(2) -0.002(2) 0.003(2) 0.003(1) C(15) 0.042(2) 0.040(2) 0.040(2) 0.005(2) 0.003(1) 0.004(1) C(16) 0.042(2) 0.034(2) 0.035(2) 0.002(1) 0.004(1) 0.000(1) C(17) 0.038(2) 0.038(2) 0.039(2) 0.000(1) 0.006(1) 0.004(1) C(18) 0.047(2) 0.065(3) 0.050(2) -0.001(2) -0.010(2) 0.015(2) C(19) 0.082(3) 0.080(3) 0.040(2) -0.006(3) -0.008(2) 0.000(2) C(20) 0.077(3) 0.063(3) 0.040(2) 0.002(2) 0.008(2) 0.006(2) C(21) 0.050(2) 0.043(2) 0.040(2) 0.001(2) 0.006(2) 0.010(1) C(22) 0.067(3) 0.070(3) 0.070(3) 0.022(3) -0.002(2) 0.027(2) C(23) 0.077(3) 0.049(2) 0.064(3) 0.009(2) 0.002(2) 0.017(2) C(24) 0.044(2) 0.048(2) 0.039(2) -0.006(2) 0.000(2) 0.001(2) C(25) 0.055(3) 0.120(5) 0.073(3) -0.028(3) -0.014(2) 0.021(3) C(26) 0.056(3) 0.132(6) 0.124(5) -0.031(3) 0.013(3) -0.009(4) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution DirectMethod _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag I(1) C(1) 2.061(4) . . yes I(2) C(14) 2.064(4) . . yes O(1) C(11) 1.330(5) . . yes O(1) C(12) 1.449(6) . . yes O(2) C(11) 1.206(5) . . yes O(3) C(24) 1.333(5) . . yes O(3) C(25) 1.445(6) . . yes O(4) C(24) 1.197(5) . . yes N(1) C(1) 1.365(5) . . yes N(1) C(4) 1.375(5) . . yes N(2) C(14) 1.358(5) . . yes N(2) C(17) 1.380(5) . . yes C(1) C(2) 1.377(5) . . yes C(2) C(3) 1.403(5) . . yes C(2) C(5) 1.484(5) . . yes C(3) C(4) 1.385(5) . . yes C(3) C(8) 1.505(5) . . yes C(4) C(11) 1.443(5) . . yes C(5) C(6) 1.536(7) . . yes C(5) C(9) 1.542(6) . . yes C(6) C(7) 1.541(7) . . yes C(7) C(8) 1.547(6) . . yes C(8) C(10) 1.547(6) . . yes C(9) C(10) 1.540(7) . . yes C(12) C(13) 1.454(9) . . yes C(14) C(15) 1.374(5) . . yes C(15) C(16) 1.401(5) . . yes C(15) C(18) 1.494(5) . . yes C(16) C(17) 1.381(5) . . yes C(16) C(21) 1.509(5) . . yes C(17) C(24) 1.447(5) . . yes C(18) C(19) 1.545(6) . . yes C(18) C(22) 1.543(7) . . yes C(19) C(20) 1.538(8) . . yes C(20) C(21) 1.552(5) . . yes C(21) C(23) 1.540(6) . . yes C(22) C(23) 1.529(7) . . yes C(25) C(26) 1.447(9) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(11) O(1) C(12) 118.1(3) . 1_555 1_555 yes C(24) O(3) C(25) 117.8(3) . 1_555 1_555 yes C(1) N(1) C(4) 109.3(3) . 1_555 1_555 yes C(14) N(2) C(17) 109.3(3) . 1_555 1_555 yes I(1) C(1) N(1) 121.9(3) . 1_555 1_555 yes I(1) C(1) C(2) 129.5(3) . 1_555 1_555 yes N(1) C(1) C(2) 108.6(3) . 1_555 1_555 yes C(1) C(2) C(3) 106.9(3) . 1_555 1_555 yes C(1) C(2) C(5) 138.3(4) . 1_555 1_555 yes C(3) C(2) C(5) 114.7(3) . 1_555 1_555 yes C(2) C(3) C(4) 108.2(3) . 1_555 1_555 yes C(2) C(3) C(8) 113.7(3) . 1_555 1_555 yes C(4) C(3) C(8) 138.1(3) . 1_555 1_555 yes N(1) C(4) C(3) 107.1(3) . 1_555 1_555 yes N(1) C(4) C(11) 120.3(3) . 1_555 1_555 yes C(3) C(4) C(11) 132.6(3) . 1_555 1_555 yes C(2) C(5) C(6) 107.7(3) . 1_555 1_555 yes C(2) C(5) C(9) 105.9(3) . 1_555 1_555 yes C(6) C(5) C(9) 107.6(4) . 1_555 1_555 yes C(5) C(6) C(7) 111.1(4) . 1_555 1_555 yes C(6) C(7) C(8) 110.2(4) . 1_555 1_555 yes C(3) C(8) C(7) 107.4(3) . 1_555 1_555 yes C(3) C(8) C(10) 106.0(3) . 1_555 1_555 yes C(7) C(8) C(10) 107.3(3) . 1_555 1_555 yes C(5) C(9) C(10) 110.6(4) . 1_555 1_555 yes C(8) C(10) C(9) 110.7(4) . 1_555 1_555 yes O(1) C(11) O(2) 123.3(4) . 1_555 1_555 yes O(1) C(11) C(4) 111.9(3) . 1_555 1_555 yes O(2) C(11) C(4) 124.8(4) . 1_555 1_555 yes O(1) C(12) C(13) 108.3(4) . 1_555 1_555 yes I(2) C(14) N(2) 122.0(3) . 1_555 1_555 yes I(2) C(14) C(15) 129.3(3) . 1_555 1_555 yes N(2) C(14) C(15) 108.7(3) . 1_555 1_555 yes C(14) C(15) C(16) 106.9(3) . 1_555 1_555 yes C(14) C(15) C(18) 138.3(4) . 1_555 1_555 yes C(16) C(15) C(18) 114.7(3) . 1_555 1_555 yes C(15) C(16) C(17) 108.3(3) . 1_555 1_555 yes C(15) C(16) C(21) 113.9(3) . 1_555 1_555 yes C(17) C(16) C(21) 137.7(3) . 1_555 1_555 yes N(2) C(17) C(16) 106.8(3) . 1_555 1_555 yes N(2) C(17) C(24) 120.1(3) . 1_555 1_555 yes C(16) C(17) C(24) 133.1(3) . 1_555 1_555 yes C(15) C(18) C(19) 106.0(3) . 1_555 1_555 yes C(15) C(18) C(22) 107.5(3) . 1_555 1_555 yes C(19) C(18) C(22) 107.2(4) . 1_555 1_555 yes C(18) C(19) C(20) 110.5(4) . 1_555 1_555 yes C(19) C(20) C(21) 111.0(4) . 1_555 1_555 yes C(16) C(21) C(20) 105.7(3) . 1_555 1_555 yes C(16) C(21) C(23) 107.2(3) . 1_555 1_555 yes C(20) C(21) C(23) 107.2(3) . 1_555 1_555 yes C(18) C(22) C(23) 111.1(4) . 1_555 1_555 yes C(21) C(23) C(22) 111.0(4) . 1_555 1_555 yes O(3) C(24) O(4) 123.5(4) . 1_555 1_555 yes O(3) C(24) C(17) 111.6(3) . 1_555 1_555 yes O(4) C(24) C(17) 124.9(4) . 1_555 1_555 yes O(3) C(25) C(26) 108.4(4) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 I(1) C(1) N(1) C(4) -178.5(2) 1_555 1_555 1_555 1_555 yes I(1) C(1) C(2) C(3) 178.5(3) 1_555 1_555 1_555 1_555 yes I(1) C(1) C(2) C(5) 3.0(7) 1_555 1_555 1_555 1_555 yes I(2) C(14) N(2) C(17) -178.6(2) 1_555 1_555 1_555 1_555 yes I(2) C(14) C(15) C(16) 178.7(3) 1_555 1_555 1_555 1_555 yes I(2) C(14) C(15) C(18) 3.4(7) 1_555 1_555 1_555 1_555 yes O(1) C(11) C(4) N(1) -176.7(3) 1_555 1_555 1_555 1_555 yes O(1) C(11) C(4) C(3) 0.6(6) 1_555 1_555 1_555 1_555 yes O(2) C(11) O(1) C(12) -4.1(6) 1_555 1_555 1_555 1_555 yes O(2) C(11) C(4) N(1) 1.6(6) 1_555 1_555 1_555 1_555 yes O(2) C(11) C(4) C(3) 178.9(4) 1_555 1_555 1_555 1_555 yes O(3) C(24) C(17) N(2) -176.4(3) 1_555 1_555 1_555 1_555 yes O(3) C(24) C(17) C(16) 1.5(6) 1_555 1_555 1_555 1_555 yes O(4) C(24) O(3) C(25) -4.0(6) 1_555 1_555 1_555 1_555 yes O(4) C(24) C(17) N(2) 1.1(6) 1_555 1_555 1_555 1_555 yes O(4) C(24) C(17) C(16) 179.0(4) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) -0.9(4) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(5) -176.5(4) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(2) 0.1(4) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(8) 177.1(4) 1_555 1_555 1_555 1_555 yes N(2) C(14) C(15) C(16) -0.7(4) 1_555 1_555 1_555 1_555 yes N(2) C(14) C(15) C(18) -176.0(4) 1_555 1_555 1_555 1_555 yes N(2) C(17) C(16) C(15) 0.2(4) 1_555 1_555 1_555 1_555 yes N(2) C(17) C(16) C(21) 177.0(4) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) -0.7(4) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(11) 177.2(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 0.5(4) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(8) -177.3(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(6) -127.6(5) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(9) 117.4(5) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) 1.0(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(11) -177.4(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(7) -56.5(4) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(10) 58.0(4) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(6) C(7) -54.2(5) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(9) C(10) 56.7(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(6) 57.1(4) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(9) -57.9(4) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(7) C(6) 55.1(4) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(10) C(9) -54.6(4) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(5) 177.2(3) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(7) 126.6(5) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(10) -118.9(5) 1_555 1_555 1_555 1_555 yes C(4) C(11) O(1) C(12) 174.3(4) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(3) C(8) -0.5(4) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) -0.8(5) 1_555 1_555 1_555 1_555 yes C(5) C(9) C(10) C(8) -1.3(5) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(9) C(10) -58.2(5) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(8) C(10) -58.6(4) 1_555 1_555 1_555 1_555 yes C(7) C(6) C(5) C(9) 59.6(5) 1_555 1_555 1_555 1_555 yes C(7) C(8) C(10) C(9) 59.9(4) 1_555 1_555 1_555 1_555 yes C(8) C(3) C(4) C(11) -0.5(7) 1_555 1_555 1_555 1_555 yes C(11) O(1) C(12) C(13) -149.6(5) 1_555 1_555 1_555 1_555 yes C(14) N(2) C(17) C(16) -0.6(4) 1_555 1_555 1_555 1_555 yes C(14) N(2) C(17) C(24) 177.8(3) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) 0.3(4) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(21) -177.4(3) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(18) C(19) 117.4(5) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(18) C(22) -128.3(5) 1_555 1_555 1_555 1_555 yes C(15) C(14) N(2) C(17) 0.8(4) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(24) -177.9(4) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(21) C(20) 58.0(4) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(21) C(23) -56.1(4) 1_555 1_555 1_555 1_555 yes C(15) C(18) C(19) C(20) 56.4(5) 1_555 1_555 1_555 1_555 yes C(15) C(18) C(22) C(23) -53.5(5) 1_555 1_555 1_555 1_555 yes C(16) C(15) C(18) C(19) -57.7(4) 1_555 1_555 1_555 1_555 yes C(16) C(15) C(18) C(22) 56.7(4) 1_555 1_555 1_555 1_555 yes C(16) C(21) C(20) C(19) -54.8(4) 1_555 1_555 1_555 1_555 yes C(16) C(21) C(23) C(22) 55.4(4) 1_555 1_555 1_555 1_555 yes C(17) C(16) C(15) C(18) 176.9(3) 1_555 1_555 1_555 1_555 yes C(17) C(16) C(21) C(20) -118.7(5) 1_555 1_555 1_555 1_555 yes C(17) C(16) C(21) C(23) 127.2(5) 1_555 1_555 1_555 1_555 yes C(17) C(24) O(3) C(25) 173.6(4) 1_555 1_555 1_555 1_555 yes C(18) C(15) C(16) C(21) -0.8(4) 1_555 1_555 1_555 1_555 yes C(18) C(19) C(20) C(21) -1.0(5) 1_555 1_555 1_555 1_555 yes C(18) C(22) C(23) C(21) -1.5(5) 1_555 1_555 1_555 1_555 yes C(19) C(18) C(22) C(23) 60.1(5) 1_555 1_555 1_555 1_555 yes C(19) C(20) C(21) C(23) 59.3(4) 1_555 1_555 1_555 1_555 yes C(20) C(19) C(18) C(22) -58.2(5) 1_555 1_555 1_555 1_555 yes C(20) C(21) C(23) C(22) -57.7(4) 1_555 1_555 1_555 1_555 yes C(21) C(16) C(17) C(24) -1.1(7) 1_555 1_555 1_555 1_555 yes C(24) O(3) C(25) C(26) -150.1(5) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(2) N(1) 2.845(4) . 2_755 ? O(2) O(2) 3.474(7) . 2_755 ? O(4) N(2) 2.853(4) . 2_664 ? O(4) O(4) 3.484(7) . 2_664 ? C(4) C(10) 3.598(6) . 2_756 ? C(9) C(11) 3.538(6) . 2_756 ? C(17) C(20) 3.600(6) . 2_665 ? C(19) C(24) 3.540(6) . 2_665 ? #============================================================================== # End of CIF #============================================================================== data_5 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H21 N O2 ' _chemical_formula_moiety 'C19 H21 N O2 ' _chemical_formula_weight 295.38 _chemical_melting_point 420-421 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x, y, z -x, -y, -z _cell_length_a 8.563(2) _cell_length_b 15.285(4) _cell_length_c 6.317(4) _cell_angle_alpha 100.97(3) _cell_angle_beta 93.04(3) _cell_angle_gamma 97.72(2) _cell_volume 801.7(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.63 _cell_measurement_theta_max 12.95 _cell_measurement_temperature 298.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.224 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.999 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 3923 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 1.0657 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.0657 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 3 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 1.45 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3909 _reflns_number_gt 2355 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1461 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3895 _refine_ls_number_parameters 284 _refine_ls_goodness_of_fit_ref 1.266 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 0.22 _refine_diff_density_min -0.16 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.056(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.2896(2) 0.14185(9) 0.4301(2) 0.0483(5) Uani 1.00 d . . . O(2) O 0.1463(2) 0.0264(1) 0.1965(3) 0.0663(6) Uani 1.00 d . . . N(1) N 0.0409(2) 0.1509(1) -0.0391(3) 0.0379(5) Uani 1.00 d . . . C(1) C 0.1483(2) 0.1743(1) 0.1405(3) 0.0363(6) Uani 1.00 d . . . C(2) C 0.1861(2) 0.2674(1) 0.1813(3) 0.0345(5) Uani 1.00 d . . . C(3) C 0.1002(2) 0.2997(1) 0.0253(3) 0.0340(5) Uani 1.00 d . . . C(4) C 0.0086(2) 0.2265(1) -0.1101(3) 0.0353(6) Uani 1.00 d . . . C(5) C 0.2905(3) 0.3390(1) 0.3403(3) 0.0390(6) Uani 1.00 d . . . C(6) C 0.4048(3) 0.3912(2) 0.2105(4) 0.0484(7) Uani 1.00 d . . . C(7) C 0.3107(3) 0.4263(2) 0.0373(4) 0.0489(7) Uani 1.00 d . . . C(8) C 0.1316(3) 0.3999(1) 0.0475(3) 0.0380(6) Uani 1.00 d . . . C(9) C 0.1829(3) 0.4047(2) 0.4480(4) 0.0471(7) Uani 1.00 d . . . C(10) C 0.0885(3) 0.4406(2) 0.2746(4) 0.0484(7) Uani 1.00 d . . . C(11) C 0.1923(3) 0.1066(1) 0.2529(4) 0.0425(6) Uani 1.00 d . . . C(12) C 0.3311(4) 0.0796(2) 0.5629(5) 0.0653(9) Uani 1.00 d . . . C(13) C 0.4381(4) 0.1305(2) 0.7492(5) 0.0635(9) Uani 1.00 d . . . C(14) C -0.1020(2) 0.2232(1) -0.2976(3) 0.0380(6) Uani 1.00 d . . . C(15) C -0.1863(3) 0.2947(2) -0.3053(4) 0.0519(7) Uani 1.00 d . . . C(16) C -0.2831(3) 0.2953(2) -0.4871(5) 0.0680(9) Uani 1.00 d . . . C(17) C -0.3011(4) 0.2245(2) -0.6605(5) 0.0726(10) Uani 1.00 d . . . C(18) C -0.2227(3) 0.1525(2) -0.6537(4) 0.0603(8) Uani 1.00 d . . . C(19) C -0.1232(3) 0.1514(2) -0.4734(4) 0.0466(7) Uani 1.00 d . . . H(1) H -0.005(3) 0.097(2) -0.086(4) 0.052(7) Uiso 1.00 calc . . . H(2) H 0.346(2) 0.315(1) 0.450(3) 0.035(5) Uiso 1.00 calc . . . H(3) H 0.249(3) 0.458(2) 0.557(4) 0.055(7) Uiso 1.00 calc . . . H(4) H 0.105(3) 0.374(2) 0.537(4) 0.072(8) Uiso 1.00 calc . . . H(5) H 0.113(3) 0.507(2) 0.297(4) 0.060(7) Uiso 1.00 calc . . . H(6) H -0.026(3) 0.423(2) 0.287(4) 0.061(7) Uiso 1.00 calc . . . H(7) H 0.077(2) 0.422(1) -0.065(3) 0.040(6) Uiso 1.00 calc . . . H(8) H 0.472(3) 0.444(2) 0.318(4) 0.065(7) Uiso 1.00 calc . . . H(9) H 0.475(3) 0.350(2) 0.135(4) 0.060(7) Uiso 1.00 calc . . . H(10) H 0.338(3) 0.494(2) 0.051(3) 0.055(7) Uiso 1.00 calc . . . H(11) H 0.343(3) 0.401(2) -0.111(4) 0.059(7) Uiso 1.00 calc . . . H(12) H -0.173(3) 0.345(2) -0.173(4) 0.065(8) Uiso 1.00 calc . . . H(13) H -0.346(4) 0.344(2) -0.486(5) 0.090(9) Uiso 1.00 calc . . . H(14) H -0.368(4) 0.221(2) -0.796(5) 0.102(10) Uiso 1.00 calc . . . H(15) H -0.232(3) 0.103(2) -0.776(4) 0.067(8) Uiso 1.00 calc . . . H(16) H -0.067(3) 0.102(1) -0.473(3) 0.044(6) Uiso 1.00 calc . . . H(17) H 0.229(6) 0.041(3) 0.593(7) 0.17(1) Uiso 1.00 calc . . . H(18) H 0.375(3) 0.035(2) 0.468(5) 0.078(9) Uiso 1.00 calc . . . H(19) H 0.462(4) 0.091(2) 0.850(5) 0.101(10) Uiso 1.00 calc . . . H(20) H 0.387(4) 0.175(2) 0.824(5) 0.09(1) Uiso 1.00 calc . . . H(21) H 0.531(4) 0.161(2) 0.703(5) 0.10(1) Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0540(10) 0.0356(8) 0.0526(9) 0.0053(7) -0.0203(8) 0.0094(7) O(2) 0.086(1) 0.0311(9) 0.074(1) 0.0012(9) -0.037(1) 0.0087(8) N(1) 0.040(1) 0.0296(9) 0.0408(10) 0.0009(8) -0.0086(8) 0.0051(8) C(1) 0.035(1) 0.034(1) 0.038(1) 0.0042(9) -0.0053(9) 0.0071(9) C(2) 0.033(1) 0.034(1) 0.036(1) 0.0039(9) -0.0034(9) 0.0075(8) C(3) 0.033(1) 0.032(1) 0.036(1) 0.0022(9) -0.0028(9) 0.0079(8) C(4) 0.032(1) 0.036(1) 0.037(1) 0.0045(9) -0.0014(9) 0.0094(9) C(5) 0.043(1) 0.036(1) 0.037(1) 0.0034(10) -0.0116(10) 0.0095(9) C(6) 0.041(1) 0.049(1) 0.052(1) -0.003(1) -0.011(1) 0.013(1) C(7) 0.043(1) 0.051(1) 0.052(1) -0.007(1) -0.006(1) 0.021(1) C(8) 0.042(1) 0.032(1) 0.039(1) 0.0005(9) -0.0101(10) 0.0124(9) C(9) 0.062(2) 0.039(1) 0.038(1) 0.006(1) -0.006(1) 0.006(1) C(10) 0.059(2) 0.037(1) 0.048(1) 0.011(1) -0.005(1) 0.005(1) C(11) 0.040(1) 0.036(1) 0.049(1) 0.0049(10) -0.009(1) 0.0077(10) C(12) 0.083(2) 0.046(2) 0.065(2) 0.017(2) -0.032(2) 0.013(1) C(13) 0.065(2) 0.075(2) 0.050(2) 0.006(2) -0.012(1) 0.019(2) C(14) 0.031(1) 0.042(1) 0.040(1) -0.0049(9) -0.0066(9) 0.0144(9) C(15) 0.041(1) 0.045(1) 0.067(2) 0.000(1) -0.016(1) 0.015(1) C(16) 0.052(2) 0.060(2) 0.092(2) 0.001(1) -0.029(2) 0.029(2) C(17) 0.064(2) 0.084(2) 0.069(2) -0.013(2) -0.032(2) 0.037(2) C(18) 0.060(2) 0.074(2) 0.040(1) -0.009(1) -0.010(1) 0.009(1) C(19) 0.043(1) 0.050(1) 0.043(1) -0.002(1) -0.005(1) 0.010(1) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(11) 1.337(3) . . yes O(1) C(12) 1.449(4) . . yes O(2) C(11) 1.214(3) . . yes N(1) C(1) 1.381(3) . . yes N(1) C(4) 1.372(3) . . yes C(1) C(2) 1.387(3) . . yes C(1) C(11) 1.440(3) . . yes C(2) C(3) 1.400(3) . . yes C(2) C(5) 1.493(3) . . yes C(3) C(4) 1.388(2) . . yes C(3) C(8) 1.497(3) . . yes C(4) C(14) 1.465(3) . . yes C(5) C(6) 1.546(4) . . yes C(5) C(9) 1.541(4) . . yes C(6) C(7) 1.544(4) . . yes C(7) C(8) 1.541(3) . . yes C(8) C(10) 1.536(3) . . yes C(9) C(10) 1.552(4) . . yes C(12) C(13) 1.475(4) . . yes C(14) C(15) 1.396(4) . . yes C(14) C(19) 1.390(3) . . yes C(15) C(16) 1.382(4) . . yes C(16) C(17) 1.371(4) . . yes C(17) C(18) 1.371(5) . . yes C(18) C(19) 1.390(4) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(11) O(1) C(12) 116.4(2) . 1_555 1_555 yes C(1) N(1) C(4) 110.4(2) . 1_555 1_555 yes N(1) C(1) C(2) 106.7(2) . 1_555 1_555 yes N(1) C(1) C(11) 120.5(2) . 1_555 1_555 yes C(2) C(1) C(11) 132.7(2) . 1_555 1_555 yes C(1) C(2) C(3) 107.9(2) . 1_555 1_555 yes C(1) C(2) C(5) 137.7(2) . 1_555 1_555 yes C(3) C(2) C(5) 114.4(2) . 1_555 1_555 yes C(2) C(3) C(4) 108.2(2) . 1_555 1_555 yes C(2) C(3) C(8) 113.8(2) . 1_555 1_555 yes C(4) C(3) C(8) 138.0(2) . 1_555 1_555 yes N(1) C(4) C(3) 106.8(2) . 1_555 1_555 yes N(1) C(4) C(14) 123.0(2) . 1_555 1_555 yes C(3) C(4) C(14) 130.2(2) . 1_555 1_555 yes C(2) C(5) C(6) 107.4(2) . 1_555 1_555 yes C(2) C(5) C(9) 106.6(2) . 1_555 1_555 yes C(6) C(5) C(9) 107.4(2) . 1_555 1_555 yes C(5) C(6) C(7) 110.2(2) . 1_555 1_555 yes C(6) C(7) C(8) 110.7(2) . 1_555 1_555 yes C(3) C(8) C(7) 107.4(2) . 1_555 1_555 yes C(3) C(8) C(10) 106.6(2) . 1_555 1_555 yes C(7) C(8) C(10) 108.1(2) . 1_555 1_555 yes C(5) C(9) C(10) 110.6(2) . 1_555 1_555 yes C(8) C(10) C(9) 110.0(2) . 1_555 1_555 yes O(1) C(11) O(2) 123.0(2) . 1_555 1_555 yes O(1) C(11) C(1) 112.4(2) . 1_555 1_555 yes O(2) C(11) C(1) 124.6(2) . 1_555 1_555 yes O(1) C(12) C(13) 108.5(2) . 1_555 1_555 yes C(4) C(14) C(15) 119.8(2) . 1_555 1_555 yes C(4) C(14) C(19) 121.9(2) . 1_555 1_555 yes C(15) C(14) C(19) 118.2(2) . 1_555 1_555 yes C(14) C(15) C(16) 120.5(2) . 1_555 1_555 yes C(15) C(16) C(17) 120.6(3) . 1_555 1_555 yes C(16) C(17) C(18) 119.8(3) . 1_555 1_555 yes C(17) C(18) C(19) 120.4(2) . 1_555 1_555 yes C(14) C(19) C(18) 120.5(2) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 O(1) C(11) C(1) N(1) -176.1(2) 1_555 1_555 1_555 1_555 yes O(1) C(11) C(1) C(2) -0.4(4) 1_555 1_555 1_555 1_555 yes O(2) C(11) O(1) C(12) -3.8(3) 1_555 1_555 1_555 1_555 yes O(2) C(11) C(1) N(1) 3.2(4) 1_555 1_555 1_555 1_555 yes O(2) C(11) C(1) C(2) 178.9(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) 0.2(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(5) -179.4(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(2) -1.1(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(8) 178.4(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(14) C(15) 149.9(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(14) C(19) -31.9(3) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) 1.2(2) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(14) -179.7(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 0.5(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(8) -179.1(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(6) 122.0(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(9) -123.2(3) 1_555 1_555 1_555 1_555 yes C(1) C(11) O(1) C(12) 175.6(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) -0.9(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(4) C(14) 180.0(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(7) 56.9(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(10) -58.8(2) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(6) C(7) 54.6(2) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(9) C(10) -55.2(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(11) -175.9(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(6) -57.7(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(9) 57.2(2) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(14) C(15) -31.3(3) 1_555 1_555 1_555 1_555 yes C(3) C(4) C(14) C(19) 147.0(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(7) C(6) -55.5(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(10) C(9) 56.0(2) 1_555 1_555 1_555 1_555 yes C(4) N(1) C(1) C(11) 175.8(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(5) -179.7(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(7) -122.5(3) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(10) 121.8(3) 1_555 1_555 1_555 1_555 yes C(4) C(14) C(15) C(16) 175.7(2) 1_555 1_555 1_555 1_555 yes C(4) C(14) C(19) C(18) -176.6(2) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(1) C(11) 4.5(4) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(3) C(8) 0.7(3) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) 0.7(3) 1_555 1_555 1_555 1_555 yes C(5) C(9) C(10) C(8) -0.3(3) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(9) C(10) 59.6(2) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(8) C(10) 59.2(3) 1_555 1_555 1_555 1_555 yes C(7) C(6) C(5) C(9) -59.7(2) 1_555 1_555 1_555 1_555 yes C(7) C(8) C(10) C(9) -59.2(3) 1_555 1_555 1_555 1_555 yes C(8) C(3) C(4) C(14) -0.6(4) 1_555 1_555 1_555 1_555 yes C(11) O(1) C(12) C(13) -180.0(2) 1_555 1_555 1_555 1_555 yes C(14) C(15) C(16) C(17) 1.7(4) 1_555 1_555 1_555 1_555 yes C(14) C(19) C(18) C(17) 0.0(4) 1_555 1_555 1_555 1_555 yes C(15) C(14) C(19) C(18) 1.7(4) 1_555 1_555 1_555 1_555 yes C(15) C(16) C(17) C(18) 0.1(5) 1_555 1_555 1_555 1_555 yes C(16) C(15) C(14) C(19) -2.6(4) 1_555 1_555 1_555 1_555 yes C(16) C(17) C(18) C(19) -0.9(5) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(2) N(1) 2.922(2) . 2_555 ? O(2) O(2) 3.336(4) . 2_555 ? O(2) C(19) 3.490(3) . 2_555 ? N(1) C(18) 3.405(3) . 1_556 ? C(1) C(19) 3.490(3) . 1_556 ? C(1) C(18) 3.494(4) . 1_556 ? C(10) C(10) 3.596(5) . 2_566 ? C(11) C(19) 3.361(3) . 1_556 ? #============================================================================== # End of CIF #============================================================================== data_anti-10 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H20 N2 O4 ' _chemical_formula_moiety 'C18 H20 N2 O4 ' _chemical_formula_weight 328.37 _chemical_melting_point 537-539 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x, y, z -x, y, 1/2-z -x, -y, -z x, -y, 1/2+z 1/2+x, 1/2+y, z 1/2-x, 1/2+y, 1/2-z 1/2-x, 1/2-y, -z 1/2+x, 1/2-y, 1/2+z _cell_length_a 10.154(3) _cell_length_b 13.488(5) _cell_length_c 12.354(7) _cell_angle_alpha 90 _cell_angle_beta 97.39(4) _cell_angle_gamma 90 _cell_volume 1677(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 12.2 _cell_measurement_theta_max 13.0 _cell_measurement_temperature 298.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.250 _exptl_crystal_density_diffrn 1.300 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.998 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2118 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_theta_max 27.51 _diffrn_measured_fraction_theta_max 0.9984 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.9984 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.49 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). The hydrogen atoms except for the ethyl group are refined isotopically and the ethyl hydrogen atoms are placed at the calculated positions. The methyl group of the ethyl ester moiety is disordered. The ethyl group is treated as an i-propyl group and occupation of the methyl groups is calculated. ; _reflns_number_total 1926 _reflns_number_gt 930 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.1001 _refine_ls_hydrogen_treatment refpar _refine_ls_number_reflns 1925 _refine_ls_number_parameters 139 _refine_ls_goodness_of_fit_ref 1.566 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.01100(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.21 _refine_diff_density_min -0.22 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.0075(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.8167(2) 0.1312(1) 0.4821(1) 0.0784(7) Uani 1.00 d . . . O(2) O 0.9631(2) 0.2048(2) 0.3864(1) 0.0852(7) Uani 1.00 d . . . N(1) N 0.7874(2) 0.1681(2) 0.1924(2) 0.0722(8) Uani 1.00 d . . . C(1) C 0.7608(2) 0.1416(2) 0.2952(2) 0.0630(9) Uani 1.00 d . . . C(2) C 0.6363(2) 0.0999(2) 0.2842(2) 0.0580(8) Uani 1.00 d . . . C(3) C 0.5875(2) 0.0996(2) 0.1716(2) 0.0593(9) Uani 1.00 d . . . C(4) C 0.6821(2) 0.1418(2) 0.1162(2) 0.0683(10) Uani 1.00 d . . . C(5) C 0.4535(2) 0.0511(2) 0.1438(2) 0.0619(9) Uani 1.00 d . . . C(6) C 0.4714(4) -0.0563(3) 0.1884(2) 0.080(1) Uani 1.00 d . . . C(7) C 0.8575(2) 0.1631(2) 0.3898(2) 0.0675(10) Uani 1.00 d . . . C(8) C 0.9062(3) 0.1476(3) 0.5830(2) 0.086(1) Uani 1.00 d . . . C(9) C 0.8377(4) 0.1146(4) 0.6690(4) 0.099(2) Uani 0.60 d P . . C(10) C 1.0044(8) 0.0643(8) 0.5925(7) 0.125(4) Uani 0.40 d P . . H(1) H 0.868(3) 0.189(2) 0.171(2) 0.11(1) Uiso 1.00 calc . . . H(2) H 0.686(2) 0.153(2) 0.036(2) 0.082(8) Uiso 1.00 calc . . . H(3) H 0.425(2) 0.052(2) 0.062(2) 0.061(7) Uiso 1.00 calc . . . H(4) H 0.385(3) -0.091(2) 0.175(2) 0.10(1) Uiso 1.00 calc . . . H(5) H 0.532(2) -0.092(2) 0.144(2) 0.084(9) Uiso 1.00 calc . . . H(6) H 0.9437 0.2121 0.5918 0.1019 Uiso 1.00 calc . . . H(7) H 0.7687 0.1596 0.6780 0.1179 Uiso 0.60 calc P . . H(8) H 0.8022 0.0507 0.6519 0.1179 Uiso 0.60 calc P . . H(9) H 0.8983 0.1114 0.7344 0.1179 Uiso 0.60 calc P . . H(10) H 0.9587 0.0031 0.5786 0.1477 Uiso 0.40 calc P . . H(11) H 1.0650 0.0732 0.5408 0.1477 Uiso 0.40 calc P . . H(12) H 1.0517 0.0633 0.6640 0.1477 Uiso 0.40 calc P . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.046(1) 0.127(2) 0.060(1) -0.007(1) -0.0026(9) 0.005(1) O(2) 0.0400(10) 0.131(2) 0.085(1) -0.011(1) 0.0101(10) -0.004(1) N(1) 0.041(1) 0.111(2) 0.065(2) 0.000(1) 0.010(1) 0.012(1) C(1) 0.038(1) 0.094(2) 0.057(2) 0.003(1) 0.006(1) 0.006(2) C(2) 0.039(1) 0.082(2) 0.052(2) 0.005(1) 0.006(1) 0.003(2) C(3) 0.042(1) 0.083(2) 0.054(2) 0.008(1) 0.007(1) 0.002(2) C(4) 0.046(2) 0.099(2) 0.059(2) 0.011(2) 0.006(1) 0.009(2) C(5) 0.054(2) 0.085(2) 0.047(2) 0.000(2) 0.005(1) -0.004(2) C(6) 0.079(2) 0.087(3) 0.074(2) -0.002(2) 0.010(2) -0.009(2) C(7) 0.041(1) 0.097(2) 0.065(2) 0.007(2) 0.009(1) 0.001(2) C(8) 0.056(2) 0.138(3) 0.060(2) -0.012(2) -0.008(1) -0.014(2) C(9) 0.060(3) 0.169(6) 0.063(3) -0.028(3) -0.009(2) 0.005(3) C(10) 0.089(6) 0.185(10) 0.094(6) 0.061(6) -0.013(5) -0.028(6) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #------------------------------------------------------------------------------ _geom_special_details ; The methyl group of the ethyl ester moiety is disordered. The ethyl group is treated as an i-propyl group and occupation of the methyl groups is calculated. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(7) 1.334(3) . . yes O(1) C(8) 1.462(3) . . yes O(2) C(7) 1.217(3) . . yes N(1) C(1) 1.380(4) . . yes N(1) C(4) 1.377(3) . . yes C(1) C(2) 1.374(3) . . yes C(1) C(7) 1.455(3) . . yes C(2) C(3) 1.416(3) . . yes C(2) C(5) 1.505(4) . 2_655 yes C(3) C(4) 1.372(4) . . yes C(3) C(5) 1.510(4) . . yes C(5) C(6) 1.553(5) . . yes C(6) C(6) 1.557(6) . 2_655 yes C(8) C(9) 1.415(6) . . yes C(8) C(10) 1.497(10) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(7) O(1) C(8) 117.0(2) . 1_555 1_555 yes C(1) N(1) C(4) 109.6(2) . 1_555 1_555 yes N(1) C(1) C(2) 107.5(2) . 1_555 1_555 yes N(1) C(1) C(7) 119.7(2) . 1_555 1_555 yes C(2) C(1) C(7) 132.7(2) . 1_555 1_555 yes C(1) C(2) C(3) 107.5(2) . 1_555 1_555 yes C(1) C(2) C(5) 137.7(2) . 1_555 2_655 yes C(3) C(2) C(5) 114.7(2) . 1_555 2_655 yes C(2) C(3) C(4) 108.0(2) . 1_555 1_555 yes C(2) C(3) C(5) 114.6(2) . 1_555 1_555 yes C(4) C(3) C(5) 137.3(2) . 1_555 1_555 yes N(1) C(4) C(3) 107.3(2) . 1_555 1_555 yes C(2) C(5) C(3) 105.9(2) . 2_655 1_555 yes C(2) C(5) C(6) 104.5(2) . 2_655 1_555 yes C(3) C(5) C(6) 105.2(2) . 1_555 1_555 yes C(5) C(6) C(6) 111.0(1) . 1_555 2_655 yes O(1) C(7) O(2) 123.4(2) . 1_555 1_555 yes O(1) C(7) C(1) 111.8(2) . 1_555 1_555 yes O(2) C(7) C(1) 124.9(2) . 1_555 1_555 yes O(1) C(8) C(9) 106.3(3) . 1_555 1_555 yes O(1) C(8) C(10) 106.7(4) . 1_555 1_555 yes C(9) C(8) C(10) 95.3(4) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 O(1) C(7) C(1) N(1) -179.1(2) 1_555 1_555 1_555 1_555 yes O(1) C(7) C(1) C(2) 3.4(4) 1_555 1_555 1_555 1_555 yes O(2) C(7) O(1) C(8) -0.5(4) 1_555 1_555 1_555 1_555 yes O(2) C(7) C(1) N(1) 0.8(4) 1_555 1_555 1_555 1_555 yes O(2) C(7) C(1) C(2) -176.7(3) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) 1.1(3) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(5) 176.3(3) 1_555 1_555 1_555 2_655 yes N(1) C(4) C(3) C(2) -0.2(3) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(5) -176.9(3) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) 0.9(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) -0.6(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(5) 177.0(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(3) 132.2(3) 1_555 1_555 2_655 2_655 yes C(1) C(2) C(5) C(6) -117.0(4) 1_555 1_555 2_655 2_655 yes C(1) C(7) O(1) C(8) 179.4(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) -1.3(3) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(5) C(6) -57.9(3) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(3) C(4) -131.1(3) 1_555 2_655 2_655 2_655 yes C(2) C(5) C(6) C(6) -57.2(4) 1_555 2_655 2_655 1_555 yes C(3) C(2) C(1) C(7) 178.8(3) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(6) 58.0(3) 1_555 1_555 2_655 2_655 yes C(3) C(5) C(6) C(6) 54.1(4) 1_555 1_555 1_555 2_655 yes C(4) N(1) C(1) C(7) -179.3(3) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(5) -177.0(2) 1_555 1_555 1_555 2_655 yes C(4) C(3) C(5) C(6) 118.6(4) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(1) C(7) -6.0(6) 1_555 2_655 2_655 2_655 yes C(5) C(6) C(6) C(5) 2.2(5) 1_555 1_555 2_655 2_655 yes C(7) O(1) C(8) C(9) 175.8(3) 1_555 1_555 1_555 1_555 yes C(7) O(1) C(8) C(10) -83.3(5) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(10) 3.396(10) . 3_756 ? O(1) O(1) 3.529(4) . 7_656 ? O(2) N(1) 2.871(3) . 2_755 ? O(2) C(6) 3.441(4) . 6_655 ? O(2) O(2) 3.545(4) . 2_755 ? C(1) C(9) 3.482(6) . 7_656 ? C(7) C(10) 3.37(1) . 3_756 ? C(9) C(10) 3.240(9) . 2_756 ? C(10) C(10) 2.86(2) . 3_756 ? #============================================================================== # End of CIF #============================================================================== data_14 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C12 H13 N O2 ' _chemical_formula_moiety 'C12 H13 N O2 ' _chemical_formula_weight 203.24 _chemical_melting_point 369-370 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x, y, z -x, y, 1/2-z -x, -y, -z x, -y, 1/2+z 1/2+x, 1/2+y, z 1/2-x, 1/2+y, 1/2-z 1/2-x, 1/2-y, -z 1/2+x, 1/2-y, 1/2+z _cell_length_a 22.057(2) _cell_length_b 6.451(2) _cell_length_c 18.070(2) _cell_angle_alpha 90 _cell_angle_beta 123.980(5) _cell_angle_gamma 90 _cell_volume 2132.2(7) _cell_formula_units_Z 8 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.5 _cell_measurement_theta_max 15.0 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.320 _exptl_crystal_density_diffrn 1.266 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_T_max 0.997 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2728 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.9996 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.9996 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 2.50 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). The hydrogen atoms except for the ethyl group are refined isotopically and the ethyl hydrogen atoms are placed at the calculated positions. ; _reflns_number_total 2439 _reflns_number_gt 1732 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1338 _refine_ls_hydrogen_treatment refpar _refine_ls_number_reflns 2439 _refine_ls_number_parameters 169 _refine_ls_goodness_of_fit_ref 1.380 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 0.21 _refine_diff_density_min -0.18 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.005(1) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.37489(7) 0.3712(2) 0.78183(8) 0.0504(4) Uani 1.00 d . . . O(2) O 0.29869(7) 0.1637(2) 0.79351(8) 0.0531(4) Uani 1.00 d . . . N(1) N 0.29715(8) -0.1111(2) 0.66974(9) 0.0440(4) Uani 1.00 d . . . C(1) C 0.33188(8) 0.0791(3) 0.69375(10) 0.0384(4) Uani 1.00 d . . . C(2) C 0.36442(8) 0.1012(3) 0.64764(10) 0.0394(4) Uani 1.00 d . . . C(3) C 0.34998(9) -0.0791(3) 0.5969(1) 0.0446(4) Uani 1.00 d . . . C(4) C 0.3082(1) -0.2081(3) 0.6111(1) 0.0482(5) Uani 1.00 d . . . C(5) C 0.4060(1) 0.2468(3) 0.6256(1) 0.0513(5) Uani 1.00 d . . . C(6) C 0.3524(1) 0.2998(3) 0.5265(1) 0.0575(6) Uani 1.00 d . . . C(7) C 0.3407(1) 0.1309(3) 0.4801(1) 0.0581(6) Uani 1.00 d . . . C(8) C 0.3838(1) -0.0449(3) 0.5437(1) 0.0533(5) Uani 1.00 d . . . C(9) C 0.4520(1) 0.0814(4) 0.6153(1) 0.0607(6) Uani 1.00 d . . . C(10) C 0.33206(8) 0.2048(3) 0.75986(10) 0.0393(4) Uani 1.00 d . . . C(11) C 0.3839(1) 0.5021(3) 0.8522(1) 0.0561(5) Uani 1.00 d . . . C(12) C 0.4433(1) 0.6497(4) 0.8764(2) 0.0753(7) Uani 1.00 d . . . H(1) H 0.2711(9) -0.163(3) 0.689(1) 0.049(5) Uiso 1.00 calc . . . H(2) H 0.2881(10) -0.352(3) 0.589(1) 0.054(5) Uiso 1.00 calc . . . H(3) H 0.432(1) 0.359(3) 0.665(1) 0.063(6) Uiso 1.00 calc . . . H(4) H 0.332(1) 0.431(4) 0.504(2) 0.088(7) Uiso 1.00 calc . . . H(5) H 0.304(1) 0.116(4) 0.413(2) 0.089(7) Uiso 1.00 calc . . . H(6) H 0.392(1) -0.170(3) 0.519(1) 0.057(5) Uiso 1.00 calc . . . H(7) H 0.476(1) 0.132(3) 0.591(1) 0.077(7) Uiso 1.00 calc . . . H(8) H 0.483(1) -0.004(3) 0.669(1) 0.063(6) Uiso 1.00 calc . . . H(9) H 0.3398 0.5751 0.8318 0.0674 Uiso 1.00 calc . . . H(10) H 0.3963 0.4202 0.9025 0.0674 Uiso 1.00 calc . . . H(11) H 0.4318 0.7246 0.8249 0.0904 Uiso 1.00 calc . . . H(12) H 0.4877 0.5760 0.8998 0.0904 Uiso 1.00 calc . . . H(13) H 0.4485 0.7436 0.9201 0.0904 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0597(7) 0.0544(8) 0.0523(7) -0.0111(6) 0.0406(6) -0.0129(6) O(2) 0.0667(8) 0.0568(8) 0.0608(7) -0.0008(6) 0.0510(7) -0.0028(6) N(1) 0.0499(8) 0.0472(8) 0.0463(7) -0.0037(7) 0.0339(7) 0.0012(6) C(1) 0.0398(8) 0.0449(9) 0.0356(7) 0.0015(7) 0.0243(6) 0.0005(7) C(2) 0.0406(8) 0.0458(9) 0.0371(7) -0.0017(7) 0.0250(7) -0.0028(7) C(3) 0.0501(9) 0.0477(9) 0.0436(8) -0.0027(8) 0.0310(7) -0.0059(7) C(4) 0.059(1) 0.045(1) 0.0485(9) -0.0071(8) 0.0347(8) -0.0068(8) C(5) 0.058(1) 0.056(1) 0.0555(10) -0.0173(9) 0.0420(9) -0.0141(9) C(6) 0.075(1) 0.057(1) 0.062(1) 0.002(1) 0.052(1) 0.0086(10) C(7) 0.063(1) 0.073(1) 0.050(1) -0.003(1) 0.0395(10) -0.0005(10) C(8) 0.064(1) 0.059(1) 0.055(1) -0.0021(9) 0.0441(9) -0.0102(9) C(9) 0.0473(10) 0.085(2) 0.065(1) -0.003(1) 0.0409(10) -0.004(1) C(10) 0.0402(8) 0.0450(9) 0.0370(7) 0.0062(7) 0.0243(7) 0.0038(7) C(11) 0.062(1) 0.059(1) 0.0540(10) -0.0054(9) 0.0366(9) -0.0153(9) C(12) 0.072(1) 0.073(1) 0.080(1) -0.018(1) 0.043(1) -0.025(1) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(10) 1.336(2) . . yes O(1) C(11) 1.445(2) . . yes O(2) C(10) 1.217(2) . . yes N(1) C(1) 1.382(2) . . yes N(1) C(4) 1.365(2) . . yes C(1) C(2) 1.378(2) . . yes C(1) C(10) 1.442(2) . . yes C(2) C(3) 1.403(2) . . yes C(2) C(5) 1.514(2) . . yes C(3) C(4) 1.368(2) . . yes C(3) C(8) 1.527(2) . . yes C(5) C(6) 1.535(3) . . yes C(5) C(9) 1.553(3) . . yes C(6) C(7) 1.310(3) . . yes C(7) C(8) 1.513(3) . . yes C(8) C(9) 1.557(3) . . yes C(11) C(12) 1.475(3) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(10) O(1) C(11) 117.2(1) . 1_555 1_555 yes C(1) N(1) C(4) 110.1(1) . 1_555 1_555 yes N(1) C(1) C(2) 106.7(1) . 1_555 1_555 yes N(1) C(1) C(10) 120.3(1) . 1_555 1_555 yes C(2) C(1) C(10) 133.0(2) . 1_555 1_555 yes C(1) C(2) C(3) 107.7(1) . 1_555 1_555 yes C(1) C(2) C(5) 145.1(2) . 1_555 1_555 yes C(3) C(2) C(5) 107.0(1) . 1_555 1_555 yes C(2) C(3) C(4) 108.3(1) . 1_555 1_555 yes C(2) C(3) C(8) 106.2(1) . 1_555 1_555 yes C(4) C(3) C(8) 145.4(2) . 1_555 1_555 yes N(1) C(4) C(3) 107.3(2) . 1_555 1_555 yes C(2) C(5) C(6) 105.1(1) . 1_555 1_555 yes C(2) C(5) C(9) 97.9(2) . 1_555 1_555 yes C(6) C(5) C(9) 98.2(1) . 1_555 1_555 yes C(5) C(6) C(7) 108.0(2) . 1_555 1_555 yes C(6) C(7) C(8) 108.8(2) . 1_555 1_555 yes C(3) C(8) C(7) 105.4(1) . 1_555 1_555 yes C(3) C(8) C(9) 97.9(1) . 1_555 1_555 yes C(7) C(8) C(9) 98.2(2) . 1_555 1_555 yes C(5) C(9) C(8) 93.9(1) . 1_555 1_555 yes O(1) C(10) O(2) 123.5(1) . 1_555 1_555 yes O(1) C(10) C(1) 111.8(1) . 1_555 1_555 yes O(2) C(10) C(1) 124.7(2) . 1_555 1_555 yes O(1) C(11) C(12) 107.5(1) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 O(1) C(10) C(1) N(1) 172.9(1) 1_555 1_555 1_555 1_555 yes O(1) C(10) C(1) C(2) -2.8(2) 1_555 1_555 1_555 1_555 yes O(2) C(10) O(1) C(11) 2.9(2) 1_555 1_555 1_555 1_555 yes O(2) C(10) C(1) N(1) -5.6(2) 1_555 1_555 1_555 1_555 yes O(2) C(10) C(1) C(2) 178.7(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) -1.0(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(5) 173.9(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(2) -0.4(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(8) -174.7(2) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) -0.3(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 0.9(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(8) 177.5(1) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(6) -110.5(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(9) 148.8(2) 1_555 1_555 1_555 1_555 yes C(1) C(10) O(1) C(11) -175.7(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) 0.8(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(7) -65.6(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(9) 35.3(2) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(6) C(7) -66.9(2) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(9) C(8) 55.3(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(10) 175.1(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(6) 64.4(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(9) -36.3(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(7) C(6) 65.5(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(9) C(5) -55.0(2) 1_555 1_555 1_555 1_555 yes C(4) N(1) C(1) C(10) -175.9(1) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(5) -176.1(1) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(7) 108.8(3) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(9) -150.3(3) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(1) C(10) -10.0(4) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(3) C(8) 0.6(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) 1.0(2) 1_555 1_555 1_555 1_555 yes C(5) C(9) C(8) C(7) 52.0(2) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(9) C(8) -51.2(2) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(8) C(9) -35.1(2) 1_555 1_555 1_555 1_555 yes C(7) C(6) C(5) C(9) 33.6(2) 1_555 1_555 1_555 1_555 yes C(10) O(1) C(11) C(12) 169.4(2) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(2) N(1) 2.931(2) . 6_556 ? O(2) C(7) 3.514(2) . 4_555 ? O(2) C(11) 3.519(2) . 6_546 ? C(4) C(4) 3.388(4) . 7_546 ? C(9) C(12) 3.568(3) . 2_646 ? #============================================================================== # End of CIF #============================================================================== data_15 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C19 H21 N3 O6 ' _chemical_formula_moiety 'C19 H21 N3 O6 ' _chemical_formula_weight 387.39 _chemical_melting_point 453-455 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x, y, z 1/2-x, 1/2+y, 1/2-z -x, -y, -z 1/2+x, 1/2-y, 1/2+z _cell_length_a 10.060(2) _cell_length_b 19.282(3) _cell_length_c 10.397(2) _cell_angle_alpha 90 _cell_angle_beta 114.62(1) _cell_angle_gamma 90 _cell_volume 1833.3(5) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.7 _cell_measurement_theta_max 13.0 _cell_measurement_temperature 298.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.600 _exptl_crystal_size_min 0.300 _exptl_crystal_density_diffrn 1.403 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.930 _exptl_absorpt_correction_T_max 0.999 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 4586 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.9998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.9998 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.49 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). The hydrogen atoms except for the ethyl group are refined isotopically and the ethyl hydrogen atoms are placed at the calculated positions. ; _reflns_number_total 4215 _reflns_number_gt 2736 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1656 _refine_ls_hydrogen_treatment refpar _refine_ls_number_reflns 4190 _refine_ls_number_parameters 318 _refine_ls_goodness_of_fit_ref 1.595 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.41 _refine_diff_density_min -0.35 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.029(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.1976(2) 0.32247(10) 0.6321(2) 0.0478(6) Uani 1.00 d . . . O(2) O 0.3600(2) 0.2745(1) 0.8314(2) 0.0635(7) Uani 1.00 d . . . O(3) O 0.3103(3) 0.0941(1) 0.3270(2) 0.0795(8) Uani 1.00 d . . . O(4) O 0.5330(3) 0.0749(1) 0.4656(3) 0.0782(9) Uani 1.00 d . . . O(5) O 0.2527(2) 0.4400(1) 0.4297(2) 0.0671(7) Uani 1.00 d . . . O(6) O 0.3758(3) 0.4644(1) 0.6489(2) 0.0739(8) Uani 1.00 d . . . N(1) N 0.5184(2) 0.2212(1) 0.6951(2) 0.0385(6) Uani 1.00 d . . . N(2) N 0.4113(3) 0.0956(1) 0.4426(3) 0.0467(7) Uani 1.00 d . . . N(3) N 0.3521(3) 0.4283(1) 0.5450(3) 0.0480(7) Uani 1.00 d . . . C(1) C 0.3693(2) 0.2476(1) 0.6073(2) 0.0319(6) Uani 1.00 d . . . C(2) C 0.2743(2) 0.1829(1) 0.5324(2) 0.0309(6) Uani 1.00 d . . . C(3) C 0.3875(3) 0.1244(1) 0.5665(2) 0.0346(6) Uani 1.00 d . . . C(4) C 0.5259(3) 0.1578(1) 0.6690(3) 0.0410(7) Uani 1.00 d . . . C(5) C 0.1691(3) 0.1525(1) 0.5960(3) 0.0401(7) Uani 1.00 d . . . C(6) C 0.0907(3) 0.0927(2) 0.4993(3) 0.0511(8) Uani 1.00 d . . . C(7) C 0.1847(3) 0.0416(2) 0.5222(3) 0.0521(9) Uani 1.00 d . . . C(8) C 0.3300(3) 0.0656(1) 0.6351(3) 0.0427(7) Uani 1.00 d . . . C(9) C 0.2765(3) 0.1116(1) 0.7236(3) 0.0446(8) Uani 1.00 d . . . C(10) C 0.3747(3) 0.3003(1) 0.4974(2) 0.0324(6) Uani 1.00 d . . . C(11) C 0.4616(3) 0.2766(2) 0.4097(3) 0.0420(8) Uani 1.00 d . . . C(12) C 0.4100(3) 0.3244(2) 0.2826(3) 0.0476(8) Uani 1.00 d . . . C(13) C 0.4628(3) 0.3867(2) 0.3270(3) 0.0502(8) Uani 1.00 d . . . C(14) C 0.5558(3) 0.3819(2) 0.4848(3) 0.0494(8) Uani 1.00 d . . . C(15) C 0.4538(3) 0.3693(1) 0.5618(3) 0.0390(7) Uani 1.00 d . . . C(16) C 0.6140(3) 0.3080(2) 0.4956(4) 0.0518(9) Uani 1.00 d . . . C(17) C 0.3115(3) 0.2824(1) 0.7057(3) 0.0403(7) Uani 1.00 d . . . C(18) C 0.1273(4) 0.3580(2) 0.7111(4) 0.065(1) Uani 1.00 d . . . C(19) C 0.0070(4) 0.3990(3) 0.6117(4) 0.091(1) Uani 1.00 d . . . H(1) H 0.219(2) 0.193(1) 0.429(2) 0.031(6) Uiso 1.00 calc . . . H(2) H 0.614(3) 0.129(1) 0.711(3) 0.055(8) Uiso 1.00 calc . . . H(3) H 0.105(3) 0.188(1) 0.612(2) 0.035(6) Uiso 1.00 calc . . . H(4) H -0.010(3) 0.098(2) 0.428(3) 0.066(9) Uiso 1.00 calc . . . H(5) H 0.174(3) -0.003(2) 0.475(3) 0.067(9) Uiso 1.00 calc . . . H(6) H 0.400(3) 0.029(2) 0.679(3) 0.073(9) Uiso 1.00 calc . . . H(7) H 0.229(3) 0.086(2) 0.770(3) 0.057(8) Uiso 1.00 calc . . . H(8) H 0.353(3) 0.139(1) 0.794(3) 0.054(8) Uiso 1.00 calc . . . H(9) H 0.274(3) 0.310(1) 0.436(2) 0.033(6) Uiso 1.00 calc . . . H(10) H 0.452(3) 0.230(1) 0.386(3) 0.046(8) Uiso 1.00 calc . . . H(11) H 0.345(3) 0.315(1) 0.190(3) 0.064(9) Uiso 1.00 calc . . . H(12) H 0.444(3) 0.430(2) 0.276(3) 0.061(9) Uiso 1.00 calc . . . H(13) H 0.630(3) 0.419(1) 0.533(3) 0.042(7) Uiso 1.00 calc . . . H(14) H 0.510(3) 0.366(1) 0.660(3) 0.046(7) Uiso 1.00 calc . . . H(15) H 0.658(3) 0.288(2) 0.588(3) 0.060(9) Uiso 1.00 calc . . . H(16) H 0.679(3) 0.301(1) 0.443(3) 0.059(8) Uiso 1.00 calc . . . H(17) H 0.0904 0.3250 0.7564 0.0789 Uiso 1.00 calc . . . H(18) H 0.1955 0.3874 0.7811 0.0789 Uiso 1.00 calc . . . H(19) H -0.0606 0.3696 0.5406 0.1077 Uiso 1.00 calc . . . H(20) H -0.0418 0.4229 0.6587 0.1077 Uiso 1.00 calc . . . H(21) H 0.0443 0.4322 0.5660 0.1077 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.056(1) 0.052(1) 0.045(1) 0.0089(9) 0.0297(9) -0.0001(9) O(2) 0.085(2) 0.071(1) 0.035(1) 0.007(1) 0.025(1) -0.0023(10) O(3) 0.080(2) 0.110(2) 0.046(1) 0.001(1) 0.023(1) -0.025(1) O(4) 0.075(2) 0.091(2) 0.085(2) 0.027(1) 0.050(1) 0.002(1) O(5) 0.070(1) 0.057(1) 0.057(1) 0.021(1) 0.010(1) 0.007(1) O(6) 0.098(2) 0.050(1) 0.069(1) -0.001(1) 0.029(1) -0.021(1) N(1) 0.033(1) 0.040(1) 0.034(1) -0.0018(9) 0.0059(9) 0.0041(9) N(2) 0.058(1) 0.038(1) 0.054(1) 0.001(1) 0.032(1) -0.003(1) N(3) 0.059(2) 0.032(1) 0.050(1) -0.005(1) 0.020(1) -0.001(1) C(1) 0.030(1) 0.032(1) 0.030(1) -0.0021(9) 0.0094(9) 0.0006(9) C(2) 0.029(1) 0.031(1) 0.030(1) -0.0002(9) 0.0104(10) 0.0004(10) C(3) 0.038(1) 0.029(1) 0.036(1) -0.0006(10) 0.014(1) -0.0001(10) C(4) 0.033(1) 0.041(1) 0.042(1) 0.005(1) 0.009(1) 0.006(1) C(5) 0.036(1) 0.040(1) 0.048(1) -0.003(1) 0.021(1) 0.004(1) C(6) 0.044(2) 0.049(2) 0.054(2) -0.017(1) 0.016(1) 0.004(1) C(7) 0.063(2) 0.038(2) 0.055(2) -0.020(1) 0.025(1) -0.005(1) C(8) 0.051(2) 0.030(1) 0.046(2) 0.000(1) 0.020(1) 0.007(1) C(9) 0.056(2) 0.040(1) 0.041(1) -0.008(1) 0.024(1) 0.005(1) C(10) 0.029(1) 0.034(1) 0.033(1) -0.0024(10) 0.0122(10) 0.0016(10) C(11) 0.042(1) 0.043(2) 0.048(2) -0.004(1) 0.026(1) 0.000(1) C(12) 0.044(2) 0.062(2) 0.043(2) -0.009(1) 0.025(1) 0.001(1) C(13) 0.046(2) 0.058(2) 0.050(2) -0.009(1) 0.024(1) 0.012(1) C(14) 0.039(1) 0.052(2) 0.053(2) -0.015(1) 0.014(1) 0.004(1) C(15) 0.038(1) 0.036(1) 0.036(1) -0.006(1) 0.008(1) 0.002(1) C(16) 0.037(1) 0.058(2) 0.062(2) 0.000(1) 0.022(1) 0.010(2) C(17) 0.050(2) 0.034(1) 0.039(1) -0.008(1) 0.021(1) -0.003(1) C(18) 0.075(2) 0.075(2) 0.064(2) 0.012(2) 0.046(2) -0.006(2) C(19) 0.066(2) 0.142(4) 0.065(2) 0.037(2) 0.027(2) -0.019(2) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(17) 1.328(3) . . yes O(1) C(18) 1.459(3) . . yes O(2) C(17) 1.199(3) . . yes O(3) N(2) 1.208(3) . . yes O(4) N(2) 1.214(3) . . yes O(5) N(3) 1.220(3) . . yes O(6) N(3) 1.223(3) . . yes N(1) C(1) 1.484(3) . . yes N(1) C(4) 1.262(3) . . yes N(2) C(3) 1.510(3) . . yes N(3) C(15) 1.491(3) . . yes C(1) C(2) 1.569(3) . . yes C(1) C(10) 1.546(3) . . yes C(1) C(17) 1.527(3) . . yes C(2) C(3) 1.536(3) . . yes C(2) C(5) 1.576(3) . . yes C(3) C(4) 1.501(3) . . yes C(3) C(8) 1.572(3) . . yes C(5) C(6) 1.516(4) . . yes C(5) C(9) 1.534(4) . . yes C(6) C(7) 1.317(4) . . yes C(7) C(8) 1.516(4) . . yes C(8) C(9) 1.529(4) . . yes C(10) C(11) 1.571(3) . . yes C(10) C(15) 1.551(3) . . yes C(11) C(12) 1.514(4) . . yes C(11) C(16) 1.540(4) . . yes C(12) C(13) 1.317(4) . . yes C(13) C(14) 1.515(4) . . yes C(14) C(15) 1.561(4) . . yes C(14) C(16) 1.527(4) . . yes C(18) C(19) 1.454(5) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(17) O(1) C(18) 117.0(2) . 1_555 1_555 yes C(1) N(1) C(4) 109.6(2) . 1_555 1_555 yes O(3) N(2) O(4) 123.3(2) . 1_555 1_555 yes O(3) N(2) C(3) 119.4(2) . 1_555 1_555 yes O(4) N(2) C(3) 117.3(2) . 1_555 1_555 yes O(5) N(3) O(6) 122.8(2) . 1_555 1_555 yes O(5) N(3) C(15) 119.9(2) . 1_555 1_555 yes O(6) N(3) C(15) 117.3(2) . 1_555 1_555 yes N(1) C(1) C(2) 106.4(2) . 1_555 1_555 yes N(1) C(1) C(10) 110.0(2) . 1_555 1_555 yes N(1) C(1) C(17) 108.0(2) . 1_555 1_555 yes C(2) C(1) C(10) 111.0(2) . 1_555 1_555 yes C(2) C(1) C(17) 111.0(2) . 1_555 1_555 yes C(10) C(1) C(17) 110.3(2) . 1_555 1_555 yes C(1) C(2) C(3) 103.3(2) . 1_555 1_555 yes C(1) C(2) C(5) 117.7(2) . 1_555 1_555 yes C(3) C(2) C(5) 101.1(2) . 1_555 1_555 yes N(2) C(3) C(2) 116.0(2) . 1_555 1_555 yes N(2) C(3) C(4) 109.5(2) . 1_555 1_555 yes N(2) C(3) C(8) 109.9(2) . 1_555 1_555 yes C(2) C(3) C(4) 103.2(2) . 1_555 1_555 yes C(2) C(3) C(8) 104.9(2) . 1_555 1_555 yes C(4) C(3) C(8) 113.3(2) . 1_555 1_555 yes N(1) C(4) C(3) 116.6(2) . 1_555 1_555 yes C(2) C(5) C(6) 105.0(2) . 1_555 1_555 yes C(2) C(5) C(9) 101.6(2) . 1_555 1_555 yes C(6) C(5) C(9) 99.7(2) . 1_555 1_555 yes C(5) C(6) C(7) 108.2(3) . 1_555 1_555 yes C(6) C(7) C(8) 107.4(3) . 1_555 1_555 yes C(3) C(8) C(7) 106.7(2) . 1_555 1_555 yes C(3) C(8) C(9) 98.2(2) . 1_555 1_555 yes C(7) C(8) C(9) 100.1(2) . 1_555 1_555 yes C(5) C(9) C(8) 94.3(2) . 1_555 1_555 yes C(1) C(10) C(11) 115.9(2) . 1_555 1_555 yes C(1) C(10) C(15) 114.4(2) . 1_555 1_555 yes C(11) C(10) C(15) 101.0(2) . 1_555 1_555 yes C(10) C(11) C(12) 105.0(2) . 1_555 1_555 yes C(10) C(11) C(16) 102.1(2) . 1_555 1_555 yes C(12) C(11) C(16) 99.4(2) . 1_555 1_555 yes C(11) C(12) C(13) 107.9(3) . 1_555 1_555 yes C(12) C(13) C(14) 107.5(3) . 1_555 1_555 yes C(13) C(14) C(15) 108.9(2) . 1_555 1_555 yes C(13) C(14) C(16) 100.5(3) . 1_555 1_555 yes C(15) C(14) C(16) 97.5(2) . 1_555 1_555 yes N(3) C(15) C(10) 113.6(2) . 1_555 1_555 yes N(3) C(15) C(14) 112.7(2) . 1_555 1_555 yes C(10) C(15) C(14) 103.9(2) . 1_555 1_555 yes C(11) C(16) C(14) 93.7(2) . 1_555 1_555 yes O(1) C(17) O(2) 124.3(2) . 1_555 1_555 yes O(1) C(17) C(1) 110.3(2) . 1_555 1_555 yes O(2) C(17) C(1) 125.4(2) . 1_555 1_555 yes O(1) C(18) C(19) 108.1(3) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 O(1) C(17) C(1) N(1) 163.4(2) 1_555 1_555 1_555 1_555 yes O(1) C(17) C(1) C(2) -80.2(2) 1_555 1_555 1_555 1_555 yes O(1) C(17) C(1) C(10) 43.2(3) 1_555 1_555 1_555 1_555 yes O(2) C(17) O(1) C(18) -0.8(4) 1_555 1_555 1_555 1_555 yes O(2) C(17) C(1) N(1) -17.3(3) 1_555 1_555 1_555 1_555 yes O(2) C(17) C(1) C(2) 99.0(3) 1_555 1_555 1_555 1_555 yes O(2) C(17) C(1) C(10) -137.5(3) 1_555 1_555 1_555 1_555 yes O(3) N(2) C(3) C(2) -32.2(3) 1_555 1_555 1_555 1_555 yes O(3) N(2) C(3) C(4) -148.3(3) 1_555 1_555 1_555 1_555 yes O(3) N(2) C(3) C(8) 86.6(3) 1_555 1_555 1_555 1_555 yes O(4) N(2) C(3) C(2) 147.9(2) 1_555 1_555 1_555 1_555 yes O(4) N(2) C(3) C(4) 31.7(3) 1_555 1_555 1_555 1_555 yes O(4) N(2) C(3) C(8) -93.4(3) 1_555 1_555 1_555 1_555 yes O(5) N(3) C(15) C(10) -48.4(3) 1_555 1_555 1_555 1_555 yes O(5) N(3) C(15) C(14) 69.5(3) 1_555 1_555 1_555 1_555 yes O(6) N(3) C(15) C(10) 133.7(2) 1_555 1_555 1_555 1_555 yes O(6) N(3) C(15) C(14) -108.4(3) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) -9.1(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(5) 101.3(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(10) C(11) 48.8(3) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(10) C(15) -68.2(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) N(2) 121.1(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(2) -3.0(3) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(8) -115.8(3) 1_555 1_555 1_555 1_555 yes N(2) C(3) C(2) C(1) -112.5(2) 1_555 1_555 1_555 1_555 yes N(2) C(3) C(2) C(5) 125.3(2) 1_555 1_555 1_555 1_555 yes N(2) C(3) C(8) C(7) -61.8(3) 1_555 1_555 1_555 1_555 yes N(2) C(3) C(8) C(9) -165.0(2) 1_555 1_555 1_555 1_555 yes N(3) C(15) C(10) C(1) -103.1(2) 1_555 1_555 1_555 1_555 yes N(3) C(15) C(10) C(11) 131.7(2) 1_555 1_555 1_555 1_555 yes N(3) C(15) C(14) C(13) -64.0(3) 1_555 1_555 1_555 1_555 yes N(3) C(15) C(14) C(16) -167.8(2) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) -3.1(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 7.2(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(8) 126.0(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(6) 178.4(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(9) -78.2(2) 1_555 1_555 1_555 1_555 yes C(1) C(10) C(11) C(12) 162.1(2) 1_555 1_555 1_555 1_555 yes C(1) C(10) C(11) C(16) -94.6(2) 1_555 1_555 1_555 1_555 yes C(1) C(10) C(15) C(14) 134.1(2) 1_555 1_555 1_555 1_555 yes C(1) C(17) O(1) C(18) 178.5(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) 7.8(3) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(10) C(11) -68.8(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) C(10) C(15) 174.3(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(7) 63.6(3) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(9) -39.6(2) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(6) C(7) 72.0(3) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(9) C(8) -58.0(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(10) 110.6(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(17) -126.3(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(6) -70.0(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(9) 33.4(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(7) C(6) -68.5(3) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(9) C(5) 58.7(2) 1_555 1_555 1_555 1_555 yes C(4) N(1) C(1) C(10) -112.5(2) 1_555 1_555 1_555 1_555 yes C(4) N(1) C(1) C(17) 127.0(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(5) -115.0(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(7) 175.4(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(9) 72.2(2) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(1) C(10) -139.0(2) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(1) C(17) -16.0(3) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(3) C(8) 3.8(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) -0.2(3) 1_555 1_555 1_555 1_555 yes C(5) C(9) C(8) C(7) -50.1(2) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(9) C(8) 49.7(2) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(8) C(9) 33.4(3) 1_555 1_555 1_555 1_555 yes C(7) C(6) C(5) C(9) -32.9(3) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(12) C(13) 70.5(3) 1_555 1_555 1_555 1_555 yes C(10) C(11) C(16) C(14) -57.0(2) 1_555 1_555 1_555 1_555 yes C(10) C(15) C(14) C(13) 59.4(3) 1_555 1_555 1_555 1_555 yes C(10) C(15) C(14) C(16) -44.4(2) 1_555 1_555 1_555 1_555 yes C(11) C(10) C(1) C(17) 167.8(2) 1_555 1_555 1_555 1_555 yes C(11) C(10) C(15) C(14) 8.8(2) 1_555 1_555 1_555 1_555 yes C(11) C(12) C(13) C(14) 1.9(3) 1_555 1_555 1_555 1_555 yes C(11) C(16) C(14) C(13) -49.9(2) 1_555 1_555 1_555 1_555 yes C(11) C(16) C(14) C(15) 61.0(2) 1_555 1_555 1_555 1_555 yes C(12) C(11) C(10) C(15) -73.7(2) 1_555 1_555 1_555 1_555 yes C(12) C(11) C(16) C(14) 50.6(2) 1_555 1_555 1_555 1_555 yes C(12) C(13) C(14) C(15) -69.5(3) 1_555 1_555 1_555 1_555 yes C(12) C(13) C(14) C(16) 32.2(3) 1_555 1_555 1_555 1_555 yes C(13) C(12) C(11) C(16) -34.9(3) 1_555 1_555 1_555 1_555 yes C(15) C(10) C(1) C(17) 50.8(3) 1_555 1_555 1_555 1_555 yes C(15) C(10) C(11) C(16) 29.7(2) 1_555 1_555 1_555 1_555 yes C(17) O(1) C(18) C(19) 179.7(3) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(2) C(6) 3.408(4) . 4_555 ? O(2) C(5) 3.478(3) . 4_555 ? O(3) C(14) 3.441(4) . 4_454 ? O(3) C(19) 3.554(4) . 4_554 ? O(3) C(15) 3.567(3) . 4_454 ? O(4) O(4) 3.112(5) . 3_656 ? O(4) C(8) 3.396(3) . 3_656 ? O(4) N(2) 3.403(3) . 3_656 ? O(4) C(18) 3.416(4) . 4_554 ? O(4) C(7) 3.581(4) . 3_656 ? O(5) C(4) 3.311(3) . 4_454 ? O(6) C(13) 3.256(4) . 3_666 ? O(6) C(14) 3.462(4) . 3_666 ? O(6) C(6) 3.549(4) . 4_555 ? C(4) C(12) 3.556(4) . 4_555 ? #============================================================================== # End of CIF #============================================================================== data_19 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C12 H15 N O2 ' _chemical_formula_moiety 'C12 H15 N O2 ' _chemical_formula_weight 205.26 _chemical_melting_point 387-389 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 9.557(2) _cell_length_b 9.576(3) _cell_length_c 6.945(2) _cell_angle_alpha 103.60(2) _cell_angle_beta 107.95(2) _cell_angle_gamma 105.87(2) _cell_volume 545.0(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.6 _cell_measurement_theta_max 15.0 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.251 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.999 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 2643 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 1.0024 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.0024 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 2.30 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2495 _reflns_number_gt 1860 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1181 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 2495 _refine_ls_number_parameters 197 _refine_ls_goodness_of_fit_ref 1.454 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.17 _refine_diff_density_min -0.15 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.07(1) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.2822(1) -0.15190(10) 0.3779(1) 0.0421(3) Uani 1.00 d . . . O(2) O 0.4001(1) -0.1530(1) 0.7122(1) 0.0536(3) Uani 1.00 d . . . N(1) N 0.4021(1) 0.1540(1) 0.8793(2) 0.0397(3) Uani 1.00 d . . . C(1) C 0.3442(1) 0.0659(1) 0.6626(2) 0.0347(3) Uani 1.00 d . . . C(2) C 0.2893(1) 0.1529(1) 0.5483(2) 0.0338(3) Uani 1.00 d . . . C(3) C 0.3133(1) 0.2942(1) 0.6969(2) 0.0361(3) Uani 1.00 d . . . C(4) C 0.3831(2) 0.2922(2) 0.9005(2) 0.0411(3) Uani 1.00 d . . . C(5) C 0.2019(2) 0.1515(1) 0.3258(2) 0.0396(3) Uani 1.00 d . . . C(6) C 0.0317(2) 0.1344(2) 0.3072(2) 0.0529(4) Uani 1.00 d . . . C(7) C 0.0572(2) 0.2891(2) 0.4736(3) 0.0559(5) Uani 1.00 d . . . C(8) C 0.2385(2) 0.3803(2) 0.5675(2) 0.0435(4) Uani 1.00 d . . . C(9) C 0.2735(2) 0.3264(2) 0.3653(2) 0.0446(4) Uani 1.00 d . . . C(10) C 0.3477(1) -0.0873(1) 0.5943(2) 0.0362(3) Uani 1.00 d . . . C(11) C 0.2721(2) -0.3083(2) 0.2863(2) 0.0441(4) Uani 1.00 d . . . C(12) C 0.1931(2) -0.3545(2) 0.0464(3) 0.0570(5) Uani 1.00 d . . . H(1) H 0.458(2) 0.132(2) 0.993(3) 0.063(5) Uiso 1.00 calc . . . H(2) H 0.419(2) 0.370(2) 1.044(2) 0.049(4) Uiso 1.00 calc . . . H(3) H 0.270(2) 0.493(2) 0.636(2) 0.048(4) Uiso 1.00 calc . . . H(4) H 0.023(2) 0.273(2) 0.590(3) 0.065(5) Uiso 1.00 calc . . . H(5) H 0.002(2) 0.348(2) 0.407(3) 0.068(5) Uiso 1.00 calc . . . H(6) H -0.023(2) 0.039(2) 0.332(3) 0.065(5) Uiso 1.00 calc . . . H(7) H -0.035(2) 0.125(2) 0.157(3) 0.072(5) Uiso 1.00 calc . . . H(8) H 0.211(2) 0.081(2) 0.202(2) 0.045(4) Uiso 1.00 calc . . . H(9) H 0.390(2) 0.366(2) 0.397(3) 0.052(4) Uiso 1.00 calc . . . H(10) H 0.213(2) 0.355(2) 0.243(3) 0.057(4) Uiso 1.00 calc . . . H(11) H 0.380(2) -0.308(2) 0.328(3) 0.054(4) Uiso 1.00 calc . . . H(12) H 0.206(2) -0.374(2) 0.342(3) 0.054(4) Uiso 1.00 calc . . . H(13) H 0.083(2) -0.357(2) 0.003(3) 0.073(5) Uiso 1.00 calc . . . H(14) H 0.247(3) -0.286(3) -0.006(4) 0.095(7) Uiso 1.00 calc . . . H(15) H 0.182(2) -0.463(2) -0.024(3) 0.071(5) Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0554(6) 0.0363(5) 0.0298(5) 0.0219(4) 0.0078(4) 0.0104(4) O(2) 0.0715(7) 0.0476(6) 0.0355(5) 0.0286(5) 0.0050(5) 0.0185(4) N(1) 0.0447(6) 0.0442(6) 0.0244(5) 0.0163(5) 0.0064(4) 0.0122(4) C(1) 0.0349(6) 0.0376(6) 0.0260(6) 0.0118(5) 0.0071(5) 0.0101(5) C(2) 0.0374(6) 0.0344(6) 0.0256(6) 0.0128(5) 0.0092(5) 0.0087(5) C(3) 0.0410(7) 0.0363(6) 0.0271(6) 0.0152(5) 0.0106(5) 0.0080(5) C(4) 0.0499(7) 0.0423(7) 0.0253(6) 0.0172(6) 0.0107(5) 0.0078(5) C(5) 0.0522(8) 0.0382(7) 0.0242(6) 0.0195(6) 0.0089(5) 0.0091(5) C(6) 0.0473(8) 0.0560(9) 0.0408(8) 0.0182(7) 0.0014(6) 0.0151(7) C(7) 0.0557(9) 0.073(1) 0.0458(9) 0.0386(8) 0.0157(7) 0.0211(8) C(8) 0.0611(9) 0.0387(7) 0.0324(6) 0.0259(6) 0.0149(6) 0.0119(5) C(9) 0.0619(9) 0.0425(7) 0.0334(7) 0.0222(7) 0.0182(6) 0.0180(6) C(10) 0.0365(6) 0.0374(6) 0.0304(6) 0.0138(5) 0.0072(5) 0.0129(5) C(11) 0.0499(8) 0.0361(7) 0.0408(7) 0.0200(6) 0.0111(6) 0.0089(6) C(12) 0.064(1) 0.0523(9) 0.0404(8) 0.0167(8) 0.0151(7) 0.0050(7) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(10) 1.343(1) . . yes O(1) C(11) 1.446(2) . . yes O(2) C(10) 1.216(2) . . yes N(1) C(1) 1.385(2) . . yes N(1) C(4) 1.365(2) . . yes C(1) C(2) 1.376(2) . . yes C(1) C(10) 1.446(2) . . yes C(2) C(3) 1.406(2) . . yes C(2) C(5) 1.508(2) . . yes C(3) C(4) 1.372(2) . . yes C(3) C(8) 1.507(2) . . yes C(5) C(6) 1.551(2) . . yes C(5) C(9) 1.546(2) . . yes C(6) C(7) 1.554(3) . . yes C(7) C(8) 1.548(2) . . yes C(8) C(9) 1.547(2) . . yes C(11) C(12) 1.495(2) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(10) O(1) C(11) 117.0(1) . 1_555 1_555 yes C(1) N(1) C(4) 109.8(1) . 1_555 1_555 yes N(1) C(1) C(2) 106.7(1) . 1_555 1_555 yes N(1) C(1) C(10) 121.3(1) . 1_555 1_555 yes C(2) C(1) C(10) 132.0(1) . 1_555 1_555 yes C(1) C(2) C(3) 108.1(1) . 1_555 1_555 yes C(1) C(2) C(5) 144.4(1) . 1_555 1_555 yes C(3) C(2) C(5) 107.2(1) . 1_555 1_555 yes C(2) C(3) C(4) 107.6(1) . 1_555 1_555 yes C(2) C(3) C(8) 106.8(1) . 1_555 1_555 yes C(4) C(3) C(8) 145.2(1) . 1_555 1_555 yes N(1) C(4) C(3) 107.8(1) . 1_555 1_555 yes C(2) C(5) C(6) 106.1(1) . 1_555 1_555 yes C(2) C(5) C(9) 99.19(9) . 1_555 1_555 yes C(6) C(5) C(9) 100.1(1) . 1_555 1_555 yes C(5) C(6) C(7) 103.4(1) . 1_555 1_555 yes C(6) C(7) C(8) 103.9(2) . 1_555 1_555 yes C(3) C(8) C(7) 106.0(1) . 1_555 1_555 yes C(3) C(8) C(9) 99.1(1) . 1_555 1_555 yes C(7) C(8) C(9) 100.3(1) . 1_555 1_555 yes C(5) C(9) C(8) 95.4(1) . 1_555 1_555 yes O(1) C(10) O(2) 123.1(1) . 1_555 1_555 yes O(1) C(10) C(1) 110.8(1) . 1_555 1_555 yes O(2) C(10) C(1) 126.1(1) . 1_555 1_555 yes O(1) C(11) C(12) 106.8(1) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 O(1) C(10) C(1) N(1) 178.6(1) 1_555 1_555 1_555 1_555 yes O(1) C(10) C(1) C(2) -0.8(2) 1_555 1_555 1_555 1_555 yes O(2) C(10) O(1) C(11) 1.5(2) 1_555 1_555 1_555 1_555 yes O(2) C(10) C(1) N(1) -0.6(2) 1_555 1_555 1_555 1_555 yes O(2) C(10) C(1) C(2) 180.0(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) -0.4(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(5) -173.4(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(2) 0.1(2) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(8) 171.7(2) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) -0.3(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) 0.2(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(8) -174.9(1) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(6) 102.6(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(5) C(9) -154.0(2) 1_555 1_555 1_555 1_555 yes C(1) C(10) O(1) C(11) -177.8(1) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) 0.4(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(7) 69.1(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(8) C(9) -34.4(1) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(6) C(7) 66.7(2) 1_555 1_555 1_555 1_555 yes C(2) C(5) C(9) C(8) -51.7(1) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(10) 179.1(1) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(6) -70.4(1) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(5) C(9) 33.0(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(7) C(6) -68.2(2) 1_555 1_555 1_555 1_555 yes C(3) C(8) C(9) C(5) 52.3(1) 1_555 1_555 1_555 1_555 yes C(4) N(1) C(1) C(10) -179.1(1) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(5) 175.9(1) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(7) -102.6(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(8) C(9) 153.9(2) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(1) C(10) 6.1(3) 1_555 1_555 1_555 1_555 yes C(5) C(2) C(3) C(8) 0.9(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) 1.0(2) 1_555 1_555 1_555 1_555 yes C(5) C(9) C(8) C(7) -55.9(1) 1_555 1_555 1_555 1_555 yes C(6) C(5) C(9) C(8) 56.6(1) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(8) C(9) 34.4(2) 1_555 1_555 1_555 1_555 yes C(7) C(6) C(5) C(9) -36.0(2) 1_555 1_555 1_555 1_555 yes C(10) O(1) C(11) C(12) 179.0(1) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) C(1) 3.553(2) . 2_656 ? O(1) C(10) 3.569(2) . 2_656 ? O(2) N(1) 2.888(2) . 2_657 ? #============================================================================== # End of CIF #============================================================================== data_syn-23 #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C17 H18 N2 O4 ' _chemical_formula_moiety 'C17 H18 N2 O4 ' _chemical_formula_weight 314.34 _chemical_melting_point 461-462 #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x, y, z 1/2-x, 1/2+y, 1/2-z -x, -y, -z 1/2+x, 1/2-y, 1/2+z _cell_length_a 5.612(2) _cell_length_b 17.640(2) _cell_length_c 16.329(2) _cell_angle_alpha 90 _cell_angle_beta 94.40(2) _cell_angle_gamma 90 _cell_volume 1611.8(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.7 _cell_measurement_theta_max 15.0 _cell_measurement_temperature 296.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.295 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.999 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 4216 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.9995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.9995 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.11 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). The hydrogen atoms except for the ethyl group are refined isotopically and the ethyl hydrogen atoms are placed at the calculated positions. ; _reflns_number_total 3707 _reflns_number_gt 1705 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1404 _refine_ls_hydrogen_treatment refpar _refine_ls_number_reflns 3707 _refine_ls_number_parameters 241 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 0.29 _refine_diff_density_min -0.22 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.012(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #============================================================================== # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O(1) O 0.7301(3) 0.53715(9) 0.79215(10) 0.0484(5) Uani 1.00 d . . . O(2) O 0.4502(3) 0.45285(10) 0.8232(1) 0.0601(6) Uani 1.00 d . . . O(3) O 0.8099(3) 0.75727(9) 0.7518(1) 0.0529(5) Uani 1.00 d . . . O(4) O 0.5967(3) 0.86309(10) 0.7691(1) 0.0642(6) Uani 1.00 d . . . N(1) N 0.1825(4) 0.4882(1) 0.6761(1) 0.0424(6) Uani 1.00 d . . . N(2) N 0.2726(4) 0.8142(1) 0.6338(1) 0.0493(7) Uani 1.00 d . . . C(1) C 0.4011(4) 0.5216(1) 0.6993(1) 0.0385(6) Uani 1.00 d . . . C(2) C 0.4429(4) 0.5737(1) 0.6391(1) 0.0353(6) Uani 1.00 d . . . C(3) C 0.2458(4) 0.5718(1) 0.5801(1) 0.0368(6) Uani 1.00 d . . . C(4) C 0.0876(4) 0.5189(1) 0.6045(1) 0.0408(7) Uani 1.00 d . . . C(5) C 0.4745(4) 0.7754(1) 0.6642(1) 0.0402(6) Uani 1.00 d . . . C(6) C 0.4790(4) 0.7091(1) 0.6203(1) 0.0379(6) Uani 1.00 d . . . C(7) C 0.2793(4) 0.7083(1) 0.5629(1) 0.0394(6) Uani 1.00 d . . . C(8) C 0.1522(5) 0.7730(1) 0.5730(2) 0.0459(7) Uani 1.00 d . . . C(9) C 0.6134(4) 0.6346(1) 0.6132(1) 0.0373(6) Uani 1.00 d . . . C(10) C 0.5643(5) 0.6248(1) 0.5175(1) 0.0434(7) Uani 1.00 d . . . C(11) C 0.2853(4) 0.6329(1) 0.5166(1) 0.0410(7) Uani 1.00 d . . . C(12) C 0.5245(4) 0.4994(1) 0.7762(1) 0.0413(7) Uani 1.00 d . . . C(13) C 0.6280(4) 0.8041(1) 0.7324(1) 0.0445(7) Uani 1.00 d . . . C(14) C 0.8587(5) 0.5216(2) 0.8705(2) 0.0608(9) Uani 1.00 d . . . C(15) C 0.7590(6) 0.5683(2) 0.9377(2) 0.089(1) Uani 1.00 d . . . C(16) C 0.9757(5) 0.7786(2) 0.8195(2) 0.0681(10) Uani 1.00 d . . . C(17) C 1.1545(5) 0.7171(2) 0.8324(2) 0.075(1) Uani 1.00 d . . . H(1) H 0.111(5) 0.453(2) 0.706(2) 0.067(8) Uiso 1.00 calc . . . H(2) H -0.074(4) 0.504(1) 0.581(1) 0.049(7) Uiso 1.00 calc . . . H(3) H 0.221(5) 0.854(1) 0.655(2) 0.062(8) Uiso 1.00 calc . . . H(4) H 0.003(4) 0.791(1) 0.546(1) 0.049(7) Uiso 1.00 calc . . . H(5) H 0.782(4) 0.632(1) 0.636(1) 0.041(6) Uiso 1.00 calc . . . H(6) H 0.618(4) 0.574(1) 0.498(1) 0.050(7) Uiso 1.00 calc . . . H(7) H 0.642(4) 0.666(1) 0.487(1) 0.050(6) Uiso 1.00 calc . . . H(8) H 0.192(3) 0.630(1) 0.463(1) 0.026(5) Uiso 1.00 calc . . . H(9) H 1.0227 0.5337 0.8674 0.0730 Uiso 1.00 calc . . . H(10) H 0.8436 0.4693 0.8831 0.0730 Uiso 1.00 calc . . . H(11) H 0.5953 0.5562 0.9410 0.1059 Uiso 1.00 calc . . . H(12) H 0.8454 0.5573 0.9886 0.1059 Uiso 1.00 calc . . . H(13) H 0.7746 0.6206 0.9254 0.1059 Uiso 1.00 calc . . . H(14) H 0.8932 0.7853 0.8676 0.0817 Uiso 1.00 calc . . . H(15) H 1.0534 0.8246 0.8070 0.0817 Uiso 1.00 calc . . . H(16) H 1.2642 0.7294 0.8777 0.0905 Uiso 1.00 calc . . . H(17) H 1.2386 0.7113 0.7845 0.0905 Uiso 1.00 calc . . . H(18) H 1.0755 0.6710 0.8435 0.0905 Uiso 1.00 calc . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.048(1) 0.048(1) 0.047(1) -0.0058(8) -0.0054(8) 0.0052(8) O(2) 0.070(1) 0.052(1) 0.057(1) -0.0155(9) -0.0056(9) 0.0211(9) O(3) 0.056(1) 0.0454(10) 0.056(1) 0.0054(8) -0.0050(9) -0.0142(9) O(4) 0.068(1) 0.045(1) 0.078(1) 0.0064(9) -0.0042(10) -0.0274(10) N(1) 0.045(1) 0.034(1) 0.048(1) -0.0032(9) 0.0028(10) 0.0029(10) N(2) 0.058(1) 0.032(1) 0.059(1) 0.007(1) 0.005(1) -0.007(1) C(1) 0.041(1) 0.032(1) 0.042(1) 0.001(1) 0.000(1) -0.002(1) C(2) 0.042(1) 0.026(1) 0.038(1) 0.0036(10) 0.002(1) -0.0026(10) C(3) 0.042(1) 0.027(1) 0.041(1) 0.0031(10) -0.001(1) -0.0060(10) C(4) 0.043(1) 0.034(1) 0.045(1) 0.002(1) -0.003(1) -0.007(1) C(5) 0.046(1) 0.029(1) 0.045(1) 0.002(1) 0.005(1) -0.003(1) C(6) 0.043(1) 0.031(1) 0.040(1) 0.0005(10) 0.006(1) 0.0016(10) C(7) 0.047(1) 0.031(1) 0.040(1) 0.001(1) 0.000(1) 0.003(1) C(8) 0.050(2) 0.035(1) 0.053(2) 0.006(1) -0.002(1) 0.001(1) C(9) 0.041(1) 0.033(1) 0.038(1) 0.003(1) 0.004(1) -0.0026(10) C(10) 0.056(2) 0.039(1) 0.036(1) 0.003(1) 0.007(1) -0.001(1) C(11) 0.053(1) 0.033(1) 0.036(1) 0.002(1) -0.005(1) -0.003(1) C(12) 0.047(1) 0.033(1) 0.044(1) -0.001(1) 0.003(1) 0.001(1) C(13) 0.049(1) 0.034(1) 0.051(2) -0.003(1) 0.008(1) -0.004(1) C(14) 0.063(2) 0.059(2) 0.057(2) 0.002(1) -0.018(1) 0.002(1) C(15) 0.103(3) 0.104(3) 0.057(2) -0.003(2) -0.003(2) -0.011(2) C(16) 0.067(2) 0.073(2) 0.062(2) 0.004(2) -0.012(1) -0.016(2) C(17) 0.063(2) 0.082(2) 0.079(2) -0.002(2) -0.002(2) 0.014(2) #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(12) 1.340(3) . . yes O(1) C(14) 1.447(3) . . yes O(2) C(12) 1.219(3) . . yes O(3) C(13) 1.333(3) . . yes O(3) C(16) 1.439(3) . . yes O(4) C(13) 1.220(3) . . yes N(1) C(1) 1.387(3) . . yes N(1) C(4) 1.360(3) . . yes N(2) C(5) 1.383(3) . . yes N(2) C(8) 1.367(3) . . yes C(1) C(2) 1.378(3) . . yes C(1) C(12) 1.440(3) . . yes C(2) C(3) 1.410(3) . . yes C(2) C(9) 1.520(3) . . yes C(3) C(4) 1.368(3) . . yes C(3) C(11) 1.524(3) . . yes C(5) C(6) 1.374(3) . . yes C(5) C(13) 1.446(3) . . yes C(6) C(7) 1.405(3) . . yes C(6) C(9) 1.524(3) . . yes C(7) C(8) 1.362(3) . . yes C(7) C(11) 1.532(3) . . yes C(9) C(10) 1.574(3) . . yes C(10) C(11) 1.571(4) . . yes C(14) C(15) 1.514(4) . . yes C(16) C(17) 1.482(4) . . yes #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(12) O(1) C(14) 116.2(2) . 1_555 1_555 yes C(13) O(3) C(16) 117.3(2) . 1_555 1_555 yes C(1) N(1) C(4) 110.2(2) . 1_555 1_555 yes C(5) N(2) C(8) 110.1(2) . 1_555 1_555 yes N(1) C(1) C(2) 106.5(2) . 1_555 1_555 yes N(1) C(1) C(12) 118.6(2) . 1_555 1_555 yes C(2) C(1) C(12) 134.8(2) . 1_555 1_555 yes C(1) C(2) C(3) 107.7(2) . 1_555 1_555 yes C(1) C(2) C(9) 144.6(2) . 1_555 1_555 yes C(3) C(2) C(9) 107.6(2) . 1_555 1_555 yes C(2) C(3) C(4) 108.1(2) . 1_555 1_555 yes C(2) C(3) C(11) 107.6(2) . 1_555 1_555 yes C(4) C(3) C(11) 144.2(2) . 1_555 1_555 yes N(1) C(4) C(3) 107.5(2) . 1_555 1_555 yes N(2) C(5) C(6) 106.3(2) . 1_555 1_555 yes N(2) C(5) C(13) 121.8(2) . 1_555 1_555 yes C(6) C(5) C(13) 131.8(2) . 1_555 1_555 yes C(5) C(6) C(7) 108.1(2) . 1_555 1_555 yes C(5) C(6) C(9) 143.4(2) . 1_555 1_555 yes C(7) C(6) C(9) 108.4(2) . 1_555 1_555 yes C(6) C(7) C(8) 108.0(2) . 1_555 1_555 yes C(6) C(7) C(11) 106.9(2) . 1_555 1_555 yes C(8) C(7) C(11) 144.9(2) . 1_555 1_555 yes N(2) C(8) C(7) 107.4(2) . 1_555 1_555 yes C(2) C(9) C(6) 105.2(2) . 1_555 1_555 yes C(2) C(9) C(10) 97.7(2) . 1_555 1_555 yes C(6) C(9) C(10) 96.9(2) . 1_555 1_555 yes C(9) C(10) C(11) 95.7(2) . 1_555 1_555 yes C(3) C(11) C(7) 105.5(2) . 1_555 1_555 yes C(3) C(11) C(10) 97.2(2) . 1_555 1_555 yes C(7) C(11) C(10) 97.7(2) . 1_555 1_555 yes O(1) C(12) O(2) 122.9(2) . 1_555 1_555 yes O(1) C(12) C(1) 112.6(2) . 1_555 1_555 yes O(2) C(12) C(1) 124.5(2) . 1_555 1_555 yes O(3) C(13) O(4) 123.2(2) . 1_555 1_555 yes O(3) C(13) C(5) 111.5(2) . 1_555 1_555 yes O(4) C(13) C(5) 125.3(2) . 1_555 1_555 yes O(1) C(14) C(15) 110.5(2) . 1_555 1_555 yes O(3) C(16) C(17) 108.0(2) . 1_555 1_555 yes #------------------------------------------------------------------------------ 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 O(1) C(12) C(1) N(1) -178.5(2) 1_555 1_555 1_555 1_555 yes O(1) C(12) C(1) C(2) -1.6(4) 1_555 1_555 1_555 1_555 yes O(2) C(12) O(1) C(14) -1.9(3) 1_555 1_555 1_555 1_555 yes O(2) C(12) C(1) N(1) -0.1(4) 1_555 1_555 1_555 1_555 yes O(2) C(12) C(1) C(2) 176.8(2) 1_555 1_555 1_555 1_555 yes O(3) C(13) C(5) N(2) 179.3(2) 1_555 1_555 1_555 1_555 yes O(3) C(13) C(5) C(6) 3.2(4) 1_555 1_555 1_555 1_555 yes O(4) C(13) O(3) C(16) -0.2(4) 1_555 1_555 1_555 1_555 yes O(4) C(13) C(5) N(2) 0.2(4) 1_555 1_555 1_555 1_555 yes O(4) C(13) C(5) C(6) -176.0(3) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(3) 0.7(2) 1_555 1_555 1_555 1_555 yes N(1) C(1) C(2) C(9) 177.0(3) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(2) -0.4(3) 1_555 1_555 1_555 1_555 yes N(1) C(4) C(3) C(11) -175.0(3) 1_555 1_555 1_555 1_555 yes N(2) C(5) C(6) C(7) 0.3(3) 1_555 1_555 1_555 1_555 yes N(2) C(5) C(6) C(9) -175.7(3) 1_555 1_555 1_555 1_555 yes N(2) C(8) C(7) C(6) 1.5(3) 1_555 1_555 1_555 1_555 yes N(2) C(8) C(7) C(11) 177.0(3) 1_555 1_555 1_555 1_555 yes C(1) N(1) C(4) C(3) 0.8(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(4) -0.2(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(3) C(11) 176.5(2) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(9) C(6) -110.4(3) 1_555 1_555 1_555 1_555 yes C(1) C(2) C(9) C(10) 150.3(3) 1_555 1_555 1_555 1_555 yes C(1) C(12) O(1) C(14) 176.5(2) 1_555 1_555 1_555 1_555 yes C(2) C(1) N(1) C(4) -1.0(3) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(11) C(7) -64.7(2) 1_555 1_555 1_555 1_555 yes C(2) C(3) C(11) C(10) 35.4(2) 1_555 1_555 1_555 1_555 yes C(2) C(9) C(6) C(5) 111.2(3) 1_555 1_555 1_555 1_555 yes C(2) C(9) C(6) C(7) -64.8(2) 1_555 1_555 1_555 1_555 yes C(2) C(9) C(10) C(11) 53.0(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(1) C(12) -176.5(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(9) C(6) 66.0(2) 1_555 1_555 1_555 1_555 yes C(3) C(2) C(9) C(10) -33.3(2) 1_555 1_555 1_555 1_555 yes C(3) C(11) C(7) C(6) 66.0(2) 1_555 1_555 1_555 1_555 yes C(3) C(11) C(7) C(8) -109.6(4) 1_555 1_555 1_555 1_555 yes C(3) C(11) C(10) C(9) -53.5(2) 1_555 1_555 1_555 1_555 yes C(4) N(1) C(1) C(12) 176.8(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(2) C(9) -178.0(2) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(11) C(7) 110.0(4) 1_555 1_555 1_555 1_555 yes C(4) C(3) C(11) C(10) -150.0(3) 1_555 1_555 1_555 1_555 yes C(5) N(2) C(8) C(7) -1.3(3) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(8) -1.2(3) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(7) C(11) -178.5(2) 1_555 1_555 1_555 1_555 yes C(5) C(6) C(9) C(10) -148.9(3) 1_555 1_555 1_555 1_555 yes C(5) C(13) O(3) C(16) -179.4(2) 1_555 1_555 1_555 1_555 yes C(6) C(5) N(2) C(8) 0.6(3) 1_555 1_555 1_555 1_555 yes C(6) C(7) C(11) C(10) -33.8(2) 1_555 1_555 1_555 1_555 yes C(6) C(9) C(10) C(11) -53.5(2) 1_555 1_555 1_555 1_555 yes C(7) C(6) C(5) C(13) 176.9(2) 1_555 1_555 1_555 1_555 yes C(7) C(6) C(9) C(10) 35.1(2) 1_555 1_555 1_555 1_555 yes C(7) C(11) C(10) C(9) 53.3(2) 1_555 1_555 1_555 1_555 yes C(8) N(2) C(5) C(13) -176.4(2) 1_555 1_555 1_555 1_555 yes C(8) C(7) C(6) C(9) 176.3(2) 1_555 1_555 1_555 1_555 yes C(8) C(7) C(11) C(10) 150.7(4) 1_555 1_555 1_555 1_555 yes C(9) C(2) C(1) C(12) -0.1(5) 1_555 1_555 1_555 1_555 yes C(9) C(2) C(3) C(11) -1.3(2) 1_555 1_555 1_555 1_555 yes C(9) C(6) C(5) C(13) 0.9(5) 1_555 1_555 1_555 1_555 yes C(9) C(6) C(7) C(11) -1.0(2) 1_555 1_555 1_555 1_555 yes C(12) O(1) C(14) C(15) -82.9(3) 1_555 1_555 1_555 1_555 yes C(13) O(3) C(16) C(17) 177.4(2) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) N(1) 3.395(3) . 1_655 ? O(1) O(4) 3.395(2) . 2_646 ? O(2) N(2) 2.859(3) . 2_546 ? O(2) O(4) 3.440(3) . 2_646 ? O(3) N(2) 3.497(3) . 1_655 ? O(4) N(1) 2.888(3) . 2_556 ? O(4) C(12) 3.330(3) . 2_656 ? C(4) C(9) 3.365(3) . 1_455 ? C(4) C(4) 3.540(5) . 3_566 ? C(5) C(17) 3.547(4) . 1_455 ? C(13) C(17) 3.570(4) . 1_455 ? #============================================================================== # End of CIF #==============================================================================