# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1412 data_1 #----------------------------------------------------------------------- _audit_creation_date '1998-05-20' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #----------------------------------------------------------------------- _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. ; #----------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #----------------------------------------------------------------------- _cell_length_a 11.245(2) _cell_length_b 16.635(2) _cell_length_c 10.714(2) _cell_angle_alpha 96.95(1) _cell_angle_beta 101.14(2) _cell_angle_gamma 73.22(1) _cell_volume 1878.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.0 _cell_measurement_theta_max 27.5 #----------------------------------------------------------------------- _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #----------------------------------------------------------------------- _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourlessneedle' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.105 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 312.45 _chemical_formula_analytical ? _chemical_formula_sum 'C20 H28 N2 O ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 680.00 _exptl_absorpt_coefficient_mu 0.495 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.896 _exptl_special_details ; The scan width was (0.89+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #----------------------------------------------------------------------- _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.44 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -2 -3 2 -1 -3 0 -4 -2 _diffrn_reflns_number 8399 _reflns_number_total 7668 _reflns_number_observed 3757 _reflns_observed_criterion >2.00\s(I) _diffrn_reflns_av_R_equivalents 0.03849 _diffrn_reflns_av_sigmaI/netI 0.110 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 79.86 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.06456 _diffrn_orient_matrix_UB_12 -0.05420 _diffrn_orient_matrix_UB_13 -0.01550 _diffrn_orient_matrix_UB_21 -0.04071 _diffrn_orient_matrix_UB_22 -0.02950 _diffrn_orient_matrix_UB_23 0.04824 _diffrn_orient_matrix_UB_31 -0.05521 _diffrn_orient_matrix_UB_32 -0.01238 _diffrn_orient_matrix_UB_33 -0.08078 #----------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 80 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 112 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 4 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #----------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 1.4372(3) 0.1982(2) -0.6209(3) 0.066(1) 1.000 . Uani d ? O(2) 2.0123(3) 0.1980(2) -0.0415(3) 0.091(1) 1.000 . Uani d ? N(1) 1.2323(3) 0.1973(2) -0.6681(3) 0.048(1) 1.000 . Uani d ? N(2) 1.2806(5) 0.4404(3) -0.4135(5) 0.099(2) 1.000 . Uani d ? N(3) 1.8750(3) 0.1962(2) -0.2252(3) 0.059(1) 1.000 . Uani d ? N(4) 1.7551(5) 0.4537(3) 0.0019(5) 0.100(2) 1.000 . Uani d ? C(1) 1.3566(3) 0.1605(3) -0.4568(4) 0.042(1) 1.000 . Uani d ? C(2) 1.3704(4) 0.0766(3) -0.4550(4) 0.051(1) 1.000 . Uani d ? C(3) 1.4112(4) 0.0344(3) -0.3421(5) 0.061(2) 1.000 . Uani d ? C(4) 1.4380(4) 0.0791(3) -0.2317(4) 0.063(2) 1.000 . Uani d ? C(5) 1.4247(4) 0.1658(3) -0.2274(4) 0.051(2) 1.000 . Uani d ? C(6) 1.4551(4) 0.2099(4) -0.1105(4) 0.069(2) 1.000 . Uani d ? C(7) 1.4442(5) 0.2921(4) -0.1038(5) 0.080(2) 1.000 . Uani d ? C(8) 1.3989(4) 0.3365(3) -0.2139(5) 0.071(2) 1.000 . Uani d ? C(9) 1.3663(4) 0.2982(3) -0.3302(4) 0.054(2) 1.000 . Uani d ? C(10) 1.3807(3) 0.2099(3) -0.3421(4) 0.045(1) 1.000 . Uani d ? C(11) 1.3431(4) 0.1890(2) -0.5880(4) 0.046(1) 1.000 . Uani d ? C(12) 1.1156(4) 0.1952(3) -0.6268(4) 0.059(2) 1.000 . Uani d ? C(13) 1.0692(4) 0.1207(3) -0.6866(5) 0.091(2) 1.000 . Uani d ? C(14) 1.0115(4) 0.2773(3) -0.6500(4) 0.083(2) 1.000 . Uani d ? C(15) 1.2240(4) 0.2088(3) -0.8045(4) 0.062(2) 1.000 . Uani d ? C(16) 1.2418(5) 0.2923(3) -0.8267(4) 0.093(2) 1.000 . Uani d ? C(17) 1.3109(5) 0.1353(3) -0.8686(4) 0.088(2) 1.000 . Uani d ? C(18) 1.3181(4) 0.3511(3) -0.4450(4) 0.072(2) 1.000 . Uani d ? C(19) 1.1591(7) 0.4628(4) -0.3691(7) 0.167(3) 1.000 . Uani d ? C(20) 1.2676(9) 0.4882(4) -0.5192(6) 0.193(4) 1.000 . Uani d ? C(21) 1.8202(4) 0.1761(3) -0.0210(4) 0.057(2) 1.000 . Uani d ? C(22) 1.8245(5) 0.0935(4) -0.0255(5) 0.087(2) 1.000 . Uani d ? C(23) 1.7708(7) 0.0623(4) 0.0582(7) 0.113(3) 1.000 . Uani d ? C(24) 1.7144(6) 0.1157(5) 0.1480(6) 0.100(3) 1.000 . Uani d ? C(25) 1.7045(5) 0.2018(4) 0.1548(5) 0.069(2) 1.000 . Uani d ? C(26) 1.6424(6) 0.2548(5) 0.2469(6) 0.099(3) 1.000 . Uani d ? C(27) 1.6327(6) 0.3373(5) 0.2580(5) 0.102(3) 1.000 . Uani d ? C(28) 1.6832(5) 0.3725(3) 0.1744(5) 0.078(2) 1.000 . Uani d ? C(29) 1.7441(4) 0.3229(3) 0.0815(4) 0.059(2) 1.000 . Uani d ? C(30) 1.7586(4) 0.2349(3) 0.0696(4) 0.053(2) 1.000 . Uani d ? C(31) 1.9084(5) 0.1931(3) -0.0979(5) 0.062(2) 1.000 . Uani d ? C(32) 1.7457(4) 0.2019(3) -0.2933(4) 0.063(2) 1.000 . Uani d ? C(33) 1.7359(5) 0.1222(3) -0.3733(5) 0.104(2) 1.000 . Uani d ? C(34) 1.6939(4) 0.2785(3) -0.3729(4) 0.084(2) 1.000 . Uani d ? C(35) 1.9723(5) 0.1957(4) -0.3031(4) 0.079(2) 1.000 . Uani d ? C(36) 2.0786(5) 0.1150(4) -0.2899(5) 0.122(2) 1.000 . Uani d ? C(37) 2.0181(5) 0.2745(4) -0.2761(5) 0.111(3) 1.000 . Uani d ? C(38) 1.7971(5) 0.3636(3) -0.0057(5) 0.093(2) 1.000 . Uani d ? C(39) 1.8439(9) 0.4898(5) -0.022(1) 0.259(6) 1.000 . Uani d ? C(40) 1.6447(8) 0.4806(4) -0.0914(8) 0.203(4) 1.000 . Uani d ? H(2) 1.3519 0.0454 -0.5331 0.060 1.000 . Uiso c ? H(3) 1.4195 -0.0242 -0.3434 0.073 1.000 . Uiso c ? H(4) 1.4670 0.0511 -0.1549 0.076 1.000 . Uiso c ? H(6) 1.4838 0.1805 -0.0349 0.083 1.000 . Uiso c ? H(7) 1.4672 0.3205 -0.0244 0.095 1.000 . Uiso c ? H(8) 1.3903 0.3953 -0.2073 0.085 1.000 . Uiso c ? H(12) 1.1346 0.1899 -0.5373 0.071 1.000 . Uiso c ? H(13a) 0.9964 0.1210 -0.6540 0.109 1.000 . Uiso c ? H(13b) 1.0489 0.1241 -0.7765 0.109 1.000 . Uiso c ? H(13c) 1.1333 0.0702 -0.6672 0.109 1.000 . Uiso c ? H(14a) 1.0403 0.3232 -0.6067 0.099 1.000 . Uiso c ? H(14b) 0.9903 0.2849 -0.7388 0.099 1.000 . Uiso c ? H(14c) 0.9391 0.2748 -0.6188 0.099 1.000 . Uiso c ? H(15) 1.1406 0.2091 -0.8443 0.074 1.000 . Uiso c ? H(16b) 1.2363 0.2963 -0.9154 0.111 1.000 . Uiso c ? H(16c) 1.1778 0.3368 -0.7952 0.111 1.000 . Uiso c ? H(16a) 1.3219 0.2965 -0.7832 0.111 1.000 . Uiso c ? H(17b) 1.3052 0.1456 -0.9551 0.105 1.000 . Uiso c ? H(17c) 1.3951 0.1288 -0.8259 0.105 1.000 . Uiso c ? H(17a) 1.2871 0.0854 -0.8648 0.105 1.000 . Uiso c ? H(18b) 1.3832 0.3394 -0.4949 0.086 1.000 . Uiso c ? H(18a) 1.2473 0.3354 -0.4936 0.086 1.000 . Uiso c ? H(19a) 1.1357 0.5211 -0.3433 0.201 1.000 . Uiso c ? H(19b) 1.0966 0.4503 -0.4358 0.201 1.000 . Uiso c ? H(19c) 1.1660 0.4311 -0.2983 0.201 1.000 . Uiso c ? H(20a) 1.3485 0.4786 -0.5441 0.232 1.000 . Uiso c ? H(20b) 1.2121 0.4713 -0.5892 0.232 1.000 . Uiso c ? H(20c) 1.2364 0.5463 -0.4966 0.232 1.000 . Uiso c ? H(22) 1.8656 0.0556 -0.0877 0.104 1.000 . Uiso c ? H(23) 1.7738 0.0044 0.0522 0.136 1.000 . Uiso c ? H(24) 1.6807 0.0945 0.2076 0.120 1.000 . Uiso c ? H(26) 1.6062 0.2318 0.3025 0.119 1.000 . Uiso c ? H(27) 1.5919 0.3722 0.3227 0.123 1.000 . Uiso c ? H(28) 1.6746 0.4313 0.1823 0.093 1.000 . Uiso c ? H(32) 1.6937 0.2094 -0.2303 0.076 1.000 . Uiso c ? H(33b) 1.7867 0.1126 -0.4378 0.124 1.000 . Uiso c ? H(33c) 1.7640 0.0760 -0.3207 0.124 1.000 . Uiso c ? H(33a) 1.6507 0.1276 -0.4119 0.124 1.000 . Uiso c ? H(35b) 1.7437 0.2733 -0.4373 0.100 1.000 . Uiso c ? H(35c) 1.6093 0.2819 -0.4114 0.100 1.000 . Uiso c ? H(35a) 1.6967 0.3281 -0.3193 0.100 1.000 . Uiso c ? H(35) 1.9325 0.1954 -0.3897 0.095 1.000 . Uiso c ? H(36c) 2.1143 0.1093 -0.2025 0.146 1.000 . Uiso c ? H(36a) 2.0464 0.0684 -0.3226 0.146 1.000 . Uiso c ? H(36b) 2.1413 0.1171 -0.3364 0.146 1.000 . Uiso c ? H(37c) 1.9491 0.3226 -0.2948 0.134 1.000 . Uiso c ? H(37a) 2.0545 0.2791 -0.1886 0.134 1.000 . Uiso c ? H(37b) 2.0795 0.2712 -0.3275 0.134 1.000 . Uiso c ? H(38a) 1.7729 0.3436 -0.0909 0.111 1.000 . Uiso c ? H(38b) 1.8863 0.3472 0.0161 0.111 1.000 . Uiso c ? H(39b) 1.8642 0.4694 -0.1053 0.310 1.000 . Uiso c ? H(39c) 1.8104 0.5493 -0.0209 0.310 1.000 . Uiso c ? H(39a) 1.9176 0.4756 0.0392 0.310 1.000 . Uiso c ? H(40b) 1.6637 0.4591 -0.1739 0.245 1.000 . Uiso c ? H(40c) 1.5797 0.4599 -0.0745 0.245 1.000 . Uiso c ? H(40a) 1.6184 0.5402 -0.0883 0.245 1.000 . Uiso c ? 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) 0.053(2) 0.093(3) 0.059(2) -0.026(2) 0.009(2) 0.020(2) O(2) 0.057(2) 0.153(3) 0.057(2) -0.032(2) -0.011(2) 0.012(2) N(1) 0.047(2) 0.057(2) 0.037(2) -0.013(2) -0.002(2) 0.007(2) N(2) 0.108(4) 0.052(3) 0.108(4) -0.008(3) -0.028(3) 0.003(3) N(3) 0.044(2) 0.081(3) 0.043(2) -0.006(2) 0.004(2) 0.003(2) N(4) 0.118(4) 0.065(3) 0.122(4) -0.029(3) 0.026(3) 0.010(3) C(1) 0.034(2) 0.046(3) 0.043(3) -0.008(2) 0.005(2) 0.007(2) C(2) 0.048(3) 0.055(3) 0.046(3) -0.010(2) 0.007(2) 0.004(2) C(3) 0.054(3) 0.058(3) 0.068(4) -0.002(2) 0.016(3) 0.019(3) C(4) 0.055(3) 0.081(4) 0.051(3) -0.006(3) 0.006(2) 0.027(3) C(5) 0.040(3) 0.070(4) 0.041(3) -0.009(2) 0.007(2) 0.007(3) C(6) 0.060(3) 0.102(4) 0.042(3) -0.015(3) 0.005(3) 0.009(3) C(7) 0.073(4) 0.100(5) 0.054(4) -0.020(4) -0.002(3) -0.013(3) C(8) 0.064(3) 0.062(4) 0.076(4) -0.018(3) -0.007(3) -0.009(3) C(9) 0.042(3) 0.055(3) 0.059(3) -0.013(2) -0.004(2) -0.001(3) C(10) 0.031(2) 0.056(3) 0.041(3) -0.005(2) 0.002(2) 0.005(2) C(11) 0.047(3) 0.046(3) 0.040(3) -0.009(2) 0.002(2) 0.004(2) C(12) 0.046(3) 0.076(4) 0.053(3) -0.014(3) -0.003(2) 0.014(3) C(13) 0.065(4) 0.087(4) 0.123(5) -0.033(3) -0.005(3) 0.020(3) C(14) 0.050(3) 0.086(4) 0.093(4) -0.001(3) -0.004(3) 0.004(3) C(15) 0.073(3) 0.068(4) 0.041(3) -0.019(3) -0.007(2) 0.014(3) C(16) 0.117(5) 0.094(4) 0.067(4) -0.027(4) -0.002(3) 0.039(3) C(17) 0.107(4) 0.104(4) 0.044(3) -0.017(4) 0.017(3) -0.003(3) C(18) 0.073(4) 0.050(3) 0.081(4) -0.014(3) -0.013(3) 0.009(3) C(19) 0.128(6) 0.086(5) 0.205(8) 0.029(5) -0.051(6) -0.036(5) C(20) 0.36(1) 0.076(5) 0.127(6) -0.073(6) -0.046(7) 0.050(5) C(21) 0.066(3) 0.061(4) 0.043(3) -0.020(3) -0.007(3) 0.017(3) C(22) 0.115(5) 0.069(4) 0.067(4) -0.025(4) -0.013(3) 0.014(3) C(23) 0.163(7) 0.092(6) 0.092(6) -0.071(5) -0.042(5) 0.042(4) C(24) 0.120(6) 0.136(7) 0.070(5) -0.084(5) -0.022(4) 0.048(4) C(25) 0.067(4) 0.105(5) 0.044(3) -0.043(3) -0.006(3) 0.022(3) C(26) 0.075(4) 0.179(7) 0.058(4) -0.057(5) 0.005(3) 0.021(5) C(27) 0.081(4) 0.164(7) 0.054(4) -0.019(5) 0.022(3) -0.004(5) C(28) 0.070(4) 0.089(4) 0.064(4) -0.013(3) 0.002(3) -0.005(3) C(29) 0.055(3) 0.074(4) 0.050(3) -0.023(3) 0.007(2) 0.007(3) C(30) 0.049(3) 0.074(4) 0.041(3) -0.025(3) -0.004(2) 0.014(3) C(31) 0.055(3) 0.073(4) 0.048(3) -0.006(3) 0.002(3) 0.005(3) C(32) 0.044(3) 0.084(4) 0.052(3) -0.009(3) 0.001(2) 0.002(3) C(33) 0.094(4) 0.102(5) 0.090(4) -0.019(4) -0.015(3) -0.019(4) C(34) 0.064(3) 0.111(4) 0.059(3) 0.005(3) 0.000(3) 0.025(3) C(35) 0.054(3) 0.121(5) 0.054(3) -0.005(3) 0.018(3) 0.009(3) C(36) 0.072(4) 0.158(6) 0.109(5) 0.031(4) 0.035(4) 0.024(4) C(37) 0.099(5) 0.161(6) 0.095(5) -0.059(5) 0.032(4) 0.006(4) C(38) 0.110(5) 0.064(4) 0.113(5) -0.026(3) 0.031(4) 0.015(3) C(39) 0.23(1) 0.121(7) 0.49(2) -0.099(7) 0.14(1) -0.006(8) C(40) 0.215(9) 0.107(6) 0.206(9) 0.029(6) -0.049(7) 0.004(5) #----------------------------------------------------------------------- _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3757 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1707 _refine_ls_R_factor_obs 0.0744 _refine_ls_wR_factor_all 0.0595 _refine_ls_wR_factor_obs 0.0551 _refine_ls_goodness_of_fit_all 2.158 _refine_ls_goodness_of_fit_obs 2.943 _refine_ls_shift/esd_max 0.0010 _refine_ls_shift/esd_mean 0.0150 _refine_diff_density_min -0.23 _refine_diff_density_max 0.34 #----------------------------------------------------------------------- _geom_special_details ; ? ; 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) 1.233(4) . . yes O(2) C(31) 1.227(5) . . yes N(1) C(11) 1.351(4) . . yes N(1) C(12) 1.475(5) . . yes N(1) C(15) 1.478(5) . . yes N(2) C(18) 1.439(5) . . yes N(2) C(19) 1.465(8) . . yes N(2) C(20) 1.422(7) . . yes N(3) C(31) 1.346(5) . . yes N(3) C(32) 1.477(5) . . yes N(3) C(35) 1.497(5) . . yes N(4) C(38) 1.434(6) . . yes N(4) C(39) 1.382(8) . . yes N(4) C(40) 1.431(7) . . yes C(1) C(2) 1.362(5) . . yes C(1) C(10) 1.419(5) . . yes C(1) C(11) 1.504(5) . . yes C(2) C(3) 1.404(5) . . yes C(2) H(2) 0.95 . . no C(3) C(4) 1.351(5) . . yes C(3) H(3) 0.95 . . no C(4) C(5) 1.403(5) . . yes C(4) H(4) 0.95 . . no C(5) C(6) 1.407(6) . . yes C(5) C(10) 1.437(5) . . yes C(6) C(7) 1.331(6) . . yes C(6) H(6) 0.95 . . no C(7) C(8) 1.399(6) . . yes C(7) H(7) 0.95 . . no C(8) C(9) 1.364(5) . . yes C(8) H(8) 0.95 . . no C(9) C(10) 1.423(5) . . yes C(9) C(18) 1.520(5) . . yes C(12) C(13) 1.507(6) . . yes C(12) C(14) 1.532(5) . . yes C(12) H(12) 0.95 . . no C(13) H(13a) 0.95 . . no C(13) H(13b) 0.95 . . no C(13) H(13c) 0.95 . . no C(14) H(14a) 0.95 . . no C(14) H(14b) 0.95 . . no C(14) H(14c) 0.95 . . no C(15) C(16) 1.512(6) . . yes C(15) C(17) 1.512(6) . . yes C(15) H(15) 0.95 . . no C(16) H(16b) 0.95 . . no C(16) H(16c) 0.95 . . no C(16) H(16a) 0.95 . . no C(17) H(17b) 0.95 . . no C(17) H(17c) 0.95 . . no C(17) H(17a) 0.95 . . no C(18) H(18b) 0.95 . . no C(18) H(18a) 0.95 . . no C(19) H(19a) 0.95 . . no C(19) H(19b) 0.95 . . no C(19) H(19c) 0.95 . . no C(20) H(20a) 0.96 . . no C(20) H(20b) 0.95 . . no C(20) H(20c) 0.95 . . no C(21) C(22) 1.358(6) . . yes C(21) C(30) 1.420(6) . . yes C(21) C(31) 1.508(6) . . yes C(22) C(23) 1.392(7) . . yes C(22) H(22) 0.95 . . no C(23) C(24) 1.349(8) . . yes C(23) H(23) 0.95 . . no C(24) C(25) 1.399(7) . . yes C(24) H(24) 0.95 . . no C(25) C(26) 1.393(7) . . yes C(25) C(30) 1.426(6) . . yes C(26) C(27) 1.339(8) . . yes C(26) H(26) 0.95 . . no C(27) C(28) 1.407(7) . . yes C(27) H(27) 0.95 . . no C(28) C(29) 1.370(6) . . yes C(28) H(28) 0.95 . . no C(29) C(30) 1.418(6) . . yes C(29) C(38) 1.512(6) . . yes C(32) C(33) 1.510(6) . . yes C(32) C(34) 1.527(5) . . yes C(32) H(32) 0.95 . . no C(33) H(33b) 0.95 . . no C(33) H(33c) 0.95 . . no C(33) H(33a) 0.95 . . no C(34) H(35b) 0.95 . . no C(34) H(35c) 0.95 . . no C(34) H(35a) 0.95 . . no C(35) C(36) 1.517(6) . . yes C(35) C(37) 1.519(7) . . yes C(35) H(35) 0.95 . . no C(36) H(36c) 0.95 . . no C(36) H(36a) 0.95 . . no C(36) H(36b) 0.95 . . no C(37) H(37c) 0.95 . . no C(37) H(37a) 0.95 . . no C(37) H(37b) 0.95 . . no C(38) H(38a) 0.95 . . no C(38) H(38b) 0.95 . . no C(39) H(39b) 0.96 . . no C(39) H(39c) 0.95 . . no C(39) H(39a) 0.94 . . no C(40) H(40b) 0.95 . . no C(40) H(40c) 0.95 . . no C(40) H(40a) 0.95 . . no #----------------------------------------------------------------------- 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) N(1) C(12) 123.1(3) . . . yes C(11) N(1) C(15) 120.1(4) . . . yes C(12) N(1) C(15) 116.8(3) . . . yes C(18) N(2) C(19) 108.9(5) . . . yes C(18) N(2) C(20) 112.7(5) . . . yes C(19) N(2) C(20) 108.3(6) . . . yes C(31) N(3) C(32) 123.5(4) . . . yes C(31) N(3) C(35) 119.0(4) . . . yes C(32) N(3) C(35) 117.5(3) . . . yes C(38) N(4) C(39) 112.5(6) . . . yes C(38) N(4) C(40) 109.4(5) . . . yes C(39) N(4) C(40) 107.0(7) . . . yes C(2) C(1) C(10) 120.7(4) . . . yes C(2) C(1) C(11) 113.8(4) . . . yes C(10) C(1) C(11) 124.2(4) . . . yes C(1) C(2) C(3) 122.5(4) . . . yes C(1) C(2) H(2) 118.7 . . . no C(3) C(2) H(2) 118.8 . . . no C(2) C(3) C(4) 118.3(4) . . . yes C(2) C(3) H(3) 120.8 . . . no C(4) C(3) H(3) 120.8 . . . no C(3) C(4) C(5) 121.8(4) . . . yes C(3) C(4) H(4) 119.1 . . . no C(5) C(4) H(4) 119.1 . . . no C(4) C(5) C(6) 119.9(5) . . . yes C(4) C(5) C(10) 120.3(4) . . . yes C(6) C(5) C(10) 119.8(4) . . . yes C(5) C(6) C(7) 121.2(5) . . . yes C(5) C(6) H(6) 119.4 . . . no C(7) C(6) H(6) 119.4 . . . no C(6) C(7) C(8) 119.9(5) . . . yes C(6) C(7) H(7) 120.1 . . . no C(8) C(7) H(7) 120.0 . . . no C(7) C(8) C(9) 122.2(5) . . . yes C(7) C(8) H(8) 118.9 . . . no C(9) C(8) H(8) 118.9 . . . no C(8) C(9) C(10) 119.6(4) . . . yes C(8) C(9) C(18) 118.8(4) . . . yes C(10) C(9) C(18) 121.6(4) . . . yes C(1) C(10) C(5) 116.4(4) . . . yes C(1) C(10) C(9) 126.3(4) . . . yes C(5) C(10) C(9) 117.3(4) . . . yes O(1) C(11) N(1) 122.5(4) . . . yes O(1) C(11) C(1) 118.0(4) . . . yes N(1) C(11) C(1) 119.4(4) . . . yes N(1) C(12) C(13) 112.9(4) . . . yes N(1) C(12) C(14) 111.7(4) . . . yes N(1) C(12) H(12) 107.1 . . . no C(13) C(12) C(14) 110.6(4) . . . yes C(13) C(12) H(12) 107.0 . . . no C(14) C(12) H(12) 107.1 . . . no C(12) C(13) H(13a) 109.5 . . . no C(12) C(13) H(13b) 109.4 . . . no C(12) C(13) H(13c) 109.4 . . . no H(13a) C(13) H(13b) 109.5 . . . no H(13a) C(13) H(13c) 109.6 . . . no H(13b) C(13) H(13c) 109.4 . . . no C(12) C(14) H(14a) 109.5 . . . no C(12) C(14) H(14b) 109.5 . . . no C(12) C(14) H(14c) 109.5 . . . no H(14a) C(14) H(14b) 109.5 . . . no H(14a) C(14) H(14c) 109.5 . . . no H(14b) C(14) H(14c) 109.4 . . . no N(1) C(15) C(16) 112.9(4) . . . yes N(1) C(15) C(17) 111.7(4) . . . yes N(1) C(15) H(15) 106.4 . . . no C(16) C(15) C(17) 112.3(4) . . . yes C(16) C(15) H(15) 106.5 . . . no C(17) C(15) H(15) 106.3 . . . no C(15) C(16) H(16b) 109.5 . . . no C(15) C(16) H(16c) 109.4 . . . no C(15) C(16) H(16a) 109.5 . . . no H(16b) C(16) H(16c) 109.4 . . . no H(16b) C(16) H(16a) 109.6 . . . no H(16c) C(16) H(16a) 109.5 . . . no C(15) C(17) H(17b) 109.5 . . . no C(15) C(17) H(17c) 109.4 . . . no C(15) C(17) H(17a) 109.5 . . . no H(17b) C(17) H(17c) 109.5 . . . no H(17b) C(17) H(17a) 109.5 . . . no H(17c) C(17) H(17a) 109.4 . . . no N(2) C(18) C(9) 114.3(4) . . . yes N(2) C(18) H(18b) 108.2 . . . no N(2) C(18) H(18a) 108.1 . . . no C(9) C(18) H(18b) 108.3 . . . no C(9) C(18) H(18a) 108.3 . . . no H(18b) C(18) H(18a) 109.5 . . . no N(2) C(19) H(19a) 109.7 . . . no N(2) C(19) H(19b) 109.7 . . . no N(2) C(19) H(19c) 109.5 . . . no H(19a) C(19) H(19b) 109.5 . . . no H(19a) C(19) H(19c) 109.2 . . . no H(19b) C(19) H(19c) 109.1 . . . no N(2) C(20) H(20a) 109.3 . . . no N(2) C(20) H(20b) 110.0 . . . no N(2) C(20) H(20c) 110.1 . . . no H(20a) C(20) H(20b) 108.7 . . . no H(20a) C(20) H(20c) 108.8 . . . no H(20b) C(20) H(20c) 109.9 . . . no C(22) C(21) C(30) 120.7(5) . . . yes C(22) C(21) C(31) 113.3(5) . . . yes C(30) C(21) C(31) 124.7(4) . . . yes C(21) C(22) C(23) 122.1(6) . . . yes C(21) C(22) H(22) 118.9 . . . no C(23) C(22) H(22) 119.0 . . . no C(22) C(23) C(24) 119.1(6) . . . yes C(22) C(23) H(23) 120.5 . . . no C(24) C(23) H(23) 120.4 . . . no C(23) C(24) C(25) 121.1(6) . . . yes C(23) C(24) H(24) 119.5 . . . no C(25) C(24) H(24) 119.3 . . . no C(24) C(25) C(26) 119.0(6) . . . yes C(24) C(25) C(30) 120.6(6) . . . yes C(26) C(25) C(30) 120.4(6) . . . yes C(25) C(26) C(27) 120.9(6) . . . yes C(25) C(26) H(26) 119.4 . . . no C(27) C(26) H(26) 119.7 . . . no C(26) C(27) C(28) 120.3(6) . . . yes C(26) C(27) H(27) 119.8 . . . no C(28) C(27) H(27) 119.9 . . . no C(27) C(28) C(29) 120.8(5) . . . yes C(27) C(28) H(28) 119.6 . . . no C(29) C(28) H(28) 119.6 . . . no C(28) C(29) C(30) 120.2(5) . . . yes C(28) C(29) C(38) 118.8(5) . . . yes C(30) C(29) C(38) 121.0(5) . . . yes C(21) C(30) C(25) 116.4(5) . . . yes C(21) C(30) C(29) 126.2(5) . . . yes C(25) C(30) C(29) 117.4(5) . . . yes O(2) C(31) N(3) 122.5(5) . . . yes O(2) C(31) C(21) 117.7(4) . . . yes N(3) C(31) C(21) 119.6(4) . . . yes N(3) C(32) C(33) 112.4(4) . . . yes N(3) C(32) C(34) 111.9(4) . . . yes N(3) C(32) H(32) 107.0 . . . no C(33) C(32) C(34) 111.1(4) . . . yes C(33) C(32) H(32) 107.0 . . . no C(34) C(32) H(32) 107.0 . . . no C(32) C(33) H(33b) 109.6 . . . no C(32) C(33) H(33c) 109.5 . . . no C(32) C(33) H(33a) 109.5 . . . no H(33b) C(33) H(33c) 109.5 . . . no H(33b) C(33) H(33a) 109.4 . . . no H(33c) C(33) H(33a) 109.4 . . . no C(32) C(34) H(35b) 109.5 . . . no C(32) C(34) H(35c) 109.6 . . . no C(32) C(34) H(35a) 109.4 . . . no H(35b) C(34) H(35c) 109.5 . . . no H(35b) C(34) H(35a) 109.3 . . . no H(35c) C(34) H(35a) 109.4 . . . no N(3) C(35) C(36) 110.7(4) . . . yes N(3) C(35) C(37) 112.7(4) . . . yes N(3) C(35) H(35) 106.6 . . . no C(36) C(35) C(37) 113.2(5) . . . yes C(36) C(35) H(35) 106.7 . . . no C(37) C(35) H(35) 106.5 . . . no C(35) C(36) H(36c) 109.4 . . . no C(35) C(36) H(36a) 109.3 . . . no C(35) C(36) H(36b) 109.4 . . . no H(36c) C(36) H(36a) 109.6 . . . no H(36c) C(36) H(36b) 109.6 . . . no H(36a) C(36) H(36b) 109.6 . . . no C(35) C(37) H(37c) 109.6 . . . no C(35) C(37) H(37a) 109.5 . . . no C(35) C(37) H(37b) 109.6 . . . no H(37c) C(37) H(37a) 109.3 . . . no H(37c) C(37) H(37b) 109.4 . . . no H(37a) C(37) H(37b) 109.3 . . . no N(4) C(38) C(29) 114.2(5) . . . yes N(4) C(38) H(38a) 108.2 . . . no N(4) C(38) H(38b) 108.3 . . . no C(29) C(38) H(38a) 108.2 . . . no C(29) C(38) H(38b) 108.2 . . . no H(38a) C(38) H(38b) 109.6 . . . no N(4) C(39) H(39b) 109.2 . . . no N(4) C(39) H(39c) 109.6 . . . no N(4) C(39) H(39a) 110.0 . . . no H(39b) C(39) H(39c) 108.8 . . . no H(39b) C(39) H(39a) 109.3 . . . no H(39c) C(39) H(39a) 109.9 . . . no N(4) C(40) H(40b) 109.3 . . . no N(4) C(40) H(40c) 109.5 . . . no N(4) C(40) H(40a) 109.5 . . . no H(40b) C(40) H(40c) 109.5 . . . no H(40b) C(40) H(40a) 109.4 . . . no H(40c) C(40) H(40a) 109.8 . . . no #----------------------------------------------------------------------- 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(26) 3.324(7) . 1_554 no O(2) C(15) 3.154(5) . 1_656 no O(2) C(17) 3.441(6) . 1_656 no C(2) C(2) 3.481(8) . 2_854 no C(2) C(3) 3.554(6) . 2_854 no C(6) C(25) 3.572(6) . . no C(7) C(30) 3.578(6) . . no C(39) C(39) 3.56(2) . 2_965 no #----------------------------------------------------------------------- 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) N(1) C(12) . . . . -173.5(4) no O(1) C(11) N(1) C(15) . . . . 6.8(6) no O(1) C(11) C(1) C(2) . . . . -99.0(5) no O(1) C(11) C(1) C(10) . . . . 67.8(5) no O(2) C(31) N(3) C(32) . . . . -171.5(4) no O(2) C(31) N(3) C(35) . . . . 7.2(7) no O(2) C(31) C(21) C(22) . . . . -95.8(5) no O(2) C(31) C(21) C(30) . . . . 71.1(6) no N(1) C(11) C(1) C(2) . . . . 76.0(5) no N(1) C(11) C(1) C(10) . . . . -117.1(4) no N(2) C(18) C(9) C(8) . . . . -15.6(6) no N(2) C(18) C(9) C(10) . . . . 165.8(4) no N(3) C(31) C(21) C(22) . . . . 79.5(5) no N(3) C(31) C(21) C(30) . . . . -113.6(5) no N(4) C(38) C(29) C(28) . . . . -12.2(7) no N(4) C(38) C(29) C(30) . . . . 168.9(4) no C(1) C(2) C(3) C(4) . . . . -0.3(7) no C(1) C(10) C(5) C(4) . . . . -2.0(6) no C(1) C(10) C(5) C(6) . . . . 177.7(4) no C(1) C(10) C(9) C(8) . . . . -176.9(4) no C(1) C(10) C(9) C(18) . . . . 1.6(6) no C(1) C(11) N(1) C(12) . . . . 11.7(6) no C(1) C(11) N(1) C(15) . . . . -168.0(4) no C(2) C(1) C(10) C(5) . . . . 2.5(5) no C(2) C(1) C(10) C(9) . . . . -178.0(4) no C(2) C(3) C(4) C(5) . . . . 0.8(7) no C(3) C(2) C(1) C(10) . . . . -1.4(6) no C(3) C(2) C(1) C(11) . . . . 165.9(4) no C(3) C(4) C(5) C(6) . . . . -179.3(4) no C(3) C(4) C(5) C(10) . . . . 0.4(7) no C(4) C(5) C(6) C(7) . . . . 179.5(5) no C(4) C(5) C(10) C(9) . . . . 178.4(4) no C(5) C(6) C(7) C(8) . . . . 1.5(8) no C(5) C(10) C(1) C(11) . . . . -163.5(4) no C(5) C(10) C(9) C(8) . . . . 2.6(6) no C(5) C(10) C(9) C(18) . . . . -178.9(4) no C(6) C(5) C(10) C(9) . . . . -1.9(6) no C(6) C(7) C(8) C(9) . . . . -0.8(8) no C(7) C(6) C(5) C(10) . . . . -0.2(7) no C(7) C(8) C(9) C(10) . . . . -1.4(7) no C(7) C(8) C(9) C(18) . . . . -179.9(4) no C(9) C(10) C(1) C(11) . . . . 16.1(6) no C(9) C(18) N(2) C(19) . . . . -75.1(5) no C(9) C(18) N(2) C(20) . . . . 164.7(5) no C(11) N(1) C(12) C(13) . . . . -114.9(4) no C(11) N(1) C(12) C(14) . . . . 119.7(4) no C(11) N(1) C(15) C(16) . . . . -67.6(5) no C(11) N(1) C(15) C(17) . . . . 60.2(5) no C(12) N(1) C(15) C(16) . . . . 112.7(4) no C(12) N(1) C(15) C(17) . . . . -119.6(4) no C(13) C(12) N(1) C(15) . . . . 64.8(5) no C(14) C(12) N(1) C(15) . . . . -60.6(5) no C(21) C(22) C(23) C(24) . . . . -1.0(9) no C(21) C(30) C(25) C(24) . . . . 0.6(6) no C(21) C(30) C(25) C(26) . . . . 179.9(4) no C(21) C(30) C(29) C(28) . . . . -179.4(4) no C(21) C(30) C(29) C(38) . . . . -0.5(7) no C(21) C(31) N(3) C(32) . . . . 13.5(6) no C(21) C(31) N(3) C(35) . . . . -167.8(4) no C(22) C(21) C(30) C(25) . . . . 1.0(6) no C(22) C(21) C(30) C(29) . . . . -177.9(4) no C(22) C(23) C(24) C(25) . . . . 2(1) no C(23) C(22) C(21) C(30) . . . . -0.8(8) no C(23) C(22) C(21) C(31) . . . . 166.6(5) no C(23) C(24) C(25) C(26) . . . . 178.3(6) no C(23) C(24) C(25) C(30) . . . . -2.5(9) no C(24) C(25) C(26) C(27) . . . . 178.9(6) no C(24) C(25) C(30) C(29) . . . . 179.6(5) no C(25) C(26) C(27) C(28) . . . . 1.3(10) no C(25) C(30) C(21) C(31) . . . . -165.0(4) no C(25) C(30) C(29) C(28) . . . . 1.8(6) no C(25) C(30) C(29) C(38) . . . . -179.4(4) no C(26) C(25) C(30) C(29) . . . . -1.2(6) no C(26) C(27) C(28) C(29) . . . . -0.7(9) no C(27) C(26) C(25) C(30) . . . . -0.3(9) no C(27) C(28) C(29) C(30) . . . . -0.9(7) no C(27) C(28) C(29) C(38) . . . . -179.8(5) no C(29) C(30) C(21) C(31) . . . . 16.2(7) no C(29) C(38) N(4) C(39) . . . . 149.4(7) no C(29) C(38) N(4) C(40) . . . . -91.8(6) no C(31) N(3) C(32) C(33) . . . . -110.6(5) no C(31) N(3) C(32) C(34) . . . . 123.5(4) no C(31) N(3) C(35) C(36) . . . . 61.6(6) no C(31) N(3) C(35) C(37) . . . . -66.2(6) no C(32) N(3) C(35) C(36) . . . . -119.6(4) no C(32) N(3) C(35) C(37) . . . . 112.6(5) no C(33) C(32) N(3) C(35) . . . . 70.6(5) no C(34) C(32) N(3) C(35) . . . . -55.2(5) no #----------------------------------------------------------------------- data_2 _audit_creation_date '1998-04-20' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #----------------------------------------------------------------------- _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; #----------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #----------------------------------------------------------------------- _cell_length_a 15.514(6) _cell_length_b 15.239(2) _cell_length_c 15.305(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3618(1) _cell_formula_units_Z 8 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 12 _cell_measurement_theta_min 38.6 _cell_measurement_theta_max 39.9 #----------------------------------------------------------------------- _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n ' _symmetry_Int_Tables_number 60 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2-y,1/2+z' '1/2+x,1/2-y, -z' ' -x, +y,1/2-z' ' -x, -y, -z' '1/2+x,1/2+y,1/2-z' '1/2-x,1/2+y, +z' ' +x, -y,1/2+z' #----------------------------------------------------------------------- _exptl_crystal_description 'block' _exptl_crystal_colour 'colourlessblock' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.096 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 298.43 _chemical_formula_analytical ? _chemical_formula_sum 'C19 H26 N2 O ' _chemical_formula_moiety 'C19 H26 N2 O ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1296.00 _exptl_absorpt_coefficient_mu 0.526 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.934 _exptl_special_details ; The scan width was (1.47+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #----------------------------------------------------------------------- _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.15 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 2 4 4 -3 -1 5 -1 -1 _diffrn_reflns_number 4041 _reflns_number_total 4041 _reflns_number_observed 2255 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.00000 _diffrn_reflns_av_sigmaI/netI 0.070 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 79.23 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.05440 _diffrn_orient_matrix_UB_12 0.03297 _diffrn_orient_matrix_UB_13 -0.01230 _diffrn_orient_matrix_UB_21 -0.03374 _diffrn_orient_matrix_UB_22 0.05565 _diffrn_orient_matrix_UB_23 -0.00546 _diffrn_orient_matrix_UB_31 0.00758 _diffrn_orient_matrix_UB_32 0.01109 _diffrn_orient_matrix_UB_33 0.06394 #----------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 152 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 208 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 16 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 8 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #---------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.7155(1) 0.1658(1) 0.3318(1) 0.0624(6) 1.000 . Uani d ? N(1) 0.7199(1) 0.0254(1) 0.3794(1) 0.0548(7) 1.000 . Uani d ? N(2) 0.9036(1) 0.1264(1) 0.3985(1) 0.0508(7) 1.000 . Uani d ? C(1) 0.7360(2) 0.1469(1) 0.4838(2) 0.0450(8) 1.000 . Uani d ? C(2) 0.6593(2) 0.1613(2) 0.5261(2) 0.0630(10) 1.000 . Uani d ? C(3) 0.6576(2) 0.1983(2) 0.6108(2) 0.075(1) 1.000 . Uani d ? C(4) 0.7314(2) 0.2195(2) 0.6508(2) 0.073(1) 1.000 . Uani d ? C(5) 0.8119(2) 0.2062(2) 0.6105(2) 0.0570(9) 1.000 . Uani d ? C(6) 0.8884(3) 0.2272(2) 0.6549(2) 0.081(1) 1.000 . Uani d ? C(7) 0.9656(2) 0.2140(2) 0.6172(2) 0.090(1) 1.000 . Uani d ? C(8) 0.9707(2) 0.1805(2) 0.5321(2) 0.073(1) 1.000 . Uani d ? C(9) 0.8983(2) 0.1588(2) 0.4862(2) 0.0498(8) 1.000 . Uani d ? C(10) 0.8152(2) 0.1700(2) 0.5243(2) 0.0452(7) 1.000 . Uani d ? C(11) 0.7261(2) 0.1130(2) 0.3909(2) 0.0476(8) 1.000 . Uani d ? C(12) 0.7274(2) -0.0376(2) 0.4523(2) 0.071(1) 1.000 . Uani d ? C(13) 0.7956(2) -0.1077(2) 0.4349(2) 0.104(1) 1.000 . Uani d ? C(14) 0.6405(2) -0.0784(2) 0.4752(2) 0.110(2) 1.000 . Uani d ? C(15) 0.7014(2) -0.0102(2) 0.2914(2) 0.077(1) 1.000 . Uani d ? C(16) 0.7734(2) 0.0099(2) 0.2273(2) 0.100(1) 1.000 . Uani d ? C(17) 0.6135(2) 0.0179(3) 0.2577(2) 0.123(2) 1.000 . Uani d ? C(18) 0.9069(2) 0.1971(2) 0.3348(2) 0.072(1) 1.000 . Uani d ? C(19) 0.9737(2) 0.0650(2) 0.3830(2) 0.081(1) 1.000 . Uani d ? H(2) 0.6065 0.1461 0.4977 0.075 1.000 . Uiso c ? H(3) 0.6038 0.2078 0.6392 0.091 1.000 . Uiso c ? H(4) 0.7291 0.2438 0.7080 0.087 1.000 . Uiso c ? H(6) 0.8860 0.2507 0.7126 0.097 1.000 . Uiso c ? H(7) 1.0175 0.2281 0.6479 0.109 1.000 . Uiso c ? H(8) 1.0256 0.1731 0.5058 0.088 1.000 . Uiso c ? H(12) 0.7471 -0.0036 0.5042 0.086 1.000 . Uiso c ? H(13b) 0.7771 -0.1398 0.3857 0.125 1.000 . Uiso c ? H(13c) 0.8491 -0.0810 0.4246 0.125 1.000 . Uiso c ? H(13a) 0.7991 -0.1454 0.4845 0.125 1.000 . Uiso c ? H(14b) 0.6227 -0.1105 0.4264 0.131 1.000 . Uiso c ? H(14c) 0.6481 -0.1159 0.5243 0.131 1.000 . Uiso c ? H(14a) 0.6013 -0.0333 0.4887 0.131 1.000 . Uiso c ? H(15) 0.6996 -0.0724 0.2972 0.093 1.000 . Uiso c ? H(16c) 0.7799 0.0714 0.2232 0.118 1.000 . Uiso c ? H(16a) 0.8247 -0.0164 0.2470 0.118 1.000 . Uiso c ? H(16b) 0.7578 -0.0133 0.1717 0.118 1.000 . Uiso c ? H(17c) 0.5702 -0.0035 0.2953 0.147 1.000 . Uiso c ? H(17a) 0.6113 0.0800 0.2551 0.147 1.000 . Uiso c ? H(17b) 0.6054 -0.0055 0.2005 0.147 1.000 . Uiso c ? H(18c) 0.8563 0.2315 0.3394 0.087 1.000 . Uiso c ? H(18a) 0.9560 0.2325 0.3460 0.087 1.000 . Uiso c ? H(18b) 0.9109 0.1729 0.2777 0.087 1.000 . Uiso c ? H(19c) 1.0270 0.0946 0.3874 0.096 1.000 . Uiso c ? H(19a) 0.9711 0.0191 0.4249 0.096 1.000 . Uiso c ? H(19b) 0.9679 0.0406 0.3259 0.096 1.000 . Uiso c ? 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) 0.082(1) 0.053(1) 0.053(1) 0.008(1) -0.010(1) 0.0106(9) N(1) 0.069(2) 0.045(1) 0.051(1) -0.002(1) -0.008(1) -0.003(1) N(2) 0.054(1) 0.058(1) 0.040(1) 0.009(1) 0.004(1) 0.003(1) C(1) 0.055(2) 0.035(1) 0.046(2) 0.007(1) 0.007(1) 0.003(1) C(2) 0.063(2) 0.058(2) 0.068(2) 0.007(2) 0.011(2) 0.002(2) C(3) 0.085(2) 0.068(2) 0.073(3) 0.018(2) 0.032(2) -0.001(2) C(4) 0.110(3) 0.061(2) 0.046(2) 0.020(2) 0.016(2) -0.003(1) C(5) 0.083(2) 0.047(2) 0.041(2) 0.013(2) 0.001(2) 0.002(1) C(6) 0.111(3) 0.086(2) 0.046(2) 0.014(2) -0.020(2) -0.015(2) C(7) 0.090(3) 0.111(3) 0.069(3) 0.004(2) -0.032(2) -0.019(2) C(8) 0.061(2) 0.092(2) 0.064(2) 0.005(2) -0.013(2) -0.007(2) C(9) 0.060(2) 0.051(2) 0.039(2) 0.006(1) -0.005(1) 0.002(1) C(10) 0.062(2) 0.038(1) 0.035(1) 0.006(1) 0.002(1) 0.004(1) C(11) 0.046(2) 0.047(1) 0.050(2) 0.006(1) -0.003(1) 0.002(1) C(12) 0.093(2) 0.045(2) 0.075(2) -0.001(2) -0.005(2) 0.009(2) C(13) 0.112(3) 0.058(2) 0.143(3) 0.016(2) -0.014(3) 0.020(2) C(14) 0.134(3) 0.072(2) 0.125(3) -0.010(2) 0.037(3) 0.017(2) C(15) 0.092(3) 0.066(2) 0.072(2) -0.010(2) -0.017(2) -0.015(2) C(16) 0.139(3) 0.093(3) 0.067(2) -0.008(3) 0.004(2) -0.027(2) C(17) 0.112(3) 0.141(4) 0.116(3) -0.014(3) -0.057(3) -0.022(3) C(18) 0.077(2) 0.085(2) 0.054(2) -0.007(2) 0.000(2) 0.014(2) C(19) 0.081(2) 0.095(2) 0.067(2) 0.026(2) 0.005(2) -0.007(2) #----------------------------------------------------------------------- _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2255 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_obs 0.0529 _refine_ls_wR_factor_all 0.0474 _refine_ls_wR_factor_obs 0.0455 _refine_ls_goodness_of_fit_all 2.843 _refine_ls_goodness_of_fit_obs 3.508 _refine_ls_shift/esd_max 0.0000 _refine_ls_shift/esd_mean 0.0120 _refine_diff_density_min -0.18 _refine_diff_density_max 0.14 #----------------------------------------------------------------------- _geom_special_details ; ? ; 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) 1.222(3) . . yes N(1) C(11) 1.350(3) . . yes N(1) C(12) 1.477(3) . . yes N(1) C(15) 1.480(3) . . yes N(2) C(9) 1.432(3) . . yes N(2) C(18) 1.453(3) . . yes N(2) C(19) 1.454(3) . . yes C(1) C(2) 1.371(3) . . yes C(1) C(10) 1.421(3) . . yes C(1) C(11) 1.520(3) . . yes C(2) C(3) 1.414(4) . . yes C(2) H(2) 0.96 . . no C(3) C(4) 1.337(4) . . yes C(3) H(3) 0.95 . . no C(4) C(5) 1.408(4) . . yes C(4) H(4) 0.95 . . no C(5) C(6) 1.405(4) . . yes C(5) C(10) 1.431(3) . . yes C(6) C(7) 1.344(4) . . yes C(6) H(6) 0.95 . . no C(7) C(8) 1.401(4) . . yes C(7) H(7) 0.96 . . no C(8) C(9) 1.365(3) . . yes C(8) H(8) 0.95 . . no C(9) C(10) 1.425(3) . . yes C(12) C(13) 1.526(4) . . yes C(12) C(14) 1.525(4) . . yes C(12) H(12) 1.00 . . no C(13) H(13b) 0.94 . . no C(13) H(13c) 0.94 . . no C(13) H(13a) 0.95 . . no C(14) H(14b) 0.93 . . no C(14) H(14c) 0.95 . . no C(14) H(14a) 0.94 . . no C(15) C(16) 1.517(4) . . yes C(15) C(17) 1.519(4) . . yes C(15) H(15) 0.95 . . no C(16) H(16c) 0.95 . . no C(16) H(16a) 0.94 . . no C(16) H(16b) 0.95 . . no C(17) H(17c) 0.94 . . no C(17) H(17a) 0.95 . . no C(17) H(17b) 0.95 . . no C(18) H(18c) 0.95 . . no C(18) H(18a) 0.95 . . no C(18) H(18b) 0.95 . . no C(19) H(19c) 0.94 . . no C(19) H(19a) 0.95 . . no C(19) H(19b) 0.95 . . no 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) N(1) C(12) 122.6(2) . . . yes C(11) N(1) C(15) 119.7(2) . . . yes C(12) N(1) C(15) 117.7(2) . . . yes C(9) N(2) C(18) 112.1(2) . . . yes C(9) N(2) C(19) 114.6(2) . . . yes C(18) N(2) C(19) 109.9(2) . . . yes C(2) C(1) C(10) 120.3(2) . . . yes C(2) C(1) C(11) 114.1(2) . . . yes C(10) C(1) C(11) 125.4(2) . . . yes C(1) C(2) C(3) 120.9(3) . . . yes C(1) C(2) H(2) 119.3 . . . no C(3) C(2) H(2) 119.8 . . . no C(2) C(3) C(4) 120.0(3) . . . yes C(2) C(3) H(3) 119.7 . . . no C(4) C(3) H(3) 120.3 . . . no C(3) C(4) C(5) 121.5(3) . . . yes C(3) C(4) H(4) 118.9 . . . no C(5) C(4) H(4) 119.5 . . . no C(4) C(5) C(6) 120.4(3) . . . yes C(4) C(5) C(10) 119.4(3) . . . yes C(6) C(5) C(10) 120.2(3) . . . yes C(5) C(6) C(7) 120.8(3) . . . yes C(5) C(6) H(6) 119.9 . . . no C(7) C(6) H(6) 119.3 . . . no C(6) C(7) C(8) 120.2(3) . . . yes C(6) C(7) H(7) 120.4 . . . no C(8) C(7) H(7) 119.4 . . . no C(7) C(8) C(9) 121.3(3) . . . yes C(7) C(8) H(8) 119.2 . . . no C(9) C(8) H(8) 119.5 . . . no N(2) C(9) C(8) 121.2(3) . . . yes N(2) C(9) C(10) 118.4(2) . . . yes C(8) C(9) C(10) 120.3(2) . . . yes C(1) C(10) C(5) 117.8(3) . . . yes C(1) C(10) C(9) 125.1(2) . . . yes C(5) C(10) C(9) 117.1(3) . . . yes O(1) C(11) N(1) 123.0(2) . . . yes O(1) C(11) C(1) 118.8(2) . . . yes N(1) C(11) C(1) 117.8(2) . . . yes N(1) C(12) C(13) 112.2(3) . . . yes N(1) C(12) C(14) 111.7(3) . . . yes N(1) C(12) H(12) 106.8 . . . no C(13) C(12) C(14) 111.6(3) . . . yes C(13) C(12) H(12) 106.9 . . . no C(14) C(12) H(12) 107.4 . . . no C(12) C(13) H(13b) 106.9 . . . no C(12) C(13) H(13c) 109.8 . . . no C(12) C(13) H(13a) 108.8 . . . no H(13b) C(13) H(13c) 111.1 . . . no H(13b) C(13) H(13a) 109.9 . . . no H(13c) C(13) H(13a) 110.2 . . . no C(12) C(14) H(14b) 106.9 . . . no C(12) C(14) H(14c) 108.5 . . . no C(12) C(14) H(14a) 108.9 . . . no H(14b) C(14) H(14c) 110.7 . . . no H(14b) C(14) H(14a) 111.5 . . . no H(14c) C(14) H(14a) 110.2 . . . no N(1) C(15) C(16) 111.8(3) . . . yes N(1) C(15) C(17) 112.3(3) . . . yes N(1) C(15) H(15) 106.6 . . . no C(16) C(15) C(17) 112.6(3) . . . yes C(16) C(15) H(15) 106.4 . . . no C(17) C(15) H(15) 106.6 . . . no C(15) C(16) H(16c) 108.8 . . . no C(15) C(16) H(16a) 109.3 . . . no C(15) C(16) H(16b) 108.4 . . . no H(16c) C(16) H(16a) 110.7 . . . no H(16c) C(16) H(16b) 109.6 . . . no H(16a) C(16) H(16b) 110.0 . . . no C(15) C(17) H(17c) 109.5 . . . no C(15) C(17) H(17a) 109.2 . . . no C(15) C(17) H(17b) 109.0 . . . no H(17c) C(17) H(17a) 110.1 . . . no H(17c) C(17) H(17b) 109.6 . . . no H(17a) C(17) H(17b) 109.3 . . . no N(2) C(18) H(18c) 109.3 . . . no N(2) C(18) H(18a) 109.2 . . . no N(2) C(18) H(18b) 109.4 . . . no H(18c) C(18) H(18a) 109.8 . . . no H(18c) C(18) H(18b) 109.6 . . . no H(18a) C(18) H(18b) 109.5 . . . no N(2) C(19) H(19c) 109.7 . . . no N(2) C(19) H(19a) 109.5 . . . no N(2) C(19) H(19b) 109.3 . . . no H(19c) C(19) H(19a) 109.9 . . . no H(19c) C(19) H(19b) 109.5 . . . no H(19a) C(19) H(19b) 109.1 . . . no #----------------------------------------------------------------------- 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(4) 3.378(4) . 2_654 no O(1) C(6) 3.549(4) . 2_654 no C(17) C(17) 3.531(8) . 4_655 no #----------------------------------------------------------------------- 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) N(1) C(12) . . . . -176.0(3) no O(1) C(11) N(1) C(15) . . . . 1.4(4) no O(1) C(11) C(1) C(2) . . . . 84.9(3) no O(1) C(11) C(1) C(10) . . . . -89.8(3) no N(1) C(11) C(1) C(2) . . . . -87.8(3) no N(1) C(11) C(1) C(10) . . . . 97.5(3) no N(2) C(9) C(8) C(7) . . . . 178.6(3) no N(2) C(9) C(10) C(1) . . . . 3.8(4) no N(2) C(9) C(10) C(5) . . . . -177.2(2) no C(1) C(2) C(3) C(4) . . . . -0.1(5) no C(1) C(10) C(5) C(4) . . . . -1.5(4) no C(1) C(10) C(5) C(6) . . . . 177.6(3) no C(1) C(10) C(9) C(8) . . . . -177.7(3) no C(1) C(11) N(1) C(12) . . . . -3.6(4) no C(1) C(11) N(1) C(15) . . . . 173.8(2) no C(2) C(1) C(10) C(5) . . . . 1.6(3) no C(2) C(1) C(10) C(9) . . . . -179.4(2) no C(2) C(3) C(4) C(5) . . . . 0.2(5) no C(3) C(2) C(1) C(10) . . . . -0.8(4) no C(3) C(2) C(1) C(11) . . . . -175.8(3) no C(3) C(4) C(5) C(6) . . . . -178.5(3) no C(3) C(4) C(5) C(10) . . . . 0.6(4) no C(4) C(5) C(6) C(7) . . . . 179.4(3) no C(4) C(5) C(10) C(9) . . . . 179.4(2) no C(5) C(6) C(7) C(8) . . . . 1.2(6) no C(5) C(10) C(1) C(11) . . . . 176.0(2) no C(5) C(10) C(9) C(8) . . . . 1.3(4) no C(6) C(5) C(10) C(9) . . . . -1.5(4) no C(6) C(7) C(8) C(9) . . . . -1.4(6) no C(7) C(6) C(5) C(10) . . . . 0.2(5) no C(7) C(8) C(9) C(10) . . . . 0.1(5) no C(8) C(9) N(2) C(18) . . . . -85.7(3) no C(8) C(9) N(2) C(19) . . . . 40.4(4) no C(9) C(10) C(1) C(11) . . . . -5.0(4) no C(10) C(9) N(2) C(18) . . . . 92.7(3) no C(10) C(9) N(2) C(19) . . . . -141.1(2) no C(11) N(1) C(12) C(13) . . . . -126.3(3) no C(11) N(1) C(12) C(14) . . . . 107.6(3) no C(11) N(1) C(15) C(16) . . . . 64.2(4) no C(11) N(1) C(15) C(17) . . . . -63.5(4) no C(12) N(1) C(15) C(16) . . . . -118.3(3) no C(12) N(1) C(15) C(17) . . . . 114.1(3) no C(13) C(12) N(1) C(15) . . . . 56.2(4) no C(14) C(12) N(1) C(15) . . . . -69.9(4) no #----------------------------------------------------------------------- data_3 #----------------------------------------------------------------------- _audit_creation_date '1998-06-15' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #----------------------------------------------------------------------- _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; #----------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #----------------------------------------------------------------------- _cell_length_a 7.956(1) _cell_length_b 14.530(1) _cell_length_c 14.392(2) _cell_angle_alpha 90 _cell_angle_beta 97.53(1) _cell_angle_gamma 90 _cell_volume 1649.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.4 _cell_measurement_theta_max 16.9 #----------------------------------------------------------------------- _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? 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' #----------------------------------------------------------------------- _exptl_crystal_description 'tabular' _exptl_crystal_colour 'colourlesstabular' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 285.39 _chemical_formula_analytical ? _chemical_formula_sum 'C18 H23 N O2 ' _chemical_formula_moiety 'C18 H23 N O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 616.00 _exptl_absorpt_coefficient_mu 0.586 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.880 _exptl_special_details ; The scan width was (1.31+0.30tan\q)\% with an \w scan speed of 8\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #----------------------------------------------------------------------- _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.16 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 4 -2 0 4 3 2 2 -3 _diffrn_reflns_number 3741 _reflns_number_total 3494 _reflns_number_observed 2654 _reflns_observed_criterion >2.00\s(I) _diffrn_reflns_av_R_equivalents 0.02207 _diffrn_reflns_av_sigmaI/netI 0.040 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 79.67 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.03092 _diffrn_orient_matrix_UB_12 0.05981 _diffrn_orient_matrix_UB_13 -0.03216 _diffrn_orient_matrix_UB_21 0.04373 _diffrn_orient_matrix_UB_22 0.03389 _diffrn_orient_matrix_UB_23 0.05868 _diffrn_orient_matrix_UB_31 0.11493 _diffrn_orient_matrix_UB_32 0.00322 _diffrn_orient_matrix_UB_33 -0.02084 #----------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 72 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 92 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 4 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 8 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #----------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.4520(2) 0.59779(9) 0.78842(9) 0.0508(4) 1.000 . Uani d ? O(2) 0.6411(2) 0.46021(9) 0.92176(9) 0.0534(4) 1.000 . Uani d ? N(1) 0.6990(2) 0.5586(1) 0.7357(1) 0.0435(5) 1.000 . Uani d ? C(1) 0.4722(2) 0.4442(1) 0.7403(1) 0.0391(5) 1.000 . Uani d ? C(2) 0.3949(3) 0.4285(2) 0.6506(1) 0.0513(7) 1.000 . Uani d ? C(3) 0.3014(3) 0.3486(2) 0.6269(2) 0.0574(7) 1.000 . Uani d ? C(4) 0.2821(3) 0.2851(2) 0.6933(2) 0.0525(7) 1.000 . Uani d ? C(5) 0.3590(2) 0.2970(1) 0.7867(1) 0.0422(6) 1.000 . Uani d ? C(6) 0.3386(3) 0.2308(1) 0.8556(2) 0.0534(7) 1.000 . Uani d ? C(7) 0.4122(3) 0.2435(2) 0.9448(2) 0.0604(8) 1.000 . Uani d ? C(8) 0.5140(3) 0.3209(2) 0.9706(2) 0.0536(7) 1.000 . Uani d ? C(9) 0.5391(2) 0.3850(1) 0.9048(1) 0.0418(6) 1.000 . Uani d ? C(10) 0.4578(2) 0.3770(1) 0.8106(1) 0.0366(5) 1.000 . Uani d ? C(11) 0.5448(2) 0.5393(1) 0.7597(1) 0.0401(5) 1.000 . Uani d ? C(12) 0.8158(2) 0.4862(1) 0.7116(1) 0.0501(6) 1.000 . Uani d ? C(13) 0.8507(4) 0.4943(2) 0.6106(2) 0.076(1) 1.000 . Uani d ? C(14) 0.9797(3) 0.4841(2) 0.7792(2) 0.0719(10) 1.000 . Uani d ? C(15) 0.7607(3) 0.6544(1) 0.7389(2) 0.0556(7) 1.000 . Uani d ? C(16) 0.6500(4) 0.7154(2) 0.6703(3) 0.083(1) 1.000 . Uani d ? C(17) 0.7851(5) 0.6938(2) 0.8378(2) 0.084(1) 1.000 . Uani d ? C(18) 0.7452(3) 0.4650(2) 1.0106(2) 0.0628(8) 1.000 . Uani d ? H(2) 0.407(2) 0.476(1) 0.603(1) 0.052(6) 1.000 . Uiso d ? H(3) 0.248(2) 0.339(1) 0.563(1) 0.054(6) 1.000 . Uiso d ? H(4) 0.214(2) 0.229(1) 0.680(1) 0.045(5) 1.000 . Uiso d ? H(6) 0.264(2) 0.179(1) 0.836(1) 0.053(6) 1.000 . Uiso d ? H(7) 0.394(2) 0.200(1) 0.993(1) 0.070(7) 1.000 . Uiso d ? H(8) 0.565(2) 0.329(1) 1.037(1) 0.054(6) 1.000 . Uiso d ? H(12) 0.755(2) 0.426(1) 0.718(1) 0.041(5) 1.000 . Uiso d ? H(13a) 0.929(3) 0.442(2) 0.595(1) 0.089(8) 1.000 . Uiso d ? H(13b) 0.740(3) 0.488(2) 0.567(2) 0.097(9) 1.000 . Uiso d ? H(13c) 0.899(3) 0.553(2) 0.599(2) 0.12(1) 1.000 . Uiso d ? H(14a) 0.956(2) 0.478(1) 0.844(1) 0.079(8) 1.000 . Uiso d ? H(14b) 1.043(3) 0.427(2) 0.764(2) 0.099(9) 1.000 . Uiso d ? H(14c) 1.042(3) 0.542(2) 0.776(2) 0.091(9) 1.000 . Uiso d ? H(15) 0.876(2) 0.651(1) 0.715(1) 0.066(6) 1.000 . Uiso d ? H(16b) 0.543(3) 0.724(2) 0.690(2) 0.12(1) 1.000 . Uiso d ? H(16c) 0.624(4) 0.680(2) 0.610(2) 0.15(1) 1.000 . Uiso d ? H(16a) 0.701(3) 0.773(2) 0.662(2) 0.094(9) 1.000 . Uiso d ? H(17a) 0.674(3) 0.706(2) 0.859(2) 0.106(10) 1.000 . Uiso d ? H(17b) 0.849(3) 0.752(2) 0.841(1) 0.090(8) 1.000 . Uiso d ? H(17c) 0.850(3) 0.651(2) 0.879(2) 0.12(1) 1.000 . Uiso d ? H(18a) 0.830(3) 0.411(2) 1.016(1) 0.088(8) 1.000 . Uiso d ? H(18b) 0.811(3) 0.520(1) 1.009(1) 0.077(8) 1.000 . Uiso d ? H(18c) 0.668(2) 0.462(1) 1.064(1) 0.070(7) 1.000 . Uiso d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0474(8) 0.0445(8) 0.0636(9) 0.0035(7) 0.0194(7) 0.0007(7) O(2) 0.0541(9) 0.0616(10) 0.0413(8) -0.0105(7) -0.0060(6) 0.0015(7) N(1) 0.0404(9) 0.0400(9) 0.052(1) -0.0029(8) 0.0140(8) -0.0030(8) C(1) 0.033(1) 0.043(1) 0.041(1) -0.0001(9) 0.0048(8) 0.0013(9) C(2) 0.052(1) 0.059(1) 0.042(1) -0.007(1) 0.0012(10) 0.008(1) C(3) 0.056(1) 0.069(2) 0.045(1) -0.013(1) -0.004(1) -0.007(1) C(4) 0.049(1) 0.050(1) 0.058(1) -0.013(1) 0.005(1) -0.009(1) C(5) 0.037(1) 0.041(1) 0.050(1) 0.0020(9) 0.0100(9) -0.0003(9) C(6) 0.054(1) 0.042(1) 0.066(2) -0.006(1) 0.016(1) 0.005(1) C(7) 0.072(2) 0.051(1) 0.062(2) 0.002(1) 0.022(1) 0.018(1) C(8) 0.059(1) 0.059(1) 0.044(1) 0.005(1) 0.008(1) 0.008(1) C(9) 0.038(1) 0.045(1) 0.043(1) 0.0044(9) 0.0065(9) 0.0008(9) C(10) 0.033(1) 0.038(1) 0.039(1) 0.0031(8) 0.0062(8) 0.0010(8) C(11) 0.041(1) 0.041(1) 0.039(1) 0.0002(9) 0.0052(9) 0.0050(9) C(12) 0.045(1) 0.047(1) 0.061(1) 0.001(1) 0.014(1) -0.007(1) C(13) 0.079(2) 0.090(2) 0.065(2) 0.007(2) 0.025(2) -0.017(2) C(14) 0.047(2) 0.086(2) 0.082(2) 0.009(2) 0.006(1) -0.006(2) C(15) 0.052(1) 0.045(1) 0.074(2) -0.011(1) 0.026(1) -0.007(1) C(16) 0.089(2) 0.051(2) 0.114(3) -0.007(2) 0.034(2) 0.025(2) C(17) 0.090(2) 0.072(2) 0.095(2) -0.032(2) 0.032(2) -0.034(2) C(18) 0.054(2) 0.083(2) 0.048(1) -0.004(2) -0.007(1) -0.005(1) #----------------------------------------------------------------------- _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00000|Fo|^2^]' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000048(2) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2654 _refine_ls_number_parameters 283 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_obs 0.0485 _refine_ls_wR_factor_all 0.0332 _refine_ls_wR_factor_obs 0.0326 _refine_ls_goodness_of_fit_all 3.405 _refine_ls_goodness_of_fit_obs 3.803 _refine_ls_shift/esd_max 0.0020 _refine_ls_shift/esd_mean 0.0910 _refine_diff_density_min -0.18 _refine_diff_density_max 0.18 #----------------------------------------------------------------------- _geom_special_details ; ? ; 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) 1.233(2) . . yes O(2) C(9) 1.364(2) . . yes O(2) C(18) 1.431(2) . . yes N(1) C(11) 1.347(2) . . yes N(1) C(12) 1.475(2) . . yes N(1) C(15) 1.475(2) . . yes C(1) C(2) 1.374(2) . . yes C(1) C(10) 1.422(2) . . yes C(1) C(11) 1.508(2) . . yes C(2) C(3) 1.397(3) . . yes C(2) H(2) 0.99(2) . . no C(3) C(4) 1.352(3) . . yes C(3) H(3) 0.96(2) . . no C(4) C(5) 1.413(3) . . yes C(4) H(4) 0.99(2) . . no C(5) C(6) 1.407(3) . . yes C(5) C(10) 1.419(2) . . yes C(6) C(7) 1.353(3) . . yes C(6) H(6) 0.98(2) . . no C(7) C(8) 1.406(3) . . yes C(7) H(7) 0.96(2) . . no C(8) C(9) 1.362(3) . . yes C(8) H(8) 0.99(2) . . no C(9) C(10) 1.428(2) . . yes C(12) C(13) 1.520(3) . . yes C(12) C(14) 1.522(3) . . yes C(12) H(12) 1.01(2) . . no C(13) H(13a) 1.03(2) . . no C(13) H(13b) 1.02(2) . . no C(13) H(13c) 0.96(3) . . no C(14) H(14a) 0.99(2) . . no C(14) H(14b) 1.01(2) . . no C(14) H(14c) 0.99(2) . . no C(15) C(16) 1.519(4) . . yes C(15) C(17) 1.522(3) . . yes C(15) H(15) 1.02(2) . . no C(16) H(16b) 0.95(2) . . no C(16) H(16c) 1.01(3) . . no C(16) H(16a) 0.95(2) . . no C(17) H(17a) 0.99(2) . . no C(17) H(17b) 0.98(2) . . no C(17) H(17c) 0.97(2) . . no C(18) H(18a) 1.03(2) . . no C(18) H(18b) 0.96(2) . . no C(18) H(18c) 1.04(2) . . no #----------------------------------------------------------------------- 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(9) O(2) C(18) 117.4(2) . . . yes C(11) N(1) C(12) 122.3(2) . . . yes C(11) N(1) C(15) 120.0(2) . . . yes C(12) N(1) C(15) 117.6(2) . . . yes C(2) C(1) C(10) 119.1(2) . . . yes C(2) C(1) C(11) 116.0(2) . . . yes C(10) C(1) C(11) 124.2(2) . . . yes C(1) C(2) C(3) 121.7(2) . . . yes C(1) C(2) H(2) 117.9(10) . . . no C(3) C(2) H(2) 120.4(10) . . . no C(2) C(3) C(4) 120.1(2) . . . yes C(2) C(3) H(3) 119(1) . . . no C(4) C(3) H(3) 119(1) . . . no C(3) C(4) C(5) 120.9(2) . . . yes C(3) C(4) H(4) 122.5(10) . . . no C(5) C(4) H(4) 116.6(10) . . . no C(4) C(5) C(6) 120.7(2) . . . yes C(4) C(5) C(10) 119.2(2) . . . yes C(6) C(5) C(10) 120.0(2) . . . yes C(5) C(6) C(7) 120.0(2) . . . yes C(5) C(6) H(6) 116(1) . . . no C(7) C(6) H(6) 123(1) . . . no C(6) C(7) C(8) 121.5(2) . . . yes C(6) C(7) H(7) 120(1) . . . no C(8) C(7) H(7) 118(1) . . . no C(7) C(8) C(9) 119.7(2) . . . yes C(7) C(8) H(8) 120(1) . . . no C(9) C(8) H(8) 120(1) . . . no O(2) C(9) C(8) 124.2(2) . . . yes O(2) C(9) C(10) 114.8(2) . . . yes C(8) C(9) C(10) 121.0(2) . . . yes C(1) C(10) C(5) 118.9(2) . . . yes C(1) C(10) C(9) 123.4(2) . . . yes C(5) C(10) C(9) 117.7(2) . . . yes O(1) C(11) N(1) 123.2(2) . . . yes O(1) C(11) C(1) 117.5(2) . . . yes N(1) C(11) C(1) 118.8(2) . . . yes N(1) C(12) C(13) 111.7(2) . . . yes N(1) C(12) C(14) 112.2(2) . . . yes N(1) C(12) H(12) 106.1(9) . . . no C(13) C(12) C(14) 111.3(2) . . . yes C(13) C(12) H(12) 107.8(9) . . . no C(14) C(12) H(12) 107.4(9) . . . no C(12) C(13) H(13a) 109(1) . . . no C(12) C(13) H(13b) 109(1) . . . no C(12) C(13) H(13c) 111(1) . . . no H(13a) C(13) H(13b) 107(1) . . . no H(13a) C(13) H(13c) 111(1) . . . no H(13b) C(13) H(13c) 107(2) . . . no C(12) C(14) H(14a) 110(1) . . . no C(12) C(14) H(14b) 106(1) . . . no C(12) C(14) H(14c) 110(1) . . . no H(14a) C(14) H(14b) 107(1) . . . no H(14a) C(14) H(14c) 106(1) . . . no H(14b) C(14) H(14c) 115(1) . . . no N(1) C(15) C(16) 111.6(2) . . . yes N(1) C(15) C(17) 112.7(2) . . . yes N(1) C(15) H(15) 104(1) . . . no C(16) C(15) C(17) 112.4(3) . . . yes C(16) C(15) H(15) 106(1) . . . no C(17) C(15) H(15) 108(1) . . . no C(15) C(16) H(16b) 110(1) . . . no C(15) C(16) H(16c) 107(1) . . . no C(15) C(16) H(16a) 112(1) . . . no H(16b) C(16) H(16c) 103(2) . . . no H(16b) C(16) H(16a) 110(1) . . . no H(16c) C(16) H(16a) 112(2) . . . no C(15) C(17) H(17a) 110(1) . . . no C(15) C(17) H(17b) 111(1) . . . no C(15) C(17) H(17c) 108(1) . . . no H(17a) C(17) H(17b) 108(1) . . . no H(17a) C(17) H(17c) 110(2) . . . no H(17b) C(17) H(17c) 107(1) . . . no O(2) C(18) H(18a) 109(1) . . . no O(2) C(18) H(18b) 105(1) . . . no O(2) C(18) H(18c) 108.9(10) . . . no H(18a) C(18) H(18b) 106(1) . . . no H(18a) C(18) H(18c) 110(1) . . . no H(18b) C(18) H(18c) 115(1) . . . no #----------------------------------------------------------------------- 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(4) 3.327(3) . 2_556 no O(1) C(6) 3.481(3) . 2_556 no O(1) C(18) 3.584(3) . 3_667 no O(2) C(18) 3.515(3) . 3_667 no O(2) O(2) 3.574(3) . 3_667 no C(9) C(18) 3.474(3) . 3_667 no C(14) C(18) 3.571(4) . 3_767 no #----------------------------------------------------------------------- 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) N(1) C(12) . . . . 173.0(2) no O(1) C(11) N(1) C(15) . . . . -2.9(3) no O(1) C(11) C(1) C(2) . . . . 90.9(2) no O(1) C(11) C(1) C(10) . . . . -79.6(2) no O(2) C(9) C(8) C(7) . . . . -177.1(2) no O(2) C(9) C(10) C(1) . . . . -3.6(2) no O(2) C(9) C(10) C(5) . . . . 175.8(1) no N(1) C(11) C(1) C(2) . . . . -82.1(2) no N(1) C(11) C(1) C(10) . . . . 107.3(2) no C(1) C(2) C(3) C(4) . . . . 1.4(3) no C(1) C(10) C(5) C(4) . . . . 1.9(3) no C(1) C(10) C(5) C(6) . . . . -178.1(2) no C(1) C(10) C(9) C(8) . . . . 176.6(2) no C(1) C(11) N(1) C(12) . . . . -14.4(3) no C(1) C(11) N(1) C(15) . . . . 169.7(2) no C(2) C(1) C(10) C(5) . . . . -2.1(3) no C(2) C(1) C(10) C(9) . . . . 177.3(2) no C(2) C(3) C(4) C(5) . . . . -1.6(3) no C(3) C(2) C(1) C(10) . . . . 0.5(3) no C(3) C(2) C(1) C(11) . . . . -170.5(2) no C(3) C(4) C(5) C(6) . . . . 180.0(2) no C(3) C(4) C(5) C(10) . . . . -0.1(3) no C(4) C(5) C(6) C(7) . . . . -179.6(2) no C(4) C(5) C(10) C(9) . . . . -177.6(2) no C(5) C(6) C(7) C(8) . . . . -1.9(3) no C(5) C(10) C(1) C(11) . . . . 168.1(2) no C(5) C(10) C(9) C(8) . . . . -3.9(3) no C(6) C(5) C(10) C(9) . . . . 2.4(3) no C(6) C(7) C(8) C(9) . . . . 0.4(3) no C(7) C(6) C(5) C(10) . . . . 0.5(3) no C(7) C(8) C(9) C(10) . . . . 2.6(3) no C(8) C(9) O(2) C(18) . . . . 8.8(3) no C(9) C(10) C(1) C(11) . . . . -12.4(3) no C(10) C(9) O(2) C(18) . . . . -171.0(2) no C(11) N(1) C(12) C(13) . . . . 116.6(2) no C(11) N(1) C(12) C(14) . . . . -117.7(2) no C(11) N(1) C(15) C(16) . . . . -63.1(3) no C(11) N(1) C(15) C(17) . . . . 64.4(3) no C(12) N(1) C(15) C(16) . . . . 120.8(2) no C(12) N(1) C(15) C(17) . . . . -111.7(2) no C(13) C(12) N(1) C(15) . . . . -67.4(3) no C(14) C(12) N(1) C(15) . . . . 58.4(3) no data_4 #----------------------------------------------------------------------- _audit_creation_date '1999-03-11' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #----------------------------------------------------------------------- _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; #----------------------------------------------------------------------- loop_ _publ_manuscript_incl_extra_item '_geom_extra_table_head_3' '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' # # #----------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #----------------------------------------------------------------------- _cell_length_a 10.790(3) _cell_length_b 25.204(4) _cell_length_c 11.938(2) _cell_angle_alpha 90 _cell_angle_beta 104.56(2) _cell_angle_gamma 90 _cell_volume 3142(1) _cell_formula_units_Z 8 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 20.2 _cell_measurement_theta_max 24.4 #----------------------------------------------------------------------- _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' _exptl_crystal_description 'block' _exptl_crystal_colour 'colourlessblock' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.147 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 271.36 _chemical_formula_analytical ? _chemical_formula_sum 'C17 H21 N O2 ' _chemical_formula_moiety '?' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1168.00 _exptl_absorpt_coefficient_mu 0.559 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.913 _exptl_special_details ; The scan width was (0.73+0.30tan\q)\% with an \w scan speed of 8\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #----------------------------------------------------------------------- _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.52 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -8 2 -2 -5 3 -3 -2 3 _diffrn_reflns_number 6753 _reflns_number_total 6392 _reflns_number_observed 2724 _reflns_observed_criterion >2.00\s(I) _diffrn_reflns_av_R_equivalents 0.02561 _diffrn_reflns_av_sigmaI/netI 0.150 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 78.27 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.02066 _diffrn_orient_matrix_UB_12 -0.03581 _diffrn_orient_matrix_UB_13 0.03592 _diffrn_orient_matrix_UB_21 0.04024 _diffrn_orient_matrix_UB_22 0.01708 _diffrn_orient_matrix_UB_23 0.07606 _diffrn_orient_matrix_UB_31 -0.08439 _diffrn_orient_matrix_UB_32 -0.00062 _diffrn_orient_matrix_UB_33 0.02037 #----------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 136 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 168 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 16 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #----------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.2824(3) 0.7336(1) 0.0646(2) 0.0662(10) 1.000 . Uani d ? O(2) 0.3759(3) 0.8471(1) 0.0095(2) 0.065(1) 1.000 . Uani d ? O(3) 0.3029(3) 0.5811(1) 0.3347(2) 0.069(1) 1.000 . Uani d ? O(4) 0.3808(3) 0.6359(1) 0.1339(3) 0.067(1) 1.000 . Uani d ? N(1) 0.1997(3) 0.8013(1) 0.1462(3) 0.054(1) 1.000 . Uani d ? N(2) 0.2761(4) 0.5275(1) 0.1786(3) 0.060(1) 1.000 . Uani d ? C(1) 0.4288(4) 0.7809(2) 0.2082(3) 0.051(1) 1.000 . Uani d ? C(2) 0.4608(4) 0.7520(2) 0.3087(4) 0.064(2) 1.000 . Uani d ? C(3) 0.5877(5) 0.7504(2) 0.3758(4) 0.075(2) 1.000 . Uani d ? C(4) 0.6805(4) 0.7765(2) 0.3418(4) 0.071(2) 1.000 . Uani d ? C(5) 0.6528(4) 0.8071(2) 0.2393(4) 0.059(2) 1.000 . Uani d ? C(6) 0.7502(4) 0.8340(2) 0.2037(4) 0.075(2) 1.000 . Uani d ? C(7) 0.7227(5) 0.8647(2) 0.1081(4) 0.078(2) 1.000 . Uani d ? C(8) 0.5962(5) 0.8698(2) 0.0430(3) 0.064(2) 1.000 . Uani d ? C(9) 0.4995(4) 0.8437(2) 0.0727(3) 0.050(1) 1.000 . Uani d ? C(10) 0.5243(4) 0.8102(1) 0.1728(3) 0.047(1) 1.000 . Uani d ? C(11) 0.2966(4) 0.7719(2) 0.1323(3) 0.051(1) 1.000 . Uani d ? C(12) 0.2187(4) 0.8479(2) 0.2235(4) 0.073(2) 1.000 . Uani d ? C(13) 0.1637(5) 0.8384(2) 0.3261(4) 0.097(2) 1.000 . Uani d ? C(14) 0.1646(5) 0.8983(2) 0.1595(5) 0.125(3) 1.000 . Uani d ? C(15) 0.0676(4) 0.7897(2) 0.0787(4) 0.072(2) 1.000 . Uani d ? C(16) 0.0511(4) 0.7998(2) -0.0501(4) 0.101(2) 1.000 . Uani d ? C(17) 0.0244(4) 0.7346(2) 0.1034(4) 0.107(2) 1.000 . Uani d ? C(18) 0.4912(5) 0.5531(2) 0.2864(3) 0.059(2) 1.000 . Uani d ? C(19) 0.5496(6) 0.5142(2) 0.3610(4) 0.083(2) 1.000 . Uani d ? C(20) 0.6822(7) 0.5118(3) 0.3974(5) 0.112(3) 1.000 . Uani d ? C(21) 0.7565(6) 0.5464(3) 0.3577(5) 0.108(3) 1.000 . Uani d ? C(22) 0.6987(5) 0.5867(2) 0.2782(5) 0.081(2) 1.000 . Uani d ? C(23) 0.7754(6) 0.6232(3) 0.2363(6) 0.111(3) 1.000 . Uani d ? C(24) 0.7183(7) 0.6615(3) 0.1619(6) 0.112(3) 1.000 . Uani d ? C(25) 0.5856(6) 0.6668(2) 0.1255(4) 0.085(2) 1.000 . Uani d ? C(26) 0.5110(5) 0.6321(2) 0.1654(4) 0.058(2) 1.000 . Uani d ? C(27) 0.5641(5) 0.5903(2) 0.2421(3) 0.055(2) 1.000 . Uani d ? C(28) 0.3487(5) 0.5558(2) 0.2656(4) 0.058(2) 1.000 . Uani d ? C(29) 0.1362(5) 0.5268(2) 0.1582(4) 0.075(2) 1.000 . Uani d ? C(30) 0.0789(4) 0.5814(2) 0.1265(4) 0.092(2) 1.000 . Uani d ? C(31) 0.0935(5) 0.5021(2) 0.2584(5) 0.110(2) 1.000 . Uani d ? C(32) 0.3334(4) 0.4975(2) 0.0970(4) 0.073(2) 1.000 . Uani d ? C(33) 0.2864(5) 0.5179(2) -0.0262(4) 0.104(2) 1.000 . Uani d ? C(34) 0.3142(5) 0.4380(2) 0.1068(5) 0.121(2) 1.000 . Uani d ? H(2) 0.3963 0.7329 0.3332 0.077 1.000 . Uiso c ? H(2o) 0.359(5) 0.871(2) -0.049(4) 0.14(2) 1.000 . Uiso d ? H(3) 0.6083 0.7307 0.4459 0.090 1.000 . Uiso c ? H(4) 0.7663 0.7745 0.3875 0.085 1.000 . Uiso c ? H(4o) 0.350(4) 0.667(2) 0.111(3) 0.09(2) 1.000 . Uiso d ? H(6) 0.8366 0.8307 0.2475 0.090 1.000 . Uiso c ? H(7) 0.7895 0.8828 0.0850 0.093 1.000 . Uiso c ? H(8) 0.5778 0.8921 -0.0233 0.077 1.000 . Uiso c ? H(12) 0.3084 0.8528 0.2523 0.087 1.000 . Uiso c ? H(13a) 0.1873 0.8667 0.3800 0.117 1.000 . Uiso c ? H(13b) 0.0728 0.8366 0.3010 0.117 1.000 . Uiso c ? H(13c) 0.1957 0.8059 0.3627 0.117 1.000 . Uiso c ? H(14a) 0.1864 0.9279 0.2097 0.149 1.000 . Uiso c ? H(14b) 0.1990 0.9030 0.0943 0.149 1.000 . Uiso c ? H(14c) 0.0738 0.8956 0.1340 0.149 1.000 . Uiso c ? H(15) 0.0130 0.8141 0.1038 0.085 1.000 . Uiso c ? H(16b) 0.1092 0.7781 -0.0777 0.121 1.000 . Uiso c ? H(16c) -0.0341 0.7916 -0.0912 0.121 1.000 . Uiso c ? H(16a) 0.0683 0.8361 -0.0621 0.121 1.000 . Uiso c ? H(17b) 0.0809 0.7088 0.0852 0.128 1.000 . Uiso c ? H(17c) 0.0255 0.7318 0.1831 0.128 1.000 . Uiso c ? H(17a) -0.0599 0.7283 0.0576 0.128 1.000 . Uiso c ? H(19) 0.4994 0.4886 0.3881 0.099 1.000 . Uiso c ? H(20) 0.7217 0.4854 0.4515 0.134 1.000 . Uiso c ? H(21) 0.8474 0.5440 0.3826 0.129 1.000 . Uiso c ? H(23) 0.8663 0.6208 0.2606 0.132 1.000 . Uiso c ? H(24) 0.7710 0.6855 0.1331 0.134 1.000 . Uiso c ? H(25) 0.5482 0.6944 0.0739 0.102 1.000 . Uiso c ? H(29) 0.1043 0.5047 0.0929 0.090 1.000 . Uiso c ? H(30c) -0.0116 0.5797 0.1149 0.110 1.000 . Uiso c ? H(30a) 0.1134 0.6056 0.1873 0.110 1.000 . Uiso c ? H(30b) 0.0983 0.5932 0.0573 0.110 1.000 . Uiso c ? H(31c) 0.1301 0.5212 0.3276 0.132 1.000 . Uiso c ? H(31a) 0.0028 0.5035 0.2431 0.132 1.000 . Uiso c ? H(31b) 0.1209 0.4662 0.2677 0.132 1.000 . Uiso c ? H(32) 0.4230 0.5038 0.1198 0.087 1.000 . Uiso c ? H(33a) 0.2970 0.5553 -0.0271 0.124 1.000 . Uiso c ? H(33b) 0.3341 0.5017 -0.0738 0.124 1.000 . Uiso c ? H(33c) 0.1981 0.5094 -0.0549 0.124 1.000 . Uiso c ? H(34a) 0.2259 0.4296 0.0782 0.145 1.000 . Uiso c ? H(34b) 0.3626 0.4195 0.0629 0.145 1.000 . Uiso c ? H(34c) 0.3418 0.4275 0.1857 0.145 1.000 . Uiso c ? 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) 0.076(2) 0.056(2) 0.059(2) 0.005(2) 0.003(2) -0.005(2) O(2) 0.063(2) 0.078(2) 0.053(2) -0.001(2) 0.011(2) 0.021(2) O(3) 0.077(2) 0.070(2) 0.065(2) -0.003(2) 0.027(2) -0.023(2) O(4) 0.068(2) 0.051(2) 0.080(2) 0.000(2) 0.015(2) 0.010(2) N(1) 0.055(3) 0.052(2) 0.057(2) -0.003(2) 0.015(2) 0.006(2) N(2) 0.073(3) 0.050(2) 0.060(2) -0.008(2) 0.020(2) -0.011(2) C(1) 0.060(3) 0.047(3) 0.044(3) 0.001(2) 0.010(2) 0.000(2) C(2) 0.072(3) 0.066(3) 0.054(3) -0.006(3) 0.014(3) 0.011(2) C(3) 0.088(4) 0.075(4) 0.055(3) 0.000(3) 0.004(3) 0.012(3) C(4) 0.058(3) 0.077(4) 0.067(3) 0.008(3) -0.006(3) 0.006(3) C(5) 0.059(3) 0.056(3) 0.060(3) 0.000(3) 0.013(3) -0.005(2) C(6) 0.052(3) 0.083(4) 0.085(4) -0.002(3) 0.005(3) -0.004(3) C(7) 0.070(4) 0.079(4) 0.090(4) -0.016(3) 0.030(3) 0.000(3) C(8) 0.071(3) 0.066(3) 0.059(3) -0.007(3) 0.023(3) 0.008(2) C(9) 0.058(3) 0.046(3) 0.049(3) -0.002(3) 0.019(3) -0.002(2) C(10) 0.053(3) 0.042(2) 0.046(3) 0.001(2) 0.012(2) -0.002(2) C(11) 0.060(3) 0.046(3) 0.047(3) -0.002(3) 0.016(3) 0.012(2) C(12) 0.082(4) 0.058(3) 0.086(4) -0.004(3) 0.036(3) -0.008(3) C(13) 0.115(5) 0.108(4) 0.076(3) -0.010(4) 0.038(3) -0.011(3) C(14) 0.201(7) 0.057(3) 0.142(5) 0.026(4) 0.088(5) 0.015(3) C(15) 0.058(3) 0.085(4) 0.073(3) 0.003(3) 0.016(3) 0.015(3) C(16) 0.091(4) 0.124(5) 0.076(4) 0.011(4) -0.004(3) 0.024(3) C(17) 0.080(4) 0.132(5) 0.099(4) -0.048(4) 0.004(3) 0.017(4) C(18) 0.076(4) 0.052(3) 0.048(3) 0.018(3) 0.016(3) -0.007(2) C(19) 0.105(5) 0.074(4) 0.069(3) 0.027(4) 0.022(3) -0.004(3) C(20) 0.121(7) 0.126(6) 0.081(4) 0.067(5) 0.010(4) -0.010(4) C(21) 0.068(5) 0.154(7) 0.089(5) 0.051(5) -0.002(4) -0.054(5) C(22) 0.052(4) 0.109(5) 0.082(4) 0.013(4) 0.019(3) -0.043(4) C(23) 0.060(5) 0.153(7) 0.127(6) -0.012(5) 0.036(4) -0.075(5) C(24) 0.097(6) 0.119(6) 0.146(7) -0.043(5) 0.080(5) -0.050(5) C(25) 0.096(5) 0.076(4) 0.099(4) -0.016(4) 0.054(4) -0.011(3) C(26) 0.058(3) 0.058(3) 0.063(3) -0.007(3) 0.024(3) -0.015(2) C(27) 0.061(4) 0.058(3) 0.049(3) 0.007(3) 0.017(2) -0.017(2) C(28) 0.079(4) 0.044(3) 0.054(3) 0.001(3) 0.022(3) 0.002(2) C(29) 0.074(4) 0.080(4) 0.072(3) -0.021(3) 0.019(3) -0.014(3) C(30) 0.074(4) 0.105(4) 0.101(4) 0.003(3) 0.026(3) 0.005(3) C(31) 0.096(4) 0.117(5) 0.128(5) -0.036(4) 0.048(4) 0.012(4) C(32) 0.089(4) 0.067(3) 0.065(3) -0.001(3) 0.024(3) -0.018(3) C(33) 0.136(5) 0.117(5) 0.062(3) 0.002(4) 0.034(3) -0.022(3) C(34) 0.179(6) 0.060(3) 0.132(5) -0.007(4) 0.054(4) -0.027(3) #----------------------------------------------------------------------- _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.00000025(6) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2724 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.1909 _refine_ls_R_factor_obs 0.0648 _refine_ls_wR_factor_all 0.0496 _refine_ls_wR_factor_obs 0.0401 _refine_ls_goodness_of_fit_all 1.408 _refine_ls_goodness_of_fit_obs 1.796 _refine_ls_shift/esd_max 0.0040 _refine_ls_shift/esd_mean 0.0140 _refine_diff_density_min -0.19 _refine_diff_density_max 0.19 #----------------------------------------------------------------------- _geom_special_details ; ? ; 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) 1.244(4) . . yes O(2) C(9) 1.360(4) . . yes O(2) H(2o) 0.90(5) . . no O(3) C(28) 1.240(4) . . yes O(4) C(26) 1.364(5) . . yes O(4) H(4o) 0.88(4) . . no N(1) C(11) 1.326(4) . . yes N(1) C(12) 1.476(5) . . yes N(1) C(15) 1.479(5) . . yes N(2) C(28) 1.339(4) . . yes N(2) C(29) 1.468(5) . . yes N(2) C(32) 1.485(5) . . yes C(1) C(2) 1.372(5) . . yes C(1) C(10) 1.417(5) . . yes C(1) C(11) 1.502(5) . . yes C(2) C(3) 1.402(5) . . yes C(2) H(2) 0.95 . . no C(3) C(4) 1.343(5) . . yes C(3) H(3) 0.95 . . no C(4) C(5) 1.413(5) . . yes C(4) H(4) 0.95 . . no C(5) C(6) 1.403(5) . . yes C(5) C(10) 1.416(5) . . yes C(6) C(7) 1.348(6) . . yes C(6) H(6) 0.95 . . no C(7) C(8) 1.396(5) . . yes C(7) H(7) 0.95 . . no C(8) C(9) 1.355(5) . . yes C(8) H(8) 0.95 . . no C(9) C(10) 1.431(5) . . yes C(12) C(13) 1.509(5) . . yes C(12) C(14) 1.522(6) . . yes C(12) H(12) 0.95 . . no C(13) H(13a) 0.95 . . no C(13) H(13b) 0.95 . . no C(13) H(13c) 0.95 . . no C(14) H(14a) 0.95 . . no C(14) H(14b) 0.95 . . no C(14) H(14c) 0.95 . . no C(15) C(16) 1.524(5) . . yes C(15) C(17) 1.518(6) . . yes C(15) H(15) 0.95 . . no C(16) H(16b) 0.95 . . no C(16) H(16c) 0.95 . . no C(16) H(16a) 0.95 . . no C(17) H(17b) 0.95 . . no C(17) H(17c) 0.95 . . no C(17) H(17a) 0.95 . . no C(18) C(19) 1.368(5) . . yes C(18) C(27) 1.409(5) . . yes C(18) C(28) 1.496(5) . . yes C(19) C(20) 1.388(7) . . yes C(19) H(19) 0.95 . . no C(20) C(21) 1.348(8) . . yes C(20) H(20) 0.95 . . no C(21) C(22) 1.422(7) . . yes C(21) H(21) 0.95 . . no C(22) C(23) 1.411(8) . . yes C(22) C(27) 1.410(6) . . yes C(23) C(24) 1.351(8) . . yes C(23) H(23) 0.95 . . no C(24) C(25) 1.395(7) . . yes C(24) H(24) 0.95 . . no C(25) C(26) 1.353(6) . . yes C(25) H(25) 0.95 . . no C(26) C(27) 1.417(5) . . yes C(29) C(30) 1.517(6) . . yes C(29) C(31) 1.519(6) . . yes C(29) H(29) 0.95 . . no C(30) H(30c) 0.95 . . no C(30) H(30a) 0.95 . . no C(30) H(30b) 0.95 . . no C(31) H(31c) 0.95 . . no C(31) H(31a) 0.95 . . no C(31) H(31b) 0.95 . . no C(32) C(33) 1.519(6) . . yes C(32) C(34) 1.522(6) . . yes C(32) H(32) 0.95 . . no C(33) H(33a) 0.95 . . no C(33) H(33b) 0.95 . . no C(33) H(33c) 0.95 . . no C(34) H(34a) 0.95 . . no C(34) H(34b) 0.95 . . no C(34) H(34c) 0.95 . . no #----------------------------------------------------------------------- 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(9) O(2) H(2o) 117(3) . . . no C(26) O(4) H(4o) 115(2) . . . no C(11) N(1) C(12) 122.2(4) . . . yes C(11) N(1) C(15) 120.3(4) . . . yes C(12) N(1) C(15) 117.4(4) . . . yes C(28) N(2) C(29) 120.7(4) . . . yes C(28) N(2) C(32) 121.5(4) . . . yes C(29) N(2) C(32) 117.8(4) . . . yes C(2) C(1) C(10) 119.8(4) . . . yes C(2) C(1) C(11) 116.0(4) . . . yes C(10) C(1) C(11) 123.4(4) . . . yes C(1) C(2) C(3) 120.6(4) . . . yes C(1) C(2) H(2) 119.7 . . . no C(3) C(2) H(2) 119.7 . . . no C(2) C(3) C(4) 120.6(4) . . . yes C(2) C(3) H(3) 119.7 . . . no C(4) C(3) H(3) 119.7 . . . no C(3) C(4) C(5) 121.1(4) . . . yes C(3) C(4) H(4) 119.5 . . . no C(5) C(4) H(4) 119.4 . . . no C(4) C(5) C(6) 120.9(5) . . . yes C(4) C(5) C(10) 118.7(4) . . . yes C(6) C(5) C(10) 120.4(4) . . . yes C(5) C(6) C(7) 120.7(4) . . . yes C(5) C(6) H(6) 119.7 . . . no C(7) C(6) H(6) 119.6 . . . no C(6) C(7) C(8) 120.1(4) . . . yes C(6) C(7) H(7) 119.9 . . . no C(8) C(7) H(7) 120.0 . . . no C(7) C(8) C(9) 121.2(4) . . . yes C(7) C(8) H(8) 119.3 . . . no C(9) C(8) H(8) 119.5 . . . no O(2) C(9) C(8) 122.5(4) . . . yes O(2) C(9) C(10) 116.8(4) . . . yes C(8) C(9) C(10) 120.6(4) . . . yes C(1) C(10) C(5) 119.1(4) . . . yes C(1) C(10) C(9) 124.0(4) . . . yes C(5) C(10) C(9) 116.9(4) . . . yes O(1) C(11) N(1) 122.9(4) . . . yes O(1) C(11) C(1) 116.9(4) . . . yes N(1) C(11) C(1) 120.0(4) . . . yes N(1) C(12) C(13) 111.2(4) . . . yes N(1) C(12) C(14) 112.1(4) . . . yes N(1) C(12) H(12) 107.4 . . . no C(13) C(12) C(14) 111.1(4) . . . yes C(13) C(12) H(12) 107.4 . . . no C(14) C(12) H(12) 107.4 . . . no C(12) C(13) H(13a) 109.8 . . . no C(12) C(13) H(13b) 109.7 . . . no C(12) C(13) H(13c) 109.7 . . . no H(13a) C(13) H(13b) 109.3 . . . no H(13a) C(13) H(13c) 109.3 . . . no H(13b) C(13) H(13c) 109.2 . . . no C(12) C(14) H(14a) 109.7 . . . no C(12) C(14) H(14b) 109.6 . . . no C(12) C(14) H(14c) 109.5 . . . no H(14a) C(14) H(14b) 109.5 . . . no H(14a) C(14) H(14c) 109.4 . . . no H(14b) C(14) H(14c) 109.2 . . . no N(1) C(15) C(16) 111.6(4) . . . yes N(1) C(15) C(17) 112.0(4) . . . yes N(1) C(15) H(15) 106.9 . . . no C(16) C(15) C(17) 112.6(4) . . . yes C(16) C(15) H(15) 106.6 . . . no C(17) C(15) H(15) 106.7 . . . no C(15) C(16) H(16b) 109.6 . . . no C(15) C(16) H(16c) 109.7 . . . no C(15) C(16) H(16a) 109.5 . . . no H(16b) C(16) H(16c) 109.4 . . . no H(16b) C(16) H(16a) 109.2 . . . no H(16c) C(16) H(16a) 109.3 . . . no C(15) C(17) H(17b) 109.6 . . . no C(15) C(17) H(17c) 109.6 . . . no C(15) C(17) H(17a) 109.7 . . . no H(17b) C(17) H(17c) 109.3 . . . no H(17b) C(17) H(17a) 109.2 . . . no H(17c) C(17) H(17a) 109.4 . . . no C(19) C(18) C(27) 120.8(5) . . . yes C(19) C(18) C(28) 115.2(5) . . . yes C(27) C(18) C(28) 123.7(4) . . . yes C(18) C(19) C(20) 120.3(6) . . . yes C(18) C(19) H(19) 120.0 . . . no C(20) C(19) H(19) 119.7 . . . no C(19) C(20) C(21) 121.3(7) . . . yes C(19) C(20) H(20) 119.6 . . . no C(21) C(20) H(20) 119.1 . . . no C(20) C(21) C(22) 119.7(6) . . . yes C(20) C(21) H(21) 120.3 . . . no C(22) C(21) H(21) 119.9 . . . no C(21) C(22) C(23) 120.3(6) . . . yes C(21) C(22) C(27) 119.7(6) . . . yes C(23) C(22) C(27) 120.0(6) . . . yes C(22) C(23) C(24) 119.2(7) . . . yes C(22) C(23) H(23) 120.2 . . . no C(24) C(23) H(23) 120.6 . . . no C(23) C(24) C(25) 122.3(7) . . . yes C(23) C(24) H(24) 118.5 . . . no C(25) C(24) H(24) 119.1 . . . no C(24) C(25) C(26) 118.9(6) . . . yes C(24) C(25) H(25) 120.5 . . . no C(26) C(25) H(25) 120.6 . . . no O(4) C(26) C(25) 121.3(5) . . . yes O(4) C(26) C(27) 116.8(4) . . . yes C(25) C(26) C(27) 121.8(5) . . . yes C(18) C(27) C(22) 118.1(5) . . . yes C(18) C(27) C(26) 124.2(5) . . . yes C(22) C(27) C(26) 117.6(5) . . . yes O(3) C(28) N(2) 122.5(4) . . . yes O(3) C(28) C(18) 118.6(4) . . . yes N(2) C(28) C(18) 118.7(4) . . . yes N(2) C(29) C(30) 111.7(4) . . . yes N(2) C(29) C(31) 112.1(4) . . . yes N(2) C(29) H(29) 106.7 . . . no C(30) C(29) C(31) 112.6(4) . . . yes C(30) C(29) H(29) 106.7 . . . no C(31) C(29) H(29) 106.6 . . . no C(29) C(30) H(30c) 109.4 . . . no C(29) C(30) H(30a) 109.5 . . . no C(29) C(30) H(30b) 109.6 . . . no H(30c) C(30) H(30a) 109.3 . . . no H(30c) C(30) H(30b) 109.4 . . . no H(30a) C(30) H(30b) 109.5 . . . no C(29) C(31) H(31c) 109.5 . . . no C(29) C(31) H(31a) 109.6 . . . no C(29) C(31) H(31b) 109.6 . . . no H(31c) C(31) H(31a) 109.4 . . . no H(31c) C(31) H(31b) 109.4 . . . no H(31a) C(31) H(31b) 109.4 . . . no N(2) C(32) C(33) 111.8(4) . . . yes N(2) C(32) C(34) 111.3(4) . . . yes N(2) C(32) H(32) 106.8 . . . no C(33) C(32) C(34) 112.8(4) . . . yes C(33) C(32) H(32) 106.8 . . . no C(34) C(32) H(32) 106.8 . . . no C(32) C(33) H(33a) 109.5 . . . no C(32) C(33) H(33b) 109.7 . . . no C(32) C(33) H(33c) 109.5 . . . no H(33a) C(33) H(33b) 109.4 . . . no H(33a) C(33) H(33c) 109.3 . . . no H(33b) C(33) H(33c) 109.4 . . . no C(32) C(34) H(34a) 109.6 . . . no C(32) C(34) H(34b) 109.7 . . . no C(32) C(34) H(34c) 109.6 . . . no H(34a) C(34) H(34b) 109.3 . . . no H(34a) C(34) H(34c) 109.2 . . . no H(34b) C(34) H(34c) 109.3 . . . no #----------------------------------------------------------------------- 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) O(4) 2.726(4) . . no O(1) C(13) 3.347(5) . 4_564 no O(1) C(26) 3.547(6) . . no O(1) C(25) 3.588(6) . . no O(2) O(3) 2.725(4) . 4_564 no O(4) C(11) 3.545(5) . . no O(4) C(2) 3.572(5) . . no C(1) C(25) 3.598(6) . . no C(2) C(25) 3.562(6) . . no C(2) C(26) 3.580(6) . . no C(8) C(18) 3.563(6) . 4_564 no C(14) C(20) 3.456(8) . 2_655 no #----------------------------------------------------------------------- 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) N(1) C(12) . . . . -177.6(4) no O(1) C(11) N(1) C(15) . . . . -0.8(6) no O(1) C(11) C(1) C(2) . . . . -84.3(5) no O(1) C(11) C(1) C(10) . . . . 85.5(5) no O(2) C(9) C(8) C(7) . . . . -178.5(4) no O(2) C(9) C(10) C(1) . . . . 0.3(6) no O(2) C(9) C(10) C(5) . . . . -179.4(3) no O(3) C(28) N(2) C(29) . . . . 2.4(6) no O(3) C(28) N(2) C(32) . . . . 179.9(4) no O(3) C(28) C(18) C(19) . . . . 84.8(5) no O(3) C(28) C(18) C(27) . . . . -89.6(5) no O(4) C(26) C(25) C(24) . . . . 179.1(5) no O(4) C(26) C(27) C(18) . . . . 0.2(6) no O(4) C(26) C(27) C(22) . . . . -178.3(4) no N(1) C(11) C(1) C(2) . . . . 90.1(5) no N(1) C(11) C(1) C(10) . . . . -100.0(4) no N(2) C(28) C(18) C(19) . . . . -90.1(5) no N(2) C(28) C(18) C(27) . . . . 95.5(5) no C(1) C(2) C(3) C(4) . . . . -1.1(7) no C(1) C(10) C(5) C(4) . . . . -2.7(6) no C(1) C(10) C(5) C(6) . . . . 177.4(4) no C(1) C(10) C(9) C(8) . . . . -178.8(4) no C(1) C(11) N(1) C(12) . . . . 8.4(6) no C(1) C(11) N(1) C(15) . . . . -174.8(3) no C(2) C(1) C(10) C(5) . . . . 3.0(6) no C(2) C(1) C(10) C(9) . . . . -176.7(4) no C(2) C(3) C(4) C(5) . . . . 1.4(7) no C(3) C(2) C(1) C(10) . . . . -1.2(6) no C(3) C(2) C(1) C(11) . . . . 169.1(4) no C(3) C(4) C(5) C(6) . . . . -179.6(5) no C(3) C(4) C(5) C(10) . . . . 0.5(7) no C(4) C(5) C(6) C(7) . . . . -177.6(4) no C(4) C(5) C(10) C(9) . . . . 177.0(4) no C(5) C(6) C(7) C(8) . . . . -0.1(7) no C(5) C(10) C(1) C(11) . . . . -166.5(4) no C(5) C(10) C(9) C(8) . . . . 1.5(6) no C(6) C(5) C(10) C(9) . . . . -2.9(6) no C(6) C(7) C(8) C(9) . . . . -1.3(7) no C(7) C(6) C(5) C(10) . . . . 2.2(7) no C(7) C(8) C(9) C(10) . . . . 0.6(7) no C(9) C(10) C(1) C(11) . . . . 13.8(6) no C(11) N(1) C(12) C(13) . . . . -112.7(4) no C(11) N(1) C(12) C(14) . . . . 122.3(4) no C(11) N(1) C(15) C(16) . . . . -66.3(5) no C(11) N(1) C(15) C(17) . . . . 61.1(5) no C(12) N(1) C(15) C(16) . . . . 110.7(4) no C(12) N(1) C(15) C(17) . . . . -122.0(4) no C(13) C(12) N(1) C(15) . . . . 70.4(5) no C(14) C(12) N(1) C(15) . . . . -54.5(5) no C(18) C(19) C(20) C(21) . . . . -2.2(9) no C(18) C(27) C(22) C(21) . . . . -0.4(6) no C(18) C(27) C(22) C(23) . . . . -179.8(4) no C(18) C(27) C(26) C(25) . . . . 179.9(4) no C(18) C(28) N(2) C(29) . . . . 177.1(4) no C(18) C(28) N(2) C(32) . . . . -5.4(6) no C(19) C(18) C(27) C(22) . . . . -0.9(6) no C(19) C(18) C(27) C(26) . . . . -179.4(4) no C(19) C(20) C(21) C(22) . . . . 0.9(10) no C(20) C(19) C(18) C(27) . . . . 2.2(7) no C(20) C(19) C(18) C(28) . . . . -172.4(5) no C(20) C(21) C(22) C(23) . . . . 179.8(6) no C(20) C(21) C(22) C(27) . . . . 0.4(8) no C(21) C(22) C(23) C(24) . . . . -179.2(6) no C(21) C(22) C(27) C(26) . . . . 178.2(4) no C(22) C(23) C(24) C(25) . . . . 0(1) no C(22) C(27) C(18) C(28) . . . . 173.2(4) no C(22) C(27) C(26) C(25) . . . . 1.4(6) no C(23) C(22) C(27) C(26) . . . . -1.2(6) no C(23) C(24) C(25) C(26) . . . . -0.5(9) no C(24) C(23) C(22) C(27) . . . . 0.1(9) no C(24) C(25) C(26) C(27) . . . . -0.6(7) no C(26) C(27) C(18) C(28) . . . . -5.3(6) no C(28) N(2) C(29) C(30) . . . . 63.5(5) no C(28) N(2) C(29) C(31) . . . . -63.9(5) no C(28) N(2) C(32) C(33) . . . . -117.4(4) no C(28) N(2) C(32) C(34) . . . . 115.4(4) no C(29) N(2) C(32) C(33) . . . . 60.1(5) no C(29) N(2) C(32) C(34) . . . . -67.1(5) no C(30) C(29) N(2) C(32) . . . . -114.1(4) no C(31) C(29) N(2) C(32) . . . . 118.5(4) no #----------------------------------------------------------------------- loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A 'O(2)' 'H(2o)' 'O(3)' '0.90' '1.83' '2.725(4)' '172.7' '4_564' 'O(4)' 'H(4o)' 'O(1)' '0.88' '1.85' '2.726(4)' '178.3' '.' data_5 #----------------------------------------------------------------------- _audit_creation_date '1998-06-15' _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; #----------------------------------------------------------------------- _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; #----------------------------------------------------------------------- _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #----------------------------------------------------------------------- _cell_length_a 8.753(2) _cell_length_b 13.781(2) _cell_length_c 12.168(1) _cell_angle_alpha 90 _cell_angle_beta 107.865(10) _cell_angle_gamma 90 _cell_volume 1397.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 39.1 _cell_measurement_theta_max 39.8 #----------------------------------------------------------------------- _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' #----------------------------------------------------------------------- _exptl_crystal_description 'block' _exptl_crystal_colour 'colourlessblock' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.35 _exptl_crystal_density_diffrn 1.152 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 242.32 _chemical_formula_analytical ? _chemical_formula_sum 'C15 H18 N2 O ' _chemical_formula_moiety 'C15 H18 N2 O ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 520.00 _exptl_absorpt_coefficient_mu 0.544 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.911 _exptl_special_details ; The scan width was (1.68+0.30tan\q)\% with an \w scan speed of 32\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #----------------------------------------------------------------------- _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.53 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 3 2 -2 -3 2 1 2 3 _diffrn_reflns_number 3079 _reflns_number_total 2911 _reflns_number_observed 2015 _reflns_observed_criterion >2.00\s(I) _diffrn_reflns_av_R_equivalents 0.02115 _diffrn_reflns_av_sigmaI/netI 0.060 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 79.20 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.05483 _diffrn_orient_matrix_UB_12 0.03866 _diffrn_orient_matrix_UB_13 0.04645 _diffrn_orient_matrix_UB_21 -0.10677 _diffrn_orient_matrix_UB_22 -0.02072 _diffrn_orient_matrix_UB_23 -0.05288 _diffrn_orient_matrix_UB_31 0.00160 _diffrn_orient_matrix_UB_32 -0.05781 _diffrn_orient_matrix_UB_33 0.05002 #----------------------------------------------------------------------- loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 60 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 72 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 8 0.031 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 4 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #----------------------------------------------------------------------- loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.2669(2) 0.4084(1) 0.3511(1) 0.0671(6) 1.000 . Uani d ? N(1) 0.2674(2) 0.5119(2) 0.2093(2) 0.0666(7) 1.000 . Uani d ? N(2) 0.2996(2) 0.2960(2) 0.1360(2) 0.0652(7) 1.000 . Uani d ? C(1) 0.5104(3) 0.4220(2) 0.3049(2) 0.0474(7) 1.000 . Uani d ? C(2) 0.6172(3) 0.4716(2) 0.3929(2) 0.0593(8) 1.000 . Uani d ? C(3) 0.7832(3) 0.4605(2) 0.4168(3) 0.0703(9) 1.000 . Uani d ? C(4) 0.8418(3) 0.4030(2) 0.3486(3) 0.0693(9) 1.000 . Uani d ? C(5) 0.7364(3) 0.3510(2) 0.2556(2) 0.0597(8) 1.000 . Uani d ? C(6) 0.7963(4) 0.2952(2) 0.1812(3) 0.082(1) 1.000 . Uani d ? C(7) 0.6957(4) 0.2460(2) 0.0908(3) 0.089(1) 1.000 . Uani d ? C(8) 0.5289(4) 0.2469(2) 0.0744(3) 0.074(1) 1.000 . Uani d ? C(9) 0.4660(3) 0.2987(2) 0.1446(2) 0.0545(7) 1.000 . Uani d ? C(10) 0.5684(3) 0.3568(2) 0.2353(2) 0.0498(7) 1.000 . Uani d ? C(11) 0.3363(3) 0.4440(2) 0.2871(2) 0.0508(7) 1.000 . Uani d ? C(12) 0.0996(5) 0.5357(4) 0.1928(5) 0.103(2) 1.000 . Uani d ? C(13) 0.3408(5) 0.5539(4) 0.1297(4) 0.104(2) 1.000 . Uani d ? C(14) 0.2668(5) 0.2224(3) 0.2144(4) 0.089(1) 1.000 . Uani d ? C(15) 0.1903(5) 0.2858(5) 0.0189(4) 0.118(2) 1.000 . Uani d ? H(2) 0.574(2) 0.518(2) 0.437(2) 0.062(7) 1.000 . Uiso d ? H(3) 0.852(3) 0.499(2) 0.488(2) 0.080(8) 1.000 . Uiso d ? H(4) 0.961(3) 0.395(1) 0.362(2) 0.056(6) 1.000 . Uiso d ? H(6) 0.915(3) 0.293(2) 0.197(2) 0.089(9) 1.000 . Uiso d ? H(7) 0.743(3) 0.206(2) 0.036(2) 0.093(9) 1.000 . Uiso d ? H(8) 0.460(3) 0.206(2) 0.008(2) 0.092(9) 1.000 . Uiso d ? H(12a) 0.086(4) 0.597(3) 0.163(3) 0.13(2) 1.000 . Uiso d ? H(12b) 0.079(6) 0.543(4) 0.256(4) 0.23(3) 1.000 . Uiso d ? H(12c) 0.025(4) 0.493(3) 0.135(3) 0.15(2) 1.000 . Uiso d ? H(13b) 0.459(4) 0.538(2) 0.142(2) 0.11(1) 1.000 . Uiso d ? H(13c) 0.335(5) 0.620(3) 0.117(3) 0.16(2) 1.000 . Uiso d ? H(13a) 0.289(4) 0.530(3) 0.047(3) 0.17(2) 1.000 . Uiso d ? H(14b) 0.149(4) 0.228(2) 0.209(2) 0.13(1) 1.000 . Uiso d ? H(14a) 0.279(4) 0.158(3) 0.186(3) 0.16(2) 1.000 . Uiso d ? H(14c) 0.356(5) 0.229(3) 0.298(3) 0.17(2) 1.000 . Uiso d ? H(15b) 0.085(4) 0.294(2) 0.028(2) 0.13(1) 1.000 . Uiso d ? H(15c) 0.205(4) 0.226(3) -0.020(3) 0.14(2) 1.000 . Uiso d ? H(15a) 0.236(4) 0.345(2) -0.026(3) 0.13(2) 1.000 . Uiso d ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.060(1) 0.080(1) 0.065(1) 0.0019(9) 0.0237(9) 0.0004(10) N(1) 0.060(1) 0.058(1) 0.076(2) 0.009(1) 0.011(1) 0.011(1) N(2) 0.054(1) 0.071(2) 0.062(1) 0.004(1) 0.004(1) -0.017(1) C(1) 0.046(1) 0.049(1) 0.044(1) -0.001(1) 0.010(1) 0.003(1) C(2) 0.058(2) 0.060(2) 0.059(2) -0.005(1) 0.017(1) -0.007(1) C(3) 0.056(2) 0.077(2) 0.069(2) -0.013(2) 0.006(1) -0.002(2) C(4) 0.042(1) 0.075(2) 0.086(2) -0.001(1) 0.013(1) 0.012(2) C(5) 0.052(2) 0.058(2) 0.071(2) 0.005(1) 0.022(1) 0.006(1) C(6) 0.062(2) 0.078(2) 0.115(3) 0.009(2) 0.042(2) -0.003(2) C(7) 0.098(3) 0.082(2) 0.107(3) 0.010(2) 0.059(2) -0.017(2) C(8) 0.085(2) 0.072(2) 0.069(2) 0.004(2) 0.030(2) -0.015(2) C(9) 0.058(2) 0.056(2) 0.051(1) 0.007(1) 0.017(1) -0.002(1) C(10) 0.047(1) 0.052(1) 0.050(1) 0.004(1) 0.014(1) 0.004(1) C(11) 0.051(1) 0.050(2) 0.050(1) 0.001(1) 0.012(1) -0.006(1) C(12) 0.061(2) 0.093(3) 0.138(4) 0.025(2) 0.005(2) 0.014(3) C(13) 0.090(3) 0.113(4) 0.100(3) 0.000(3) 0.016(2) 0.049(3) C(14) 0.069(2) 0.072(2) 0.135(4) -0.006(2) 0.045(2) -0.001(2) C(15) 0.071(3) 0.175(5) 0.087(3) 0.014(3) -0.007(2) -0.046(3) #----------------------------------------------------------------------- _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00001|Fo|^2^]' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.0000080(5) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2015 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0830 _refine_ls_R_factor_obs 0.0561 _refine_ls_wR_factor_all 0.0513 _refine_ls_wR_factor_obs 0.0497 _refine_ls_goodness_of_fit_all 2.898 _refine_ls_goodness_of_fit_obs 3.354 _refine_ls_shift/esd_max 0.0010 _refine_ls_shift/esd_mean 0.0010 _refine_diff_density_min -0.15 _refine_diff_density_max 0.15 #----------------------------------------------------------------------- _geom_special_details ; ? ; 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) 1.227(2) . . yes N(1) C(11) 1.337(3) . . yes N(1) C(12) 1.458(4) . . yes N(1) C(13) 1.438(4) . . yes N(2) C(9) 1.429(3) . . yes N(2) C(14) 1.479(4) . . yes N(2) C(15) 1.459(4) . . yes C(1) C(2) 1.370(3) . . yes C(1) C(10) 1.430(3) . . yes C(1) C(11) 1.503(3) . . yes C(2) C(3) 1.399(3) . . yes C(2) H(2) 0.98(2) . . no C(3) C(4) 1.357(4) . . yes C(3) H(3) 1.04(2) . . no C(4) C(5) 1.417(3) . . yes C(4) H(4) 1.01(2) . . no C(5) C(6) 1.406(4) . . yes C(5) C(10) 1.416(3) . . yes C(6) C(7) 1.360(4) . . yes C(6) H(6) 1.00(2) . . no C(7) C(8) 1.412(4) . . yes C(7) H(7) 1.04(3) . . no C(8) C(9) 1.353(3) . . yes C(8) H(8) 1.02(3) . . no C(9) C(10) 1.435(3) . . yes C(12) H(12a) 0.91(3) . . no C(12) H(12b) 0.85(5) . . no C(12) H(12c) 0.99(4) . . no C(13) H(13b) 1.02(3) . . no C(13) H(13c) 0.92(4) . . no C(13) H(13a) 1.02(4) . . no C(14) H(14b) 1.01(3) . . no C(14) H(14a) 0.97(4) . . no C(14) H(14c) 1.08(4) . . no C(15) H(15b) 0.97(3) . . no C(15) H(15c) 0.98(4) . . no C(15) H(15a) 1.12(3) . . no #----------------------------------------------------------------------- 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) N(1) C(12) 118.2(3) . . . yes C(11) N(1) C(13) 124.2(3) . . . yes C(12) N(1) C(13) 117.1(3) . . . yes C(9) N(2) C(14) 111.5(2) . . . yes C(9) N(2) C(15) 114.9(3) . . . yes C(14) N(2) C(15) 111.5(4) . . . yes C(2) C(1) C(10) 119.7(2) . . . yes C(2) C(1) C(11) 115.5(2) . . . yes C(10) C(1) C(11) 124.8(2) . . . yes C(1) C(2) C(3) 121.6(3) . . . yes C(1) C(2) H(2) 117(1) . . . no C(3) C(2) H(2) 120(1) . . . no C(2) C(3) C(4) 120.0(3) . . . yes C(2) C(3) H(3) 114(1) . . . no C(4) C(3) H(3) 125(1) . . . no C(3) C(4) C(5) 120.5(3) . . . yes C(3) C(4) H(4) 121(1) . . . no C(5) C(4) H(4) 117(1) . . . no C(4) C(5) C(6) 120.7(3) . . . yes C(4) C(5) C(10) 119.8(2) . . . yes C(6) C(5) C(10) 119.4(3) . . . yes C(5) C(6) C(7) 121.1(3) . . . yes C(5) C(6) H(6) 117(1) . . . no C(7) C(6) H(6) 121(1) . . . no C(6) C(7) C(8) 119.7(3) . . . yes C(6) C(7) H(7) 119(1) . . . no C(8) C(7) H(7) 120(1) . . . no C(7) C(8) C(9) 121.2(3) . . . yes C(7) C(8) H(8) 116(1) . . . no C(9) C(8) H(8) 122(1) . . . no N(2) C(9) C(8) 122.9(2) . . . yes N(2) C(9) C(10) 117.0(2) . . . yes C(8) C(9) C(10) 120.1(2) . . . yes C(1) C(10) C(5) 118.1(2) . . . yes C(1) C(10) C(9) 123.7(2) . . . yes C(5) C(10) C(9) 118.2(2) . . . yes O(1) C(11) N(1) 121.7(2) . . . yes O(1) C(11) C(1) 120.4(2) . . . yes N(1) C(11) C(1) 117.4(2) . . . yes N(1) C(12) H(12a) 105(2) . . . no N(1) C(12) H(12b) 112(3) . . . no N(1) C(12) H(12c) 112(2) . . . no H(12a) C(12) H(12b) 102(4) . . . no H(12a) C(12) H(12c) 106(2) . . . no H(12b) C(12) H(12c) 116(4) . . . no N(1) C(13) H(13b) 117(1) . . . no N(1) C(13) H(13c) 119(2) . . . no N(1) C(13) H(13a) 112(2) . . . no H(13b) C(13) H(13c) 103(3) . . . no H(13b) C(13) H(13a) 101(2) . . . no H(13c) C(13) H(13a) 99(3) . . . no N(2) C(14) H(14b) 107(1) . . . no N(2) C(14) H(14a) 109(2) . . . no N(2) C(14) H(14c) 109(2) . . . no H(14b) C(14) H(14a) 105(2) . . . no H(14b) C(14) H(14c) 118(2) . . . no H(14a) C(14) H(14c) 106(3) . . . no N(2) C(15) H(15b) 103(1) . . . no N(2) C(15) H(15c) 114(2) . . . no N(2) C(15) H(15a) 100(1) . . . no H(15b) C(15) H(15c) 115(2) . . . no H(15b) C(15) H(15a) 117(2) . . . no H(15c) C(15) H(15a) 104(2) . . . no #----------------------------------------------------------------------- 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(2) 3.396(3) . 3_666 no O(1) C(3) 3.492(4) . 3_666 no O(1) C(15) 3.553(6) . 4 no #----------------------------------------------------------------------- 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) N(1) C(12) . . . . -6.7(4) no O(1) C(11) N(1) C(13) . . . . -178.0(3) no O(1) C(11) C(1) C(2) . . . . -78.0(3) no O(1) C(11) C(1) C(10) . . . . 104.0(3) no N(1) C(11) C(1) C(2) . . . . 94.1(3) no N(1) C(11) C(1) C(10) . . . . -83.9(3) no N(2) C(9) C(8) C(7) . . . . -175.4(3) no N(2) C(9) C(10) C(1) . . . . -9.6(3) no N(2) C(9) C(10) C(5) . . . . 171.8(2) no C(1) C(2) C(3) C(4) . . . . 3.3(4) no C(1) C(10) C(5) C(4) . . . . 4.9(3) no C(1) C(10) C(5) C(6) . . . . -173.6(2) no C(1) C(10) C(9) C(8) . . . . 172.8(2) no C(1) C(11) N(1) C(12) . . . . -178.6(3) no C(1) C(11) N(1) C(13) . . . . 10.1(4) no C(2) C(1) C(10) C(5) . . . . -4.1(3) no C(2) C(1) C(10) C(9) . . . . 177.3(2) no C(2) C(3) C(4) C(5) . . . . -2.5(4) no C(3) C(2) C(1) C(10) . . . . 0.1(4) no C(3) C(2) C(1) C(11) . . . . -178.0(2) no C(3) C(4) C(5) C(6) . . . . 176.8(3) no C(3) C(4) C(5) C(10) . . . . -1.7(4) no C(4) C(5) C(6) C(7) . . . . -179.1(3) no C(4) C(5) C(10) C(9) . . . . -176.4(2) no C(5) C(6) C(7) C(8) . . . . -3.1(5) no C(5) C(10) C(1) C(11) . . . . 173.8(2) no C(5) C(10) C(9) C(8) . . . . -5.8(3) no C(6) C(5) C(10) C(9) . . . . 5.1(4) no C(6) C(7) C(8) C(9) . . . . 2.4(5) no C(7) C(6) C(5) C(10) . . . . -0.7(4) no C(7) C(8) C(9) C(10) . . . . 2.1(4) no C(8) C(9) N(2) C(14) . . . . 93.2(3) no C(8) C(9) N(2) C(15) . . . . -34.9(4) no C(9) C(10) C(1) C(11) . . . . -4.8(3) no C(10) C(9) N(2) C(14) . . . . -84.4(3) no C(10) C(9) N(2) C(15) . . . . 147.5(3) no #-----------------------------------------------------------------------