# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/195 # Authors: Moises Canle L., Ibrahim Demirtas, Mark R.J. Elsegood # William Clegg and Howard Maskill. # Title: Preparations, X-ray crystal structure determinations, # and base strength measurements of substituted tritylaminines. # Manuscript submitted ca. 17/8/99 to J. Chem. Soc., Perkin Trans II. # Crystallographic communicationg author mark.elsegood@ncl.ac.uk data_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 Cl N O' _chemical_formula_weight 353.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7123(12) _cell_length_b 9.3000(13) _cell_length_c 13.4414(19) _cell_angle_alpha 88.445(4) _cell_angle_beta 75.459(3) _cell_angle_gamma 64.682(3) _cell_volume 948.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 3714 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 28.08 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.731 _exptl_absorpt_correction_T_max 0.928 _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6335 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.54 _reflns_number_total 4164 _reflns_number_gt 3090 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.1044P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except NH3 H coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4164 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1139 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.61550(6) 0.16678(5) 0.45332(4) 0.02406(15) Uani 1 d . . . N1 N 0.6562(2) -0.1458(2) 0.35356(12) 0.0198(4) Uani 1 d . . . H1A H 0.573(3) -0.168(2) 0.4033(17) 0.030 Uiso 1 d . . . H1B H 0.637(3) -0.038(3) 0.3769(16) 0.030 Uiso 1 d . . . H1C H 0.769(3) -0.222(3) 0.3623(16) 0.030 Uiso 1 d . . . C1 C 0.6453(2) -0.1598(2) 0.24350(14) 0.0179(4) Uani 1 d . . . C2 C 0.8213(2) -0.1745(2) 0.17278(14) 0.0194(4) Uani 1 d . . . C3 C 0.9178(2) -0.2905(2) 0.09051(15) 0.0248(4) Uani 1 d . . . H3 H 0.8761 -0.3653 0.0772 0.030 Uiso 1 calc R . . C4 C 1.0747(3) -0.2989(3) 0.02717(16) 0.0313(5) Uani 1 d . . . H4 H 1.1394 -0.3792 -0.0290 0.038 Uiso 1 calc R . . C5 C 1.1374(3) -0.1913(3) 0.04536(16) 0.0299(5) Uani 1 d . . . H5 H 1.2450 -0.1975 0.0021 0.036 Uiso 1 calc R . . C6 C 1.0421(3) -0.0746(3) 0.12704(16) 0.0288(5) Uani 1 d . . . H6 H 1.0845 -0.0003 0.1401 0.035 Uiso 1 calc R . . C7 C 0.8847(3) -0.0654(2) 0.19008(15) 0.0239(4) Uani 1 d . . . H7 H 0.8195 0.0161 0.2456 0.029 Uiso 1 calc R . . C8 C 0.4910(2) -0.0076(2) 0.22705(14) 0.0191(4) Uani 1 d . . . C9 C 0.5003(3) 0.0545(2) 0.13139(15) 0.0239(4) Uani 1 d . . . H9 H 0.6042 0.0038 0.0766 0.029 Uiso 1 calc R . . C10 C 0.3600(3) 0.1894(2) 0.11507(17) 0.0297(5) Uani 1 d . . . H10 H 0.3679 0.2298 0.0492 0.036 Uiso 1 calc R . . C11 C 0.2090(3) 0.2649(3) 0.19415(17) 0.0335(5) Uani 1 d . . . H11 H 0.1133 0.3580 0.1834 0.040 Uiso 1 calc R . . C12 C 0.1982(3) 0.2038(3) 0.28940(18) 0.0361(5) Uani 1 d . . . H12 H 0.0944 0.2554 0.3440 0.043 Uiso 1 calc R . . C13 C 0.3375(2) 0.0679(2) 0.30592(16) 0.0281(5) Uani 1 d . . . H13 H 0.3278 0.0264 0.3714 0.034 Uiso 1 calc R . . C14 C 0.6175(2) -0.3094(2) 0.23065(14) 0.0188(4) Uani 1 d . . . C15 C 0.4961(2) -0.3108(2) 0.18041(16) 0.0252(4) Uani 1 d . . . H15 H 0.4273 -0.2167 0.1532 0.030 Uiso 1 calc R . . C16 C 0.4755(3) -0.4493(2) 0.17011(17) 0.0308(5) Uani 1 d . . . H16 H 0.3930 -0.4493 0.1354 0.037 Uiso 1 calc R . . C17 C 0.5732(3) -0.5867(2) 0.20960(16) 0.0280(5) Uani 1 d . . . H17 H 0.5568 -0.6803 0.2033 0.034 Uiso 1 calc R . . C18 C 0.6953(3) -0.5870(2) 0.25860(15) 0.0264(5) Uani 1 d . . . H18 H 0.7641 -0.6815 0.2854 0.032 Uiso 1 calc R . . C19 C 0.7175(3) -0.4501(2) 0.26852(15) 0.0238(4) Uani 1 d . . . H19 H 0.8024 -0.4519 0.3018 0.029 Uiso 1 calc R . . O1 O 1.01546(19) 0.37333(17) 0.61915(12) 0.0362(4) Uani 1 d . . . C20 C 0.9090(2) 0.3422(2) 0.59137(15) 0.0259(5) Uani 1 d . . . C21 C 0.9232(3) 0.1771(3) 0.5902(2) 0.0429(6) Uani 1 d . . . H21A H 1.0456 0.1005 0.5838 0.064 Uiso 1 calc R . . H21B H 0.8856 0.1562 0.5315 0.064 Uiso 1 calc R . . H21C H 0.8476 0.1659 0.6546 0.064 Uiso 1 calc R . . C22 C 0.7608(3) 0.4670(3) 0.55766(18) 0.0359(5) Uani 1 d . . . H22A H 0.7451 0.5729 0.5802 0.054 Uiso 1 calc R . . H22B H 0.6526 0.4553 0.5883 0.054 Uiso 1 calc R . . H22C H 0.7868 0.4553 0.4822 0.054 Uiso 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0272(3) 0.0219(3) 0.0234(3) 0.00095(19) -0.00539(19) -0.0116(2) N1 0.0223(8) 0.0208(9) 0.0173(8) 0.0008(7) -0.0066(7) -0.0094(7) C1 0.0195(9) 0.0193(10) 0.0156(9) 0.0004(7) -0.0060(7) -0.0082(8) C2 0.0180(9) 0.0195(10) 0.0216(10) 0.0047(8) -0.0075(8) -0.0079(8) C3 0.0261(10) 0.0247(11) 0.0236(11) 0.0002(8) -0.0049(9) -0.0120(9) C4 0.0294(11) 0.0306(12) 0.0283(12) -0.0025(9) -0.0001(9) -0.0116(10) C5 0.0221(10) 0.0376(13) 0.0287(12) 0.0088(10) -0.0034(9) -0.0140(10) C6 0.0298(11) 0.0319(12) 0.0329(12) 0.0065(9) -0.0114(10) -0.0195(10) C7 0.0264(10) 0.0213(10) 0.0245(11) 0.0017(8) -0.0076(8) -0.0104(9) C8 0.0218(9) 0.0158(9) 0.0218(10) -0.0017(8) -0.0083(8) -0.0085(8) C9 0.0250(10) 0.0236(10) 0.0232(10) 0.0012(8) -0.0072(8) -0.0102(9) C10 0.0337(12) 0.0261(11) 0.0324(12) 0.0080(9) -0.0159(10) -0.0123(10) C11 0.0293(11) 0.0257(12) 0.0411(13) 0.0028(10) -0.0171(10) -0.0036(10) C12 0.0257(11) 0.0344(13) 0.0337(13) -0.0040(10) -0.0067(9) 0.0001(10) C13 0.0243(10) 0.0294(12) 0.0259(11) 0.0019(9) -0.0065(9) -0.0073(9) C14 0.0183(9) 0.0187(10) 0.0184(9) -0.0011(8) -0.0017(7) -0.0085(8) C15 0.0250(10) 0.0228(11) 0.0301(11) 0.0011(9) -0.0103(9) -0.0108(9) C16 0.0313(11) 0.0331(12) 0.0358(12) -0.0010(10) -0.0145(10) -0.0180(10) C17 0.0338(11) 0.0249(11) 0.0299(11) -0.0025(9) -0.0031(9) -0.0198(10) C18 0.0317(11) 0.0210(11) 0.0263(11) 0.0040(8) -0.0070(9) -0.0118(9) C19 0.0263(10) 0.0230(10) 0.0244(10) 0.0022(8) -0.0085(9) -0.0118(9) O1 0.0311(8) 0.0322(9) 0.0509(10) 0.0040(7) -0.0212(8) -0.0133(7) C20 0.0210(10) 0.0307(12) 0.0226(10) -0.0002(9) -0.0046(8) -0.0086(9) C21 0.0406(13) 0.0332(13) 0.0628(17) 0.0024(12) -0.0279(13) -0.0154(11) C22 0.0285(11) 0.0371(13) 0.0396(13) 0.0065(11) -0.0138(10) -0.0095(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.519(2) . ? C1 C14 1.532(2) . ? C1 C8 1.538(2) . ? C1 C2 1.540(2) . ? C2 C3 1.384(3) . ? C2 C7 1.395(3) . ? C3 C4 1.389(3) . ? C4 C5 1.381(3) . ? C5 C6 1.382(3) . ? C6 C7 1.387(3) . ? C8 C13 1.390(3) . ? C8 C9 1.393(3) . ? C9 C10 1.387(3) . ? C10 C11 1.379(3) . ? C11 C12 1.384(3) . ? C12 C13 1.388(3) . ? C14 C19 1.393(3) . ? C14 C15 1.395(3) . ? C15 C16 1.390(3) . ? C16 C17 1.378(3) . ? C17 C18 1.384(3) . ? C18 C19 1.381(3) . ? O1 C20 1.221(2) . ? C20 C22 1.484(3) . ? C20 C21 1.487(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C14 107.01(14) . . ? N1 C1 C8 108.36(14) . . ? C14 C1 C8 111.92(14) . . ? N1 C1 C2 106.41(14) . . ? C14 C1 C2 112.12(15) . . ? C8 C1 C2 110.72(15) . . ? C3 C2 C7 118.45(18) . . ? C3 C2 C1 122.21(16) . . ? C7 C2 C1 119.32(17) . . ? C2 C3 C4 120.78(18) . . ? C5 C4 C3 120.41(19) . . ? C4 C5 C6 119.38(19) . . ? C5 C6 C7 120.33(19) . . ? C6 C7 C2 120.64(19) . . ? C13 C8 C9 118.59(17) . . ? C13 C8 C1 120.89(17) . . ? C9 C8 C1 120.48(17) . . ? C10 C9 C8 120.88(18) . . ? C11 C10 C9 120.17(19) . . ? C10 C11 C12 119.40(19) . . ? C11 C12 C13 120.7(2) . . ? C12 C13 C8 120.24(19) . . ? C19 C14 C15 118.28(17) . . ? C19 C14 C1 119.68(16) . . ? C15 C14 C1 122.03(16) . . ? C16 C15 C14 120.16(18) . . ? C17 C16 C15 120.84(19) . . ? C16 C17 C18 119.42(18) . . ? C19 C18 C17 120.09(19) . . ? C18 C19 C14 121.20(18) . . ? O1 C20 C22 121.55(19) . . ? O1 C20 C21 121.06(19) . . ? C22 C20 C21 117.39(18) . . ? _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.258 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.053 #===END data_1c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 N O2' _chemical_formula_weight 331.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.574(2) _cell_length_b 12.5221(18) _cell_length_c 17.769(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.757(3) _cell_angle_gamma 90.00 _cell_volume 3549.3(9) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 6142 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 28.21 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10748 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4053 _reflns_number_gt 2711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+0.3934P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom except H1 coords freely refined' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0044(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4053 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1354 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.19240(10) 0.60518(13) 0.17373(9) 0.0276(4) Uani 1 1 d . . . N1 N 0.11894(9) 0.67364(11) 0.13782(9) 0.0308(3) Uani 1 1 d . . . H1 H 0.1130(12) 0.6788(16) 0.0851(13) 0.048(6) Uiso 1 1 d . . . C2 C 0.12484(11) 0.78216(13) 0.16916(11) 0.0379(4) Uani 1 1 d . . . H2A H 0.1794 0.8137 0.1685 0.045 Uiso 1 1 calc R . . H2B H 0.1220 0.7799 0.2241 0.045 Uiso 1 1 calc R . . C3 C 0.05550(11) 0.85037(13) 0.12214(10) 0.0342(4) Uani 1 1 d . . . O1 O 0.01981(9) 0.83704(10) 0.05437(8) 0.0517(4) Uani 1 1 d . . . O2 O 0.04147(8) 0.93261(10) 0.16488(8) 0.0459(4) Uani 1 1 d . . . C4 C -0.01881(15) 1.01119(18) 0.12421(14) 0.0650(7) Uani 1 1 d . . . H4A H -0.0268 1.0652 0.1615 0.097 Uiso 1 1 calc R . . H4B H -0.0724 0.9760 0.1000 0.097 Uiso 1 1 calc R . . H4C H 0.0020 1.0456 0.0836 0.097 Uiso 1 1 calc R . . C5 C 0.27216(10) 0.66133(12) 0.16503(9) 0.0282(4) Uani 1 1 d . . . C6 C 0.32113(10) 0.72662(14) 0.22297(10) 0.0344(4) Uani 1 1 d . . . H6 H 0.3101 0.7297 0.2727 0.041 Uiso 1 1 calc R . . C7 C 0.38596(11) 0.78746(15) 0.20942(11) 0.0409(4) Uani 1 1 d . . . H7 H 0.4185 0.8320 0.2496 0.049 Uiso 1 1 calc R . . C8 C 0.40320(11) 0.78343(15) 0.13790(11) 0.0419(5) Uani 1 1 d . . . H8 H 0.4481 0.8241 0.1289 0.050 Uiso 1 1 calc R . . C9 C 0.35482(11) 0.71997(14) 0.07940(11) 0.0392(4) Uani 1 1 d . . . H9 H 0.3663 0.7172 0.0299 0.047 Uiso 1 1 calc R . . C10 C 0.28973(10) 0.66037(13) 0.09254(10) 0.0325(4) Uani 1 1 d . . . H10 H 0.2563 0.6180 0.0514 0.039 Uiso 1 1 calc R . . C11 C 0.19301(10) 0.58210(12) 0.25900(9) 0.0296(4) Uani 1 1 d . . . C12 C 0.26463(11) 0.54525(13) 0.31324(10) 0.0347(4) Uani 1 1 d . . . H12 H 0.3149 0.5354 0.2981 0.042 Uiso 1 1 calc R . . C13 C 0.26336(13) 0.52263(14) 0.38937(10) 0.0407(4) Uani 1 1 d . . . H13 H 0.3126 0.4970 0.4259 0.049 Uiso 1 1 calc R . . C14 C 0.19115(13) 0.53708(14) 0.41232(10) 0.0424(5) Uani 1 1 d . . . H14 H 0.1910 0.5238 0.4649 0.051 Uiso 1 1 calc R . . C15 C 0.11900(13) 0.57097(15) 0.35857(11) 0.0430(5) Uani 1 1 d . . . H15 H 0.0687 0.5800 0.3738 0.052 Uiso 1 1 calc R . . C16 C 0.12022(11) 0.59186(14) 0.28211(10) 0.0360(4) Uani 1 1 d . . . H16 H 0.0700 0.6133 0.2450 0.043 Uiso 1 1 calc R . . C17 C 0.17970(10) 0.49641(13) 0.13137(9) 0.0292(4) Uani 1 1 d . . . C18 C 0.10043(11) 0.46186(14) 0.08918(9) 0.0329(4) Uani 1 1 d . . . H18 H 0.0533 0.5071 0.0844 0.039 Uiso 1 1 calc R . . C19 C 0.08972(12) 0.36131(14) 0.05391(10) 0.0385(4) Uani 1 1 d . . . H19 H 0.0353 0.3390 0.0251 0.046 Uiso 1 1 calc R . . C20 C 0.15701(12) 0.29408(14) 0.06036(10) 0.0397(4) Uani 1 1 d . . . H20 H 0.1494 0.2258 0.0362 0.048 Uiso 1 1 calc R . . C21 C 0.23611(12) 0.32752(14) 0.10274(10) 0.0378(4) Uani 1 1 d . . . H21 H 0.2830 0.2819 0.1075 0.045 Uiso 1 1 calc R . . C22 C 0.24706(11) 0.42706(13) 0.13825(10) 0.0340(4) Uani 1 1 d . . . H22 H 0.3015 0.4484 0.1678 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0296(8) 0.0276(8) 0.0252(8) 0.0008(6) 0.0066(6) 0.0016(6) N1 0.0333(8) 0.0279(7) 0.0292(7) -0.0007(6) 0.0051(6) 0.0035(6) C2 0.0361(10) 0.0282(9) 0.0443(10) -0.0028(8) 0.0024(8) 0.0038(7) C3 0.0343(9) 0.0287(9) 0.0391(10) -0.0010(7) 0.0088(8) -0.0003(7) O1 0.0630(9) 0.0432(8) 0.0402(8) 0.0001(6) -0.0008(7) 0.0120(7) O2 0.0466(8) 0.0376(7) 0.0500(8) -0.0046(6) 0.0073(6) 0.0147(6) C4 0.0651(15) 0.0509(13) 0.0732(15) 0.0002(12) 0.0088(12) 0.0317(11) C5 0.0293(8) 0.0268(8) 0.0282(8) 0.0029(6) 0.0072(7) 0.0045(6) C6 0.0322(9) 0.0371(9) 0.0337(9) -0.0019(7) 0.0086(7) 0.0007(7) C7 0.0342(10) 0.0416(10) 0.0460(10) -0.0034(8) 0.0091(8) -0.0044(8) C8 0.0333(9) 0.0398(10) 0.0545(11) 0.0080(9) 0.0151(8) -0.0011(8) C9 0.0424(10) 0.0395(10) 0.0393(9) 0.0096(8) 0.0174(8) 0.0060(8) C10 0.0356(9) 0.0331(9) 0.0292(8) 0.0039(7) 0.0098(7) 0.0048(7) C11 0.0375(9) 0.0249(8) 0.0266(8) -0.0016(6) 0.0090(7) -0.0011(7) C12 0.0432(10) 0.0314(9) 0.0297(8) 0.0015(7) 0.0100(7) 0.0050(7) C13 0.0578(12) 0.0324(9) 0.0302(9) 0.0033(7) 0.0090(8) 0.0064(8) C14 0.0671(13) 0.0349(10) 0.0284(9) -0.0003(7) 0.0183(9) -0.0036(9) C15 0.0517(11) 0.0450(11) 0.0389(10) -0.0039(8) 0.0234(9) -0.0067(9) C16 0.0379(10) 0.0397(10) 0.0313(9) -0.0024(7) 0.0113(7) -0.0028(8) C17 0.0380(9) 0.0277(8) 0.0239(8) 0.0014(6) 0.0116(7) 0.0007(7) C18 0.0372(9) 0.0331(9) 0.0295(8) -0.0016(7) 0.0108(7) -0.0004(7) C19 0.0476(11) 0.0360(9) 0.0326(9) -0.0056(7) 0.0122(8) -0.0090(8) C20 0.0642(13) 0.0272(8) 0.0287(9) -0.0021(7) 0.0143(8) 0.0005(8) C21 0.0522(11) 0.0312(9) 0.0318(9) 0.0034(7) 0.0146(8) 0.0107(8) C22 0.0416(10) 0.0321(9) 0.0280(8) 0.0036(7) 0.0090(7) 0.0048(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.484(2) . ? C1 C11 1.540(2) . ? C1 C5 1.542(2) . ? C1 C17 1.543(2) . ? N1 H1 0.92(2) . ? N1 C2 1.462(2) . ? C2 C3 1.492(2) . ? C3 O1 1.200(2) . ? C3 O2 1.337(2) . ? O2 C4 1.448(2) . ? C5 C6 1.390(2) . ? C5 C10 1.396(2) . ? C6 C7 1.391(2) . ? C7 C8 1.377(3) . ? C8 C9 1.379(3) . ? C9 C10 1.383(2) . ? C11 C16 1.381(2) . ? C11 C12 1.389(2) . ? C12 C13 1.388(2) . ? C13 C14 1.377(3) . ? C14 C15 1.379(3) . ? C15 C16 1.389(2) . ? C17 C18 1.393(2) . ? C17 C22 1.393(2) . ? C18 C19 1.396(2) . ? C19 C20 1.377(3) . ? C20 C21 1.387(3) . ? C21 C22 1.387(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C11 108.48(13) . . ? N1 C1 C5 108.61(12) . . ? C11 C1 C5 114.05(13) . . ? N1 C1 C17 108.23(12) . . ? C11 C1 C17 106.14(12) . . ? C5 C1 C17 111.15(12) . . ? H1 N1 C2 107.5(13) . . ? H1 N1 C1 109.2(13) . . ? C2 N1 C1 114.27(13) . . ? N1 C2 C3 110.93(14) . . ? O1 C3 O2 124.24(16) . . ? O1 C3 C2 125.23(16) . . ? O2 C3 C2 110.43(15) . . ? C3 O2 C4 116.28(15) . . ? C6 C5 C10 117.54(15) . . ? C6 C5 C1 122.54(14) . . ? C10 C5 C1 119.21(14) . . ? C5 C6 C7 121.14(16) . . ? C8 C7 C6 120.22(17) . . ? C7 C8 C9 119.53(17) . . ? C8 C9 C10 120.27(16) . . ? C9 C10 C5 121.27(16) . . ? C16 C11 C12 118.29(15) . . ? C16 C11 C1 120.20(14) . . ? C12 C11 C1 121.40(14) . . ? C13 C12 C11 120.51(17) . . ? C14 C13 C12 120.43(17) . . ? C13 C14 C15 119.68(16) . . ? C14 C15 C16 119.68(18) . . ? C11 C16 C15 121.33(17) . . ? C18 C17 C22 118.02(15) . . ? C18 C17 C1 121.37(14) . . ? C22 C17 C1 120.51(14) . . ? C17 C18 C19 120.54(16) . . ? C20 C19 C18 120.84(17) . . ? C19 C20 C21 119.03(16) . . ? C22 C21 C20 120.39(17) . . ? C21 C22 C17 121.18(17) . . ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.222 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.049 #===END data_1d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 N O2' _chemical_formula_weight 317.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.2290(18) _cell_length_b 9.6725(18) _cell_length_c 18.700(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1669.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 3306 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 23.51 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 8809 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0576 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2939 _reflns_number_gt 1964 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.2422P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4(3) _refine_ls_number_reflns 2939 _refine_ls_number_parameters 264 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1575 _refine_ls_wR_factor_gt 0.1385 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4214(4) 0.4659(3) 0.86850(17) 0.0531(10) Uani 1 1 d D . . N1 N 0.3729(7) 0.3881(6) 0.9370(3) 0.0295(15) Uani 0.546(6) 1 d PD A 1 H1A H 0.4006 0.4385 0.9764 0.035 Uiso 0.546(6) 1 calc PR A 1 H1B H 0.2734 0.3820 0.9373 0.035 Uiso 0.546(6) 1 calc PR A 1 C2 C 0.4347(6) 0.2474(7) 0.9424(3) 0.0354(16) Uani 0.546(6) 1 d PD A 1 H2A H 0.4760 0.2197 0.8957 0.043 Uiso 0.546(6) 1 calc PR A 1 H2B H 0.3573 0.1808 0.9550 0.043 Uiso 0.546(6) 1 calc PR A 1 C3 C 0.551(2) 0.2450(19) 0.9984(11) 0.058(6) Uani 0.546(6) 1 d PD A 1 O1 O 0.5581(5) 0.3455(5) 1.0423(2) 0.0498(17) Uani 0.546(6) 1 d PD A 1 O2 O 0.6135(5) 0.1296(5) 1.0074(4) 0.0497(15) Uani 0.546(6) 1 d PD A 1 N1A N 0.4106(9) 0.3376(8) 0.9181(4) 0.037(2) Uani 0.454(6) 1 d PD A 2 H1A1 H 0.3154 0.3094 0.9189 0.044 Uiso 0.454(6) 1 calc PR A 2 H1B2 H 0.4636 0.2674 0.8976 0.044 Uiso 0.454(6) 1 calc PR A 2 C2A C 0.4603(7) 0.3536(7) 0.9939(3) 0.037(2) Uani 0.454(6) 1 d PD A 2 H2A1 H 0.3773 0.3420 1.0268 0.045 Uiso 0.454(6) 1 calc PR A 2 H2B2 H 0.5012 0.4472 1.0011 0.045 Uiso 0.454(6) 1 calc PR A 2 C3A C 0.573(2) 0.2465(19) 1.0092(10) 0.029(4) Uani 0.454(6) 1 d PD A 2 O1A O 0.6527(5) 0.2674(5) 1.0647(2) 0.0444(17) Uani 0.454(6) 1 d PD A 2 O2A O 0.6051(6) 0.1601(7) 0.9607(4) 0.0415(15) Uani 0.454(6) 1 d PD A 2 C4 C 0.3334(5) 0.4240(3) 0.80241(18) 0.0589(11) Uani 1 1 d . A . C5 C 0.3229(5) 0.5147(4) 0.74616(18) 0.0659(12) Uani 1 1 d . . . H5 H 0.3699 0.6019 0.7489 0.079 Uiso 1 1 calc R A . C6 C 0.2442(6) 0.4804(7) 0.6853(2) 0.0940(18) Uani 1 1 d . A . H6 H 0.2392 0.5435 0.6465 0.113 Uiso 1 1 calc R . . C7 C 0.1739(6) 0.3561(7) 0.6810(3) 0.109(2) Uani 1 1 d . . . H7 H 0.1188 0.3333 0.6398 0.131 Uiso 1 1 calc R A . C8 C 0.1832(6) 0.2681(5) 0.7348(3) 0.117(2) Uani 1 1 d . A . H8 H 0.1359 0.1812 0.7311 0.140 Uiso 1 1 calc R . . C9 C 0.2597(6) 0.2987(4) 0.7961(3) 0.100(2) Uani 1 1 d . . . H9 H 0.2621 0.2340 0.8343 0.119 Uiso 1 1 calc R A . C10 C 0.5867(4) 0.4547(3) 0.85503(17) 0.0542(10) Uani 1 1 d . A . C11 C 0.6840(5) 0.5017(4) 0.90656(19) 0.0602(10) Uani 1 1 d . . . H11 H 0.6484 0.5475 0.9479 0.072 Uiso 1 1 calc R A . C12 C 0.8327(5) 0.4828(4) 0.8984(2) 0.0649(12) Uani 1 1 d . A . H12 H 0.8973 0.5132 0.9346 0.078 Uiso 1 1 calc R . . C13 C 0.8861(5) 0.4200(4) 0.8379(2) 0.0714(12) Uani 1 1 d . . . H13 H 0.9874 0.4077 0.8317 0.086 Uiso 1 1 calc R A . C14 C 0.7905(5) 0.3753(4) 0.7864(2) 0.0750(13) Uani 1 1 d . A . H14 H 0.8267 0.3321 0.7444 0.090 Uiso 1 1 calc R . . C15 C 0.6415(5) 0.3924(4) 0.7946(2) 0.0664(12) Uani 1 1 d . . . H15 H 0.5774 0.3609 0.7584 0.080 Uiso 1 1 calc R A . C16 C 0.3726(4) 0.6095(4) 0.89157(18) 0.0585(11) Uani 1 1 d . A . C17 C 0.4553(4) 0.7273(4) 0.87966(16) 0.0520(9) Uani 1 1 d . . . H17 H 0.5503 0.7187 0.8606 0.062 Uiso 1 1 calc R A . C18 C 0.4008(5) 0.8570(4) 0.89522(19) 0.0626(11) Uani 1 1 d . A . H18 H 0.4597 0.9362 0.8877 0.075 Uiso 1 1 calc R . . C19 C 0.2621(5) 0.8730(5) 0.9215(2) 0.0906(16) Uani 1 1 d . . . H19 H 0.2249 0.9626 0.9313 0.109 Uiso 1 1 calc R A . C20 C 0.1790(6) 0.7584(6) 0.9332(3) 0.116(2) Uani 1 1 d . A . H20 H 0.0835 0.7687 0.9515 0.139 Uiso 1 1 calc R . . C21 C 0.2319(5) 0.6285(5) 0.9190(2) 0.0982(19) Uani 1 1 d . . . H21 H 0.1724 0.5501 0.9278 0.118 Uiso 1 1 calc R A . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.071(3) 0.050(2) 0.0390(17) -0.0011(15) -0.0047(17) -0.0261(19) N1 0.026(3) 0.031(3) 0.032(3) -0.001(2) 0.001(3) -0.007(3) C2 0.030(3) 0.032(3) 0.044(3) 0.006(3) -0.009(3) -0.001(3) C3 0.048(8) 0.068(12) 0.057(10) 0.021(8) -0.010(6) -0.015(7) O1 0.041(3) 0.054(3) 0.055(3) -0.009(2) -0.009(2) -0.009(2) O2 0.031(2) 0.054(4) 0.064(4) 0.000(3) -0.009(3) -0.001(2) N1A 0.030(4) 0.045(6) 0.035(4) -0.013(4) 0.004(3) 0.004(4) C2A 0.032(4) 0.043(4) 0.037(4) -0.007(3) -0.005(3) 0.006(3) C3A 0.049(9) 0.030(8) 0.009(5) -0.013(4) -0.009(5) 0.012(6) O1A 0.031(3) 0.059(3) 0.043(3) -0.003(3) 0.000(2) 0.005(3) O2A 0.036(3) 0.040(3) 0.049(4) -0.011(3) 0.002(3) 0.005(3) C4 0.091(3) 0.0349(18) 0.051(2) -0.0121(16) -0.025(2) 0.0066(19) C5 0.097(3) 0.059(2) 0.042(2) -0.0051(18) 0.003(2) 0.023(2) C6 0.122(4) 0.123(4) 0.037(2) -0.002(3) -0.008(2) 0.074(4) C7 0.117(5) 0.123(4) 0.088(4) -0.069(4) -0.052(3) 0.081(4) C8 0.143(5) 0.055(3) 0.152(5) -0.044(3) -0.111(4) 0.036(3) C9 0.139(4) 0.035(2) 0.125(4) 0.000(2) -0.098(4) -0.011(3) C10 0.082(3) 0.0352(17) 0.0456(19) -0.0026(15) -0.0026(19) -0.0223(18) C11 0.075(3) 0.046(2) 0.060(2) -0.0019(17) -0.013(2) -0.017(2) C12 0.082(3) 0.050(2) 0.063(3) 0.0076(19) -0.012(2) -0.023(2) C13 0.080(3) 0.057(2) 0.077(3) -0.002(2) 0.006(2) -0.027(2) C14 0.094(4) 0.062(3) 0.069(3) -0.015(2) 0.015(2) -0.029(2) C15 0.078(3) 0.062(3) 0.058(2) -0.0149(19) 0.004(2) -0.037(2) C16 0.071(3) 0.061(2) 0.0434(19) -0.0226(17) 0.0194(18) -0.032(2) C17 0.059(2) 0.050(2) 0.0470(18) -0.0144(17) 0.0086(16) -0.0146(18) C18 0.067(3) 0.060(2) 0.061(2) -0.0266(19) 0.023(2) -0.011(2) C19 0.094(4) 0.089(3) 0.089(3) -0.057(3) 0.044(3) -0.017(3) C20 0.098(4) 0.128(4) 0.122(4) -0.088(4) 0.076(3) -0.052(4) C21 0.100(4) 0.108(4) 0.087(3) -0.065(3) 0.056(3) -0.067(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C16 1.522(5) . ? C1 C4 1.534(5) . ? C1 C10 1.550(5) . ? C1 N1 1.551(7) . ? C1 N1A 1.553(8) . ? N1 C2 1.479(8) . ? C2 C3 1.497(13) . ? C3 O2 1.269(12) . ? C3 O1 1.274(12) . ? N1A C2A 1.497(9) . ? C2A C3A 1.498(12) . ? C3A O2A 1.267(12) . ? C3A O1A 1.286(12) . ? C4 C5 1.373(5) . ? C4 C9 1.395(5) . ? C5 C6 1.390(6) . ? C6 C7 1.369(8) . ? C7 C8 1.319(8) . ? C8 C9 1.379(6) . ? C10 C15 1.377(5) . ? C10 C11 1.393(5) . ? C11 C12 1.393(6) . ? C12 C13 1.375(5) . ? C13 C14 1.376(6) . ? C14 C15 1.393(6) . ? C16 C17 1.390(5) . ? C16 C21 1.408(6) . ? C17 C18 1.382(5) . ? C18 C19 1.381(6) . ? C19 C20 1.365(6) . ? C20 C21 1.375(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C1 C4 108.2(3) . . ? C16 C1 C10 113.6(3) . . ? C4 C1 C10 111.8(3) . . ? C16 C1 N1 97.1(3) . . ? C4 C1 N1 112.6(3) . . ? C10 C1 N1 112.6(4) . . ? C16 C1 N1A 122.8(4) . . ? C4 C1 N1A 103.7(4) . . ? C10 C1 N1A 96.0(4) . . ? N1 C1 N1A 25.9(2) . . ? C2 N1 C1 113.1(5) . . ? N1 C2 C3 109.7(7) . . ? O2 C3 O1 124.1(12) . . ? O2 C3 C2 115.7(11) . . ? O1 C3 C2 118.5(9) . . ? C2A N1A C1 117.6(6) . . ? N1A C2A C3A 108.8(7) . . ? O2A C3A O1A 123.3(12) . . ? O2A C3A C2A 118.7(11) . . ? O1A C3A C2A 116.3(7) . . ? C5 C4 C9 117.1(3) . . ? C5 C4 C1 119.1(3) . . ? C9 C4 C1 123.8(3) . . ? C4 C5 C6 120.8(4) . . ? C7 C6 C5 120.3(4) . . ? C8 C7 C6 119.4(4) . . ? C7 C8 C9 121.9(5) . . ? C8 C9 C4 120.4(4) . . ? C15 C10 C11 118.3(4) . . ? C15 C10 C1 121.7(3) . . ? C11 C10 C1 119.9(3) . . ? C12 C11 C10 121.0(4) . . ? C13 C12 C11 120.1(4) . . ? C12 C13 C14 119.0(5) . . ? C13 C14 C15 121.2(4) . . ? C10 C15 C14 120.4(4) . . ? C17 C16 C21 117.2(4) . . ? C17 C16 C1 122.7(3) . . ? C21 C16 C1 119.7(3) . . ? C18 C17 C16 120.7(4) . . ? C19 C18 C17 120.9(4) . . ? C20 C19 C18 119.1(4) . . ? C19 C20 C21 120.8(4) . . ? C20 C21 C16 121.2(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.226 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.043 #===END data_4a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H23 N O3' _chemical_formula_weight 349.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.497(2) _cell_length_b 18.498(2) _cell_length_c 19.597(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.780(17) _cell_angle_gamma 90.00 _cell_volume 3710.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 44 _cell_measurement_theta_min 20.78 _cell_measurement_theta_max 24.94 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.79 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6222 _exptl_absorpt_correction_T_max 0.9488 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe-Siemens diffractometer' _diffrn_measurement_method '\w/\q scans with on-line profile fitting' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11167 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 67.62 _reflns_number_total 6506 _reflns_number_gt 5007 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe DIF4' _computing_cell_refinement 'Stoe DIF4' _computing_data_reduction 'local programs' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXTL and local programs' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+1.4193P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00077(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6506 _refine_ls_number_parameters 488 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.50021(16) 0.45856(9) 0.10086(9) 0.0300(4) Uani 1 1 d . . . H1A H 0.534(2) 0.4139(12) 0.1207(11) 0.036 Uiso 1 1 d . . . H1B H 0.508(2) 0.4565(12) 0.0590(12) 0.036 Uiso 1 1 d . . . C1 C 0.58464(18) 0.51758(10) 0.13708(9) 0.0249(4) Uani 1 1 d . . . C2 C 0.72880(18) 0.50574(9) 0.13476(9) 0.0247(4) Uani 1 1 d . . . C3 C 0.83090(18) 0.51114(10) 0.19311(9) 0.0259(4) Uani 1 1 d . . . H3 H 0.8119 0.5230 0.2370 0.031 Uiso 1 1 calc R . . C4 C 0.96039(18) 0.49972(10) 0.18940(10) 0.0277(4) Uani 1 1 d . . . H4 H 1.0282 0.5033 0.2303 0.033 Uiso 1 1 calc R . . C5 C 0.98957(18) 0.48318(10) 0.12562(10) 0.0278(4) Uani 1 1 d . . . C6 C 0.8898(2) 0.47811(11) 0.06627(10) 0.0336(5) Uani 1 1 d . . . H6 H 0.9094 0.4670 0.0224 0.040 Uiso 1 1 calc R . . C7 C 0.76172(19) 0.48925(11) 0.07103(10) 0.0320(4) Uani 1 1 d . . . H7 H 0.6942 0.4856 0.0299 0.038 Uiso 1 1 calc R . . O1 O 1.11363(13) 0.47208(8) 0.11582(7) 0.0382(3) Uani 1 1 d . . . C8 C 1.2163(2) 0.46780(13) 0.17682(12) 0.0414(5) Uani 1 1 d . . . H8A H 1.2283 0.5151 0.1998 0.062 Uiso 1 1 calc R . . H8B H 1.2974 0.4534 0.1636 0.062 Uiso 1 1 calc R . . H8C H 1.1938 0.4319 0.2090 0.062 Uiso 1 1 calc R . . C9 C 0.53183(18) 0.58820(9) 0.10011(9) 0.0244(4) Uani 1 1 d . . . C10 C 0.61215(19) 0.64198(10) 0.08239(9) 0.0283(4) Uani 1 1 d . . . H10 H 0.7036 0.6340 0.0903 0.034 Uiso 1 1 calc R . . C11 C 0.5603(2) 0.70705(11) 0.05338(10) 0.0333(5) Uani 1 1 d . . . H11 H 0.6164 0.7428 0.0412 0.040 Uiso 1 1 calc R . . C12 C 0.4269(2) 0.72006(11) 0.04208(9) 0.0319(4) Uani 1 1 d . . . C13 C 0.34549(19) 0.66694(11) 0.05818(9) 0.0313(4) Uani 1 1 d . . . H13 H 0.2539 0.6748 0.0495 0.038 Uiso 1 1 calc R . . C14 C 0.39817(19) 0.60213(10) 0.08700(10) 0.0297(4) Uani 1 1 d . . . H14 H 0.3414 0.5662 0.0981 0.036 Uiso 1 1 calc R . . O2 O 0.38677(16) 0.78708(8) 0.01612(8) 0.0447(4) Uani 1 1 d . . . C15 C 0.2534(3) 0.80586(14) 0.01091(12) 0.0552(7) Uani 1 1 d . . . H15A H 0.2324 0.8019 0.0571 0.083 Uiso 1 1 calc R . . H15B H 0.1974 0.7730 -0.0218 0.083 Uiso 1 1 calc R . . H15C H 0.2385 0.8556 -0.0061 0.083 Uiso 1 1 calc R . . C16 C 0.57107(17) 0.51958(10) 0.21364(9) 0.0242(4) Uani 1 1 d . . . C17 C 0.56457(19) 0.45603(10) 0.25109(10) 0.0311(4) Uani 1 1 d . . . H17 H 0.5639 0.4108 0.2281 0.037 Uiso 1 1 calc R . . C18 C 0.5591(2) 0.45749(11) 0.32078(11) 0.0370(5) Uani 1 1 d . . . H18 H 0.5533 0.4134 0.3448 0.044 Uiso 1 1 calc R . . C19 C 0.5619(2) 0.52270(11) 0.35599(10) 0.0334(4) Uani 1 1 d . . . C20 C 0.5695(2) 0.58625(11) 0.32027(11) 0.0358(5) Uani 1 1 d . . . H20 H 0.5720 0.6314 0.3437 0.043 Uiso 1 1 calc R . . C21 C 0.5735(2) 0.58402(10) 0.24979(10) 0.0330(5) Uani 1 1 d . . . H21 H 0.5781 0.6282 0.2257 0.040 Uiso 1 1 calc R . . O3 O 0.56011(19) 0.51835(8) 0.42547(8) 0.0534(5) Uani 1 1 d . . . C22 C 0.5665(3) 0.58492(14) 0.46344(13) 0.0644(8) Uani 1 1 d . . . H22A H 0.5655 0.5747 0.5124 0.097 Uiso 1 1 calc R . . H22B H 0.4911 0.6151 0.4427 0.097 Uiso 1 1 calc R . . H22C H 0.6473 0.6105 0.4612 0.097 Uiso 1 1 calc R . . N2 N 0.90601(18) 0.31390(9) 0.18407(10) 0.0328(4) Uani 1 1 d . . . H2A H 0.880(2) 0.3572(13) 0.1990(11) 0.039 Uiso 1 1 d . . . H2B H 0.872(2) 0.3128(12) 0.1388(12) 0.039 Uiso 1 1 d . . . C23 C 0.85649(18) 0.25244(10) 0.21917(9) 0.0253(4) Uani 1 1 d . . . C24 C 0.88229(18) 0.18309(10) 0.18082(9) 0.0255(4) Uani 1 1 d . . . C25 C 0.79646(18) 0.12458(10) 0.16994(9) 0.0272(4) Uani 1 1 d . . . H25 H 0.7150 0.1286 0.1832 0.033 Uiso 1 1 calc R . . C26 C 0.82698(19) 0.06074(10) 0.14034(10) 0.0304(4) Uani 1 1 d . . . H26 H 0.7667 0.0217 0.1332 0.037 Uiso 1 1 calc R . . C27 C 0.9466(2) 0.05396(10) 0.12100(9) 0.0300(4) Uani 1 1 d . . . C28 C 1.0323(2) 0.11183(11) 0.12985(10) 0.0341(5) Uani 1 1 d . . . H28 H 1.1129 0.1081 0.1157 0.041 Uiso 1 1 calc R . . C29 C 0.99934(19) 0.17543(11) 0.15963(10) 0.0323(4) Uani 1 1 d . . . H29 H 1.0588 0.2149 0.1657 0.039 Uiso 1 1 calc R . . O4 O 0.97124(15) -0.01182(8) 0.09401(8) 0.0412(4) Uani 1 1 d . . . C30 C 1.0990(2) -0.02263(13) 0.08211(14) 0.0512(6) Uani 1 1 d . . . H30A H 1.1166 0.0138 0.0490 0.077 Uiso 1 1 calc R . . H30B H 1.1049 -0.0710 0.0627 0.077 Uiso 1 1 calc R . . H30C H 1.1635 -0.0181 0.1264 0.077 Uiso 1 1 calc R . . C31 C 0.93567(17) 0.24892(10) 0.29539(10) 0.0262(4) Uani 1 1 d . . . C32 C 0.95205(19) 0.18406(10) 0.33169(10) 0.0306(4) Uani 1 1 d . . . H32 H 0.9171 0.1412 0.3080 0.037 Uiso 1 1 calc R . . C33 C 1.01747(19) 0.17931(11) 0.40119(10) 0.0330(4) Uani 1 1 d . . . H33 H 1.0262 0.1340 0.4245 0.040 Uiso 1 1 calc R . . C34 C 1.07005(18) 0.24117(11) 0.43643(10) 0.0317(4) Uani 1 1 d . . . C35 C 1.0561(2) 0.30668(11) 0.40104(11) 0.0351(5) Uani 1 1 d . . . H35 H 1.0929 0.3493 0.4245 0.042 Uiso 1 1 calc R . . C36 C 0.98917(19) 0.31041(10) 0.33193(10) 0.0320(4) Uani 1 1 d . . . H36 H 0.9794 0.3559 0.3088 0.038 Uiso 1 1 calc R . . O5 O 1.13652(15) 0.24260(8) 0.50479(7) 0.0433(4) Uani 1 1 d . . . C37 C 1.1356(2) 0.17745(13) 0.54383(11) 0.0453(6) Uani 1 1 d . . . H37A H 1.1779 0.1861 0.5930 0.068 Uiso 1 1 calc R . . H37B H 1.1831 0.1396 0.5247 0.068 Uiso 1 1 calc R . . H37C H 1.0452 0.1619 0.5406 0.068 Uiso 1 1 calc R . . C38 C 0.71025(18) 0.26074(9) 0.21814(9) 0.0235(4) Uani 1 1 d . . . C39 C 0.66030(18) 0.25845(10) 0.27811(9) 0.0256(4) Uani 1 1 d . . . H39 H 0.7187 0.2514 0.3221 0.031 Uiso 1 1 calc R . . C40 C 0.52782(18) 0.26617(9) 0.27597(9) 0.0260(4) Uani 1 1 d . . . H40 H 0.4968 0.2647 0.3180 0.031 Uiso 1 1 calc R . . C41 C 0.44198(18) 0.27600(9) 0.21264(9) 0.0252(4) Uani 1 1 d . . . C42 C 0.48836(18) 0.27777(10) 0.15121(9) 0.0272(4) Uani 1 1 d . . . H42 H 0.4292 0.2839 0.1073 0.033 Uiso 1 1 calc R . . C43 C 0.62008(19) 0.27059(10) 0.15444(9) 0.0270(4) Uani 1 1 d . . . H43 H 0.6507 0.2723 0.1123 0.032 Uiso 1 1 calc R . . O6 O 0.30969(12) 0.28401(8) 0.20482(7) 0.0337(3) Uani 1 1 d . . . C44 C 0.2607(2) 0.28912(13) 0.26698(11) 0.0389(5) Uani 1 1 d . . . H44A H 0.3076 0.3273 0.2970 0.058 Uiso 1 1 calc R . . H44B H 0.2736 0.2429 0.2920 0.058 Uiso 1 1 calc R . . H44C H 0.1673 0.3007 0.2546 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0275(9) 0.0272(8) 0.0336(9) -0.0044(7) 0.0028(7) -0.0011(7) C1 0.0215(9) 0.0245(9) 0.0276(9) -0.0012(7) 0.0031(7) 0.0005(7) C2 0.0245(10) 0.0213(9) 0.0278(9) -0.0009(7) 0.0049(8) 0.0020(7) C3 0.0263(10) 0.0259(9) 0.0255(9) -0.0016(7) 0.0057(8) -0.0007(8) C4 0.0247(10) 0.0275(9) 0.0296(10) 0.0007(7) 0.0032(8) -0.0004(8) C5 0.0234(10) 0.0260(9) 0.0356(10) 0.0027(8) 0.0097(8) 0.0020(8) C6 0.0332(11) 0.0414(11) 0.0279(10) -0.0016(8) 0.0103(8) 0.0069(9) C7 0.0270(10) 0.0410(11) 0.0258(9) -0.0029(8) 0.0013(8) 0.0046(9) O1 0.0233(7) 0.0520(9) 0.0412(8) 0.0007(7) 0.0112(6) 0.0057(6) C8 0.0240(11) 0.0489(13) 0.0512(13) 0.0052(10) 0.0085(10) 0.0052(9) C9 0.0251(10) 0.0255(9) 0.0224(9) -0.0015(7) 0.0046(7) 0.0031(7) C10 0.0256(10) 0.0321(10) 0.0284(9) 0.0012(8) 0.0086(8) 0.0033(8) C11 0.0398(12) 0.0303(10) 0.0324(10) 0.0045(8) 0.0135(9) 0.0028(9) C12 0.0431(12) 0.0313(10) 0.0211(9) 0.0024(8) 0.0065(8) 0.0112(9) C13 0.0276(10) 0.0371(11) 0.0274(9) -0.0018(8) 0.0026(8) 0.0104(8) C14 0.0251(10) 0.0318(10) 0.0308(10) 0.0006(8) 0.0034(8) 0.0008(8) O2 0.0558(10) 0.0389(8) 0.0426(8) 0.0142(7) 0.0178(7) 0.0210(7) C15 0.0653(17) 0.0611(15) 0.0445(13) 0.0206(11) 0.0235(12) 0.0400(14) C16 0.0167(9) 0.0254(9) 0.0310(9) -0.0004(7) 0.0060(7) 0.0011(7) C17 0.0352(11) 0.0242(9) 0.0334(10) -0.0025(8) 0.0066(9) -0.0028(8) C18 0.0483(13) 0.0272(10) 0.0377(11) 0.0048(8) 0.0141(10) -0.0047(9) C19 0.0365(11) 0.0345(11) 0.0330(10) 0.0006(8) 0.0160(9) 0.0016(9) C20 0.0493(13) 0.0257(10) 0.0365(11) -0.0025(8) 0.0181(10) 0.0057(9) C21 0.0425(12) 0.0246(10) 0.0351(11) 0.0025(8) 0.0153(9) 0.0033(9) O3 0.0912(14) 0.0402(9) 0.0364(8) -0.0005(7) 0.0307(9) -0.0027(9) C22 0.113(3) 0.0486(15) 0.0401(13) -0.0068(11) 0.0357(15) -0.0041(15) N2 0.0374(10) 0.0268(9) 0.0367(9) 0.0041(7) 0.0134(8) 0.0007(7) C23 0.0238(10) 0.0247(9) 0.0281(9) 0.0013(7) 0.0075(8) 0.0004(7) C24 0.0253(10) 0.0278(10) 0.0232(9) 0.0025(7) 0.0048(7) 0.0043(8) C25 0.0252(10) 0.0283(9) 0.0289(9) 0.0024(8) 0.0073(8) 0.0028(8) C26 0.0304(11) 0.0266(10) 0.0337(10) 0.0018(8) 0.0058(8) 0.0003(8) C27 0.0331(11) 0.0301(10) 0.0258(9) -0.0012(8) 0.0047(8) 0.0074(8) C28 0.0266(11) 0.0413(12) 0.0361(11) -0.0046(9) 0.0109(9) 0.0032(9) C29 0.0272(10) 0.0336(10) 0.0369(10) -0.0032(8) 0.0090(8) -0.0011(8) O4 0.0418(9) 0.0341(8) 0.0506(9) -0.0095(7) 0.0164(7) 0.0078(7) C30 0.0472(15) 0.0450(13) 0.0661(16) -0.0103(12) 0.0230(12) 0.0154(11) C31 0.0207(9) 0.0266(9) 0.0326(10) -0.0014(8) 0.0085(8) 0.0006(7) C32 0.0305(11) 0.0258(10) 0.0329(10) -0.0041(8) 0.0013(8) 0.0005(8) C33 0.0331(11) 0.0302(10) 0.0333(10) -0.0010(8) 0.0024(9) 0.0025(8) C34 0.0224(10) 0.0420(11) 0.0304(10) -0.0066(8) 0.0049(8) 0.0010(8) C35 0.0328(11) 0.0335(11) 0.0382(11) -0.0115(9) 0.0061(9) -0.0085(9) C36 0.0318(11) 0.0274(10) 0.0384(11) -0.0033(8) 0.0113(9) -0.0034(8) O5 0.0420(9) 0.0520(9) 0.0310(7) -0.0062(7) -0.0028(6) -0.0076(7) C37 0.0419(13) 0.0617(15) 0.0288(11) 0.0004(10) 0.0003(9) -0.0025(11) C38 0.0246(10) 0.0184(8) 0.0279(9) -0.0002(7) 0.0068(7) 0.0021(7) C39 0.0249(10) 0.0256(9) 0.0253(9) 0.0028(7) 0.0036(7) 0.0009(7) C40 0.0289(10) 0.0245(9) 0.0255(9) 0.0026(7) 0.0083(8) 0.0009(8) C41 0.0228(10) 0.0221(9) 0.0301(9) 0.0001(7) 0.0044(8) 0.0016(7) C42 0.0272(10) 0.0277(9) 0.0251(9) 0.0001(7) 0.0024(8) 0.0032(8) C43 0.0322(11) 0.0262(9) 0.0243(9) 0.0008(7) 0.0098(8) 0.0043(8) O6 0.0221(7) 0.0473(8) 0.0310(7) 0.0015(6) 0.0045(6) 0.0029(6) C44 0.0272(11) 0.0515(13) 0.0412(12) 0.0025(10) 0.0143(9) 0.0030(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.484(2) . ? C1 C9 1.537(2) . ? C1 C16 1.539(2) . ? C1 C2 1.540(3) . ? C2 C3 1.387(2) . ? C2 C7 1.401(3) . ? C3 C4 1.393(3) . ? C4 C5 1.385(3) . ? C5 O1 1.373(2) . ? C5 C6 1.385(3) . ? C6 C7 1.384(3) . ? O1 C8 1.424(2) . ? C9 C14 1.393(3) . ? C9 C10 1.397(3) . ? C10 C11 1.390(3) . ? C11 C12 1.390(3) . ? C12 O2 1.371(2) . ? C12 C13 1.384(3) . ? C13 C14 1.387(3) . ? O2 C15 1.424(3) . ? C16 C21 1.384(3) . ? C16 C17 1.395(3) . ? C17 C18 1.380(3) . ? C18 C19 1.387(3) . ? C19 O3 1.368(2) . ? C19 C20 1.379(3) . ? C20 C21 1.392(3) . ? O3 C22 1.433(3) . ? N2 C23 1.481(2) . ? C23 C38 1.538(2) . ? C23 C24 1.541(2) . ? C23 C31 1.542(2) . ? C24 C29 1.388(3) . ? C24 C25 1.394(3) . ? C25 C26 1.384(3) . ? C26 C27 1.395(3) . ? C27 O4 1.374(2) . ? C27 C28 1.384(3) . ? C28 C29 1.390(3) . ? O4 C30 1.426(3) . ? C31 C32 1.386(3) . ? C31 C36 1.394(3) . ? C32 C33 1.386(3) . ? C33 C34 1.387(3) . ? C34 O5 1.367(2) . ? C34 C35 1.388(3) . ? C35 C36 1.383(3) . ? O5 C37 1.429(3) . ? C38 C39 1.389(2) . ? C38 C43 1.402(3) . ? C39 C40 1.389(3) . ? C40 C41 1.375(2) . ? C41 O6 1.371(2) . ? C41 C42 1.395(2) . ? C42 C43 1.376(3) . ? O6 C44 1.426(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C9 106.55(14) . . ? N1 C1 C16 108.04(15) . . ? C9 C1 C16 109.75(14) . . ? N1 C1 C2 111.59(15) . . ? C9 C1 C2 111.19(15) . . ? C16 C1 C2 109.62(14) . . ? C3 C2 C7 116.91(17) . . ? C3 C2 C1 123.41(16) . . ? C7 C2 C1 119.67(16) . . ? C2 C3 C4 122.06(17) . . ? C5 C4 C3 119.57(17) . . ? O1 C5 C6 115.87(17) . . ? O1 C5 C4 124.40(17) . . ? C6 C5 C4 119.72(17) . . ? C7 C6 C5 119.89(18) . . ? C6 C7 C2 121.83(18) . . ? C5 O1 C8 117.13(15) . . ? C14 C9 C10 117.46(17) . . ? C14 C9 C1 119.19(16) . . ? C10 C9 C1 123.24(16) . . ? C11 C10 C9 121.04(18) . . ? C10 C11 C12 120.30(19) . . ? O2 C12 C13 124.94(19) . . ? O2 C12 C11 115.58(18) . . ? C13 C12 C11 119.48(18) . . ? C12 C13 C14 119.74(18) . . ? C13 C14 C9 121.97(18) . . ? C12 O2 C15 117.62(18) . . ? C21 C16 C17 117.00(16) . . ? C21 C16 C1 121.63(16) . . ? C17 C16 C1 121.23(16) . . ? C18 C17 C16 121.44(17) . . ? C17 C18 C19 120.56(18) . . ? O3 C19 C20 124.76(18) . . ? O3 C19 C18 116.13(18) . . ? C20 C19 C18 119.08(18) . . ? C19 C20 C21 119.75(18) . . ? C16 C21 C20 122.15(18) . . ? C19 O3 C22 117.19(17) . . ? N2 C23 C38 111.64(15) . . ? N2 C23 C24 107.16(14) . . ? C38 C23 C24 111.06(15) . . ? N2 C23 C31 108.23(15) . . ? C38 C23 C31 109.84(14) . . ? C24 C23 C31 108.80(14) . . ? C29 C24 C25 117.37(17) . . ? C29 C24 C23 119.57(17) . . ? C25 C24 C23 122.93(16) . . ? C26 C25 C24 121.65(17) . . ? C25 C26 C27 119.75(18) . . ? O4 C27 C28 124.10(18) . . ? O4 C27 C26 116.22(18) . . ? C28 C27 C26 119.69(17) . . ? C27 C28 C29 119.47(18) . . ? C24 C29 C28 122.03(19) . . ? C27 O4 C30 116.83(17) . . ? C32 C31 C36 116.90(17) . . ? C32 C31 C23 120.85(16) . . ? C36 C31 C23 122.20(17) . . ? C33 C32 C31 122.51(18) . . ? C32 C33 C34 119.56(19) . . ? O5 C34 C33 124.39(19) . . ? O5 C34 C35 116.58(18) . . ? C33 C34 C35 119.04(18) . . ? C36 C35 C34 120.51(18) . . ? C35 C36 C31 121.47(18) . . ? C34 O5 C37 116.48(16) . . ? C39 C38 C43 116.77(17) . . ? C39 C38 C23 123.23(16) . . ? C43 C38 C23 120.00(16) . . ? C40 C39 C38 122.26(17) . . ? C41 C40 C39 119.50(17) . . ? O6 C41 C40 124.08(16) . . ? O6 C41 C42 116.05(16) . . ? C40 C41 C42 119.86(17) . . ? C43 C42 C41 119.79(17) . . ? C42 C43 C38 121.81(17) . . ? C41 O6 C44 117.33(14) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 67.62 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.227 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.041 #===END