Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Peter Brian Wyatt' _publ_contact_author_address ; Department of Chemistry Queen Mary, University of London Mile End Rd London E1 4NS UNITED KINGDOM ; _publ_contact_author_email P.B.WYATT@QMUL.AC.UK _publ_section_title ; Synthesis of phenazine derivatives for use as precursors to electrochemically generated bases ; loop_ _publ_author_name 'Peter Brian Wyatt' 'A.Mateo Alonso' 'Reshma Chudasama' 'Helen J. Groombridge' 'Roberto Horcajada' ; M.Motevalli ; 'James H.P. Utley' data_ama71-a _database_code_depnum_ccdc_archive 'CCDC 266538' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 N2 O5' _chemical_formula_weight 370.40 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 P21/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 14.5548(2) _cell_length_b 7.20830(10) _cell_length_c 17.2662(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.9380(10) _cell_angle_gamma 90.00 _cell_volume 1758.15(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9644 _exptl_absorpt_correction_T_max 0.9800 _exptl_absorpt_process_details ; Using multiple and symmetry-related data measurements via the program SORTAV See R.H. Blessing, Acta Crysta (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 7.35 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23675 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4011 _reflns_number_gt 2942 _reflns_threshold_expression >2sigma(I) loop_ _computing_data_collection ; DENZO (Otwinowski and Minor, 1997 COLLECT (Hooft, 1998) ; _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. (1997)' _computing_publication_material 'WINGX(L.J. Farrugia, 1999' _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^)+(0.0689P)^2^+0.1093P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4011 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _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 0.29120(7) 0.12482(14) 0.65508(6) 0.0201(2) Uani 1 1 d . . . N2 N 0.23753(7) 0.11800(14) 0.80302(6) 0.0196(2) Uani 1 1 d . . . O1 O 0.15867(6) 0.17022(14) 0.51797(5) 0.0277(2) Uani 1 1 d . . . O2 O 0.12579(6) 0.56508(15) 0.53778(6) 0.0318(3) Uani 1 1 d . . . O3 O 0.26212(6) 0.62526(14) 0.73868(5) 0.0290(3) Uani 1 1 d . . . O4 O 0.38843(6) 0.51647(12) 0.90639(5) 0.0215(2) Uani 1 1 d . . . O5 O 0.37183(6) 0.12014(12) 0.94239(5) 0.0237(2) Uani 1 1 d . . . C1 C 0.12703(9) 0.14917(18) 0.58589(8) 0.0220(3) Uani 1 1 d . . . C2 C 0.03374(9) 0.1425(2) 0.58813(8) 0.0263(3) Uani 1 1 d . . . H2 H -0.0143 0.1525 0.5401 0.032 Uiso 1 1 calc R . . C3 C 0.00869(9) 0.12050(19) 0.66217(8) 0.0269(3) Uani 1 1 d . . . H3 H -0.0564 0.1121 0.6624 0.032 Uiso 1 1 calc R . . C4 C 0.07450(9) 0.11110(19) 0.73242(8) 0.0240(3) Uani 1 1 d . . . H4 H 0.0555 0.0994 0.7811 0.029 Uiso 1 1 calc R . . C5 C 0.17244(9) 0.11892(17) 0.73282(7) 0.0193(3) Uani 1 1 d . . . C6 C 0.19973(9) 0.12959(17) 0.65839(7) 0.0190(3) Uani 1 1 d . . . C7 C 0.35633(9) 0.11644(16) 0.72506(7) 0.0188(3) Uani 1 1 d . . . C8 C 0.45395(9) 0.10571(18) 0.72531(8) 0.0232(3) Uani 1 1 d . . . H8 H 0.4727 0.0987 0.6764 0.028 Uiso 1 1 calc R . . C9 C 0.52016(9) 0.10549(18) 0.79570(8) 0.0244(3) Uani 1 1 d . . . H9 H 0.5852 0.0990 0.7953 0.029 Uiso 1 1 calc R . . C10 C 0.49438(9) 0.11470(17) 0.87015(8) 0.0229(3) Uani 1 1 d . . . H10 H 0.5423 0.1155 0.9185 0.028 Uiso 1 1 calc R . . C11 C 0.40168(9) 0.12236(16) 0.87258(7) 0.0199(3) Uani 1 1 d . . . C12 C 0.32867(9) 0.12005(16) 0.79987(7) 0.0178(3) Uani 1 1 d . . . C13 C 0.10645(9) 0.2897(2) 0.45563(8) 0.0264(3) Uani 1 1 d . . . H13A H 0.0386 0.2885 0.4563 0.032 Uiso 1 1 calc R . . H13B H 0.1121 0.2425 0.4031 0.032 Uiso 1 1 calc R . . C14 C 0.14347(10) 0.4851(2) 0.46687(8) 0.0291(3) Uani 1 1 d . . . H14A H 0.2124 0.4850 0.4706 0.035 Uiso 1 1 calc R . . H14B H 0.1124 0.5611 0.4201 0.035 Uiso 1 1 calc R . . C15 C 0.20852(9) 0.5945(2) 0.59965(8) 0.0268(3) Uani 1 1 d . . . H15A H 0.2413 0.7087 0.5892 0.032 Uiso 1 1 calc R . . H15B H 0.2525 0.4885 0.6027 0.032 Uiso 1 1 calc R . . C16 C 0.17809(9) 0.61299(19) 0.67696(8) 0.0247(3) Uani 1 1 d . . . H16A H 0.1390 0.7258 0.6761 0.030 Uiso 1 1 calc R . . H16B H 0.1404 0.5037 0.6853 0.030 Uiso 1 1 calc R . . C17 C 0.24495(9) 0.64476(19) 0.81603(8) 0.0233(3) Uani 1 1 d . . . H17A H 0.2154 0.5303 0.8306 0.028 Uiso 1 1 calc R . . H17B H 0.2011 0.7496 0.8164 0.028 Uiso 1 1 calc R . . C18 C 0.33814(9) 0.68004(18) 0.87559(8) 0.0232(3) Uani 1 1 d . . . H18A H 0.3787 0.7563 0.8496 0.028 Uiso 1 1 calc R . . H18B H 0.3258 0.7529 0.9206 0.028 Uiso 1 1 calc R . . C19 C 0.35963(10) 0.4471(2) 0.97415(8) 0.0263(3) Uani 1 1 d . . . H19A H 0.2901 0.4301 0.9608 0.032 Uiso 1 1 calc R . . H19B H 0.3766 0.5371 1.0186 0.032 Uiso 1 1 calc R . . C20 C 0.40755(9) 0.26518(18) 0.99919(7) 0.0237(3) Uani 1 1 d . . . H20A H 0.4765 0.2791 1.0047 0.028 Uiso 1 1 calc R . . H20B H 0.3975 0.2297 1.0519 0.028 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 0.0197(5) 0.0215(6) 0.0201(6) 0.0019(4) 0.0065(4) 0.0029(4) N2 0.0204(5) 0.0197(5) 0.0190(6) -0.0002(4) 0.0054(4) -0.0014(4) O1 0.0255(5) 0.0419(6) 0.0167(5) 0.0064(4) 0.0070(4) 0.0112(4) O2 0.0228(5) 0.0457(6) 0.0254(5) -0.0089(5) 0.0027(4) 0.0057(4) O3 0.0190(5) 0.0452(6) 0.0230(5) -0.0028(4) 0.0052(4) -0.0001(4) O4 0.0217(4) 0.0225(5) 0.0214(5) 0.0021(4) 0.0070(4) -0.0003(4) O5 0.0277(5) 0.0260(5) 0.0172(5) -0.0026(4) 0.0050(4) -0.0091(4) C1 0.0224(7) 0.0268(7) 0.0175(6) 0.0002(5) 0.0060(5) 0.0048(5) C2 0.0205(7) 0.0360(8) 0.0206(7) -0.0008(6) 0.0015(5) 0.0038(6) C3 0.0178(6) 0.0368(8) 0.0273(7) -0.0037(6) 0.0077(6) 0.0002(5) C4 0.0216(6) 0.0320(8) 0.0203(7) -0.0006(5) 0.0090(5) -0.0008(5) C5 0.0214(6) 0.0189(6) 0.0181(6) -0.0004(5) 0.0055(5) 0.0001(5) C6 0.0193(6) 0.0189(6) 0.0196(7) 0.0004(5) 0.0063(5) 0.0020(5) C7 0.0203(6) 0.0172(6) 0.0195(7) 0.0020(5) 0.0058(5) 0.0009(5) C8 0.0213(7) 0.0252(7) 0.0246(7) 0.0034(5) 0.0088(5) 0.0025(5) C9 0.0175(6) 0.0258(7) 0.0301(8) 0.0028(6) 0.0061(5) 0.0009(5) C10 0.0208(6) 0.0220(7) 0.0234(7) 0.0014(5) 0.0002(5) -0.0015(5) C11 0.0245(6) 0.0159(6) 0.0196(7) 0.0009(5) 0.0059(5) -0.0027(5) C12 0.0198(6) 0.0135(6) 0.0202(7) 0.0009(5) 0.0052(5) -0.0005(5) C13 0.0254(7) 0.0361(8) 0.0158(6) 0.0021(6) 0.0016(5) 0.0064(6) C14 0.0285(7) 0.0381(8) 0.0215(7) -0.0004(6) 0.0076(6) 0.0042(6) C15 0.0213(7) 0.0308(7) 0.0264(8) -0.0008(6) 0.0023(6) -0.0003(5) C16 0.0194(6) 0.0268(7) 0.0270(7) -0.0021(6) 0.0038(5) 0.0005(5) C17 0.0217(6) 0.0243(7) 0.0255(7) 0.0009(5) 0.0087(5) 0.0014(5) C18 0.0253(7) 0.0184(6) 0.0266(7) 0.0000(5) 0.0074(6) -0.0002(5) C19 0.0310(7) 0.0271(7) 0.0240(7) 0.0009(6) 0.0127(6) -0.0017(6) C20 0.0284(7) 0.0259(7) 0.0153(6) -0.0021(5) 0.0023(5) -0.0053(5) _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 C7 1.3455(16) . ? N1 C6 1.3466(16) . ? N2 C12 1.3407(16) . ? N2 C5 1.3467(16) . ? O1 C1 1.3676(15) . ? O1 C13 1.4434(16) . ? O2 C15 1.4200(16) . ? O2 C14 1.4315(16) . ? O3 C16 1.4181(15) . ? O3 C17 1.4236(16) . ? O4 C18 1.4217(16) . ? O4 C19 1.4251(15) . ? O5 C11 1.3762(15) . ? O5 C20 1.4421(15) . ? C1 C2 1.3686(18) . ? C1 C6 1.4383(18) . ? C2 C3 1.4201(19) . ? C2 H2 0.9500 . ? C3 C4 1.3541(19) . ? C3 H3 0.9500 . ? C4 C5 1.4249(18) . ? C4 H4 0.9500 . ? C5 C6 1.4356(17) . ? C7 C8 1.4219(18) . ? C7 C12 1.4429(17) . ? C8 C9 1.3570(19) . ? C8 H8 0.9500 . ? C9 C10 1.4248(19) . ? C9 H9 0.9500 . ? C10 C11 1.3611(19) . ? C10 H10 0.9500 . ? C11 C12 1.4363(17) . ? C13 C14 1.504(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.5101(19) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.5133(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.499(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? 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 C7 N1 C6 116.92(11) . . ? C12 N2 C5 116.87(11) . . ? C1 O1 C13 118.69(10) . . ? C15 O2 C14 114.14(10) . . ? C16 O3 C17 113.37(9) . . ? C18 O4 C19 111.81(10) . . ? C11 O5 C20 116.68(9) . . ? O1 C1 C2 124.71(12) . . ? O1 C1 C6 115.36(10) . . ? C2 C1 C6 119.92(12) . . ? C1 C2 C3 120.07(12) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 122.16(12) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C3 C4 C5 119.56(12) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N2 C5 C4 119.35(11) . . ? N2 C5 C6 121.30(11) . . ? C4 C5 C6 119.35(11) . . ? N1 C6 C5 121.75(11) . . ? N1 C6 C1 119.54(11) . . ? C5 C6 C1 118.70(11) . . ? N1 C7 C8 119.50(11) . . ? N1 C7 C12 121.00(11) . . ? C8 C7 C12 119.50(11) . . ? C9 C8 C7 119.75(12) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.57(12) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 120.54(12) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 O5 123.43(11) . . ? C10 C11 C12 120.19(12) . . ? O5 C11 C12 116.24(11) . . ? N2 C12 C11 119.72(11) . . ? N2 C12 C7 121.88(11) . . ? C11 C12 C7 118.39(11) . . ? O1 C13 C14 110.78(11) . . ? O1 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? O1 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? O2 C14 C13 110.79(12) . . ? O2 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? O2 C15 C16 107.59(10) . . ? O2 C15 H15A 110.2 . . ? C16 C15 H15A 110.2 . . ? O2 C15 H15B 110.2 . . ? C16 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? O3 C16 C15 106.64(10) . . ? O3 C16 H16A 110.4 . . ? C15 C16 H16A 110.4 . . ? O3 C16 H16B 110.4 . . ? C15 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? O3 C17 C18 108.85(10) . . ? O3 C17 H17A 109.9 . . ? C18 C17 H17A 109.9 . . ? O3 C17 H17B 109.9 . . ? C18 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? O4 C18 C17 114.28(10) . . ? O4 C18 H18A 108.7 . . ? C17 C18 H18A 108.7 . . ? O4 C18 H18B 108.7 . . ? C17 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? O4 C19 C20 109.60(10) . . ? O4 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? O4 C19 H19B 109.8 . . ? C20 C19 H19B 109.8 . . ? H19A C19 H19B 108.2 . . ? O5 C20 C19 111.81(10) . . ? O5 C20 H20A 109.3 . . ? C19 C20 H20A 109.3 . . ? O5 C20 H20B 109.3 . . ? C19 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.265 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.047 data_ama95-14 _database_code_depnum_ccdc_archive 'CCDC 269351' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 N2 O2' _chemical_formula_weight 350.45 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 21.854(12) _cell_length_b 10.992(5) _cell_length_c 7.770(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.01(7) _cell_angle_gamma 90.00 _cell_volume 1867(3) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.3215 _cell_measurement_theta_max 12.4115 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9611 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_process_details ? _exptl_special_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _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 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_reflns_number 3598 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0639 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3265 _reflns_number_gt 1953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 /PC (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 /PC (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0752P)^2^+2.6177P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3265 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1357 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1887 _refine_ls_wR_factor_gt 0.1564 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 O1 O 0.27217(10) 0.5981(2) 0.1093(3) 0.0306(6) Uani 1 1 d . . . O2 O -0.04832(10) 0.7809(2) 0.2005(3) 0.0324(6) Uani 1 1 d . . . N1 N 0.05343(12) 0.6331(3) 0.1154(4) 0.0256(7) Uani 1 1 d . . . N2 N 0.17133(12) 0.7399(3) 0.1196(3) 0.0244(7) Uani 1 1 d . . . C1 C 0.21655(15) 0.5414(3) 0.0909(4) 0.0258(8) Uani 1 1 d . . . C2 C 0.20906(16) 0.4209(3) 0.0614(4) 0.0296(8) Uani 1 1 d . . . H2 H 0.2440 0.3700 0.0520 0.036 Uiso 1 1 calc R . . C3 C 0.14974(16) 0.3695(3) 0.0443(4) 0.0295(8) Uani 1 1 d . . . H3 H 0.1458 0.2850 0.0214 0.035 Uiso 1 1 calc R . . C4 C 0.09829(16) 0.4389(3) 0.0601(4) 0.0276(8) Uani 1 1 d . . . H4 H 0.0590 0.4029 0.0494 0.033 Uiso 1 1 calc R . . C5 C 0.10405(15) 0.5656(3) 0.0928(4) 0.0235(7) Uani 1 1 d . . . C6 C 0.16363(15) 0.6200(3) 0.1023(4) 0.0241(8) Uani 1 1 d . . . C7 C 0.06117(15) 0.7520(3) 0.1443(4) 0.0248(8) Uani 1 1 d . . . C8 C 0.12032(15) 0.8080(3) 0.1385(4) 0.0241(8) Uani 1 1 d . . . C9 C 0.12567(16) 0.9357(3) 0.1519(4) 0.0290(8) Uani 1 1 d . . . H9 H 0.1649 0.9729 0.1461 0.035 Uiso 1 1 calc R . . C10 C 0.07511(17) 1.0052(3) 0.1728(5) 0.0346(9) Uani 1 1 d . . . H10 H 0.0788 1.0913 0.1749 0.042 Uiso 1 1 calc R . . C11 C 0.01643(17) 0.9504(3) 0.1917(5) 0.0317(9) Uani 1 1 d . . . H11 H -0.0183 1.0004 0.2111 0.038 Uiso 1 1 calc R . . C12 C 0.00943(15) 0.8282(3) 0.1824(5) 0.0276(8) Uani 1 1 d . . . C13 C 0.31438(16) 0.5418(4) 0.2288(5) 0.0345(9) Uani 1 1 d . . . H13A H 0.3528 0.5895 0.2319 0.041 Uiso 1 1 calc R . . H13B H 0.3244 0.4588 0.1879 0.041 Uiso 1 1 calc R . . C14 C 0.28827(17) 0.5340(4) 0.4080(5) 0.0359(9) Uani 1 1 d . . . H14A H 0.3190 0.4951 0.4838 0.043 Uiso 1 1 calc R . . H14B H 0.2519 0.4804 0.4051 0.043 Uiso 1 1 calc R . . C15 C 0.26977(17) 0.6551(4) 0.4875(5) 0.0404(10) Uani 1 1 d . . . H15A H 0.3071 0.7027 0.5140 0.048 Uiso 1 1 calc R . . H15B H 0.2453 0.7018 0.4031 0.048 Uiso 1 1 calc R . . C16 C 0.23288(19) 0.6389(5) 0.6503(6) 0.0590(14) Uani 1 1 d . . . H16A H 0.2319 0.7179 0.7113 0.071 Uiso 1 1 calc R . . H16B H 0.2548 0.5805 0.7252 0.071 Uiso 1 1 calc R . . C17 C 0.1676(2) 0.5947(5) 0.6301(7) 0.0673(16) Uani 1 1 d . . . H17A H 0.1647 0.5468 0.5225 0.081 Uiso 1 1 calc R . . H17B H 0.1580 0.5393 0.7269 0.081 Uiso 1 1 calc R . . C18 C 0.1221(2) 0.6890(5) 0.6251(7) 0.0659(15) Uani 1 1 d . . . H18A H 0.1341 0.7478 0.5346 0.079 Uiso 1 1 calc R . . H18B H 0.1234 0.7327 0.7364 0.079 Uiso 1 1 calc R . . C19 C 0.05505(18) 0.6505(4) 0.5912(5) 0.0429(10) Uani 1 1 d . . . H19A H 0.0526 0.6045 0.4819 0.052 Uiso 1 1 calc R . . H19B H 0.0408 0.5967 0.6853 0.052 Uiso 1 1 calc R . . C20 C 0.01469(17) 0.7613(4) 0.5811(5) 0.0369(9) Uani 1 1 d . . . H20A H 0.0346 0.8217 0.5050 0.044 Uiso 1 1 calc R . . H20B H 0.0119 0.7977 0.6973 0.044 Uiso 1 1 calc R . . C21 C -0.05042(17) 0.7387(4) 0.5145(5) 0.0438(10) Uani 1 1 d . . . H21A H -0.0705 0.6804 0.5935 0.053 Uiso 1 1 calc R . . H21B H -0.0732 0.8163 0.5223 0.053 Uiso 1 1 calc R . . C22 C -0.05737(16) 0.6908(3) 0.3339(5) 0.0331(9) Uani 1 1 d . . . H22A H -0.0276 0.6241 0.3166 0.040 Uiso 1 1 calc R . . H22B H -0.0989 0.6559 0.3213 0.040 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 O1 0.0185(12) 0.0399(15) 0.0333(14) 0.0032(11) 0.0003(10) -0.0003(11) O2 0.0209(13) 0.0307(14) 0.0454(15) -0.0011(12) -0.0010(11) 0.0001(11) N1 0.0230(15) 0.0252(16) 0.0286(16) -0.0048(13) 0.0007(12) 0.0001(13) N2 0.0253(15) 0.0272(16) 0.0208(14) -0.0023(12) 0.0002(12) -0.0026(12) C1 0.0190(17) 0.037(2) 0.0214(18) 0.0054(15) 0.0010(13) -0.0013(15) C2 0.0252(19) 0.033(2) 0.0307(19) 0.0033(16) 0.0034(15) 0.0086(16) C3 0.033(2) 0.0231(18) 0.0323(19) -0.0023(16) 0.0013(16) 0.0027(16) C4 0.0258(19) 0.0262(19) 0.0308(19) -0.0041(15) 0.0041(15) -0.0035(15) C5 0.0232(18) 0.0267(18) 0.0205(17) -0.0013(14) 0.0004(13) 0.0016(15) C6 0.0235(17) 0.030(2) 0.0188(16) -0.0011(15) -0.0004(14) -0.0009(15) C7 0.0256(18) 0.0266(19) 0.0222(17) -0.0016(15) -0.0005(14) -0.0006(15) C8 0.0272(18) 0.0269(18) 0.0182(17) -0.0013(14) 0.0002(14) -0.0018(15) C9 0.032(2) 0.0272(19) 0.0281(19) -0.0013(16) 0.0037(15) -0.0080(16) C10 0.047(2) 0.0220(19) 0.034(2) -0.0017(16) 0.0022(18) -0.0031(17) C11 0.031(2) 0.027(2) 0.037(2) -0.0017(16) -0.0002(16) 0.0075(16) C12 0.0243(18) 0.0263(19) 0.032(2) -0.0024(16) -0.0026(15) 0.0008(15) C13 0.0200(18) 0.046(2) 0.037(2) -0.0016(18) -0.0034(15) 0.0050(17) C14 0.0275(19) 0.047(2) 0.034(2) 0.0010(18) -0.0033(16) 0.0043(18) C15 0.027(2) 0.058(3) 0.037(2) -0.012(2) -0.0042(17) 0.0008(18) C16 0.040(2) 0.092(4) 0.046(3) -0.032(3) 0.006(2) -0.005(2) C17 0.041(3) 0.090(4) 0.072(3) -0.033(3) 0.011(2) -0.004(3) C18 0.048(3) 0.077(4) 0.073(3) -0.033(3) -0.022(2) 0.015(3) C19 0.043(2) 0.041(2) 0.044(2) -0.014(2) -0.0100(19) 0.0108(19) C20 0.040(2) 0.036(2) 0.035(2) -0.0083(18) -0.0032(17) 0.0037(18) C21 0.032(2) 0.057(3) 0.043(2) -0.009(2) 0.0028(18) 0.012(2) C22 0.0239(19) 0.032(2) 0.044(2) -0.0049(18) 0.0034(16) -0.0021(16) _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 O1 C1 1.374(4) . ? O1 C13 1.448(4) . ? O2 C12 1.372(4) . ? O2 C22 1.447(4) . ? N1 C7 1.336(4) . ? N1 C5 1.344(4) . ? N2 C6 1.335(4) . ? N2 C8 1.351(4) . ? C1 C2 1.354(5) . ? C1 C6 1.446(5) . ? C2 C3 1.420(5) . ? C2 H2 0.9500 . ? C3 C4 1.364(5) . ? C3 H3 0.9500 . ? C4 C5 1.421(5) . ? C4 H4 0.9500 . ? C5 C6 1.435(5) . ? C7 C8 1.433(5) . ? C7 C12 1.438(5) . ? C8 C9 1.412(5) . ? C9 C10 1.353(5) . ? C9 H9 0.9500 . ? C10 C11 1.424(5) . ? C10 H10 0.9500 . ? C11 C12 1.355(5) . ? C11 H11 0.9500 . ? C13 C14 1.507(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.522(5) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.510(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.515(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.436(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.548(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.506(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.534(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.506(5) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 C1 O1 C13 115.9(3) . . ? C12 O2 C22 117.3(3) . . ? C7 N1 C5 117.3(3) . . ? C6 N2 C8 117.0(3) . . ? C2 C1 O1 124.7(3) . . ? C2 C1 C6 119.9(3) . . ? O1 C1 C6 115.5(3) . . ? C1 C2 C3 121.0(3) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 121.4(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 119.5(3) . . ? N1 C5 C6 120.7(3) . . ? C4 C5 C6 119.9(3) . . ? N2 C6 C5 122.1(3) . . ? N2 C6 C1 119.7(3) . . ? C5 C6 C1 118.3(3) . . ? N1 C7 C8 121.9(3) . . ? N1 C7 C12 120.3(3) . . ? C8 C7 C12 117.8(3) . . ? N2 C8 C9 119.4(3) . . ? N2 C8 C7 120.7(3) . . ? C9 C8 C7 120.0(3) . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 121.0(3) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 O2 118.3(3) . . ? C11 C12 C7 120.0(3) . . ? O2 C12 C7 121.6(3) . . ? O1 C13 C14 112.0(3) . . ? O1 C13 H13A 109.2 . . ? C14 C13 H13A 109.2 . . ? O1 C13 H13B 109.2 . . ? C14 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C13 C14 C15 115.2(3) . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? C15 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C16 C15 C14 112.3(4) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 C17 117.0(4) . . ? C15 C16 H16A 108.0 . . ? C17 C16 H16A 108.0 . . ? C15 C16 H16B 108.0 . . ? C17 C16 H16B 108.0 . . ? H16A C16 H16B 107.3 . . ? C18 C17 C16 115.0(5) . . ? C18 C17 H17A 108.5 . . ? C16 C17 H17A 108.5 . . ? C18 C17 H17B 108.5 . . ? C16 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C17 C18 C19 117.5(4) . . ? C17 C18 H18A 107.9 . . ? C19 C18 H18A 107.9 . . ? C17 C18 H18B 107.9 . . ? C19 C18 H18B 107.9 . . ? H18A C18 H18B 107.2 . . ? C20 C19 C18 110.0(4) . . ? C20 C19 H19A 109.7 . . ? C18 C19 H19A 109.7 . . ? C20 C19 H19B 109.7 . . ? C18 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? C19 C20 C21 115.5(3) . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20B 108.4 . . ? C21 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? C22 C21 C20 117.7(3) . . ? C22 C21 H21A 107.9 . . ? C20 C21 H21A 107.9 . . ? C22 C21 H21B 107.9 . . ? C20 C21 H21B 107.9 . . ? H21A C21 H21B 107.2 . . ? O2 C22 C21 114.5(3) . . ? O2 C22 H22A 108.6 . . ? C21 C22 H22A 108.6 . . ? O2 C22 H22B 108.6 . . ? C21 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.033 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.061