# Supplementary Material (ESI) 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 _audit_creation_method 'SHELXL-97 and manual editing' # ============== SUBMISSION DETAILS =============================== _publ_contact_author ; Volkhard Austel Department of Organic Chemistry II University of Ulm D-89069 Ulm, Germany ; _publ_contact_author_email volkhard.austel@chemie.uni-ulm.de _publ_contact_author_fax +49-(0)731-50-22840 _publ_contact_author_phone +49-(0)731-50-22855 _publ_contact_letter ? # ============== TITLE AND AUTHOR LIST ============================= _publ_section_title ; Synthesis and Conformational Properties of 2,6-Bis-arylamino-3-nitropyridines ; _publ_section_title_footnote ? loop_ _publ_author_name _publ_author_address V.Austel ; Department of Organic Chemistry II University of Ulm D-89069 Ulm, Germany ; S.Schmid ; Department of Organic Chemistry II University of Ulm D-89069 Ulm, Germany ; U.Thewalt ; Section for X-Ray and Electron Diffraction University of Ulm D-89069 Ulm, Germany ; M.Rottgen ; Department of Organic Chemistry II University of Ulm D-89069 Ulm, Germany ; D.Meinhard ; Department of Organic Chemistry II University of Ulm D-89069 Ulm, Germany ; _publ_contact_author_name 'Volkhard Austel' # ================== Results ================================== data_7c _database_code_depnum_ccdc_archive 'CCDC 243005' _chemical_name_systematic ; 2-Anilino-6-(N-tert-butyloxycarbonylmethylanilino)-3-nitropyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H24 N4 O4' _chemical_formula_weight 420.46 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 7.6072(17) _cell_length_b 24.695(4) _cell_length_c 11.851(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.06(3) _cell_angle_gamma 90.00 _cell_volume 2116.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9641 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'IPDS system of STOE' _diffrn_measurement_method 'imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16630 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.97 _reflns_number_total 4066 _reflns_number_gt 2797 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS software (STOE, 1997)' _computing_cell_refinement 'IPDS software (STOE, 1997)' _computing_data_reduction 'IPDS software (STOE, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Johnson & Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0420P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0071(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4066 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0595 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.006 _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 0.20353(16) 0.13283(4) 0.18974(11) 0.0464(3) Uani 1 1 d . . . O2 O 0.3814(2) 0.12317(4) 0.36941(13) 0.0746(5) Uani 1 1 d . . . O3 O 0.00996(13) 0.43862(4) 0.14412(8) 0.0301(2) Uani 1 1 d . . . O4 O 0.05095(14) 0.39888(4) 0.32288(9) 0.0331(2) Uani 1 1 d . . . N1 N 0.28035(16) 0.30057(4) 0.22199(10) 0.0280(3) Uani 1 1 d . . . N2 N 0.3048(2) 0.15263(5) 0.28478(13) 0.0452(4) Uani 1 1 d . . . N3 N 0.13910(18) 0.23018(5) 0.09633(11) 0.0348(3) Uani 1 1 d . . . HN3 H 0.127(3) 0.1945(8) 0.0921(16) 0.055(5) Uiso 1 1 d . . . N4 N 0.41494(15) 0.37300(4) 0.33724(10) 0.0277(3) Uani 1 1 d . . . C1 C 0.52525(19) 0.39766(5) 0.44638(12) 0.0274(3) Uani 1 1 d . . . C2 C 0.7105(2) 0.40706(5) 0.46399(13) 0.0333(3) Uani 1 1 d . . . H2 H 0.7653 0.3963 0.4056 0.040 Uiso 1 1 calc R . . C3 C 0.8162(2) 0.43224(6) 0.56711(14) 0.0393(4) Uani 1 1 d . . . H3 H 0.9436 0.4390 0.5790 0.047 Uiso 1 1 calc R . . C4 C 0.7378(2) 0.44758(6) 0.65278(14) 0.0387(4) Uani 1 1 d . . . H4 H 0.8108 0.4650 0.7233 0.046 Uiso 1 1 calc R . . C5 C 0.5537(2) 0.43755(6) 0.63553(15) 0.0450(4) Uani 1 1 d . . . H5 H 0.5000 0.4474 0.6950 0.054 Uiso 1 1 calc R . . C6 C 0.4459(2) 0.41316(6) 0.53203(14) 0.0401(4) Uani 1 1 d . . . H6 H 0.3180 0.4071 0.5198 0.048 Uiso 1 1 calc R . . C7 C 0.30632(19) 0.40828(5) 0.24383(13) 0.0272(3) Uani 1 1 d . . . H7A H 0.3073 0.3938 0.1662 0.033 Uiso 1 1 calc R . . H7B H 0.3645 0.4446 0.2537 0.033 Uiso 1 1 calc R . . C8 C 0.10731(19) 0.41394(5) 0.24347(12) 0.0256(3) Uani 1 1 d . . . C9 C -0.1910(2) 0.44940(6) 0.11925(13) 0.0349(3) Uani 1 1 d . . . C10 C -0.2921(2) 0.39643(7) 0.11746(15) 0.0459(4) Uani 1 1 d . . . H10A H -0.2538 0.3702 0.0675 0.055 Uiso 1 1 calc R . . H10B H -0.4257 0.4025 0.0853 0.055 Uiso 1 1 calc R . . H10C H -0.2624 0.3822 0.1984 0.055 Uiso 1 1 calc R . . C11 C -0.2433(2) 0.47430(8) -0.00397(16) 0.0569(5) Uani 1 1 d . . . H11A H -0.1694 0.5070 -0.0020 0.068 Uiso 1 1 calc R . . H11B H -0.3748 0.4838 -0.0297 0.068 Uiso 1 1 calc R . . H11C H -0.2192 0.4482 -0.0597 0.068 Uiso 1 1 calc R . . C12 C -0.2179(2) 0.48946(6) 0.21002(15) 0.0439(4) Uani 1 1 d . . . H12A H -0.1671 0.4742 0.2899 0.053 Uiso 1 1 calc R . . H12B H -0.3501 0.4967 0.1937 0.053 Uiso 1 1 calc R . . H12C H -0.1537 0.5233 0.2050 0.053 Uiso 1 1 calc R . . C13 C 0.39009(19) 0.31813(5) 0.32655(12) 0.0270(3) Uani 1 1 d . . . C14 C 0.4778(2) 0.28313(5) 0.42201(14) 0.0359(4) Uani 1 1 d . . . H14 H 0.5555 0.2968 0.4955 0.043 Uiso 1 1 calc R . . C15 C 0.4462(2) 0.22925(6) 0.40414(14) 0.0396(4) Uani 1 1 d . . . H15 H 0.5022 0.2046 0.4664 0.048 Uiso 1 1 calc R . . C16 C 0.3330(2) 0.20956(5) 0.29601(14) 0.0357(4) Uani 1 1 d . . . C17 C 0.2494(2) 0.24728(5) 0.20348(13) 0.0294(3) Uani 1 1 d . . . C18 C 0.0419(2) 0.25842(5) -0.00753(13) 0.0319(3) Uani 1 1 d . . . C19 C 0.0250(3) 0.31413(6) -0.01937(15) 0.0523(5) Uani 1 1 d . . . H19 H 0.0819 0.3369 0.0464 0.063 Uiso 1 1 calc R . . C20 C -0.0751(3) 0.33654(7) -0.12724(15) 0.0570(5) Uani 1 1 d . . . H20 H -0.0848 0.3748 -0.1345 0.068 Uiso 1 1 calc R . . C21 C -0.1602(3) 0.30512(7) -0.22357(15) 0.0472(4) Uani 1 1 d . . . H21 H -0.2302 0.3211 -0.2966 0.057 Uiso 1 1 calc R . . C22 C -0.1422(3) 0.24960(7) -0.21245(15) 0.0482(4) Uani 1 1 d . . . H22 H -0.1988 0.2271 -0.2788 0.058 Uiso 1 1 calc R . . C23 C -0.0432(2) 0.22652(6) -0.10621(14) 0.0406(4) Uani 1 1 d . . . H23 H -0.0327 0.1882 -0.1000 0.049 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 0.0521(7) 0.0291(5) 0.0474(8) -0.0060(5) -0.0001(6) 0.0011(5) O2 0.0959(11) 0.0270(6) 0.0645(9) 0.0107(6) -0.0282(8) 0.0017(6) O3 0.0242(5) 0.0358(5) 0.0289(6) 0.0075(4) 0.0062(5) 0.0042(4) O4 0.0320(6) 0.0368(5) 0.0316(6) 0.0063(4) 0.0114(5) 0.0004(4) N1 0.0282(6) 0.0264(6) 0.0280(7) -0.0005(5) 0.0066(6) 0.0037(5) N2 0.0487(8) 0.0265(6) 0.0470(9) 0.0013(6) -0.0048(8) 0.0038(6) N3 0.0423(8) 0.0259(6) 0.0306(8) -0.0044(5) 0.0032(7) 0.0039(5) N4 0.0275(6) 0.0236(5) 0.0286(7) 0.0014(5) 0.0038(6) 0.0023(5) C1 0.0296(8) 0.0210(6) 0.0284(8) 0.0027(5) 0.0042(7) 0.0026(5) C2 0.0298(8) 0.0370(8) 0.0325(9) 0.0004(6) 0.0088(7) 0.0007(6) C3 0.0320(8) 0.0394(8) 0.0416(10) 0.0015(7) 0.0042(8) -0.0052(6) C4 0.0459(10) 0.0288(7) 0.0334(9) -0.0030(6) 0.0006(8) -0.0010(7) C5 0.0483(10) 0.0492(9) 0.0397(10) -0.0117(8) 0.0169(9) 0.0016(8) C6 0.0326(8) 0.0473(9) 0.0413(10) -0.0070(7) 0.0129(8) -0.0014(7) C7 0.0273(7) 0.0232(6) 0.0301(8) 0.0047(5) 0.0072(7) 0.0010(5) C8 0.0274(7) 0.0201(6) 0.0273(8) -0.0005(5) 0.0055(7) -0.0003(5) C9 0.0209(7) 0.0502(9) 0.0308(9) 0.0033(7) 0.0041(7) 0.0055(6) C10 0.0319(9) 0.0683(11) 0.0363(10) -0.0136(8) 0.0088(8) -0.0115(8) C11 0.0344(10) 0.0929(14) 0.0399(11) 0.0212(10) 0.0065(9) 0.0212(9) C12 0.0357(9) 0.0464(9) 0.0481(11) 0.0014(8) 0.0108(9) 0.0130(7) C13 0.0236(7) 0.0268(7) 0.0301(8) 0.0010(6) 0.0075(7) 0.0029(5) C14 0.0365(9) 0.0291(7) 0.0333(9) 0.0019(6) -0.0019(7) 0.0010(6) C15 0.0406(9) 0.0291(7) 0.0377(10) 0.0072(6) -0.0047(8) 0.0041(7) C16 0.0368(9) 0.0241(7) 0.0397(9) 0.0004(6) 0.0025(8) 0.0031(6) C17 0.0288(7) 0.0280(7) 0.0302(8) -0.0011(6) 0.0073(7) 0.0047(6) C18 0.0336(8) 0.0339(7) 0.0275(8) -0.0042(6) 0.0083(7) 0.0067(6) C19 0.0748(13) 0.0357(8) 0.0313(9) -0.0096(7) -0.0054(9) 0.0155(8) C20 0.0852(15) 0.0367(8) 0.0358(10) -0.0035(7) -0.0005(10) 0.0189(9) C21 0.0579(11) 0.0493(9) 0.0277(9) 0.0003(7) 0.0035(9) 0.0094(8) C22 0.0595(11) 0.0484(9) 0.0291(9) -0.0090(7) 0.0027(9) -0.0068(8) C23 0.0504(10) 0.0335(8) 0.0355(9) -0.0056(7) 0.0097(9) -0.0038(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 O1 N2 1.2502(18) . ? O2 N2 1.2299(18) . ? O3 C8 1.3287(17) . ? O3 C9 1.4886(17) . ? O4 C8 1.2074(16) . ? N1 C13 1.3339(19) . ? N1 C17 1.3429(17) . ? N2 C16 1.4222(18) . ? N3 C17 1.3543(19) . ? N3 C18 1.4087(19) . ? N4 C13 1.3686(17) . ? N4 C1 1.4405(18) . ? N4 C7 1.4492(17) . ? C1 C2 1.378(2) . ? C1 C6 1.386(2) . ? C2 C3 1.385(2) . ? C3 C4 1.380(2) . ? C4 C5 1.374(2) . ? C5 C6 1.384(2) . ? C7 C8 1.5191(19) . ? C9 C10 1.514(2) . ? C9 C11 1.520(2) . ? C9 C12 1.521(2) . ? C13 C14 1.416(2) . ? C14 C15 1.357(2) . ? C15 C16 1.391(2) . ? C16 C17 1.429(2) . ? C18 C19 1.385(2) . ? C18 C23 1.392(2) . ? C19 C20 1.384(2) . ? C20 C21 1.366(2) . ? C21 C22 1.380(2) . ? C22 C23 1.375(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 C8 O3 C9 120.91(10) . . ? C13 N1 C17 119.87(11) . . ? O2 N2 O1 120.48(12) . . ? O2 N2 C16 119.26(14) . . ? O1 N2 C16 120.25(13) . . ? C17 N3 C18 132.05(12) . . ? C13 N4 C1 121.81(11) . . ? C13 N4 C7 119.65(12) . . ? C1 N4 C7 117.86(10) . . ? C2 C1 C6 119.96(14) . . ? C2 C1 N4 119.39(12) . . ? C6 C1 N4 120.63(13) . . ? C1 C2 C3 119.76(14) . . ? C4 C3 C2 120.45(15) . . ? C5 C4 C3 119.61(15) . . ? C4 C5 C6 120.47(15) . . ? C1 C6 C5 119.73(15) . . ? N4 C7 C8 112.91(11) . . ? O4 C8 O3 126.65(13) . . ? O4 C8 C7 124.32(13) . . ? O3 C8 C7 109.02(11) . . ? O3 C9 C10 109.54(12) . . ? O3 C9 C11 102.08(11) . . ? C10 C9 C11 110.84(14) . . ? O3 C9 C12 109.33(13) . . ? C10 C9 C12 113.12(13) . . ? C11 C9 C12 111.34(14) . . ? N1 C13 N4 115.89(12) . . ? N1 C13 C14 123.24(12) . . ? N4 C13 C14 120.87(13) . . ? C15 C14 C13 117.20(14) . . ? C14 C15 C16 121.03(14) . . ? C15 C16 N2 117.64(13) . . ? C15 C16 C17 118.70(12) . . ? N2 C16 C17 123.65(14) . . ? N1 C17 N3 119.01(13) . . ? N1 C17 C16 119.97(13) . . ? N3 C17 C16 121.02(12) . . ? C19 C18 C23 118.20(14) . . ? C19 C18 N3 125.99(14) . . ? C23 C18 N3 115.81(12) . . ? C18 C19 C20 119.86(15) . . ? C21 C20 C19 121.81(16) . . ? C20 C21 C22 118.50(16) . . ? C23 C22 C21 120.61(15) . . ? C22 C23 C18 121.00(14) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.174 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.038 # ================================================================= # ================================================================= data_7e _database_code_depnum_ccdc_archive 'CCDC 243006' _chemical_name_systematic ; 6-Anilino-2-(N-methylanilino)-3-nitropyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 N4 O2' _chemical_formula_weight 320.35 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.113(2) _cell_length_b 12.417(3) _cell_length_c 14.105(3) _cell_angle_alpha 107.48(3) _cell_angle_beta 95.21(3) _cell_angle_gamma 102.18(3) _cell_volume 1628.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9655 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'STOE IPDS system' _diffrn_measurement_method 'imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14892 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.08 _reflns_number_total 5971 _reflns_number_gt 3473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS software (STOE, 1997)' _computing_cell_refinement 'IPDS software (STOE, 1997)' _computing_data_reduction 'IPDS software (STOE, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Johnson & Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0196(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5971 _refine_ls_number_parameters 444 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.010 _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 0.44355(15) 0.33582(12) 0.75337(10) 0.0524(4) Uani 1 1 d . . . N2 N 0.6369(2) 0.41271(15) 0.56267(13) 0.0690(5) Uani 1 1 d . . . N3 N 0.64152(17) 0.48084(14) 0.78660(10) 0.0615(4) Uani 1 1 d . . . N4 N 0.24576(18) 0.18675(14) 0.72379(11) 0.0589(4) Uani 1 1 d . . . HN4 H 0.179(2) 0.1348(18) 0.6748(14) 0.072(6) Uiso 1 1 d . . . N5 N 0.95255(16) 0.60443(13) 0.31143(10) 0.0556(4) Uani 1 1 d . . . N6 N 1.11212(17) 0.90906(14) 0.47017(12) 0.0628(4) Uani 1 1 d . . . N7 N 1.08552(17) 0.74312(13) 0.25976(10) 0.0602(4) Uani 1 1 d . . . HN7 H 0.783(3) 0.434(2) 0.4030(18) 0.103(8) Uiso 1 1 d . . . N8 N 0.81842(19) 0.45624(15) 0.35445(13) 0.0694(5) Uani 1 1 d . . . O1 O 0.75648(17) 0.43842(13) 0.60558(11) 0.0782(4) Uani 1 1 d . . . O2 O 0.6092(2) 0.40990(18) 0.47463(11) 0.1134(7) Uani 1 1 d . . . O3 O 1.17748(16) 0.95838(13) 0.55682(10) 0.0846(5) Uani 1 1 d . . . O4 O 1.09125(15) 0.96331(12) 0.41207(10) 0.0733(4) Uani 1 1 d . . . C1 C 0.24552(19) 0.16611(15) 0.81641(12) 0.0531(4) Uani 1 1 d . . . C2 C 0.3482(2) 0.2192(2) 0.89892(13) 0.0742(6) Uani 1 1 d . . . H2 H 0.4255 0.2732 0.8959 0.089 Uiso 1 1 calc R . . C3 C 0.3356(3) 0.1916(2) 0.98681(14) 0.0837(7) Uani 1 1 d . . . H3 H 0.4050 0.2277 1.0425 0.100 Uiso 1 1 calc R . . C4 C 0.2239(3) 0.1130(2) 0.99256(15) 0.0795(6) Uani 1 1 d . . . H4 H 0.2161 0.0958 1.0519 0.095 Uiso 1 1 calc R . . C5 C 0.1220(3) 0.0587(2) 0.90997(16) 0.0828(7) Uani 1 1 d . . . H5 H 0.0457 0.0038 0.9131 0.099 Uiso 1 1 calc R . . C6 C 0.1327(2) 0.08557(18) 0.82285(14) 0.0701(5) Uani 1 1 d . . . H6 H 0.0629 0.0490 0.7675 0.084 Uiso 1 1 calc R . . C7 C 0.33644(19) 0.25819(15) 0.69018(12) 0.0520(4) Uani 1 1 d . . . C8 C 0.3084(2) 0.24660(17) 0.58716(12) 0.0602(5) Uani 1 1 d . . . H8 H 0.2264 0.1992 0.5467 0.072 Uiso 1 1 calc R . . C9 C 0.4051(2) 0.30712(17) 0.54960(13) 0.0611(5) Uani 1 1 d . . . H9 H 0.3907 0.3012 0.4819 0.073 Uiso 1 1 calc R . . C10 C 0.52613(19) 0.37825(16) 0.61182(12) 0.0547(4) Uani 1 1 d . . . C11 C 0.53793(19) 0.39844(15) 0.71663(12) 0.0527(4) Uani 1 1 d . . . C12 C 0.7021(2) 0.58776(16) 0.77096(12) 0.0571(5) Uani 1 1 d . . . C13 C 0.8426(2) 0.63139(19) 0.79153(16) 0.0748(6) Uani 1 1 d . . . H13 H 0.8985 0.5913 0.8155 0.090 Uiso 1 1 calc R . . C14 C 0.8999(3) 0.7350(2) 0.77634(17) 0.0836(7) Uani 1 1 d . . . H14 H 0.9945 0.7651 0.7902 0.100 Uiso 1 1 calc R . . C15 C 0.8167(3) 0.79346(19) 0.74069(15) 0.0798(7) Uani 1 1 d . . . H15 H 0.8555 0.8626 0.7296 0.096 Uiso 1 1 calc R . . C16 C 0.6771(3) 0.75087(18) 0.72131(14) 0.0717(6) Uani 1 1 d . . . H16 H 0.6214 0.7914 0.6980 0.086 Uiso 1 1 calc R . . C17 C 0.6199(2) 0.64814(17) 0.73638(12) 0.0614(5) Uani 1 1 d . . . H17 H 0.5251 0.6191 0.7232 0.074 Uiso 1 1 calc R . . C18 C 0.6550(3) 0.4813(2) 0.89074(14) 0.0892(7) Uani 1 1 d . . . H18A H 0.5801 0.5059 0.9205 0.116 Uiso 1 1 calc R . . H18B H 0.7400 0.5341 0.9283 0.116 Uiso 1 1 calc R . . H18C H 0.6536 0.4041 0.8918 0.116 Uiso 1 1 calc R . . C19 C 0.7737(2) 0.36932(17) 0.25950(13) 0.0607(5) Uani 1 1 d . . . C20 C 0.7719(3) 0.3897(2) 0.16823(16) 0.0837(7) Uani 1 1 d . . . H20 H 0.7991 0.4654 0.1667 0.100 Uiso 1 1 calc R . . C21 C 0.7294(3) 0.2969(2) 0.07931(17) 0.1014(9) Uani 1 1 d . . . H21 H 0.7302 0.3111 0.0183 0.122 Uiso 1 1 calc R . . C22 C 0.6867(3) 0.1858(2) 0.07888(18) 0.0967(8) Uani 1 1 d . . . H22 H 0.6585 0.1244 0.0183 0.116 Uiso 1 1 calc R . . C23 C 0.6856(2) 0.1651(2) 0.16897(17) 0.0814(6) Uani 1 1 d . . . H23 H 0.6555 0.0893 0.1696 0.098 Uiso 1 1 calc R . . C24 C 0.7286(2) 0.25552(18) 0.25806(15) 0.0687(5) Uani 1 1 d . . . H24 H 0.7275 0.2402 0.3186 0.082 Uiso 1 1 calc R . . C25 C 0.9037(2) 0.56394(17) 0.38220(13) 0.0584(5) Uani 1 1 d . . . C26 C 0.9403(2) 0.62826(18) 0.48619(13) 0.0657(5) Uani 1 1 d . . . H26 H 0.9135 0.5951 0.5346 0.079 Uiso 1 1 calc R . . C27 C 1.0153(2) 0.73899(19) 0.51266(13) 0.0643(5) Uani 1 1 d . . . H27 H 1.0396 0.7842 0.5804 0.077 Uiso 1 1 calc R . . C28 C 1.05682(19) 0.78641(16) 0.43881(12) 0.0558(5) Uani 1 1 d . . . C29 C 1.03150(19) 0.71235(16) 0.33723(12) 0.0528(4) Uani 1 1 d . . . C30 C 1.2159(2) 0.82174(15) 0.27433(13) 0.0565(5) Uani 1 1 d . . . C31 C 1.2413(2) 0.88639(17) 0.21004(15) 0.0685(5) Uani 1 1 d . . . H31 H 1.1725 0.8799 0.1587 0.082 Uiso 1 1 calc R . . C32 C 1.3687(3) 0.96015(19) 0.22262(17) 0.0787(6) Uani 1 1 d . . . H32 H 1.3859 1.0020 0.1784 0.094 Uiso 1 1 calc R . . C33 C 1.4713(3) 0.97309(19) 0.29956(18) 0.0779(6) Uani 1 1 d . . . H33 H 1.5565 1.0243 0.3081 0.093 Uiso 1 1 calc R . . C34 C 1.4465(2) 0.90968(18) 0.36336(16) 0.0711(5) Uani 1 1 d . . . H34 H 1.5149 0.9184 0.4158 0.085 Uiso 1 1 calc R . . C35 C 1.3210(2) 0.83332(17) 0.35030(15) 0.0637(5) Uani 1 1 d . . . H35 H 1.3062 0.7889 0.3927 0.076 Uiso 1 1 calc R . . C36 C 1.0246(3) 0.66755(18) 0.15665(13) 0.0777(6) Uani 1 1 d . . . H36A H 1.0474 0.5938 0.1443 0.101 Uiso 1 1 calc R . . H36B H 1.0598 0.7039 0.1098 0.101 Uiso 1 1 calc R . . H36C H 0.9268 0.6554 0.1484 0.101 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0532(10) 0.0532(8) 0.0514(7) 0.0192(7) 0.0150(7) 0.0092(8) N2 0.0756(15) 0.0677(11) 0.0720(11) 0.0295(8) 0.0327(9) 0.0174(10) N3 0.0571(11) 0.0652(10) 0.0611(9) 0.0302(8) 0.0054(7) 0.0011(8) N4 0.0583(12) 0.0627(10) 0.0515(8) 0.0224(7) 0.0090(7) 0.0009(9) N5 0.0572(11) 0.0557(9) 0.0583(8) 0.0228(7) 0.0206(7) 0.0128(8) N6 0.0574(11) 0.0620(10) 0.0650(10) 0.0118(8) 0.0156(8) 0.0176(9) N7 0.0672(12) 0.0586(9) 0.0536(8) 0.0188(7) 0.0203(7) 0.0080(9) N8 0.0760(14) 0.0653(11) 0.0692(10) 0.0287(9) 0.0280(9) 0.0063(10) O1 0.0613(11) 0.0818(10) 0.1031(10) 0.0396(8) 0.0349(8) 0.0202(9) O2 0.1103(15) 0.1621(18) 0.0688(9) 0.0562(11) 0.0333(9) 0.0018(13) O3 0.0874(12) 0.0771(10) 0.0692(9) 0.0040(7) 0.0000(8) 0.0130(9) O4 0.0861(11) 0.0617(8) 0.0780(8) 0.0234(7) 0.0214(7) 0.0268(8) C1 0.0577(13) 0.0521(10) 0.0502(9) 0.0175(8) 0.0165(8) 0.0114(9) C2 0.0712(16) 0.0848(14) 0.0544(11) 0.0235(10) 0.0098(9) -0.0068(12) C3 0.0875(19) 0.0981(17) 0.0531(11) 0.0238(11) 0.0090(10) -0.0004(15) C4 0.0935(19) 0.0911(16) 0.0586(12) 0.0330(11) 0.0263(12) 0.0150(14) C5 0.0820(18) 0.0893(16) 0.0756(13) 0.0384(12) 0.0243(12) -0.0029(13) C6 0.0651(15) 0.0763(13) 0.0649(11) 0.0298(10) 0.0125(9) -0.0009(11) C7 0.0517(12) 0.0546(10) 0.0530(9) 0.0207(8) 0.0149(8) 0.0135(10) C8 0.0575(13) 0.0687(12) 0.0538(10) 0.0242(9) 0.0065(8) 0.0101(10) C9 0.0682(15) 0.0687(12) 0.0513(9) 0.0263(9) 0.0147(9) 0.0161(11) C10 0.0567(13) 0.0599(11) 0.0563(10) 0.0276(8) 0.0221(9) 0.0156(10) C11 0.0509(12) 0.0544(10) 0.0586(10) 0.0245(8) 0.0141(8) 0.0147(10) C12 0.0519(13) 0.0582(11) 0.0615(10) 0.0226(9) 0.0121(8) 0.0087(10) C13 0.0536(15) 0.0695(13) 0.0985(15) 0.0274(11) 0.0129(10) 0.0099(12) C14 0.0624(16) 0.0713(15) 0.1037(16) 0.0174(13) 0.0279(12) -0.0011(13) C15 0.111(2) 0.0544(12) 0.0709(12) 0.0185(10) 0.0319(12) 0.0089(14) C16 0.0924(19) 0.0572(12) 0.0602(11) 0.0168(9) 0.0078(10) 0.0132(12) C17 0.0623(14) 0.0608(12) 0.0568(10) 0.0155(9) 0.0082(8) 0.0129(10) C18 0.0952(19) 0.0947(16) 0.0670(12) 0.0392(12) -0.0074(11) -0.0084(14) C19 0.0487(13) 0.0681(12) 0.0686(11) 0.0288(10) 0.0157(8) 0.0096(10) C20 0.0869(18) 0.0825(15) 0.0781(14) 0.0408(12) 0.0011(11) -0.0021(13) C21 0.112(2) 0.104(2) 0.0714(14) 0.0362(14) -0.0045(13) -0.0109(17) C22 0.102(2) 0.0882(18) 0.0783(15) 0.0196(13) 0.0090(13) -0.0073(15) C23 0.0765(17) 0.0700(14) 0.0924(15) 0.0242(12) 0.0213(12) 0.0079(12) C24 0.0613(15) 0.0726(14) 0.0776(13) 0.0329(11) 0.0222(10) 0.0114(11) C25 0.0571(13) 0.0626(12) 0.0630(10) 0.0254(9) 0.0220(9) 0.0184(10) C26 0.0735(15) 0.0748(14) 0.0590(11) 0.0302(10) 0.0231(9) 0.0225(12) C27 0.0664(14) 0.0764(14) 0.0535(10) 0.0209(9) 0.0167(9) 0.0231(12) C28 0.0541(13) 0.0568(11) 0.0565(10) 0.0159(8) 0.0146(8) 0.0154(10) C29 0.0508(12) 0.0563(11) 0.0563(9) 0.0216(8) 0.0171(8) 0.0163(9) C30 0.0612(13) 0.0482(10) 0.0647(10) 0.0188(8) 0.0262(9) 0.0162(10) C31 0.0754(16) 0.0635(12) 0.0715(12) 0.0296(10) 0.0244(10) 0.0118(12) C32 0.0896(19) 0.0679(13) 0.0873(14) 0.0365(11) 0.0358(13) 0.0130(13) C33 0.0681(16) 0.0655(13) 0.0981(15) 0.0263(12) 0.0295(13) 0.0070(12) C34 0.0583(15) 0.0709(13) 0.0891(13) 0.0273(11) 0.0213(10) 0.0215(12) C35 0.0628(15) 0.0620(12) 0.0805(12) 0.0325(10) 0.0271(10) 0.0258(11) C36 0.0971(18) 0.0681(13) 0.0574(11) 0.0147(9) 0.0244(10) 0.0021(12) _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 1.328(2) . ? N1 C11 1.343(2) . ? N2 O1 1.232(2) . ? N2 O2 1.236(2) . ? N2 C10 1.427(2) . ? N3 C11 1.368(2) . ? N3 C12 1.429(2) . ? N3 C18 1.461(2) . ? N4 C7 1.357(2) . ? N4 C1 1.405(2) . ? N5 C29 1.330(2) . ? N5 C25 1.334(2) . ? N6 O4 1.2370(19) . ? N6 O3 1.240(2) . ? N6 C28 1.421(2) . ? N7 C29 1.382(2) . ? N7 C30 1.422(2) . ? N7 C36 1.466(2) . ? N8 C25 1.350(3) . ? N8 C19 1.407(3) . ? C1 C2 1.377(3) . ? C1 C6 1.379(3) . ? C2 C3 1.391(3) . ? C3 C4 1.355(3) . ? C4 C5 1.375(3) . ? C5 C6 1.374(3) . ? C7 C8 1.412(2) . ? C8 C9 1.351(3) . ? C9 C10 1.389(3) . ? C10 C11 1.412(2) . ? C12 C17 1.378(3) . ? C12 C13 1.380(3) . ? C13 C14 1.382(3) . ? C14 C15 1.374(3) . ? C15 C16 1.369(3) . ? C16 C17 1.371(3) . ? C19 C24 1.384(3) . ? C19 C20 1.384(3) . ? C20 C21 1.382(3) . ? C21 C22 1.353(3) . ? C22 C23 1.371(3) . ? C23 C24 1.369(3) . ? C25 C26 1.414(3) . ? C26 C27 1.343(3) . ? C27 C28 1.397(3) . ? C28 C29 1.416(2) . ? C30 C31 1.387(2) . ? C30 C35 1.391(3) . ? C31 C32 1.376(3) . ? C32 C33 1.379(3) . ? C33 C34 1.370(3) . ? C34 C35 1.374(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 C7 N1 C11 119.02(14) . . ? O1 N2 O2 121.55(17) . . ? O1 N2 C10 120.42(16) . . ? O2 N2 C10 117.92(19) . . ? C11 N3 C12 120.65(14) . . ? C11 N3 C18 118.76(15) . . ? C12 N3 C18 116.65(16) . . ? C7 N4 C1 132.69(17) . . ? C29 N5 C25 119.86(15) . . ? O4 N6 O3 122.27(17) . . ? O4 N6 C28 119.64(15) . . ? O3 N6 C28 118.06(17) . . ? C29 N7 C30 122.92(15) . . ? C29 N7 C36 117.08(16) . . ? C30 N7 C36 117.70(15) . . ? C25 N8 C19 131.05(16) . . ? C2 C1 C6 118.84(16) . . ? C2 C1 N4 125.12(17) . . ? C6 C1 N4 116.03(16) . . ? C1 C2 C3 119.7(2) . . ? C4 C3 C2 121.0(2) . . ? C3 C4 C5 119.50(19) . . ? C6 C5 C4 120.1(2) . . ? C5 C6 C1 120.9(2) . . ? N1 C7 N4 120.28(15) . . ? N1 C7 C8 123.13(16) . . ? N4 C7 C8 116.58(17) . . ? C9 C8 C7 117.43(18) . . ? C8 C9 C10 120.15(16) . . ? C9 C10 C11 118.80(15) . . ? C9 C10 N2 116.35(16) . . ? C11 C10 N2 124.26(17) . . ? N1 C11 N3 115.77(15) . . ? N1 C11 C10 120.28(16) . . ? N3 C11 C10 123.95(16) . . ? C17 C12 C13 119.89(19) . . ? C17 C12 N3 119.98(18) . . ? C13 C12 N3 120.13(18) . . ? C12 C13 C14 119.6(2) . . ? C15 C14 C13 119.9(2) . . ? C16 C15 C14 120.6(2) . . ? C15 C16 C17 119.7(2) . . ? C16 C17 C12 120.4(2) . . ? C24 C19 C20 118.1(2) . . ? C24 C19 N8 117.16(17) . . ? C20 C19 N8 124.73(19) . . ? C21 C20 C19 119.7(2) . . ? C22 C21 C20 121.6(2) . . ? C21 C22 C23 119.0(2) . . ? C24 C23 C22 120.4(2) . . ? C23 C24 C19 121.11(19) . . ? N5 C25 N8 119.22(17) . . ? N5 C25 C26 122.62(19) . . ? N8 C25 C26 118.14(17) . . ? C27 C26 C25 117.67(17) . . ? C26 C27 C28 120.23(17) . . ? C27 C28 C29 118.78(18) . . ? C27 C28 N6 116.99(16) . . ? C29 C28 N6 124.02(16) . . ? N5 C29 N7 115.49(15) . . ? N5 C29 C28 119.98(15) . . ? N7 C29 C28 124.52(17) . . ? C31 C30 C35 118.7(2) . . ? C31 C30 N7 119.77(18) . . ? C35 C30 N7 121.46(16) . . ? C32 C31 C30 119.7(2) . . ? C31 C32 C33 121.2(2) . . ? C34 C33 C32 119.3(2) . . ? C33 C34 C35 120.3(2) . . ? C34 C35 C30 120.74(18) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.141 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.031 # ========================================================= # ========================================================= data_7i _database_code_depnum_ccdc_archive 'CCDC 243007' _chemical_name_systematic ; 2-Anilino-6-(N-tert-bytyloxycarbonylanilino)-3-nitropyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 N4 O4' _chemical_formula_weight 406.44 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5952(16) _cell_length_b 9.790(2) _cell_length_c 13.308(2) _cell_angle_alpha 72.57(2) _cell_angle_beta 83.91(2) _cell_angle_gamma 75.36(2) _cell_volume 1033.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.307 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9641 _exptl_absorpt_correction_T_max 0.9729 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'STOE IPDS system' _diffrn_measurement_method 'Imaging plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11455 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.01 _reflns_number_total 3763 _reflns_number_gt 2720 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPDS software (STOE, 1997)' _computing_cell_refinement 'IPDS software (STOE, 1997)' _computing_data_reduction 'IPDS software (STOE, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Johnson & Burnett, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0640P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3763 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.001 _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 0.38303(16) 0.02863(14) 0.27324(8) 0.0416(3) Uani 1 1 d . . . O2 O 0.4427(2) 0.23938(16) 0.21777(9) 0.0620(5) Uani 1 1 d . . . O3 O 0.48501(15) 0.32955(14) 0.69824(8) 0.0385(3) Uani 1 1 d . . . O4 O 0.28044(14) 0.31405(13) 0.82165(8) 0.0342(3) Uani 1 1 d . . . N1 N 0.27739(16) 0.09250(14) 0.57211(9) 0.0269(3) Uani 1 1 d . . . N2 N 0.40037(19) 0.14224(16) 0.28892(10) 0.0356(3) Uani 1 1 d . . . N3 N 0.26117(18) -0.05463(15) 0.46781(10) 0.0306(3) Uani 1 1 d . . . HN3 H 0.286(3) -0.073(2) 0.4058(16) 0.053(6) Uiso 1 1 d . . . N4 N 0.27824(16) 0.22463(14) 0.68791(9) 0.0273(3) Uani 1 1 d . . . C1 C 0.1559(2) 0.15377(18) 0.74883(11) 0.0284(4) Uani 1 1 d . . . C2 C 0.1993(2) 0.02240(19) 0.82700(11) 0.0359(4) Uani 1 1 d . . . H2 H 0.3093 -0.0212 0.8425 0.043 Uiso 1 1 calc R . . C3 C 0.0796(3) -0.0444(2) 0.88236(13) 0.0441(5) Uani 1 1 d . . . H3 H 0.1076 -0.1341 0.9368 0.053 Uiso 1 1 calc R . . C4 C -0.0800(3) 0.0183(2) 0.85912(13) 0.0454(5) Uani 1 1 d . . . H4 H -0.1613 -0.0283 0.8974 0.055 Uiso 1 1 calc R . . C5 C -0.1217(2) 0.1485(2) 0.78042(13) 0.0419(4) Uani 1 1 d . . . H5 H -0.2314 0.1908 0.7638 0.050 Uiso 1 1 calc R . . C6 C -0.0032(2) 0.21770(19) 0.72548(12) 0.0332(4) Uani 1 1 d . . . H6 H -0.0316 0.3085 0.6722 0.040 Uiso 1 1 calc R . . C7 C 0.3619(2) 0.29413(17) 0.73399(11) 0.0283(4) Uani 1 1 d . . . C8 C 0.3509(2) 0.35591(18) 0.90170(11) 0.0323(4) Uani 1 1 d . . . C9 C 0.4808(3) 0.2253(3) 0.95444(15) 0.0573(6) Uani 1 1 d . . . H9A H 0.4363 0.1378 0.9804 0.069 Uiso 1 1 calc R . . H9B H 0.5210 0.2450 1.0137 0.069 Uiso 1 1 calc R . . H9C H 0.5694 0.2085 0.9035 0.069 Uiso 1 1 calc R . . C10 C 0.4097(3) 0.4936(2) 0.85465(15) 0.0614(7) Uani 1 1 d . . . H10A H 0.5072 0.4728 0.8112 0.074 Uiso 1 1 calc R . . H10B H 0.4341 0.5295 0.9111 0.074 Uiso 1 1 calc R . . H10C H 0.3263 0.5688 0.8108 0.074 Uiso 1 1 calc R . . C11 C 0.2091(3) 0.3799(3) 0.97691(15) 0.0556(6) Uani 1 1 d . . . H11A H 0.1256 0.4641 0.9410 0.067 Uiso 1 1 calc R . . H11B H 0.2439 0.3996 1.0379 0.067 Uiso 1 1 calc R . . H11C H 0.1657 0.2916 1.0006 0.067 Uiso 1 1 calc R . . C12 C 0.31758(19) 0.20754(17) 0.58594(11) 0.0263(3) Uani 1 1 d . . . C13 C 0.3857(2) 0.30780(18) 0.50643(11) 0.0299(4) Uani 1 1 d . . . H13 H 0.4131 0.3892 0.5191 0.036 Uiso 1 1 calc R . . C14 C 0.4106(2) 0.28248(18) 0.40936(11) 0.0308(4) Uani 1 1 d . . . H14 H 0.4556 0.3481 0.3528 0.037 Uiso 1 1 calc R . . C15 C 0.3710(2) 0.16214(17) 0.39262(11) 0.0284(4) Uani 1 1 d . . . C16 C 0.30196(19) 0.06527(17) 0.47765(11) 0.0270(4) Uani 1 1 d . . . C17 C 0.1828(2) -0.15647(17) 0.54002(11) 0.0288(4) Uani 1 1 d . . . C18 C 0.0983(2) -0.13503(18) 0.63132(13) 0.0353(4) Uani 1 1 d . . . H18 H 0.0933 -0.0483 0.6510 0.042 Uiso 1 1 calc R . . C19 C 0.0216(2) -0.24153(19) 0.69318(14) 0.0393(4) Uani 1 1 d . . . H19 H -0.0349 -0.2274 0.7560 0.047 Uiso 1 1 calc R . . C20 C 0.0251(2) -0.36750(19) 0.66593(14) 0.0395(4) Uani 1 1 d . . . H20 H -0.0293 -0.4388 0.7089 0.047 Uiso 1 1 calc R . . C21 C 0.1092(2) -0.38848(19) 0.57512(14) 0.0389(4) Uani 1 1 d . . . H21 H 0.1125 -0.4748 0.5555 0.047 Uiso 1 1 calc R . . C22 C 0.1880(2) -0.28501(18) 0.51302(12) 0.0347(4) Uani 1 1 d . . . H22 H 0.2465 -0.3011 0.4513 0.042 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 0.0544(9) 0.0479(8) 0.0318(6) -0.0192(5) 0.0036(5) -0.0208(6) O2 0.1095(14) 0.0635(9) 0.0246(6) -0.0100(6) 0.0139(7) -0.0502(9) O3 0.0338(8) 0.0587(8) 0.0314(6) -0.0170(5) 0.0043(5) -0.0231(6) O4 0.0347(8) 0.0457(7) 0.0312(5) -0.0200(5) 0.0064(5) -0.0175(5) N1 0.0277(8) 0.0300(7) 0.0236(6) -0.0069(5) -0.0007(5) -0.0087(6) N2 0.0428(10) 0.0431(8) 0.0252(7) -0.0105(6) 0.0008(6) -0.0173(7) N3 0.0378(9) 0.0321(7) 0.0251(6) -0.0093(5) 0.0005(5) -0.0129(6) N4 0.0268(8) 0.0353(7) 0.0238(6) -0.0107(5) 0.0031(5) -0.0131(6) C1 0.0306(10) 0.0362(9) 0.0235(7) -0.0135(6) 0.0041(6) -0.0129(7) C2 0.0400(12) 0.0414(10) 0.0258(7) -0.0074(7) 0.0007(7) -0.0116(8) C3 0.0591(15) 0.0458(11) 0.0282(8) -0.0058(7) 0.0058(8) -0.0222(10) C4 0.0505(14) 0.0588(12) 0.0366(9) -0.0176(8) 0.0179(8) -0.0327(10) C5 0.0307(12) 0.0587(12) 0.0420(9) -0.0202(9) 0.0068(7) -0.0168(9) C6 0.0323(11) 0.0389(9) 0.0307(8) -0.0113(7) 0.0017(6) -0.0121(8) C7 0.0277(10) 0.0342(9) 0.0243(7) -0.0086(6) 0.0012(6) -0.0097(7) C8 0.0401(11) 0.0378(9) 0.0236(7) -0.0124(6) -0.0009(6) -0.0129(8) C9 0.0593(16) 0.0672(14) 0.0369(10) -0.0145(9) -0.0070(9) 0.0022(11) C10 0.099(2) 0.0589(14) 0.0422(10) -0.0157(9) -0.0057(11) -0.0438(13) C11 0.0592(16) 0.0724(15) 0.0467(10) -0.0360(10) 0.0140(9) -0.0193(11) C12 0.0235(10) 0.0315(8) 0.0244(7) -0.0087(6) -0.0019(6) -0.0058(7) C13 0.0335(10) 0.0317(8) 0.0274(7) -0.0087(6) 0.0007(6) -0.0127(7) C14 0.0299(10) 0.0360(9) 0.0259(7) -0.0054(6) 0.0024(6) -0.0121(7) C15 0.0295(10) 0.0345(9) 0.0216(7) -0.0080(6) -0.0014(6) -0.0079(7) C16 0.0254(10) 0.0303(8) 0.0247(7) -0.0067(6) -0.0031(6) -0.0058(7) C17 0.0270(10) 0.0294(8) 0.0300(7) -0.0058(6) -0.0058(6) -0.0076(7) C18 0.0358(11) 0.0311(9) 0.0405(9) -0.0113(7) 0.0019(7) -0.0102(8) C19 0.0389(12) 0.0377(10) 0.0419(9) -0.0107(7) 0.0064(7) -0.0138(8) C20 0.0367(12) 0.0326(9) 0.0476(10) -0.0055(7) 0.0000(8) -0.0131(8) C21 0.0403(12) 0.0298(9) 0.0497(10) -0.0133(7) -0.0066(8) -0.0092(8) C22 0.0367(11) 0.0351(9) 0.0350(8) -0.0128(7) -0.0036(7) -0.0086(8) _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 N2 1.2379(18) . ? O2 N2 1.2228(18) . ? O3 C7 1.2025(19) . ? O4 C7 1.3354(19) . ? O4 C8 1.4811(18) . ? N1 C12 1.325(2) . ? N1 C16 1.3460(19) . ? N2 C15 1.4381(19) . ? N3 C16 1.352(2) . ? N3 C17 1.414(2) . ? N4 C7 1.395(2) . ? N4 C12 1.4121(18) . ? N4 C1 1.448(2) . ? C1 C6 1.378(2) . ? C1 C2 1.383(2) . ? C2 C3 1.386(3) . ? C3 C4 1.380(3) . ? C4 C5 1.378(3) . ? C5 C6 1.387(2) . ? C8 C10 1.495(3) . ? C8 C9 1.510(3) . ? C8 C11 1.510(3) . ? C12 C13 1.401(2) . ? C13 C14 1.372(2) . ? C14 C15 1.389(2) . ? C15 C16 1.425(2) . ? C17 C18 1.392(2) . ? C17 C22 1.398(2) . ? C18 C19 1.385(2) . ? C19 C20 1.378(3) . ? C20 C21 1.383(3) . ? C21 C22 1.376(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 C7 O4 C8 122.29(13) . . ? C12 N1 C16 120.40(13) . . ? O2 N2 O1 121.43(13) . . ? O2 N2 C15 118.51(14) . . ? O1 N2 C15 120.06(13) . . ? C16 N3 C17 130.59(14) . . ? C7 N4 C12 122.68(13) . . ? C7 N4 C1 119.90(12) . . ? C12 N4 C1 117.15(12) . . ? C6 C1 C2 121.07(16) . . ? C6 C1 N4 118.74(14) . . ? C2 C1 N4 120.17(15) . . ? C1 C2 C3 118.80(18) . . ? C4 C3 C2 120.55(17) . . ? C5 C4 C3 120.09(17) . . ? C4 C5 C6 119.96(19) . . ? C1 C6 C5 119.51(16) . . ? O3 C7 O4 127.52(14) . . ? O3 C7 N4 124.46(14) . . ? O4 C7 N4 108.02(14) . . ? O4 C8 C10 111.74(13) . . ? O4 C8 C9 107.42(14) . . ? C10 C8 C9 113.36(19) . . ? O4 C8 C11 101.81(14) . . ? C10 C8 C11 111.18(17) . . ? C9 C8 C11 110.67(15) . . ? N1 C12 C13 123.88(13) . . ? N1 C12 N4 113.63(13) . . ? C13 C12 N4 122.42(14) . . ? C14 C13 C12 116.59(15) . . ? C13 C14 C15 120.88(14) . . ? C14 C15 C16 119.10(13) . . ? C14 C15 N2 117.95(14) . . ? C16 C15 N2 122.95(14) . . ? N1 C16 N3 118.22(14) . . ? N1 C16 C15 119.15(14) . . ? N3 C16 C15 122.62(13) . . ? C18 C17 C22 119.13(15) . . ? C18 C17 N3 125.11(15) . . ? C22 C17 N3 115.71(14) . . ? C19 C18 C17 119.22(16) . . ? C20 C19 C18 121.66(16) . . ? C19 C20 C21 118.98(16) . . ? C22 C21 C20 120.42(16) . . ? C21 C22 C17 120.57(16) . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 0.365 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.039