Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email AKAIFER@MIAMI.EDU _publ_contact_author_name 'Prof Angel E Kaifer' _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_address ; Department of Chemistry University of Miami PO Box 249118 Coral Gables Florida 33124-0431 UNITED STATES OF AMERICA ; _publ_section_title ; A unique hydrogen bonding network in the crystal structure of 3a,6a-diphenylglycoluril ; loop_ _publ_author_name A.Kaifer 'Weizhong Chen' 'Kwangyul Moon' 'Tong Ren' data_compd1 _database_code_depnum_ccdc_archive 'CCDC 211173' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 N5 O2' _chemical_formula_weight 373.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 Pbca 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' '-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 12.4638(12) _cell_length_b 11.6208(12) _cell_length_c 26.636(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3857.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 6288 _cell_measurement_theta_min 2.238 _cell_measurement_theta_max 27.14 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.086 _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 300(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19016 _diffrn_reflns_av_R_equivalents 0.1159 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3402 _reflns_number_gt 1980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0758P)^2^+0.8940P] 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 3402 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1658 _refine_ls_wR_factor_gt 0.1343 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 O2 O 0.06057(14) 0.78034(16) 0.23023(7) 0.0447(5) Uani 1 1 d . . . O1 O -0.30919(14) 1.07137(16) 0.25707(7) 0.0415(5) Uani 1 1 d . . . N4 N -0.08320(16) 0.77841(18) 0.28479(8) 0.0366(6) Uani 1 1 d . . . H4A H -0.0970 0.7060 0.2833 0.044 Uiso 1 1 calc R . . N1 N -0.14421(16) 1.05910(18) 0.29585(8) 0.0349(6) Uani 1 1 d . . . H1A H -0.1303 1.1315 0.2971 0.042 Uiso 1 1 calc R . . N3 N 0.00648(17) 0.93924(18) 0.27469(8) 0.0365(6) Uani 1 1 d . . . H3A H 0.0525 0.9867 0.2624 0.044 Uiso 1 1 calc R . . N2 N -0.23897(16) 0.90144(18) 0.28592(8) 0.0362(6) Uani 1 1 d . . . H2A H -0.2902 0.8575 0.2759 0.043 Uiso 1 1 calc R . . C3 C -0.07126(19) 0.9715(2) 0.31284(9) 0.0308(6) Uani 1 1 d . . . C1 C -0.23731(19) 1.0154(2) 0.27760(9) 0.0325(6) Uani 1 1 d . . . C2 C -0.00002(19) 0.8288(2) 0.26039(9) 0.0336(6) Uani 1 1 d . . . C4 C -0.14608(18) 0.8592(2) 0.31344(9) 0.0303(6) Uani 1 1 d . . . C11 C -0.1774(2) 0.8145(2) 0.36482(10) 0.0360(7) Uani 1 1 d . . . C5 C -0.0165(2) 1.0012(2) 0.36206(10) 0.0372(7) Uani 1 1 d . . . C10 C 0.0712(3) 0.9381(3) 0.37747(13) 0.0613(9) Uani 1 1 d . . . H10A H 0.0979 0.8797 0.3571 0.074 Uiso 1 1 calc R . . C16 C -0.1293(2) 0.7191(3) 0.38552(12) 0.0539(8) Uani 1 1 d . . . H16A H -0.0785 0.6782 0.3672 0.065 Uiso 1 1 calc R . . C6 C -0.0533(3) 1.0877(3) 0.39252(12) 0.0582(9) Uani 1 1 d . . . H6A H -0.1124 1.1310 0.3826 0.070 Uiso 1 1 calc R . . C12 C -0.2523(2) 0.8743(3) 0.39312(11) 0.0519(8) Uani 1 1 d . . . H12A H -0.2862 0.9386 0.3796 0.062 Uiso 1 1 calc R . . C13 C -0.2769(3) 0.8388(4) 0.44131(12) 0.0677(10) Uani 1 1 d . . . H13A H -0.3262 0.8802 0.4602 0.081 Uiso 1 1 calc R . . C14 C -0.2298(3) 0.7442(4) 0.46123(13) 0.0730(11) Uani 1 1 d . . . H14A H -0.2474 0.7205 0.4935 0.088 Uiso 1 1 calc R . . C9 C 0.1195(3) 0.9611(4) 0.42300(16) 0.0794(12) Uani 1 1 d . . . H9A H 0.1780 0.9174 0.4333 0.095 Uiso 1 1 calc R . . C15 C -0.1562(3) 0.6837(4) 0.43380(14) 0.0744(11) Uani 1 1 d . . . H15A H -0.1241 0.6186 0.4475 0.089 Uiso 1 1 calc R . . C7 C -0.0036(4) 1.1114(4) 0.43785(13) 0.0839(13) Uani 1 1 d . . . H7A H -0.0286 1.1710 0.4580 0.101 Uiso 1 1 calc R . . C8 C 0.0824(4) 1.0471(4) 0.45287(14) 0.0810(13) Uani 1 1 d . . . H8A H 0.1154 1.0622 0.4835 0.097 Uiso 1 1 calc R . . N5 N -0.1032(5) 1.0491(8) 0.0555(2) 0.150(3) Uani 1 1 d . . . C21 C -0.1475(5) 1.1165(6) 0.0908(3) 0.133(2) Uani 1 1 d . . . H21A H -0.1720 1.1892 0.0818 0.160 Uiso 1 1 calc R . . C19 C -0.1209(5) 0.9795(8) 0.1517(2) 0.144(3) Uani 1 1 d . . . H19A H -0.1250 0.9540 0.1847 0.173 Uiso 1 1 calc R . . C17 C -0.0706(5) 0.9505(9) 0.0697(3) 0.147(3) Uani 1 1 d . . . H17A H -0.0399 0.9027 0.0456 0.176 Uiso 1 1 calc R . . C20 C -0.1576(5) 1.0820(7) 0.1395(3) 0.127(2) Uani 1 1 d . . . H20A H -0.1895 1.1294 0.1634 0.152 Uiso 1 1 calc R . . C18 C -0.0772(5) 0.9114(7) 0.1161(3) 0.167(3) Uani 1 1 d . . . H18A H -0.0523 0.8383 0.1241 0.201 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 O2 0.0371(11) 0.0362(11) 0.0608(12) -0.0090(10) 0.0124(9) 0.0033(9) O1 0.0344(10) 0.0332(11) 0.0568(12) 0.0004(9) -0.0090(9) 0.0079(9) N4 0.0312(11) 0.0234(12) 0.0553(14) -0.0013(11) 0.0079(10) -0.0029(9) N1 0.0313(12) 0.0232(12) 0.0503(13) -0.0025(10) -0.0060(10) -0.0015(10) N3 0.0318(12) 0.0289(12) 0.0488(13) -0.0054(11) 0.0102(10) -0.0063(10) N2 0.0274(11) 0.0294(13) 0.0518(13) 0.0023(11) -0.0079(10) -0.0046(9) C3 0.0250(13) 0.0270(14) 0.0406(14) -0.0002(12) 0.0010(11) -0.0018(11) C1 0.0287(13) 0.0313(15) 0.0373(14) -0.0044(12) 0.0019(12) 0.0030(12) C2 0.0258(13) 0.0292(15) 0.0459(15) -0.0015(12) -0.0031(12) 0.0021(12) C4 0.0225(12) 0.0262(14) 0.0424(14) -0.0017(12) -0.0008(11) 0.0000(11) C11 0.0314(14) 0.0332(16) 0.0434(15) 0.0021(13) -0.0031(12) -0.0086(12) C5 0.0336(14) 0.0357(15) 0.0423(15) 0.0001(13) -0.0036(12) -0.0102(12) C10 0.053(2) 0.063(2) 0.068(2) -0.0014(18) -0.0242(17) 0.0056(17) C16 0.0532(19) 0.052(2) 0.056(2) 0.0128(17) 0.0000(15) 0.0021(16) C6 0.055(2) 0.066(2) 0.0537(18) -0.0162(18) -0.0059(16) -0.0017(17) C12 0.0515(17) 0.052(2) 0.0523(18) 0.0011(16) 0.0097(15) 0.0017(15) C13 0.071(2) 0.081(3) 0.051(2) -0.004(2) 0.0171(17) -0.007(2) C14 0.087(3) 0.087(3) 0.0447(19) 0.011(2) 0.0011(19) -0.023(2) C9 0.067(2) 0.092(3) 0.080(3) 0.008(2) -0.039(2) -0.007(2) C15 0.085(3) 0.075(3) 0.063(2) 0.027(2) -0.008(2) -0.001(2) C7 0.090(3) 0.102(3) 0.059(2) -0.031(2) -0.014(2) -0.007(3) C8 0.084(3) 0.108(4) 0.052(2) 0.001(2) -0.024(2) -0.036(3) N5 0.099(4) 0.262(9) 0.088(4) 0.038(5) -0.014(3) -0.053(5) C21 0.115(5) 0.138(6) 0.148(6) 0.035(5) -0.039(5) -0.042(4) C19 0.144(6) 0.225(8) 0.064(3) 0.022(4) -0.011(3) 0.054(5) C17 0.088(4) 0.273(11) 0.078(4) -0.006(5) 0.002(3) 0.035(5) C20 0.103(4) 0.175(7) 0.102(5) -0.014(4) -0.018(3) -0.001(4) C18 0.146(6) 0.242(8) 0.114(5) 0.008(6) -0.008(4) 0.095(6) _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 O2 C2 1.238(3) . ? O1 C1 1.235(3) . ? N4 C2 1.356(3) . ? N4 C4 1.442(3) . ? N1 C1 1.357(3) . ? N1 C3 1.438(3) . ? N3 C2 1.342(3) . ? N3 C3 1.454(3) . ? N2 C1 1.343(3) . ? N2 C4 1.455(3) . ? C3 C5 1.518(4) . ? C3 C4 1.604(3) . ? C4 C11 1.515(4) . ? C11 C16 1.376(4) . ? C11 C12 1.386(4) . ? C5 C6 1.371(4) . ? C5 C10 1.379(4) . ? C10 C9 1.380(5) . ? C16 C15 1.391(4) . ? C6 C7 1.385(5) . ? C12 C13 1.383(4) . ? C13 C14 1.354(5) . ? C14 C15 1.367(5) . ? C9 C8 1.359(6) . ? C7 C8 1.366(6) . ? N5 C17 1.273(9) . ? N5 C21 1.343(9) . ? C21 C20 1.363(8) . ? C19 C20 1.317(8) . ? C19 C18 1.349(8) . ? C17 C18 1.320(9) . ? 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 C2 N4 C4 112.8(2) . . ? C1 N1 C3 112.9(2) . . ? C2 N3 C3 113.9(2) . . ? C1 N2 C4 113.8(2) . . ? N1 C3 N3 112.6(2) . . ? N1 C3 C5 113.3(2) . . ? N3 C3 C5 111.3(2) . . ? N1 C3 C4 102.20(18) . . ? N3 C3 C4 100.61(19) . . ? C5 C3 C4 116.0(2) . . ? O1 C1 N2 125.5(2) . . ? O1 C1 N1 125.6(2) . . ? N2 C1 N1 108.8(2) . . ? O2 C2 N3 125.6(2) . . ? O2 C2 N4 125.5(2) . . ? N3 C2 N4 108.8(2) . . ? N4 C4 N2 112.7(2) . . ? N4 C4 C11 113.2(2) . . ? N2 C4 C11 111.42(19) . . ? N4 C4 C3 102.06(18) . . ? N2 C4 C3 100.55(19) . . ? C11 C4 C3 116.0(2) . . ? C16 C11 C12 118.7(3) . . ? C16 C11 C4 121.7(3) . . ? C12 C11 C4 119.5(2) . . ? C6 C5 C10 118.6(3) . . ? C6 C5 C3 121.8(3) . . ? C10 C5 C3 119.5(3) . . ? C5 C10 C9 120.3(4) . . ? C11 C16 C15 120.2(3) . . ? C5 C6 C7 120.8(3) . . ? C13 C12 C11 120.3(3) . . ? C14 C13 C12 120.7(3) . . ? C13 C14 C15 119.9(3) . . ? C8 C9 C10 120.6(4) . . ? C14 C15 C16 120.3(4) . . ? C8 C7 C6 119.8(4) . . ? C9 C8 C7 119.9(3) . . ? C17 N5 C21 116.6(7) . . ? N5 C21 C20 122.2(7) . . ? C20 C19 C18 119.8(6) . . ? N5 C17 C18 124.6(8) . . ? C19 C20 C21 117.9(7) . . ? C17 C18 C19 118.8(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 C3 N3 95.0(2) . . . . ? C1 N1 C3 C5 -137.6(2) . . . . ? C1 N1 C3 C4 -12.1(3) . . . . ? C2 N3 C3 N1 -117.8(2) . . . . ? C2 N3 C3 C5 113.7(2) . . . . ? C2 N3 C3 C4 -9.7(3) . . . . ? C4 N2 C1 O1 -176.6(2) . . . . ? C4 N2 C1 N1 2.8(3) . . . . ? C3 N1 C1 O1 -173.8(2) . . . . ? C3 N1 C1 N2 6.8(3) . . . . ? C3 N3 C2 O2 -176.6(2) . . . . ? C3 N3 C2 N4 2.8(3) . . . . ? C4 N4 C2 O2 -173.9(2) . . . . ? C4 N4 C2 N3 6.8(3) . . . . ? C2 N4 C4 N2 94.8(2) . . . . ? C2 N4 C4 C11 -137.6(2) . . . . ? C2 N4 C4 C3 -12.2(3) . . . . ? C1 N2 C4 N4 -117.6(2) . . . . ? C1 N2 C4 C11 113.8(2) . . . . ? C1 N2 C4 C3 -9.7(3) . . . . ? N1 C3 C4 N4 128.4(2) . . . . ? N3 C3 C4 N4 12.3(2) . . . . ? C5 C3 C4 N4 -107.8(2) . . . . ? N1 C3 C4 N2 12.3(2) . . . . ? N3 C3 C4 N2 -103.9(2) . . . . ? C5 C3 C4 N2 136.0(2) . . . . ? N1 C3 C4 C11 -108.0(2) . . . . ? N3 C3 C4 C11 135.9(2) . . . . ? C5 C3 C4 C11 15.7(3) . . . . ? N4 C4 C11 C16 14.3(3) . . . . ? N2 C4 C11 C16 142.5(3) . . . . ? C3 C4 C11 C16 -103.3(3) . . . . ? N4 C4 C11 C12 -169.4(2) . . . . ? N2 C4 C11 C12 -41.1(3) . . . . ? C3 C4 C11 C12 73.1(3) . . . . ? N1 C3 C5 C6 15.2(4) . . . . ? N3 C3 C5 C6 143.3(3) . . . . ? C4 C3 C5 C6 -102.5(3) . . . . ? N1 C3 C5 C10 -166.3(3) . . . . ? N3 C3 C5 C10 -38.3(4) . . . . ? C4 C3 C5 C10 75.9(3) . . . . ? C6 C5 C10 C9 0.9(5) . . . . ? C3 C5 C10 C9 -177.6(3) . . . . ? C12 C11 C16 C15 0.4(4) . . . . ? C4 C11 C16 C15 176.8(3) . . . . ? C10 C5 C6 C7 0.0(5) . . . . ? C3 C5 C6 C7 178.4(3) . . . . ? C16 C11 C12 C13 0.6(4) . . . . ? C4 C11 C12 C13 -175.9(3) . . . . ? C11 C12 C13 C14 -1.2(5) . . . . ? C12 C13 C14 C15 0.7(6) . . . . ? C5 C10 C9 C8 -0.9(6) . . . . ? C13 C14 C15 C16 0.2(6) . . . . ? C11 C16 C15 C14 -0.8(5) . . . . ? C5 C6 C7 C8 -0.8(6) . . . . ? C10 C9 C8 C7 0.0(6) . . . . ? C6 C7 C8 C9 0.8(6) . . . . ? C17 N5 C21 C20 -0.2(10) . . . . ? C21 N5 C17 C18 -0.1(12) . . . . ? C18 C19 C20 C21 -1.5(11) . . . . ? N5 C21 C20 C19 1.0(10) . . . . ? N5 C17 C18 C19 -0.4(12) . . . . ? C20 C19 C18 C17 1.3(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.252 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.046 data_compd2 _database_code_depnum_ccdc_archive 'CCDC 211174' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 N4 O2' _chemical_formula_weight 350.42 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 8.7863(6) _cell_length_b 8.9879(6) _cell_length_c 12.6434(9) _cell_angle_alpha 96.4150(10) _cell_angle_beta 90.7830(10) _cell_angle_gamma 108.9400(10) _cell_volume 937.16(11) _cell_formula_units_Z 2 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 2889 _cell_measurement_theta_min 2.454 _cell_measurement_theta_max 28.075 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.804350 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ; SADABS, Absorption corrections using Bruker CCD based on the method of Bob Blessing. Acta Cryst. 1995, A51, 33 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5023 _diffrn_reflns_av_R_equivalents 0.0110 _diffrn_reflns_av_sigmaI/netI 0.0274 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3278 _reflns_number_gt 2286 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1030P)^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 3278 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0644 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1556 _refine_ls_wR_factor_gt 0.1485 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 N4 N 0.27278(18) 0.11861(18) 0.63673(12) 0.0531(4) Uani 1 1 d . . . O2 O 0.08781(18) -0.12861(17) 0.64201(12) 0.0726(5) Uani 1 1 d . . . N3 N 0.25937(18) 0.00685(18) 0.78549(12) 0.0523(4) Uani 1 1 d . . . N1 N 0.36725(19) 0.2567(2) 0.89999(12) 0.0562(5) Uani 1 1 d . . . C15 C 0.5324(2) 0.3363(2) 0.66695(14) 0.0425(4) Uani 1 1 d . . . C1 C 0.39346(19) 0.1551(2) 0.81026(13) 0.0422(4) Uani 1 1 d . . . C2 C 0.37421(19) 0.24637(19) 0.71261(13) 0.0412(4) Uani 1 1 d . . . C9 C 0.5556(2) 0.1289(2) 0.81943(14) 0.0468(4) Uani 1 1 d . . . N2 N 0.29131(19) 0.35058(19) 0.76093(14) 0.0565(5) Uani 1 1 d . . . C7 C 0.1951(2) -0.0122(2) 0.68429(15) 0.0499(5) Uani 1 1 d . . . O1 O 0.2465(2) 0.4487(2) 0.92935(15) 0.0920(6) Uani 1 1 d . . . C20 C 0.6007(2) 0.2645(2) 0.58754(16) 0.0571(5) Uani 1 1 d . . . H20A H 0.5445 0.1622 0.5561 0.069 Uiso 1 1 calc R . . C4 C 0.2959(2) 0.3602(2) 0.86875(19) 0.0601(6) Uani 1 1 d . . . C10 C 0.6860(2) 0.2452(3) 0.87609(17) 0.0602(5) Uani 1 1 d . . . H10A H 0.6705 0.3328 0.9150 0.072 Uiso 1 1 calc R . . C16 C 0.6191(2) 0.4889(2) 0.71153(17) 0.0563(5) Uani 1 1 d . . . H16A H 0.5754 0.5399 0.7649 0.068 Uiso 1 1 calc R . . C17 C 0.7701(3) 0.5662(2) 0.6775(2) 0.0673(6) Uani 1 1 d . . . H17A H 0.8271 0.6684 0.7087 0.081 Uiso 1 1 calc R . . C14 C 0.5805(3) -0.0004(3) 0.76242(17) 0.0653(6) Uani 1 1 d . . . H14A H 0.4946 -0.0792 0.7248 0.078 Uiso 1 1 calc R . . C18 C 0.8360(3) 0.4949(3) 0.5993(2) 0.0699(6) Uani 1 1 d . . . H18A H 0.9371 0.5483 0.5764 0.084 Uiso 1 1 calc R . . C19 C 0.7524(3) 0.3434(3) 0.55423(19) 0.0725(6) Uani 1 1 d . . . H19A H 0.7976 0.2934 0.5012 0.087 Uiso 1 1 calc R . . C6 C 0.2104(3) -0.1170(3) 0.8540(2) 0.0780(7) Uani 1 1 d . . . H6A H 0.1201 -0.2024 0.8205 0.117 Uiso 1 1 calc R . . H6B H 0.1803 -0.0754 0.9208 0.117 Uiso 1 1 calc R . . H6C H 0.2983 -0.1554 0.8664 0.117 Uiso 1 1 calc R . . C8 C 0.2124(3) 0.1423(3) 0.53480(18) 0.0884(8) Uani 1 1 d . . . H8A H 0.1488 0.0418 0.4974 0.133 Uiso 1 1 calc R . . H8B H 0.3014 0.1915 0.4933 0.133 Uiso 1 1 calc R . . H8C H 0.1469 0.2093 0.5463 0.133 Uiso 1 1 calc R . . C12 C 0.8612(4) 0.1022(5) 0.8177(3) 0.0979(10) Uani 1 1 d . . . H12A H 0.9634 0.0926 0.8171 0.118 Uiso 1 1 calc R . . C11 C 0.8376(3) 0.2311(4) 0.8748(2) 0.0823(8) Uani 1 1 d . . . H11A H 0.9240 0.3090 0.9126 0.099 Uiso 1 1 calc R . . C13 C 0.7341(4) -0.0132(4) 0.7611(2) 0.0875(9) Uani 1 1 d . . . H13A H 0.7509 -0.0999 0.7220 0.105 Uiso 1 1 calc R . . C5 C 0.2355(4) 0.4567(3) 0.7043(3) 0.1000(10) Uani 1 1 d . . . H5A H 0.1849 0.5138 0.7526 0.150 Uiso 1 1 calc R . . H5B H 0.1593 0.3961 0.6476 0.150 Uiso 1 1 calc R . . H5C H 0.3256 0.5302 0.6751 0.150 Uiso 1 1 calc R . . C3 C 0.3705(3) 0.2276(4) 1.01042(17) 0.0893(8) Uani 1 1 d . . . H3A H 0.3496 0.3118 1.0550 0.134 Uiso 1 1 calc R . . H3B H 0.4745 0.2231 1.0305 0.134 Uiso 1 1 calc R . . H3C H 0.2893 0.1287 1.0188 0.134 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 N4 0.0476(9) 0.0526(9) 0.0442(9) 0.0072(7) -0.0079(7) -0.0036(7) O2 0.0624(9) 0.0575(9) 0.0698(10) -0.0043(7) -0.0038(7) -0.0144(7) N3 0.0474(9) 0.0471(9) 0.0535(10) 0.0130(7) 0.0007(7) 0.0009(7) N1 0.0502(9) 0.0754(11) 0.0410(9) -0.0080(8) 0.0025(7) 0.0226(9) C15 0.0410(10) 0.0391(9) 0.0452(10) 0.0076(7) 0.0006(7) 0.0095(8) C1 0.0372(9) 0.0450(10) 0.0407(9) 0.0020(8) 0.0024(7) 0.0093(8) C2 0.0367(9) 0.0386(9) 0.0448(10) 0.0030(7) -0.0001(7) 0.0081(7) C9 0.0449(10) 0.0559(11) 0.0436(10) 0.0139(8) 0.0085(7) 0.0194(9) N2 0.0476(9) 0.0544(10) 0.0737(12) 0.0094(8) 0.0096(8) 0.0242(8) C7 0.0435(10) 0.0473(11) 0.0484(11) 0.0001(8) 0.0031(8) 0.0021(8) O1 0.0703(11) 0.0881(12) 0.1127(14) -0.0345(10) 0.0173(9) 0.0341(10) C20 0.0614(13) 0.0478(11) 0.0559(12) 0.0043(9) 0.0127(9) 0.0097(9) C4 0.0382(10) 0.0559(12) 0.0773(15) -0.0145(11) 0.0040(9) 0.0105(9) C10 0.0414(11) 0.0767(14) 0.0606(12) 0.0172(10) -0.0005(9) 0.0142(10) C16 0.0514(11) 0.0416(10) 0.0687(13) 0.0019(9) 0.0059(9) 0.0069(9) C17 0.0549(13) 0.0456(11) 0.0902(16) 0.0109(11) 0.0055(11) 0.0001(10) C14 0.0793(15) 0.0699(14) 0.0603(13) 0.0165(11) 0.0139(11) 0.0398(12) C18 0.0516(12) 0.0626(14) 0.0926(17) 0.0267(12) 0.0194(11) 0.0087(11) C19 0.0728(15) 0.0708(15) 0.0762(15) 0.0152(12) 0.0335(12) 0.0235(12) C6 0.0797(16) 0.0640(14) 0.0821(16) 0.0319(12) 0.0066(12) 0.0047(12) C8 0.0816(17) 0.0958(18) 0.0625(15) 0.0232(13) -0.0259(12) -0.0085(14) C12 0.0676(17) 0.148(3) 0.109(2) 0.061(2) 0.0301(16) 0.061(2) C11 0.0457(13) 0.115(2) 0.0911(18) 0.0373(16) 0.0046(11) 0.0245(13) C13 0.107(2) 0.107(2) 0.0843(18) 0.0342(16) 0.0353(16) 0.075(2) C5 0.100(2) 0.0904(19) 0.137(3) 0.0350(18) 0.0090(18) 0.0611(18) C3 0.0896(19) 0.121(2) 0.0447(13) -0.0034(13) 0.0118(11) 0.0220(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 N4 C7 1.363(3) . ? N4 C2 1.449(2) . ? N4 C8 1.451(3) . ? O2 C7 1.221(2) . ? N3 C7 1.361(2) . ? N3 C1 1.463(2) . ? N3 C6 1.446(3) . ? N1 C4 1.367(3) . ? N1 C1 1.444(2) . ? N1 C3 1.450(3) . ? C15 C16 1.385(3) . ? C15 C20 1.382(3) . ? C15 C2 1.521(2) . ? C1 C9 1.523(2) . ? C1 C2 1.593(2) . ? C2 N2 1.452(2) . ? C9 C14 1.379(3) . ? C9 C10 1.397(3) . ? N2 C4 1.356(3) . ? N2 C5 1.452(3) . ? O1 C4 1.227(2) . ? C20 C19 1.387(3) . ? C10 C11 1.379(3) . ? C16 C17 1.382(3) . ? C17 C18 1.356(3) . ? C14 C13 1.391(3) . ? C18 C19 1.373(3) . ? C12 C13 1.376(4) . ? C12 C11 1.371(4) . ? 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 N4 C2 111.89(15) . . ? C7 N4 C8 120.71(17) . . ? C2 N4 C8 123.61(17) . . ? C7 N3 C1 112.59(15) . . ? C7 N3 C6 122.13(17) . . ? C1 N3 C6 124.87(16) . . ? C4 N1 C1 111.77(16) . . ? C4 N1 C3 120.90(18) . . ? C1 N1 C3 125.15(18) . . ? C16 C15 C20 118.09(17) . . ? C16 C15 C2 120.10(16) . . ? C20 C15 C2 121.53(16) . . ? N1 C1 N3 113.22(14) . . ? N1 C1 C9 112.88(14) . . ? N3 C1 C9 112.67(15) . . ? N1 C1 C2 102.07(13) . . ? N3 C1 C2 100.94(12) . . ? C9 C1 C2 114.05(14) . . ? N4 C2 N2 113.42(14) . . ? N4 C2 C15 112.32(14) . . ? N2 C2 C15 112.67(14) . . ? N4 C2 C1 102.00(13) . . ? N2 C2 C1 101.09(13) . . ? C15 C2 C1 114.42(13) . . ? C14 C9 C10 119.08(18) . . ? C14 C9 C1 120.51(18) . . ? C10 C9 C1 120.00(16) . . ? C4 N2 C2 112.64(15) . . ? C4 N2 C5 121.93(19) . . ? C2 N2 C5 124.48(18) . . ? O2 C7 N3 125.74(18) . . ? O2 C7 N4 125.38(18) . . ? N3 C7 N4 108.87(15) . . ? C19 C20 C15 120.66(19) . . ? O1 C4 N2 126.0(2) . . ? O1 C4 N1 125.0(2) . . ? N2 C4 N1 109.00(16) . . ? C11 C10 C9 120.5(2) . . ? C17 C16 C15 120.64(19) . . ? C16 C17 C18 120.8(2) . . ? C9 C14 C13 120.0(2) . . ? C19 C18 C17 119.5(2) . . ? C18 C19 C20 120.2(2) . . ? C13 C12 C11 120.3(2) . . ? C12 C11 C10 120.0(3) . . ? C12 C13 C14 120.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 N3 -91.21(19) . . . . ? C3 N1 C1 N3 72.0(2) . . . . ? C4 N1 C1 C9 139.28(17) . . . . ? C3 N1 C1 C9 -57.5(3) . . . . ? C4 N1 C1 C2 16.42(19) . . . . ? C3 N1 C1 C2 179.63(19) . . . . ? C7 N3 C1 N1 121.37(17) . . . . ? C6 N3 C1 N1 -65.9(2) . . . . ? C7 N3 C1 C9 -109.01(17) . . . . ? C6 N3 C1 C9 63.7(2) . . . . ? C7 N3 C1 C2 13.03(18) . . . . ? C6 N3 C1 C2 -174.21(19) . . . . ? C7 N4 C2 N2 -89.48(19) . . . . ? C8 N4 C2 N2 68.6(2) . . . . ? C7 N4 C2 C15 141.33(16) . . . . ? C8 N4 C2 C15 -60.6(2) . . . . ? C7 N4 C2 C1 18.37(19) . . . . ? C8 N4 C2 C1 176.49(19) . . . . ? C16 C15 C2 N4 158.71(17) . . . . ? C20 C15 C2 N4 -27.4(2) . . . . ? C16 C15 C2 N2 29.1(2) . . . . ? C20 C15 C2 N2 -156.99(16) . . . . ? C16 C15 C2 C1 -85.6(2) . . . . ? C20 C15 C2 C1 88.3(2) . . . . ? N1 C1 C2 N4 -134.71(14) . . . . ? N3 C1 C2 N4 -17.83(16) . . . . ? C9 C1 C2 N4 103.24(16) . . . . ? N1 C1 C2 N2 -17.59(15) . . . . ? N3 C1 C2 N2 99.28(14) . . . . ? C9 C1 C2 N2 -139.65(15) . . . . ? N1 C1 C2 C15 103.77(15) . . . . ? N3 C1 C2 C15 -139.36(14) . . . . ? C9 C1 C2 C15 -18.29(19) . . . . ? N1 C1 C9 C14 158.72(18) . . . . ? N3 C1 C9 C14 28.9(2) . . . . ? C2 C1 C9 C14 -85.4(2) . . . . ? N1 C1 C9 C10 -28.6(2) . . . . ? N3 C1 C9 C10 -158.43(16) . . . . ? C2 C1 C9 C10 87.3(2) . . . . ? N4 C2 N2 C4 122.82(17) . . . . ? C15 C2 N2 C4 -108.17(17) . . . . ? C1 C2 N2 C4 14.41(19) . . . . ? N4 C2 N2 C5 -68.2(3) . . . . ? C15 C2 N2 C5 60.8(2) . . . . ? C1 C2 N2 C5 -176.6(2) . . . . ? C1 N3 C7 O2 176.16(18) . . . . ? C6 N3 C7 O2 3.2(3) . . . . ? C1 N3 C7 N4 -2.4(2) . . . . ? C6 N3 C7 N4 -175.39(19) . . . . ? C2 N4 C7 O2 170.31(18) . . . . ? C8 N4 C7 O2 11.5(3) . . . . ? C2 N4 C7 N3 -11.1(2) . . . . ? C8 N4 C7 N3 -169.97(19) . . . . ? C16 C15 C20 C19 0.4(3) . . . . ? C2 C15 C20 C19 -173.64(18) . . . . ? C2 N2 C4 O1 174.03(19) . . . . ? C5 N2 C4 O1 4.7(3) . . . . ? C2 N2 C4 N1 -5.0(2) . . . . ? C5 N2 C4 N1 -174.3(2) . . . . ? C1 N1 C4 O1 172.62(19) . . . . ? C3 N1 C4 O1 8.6(3) . . . . ? C1 N1 C4 N2 -8.3(2) . . . . ? C3 N1 C4 N2 -172.31(19) . . . . ? C14 C9 C10 C11 0.2(3) . . . . ? C1 C9 C10 C11 -172.55(19) . . . . ? C20 C15 C16 C17 -0.3(3) . . . . ? C2 C15 C16 C17 173.78(18) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C10 C9 C14 C13 -0.5(3) . . . . ? C1 C9 C14 C13 172.2(2) . . . . ? C16 C17 C18 C19 -0.7(4) . . . . ? C17 C18 C19 C20 0.8(4) . . . . ? C15 C20 C19 C18 -0.6(4) . . . . ? C13 C12 C11 C10 0.3(4) . . . . ? C9 C10 C11 C12 -0.1(4) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? C9 C14 C13 C12 0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.199 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.048