Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 1048 _publ_requested_journal 'Green Chemistry' loop_ _publ_author_name 'Scott, Janet' 'Correa, Waldo H.' 'Papadopoulos, Stavroula' 'Radnidge, Peta' 'Roberts, Brett A.' _publ_contact_author_name 'Dr Janet L Scott' _publ_contact_author_address ; Centre for Green Chemistry and School of Chemistry Monash University Victoria 3800 AUSTRALIA ; _publ_contact_author_email 'JANET.SCOTT@SCI.MONASH.EDU.AU' _publ_section_title ; Direct, efficient, solvent-free synthesis of 2-aryl-1,2,3,4 tetrahydroquinazolines ; data_3h _database_code_CSD 177047 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-[(2'-amino-benzylimino)-methyl]-4-bromo-phenol ; _chemical_name_common '2-(5'-bromo-2'-hydroxyphenyl)-1,2,3,4-tetrahydroquinazoline' _chemical_melting_point '147.7-152 deg. C' _chemical_formula_sum 'C14 H13 Br N2 O' _chemical_formula_weight 305.17 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' 'Br' 'Br' -0.2901 2.4595 '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 24.9478(9) _cell_length_b 6.0316(2) _cell_length_c 8.3285(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.3910(10) _cell_angle_gamma 90.00 _cell_volume 1239.82(8) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description rhombs _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 3.304 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ? _diffrn_ambient_temperature 123(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 Kappa CCD' _diffrn_measurement_method 'phi + omega scans' _diffrn_reflns_number 5161 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 26.39 _reflns_number_total 2494 _reflns_number_gt 2155 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Xseed' _computing_publication_material 'Ciftab' _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^)+(0.0594P)^2^+1.0368P] 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_number_reflns 2494 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1060 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 Br1 Br 0.468686(12) 0.31148(5) 0.85452(4) 0.02452(15) Uani 1 1 d . . . O1 O 0.28166(9) -0.2629(4) 0.5586(3) 0.0226(5) Uani 1 1 d . . . C3' C 0.36067(13) -0.2110(5) 0.7527(4) 0.0200(7) Uani 1 1 d . . . H3' H 0.3566 -0.3569 0.7920 0.024 Uiso 1 1 calc R . . C7' C 0.28824(13) 0.1827(5) 0.4434(4) 0.0173(6) Uani 1 1 d . . . H7' H 0.2910 0.3338 0.4135 0.021 Uiso 1 1 calc R . . C6' C 0.37218(12) 0.2171(5) 0.6403(4) 0.0180(6) Uani 1 1 d . . . H6' H 0.3764 0.3637 0.6023 0.022 Uiso 1 1 calc R . . N1 N 0.24974(10) 0.0639(5) 0.3722(3) 0.0194(6) Uani 1 1 d . . . C7 C 0.20869(13) 0.1676(6) 0.2514(4) 0.0228(7) Uani 1 1 d . . . H7A H 0.2144 0.1219 0.1410 0.027 Uiso 1 1 calc R . . H7B H 0.2121 0.3310 0.2587 0.027 Uiso 1 1 calc R . . C6 C 0.12163(14) 0.2411(6) 0.3620(4) 0.0245(7) Uani 1 1 d . . . H6 H 0.1357 0.3823 0.3966 0.029 Uiso 1 1 calc R . . C1' C 0.32826(12) 0.0879(5) 0.5708(3) 0.0163(6) Uani 1 1 d . . . N2 N 0.16242(13) -0.2637(6) 0.1567(4) 0.0315(7) Uani 1 1 d . . . C4' C 0.40389(12) -0.0829(5) 0.8214(4) 0.0202(7) Uani 1 1 d . . . H4' H 0.4296 -0.1403 0.9066 0.024 Uiso 1 1 calc R . . C5 C 0.07043(15) 0.1807(6) 0.3925(4) 0.0280(8) Uani 1 1 d . . . H5 H 0.0500 0.2774 0.4503 0.034 Uiso 1 1 calc R . . C2' C 0.32299(12) -0.1294(6) 0.6267(4) 0.0185(6) Uani 1 1 d . . . C5' C 0.40929(12) 0.1326(5) 0.7637(4) 0.0185(6) Uani 1 1 d . . . C2 C 0.13171(13) -0.1107(6) 0.2299(4) 0.0225(7) Uani 1 1 d . . . C3 C 0.07986(14) -0.1668(6) 0.2574(4) 0.0268(8) Uani 1 1 d . . . H3 H 0.0650 -0.3060 0.2210 0.032 Uiso 1 1 calc R . . C1 C 0.15295(12) 0.0984(6) 0.2812(4) 0.0202(7) Uani 1 1 d . . . C4 C 0.04956(13) -0.0226(6) 0.3374(4) 0.0293(8) Uani 1 1 d . . . H4 H 0.0141 -0.0636 0.3545 0.035 Uiso 1 1 calc R . . H1N H 0.1929 -0.2116 0.1264 0.062(17) Uiso 1 1 d R . . H2N H 0.1397(18) -0.366(8) 0.086(5) 0.039(11) Uiso 1 1 d . . . H1O H 0.260(2) -0.176(9) 0.461(7) 0.068(17) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0253(2) 0.0227(2) 0.0242(2) -0.00359(13) -0.00129(14) -0.00453(12) O1 0.0264(12) 0.0167(11) 0.0241(12) 0.0011(10) 0.0017(10) -0.0059(10) C3' 0.0292(17) 0.0127(16) 0.0191(15) 0.0023(13) 0.0072(13) 0.0024(12) C7' 0.0223(15) 0.0140(16) 0.0164(14) -0.0003(12) 0.0057(12) -0.0011(12) C6' 0.0244(16) 0.0151(15) 0.0155(14) -0.0010(13) 0.0062(12) -0.0009(12) N1 0.0208(13) 0.0192(14) 0.0182(12) 0.0012(11) 0.0027(10) 0.0010(11) C7 0.0246(16) 0.0195(17) 0.0234(16) 0.0015(13) 0.0004(13) 0.0001(13) C6 0.0300(17) 0.0220(16) 0.0196(16) -0.0003(15) -0.0025(13) 0.0025(15) C1' 0.0213(14) 0.0150(15) 0.0130(13) -0.0015(13) 0.0041(11) 0.0043(12) N2 0.0332(17) 0.0247(15) 0.0376(18) -0.0066(15) 0.0085(14) 0.0005(14) C4' 0.0254(15) 0.0178(16) 0.0172(14) -0.0022(13) 0.0027(12) 0.0044(13) C5 0.0290(18) 0.031(2) 0.0244(17) -0.0012(15) 0.0043(14) 0.0072(14) C2' 0.0221(15) 0.0174(15) 0.0166(14) -0.0035(13) 0.0048(12) -0.0025(12) C5' 0.0213(15) 0.0165(15) 0.0178(14) -0.0031(13) 0.0028(12) -0.0003(12) C2 0.0267(16) 0.0225(17) 0.0170(15) -0.0004(14) -0.0006(12) 0.0031(14) C3 0.0289(18) 0.0211(18) 0.0289(18) 0.0001(15) -0.0006(14) -0.0023(13) C1 0.0244(15) 0.0207(17) 0.0137(14) 0.0031(13) -0.0032(12) 0.0016(13) C4 0.0190(15) 0.036(2) 0.0325(18) 0.0045(17) 0.0031(14) 0.0016(14) _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 Br1 C5' 1.899(3) . ? O1 C2' 1.365(4) . ? C3' C4' 1.381(5) . ? C3' C2' 1.393(5) . ? C7' N1 1.273(4) . ? C7' C1' 1.463(4) . ? C6' C5' 1.377(4) . ? C6' C1' 1.400(4) . ? N1 C7 1.467(4) . ? C7 C1 1.507(5) . ? C6 C5 1.387(5) . ? C6 C1 1.399(5) . ? C1' C2' 1.403(5) . ? N2 C2 1.395(5) . ? C4' C5' 1.399(5) . ? C5 C4 1.384(5) . ? C2 C3 1.388(5) . ? C2 C1 1.410(5) . ? C3 C4 1.385(5) . ? 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 C4' C3' C2' 121.0(3) . . ? N1 C7' C1' 120.4(3) . . ? C5' C6' C1' 120.2(3) . . ? C7' N1 C7 118.9(3) . . ? N1 C7 C1 109.7(3) . . ? C5 C6 C1 121.4(3) . . ? C6' C1' C2' 119.2(3) . . ? C6' C1' C7' 119.5(3) . . ? C2' C1' C7' 121.2(3) . . ? C3' C4' C5' 119.1(3) . . ? C4 C5 C6 118.9(3) . . ? O1 C2' C3' 119.4(3) . . ? O1 C2' C1' 121.0(3) . . ? C3' C2' C1' 119.6(3) . . ? C6' C5' C4' 120.8(3) . . ? C6' C5' Br1 119.2(2) . . ? C4' C5' Br1 120.0(2) . . ? C3 C2 N2 119.7(3) . . ? C3 C2 C1 119.1(3) . . ? N2 C2 C1 121.2(3) . . ? C4 C3 C2 120.9(3) . . ? C6 C1 C2 119.0(3) . . ? C6 C1 C7 120.2(3) . . ? C2 C1 C7 120.9(3) . . ? C5 C4 C3 120.7(3) . . ? 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' C7' N1 C7 176.7(3) . . . . ? C7' N1 C7 C1 -133.5(3) . . . . ? C5' C6' C1' C2' -0.9(4) . . . . ? C5' C6' C1' C7' 178.1(3) . . . . ? N1 C7' C1' C6' 176.0(3) . . . . ? N1 C7' C1' C2' -5.1(5) . . . . ? C2' C3' C4' C5' 0.6(5) . . . . ? C1 C6 C5 C4 -1.9(5) . . . . ? C4' C3' C2' O1 178.1(3) . . . . ? C4' C3' C2' C1' -1.4(5) . . . . ? C6' C1' C2' O1 -178.0(3) . . . . ? C7' C1' C2' O1 3.1(4) . . . . ? C6' C1' C2' C3' 1.6(4) . . . . ? C7' C1' C2' C3' -177.4(3) . . . . ? C1' C6' C5' C4' 0.1(5) . . . . ? C1' C6' C5' Br1 179.6(2) . . . . ? C3' C4' C5' C6' 0.1(5) . . . . ? C3' C4' C5' Br1 -179.4(2) . . . . ? N2 C2 C3 C4 176.6(3) . . . . ? C1 C2 C3 C4 -1.4(5) . . . . ? C5 C6 C1 C2 0.1(5) . . . . ? C5 C6 C1 C7 -179.3(3) . . . . ? C3 C2 C1 C6 1.5(4) . . . . ? N2 C2 C1 C6 -176.5(3) . . . . ? C3 C2 C1 C7 -179.0(3) . . . . ? N2 C2 C1 C7 3.0(5) . . . . ? N1 C7 C1 C6 100.3(3) . . . . ? N1 C7 C1 C2 -79.1(4) . . . . ? C6 C5 C4 C3 2.0(5) . . . . ? C2 C3 C4 C5 -0.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.652 _refine_diff_density_min -1.033 _refine_diff_density_rms 0.113 data_4a _database_code_CSD 177048 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-phenyl-1,2,3,4-tetrahydroquinazoline ; _chemical_name_common 2-phenyl-1,2,3,4-tetrahydroquinazoline _chemical_melting_point '98.1-101.5 deg. C' _chemical_formula_sum 'C14 H14 N2' _chemical_formula_weight 210.27 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' _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 9.4360(5) _cell_length_b 10.4454(5) _cell_length_c 12.0165(8) _cell_angle_alpha 99.837(2) _cell_angle_beta 98.858(2) _cell_angle_gamma 101.754(4) _cell_volume 1120.40(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description prisms _exptl_crystal_colour beige _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 Kappa CCD' _diffrn_measurement_method '\phi + w scans' _diffrn_reflns_number 6463 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0926 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4502 _reflns_number_gt 2658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Xseed' _computing_publication_material 'Ciftab' _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^)+(0.1415P)^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_number_reflns 4502 _refine_ls_number_parameters 297 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1408 _refine_ls_R_factor_gt 0.0822 _refine_ls_wR_factor_ref 0.2397 _refine_ls_wR_factor_gt 0.2063 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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 N11 N 0.2475(3) 0.5094(2) 0.9274(2) 0.0253(6) Uani 1 1 d D . . C15 C 0.1406(3) 0.2931(3) 0.6365(2) 0.0250(7) Uani 1 1 d . . . H15 H 0.1157 0.2008 0.6011 0.030 Uiso 1 1 calc R . . C18 C 0.2151(3) 0.5621(3) 0.7382(2) 0.0237(7) Uani 1 1 d . . . H18 H 0.2415 0.6547 0.7726 0.028 Uiso 1 1 calc R . . C110 C 0.1744(3) 0.3306(3) 0.7560(2) 0.0233(6) Uani 1 1 d . . . C16' C 0.1480(3) 0.4691(3) 1.1886(3) 0.0260(7) Uani 1 1 d . . . H16' H 0.0460 0.4368 1.1552 0.031 Uiso 1 1 calc R . . C19 C 0.2113(3) 0.4682(3) 0.8075(2) 0.0204(6) Uani 1 1 d . . . C13' C 0.4445(3) 0.5598(3) 1.2877(3) 0.0298(7) Uani 1 1 d . . . H13' H 0.5464 0.5893 1.3217 0.036 Uiso 1 1 calc R . . C11' C 0.2516(3) 0.4639(3) 1.1198(2) 0.0253(7) Uani 1 1 d . . . N13 N 0.2456(3) 0.2873(3) 0.9544(2) 0.0431(8) Uani 1 1 d . . . C15' C 0.1907(3) 0.5206(3) 1.3055(3) 0.0294(7) Uani 1 1 d . . . H15' H 0.1180 0.5248 1.3518 0.035 Uiso 1 1 calc R . . C14' C 0.3385(3) 0.5662(3) 1.3556(3) 0.0283(7) Uani 1 1 d . . . H14' H 0.3676 0.6018 1.4361 0.034 Uiso 1 1 calc R . . C14 C 0.1786(4) 0.2290(3) 0.8312(3) 0.0335(8) Uani 1 1 d . . . H14A H 0.0765 0.1776 0.8261 0.040 Uiso 1 1 calc R . . H14B H 0.2351 0.1655 0.8007 0.040 Uiso 1 1 calc R . . C12' C 0.4006(3) 0.5098(3) 1.1697(3) 0.0286(7) Uani 1 1 d . . . H12' H 0.4728 0.5070 1.1228 0.034 Uiso 1 1 calc R . . C17 C 0.1810(3) 0.5219(3) 0.6199(2) 0.0245(7) Uani 1 1 d . . . H17 H 0.1838 0.5872 0.5736 0.029 Uiso 1 1 calc R . . C16 C 0.1423(3) 0.3866(3) 0.5676(2) 0.0254(7) Uani 1 1 d . . . H16 H 0.1175 0.3591 0.4861 0.030 Uiso 1 1 calc R . . C12 C 0.2009(4) 0.4086(3) 0.9916(3) 0.0335(8) Uani 1 1 d . . . H12 H 0.0906 0.3859 0.9756 0.040 Uiso 1 1 calc R . . N21 N 0.2824(3) 0.0450(2) 0.0762(2) 0.0262(6) Uani 1 1 d D . . C29 C 0.3051(3) 0.0611(3) 0.1961(2) 0.0202(6) Uani 1 1 d . . . C21' C 0.1936(3) -0.0920(3) -0.1174(2) 0.0254(7) Uani 1 1 d . . . C26' C 0.0560(3) -0.1184(3) -0.1872(3) 0.0271(7) Uani 1 1 d . . . H26' H -0.0296 -0.1341 -0.1543 0.033 Uiso 1 1 calc R . . C23' C 0.3038(3) -0.0779(3) -0.2855(3) 0.0293(7) Uani 1 1 d . . . H23' H 0.3889 -0.0651 -0.3193 0.035 Uiso 1 1 calc R . . C25' C 0.0408(3) -0.1222(3) -0.3033(3) 0.0284(7) Uani 1 1 d . . . H25' H -0.0548 -0.1381 -0.3494 0.034 Uiso 1 1 calc R . . C210 C 0.2948(3) -0.0512(3) 0.2462(2) 0.0233(6) Uani 1 1 d . . . C22' C 0.3185(3) -0.0713(3) -0.1675(3) 0.0296(7) Uani 1 1 d . . . H22' H 0.4141 -0.0526 -0.1207 0.036 Uiso 1 1 calc R . . C28 C 0.3433(3) 0.1890(3) 0.2656(2) 0.0243(7) Uani 1 1 d . . . H28 H 0.3527 0.2652 0.2315 0.029 Uiso 1 1 calc R . . N23 N 0.2670(3) -0.1900(3) 0.0482(2) 0.0449(8) Uani 1 1 d . . . C26 C 0.3567(3) 0.0946(3) 0.4356(3) 0.0283(7) Uani 1 1 d . . . H26 H 0.3740 0.1060 0.5170 0.034 Uiso 1 1 calc R . . C25 C 0.3204(3) -0.0319(3) 0.3660(3) 0.0278(7) Uani 1 1 d . . . H25 H 0.3128 -0.1076 0.4007 0.033 Uiso 1 1 calc R . . C24' C 0.1638(3) -0.1033(3) -0.3538(3) 0.0271(7) Uani 1 1 d . . . H24' H 0.1527 -0.1075 -0.4344 0.033 Uiso 1 1 calc R . . C27 C 0.3673(3) 0.2051(3) 0.3838(3) 0.0273(7) Uani 1 1 d . . . H27 H 0.3915 0.2925 0.4306 0.033 Uiso 1 1 calc R . . C24 C 0.2614(4) -0.1898(3) 0.1702(3) 0.0346(8) Uani 1 1 d . . . H24A H 0.3332 -0.2386 0.2005 0.042 Uiso 1 1 calc R . . H24B H 0.1618 -0.2390 0.1750 0.042 Uiso 1 1 calc R . . C22 C 0.2054(4) -0.0864(3) 0.0107(3) 0.0344(8) Uani 1 1 d . . . H22 H 0.1024 -0.1017 0.0253 0.041 Uiso 1 1 calc R . . H11N H 0.250(3) 0.604(2) 0.960(3) 0.041(9) Uiso 1 1 d D . . H21N H 0.266(4) 0.124(3) 0.046(3) 0.063(12) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0400(15) 0.0201(13) 0.0174(13) 0.0029(10) 0.0074(10) 0.0104(11) C15 0.0326(16) 0.0216(15) 0.0198(16) -0.0013(12) 0.0064(12) 0.0080(12) C18 0.0314(16) 0.0187(14) 0.0203(16) -0.0001(12) 0.0048(12) 0.0081(12) C110 0.0299(16) 0.0220(15) 0.0221(16) 0.0061(12) 0.0095(12) 0.0111(12) C16' 0.0260(15) 0.0252(15) 0.0271(17) 0.0064(13) 0.0028(12) 0.0075(12) C19 0.0216(14) 0.0248(15) 0.0175(15) 0.0041(12) 0.0068(11) 0.0095(11) C13' 0.0252(16) 0.0321(17) 0.0331(19) 0.0104(14) 0.0043(13) 0.0068(13) C11' 0.0344(17) 0.0199(15) 0.0232(16) 0.0063(12) 0.0073(13) 0.0072(12) N13 0.084(2) 0.0225(14) 0.0237(15) 0.0023(12) 0.0092(14) 0.0175(14) C15' 0.0289(16) 0.0345(17) 0.0267(17) 0.0046(14) 0.0097(13) 0.0103(13) C14' 0.0304(16) 0.0358(18) 0.0163(15) 0.0037(13) 0.0021(12) 0.0057(13) C14 0.056(2) 0.0190(15) 0.0247(18) 0.0014(13) 0.0082(15) 0.0099(14) C12' 0.0361(17) 0.0258(16) 0.0304(18) 0.0094(13) 0.0182(14) 0.0103(13) C17 0.0276(16) 0.0264(15) 0.0221(16) 0.0060(12) 0.0049(12) 0.0120(12) C16 0.0282(16) 0.0315(17) 0.0170(15) 0.0032(13) 0.0051(12) 0.0096(12) C12 0.0485(19) 0.0244(16) 0.0276(18) 0.0052(14) 0.0105(14) 0.0063(14) N21 0.0365(14) 0.0214(13) 0.0201(13) 0.0023(10) 0.0029(10) 0.0093(11) C29 0.0209(14) 0.0223(14) 0.0182(15) 0.0029(11) 0.0022(11) 0.0093(11) C21' 0.0401(18) 0.0140(14) 0.0200(16) -0.0001(11) 0.0044(13) 0.0062(12) C26' 0.0300(16) 0.0229(15) 0.0303(18) 0.0055(13) 0.0118(13) 0.0059(12) C23' 0.0251(16) 0.0274(16) 0.0361(19) 0.0035(14) 0.0118(13) 0.0061(12) C25' 0.0276(16) 0.0296(16) 0.0270(17) 0.0046(13) 0.0037(13) 0.0072(12) C210 0.0244(15) 0.0227(15) 0.0228(16) 0.0037(12) 0.0020(11) 0.0087(11) C22' 0.0279(16) 0.0231(15) 0.036(2) 0.0060(13) 0.0000(13) 0.0069(12) C28 0.0284(16) 0.0239(15) 0.0229(16) 0.0058(12) 0.0067(12) 0.0097(12) N23 0.089(2) 0.0218(14) 0.0240(15) 0.0033(12) 0.0067(14) 0.0170(14) C26 0.0271(16) 0.0397(18) 0.0191(16) 0.0039(13) 0.0038(12) 0.0126(13) C25 0.0301(16) 0.0314(17) 0.0261(17) 0.0120(13) 0.0070(12) 0.0108(13) C24' 0.0367(17) 0.0249(16) 0.0182(16) 0.0014(12) 0.0061(12) 0.0059(13) C27 0.0261(16) 0.0260(16) 0.0273(17) -0.0028(13) 0.0020(12) 0.0101(12) C24 0.054(2) 0.0224(16) 0.0261(18) 0.0056(13) 0.0021(15) 0.0098(14) C22 0.054(2) 0.0214(16) 0.0241(18) 0.0049(13) 0.0033(14) 0.0033(14) _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 N11 C19 1.398(3) . ? N11 C12 1.446(4) . ? C15 C16 1.383(4) . ? C15 C110 1.391(4) . ? C18 C17 1.378(4) . ? C18 C19 1.389(4) . ? C110 C19 1.413(4) . ? C110 C14 1.509(4) . ? C16' C11' 1.377(4) . ? C16' C15' 1.380(4) . ? C13' C14' 1.390(4) . ? C13' C12' 1.390(4) . ? C11' C12' 1.391(4) . ? C11' C12 1.514(4) . ? N13 C12 1.437(4) . ? N13 C14 1.485(4) . ? C15' C14' 1.381(4) . ? C17 C16 1.393(4) . ? N21 C29 1.399(4) . ? N21 C22 1.442(4) . ? C29 C28 1.394(4) . ? C29 C210 1.400(4) . ? C21' C26' 1.380(4) . ? C21' C22' 1.399(4) . ? C21' C22 1.516(4) . ? C26' C25' 1.374(4) . ? C23' C22' 1.391(4) . ? C23' C24' 1.392(4) . ? C25' C24' 1.385(4) . ? C210 C25 1.395(4) . ? C210 C24 1.517(4) . ? C28 C27 1.378(4) . ? N23 C22 1.432(4) . ? N23 C24 1.475(4) . ? C26 C25 1.383(4) . ? C26 C27 1.395(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 C19 N11 C12 115.8(2) . . ? C16 C15 C110 121.8(3) . . ? C17 C18 C19 120.6(3) . . ? C15 C110 C19 118.5(3) . . ? C15 C110 C14 121.9(2) . . ? C19 C110 C14 119.5(3) . . ? C11' C16' C15' 120.7(3) . . ? C18 C19 N11 120.4(2) . . ? C18 C19 C110 119.6(3) . . ? N11 C19 C110 120.0(3) . . ? C14' C13' C12' 119.7(3) . . ? C16' C11' C12' 119.2(3) . . ? C16' C11' C12 119.4(3) . . ? C12' C11' C12 121.4(3) . . ? C12 N13 C14 110.3(2) . . ? C16' C15' C14' 120.4(3) . . ? C15' C14' C13' 119.6(3) . . ? N13 C14 C110 114.4(2) . . ? C13' C12' C11' 120.4(3) . . ? C18 C17 C16 120.7(3) . . ? C15 C16 C17 118.8(3) . . ? N13 C12 N11 112.3(3) . . ? N13 C12 C11' 112.6(3) . . ? N11 C12 C11' 110.7(2) . . ? C29 N21 C22 116.1(2) . . ? C28 C29 N21 120.0(3) . . ? C28 C29 C210 120.1(3) . . ? N21 C29 C210 119.9(2) . . ? C26' C21' C22' 118.6(3) . . ? C26' C21' C22 119.4(3) . . ? C22' C21' C22 121.9(3) . . ? C25' C26' C21' 121.2(3) . . ? C22' C23' C24' 119.7(3) . . ? C26' C25' C24' 120.5(3) . . ? C25 C210 C29 118.6(3) . . ? C25 C210 C24 121.5(3) . . ? C29 C210 C24 119.8(3) . . ? C23' C22' C21' 120.5(3) . . ? C27 C28 C29 120.1(3) . . ? C22 N23 C24 111.0(2) . . ? C25 C26 C27 118.7(3) . . ? C26 C25 C210 121.7(3) . . ? C25' C24' C23' 119.4(3) . . ? C28 C27 C26 120.8(3) . . ? N23 C24 C210 114.1(2) . . ? N23 C22 N21 112.6(3) . . ? N23 C22 C21' 112.9(2) . . ? N21 C22 C21' 110.8(2) . . ? _diffrn_measured_fraction_theta_max 0.810 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.810 _refine_diff_density_max 0.572 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.076 data_4b _database_code_CSD 177049 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(2'-nitrophenyl)-1,2,3,4-tetrahydroquinazoline ; _chemical_name_common '2-(2'-nitrophenyl)-1,2,3,4-tetrahydroquinazoline' _chemical_melting_point '117.6-119.2 Deg. C' _chemical_formula_moiety 'C14 H13 N3 O2' _chemical_formula_sum 'C14 H13 N3 O2' _chemical_formula_weight 255.27 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 12.1392(2) _cell_length_b 7.7897(2) _cell_length_c 13.5753(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.140(8) _cell_angle_gamma 90.00 _cell_volume 1197.30(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description needles _exptl_crystal_colour 'light orange' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 Kappa CCD' _diffrn_measurement_method 'phi + w scans' _diffrn_reflns_number 9206 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 28.30 _reflns_number_total 2769 _reflns_number_gt 2184 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Xseed' _computing_publication_material 'Ciftab' _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^)+(0.0961P)^2^+0.0702P] 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_number_reflns 2769 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1524 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 0.19022(10) 0.85021(16) 0.10337(9) 0.0315(3) Uani 1 1 d . . . N1 N 0.30096(11) 0.36801(17) 0.01808(10) 0.0214(3) Uani 1 1 d . . . N1' N 0.13792(11) 0.87534(16) 0.00853(10) 0.0229(3) Uani 1 1 d . . . C6' C 0.06107(13) 0.44055(19) -0.11251(11) 0.0201(3) Uani 1 1 d . . . H6' H 0.0934 0.3286 -0.1086 0.024 Uiso 1 1 calc R . . O2' O 0.13086(11) 1.01721(15) -0.03325(10) 0.0345(3) Uani 1 1 d . . . C8 C 0.37301(12) 0.14733(19) -0.06968(12) 0.0205(3) Uani 1 1 d . . . H8 H 0.3661 0.0638 -0.0213 0.025 Uiso 1 1 calc R . . N3 N 0.32777(11) 0.66747(16) -0.01247(11) 0.0224(3) Uani 1 1 d . . . C9 C 0.34123(11) 0.31842(18) -0.06130(11) 0.0168(3) Uani 1 1 d . . . C5' C -0.05328(13) 0.4717(2) -0.18229(12) 0.0245(4) Uani 1 1 d . . . H5' H -0.0983 0.3807 -0.2244 0.029 Uiso 1 1 calc R . . C2' C 0.07553(12) 0.73152(19) -0.05824(11) 0.0182(3) Uani 1 1 d . . . C1' C 0.12928(12) 0.56983(19) -0.04829(11) 0.0170(3) Uani 1 1 d . . . C6 C 0.42427(12) 0.2199(2) -0.22060(12) 0.0222(3) Uani 1 1 d . . . H6 H 0.4511 0.1864 -0.2754 0.027 Uiso 1 1 calc R . . C5 C 0.39423(12) 0.3891(2) -0.21132(12) 0.0205(3) Uani 1 1 d . . . H5 H 0.4008 0.4715 -0.2605 0.025 Uiso 1 1 calc R . . C4 C 0.32698(13) 0.62672(19) -0.11838(13) 0.0225(4) Uani 1 1 d . . . H4A H 0.3856 0.7005 -0.1332 0.027 Uiso 1 1 calc R . . H4B H 0.2482 0.6547 -0.1710 0.027 Uiso 1 1 calc R . . C3' C -0.03659(12) 0.7661(2) -0.12858(12) 0.0229(4) Uani 1 1 d . . . H3' H -0.0686 0.8785 -0.1343 0.028 Uiso 1 1 calc R . . C10 C 0.35468(12) 0.44140(18) -0.13191(11) 0.0178(3) Uani 1 1 d . . . C7 C 0.41444(12) 0.1000(2) -0.14839(12) 0.0226(4) Uani 1 1 d . . . H7 H 0.4364 -0.0159 -0.1531 0.027 Uiso 1 1 calc R . . C4' C -0.10192(13) 0.6337(2) -0.19095(12) 0.0253(4) Uani 1 1 d . . . H4' H -0.1797 0.6545 -0.2394 0.030 Uiso 1 1 calc R . . C2 C 0.25946(13) 0.54257(19) 0.02138(11) 0.0198(3) Uani 1 1 d . . . H2 H 0.2688 0.5693 0.0960 0.024 Uiso 1 1 calc R . . H1N H 0.2736(17) 0.288(3) 0.0481(16) 0.039(6) Uiso 1 1 d . . . H2N H 0.4047(15) 0.665(2) 0.0323(14) 0.023(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1' 0.0312(7) 0.0330(7) 0.0257(6) -0.0111(5) 0.0047(5) -0.0012(5) N1 0.0226(7) 0.0201(7) 0.0223(6) 0.0054(5) 0.0090(5) 0.0035(5) N1' 0.0225(7) 0.0206(7) 0.0285(7) -0.0052(5) 0.0126(6) -0.0008(5) C6' 0.0214(8) 0.0191(7) 0.0209(7) -0.0010(6) 0.0090(6) -0.0025(6) O2' 0.0454(8) 0.0186(6) 0.0447(8) -0.0013(5) 0.0223(6) -0.0036(5) C8 0.0137(7) 0.0176(7) 0.0259(8) 0.0058(6) 0.0021(6) 0.0011(5) N3 0.0143(7) 0.0210(7) 0.0290(7) -0.0037(5) 0.0042(5) -0.0018(5) C9 0.0109(7) 0.0179(7) 0.0183(7) 0.0015(5) 0.0011(6) -0.0001(5) C5' 0.0212(9) 0.0298(9) 0.0214(7) -0.0048(6) 0.0065(6) -0.0093(6) C2' 0.0180(7) 0.0198(7) 0.0187(7) -0.0020(6) 0.0090(6) -0.0018(5) C1' 0.0155(8) 0.0200(7) 0.0164(7) 0.0004(5) 0.0068(6) -0.0013(5) C6 0.0149(8) 0.0270(8) 0.0223(7) -0.0025(6) 0.0039(6) 0.0014(6) C5 0.0157(7) 0.0222(8) 0.0226(7) 0.0045(6) 0.0057(6) 0.0005(6) C4 0.0211(8) 0.0164(7) 0.0334(8) 0.0047(6) 0.0141(7) 0.0012(6) C3' 0.0201(8) 0.0271(8) 0.0237(8) 0.0034(6) 0.0103(6) 0.0045(6) C10 0.0109(7) 0.0176(7) 0.0225(7) 0.0031(6) 0.0033(6) 0.0000(5) C7 0.0142(8) 0.0188(8) 0.0301(8) -0.0018(6) 0.0024(6) 0.0020(5) C4' 0.0141(8) 0.0381(10) 0.0217(8) 0.0031(7) 0.0041(6) 0.0006(6) C2 0.0172(8) 0.0216(8) 0.0186(7) -0.0016(6) 0.0039(6) 0.0014(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 O1' N1' 1.2286(18) . ? N1 C9 1.3891(19) . ? N1 C2 1.4564(19) . ? N1' O2' 1.2309(17) . ? N1' C2' 1.4681(19) . ? C6' C1' 1.393(2) . ? C6' C5' 1.391(2) . ? C8 C7 1.385(2) . ? C8 C9 1.403(2) . ? N3 C2 1.456(2) . ? N3 C4 1.469(2) . ? C9 C10 1.406(2) . ? C5' C4' 1.380(2) . ? C2' C3' 1.378(2) . ? C2' C1' 1.402(2) . ? C1' C2 1.536(2) . ? C6 C5 1.386(2) . ? C6 C7 1.390(2) . ? C5 C10 1.390(2) . ? C4 C10 1.508(2) . ? C3' C4' 1.387(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N1 C2 120.39(12) . . ? O1' N1' O2' 123.34(13) . . ? O1' N1' C2' 118.81(12) . . ? O2' N1' C2' 117.78(13) . . ? C1' C6' C5' 121.48(14) . . ? C7 C8 C9 120.15(14) . . ? C2 N3 C4 111.16(12) . . ? N1 C9 C8 120.73(13) . . ? N1 C9 C10 119.96(13) . . ? C8 C9 C10 119.27(13) . . ? C4' C5' C6' 120.58(14) . . ? C3' C2' C1' 123.44(14) . . ? C3' C2' N1' 116.07(13) . . ? C1' C2' N1' 120.49(13) . . ? C6' C1' C2' 116.00(13) . . ? C6' C1' C2 122.20(13) . . ? C2' C1' C2 121.54(13) . . ? C5 C6 C7 118.87(14) . . ? C6 C5 C10 121.67(14) . . ? N3 C4 C10 113.76(12) . . ? C2' C3' C4' 118.82(15) . . ? C5 C10 C9 119.13(13) . . ? C5 C10 C4 121.96(13) . . ? C9 C10 C4 118.90(13) . . ? C8 C7 C6 120.83(14) . . ? C5' C4' C3' 119.65(14) . . ? N3 C2 N1 111.80(12) . . ? N3 C2 C1' 106.85(12) . . ? N1 C2 C1' 113.63(12) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.483 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.222 data_4f _database_code_CSD 177050 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(1,2,3,4-tetrahydro-quinazolin-2-yl)-phenol ; _chemical_name_common '2-(4'-hydroxyphenyl)-1,2,3,4-tetrahydroquinazoline' _chemical_melting_point '147.9-151.3 Deg. C' _chemical_formula_moiety 'C14 H14 N2 O' _chemical_formula_sum 'C14 H14 N2 O' _chemical_formula_weight 226.27 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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.3431(4) _cell_length_b 8.7088(2) _cell_length_c 23.4287(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2314.40(11) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _exptl_crystal_description rhombs _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.35 _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 Kappa CCD' _diffrn_measurement_method '\phi +w scans' _diffrn_reflns_number 13743 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.92 _diffrn_reflns_theta_max 28.51 _reflns_number_total 2867 _reflns_number_gt 2074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Xseed' _computing_publication_material 'Ciftab' _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^)+(0.0540P)^2^+0.6160P] 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_number_reflns 2867 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.69854(9) 0.14928(13) 0.68005(4) 0.0340(3) Uani 1 1 d . . . N1 N 0.49806(12) 0.22784(15) 0.93241(5) 0.0321(3) Uani 1 1 d . . . C2' C 0.64516(13) 0.35970(18) 0.81095(6) 0.0342(4) Uani 1 1 d . . . H2' H 0.6780 0.4447 0.8308 0.041 Uiso 1 1 calc R . . C10 C 0.44263(12) 0.26025(16) 0.98439(6) 0.0284(3) Uani 1 1 d . . . C4' C 0.64828(12) 0.18962(16) 0.73062(6) 0.0270(3) Uani 1 1 d . . . C7 C 0.32268(15) 0.31325(19) 1.08637(6) 0.0377(4) Uani 1 1 d . . . H7 H 0.2803 0.3301 1.1208 0.045 Uiso 1 1 calc R . . C6 C 0.29348(14) 0.39441(18) 1.03735(6) 0.0341(4) Uani 1 1 d . . . H6 H 0.2322 0.4687 1.0389 0.041 Uiso 1 1 calc R . . C3' C 0.69605(13) 0.31207(18) 0.76047(6) 0.0338(4) Uani 1 1 d . . . H3' H 0.7639 0.3632 0.7462 0.041 Uiso 1 1 calc R . . C5' C 0.55225(14) 0.11205(18) 0.75332(7) 0.0374(4) Uani 1 1 d . . . H5' H 0.5205 0.0256 0.7340 0.045 Uiso 1 1 calc R . . C1' C 0.54748(14) 0.28644(17) 0.83334(6) 0.0316(3) Uani 1 1 d . . . C5 C 0.35226(13) 0.36899(16) 0.98606(6) 0.0292(3) Uani 1 1 d . . . C4 C 0.32092(14) 0.45932(18) 0.93303(6) 0.0329(3) Uani 1 1 d . B . H4A H 0.2340 0.4643 0.9298 0.039 Uiso 1 1 calc R A 1 H4B H 0.3503 0.5657 0.9375 0.039 Uiso 1 1 calc R A 1 C9 C 0.47402(14) 0.18166(18) 1.03431(6) 0.0338(4) Uani 1 1 d . . . H9 H 0.5371 0.1099 1.0336 0.041 Uiso 1 1 calc R B . C6' C 0.50263(14) 0.16090(18) 0.80430(7) 0.0388(4) Uani 1 1 d . . . H6' H 0.4368 0.1073 0.8195 0.047 Uiso 1 1 calc R . . C8 C 0.41349(15) 0.20805(18) 1.08488(6) 0.0379(4) Uani 1 1 d . . . H8 H 0.4347 0.1536 1.1185 0.046 Uiso 1 1 calc R . . H1'O H 0.6605(18) 0.064(3) 0.6640(9) 0.070(7) Uiso 1 1 d . . . H1N H 0.5686(17) 0.182(2) 0.9349(7) 0.047(5) Uiso 1 1 d . . . N3 N 0.36992(13) 0.39407(18) 0.87874(6) 0.0210(3) Uani 0.80 1 d P B 1 H3N H 0.3283(16) 0.315(2) 0.8684(7) 0.022(5) Uiso 0.80 1 d P C 1 C2 C 0.49448(17) 0.3484(2) 0.88799(7) 0.0212(4) Uani 0.80 1 d P B 1 H2 H 0.5409 0.4395 0.9011 0.025 Uiso 0.80 1 calc PR B 1 N3A N 0.4092(9) 0.4471(12) 0.8913(4) 0.059(3) Uiso 0.20 1 d P B 2 C2A C 0.4507(11) 0.3019(14) 0.8860(5) 0.052(3) Uiso 0.20 1 d P B 2 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 0.0369(6) 0.0360(6) 0.0291(5) -0.0070(4) 0.0078(4) -0.0062(5) N1 0.0332(7) 0.0382(7) 0.0250(6) 0.0039(5) 0.0027(5) 0.0099(6) C2' 0.0368(8) 0.0338(8) 0.0321(8) -0.0084(6) -0.0053(6) 0.0009(7) C10 0.0292(7) 0.0296(7) 0.0264(7) -0.0015(6) 0.0012(6) -0.0048(6) C4' 0.0291(7) 0.0278(7) 0.0243(7) -0.0013(5) 0.0013(5) 0.0019(6) C7 0.0477(9) 0.0375(9) 0.0278(8) -0.0066(6) 0.0094(7) -0.0155(7) C6 0.0351(8) 0.0319(8) 0.0354(8) -0.0056(6) 0.0075(6) -0.0061(6) C3' 0.0328(8) 0.0321(8) 0.0365(8) -0.0045(6) 0.0010(6) -0.0036(6) C5' 0.0370(9) 0.0345(8) 0.0409(8) -0.0130(7) 0.0079(7) -0.0089(7) C1' 0.0391(8) 0.0324(8) 0.0234(7) -0.0002(6) -0.0015(6) 0.0101(7) C5 0.0300(8) 0.0280(7) 0.0297(7) -0.0028(6) 0.0037(6) -0.0052(6) C4 0.0315(8) 0.0335(8) 0.0337(8) 0.0019(6) 0.0090(6) 0.0064(6) C9 0.0394(9) 0.0318(8) 0.0302(8) 0.0014(6) -0.0026(6) -0.0039(7) C6' 0.0377(9) 0.0361(9) 0.0425(9) -0.0023(7) 0.0139(7) -0.0042(7) C8 0.0527(10) 0.0349(8) 0.0261(7) 0.0011(6) -0.0016(7) -0.0141(8) N3 0.0202(7) 0.0212(7) 0.0217(7) -0.0023(6) -0.0005(6) -0.0012(6) C2 0.0191(8) 0.0233(9) 0.0211(8) 0.0003(6) 0.0000(6) -0.0017(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 C4' 1.3609(16) . ? N1 C2A 1.374(11) . ? N1 C10 1.3994(18) . ? N1 C2 1.479(2) . ? C2' C3' 1.380(2) . ? C2' C1' 1.382(2) . ? C10 C5 1.396(2) . ? C10 C9 1.401(2) . ? C4' C3' 1.386(2) . ? C4' C5' 1.388(2) . ? C7 C8 1.379(2) . ? C7 C6 1.389(2) . ? C6 C5 1.392(2) . ? C5' C6' 1.387(2) . ? C1' C6' 1.385(2) . ? C1' C2 1.514(2) . ? C1' C2A 1.657(11) . ? C5 C4 1.513(2) . ? C4 N3A 1.403(10) . ? C4 N3 1.4999(19) . ? C9 C8 1.388(2) . ? N3 C2 1.484(2) . ? N3A C2A 1.355(15) . ? 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 C2A N1 C10 114.7(5) . . ? C2A N1 C2 25.7(5) . . ? C10 N1 C2 117.18(13) . . ? C3' C2' C1' 121.46(14) . . ? C5 C10 N1 119.41(12) . . ? C5 C10 C9 119.64(13) . . ? N1 C10 C9 120.92(13) . . ? O1 C4' C3' 118.31(13) . . ? O1 C4' C5' 122.47(13) . . ? C3' C4' C5' 119.22(13) . . ? C8 C7 C6 119.70(14) . . ? C7 C6 C5 121.25(15) . . ? C2' C3' C4' 120.02(14) . . ? C6' C5' C4' 119.95(14) . . ? C2' C1' C6' 118.20(13) . . ? C2' C1' C2 118.34(15) . . ? C6' C1' C2 123.45(15) . . ? C2' C1' C2A 140.9(5) . . ? C6' C1' C2A 100.8(5) . . ? C2 C1' C2A 22.8(4) . . ? C6 C5 C10 118.92(13) . . ? C6 C5 C4 120.91(13) . . ? C10 C5 C4 120.15(12) . . ? N3A C4 N3 27.9(4) . . ? N3A C4 C5 111.4(4) . . ? N3 C4 C5 114.35(12) . . ? C8 C9 C10 120.38(15) . . ? C1' C6' C5' 121.08(15) . . ? C7 C8 C9 120.06(14) . . ? C2 N3 C4 109.31(13) . . ? N1 C2 N3 108.61(14) . . ? N1 C2 C1' 109.32(13) . . ? N3 C2 C1' 110.50(14) . . ? C2A N3A C4 112.5(9) . . ? N3A C2A N1 120.1(9) . . ? N3A C2A C1' 112.0(9) . . ? N1 C2A C1' 107.0(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 C2A N1 C10 C5 -4.2(6) . . . . ? C2 N1 C10 C5 24.3(2) . . . . ? C2A N1 C10 C9 173.7(6) . . . . ? C2 N1 C10 C9 -157.77(14) . . . . ? C8 C7 C6 C5 1.6(2) . . . . ? C1' C2' C3' C4' 0.9(2) . . . . ? O1 C4' C3' C2' 177.83(13) . . . . ? C5' C4' C3' C2' -2.7(2) . . . . ? O1 C4' C5' C6' -178.25(14) . . . . ? C3' C4' C5' C6' 2.3(2) . . . . ? C3' C2' C1' C6' 1.3(2) . . . . ? C3' C2' C1' C2 -178.19(14) . . . . ? C3' C2' C1' C2A -173.9(6) . . . . ? C7 C6 C5 C10 -0.4(2) . . . . ? C7 C6 C5 C4 -179.23(14) . . . . ? N1 C10 C5 C6 176.61(13) . . . . ? C9 C10 C5 C6 -1.4(2) . . . . ? N1 C10 C5 C4 -4.5(2) . . . . ? C9 C10 C5 C4 177.46(13) . . . . ? C6 C5 C4 N3A 163.9(5) . . . . ? C10 C5 C4 N3A -14.9(5) . . . . ? C6 C5 C4 N3 -165.89(14) . . . . ? C10 C5 C4 N3 15.3(2) . . . . ? C5 C10 C9 C8 1.9(2) . . . . ? N1 C10 C9 C8 -176.03(14) . . . . ? C2' C1' C6' C5' -1.7(2) . . . . ? C2 C1' C6' C5' 177.77(15) . . . . ? C2A C1' C6' C5' 175.2(4) . . . . ? C4' C5' C6' C1' -0.1(3) . . . . ? C6 C7 C8 C9 -1.1(2) . . . . ? C10 C9 C8 C7 -0.7(2) . . . . ? N3A C4 N3 C2 46.1(9) . . . . ? C5 C4 N3 C2 -43.93(19) . . . . ? C2A N1 C2 N3 37.4(11) . . . . ? C10 N1 C2 N3 -53.57(19) . . . . ? C2A N1 C2 C1' -83.2(11) . . . . ? C10 N1 C2 C1' -174.21(13) . . . . ? C4 N3 C2 N1 61.78(18) . . . . ? C4 N3 C2 C1' -178.31(14) . . . . ? C2' C1' C2 N1 -120.04(16) . . . . ? C6' C1' C2 N1 60.5(2) . . . . ? C2A C1' C2 N1 67.0(11) . . . . ? C2' C1' C2 N3 120.48(17) . . . . ? C6' C1' C2 N3 -58.9(2) . . . . ? C2A C1' C2 N3 -52.5(11) . . . . ? N3 C4 N3A C2A -59.1(9) . . . . ? C5 C4 N3A C2A 42.8(10) . . . . ? C4 N3A C2A N1 -57.5(14) . . . . ? C4 N3A C2A C1' 175.7(6) . . . . ? C10 N1 C2A N3A 36.1(13) . . . . ? C2 N1 C2A N3A -65.5(12) . . . . ? C10 N1 C2A C1' 165.2(4) . . . . ? C2 N1 C2A C1' 63.6(10) . . . . ? C2' C1' C2A N3A 45.8(12) . . . . ? C6' C1' C2A N3A -129.9(9) . . . . ? C2 C1' C2A N3A 55.6(10) . . . . ? C2' C1' C2A N1 -87.8(9) . . . . ? C6' C1' C2A N1 96.5(7) . . . . ? C2 C1' C2A N1 -78.0(11) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.51 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.248 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.043 data_5h _database_code_CSD 177051 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-2-[5'-bromosalicylideneimino)benzyl]-5''-bromosalicylideneimine ; _chemical_name_common 'N-2-[5'-bromosalicylideneimino)benzyl]-5''-bromosalicylideneimine' _chemical_melting_point '150.2-151.9 Deg. C' _chemical_formula_moiety 'C21 H16 Br2 N2 O2' _chemical_formula_sum 'C21 H16 Br2 N2 O2' _chemical_formula_weight 488.18 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' 'Br' 'Br' -0.2901 2.4595 '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 24.8822(8) _cell_length_b 4.6291(2) _cell_length_c 16.5755(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.263(2) _cell_angle_gamma 90.00 _cell_volume 1832.81(11) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description needles _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 4.443 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 Kappa CCD' _diffrn_measurement_method '\phi + w scans' _diffrn_reflns_number 14392 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1760 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 29.57 _reflns_number_total 4997 _reflns_number_gt 2316 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Xseed' _computing_publication_material 'Ciftab' _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^)+(0.0213P)^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_number_reflns 4997 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1609 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _refine_ls_shift/su_max 0.003 _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 Br1" Br 0.409348(18) 0.29282(10) 0.04733(3) 0.02857(15) Uani 1 1 d . . . Br1' Br -0.023112(18) -1.77485(10) -0.36783(3) 0.02675(14) Uani 1 1 d . . . C1" C 0.37658(16) -0.1858(8) -0.1754(3) 0.0167(10) Uani 1 1 d . . . O1" O 0.42102(13) -0.1814(7) -0.2870(2) 0.0247(8) Uani 1 1 d . . . C5 C 0.23486(16) -0.3058(9) -0.5330(3) 0.0192(10) Uani 1 1 d . . . H5 H 0.2480 -0.1659 -0.5650 0.023 Uiso 1 1 calc R . . C7 C 0.29016(16) -0.7087(8) -0.3259(3) 0.0200(10) Uani 1 1 d . . . H7A H 0.2678 -0.7469 -0.2862 0.024 Uiso 1 1 calc R . . H7B H 0.3081 -0.8924 -0.3348 0.024 Uiso 1 1 calc R . . O1' O 0.20792(13) -1.2550(7) -0.2565(2) 0.0231(8) Uani 1 1 d . . . C3 C 0.16254(18) -0.6220(8) -0.5167(3) 0.0186(10) Uani 1 1 d . . . H3 H 0.1258 -0.6981 -0.5372 0.022 Uiso 1 1 calc R . . C1 C 0.25171(17) -0.6070(8) -0.4087(3) 0.0180(10) Uani 1 1 d . . . C2 C 0.19793(16) -0.7211(8) -0.4397(3) 0.0167(9) Uani 1 1 d . . . C1' C 0.11774(16) -1.2798(8) -0.3595(3) 0.0175(10) Uani 1 1 d . . . N2 N 0.18109(14) -0.9373(7) -0.3899(2) 0.0183(9) Uani 1 1 d . . . C7' C 0.13348(17) -1.0586(8) -0.4109(3) 0.0177(10) Uani 1 1 d . . . H7' H 0.1072 -1.0030 -0.4620 0.021 Uiso 1 1 calc R . . C2' C 0.15611(17) -1.3716(9) -0.2847(3) 0.0198(11) Uani 1 1 d . . . N1 N 0.33347(13) -0.4977(7) -0.2890(3) 0.0204(9) Uani 1 1 d . . . C3" C 0.45603(18) 0.1213(9) -0.1695(3) 0.0252(12) Uani 1 1 d . . . H3" H 0.4842 0.1874 -0.1937 0.030 Uiso 1 1 calc R . . C4' C 0.08801(17) -1.7049(9) -0.2608(3) 0.0215(10) Uani 1 1 d . . . H4' H 0.0773 -1.8491 -0.2276 0.026 Uiso 1 1 calc R . . C2" C 0.41806(17) -0.0824(9) -0.2112(3) 0.0191(10) Uani 1 1 d . . . C5' C 0.05040(18) -1.6131(9) -0.3351(3) 0.0213(11) Uani 1 1 d . . . C6' C 0.06467(17) -1.4041(8) -0.3842(3) 0.0185(10) Uani 1 1 d . . . H6' H 0.0384 -1.3444 -0.4349 0.022 Uiso 1 1 calc R . . C7" C 0.33613(17) -0.3986(9) -0.2161(3) 0.0220(11) Uani 1 1 d . . . H7" H 0.3104 -0.4683 -0.1878 0.026 Uiso 1 1 calc R . . C4" C 0.45387(17) 0.2311(9) -0.0929(3) 0.0232(11) Uani 1 1 d . . . H4" H 0.4804 0.3713 -0.0648 0.028 Uiso 1 1 calc R . . C6 C 0.26923(18) -0.4009(9) -0.4574(3) 0.0207(11) Uani 1 1 d . . . H6 H 0.3060 -0.3240 -0.4378 0.025 Uiso 1 1 calc R . . C4 C 0.18110(18) -0.4151(9) -0.5623(3) 0.0228(11) Uani 1 1 d . . . H4 H 0.1570 -0.3472 -0.6139 0.027 Uiso 1 1 calc R . . C6" C 0.37483(17) -0.0706(9) -0.0980(3) 0.0219(11) Uani 1 1 d . . . H6" H 0.3469 -0.1360 -0.0732 0.026 Uiso 1 1 calc R . . C3' C 0.14106(18) -1.5867(9) -0.2352(3) 0.0225(11) Uani 1 1 d . . . H3' H 0.1671 -1.6501 -0.1847 0.027 Uiso 1 1 calc R . . C5" C 0.41267(18) 0.1357(9) -0.0571(3) 0.0219(11) Uani 1 1 d . . . H1"O H 0.397(2) -0.292(11) -0.303(4) 0.05(2) Uiso 1 1 d . . . H1'O H 0.219(4) -1.242(17) -0.284(6) 0.17(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1" 0.0316(3) 0.0321(3) 0.0216(3) -0.0058(2) 0.0069(2) -0.0049(2) Br1' 0.0220(2) 0.0279(3) 0.0312(3) -0.0014(2) 0.0090(2) -0.0054(2) C1" 0.019(2) 0.015(2) 0.015(3) 0.000(2) 0.0026(19) 0.0014(18) O1" 0.0240(17) 0.0316(19) 0.018(2) -0.0043(16) 0.0057(15) -0.0029(16) C5 0.020(2) 0.018(2) 0.021(3) 0.002(2) 0.008(2) -0.0005(19) C7 0.017(2) 0.019(2) 0.020(3) 0.000(2) -0.0009(19) -0.0033(19) O1' 0.0211(16) 0.0240(18) 0.023(2) -0.0003(16) 0.0043(14) -0.0010(14) C3 0.020(2) 0.017(2) 0.017(3) 0.000(2) 0.003(2) 0.0005(18) C1 0.025(2) 0.010(2) 0.022(3) -0.0050(19) 0.011(2) 0.0005(18) C2 0.021(2) 0.016(2) 0.016(3) 0.002(2) 0.0079(19) 0.0001(19) C1' 0.020(2) 0.015(2) 0.018(3) -0.002(2) 0.0079(19) 0.0019(19) N2 0.019(2) 0.0181(19) 0.019(3) -0.0045(17) 0.0069(17) 0.0025(16) C7' 0.021(2) 0.018(2) 0.015(3) 0.004(2) 0.006(2) 0.0058(19) C2' 0.020(2) 0.018(2) 0.023(3) -0.005(2) 0.008(2) 0.0026(18) N1 0.0139(19) 0.0179(19) 0.028(3) 0.0022(18) 0.0039(18) 0.0011(15) C3" 0.020(2) 0.025(3) 0.033(3) 0.001(2) 0.012(2) -0.006(2) C4' 0.029(2) 0.018(2) 0.019(3) 0.001(2) 0.009(2) 0.003(2) C2" 0.021(2) 0.019(2) 0.015(3) 0.001(2) 0.001(2) 0.0063(19) C5' 0.024(2) 0.017(2) 0.026(3) -0.006(2) 0.012(2) -0.0044(19) C6' 0.019(2) 0.018(2) 0.018(3) -0.005(2) 0.003(2) 0.0000(18) C7" 0.018(2) 0.020(2) 0.028(3) 0.003(2) 0.006(2) 0.0000(18) C4" 0.024(2) 0.018(2) 0.025(3) -0.002(2) 0.003(2) -0.0035(19) C6 0.022(2) 0.020(2) 0.020(3) -0.003(2) 0.007(2) -0.0023(19) C4 0.031(3) 0.022(2) 0.016(3) 0.001(2) 0.008(2) 0.002(2) C6" 0.017(2) 0.020(2) 0.027(3) 0.000(2) 0.005(2) -0.0001(19) C3' 0.027(3) 0.024(2) 0.015(3) -0.001(2) 0.002(2) 0.008(2) C5" 0.026(2) 0.021(2) 0.021(3) -0.001(2) 0.009(2) 0.0015(19) _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 Br1" C5" 1.901(4) . ? Br1' C5' 1.909(4) . ? C1" C6" 1.400(6) . ? C1" C2" 1.410(5) . ? C1" C7" 1.435(6) . ? O1" C2" 1.359(5) . ? C5 C6 1.377(6) . ? C5 C4 1.385(6) . ? C7 N1 1.456(5) . ? C7 C1 1.512(6) . ? O1' C2' 1.354(5) . ? C3 C4 1.378(5) . ? C3 C2 1.409(6) . ? C1 C2 1.396(6) . ? C1 C6 1.396(5) . ? C2 N2 1.433(5) . ? C1' C6' 1.393(5) . ? C1' C2' 1.402(6) . ? C1' C7' 1.454(5) . ? N2 C7' 1.269(5) . ? C2' C3' 1.405(6) . ? N1 C7" 1.276(5) . ? C3" C2" 1.376(6) . ? C3" C4" 1.382(6) . ? C4' C3' 1.382(6) . ? C4' C5' 1.388(6) . ? C5' C6' 1.373(6) . ? C4" C5" 1.393(5) . ? C6" C5" 1.378(6) . ? 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 C6" C1" C2" 118.0(4) . . ? C6" C1" C7" 119.7(4) . . ? C2" C1" C7" 122.3(4) . . ? C6 C5 C4 119.7(4) . . ? N1 C7 C1 112.2(3) . . ? C4 C3 C2 120.2(4) . . ? C2 C1 C6 117.9(4) . . ? C2 C1 C7 121.0(4) . . ? C6 C1 C7 121.1(4) . . ? C1 C2 C3 120.1(4) . . ? C1 C2 N2 117.2(4) . . ? C3 C2 N2 122.7(4) . . ? C6' C1' C2' 119.3(4) . . ? C6' C1' C7' 120.5(4) . . ? C2' C1' C7' 120.2(4) . . ? C7' N2 C2 123.5(4) . . ? N2 C7' C1' 122.4(4) . . ? O1' C2' C1' 122.1(4) . . ? O1' C2' C3' 117.7(4) . . ? C1' C2' C3' 120.2(4) . . ? C7" N1 C7 118.4(4) . . ? C2" C3" C4" 121.0(4) . . ? C3' C4' C5' 120.0(4) . . ? O1" C2" C3" 119.2(4) . . ? O1" C2" C1" 120.7(4) . . ? C3" C2" C1" 120.1(4) . . ? C6' C5' C4' 121.3(4) . . ? C6' C5' Br1' 119.6(4) . . ? C4' C5' Br1' 119.1(3) . . ? C5' C6' C1' 119.9(4) . . ? N1 C7" C1" 122.4(4) . . ? C3" C4" C5" 119.8(4) . . ? C5 C6 C1 122.0(4) . . ? C3 C4 C5 120.1(4) . . ? C5" C6" C1" 121.5(4) . . ? C4' C3' C2' 119.3(4) . . ? C6" C5" C4" 119.5(4) . . ? C6" C5" Br1" 121.0(3) . . ? C4" C5" Br1" 119.5(3) . . ? 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 N1 C7 C1 C2 -157.7(4) . . . . ? N1 C7 C1 C6 23.8(5) . . . . ? C6 C1 C2 C3 -1.9(6) . . . . ? C7 C1 C2 C3 179.5(4) . . . . ? C6 C1 C2 N2 178.6(3) . . . . ? C7 C1 C2 N2 0.0(6) . . . . ? C4 C3 C2 C1 0.9(6) . . . . ? C4 C3 C2 N2 -179.6(4) . . . . ? C1 C2 N2 C7' -179.9(4) . . . . ? C3 C2 N2 C7' 0.6(6) . . . . ? C2 N2 C7' C1' 179.3(3) . . . . ? C6' C1' C7' N2 178.9(4) . . . . ? C2' C1' C7' N2 -1.5(6) . . . . ? C6' C1' C2' O1' -178.7(4) . . . . ? C7' C1' C2' O1' 1.7(6) . . . . ? C6' C1' C2' C3' 0.0(6) . . . . ? C7' C1' C2' C3' -179.6(4) . . . . ? C1 C7 N1 C7" 121.0(4) . . . . ? C4" C3" C2" O1" 178.9(4) . . . . ? C4" C3" C2" C1" -0.9(7) . . . . ? C6" C1" C2" O1" -178.5(4) . . . . ? C7" C1" C2" O1" 0.4(6) . . . . ? C6" C1" C2" C3" 1.3(6) . . . . ? C7" C1" C2" C3" -179.8(4) . . . . ? C3' C4' C5' C6' -0.3(6) . . . . ? C3' C4' C5' Br1' -178.8(3) . . . . ? C4' C5' C6' C1' -0.2(6) . . . . ? Br1' C5' C6' C1' 178.3(3) . . . . ? C2' C1' C6' C5' 0.3(6) . . . . ? C7' C1' C6' C5' 179.9(4) . . . . ? C7 N1 C7" C1" -178.7(4) . . . . ? C6" C1" C7" N1 175.5(4) . . . . ? C2" C1" C7" N1 -3.4(7) . . . . ? C2" C3" C4" C5" -0.1(7) . . . . ? C4 C5 C6 C1 0.3(7) . . . . ? C2 C1 C6 C5 1.3(6) . . . . ? C7 C1 C6 C5 179.9(4) . . . . ? C2 C3 C4 C5 0.7(6) . . . . ? C6 C5 C4 C3 -1.3(6) . . . . ? C2" C1" C6" C5" -0.6(6) . . . . ? C7" C1" C6" C5" -179.6(4) . . . . ? C5' C4' C3' C2' 0.6(6) . . . . ? O1' C2' C3' C4' 178.3(4) . . . . ? C1' C2' C3' C4' -0.5(6) . . . . ? C1" C6" C5" C4" -0.4(6) . . . . ? C1" C6" C5" Br1" 179.4(3) . . . . ? C3" C4" C5" C6" 0.8(6) . . . . ? C3" C4" C5" Br1" -179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 29.57 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.673 _refine_diff_density_min -0.915 _refine_diff_density_rms 0.133 data_4j _database_code_CSD 177052 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydroquinazoline ; _chemical_name_common '2-(veratryl)-1,2,3,4-tetrahydroquinazoline' _chemical_melting_point '89.1-98.7Deg. C' _chemical_formula_moiety 'C16 H18 N2 O2' _chemical_formula_sum 'C16 H18 N2 O2' _chemical_formula_weight 270.32 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 Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 20.4722(3) _cell_length_b 13.2281(2) _cell_length_c 20.7521(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5619.84(16) _cell_formula_units_Z 16 _cell_measurement_temperature 123(2) _exptl_crystal_description colourless _exptl_crystal_colour needles _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 0.085 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 Kappa CCd' _diffrn_measurement_method 'phi + w scans' _diffrn_reflns_number 30579 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.1351 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.29 _reflns_number_total 13156 _reflns_number_gt 7466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Xseed' _computing_publication_material 'Ciftab' _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^)+(0.0415P)^2^+0.7967P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(10) _refine_ls_number_reflns 13156 _refine_ls_number_parameters 761 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1532 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.1197 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 O13' O 0.74710(10) 0.61716(16) 0.80905(11) 0.0261(5) Uani 1 1 d . . . O23' O 0.87114(10) 0.59943(15) 0.82641(10) 0.0229(5) Uani 1 1 d . . . N13 N 0.73460(13) 0.86718(18) 0.61283(12) 0.0196(6) Uani 1 1 d . . . N33 N 0.74247(14) 0.98534(19) 0.70087(13) 0.0212(6) Uani 1 1 d . . . C43' C 0.85275(15) 0.6753(2) 0.78553(14) 0.0185(7) Uani 1 1 d . . . C93 C 0.68640(15) 0.9130(2) 0.51024(15) 0.0205(7) Uani 1 1 d . . . H93 H 0.6913 0.8452 0.4960 0.025 Uiso 1 1 calc R . . C103 C 0.70622(14) 0.9396(2) 0.57220(15) 0.0170(7) Uani 1 1 d . . . C53' C 0.8949(2) 0.7366(2) 0.75151(16) 0.0216(8) Uani 1 1 d . . . H53' H 0.9407 0.7274 0.7554 0.026 Uiso 1 1 calc R . . C63 C 0.66916(14) 1.1099(2) 0.55172(16) 0.0220(8) Uani 1 1 d . . . H63 H 0.6624 1.1773 0.5661 0.026 Uiso 1 1 calc R . . C13' C 0.80354(15) 0.8268(2) 0.70507(15) 0.0183(7) Uani 1 1 d . . . C53 C 0.69724(15) 1.0393(2) 0.59354(15) 0.0180(7) Uani 1 1 d . . . C23' C 0.76079(19) 0.7626(2) 0.73823(15) 0.0194(8) Uani 1 1 d . . . H23' H 0.7150 0.7714 0.7337 0.023 Uiso 1 1 calc R . . C73 C 0.65110(15) 1.0834(2) 0.48990(16) 0.0237(8) Uani 1 1 d . . . H73 H 0.6330 1.1325 0.4617 0.028 Uiso 1 1 calc R . . C63' C 0.87005(16) 0.8127(2) 0.71116(15) 0.0210(7) Uani 1 1 d . . . H63' H 0.8993 0.8549 0.6879 0.025 Uiso 1 1 calc R . . C83' C 0.94033(15) 0.5884(2) 0.83694(17) 0.0265(8) Uani 1 1 d . . . H83A H 0.9580 0.6516 0.8544 0.040 Uiso 1 1 calc R . . H83B H 0.9619 0.5728 0.7960 0.040 Uiso 1 1 calc R . . H83C H 0.9481 0.5334 0.8676 0.040 Uiso 1 1 calc R . . C83 C 0.65957(15) 0.9843(2) 0.46912(16) 0.0229(7) Uani 1 1 d . . . H83 H 0.6470 0.9655 0.4267 0.027 Uiso 1 1 calc R . . C43 C 0.71944(16) 1.0705(2) 0.66019(15) 0.0209(7) Uani 1 1 d . . . H43A H 0.7553 1.1203 0.6559 0.025 Uiso 1 1 calc R . . H43B H 0.6827 1.1045 0.6824 0.025 Uiso 1 1 calc R . . C23 C 0.77702(15) 0.9104(2) 0.66277(16) 0.0196(7) Uani 1 1 d . . . H23 H 0.8147 0.9444 0.6411 0.024 Uiso 1 1 calc R . . C73' C 0.67875(14) 0.6206(2) 0.79562(17) 0.0271(8) Uani 1 1 d . . . H73A H 0.6719 0.6191 0.7489 0.041 Uiso 1 1 calc R . . H73B H 0.6602 0.6830 0.8134 0.041 Uiso 1 1 calc R . . H73C H 0.6572 0.5622 0.8154 0.041 Uiso 1 1 calc R . . C33' C 0.78457(14) 0.6867(2) 0.77736(15) 0.0180(7) Uani 1 1 d . . . O22' O 0.49679(10) 0.62719(15) 0.97722(10) 0.0236(5) Uani 1 1 d . . . O24' O 0.82229(11) 0.85306(15) 1.10798(10) 0.0270(5) Uani 1 1 d . . . O12' O 0.62085(10) 0.61174(15) 0.96297(10) 0.0239(5) Uani 1 1 d . . . N34 N 0.67460(17) 1.24813(19) 1.02147(16) 0.0245(8) Uani 1 1 d . . . O14' O 0.78552(10) 0.87707(16) 0.98926(10) 0.0272(5) Uani 1 1 d . . . N12 N 0.48011(13) 0.8795(2) 1.17335(13) 0.0205(6) Uani 1 1 d . . . N32 N 0.48776(15) 1.00055(19) 1.08712(13) 0.0252(7) Uani 1 1 d . . . C44' C 0.77722(15) 0.9288(2) 1.09760(16) 0.0211(8) Uani 1 1 d . . . C24 C 0.63961(16) 1.1623(2) 1.04918(16) 0.0227(8) Uani 1 1 d . . . H24 H 0.6180 1.1855 1.0898 0.027 Uiso 1 1 calc R . . C92 C 0.43331(15) 0.9196(2) 1.27778(16) 0.0229(8) Uani 1 1 d . . . H92 H 0.4388 0.8514 1.2910 0.028 Uiso 1 1 calc R . . C62 C 0.41655(15) 1.1183(2) 1.23936(16) 0.0236(8) Uani 1 1 d . . . H62 H 0.4103 1.1866 1.2265 0.028 Uiso 1 1 calc R . . C104 C 0.54716(16) 1.2009(2) 0.97951(15) 0.0194(8) Uani 1 1 d . . . N14 N 0.58875(13) 1.12630(19) 1.00523(13) 0.0226(6) Uani 1 1 d . . . C54 C 0.56657(17) 1.3033(2) 0.97859(16) 0.0213(8) Uani 1 1 d . . . C12' C 0.54922(16) 0.8413(2) 1.08020(15) 0.0220(8) Uani 1 1 d . . . C32' C 0.53283(15) 0.6994(2) 1.00849(15) 0.0184(7) Uani 1 1 d . . . C42' C 0.60082(15) 0.6900(2) 1.00155(15) 0.0194(7) Uani 1 1 d . . . C22 C 0.52228(16) 0.9230(2) 1.12324(16) 0.0234(8) Uani 1 1 d . . . H22 H 0.5601 0.9561 1.1453 0.028 Uiso 1 1 calc R . . C34' C 0.75869(15) 0.9433(2) 1.03268(16) 0.0225(8) Uani 1 1 d . . . C72 C 0.39788(15) 1.0893(2) 1.30086(17) 0.0251(8) Uani 1 1 d . . . H72 H 0.3795 1.1371 1.3298 0.030 Uiso 1 1 calc R . . C24' C 0.71402(15) 1.0186(2) 1.01728(16) 0.0234(8) Uani 1 1 d . . . H24' H 0.7020 1.0295 0.9736 0.028 Uiso 1 1 calc R . . C42 C 0.46569(16) 1.0828(2) 1.12985(16) 0.0250(8) Uani 1 1 d . . . H42A H 0.4289 1.1182 1.1087 0.030 Uiso 1 1 calc R . . H42B H 0.5018 1.1320 1.1346 0.030 Uiso 1 1 calc R . . C62' C 0.61543(16) 0.8294(2) 1.07427(16) 0.0239(8) Uani 1 1 d . . . H62' H 0.6439 0.8729 1.0974 0.029 Uiso 1 1 calc R . . C102 C 0.45244(15) 0.9491(2) 1.21593(15) 0.0187(7) Uani 1 1 d . . . C94 C 0.48664(17) 1.1743(2) 0.95367(15) 0.0236(8) Uani 1 1 d . . . H94 H 0.4733 1.1055 0.9545 0.028 Uiso 1 1 calc R . . C22' C 0.50734(19) 0.7755(2) 1.04664(15) 0.0206(8) Uani 1 1 d . . . H22' H 0.4614 0.7833 1.0502 0.025 Uiso 1 1 calc R . . C84 C 0.4458(2) 1.2460(2) 0.92687(17) 0.0270(9) Uani 1 1 d . . . H84 H 0.4046 1.2267 0.9099 0.032 Uiso 1 1 calc R . . C52' C 0.64183(19) 0.7539(2) 1.03472(17) 0.0219(9) Uani 1 1 d . . . H52' H 0.6878 0.7469 1.0308 0.026 Uiso 1 1 calc R . . C14' C 0.68658(15) 1.0786(2) 1.06597(16) 0.0224(8) Uani 1 1 d . . . C64' C 0.70426(16) 1.0626(2) 1.12897(17) 0.0240(8) Uani 1 1 d . . . H64' H 0.6855 1.1028 1.1620 0.029 Uiso 1 1 calc R . . C82 C 0.40655(15) 0.9888(2) 1.31953(17) 0.0258(8) Uani 1 1 d . . . H82 H 0.3938 0.9681 1.3615 0.031 Uiso 1 1 calc R . . C84' C 0.84529(18) 0.8403(3) 1.17266(16) 0.0327(9) Uani 1 1 d . . . H84A H 0.8086 0.8217 1.2006 0.049 Uiso 1 1 calc R . . H84B H 0.8646 0.9037 1.1879 0.049 Uiso 1 1 calc R . . H84C H 0.8783 0.7867 1.1737 0.049 Uiso 1 1 calc R . . C44 C 0.63034(17) 1.3338(2) 1.00881(18) 0.0277(8) Uani 1 1 d . . . H44A H 0.6527 1.3823 0.9800 0.033 Uiso 1 1 calc R . . H44B H 0.6213 1.3689 1.0500 0.033 Uiso 1 1 calc R . . C82' C 0.42716(15) 0.6316(3) 0.98458(17) 0.0288(8) Uani 1 1 d . . . H82A H 0.4108 0.6949 0.9661 0.043 Uiso 1 1 calc R . . H82B H 0.4160 0.6287 1.0305 0.043 Uiso 1 1 calc R . . H82C H 0.4072 0.5742 0.9622 0.043 Uiso 1 1 calc R . . C64 C 0.52525(18) 1.3742(2) 0.95049(16) 0.0285(8) Uani 1 1 d . . . H64 H 0.5385 1.4430 0.9488 0.034 Uiso 1 1 calc R . . C52 C 0.44418(15) 1.0503(2) 1.19574(15) 0.0192(7) Uani 1 1 d . . . C72' C 0.69021(15) 0.5974(2) 0.95849(16) 0.0262(8) Uani 1 1 d . . . H72A H 0.7080 0.5841 1.0015 0.039 Uiso 1 1 calc R . . H72B H 0.7104 0.6585 0.9407 0.039 Uiso 1 1 calc R . . H72C H 0.6995 0.5398 0.9302 0.039 Uiso 1 1 calc R . . C74 C 0.46521(19) 1.3468(3) 0.92489(16) 0.0310(9) Uani 1 1 d . . . H74 H 0.4376 1.3964 0.9061 0.037 Uiso 1 1 calc R . . C54' C 0.74955(16) 0.9876(2) 1.14492(16) 0.0241(8) Uani 1 1 d . . . H54' H 0.7613 0.9772 1.1887 0.029 Uiso 1 1 calc R . . C74' C 0.76693(19) 0.8879(3) 0.92339(17) 0.0410(10) Uani 1 1 d . . . H74A H 0.7799 0.9550 0.9079 0.062 Uiso 1 1 calc R . . H74B H 0.7195 0.8804 0.9195 0.062 Uiso 1 1 calc R . . H74C H 0.7887 0.8359 0.8975 0.062 Uiso 1 1 calc R . . O11' O 0.53951(10) 0.63465(15) 0.77552(10) 0.0233(5) Uani 1 1 d . . . N31 N 0.42897(18) 0.2587(2) 0.75428(17) 0.0272(8) Uani 1 1 d . . . O21' O 0.57564(11) 0.64853(16) 0.65731(10) 0.0266(5) Uani 1 1 d . . . C41' C 0.53010(16) 0.5750(2) 0.66950(16) 0.0206(7) Uani 1 1 d . . . C31' C 0.51241(15) 0.5644(2) 0.73461(15) 0.0198(7) Uani 1 1 d . . . N11 N 0.34463(14) 0.3812(2) 0.77263(14) 0.0232(7) Uani 1 1 d . . . C81 C 0.1993(2) 0.2652(3) 0.84732(17) 0.0270(9) Uani 1 1 d . . . H81 H 0.1585 0.2855 0.8649 0.032 Uiso 1 1 calc R . . C21 C 0.39354(16) 0.3443(2) 0.72649(16) 0.0234(8) Uani 1 1 d . . . H21 H 0.3702 0.3201 0.6871 0.028 Uiso 1 1 calc R . . C101 C 0.30177(17) 0.3080(2) 0.79687(16) 0.0216(8) Uani 1 1 d . . . C61' C 0.45474(16) 0.4412(2) 0.64316(17) 0.0262(8) Uani 1 1 d . . . H61' H 0.4338 0.4009 0.6114 0.031 Uiso 1 1 calc R . . C91 C 0.24143(16) 0.3369(2) 0.82257(16) 0.0231(8) Uani 1 1 d . . . H91 H 0.2294 0.4062 0.8230 0.028 Uiso 1 1 calc R . . C51 C 0.31921(17) 0.2057(2) 0.79614(16) 0.0219(8) Uani 1 1 d . . . C61 C 0.27595(17) 0.1348(2) 0.82142(15) 0.0258(8) Uani 1 1 d . . . H61 H 0.2878 0.0653 0.8214 0.031 Uiso 1 1 calc R . . C21' C 0.46928(15) 0.4901(2) 0.75326(15) 0.0206(7) Uani 1 1 d . . . H21' H 0.4591 0.4814 0.7976 0.025 Uiso 1 1 calc R . . C81' C 0.59873(18) 0.6569(3) 0.59211(16) 0.0321(9) Uani 1 1 d . . . H81A H 0.5625 0.6767 0.5639 0.048 Uiso 1 1 calc R . . H81B H 0.6162 0.5915 0.5780 0.048 Uiso 1 1 calc R . . H81C H 0.6333 0.7081 0.5899 0.048 Uiso 1 1 calc R . . C11' C 0.44019(15) 0.4270(2) 0.70677(16) 0.0215(7) Uani 1 1 d . . . C51' C 0.50053(17) 0.5151(2) 0.62407(16) 0.0251(8) Uani 1 1 d . . . H51' H 0.5109 0.5233 0.5798 0.030 Uiso 1 1 calc R . . C71 C 0.21617(19) 0.1632(3) 0.84662(16) 0.0286(9) Uani 1 1 d . . . H71 H 0.1870 0.1138 0.8632 0.034 Uiso 1 1 calc R . . C71' C 0.52083(16) 0.6289(2) 0.84144(15) 0.0261(8) Uani 1 1 d . . . H71A H 0.5349 0.5639 0.8594 0.039 Uiso 1 1 calc R . . H71B H 0.4732 0.6348 0.8449 0.039 Uiso 1 1 calc R . . H71C H 0.5415 0.6841 0.8655 0.039 Uiso 1 1 calc R . . C41 C 0.38383(17) 0.1744(2) 0.76819(17) 0.0269(9) Uani 1 1 d . . . H41A H 0.4054 0.1275 0.7987 0.032 Uiso 1 1 calc R . . H41B H 0.3757 0.1367 0.7277 0.032 Uiso 1 1 calc R . . H31N H 0.445(2) 0.280(3) 0.792(2) 0.054(14) Uiso 1 1 d . . . H34N H 0.6929(16) 1.225(2) 0.9822(17) 0.023(9) Uiso 1 1 d . . . H14N H 0.5618(17) 1.069(3) 1.0233(17) 0.044(11) Uiso 1 1 d . . . H11N H 0.3268(16) 0.432(2) 0.7598(16) 0.026(10) Uiso 1 1 d . . . H32N H 0.4497(18) 0.965(3) 1.0714(18) 0.047(12) Uiso 1 1 d . . . H12N H 0.4977(15) 0.830(2) 1.1896(14) 0.016(9) Uiso 1 1 d . . . H33N H 0.7068(18) 0.950(3) 0.7173(17) 0.041(11) Uiso 1 1 d . . . H13N H 0.7572(15) 0.812(2) 0.5879(16) 0.033(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O13' 0.0130(12) 0.0341(13) 0.0311(13) 0.0137(11) 0.0033(10) -0.0008(10) O23' 0.0135(11) 0.0291(12) 0.0260(13) 0.0107(10) -0.0008(10) 0.0036(10) N13 0.0219(15) 0.0162(13) 0.0207(16) 0.0012(11) -0.0033(12) 0.0034(12) N33 0.0221(17) 0.0191(14) 0.0224(16) 0.0000(12) -0.0006(13) 0.0005(13) C43' 0.0188(18) 0.0209(16) 0.0158(18) 0.0005(13) -0.0006(14) -0.0017(14) C93 0.0190(17) 0.0187(16) 0.0239(19) 0.0003(14) -0.0007(15) 0.0004(14) C103 0.0119(16) 0.0183(17) 0.0207(19) 0.0031(14) 0.0022(13) 0.0001(13) C53' 0.017(2) 0.0267(18) 0.021(2) -0.0014(14) -0.0029(16) -0.0010(15) C63 0.0160(17) 0.0226(17) 0.027(2) -0.0005(14) 0.0012(15) 0.0025(14) C13' 0.0178(18) 0.0175(16) 0.0197(18) -0.0010(13) -0.0013(14) -0.0002(14) C53 0.0110(17) 0.0223(16) 0.0207(18) -0.0009(14) 0.0028(14) 0.0030(14) C23' 0.0104(18) 0.0234(17) 0.024(2) 0.0004(14) 0.0019(15) 0.0011(14) C73 0.0176(18) 0.0238(17) 0.030(2) 0.0055(15) -0.0008(15) 0.0068(14) C63' 0.0207(19) 0.0231(17) 0.0191(18) 0.0002(14) -0.0013(15) -0.0058(15) C83' 0.0129(17) 0.0324(19) 0.034(2) 0.0071(15) -0.0009(15) 0.0044(15) C83 0.0155(17) 0.0321(18) 0.0211(19) -0.0040(15) 0.0004(14) 0.0000(15) C43 0.0189(17) 0.0198(16) 0.0239(19) 0.0002(14) 0.0003(15) -0.0001(14) C23 0.0176(18) 0.0212(16) 0.0202(18) 0.0001(14) 0.0008(14) -0.0023(15) C73' 0.0137(17) 0.0286(18) 0.039(2) 0.0127(16) -0.0024(16) -0.0040(15) C33' 0.0141(17) 0.0236(16) 0.0164(18) 0.0024(13) 0.0024(14) -0.0016(15) O22' 0.0146(11) 0.0271(12) 0.0291(14) -0.0072(10) -0.0017(10) -0.0017(10) O24' 0.0253(13) 0.0315(12) 0.0242(14) -0.0008(10) -0.0038(11) 0.0054(11) O12' 0.0137(11) 0.0318(12) 0.0262(13) -0.0051(10) 0.0002(10) 0.0038(10) N34 0.024(2) 0.0228(16) 0.0261(19) 0.0008(13) 0.0004(16) -0.0044(13) O14' 0.0220(13) 0.0379(13) 0.0217(13) -0.0059(10) 0.0018(10) 0.0074(11) N12 0.0180(15) 0.0201(15) 0.0235(16) 0.0037(13) 0.0034(12) 0.0018(13) N32 0.0282(18) 0.0212(15) 0.0262(17) 0.0025(13) 0.0033(13) 0.0029(14) C44' 0.0145(18) 0.0206(17) 0.028(2) 0.0005(15) -0.0007(15) -0.0017(15) C24 0.0176(18) 0.0223(17) 0.028(2) 0.0019(15) -0.0007(16) -0.0016(15) C92 0.0146(17) 0.0238(16) 0.030(2) 0.0045(15) 0.0024(15) -0.0006(15) C62 0.0135(17) 0.0218(17) 0.035(2) -0.0003(15) -0.0033(15) 0.0005(15) C104 0.023(2) 0.0226(17) 0.0125(17) -0.0001(14) -0.0008(15) 0.0004(16) N14 0.0192(16) 0.0183(14) 0.0302(17) 0.0008(12) -0.0059(13) -0.0037(13) C54 0.022(2) 0.0233(18) 0.0184(19) 0.0000(14) 0.0045(15) -0.0014(16) C12' 0.028(2) 0.0188(16) 0.0191(18) 0.0015(14) 0.0012(15) -0.0040(15) C32' 0.0162(18) 0.0224(17) 0.0166(17) 0.0036(14) -0.0013(14) -0.0012(14) C42' 0.0211(18) 0.0205(16) 0.0167(18) -0.0028(13) 0.0023(14) 0.0003(14) C22 0.0206(19) 0.0249(17) 0.0247(19) 0.0004(15) 0.0029(15) -0.0019(15) C34' 0.0157(17) 0.0264(17) 0.026(2) -0.0039(15) 0.0020(14) -0.0065(15) C72 0.0189(18) 0.0272(18) 0.029(2) -0.0081(15) 0.0020(15) 0.0005(15) C24' 0.0144(17) 0.0304(18) 0.0254(19) 0.0014(15) -0.0024(15) -0.0038(15) C42 0.0222(19) 0.0229(17) 0.030(2) -0.0028(15) -0.0014(16) 0.0013(15) C62' 0.0213(19) 0.0247(17) 0.026(2) -0.0033(14) 0.0000(15) -0.0075(15) C102 0.0100(16) 0.0210(16) 0.0252(19) -0.0020(14) -0.0016(14) 0.0003(14) C94 0.027(2) 0.0258(17) 0.0179(19) 0.0004(15) -0.0020(16) -0.0022(16) C22' 0.019(2) 0.0238(17) 0.0191(19) 0.0038(15) 0.0035(15) 0.0032(16) C84 0.025(2) 0.037(2) 0.020(2) -0.0002(15) -0.0035(17) -0.0015(16) C52' 0.010(2) 0.0296(19) 0.026(2) -0.0002(15) 0.0002(16) -0.0009(14) C14' 0.0165(17) 0.0238(17) 0.027(2) -0.0023(15) -0.0026(15) -0.0049(15) C64' 0.0238(19) 0.0220(17) 0.026(2) -0.0068(15) 0.0017(16) -0.0050(16) C82 0.0176(18) 0.0327(19) 0.027(2) -0.0033(16) 0.0052(15) -0.0040(15) C84' 0.035(2) 0.035(2) 0.028(2) -0.0010(16) -0.0082(17) 0.0031(17) C44 0.032(2) 0.0206(17) 0.030(2) 0.0051(15) -0.0005(17) -0.0026(17) C82' 0.0154(18) 0.038(2) 0.033(2) -0.0053(16) -0.0006(16) -0.0017(15) C64 0.034(2) 0.0239(17) 0.028(2) 0.0054(15) 0.0034(17) 0.0021(17) C52 0.0121(17) 0.0230(17) 0.0226(19) 0.0004(14) -0.0020(14) -0.0031(14) C72' 0.0182(18) 0.0324(18) 0.028(2) -0.0046(15) 0.0022(15) 0.0045(16) C74 0.034(2) 0.0316(19) 0.027(2) 0.0053(16) -0.0038(17) 0.0083(18) C54' 0.0226(19) 0.0273(18) 0.022(2) -0.0020(15) -0.0043(15) -0.0019(16) C74' 0.041(2) 0.059(2) 0.024(2) -0.0144(18) -0.0040(18) 0.019(2) O11' 0.0213(12) 0.0319(12) 0.0168(12) -0.0024(10) 0.0003(10) -0.0059(10) N31 0.026(2) 0.0191(16) 0.036(2) -0.0007(13) 0.0010(16) 0.0025(13) O21' 0.0255(13) 0.0318(12) 0.0226(14) 0.0031(10) 0.0040(10) -0.0049(11) C41' 0.0168(18) 0.0236(17) 0.0214(19) 0.0016(15) 0.0018(15) 0.0027(15) C31' 0.0168(17) 0.0208(17) 0.0219(19) -0.0028(14) -0.0049(14) 0.0022(15) N11 0.0215(16) 0.0191(15) 0.0290(17) 0.0031(13) 0.0013(13) 0.0017(14) C81 0.028(3) 0.031(2) 0.021(2) 0.0039(15) 0.0039(18) 0.0009(17) C21 0.0200(18) 0.0236(17) 0.027(2) -0.0028(15) -0.0019(15) 0.0065(15) C101 0.021(2) 0.0230(18) 0.0202(19) 0.0003(14) -0.0050(15) -0.0013(16) C61' 0.0221(19) 0.0255(18) 0.031(2) -0.0086(15) 0.0000(16) -0.0001(16) C91 0.0224(19) 0.0231(18) 0.024(2) 0.0023(14) -0.0019(16) 0.0032(16) C51 0.027(2) 0.0216(17) 0.0170(18) 0.0003(14) -0.0023(15) 0.0005(16) C61 0.035(2) 0.0214(18) 0.0209(19) 0.0025(14) -0.0064(16) 0.0019(16) C21' 0.0208(18) 0.0252(17) 0.0159(18) 0.0027(13) 0.0016(14) 0.0023(15) C81' 0.033(2) 0.036(2) 0.027(2) 0.0032(16) 0.0143(17) -0.0011(17) C11' 0.0179(17) 0.0194(16) 0.027(2) -0.0021(14) -0.0005(15) 0.0020(15) C51' 0.028(2) 0.0288(18) 0.0190(19) -0.0050(15) 0.0029(16) 0.0052(17) C71 0.034(2) 0.027(2) 0.025(2) 0.0087(16) -0.0015(17) -0.0059(18) C71' 0.0225(18) 0.0364(19) 0.0195(19) -0.0009(15) -0.0006(15) -0.0025(16) C41 0.032(2) 0.0150(17) 0.033(2) -0.0016(15) -0.0011(17) 0.0014(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 O13' C33' 1.367(3) . ? O13' C73' 1.428(4) . ? O23' C43' 1.367(3) . ? O23' C83' 1.441(4) . ? N13 C103 1.402(4) . ? N13 C23 1.468(4) . ? N33 C23 1.452(4) . ? N33 C43 1.484(4) . ? C43' C53' 1.379(4) . ? C43' C33' 1.414(4) . ? C93 C83 1.386(4) . ? C93 C103 1.393(4) . ? C103 C53 1.404(4) . ? C53' C63' 1.405(4) . ? C63 C73 1.381(4) . ? C63 C53 1.399(4) . ? C13' C63' 1.380(4) . ? C13' C23' 1.400(4) . ? C13' C23 1.512(4) . ? C53 C43 1.513(4) . ? C23' C33' 1.380(4) . ? C73 C83 1.390(4) . ? O22' C32' 1.370(4) . ? O22' C82' 1.435(4) . ? O24' C44' 1.379(4) . ? O24' C84' 1.433(4) . ? O12' C42' 1.372(3) . ? O12' C72' 1.436(4) . ? N34 C24 1.460(4) . ? N34 C44 1.474(4) . ? O14' C34' 1.371(4) . ? O14' C74' 1.426(4) . ? N12 C102 1.396(4) . ? N12 C22 1.469(4) . ? N32 C22 1.454(4) . ? N32 C42 1.474(4) . ? C44' C54' 1.374(4) . ? C44' C34' 1.413(4) . ? C24 N14 1.464(4) . ? C24 C14' 1.508(4) . ? C92 C82 1.374(4) . ? C92 C102 1.397(4) . ? C62 C72 1.387(4) . ? C62 C52 1.396(4) . ? C104 C94 1.395(5) . ? C104 N14 1.408(4) . ? C104 C54 1.412(4) . ? C54 C64 1.391(5) . ? C54 C44 1.503(5) . ? C12' C62' 1.370(4) . ? C12' C22' 1.407(5) . ? C12' C22 1.506(4) . ? C32' C22' 1.383(4) . ? C32' C42' 1.405(4) . ? C42' C52' 1.376(5) . ? C34' C24' 1.390(4) . ? C72 C82 1.396(4) . ? C24' C14' 1.402(4) . ? C42 C52 1.499(4) . ? C62' C52' 1.400(5) . ? C102 C52 1.414(4) . ? C94 C84 1.382(5) . ? C84 C74 1.391(5) . ? C14' C64' 1.373(5) . ? C64' C54' 1.397(4) . ? C64 C74 1.388(5) . ? O11' C31' 1.376(3) . ? O11' C71' 1.422(4) . ? N31 C21 1.463(4) . ? N31 C41 1.477(4) . ? O21' C41' 1.371(4) . ? O21' C81' 1.437(4) . ? C41' C51' 1.372(4) . ? C41' C31' 1.406(4) . ? C31' C21' 1.377(4) . ? N11 C101 1.400(4) . ? N11 C21 1.469(4) . ? C81 C91 1.382(5) . ? C81 C71 1.392(5) . ? C21 C11' 1.509(4) . ? C101 C91 1.399(5) . ? C101 C51 1.400(4) . ? C61' C11' 1.366(5) . ? C61' C51' 1.411(5) . ? C51 C61 1.393(4) . ? C51 C41 1.503(5) . ? C61 C71 1.383(5) . ? C21' C11' 1.408(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 C33' O13' C73' 115.8(2) . . ? C43' O23' C83' 116.0(2) . . ? C103 N13 C23 113.8(2) . . ? C23 N33 C43 111.3(3) . . ? O23' C43' C53' 125.3(3) . . ? O23' C43' C33' 115.1(3) . . ? C53' C43' C33' 119.6(3) . . ? C83 C93 C103 120.8(3) . . ? C93 C103 N13 120.2(3) . . ? C93 C103 C53 119.4(3) . . ? N13 C103 C53 120.4(3) . . ? C43' C53' C63' 120.0(3) . . ? C73 C63 C53 121.1(3) . . ? C63' C13' C23' 119.3(3) . . ? C63' C13' C23 120.4(3) . . ? C23' C13' C23 120.3(3) . . ? C63 C53 C103 119.1(3) . . ? C63 C53 C43 120.6(3) . . ? C103 C53 C43 120.4(3) . . ? C33' C23' C13' 120.7(3) . . ? C63 C73 C83 119.7(3) . . ? C13' C63' C53' 120.6(3) . . ? C93 C83 C73 120.0(3) . . ? N33 C43 C53 114.1(2) . . ? N33 C23 N13 111.2(3) . . ? N33 C23 C13' 111.0(3) . . ? N13 C23 C13' 109.7(2) . . ? O13' C33' C23' 125.1(3) . . ? O13' C33' C43' 115.1(3) . . ? C23' C33' C43' 119.8(3) . . ? C32' O22' C82' 117.2(2) . . ? C44' O24' C84' 116.9(2) . . ? C42' O12' C72' 115.7(2) . . ? C24 N34 C44 111.5(3) . . ? C34' O14' C74' 117.3(2) . . ? C102 N12 C22 115.3(2) . . ? C22 N32 C42 111.1(3) . . ? C54' C44' O24' 125.1(3) . . ? C54' C44' C34' 119.6(3) . . ? O24' C44' C34' 115.3(3) . . ? N34 C24 N14 110.9(3) . . ? N34 C24 C14' 110.4(3) . . ? N14 C24 C14' 111.0(3) . . ? C82 C92 C102 120.4(3) . . ? C72 C62 C52 122.0(3) . . ? C94 C104 N14 120.4(3) . . ? C94 C104 C54 119.1(3) . . ? N14 C104 C54 120.5(3) . . ? C104 N14 C24 116.0(2) . . ? C64 C54 C104 118.8(3) . . ? C64 C54 C44 121.5(3) . . ? C104 C54 C44 119.7(3) . . ? C62' C12' C22' 119.1(3) . . ? C62' C12' C22 119.9(3) . . ? C22' C12' C22 121.0(3) . . ? O22' C32' C22' 125.1(3) . . ? O22' C32' C42' 115.1(3) . . ? C22' C32' C42' 119.8(3) . . ? O12' C42' C52' 125.0(3) . . ? O12' C42' C32' 115.0(3) . . ? C52' C42' C32' 119.9(3) . . ? N32 C22 N12 110.8(3) . . ? N32 C22 C12' 112.2(3) . . ? N12 C22 C12' 110.7(2) . . ? O14' C34' C24' 124.8(3) . . ? O14' C34' C44' 115.6(3) . . ? C24' C34' C44' 119.5(3) . . ? C62 C72 C82 118.9(3) . . ? C34' C24' C14' 120.2(3) . . ? N32 C42 C52 115.3(3) . . ? C12' C62' C52' 121.1(3) . . ? N12 C102 C92 120.7(3) . . ? N12 C102 C52 119.1(3) . . ? C92 C102 C52 120.2(3) . . ? C84 C94 C104 121.2(3) . . ? C32' C22' C12' 120.3(3) . . ? C94 C84 C74 119.8(4) . . ? C42' C52' C62' 119.7(3) . . ? C64' C14' C24' 119.5(3) . . ? C64' C14' C24 120.1(3) . . ? C24' C14' C24 120.3(3) . . ? C14' C64' C54' 120.7(3) . . ? C92 C82 C72 120.7(3) . . ? N34 C44 C54 113.7(3) . . ? C74 C64 C54 121.5(3) . . ? C62 C52 C102 117.8(3) . . ? C62 C52 C42 121.8(3) . . ? C102 C52 C42 120.4(3) . . ? C64 C74 C84 119.5(3) . . ? C44' C54' C64' 120.4(3) . . ? C31' O11' C71' 116.7(2) . . ? C21 N31 C41 110.6(3) . . ? C41' O21' C81' 116.8(2) . . ? O21' C41' C51' 125.7(3) . . ? O21' C41' C31' 115.0(3) . . ? C51' C41' C31' 119.3(3) . . ? O11' C31' C21' 124.6(3) . . ? O11' C31' C41' 115.0(3) . . ? C21' C31' C41' 120.4(3) . . ? C101 N11 C21 115.6(3) . . ? C91 C81 C71 120.4(4) . . ? N31 C21 N11 109.8(3) . . ? N31 C21 C11' 110.7(3) . . ? N11 C21 C11' 111.5(2) . . ? C91 C101 N11 120.1(3) . . ? C91 C101 C51 119.6(3) . . ? N11 C101 C51 120.3(3) . . ? C11' C61' C51' 120.8(3) . . ? C81 C91 C101 120.4(3) . . ? C61 C51 C101 119.0(3) . . ? C61 C51 C41 121.3(3) . . ? C101 C51 C41 119.7(3) . . ? C71 C61 C51 121.4(3) . . ? C31' C21' C11' 120.1(3) . . ? C61' C11' C21' 119.2(3) . . ? C61' C11' C21 120.0(3) . . ? C21' C11' C21 120.8(3) . . ? C41' C51' C61' 120.0(3) . . ? C61 C71 C81 119.2(3) . . ? N31 C41 C51 114.7(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.251 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.060 data_5e _database_code_CSD 177053 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-2[(salicylideneimino)benzyl]-salicylideneimine ; _chemical_name_common 'N-2[(salicylideneimino)benzyl]-salicylideneimine' _chemical_melting_point '102.8-105.8 Deg. C' _chemical_formula_moiety 'C21 H18 N2 O2' _chemical_formula_sum 'C21 H18 N2 O2' _chemical_formula_weight 330.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 9.7200(2) _cell_length_b 14.0370(2) _cell_length_c 12.20580(10) _cell_angle_alpha 90.00 _cell_angle_beta 97.056(2) _cell_angle_gamma 90.00 _cell_volume 1652.74(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _exptl_crystal_description rhombs _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 Kappa CCD' _diffrn_measurement_method '\phi + w scans' _diffrn_reflns_number 24372 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 29.75 _reflns_number_total 4542 _reflns_number_gt 2820 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement 'Nonius Collect' _computing_data_reduction 'Nonius Collect' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Xseed' _computing_publication_material 'Ciftab' _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^)+(0.0693P)^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_number_reflns 4542 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1256 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.82202(11) 0.12898(7) 0.50313(8) 0.0278(3) Uani 1 1 d . . . N2 N 0.56579(11) 0.09743(7) 0.75601(8) 0.0255(2) Uani 1 1 d . . . O1" O 0.94594(10) 0.04154(6) 0.35714(8) 0.0344(2) Uani 1 1 d . . . O1' O 0.75978(9) 0.02774(7) 0.89987(8) 0.0358(2) Uani 1 1 d . . . C7' C 0.50465(13) 0.12705(8) 0.83628(10) 0.0263(3) Uani 1 1 d . . . H7' H 0.4192 0.1601 0.8207 0.032 Uiso 1 1 calc R . . C7 C 0.74349(13) 0.13048(10) 0.59706(10) 0.0300(3) Uani 1 1 d . . . H7A H 0.7622 0.1911 0.6377 0.036 Uiso 1 1 calc R . . H7B H 0.7757 0.0778 0.6477 0.036 Uiso 1 1 calc R . . C2 C 0.58895(13) 0.12078(8) 0.56428(10) 0.0242(3) Uani 1 1 d . . . C1 C 0.50264(13) 0.10827(8) 0.64648(10) 0.0239(3) Uani 1 1 d . . . C1" C 0.95104(13) 0.21200(9) 0.37958(11) 0.0270(3) Uani 1 1 d . . . C6 C 0.35910(13) 0.10197(8) 0.61888(10) 0.0272(3) Uani 1 1 d . . . H6 H 0.3014 0.0925 0.6753 0.033 Uiso 1 1 calc R . . C4 C 0.38497(14) 0.12213(9) 0.42940(11) 0.0297(3) Uani 1 1 d . . . H4 H 0.3453 0.1272 0.3545 0.036 Uiso 1 1 calc R . . C3 C 0.52830(14) 0.12756(8) 0.45649(10) 0.0279(3) Uani 1 1 d . . . H3 H 0.5854 0.1361 0.3994 0.033 Uiso 1 1 calc R . . C2" C 0.98497(13) 0.12892(9) 0.32495(10) 0.0275(3) Uani 1 1 d . . . C5 C 0.30079(14) 0.10939(9) 0.51114(11) 0.0298(3) Uani 1 1 d . . . H5 H 0.2031 0.1058 0.4930 0.036 Uiso 1 1 calc R . . C6" C 0.99413(14) 0.30014(10) 0.34271(12) 0.0351(3) Uani 1 1 d . . . H6" H 0.9722 0.3566 0.3798 0.042 Uiso 1 1 calc R . . C1' C 0.56072(13) 0.11202(8) 0.94957(10) 0.0262(3) Uani 1 1 d . . . C5' C 0.54103(16) 0.13328(9) 1.14216(11) 0.0353(3) Uani 1 1 d . . . H5' H 0.4918 0.1569 1.1990 0.042 Uiso 1 1 calc R . . C3' C 0.73837(15) 0.05065(10) 1.08741(11) 0.0338(3) Uani 1 1 d . . . H3' H 0.8237 0.0182 1.1067 0.041 Uiso 1 1 calc R . . C3" C 1.06111(14) 0.13562(10) 0.23648(12) 0.0341(3) Uani 1 1 d . . . H3" H 1.0856 0.0796 0.1997 0.041 Uiso 1 1 calc R . . C2' C 0.68660(14) 0.06244(9) 0.97787(11) 0.0283(3) Uani 1 1 d . . . C7" C 0.87141(13) 0.20752(9) 0.47234(10) 0.0271(3) Uani 1 1 d . . . H7" H 0.8556 0.2643 0.5112 0.033 Uiso 1 1 calc R . . C6' C 0.48906(15) 0.14566(9) 1.03365(10) 0.0312(3) Uani 1 1 d . . . H6' H 0.4031 0.1776 1.0155 0.037 Uiso 1 1 calc R . . C4" C 1.10125(14) 0.22393(11) 0.20197(12) 0.0392(4) Uani 1 1 d . . . H4" H 1.1533 0.2281 0.1411 0.047 Uiso 1 1 calc R . . C5" C 1.06717(15) 0.30639(11) 0.25426(13) 0.0414(4) Uani 1 1 d . . . H5" H 1.0942 0.3668 0.2290 0.050 Uiso 1 1 calc R . . C4' C 0.66626(16) 0.08598(9) 1.16845(11) 0.0359(3) Uani 1 1 d . . . H4' H 0.7026 0.0779 1.2437 0.043 Uiso 1 1 calc R . . H1'O H 0.7131 0.0396 0.8259 0.079(6) Uiso 1 1 d R . . H1"O H 0.8981 0.0554 0.4168 0.081(7) Uiso 1 1 d 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 0.0260(6) 0.0352(6) 0.0228(6) 0.0004(4) 0.0062(5) -0.0009(5) N2 0.0274(6) 0.0285(5) 0.0216(6) 0.0022(4) 0.0066(5) -0.0008(4) O1" 0.0397(6) 0.0316(5) 0.0334(6) -0.0013(4) 0.0106(5) 0.0007(4) O1' 0.0296(5) 0.0498(6) 0.0287(6) 0.0033(4) 0.0060(4) 0.0054(4) C7' 0.0270(7) 0.0274(6) 0.0252(7) 0.0022(5) 0.0057(5) 0.0001(5) C7 0.0274(7) 0.0410(8) 0.0225(7) -0.0002(5) 0.0066(5) -0.0022(6) C2 0.0271(7) 0.0231(6) 0.0227(7) 0.0005(5) 0.0047(5) 0.0009(5) C1 0.0270(7) 0.0235(6) 0.0214(6) 0.0014(4) 0.0043(5) 0.0028(5) C1" 0.0204(6) 0.0335(7) 0.0271(7) 0.0039(5) 0.0033(5) 0.0005(5) C6 0.0261(7) 0.0285(6) 0.0282(7) 0.0007(5) 0.0079(6) 0.0036(5) C4 0.0342(8) 0.0316(7) 0.0222(7) -0.0001(5) -0.0011(6) 0.0020(6) C3 0.0326(7) 0.0294(7) 0.0226(7) -0.0002(5) 0.0071(5) 0.0009(5) C2" 0.0212(6) 0.0352(7) 0.0254(7) 0.0034(5) 0.0005(5) 0.0006(5) C5 0.0256(7) 0.0321(7) 0.0314(8) 0.0003(5) 0.0017(6) 0.0036(5) C6" 0.0275(7) 0.0333(7) 0.0452(9) 0.0053(6) 0.0070(6) -0.0002(6) C1' 0.0296(7) 0.0252(6) 0.0242(7) 0.0016(5) 0.0052(5) -0.0042(5) C5' 0.0495(9) 0.0345(7) 0.0233(7) -0.0010(5) 0.0100(6) -0.0049(6) C3' 0.0318(7) 0.0372(7) 0.0313(8) 0.0058(6) -0.0006(6) -0.0052(6) C3" 0.0255(7) 0.0484(9) 0.0287(7) -0.0020(6) 0.0039(6) 0.0042(6) C2' 0.0280(7) 0.0308(7) 0.0267(7) 0.0013(5) 0.0051(6) -0.0052(5) C7" 0.0233(7) 0.0303(7) 0.0280(7) -0.0009(5) 0.0038(5) 0.0011(5) C6' 0.0396(8) 0.0293(7) 0.0261(7) 0.0014(5) 0.0090(6) 0.0009(6) C4" 0.0238(7) 0.0625(10) 0.0323(8) 0.0106(7) 0.0070(6) -0.0006(6) C5" 0.0295(8) 0.0466(9) 0.0499(10) 0.0178(7) 0.0116(7) -0.0020(6) C4' 0.0468(9) 0.0375(8) 0.0223(7) 0.0038(5) -0.0008(6) -0.0104(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 N1 C7" 1.2773(15) . ? N1 C7 1.4535(16) . ? N2 C7' 1.2764(16) . ? N2 C1 1.4091(16) . ? O1" C2" 1.3562(15) . ? O1' C2' 1.3477(15) . ? C7' C1' 1.4382(17) . ? C7 C2 1.5124(18) . ? C2 C3 1.3773(17) . ? C2 C1 1.3958(17) . ? C1 C6 1.3973(17) . ? C1" C6" 1.3982(18) . ? C1" C2" 1.4027(17) . ? C1" C7" 1.4493(17) . ? C6 C5 1.3705(17) . ? C4 C5 1.3774(18) . ? C4 C3 1.3939(19) . ? C2" C3" 1.3852(19) . ? C6" C5" 1.3659(19) . ? C1' C6' 1.3916(17) . ? C1' C2' 1.4131(19) . ? C5' C6' 1.3694(18) . ? C5' C4' 1.389(2) . ? C3' C4' 1.3734(19) . ? C3' C2' 1.3794(18) . ? C3" C4" 1.381(2) . ? C4" C5" 1.382(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" N1 C7 118.19(11) . . ? C7' N2 C1 120.23(11) . . ? N2 C7' C1' 122.21(12) . . ? N1 C7 C2 113.00(10) . . ? C3 C2 C1 118.09(12) . . ? C3 C2 C7 122.77(11) . . ? C1 C2 C7 119.10(11) . . ? C2 C1 C6 120.34(11) . . ? C2 C1 N2 117.73(11) . . ? C6 C1 N2 121.84(11) . . ? C6" C1" C2" 119.05(12) . . ? C6" C1" C7" 119.98(12) . . ? C2" C1" C7" 120.97(11) . . ? C5 C6 C1 120.63(12) . . ? C5 C4 C3 120.04(12) . . ? C2 C3 C4 121.39(12) . . ? O1" C2" C3" 118.85(12) . . ? O1" C2" C1" 121.58(11) . . ? C3" C2" C1" 119.57(12) . . ? C6 C5 C4 119.50(12) . . ? C5" C6" C1" 121.10(13) . . ? C6' C1' C2' 118.92(12) . . ? C6' C1' C7' 119.63(12) . . ? C2' C1' C7' 121.45(12) . . ? C6' C5' C4' 119.52(13) . . ? C4' C3' C2' 119.80(13) . . ? C4" C3" C2" 119.79(13) . . ? O1' C2' C3' 118.68(12) . . ? O1' C2' C1' 121.44(11) . . ? C3' C2' C1' 119.86(12) . . ? N1 C7" C1" 121.56(11) . . ? C5' C6' C1' 120.77(13) . . ? C3" C4" C5" 121.23(13) . . ? C6" C5" C4" 119.26(13) . . ? C3' C4' C5' 121.10(13) . . ? 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 N2 C7' C1' 175.84(10) . . . . ? C7" N1 C7 C2 105.17(13) . . . . ? N1 C7 C2 C3 -11.20(16) . . . . ? N1 C7 C2 C1 171.49(11) . . . . ? C3 C2 C1 C6 0.63(17) . . . . ? C7 C2 C1 C6 178.07(11) . . . . ? C3 C2 C1 N2 177.42(10) . . . . ? C7 C2 C1 N2 -5.14(16) . . . . ? C7' N2 C1 C2 148.81(12) . . . . ? C7' N2 C1 C6 -34.45(16) . . . . ? C2 C1 C6 C5 -0.98(18) . . . . ? N2 C1 C6 C5 -177.64(11) . . . . ? C1 C2 C3 C4 -0.03(17) . . . . ? C7 C2 C3 C4 -177.37(12) . . . . ? C5 C4 C3 C2 -0.23(18) . . . . ? C6" C1" C2" O1" 179.98(12) . . . . ? C7" C1" C2" O1" -0.59(19) . . . . ? C6" C1" C2" C3" 0.51(19) . . . . ? C7" C1" C2" C3" 179.94(12) . . . . ? C1 C6 C5 C4 0.71(18) . . . . ? C3 C4 C5 C6 -0.11(18) . . . . ? C2" C1" C6" C5" 0.6(2) . . . . ? C7" C1" C6" C5" -178.84(12) . . . . ? N2 C7' C1' C6' -179.75(11) . . . . ? N2 C7' C1' C2' -0.67(18) . . . . ? O1" C2" C3" C4" 179.64(12) . . . . ? C1" C2" C3" C4" -0.9(2) . . . . ? C4' C3' C2' O1' 179.52(11) . . . . ? C4' C3' C2' C1' 0.93(19) . . . . ? C6' C1' C2' O1' 179.53(11) . . . . ? C7' C1' C2' O1' 0.45(18) . . . . ? C6' C1' C2' C3' -1.92(18) . . . . ? C7' C1' C2' C3' 178.99(11) . . . . ? C7 N1 C7" C1" 179.90(11) . . . . ? C6" C1" C7" N1 174.93(12) . . . . ? C2" C1" C7" N1 -4.50(19) . . . . ? C4' C5' C6' C1' -0.47(19) . . . . ? C2' C1' C6' C5' 1.69(18) . . . . ? C7' C1' C6' C5' -179.21(11) . . . . ? C2" C3" C4" C5" 0.1(2) . . . . ? C1" C6" C5" C4" -1.3(2) . . . . ? C3" C4" C5" C6" 1.0(2) . . . . ? C2' C3' C4' C5' 0.3(2) . . . . ? C6' C5' C4' C3' -0.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 29.75 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.200 _refine_diff_density_min -0.260 _refine_diff_density_rms 0.053