data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; AG-4 2-(2,6-dichlorophenylamino)-PhCH2COOH, 2-aminopyrimidine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C14 H11 N O2 Cl2) (C4 H5 N3) ; _chemical_formula_sum 'C18 H16 Cl2 N4 O2' _chemical_formula_weight 391.25 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' 'Cl' 'Cl' 0.1484 0.1585 '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 7.4961(7) _cell_length_b 8.7028(8) _cell_length_c 13.8697(12) _cell_angle_alpha 76.747(2) _cell_angle_beta 87.392(3) _cell_angle_gamma 86.408(2) _cell_volume 878.54(14) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9964 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 32.15 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.391 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8985 _exptl_absorpt_correction_T_max 0.9473 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27648 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 32.54 _reflns_number_total 6204 _reflns_number_gt 4910 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6204 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1072 _refine_ls_wR_factor_gt 0.0996 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 Cl1 Cl 0.71638(4) 0.09097(4) 0.01874(3) 0.02913(9) Uani 1 1 d . . . Cl2 Cl 0.83026(5) 0.14053(5) 0.39341(3) 0.03810(10) Uani 1 1 d . . . C11 C 0.43489(15) 0.43605(13) 0.13029(8) 0.0179(2) Uani 1 1 d . . . C17 C 0.55385(17) 0.57250(14) 0.12473(9) 0.0209(2) Uani 1 1 d . . . H17A H 0.6791 0.5392 0.1105 0.025 Uiso 1 1 calc R . . H17B H 0.5161 0.6618 0.0701 0.025 Uiso 1 1 calc R . . C18 C 0.54269(16) 0.62542(13) 0.22129(9) 0.0201(2) Uani 1 1 d . . . O11 O 0.63549(13) 0.53067(11) 0.29151(7) 0.02580(19) Uani 1 1 d . . . H11 H 0.628(2) 0.568(2) 0.3500(13) 0.031 Uiso 1 1 d . . . O12 O 0.45282(13) 0.74196(11) 0.23264(7) 0.0275(2) Uani 1 1 d . . . C12 C 0.50056(15) 0.27836(13) 0.16162(8) 0.0172(2) Uani 1 1 d . . . N12 N 0.67806(13) 0.24968(12) 0.19366(8) 0.02016(19) Uani 1 1 d . . . H12 H 0.703(2) 0.3015(19) 0.2378(12) 0.024 Uiso 1 1 d . . . C13 C 0.38975(15) 0.15536(14) 0.16100(9) 0.0196(2) Uani 1 1 d . . . H13 H 0.4348 0.0487 0.1804 0.024 Uiso 1 1 calc R . . C14 C 0.21427(16) 0.18852(15) 0.13214(9) 0.0216(2) Uani 1 1 d . . . H14 H 0.1402 0.1043 0.1312 0.026 Uiso 1 1 calc R . . C15 C 0.14568(16) 0.34396(15) 0.10456(10) 0.0236(2) Uani 1 1 d . . . H15 H 0.0244 0.3663 0.0865 0.028 Uiso 1 1 calc R . . C16 C 0.25685(16) 0.46610(14) 0.10373(9) 0.0212(2) Uani 1 1 d . . . H16 H 0.2105 0.5724 0.0846 0.025 Uiso 1 1 calc R . . C21 C 0.76993(15) 0.10186(14) 0.20983(10) 0.0216(2) Uani 1 1 d . . . C22 C 0.79654(16) 0.01542(14) 0.13614(11) 0.0246(2) Uani 1 1 d . . . C23 C 0.89660(19) -0.12750(16) 0.15180(14) 0.0362(4) Uani 1 1 d . . . H23 H 0.9072 -0.1862 0.1017 0.043 Uiso 1 1 calc R . . C24 C 0.9806(2) -0.18375(18) 0.24077(16) 0.0472(5) Uani 1 1 d . . . H24 H 1.0524 -0.2797 0.2510 0.057 Uiso 1 1 calc R . . C25 C 0.9605(2) -0.1010(2) 0.31456(14) 0.0435(4) Uani 1 1 d . . . H25 H 1.0186 -0.1394 0.3756 0.052 Uiso 1 1 calc R . . C26 C 0.85514(18) 0.03851(17) 0.29922(11) 0.0297(3) Uani 1 1 d . . . N31 N 0.65257(14) 0.62621(12) 0.45608(8) 0.0218(2) Uani 1 1 d . . . C32 C 0.58917(16) 0.76479(14) 0.47647(9) 0.0209(2) Uani 1 1 d . . . N32 N 0.47411(16) 0.85520(14) 0.41405(9) 0.0270(2) Uani 1 1 d . . . H32A H 0.454(2) 0.828(2) 0.3544(14) 0.032 Uiso 1 1 d . . . H32B H 0.442(2) 0.951(2) 0.4200(13) 0.032 Uiso 1 1 d . . . N33 N 0.63314(15) 0.81671(13) 0.55687(8) 0.0235(2) Uani 1 1 d . . . C34 C 0.74532(18) 0.72303(16) 0.61846(10) 0.0254(2) Uani 1 1 d . . . H34 H 0.7785 0.7563 0.6754 0.031 Uiso 1 1 calc R . . C35 C 0.8164(2) 0.57914(17) 0.60375(10) 0.0302(3) Uani 1 1 d . . . H35 H 0.8968 0.5141 0.6487 0.036 Uiso 1 1 calc R . . C36 C 0.76409(19) 0.53554(15) 0.52053(10) 0.0273(3) Uani 1 1 d . . . H36 H 0.8091 0.4370 0.5084 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.02603(15) 0.03168(16) 0.03435(18) -0.01837(13) 0.00359(12) -0.00033(11) Cl2 0.02870(18) 0.0565(2) 0.02611(17) -0.00159(15) -0.00542(13) -0.00521(15) C11 0.0192(5) 0.0184(5) 0.0176(5) -0.0072(4) 0.0002(4) -0.0008(4) C17 0.0233(6) 0.0191(5) 0.0211(5) -0.0065(4) 0.0012(4) -0.0025(4) C18 0.0208(5) 0.0166(5) 0.0242(6) -0.0073(4) 0.0001(4) -0.0025(4) O11 0.0335(5) 0.0222(4) 0.0240(4) -0.0110(3) -0.0061(4) 0.0058(3) O12 0.0324(5) 0.0228(4) 0.0295(5) -0.0117(4) -0.0048(4) 0.0063(4) C12 0.0152(5) 0.0198(5) 0.0177(5) -0.0074(4) 0.0010(4) 0.0000(4) N12 0.0163(4) 0.0189(4) 0.0270(5) -0.0086(4) -0.0039(4) 0.0011(3) C13 0.0179(5) 0.0196(5) 0.0227(5) -0.0081(4) 0.0019(4) -0.0011(4) C14 0.0172(5) 0.0268(6) 0.0234(6) -0.0111(4) 0.0016(4) -0.0037(4) C15 0.0162(5) 0.0312(6) 0.0250(6) -0.0104(5) -0.0014(4) 0.0014(4) C16 0.0196(5) 0.0230(5) 0.0211(5) -0.0065(4) -0.0018(4) 0.0034(4) C21 0.0140(5) 0.0190(5) 0.0297(6) -0.0016(4) 0.0017(4) -0.0016(4) C22 0.0174(5) 0.0180(5) 0.0381(7) -0.0066(5) 0.0055(5) -0.0015(4) C23 0.0260(7) 0.0173(6) 0.0628(10) -0.0069(6) 0.0136(7) 0.0001(5) C24 0.0328(8) 0.0233(7) 0.0726(13) 0.0102(7) 0.0123(8) 0.0091(6) C25 0.0273(7) 0.0382(8) 0.0500(10) 0.0182(7) 0.0018(7) 0.0073(6) C26 0.0189(6) 0.0325(7) 0.0318(7) 0.0046(5) 0.0013(5) -0.0005(5) N31 0.0238(5) 0.0194(5) 0.0232(5) -0.0074(4) 0.0000(4) -0.0010(4) C32 0.0210(5) 0.0215(5) 0.0216(5) -0.0082(4) 0.0023(4) -0.0012(4) N32 0.0314(6) 0.0254(5) 0.0274(6) -0.0139(4) -0.0067(5) 0.0070(4) N33 0.0235(5) 0.0268(5) 0.0223(5) -0.0106(4) 0.0002(4) 0.0003(4) C34 0.0244(6) 0.0331(6) 0.0200(6) -0.0090(5) 0.0003(5) -0.0004(5) C35 0.0354(7) 0.0283(6) 0.0258(6) -0.0044(5) -0.0057(5) 0.0039(5) C36 0.0324(7) 0.0211(6) 0.0283(6) -0.0061(5) -0.0012(5) 0.0021(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 Cl1 C22 1.7301(15) . ? Cl2 C26 1.7374(17) . ? C11 C16 1.3936(17) . ? C11 C12 1.4056(16) . ? C11 C17 1.5152(16) . ? C17 C18 1.5102(16) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O12 1.2187(14) . ? C18 O11 1.3168(15) . ? O11 H11 0.940(18) . ? C12 C13 1.3973(16) . ? C12 N12 1.4112(15) . ? N12 C21 1.3965(15) . ? N12 H12 0.873(17) . ? C13 C14 1.3861(17) . ? C13 H13 0.9500 . ? C14 C15 1.3908(18) . ? C14 H14 0.9500 . ? C15 C16 1.3889(17) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.4013(19) . ? C21 C22 1.4019(18) . ? C22 C23 1.3895(18) . ? C23 C24 1.384(3) . ? C23 H23 0.9500 . ? C24 C25 1.378(3) . ? C24 H24 0.9500 . ? C25 C26 1.386(2) . ? C25 H25 0.9500 . ? N31 C36 1.3351(17) . ? N31 C32 1.3537(15) . ? C32 N32 1.3353(17) . ? C32 N33 1.3563(15) . ? N32 H32A 0.931(18) . ? N32 H32B 0.876(18) . ? N33 C34 1.3273(17) . ? C34 C35 1.3846(19) . ? C34 H34 0.9500 . ? C35 C36 1.3749(19) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C11 C12 118.87(10) . . ? C16 C11 C17 119.85(10) . . ? C12 C11 C17 121.27(10) . . ? C18 C17 C11 110.46(10) . . ? C18 C17 H17A 109.6 . . ? C11 C17 H17A 109.6 . . ? C18 C17 H17B 109.6 . . ? C11 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? O12 C18 O11 124.15(11) . . ? O12 C18 C17 122.76(11) . . ? O11 C18 C17 113.07(10) . . ? C18 O11 H11 111.0(11) . . ? C13 C12 C11 119.74(11) . . ? C13 C12 N12 121.97(10) . . ? C11 C12 N12 118.29(10) . . ? C21 N12 C12 124.02(10) . . ? C21 N12 H12 111.3(11) . . ? C12 N12 H12 113.9(11) . . ? C14 C13 C12 120.18(11) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.62(11) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 119.09(11) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C11 121.42(11) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? N12 C21 C26 120.84(12) . . ? N12 C21 C22 122.78(12) . . ? C26 C21 C22 116.13(12) . . ? C23 C22 C21 122.03(14) . . ? C23 C22 Cl1 117.47(12) . . ? C21 C22 Cl1 120.37(9) . . ? C24 C23 C22 119.60(16) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C25 C24 C23 120.18(14) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 119.58(16) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C25 C26 C21 122.41(15) . . ? C25 C26 Cl2 118.92(13) . . ? C21 C26 Cl2 118.66(10) . . ? C36 N31 C32 117.06(11) . . ? N32 C32 N31 117.86(11) . . ? N32 C32 N33 117.90(11) . . ? N31 C32 N33 124.23(11) . . ? C32 N32 H32A 119.1(11) . . ? C32 N32 H32B 120.3(12) . . ? H32A N32 H32B 118.3(16) . . ? C34 N33 C32 116.52(11) . . ? N33 C34 C35 123.23(12) . . ? N33 C34 H34 118.4 . . ? C35 C34 H34 118.4 . . ? C36 C35 C34 116.34(13) . . ? C36 C35 H35 121.8 . . ? C34 C35 H35 121.8 . . ? N31 C36 C35 122.61(12) . . ? N31 C36 H36 118.7 . . ? C35 C36 H36 118.7 . . ? 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 C16 C11 C17 C18 89.11(13) . . . . ? C12 C11 C17 C18 -91.07(13) . . . . ? C11 C17 C18 O12 -101.19(14) . . . . ? C11 C17 C18 O11 77.08(13) . . . . ? C16 C11 C12 C13 3.10(16) . . . . ? C17 C11 C12 C13 -176.72(10) . . . . ? C16 C11 C12 N12 -176.46(10) . . . . ? C17 C11 C12 N12 3.72(16) . . . . ? C13 C12 N12 C21 12.25(18) . . . . ? C11 C12 N12 C21 -168.20(11) . . . . ? C11 C12 C13 C14 -1.72(17) . . . . ? N12 C12 C13 C14 177.82(11) . . . . ? C12 C13 C14 C15 -0.71(18) . . . . ? C13 C14 C15 C16 1.71(18) . . . . ? C14 C15 C16 C11 -0.27(18) . . . . ? C12 C11 C16 C15 -2.13(18) . . . . ? C17 C11 C16 C15 177.70(11) . . . . ? C12 N12 C21 C26 -128.50(13) . . . . ? C12 N12 C21 C22 57.43(17) . . . . ? N12 C21 C22 C23 176.42(12) . . . . ? C26 C21 C22 C23 2.08(18) . . . . ? N12 C21 C22 Cl1 0.60(16) . . . . ? C26 C21 C22 Cl1 -173.73(9) . . . . ? C21 C22 C23 C24 -3.3(2) . . . . ? Cl1 C22 C23 C24 172.65(11) . . . . ? C22 C23 C24 C25 2.1(2) . . . . ? C23 C24 C25 C26 0.2(2) . . . . ? C24 C25 C26 C21 -1.4(2) . . . . ? C24 C25 C26 Cl2 179.60(12) . . . . ? N12 C21 C26 C25 -174.17(13) . . . . ? C22 C21 C26 C25 0.28(19) . . . . ? N12 C21 C26 Cl2 4.80(16) . . . . ? C22 C21 C26 Cl2 179.25(9) . . . . ? C36 N31 C32 N32 -178.42(12) . . . . ? C36 N31 C32 N33 0.66(18) . . . . ? N32 C32 N33 C34 178.85(12) . . . . ? N31 C32 N33 C34 -0.23(18) . . . . ? C32 N33 C34 C35 0.0(2) . . . . ? N33 C34 C35 C36 -0.2(2) . . . . ? C32 N31 C36 C35 -0.9(2) . . . . ? C34 C35 C36 N31 0.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O11 H11 N31 0.940(18) 1.682(18) 2.6130(14) 170.2(17) . N12 H12 O11 0.873(17) 2.305(17) 3.0510(13) 143.5(14) . N32 H32A O12 0.931(18) 2.000(19) 2.9191(15) 168.7(16) . N32 H32B N33 0.876(18) 2.153(19) 3.0286(15) 176.9(17) 2_676 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 32.54 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.461 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.059 #END data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; AG-2 2-(2,6-dichlorophenylamino)-PhCH2COOH, 2-amino-4,6-dimethypyrimidine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C14 H11 N O2 Cl2) (C6 H9 N3) ; _chemical_formula_sum 'C20 H20 Cl2 N4 O2' _chemical_formula_weight 419.30 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.270(2) _cell_length_b 4.6992(5) _cell_length_c 20.494(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.562(7) _cell_angle_gamma 90.00 _cell_volume 1950.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3792 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 29.66 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9066 _exptl_absorpt_correction_T_max 0.9859 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19020 _diffrn_reflns_av_R_equivalents 0.0952 _diffrn_reflns_av_sigmaI/netI 0.1038 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 30.03 _reflns_number_total 5670 _reflns_number_gt 3166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.041(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5670 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1340 _refine_ls_R_factor_gt 0.0787 _refine_ls_wR_factor_ref 0.2152 _refine_ls_wR_factor_gt 0.1862 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 Cl1 Cl 0.95433(4) 0.75154(18) 0.51965(5) 0.0310(2) Uani 1 1 d . . . Cl2 Cl 0.78560(4) 0.1069(2) 0.58525(5) 0.0353(3) Uani 1 1 d . . . C11 C 0.76051(14) 0.6332(7) 0.36812(18) 0.0257(7) Uani 1 1 d . . . C17 C 0.71595(15) 0.8367(7) 0.38498(19) 0.0286(7) Uani 1 1 d . . . H17A H 0.6953 0.9702 0.3443 0.034 Uiso 1 1 calc R . . H17B H 0.7430 0.9499 0.4279 0.034 Uiso 1 1 calc R . . C18 C 0.66196(14) 0.6841(7) 0.39856(17) 0.0246(7) Uani 1 1 d . . . O11 O 0.60287(10) 0.7843(5) 0.36182(13) 0.0296(6) Uani 1 1 d . . . H11 H 0.5684(18) 0.696(8) 0.373(2) 0.036 Uiso 1 1 d . . . O12 O 0.67431(11) 0.4867(5) 0.44107(14) 0.0359(6) Uani 1 1 d . . . C12 C 0.81164(14) 0.4840(7) 0.42223(17) 0.0242(7) Uani 1 1 d . . . N12 N 0.81958(13) 0.5172(6) 0.49440(15) 0.0279(6) Uani 1 1 d . . . H12 H 0.7775(18) 0.503(7) 0.5005(19) 0.034 Uiso 1 1 d . . . C13 C 0.85189(15) 0.3035(7) 0.40411(19) 0.0286(7) Uani 1 1 d . . . H13 H 0.8863 0.2016 0.4408 0.034 Uiso 1 1 calc R . . C14 C 0.84235(15) 0.2706(8) 0.33334(19) 0.0308(8) Uani 1 1 d . . . H14 H 0.8705 0.1485 0.3218 0.037 Uiso 1 1 calc R . . C15 C 0.79219(16) 0.4145(8) 0.27983(19) 0.0338(8) Uani 1 1 d . . . H15 H 0.7852 0.3907 0.2312 0.041 Uiso 1 1 calc R . . C16 C 0.75171(15) 0.5954(8) 0.29754(18) 0.0294(8) Uani 1 1 d . . . H16 H 0.7173 0.6954 0.2604 0.035 Uiso 1 1 calc R . . C21 C 0.87362(15) 0.4076(7) 0.55331(17) 0.0254(7) Uani 1 1 d . . . C22 C 0.93888(15) 0.4933(7) 0.57127(18) 0.0284(7) Uani 1 1 d . . . C23 C 0.99215(15) 0.3823(7) 0.62929(18) 0.0294(7) Uani 1 1 d . . . H23 H 1.0359 0.4376 0.6379 0.035 Uiso 1 1 calc R . . C24 C 0.98141(16) 0.1913(8) 0.67441(19) 0.0319(8) Uani 1 1 d . . . H24 H 1.0177 0.1155 0.7145 0.038 Uiso 1 1 calc R . . C25 C 0.91751(16) 0.1103(8) 0.66107(18) 0.0315(8) Uani 1 1 d . . . H25 H 0.9096 -0.0175 0.6925 0.038 Uiso 1 1 calc R . . C26 C 0.86541(15) 0.2174(8) 0.60150(19) 0.0292(8) Uani 1 1 d . . . N31 N 0.50173(12) 0.5381(6) 0.37480(15) 0.0252(6) Uani 1 1 d . . . C32 C 0.50157(14) 0.3353(7) 0.42187(17) 0.0227(7) Uani 1 1 d . . . N32 N 0.55917(13) 0.2115(7) 0.46332(16) 0.0283(7) Uani 1 1 d . . . H32A H 0.5972(17) 0.281(7) 0.459(2) 0.034 Uiso 1 1 d . . . H32B H 0.5639(17) 0.076(8) 0.493(2) 0.034 Uiso 1 1 d . . . N33 N 0.44738(12) 0.2486(6) 0.43069(15) 0.0257(6) Uani 1 1 d . . . C34 C 0.39009(15) 0.3709(7) 0.38849(18) 0.0257(7) Uani 1 1 d . . . C35 C 0.38581(15) 0.5733(7) 0.33769(18) 0.0274(7) Uani 1 1 d . . . H35 H 0.3445 0.6550 0.3075 0.033 Uiso 1 1 calc R . . C36 C 0.44346(14) 0.6541(7) 0.33195(18) 0.0239(7) Uani 1 1 d . . . C44 C 0.33075(16) 0.2730(8) 0.3990(2) 0.0319(8) Uani 1 1 d . . . H44A H 0.3267 0.0659 0.3935 0.048 Uiso 1 1 calc R . . H44B H 0.2911 0.3635 0.3632 0.048 Uiso 1 1 calc R . . H44C H 0.3356 0.3257 0.4472 0.048 Uiso 1 1 calc R . . C46 C 0.44258(16) 0.8651(8) 0.27754(19) 0.0303(8) Uani 1 1 d . . . H46A H 0.4852 0.9632 0.2949 0.045 Uiso 1 1 calc R . . H46B H 0.4074 1.0043 0.2694 0.045 Uiso 1 1 calc R . . H46C H 0.4345 0.7669 0.2325 0.045 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0294(4) 0.0346(5) 0.0344(5) 0.0033(4) 0.0187(4) -0.0006(3) Cl2 0.0290(4) 0.0541(6) 0.0297(5) 0.0017(4) 0.0190(4) -0.0058(4) C11 0.0203(14) 0.0341(18) 0.0247(18) 0.0019(14) 0.0112(13) -0.0027(12) C17 0.0230(15) 0.0348(19) 0.030(2) 0.0044(15) 0.0126(14) 0.0004(13) C18 0.0221(14) 0.0347(19) 0.0184(17) 0.0005(13) 0.0097(13) 0.0030(12) O11 0.0205(10) 0.0413(15) 0.0310(14) 0.0045(11) 0.0146(10) 0.0029(9) O12 0.0253(11) 0.0500(16) 0.0368(15) 0.0122(12) 0.0172(11) 0.0029(11) C12 0.0209(14) 0.0345(18) 0.0208(17) -0.0012(14) 0.0123(13) -0.0024(12) N12 0.0245(13) 0.0419(17) 0.0223(15) 0.0033(13) 0.0146(12) 0.0045(12) C13 0.0273(16) 0.0316(19) 0.030(2) 0.0035(15) 0.0155(15) 0.0024(13) C14 0.0270(16) 0.040(2) 0.030(2) -0.0023(16) 0.0169(15) -0.0014(14) C15 0.0305(17) 0.052(2) 0.0233(19) -0.0030(17) 0.0157(15) -0.0035(15) C16 0.0233(15) 0.045(2) 0.0201(17) 0.0018(15) 0.0097(13) -0.0012(13) C21 0.0250(15) 0.0337(19) 0.0199(17) 0.0017(14) 0.0116(13) 0.0021(13) C22 0.0282(15) 0.0326(19) 0.0278(19) -0.0003(15) 0.0151(14) 0.0012(13) C23 0.0257(15) 0.038(2) 0.0239(18) -0.0010(15) 0.0101(14) -0.0005(13) C24 0.0304(17) 0.040(2) 0.0220(18) 0.0022(15) 0.0076(14) 0.0007(14) C25 0.0338(17) 0.041(2) 0.0213(18) 0.0001(15) 0.0134(15) -0.0043(15) C26 0.0267(15) 0.042(2) 0.0224(18) -0.0015(15) 0.0141(14) 0.0000(14) N31 0.0234(12) 0.0323(15) 0.0238(15) 0.0012(12) 0.0138(11) 0.0017(10) C32 0.0244(14) 0.0284(16) 0.0186(16) -0.0026(13) 0.0121(13) -0.0008(12) N32 0.0255(14) 0.0350(17) 0.0276(17) 0.0050(13) 0.0143(13) 0.0030(11) N33 0.0271(13) 0.0324(16) 0.0228(15) -0.0028(12) 0.0154(12) -0.0030(11) C34 0.0240(14) 0.0350(18) 0.0243(18) -0.0033(14) 0.0162(13) -0.0014(13) C35 0.0239(15) 0.0334(19) 0.0278(19) 0.0014(15) 0.0137(14) 0.0021(13) C36 0.0240(14) 0.0272(16) 0.0226(17) -0.0013(13) 0.0117(13) 0.0008(12) C44 0.0315(17) 0.040(2) 0.031(2) -0.0020(16) 0.0202(15) -0.0026(14) C46 0.0291(16) 0.035(2) 0.031(2) 0.0049(15) 0.0166(15) 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 Cl1 C22 1.736(4) . ? Cl2 C26 1.746(3) . ? C11 C16 1.388(5) . ? C11 C12 1.403(4) . ? C11 C17 1.518(4) . ? C17 C18 1.522(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O12 1.223(4) . ? C18 O11 1.302(4) . ? O11 H11 0.98(4) . ? C12 C13 1.392(4) . ? C12 N12 1.423(4) . ? N12 C21 1.401(4) . ? N12 H12 1.00(4) . ? C13 C14 1.384(5) . ? C13 H13 0.9500 . ? C14 C15 1.374(5) . ? C14 H14 0.9500 . ? C15 C16 1.393(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.399(5) . ? C21 C22 1.402(4) . ? C22 C23 1.386(5) . ? C23 C24 1.379(5) . ? C23 H23 0.9500 . ? C24 C25 1.386(5) . ? C24 H24 0.9500 . ? C25 C26 1.383(5) . ? C25 H25 0.9500 . ? N31 C36 1.344(4) . ? N31 C32 1.357(4) . ? C32 N32 1.342(4) . ? C32 N33 1.355(4) . ? N32 H32A 0.94(4) . ? N32 H32B 0.86(4) . ? N33 C34 1.337(4) . ? C34 C35 1.384(5) . ? C34 C44 1.497(4) . ? C35 C36 1.390(4) . ? C35 H35 0.9500 . ? C36 C46 1.486(5) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C11 C12 118.5(3) . . ? C16 C11 C17 119.7(3) . . ? C12 C11 C17 121.8(3) . . ? C11 C17 C18 112.7(3) . . ? C11 C17 H17A 109.1 . . ? C18 C17 H17A 109.1 . . ? C11 C17 H17B 109.1 . . ? C18 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? O12 C18 O11 124.0(3) . . ? O12 C18 C17 121.8(3) . . ? O11 C18 C17 114.2(3) . . ? C18 O11 H11 114(2) . . ? C13 C12 C11 119.6(3) . . ? C13 C12 N12 121.9(3) . . ? C11 C12 N12 118.4(3) . . ? C21 N12 C12 123.1(3) . . ? C21 N12 H12 112(2) . . ? C12 N12 H12 114(2) . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 119.5(3) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C11 C16 C15 121.6(3) . . ? C11 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C26 C21 N12 121.7(3) . . ? C26 C21 C22 115.1(3) . . ? N12 C21 C22 123.1(3) . . ? C23 C22 C21 122.8(3) . . ? C23 C22 Cl1 118.0(2) . . ? C21 C22 Cl1 119.2(2) . . ? C24 C23 C22 119.7(3) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 119.8(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 119.3(3) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C21 123.2(3) . . ? C25 C26 Cl2 118.3(3) . . ? C21 C26 Cl2 118.5(2) . . ? C36 N31 C32 117.5(3) . . ? N32 C32 N33 117.1(3) . . ? N32 C32 N31 118.1(3) . . ? N33 C32 N31 124.9(3) . . ? C32 N32 H32A 117(2) . . ? C32 N32 H32B 125(2) . . ? H32A N32 H32B 118(3) . . ? C34 N33 C32 116.6(3) . . ? N33 C34 C35 122.1(3) . . ? N33 C34 C44 115.9(3) . . ? C35 C34 C44 122.0(3) . . ? C34 C35 C36 118.3(3) . . ? C34 C35 H35 120.8 . . ? C36 C35 H35 120.8 . . ? N31 C36 C35 120.6(3) . . ? N31 C36 C46 118.0(3) . . ? C35 C36 C46 121.4(3) . . ? C34 C44 H44A 109.5 . . ? C34 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C34 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C36 C46 H46A 109.5 . . ? C36 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C36 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? 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 C16 C11 C17 C18 101.5(4) . . . . ? C12 C11 C17 C18 -79.7(4) . . . . ? C11 C17 C18 O12 51.0(4) . . . . ? C11 C17 C18 O11 -129.7(3) . . . . ? C16 C11 C12 C13 0.0(5) . . . . ? C17 C11 C12 C13 -178.9(3) . . . . ? C16 C11 C12 N12 -178.4(3) . . . . ? C17 C11 C12 N12 2.7(4) . . . . ? C13 C12 N12 C21 9.9(5) . . . . ? C11 C12 N12 C21 -171.7(3) . . . . ? C11 C12 C13 C14 0.4(5) . . . . ? N12 C12 C13 C14 178.7(3) . . . . ? C12 C13 C14 C15 -0.7(5) . . . . ? C13 C14 C15 C16 0.7(5) . . . . ? C12 C11 C16 C15 0.0(5) . . . . ? C17 C11 C16 C15 178.9(3) . . . . ? C14 C15 C16 C11 -0.4(5) . . . . ? C12 N12 C21 C26 -122.2(4) . . . . ? C12 N12 C21 C22 62.3(5) . . . . ? C26 C21 C22 C23 4.8(5) . . . . ? N12 C21 C22 C23 -179.5(3) . . . . ? C26 C21 C22 Cl1 -174.6(2) . . . . ? N12 C21 C22 Cl1 1.1(5) . . . . ? C21 C22 C23 C24 -3.8(5) . . . . ? Cl1 C22 C23 C24 175.6(3) . . . . ? C22 C23 C24 C25 0.5(5) . . . . ? C23 C24 C25 C26 1.6(5) . . . . ? C24 C25 C26 C21 -0.4(5) . . . . ? C24 C25 C26 Cl2 178.9(3) . . . . ? N12 C21 C26 C25 -178.5(3) . . . . ? C22 C21 C26 C25 -2.6(5) . . . . ? N12 C21 C26 Cl2 2.2(5) . . . . ? C22 C21 C26 Cl2 178.0(2) . . . . ? C36 N31 C32 N32 177.9(3) . . . . ? C36 N31 C32 N33 -2.5(5) . . . . ? N32 C32 N33 C34 -179.2(3) . . . . ? N31 C32 N33 C34 1.2(5) . . . . ? C32 N33 C34 C35 0.7(5) . . . . ? C32 N33 C34 C44 -179.9(3) . . . . ? N33 C34 C35 C36 -1.3(5) . . . . ? C44 C34 C35 C36 179.4(3) . . . . ? C32 N31 C36 C35 1.8(5) . . . . ? C32 N31 C36 C46 -176.8(3) . . . . ? C34 C35 C36 N31 0.0(5) . . . . ? C34 C35 C36 C46 178.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O11 H11 N31 0.98(4) 1.68(4) 2.642(3) 169(4) . N12 H12 O12 1.00(4) 2.11(4) 2.957(3) 142(3) . N32 H32A O12 0.94(4) 2.13(4) 3.071(4) 172(3) . N32 H32B N33 0.86(4) 2.27(4) 3.111(4) 166(3) 3_656 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.705 _refine_diff_density_min -0.677 _refine_diff_density_rms 0.148 #END data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; D-ACMP 2-(2,6-dichlorophenylamino)-PhCH2COOH, 2-amino-4-chloro-6-methylpyrimidine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C14 H11 N O2 Cl2) (C5 H6 Cl N3) ; _chemical_formula_sum 'C19 H17 Cl3 N4 O2' _chemical_formula_weight 439.72 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.3435(14) _cell_length_b 4.7003(3) _cell_length_c 20.4210(14) _cell_angle_alpha 90.00 _cell_angle_beta 115.092(3) _cell_angle_gamma 90.00 _cell_volume 1942.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8088 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 31.51 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.504 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8988 _exptl_absorpt_correction_T_max 0.9614 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35367 _diffrn_reflns_av_R_equivalents 0.0571 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 33.14 _reflns_number_total 7404 _reflns_number_gt 5098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7404 _refine_ls_number_parameters 296 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0734 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.097 _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 Cl1 Cl 0.455084(17) 0.75320(7) 0.51968(2) 0.02113(9) Uani 1 1 d . . . Cl2 Cl 0.284958(18) 0.11837(8) 0.58341(2) 0.02692(10) Uani 1 1 d . . . C11 C 0.26104(6) 0.6411(3) 0.36583(7) 0.0159(3) Uani 1 1 d . . . C12 C 0.31188(6) 0.4894(3) 0.42076(7) 0.0155(3) Uani 1 1 d . . . N12 N 0.32014(6) 0.5230(3) 0.49282(6) 0.0183(2) Uani 1 1 d . . . H12 H 0.2854(8) 0.511(3) 0.4964(9) 0.022 Uiso 1 1 d . . . C13 C 0.35190(7) 0.3061(3) 0.40295(8) 0.0192(3) Uani 1 1 d . . . H13 H 0.3863 0.2035 0.4400 0.023 Uiso 1 1 calc R . . C14 C 0.34178(7) 0.2729(3) 0.33163(8) 0.0225(3) Uani 1 1 d . . . H14 H 0.3694 0.1484 0.3201 0.027 Uiso 1 1 calc R . . C15 C 0.29175(7) 0.4195(3) 0.27699(8) 0.0242(3) Uani 1 1 d . . . H15 H 0.2847 0.3957 0.2280 0.029 Uiso 1 1 calc R . . C16 C 0.25187(7) 0.6027(3) 0.29477(8) 0.0212(3) Uani 1 1 d . . . H16 H 0.2175 0.7040 0.2573 0.025 Uiso 1 1 calc R . . C17 C 0.21675(7) 0.8439(3) 0.38247(8) 0.0186(3) Uani 1 1 d . . . H17A H 0.2440 0.9566 0.4259 0.022 Uiso 1 1 calc R . . H17B H 0.1961 0.9777 0.3415 0.022 Uiso 1 1 calc R . . C18 C 0.16313(7) 0.6924(3) 0.39548(8) 0.0167(3) Uani 1 1 d . . . O11 O 0.10420(5) 0.8063(2) 0.36041(6) 0.0211(2) Uani 1 1 d . . . H11 H 0.0748(9) 0.714(3) 0.3690(9) 0.025 Uiso 1 1 d . . . O12 O 0.17352(5) 0.4859(2) 0.43503(6) 0.0256(2) Uani 1 1 d . . . C21 C 0.37378(7) 0.4121(3) 0.55223(7) 0.0167(3) Uani 1 1 d . . . C22 C 0.43949(7) 0.4947(3) 0.57091(7) 0.0174(3) Uani 1 1 d . . . C23 C 0.49241(7) 0.3823(3) 0.62966(8) 0.0203(3) Uani 1 1 d . . . H23 H 0.5363 0.4374 0.6392 0.024 Uiso 1 1 calc R . . C24 C 0.48129(7) 0.1891(3) 0.67453(8) 0.0235(3) Uani 1 1 d . . . H24 H 0.5175 0.1100 0.7147 0.028 Uiso 1 1 calc R . . C25 C 0.41688(8) 0.1112(3) 0.66062(8) 0.0227(3) Uani 1 1 d . . . H25 H 0.4087 -0.0157 0.6921 0.027 Uiso 1 1 calc R . . C26 C 0.36509(7) 0.2207(3) 0.60053(8) 0.0193(3) Uani 1 1 d . . . Cl3A Cl -0.17358(7) 0.2790(4) 0.40513(11) 0.02508(15) Uani 0.7908(17) 1 d PD A 1 N31A N 0.0030(3) 0.546(4) 0.3743(10) 0.0156(3) Uani 0.7908(17) 1 d PD A 1 C32A C 0.0045(2) 0.344(2) 0.4225(6) 0.0150(6) Uani 0.7908(17) 1 d PD A 1 N32A N 0.0620(3) 0.214(2) 0.4614(4) 0.0181(8) Uani 0.7908(17) 1 d PD A 1 H32A H 0.0952(11) 0.254(5) 0.4530(12) 0.022 Uiso 0.7908(17) 1 d P A 1 H32B H 0.0625(11) 0.105(5) 0.4891(13) 0.022 Uiso 0.7908(17) 1 d P A 1 N33A N -0.0486(3) 0.257(3) 0.4329(7) 0.0159(7) Uani 0.7908(17) 1 d PD A 1 C34A C -0.1045(2) 0.382(2) 0.3918(5) 0.0163(5) Uani 0.7908(17) 1 d PD A 1 C35A C -0.11256(17) 0.5923(17) 0.3410(4) 0.0179(7) Uani 0.7908(17) 1 d PD A 1 H35A H -0.1540 0.6815 0.3140 0.021 Uiso 0.7908(17) 1 calc PR A 1 C36A C -0.0563(2) 0.663(2) 0.3322(5) 0.0158(6) Uani 0.7908(17) 1 d PD A 1 C37A C -0.0582(5) 0.8743(19) 0.2761(5) 0.0221(6) Uani 0.7908(17) 1 d PD A 1 H37A H -0.0164 0.9788 0.2939 0.027 Uiso 0.7908(17) 1 calc PR A 1 H37B H -0.0947 1.0081 0.2662 0.027 Uiso 0.7908(17) 1 calc PR A 1 H37C H -0.0650 0.7734 0.2315 0.027 Uiso 0.7908(17) 1 calc PR A 1 Cl3B Cl -0.0608(4) 0.9106(17) 0.2741(5) 0.0221(6) Uani 0.2092(17) 1 d PD A 2 N31B N -0.0548(11) 0.244(10) 0.430(3) 0.0159(7) Uani 0.2092(17) 1 d PD A 2 C32B C -0.0009(10) 0.328(9) 0.421(2) 0.0150(6) Uani 0.2092(17) 1 d PD A 2 N32B N 0.0580(11) 0.224(9) 0.4657(18) 0.0181(8) Uani 0.2092(17) 1 d PD A 2 H32C H 0.0943 0.2914 0.4647 0.022 Uiso 0.2092(17) 1 calc PR A 2 H32D H 0.0604 0.0880 0.4964 0.022 Uiso 0.2092(17) 1 calc PR A 2 N33B N -0.0007(10) 0.537(16) 0.375(4) 0.0156(3) Uani 0.2092(17) 1 d PD A 2 C34B C -0.0583(7) 0.658(9) 0.338(2) 0.0158(6) Uani 0.2092(17) 1 d PD A 2 C35B C -0.1179(7) 0.570(7) 0.3371(18) 0.0179(7) Uani 0.2092(17) 1 d PD A 2 H35B H -0.1594 0.6363 0.3024 0.021 Uiso 0.2092(17) 1 calc PR A 2 C36B C -0.1126(10) 0.377(9) 0.391(2) 0.0163(5) Uani 0.2092(17) 1 d PD A 2 C37B C -0.1714(12) 0.294(7) 0.4040(18) 0.02508(15) Uani 0.2092(17) 1 d PD A 2 H37D H -0.1741 0.4174 0.4413 0.030 Uiso 0.2092(17) 1 calc PR A 2 H37E H -0.1668 0.0956 0.4201 0.030 Uiso 0.2092(17) 1 calc PR A 2 H37F H -0.2118 0.3149 0.3591 0.030 Uiso 0.2092(17) 1 calc PR A 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 Cl1 0.02107(17) 0.01702(15) 0.0270(2) 0.00364(12) 0.01183(15) -0.00052(12) Cl2 0.02127(19) 0.0388(2) 0.0237(2) 0.00268(15) 0.01241(16) -0.00619(15) C11 0.0129(6) 0.0174(6) 0.0188(7) 0.0006(5) 0.0080(5) -0.0023(5) C12 0.0142(6) 0.0167(6) 0.0170(7) -0.0008(5) 0.0079(5) -0.0034(5) N12 0.0137(6) 0.0268(6) 0.0159(6) 0.0025(5) 0.0078(5) 0.0029(5) C13 0.0165(7) 0.0193(6) 0.0218(8) 0.0006(5) 0.0081(6) 0.0009(5) C14 0.0198(7) 0.0252(7) 0.0249(8) -0.0060(6) 0.0119(6) -0.0021(5) C15 0.0231(8) 0.0344(8) 0.0169(8) -0.0040(6) 0.0102(6) -0.0039(6) C16 0.0167(7) 0.0275(7) 0.0176(7) 0.0032(5) 0.0054(6) -0.0012(5) C17 0.0164(6) 0.0173(6) 0.0218(8) 0.0023(5) 0.0079(6) 0.0001(5) C18 0.0141(6) 0.0199(6) 0.0164(7) -0.0025(5) 0.0069(5) 0.0004(5) O11 0.0137(5) 0.0236(5) 0.0272(6) 0.0039(4) 0.0096(4) 0.0014(4) O12 0.0185(5) 0.0308(5) 0.0291(6) 0.0108(4) 0.0114(5) 0.0020(4) C21 0.0162(6) 0.0182(6) 0.0158(7) -0.0012(5) 0.0070(5) 0.0015(5) C22 0.0195(7) 0.0153(6) 0.0185(7) 0.0003(5) 0.0091(6) -0.0005(5) C23 0.0183(7) 0.0191(6) 0.0212(8) -0.0021(5) 0.0061(6) -0.0012(5) C24 0.0218(7) 0.0246(7) 0.0179(8) 0.0017(6) 0.0025(6) 0.0015(6) C25 0.0270(8) 0.0246(7) 0.0159(7) 0.0025(5) 0.0086(6) -0.0013(6) C26 0.0180(7) 0.0243(7) 0.0168(7) -0.0005(5) 0.0084(6) -0.0022(5) Cl3A 0.0181(3) 0.0321(4) 0.0281(3) 0.0027(2) 0.0127(2) -0.00362(19) N31A 0.0138(9) 0.0162(14) 0.0174(7) -0.0006(6) 0.0072(12) -0.0008(14) C32A 0.0151(11) 0.0147(14) 0.0157(9) -0.0040(11) 0.0070(12) -0.0022(12) N32A 0.0158(10) 0.0213(10) 0.0199(13) 0.0041(11) 0.0103(7) 0.0027(7) N33A 0.0148(13) 0.0173(13) 0.0172(11) -0.0024(11) 0.0082(15) -0.0029(14) C34A 0.0124(15) 0.0200(7) 0.0191(8) -0.0035(6) 0.0092(15) -0.0032(15) C35A 0.0137(9) 0.0179(16) 0.0200(12) -0.0018(13) 0.0051(10) 0.0001(10) C36A 0.0184(7) 0.0132(7) 0.0157(18) -0.0018(9) 0.0072(6) -0.0007(6) C37A 0.0219(7) 0.0216(17) 0.0230(6) 0.0033(8) 0.0098(5) 0.0024(10) Cl3B 0.0219(7) 0.0216(17) 0.0230(6) 0.0033(8) 0.0098(5) 0.0024(10) N31B 0.0148(13) 0.0173(13) 0.0172(11) -0.0024(11) 0.0082(15) -0.0029(14) C32B 0.0151(11) 0.0147(14) 0.0157(9) -0.0040(11) 0.0070(12) -0.0022(12) N32B 0.0158(10) 0.0213(10) 0.0199(13) 0.0041(11) 0.0103(7) 0.0027(7) N33B 0.0138(9) 0.0162(14) 0.0174(7) -0.0006(6) 0.0072(12) -0.0008(14) C34B 0.0184(7) 0.0132(7) 0.0157(18) -0.0018(9) 0.0072(6) -0.0007(6) C35B 0.0137(9) 0.0179(16) 0.0200(12) -0.0018(13) 0.0051(10) 0.0001(10) C36B 0.0124(15) 0.0200(7) 0.0191(8) -0.0035(6) 0.0092(15) -0.0032(15) C37B 0.0181(3) 0.0321(4) 0.0281(3) 0.0027(2) 0.0127(2) -0.00362(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 Cl1 C22 1.7323(13) . ? Cl2 C26 1.7401(14) . ? C11 C16 1.388(2) . ? C11 C12 1.4057(19) . ? C11 C17 1.5129(18) . ? C12 C13 1.3964(18) . ? C12 N12 1.4122(18) . ? N12 C21 1.3953(18) . ? N12 H12 0.812(16) . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 C15 1.382(2) . ? C14 H14 0.9500 . ? C15 C16 1.394(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.5109(18) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 O12 1.2204(16) . ? C18 O11 1.3164(17) . ? O11 H11 0.866(17) . ? C21 C22 1.4060(19) . ? C21 C26 1.4082(19) . ? C22 C23 1.383(2) . ? C23 C24 1.385(2) . ? C23 H23 0.9500 . ? C24 C25 1.392(2) . ? C24 H24 0.9500 . ? C25 C26 1.380(2) . ? C25 H25 0.9500 . ? Cl3A C34A 1.745(3) . ? N31A C36A 1.353(3) . ? N31A C32A 1.358(3) . ? C32A N32A 1.337(3) . ? C32A N33A 1.356(3) . ? N32A H32A 0.85(2) . ? N32A H32B 0.76(2) . ? N33A C34A 1.313(3) . ? C34A C35A 1.388(3) . ? C35A C36A 1.384(4) . ? C35A H35A 0.9500 . ? C36A C37A 1.503(6) . ? C37A H37A 0.9800 . ? C37A H37B 0.9800 . ? C37A H37C 0.9800 . ? Cl3B C34B 1.746(5) . ? N31B C36B 1.353(5) . ? N31B C32B 1.358(5) . ? C32B N32B 1.338(5) . ? C32B N33B 1.357(5) . ? N32B H32A 0.98(4) . ? N32B H32B 0.71(3) . ? N32B H32C 0.8800 . ? N32B H32D 0.8800 . ? N33B C34B 1.314(5) . ? C34B C35B 1.389(5) . ? C35B C36B 1.385(5) . ? C35B H35B 0.9500 . ? C36B C37B 1.502(7) . ? C37B H37D 0.9800 . ? C37B H37E 0.9800 . ? C37B H37F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C11 C12 118.64(12) . . ? C16 C11 C17 119.72(12) . . ? C12 C11 C17 121.64(12) . . ? C13 C12 C11 119.68(13) . . ? C13 C12 N12 121.69(12) . . ? C11 C12 N12 118.62(12) . . ? C21 N12 C12 123.28(11) . . ? C21 N12 H12 113.5(12) . . ? C12 N12 H12 112.3(12) . . ? C14 C13 C12 120.43(13) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 120.55(13) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.02(14) . . ? C14 C15 H15 120.5 . . ? C16 C15 H15 120.5 . . ? C11 C16 C15 121.68(13) . . ? C11 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C18 C17 C11 112.69(11) . . ? C18 C17 H17A 109.1 . . ? C11 C17 H17A 109.1 . . ? C18 C17 H17B 109.1 . . ? C11 C17 H17B 109.1 . . ? H17A C17 H17B 107.8 . . ? O12 C18 O11 123.31(13) . . ? O12 C18 C17 123.27(12) . . ? O11 C18 C17 113.42(11) . . ? C18 O11 H11 110.7(12) . . ? N12 C21 C22 123.08(12) . . ? N12 C21 C26 121.67(12) . . ? C22 C21 C26 115.14(13) . . ? C23 C22 C21 122.68(12) . . ? C23 C22 Cl1 118.34(11) . . ? C21 C22 Cl1 118.96(10) . . ? C22 C23 C24 119.79(13) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C25 119.82(13) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 119.19(13) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C25 C26 C21 123.24(13) . . ? C25 C26 Cl2 118.62(11) . . ? C21 C26 Cl2 118.14(11) . . ? C36A N31A C32A 117.4(2) . . ? N32A C32A N33A 116.9(3) . . ? N32A C32A N31A 118.2(3) . . ? N33A C32A N31A 124.90(16) . . ? C32A N32A H32A 118.6(14) . . ? C32A N32A H32B 117.4(16) . . ? H32A N32A H32B 124(2) . . ? C34A N33A C32A 115.0(2) . . ? N33A C34A C35A 125.7(2) . . ? N33A C34A Cl3A 116.1(2) . . ? C35A C34A Cl3A 118.2(2) . . ? C36A C35A C34A 115.56(19) . . ? C36A C35A H35A 122.2 . . ? C34A C35A H35A 122.2 . . ? N31A C36A C35A 121.3(2) . . ? N31A C36A C37A 117.1(4) . . ? C35A C36A C37A 121.6(4) . . ? C36B N31B C32B 117.4(6) . . ? N32B C32B N33B 116.7(8) . . ? N32B C32B N31B 117.9(9) . . ? N33B C32B N31B 124.9(5) . . ? C32B N32B H32A 117(2) . . ? C32B N32B H32B 124(4) . . ? H32A N32B H32B 113(4) . . ? C32B N32B H32C 120.0 . . ? C32B N32B H32D 120.0 . . ? H32C N32B H32D 120.0 . . ? C34B N33B C32B 115.0(6) . . ? N33B C34B C35B 125.2(7) . . ? N33B C34B Cl3B 115.9(7) . . ? C35B C34B Cl3B 118.0(7) . . ? C36B C35B C34B 115.3(6) . . ? C36B C35B H35B 122.4 . . ? C34B C35B H35B 122.4 . . ? N31B C36B C35B 121.0(6) . . ? N31B C36B C37B 117.3(7) . . ? C35B C36B C37B 121.7(7) . . ? C36B C37B H37D 109.5 . . ? C36B C37B H37E 109.5 . . ? H37D C37B H37E 109.5 . . ? C36B C37B H37F 109.5 . . ? H37D C37B H37F 109.5 . . ? H37E C37B H37F 109.5 . . ? 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 C16 C11 C12 C13 0.28(19) . . . . ? C17 C11 C12 C13 -179.50(12) . . . . ? C16 C11 C12 N12 -178.45(12) . . . . ? C17 C11 C12 N12 1.77(18) . . . . ? C13 C12 N12 C21 9.7(2) . . . . ? C11 C12 N12 C21 -171.58(12) . . . . ? C11 C12 C13 C14 -0.03(19) . . . . ? N12 C12 C13 C14 178.65(12) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C13 C14 C15 C16 0.4(2) . . . . ? C12 C11 C16 C15 -0.2(2) . . . . ? C17 C11 C16 C15 179.59(13) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C16 C11 C17 C18 101.14(15) . . . . ? C12 C11 C17 C18 -79.08(16) . . . . ? C11 C17 C18 O12 47.30(18) . . . . ? C11 C17 C18 O11 -133.17(13) . . . . ? C12 N12 C21 C22 62.28(18) . . . . ? C12 N12 C21 C26 -121.74(14) . . . . ? N12 C21 C22 C23 -179.59(13) . . . . ? C26 C21 C22 C23 4.19(19) . . . . ? N12 C21 C22 Cl1 1.82(18) . . . . ? C26 C21 C22 Cl1 -174.39(10) . . . . ? C21 C22 C23 C24 -2.8(2) . . . . ? Cl1 C22 C23 C24 175.76(11) . . . . ? C22 C23 C24 C25 -0.6(2) . . . . ? C23 C24 C25 C26 2.3(2) . . . . ? C24 C25 C26 C21 -0.8(2) . . . . ? C24 C25 C26 Cl2 179.36(11) . . . . ? N12 C21 C26 C25 -178.66(13) . . . . ? C22 C21 C26 C25 -2.4(2) . . . . ? N12 C21 C26 Cl2 1.22(18) . . . . ? C22 C21 C26 Cl2 177.49(10) . . . . ? C36A N31A C32A N32A 176.0(17) . . . . ? C36A N31A C32A N33A -2(3) . . . . ? N32A C32A N33A C34A -177.6(14) . . . . ? N31A C32A N33A C34A 0(2) . . . . ? C32A N33A C34A C35A -1(2) . . . . ? C32A N33A C34A Cl3A -178.9(11) . . . . ? N33A C34A C35A C36A 2.6(18) . . . . ? Cl3A C34A C35A C36A -179.3(10) . . . . ? C32A N31A C36A C35A 4(2) . . . . ? C32A N31A C36A C37A -176.5(17) . . . . ? C34A C35A C36A N31A -4.2(17) . . . . ? C34A C35A C36A C37A 176.3(11) . . . . ? C36B N31B C32B N32B 172(6) . . . . ? C36B N31B C32B N33B 1(9) . . . . ? N32B C32B N33B C34B -172(6) . . . . ? N31B C32B N33B C34B -1(10) . . . . ? C32B N33B C34B C35B -7(9) . . . . ? C32B N33B C34B Cl3B -176(6) . . . . ? N33B C34B C35B C36B 13(7) . . . . ? Cl3B C34B C35B C36B -178(4) . . . . ? C32B N31B C36B C35B 6(8) . . . . ? C32B N31B C36B C37B -177(5) . . . . ? C34B C35B C36B N31B -13(7) . . . . ? C34B C35B C36B C37B 171(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O11 H11 N31A 0.866(17) 1.830(18) 2.688(5) 170.7(17) . N12 H12 O12 0.812(16) 2.275(17) 2.9793(16) 145.4(16) . N32A H32A O12 0.85(2) 2.22(2) 3.045(7) 163.4(18) . N32A H32B N33A 0.76(2) 2.44(2) 3.193(8) 172(2) 3_556 N32B H32C O12 0.88 2.29 3.15(3) 167.0 . N32B H32D N33A 0.88 2.26 3.13(2) 170.8 3_556 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.481 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.077 #END