# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Andrew Wilson' _publ_contact_author_address ; Department of Chemistry University of Leeds Leeds LS2 9JT UNITED KINGDOM ; _publ_contact_author_email A.J.WILSON@LEEDS.AC.UK _publ_section_title ; Conformer Independent Heterodimerisation of Linear Arrays Using Three Hydrogen-Bonds ; loop_ _publ_author_name 'Andrew Wilson' 'Colin Kilner' 'Andrea M. McGhee' data_compound_1a _database_code_depnum_ccdc_archive 'CCDC 660530' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Ureidoimidazole _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N4 O' _chemical_formula_sum 'C10 H10 N4 O' _chemical_formula_weight 202.22 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/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.7156(3) _cell_length_b 6.0176(2) _cell_length_c 13.3965(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.3690(10) _cell_angle_gamma 90.00 _cell_volume 943.64(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8046 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12808 _diffrn_reflns_av_R_equivalents 0.0978 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.98 _reflns_number_total 1854 _reflns_number_gt 1533 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2004)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; The structure ajw095 solved in the monoclinic spacegroup P21/n. All hydrogen atoms could be located in the Fourier difference map but in the final stages of refinement, they were placed geometrically and refined using a riding model: C-H aromatic, 0.95\A; N-H, 0.88\A. Uiso(H) values were constrained to be 1.2 times Ueq of the carrier atom. The angle between the phenyl and imidazyl rings was calculated as 43.27(6) degrees. C.Kilner 1 December 2005 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^)+(0.0609P)^2^+0.2321P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1854 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.36678(10) -0.4279(2) 0.22786(9) 0.0296(3) Uani 1 1 d . . . C2 C 0.45293(12) -0.5827(3) 0.21423(11) 0.0304(4) Uani 1 1 d . . . H2 H 0.4631 -0.7156 0.2519 0.037 Uiso 1 1 calc R . . C3 C 0.51996(12) -0.5182(3) 0.14018(11) 0.0304(3) Uani 1 1 d . . . H3 H 0.5840 -0.5951 0.1160 0.036 Uiso 1 1 calc R . . N4 N 0.47625(10) -0.3168(2) 0.10661(9) 0.0292(3) Uani 1 1 d . . . H4 H 0.5031 -0.2339 0.0588 0.035 Uiso 1 1 calc R . . C5 C 0.38504(12) -0.2716(2) 0.16087(10) 0.0261(3) Uani 1 1 d . . . N6 N 0.31734(10) -0.0851(2) 0.15026(9) 0.0285(3) Uani 1 1 d . . . H6 H 0.2776 -0.0441 0.2015 0.034 Uiso 1 1 calc R . . O7 O 0.37116(9) 0.01789(18) -0.00549(8) 0.0336(3) Uani 1 1 d . . . C7 C 0.30783(12) 0.0418(2) 0.06419(10) 0.0273(3) Uani 1 1 d . . . N8 N 0.22122(11) 0.1921(2) 0.06696(9) 0.0299(3) Uani 1 1 d . . . H8 H 0.1802 0.1924 0.1206 0.036 Uiso 1 1 calc R . . C9 C 0.19126(12) 0.3479(2) -0.00879(11) 0.0290(3) Uani 1 1 d . . . C10 C 0.19958(13) 0.2987(3) -0.10988(11) 0.0338(4) Uani 1 1 d . . . H10 H 0.2286 0.1589 -0.1299 0.041 Uiso 1 1 calc R . . C11 C 0.16520(14) 0.4551(3) -0.18131(13) 0.0389(4) Uani 1 1 d . . . H11 H 0.1715 0.4221 -0.2502 0.047 Uiso 1 1 calc R . . C12 C 0.12190(14) 0.6582(3) -0.15314(13) 0.0420(4) Uani 1 1 d . . . H12 H 0.0992 0.7647 -0.2024 0.050 Uiso 1 1 calc R . . C13 C 0.11179(14) 0.7057(3) -0.05250(14) 0.0426(4) Uani 1 1 d . . . H13 H 0.0809 0.8442 -0.0329 0.051 Uiso 1 1 calc R . . C14 C 0.14675(13) 0.5516(3) 0.01951(13) 0.0352(4) Uani 1 1 d . . . H14 H 0.1403 0.5853 0.0883 0.042 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0300(6) 0.0338(7) 0.0253(6) 0.0029(5) 0.0041(5) -0.0021(5) C2 0.0319(8) 0.0305(8) 0.0288(8) 0.0025(6) 0.0008(6) -0.0020(6) C3 0.0300(8) 0.0335(8) 0.0278(7) -0.0017(6) 0.0028(6) 0.0028(6) N4 0.0304(6) 0.0350(7) 0.0228(6) 0.0029(5) 0.0069(5) -0.0002(5) C5 0.0270(7) 0.0317(8) 0.0196(7) -0.0017(6) 0.0024(5) -0.0036(6) N6 0.0325(6) 0.0321(7) 0.0215(6) 0.0008(5) 0.0073(5) 0.0026(5) O7 0.0309(6) 0.0431(6) 0.0273(6) 0.0068(5) 0.0093(4) 0.0025(5) C7 0.0260(7) 0.0320(8) 0.0240(7) 0.0007(6) 0.0028(6) -0.0040(6) N8 0.0322(6) 0.0344(7) 0.0237(6) 0.0025(5) 0.0069(5) 0.0031(5) C9 0.0255(7) 0.0321(8) 0.0296(8) 0.0027(6) 0.0015(6) -0.0034(6) C10 0.0344(8) 0.0373(8) 0.0299(8) 0.0025(6) 0.0035(6) -0.0012(7) C11 0.0355(8) 0.0486(10) 0.0325(8) 0.0090(7) -0.0007(7) -0.0059(7) C12 0.0368(9) 0.0424(10) 0.0459(10) 0.0147(8) -0.0088(7) -0.0051(7) C13 0.0367(9) 0.0321(9) 0.0583(11) 0.0006(7) -0.0057(8) -0.0001(7) C14 0.0324(8) 0.0359(8) 0.0370(9) -0.0025(7) -0.0017(7) -0.0020(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.3234(18) . ? N1 C2 1.3914(19) . ? C2 C3 1.348(2) . ? C2 H2 0.9500 . ? C3 N4 1.384(2) . ? C3 H3 0.9500 . ? N4 C5 1.3448(18) . ? N4 H4 0.8800 . ? C5 N6 1.3780(19) . ? N6 C7 1.3838(18) . ? N6 H6 0.8800 . ? O7 C7 1.2247(17) . ? C7 N8 1.3608(19) . ? N8 C9 1.4153(18) . ? N8 H8 0.8800 . ? C9 C14 1.391(2) . ? C9 C10 1.394(2) . ? C10 C11 1.390(2) . ? C10 H10 0.9500 . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 H14 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 C5 N1 C2 104.40(12) . . ? C3 C2 N1 110.57(13) . . ? C3 C2 H2 124.7 . . ? N1 C2 H2 124.7 . . ? C2 C3 N4 105.82(13) . . ? C2 C3 H3 127.1 . . ? N4 C3 H3 127.1 . . ? C5 N4 C3 107.05(12) . . ? C5 N4 H4 126.5 . . ? C3 N4 H4 126.5 . . ? N1 C5 N4 112.16(13) . . ? N1 C5 N6 122.69(13) . . ? N4 C5 N6 125.15(13) . . ? C5 N6 C7 124.17(12) . . ? C5 N6 H6 117.9 . . ? C7 N6 H6 117.9 . . ? O7 C7 N8 125.09(13) . . ? O7 C7 N6 122.66(13) . . ? N8 C7 N6 112.24(12) . . ? C7 N8 C9 125.72(12) . . ? C7 N8 H8 117.1 . . ? C9 N8 H8 117.1 . . ? C14 C9 C10 119.63(14) . . ? C14 C9 N8 118.24(13) . . ? C10 C9 N8 122.04(14) . . ? C11 C10 C9 119.67(15) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 120.68(16) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.64(16) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.19(16) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 120.18(16) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? 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 C5 N1 C2 C3 -0.28(16) . . . . ? N1 C2 C3 N4 0.59(17) . . . . ? C2 C3 N4 C5 -0.67(16) . . . . ? C2 N1 C5 N4 -0.17(16) . . . . ? C2 N1 C5 N6 -179.73(13) . . . . ? C3 N4 C5 N1 0.54(16) . . . . ? C3 N4 C5 N6 -179.91(13) . . . . ? N1 C5 N6 C7 -157.70(14) . . . . ? N4 C5 N6 C7 22.8(2) . . . . ? C5 N6 C7 O7 -10.7(2) . . . . ? C5 N6 C7 N8 169.22(13) . . . . ? O7 C7 N8 C9 -1.3(2) . . . . ? N6 C7 N8 C9 178.83(13) . . . . ? C7 N8 C9 C14 -147.80(15) . . . . ? C7 N8 C9 C10 35.6(2) . . . . ? C14 C9 C10 C11 1.1(2) . . . . ? N8 C9 C10 C11 177.73(14) . . . . ? C9 C10 C11 C12 -0.6(2) . . . . ? C10 C11 C12 C13 -0.5(2) . . . . ? C11 C12 C13 C14 1.1(2) . . . . ? C12 C13 C14 C9 -0.5(2) . . . . ? C10 C9 C14 C13 -0.6(2) . . . . ? N8 C9 C14 C13 -177.32(13) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.214 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.052 # Attachment 'compound_3.CIF' data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 660531' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Amidoisocytosine _chemical_melting_point ? _chemical_formula_moiety '4(C12 H11 N3 O2), 3(C H2 Cl2)' _chemical_formula_sum 'C51 H50 Cl6 N12 O8' _chemical_formula_weight 1171.73 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.5748(2) _cell_length_b 11.2109(2) _cell_length_c 11.8373(3) _cell_angle_alpha 101.7370(8) _cell_angle_beta 100.6000(8) _cell_angle_gamma 96.1140(13) _cell_volume 1335.37(5) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13823 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description fragment _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.457 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 25222 _diffrn_reflns_av_R_equivalents 0.1037 _diffrn_reflns_av_sigmaI/netI 0.0612 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5222 _reflns_number_gt 3827 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material 'local program' _refine_special_details ; The structure ajw013 solved in the triclinic spacegroup P-1. The asymmetric unit contains two molecules of the title compound (C12 H11 N3 O2) and one-and-a-half molecules of dichloromethane. One molecule of dichloromethane is disordered about the inversion centre with none of its atoms on special positions. All hydrogen atoms could be located in the Fourier difference map and this showed that N16 and N36 in their respective pyrimidine rings were protonated while N12 and N32 were not. In addition the hydrogens bonded to N1 and N21 were in a planar configuration. All hydrogen atoms attached to nitrogen were freely refined. In the final stages of refinement, the hydrogen atoms bonded to carbon were placed geometrically and refined using a riding model. C-H distances: CH3, 0.98\A; CH2, 0.99\A; aromatic, 0.95\A. C.Kilner 5 April 2005 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^)+(0.1090P)^2^+2.4550P] 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 5222 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1071 _refine_ls_R_factor_gt 0.0799 _refine_ls_wR_factor_ref 0.2314 _refine_ls_wR_factor_gt 0.2069 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 C1S C 0.4303(8) 0.0313(9) 0.4806(7) 0.048(2) Uani 0.50 1 d P . -1 H1S1 H 0.3919 0.0900 0.5340 0.058 Uiso 0.50 1 calc PR . -1 H1S2 H 0.3803 0.0237 0.3994 0.058 Uiso 0.50 1 calc PR . -1 C2S C 0.1932(4) -0.2647(4) 0.9090(4) 0.0482(11) Uani 1 1 d . . . H2SA H 0.2053 -0.2704 0.9926 0.058 Uiso 1 1 calc R . . H2SB H 0.2246 -0.1789 0.9073 0.058 Uiso 1 1 calc R . . C2 C 0.0242(3) 0.0382(3) 0.3572(3) 0.0270(7) Uani 1 1 d . . . C3 C 0.0076(3) 0.1574(3) 0.4324(3) 0.0258(7) Uani 1 1 d . . . C4 C 0.1120(3) 0.2144(3) 0.5247(3) 0.0281(7) Uani 1 1 d . . . H4 H 0.1883 0.1768 0.5368 0.034 Uiso 1 1 calc R . . C5 C 0.1056(4) 0.3255(3) 0.5989(3) 0.0308(8) Uani 1 1 d . . . H5 H 0.1770 0.3633 0.6620 0.037 Uiso 1 1 calc R . . C6 C -0.0049(4) 0.3813(3) 0.5811(3) 0.0338(8) Uani 1 1 d . . . H6 H -0.0099 0.4572 0.6321 0.041 Uiso 1 1 calc R . . C7 C -0.1086(4) 0.3254(4) 0.4879(4) 0.0389(9) Uani 1 1 d . . . H7 H -0.1837 0.3644 0.4745 0.047 Uiso 1 1 calc R . . C8 C -0.1033(4) 0.2137(3) 0.4147(3) 0.0346(8) Uani 1 1 d . . . H8 H -0.1753 0.1754 0.3524 0.041 Uiso 1 1 calc R . . C11 C -0.0920(3) -0.1463(3) 0.2075(3) 0.0258(7) Uani 1 1 d . . . C13 C -0.2147(3) -0.3179(3) 0.0808(3) 0.0283(7) Uani 1 1 d . . . C14 C -0.1091(3) -0.3755(3) 0.0731(3) 0.0278(7) Uani 1 1 d . . . H14 H -0.1187 -0.4559 0.0246 0.033 Uiso 1 1 calc R . . C15 C 0.0163(3) -0.3150(3) 0.1381(3) 0.0257(7) Uani 1 1 d . . . C17 C -0.3489(3) -0.3765(4) 0.0135(4) 0.0362(9) Uani 1 1 d . . . H17A H -0.4056 -0.3852 0.0690 0.043 Uiso 1 1 calc R . . H17B H -0.3449 -0.4580 -0.0341 0.043 Uiso 1 1 calc R . . H17C H -0.3837 -0.3246 -0.0385 0.043 Uiso 1 1 calc R . . C22 C 0.5226(3) 0.3298(3) 0.7191(3) 0.0277(7) Uani 1 1 d . . . C23 C 0.5700(3) 0.4470(3) 0.6889(3) 0.0272(7) Uani 1 1 d . . . C24 C 0.4776(4) 0.5221(4) 0.6614(4) 0.0370(9) Uani 1 1 d . . . H24 H 0.3893 0.4971 0.6625 0.044 Uiso 1 1 calc R . . C25 C 0.5127(4) 0.6325(4) 0.6325(4) 0.0445(10) Uani 1 1 d . . . H25 H 0.4492 0.6841 0.6165 0.053 Uiso 1 1 calc R . . C26 C 0.6393(4) 0.6676(4) 0.6269(4) 0.0393(9) Uani 1 1 d . . . H26 H 0.6634 0.7432 0.6063 0.047 Uiso 1 1 calc R . . C27 C 0.7319(4) 0.5925(4) 0.6514(4) 0.0403(9) Uani 1 1 d . . . H27 H 0.8191 0.6162 0.6460 0.048 Uiso 1 1 calc R . . C28 C 0.6985(4) 0.4837(4) 0.6836(3) 0.0340(8) Uani 1 1 d . . . H28 H 0.7631 0.4339 0.7022 0.041 Uiso 1 1 calc R . . C31 C 0.5911(3) 0.1556(3) 0.7998(3) 0.0249(7) Uani 1 1 d . . . C33 C 0.6699(3) -0.0090(3) 0.8586(3) 0.0281(7) Uani 1 1 d . . . C34 C 0.5482(3) -0.0653(3) 0.8552(3) 0.0300(8) Uani 1 1 d . . . H34 H 0.5372 -0.1424 0.8765 0.036 Uiso 1 1 calc R . . C35 C 0.4372(3) -0.0092(3) 0.8198(3) 0.0287(8) Uani 1 1 d . . . C37 C 0.7894(4) -0.0646(4) 0.8953(4) 0.0387(9) Uani 1 1 d . . . H37A H 0.8329 -0.0830 0.8288 0.046 Uiso 1 1 calc R . . H37B H 0.7647 -0.1408 0.9195 0.046 Uiso 1 1 calc R . . H37C H 0.8489 -0.0062 0.9616 0.046 Uiso 1 1 calc R . . N1 N -0.0833(3) -0.0284(3) 0.2762(3) 0.0274(7) Uani 1 1 d . . . H1 H -0.149(5) -0.001(5) 0.273(5) 0.058(16) Uiso 1 1 d . . . N12 N -0.2084(3) -0.2017(3) 0.1507(3) 0.0261(6) Uani 1 1 d . . . N16 N 0.0183(3) -0.1962(3) 0.2025(3) 0.0257(6) Uani 1 1 d . . . H16 H 0.096(4) -0.151(4) 0.246(4) 0.034(10) Uiso 1 1 d . . . N21 N 0.6141(3) 0.2693(3) 0.7733(3) 0.0269(6) Uani 1 1 d . . . H21 H 0.684(4) 0.299(4) 0.791(3) 0.025(11) Uiso 1 1 d . . . N32 N 0.6931(3) 0.1021(3) 0.8284(2) 0.0266(6) Uani 1 1 d . . . N36 N 0.4674(3) 0.1061(3) 0.7967(3) 0.0276(7) Uani 1 1 d . . . H36 H 0.411(5) 0.149(5) 0.776(4) 0.052(14) Uiso 1 1 d . . . O2 O 0.1298(2) 0.0007(2) 0.3680(2) 0.0378(6) Uani 1 1 d . . . O15 O 0.1200(2) -0.3595(2) 0.1400(2) 0.0299(6) Uani 1 1 d . . . O22 O 0.4064(2) 0.2894(2) 0.6972(3) 0.0372(6) Uani 1 1 d . . . O35 O 0.3218(2) -0.0528(2) 0.8086(2) 0.0345(6) Uani 1 1 d . . . Cl1S Cl 0.40633(16) -0.09991(14) 0.51239(12) 0.0723(4) Uani 1 1 d . . . Cl2S Cl 0.28421(16) -0.36461(14) 0.83607(19) 0.0854(6) Uani 1 1 d . . . Cl3S Cl 0.02823(14) -0.3019(2) 0.84223(13) 0.0853(6) Uani 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 C1S 0.041(5) 0.073(6) 0.026(4) -0.005(4) -0.001(3) 0.031(4) C2S 0.057(3) 0.046(3) 0.038(2) 0.0064(19) 0.0135(19) -0.010(2) C2 0.0253(18) 0.0251(17) 0.0315(18) 0.0081(14) 0.0069(14) 0.0033(14) C3 0.0236(17) 0.0225(17) 0.0317(18) 0.0070(14) 0.0074(14) 0.0015(13) C4 0.0238(17) 0.0272(18) 0.0333(18) 0.0082(14) 0.0064(14) 0.0011(14) C5 0.0286(19) 0.0307(19) 0.0309(18) 0.0057(15) 0.0049(14) -0.0003(14) C6 0.038(2) 0.0270(19) 0.0347(19) 0.0005(15) 0.0099(16) 0.0044(15) C7 0.035(2) 0.035(2) 0.043(2) 0.0000(17) 0.0035(17) 0.0136(17) C8 0.0285(19) 0.032(2) 0.039(2) 0.0025(16) 0.0001(15) 0.0050(15) C11 0.0245(17) 0.0225(17) 0.0319(17) 0.0078(14) 0.0079(14) 0.0030(13) C13 0.0272(18) 0.0250(18) 0.0320(18) 0.0076(14) 0.0054(14) 0.0006(14) C14 0.0272(18) 0.0207(17) 0.0344(18) 0.0046(14) 0.0080(14) -0.0009(13) C15 0.0252(18) 0.0215(17) 0.0311(17) 0.0072(14) 0.0074(14) 0.0014(13) C17 0.0237(19) 0.036(2) 0.043(2) 0.0011(17) 0.0004(15) 0.0027(15) C22 0.0270(19) 0.0261(18) 0.0284(17) 0.0047(14) 0.0036(14) 0.0040(14) C23 0.0266(18) 0.0240(17) 0.0298(18) 0.0058(14) 0.0031(14) 0.0040(14) C24 0.029(2) 0.033(2) 0.052(2) 0.0141(18) 0.0082(17) 0.0065(15) C25 0.044(2) 0.031(2) 0.065(3) 0.021(2) 0.011(2) 0.0126(17) C26 0.043(2) 0.029(2) 0.048(2) 0.0166(18) 0.0087(18) 0.0018(17) C27 0.034(2) 0.040(2) 0.050(2) 0.0193(19) 0.0088(18) 0.0027(17) C28 0.0287(19) 0.036(2) 0.040(2) 0.0159(17) 0.0066(16) 0.0055(15) C31 0.0244(17) 0.0210(17) 0.0270(17) 0.0026(13) 0.0038(13) 0.0017(13) C33 0.0276(18) 0.0266(18) 0.0306(18) 0.0077(14) 0.0046(14) 0.0073(14) C34 0.0296(19) 0.0234(18) 0.0366(19) 0.0101(15) 0.0023(15) 0.0041(14) C35 0.0249(18) 0.0245(18) 0.0343(19) 0.0051(14) 0.0036(14) 0.0005(14) C37 0.027(2) 0.037(2) 0.058(3) 0.0218(19) 0.0075(17) 0.0111(16) N1 0.0225(16) 0.0210(15) 0.0361(17) 0.0025(12) 0.0047(13) 0.0024(12) N12 0.0214(14) 0.0213(14) 0.0334(15) 0.0042(12) 0.0044(12) 0.0007(11) N16 0.0190(14) 0.0213(14) 0.0346(16) 0.0037(12) 0.0037(12) 0.0015(11) N21 0.0199(16) 0.0237(15) 0.0363(16) 0.0090(12) 0.0025(12) 0.0014(12) N32 0.0240(15) 0.0241(15) 0.0321(15) 0.0076(12) 0.0038(12) 0.0060(11) N36 0.0224(15) 0.0220(15) 0.0371(17) 0.0081(13) 0.0018(12) 0.0021(12) O2 0.0245(13) 0.0354(15) 0.0469(16) -0.0027(12) 0.0023(11) 0.0075(11) O15 0.0232(13) 0.0236(12) 0.0426(14) 0.0052(11) 0.0077(10) 0.0051(10) O22 0.0221(14) 0.0341(15) 0.0579(17) 0.0210(13) 0.0035(11) 0.0036(11) O35 0.0240(13) 0.0257(13) 0.0519(16) 0.0117(12) 0.0017(11) 0.0001(10) Cl1S 0.0888(11) 0.0690(9) 0.0565(8) 0.0074(6) 0.0225(7) 0.0015(7) Cl2S 0.0752(10) 0.0573(9) 0.1486(16) 0.0461(9) 0.0522(10) 0.0261(7) Cl3S 0.0497(8) 0.1544(17) 0.0676(9) 0.0511(10) 0.0190(6) 0.0240(9) _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 C1S Cl1S 1.597(10) . ? C1S Cl1S 1.795(10) 2_656 ? C1S H1S1 0.9900 . ? C1S H1S2 0.9900 . ? C2S Cl3S 1.745(5) . ? C2S Cl2S 1.752(5) . ? C2S H2SA 0.9900 . ? C2S H2SB 0.9900 . ? C2 O2 1.229(4) . ? C2 N1 1.377(5) . ? C2 C3 1.494(5) . ? C3 C8 1.392(5) . ? C3 C4 1.393(5) . ? C4 C5 1.387(5) . ? C4 H4 0.9500 . ? C5 C6 1.386(5) . ? C5 H5 0.9500 . ? C6 C7 1.392(5) . ? C6 H6 0.9500 . ? C7 C8 1.384(5) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C11 N12 1.309(4) . ? C11 N16 1.352(4) . ? C11 N1 1.388(4) . ? C13 C14 1.356(5) . ? C13 N12 1.382(4) . ? C13 C17 1.501(5) . ? C14 C15 1.425(5) . ? C14 H14 0.9500 . ? C15 O15 1.251(4) . ? C15 N16 1.390(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C22 O22 1.224(4) . ? C22 N21 1.377(5) . ? C22 C23 1.490(5) . ? C23 C24 1.393(5) . ? C23 C28 1.394(5) . ? C24 C25 1.381(6) . ? C24 H24 0.9500 . ? C25 C26 1.372(6) . ? C25 H25 0.9500 . ? C26 C27 1.387(6) . ? C26 H26 0.9500 . ? C27 C28 1.380(5) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C31 N32 1.312(4) . ? C31 N36 1.356(4) . ? C31 N21 1.381(4) . ? C33 C34 1.362(5) . ? C33 N32 1.375(4) . ? C33 C37 1.500(5) . ? C34 C35 1.425(5) . ? C34 H34 0.9500 . ? C35 O35 1.238(4) . ? C35 N36 1.392(5) . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? N1 H1 0.78(5) . ? N16 H16 0.92(4) . ? N21 H21 0.75(4) . ? N36 H36 0.83(5) . ? Cl1S C1S 1.795(10) 2_656 ? 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 Cl1S C1S Cl1S 119.2(5) . 2_656 ? Cl1S C1S H1S1 107.5 . . ? Cl1S C1S H1S1 107.5 2_656 . ? Cl1S C1S H1S2 107.5 . . ? Cl1S C1S H1S2 107.5 2_656 . ? H1S1 C1S H1S2 107.0 . . ? Cl3S C2S Cl2S 110.8(3) . . ? Cl3S C2S H2SA 109.5 . . ? Cl2S C2S H2SA 109.5 . . ? Cl3S C2S H2SB 109.5 . . ? Cl2S C2S H2SB 109.5 . . ? H2SA C2S H2SB 108.1 . . ? O2 C2 N1 121.3(3) . . ? O2 C2 C3 121.1(3) . . ? N1 C2 C3 117.6(3) . . ? C8 C3 C4 119.3(3) . . ? C8 C3 C2 124.2(3) . . ? C4 C3 C2 116.5(3) . . ? C5 C4 C3 120.6(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 119.5(3) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 120.6(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C3 120.0(3) . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? N12 C11 N16 124.3(3) . . ? N12 C11 N1 116.9(3) . . ? N16 C11 N1 118.8(3) . . ? C14 C13 N12 123.3(3) . . ? C14 C13 C17 122.2(3) . . ? N12 C13 C17 114.5(3) . . ? C13 C14 C15 119.8(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? O15 C15 N16 119.7(3) . . ? O15 C15 C14 125.7(3) . . ? N16 C15 C14 114.6(3) . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O22 C22 N21 121.3(3) . . ? O22 C22 C23 121.1(3) . . ? N21 C22 C23 117.6(3) . . ? C24 C23 C28 118.6(3) . . ? C24 C23 C22 116.9(3) . . ? C28 C23 C22 124.4(3) . . ? C25 C24 C23 120.9(4) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C26 C25 C24 120.0(4) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 119.8(4) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C28 C27 C26 120.6(4) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 C23 120.0(3) . . ? C27 C28 H28 120.0 . . ? C23 C28 H28 120.0 . . ? N32 C31 N36 123.7(3) . . ? N32 C31 N21 116.8(3) . . ? N36 C31 N21 119.4(3) . . ? C34 C33 N32 122.9(3) . . ? C34 C33 C37 122.3(3) . . ? N32 C33 C37 114.8(3) . . ? C33 C34 C35 120.4(3) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? O35 C35 N36 119.4(3) . . ? O35 C35 C34 126.7(3) . . ? N36 C35 C34 113.9(3) . . ? C33 C37 H37A 109.5 . . ? C33 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C33 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C2 N1 C11 126.5(3) . . ? C2 N1 H1 118(4) . . ? C11 N1 H1 115(4) . . ? C11 N12 C13 116.0(3) . . ? C11 N16 C15 121.8(3) . . ? C11 N16 H16 119(2) . . ? C15 N16 H16 119(2) . . ? C22 N21 C31 126.4(3) . . ? C22 N21 H21 119(3) . . ? C31 N21 H21 114(3) . . ? C31 N32 C33 116.5(3) . . ? C31 N36 C35 122.4(3) . . ? C31 N36 H36 114(3) . . ? C35 N36 H36 123(3) . . ? C1S Cl1S C1S 60.8(5) . 2_656 ? 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 O2 C2 C3 C8 170.9(4) . . . . ? N1 C2 C3 C8 -9.5(5) . . . . ? O2 C2 C3 C4 -8.3(5) . . . . ? N1 C2 C3 C4 171.2(3) . . . . ? C8 C3 C4 C5 0.5(5) . . . . ? C2 C3 C4 C5 179.8(3) . . . . ? C3 C4 C5 C6 -0.5(5) . . . . ? C4 C5 C6 C7 -0.4(6) . . . . ? C5 C6 C7 C8 1.4(6) . . . . ? C6 C7 C8 C3 -1.4(6) . . . . ? C4 C3 C8 C7 0.4(6) . . . . ? C2 C3 C8 C7 -178.8(4) . . . . ? N12 C13 C14 C15 -0.8(5) . . . . ? C17 C13 C14 C15 179.4(3) . . . . ? C13 C14 C15 O15 178.5(3) . . . . ? C13 C14 C15 N16 -2.2(5) . . . . ? O22 C22 C23 C24 14.7(5) . . . . ? N21 C22 C23 C24 -164.8(3) . . . . ? O22 C22 C23 C28 -163.5(4) . . . . ? N21 C22 C23 C28 17.0(5) . . . . ? C28 C23 C24 C25 -1.7(6) . . . . ? C22 C23 C24 C25 179.9(4) . . . . ? C23 C24 C25 C26 2.1(7) . . . . ? C24 C25 C26 C27 -0.6(7) . . . . ? C25 C26 C27 C28 -1.2(7) . . . . ? C26 C27 C28 C23 1.6(6) . . . . ? C24 C23 C28 C27 -0.1(6) . . . . ? C22 C23 C28 C27 178.1(4) . . . . ? N32 C33 C34 C35 -0.4(5) . . . . ? C37 C33 C34 C35 180.0(4) . . . . ? C33 C34 C35 O35 177.0(4) . . . . ? C33 C34 C35 N36 -3.0(5) . . . . ? O2 C2 N1 C11 7.0(6) . . . . ? C3 C2 N1 C11 -172.6(3) . . . . ? N12 C11 N1 C2 168.7(3) . . . . ? N16 C11 N1 C2 -11.8(5) . . . . ? N16 C11 N12 C13 -0.9(5) . . . . ? N1 C11 N12 C13 178.6(3) . . . . ? C14 C13 N12 C11 2.4(5) . . . . ? C17 C13 N12 C11 -177.8(3) . . . . ? N12 C11 N16 C15 -2.4(5) . . . . ? N1 C11 N16 C15 178.2(3) . . . . ? O15 C15 N16 C11 -176.9(3) . . . . ? C14 C15 N16 C11 3.8(5) . . . . ? O22 C22 N21 C31 5.9(6) . . . . ? C23 C22 N21 C31 -174.6(3) . . . . ? N32 C31 N21 C22 166.0(3) . . . . ? N36 C31 N21 C22 -14.8(5) . . . . ? N36 C31 N32 C33 -1.4(5) . . . . ? N21 C31 N32 C33 177.8(3) . . . . ? C34 C33 N32 C31 2.7(5) . . . . ? C37 C33 N32 C31 -177.7(3) . . . . ? N32 C31 N36 C35 -2.3(5) . . . . ? N21 C31 N36 C35 178.5(3) . . . . ? O35 C35 N36 C31 -175.6(3) . . . . ? C34 C35 N36 C31 4.4(5) . . . . ? Cl1S C1S Cl1S C1S 0.0 2_656 . . 2_656 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.314 _refine_diff_density_min -1.283 _refine_diff_density_rms 0.093