# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Michal Hocek' _publ_contact_author_email HOCEK@UOCHB.CAS.CZ _publ_section_title ; Synthesis of Substituted 6-Cyclopropylpurine Bases and Nucleosides by Cross-coupling Reactions or Cyclopropanations ; loop_ _publ_author_name 'Michal Hocek' 'Blanka Klepetarova' 'Martin Kuchar' 'Radek Pohl' 'Ivan Votruba' # Attachment '2g.cif' data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 677191' _audit_creation_date 08-02-06 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 6-cyclopropyl-9H-purine _cell_length_a 13.6246(3) _cell_length_b 7.01430(10) _cell_length_c 7.8922(2) _cell_angle_alpha 90 _cell_angle_beta 99.789(2) _cell_angle_gamma 90 _cell_volume 743.25(3) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/m' _symmetry_int_tables_number 12 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z x,-y,z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C8 H8 N4 # Dc = 1.43 Fooo = 336.00 Mu = 7.62 M = 80.09 # Found Formula = C8 H8 N4 # Dc = 1.43 FOOO = 336.00 Mu = 7.62 M = 80.09 _chemical_formula_sum 'C8 H8 N4' _chemical_formula_moiety 'C8 H8 N4' _chemical_formula_weight 160.18 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 6 _cell_measurement_theta_max 76 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.762 # Sheldrick geometric approximatio 0.75 0.95 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.95 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 11926 _reflns_number_total 820 _diffrn_reflns_av_R_equivalents 0.046 # Number of reflections with Friedels Law is 820 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 777 _diffrn_reflns_theta_min 5.689 _diffrn_reflns_theta_max 76.147 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 69.294 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 9 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.29 _refine_diff_density_max 0.27 _refine_ls_number_reflns 723 _refine_ls_number_restraints 0 _refine_ls_number_parameters 75 #_refine_ls_R_factor_ref 0.0409 _refine_ls_wR_factor_ref 0.0577 _refine_ls_goodness_of_fit_ref 0.9440 #_reflns_number_all 815 _refine_ls_R_factor_all 0.0446 _refine_ls_wR_factor_all 0.0588 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 723 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_gt 0.0577 _refine_ls_shift/su_max 0.000275 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 15.4 2.45 13.6 ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens N1 N 0.71827(10) 1.0000 0.16586(17) 0.0260 1.0000 Uani S T . . . . N3 N 0.57918(9) 1.0000 0.31824(17) 0.0270 1.0000 Uani S T . . . . N7 N 0.79911(10) 1.0000 0.63791(17) 0.0289 1.0000 Uani S T . . . . N9 N 0.63303(10) 1.000000(7) 0.62823(17) 0.0265 1.0000 Uani S T . . . . C2 C 0.62186(11) 1.000000(7) 0.1773(2) 0.0279 1.0000 Uani S T . . . . C4 C 0.64737(11) 1.0000 0.4614(2) 0.0233 1.0000 Uani S T . . . . C5 C 0.75080(11) 1.0000 0.46833(19) 0.0232 1.0000 Uani S T . . . . C6 C 0.78523(11) 1.0000 0.3115(2) 0.0245 1.0000 Uani S T . . . . C8 C 0.72605(12) 1.000000(7) 0.7265(2) 0.0292 1.0000 Uani S T . . . . C10 C 0.89164(12) 1.000000(7) 0.3009(2) 0.0360 1.0000 Uani S T . . . . C11 C 0.92658(9) 0.8953(2) 0.15432(17) 0.0371 1.0000 Uani . . . . . . H21 H 0.9371 1.0000 0.4097 0.0324 1.0000 Uiso RS . . . . . H81 H 0.7368 1.0000 0.8461 0.0262 1.0000 Uiso RS . . . . . H91 H 0.5770 1.0000 0.6638 0.0223 1.0000 Uiso RS . . . . . H101 H 0.5781 1.0000 0.0732 0.0232 1.0000 Uiso RS . . . . . H111 H 0.9881 0.8211 0.1786 0.0360 1.0000 Uiso R . . . . . H112 H 0.8773 0.8209 0.0757 0.0359 1.0000 Uiso 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 0.0221(7) 0.0371(7) 0.0196(7) 0.0000 0.0052(5) 0.0000 N3 0.0203(6) 0.0381(8) 0.0232(8) 0.0000 0.0057(5) 0.0000 N7 0.0255(7) 0.0423(8) 0.0187(7) 0.0000 0.0033(5) 0.0000 N9 0.0237(7) 0.0374(7) 0.0203(7) 0.0000 0.0096(5) 0.0000 C2 0.0209(7) 0.0426(9) 0.0200(8) 0.0000 0.0029(6) 0.0000 C4 0.0226(8) 0.0274(7) 0.0211(8) 0.0000 0.0070(6) 0.0000 C5 0.0208(7) 0.0296(8) 0.0195(8) 0.0000 0.0046(6) 0.0000 C6 0.0226(8) 0.0313(7) 0.0202(8) 0.0000 0.0052(6) 0.0000 C8 0.0285(8) 0.0401(8) 0.0193(8) 0.0000 0.0051(6) 0.0000 C10 0.0206(8) 0.0680(12) 0.0201(8) 0.0000 0.0048(6) 0.0000 C11 0.0311(6) 0.0465(8) 0.0378(7) 0.0057(5) 0.0180(5) 0.0101(5) _refine_ls_extinction_coef 52(7) _refine_ls_extinction_method 'Larson (1970), Equation 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.332(2) yes N1 . C6 . 1.340(2) yes N3 . C2 . 1.3396(19) yes N3 . C4 . 1.335(2) yes N7 . C5 . 1.387(2) yes N7 . C8 . 1.310(2) yes N9 . C4 . 1.363(2) yes N9 . C8 . 1.369(2) yes N9 . H91 . 0.857 no C2 . H101 . 0.930 no C4 . C5 . 1.401(2) yes C5 . C6 . 1.396(2) yes C6 . C10 . 1.466(2) yes C8 . H81 . 0.931 no C10 . C11 6_575 1.5138(18) yes C10 . C11 . 1.5138(18) yes C10 . H21 . 0.970 no C11 . C11 6_575 1.469(3) yes C11 . H111 . 0.977 no C11 . H112 . 0.983 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C6 . 118.49(14) yes C2 . N3 . C4 . 111.40(12) yes C5 . N7 . C8 . 103.65(13) yes C4 . N9 . C8 . 106.03(13) yes C4 . N9 . H91 . 126.7 no C8 . N9 . H91 . 127.2 no N3 . C2 . N1 . 128.96(14) yes N3 . C2 . H101 . 115.5 no N1 . C2 . H101 . 115.6 no N9 . C4 . N3 . 128.61(14) yes N9 . C4 . C5 . 105.71(14) yes N3 . C4 . C5 . 125.68(15) yes C4 . C5 . N7 . 110.27(14) yes C4 . C5 . C6 . 116.93(15) yes N7 . C5 . C6 . 132.80(15) yes C5 . C6 . N1 . 118.55(14) yes C5 . C6 . C10 . 122.34(15) yes N1 . C6 . C10 . 119.11(14) yes N9 . C8 . N7 . 114.33(15) yes N9 . C8 . H81 . 123.1 no N7 . C8 . H81 . 122.6 no C11 6_575 C10 . C6 . 119.08(12) yes C11 6_575 C10 . C11 . 58.06(12) yes C6 . C10 . C11 . 119.08(12) yes C11 6_575 C10 . H21 . 116.1 no C6 . C10 . H21 . 116.0 no C11 . C10 . H21 . 116.1 no C10 . C11 . C11 6_575 60.97(6) yes C10 . C11 . H111 . 118.6 no C11 6_575 C11 . H111 . 122.2 no C10 . C11 . H112 . 118.1 no C11 6_575 C11 . H112 . 122.1 no H111 . C11 . H112 . 108.2 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N9 . H91 . N3 2_676 165 0.86 2.16 2.992(2) yes _chemical_name_common 6-cyclopropyl-9H-purine # Attachment '6a.cif' data_CRYSTALS1_cif _database_code_depnum_ccdc_archive 'CCDC 677192' _audit_creation_date 08-02-07 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic 9-Benzyl-6-[2-(diethylcarbamoyl)cyclopropyl]purine _cell_length_a 22.2791(2) _cell_length_b 16.20300(10) _cell_length_c 4.98 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1797.72(2) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_int_tables_number 33 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,z+1/2 x+1/2,-y+1/2,z -x,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C20 H23 N5 O1 # Dc = 1.29 Fooo = 744.00 Mu = 6.64 M = 349.44 # Found Formula = C20 H23 N5 O1 # Dc = 1.29 FOOO = 744.00 Mu = 6.64 M = 349.44 _chemical_formula_sum 'C20 H23 N5 O1' _chemical_formula_moiety 'C20 H23 N5 O1' _chemical_formula_weight 349.44 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 4 _cell_measurement_theta_max 76 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_max 0.59 _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.664 # Sheldrick geometric approximatio 0.94 0.94 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.94 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 26954 _reflns_number_total 3604 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections with Friedels Law is 2097 # Number of reflections without Friedels Law is 3604 # Theoretical number of reflections is about 1892 _diffrn_reflns_theta_min 3.968 _diffrn_reflns_theta_max 76.697 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 74.396 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 6 _reflns_limit_h_min 0 _reflns_limit_h_max 27 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min -5 _reflns_limit_l_max 6 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.16 _refine_diff_density_max 0.12 _refine_ls_number_reflns 2807 _refine_ls_number_restraints 0 _refine_ls_number_parameters 237 #_refine_ls_R_factor_ref 0.0296 _refine_ls_wR_factor_ref 0.0328 _refine_ls_goodness_of_fit_ref 1.0836 #_reflns_number_all 3594 _refine_ls_R_factor_all 0.0361 _refine_ls_wR_factor_all 0.0402 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2807 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_gt 0.0328 _refine_ls_shift/su_max 0.000574 _refine_ls_abs_structure_Flack 0.0(2) _refine_ls_abs_structure_details 'Flack (1983), 1507 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 2.28 1.47 0.608 ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O21 O 0.71005(5) 0.45761(7) 0.3884(3) 0.0346 1.0000 Uani . . . . . . N1 N 0.57477(6) 0.70738(8) 0.5710(3) 0.0319 1.0000 Uani . . . . . . N3 N 0.55737(6) 0.83684(8) 0.3461(3) 0.0327 1.0000 Uani . . . . . . N7 N 0.69444(6) 0.75605(8) 0.0795(3) 0.0314 1.0000 Uani . . . . . . N9 N 0.63601(6) 0.86892(7) 0.0243(3) 0.0294 1.0000 Uani . . . . . . N22 N 0.62040(6) 0.40009(8) 0.2919(3) 0.0302 1.0000 Uani . . . . . . C2 C 0.54419(8) 0.77654(10) 0.5197(4) 0.0338 1.0000 Uani . . . . . . C4 C 0.60850(7) 0.82164(9) 0.2167(3) 0.0273 1.0000 Uani . . . . . . C5 C 0.64492(7) 0.75185(9) 0.2486(3) 0.0268 1.0000 Uani . . . . . . C6 C 0.62596(7) 0.69361(9) 0.4360(3) 0.0281 1.0000 Uani . . . . . . C8 C 0.68701(7) 0.82635(10) -0.0486(4) 0.0317 1.0000 Uani . . . . . . C10 C 0.61690(8) 0.95005(9) -0.0755(3) 0.0311 1.0000 Uani . . . . . . C11 C 0.61962(7) 1.01511(10) 0.1423(3) 0.0295 1.0000 Uani . . . . . . C12 C 0.67489(8) 1.04658(10) 0.2232(4) 0.0350 1.0000 Uani . . . . . . C13 C 0.67800(8) 1.10541(10) 0.4266(4) 0.0393 1.0000 Uani . . . . . . C14 C 0.62547(8) 1.13182(10) 0.5503(4) 0.0369 1.0000 Uani . . . . . . C15 C 0.57066(8) 1.10169(10) 0.4690(4) 0.0378 1.0000 Uani . . . . . . C16 C 0.56770(8) 1.04358(10) 0.2632(4) 0.0351 1.0000 Uani . . . . . . C17 C 0.66021(7) 0.61717(9) 0.4885(3) 0.0294 1.0000 Uani . . . . . . C18 C 0.65239(8) 0.57293(10) 0.7493(4) 0.0332 1.0000 Uani . . . . . . C19 C 0.62434(7) 0.53691(9) 0.5003(3) 0.0282 1.0000 Uani . . . . . . C20 C 0.65473(7) 0.46216(10) 0.3877(4) 0.0297 1.0000 Uani . . . . . . C23 C 0.55472(7) 0.40095(11) 0.2778(3) 0.0338 1.0000 Uani . . . . . . C24 C 0.52501(8) 0.37363(13) 0.5367(4) 0.0438 1.0000 Uani . . . . . . C25 C 0.65094(8) 0.32323(10) 0.2140(4) 0.0327 1.0000 Uani . . . . . . C26 C 0.67870(8) 0.32791(12) -0.0612(4) 0.0407 1.0000 Uani . . . . . . H21 H 0.5082 0.7847 0.6238 0.0389 1.0000 Uiso R . . . . . H81 H 0.7140 0.8475 -0.1846 0.0370 1.0000 Uiso R . . . . . H101 H 0.6430 0.9669 -0.2298 0.0378 1.0000 Uiso R . . . . . H102 H 0.5753 0.9451 -0.1433 0.0364 1.0000 Uiso R . . . . . H121 H 0.7104 1.0277 0.1376 0.0410 1.0000 Uiso R . . . . . H131 H 0.7154 1.1258 0.4770 0.0473 1.0000 Uiso R . . . . . H141 H 0.6285 1.1707 0.7012 0.0448 1.0000 Uiso R . . . . . H151 H 0.5348 1.1206 0.5532 0.0433 1.0000 Uiso R . . . . . H161 H 0.5291 1.0240 0.2087 0.0428 1.0000 Uiso R . . . . . H171 H 0.6995 0.6146 0.4027 0.0336 1.0000 Uiso R . . . . . H181 H 0.6882 0.5460 0.8248 0.0393 1.0000 Uiso R . . . . . H182 H 0.6262 0.5962 0.8885 0.0382 1.0000 Uiso R . . . . . H191 H 0.5806 0.5427 0.4786 0.0313 1.0000 Uiso R . . . . . H231 H 0.5417 0.4590 0.2314 0.0393 1.0000 Uiso R . . . . . H232 H 0.5435 0.3640 0.1319 0.0396 1.0000 Uiso R . . . . . H241 H 0.4807 0.3730 0.5162 0.0642 1.0000 Uiso R . . . . . H242 H 0.5358 0.4121 0.6844 0.0639 1.0000 Uiso R . . . . . H243 H 0.5397 0.3186 0.5896 0.0649 1.0000 Uiso R . . . . . H251 H 0.6837 0.3088 0.3432 0.0396 1.0000 Uiso R . . . . . H252 H 0.6206 0.2771 0.2151 0.0386 1.0000 Uiso R . . . . . H261 H 0.6997 0.2747 -0.0969 0.0597 1.0000 Uiso R . . . . . H262 H 0.7075 0.3743 -0.0717 0.0601 1.0000 Uiso R . . . . . H263 H 0.6470 0.3380 -0.1979 0.0591 1.0000 Uiso 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 O21 0.0321(6) 0.0274(6) 0.0445(7) -0.0024(5) -0.0021(5) 0.0031(5) N1 0.0348(7) 0.0248(6) 0.0361(8) 0.0021(6) 0.0024(6) 0.0003(5) N3 0.0318(7) 0.0271(6) 0.0391(8) 0.0006(6) 0.0028(6) 0.0027(6) N7 0.0308(7) 0.0264(7) 0.0370(8) -0.0025(6) 0.0028(6) -0.0014(5) N9 0.0328(7) 0.0228(6) 0.0325(7) 0.0019(6) 0.0017(6) -0.0002(5) N22 0.0329(7) 0.0241(6) 0.0337(8) -0.0031(6) -0.0004(6) -0.0013(6) C2 0.0351(8) 0.0273(8) 0.0390(10) 0.0008(7) 0.0063(7) 0.0006(7) C4 0.0301(8) 0.0230(7) 0.0289(8) -0.0001(6) -0.0011(6) -0.0010(6) C5 0.0293(8) 0.0217(7) 0.0293(8) -0.0012(6) -0.0015(7) -0.0001(6) C6 0.0310(8) 0.0239(7) 0.0294(8) -0.0016(6) -0.0022(7) -0.0010(6) C8 0.0328(8) 0.0291(8) 0.0333(9) -0.0007(7) 0.0046(7) -0.0016(7) C10 0.0376(9) 0.0251(7) 0.0307(9) 0.0036(7) -0.0021(7) 0.0010(6) C11 0.0355(8) 0.0222(7) 0.0306(8) 0.0055(6) 0.0003(6) 0.0013(6) C12 0.0327(8) 0.0320(8) 0.0404(10) 0.0007(8) 0.0006(8) 0.0001(7) C13 0.0408(10) 0.0339(9) 0.0431(10) -0.0010(8) -0.0034(8) -0.0043(7) C14 0.0526(11) 0.0239(7) 0.0341(10) 0.0013(7) 0.0000(9) 0.0020(7) C15 0.0409(9) 0.0293(8) 0.0431(11) 0.0019(8) 0.0065(8) 0.0063(7) C16 0.0350(9) 0.0290(8) 0.0413(10) 0.0032(7) -0.0007(8) -0.0010(7) C17 0.0315(8) 0.0245(7) 0.0322(9) 0.0012(6) -0.0031(7) -0.0004(6) C18 0.0396(9) 0.0312(8) 0.0289(9) -0.0001(7) -0.0021(7) 0.0032(7) C19 0.0288(8) 0.0238(7) 0.0321(8) 0.0001(6) 0.0004(6) 0.0006(6) C20 0.0341(8) 0.0241(7) 0.0309(9) 0.0023(6) -0.0009(7) 0.0018(6) C23 0.0345(8) 0.0356(9) 0.0312(9) -0.0016(7) -0.0051(7) -0.0019(7) C24 0.0400(10) 0.0541(11) 0.0373(10) -0.0013(9) 0.0013(8) -0.0030(8) C25 0.0407(9) 0.0234(8) 0.0341(9) -0.0013(7) 0.0001(7) 0.0006(7) C26 0.0498(11) 0.0408(9) 0.0316(9) -0.0042(8) -0.0008(8) 0.0055(8) _refine_ls_extinction_coef 24(4) _refine_ls_extinction_method 'Larson (1970), Equation 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O21 . C20 . 1.2347(19) yes N1 . C2 . 1.336(2) yes N1 . C6 . 1.343(2) yes N3 . C2 . 1.337(2) yes N3 . C4 . 1.332(2) yes N7 . C5 . 1.389(2) yes N7 . C8 . 1.316(2) yes N9 . C4 . 1.371(2) yes N9 . C8 . 1.378(2) yes N9 . C10 . 1.4684(18) yes N22 . C20 . 1.351(2) yes N22 . C23 . 1.465(2) yes N22 . C25 . 1.471(2) yes C2 . H21 . 0.964 no C4 . C5 . 1.401(2) yes C5 . C6 . 1.392(2) yes C6 . C17 . 1.478(2) yes C8 . H81 . 0.968 no C10 . C11 . 1.513(2) yes C10 . H101 . 1.001 no C10 . H102 . 0.990 no C11 . C12 . 1.392(2) yes C11 . C16 . 1.383(2) yes C12 . C13 . 1.392(3) yes C12 . H121 . 0.950 no C13 . C14 . 1.390(3) yes C13 . H131 . 0.931 no C14 . C15 . 1.376(2) yes C14 . H141 . 0.982 no C15 . C16 . 1.393(2) yes C15 . H151 . 0.953 no C16 . H161 . 0.956 no C17 . C18 . 1.493(2) yes C17 . C19 . 1.527(2) yes C17 . H171 . 0.975 no C18 . C19 . 1.505(2) yes C18 . H181 . 0.983 no C18 . H182 . 0.981 no C19 . C20 . 1.496(2) yes C19 . H191 . 0.985 no C23 . C24 . 1.515(2) yes C23 . H231 . 1.011 no C23 . H232 . 0.975 no C24 . H241 . 0.992 no C24 . H242 . 0.993 no C24 . H243 . 0.985 no C25 . C26 . 1.504(3) yes C25 . H251 . 1.000 no C25 . H252 . 1.007 no C26 . H261 . 0.997 no C26 . H262 . 0.990 no C26 . H263 . 0.994 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C6 . 118.48(14) yes C2 . N3 . C4 . 111.43(14) yes C5 . N7 . C8 . 103.65(13) yes C4 . N9 . C8 . 105.84(13) yes C4 . N9 . C10 . 127.37(14) yes C8 . N9 . C10 . 126.74(14) yes C20 . N22 . C23 . 125.14(14) yes C20 . N22 . C25 . 117.48(13) yes C23 . N22 . C25 . 117.22(13) yes N3 . C2 . N1 . 128.65(16) yes N3 . C2 . H21 . 115.4 no N1 . C2 . H21 . 115.9 no N9 . C4 . N3 . 128.11(14) yes N9 . C4 . C5 . 105.74(14) yes N3 . C4 . C5 . 126.14(15) yes C4 . C5 . N7 . 110.59(14) yes C4 . C5 . C6 . 116.58(14) yes N7 . C5 . C6 . 132.83(14) yes C5 . C6 . N1 . 118.71(14) yes C5 . C6 . C17 . 121.99(15) yes N1 . C6 . C17 . 119.30(14) yes N9 . C8 . N7 . 114.17(14) yes N9 . C8 . H81 . 121.3 no N7 . C8 . H81 . 124.5 no N9 . C10 . C11 . 111.69(13) yes N9 . C10 . H101 . 109.6 no C11 . C10 . H101 . 109.7 no N9 . C10 . H102 . 108.3 no C11 . C10 . H102 . 109.8 no H101 . C10 . H102 . 107.8 no C10 . C11 . C12 . 119.86(15) yes C10 . C11 . C16 . 120.70(15) yes C12 . C11 . C16 . 119.44(16) yes C11 . C12 . C13 . 120.35(17) yes C11 . C12 . H121 . 119.3 no C13 . C12 . H121 . 120.4 no C12 . C13 . C14 . 119.39(17) yes C12 . C13 . H131 . 118.9 no C14 . C13 . H131 . 121.7 no C13 . C14 . C15 . 120.52(17) yes C13 . C14 . H141 . 118.6 no C15 . C14 . H141 . 120.8 no C14 . C15 . C16 . 119.87(16) yes C14 . C15 . H151 . 120.0 no C16 . C15 . H151 . 120.1 no C15 . C16 . C11 . 120.39(16) yes C15 . C16 . H161 . 118.4 no C11 . C16 . H161 . 121.2 no C6 . C17 . C18 . 119.72(15) yes C6 . C17 . C19 . 116.75(13) yes C18 . C17 . C19 . 59.77(11) yes C6 . C17 . H171 . 115.0 no C18 . C17 . H171 . 117.7 no C19 . C17 . H171 . 116.8 no C17 . C18 . C19 . 61.25(11) yes C17 . C18 . H181 . 116.8 no C19 . C18 . H181 . 118.6 no C17 . C18 . H182 . 120.0 no C19 . C18 . H182 . 118.9 no H181 . C18 . H182 . 112.5 no C17 . C19 . C18 . 58.98(10) yes C17 . C19 . C20 . 115.97(13) yes C18 . C19 . C20 . 115.74(14) yes C17 . C19 . H191 . 115.6 no C18 . C19 . H191 . 117.6 no C20 . C19 . H191 . 119.0 no C19 . C20 . N22 . 118.60(14) yes C19 . C20 . O21 . 119.93(14) yes N22 . C20 . O21 . 121.45(15) yes N22 . C23 . C24 . 113.13(14) yes N22 . C23 . H231 . 107.9 no C24 . C23 . H231 . 109.9 no N22 . C23 . H232 . 106.7 no C24 . C23 . H232 . 110.0 no H231 . C23 . H232 . 109.1 no C23 . C24 . H241 . 110.5 no C23 . C24 . H242 . 109.9 no H241 . C24 . H242 . 108.8 no C23 . C24 . H243 . 110.3 no H241 . C24 . H243 . 110.4 no H242 . C24 . H243 . 106.9 no N22 . C25 . C26 . 112.79(14) yes N22 . C25 . H251 . 111.4 no C26 . C25 . H251 . 107.3 no N22 . C25 . H252 . 108.5 no C26 . C25 . H252 . 108.5 no H251 . C25 . H252 . 108.1 no C25 . C26 . H261 . 108.2 no C25 . C26 . H262 . 110.7 no H261 . C26 . H262 . 110.1 no C25 . C26 . H263 . 109.8 no H261 . C26 . H263 . 110.7 no H262 . C26 . H263 . 107.4 no _chemical_name_common 9-Benzyl-6-(2-(diethylcarbamoyl)cyclopropyl)purine