data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Verma, Sandeep' _publ_contact_author_email sverma@iitk.ac.in _publ_section_title ; Characterization of an unprecedented organomercury adduct via Hg(II)-mediated cyclization of N9-propargylguanine ; _publ_author_name S.Verma data_complex2 _database_code_depnum_ccdc_archive 'CCDC 778728' #TrackingRef '- SV_NP merged.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'cyclised guanine organomercury adduct' _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 Cl Hg N5 O' _chemical_formula_sum 'C8 H6 Cl Hg N5 O' _chemical_formula_weight 424.22 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P1 21/n 1' 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 3.8929(13) _cell_length_b 12.593(4) _cell_length_c 19.667(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.034(5) _cell_angle_gamma 90.00 _cell_volume 961.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2359 _cell_measurement_theta_min 2.08 _cell_measurement_theta_max 28.38 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.930 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 16.264 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.1177 _exptl_absorpt_correction_T_max 0.1394 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method 'Phi-Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6115 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.38 _reflns_number_total 2359 _reflns_number_gt 1867 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0318P)^2^+23.4427P] 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 2359 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1219 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _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 C2 C -0.145(3) 0.3869(8) 0.0648(6) 0.020(2) Uani 1 1 d . . . C4 C -0.113(2) 0.3205(8) 0.1764(5) 0.0159(19) Uani 1 1 d . . . C5 C 0.066(3) 0.4036(8) 0.2046(5) 0.018(2) Uani 1 1 d . . . C6 C 0.178(3) 0.4854(8) 0.1598(6) 0.020(2) Uani 1 1 d . . . C8 C -0.029(3) 0.2963(7) 0.2844(5) 0.017(2) Uani 1 1 d . . . H8 H -0.0342 0.2642 0.3280 0.021 Uiso 1 1 calc R . . C9 C -0.356(3) 0.1492(8) 0.2124(5) 0.018(2) Uani 1 1 d . . . H9A H -0.5567 0.1447 0.2405 0.022 Uiso 1 1 calc R . . H9B H -0.1995 0.0894 0.2251 0.022 Uiso 1 1 calc R . . C10 C -0.476(3) 0.1412(8) 0.1380(5) 0.0154(19) Uani 1 1 d . . . C11 C -0.412(3) 0.2139(7) 0.0906(5) 0.0152(19) Uani 1 1 d . . . H11 H -0.4917 0.2030 0.0444 0.018 Uiso 1 1 calc R . . N1 N 0.055(2) 0.4694(7) 0.0921(4) 0.0196(18) Uani 1 1 d . . . N2 N -0.240(2) 0.3828(6) 0.0042(4) 0.0151(17) Uani 1 1 d . . . H2A H -0.1807 0.4333 -0.0236 0.018 Uiso 1 1 calc R . . H2B H -0.3667 0.3292 -0.0116 0.018 Uiso 1 1 calc R . . N3 N -0.224(2) 0.3072(6) 0.1098(4) 0.0130(16) Uani 1 1 d . . . N7 N 0.119(2) 0.3879(7) 0.2749(4) 0.0179(17) Uani 1 1 d . . . N9 N -0.175(2) 0.2503(6) 0.2259(4) 0.0150(17) Uani 1 1 d . . . O1 O 0.345(2) 0.5647(6) 0.1758(4) 0.0217(16) Uani 1 1 d . . . Cl1 Cl -1.0969(7) -0.1270(2) 0.05928(13) 0.0203(5) Uani 1 1 d . . . Hg1 Hg -0.75036(10) 0.00786(3) 0.105766(19) 0.01716(15) 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 C2 0.016(5) 0.017(5) 0.025(5) 0.001(4) -0.003(4) 0.000(4) C4 0.010(5) 0.016(5) 0.020(5) -0.001(4) -0.006(4) 0.004(4) C5 0.014(5) 0.022(5) 0.018(5) -0.004(4) 0.001(4) 0.003(4) C6 0.016(5) 0.023(5) 0.021(5) -0.010(4) 0.000(4) 0.009(4) C8 0.034(6) 0.009(4) 0.008(4) 0.000(3) -0.005(4) 0.004(4) C9 0.016(5) 0.018(5) 0.020(5) -0.011(4) -0.002(4) 0.006(4) C10 0.013(5) 0.012(4) 0.021(5) -0.006(4) -0.005(4) 0.008(4) C11 0.021(5) 0.012(4) 0.013(4) -0.004(4) 0.002(4) -0.005(4) N1 0.022(5) 0.018(4) 0.018(4) -0.001(3) -0.001(4) -0.007(4) N2 0.026(5) 0.013(4) 0.006(4) -0.001(3) -0.006(3) -0.004(3) N3 0.013(4) 0.010(4) 0.016(4) 0.003(3) 0.004(3) -0.001(3) N7 0.012(4) 0.021(4) 0.020(4) -0.005(3) -0.005(3) 0.002(3) N9 0.025(5) 0.004(3) 0.016(4) 0.003(3) 0.001(3) 0.004(3) O1 0.026(4) 0.015(4) 0.023(4) -0.005(3) -0.003(3) -0.003(3) Cl1 0.0204(12) 0.0216(12) 0.0187(12) -0.0027(9) -0.0003(9) -0.0047(10) Hg1 0.0151(2) 0.0166(2) 0.0193(2) -0.00169(14) -0.00181(15) -0.00163(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 C2 N2 1.222(13) . ? C2 N1 1.384(13) . ? C2 N3 1.387(13) . ? C4 N9 1.350(13) . ? C4 C5 1.354(14) . ? C4 N3 1.361(13) . ? C5 N7 1.397(13) . ? C5 C6 1.442(15) . ? C6 O1 1.221(13) . ? C6 N1 1.397(14) . ? C8 N7 1.307(13) . ? C8 N9 1.375(13) . ? C9 N9 1.469(13) . ? C9 C10 1.507(14) . ? C10 C11 1.342(14) . ? C10 Hg1 2.066(10) . ? C11 N3 1.421(12) . ? Cl1 Hg1 2.317(3) . ? 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 N2 C2 N1 122.3(10) . . ? N2 C2 N3 121.7(10) . . ? N1 C2 N3 116.0(9) . . ? N9 C4 C5 108.9(9) . . ? N9 C4 N3 123.5(9) . . ? C5 C4 N3 127.5(10) . . ? C4 C5 N7 109.3(9) . . ? C4 C5 C6 118.0(9) . . ? N7 C5 C6 132.6(10) . . ? O1 C6 N1 120.2(10) . . ? O1 C6 C5 127.2(10) . . ? N1 C6 C5 112.5(9) . . ? N7 C8 N9 114.4(9) . . ? N9 C9 C10 110.2(9) . . ? C11 C10 C9 124.6(9) . . ? C11 C10 Hg1 117.3(7) . . ? C9 C10 Hg1 118.1(7) . . ? C10 C11 N3 119.9(9) . . ? C2 N1 C6 128.6(9) . . ? C4 N3 C2 117.2(8) . . ? C4 N3 C11 118.6(8) . . ? C2 N3 C11 124.2(8) . . ? C8 N7 C5 103.3(8) . . ? C4 N9 C8 104.0(8) . . ? C4 N9 C9 123.1(9) . . ? C8 N9 C9 132.9(8) . . ? C10 Hg1 Cl1 172.4(3) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 3.349 _refine_diff_density_min -3.229 _refine_diff_density_rms 0.470 # Attachment '- SV_NP merged.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 778729' #TrackingRef '- SV_NP merged.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 9-propargylguanine _chemical_melting_point ? _chemical_formula_moiety 'C8 H7 N5 O' _chemical_formula_sum 'C8 H7 N5 O' _chemical_formula_weight 189.19 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 'P 1 21/c 1' 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 4.011(2) _cell_length_b 11.194(6) _cell_length_c 19.934(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.72(2) _cell_angle_gamma 90.00 _cell_volume 894.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1602 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 25.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9770 _exptl_absorpt_correction_T_max 0.9800 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4459 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.48 _reflns_number_total 1602 _reflns_number_gt 1209 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1538P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1602 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0942 _refine_ls_R_factor_gt 0.0769 _refine_ls_wR_factor_ref 0.2243 _refine_ls_wR_factor_gt 0.1984 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 C2 C 0.2878(7) 0.4711(2) 0.16194(14) 0.0467(7) Uani 1 1 d . . . C4 C 0.3461(6) 0.2774(2) 0.14082(13) 0.0392(7) Uani 1 1 d . . . C5 C 0.1770(6) 0.2403(2) 0.19625(13) 0.0395(7) Uani 1 1 d . . . C6 C 0.0523(7) 0.3272(2) 0.23954(14) 0.0416(7) Uani 1 1 d . . . C8 C 0.3297(7) 0.0818(2) 0.14673(13) 0.0444(7) Uani 1 1 d . . . H8 H 0.3648 0.0021 0.1360 0.053 Uiso 1 1 calc R . . C9 C 0.6331(7) 0.1691(3) 0.04847(14) 0.0481(8) Uani 1 1 d . . . H9A H 0.7881 0.2356 0.0483 0.058 Uiso 1 1 calc R . . H9B H 0.7633 0.0960 0.0499 0.058 Uiso 1 1 calc R . . C10 C 0.4271(7) 0.1712(2) -0.01366(14) 0.0485(8) Uani 1 1 d . . . N1 N 0.1225(5) 0.4427(2) 0.21829(10) 0.0422(7) Uani 1 1 d . . . H1 H 0.0567 0.5009 0.2426 0.051 Uiso 1 1 calc R . . N2 N 0.3300(8) 0.5869(2) 0.14882(14) 0.0636(8) Uani 1 1 d . . . H2A H 0.4355 0.6083 0.1142 0.076 Uiso 1 1 calc R . . H2B H 0.2517 0.6401 0.1749 0.076 Uiso 1 1 calc R . . N3 N 0.4091(6) 0.3905(2) 0.12145(11) 0.0460(7) Uani 1 1 d . . . N7 N 0.1689(6) 0.1162(2) 0.19869(12) 0.0463(7) Uani 1 1 d . . . N9 N 0.4424(5) 0.1760(2) 0.10934(11) 0.0423(7) Uani 1 1 d . . . O1 O -0.1010(5) 0.31152(18) 0.29148(9) 0.0497(6) Uani 1 1 d . . . C11 C 0.2645(8) 0.1735(3) -0.06472(17) 0.0591(9) Uani 1 1 d . . . H11 H 0.1367 0.1754 -0.1049 0.071 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 C2 0.0589(17) 0.0448(16) 0.0366(15) -0.0007(11) 0.0048(12) 0.0001(12) C4 0.0397(13) 0.0443(16) 0.0332(13) -0.0024(11) -0.0013(10) 0.0004(10) C5 0.0457(14) 0.0380(14) 0.0345(13) -0.0029(10) 0.0003(10) -0.0011(11) C6 0.0461(14) 0.0443(16) 0.0342(14) 0.0007(10) 0.0000(11) -0.0020(11) C8 0.0511(15) 0.0422(15) 0.0400(15) -0.0044(11) 0.0045(12) 0.0040(12) C9 0.0413(14) 0.0615(18) 0.0421(16) -0.0070(12) 0.0078(12) 0.0046(12) C10 0.0501(16) 0.0542(18) 0.0422(17) -0.0044(12) 0.0129(13) 0.0023(12) N1 0.0545(14) 0.0402(13) 0.0324(12) -0.0049(9) 0.0073(10) 0.0002(9) N2 0.098(2) 0.0415(15) 0.0530(17) 0.0032(11) 0.0277(14) -0.0020(13) N3 0.0540(14) 0.0469(14) 0.0381(13) 0.0002(10) 0.0107(10) -0.0034(10) N7 0.0555(14) 0.0412(14) 0.0425(13) 0.0002(10) 0.0052(10) -0.0012(10) N9 0.0447(13) 0.0466(14) 0.0359(13) -0.0055(9) 0.0056(9) 0.0032(9) O1 0.0655(13) 0.0479(12) 0.0372(12) -0.0026(8) 0.0188(9) -0.0030(8) C11 0.0586(19) 0.074(2) 0.0444(18) -0.0029(14) 0.0026(15) 0.0023(15) _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 C2 N3 1.319(4) . ? C2 N2 1.335(4) . ? C2 N1 1.369(4) . ? C4 N3 1.351(3) . ? C4 N9 1.362(3) . ? C4 C5 1.387(4) . ? C5 N7 1.391(4) . ? C5 C6 1.408(4) . ? C6 O1 1.242(3) . ? C6 N1 1.393(4) . ? C8 N7 1.304(4) . ? C8 N9 1.380(4) . ? C9 C10 1.456(4) . ? C9 N9 1.467(3) . ? C10 C11 1.183(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C2 N2 119.4(3) . . ? N3 C2 N1 123.4(3) . . ? N2 C2 N1 117.2(3) . . ? N3 C4 N9 126.0(2) . . ? N3 C4 C5 127.8(2) . . ? N9 C4 C5 106.1(2) . . ? C4 C5 N7 109.9(2) . . ? C4 C5 C6 118.9(2) . . ? N7 C5 C6 131.3(3) . . ? O1 C6 N1 120.0(2) . . ? O1 C6 C5 128.1(3) . . ? N1 C6 C5 111.8(2) . . ? N7 C8 N9 113.0(2) . . ? C10 C9 N9 113.9(2) . . ? C11 C10 C9 178.8(3) . . ? C2 N1 C6 125.3(2) . . ? C2 N3 C4 112.7(2) . . ? C8 N7 C5 104.7(2) . . ? C4 N9 C8 106.3(2) . . ? C4 N9 C9 126.6(2) . . ? C8 N9 C9 127.1(2) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.784 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.102 data_3 _database_code_depnum_ccdc_archive 'CCDC 778730' #TrackingRef '- SV_NP merged.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '7-protonated 9-propargylguanine' _chemical_melting_point ? _chemical_formula_moiety ' C8 H8 N5 O, Cl O4, H2 O ' _chemical_formula_sum 'C8 H10 Cl N5 O6' _chemical_formula_weight 307.66 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 7.4810(18) _cell_length_b 13.111(3) _cell_length_c 13.431(3) _cell_angle_alpha 72.577(4) _cell_angle_beta 84.086(5) _cell_angle_gamma 76.667(4) _cell_volume 1222.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5671 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 28.4 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.350 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9238 _exptl_absorpt_correction_T_max 0.9333 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7842 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 28.35 _reflns_number_total 5671 _reflns_number_gt 4694 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SMART 5.628 (Bruker, 2003)' _computing_data_reduction 'SAINT+ 6.45 (Bruker, 2003)' _computing_structure_solution Sir92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'diamond 3.1d' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1232P)^2^+2.8260P] 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 5671 _refine_ls_number_parameters 369 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.2393 _refine_ls_wR_factor_gt 0.1608 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.147 _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 0.48345(11) 0.35133(7) -0.38453(6) 0.0202(2) Uani 1 1 d . . . Cl1 Cl 0.14376(11) 1.13370(7) -0.75892(6) 0.0214(2) Uani 1 1 d . . . O1 O 0.0797(3) 0.59286(19) -0.67751(19) 0.0216(5) Uani 1 1 d . . . O5' O 0.3282(4) 0.3961(2) -0.4508(2) 0.0260(6) Uani 1 1 d . . . O1W O 0.0801(4) 0.5861(2) -0.40728(19) 0.0214(5) Uani 1 1 d D . . O3 O 0.1713(4) 1.1934(2) -0.6903(2) 0.0294(6) Uani 1 1 d . . . O1' O 0.1307(4) 1.5968(2) -0.9432(2) 0.0270(6) Uani 1 1 d . . . O5 O -0.0032(4) 1.1989(2) -0.8279(2) 0.0334(7) Uani 1 1 d . . . O2' O 0.4880(4) 0.4236(2) -0.3230(2) 0.0320(6) Uani 1 1 d . . . O2 O 0.3075(4) 1.1107(3) -0.8209(2) 0.0303(6) Uani 1 1 d . . . O4' O 0.4663(4) 0.2463(2) -0.3152(2) 0.0317(6) Uani 1 1 d . . . N1 N -0.0463(4) 0.7305(2) -0.8180(2) 0.0234(6) Uani 1 1 d . . . H1 H -0.0113 0.6869 -0.8564 0.028 Uiso 1 1 calc R . . O3' O 0.6481(4) 0.3391(2) -0.4485(2) 0.0282(6) Uani 1 1 d . . . N2' N 0.4464(5) 1.3563(3) -0.6611(2) 0.0271(7) Uani 1 1 d . . . H2C H 0.5201 1.2973 -0.6293 0.033 Uiso 1 1 calc R . . H2D H 0.3911 1.4019 -0.6276 0.033 Uiso 1 1 calc R . . N9 N -0.2216(4) 0.9286(2) -0.6422(2) 0.0224(6) Uani 1 1 d . . . O2W O 0.1147(4) 1.5852(2) -1.2027(2) 0.0304(6) Uani 1 1 d D . . N1' N 0.2966(4) 1.4721(2) -0.8058(2) 0.0240(6) Uani 1 1 d . . . H1' H 0.2514 1.5137 -0.7666 0.029 Uiso 1 1 calc R . . N2 N -0.1669(5) 0.8565(3) -0.9671(2) 0.0311(8) Uani 1 1 d . . . H2A H -0.2265 0.9201 -1.0003 0.037 Uiso 1 1 calc R . . H2B H -0.1257 0.8077 -0.9992 0.037 Uiso 1 1 calc R . . N3 N -0.2019(4) 0.9093(2) -0.8168(2) 0.0215(6) Uani 1 1 d . . . N7 N -0.0725(4) 0.7670(2) -0.5579(2) 0.0215(6) Uani 1 1 d . . . H7 H -0.0234 0.7119 -0.5083 0.026 Uiso 1 1 calc R . . O4 O 0.0952(4) 1.0323(2) -0.6985(2) 0.0343(7) Uani 1 1 d . . . N3' N 0.5035(4) 1.3068(2) -0.8130(2) 0.0221(6) Uani 1 1 d . . . N9' N 0.5140(4) 1.2815(2) -0.9849(2) 0.0216(6) Uani 1 1 d . . . C4 C -0.1658(5) 0.8726(3) -0.7148(3) 0.0207(7) Uani 1 1 d . . . C10 C -0.3389(6) 1.0835(3) -0.5740(3) 0.0304(8) Uani 1 1 d . . . C8 C -0.1622(5) 0.8633(3) -0.5473(3) 0.0203(7) Uani 1 1 d . . . H8 H -0.1812 0.8827 -0.4853 0.024 Uiso 1 1 calc R . . N7' N 0.3186(4) 1.4293(3) -1.0648(2) 0.0243(6) Uani 1 1 d . . . H7' H 0.2529 1.4784 -1.1126 0.029 Uiso 1 1 calc R . . C5' C 0.3246(5) 1.4309(3) -0.9628(3) 0.0233(7) Uani 1 1 d . . . C2' C 0.4180(5) 1.3772(3) -0.7617(3) 0.0231(7) Uani 1 1 d . . . C11' C 0.7213(6) 1.1121(3) -1.1351(3) 0.0292(8) Uani 1 1 d . . . H11' H 0.7430 1.0907 -1.1961 0.035 Uiso 1 1 calc R . . C9' C 0.6512(5) 1.1776(3) -0.9632(3) 0.0254(7) Uani 1 1 d . . . H9C H 0.7627 1.1878 -0.9401 0.031 Uiso 1 1 calc R . . H9D H 0.6040 1.1227 -0.9076 0.031 Uiso 1 1 calc R . . C4' C 0.4498(5) 1.3373(3) -0.9132(3) 0.0214(7) Uani 1 1 d . . . C6 C -0.0036(5) 0.6887(3) -0.7131(3) 0.0192(6) Uani 1 1 d . . . C9 C -0.3247(5) 1.0435(3) -0.6655(3) 0.0243(7) Uani 1 1 d . . . H9A H -0.2626 1.0890 -0.7226 0.029 Uiso 1 1 calc R . . H9B H -0.4470 1.0484 -0.6870 0.029 Uiso 1 1 calc R . . C8' C 0.4321(5) 1.3388(3) -1.0765(3) 0.0228(7) Uani 1 1 d . . . H8' H 0.4520 1.3180 -1.1378 0.027 Uiso 1 1 calc R . . C11 C -0.3421(6) 1.1135(3) -0.4990(3) 0.0345(9) Uani 1 1 d . . . H11 H -0.3445 1.1370 -0.4400 0.041 Uiso 1 1 calc R . . C10' C 0.6935(5) 1.1395(3) -1.0567(3) 0.0250(7) Uani 1 1 d . . . C5 C -0.0712(5) 0.7699(3) -0.6605(3) 0.0217(7) Uani 1 1 d . . . C6' C 0.2384(5) 1.5082(3) -0.9094(3) 0.0226(7) Uani 1 1 d . . . C2 C -0.1384(5) 0.8338(3) -0.8660(3) 0.0226(7) Uani 1 1 d . . . H2W1 H 0.0965 1.6509 -1.1986 0.034 Uiso 1 1 d D . . H2W2 H 0.1407 1.5941 -1.2635 0.084 Uiso 1 1 d D . . H1W1 H 0.177(4) 0.567(4) -0.437(3) 0.026(11) Uiso 1 1 d D . . H1W2 H 0.025(10) 0.529(6) -0.403(6) 0.07(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1' 0.0221(4) 0.0188(4) 0.0190(4) -0.0051(3) -0.0001(3) -0.0039(3) Cl1 0.0227(4) 0.0224(4) 0.0186(4) -0.0062(3) -0.0027(3) -0.0024(3) O1 0.0240(12) 0.0160(11) 0.0222(12) -0.0045(9) -0.0032(9) 0.0007(10) O5' 0.0249(13) 0.0270(13) 0.0229(12) -0.0061(10) -0.0076(10) 0.0024(11) O1W 0.0214(12) 0.0205(12) 0.0199(12) -0.0046(10) 0.0006(9) -0.0017(10) O3 0.0379(15) 0.0363(15) 0.0196(12) -0.0150(11) -0.0051(11) -0.0078(12) O1' 0.0331(14) 0.0198(12) 0.0238(13) -0.0060(10) -0.0010(10) 0.0025(11) O5 0.0377(16) 0.0293(14) 0.0307(14) -0.0094(12) -0.0225(12) 0.0079(12) O2' 0.0413(16) 0.0384(16) 0.0237(13) -0.0191(12) 0.0025(11) -0.0111(13) O2 0.0254(13) 0.0406(16) 0.0278(14) -0.0155(12) 0.0040(11) -0.0073(12) O4' 0.0343(15) 0.0201(13) 0.0321(14) 0.0083(11) -0.0034(12) -0.0089(11) N1 0.0296(16) 0.0222(15) 0.0179(14) -0.0069(11) -0.0002(12) -0.0035(13) O3' 0.0258(13) 0.0305(14) 0.0299(14) -0.0128(11) 0.0070(11) -0.0073(11) N2' 0.0354(17) 0.0207(15) 0.0250(16) -0.0097(12) -0.0030(13) -0.0004(13) N9 0.0259(15) 0.0218(15) 0.0178(13) -0.0052(11) -0.0019(11) -0.0018(12) O2W 0.0447(16) 0.0189(12) 0.0239(13) -0.0061(10) -0.0098(11) 0.0043(12) N1' 0.0300(16) 0.0196(14) 0.0233(15) -0.0094(12) 0.0016(12) -0.0041(12) N2 0.047(2) 0.0210(15) 0.0202(15) -0.0070(12) -0.0032(14) 0.0045(14) N3 0.0249(14) 0.0201(14) 0.0179(13) -0.0050(11) -0.0006(11) -0.0020(12) N7 0.0218(14) 0.0203(14) 0.0209(14) -0.0036(11) -0.0042(11) -0.0033(12) O4 0.0394(16) 0.0257(14) 0.0354(15) -0.0049(12) 0.0075(13) -0.0107(12) N3' 0.0254(15) 0.0210(14) 0.0194(14) -0.0072(11) 0.0008(11) -0.0032(12) N9' 0.0238(14) 0.0189(14) 0.0210(14) -0.0051(11) 0.0000(11) -0.0036(12) C4 0.0239(16) 0.0219(16) 0.0170(15) -0.0066(13) 0.0002(12) -0.0051(13) C10 0.0302(19) 0.0234(18) 0.035(2) -0.0079(16) -0.0043(16) 0.0010(16) C8 0.0228(16) 0.0160(15) 0.0181(15) -0.0025(12) -0.0020(12) 0.0013(13) N7' 0.0278(15) 0.0210(15) 0.0222(14) -0.0050(12) -0.0020(12) -0.0025(12) C5' 0.0287(18) 0.0198(16) 0.0218(16) -0.0079(13) 0.0015(13) -0.0045(14) C2' 0.0303(18) 0.0193(16) 0.0194(16) -0.0064(13) -0.0003(13) -0.0037(14) C11' 0.039(2) 0.0239(18) 0.0212(17) -0.0070(14) 0.0012(15) 0.0004(16) C9' 0.0266(17) 0.0255(18) 0.0228(17) -0.0094(14) 0.0007(13) -0.0001(15) C4' 0.0235(16) 0.0224(16) 0.0189(16) -0.0062(13) -0.0002(12) -0.0059(14) C6 0.0191(15) 0.0172(15) 0.0210(15) -0.0039(12) -0.0019(12) -0.0049(12) C9 0.0280(18) 0.0189(16) 0.0231(17) -0.0058(13) -0.0063(14) 0.0028(14) C8' 0.0253(17) 0.0193(16) 0.0234(17) -0.0063(13) -0.0030(13) -0.0025(14) C11 0.049(3) 0.0257(19) 0.0285(19) -0.0144(16) -0.0087(17) 0.0039(18) C10' 0.0222(16) 0.0266(18) 0.0253(17) -0.0092(14) 0.0002(13) -0.0017(14) C5 0.0256(17) 0.0175(16) 0.0221(16) -0.0066(13) -0.0017(13) -0.0029(13) C6' 0.0263(17) 0.0169(16) 0.0222(16) -0.0038(13) 0.0027(13) -0.0034(13) C2 0.0271(17) 0.0209(16) 0.0190(16) -0.0059(13) 0.0019(13) -0.0042(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' O3' 1.433(3) . ? Cl1' O4' 1.438(3) . ? Cl1' O5' 1.439(3) . ? Cl1' O2' 1.440(3) . ? Cl1 O3 1.431(3) . ? Cl1 O2 1.434(3) . ? Cl1 O4 1.440(3) . ? Cl1 O5 1.449(3) . ? O1 C6 1.240(4) . ? O1' C6' 1.238(4) . ? N1 C2 1.366(5) . ? N1 C6 1.392(4) . ? N2' C2' 1.325(5) . ? N9 C8 1.357(4) . ? N9 C4 1.368(4) . ? N9 C9 1.481(4) . ? N1' C2' 1.369(5) . ? N1' C6' 1.408(5) . ? N2 C2 1.329(5) . ? N3 C2 1.323(4) . ? N3 C4 1.342(4) . ? N7 C8 1.327(4) . ? N7 C5 1.367(4) . ? N3' C2' 1.325(4) . ? N3' C4' 1.359(4) . ? N9' C8' 1.358(5) . ? N9' C4' 1.363(4) . ? N9' C9' 1.474(5) . ? C4 C5 1.388(5) . ? C10 C11 1.182(6) . ? C10 C9 1.459(5) . ? N7' C8' 1.332(5) . ? N7' C5' 1.382(5) . ? C5' C4' 1.392(5) . ? C5' C6' 1.412(5) . ? C11' C10' 1.194(5) . ? C9' C10' 1.465(5) . ? C6 C5 1.419(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3' Cl1' O4' 109.43(17) . . ? O3' Cl1' O5' 108.91(16) . . ? O4' Cl1' O5' 109.93(17) . . ? O3' Cl1' O2' 110.82(17) . . ? O4' Cl1' O2' 108.64(18) . . ? O5' Cl1' O2' 109.10(17) . . ? O3 Cl1 O2 110.68(17) . . ? O3 Cl1 O4 109.58(18) . . ? O2 Cl1 O4 109.15(18) . . ? O3 Cl1 O5 108.97(17) . . ? O2 Cl1 O5 108.71(18) . . ? O4 Cl1 O5 109.72(19) . . ? C2 N1 C6 126.3(3) . . ? C8 N9 C4 109.1(3) . . ? C8 N9 C9 126.1(3) . . ? C4 N9 C9 124.8(3) . . ? C2' N1' C6' 126.2(3) . . ? C2 N3 C4 112.4(3) . . ? C8 N7 C5 108.7(3) . . ? C2' N3' C4' 112.0(3) . . ? C8' N9' C4' 108.3(3) . . ? C8' N9' C9' 127.6(3) . . ? C4' N9' C9' 124.1(3) . . ? N3 C4 N9 126.5(3) . . ? N3 C4 C5 127.7(3) . . ? N9 C4 C5 105.8(3) . . ? C11 C10 C9 176.9(4) . . ? N7 C8 N9 108.6(3) . . ? C8' N7' C5' 108.4(3) . . ? N7' C5' C4' 106.8(3) . . ? N7' C5' C6' 132.4(3) . . ? C4' C5' C6' 120.7(3) . . ? N2' C2' N3' 119.8(3) . . ? N2' C2' N1' 116.3(3) . . ? N3' C2' N1' 123.9(3) . . ? C10' C9' N9' 110.8(3) . . ? N3' C4' N9' 125.5(3) . . ? N3' C4' C5' 127.3(3) . . ? N9' C4' C5' 107.2(3) . . ? O1 C6 N1 120.9(3) . . ? O1 C6 C5 129.1(3) . . ? N1 C6 C5 110.0(3) . . ? C10 C9 N9 110.8(3) . . ? N7' C8' N9' 109.3(3) . . ? C11' C10' C9' 177.0(4) . . ? N7 C5 C4 107.9(3) . . ? N7 C5 C6 132.0(3) . . ? C4 C5 C6 120.0(3) . . ? O1' C6' N1' 121.6(3) . . ? O1' C6' C5' 128.6(3) . . ? N1' C6' C5' 109.7(3) . . ? N3 C2 N2 119.8(3) . . ? N3 C2 N1 123.6(3) . . ? N2 C2 N1 116.6(3) . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.726 _refine_diff_density_min -0.899 _refine_diff_density_rms 0.144