#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/36/2003660.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2003660 loop_ _publ_author_name 'Beagley, B.' 'Booth, B. L.' 'Eastwood, P. R.' 'Kieger, S.' 'Pritchard, R. G.' 'Alves, M. J.' 'Carvalho, A.' 'Proen\,ca, M. F. J. R. P.' _publ_section_title ; A Tautomeric Pair of 2,2-Dimethyl-6-carbamoyl-9-phenyldihydropurines ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1467 _journal_page_last 1470 _journal_paper_doi 10.1107/S0108270194009558 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C14 H15 N5 O' _chemical_formula_sum 'C14 H15 N5 O' _chemical_formula_weight 269.31 _chemical_melting_point 187 _chemical_name_systematic ' 2,2-dimethyl-9-phenyl-1,2H-dihydropurine-6-carboxamide' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_type_scat_source 'International Tables Vol. IV' _cell_angle_alpha 90 _cell_angle_beta 115.0(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.33(3) _cell_length_b 8.26(4) _cell_length_c 14.25(3) _cell_measurement_reflns_used 22 _cell_measurement_temperature 296 _cell_measurement_theta_max 14.64 _cell_measurement_theta_min 5.79 _cell_volume 1315(9) _computing_cell_refinement TEXSAN _computing_data_collection 'TEXSAN (Molecular Structure Corporation,1985)' _computing_data_reduction TEXSAN _computing_molecular_graphics 'PLUTO (Motherwell & Clegg, 1978)' _computing_publication_material 'CIF (Hall, Allen & Brown, 1991)' _computing_structure_refinement TEXSAN _computing_structure_solution 'MITHRIL (Gilmore, 1984)' _diffrn_ambient_temperature 296 _diffrn_measurement_device 'Rigaku AFC6S diffractometer' _diffrn_measurement_method \w _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents .086 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5599 _diffrn_reflns_theta_max 25 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_crystal_colour orange-red _exptl_crystal_density_diffrn 1.361 _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _refine_diff_density_max .20 _refine_diff_density_min -.25 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.49 _refine_ls_hydrogen_treatment 'Some H-atom parameters refined' _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 184 _refine_ls_number_reflns 738 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs .049 _refine_ls_shift/esd_max 0.002 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'weights: default scheme in TEXSAN' _refine_ls_wR_factor_obs .052 _reflns_number_observed 738 _reflns_number_total 4972 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ha1128.cif _cod_data_source_block A _cod_original_cell_volume 1314(6) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2003660 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 O13 0.105(5) -0.001(4) 0.037(4) 0.045(4) -0.011(3) 0.041(4) N1 0.070(6) 0.001(4) 0.020(4) 0.035(5) -0.004(4) 0.025(5) N3 0.040(5) 0.000(4) 0.010(4) 0.027(4) -0.000(3) 0.024(4) N7 0.078(6) -0.008(5) 0.024(4) 0.034(4) -0.005(4) 0.034(5) N9 0.055(5) -0.005(4) 0.020(4) 0.034(4) -0.000(4) 0.026(4) N14 0.072(6) -0.004(4) 0.019(4) 0.022(4) -0.006(4) 0.047(5) C2 0.045(6) -0.000(5) 0.010(5) 0.033(6) -0.001(4) 0.024(6) C4 0.033(6) 0.003(5) 0.018(5) 0.025(5) -0.005(5) 0.042(6) C5 0.053(6) 0.001(5) 0.016(5) 0.025(5) -0.002(4) 0.028(5) C6 0.040(5) 0.004(5) 0.017(5) 0.026(5) 0.002(5) 0.039(6) C8 0.062(7) -0.003(5) 0.028(5) 0.045(6) 0.012(5) 0.041(6) C15 0.029(6) -0.003(4) 0.011(4) 0.028(5) -0.003(4) 0.029(5) C16 0.051(6) -0.016(5) 0.017(4) 0.047(6) -0.014(4) 0.027(5) C17 0.067(7) -0.012(6) 0.022(6) 0.052(7) -0.002(5) 0.047(6) C18 0.073(8) -0.007(6) 0.022(6) 0.058(7) -0.019(6) 0.050(7) C19 0.067(8) 0.004(6) 0.031(6) 0.066(7) -0.011(6) 0.045(6) C20 0.056(6) 0.001(5) 0.028(5) 0.039(6) 0.002(5) 0.045(6) C10 0.052(6) -0.000(5) 0.020(5) 0.043(6) 0.002(4) 0.032(5) C11 0.052(7) -0.003(5) 0.014(5) 0.049(5) -0.001(4) 0.035(5) C12 0.051(6) 0.007(5) 0.016(5) 0.024(5) 0.004(5) 0.044(6) H1 0.044 0 0 0.044 0 0.044 H8 0.057 0 0 0.057 0 0.057 H16 0.050 0 0 0.050 0 0.050 H17 0.067 0 0 0.067 0 0.067 H18 0.074 0 0 0.074 0 0.074 H19 0.068 0 0 0.068 0 0.068 H20 0.053 0 0 0.053 0 0.053 H10A 0.050 0 0 0.050 0 0.050 H10B 0.050 0 0 0.050 0 0.050 H10C 0.050 0 0 0.050 0 0.050 H11A 0.056 0 0 0.056 0 0.056 H11B 0.056 0 0 0.056 0 0.056 H11C 0.056 0 0 0.056 0 0.056 H14A 0.059 0 0 0.059 0 0.059 H14B 0.059 0 0 0.059 0 0.059 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O13 0.9519(5) 0.6847(6) 0.8994(4) 4.8(3) Uani ? ? N1 0.9371(6) 0.3665(8) 0.8477(5) 3.4(3) Uani ? ? N3 0.9037(5) 0.1411(7) 0.7272(4) 2.5(3) Uani ? ? N7 0.9303(6) 0.5078(8) 0.6027(5) 3.8(3) Uani ? ? N9 0.8809(6) 0.2450(8) 0.5605(5) 2.9(3) Uani ? ? N14 0.9376(6) 0.7597(8) 0.7409(5) 3.8(3) Uani ? ? C2 0.9531(7) 0.1902(9) 0.8374(5) 2.8(4) Uani ? ? C4 0.9090(7) 0.2545(10) 0.6671(6) 2.6(4) Uani ? ? C5 0.9381(7) 0.4224(9) 0.6907(6) 2.8(4) Uani ? ? C6 0.9439(7) 0.4794(9) 0.7818(6) 2.8(4) Uani ? ? C8 0.8977(8) 0.3998(10) 0.5308(6) 3.7(4) Uani ? ? C15 0.8490(7) 0.1068(10) 0.4948(5) 2.3(4) Uani ? ? C16 0.7870(8) -0.0192(11) 0.5126(5) 3.3(4) Uani ? ? C17 0.7555(8) -0.1518(10) 0.4473(7) 4.4(5) Uani ? ? C18 0.7856(9) -0.1569(12) 0.3653(7) 4.9(5) Uani ? ? C19 0.8471(8) -0.0311(12) 0.3480(6) 4.5(5) Uani ? ? C20 0.8799(7) 0.1027(9) 0.4126(6) 3.5(4) Uani ? ? C10 0.8840(7) 0.1028(9) 0.8886(5) 3.3(4) Uani ? ? C11 1.0858(8) 0.1500(9) 0.8884(5) 3.7(4) Uani ? ? C12 0.9446(7) 0.6528(10) 0.8131(7) 3.2(4) Uani ? ? H1 0.949(6) 0.396(8) 0.909(5) 3.5 Uiso ? ? H8 0.886 0.424 0.462 4.5 Uiso calc C8 H16 0.766 -0.015 0.569 3.9 Uiso calc C16 H17 0.713 -0.239 0.459 5.3 Uiso calc C17 H18 0.764 -0.248 0.320 5.8 Uiso calc C18 H19 0.868 -0.036 0.291 5.4 Uiso calc C19 H20 0.923 0.190 0.401 4.2 Uiso calc C20 H10A 0.893 -0.011 0.884 3.9 Uiso calc C10 H10B 0.914 0.134 0.959 3.9 Uiso calc C10 H10C 0.802 0.131 0.855 3.9 Uiso calc C10 H11A 1.096 0.037 0.884 4.4 Uiso calc C11 H11B 1.118 0.182 0.959 4.4 Uiso calc C11 H11C 1.126 0.206 0.854 4.4 Uiso calc C11 H14A 0.938 0.872 0.755 4.6 Uiso calc N14 H14B 0.932 0.723 0.676 4.6 Uiso calc N14 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 N1 C6 124.0(7) yes C2 N1 H1 114(5) no C6 N1 H1 119(5) no C2 N3 C4 113.1(7) yes C5 N7 C8 104.1(8) yes C4 N9 C8 106.2(6) yes C4 N9 C15 128.7(6) yes C8 N9 C15 125.0(7) yes C12 N14 H14A 120.00 no C12 N14 H14B 120.00 no H14A N14 H14B 119.99 no N1 C2 N3 111.1(6) yes N1 C2 C10 107.2(6) yes N1 C2 C11 109.1(6) yes N3 C2 C10 108.5(7) yes N3 C2 C11 108.9(8) yes C10 C2 C11 112.1(7) yes N3 C4 N9 128.2(7) yes N3 C4 C5 128.6(8) yes N9 C4 C5 103.2(6) yes N7 C5 C4 111.1(7) yes N7 C5 C6 129.6(8) yes C4 C5 C6 117.8(7) yes N1 C6 C5 115.7(8) yes N1 C6 C12 116.5(7) yes C5 C6 C12 127.4(7) yes N7 C8 N9 115.5(7) yes N7 C8 H8 122.24 no N9 C8 H8 122.25 no N9 C15 C16 120.5(7) yes N9 C15 C20 118.6(7) yes C16 C15 C20 120.9(8) yes C15 C16 C17 119.7(8) yes C15 C16 H16 120.17 no C17 C16 H16 120.15 no C16 C17 C18 119.9(8) yes C16 C17 H17 120.07 no C18 C17 H17 120.07 no C17 C18 C19 120.2(8) yes C17 C18 H18 119.92 no C19 C18 H18 119.92 no C18 C19 C20 120.9(8) yes C18 C19 H19 119.52 no C20 C19 H19 119.54 no C15 C20 C19 118.4(8) yes C15 C20 H20 120.80 no C19 C20 H20 120.77 no C2 C10 H10A 109.46 no C2 C10 H10B 109.46 no C2 C10 H10C 109.47 no H10A C10 H10B 109.47 no H10A C10 H10C 109.48 no H10B C10 H10C 109.49 no C2 C11 H11A 109.47 no C2 C11 H11B 109.49 no C2 C11 H11C 109.48 no H11A C11 H11B 109.46 no H11A C11 H11C 109.45 no H11B C11 H11C 109.47 no O13 C12 N14 126.0(9) yes O13 C12 C6 119.5(7) yes N14 C12 C6 114.5(8) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O13 C12 1.223(8) yes N1 C2 1.480(10) yes N1 C6 1.352(9) yes N1 H1 0.86(6) yes N3 C2 1.480(10) yes N3 C4 1.291(9) yes N7 C5 1.408(9) yes N7 C8 1.290(10) yes N9 C4 1.411(9) yes N9 C8 1.390(10) yes N9 C15 1.420(10) yes N14 C12 1.332(9) yes N14 H14A 0.950 no N14 H14B 0.950 no C2 C10 1.520(10) yes C2 C11 1.520(10) yes C4 C5 1.440(10) yes C5 C6 1.352(9) yes C6 C12 1.500(10) yes C8 H8 0.950 no C15 C16 1.380(10) yes C15 C20 1.378(9) yes C16 C17 1.380(10) yes C16 H16 0.950 no C17 C18 1.370(10) yes C17 H17 0.950 no C18 C19 1.370(10) yes C18 H18 0.950 no C19 C20 1.380(10) yes C19 H19 0.950 no C20 H20 0.950 no C10 H10A 0.950 no C10 H10B 0.950 no C10 H10C 0.950 no C11 H11A 0.950 no C11 H11B 0.950 no C11 H11C 0.950 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O13 H1 2.56(7) 1 3_767 no O13 N1 3.30(2) 1 3_767 no O13 C10 3.33(2) 1 3_767 no O13 C17 3.52(2) 1 4 no O13 C11 3.520(10) 1 3_767 no O13 C10 3.54(2) 1 1_565 no O13 C2 3.57(2) 1 3_767 no N3 H14A 2.261 1 1_545 no N3 N14 3.17(2) 1 1_545 no N7 C8 3.480(10) 1 3_766 no N9 C19 3.52(2) 1 3_756 no N9 C11 3.53(2) 1 4_454 no N14 C16 3.50(2) 1 1_565 no C8 C8 3.43(2) 1 3_766 no C8 C11 3.53(2) 1 4_454 no C15 C20 3.49(2) 1 3_756 no C15 C19 3.51(2) 1 3_756 no C15 C11 3.56(2) 1 4_454 no C17 C12 3.49(2) 1 4_454 no C20 C20 3.41(2) 1 3_756 no 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_publ_flag O13 C12 C6 N1 8.0(10) no O13 C12 C6 C5 -179.0(9) no N1 C2 N3 C4 30.1(9) no N1 C6 C5 N7 172.8(8) no N1 C6 C5 C4 8.0(10) no N1 C6 C12 N14 -172.7(8) no N3 C2 N1 C6 -35.0(10) no N3 C4 N9 C8 178.3(8) no N3 C4 N9 C15 -5.0(10) no N3 C4 C5 N7 -178.1(7) no N3 C4 C5 C6 -11.0(10) no N7 C5 C4 N9 -1.3(9) no N7 C5 C6 C12 -1.0(10) no N7 C8 N9 C4 -1.0(10) no N7 C8 N9 C15 -177.8(7) no N9 C4 N3 C2 173.4(7) no N9 C4 C5 C6 165.8(7) no N9 C8 N7 C5 .0(10) no N9 C15 C16 C17 179.3(7) no N9 C15 C20 C19 -179.1(8) no N14 C12 C6 C5 1.0(10) no C2 N1 C6 C5 15.0(10) no C2 N1 C6 C12 -170.7(7) no C2 N3 C4 C5 -11.0(10) no C4 N3 C2 C10 147.7(7) no C4 N3 C2 C11 -90.1(8) no C4 N9 C15 C16 32.0(10) no C4 N9 C15 C20 -149.1(8) no C4 C5 N7 C8 1.0(10) no C4 C5 C6 C12 -164.9(8) no C5 C4 N9 C8 1.5(8) no C5 C4 N9 C15 177.8(7) no C6 N1 C2 C10 -153.6(8) no C6 N1 C2 C11 84.8(9) no C6 C5 N7 C8 -164.6(9) no C8 N9 C15 C16 -152.6(8) no C8 N9 C15 C20 27.0(10) no C15 C16 C17 C18 .0(10) no C15 C20 C19 C18 .0(10) no C16 C15 C20 C19 .0(10) no C16 C17 C18 C19 .0(10) no C17 C16 C15 C20 .0(10) no C17 C18 C19 C20 0(2) no