#------------------------------------------------------------------------------ #$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201954 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/50/1505029.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1505029 loop_ _publ_author_name 'Robins, Morris J.' 'Nowak, Ireneusz' 'Rajwanshi, Vivek K.' 'Miranda, Karl' 'Cannon, John F.' 'Peterson, Matt A.' 'Andrei, Graciela' 'Snoeck, Robert' 'De Clercq, Erik' 'Balzarini, Jan' _publ_section_title ; Synthesis and antiviral evaluation of 6-(alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one nucleosides and analogues with ethynyl, ethenyl, and ethyl spacers at C6 of the furopyrimidine core. ; _journal_issue 16 _journal_name_full 'Journal of medicinal chemistry' _journal_page_first 3897 _journal_page_last 3905 _journal_paper_doi 10.1021/jm070210n _journal_volume 50 _journal_year 2007 _chemical_absolute_configuration rm _chemical_formula_sum 'C22 H27 N3 O5' _chemical_formula_weight 413.47 _chemical_name_systematic ; ? ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 95.90(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 6.6883(13) _cell_length_b 5.6677(11) _cell_length_c 27.611(6) _cell_measurement_temperature 173(2) _cell_volume 1041.1(4) _computing_cell_refinement 'Bruker XSCANS' _computing_data_collection 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.959 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_device_type 'Bruker Nonius Apex II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator 'Montel 200 mirrors' _diffrn_radiation_source 'Bruker Nonius FR591' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 5148 _diffrn_reflns_theta_full 67.48 _diffrn_reflns_theta_max 67.48 _diffrn_reflns_theta_min 6.65 _exptl_absorpt_coefficient_mu 0.775 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_correction_T_min 0.7896 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS; Sheldrick, 2003' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_description PLATE _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.01 _refine_diff_density_max 0.139 _refine_diff_density_min -0.119 _refine_diff_density_rms 0.030 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 3117 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0356 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.2488P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0819 _refine_ls_wR_factor_ref 0.0854 _reflns_number_gt 2800 _reflns_number_total 3117 _reflns_threshold_expression >2sigma(I) _cod_data_source_file jm070210nsi20070222_061706.cif _cod_data_source_block xl1089_0m _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P2(1) _cod_database_code 1505029 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 C2 C 0.8410(3) -0.0818(4) 0.33777(8) 0.0368(5) Uani 1 1 d . C4 C 0.4782(3) -0.1444(4) 0.33352(8) 0.0359(5) Uani 1 1 d . H4 H 0.3670 -0.2322 0.3426 0.043 Uiso 1 1 calc R C5 C 0.2864(3) 0.1825(5) 0.28083(8) 0.0408(6) Uani 1 1 d . H5 H 0.1473 0.1514 0.2819 0.049 Uiso 1 1 calc R C6 C 0.3666(3) 0.3628(5) 0.25738(8) 0.0384(5) Uani 1 1 d . C2" C 0.2728(3) 0.5573(5) 0.22859(8) 0.0387(5) Uani 1 1 d . C3" C 0.0668(3) 0.5967(5) 0.22815(9) 0.0466(6) Uani 1 1 d . H3" H -0.0112 0.5027 0.2476 0.056 Uiso 1 1 calc R C4" C -0.0230(4) 0.7740(5) 0.19915(9) 0.0471(6) Uani 1 1 d . H4" H -0.1633 0.8022 0.1986 0.056 Uiso 1 1 calc R C5" C 0.0925(4) 0.9113(5) 0.17068(8) 0.0461(6) Uani 1 1 d . C6" C 0.2985(4) 0.8612(5) 0.17488(9) 0.0498(7) Uani 1 1 d . H6" H 0.3803 0.9572 0.1567 0.060 Uiso 1 1 calc R C7" C 0.0138(4) 1.1096(6) 0.13703(10) 0.0547(7) Uani 1 1 d . H7"1 H 0.0534 1.0765 0.1041 0.066 Uiso 1 1 calc R H7"2 H 0.0815 1.2576 0.1485 0.066 Uiso 1 1 calc R C8" C -0.2129(4) 1.1513(6) 0.13257(9) 0.0509(6) Uani 1 1 d . H8"1 H -0.2542 1.1921 0.1650 0.061 Uiso 1 1 calc R H8"2 H -0.2831 1.0041 0.1215 0.061 Uiso 1 1 calc R C9" C -0.2760(4) 1.3495(6) 0.09675(10) 0.0563(7) Uani 1 1 d . H9"1 H -0.2166 1.4995 0.1098 0.068 Uiso 1 1 calc R H9"2 H -0.2203 1.3169 0.0656 0.068 Uiso 1 1 calc R C10" C -0.5024(4) 1.3803(6) 0.08686(10) 0.0546(7) Uani 1 1 d . H10A H -0.5588 1.4083 0.1181 0.066 Uiso 1 1 calc R H10B H -0.5616 1.2321 0.0728 0.066 Uiso 1 1 calc R C11" C -0.5644(4) 1.5842(6) 0.05203(10) 0.0609(8) Uani 1 1 d . H11A H -0.5083 1.7333 0.0663 0.073 Uiso 1 1 calc R H11B H -0.5061 1.5582 0.0209 0.073 Uiso 1 1 calc R C12" C -0.7920(5) 1.6089(8) 0.04173(12) 0.0825(11) Uani 1 1 d . H12A H -0.8462 1.4719 0.0231 0.124 Uiso 1 1 calc R H12B H -0.8238 1.7530 0.0229 0.124 Uiso 1 1 calc R H12C H -0.8521 1.6176 0.0726 0.124 Uiso 1 1 calc R C1' C 0.7052(3) -0.4113(4) 0.38409(8) 0.0370(5) Uani 1 1 d . H1' H 0.8322 -0.4944 0.3781 0.044 Uiso 1 1 calc R C2' C 0.7117(3) -0.3426(4) 0.43772(8) 0.0369(5) Uani 1 1 d . H2'1 H 0.6272 -0.2024 0.4421 0.044 Uiso 1 1 calc R H2'2 H 0.8510 -0.3101 0.4519 0.044 Uiso 1 1 calc R C3' C 0.6270(3) -0.5620(4) 0.46052(9) 0.0378(5) Uani 1 1 d . H3' H 0.5607 -0.5208 0.4903 0.045 Uiso 1 1 calc R C4' C 0.4742(3) -0.6534(4) 0.41991(8) 0.0391(5) Uani 1 1 d . H4' H 0.4828 -0.8295 0.4196 0.047 Uiso 1 1 calc R C5' C 0.2557(3) -0.5853(4) 0.42278(10) 0.0429(6) Uani 1 1 d . H5'1 H 0.1753 -0.6266 0.3918 0.051 Uiso 1 1 calc R H5'2 H 0.2017 -0.6749 0.4493 0.051 Uiso 1 1 calc R C4A C 0.4498(3) 0.0474(4) 0.30378(8) 0.0350(5) Uani 1 1 d . C7A C 0.6269(3) 0.1621(4) 0.29212(8) 0.0350(5) Uani 1 1 d . N1 N 0.8126(3) 0.1090(4) 0.30671(7) 0.0379(4) Uani 1 1 d . N3 N 0.6702(3) -0.2070(3) 0.34983(6) 0.0340(4) Uani 1 1 d . N1" N 0.3901(3) 0.6905(4) 0.20208(7) 0.0442(5) Uani 1 1 d . O2 O 1.0100(2) -0.1449(3) 0.35540(6) 0.0468(4) Uani 1 1 d . O7 O 0.5793(2) 0.3524(3) 0.26333(5) 0.0389(4) Uani 1 1 d . O3' O 0.7816(3) -0.7326(3) 0.47119(6) 0.0504(5) Uani 1 1 d . H3'1 H 0.7907 -0.7659 0.5010 0.076 Uiso 1 1 calc R O4' O 0.5401(2) -0.5656(3) 0.37473(6) 0.0392(4) Uani 1 1 d . O5' O 0.2384(2) -0.3357(3) 0.43174(6) 0.0461(4) Uani 1 1 d . H5' H 0.1601 -0.2746 0.4095 0.069 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 0.0252(12) 0.0426(14) 0.0436(12) -0.0021(11) 0.0080(9) -0.0022(10) C4 0.0236(11) 0.0420(13) 0.0429(11) -0.0057(11) 0.0078(9) -0.0079(10) C5 0.0244(11) 0.0517(16) 0.0465(12) -0.0011(12) 0.0047(9) -0.0057(11) C6 0.0256(11) 0.0521(15) 0.0378(11) -0.0016(12) 0.0040(8) -0.0041(11) C2" 0.0319(12) 0.0488(15) 0.0357(11) -0.0041(11) 0.0048(9) -0.0019(11) C3" 0.0319(12) 0.0610(18) 0.0466(13) 0.0063(13) 0.0020(10) -0.0021(12) C4" 0.0305(13) 0.0627(18) 0.0474(13) -0.0002(13) 0.0015(10) 0.0070(12) C5" 0.0394(13) 0.0592(18) 0.0395(12) 0.0000(13) 0.0027(10) 0.0017(12) C6" 0.0401(14) 0.0631(18) 0.0470(13) 0.0101(14) 0.0083(10) -0.0001(13) C7" 0.0467(15) 0.0637(19) 0.0537(14) 0.0055(15) 0.0055(11) 0.0065(14) C8" 0.0432(14) 0.0586(18) 0.0501(13) 0.0055(14) 0.0015(11) 0.0033(13) C9" 0.0493(15) 0.0628(18) 0.0560(15) 0.0039(15) 0.0016(12) 0.0060(14) C10" 0.0493(15) 0.0614(19) 0.0523(14) 0.0037(14) 0.0009(11) 0.0037(14) C11" 0.0594(17) 0.062(2) 0.0593(16) 0.0084(16) -0.0019(13) 0.0066(15) C12" 0.063(2) 0.101(3) 0.081(2) 0.025(2) -0.0041(16) 0.017(2) C1' 0.0283(11) 0.0312(13) 0.0525(13) -0.0024(11) 0.0094(9) -0.0012(10) C2' 0.0284(11) 0.0334(12) 0.0493(12) 0.0016(11) 0.0057(9) 0.0009(10) C3' 0.0313(12) 0.0348(13) 0.0489(12) 0.0044(11) 0.0122(9) 0.0059(10) C4' 0.0377(12) 0.0269(11) 0.0545(13) -0.0010(11) 0.0129(10) 0.0012(10) C5' 0.0340(13) 0.0410(15) 0.0553(13) -0.0002(12) 0.0121(10) -0.0030(11) C4A 0.0259(11) 0.0413(14) 0.0382(11) -0.0058(10) 0.0055(9) -0.0055(10) C7A 0.0293(11) 0.0406(13) 0.0359(10) -0.0020(11) 0.0068(8) -0.0048(10) N1 0.0243(9) 0.0426(12) 0.0481(10) 0.0052(9) 0.0100(7) -0.0014(8) N3 0.0267(9) 0.0356(11) 0.0413(10) -0.0012(9) 0.0110(7) -0.0020(8) N1" 0.0362(11) 0.0543(14) 0.0431(10) 0.0070(10) 0.0082(8) 0.0014(10) O2 0.0235(8) 0.0555(11) 0.0621(10) 0.0146(10) 0.0082(7) 0.0014(8) O7 0.0250(8) 0.0468(10) 0.0455(8) 0.0052(8) 0.0067(6) -0.0015(7) O3' 0.0465(10) 0.0466(11) 0.0594(11) 0.0125(9) 0.0121(8) 0.0161(8) O4' 0.0356(8) 0.0360(9) 0.0478(9) -0.0051(8) 0.0124(7) -0.0057(7) O5' 0.0350(9) 0.0496(10) 0.0534(9) -0.0027(9) 0.0032(7) 0.0100(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O2 C2 N1 122.2(2) O2 C2 N3 119.4(2) N1 C2 N3 118.45(19) C4A C4 N3 118.3(2) C4A C4 H4 120.9 N3 C4 H4 120.9 C6 C5 C4A 107.1(2) C6 C5 H5 126.4 C4A C5 H5 126.4 C5 C6 O7 110.9(2) C5 C6 C2" 131.4(2) O7 C6 C2" 117.67(19) N1" C2" C3" 122.1(2) N1" C2" C6 118.2(2) C3" C2" C6 119.6(2) C4" C3" C2" 119.4(2) C4" C3" H3" 120.3 C2" C3" H3" 120.3 C3" C4" C5" 119.9(2) C3" C4" H4" 120.0 C5" C4" H4" 120.0 C4" C5" C6" 115.9(2) C4" C5" C7" 125.5(2) C6" C5" C7" 118.5(2) N1" C6" C5" 125.8(2) N1" C6" H6" 117.1 C5" C6" H6" 117.1 C5" C7" C8" 116.3(2) C5" C7" H7"1 108.2 C8" C7" H7"1 108.2 C5" C7" H7"2 108.2 C8" C7" H7"2 108.2 H7"1 C7" H7"2 107.4 C7" C8" C9" 111.8(2) C7" C8" H8"1 109.2 C9" C8" H8"1 109.2 C7" C8" H8"2 109.2 C9" C8" H8"2 109.2 H8"1 C8" H8"2 107.9 C10" C9" C8" 113.8(2) C10" C9" H9"1 108.8 C8" C9" H9"1 108.8 C10" C9" H9"2 108.8 C8" C9" H9"2 108.8 H9"1 C9" H9"2 107.7 C9" C10" C11" 113.5(2) C9" C10" H10A 108.9 C11" C10" H10A 108.9 C9" C10" H10B 108.9 C11" C10" H10B 108.9 H10A C10" H10B 107.7 C12" C11" C10" 112.7(3) C12" C11" H11A 109.1 C10" C11" H11A 109.1 C12" C11" H11B 109.1 C10" C11" H11B 109.1 H11A C11" H11B 107.8 C11" C12" H12A 109.5 C11" C12" H12B 109.5 H12A C12" H12B 109.5 C11" C12" H12C 109.5 H12A C12" H12C 109.5 H12B C12" H12C 109.5 O4' C1' N3 107.16(17) O4' C1' C2' 106.22(18) N3 C1' C2' 113.73(19) O4' C1' H1' 109.9 N3 C1' H1' 109.9 C2' C1' H1' 109.9 C1' C2' C3' 102.54(19) C1' C2' H2'1 111.3 C3' C2' H2'1 111.3 C1' C2' H2'2 111.3 C3' C2' H2'2 111.3 H2'1 C2' H2'2 109.2 O3' C3' C4' 109.8(2) O3' C3' C2' 110.20(18) C4' C3' C2' 102.81(19) O3' C3' H3' 111.2 C4' C3' H3' 111.2 C2' C3' H3' 111.2 O4' C4' C5' 109.62(19) O4' C4' C3' 105.94(17) C5' C4' C3' 116.70(19) O4' C4' H4' 108.1 C5' C4' H4' 108.1 C3' C4' H4' 108.1 O5' C5' C4' 110.61(19) O5' C5' H5'1 109.5 C4' C5' H5'1 109.5 O5' C5' H5'2 109.5 C4' C5' H5'2 109.5 H5'1 C5' H5'2 108.1 C4 C4A C7A 115.8(2) C4 C4A C5 138.3(2) C7A C4A C5 105.8(2) N1 C7A O7 121.6(2) N1 C7A C4A 128.1(2) O7 C7A C4A 110.24(19) C7A N1 C2 116.06(19) C4 N3 C2 123.3(2) C4 N3 C1' 119.32(18) C2 N3 C1' 117.35(18) C6" N1" C2" 116.7(2) C7A O7 C6 105.87(17) C3' O3' H3'1 109.5 C1' O4' C4' 110.84(16) C5' O5' H5' 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C2 O2 1.237(3) C2 N1 1.381(3) C2 N3 1.413(3) C4 C4A 1.364(3) C4 N3 1.364(3) C4 H4 0.9500 C5 C6 1.350(3) C5 C4A 1.429(3) C5 H5 0.9500 C6 O7 1.416(3) C6 C2" 1.462(3) C2" N1" 1.356(3) C2" C3" 1.395(3) C3" C4" 1.383(4) C3" H3" 0.9500 C4" C5" 1.395(4) C4" H4" 0.9500 C5" C6" 1.400(3) C5" C7" 1.517(4) C6" N1" 1.335(3) C6" H6" 0.9500 C7" C8" 1.527(3) C7" H7"1 0.9900 C7" H7"2 0.9900 C8" C9" 1.527(4) C8" H8"1 0.9900 C8" H8"2 0.9900 C9" C10" 1.521(4) C9" H9"1 0.9900 C9" H9"2 0.9900 C10" C11" 1.533(4) C10" H10A 0.9900 C10" H10B 0.9900 C11" C12" 1.526(4) C11" H11A 0.9900 C11" H11B 0.9900 C12" H12A 0.9800 C12" H12B 0.9800 C12" H12C 0.9800 C1' O4' 1.411(3) C1' N3 1.498(3) C1' C2' 1.527(3) C1' H1' 1.0000 C2' C3' 1.529(3) C2' H2'1 0.9900 C2' H2'2 0.9900 C3' O3' 1.424(3) C3' C4' 1.528(3) C3' H3' 1.0000 C4' O4' 1.453(3) C4' C5' 1.521(3) C4' H4' 1.0000 C5' O5' 1.443(3) C5' H5'1 0.9900 C5' H5'2 0.9900 C4A C7A 1.417(3) C7A N1 1.301(3) C7A O7 1.358(3) O3' H3'1 0.8400 O5' H5' 0.8400 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3' H3'1 O5' 0.84 1.93 2.760(2) 170.0 2_646 O5' H5' O2 0.84 1.86 2.699(2) 173.3 1_455 loop_ _cod_related_entry_id _cod_related_entry_code _cod_related_entry_database 1 23288008 ChemSpider