#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/87/2018793.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_2018793 loop_ _publ_author_name 'Novotn\'a, Radka' 'Tr\'avn\'i\H-pyrrolo[3,2-d]pyrimidin-4(5H)-one ; _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_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 104.69(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.8315(12) _cell_length_b 19.976(5) _cell_length_c 6.3551(13) _cell_measurement_reflns_used 1593 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 33.28 _cell_measurement_theta_min 3.05 _cell_volume 593.3(2) _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2009)' _computing_molecular_graphics ; Mercury (Macrae et al., 2008) and DIAMOND (Brandenburg, 2011) ; _computing_publication_material ; publCIF (Westrip, 2010) and PARST (Nardelli, 1995) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 8.3611 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Oxford Xcalibur diffractometer with Sapphire2 detector (large Be window)' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_av_sigmaI/netI 0.0689 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 3740 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 3.47 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 0.9891 _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2009)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.513 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 280 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.271 _refine_diff_density_min -0.166 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.937 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 91 _refine_ls_number_reflns 1050 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.937 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0485 _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^)+(0.0548P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0919 _refine_ls_wR_factor_ref 0.1017 _reflns_number_gt 693 _reflns_number_total 1050 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL dr_11_03_slow in P2(1)/n REM P2(1)/n (#14 in standard setting) CELL 0.71073 4.831528 19.975637 6.355146 90.0000 104.6913 90.0000 ZERR 4.00 0.001166 0.004536 0.001337 0.0000 0.0243 0.0000 LATT 1 SYMM -x+1/2, y+1/2,-z+1/2 SFAC C H N O UNIT 24 20 12 4 TEMP -173 SIZE 0.2 0.15 0.1 OMIT -3 50.1 L.S. 40 BOND BOND $H LIST EQIV $1 -x+2, -y, -z+1 EQIV $2 x, y, z+1 HTAB N1 O1_$1 HTAB N7 N3_$2 MERG ACTA FMAP 2 PLAN 20 WGHT 0.054800 FVAR 3.60784 N1 3 0.758487 0.050600 0.290975 11.00000 0.01378 0.02106 = 0.02015 0.00177 0.00323 0.00404 AFIX 43 H1 2 0.892853 0.020064 0.302827 11.00000 -1.20000 AFIX 0 O1 4 0.793482 0.041771 0.656268 11.00000 0.01846 0.02745 = 0.01977 0.00372 0.00447 0.00447 C2 1 0.645336 0.077210 0.090943 11.00000 0.01830 0.02572 = 0.01958 -0.00150 0.00400 -0.00071 AFIX 43 H2 2 0.718691 0.061597 -0.025402 11.00000 -1.20000 AFIX 0 N3 3 0.443984 0.122496 0.045405 11.00000 0.01676 0.02339 = 0.02368 0.00040 0.00392 0.00061 C4 1 0.350369 0.143084 0.223371 11.00000 0.01284 0.01880 = 0.02280 -0.00130 0.00456 -0.00425 C5 1 0.458282 0.117200 0.432245 11.00000 0.01353 0.01794 = 0.02088 -0.00059 0.00536 -0.00341 C6 1 0.678008 0.067984 0.476274 11.00000 0.01450 0.01733 = 0.01965 -0.00140 0.00516 -0.00505 N7 3 0.318998 0.147451 0.570726 11.00000 0.01615 0.02126 = 0.02016 0.00119 0.00423 0.00100 AFIX 43 H7 2 0.347455 0.139575 0.710835 11.00000 -1.20000 AFIX 0 C8 1 0.128202 0.192012 0.450410 11.00000 0.01133 0.01763 = 0.03300 -0.00040 0.00446 -0.00007 AFIX 43 H8 2 0.003607 0.219673 0.506329 11.00000 -1.20000 AFIX 0 C9 1 0.142141 0.191124 0.237794 11.00000 0.01218 0.02067 = 0.02783 0.00369 -0.00010 0.00131 AFIX 43 H9 2 0.032730 0.217717 0.122440 11.00000 -1.20000 HKLF 4 REM dr_11_03_slow in P2(1)/n REM R1 = 0.0485 for 693 Fo > 4sig(Fo) and 0.0879 for all 1050 data REM 91 parameters refined using 0 restraints END WGHT 0.0552 0.0000 REM Highest difference peak 0.271, deepest hole -0.166, 1-sigma level 0.056 Q1 1 0.3694 0.1445 -0.1087 11.00000 0.05 0.27 Q2 1 0.7842 0.0575 0.8025 11.00000 0.05 0.25 Q3 1 0.4443 0.1217 0.3048 11.00000 0.05 0.23 Q4 1 0.6513 0.0823 -0.1862 11.00000 0.05 0.22 Q5 1 0.4220 0.1324 0.4817 11.00000 0.05 0.20 Q6 1 0.8179 0.0270 0.4878 11.00000 0.05 0.20 Q7 1 0.2553 0.1433 0.2589 11.00000 0.05 0.19 Q8 1 0.6660 0.0485 0.3775 11.00000 0.05 0.19 Q9 1 0.5439 0.0400 -0.1600 11.00000 0.05 0.18 Q10 1 0.6306 0.0785 0.6620 11.00000 0.05 0.18 Q11 1 0.0087 0.2180 0.5927 11.00000 0.05 0.18 Q12 1 0.3692 0.1342 0.1300 11.00000 0.05 0.17 Q13 1 0.4729 0.1212 0.6910 11.00000 0.05 0.17 Q14 1 0.5172 0.0957 0.4630 11.00000 0.05 0.16 Q15 1 0.0262 0.2030 0.5690 11.00000 0.05 0.16 Q16 1 0.1127 0.1954 -0.1042 11.00000 0.05 0.16 Q17 1 0.8319 0.0981 0.6673 11.00000 0.05 0.16 Q18 1 0.0977 0.2333 0.1909 11.00000 0.05 0.15 Q19 1 0.2616 0.1958 0.1036 11.00000 0.05 0.14 Q20 1 0.3748 0.1718 0.2419 11.00000 0.05 0.12 ; _cod_data_source_file sk3467.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2018793 _cod_database_fobs_code 2018793 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' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity N N1 0.7585(4) 0.05060(9) 0.2910(3) 0.0185(5) Uani d . 1 1 H H1 0.8929 0.0201 0.3028 0.022 Uiso calc R 1 1 O O1 0.7935(3) 0.04177(8) 0.6563(2) 0.0220(4) Uani d . 1 1 C C2 0.6453(5) 0.07721(12) 0.0909(4) 0.0213(6) Uani d . 1 1 H H2 0.7187 0.0616 -0.0254 0.026 Uiso calc R 1 1 N N3 0.4440(4) 0.12250(10) 0.0454(3) 0.0215(5) Uani d . 1 1 C C4 0.3504(5) 0.14308(11) 0.2234(4) 0.0181(6) Uani d . 1 1 C C5 0.4583(5) 0.11720(12) 0.4322(4) 0.0173(5) Uani d . 1 1 C C6 0.6780(5) 0.06798(11) 0.4763(4) 0.0170(5) Uani d . 1 1 N N7 0.3190(4) 0.14745(9) 0.5707(3) 0.0193(5) Uani d . 1 1 H H7 0.3475 0.1396 0.7108 0.023 Uiso calc R 1 1 C C8 0.1282(5) 0.19201(12) 0.4504(4) 0.0209(6) Uani d . 1 1 H H8 0.0036 0.2197 0.5063 0.025 Uiso calc R 1 1 C C9 0.1421(5) 0.19112(12) 0.2378(4) 0.0212(6) Uani d . 1 1 H H9 0.0327 0.2177 0.1224 0.025 Uiso calc R 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 0.0138(10) 0.0211(11) 0.0202(11) 0.0040(9) 0.0032(8) 0.0018(8) O1 0.0185(9) 0.0274(10) 0.0198(9) 0.0045(7) 0.0045(7) 0.0037(7) C2 0.0183(13) 0.0257(14) 0.0196(13) -0.0007(12) 0.0040(10) -0.0015(11) N3 0.0168(11) 0.0234(12) 0.0237(12) 0.0006(9) 0.0039(9) 0.0004(9) C4 0.0128(12) 0.0188(13) 0.0228(14) -0.0042(10) 0.0046(10) -0.0013(10) C5 0.0135(12) 0.0179(13) 0.0209(13) -0.0034(10) 0.0054(10) -0.0006(10) C6 0.0145(12) 0.0173(12) 0.0197(13) -0.0050(10) 0.0052(10) -0.0014(10) N7 0.0161(11) 0.0213(11) 0.0202(11) 0.0010(9) 0.0042(8) 0.0012(8) C8 0.0113(11) 0.0176(13) 0.0330(15) -0.0001(10) 0.0045(10) -0.0004(11) C9 0.0122(12) 0.0207(14) 0.0278(15) 0.0013(10) -0.0001(10) 0.0037(11) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 N1 C6 124.7(2) C2 N1 H1 117.7 C6 N1 H1 117.7 N3 C2 N1 125.4(2) N3 C2 H2 117.3 N1 C2 H2 117.3 C2 N3 C4 113.9(2) N3 C4 C5 123.1(2) N3 C4 C9 130.0(2) C5 C4 C9 106.9(2) N7 C5 C4 108.7(2) N7 C5 C6 129.8(2) C4 C5 C6 121.6(2) O1 C6 N1 121.3(2) O1 C6 C5 127.3(2) N1 C6 C5 111.4(2) C8 N7 C5 107.34(18) C8 N7 H7 126.3 C5 N7 H7 126.3 N7 C8 C9 110.4(2) N7 C8 H8 124.8 C9 C8 H8 124.8 C8 C9 C4 106.7(2) C8 C9 H9 126.7 C4 C9 H9 126.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.358(3) N1 C6 1.375(3) N1 H1 0.8800 O1 C6 1.253(3) C2 N3 1.306(3) C2 H2 0.9500 N3 C4 1.383(3) C4 C5 1.396(3) C4 C9 1.410(3) C5 N7 1.376(3) C5 C6 1.422(3) N7 C8 1.367(3) N7 H7 0.8800 C8 C9 1.370(3) C8 H8 0.9500 C9 H9 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1 O1 3_756 0.88 1.92 2.799(3) 175 N7 H7 N3 1_556 0.88 2.09 2.965(3) 176 C2 H2 O1 1_554 0.95 2.18 3.106(3) 165