#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011614.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_2011614 loop_ _publ_author_name 'Quiroga, Jairo' 'Insuasty, Braulio' 'Abonia, Rodrigo' 'Mej\'ia, Diana' 'Nogueras, Manuel' 'S\'anchez, Adolfo' 'Cobo, Justo' 'Low, John Nicolson' _publ_section_title ; 2-Hydroxyphenyl 2-methylpyrazolo[1,5-a]pyrimidin-6-yl ketone ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1455 _journal_page_last 1456 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C14 H11 N3 O2' _chemical_formula_sum 'C14 H11 N3 O2' _chemical_formula_weight 253.26 _chemical_name_systematic ; 2-Hydroxyphenyl 2-methylpyrazolo[1,5-a]pyrimidin-6-yl ketone ; _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' _cell_angle_alpha 90.00 _cell_angle_beta 98.71(16) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.6004(2) _cell_length_b 11.8172(5) _cell_length_c 17.865(7) _cell_measurement_reflns_used 2591 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 3.64 _cell_volume 1168.7(7) _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_collection 'Kappa-CCD Server Software (Nonius, 1997)' _computing_data_reduction DENZO _computing_molecular_graphics 'PLATON (Spek, 2000)' _computing_publication_material 'SHELXL97 and PRPKAPPA (Ferguson, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full .967 _diffrn_measured_fraction_theta_max .967 _diffrn_measurement_device_type 'Nonius KAPPA CCD' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .026 _diffrn_reflns_av_sigmaI/netI .068 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 8919 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 3.64 _diffrn_standards_decay_% negligible _exptl_absorpt_coefficient_mu .100 _exptl_absorpt_correction_T_max .993 _exptl_absorpt_correction_T_min .980 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1995, 1997)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 528 _exptl_crystal_size_max .20 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .08 _refine_diff_density_max .207 _refine_diff_density_min -.286 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2591 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all .093 _refine_ls_R_factor_gt .052 _refine_ls_shift/su_max .012 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.0357P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .144 _reflns_number_gt 1681 _reflns_number_total 2591 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file gs1109.cif _[local]_cod_data_source_block IV _[local]_cod_cif_authors_sg_H-M P21/n _cod_original_cell_volume 1168.67(8) _cod_database_code 2011614 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_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_type_symbol N1 .1100(3) .17904(14) .57168(9) .0311(4) Uani d . 1 N C2 -.1011(3) .19732(17) .52727(10) .0305(5) Uani d . 1 C C21 -.1395(4) .3051(2) .48346(12) .0425(6) Uani d . 1 C C3 -.2660(3) .10919(18) .52987(11) .0325(5) Uani d . 1 C C3a -.1491(3) .03148(17) .57953(10) .0273(4) Uani d . 1 C N4 -.2130(3) -.07073(14) .60574(9) .0306(4) Uani d . 1 N C5 -.0481(3) -.12267(18) .65346(10) .0292(5) Uani d . 1 C C6 .1862(3) -.07906(16) .68062(10) .0268(4) Uani d . 1 C C7 .2486(3) .02342(17) .65371(10) .0270(4) Uani d . 1 C N8 .0800(3) .07713(13) .60410(8) .0267(4) Uani d . 1 N C9 .3563(3) -.15406(17) .72926(10) .0284(5) Uani d . 1 C O9 .3277(3) -.25768(12) .72083(8) .0386(4) Uani d . 1 O C11 .5575(3) -.10958(16) .78422(10) .0256(4) Uani d . 1 C C12 .5663(3) .00237(17) .81077(11) .0307(5) Uani d . 1 C C13 .7652(4) .04235(18) .85895(11) .0331(5) Uani d . 1 C C14 .9587(3) -.03014(18) .88131(11) .0348(5) Uani d . 1 C C15 .9530(3) -.14124(18) .85838(11) .0325(5) Uani d . 1 C C16 .7520(3) -.18242(17) .81126(10) .0265(4) Uani d . 1 C O16 .7557(2) -.29223(11) .79074(7) .0331(4) Uani d . 1 O H21A -.2643 .3500 .5026 .064 Uiso calc R 1 H H21B -.1913 .2878 .4298 .064 Uiso calc R 1 H H21C .0118 .3481 .4892 .064 Uiso calc R 1 H H3 -.4254 .1041 .5029 .039 Uiso calc R 1 H H5 -.0879 -.1949 .6713 .035 Uiso calc R 1 H H7 .4038 .0555 .6692 .032 Uiso calc R 1 H H12 .4336 .0515 .7954 .037 Uiso calc R 1 H H13 .7696 .1183 .8765 .040 Uiso calc R 1 H H14 1.0977 -.0022 .9131 .042 Uiso calc R 1 H H15 1.0861 -.1897 .8747 .039 Uiso calc R 1 H H16 .6027 -.3122 .7636 .040 Uiso d R 1 H 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 .0330(9) .0262(10) .0329(9) .0001(7) .0006(7) .0034(7) C2 .0337(11) .0309(12) .0261(10) .0048(9) .0017(8) -.0014(8) C21 .0513(13) .0384(14) .0365(12) .0067(10) .0026(10) .0074(10) C3 .0273(10) .0360(13) .0317(10) .0021(9) -.0035(8) -.0034(9) C3a .0235(9) .0297(11) .0279(10) -.0005(8) .0014(8) -.0052(8) N4 .0275(9) .0329(10) .0304(9) -.0037(7) .0012(7) -.0018(7) C5 .0312(10) .0276(11) .0284(10) -.0025(8) .0033(8) -.0007(8) C6 .0253(10) .0271(11) .0275(10) -.0001(8) .0024(8) -.0023(8) C7 .0223(9) .0290(11) .0279(10) .0031(8) -.0016(7) -.0030(8) N8 .0251(8) .0243(9) .0295(8) -.0007(6) .0009(6) -.0008(7) C9 .0292(10) .0247(11) .0314(10) .0000(8) .0047(8) -.0001(8) O9 .0423(9) .0246(9) .0460(9) -.0004(6) -.0029(7) -.0005(6) C11 .0281(10) .0230(11) .0258(9) .0004(8) .0039(7) .0005(8) C12 .0305(10) .0267(11) .0337(10) .0048(8) .0010(8) .0031(9) C13 .0399(11) .0245(12) .0332(11) .0017(9) .0000(9) -.0011(8) C14 .0327(11) .0336(13) .0351(11) -.0032(9) -.0045(9) -.0002(9) C15 .0304(10) .0327(12) .0326(10) .0062(9) -.0012(8) .0005(9) C16 .0317(10) .0230(11) .0254(9) .0036(8) .0064(8) .0031(8) O16 .0390(8) .0237(8) .0351(8) .0051(6) .0001(6) -.0018(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 _geom_angle_publ_flag C2 N1 N8 103.94(15) no N1 C2 C3 112.89(18) no N1 C2 C21 119.54(18) no C3 C2 C21 127.55(18) no C2 C21 H21A 109.5 no C2 C21 H21B 109.5 no H21A C21 H21B 109.5 no C2 C21 H21C 109.5 no H21A C21 H21C 109.5 no H21B C21 H21C 109.5 no C3a C3 C2 105.50(17) no C3a C3 H3 127.2 no C2 C3 H3 127.2 no N4 C3a C3 133.71(18) no N4 C3a N8 120.65(16) no C3 C3a N8 105.64(18) no C5 N4 C3a 116.29(16) no N4 C5 C6 125.0(2) no N4 C5 H5 117.5 no C6 C5 H5 117.5 no C7 C6 C5 118.14(17) no C7 C6 C9 124.04(16) no C5 C6 C9 117.41(18) no N8 C7 C6 117.13(17) no N8 C7 H7 121.4 no C6 C7 H7 121.4 no C7 N8 N1 125.23(16) no C7 N8 C3a 122.75(17) no N1 N8 C3a 112.02(15) no O9 C9 C11 120.27(17) no O9 C9 C6 117.32(17) no C11 C9 C6 122.38(18) no C12 C11 C16 118.18(17) no C12 C11 C9 123.04(17) no C16 C11 C9 118.79(18) no C13 C12 C11 121.05(18) no C13 C12 H12 119.5 no C11 C12 H12 119.5 no C12 C13 C14 119.14(19) no C12 C13 H13 120.4 no C14 C13 H13 120.4 no C15 C14 C13 121.36(18) no C15 C14 H14 119.3 no C13 C14 H14 119.3 no C14 C15 C16 119.74(18) no C14 C15 H15 120.1 no C16 C15 H15 120.1 no O16 C16 C15 117.22(16) no O16 C16 C11 122.36(16) no C15 C16 C11 120.38(18) no C16 O16 H16 109.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.338(2) yes N1 N8 1.358(2) yes C2 C3 1.397(3) no C2 C21 1.493(3) no C21 H21A .9800 no C21 H21B .9800 no C21 H21C .9800 no C3 C3a 1.372(3) no C3 H3 .9500 no C3a N4 1.363(2) yes C3a N8 1.400(2) yes N4 C5 1.310(2) yes C5 C6 1.425(3) no C5 H5 .9500 no C6 C7 1.368(3) no C6 C9 1.482(3) no C7 N8 1.352(2) no C7 H7 .9500 no C9 O9 1.241(2) yes C9 C11 1.474(3) no C11 C12 1.404(3) no C11 C16 1.415(3) no C12 C13 1.384(3) no C12 H12 .9500 no C13 C14 1.392(3) no C13 H13 .9500 no C14 C15 1.374(3) no C14 H14 .9500 no C15 C16 1.388(3) no C15 H15 .9500 no C16 O16 1.349(2) yes O16 H16 .9483 no 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 _geom_hbond_publ_flag O16 H16 O9 . .95 1.74 2.562(2) 143.6 y C3 H3 N4 3_456 .95 2.61 3.528(2) 161.6 y C15 H15 N1 2_646 .95 2.39 3.337(3) 172.3 y 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 N8 N1 C2 C3 -.4(2) no N8 N1 C2 C21 178.08(16) no N1 C2 C3 C3a .3(2) no C21 C2 C3 C3a -178.08(18) no C2 C3 C3a N4 179.8(2) no C2 C3 C3a N8 .0(2) no C3 C3a N4 C5 179.25(19) no N8 C3a N4 C5 -.9(2) no C3a N4 C5 C6 1.6(3) no N4 C5 C6 C7 -1.9(3) no N4 C5 C6 C9 -174.82(17) no C5 C6 C7 N8 1.3(3) no C9 C6 C7 N8 173.76(16) no C6 C7 N8 N1 -179.99(16) no C6 C7 N8 C3a -.7(3) no C2 N1 N8 C7 179.72(16) no C2 N1 N8 C3a .41(19) no N4 C3a N8 C7 .5(3) no C3 C3a N8 C7 -179.59(16) no N4 C3a N8 N1 179.88(16) no C3 C3a N8 N1 -.3(2) no C7 C6 C9 O9 -145.85(19) no C5 C6 C9 O9 26.7(2) no C7 C6 C9 C11 32.3(3) no C5 C6 C9 C11 -155.16(17) no O9 C9 C11 C12 -163.23(18) no C6 C9 C11 C12 18.6(3) no O9 C9 C11 C16 17.2(3) no C6 C9 C11 C16 -160.87(17) no C16 C11 C12 C13 3.3(3) no C9 C11 C12 C13 -176.18(17) no C11 C12 C13 C14 -.1(3) no C12 C13 C14 C15 -2.0(3) no C13 C14 C15 C16 .7(3) no C14 C15 C16 O16 -179.77(17) no C14 C15 C16 C11 2.6(3) no C12 C11 C16 O16 177.91(16) no C9 C11 C16 O16 -2.5(3) no C12 C11 C16 C15 -4.6(3) no C9 C11 C16 C15 174.95(16) no