#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204099.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_2204099 loop_ _publ_author_name 'Li-Rong Wen' 'Shu-Wen Wang' 'Hai-Zhen Xu' 'Xiu-Li Zhang' 'Ming Li' 'Jin-Hong Liu' _publ_section_title ; 7-(4-Methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1294 _journal_page_last o1295 _journal_paper_doi 10.1107/S1600536804015673 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H10 N4' _chemical_formula_moiety 'C14 H10 N4' _chemical_formula_sum 'C14 H10 N4' _chemical_formula_weight 234.26 _chemical_name_systematic ; 7-(4-Methylphenyl)pyrazolo[2,3-a]pyrimidine-3-carbonitrile ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.404(3) _cell_length_b 10.276(4) _cell_length_c 14.963(5) _cell_measurement_reflns_used 696 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.08 _cell_measurement_theta_min 3.37 _cell_volume 1138.4(7) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART 1K CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 6603 _diffrn_reflns_theta_full 26.38 _diffrn_reflns_theta_max 26.38 _diffrn_reflns_theta_min 2.40 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_crystal_colour ' yellow ' _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_description ' prism ' _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.139 _refine_diff_density_min -0.124 _refine_ls_extinction_coef 0.035(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 165 _refine_ls_number_reflns 1364 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0361 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0427P)^2^+0.1275P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.0873 _reflns_number_gt 1097 _reflns_number_total 1364 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6260.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_database_code 2204099 _cod_database_fobs_code 2204099 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -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 0.0356(3) 0.48741(19) 0.57263(12) 0.0447(5) Uani d . 1 N N2 0.1152(3) 0.52414(18) 0.49387(12) 0.0368(5) Uani d . 1 N N3 0.1765(3) 0.44069(19) 0.34719(13) 0.0459(5) Uani d . 1 N N4 -0.0517(4) 0.1074(2) 0.39411(16) 0.0628(7) Uani d . 1 N C1 -0.0176(4) 0.3665(2) 0.55726(17) 0.0471(6) Uani d . 1 C H1 -0.0774 0.3158 0.5994 0.057 Uiso calc R 1 H C2 0.0251(4) 0.3226(2) 0.47122(16) 0.0429(6) Uani d . 1 C C3 -0.0183(4) 0.2020(2) 0.42924(17) 0.0464(6) Uani d . 1 C C4 0.1112(3) 0.4263(2) 0.43020(15) 0.0388(5) Uani d . 1 C C5 0.2399(4) 0.5571(2) 0.32872(15) 0.0476(6) Uani d . 1 C H5 0.2827 0.5719 0.2712 0.057 Uiso calc R 1 H C6 0.2475(3) 0.6600(2) 0.38950(15) 0.0430(6) Uani d . 1 C H6 0.2944 0.7398 0.3716 0.052 Uiso calc R 1 H C7 0.1863(3) 0.6445(2) 0.47547(14) 0.0360(5) Uani d . 1 C C8 0.1957(3) 0.7464(2) 0.54441(14) 0.0366(5) Uani d . 1 C C9 0.2463(4) 0.7203(2) 0.63219(15) 0.0442(6) Uani d . 1 C H9 0.2704 0.6352 0.6498 0.053 Uiso calc R 1 H C10 0.2606(4) 0.8202(2) 0.69288(15) 0.0474(6) Uani d . 1 C H10 0.2957 0.8014 0.7511 0.057 Uiso calc R 1 H C11 0.2241(4) 0.9484(2) 0.66965(15) 0.0440(6) Uani d . 1 C C12 0.1738(4) 0.9728(2) 0.58231(15) 0.0450(6) Uani d . 1 C H12 0.1484 1.0578 0.5650 0.054 Uiso calc R 1 H C13 0.1602(3) 0.8744(2) 0.52041(15) 0.0414(6) Uani d . 1 C H13 0.1269 0.8937 0.4620 0.050 Uiso calc R 1 H C14 0.2359(4) 1.0580(2) 0.73653(17) 0.0595(8) Uani d . 1 C H14A 0.1204 1.0699 0.7646 0.089 Uiso calc R 1 H H14B 0.2702 1.1367 0.7065 0.089 Uiso calc R 1 H H14C 0.3245 1.0371 0.7811 0.089 Uiso calc 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 0.0496(12) 0.0465(11) 0.0381(11) -0.0023(10) 0.0068(10) 0.0017(9) N2 0.0374(10) 0.0382(10) 0.0348(10) 0.0004(9) 0.0025(9) 0.0002(8) N3 0.0473(12) 0.0515(13) 0.0390(11) -0.0006(11) 0.0025(10) -0.0056(10) N4 0.0706(16) 0.0488(13) 0.0690(15) -0.0117(12) 0.0016(13) -0.0038(12) C1 0.0483(16) 0.0445(14) 0.0486(15) -0.0041(13) 0.0037(13) 0.0043(12) C2 0.0452(14) 0.0395(13) 0.0438(14) 0.0001(12) -0.0026(12) 0.0008(10) C3 0.0468(15) 0.0415(14) 0.0511(14) -0.0017(12) -0.0018(13) 0.0027(12) C4 0.0373(13) 0.0389(12) 0.0402(12) 0.0059(11) -0.0052(11) -0.0039(11) C5 0.0508(16) 0.0567(17) 0.0354(12) -0.0045(14) 0.0045(12) -0.0006(12) C6 0.0443(14) 0.0469(14) 0.0378(12) -0.0035(12) -0.0008(12) 0.0036(11) C7 0.0322(11) 0.0390(12) 0.0367(12) 0.0007(10) -0.0025(11) 0.0030(10) C8 0.0352(12) 0.0387(12) 0.0358(12) -0.0006(11) 0.0003(10) -0.0005(10) C9 0.0527(15) 0.0390(13) 0.0408(13) 0.0029(12) -0.0010(12) 0.0029(10) C10 0.0585(17) 0.0506(15) 0.0331(12) -0.0016(14) -0.0009(12) 0.0005(11) C11 0.0466(15) 0.0463(15) 0.0392(13) -0.0067(12) 0.0075(12) -0.0061(11) C12 0.0492(14) 0.0360(12) 0.0499(15) -0.0031(11) 0.0029(12) 0.0027(11) C13 0.0455(14) 0.0412(13) 0.0376(12) -0.0064(11) -0.0022(11) 0.0048(11) C14 0.074(2) 0.0559(16) 0.0485(14) -0.0081(16) 0.0106(15) -0.0135(13) 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 0.0000 '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 0.0000 '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 C1 N1 N2 103.7(2) yes N1 N2 C7 125.9(2) no N1 N2 C4 112.5(2) yes C7 N2 C4 121.6(2) no C5 N3 C4 115.1(2) yes N1 C1 C2 113.3(2) yes N1 C1 H1 123.4 no C2 C1 H1 123.4 no C4 C2 C1 105.3(2) yes C4 C2 C3 125.2(2) no C1 C2 C3 129.4(2) no N4 C3 C2 178.5(3) no N3 C4 N2 123.3(2) no N3 C4 C2 131.4(2) no N2 C4 C2 105.3(2) yes N3 C5 C6 124.5(2) no N3 C5 H5 117.7 no C6 C5 H5 117.7 no C7 C6 C5 120.6(2) no C7 C6 H6 119.7 no C5 C6 H6 119.7 no N2 C7 C6 114.8(2) no N2 C7 C8 121.2(2) no C6 C7 C8 124.0(2) no C13 C8 C9 118.5(2) no C13 C8 C7 118.9(2) no C9 C8 C7 122.5(2) no C10 C9 C8 120.0(2) no C10 C9 H9 120.0 no C8 C9 H9 120.0 no C9 C10 C11 121.9(2) no C9 C10 H10 119.1 no C11 C10 H10 119.1 no C12 C11 C10 117.5(2) no C12 C11 C14 120.5(2) no C10 C11 C14 122.0(2) no C13 C12 C11 121.5(2) no C13 C12 H12 119.2 no C11 C12 H12 119.2 no C12 C13 C8 120.6(2) no C12 C13 H13 119.7 no C8 C13 H13 119.7 no C11 C14 H14A 109.5 no C11 C14 H14B 109.5 no H14A C14 H14B 109.5 no C11 C14 H14C 109.5 no H14A C14 H14C 109.5 no H14B C14 H14C 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 1.323(3) yes N1 N2 1.371(2) yes N2 C7 1.372(3) yes N2 C4 1.385(3) yes N3 C5 1.314(3) yes N3 C4 1.341(3) yes N4 C3 1.133(3) yes C1 C2 1.400(3) yes C1 H1 0.9300 no C2 C4 1.385(3) yes C2 C3 1.426(3) yes C5 C6 1.396(3) yes C5 H5 0.9300 yes C6 C7 1.373(3) no C6 H6 0.9300 no C7 C8 1.472(3) no C8 C13 1.388(3) no C8 C9 1.392(3) no C9 C10 1.375(3) no C9 H9 0.9300 no C10 C11 1.389(3) no C10 H10 0.9300 no C11 C12 1.382(3) no C11 C14 1.509(3) no C12 C13 1.375(3) no C12 H12 0.9300 no C13 H13 0.9300 no C14 H14A 0.9600 no C14 H14B 0.9600 no C14 H14C 0.9600 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 C1 N1 N2 C7 177.5(2) yes C1 N1 N2 C4 0.0(3) yes N2 N1 C1 C2 0.2(3) yes N1 C1 C2 C4 -0.4(3) yes N1 C1 C2 C3 -176.3(3) yes C4 C2 C3 N4 -0.90(10) yes C1 C2 C3 N4 166(11) yes C5 N3 C4 N2 -2.4(3) yes C5 N3 C4 C2 175.6(3) yes N1 N2 C4 N3 178.1(2) yes C7 N2 C4 N3 0.5(3) yes N1 N2 C4 C2 -0.2(3) no C7 N2 C4 C2 -177.8(2) no C1 C2 C4 N3 -177.8(3) no C3 C2 C4 N3 -1.7(4) no C1 C2 C4 N2 0.4(3) no C3 C2 C4 N2 176.5(2) no C4 N3 C5 C6 2.1(4) no N3 C5 C6 C7 -0.1(4) no N1 N2 C7 C6 -175.7(2) no C4 N2 C7 C6 1.6(3) no N1 N2 C7 C8 4.8(3) no C4 N2 C7 C8 -177.9(2) no C5 C6 C7 N2 -1.8(3) no C5 C6 C7 C8 177.7(2) no N2 C7 C8 C13 -141.1(2) no C6 C7 C8 C13 39.5(3) no N2 C7 C8 C9 41.7(3) no C6 C7 C8 C9 -137.7(3) no C13 C8 C9 C10 -0.2(4) no C7 C8 C9 C10 177.0(2) no C8 C9 C10 C11 0.6(4) no C9 C10 C11 C12 -0.5(4) no C9 C10 C11 C14 178.7(3) no C10 C11 C12 C13 -0.1(4) no C14 C11 C12 C13 -179.3(2) no C11 C12 C13 C8 0.5(4) no C9 C8 C13 C12 -0.4(4) no C7 C8 C13 C12 -177.7(2) no