#------------------------------------------------------------------------------ #$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2215924.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_2215924 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Zhang, Cunyan' 'Li, Hui' 'Liu, Dengke' 'Liu, Mo' _publ_section_title ; 1-Methyl-3-propyl-1H-pyrazole-5-carboxylic acid ; _journal_coeditor_code HB2523 _journal_issue 11 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o4209 _journal_page_last o4209 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C8 H12 N2 O2' _chemical_formula_moiety 'C8 H12 N2 O2' _chemical_formula_sum 'C8 H12 N2 O2' _chemical_formula_weight 168.20 _chemical_name_systematic ; 1-Methyl-3-propyl-1H-pyrazole-5-carboxylic acid ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens 'difmap and geom' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 92.136(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.9336(19) _cell_length_b 19.121(7) _cell_length_c 9.568(4) _cell_measurement_reflns_used 1522 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 26.25 _cell_measurement_theta_min 2.38 _cell_volume 902.0(6) _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _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 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4542 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.13 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 360 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.261 _refine_diff_density_min -0.233 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 114 _refine_ls_number_reflns 1585 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0801 _refine_ls_R_factor_gt 0.0538 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0772P)^2^+0.3462P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1378 _refine_ls_wR_factor_ref 0.1569 _reflns_number_gt 1090 _reflns_number_total 1585 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hb2523.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_ _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 O O1 0.7756(3) 0.22535(10) -0.19643(18) 0.0556(6) Uani d . 1 H H1 0.887(7) 0.2471(16) -0.245(3) 0.083 Uiso d . 1 O O2 0.6976(4) 0.33056(10) -0.1072(2) 0.0638(6) Uani d . 1 N N1 0.2945(4) 0.26597(10) 0.06131(19) 0.0405(5) Uani d . 1 N N2 0.1416(4) 0.21980(10) 0.1296(2) 0.0448(5) Uani d . 1 C C1 0.6546(5) 0.26908(13) -0.1126(2) 0.0434(6) Uani d . 1 C C2 0.4590(4) 0.23211(12) -0.0261(2) 0.0394(6) Uani d . 1 C C3 0.4085(5) 0.16227(12) -0.0133(2) 0.0458(6) Uani d . 1 H H3 0.4905 0.1260 -0.0607 0.055 Uiso calc R 1 C C4 0.2087(5) 0.15646(12) 0.0855(2) 0.0452(6) Uani d . 1 C C5 0.0766(5) 0.09284(13) 0.1413(3) 0.0594(8) Uani d . 1 H H5A -0.0493 0.1070 0.2115 0.071 Uiso calc R 1 H H5B -0.0278 0.0706 0.0658 0.071 Uiso calc R 1 C C6 0.2655(7) 0.04127(16) 0.2037(4) 0.0884(11) Uani d . 1 H H6A 0.3816 0.0643 0.2737 0.106 Uiso calc R 1 H H6B 0.3800 0.0234 0.1317 0.106 Uiso calc R 1 C C7 0.1225(9) -0.01936(19) 0.2712(5) 0.1121(15) Uani d . 1 H H7A 0.0049 -0.0019 0.3409 0.168 Uiso calc R 1 H H7B 0.2545 -0.0502 0.3143 0.168 Uiso calc R 1 H H7C 0.0173 -0.0444 0.2012 0.168 Uiso calc R 1 C C8 0.2658(5) 0.33973(12) 0.0891(3) 0.0549(7) Uani d . 1 H H8A 0.4412 0.3597 0.1098 0.082 Uiso calc R 1 H H8B 0.1528 0.3462 0.1677 0.082 Uiso calc R 1 H H8C 0.1842 0.3624 0.0085 0.082 Uiso calc R 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 O1 0.0502(11) 0.0624(12) 0.0563(11) -0.0052(8) 0.0315(9) -0.0021(9) O2 0.0663(13) 0.0528(12) 0.0744(13) -0.0101(9) 0.0330(10) 0.0005(9) N1 0.0359(10) 0.0442(11) 0.0423(11) 0.0006(8) 0.0138(9) -0.0002(8) N2 0.0406(11) 0.0489(12) 0.0462(12) -0.0010(9) 0.0193(9) 0.0035(9) C1 0.0354(13) 0.0546(16) 0.0409(13) 0.0004(11) 0.0102(10) 0.0029(11) C2 0.0328(12) 0.0492(14) 0.0370(12) 0.0008(10) 0.0124(10) -0.0005(10) C3 0.0421(14) 0.0479(15) 0.0485(14) 0.0058(10) 0.0176(11) -0.0010(11) C4 0.0403(13) 0.0466(14) 0.0498(15) 0.0019(10) 0.0158(11) 0.0032(11) C5 0.0573(17) 0.0537(16) 0.0690(18) -0.0030(12) 0.0266(14) 0.0048(13) C6 0.081(2) 0.063(2) 0.122(3) -0.0029(17) 0.015(2) 0.0266(19) C7 0.121(3) 0.070(2) 0.147(4) -0.003(2) 0.024(3) 0.045(2) C8 0.0584(17) 0.0454(15) 0.0622(17) -0.0001(12) 0.0198(13) -0.0057(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.317(3) O1 H1 0.84(3) O2 C1 1.195(3) N1 N2 1.346(2) N1 C2 1.352(3) N1 C8 1.443(3) N2 C4 1.328(3) C1 C2 1.475(3) C2 C3 1.365(3) C3 C4 1.396(3) C3 H3 0.9300 C4 C5 1.488(3) C5 C6 1.468(4) C5 H5A 0.9700 C5 H5B 0.9700 C6 C7 1.514(4) C6 H6A 0.9700 C6 H6B 0.9700 C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 H1 110(2) N2 N1 C2 110.26(19) N2 N1 C8 119.39(17) C2 N1 C8 130.34(19) C4 N2 N1 107.06(17) O2 C1 O1 124.6(2) O2 C1 C2 124.5(2) O1 C1 C2 111.0(2) N1 C2 C3 107.28(18) N1 C2 C1 122.6(2) C3 C2 C1 130.2(2) C2 C3 C4 105.9(2) C2 C3 H3 127.0 C4 C3 H3 127.0 N2 C4 C3 109.5(2) N2 C4 C5 120.9(2) C3 C4 C5 129.6(2) C6 C5 C4 114.5(2) C6 C5 H5A 108.6 C4 C5 H5A 108.6 C6 C5 H5B 108.6 C4 C5 H5B 108.6 H5A C5 H5B 107.6 C5 C6 C7 112.9(3) C5 C6 H6A 109.0 C7 C6 H6A 109.0 C5 C6 H6B 109.0 C7 C6 H6B 109.0 H6A C6 H6B 107.8 C6 C7 H7A 109.5 C6 C7 H7B 109.5 H7A C7 H7B 109.5 C6 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 N1 C8 H8A 109.5 N1 C8 H8B 109.5 H8A C8 H8B 109.5 N1 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 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 C2 N1 N2 C4 0.0(2) C8 N1 N2 C4 -179.6(2) N2 N1 C2 C3 0.2(2) C8 N1 C2 C3 179.7(2) N2 N1 C2 C1 -178.6(2) C8 N1 C2 C1 1.0(4) O2 C1 C2 N1 4.9(4) O1 C1 C2 N1 -175.1(2) O2 C1 C2 C3 -173.5(3) O1 C1 C2 C3 6.4(3) N1 C2 C3 C4 -0.2(3) C1 C2 C3 C4 178.4(2) N1 N2 C4 C3 -0.1(3) N1 N2 C4 C5 179.8(2) C2 C3 C4 N2 0.2(3) C2 C3 C4 C5 -179.6(3) N2 C4 C5 C6 -123.6(3) C3 C4 C5 C6 56.3(4) C4 C5 C6 C7 174.6(3) 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 O1 H1 N2 4_665 0.84(3) 1.88(3) 2.712(3) 169(3) C5 H5A O2 4_466 0.97 2.48 3.430(4) 166 _cod_database_code 2215924