#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/60/2216060.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_2216060 loop_ _publ_author_name 'Zhou, Guanghua' 'An, Yue' 'Han, Jing' 'Ge, Maofa' 'Xing, Yongheng' _publ_section_title ; Methyl 5-phenyl-1H-pyrazole-3-carboxylate ; _journal_coeditor_code LX2019 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o4474 _journal_page_last o4474 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C11 H10 N2 O2' _chemical_formula_moiety 'C11 H10 N2 O2' _chemical_formula_sum 'C11 H10 N2 O2' _chemical_formula_weight 202.21 _chemical_melting_point 185.7(2) _chemical_name_systematic ; Methyl 5-phenyl-1H-pyrazole-3-carboxylate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 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 122.933(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 24.540(6) _cell_length_b 5.9800(10) _cell_length_c 16.387(4) _cell_measurement_reflns_used 2416 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.97 _cell_measurement_theta_min 2.51 _cell_volume 2018.3(8) _computing_cell_refinement 'XSCANS (Siemens, 1996)' _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction 'SHELXTL (Sheldrick, 1997a)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997a) and DIAMOND (Brandenburg, 1998)' _computing_publication_material 'SHELXTL (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997b)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997b)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.0 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Bruker P4' _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 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 5591 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.51 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rhombic _exptl_crystal_F_000 848 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.209 _refine_diff_density_min -0.216 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 2185 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0436 _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^+0.752P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1079 _refine_ls_wR_factor_ref 0.1197 _reflns_number_gt 1612 _reflns_number_total 2185 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lx2019.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'C 2/c' _[local]_cod_cif_authors_sg_Hall -c_2yc _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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '185.5-185.9' was changed to '185.7(2)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '185.5-185.9' was changed to '185.7(2)' - the average value was taken and precision was estimated. '_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_database_code 2216060 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 C C1 0.17604(8) -0.1789(3) 0.03661(12) 0.0476(4) Uani d . 1 H H1 0.2185 -0.1488 0.0870 0.057 Uiso calc R 1 C C2 0.16326(10) -0.3570(3) -0.02517(13) 0.0580(5) Uani d . 1 H H2 0.1973 -0.4456 -0.0162 0.070 Uiso calc R 1 C C3 0.10077(10) -0.4042(3) -0.09971(14) 0.0594(5) Uani d . 1 H H3 0.0924 -0.5242 -0.1410 0.071 Uiso calc R 1 C C4 0.05089(9) -0.2733(3) -0.11276(13) 0.0563(5) Uani d . 1 H H4 0.0085 -0.3054 -0.1631 0.068 Uiso calc R 1 C C5 0.06269(8) -0.0947(3) -0.05225(11) 0.0471(4) Uani d . 1 H H5 0.0283 -0.0069 -0.0623 0.057 Uiso calc R 1 C C6 0.12571(7) -0.0444(3) 0.02380(10) 0.0365(4) Uani d . 1 C C7 0.13661(7) 0.1465(3) 0.08722(10) 0.0349(3) Uani d . 1 C C8 0.09485(7) 0.3081(3) 0.08165(10) 0.0373(4) Uani d . 1 H H8 0.0508 0.3221 0.0345 0.045 Uiso calc R 1 C C9 0.13253(7) 0.4464(3) 0.16157(10) 0.0358(4) Uani d . 1 C C10 0.11091(8) 0.6429(3) 0.19061(11) 0.0398(4) Uani d . 1 C C11 0.14358(11) 0.9382(3) 0.30373(15) 0.0663(6) Uani d . 1 H H11A 0.1821 0.9962 0.3604 0.099 Uiso calc R 1 H H11B 0.1126 0.8983 0.3198 0.099 Uiso calc R 1 H H11C 0.1252 1.0502 0.2537 0.099 Uiso calc R 1 N N1 0.19519(6) 0.1955(2) 0.16806(9) 0.0405(3) Uani d . 1 H H1N 0.2296 0.1177 0.1872 0.049 Uiso calc R 1 N N2 0.19433(6) 0.3774(2) 0.21536(9) 0.0413(3) Uani d . 1 O O1 0.05575(6) 0.7053(2) 0.14871(10) 0.0640(4) Uani d . 1 O O2 0.15988(6) 0.7429(2) 0.26949(8) 0.0522(3) Uani d . 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 C1 0.0431(9) 0.0528(11) 0.0442(9) 0.0067(8) 0.0219(8) -0.0001(8) C2 0.0669(13) 0.0531(11) 0.0609(11) 0.0143(9) 0.0392(10) 0.0002(9) C3 0.0805(14) 0.0510(11) 0.0535(11) -0.0026(10) 0.0409(11) -0.0100(9) C4 0.0554(11) 0.0605(12) 0.0454(9) -0.0107(9) 0.0225(8) -0.0135(9) C5 0.0383(9) 0.0530(10) 0.0430(9) -0.0004(8) 0.0176(7) -0.0066(8) C6 0.0374(8) 0.0391(8) 0.0326(7) 0.0008(6) 0.0188(7) 0.0036(6) C7 0.0292(7) 0.0378(8) 0.0328(7) -0.0017(6) 0.0138(6) 0.0023(6) C8 0.0254(7) 0.0401(9) 0.0361(8) 0.0004(6) 0.0100(6) 0.0011(6) C9 0.0296(8) 0.0363(8) 0.0371(8) -0.0011(6) 0.0152(6) 0.0030(6) C10 0.0383(9) 0.0364(9) 0.0426(8) -0.0022(7) 0.0207(7) 0.0010(7) C11 0.0917(16) 0.0487(12) 0.0713(13) -0.0093(10) 0.0526(12) -0.0182(10) N1 0.0269(7) 0.0431(8) 0.0414(7) 0.0048(5) 0.0121(6) -0.0022(6) N2 0.0322(7) 0.0402(7) 0.0412(7) 0.0002(6) 0.0132(6) -0.0041(6) O1 0.0428(7) 0.0590(8) 0.0755(9) 0.0109(6) 0.0227(7) -0.0104(7) O2 0.0491(7) 0.0479(7) 0.0538(7) -0.0055(5) 0.0242(6) -0.0153(6) 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 C1 C6 120.36(16) C2 C1 H1 119.8 C6 C1 H1 119.8 C3 C2 C1 120.56(17) C3 C2 H2 119.7 C1 C2 H2 119.7 C4 C3 C2 119.54(17) C4 C3 H3 120.2 C2 C3 H3 120.2 C3 C4 C5 120.74(17) C3 C4 H4 119.6 C5 C4 H4 119.6 C4 C5 C6 120.56(16) C4 C5 H5 119.7 C6 C5 H5 119.7 C1 C6 C5 118.25(15) C1 C6 C7 122.54(14) C5 C6 C7 119.21(14) N1 C7 C8 105.59(13) N1 C7 C6 123.29(13) C8 C7 C6 131.11(13) C7 C8 C9 105.38(13) C7 C8 H8 127.3 C9 C8 H8 127.3 N2 C9 C8 111.80(13) N2 C9 C10 120.80(13) C8 C9 C10 127.38(14) O1 C10 O2 123.87(15) O1 C10 C9 123.93(14) O2 C10 C9 112.21(13) O2 C11 H11A 109.5 O2 C11 H11B 109.5 H11A C11 H11B 109.5 O2 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 N2 N1 C7 113.48(12) N2 N1 H1N 123.3 C7 N1 H1N 123.3 C9 N2 N1 103.74(12) C10 O2 C11 116.42(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.383(2) C1 C6 1.391(2) C1 H1 0.9300 C2 C3 1.374(3) C2 H2 0.9300 C3 C4 1.368(3) C3 H3 0.9300 C4 C5 1.377(2) C4 H4 0.9300 C5 C6 1.393(2) C5 H5 0.9300 C6 C7 1.467(2) C7 N1 1.355(2) C7 C8 1.375(2) C8 C9 1.392(2) C8 H8 0.9300 C9 N2 1.339(2) C9 C10 1.471(2) C10 O1 1.197(2) C10 O2 1.336(2) C11 O2 1.443(2) C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600 N1 N2 1.342(2) N1 H1N 0.8600 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 H1N N2 4_545 0.86 2.20 2.998(2) 153.4 N1 H1N O2 4_545 0.86 2.52 3.134(2) 129.5 C5 H5 O1 5_565 0.93 2.52 3.372(2) 153.0 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 C6 C1 C2 C3 -0.3(3) C1 C2 C3 C4 0.1(3) C2 C3 C4 C5 0.2(3) C3 C4 C5 C6 -0.3(3) C2 C1 C6 C5 0.2(2) C2 C1 C6 C7 -179.99(15) C4 C5 C6 C1 0.1(2) C4 C5 C6 C7 -179.73(15) C1 C6 C7 N1 -6.1(2) C5 C6 C7 N1 173.74(14) C1 C6 C7 C8 173.71(16) C5 C6 C7 C8 -6.5(2) N1 C7 C8 C9 0.19(16) C6 C7 C8 C9 -179.64(15) C7 C8 C9 N2 -0.41(18) C7 C8 C9 C10 -178.60(15) N2 C9 C10 O1 -175.69(16) C8 C9 C10 O1 2.4(3) N2 C9 C10 O2 4.0(2) C8 C9 C10 O2 -178.00(14) C8 C7 N1 N2 0.08(17) C6 C7 N1 N2 179.93(13) C8 C9 N2 N1 0.45(17) C10 C9 N2 N1 178.78(13) C7 N1 N2 C9 -0.33(17) O1 C10 O2 C11 -0.4(2) C9 C10 O2 C11 179.90(14) _cod_database_fobs_code 2216060 _journal_paper_doi 10.1107/S1600536807052452