#------------------------------------------------------------------------------ #$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201972 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/15/2101550.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_2101550 loop_ _publ_author_name 'Halcrow, M. A.' 'Powell, H. R.' 'Duer, M. J.' _publ_section_title ; Tautomerism in 3{5}-(dimethoxyphenyl)pyrazoles ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 746 _journal_page_last 752 _journal_paper_doi 10.1107/S0108768196005204 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C11 H12 N2 O2' _chemical_formula_weight 204.23 _chemical_name_systematic ; 3{5}-(2',5'-dimethoxyphenyl)pyrazole (III) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.01(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.376(2) _cell_length_b 6.4421(8) _cell_length_c 14.419(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 60.0 _cell_measurement_theta_min 59.2 _cell_volume 1056.7(3) _computing_molecular_graphics XP _computing_publication_material XP _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal focus rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 3130 _diffrn_reflns_theta_max 60.15 _diffrn_reflns_theta_min 3.89 _diffrn_standards_decay_% 0.44 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.738 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_correction_T_min 0.904 _exptl_absorpt_correction_type '\y scans' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.284 _exptl_crystal_description Block _exptl_crystal_F_000 432 _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.158 _refine_diff_density_min -0.166 _refine_ls_extinction_coef 0.022(3) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 0.901 _refine_ls_goodness_of_fit_obs 0.872 _refine_ls_hydrogen_treatment 'H atoms placed in calculated positions' _refine_ls_matrix_type full _refine_ls_number_parameters 137 _refine_ls_number_reflns 1571 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.901 _refine_ls_restrained_S_obs 0.872 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_obs 0.0372 _refine_ls_shift/esd_max -0.015 _refine_ls_shift/esd_mean 0.004 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1608P)^2^+0.0311P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1588 _refine_ls_wR_factor_obs 0.1471 _reflns_number_observed 1444 _reflns_number_total 1571 _reflns_observed_criterion >2sigma(I) _cod_data_source_file bm0005.cif _cod_data_source_block mh105 _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: '_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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1608P)^2^+0.0311P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.1608P)^2^+0.0311P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1056.8(3) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2101550 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_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 0.0497(7) 0.0504(8) 0.0475(7) 0.0101(5) -0.0007(5) -0.0061(5) N2 0.0604(8) 0.0607(9) 0.0451(7) 0.0104(6) -0.0041(5) -0.0090(5) C3 0.0602(10) 0.0595(10) 0.0523(9) 0.0159(8) 0.0002(7) -0.0148(7) C4 0.0518(9) 0.0602(10) 0.0543(9) 0.0164(7) -0.0014(6) -0.0096(7) C5 0.0439(8) 0.0465(9) 0.0444(8) 0.0038(6) 0.0035(6) -0.0002(6) C1' 0.0401(8) 0.0457(8) 0.0464(8) -0.0029(6) 0.0068(6) -0.0030(6) C2' 0.0450(8) 0.0457(9) 0.0556(9) -0.0004(6) 0.0080(6) -0.0033(6) C3' 0.0622(10) 0.0502(10) 0.0621(10) 0.0030(7) 0.0092(7) -0.0122(7) C4' 0.0655(10) 0.0586(10) 0.0525(9) -0.0047(7) 0.0059(7) -0.0144(7) C5' 0.0490(8) 0.0576(10) 0.0441(8) -0.0046(7) 0.0038(6) -0.0045(6) C6' 0.0472(8) 0.0480(8) 0.0474(9) 0.0007(6) 0.0043(6) -0.0048(6) O11 0.0604(8) 0.0521(8) 0.0729(8) 0.0156(5) -0.0063(6) -0.0108(5) C12 0.0683(11) 0.0556(11) 0.0876(12) 0.0174(8) 0.0076(9) -0.0040(9) O13 0.0647(8) 0.0738(8) 0.0532(7) 0.0054(6) -0.0091(5) -0.0139(5) C14 0.0679(11) 0.0781(13) 0.0579(10) 0.0125(9) -0.0105(8) -0.0080(8) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol N1 0.87856(11) 0.0161(2) 0.44422(8) 0.0492(4) Uani d . 1 N H1 0.93095(11) -0.0772(2) 0.43366(8) 0.059 Uiso calc R 1 H N2 0.88693(11) 0.1552(2) 0.51353(8) 0.0554(5) Uani d . 1 N C3 0.78953(14) 0.2652(3) 0.50582(11) 0.0573(5) Uani d . 1 C H3 0.76994(14) 0.3745(3) 0.54502(11) 0.069 Uiso calc R 1 H C4 0.72014(13) 0.1998(3) 0.43314(11) 0.0555(5) Uani d . 1 C H4 0.64795(13) 0.2539(3) 0.41493(11) 0.067 Uiso calc R 1 H C5 0.78050(11) 0.0369(2) 0.39307(9) 0.0449(5) Uani d . 1 C C1' 0.75336(11) -0.0846(2) 0.30959(10) 0.0441(4) Uani d . 1 C C2' 0.81281(12) -0.2681(2) 0.28686(11) 0.0488(5) Uani d . 1 C C3' 0.78465(14) -0.3725(3) 0.20577(12) 0.0582(5) Uani d . 1 C H3' 0.82416(14) -0.4944(3) 0.19080(12) 0.070 Uiso calc R 1 H C4' 0.69931(15) -0.2984(3) 0.14739(11) 0.0589(5) Uani d . 1 C H4' 0.68142(15) -0.3702(3) 0.09324(11) 0.071 Uiso calc R 1 H C5' 0.63946(13) -0.1168(2) 0.16863(10) 0.0503(5) Uani d . 1 C C6' 0.66711(12) -0.0115(2) 0.24916(10) 0.0475(5) Uani d . 1 C H6' 0.62739(12) 0.1106(2) 0.26335(10) 0.057 Uiso calc R 1 H O11 0.89773(9) -0.3306(2) 0.34770(9) 0.0618(4) Uani d . 1 O C12 0.9675(2) -0.5057(3) 0.32532(15) 0.0705(6) Uani d . 1 C H12A 1.0229(2) -0.5306(3) 0.37429(15) 0.106 Uiso calc R 1 H H12B 1.0090(2) -0.4801(3) 0.26850(15) 0.106 Uiso calc R 1 H H12C 0.9178(2) -0.6251(3) 0.31799(15) 0.106 Uiso calc R 1 H O13 0.55723(10) -0.0533(2) 0.10512(8) 0.0639(4) Uani d . 1 O C14 0.4945(2) 0.1314(3) 0.12400(12) 0.0680(6) Uani d . 1 C H14A 0.4402(2) 0.1582(3) 0.07450(12) 0.102 Uiso calc R 1 H H14B 0.5487(2) 0.2451(3) 0.12914(12) 0.102 Uiso calc R 1 H H14C 0.4522(2) 0.1163(3) 0.18118(12) 0.102 Uiso calc R 1 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C5 N1 N2 113.57(11) y C3 N2 N1 103.63(12) y N2 C3 C4 112.37(13) y C3 C4 C5 105.42(13) y N1 C5 C4 105.00(12) y N1 C5 C1' 124.83(12) y C4 C5 C1' 130.05(13) y C6' C1' C2' 118.58(13) y C6' C1' C5 118.71(13) y C2' C1' C5 122.69(13) y O11 C2' C3' 124.20(14) y O11 C2' C1' 116.10(13) y C3' C2' C1' 119.69(14) y C4' C3' C2' 120.83(15) y C3' C4' C5' 120.37(14) y O13 C5' C6' 124.76(14) y O13 C5' C4' 116.03(13) y C6' C5' C4' 119.20(15) y C5' C6' C1' 121.33(14) y C2' O11 C12 118.99(14) y C5' O13 C14 117.81(12) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 1.344(2) y N1 N2 1.346(2) y N2 C3 1.320(2) y C3 C4 1.378(2) y C4 C5 1.381(2) y C5 C1' 1.469(2) y C1' C6' 1.394(2) y C1' C2' 1.401(2) y C2' O11 1.365(2) y C2' C3' 1.386(2) y C3' C4' 1.371(2) y C4' C5' 1.388(2) y C5' O13 1.372(2) y C5' C6' 1.381(2) y O11 C12 1.416(2) y O13 C14 1.413(2) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 11879103