#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/63/2006392.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_2006392 loop_ _publ_author_name 'Blake, Alexander J.' 'McNab, Hamish' 'Thornley, Craig' _publ_section_title ; Four Methyl Azolyl-3-propenoates ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1093 _journal_page_last 1097 _journal_paper_doi 10.1107/S0108270197004952 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C8 H9 N O2' _chemical_formula_sum 'C8 H9 N O2' _chemical_formula_weight 151.16 _chemical_name_systematic ; methyl (E)-3-(pyrrol-2-yl)propenoate ; _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 92.957(15) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.795(3) _cell_length_b 8.2710(10) _cell_length_c 17.803(3) _cell_measurement_reflns_used 27 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 12 _cell_volume 1587.4(6) _computing_cell_refinement DIF4 _computing_data_collection 'DIF4 (Stoe & Cie, 1991a)' _computing_data_reduction 'REDU4 (Stoe & Cie, 1991b)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1994)' _computing_publication_material SHELXL-96 _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measurement_device 'Stoe Stadi4 four-circle' _diffrn_measurement_method \w-2\q _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 0.0 _diffrn_reflns_av_sigmaI/netI 0.1114 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2589 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.72 _diffrn_standards_decay_% 16 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_meas ? _exptl_crystal_description lath _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.930 _exptl_crystal_size_mid 0.175 _exptl_crystal_size_min 0.078 _refine_diff_density_max 0.17 _refine_diff_density_min -0.18 _refine_ls_extinction_coef 0.0038(13) _refine_ls_extinction_method 'SHELXL96 (Sheldrick, 1996)' _refine_ls_goodness_of_fit_all 1.014 _refine_ls_goodness_of_fit_obs 1.205 _refine_ls_hydrogen_treatment ;H atoms freely refined (for H1 and H1', on N1 and N1', respectively) and riding model for all others ; _refine_ls_matrix_type full _refine_ls_number_parameters 206 _refine_ls_number_reflns 2589 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.014 _refine_ls_restrained_S_obs 1.203 _refine_ls_R_factor_all 0.2221 _refine_ls_R_factor_obs .0580 _refine_ls_shift/esd_max 0.005 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.079P)^2^+0.352P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.2147 _refine_ls_wR_factor_obs .1413 _reflns_number_observed 918 _reflns_number_total 2589 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ha1192.cif _cod_data_source_block 3 _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (11 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.079P)^2^+0.352P] 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^)+(0.079P)^2^+0.352P] 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 1587.5(6) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2006392 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, 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 .042(2) .068(3) .054(2) .001(2) .012(2) .005(3) C2 .039(3) .056(3) .059(3) -.002(3) .012(2) -.003(3) C3 .052(3) .072(4) .074(3) -.003(3) .024(3) -.010(3) C4 .064(4) .082(5) .063(3) -.002(4) .006(3) -.020(3) C5 .048(3) .070(4) .075(4) -.001(3) .001(3) -.002(3) C6 .043(3) .062(4) .072(3) -.003(3) .015(3) .007(3) C7 .043(3) .065(4) .059(3) .000(3) .009(3) .004(3) C8 .049(3) .052(4) .055(3) .005(3) .011(3) .006(3) O8 .049(2) .083(3) .074(2) -.007(2) .0136(18) -.010(2) O9 .049(2) .077(3) .063(2) .001(2) .0096(18) -.009(2) C9 .070(4) .092(5) .062(3) .007(4) -.002(3) -.009(3) N1' .045(2) .073(3) .060(3) -.002(3) .012(2) -.006(3) C2' .041(3) .062(4) .060(3) -.006(3) .015(3) -.013(3) C3' .060(3) .078(5) .063(3) .002(3) .016(3) .001(3) C4' .074(4) .077(5) .063(3) .004(4) .005(3) .000(3) C5' .050(3) .082(5) .070(4) .009(3) .003(3) -.012(4) C6' .045(3) .060(4) .063(3) .000(3) .010(3) -.009(3) C7' .042(3) .067(4) .063(3) -.011(3) .013(2) -.004(3) C8' .047(3) .054(4) .052(3) -.010(3) .012(2) -.005(3) O8' .048(2) .098(3) .075(2) .002(2) .0202(18) .005(2) O9' .051(2) .073(3) .066(2) -.004(2) .0139(18) .002(2) C9' .071(4) .084(5) .064(3) -.001(4) .005(3) .003(4) 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_disorder_group _atom_site_type_symbol N1 .8397(4) .2079(6) .1729(2) .0542(12) Uani d D 1 . N H1 .793(3) .225(6) .2128(16) .065 Uiso d D 1 . H C2 .9616(4) .2447(7) .1644(3) .0511(13) Uani d . 1 . C C3 .9912(5) .1864(7) .0959(3) .0655(16) Uani d . 1 . C H3 1.0687 .1937 .0755 .079 Uiso calc R 1 . H C4 .8868(5) .1143(7) .0616(3) .0697(17) Uani d . 1 . C H4 .8807 .0660 .0143 .084 Uiso calc R 1 . H C5 .7953(5) .1286(7) .1108(3) .0645(16) Uani d . 1 . C H5 .7148 .0898 .1030 .077 Uiso calc R 1 . H C6 1.0364(5) .3355(7) .2182(3) .0585(15) Uani d . 1 . C H6 1.1191 .3492 .2072 .070 Uiso calc R 1 . H C7 1.0026(4) .4022(6) .2814(3) .0556(15) Uani d . 1 . C H7 .9209 .3917 .2950 .067 Uiso calc R 1 . H C8 1.0907(5) .4920(7) .3303(3) .0519(14) Uani d . 1 . C O8 1.1979(3) .5203(5) .31773(18) .0684(11) Uani d . 1 . O O9 1.0392(3) .5442(4) .39300(18) .0627(11) Uani d . 1 . O C9 1.1198(5) .6312(7) .4456(3) .0744(18) Uani d . 1 . C H9A 1.0743 .6629 .4881 .112 Uiso calc R 1 . H H9B 1.1511 .7256 .4216 .112 Uiso calc R 1 . H H9C 1.1878 .5630 .4621 .112 Uiso calc R 1 . H N1' 1.3299(4) .5310(6) .1795(2) .0588(13) Uani d D 1 . N H1' 1.292(4) .509(6) .2219(15) .071 Uiso d D 1 . H C2' 1.4513(4) .4972(7) .1662(3) .0540(14) Uani d . 1 . C C3' 1.4718(5) .5582(7) .0969(3) .0663(17) Uani d . 1 . C H3' 1.5463 .5525 .0730 .080 Uiso calc R 1 . H C4' 1.3623(5) .6311(7) .0673(3) .0711(17) Uani d . 1 . C H4' 1.3504 .6832 .0211 .085 Uiso calc R 1 . H C5' 1.2777(5) .6098(7) .1199(3) .0672(16) Uani d . 1 . C H5' 1.1957 .6445 .1156 .081 Uiso calc R 1 . H C6' 1.5323(4) .4066(6) .2166(3) .0556(14) Uani d . 1 . C H6' 1.6134 .3952 .2023 .067 Uiso calc R 1 . H C7' 1.5071(4) .3370(7) .2809(3) .0567(15) Uani d . 1 . C H7' 1.4275 .3451 .2983 .068 Uiso calc R 1 . H C8' 1.6015(5) .2481(7) .3248(3) .0507(13) Uani d . 1 . C O8' 1.7076(3) .2259(5) .30822(18) .0733(12) Uani d . 1 . O O9' 1.5578(3) .1878(4) .38824(19) .0629(11) Uani d . 1 . O C9' 1.6448(5) .0973(7) .4357(3) .0730(17) Uani d . 1 . C H9A' 1.6044 .0591 .4792 .109 Uiso calc R 1 . H H9B' 1.7132 .1657 .4515 .109 Uiso calc R 1 . H H9C' 1.6749 .0067 .4083 .109 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 0.0033 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 _geom_angle_publ_flag C5 N1 C2 108.6(4) yes C3 C2 N1 107.0(5) yes C3 C2 C6 129.2(5) yes N1 C2 C6 123.7(5) yes C2 C3 C4 108.8(5) yes C5 C4 C3 106.2(5) yes N1 C5 C4 109.3(5) yes C7 C6 C2 128.1(5) yes C6 C7 C8 121.4(5) yes O8 C8 O9 122.1(5) yes O8 C8 C7 125.9(5) yes O9 C8 C7 112.0(4) yes C8 O9 C9 116.1(4) yes C5' N1' C2' 109.2(4) ? C3' C2' N1' 106.4(5) ? C3' C2' C6' 129.8(5) ? N1' C2' C6' 123.8(5) ? C2' C3' C4' 109.0(5) ? C5' C4' C3' 105.6(5) ? N1' C5' C4' 109.8(5) ? C7' C6' C2' 128.6(5) ? C6' C7' C8' 121.1(5) ? O8' C8' O9' 121.8(5) ? O8' C8' C7' 126.2(5) ? O9' C8' C7' 112.0(4) ? C8' O9' C9' 116.1(4) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 . 1.352(6) yes N1 C2 . 1.366(6) yes C2 C3 . 1.365(6) yes C2 C6 . 1.433(7) yes C3 C4 . 1.389(7) yes C4 C5 . 1.359(6) yes C6 C7 . 1.322(6) yes C7 C8 . 1.459(7) yes C8 O8 . 1.213(5) yes C8 O9 . 1.343(5) yes O9 C9 . 1.437(6) yes N1' C5' . 1.343(6) ? N1' C2' . 1.372(5) ? C2' C3' . 1.361(6) ? C2' C6' . 1.433(7) ? C3' C4' . 1.405(7) ? C4' C5' . 1.354(6) ? C6' C7' . 1.322(6) ? C7' C8' . 1.452(7) ? C8' O8' . 1.212(5) ? C8' O9' . 1.342(5) ? O9' C9' . 1.441(6) ? 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 C5 N1 C2 C3 -0.1(6) C5 N1 C2 C6 177.1(5) N1 C2 C3 C4 0.5(6) C6 C2 C3 C4 -176.4(6) C2 C3 C4 C5 -0.8(7) C2 N1 C5 C4 -0.4(6) C3 C4 C5 N1 0.8(7) C3 C2 C6 C7 173.8(6) N1 C2 C6 C7 -2.6(9) C2 C6 C7 C8 -179.8(6) C6 C7 C8 O8 3.2(8) C6 C7 C8 O9 -177.4(4) O8 C8 O9 C9 -1.9(7) C7 C8 O9 C9 178.7(5) C5' N1' C2' C3' 0.2(6) C5' N1' C2' C6' -176.7(5) N1' C2' C3' C4' 0.3(6) C6' C2' C3' C4' 177.0(6) C2' C3' C4' C5' -0.7(7) C2' N1' C5' C4' -0.7(7) C3' C4' C5' N1' 0.9(7) C3' C2' C6' C7' -173.7(6) N1' C2' C6' C7' 2.4(9) C2' C6' C7' C8' 179.5(6) C6' C7' C8' O8' -1.3(8) C6' C7' C8' O9' 179.6(4) O8' C8' O9' C9' 0.8(7) C7' C8' O9' C9' 180.0(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 14216444 2 PubChem 139055605