#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/37/2203714.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_2203714 loop_ _publ_author_name 'Wu, Hai-Qiang' 'An, Lin-Kun' 'Huang, Zhi-Shu' 'Gu, Lian-Quan' 'Zain, Sharifuddin M.' 'Ng, Seik Weng' _publ_section_title ; Ethyl 3-methyl-5-nitro-1H-imidazole-2-carboxylate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o994 _journal_page_last o995 _journal_paper_doi 10.1107/S1600536804011080 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C7 H9 N3 O4' _chemical_formula_moiety 'C7 H9 N3 O4' _chemical_formula_sum 'C7 H9 N3 O4' _chemical_formula_weight 199.17 _chemical_name_systematic ; Ethyl 3-methyl-5-nitro-1H-imidazole-2-carboxylate ; _space_group_IT_number 62 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_space_group_name_H-M 'P n m a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.9400(10) _cell_length_b 6.7680(10) _cell_length_c 15.028(2) _cell_measurement_reflns_used 861 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.1 _cell_measurement_theta_min 2.7 _cell_volume 909.3(2) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _diffrn_measurement_device_type 'Bruker SMART area-detector' _diffrn_measurement_method '\f and \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 0.017 _diffrn_reflns_av_sigmaI/netI 0.008 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 11054 _diffrn_reflns_theta_full 27.1 _diffrn_reflns_theta_max 27.1 _diffrn_reflns_theta_min 2.7 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type none _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 416 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.21 _refine_diff_density_min -0.16 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 99 _refine_ls_number_reflns 1089 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.02 _refine_ls_R_factor_all 0.042 _refine_ls_R_factor_gt 0.038 _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^)+(0.0803P)^2^+0.1466P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.115 _refine_ls_wR_factor_ref 0.124 _reflns_number_gt 954 _reflns_number_total 1089 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6461.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_original_cell_volume 909.2(2) _cod_database_code 2203714 _cod_database_fobs_code 2203714 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.5077(2) 0.1981(2) 0.67890(10) 0.0518(6) Uani d P 0.50 A -1 O O2 0.2765(2) 0.279(2) 0.62500(10) 0.064(2) Uani d P 0.50 A -1 O O3 0.7800(2) 0.2500 0.29940(10) 0.0646(4) Uani d S 1 . . O O4 0.8913(2) 0.2500 0.42570(10) 0.0856(6) Uani d S 1 . . O N1 0.6255(2) 0.2500 0.51300(10) 0.0426(4) Uani d S 1 . . N N2 0.4010(2) 0.2500 0.44920(10) 0.0420(3) Uani d S 1 . . N N3 0.7798(2) 0.2500 0.38080(10) 0.0517(4) Uani d S 1 . . N C1 0.4506(4) 0.1661(4) 0.7683(2) 0.0559(6) Uani d P 0.50 A -1 C C2 0.4181(4) 0.3511(5) 0.8151(2) 0.0691(8) Uani d P 0.50 A -1 C C3 0.4082(2) 0.2500 0.61500(10) 0.0541(5) Uani d S 1 . . C C4 0.2380(2) 0.2500 0.4370(2) 0.0613(5) Uani d S 1 . . C C5 0.4806(2) 0.2500 0.52690(10) 0.0396(4) Uani d S 1 A . C C6 0.5012(2) 0.2500 0.38270(10) 0.0450(4) Uani d S 1 . . C C7 0.6370(2) 0.2500 0.42390(10) 0.0412(4) Uani d S 1 . . C H1a 0.5236 0.0915 0.8022 0.067 Uiso calc PR 0.50 A -1 H H1b 0.3599 0.0878 0.7650 0.067 Uiso calc PR 0.50 A -1 H H2a 0.3956 0.3232 0.8763 0.104 Uiso calc PR 0.50 A -1 H H2b 0.3338 0.4147 0.7877 0.104 Uiso calc PR 0.50 A -1 H H2c 0.5036 0.4366 0.8119 0.104 Uiso calc PR 0.50 A -1 H H4a 0.2146 0.2852 0.3767 0.092 Uiso calc PR 0.50 . . H H4b 0.1935 0.3442 0.4768 0.092 Uiso calc PR 0.50 . . H H4c 0.1993 0.1207 0.4496 0.092 Uiso calc PR 0.50 . . H H6 0.4821 0.2500 0.3218 0.054 Uiso calc SR 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 O1 0.0530(10) 0.070(2) 0.0330(10) 0.0030(10) -0.0010(10) -0.0020(10) O2 0.0430(10) 0.099(7) 0.0500(10) 0.0040(10) 0.0090(10) -0.0040(10) O3 0.0630(10) 0.0860(10) 0.0440(10) 0.000 0.0160(10) 0.000 O4 0.0370(10) 0.152(2) 0.0670(10) 0.000 0.0010(10) 0.000 N1 0.0370(10) 0.0540(10) 0.0370(10) 0.000 -0.0010(10) 0.000 N2 0.0350(10) 0.0520(10) 0.0390(10) 0.000 -0.0030(10) 0.000 N3 0.0410(10) 0.0660(10) 0.0480(10) 0.000 0.0070(10) 0.000 C1 0.067(2) 0.0640(10) 0.0370(10) -0.0010(10) 0.0020(10) 0.0050(10) C2 0.079(2) 0.081(2) 0.048(2) 0.004(2) 0.007(2) -0.009(2) C3 0.0420(10) 0.0810(10) 0.0400(10) 0.000 0.0020(10) 0.000 C4 0.0350(10) 0.095(2) 0.0540(10) 0.000 -0.0090(10) 0.000 C5 0.0370(10) 0.0470(10) 0.0350(10) 0.000 -0.0010(10) 0.000 C6 0.0450(10) 0.0550(10) 0.0350(10) 0.000 -0.0020(10) 0.000 C7 0.0380(10) 0.0490(10) 0.0370(10) 0.000 0.0030(10) 0.000 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 C1 O1 C3 117.6(2) yes C5 N1 C7 103.50(10) yes C4 N2 C5 128.5(2) yes C4 N2 C6 124.7(2) yes C5 N2 C6 106.80(10) yes O4 N3 O3 124.1(2) yes O3 N3 C7 117.0(2) yes O4 N3 C7 119.0(2) yes O1 C1 C2 112.7(2) yes O2 C3 O1 126.6(2) yes O1 C3 C5 110.4(2) yes O2 C3 C5 122.8(2) yes N1 C5 N2 112.20(10) yes N1 C5 C3 125.2(2) yes N2 C5 C3 122.6(2) yes N2 C6 C7 104.80(10) yes N1 C7 C6 112.70(10) yes N1 C7 N3 121.30(10) yes N3 C7 C6 126.1(2) yes O1 C1 H1a 109.1 no C2 C1 H1a 109.1 no O1 C1 H1b 109.1 no C2 C1 H1b 109.1 no H1a C1 H1b 107.8 no N2 C4 H4a 109.5 no N2 C4 H4b 109.5 no H4a C4 H4b 109.5 no N2 C4 H4c 109.5 no H4a C4 H4c 109.5 no H4b C4 H4c 109.5 no N2 C6 H6 127.6 no C7 C6 H6 127.6 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.453(3) yes O1 C3 1.355(2) yes O2 C3 1.203(4) yes O3 N3 1.223(2) yes O4 N3 1.203(2) yes N1 C5 1.312(2) yes N1 C7 1.343(2) yes N2 C4 1.469(2) yes N2 C6 1.342(2) yes N2 C5 1.367(2) yes N3 C7 1.432(2) yes C1 C2 1.464(4) yes C3 C5 1.475(2) yes C6 C7 1.363(2) yes C1 H1a 0.97 no C1 H1b 0.97 no C2 H2a 0.96 no C2 H2b 0.96 no C2 H2c 0.96 no C4 H4a 0.96 no C4 H4b 0.96 no C4 H4c 0.96 no C6 H6 0.93 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 O1 C1 C2 . . -76.5(3) no C1 O1 C3 O2 . 7_565 -18.9(7) no C1 O1 C3 O2 . . 2.5(8) no C1 O1 C3 O1 . 7_565 91.9(2) no C1 O1 C3 C5 . . -172.4(2) no C7 N1 C5 N2 . . 0.0 no C7 N1 C5 C3 . . 180.0 no C6 N2 C5 N1 . . 0.0 no C4 N2 C5 N1 . . 180.0 no C6 N2 C5 C3 . . 180.0 no C4 N2 C5 C3 . . 0.0 no O2 C3 C5 N1 7_565 . -168.8(8) no O2 C3 C5 N1 . . 168.8(8) no O1 C3 C5 N1 . . -16.10(10) no O1 C3 C5 N1 7_565 . 16.10(10) no O2 C3 C5 N2 7_565 . 11.2(8) no O2 C3 C5 N2 . . -11.2(8) no O1 C3 C5 N2 . . 163.90(10) no O1 C3 C5 N2 7_565 . -163.90(10) no C5 N2 C6 C7 . . 0.0 no C4 N2 C6 C7 . . 180.0 no C5 N1 C7 C6 . . 0.0 no C5 N1 C7 N3 . . 180.0 no N2 C6 C7 N1 . . 0.0 no N2 C6 C7 N3 . . 180.0 no O4 N3 C7 N1 . . 0.0 no O3 N3 C7 N1 . . 180.0 no O4 N3 C7 C6 . . 180.0 no O3 N3 C7 C6 . . 0.0 no