#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2204092.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_2204092 loop_ _publ_author_name 'Zeng, Xiang Chao' 'Xu, Shi Hai' 'Deng, Qin Ying' 'Cai, Ji Wen' 'Guo, Shu Hao' 'Gu, Jian' 'He, Dong Hong' _publ_section_title ; Methyl (4,5-dibromo-1-methyl-1H-pyrrole-2-carbonylamino)acetate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1283 _journal_page_last o1284 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C9 H10 Br2 N2 O3' _chemical_formula_moiety 'C9 H10 Br2 N2 O3' _chemical_formula_sum 'C9 H10 Br2 N2 O3' _chemical_formula_weight 354.01 _chemical_melting_point 389 _chemical_name_systematic ; ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.4237(18) _cell_length_b 13.445(4) _cell_length_c 14.054(4) _cell_measurement_reflns_used 907 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 26.14 _cell_measurement_theta_min 2.90 _cell_volume 1213.8(6) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'SHELXTL (Bruker, 1998)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD 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 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7341 _diffrn_reflns_theta_full 27.04 _diffrn_reflns_theta_max 27.04 _diffrn_reflns_theta_min 2.10 _exptl_absorpt_coefficient_mu 6.672 _exptl_absorpt_correction_T_max 0.322 _exptl_absorpt_correction_T_min 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.937 _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 688 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.274 _refine_diff_density_min -0.584 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.028(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 2621 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0275 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.0575P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.0682 _reflns_number_gt 2257 _reflns_number_total 2621 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wk6020.cif _[local]_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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2204092 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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_type_symbol Br1 0.80110(6) 0.93562(3) 0.86822(3) 0.05792(13) Uani d . 1 Br Br2 0.34587(7) 0.78812(4) 0.92941(2) 0.06719(15) Uani d . 1 Br C1 0.5839(5) 0.8972(3) 0.7897(2) 0.0387(7) Uani d . 1 C C2 0.4104(5) 0.8420(3) 0.8109(2) 0.0395(7) Uani d . 1 C C3 0.2917(5) 0.8336(3) 0.7281(2) 0.0399(7) Uani d . 1 C H3A 0.1661 0.7998 0.7219 0.048 Uiso calc R 1 H C4 0.3940(5) 0.8845(2) 0.6576(2) 0.0341(7) Uani d . 1 C C5 0.7331(6) 0.9813(4) 0.6468(3) 0.0624(10) Uani d . 1 C H5A 0.8414 0.9986 0.6909 0.094 Uiso calc R 1 H H5B 0.6721 1.0409 0.6215 0.094 Uiso calc R 1 H H5C 0.7908 0.9426 0.5959 0.094 Uiso calc R 1 H C6 0.3315(5) 0.9014(2) 0.5578(2) 0.0388(7) Uani d . 1 C C7 0.0871(5) 0.8657(3) 0.4341(2) 0.0449(8) Uani d . 1 C H7A 0.0590 0.9364 0.4284 0.054 Uiso calc R 1 H H7B -0.0442 0.8308 0.4275 0.054 Uiso calc R 1 H C8 0.2300(5) 0.8346(2) 0.3548(2) 0.0373(7) Uani d . 1 C C9 0.2957(7) 0.8563(3) 0.1911(2) 0.0581(10) Uani d . 1 C H9A 0.2413 0.8925 0.1378 0.087 Uiso calc R 1 H H9B 0.2885 0.7863 0.1783 0.087 Uiso calc R 1 H H9C 0.4381 0.8751 0.2016 0.087 Uiso calc R 1 H N1 0.5750(4) 0.9239(2) 0.69537(17) 0.0377(6) Uani d . 1 N N2 0.1711(4) 0.8461(2) 0.52682(16) 0.0411(6) Uani d . 1 N H2A 0.1197 0.7998 0.5619 0.049 Uiso calc R 1 H O1 0.4118(4) 0.9631(2) 0.50695(17) 0.0620(7) Uani d . 1 O O2 0.3706(4) 0.7764(2) 0.36135(17) 0.0587(7) Uani d . 1 O O3 0.1756(4) 0.87870(18) 0.27403(15) 0.0513(6) Uani d . 1 O 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 Br1 0.04399(19) 0.0715(3) 0.0582(2) 0.00563(18) -0.01661(16) -0.02274(19) Br2 0.0695(3) 0.1003(3) 0.03177(17) 0.0035(2) 0.00218(17) 0.0141(2) C1 0.0331(14) 0.0463(19) 0.0366(16) 0.0069(14) -0.0040(12) -0.0141(13) C2 0.0417(17) 0.050(2) 0.0269(14) 0.0032(15) 0.0012(12) -0.0005(14) C3 0.0364(15) 0.0482(18) 0.0350(15) -0.0044(16) 0.0030(13) 0.0009(14) C4 0.0327(14) 0.0389(17) 0.0305(15) -0.0010(13) -0.0001(11) -0.0029(12) C5 0.0449(19) 0.076(3) 0.066(2) -0.0219(19) 0.0044(17) 0.007(2) C6 0.0411(16) 0.0446(18) 0.0308(14) -0.0046(14) 0.0046(13) 0.0024(13) C7 0.0420(16) 0.056(2) 0.0366(16) 0.0061(16) -0.0033(14) -0.0013(16) C8 0.0412(16) 0.0377(16) 0.0331(15) -0.0001(14) -0.0041(12) 0.0010(13) C9 0.082(3) 0.060(2) 0.0333(17) -0.012(2) 0.0102(18) 0.0009(16) N1 0.0337(12) 0.0423(16) 0.0371(13) -0.0052(12) 0.0026(10) -0.0056(12) N2 0.0434(14) 0.0517(16) 0.0281(12) -0.0061(15) -0.0003(11) 0.0023(12) O1 0.0747(18) 0.0682(17) 0.0431(13) -0.0267(15) 0.0005(12) 0.0148(13) O2 0.0620(16) 0.0673(17) 0.0467(13) 0.0279(14) 0.0008(12) 0.0033(13) O3 0.0672(15) 0.0527(14) 0.0341(11) 0.0146(14) -0.0021(12) 0.0074(10) 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' Br Br -0.2901 2.4595 '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 N1 108.5(3) C2 C1 Br1 129.3(2) N1 C1 Br1 122.2(2) C1 C2 C3 107.8(3) C1 C2 Br2 125.8(2) C3 C2 Br2 126.3(2) C4 C3 C2 107.5(3) C3 C4 N1 108.4(3) C3 C4 C6 129.2(3) N1 C4 C6 122.3(3) O1 C6 N2 121.0(3) O1 C6 C4 123.4(3) N2 C6 C4 115.6(3) N2 C7 C8 113.1(3) O2 C8 O3 123.7(3) O2 C8 C7 125.8(3) O3 C8 C7 110.4(3) C1 N1 C4 107.8(3) C1 N1 C5 124.4(3) C4 N1 C5 127.8(3) C6 N2 C7 118.7(3) C8 O3 C9 117.5(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C1 1.853(3) Br2 C2 1.863(3) C1 C2 1.372(5) C1 N1 1.374(4) C2 C3 1.396(4) C3 C4 1.372(4) C4 N1 1.384(4) C4 C6 1.476(4) C5 N1 1.447(4) C6 O1 1.211(4) C6 N2 1.343(4) C7 N2 1.435(4) C7 C8 1.503(4) C8 O2 1.199(4) C8 O3 1.328(4) C9 O3 1.430(4) 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 N2 H2A O2 4_466 0.86 2.18 2.984(4) 155 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 N1 C1 C2 C3 0.4(4) Br1 C1 C2 C3 179.5(3) N1 C1 C2 Br2 -179.6(2) Br1 C1 C2 Br2 -0.5(5) C1 C2 C3 C4 -0.4(4) Br2 C2 C3 C4 179.6(3) C2 C3 C4 N1 0.3(4) C2 C3 C4 C6 -177.8(3) C3 C4 C6 O1 164.9(4) N1 C4 C6 O1 -12.9(5) C3 C4 C6 N2 -12.5(5) N1 C4 C6 N2 169.8(3) N2 C7 C8 O2 19.6(5) N2 C7 C8 O3 -162.3(3) C2 C1 N1 C4 -0.2(4) Br1 C1 N1 C4 -179.4(2) C2 C1 N1 C5 -178.9(3) Br1 C1 N1 C5 1.9(5) C3 C4 N1 C1 0.0(4) C6 C4 N1 C1 178.1(3) C3 C4 N1 C5 178.7(4) C6 C4 N1 C5 -3.2(5) O1 C6 N2 C7 -4.0(5) C4 C6 N2 C7 173.4(3) C8 C7 N2 C6 71.0(4) O2 C8 O3 C9 -1.4(5) C7 C8 O3 C9 -179.6(3)